3alpha-trans-coumaroyloxy-2alpha-hydroxy-12,20(30)-diene-28-ursolic acid

ID: ALA3793675

Chembl Id: CHEMBL3793675

PubChem CID: 127029185

Max Phase: Preclinical

Molecular Formula: C39H52O6

Molecular Weight: 616.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@@H](OC(=O)/C=C/c6ccc(O)cc6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2[C@H]1C

Standard InChI:  InChI=1S/C39H52O6/c1-23-16-19-39(34(43)44)21-20-37(6)27(32(39)24(23)2)13-14-30-36(5)22-28(41)33(35(3,4)29(36)17-18-38(30,37)7)45-31(42)15-10-25-8-11-26(40)12-9-25/h8-13,15,24,28-30,32-33,40-41H,1,14,16-22H2,2-7H3,(H,43,44)/b15-10+/t24-,28+,29-,30+,32-,33+,36-,37+,38+,39-/m0/s1

Standard InChI Key:  NXSZULOVDUOZKO-GYTPSKCOSA-N

Alternative Forms

1. Parent:

   

   ALA3793675

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Molecule Features

Natural Product: No

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: 616.84

Molecular Weight (Monoisotopic): 616.3764

AlogP: 7.95

#Rotatable Bonds: 4

Polar Surface Area: 104.06

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.72

CX Basic pKa: ┄

CX LogP: 7.89

CX LogD: 5.26

Aromatic Rings: 1

Heavy Atoms: 45

QED Weighted: 0.18

Np Likeness Score: 2.99

References

1. Cai YH, Guo Y, Li Z, Wu D, Li X, Zhang H, Yang J, Lu H, Sun Z, Luo HB, Yin S, Wu Y..  (2016)  Discovery and modelling studies of natural ingredients from Gaultheria yunnanensis (FRANCH.) against phosphodiesterase-4.,  114  [PMID:26978121] [10.1016/j.ejmech.2015.12.002]

Source

Source(1):

• Scientific Literature