2,3-secofriedelan-2,3-dioic acid

ID: ALA2043062

Chembl Id: CHEMBL2043062

PubChem CID: 15700263

Max Phase: Preclinical

Molecular Formula: C30H50O4

Molecular Weight: 474.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](C(=O)O)[C@@]1(C)CC[C@H]2[C@@](C)(CC[C@@]3(C)[C@@H]4CC(C)(C)CC[C@]4(C)CC[C@]23C)[C@@H]1CC(=O)O

Standard InChI:  InChI=1S/C30H50O4/c1-19(24(33)34)27(5)10-9-20-28(6,21(27)17-23(31)32)14-16-30(8)22-18-25(2,3)11-12-26(22,4)13-15-29(20,30)7/h19-22H,9-18H2,1-8H3,(H,31,32)(H,33,34)/t19-,20-,21+,22+,26+,27+,28+,29+,30-/m0/s1

Standard InChI Key:  PYRAZHRKJLQCON-NBNHYRBJSA-N

Alternative Forms

1. Parent:

   

   ALA2043062

   (2R)-2-[(1S,2S,4aS,4bR,6aR,10aR,10bS,12aS)-1-(carboxymethyl)-2,4b,6a,9,9,10b,12a-heptamethyl-1,3,4,4a,5,6,7,8,10,10a,11,12-dodecahydrochrysen-2-yl]propanoic 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: 474.73

Molecular Weight (Monoisotopic): 474.3709

AlogP: 7.65

#Rotatable Bonds: 4

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.28

CX Basic pKa: ┄

CX LogP: 7.12

CX LogD: 1.70

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: 2.27

References

1. Mandal A, Ghosh S, Bothra AK, Nanda AK, Ghosh P..  (2012)  Synthesis of friedelan triterpenoid analogs with DNA topoisomerase IIα inhibitory activity and their molecular docking studies.,  54  [PMID:22633831] [10.1016/j.ejmech.2012.04.037]

2. Kim HJ, Fei X, Cho SC, Choi BY, Ahn HC, Lee K, Seo SY, Keum YS..  (2015)  Discovery of α-mangostin as a novel competitive inhibitor against mutant isocitrate dehydrogenase-1.,  25  (23): [PMID:26508549] [10.1016/j.bmcl.2015.10.034]

Source

Source(1):

• Scientific Literature