Colforsin

Identification

Generic Name
Colforsin
DrugBank Accession Number
DB02587
Background

Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant Coleus forskohlii. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.

Type
Small Molecule
Groups
Experimental, Investigational
Structure
Thumb
Weight
Average: 410.5012
Monoisotopic: 410.230453442
Chemical Formula
C22H34O7
Synonyms
  • 7β-acetoxy-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one
  • Coleonolk
  • Colforsin
  • colforsina
  • colforsine
  • colforsinum
  • Forskolin
External IDs
  • 266-410-9
  • HL-362
  • L-75-1362B
  • NSC-357088
  • NSC-375489

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAdenylate cyclase type 2Not AvailableHumans
UGuanine nucleotide-binding protein G(s) subunit alpha isoforms shortNot AvailableHumans
UAdenylate cyclase type 5Not AvailableHumans
UCystic fibrosis transmembrane conductance regulator
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Isosorbide mononitrateColforsin may increase the vasodilatory activities of Isosorbide mononitrate.
Patent BlueThe therapeutic efficacy of Colforsin can be decreased when used in combination with Patent Blue.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Triterpenoids
Direct Parent
Triterpenoids
Alternative Parents
Naphthopyrans / Naphthalenes / Pyrans / Oxanes / Tertiary alcohols / Secondary alcohols / Ketones / Cyclic alcohols and derivatives / Carboxylic acid esters / Polyols
show 5 more
Substituents
Alcohol / Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Dialkyl ether / Ether / Hydrocarbon derivative / Ketone
show 15 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
cyclic ketone, organic heterotricyclic compound, acetate ester, triol, labdane diterpenoid (CHEBI:42471) / Labdane and halimane diterpenoids, Diterpenoids (C20) (C09076) / Labdane and halimane diterpenoids (LMPR0104030004)
Affected organisms
Not Available

Chemical Identifiers

UNII
1F7A44V6OU
CAS number
66575-29-9
InChI Key
OHCQJHSOBUTRHG-KGGHGJDLSA-N
InChI
InChI=1S/C22H34O7/c1-8-19(5)11-14(25)22(27)20(6)13(24)9-10-18(3,4)16(20)15(26)17(28-12(2)23)21(22,7)29-19/h8,13,15-17,24,26-27H,1,9-11H2,2-7H3/t13-,15-,16-,17-,19-,20-,21+,22-/m0/s1
IUPAC Name
(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate
SMILES
[H][C@]1(O)CCC(C)(C)[C@]2([H])[C@]([H])(O)[C@]([H])(OC(C)=O)[C@@]3(C)O[C@](C)(CC(=O)[C@]3(O)[C@@]12C)C=C

References

Synthesis Reference

Emiko Yamasaki, Takaaki Ohkuma, "Lyophilized preparation of 6-(3-dimethylaminopropionyl)forskolin." U.S. Patent US5051132, issued June, 1974.

US5051132
General References
Not Available
KEGG Drug
D03584
KEGG Compound
C09076
PubChem Compound
47936
PubChem Substance
46509044
ChemSpider
43607
BindingDB
50010261
ChEBI
42471
ChEMBL
CHEMBL52606
ZINC
ZINC000003977779
PharmGKB
PA146096022
PDBe Ligand
FOK
Drugs.com
Drugs.com Drug Page
Wikipedia
Forskolin
PDB Entries
1ab8 / 1cjk / 1cjt / 1cju / 1cjv / 1cs4 / 1cul / 1tl7 / 1u0h / 3c14
show 4 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedNot AvailableGlaucoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.1 mg/mLALOGPS
logP1.28ALOGPS
logP1.36ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)11.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity104.47 m3·mol-1ChemAxon
Polarizability43.33 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6195
Blood Brain Barrier+0.6888
Caco-2 permeable-0.6796
P-glycoprotein substrateSubstrate0.8361
P-glycoprotein inhibitor IInhibitor0.8198
P-glycoprotein inhibitor IIInhibitor0.6788
Renal organic cation transporterNon-inhibitor0.8998
CYP450 2C9 substrateNon-substrate0.7961
CYP450 2D6 substrateNon-substrate0.892
CYP450 3A4 substrateSubstrate0.7016
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.935
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9606
Ames testNon AMES toxic0.6284
CarcinogenicityNon-carcinogens0.9539
BiodegradationNot ready biodegradable0.9792
Rat acute toxicity2.2384 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9911
hERG inhibition (predictor II)Non-inhibitor0.8782
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0001900000-7d8f5636999f6b276cd0
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0k92-0349200000-7e9f95896c6366092dc4
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0zgi-0895000000-d5ffd6e415b7071865cd
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0zfr-0941000000-0d4b697cc719902e9cd2

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein heterodimerization activity
Specific Function
Catalyzes the formation of the signaling molecule cAMP in response to G-protein signaling (PubMed:15385642). Down-stream signaling cascades mediate changes in gene expression patterns and lead to i...
Gene Name
ADCY2
Uniprot ID
Q08462
Uniprot Name
Adenylate cyclase type 2
Molecular Weight
123602.25 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Signal transducer activity
Specific Function
Guanine nucleotide-binding proteins (G proteins) function as transducers in numerous signaling pathways controlled by G protein-coupled receptors (GPCRs) (PubMed:17110384). Signaling involves the a...
Gene Name
GNAS
Uniprot ID
P63092
Uniprot Name
Guanine nucleotide-binding protein G(s) subunit alpha isoforms short
Molecular Weight
45664.205 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein heterodimerization activity
Specific Function
Catalyzes the formation of the signaling molecule cAMP in response to G-protein signaling (PubMed:15385642, PubMed:26206488, PubMed:24700542). Mediates signaling downstream of ADRB1 (PubMed:2470054...
Gene Name
ADCY5
Uniprot ID
O95622
Uniprot Name
Adenylate cyclase type 5
Molecular Weight
138906.37 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Pdz domain binding
Specific Function
Involved in the transport of chloride ions. May regulate bicarbonate secretion and salvage in epithelial cells by regulating the SLC4A7 transporter. Can inhibit the chloride channel activity of ANO...
Gene Name
CFTR
Uniprot ID
P13569
Uniprot Name
Cystic fibrosis transmembrane conductance regulator
Molecular Weight
168139.895 Da
References
  1. Ramesh Babu PB, Chidekel A, Utidjian L, Shaffer TH: Regulation of apical surface fluid and protein secretion in human airway epithelial cell line Calu-3. Biochem Biophys Res Commun. 2004 Jul 9;319(4):1132-7. [Article]

Transporters

Details
1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 25, 2021 00:50