Cytochrome P450 1B1
Details
- Name
- Cytochrome P450 1B1
- Synonyms
- 1.14.14.1
- CYPIB1
- Hydroperoxy icosatetraenoate dehydratase
- Gene Name
- CYP1B1
- UniProtKB Entry
- Q16678Swiss-Prot
- Organism
- Humans
- NCBI Taxonomy ID
- 9606
- Amino acid sequence
>lcl|BSEQ0016314|Cytochrome P450 1B1 MGTSLSPNDPWPLNPLSIQQTTLLLLLSVLATVHVGQRLLRQRRRQLRSAPPGPFAWPLI GNAAAVGQAAHLSFARLARRYGDVFQIRLGSCPIVVLNGERAIHQALVQQGSAFADRPAF ASFRVVSGGRSMAFGHYSEHWKVQRRAAHSMMRNFFTRQPRSRQVLEGHVLSEARELVAL LVRGSADGAFLDPRPLTVVAVANVMSAVCFGCRYSHDDPEFRELLSHNEEFGRTVGAGSL VDVMPWLQYFPNPVRTVFREFEQLNRNFSNFILDKFLRHCESLRPGAAPRDMMDAFILSA EKKAAGDSHGGGARLDLENVPATITDIFGASQDTLSTALQWLLLLFTRYPDVQTRVQAEL DQVVGRDRLPCMGDQPNLPYVLAFLYEAMRFSSFVPVTIPHATTANTSVLGYHIPKDTVV FVNQWSVNHDPLKWPNPENFDPARFLDKDGLINKDLTSRVMIFSVGKRRCIGEELSKMQL FLFISILAHQCDFRANPNEPAKMNFSYGLTIKPKSFKVNVTLRESMELLDSAVQNLQAKE TCQ
- Number of residues
- 543
- Molecular Weight
- 60845.33
- Theoretical pI
- 9.23
- GO Classification
- Functionsestrogen 16-alpha-hydroxylase activity / hydroperoxy icosatetraenoate dehydratase activityProcessesadrenal gland development / benzene-containing compound metabolic process / blood vessel endothelial cell migration / cellular response to cAMP / cellular response to cortisol stimulus / cellular response to luteinizing hormone stimulus / cellular response to progesterone stimulus / cellular response to toxic substance / cellular response to tumor necrosis factor / DNA modification / estrous cycle / ganglion development / male gonad development / negative regulation of cell population proliferation / positive regulation of DNA biosynthetic process / positive regulation of reactive oxygen species metabolic process / positive regulation of receptor signaling pathway via JAK-STAT / positive regulation of smooth muscle cell migration / positive regulation of translation / response to 3-methylcholanthrene / response to arsenic-containing substance / response to dexamethasone / response to estradiol / response to follicle-stimulating hormone / response to indole-3-methanol / response to nutrientComponentsintracellular membrane-bounded organelle
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:15258110, PubMed:20972997). Exhibits catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2- and 4-hydroxy E1 and E2. Displays a predominant hydroxylase activity toward E2 at the C-4 position (PubMed:11555828, PubMed:12865317). Metabolizes testosterone and progesterone to B or D ring hydroxylated metabolites (PubMed:10426814). May act as a major enzyme for all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376, PubMed:15258110). Catalyzes the epoxidation of double bonds of certain PUFA. Converts arachidonic acid toward epoxyeicosatrienoic acid (EpETrE) regioisomers, 8,9-, 11,12-, and 14,15- EpETrE, that function as lipid mediators in the vascular system (PubMed:20972997). Additionally, displays dehydratase activity toward oxygenated eicosanoids hydroperoxyeicosatetraenoates (HpETEs). This activity is independent of cytochrome P450 reductase, NADPH, and O2 (PubMed:21068195). Also involved in the oxidative metabolism of xenobiotics, particularly converting polycyclic aromatic hydrocarbons and heterocyclic aryl amines procarcinogens to DNA-damaging products (PubMed:10426814). Plays an important role in retinal vascular development. Under hyperoxic O2 conditions, promotes retinal angiogenesis and capillary morphogenesis, likely by metabolizing the oxygenated products generated during the oxidative stress. Also, contributes to oxidative homeostasis and ultrastructural organization and function of trabecular meshwork tissue through modulation of POSTN expression (By similarity)
- Specific Function
- aromatase activity
- Pfam Domain Function
- p450 (PF00067)
- Signal Regions
- Not Available
- Transmembrane Regions
- Not Available
- Cellular Location
- Endoplasmic reticulum membrane
- Gene sequence
>lcl|BSEQ0016315|Cytochrome P450 1B1 (CYP1B1) ATGGGCACCAGCCTCAGCCCGAACGACCCTTGGCCGCTAAACCCGCTGTCCATCCAGCAG ACCACGCTCCTGCTACTCCTGTCGGTGCTGGCCACTGTGCATGTGGGCCAGCGGCTGCTG AGGCAACGGAGGCGGCAGCTCCGGTCCGCGCCCCCGGGCCCGTTTGCGTGGCCACTGATC GGAAACGCGGCGGCGGTGGGCCAGGCGGCTCACCTCTCGTTCGCTCGCCTGGCGCGGCGC TACGGCGACGTTTTCCAGATCCGCCTGGGCAGCTGCCCCATAGTGGTGCTGAATGGCGAG CGCGCCATCCACCAGGCCCTGGTGCAGCAGGGCTCGGCCTTCGCCGACCGGCCGGCCTTC GCCTCCTTCCGTGTGGTGTCCGGCGGCCGCAGCATGGCTTTCGGCCACTACTCGGAGCAC TGGAAGGTGCAGCGGCGCGCAGCCCACAGCATGATGCGCAACTTCTTCACGCGCCAGCCG CGCAGCCGCCAAGTCCTCGAGGGCCACGTGCTGAGCGAGGCGCGCGAGCTGGTGGCGCTG CTGGTGCGCGGCAGCGCGGACGGCGCCTTCCTCGACCCGAGGCCGCTGACCGTCGTGGCC GTGGCCAACGTCATGAGTGCCGTGTGTTTCGGCTGCCGCTACAGCCACGACGACCCCGAG TTCCGTGAGCTGCTCAGCCACAACGAAGAGTTCGGGCGCACGGTGGGCGCGGGCAGCCTG GTGGACGTGATGCCCTGGCTGCAGTACTTCCCCAACCCGGTGCGCACCGTTTTCCGCGAA TTCGAGCAGCTCAACCGCAACTTCAGCAACTTCATCCTGGACAAGTTCTTGAGGCACTGC GAAAGCCTTCGGCCCGGGGCCGCCCCCCGCGACATGATGGACGCCTTTATCCTCTCTGCG GAAAAGAAGGCGGCCGGGGACTCGCACGGTGGTGGCGCGCGGCTGGATTTGGAGAACGTA CCGGCCACTATCACTGACATCTTCGGCGCCAGCCAGGACACCCTGTCCACCGCGCTGCAG TGGCTGCTCCTCCTCTTCACCAGGTATCCTGATGTGCAGACTCGAGTGCAGGCAGAATTG GATCAGGTCGTGGGGAGGGACCGTCTGCCTTGTATGGGTGACCAGCCCAACCTGCCCTAT GTCCTGGCCTTCCTTTATGAAGCCATGCGCTTCTCCAGCTTTGTGCCTGTCACTATTCCT CATGCCACCACTGCCAACACCTCTGTCTTGGGCTACCACATTCCCAAGGACACTGTGGTT TTTGTCAACCAGTGGTCTGTGAATCATGACCCACTGAAGTGGCCTAACCCGGAGAACTTT GATCCAGCTCGATTCTTGGACAAGGATGGCCTCATCAACAAGGACCTGACCAGCAGAGTG ATGATTTTTTCAGTGGGCAAAAGGCGGTGCATTGGCGAAGAACTTTCTAAGATGCAGCTT TTTCTCTTCATCTCCATCCTGGCTCACCAGTGCGATTTCAGGGCCAACCCAAATGAGCCT GCGAAAATGAATTTCAGTTATGGTCTAACCATTAAACCCAAGTCATTTAAAGTCAATGTC ACTCTCAGAGAGTCCATGGAGCTCCTTGATAGTGCTGTCCAAAATTTACAAGCCAAGGAA ACTTGCCAATAA
- Chromosome Location
- 2
- Locus
- 2p22.2
- External Identifiers
Resource Link UniProtKB ID Q16678 UniProtKB Entry Name CP1B1_HUMAN GenBank Protein ID 501031 GenBank Gene ID U03688 GeneCard ID CYP1B1 GenAtlas ID CYP1B1 HGNC ID HGNC:2597 PDB ID(s) 3PM0, 6IQ5 KEGG ID hsa:1545 IUPHAR/Guide To Pharmacology ID 1320 NCBI Gene ID 1545 - General References
- Sutter TR, Tang YM, Hayes CL, Wo YY, Jabs EW, Li X, Yin H, Cody CW, Greenlee WF: Complete cDNA sequence of a human dioxin-inducible mRNA identifies a new gene subfamily of cytochrome P450 that maps to chromosome 2. J Biol Chem. 1994 May 6;269(18):13092-9. [Article]
- Tang YM, Wo YY, Stewart J, Hawkins AL, Griffin CA, Sutter TR, Greenlee WF: Isolation and characterization of the human cytochrome P450 CYP1B1 gene. J Biol Chem. 1996 Nov 8;271(45):28324-30. [Article]
