2alpha,3alpha-dihydroxyurs-12,20(30)-dien-28-oic acid

ID: ALA3342057

PubChem CID: 118716213

Max Phase: Preclinical

Molecular Formula: C30H46O4

Molecular Weight: 470.69

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](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2[C@H]1C

Standard InChI:  InChI=1S/C30H46O4/c1-17-10-13-30(25(33)34)15-14-28(6)19(23(30)18(17)2)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h8,18,20-24,31-32H,1,9-16H2,2-7H3,(H,33,34)/t18-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

Standard InChI Key:  PYUUJQUMSQBUIN-YKEAIUOESA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   16.2819  -18.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4064  -23.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0020  -22.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5930  -23.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3004  -21.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3004  -22.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0056  -20.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7109  -21.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7120  -22.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4163  -22.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1241  -22.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4142  -20.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1226  -21.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1305  -19.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4150  -20.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8389  -20.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8288  -20.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5310  -21.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2478  -21.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2603  -20.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9780  -19.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9929  -18.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5552  -19.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5599  -18.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5914  -20.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5932  -22.6141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7036  -20.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7077  -23.0176    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4094  -21.7918    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1151  -20.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8209  -21.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5473  -20.5825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.9629  -20.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9634  -21.4079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6704  -20.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8564  -18.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2943  -17.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  5  6  1  0
  5  7  1  0
  6  3  1  0
  3  9  1  0
  8  7  1  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12 13  1  0
 12 15  1  0
 13 17  1  0
 16 14  2  0
 14 15  1  0
 16 17  1  0
 16 23  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 23 20  1  0
 20 21  1  0
 21 22  1  0
 22  1  1  0
  1 24  1  0
 23 24  1  0
  5 25  1  6
  6 26  1  6
  8 27  1  1
  9 28  1  6
 12 29  1  6
 13 30  1  1
 17 31  1  6
 23 32  1  1
 20 33  1  1
 33 34  2  0
 33 35  1  0
 24 36  1  1
  1 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3342057

   ---

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: 470.69

Molecular Weight (Monoisotopic): 470.3396

AlogP: 5.98

#Rotatable Bonds: 1

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.72

CX Basic pKa: ┄

CX LogP: 5.16

CX LogD: 2.53

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.41

Np Likeness Score: 3.48

References

1. Li MM, Su XQ, Sun J, Gu YF, Huang Z, Zeng KW, Zhang Q, Zhao YF, Ferreira D, Zjawiony JK, Li J, Tu PF..  (2014)  Anti-inflammatory ursane- and oleanane-type triterpenoids from Vitex negundo var. cannabifolia.,  77  (10): [PMID:25245917] [10.1021/np500509q]

2. 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