Hyocholic Acid

ID: ALA1908063

Cas Number: 547-75-1

PubChem CID: 92805

Product Number: H336518, Order Now?

Max Phase: Preclinical

Molecular Formula: C24H40O5

Molecular Weight: 408.58

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Hyocholic Acid | Hyocholic acid|547-75-1|gamma-Muricholic acid|Iocholic acid|3alpha,6alpha,7alpha-Trihydroxy-5beta-cholan-24-oic acid|2H5H0Q47FL|(4R)-4-[(3R,5R,6R,7S,8S,9S,10R,13R,14S,17R)-3,6,7-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|CHEBI:81244|6alpha-Hydroxychenodeoxycholic acid|gamma-Muricholate|alpha-Hyocholic acid|(3alpha,5beta,6alpha,7alpha)-3,6,7-Trihydroxycholan-24-oic acid|Cholan-24-oic acid, 3,6,7-trihShow More⌵

Canonical SMILES:  C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)[C@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22+,23-,24-/m1/s1

Standard InChI Key:  DKPMWHFRUGMUKF-KWXDGCAGSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  1  0  0  0  0  0999 V2000
    2.7136    2.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0894    1.8783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182    3.6252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5327    6.1980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3372    4.7825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4621    3.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9303    4.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742    3.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1182    4.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545    4.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8379    3.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1818    2.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3697    2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106    4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3791    4.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227    5.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256    3.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864    4.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258    3.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6084    3.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3985    4.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9144    5.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855    5.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5061    3.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2258    4.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7027    5.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746    5.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2091    5.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0263    5.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6767    4.4021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5576    2.5090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2041    4.4697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    2.9196    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168    3.4092    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  6
 13  2  1  6
 24  3  1  6
  4 29  2  0
  5 29  1  0
  6  7  1  0
  6  8  1  0
  6 12  1  0
  6 30  1  1
  7  9  1  0
  7 14  1  0
  8 10  1  0
  8 17  1  0
  9 11  1  0
  9 18  1  0
  9 21  1  1
 10 15  1  0
 10 16  1  0
 10 22  1  1
 11 13  1  0
 11 19  1  0
 11 31  1  1
 12 13  1  0
 14 16  1  0
 15 20  1  0
 15 23  1  0
 17 20  1  0
 18 25  1  0
 19 24  1  0
 23 26  1  0
 23 27  1  6
 24 25  1  0
 26 28  1  0
 28 29  1  0
 15 32  1  6
  8 33  1  6
  7 34  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1908063

   Hyocholic Acid

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 408.58

Molecular Weight (Monoisotopic): 408.2876

AlogP: 3.45

#Rotatable Bonds: 4

Polar Surface Area: 97.99

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.60

CX Basic pKa: ┄

CX LogP: 2.72

CX LogD: -0.01

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.57

Np Likeness Score: 2.41

References

1. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

2. PubChem BioAssay data set, 

3. Leverrier A, Bero J, Cabrera J, Frédérich M, Quetin-Leclercq J, Palermo JA..  (2015)  Structure-activity relationship of hybrids of Cinchona alkaloids and bile acids with in vitro antiplasmodial and antitrypanosomal activities.,  100  [PMID:26063305] [10.1016/j.ejmech.2015.05.044]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays