22beta-hydroxy-3-oxoolean-12-en-28-oic acid

ID: ALA461093

Chembl Id: CHEMBL461093

PubChem CID: 44560837

Max Phase: Preclinical

Molecular Formula: C30H46O4

Molecular Weight: 470.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C[C@@H](O)[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Standard InChI:  InChI=1S/C30H46O4/c1-25(2)16-19-18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-29(21,7)28(18,6)14-15-30(19,24(33)34)23(32)17-25/h8,19-21,23,32H,9-17H2,1-7H3,(H,33,34)/t19-,20-,21+,23+,27-,28+,29+,30-/m0/s1

Standard InChI Key:  SSGQNTBKIXJPSE-FHXXJBRDSA-N

Alternative Forms

1. Parent:

   

   ALA461093

   (4R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)-4-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic 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: 470.69

Molecular Weight (Monoisotopic): 470.3396

AlogP: 6.41

#Rotatable Bonds: 1

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.61

CX Basic pKa:

CX LogP: 5.93

CX LogD: 3.21

Aromatic Rings: 0

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: 3.35

References

1. Sharma M, Sharma PD, Bansal MP..  (2008)  Lantadenes and their esters as potential antitumor agents.,  71  (7): [PMID:18553923] [10.1021/np800167x]

2. Tailor NK, Boon HL, Sharma M..  (2013)  Synthesis and in vitro anticancer studies of novel C-2 arylidene congeners of lantadenes.,  64  [PMID:23644211] [10.1016/j.ejmech.2013.04.009]

3. Suthar SK, Boon HL, Sharma M..  (2014)  Novel lung adenocarcinoma and nuclear factor-kappa B (NF-κB) inhibitors: synthesis and evaluation of lantadene congeners.,  74  [PMID:24457265] [10.1016/j.ejmech.2013.12.052]

4. Monika, Sharma A, Suthar SK, Aggarwal V, Lee HB, Sharma M..  (2014)  Synthesis of lantadene analogs with marked in vitro inhibition of lung adenocarcinoma and TNF-α induced nuclear factor-kappa B (NF-κB) activation.,  24  (16): [PMID:25027934] [10.1016/j.bmcl.2014.06.068]

5. Romero-Benavides JC, Ruano AL, Silva-Rivas R, Castillo-Veintimilla P, Vivanco-Jaramillo S, Bailon-Moscoso N..  (2017)  Medicinal plants used as anthelmintics: Ethnomedical, pharmacological, and phytochemical studies.,  129  [PMID:28231520] [10.1016/j.ejmech.2017.02.005]

Source

Source(1):

• Scientific Literature