- Gerhard DS, Wagner L, Feingold EA, Shenmen CM, Grouse LH, Schuler G, Klein SL, Old S, Rasooly R, Good P, Guyer M, Peck AM, Derge JG, Lipman D, Collins FS, Jang W, Sherry S, Feolo M, Misquitta L, Lee E, Rotmistrovsky K, Greenhut SF, Schaefer CF, Buetow K, Bonner TI, Haussler D, Kent J, Kiekhaus M, Furey T, Brent M, Prange C, Schreiber K, Shapiro N, Bhat NK, Hopkins RF, Hsie F, Driscoll T, Soares MB, Casavant TL, Scheetz TE, Brown-stein MJ, Usdin TB, Toshiyuki S, Carninci P, Piao Y, Dudekula DB, Ko MS, Kawakami K, Suzuki Y, Sugano S, Gruber CE, Smith MR, Simmons B, Moore T, Waterman R, Johnson SL, Ruan Y, Wei CL, Mathavan S, Gunaratne PH, Wu J, Garcia AM, Hulyk SW, Fuh E, Yuan Y, Sneed A, Kowis C, Hodgson A, Muzny DM, McPherson J, Gibbs RA, Fahey J, Helton E, Ketteman M, Madan A, Rodrigues S, Sanchez A, Whiting M, Madari A, Young AC, Wetherby KD, Granite SJ, Kwong PN, Brinkley CP, Pearson RL, Bouffard GG, Blakesly RW, Green ED, Dickson MC, Rodriguez AC, Grimwood J, Schmutz J, Myers RM, Butterfield YS, Griffith M, Griffith OL, Krzywinski MI, Liao N, Morin R, Palmquist D, Petrescu AS, Skalska U, Smailus DE, Stott JM, Schnerch A, Schein JE, Jones SJ, Holt RA, Baross A, Marra MA, Clifton S, Makowski KA, Bosak S, Malek J: The status, quality, and expansion of the NIH full-length cDNA project: the Mammalian Gene Collection (MGC). Genome Res. 2004 Oct;14(10B):2121-7. [Article]
- Shimada T, Watanabe J, Kawajiri K, Sutter TR, Guengerich FP, Gillam EM, Inoue K: Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13. doi: 10.1093/carcin/20.8.1607. [Article]
- Vincent A, Billingsley G, Priston M, Williams-Lyn D, Sutherland J, Glaser T, Oliver E, Walter MA, Heathcote G, Levin A, Heon E: Phenotypic heterogeneity of CYP1B1: mutations in a patient with Peters' anomaly. J Med Genet. 2001 May;38(5):324-6. [Article]
- Choudhary D, Jansson I, Stoilov I, Sarfarazi M, Schenkman JB: Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1. Drug Metab Dispos. 2004 Aug;32(8):840-7. [Article]
- Jang HH, Kim SY, Kang JY, Park SH, Ryu SH, Ahn T, Yun CH: Increase of human CYP1B1 activities by acidic phospholipids and kinetic deuterium isotope effects on CYP1B1 substrate oxidation. J Biochem. 2012 Nov;152(5):433-42. doi: 10.1093/jb/mvs087. Epub 2012 Aug 9. [Article]
- Nishida CR, Everett S, Ortiz de Montellano PR: Specificity determinants of CYP1B1 estradiol hydroxylation. Mol Pharmacol. 2013 Sep;84(3):451-8. doi: 10.1124/mol.113.087700. Epub 2013 Jul 2. [Article]
- Poon CH, Wong TY, Wang Y, Tsuchiya Y, Nakajima M, Yokoi T, Leung LK: The citrus flavanone naringenin suppresses CYP1B1 transactivation through antagonising xenobiotic-responsive element binding. Br J Nutr. 2013 May;109(9):1598-605. doi: 10.1017/S0007114512003595. Epub 2012 Aug 31. [Article]
- Wang A, Savas U, Stout CD, Johnson EF: Structural characterization of the complex between alpha-naphthoflavone and human cytochrome P450 1B1. J Biol Chem. 2011 Feb 18;286(7):5736-43. doi: 10.1074/jbc.M110.204420. Epub 2010 Dec 8. [Article]
- Bejjani BA, Lewis RA, Tomey KF, Anderson KL, Dueker DK, Jabak M, Astle WF, Otterud B, Leppert M, Lupski JR: Mutations in CYP1B1, the gene for cytochrome P4501B1, are the predominant cause of primary congenital glaucoma in Saudi Arabia. Am J Hum Genet. 1998 Feb;62(2):325-33. [Article]
- Stoilov I, Akarsu AN, Alozie I, Child A, Barsoum-Homsy M, Turacli ME, Or M, Lewis RA, Ozdemir N, Brice G, Aktan SG, Chevrette L, Coca-Prados M, Sarfarazi M: Sequence analysis and homology modeling suggest that primary congenital glaucoma on 2p21 results from mutations disrupting either the hinge region or the conserved core structures of cytochrome P4501B1. Am J Hum Genet. 1998 Mar;62(3):573-84. [Article]
- Bailey LR, Roodi N, Dupont WD, Parl FF: Association of cytochrome P450 1B1 (CYP1B1) polymorphism with steroid receptor status in breast cancer. Cancer Res. 1998 Nov 15;58(22):5038-41. [Article]
- Plasilova M, Stoilov I, Sarfarazi M, Kadasi L, Ferakova E, Ferak V: Identification of a single ancestral CYP1B1 mutation in Slovak Gypsies (Roms) affected with primary congenital glaucoma. J Med Genet. 1999 Apr;36(4):290-4. [Article]
- Bejjani BA, Stockton DW, Lewis RA, Tomey KF, Dueker DK, Jabak M, Astle WF, Lupski JR: Multiple CYP1B1 mutations and incomplete penetrance in an inbred population segregating primary congenital glaucoma suggest frequent de novo events and a dominant modifier locus. Hum Mol Genet. 2000 Feb 12;9(3):367-74. [Article]
- Ohtake Y, Kubota R, Tanino T, Miyata H, Mashima Y: Novel compound heterozygous mutations in the cytochrome P4501B1 gene (CYP1B1) in a Japanese patient with primary congenital glaucoma. Ophthalmic Genet. 2000 Sep;21(3):191-3. [Article]
- Watanabe J, Shimada T, Gillam EM, Ikuta T, Suemasu K, Higashi Y, Gotoh O, Kawajiri K: Association of CYP1B1 genetic polymorphism with incidence to breast and lung cancer. Pharmacogenetics. 2000 Feb;10(1):25-33. [Article]
- Mashima Y, Suzuki Y, Sergeev Y, Ohtake Y, Tanino T, Kimura I, Miyata H, Aihara M, Tanihara H, Inatani M, Azuma N, Iwata T, Araie M: Novel cytochrome P4501B1 (CYP1B1) gene mutations in Japanese patients with primary congenital glaucoma. Invest Ophthalmol Vis Sci. 2001 Sep;42(10):2211-6. [Article]
- Vincent AL, Billingsley G, Buys Y, Levin AV, Priston M, Trope G, Williams-Lyn D, Heon E: Digenic inheritance of early-onset glaucoma: CYP1B1, a potential modifier gene. Am J Hum Genet. 2002 Feb;70(2):448-60. Epub 2002 Jan 3. [Article]
- Panicker SG, Reddy AB, Mandal AK, Ahmed N, Nagarajaram HA, Hasnain SE, Balasubramanian D: Identification of novel mutations causing familial primary congenital glaucoma in Indian pedigrees. Invest Ophthalmol Vis Sci. 2002 May;43(5):1358-66. [Article]
- Stoilov IR, Costa VP, Vasconcellos JP, Melo MB, Betinjane AJ, Carani JC, Oltrogge EV, Sarfarazi M: Molecular genetics of primary congenital glaucoma in Brazil. Invest Ophthalmol Vis Sci. 2002 Jun;43(6):1820-7. [Article]
- Aklillu E, Oscarson M, Hidestrand M, Leidvik B, Otter C, Ingelman-Sundberg M: Functional analysis of six different polymorphic CYP1B1 enzyme variants found in an Ethiopian population. Mol Pharmacol. 2002 Mar;61(3):586-94. [Article]
- Chakrabarti S, Komatireddy S, Mandal AK, Balasubramanian D: Gene symbol: CYP1B1. Disease: glaucoma, primary congenital. Hum Genet. 2003 Nov;113(6):556. [Article]
