Natural Product: ENC001007

NPs Basic Information

Download MOL File
Name
Cholic acid
Molecular Formula C24H40O5
IUPAC Name*
(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
InChI
InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
InChIKey
BHQCQFFYRZLCQQ-OELDTZBJSA-N
Synonyms
cholic acid; 81-25-4; Cholalic acid; cholate; Colalin; Cholalin; Cholbam; Cholsaeure; cholicacid; NSC-6135; kolbam; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic acid; Cholic acid [USAN]; Cholic acid, 5beta-; 3,7,12-Trihydroxycholanic acid; (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid; SODIUM CHOLATE; MFCD00003672; HSDB 982; (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid; Cholan-24-oic acid, 3,7,12-trihydroxy-, (3a,5b,7a,12a)-; TERPENES AND TERPENOIDS; CHEMBL205596; G1JO7801AE; CHEBI:16359; NSC6135; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate; CHD; Cholic acid (USAN); orphacol; 3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholan-24-oic acid; 5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy-; C24H40O5; 3,7,12-Trihydroxycholan-24-oic acid, (3alpha,5beta,7alpha,12alpha)-; 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3alpha,7alpha,12alpha-triol; 3,7,12-Trihydroxy-cholan-24-oic acid (3-alpha,5-beta,7-alpha,12-alpha); Cholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7alpha,12alpha)-; 129874-08-4; 4-[(3R,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid; (3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholan-24-oic acid; (3alpha,5beta,7alpha,8x,12alpha)-3,7,12-trihydroxycholan-24-oic acid; Cholan-24-oic acid, 3,7,12-trihydroxy-, (3-alpha,5-beta,7-alpha,12-alpha)-; (4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-trihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid; SMR000112165; Colalin (VAN); Cholsaeure [German]; 5beta-Cholanic acid-3alpha,7alpha,12alpha-triol; Cholan-24-oic acid, 3,7,12-trihydroxy-, (3.alpha.,5.beta.,7.alpha.,12.alpha.)-; UNII-G1JO7801AE; Cholalate; OrphacolReg; cholic-acid; CCRIS 1626; (3alpha,5beta,7alpha,8xi,12alpha)-3,7,12-trihydroxycholan-24-oic acid; 5b-Cholate; 5b-Cholic acid; CholsA currencyure; Cholbam (TN); EINECS 201-337-8; Cholic acid (8CI); 5.beta.-Cholic acid; BRN 2822009; 361-09-1; Spectrum5_002005; CHOLIC ACID [MI]; 3alpha,7alpha,12alpha-Trihydroxycholanic acid; bmse000650; CHOLIC ACID [FCC]; CHOLIC ACID [JAN]; EC 201-337-8; CHOLIC ACID [HSDB]; 3-alpha,7-alpha,12-alpha-Trihydroxycholansaeure; BIDD:PXR0196; SCHEMBL27461; GTPL609; 3.alpha.,7.alpha.,12.alpha.-Trihydroxy-5.beta.-cholanic acid; 4-10-00-02072 (Beilstein Handbook Reference); MLS001066422; MLS002207051; CHOLIC ACID [USP-RS]; CHOLIC ACID [WHO-DD]; 3a,7a,12a-Trihydroxycholanate; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanoic acid; CHOLIC ACID [EMA EPAR]; DTXSID6040660; BDBM21680; 3-alpha,7-alpha,12-alpha-Trihydroxycholansaeure [German]; CHOLIC ACID [EP IMPURITY]; CHOLIC ACID [ORANGE BOOK]; HMS2268L18; 3a,7a,12a-Trihydroxy-b-cholanate; 3a,7a,12a-Trihydroxycholanic acid; HY-N0324; ZINC6858022; 3a,7a,12a-Trihydroxy-5b-cholanate; 5b-Cholanic acid-3a,7a,12a-triol; BBL029799; LMST04010001; s3742; STK801993; 3a,7a,12a-Trihydroxy-5b-cholanoate; 3a,7a,12a-Trihydroxy-beta-cholanate; AKOS005622502; 3a,7a,12a-Trihydroxy-b-cholanic acid; CCG-268746; CS-6608; DB02659; 3a,7a,12a-Trihydroxy-5A-cholanic acid; 3a,7a,12a-Trihydroxy-5b-cholanic acid; NCGC00142384-03; 3a,7a,12a-Trihydroxy-5b-cholanoic acid; 3a,7a,12a-Trihydroxy-beta-cholanic acid; 4-((1S,2S,7S,11S,16S,5R,9R,10R,14R,15R)-5,9,16-trihydroxy-2,15-dimethyltetracy clo[8.7.0.0<2,7>.0<11,15>]heptadec-14-yl)pentanoic acid; AS-69849; BP-30084; 3a,7a,12a-Trihydroxy-5b-cholan-24-oate; Cholic acid, Vetec(TM) reagent grade, 98%; Cholic acid, from ox or sheep bile, >=98%; 3a,7a,12a-Trihydroxy-5b-cholan-24-oic acid; C-5900; C00695; D10699; EN300-6766788; A830252; Q287415; SR-01000765698; 3alpha,7alpha,12alpha-Trihydroxy-beta-cholanic acid; SR-01000765698-4; 3.alpha.,12.alpha.-Trihydroxy-5.beta.-cholanic acid; URSODEOXYCHOLIC ACID IMPURITY B [EP IMPURITY]; 3-.alpha.,7-.alpha.,12-.alpha.-Trihydroxycholansaeure; 3alpha, 7alpha, 12alpha-trihydroxy-5beta-cholanic acid; 3alpha, 7alpha, 12alpha-trihydroxy-5beta-cholanoic acid; Z1954806455; 3-&alpha,7-&alpha,12-&alpha-trihydroxy-5-&beta-cholanate; Cholic acid, British Pharmacopoeia (BP) Reference Standard; Cholic acid, European Pharmacopoeia (EP) Reference Standard; 17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triol; 5.beta.-Cholan-24-oic acid,7.alpha.,12.alpha.-trihydroxy-; 5beta-Cholanic acid, 3alpha,7alpha,12alpha-trihydroxy- (7CI); 5beta-Cholanic acid-3alpha,7alpha,12alpha-triol 5beta-Cholic acid; Cholic acid, 500 mug/mL in methanol, certified reference material; Cholic acid, United States Pharmacopeia (USP) Reference Standard; 17beta-[1-Methyl-3-carboxypropyl]etiocholane-3alpha,7alpha,12alpha-triol; 3-.alpha.,7-.alpha.,12-.alpha.-Trihydroxy-5-.beta.-cholan-24-oic acid; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic Acid (Cholic Acid); 5.beta.-Cholan-24-oic acid, 3.alpha.,7.alpha.,12.alpha.-trihydroxy-; (3.alpha.,5.beta.,7.alpha.,12.alpha.)-3,7,12-Trihydroxycholan-24-oic acid sodium salt; (3alpha,5beta,7alpha,8alpha,12alpha,14beta,17alpha)-3,7,12-trihydroxycholan-24-oic acid; 17.beta.-(1-Methyl-3-carboxypropyl)etiocholane-3.alpha.,7.alpha.,12.alpha.-triol; 3,7,12-Trihydroxy-cholan-24-oic acid, (3.alpha.,5.beta.,7.alpha.,12.alpha.)-; Cholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7alpha,12alpha)- (9CI); Cholan-24-oic acid,7,12-trihydroxy-, (3.alpha.,5.beta.,7.alpha.,12.alpha.)-; (4R)-4-((3R,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid; (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid; (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoicacid; (R)-4-((3R,5S,7R,8R,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid; 10321-98-9; CHOLAN-24-OIC ACID, 3,7,12-TRIHYDROXY-, (3-.ALPHA.,5-.BETA.,7-.ALPHA.,12-.ALPHA.)-
CAS 81-25-4
PubChem CID 221493
ChEMBL ID CHEMBL205596
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Lipids and lipid-like mol
      • Class: Steroids and steroid deri
        • Subclass: Bile acids, alcohols and
          • Direct Parent: Trihydroxy bile acids, al

