3beta-O-[3'-Carboxybicyclo[2.2.1]hept-50-enecarbonyl]-betulinic acid

ID: ALA1089646

PubChem CID: 46203832

Max Phase: Preclinical

Molecular Formula: C39H56O6

Molecular Weight: 620.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC(=O)C6C7C=CC(C7)C6C(=O)O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Standard InChI:  InChI=1S/C39H56O6/c1-21(2)24-12-17-39(34(43)44)19-18-37(6)25(31(24)39)10-11-27-36(5)15-14-28(35(3,4)26(36)13-16-38(27,37)7)45-33(42)30-23-9-8-22(20-23)29(30)32(40)41/h8-9,22-31H,1,10-20H2,2-7H3,(H,40,41)(H,43,44)/t22?,23?,24-,25+,26-,27+,28-,29?,30?,31+,36-,37+,38+,39-/m0/s1

Standard InChI Key:  MHGBKDWPTQXWRB-KOUWFRPVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1089646

   (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(3-carboxybicyclo[2.2.1]hept-5-ene-2-carbonyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

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: 620.87

Molecular Weight (Monoisotopic): 620.4077

AlogP: 8.16

#Rotatable Bonds: 5

Polar Surface Area: 100.90

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.13

CX Basic pKa: ┄

CX LogP: 7.72

CX LogD: 2.12

Aromatic Rings: ┄

Heavy Atoms: 45

QED Weighted: 0.24

Np Likeness Score: 2.36

References

1. Qian K, Kuo RY, Chen CH, Huang L, Morris-Natschke SL, Lee KH..  (2010)  Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors.,  53  (8): [PMID:20329730] [10.1021/jm901782m]

Source

Source(1):

• Scientific Literature