- Colomb E, Kaplan J, Garchon HJ: Novel cytochrome P450 1B1 (CYP1B1) mutations in patients with primary congenital glaucoma in France. Hum Mutat. 2003 Dec;22(6):496. [Article]
- Sitorus R, Ardjo SM, Lorenz B, Preising M: CYP1B1 gene analysis in primary congenital glaucoma in Indonesian and European patients. J Med Genet. 2003 Jan;40(1):e9. [Article]
- Melki R, Colomb E, Lefort N, Brezin AP, Garchon HJ: CYP1B1 mutations in French patients with early-onset primary open-angle glaucoma. J Med Genet. 2004 Sep;41(9):647-51. [Article]
- Reddy AB, Kaur K, Mandal AK, Panicker SG, Thomas R, Hasnain SE, Balasubramanian D, Chakrabarti S: Mutation spectrum of the CYP1B1 gene in Indian primary congenital glaucoma patients. Mol Vis. 2004 Sep 30;10:696-702. [Article]
- Curry SM, Daou AG, Hermanns P, Molinari A, Lewis RA, Bejjani BA: Cytochrome P4501B1 mutations cause only part of primary congenital glaucoma in Ecuador. Ophthalmic Genet. 2004 Mar;25(1):3-9. [Article]
- Alfadhli S, Behbehani A, Elshafey A, Abdelmoaty S, Al-Awadi S: Molecular and clinical evaluation of primary congenital glaucoma in Kuwait. Am J Ophthalmol. 2006 Mar;141(3):512-6. [Article]
- Acharya M, Mookherjee S, Bhattacharjee A, Bandyopadhyay AK, Daulat Thakur SK, Bhaduri G, Sen A, Ray K: Primary role of CYP1B1 in Indian juvenile-onset POAG patients. Mol Vis. 2006 Apr 20;12:399-404. [Article]
- Chavarria-Soley G, Michels-Rautenstrauss K, Pasutto F, Flikier D, Flikier P, Cirak S, Bejjani B, Winters DL, Lewis RA, Mardin C, Reis A, Rautenstrauss B: Primary congenital glaucoma and Rieger's anomaly: extended haplotypes reveal founder effects for eight distinct CYP1B1 mutations. Mol Vis. 2006 May 22;12:523-31. [Article]
- Lopez-Garrido MP, Sanchez-Sanchez F, Lopez-Martinez F, Aroca-Aguilar JD, Blanco-Marchite C, Coca-Prados M, Escribano J: Heterozygous CYP1B1 gene mutations in Spanish patients with primary open-angle glaucoma. Mol Vis. 2006 Jul 11;12:748-55. [Article]
- Chavarria-Soley G, Sticht H, Aklillu E, Ingelman-Sundberg M, Pasutto F, Reis A, Rautenstrauss B: Mutations in CYP1B1 cause primary congenital glaucoma by reduction of either activity or abundance of the enzyme. Hum Mutat. 2008 Sep;29(9):1147-53. doi: 10.1002/humu.20786. [Article]
Associated Data
- Bio-Entities
Bio-Entity Type Cytochrome P450 1B1 (Humans) protein primaryCytochrome P450 1A Subfamily (Humans) protein - Drug Relations
Drug Drug group Pharmacological action? Type Actions Details Melatonin approved, nutraceutical, vet_approved unknown enzyme substrateinhibitor Details Tamoxifen approved unknown enzyme substrateinhibitor Details Propofol approved, investigational, vet_approved unknown enzyme inhibitor Details Resveratrol investigational no enzyme substrateinhibitor Details Amodiaquine approved, investigational unknown enzyme substrate Details Biotin approved, investigational, nutraceutical unknown enzyme inducer Details Caffeine approved unknown enzyme substrate Details Daunorubicin approved unknown enzyme inhibitor Details Docetaxel approved, investigational unknown enzyme binder Details Doxorubicin approved, investigational no enzyme inhibitorinducer Details Estradiol approved, investigational, vet_approved unknown enzyme substrate Details Estrone approved unknown