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 408.6 ALogp: 3.6
HBD: 4 HBA: 5
Rotatable Bonds: 4 Lipinski's rule of five: Accepted
Polar Surface Area: 98.0 Aromatic Rings: 4
Heavy Atoms: 29 QED Weighted: 0.559

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -5.443 MDCK Permeability: 0.00002870
Pgp-inhibitor: 0.975 Pgp-substrate: 0.99
Human Intestinal Absorption (HIA): 0.037 20% Bioavailability (F20%): 0.019
30% Bioavailability (F30%): 0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.345 Plasma Protein Binding (PPB): 78.28%
Volume Distribution (VD): 0.387 Fu: 17.95%

ADMET: Metabolism

CYP1A2-inhibitor: 0.019 CYP1A2-substrate: 0.149
CYP2C19-inhibitor: 0.008 CYP2C19-substrate: 0.733
CYP2C9-inhibitor: 0.005 CYP2C9-substrate: 0.788
CYP2D6-inhibitor: 0.003 CYP2D6-substrate: 0.139
CYP3A4-inhibitor: 0.013 CYP3A4-substrate: 0.055

ADMET: Excretion

Clearance (CL): 8.834 Half-life (T1/2): 0.939

ADMET: Toxicity

hERG Blockers: 0.35 Human Hepatotoxicity (H-HT): 0.487
Drug-inuced Liver Injury (DILI): 0.033 AMES Toxicity: 0.006
Rat Oral Acute Toxicity: 0.694 Maximum Recommended Daily Dose: 0.898
Skin Sensitization: 0.929 Carcinogencity: 0.067
Eye Corrosion: 0.016 Eye Irritation: 0.122
Respiratory Toxicity: 0.932
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC004228 0.813 D0OR2L 1.000
ENC000609 0.753 D03ZTE 0.753
ENC001009 0.753 D0G3SH 0.753
ENC005147 0.432 D0M4WA 0.578
ENC001603 0.395 D00VZZ 0.402
ENC005145 0.395 D0Y7LD 0.339
ENC005968 0.395 D0B4RU 0.324
ENC005144 0.365 D04DJN 0.314
ENC002795 0.357 D09NNA 0.291
ENC000125 0.353 D0X7XG 0.290
*Note: the compound similarity was calculated by RDKIT.