Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Carboxyatractyloside
- DrugBank Accession Number
- DB02426
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Carboxyatractyloside (DB02426)
- Weight
- Average: 786.816
Monoisotopic: 786.20747067 - Chemical Formula
- C31H46O19S2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism UADP/ATP translocase 1 Not Available 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Terpene glycosides
- Direct Parent
- Diterpene glycosides
- Alternative Parents
- Kaurane diterpenoids / Saccharolipids / Fatty acyl glycosides of mono- and disaccharides / O-glycosyl compounds / Monosaccharide sulfates / Tricarboxylic acids and derivatives / Fatty acid esters / Alkyl sulfates / Sulfuric acid monoesters / Oxanes show 11 more
- Substituents
- Acetal / Alcohol / Aliphatic heteropolycyclic compound / Alkyl hydroperoxide / Alkyl sulfate / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol show 27 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- PH9ATM6F5U
- CAS number
- 33286-30-5
- InChI Key
- CYBVQIBJEFQVPD-GWDNDVLHSA-N
- InChI
- InChI=1S/C31H46O19S2/c1-14(2)9-21(32)48-24-23(50-52(42,43)44)22(49-51(39,40)41)18(13-45-38)47-26(24)46-17-11-29(4)19-6-5-16-10-30(19,25(33)15(16)3)8-7-20(29)31(12-17,27(34)35)28(36)37/h14,16-20,22-26,33,38H,3,5-13H2,1-2,4H3,(H,34,35)(H,36,37)(H,39,40,41)(H,42,43,44)/t16-,17-,18+,19-,20-,22+,23+,24-,25+,26+,29-,30-/m1/s1
- IUPAC Name
- (1R,4R,7R,9R,10R,13R,15S)-7-{[(2S,3R,4R,5S,6S)-6-(hydroperoxymethyl)-3-[(3-methylbutanoyl)oxy]-4,5-bis(sulfooxy)oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5,5-dicarboxylic acid
- SMILES
- CC(C)CC(=O)O[C@H]1[C@@H](O[C@@H]2C[C@]3(C)[C@H]4CC[C@@H]5C[C@@]4(CC[C@H]3C(C2)(C(O)=O)C(O)=O)[C@@H](O)C5=C)O[C@@H](COO)[C@H](OS(O)(=O)=O)[C@@H]1OS(O)(=O)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 46936378
- PubChem Substance
- 46505904
- ChemSpider
- 26329724
- ZINC
- ZINC000096006053
- PDBe Ligand
- CXT
- Wikipedia
- Carboxyatractyloside
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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
Property Value Source Water Solubility 2.17 mg/mL ALOGPS logP -0.38 ALOGPS logP -1.5 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) -2.3 Chemaxon pKa (Strongest Basic) -0.69 Chemaxon Physiological Charge -4 Chemaxon Hydrogen Acceptor Count 16 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 296.25 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 168.79 m3·mol-1 Chemaxon Polarizability 75.05 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6729 Blood Brain Barrier + 0.8116 Caco-2 permeable - 0.663 P-glycoprotein substrate Substrate 0.7666 P-glycoprotein inhibitor I Inhibitor 0.8334 P-glycoprotein inhibitor II Non-inhibitor 0.8965 Renal organic cation transporter Non-inhibitor 0.8597 CYP450 2C9 substrate Non-substrate 0.8639 CYP450 2D6 substrate Non-substrate 0.8248 CYP450 3A4 substrate Substrate 0.6721 CYP450 1A2 substrate Non-inhibitor 0.7302 CYP450 2C9 inhibitor Non-inhibitor 0.7232 CYP450 2D6 inhibitor Non-inhibitor 0.8683 CYP450 2C19 inhibitor Non-inhibitor 0.7042 CYP450 3A4 inhibitor Non-inhibitor 0.8245 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8464 Ames test Non AMES toxic 0.6048 Carcinogenicity Non-carcinogens 0.7699 Biodegradation Not ready biodegradable 0.9679 Rat acute toxicity 2.7066 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8288 hERG inhibition (predictor II) Inhibitor 0.5079
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 262.94748 predictedDeepCCS 1.0 (2019) [M+H]+ 264.67117 predictedDeepCCS 1.0 (2019) [M+Na]+ 271.205 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- ADP:ATP antiporter that mediates import of ADP into the mitochondrial matrix for ATP synthesis, and export of ATP out to fuel the cell (PubMed:21586654, PubMed:27693233). Cycles between the cytoplasmic-open state (c-state) and the matrix-open state (m-state): operates by the alternating access mechanism with a single substrate-binding site intermittently exposed to either the cytosolic (c-state) or matrix (m-state) side of the inner mitochondrial membrane (By similarity). In addition to its ADP:ATP antiporter activity, also involved in mitochondrial uncoupling and mitochondrial permeability transition pore (mPTP) activity (PubMed:31883789). Plays a role in mitochondrial uncoupling by acting as a proton transporter: proton transport uncouples the proton flows via the electron transport chain and ATP synthase to reduce the efficiency of ATP production and cause mitochondrial thermogenesis (By similarity). Proton transporter activity is inhibited by ADP:ATP antiporter activity, suggesting that SLC25A4/ANT1 acts as a master regulator of mitochondrial energy output by maintaining a delicate balance between ATP production (ADP:ATP antiporter activity) and thermogenesis (proton transporter activity) (By similarity). Proton transporter activity requires free fatty acids as cofactor, but does not transport it (By similarity). Also plays a key role in mPTP opening, a non-specific pore that enables free passage of the mitochondrial membranes to solutes of up to 1.5 kDa, and which contributes to cell death (PubMed:31883789). It is however unclear if SLC25A4/ANT1 constitutes a pore-forming component of mPTP or regulates it (By similarity). Acts as a regulator of mitophagy independently of ADP:ATP antiporter activity: promotes mitophagy via interaction with TIMM44, leading to inhibit the presequence translocase TIMM23, thereby promoting stabilization of PINK1 (By similarity)
- Specific Function
- Adenine transmembrane transporter activity
- Gene Name
- SLC25A4
- Uniprot ID
- P12235
- Uniprot Name
- ADP/ATP translocase 1
- Molecular Weight
- 33064.265 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- 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]
Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:16