enzyme substrate Details Flutamide approved, investigational unknown enzyme substrate Details Ketoconazole approved, investigational unknown enzyme inhibitor Details Lansoprazole approved, investigational unknown enzyme inducer Details Mitoxantrone approved, investigational unknown enzyme inhibitor Details Omeprazole approved, investigational, vet_approved unknown enzyme inducer Details Paclitaxel approved, vet_approved unknown enzyme inhibitor Details Primaquine approved unknown enzyme inducer Details Progesterone approved, vet_approved unknown enzyme substrate Details Testosterone approved, investigational unknown enzyme substrate Details Theophylline approved unknown enzyme substrate Details Erlotinib approved, investigational unknown enzyme substrate Details Dasatinib approved, investigational unknown enzyme substrate Details 2-Methoxyestradiol investigational unknown target Details beta-Naphthoflavone experimental unknown target Details Flavone approved, experimental unknown target Details Genistein investigational unknown target Details Naringenin experimental unknown target Details Quercetin experimental, investigational unknown target Details Testosterone undecanoate approved, investigational unknown enzyme substrate Details Estradiol acetate approved, investigational, vet_approved unknown enzyme substrate Details Estradiol benzoate approved, investigational, vet_approved unknown enzyme substrate Details Estradiol cypionate approved, investigational, vet_approved unknown enzyme substrate Details Estradiol dienanthate approved, investigational, vet_approved unknown enzyme substrate Details Estradiol valerate approved, investigational, vet_approved unknown enzyme substrate Details Medical Cannabis experimental, investigational unknown enzyme inhibitor Details Triclocarban approved unknown enzyme inducer Details Triclabendazole approved, investigational unknown enzyme substrate Details Cannabidiol approved, investigational unknown target inhibitor Details Nabiximols investigational unknown target inhibitor Details Prednisone approved, vet_approved unknown enzyme inducer Details Hydrocortisone approved, vet_approved unknown enzyme inducer Details Budesonide approved unknown enzyme inducer Details Methylprednisolone approved, vet_approved unknown enzyme inducer Details Betamethasone approved, vet_approved unknown enzyme inducer Details Prednisolone phosphate approved, vet_approved unknown enzyme inducer Details Menadione approved, nutraceutical unknown enzyme inhibitor Details Ginkgo biloba approved, investigational, nutraceutical no enzyme inhibitor Details Isoprenaline approved, investigational unknown enzyme inducer Details Cannabidiol approved, investigational unknown enzyme inhibitor Details Dronabinol approved, illicit no enzyme inhibitor Details Cannabinol experimental, investigational unknown enzyme inhibitor Details Apigenin experimental yes target inhibitor Details Chrysin experimental yes target inhibitor Details Kaempherol experimental yes target inhibitor Details Isorhamnetin experimental yes target inhibitor Details Diosmetin experimental yes target inhibitor Details Chrysoeriol investigational yes target inhibitor Details