(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-11-hydroxy-4,4,10,13-tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-2,3-diyl dibenzoate

ID: ALA449270

Chembl Id: CHEMBL449270

PubChem CID: 3011633

Max Phase: Preclinical

Molecular Formula: C46H58O7

Molecular Weight: 722.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(CC[C@@H](C)[C@H]1CC=C2C3=C([C@@H](O)[C@H](OC(C)=O)[C@@]21C)[C@@]1(C)C[C@@H](OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)C(C)(C)[C@@H]1CC3)C(C)C

Standard InChI:  InChI=1S/C46H58O7/c1-27(2)28(3)20-21-29(4)34-23-24-35-33-22-25-37-44(6,7)40(53-43(50)32-18-14-11-15-19-32)36(52-42(49)31-16-12-10-13-17-31)26-45(37,8)38(33)39(48)41(46(34,35)9)51-30(5)47/h10-19,24,27,29,34,36-37,39-41,48H,3,20-23,25-26H2,1-2,4-9H3/t29-,34-,36-,37+,39-,40+,41+,45+,46-/m1/s1

Standard InChI Key:  VKQXVHLNBAARHD-UDLWUWCOSA-N

Alternative Forms

1. Parent:

   

   ALA449270

   [(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-3-benzoyloxy-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-11-hydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-2-yl] benzoate

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: 722.96

Molecular Weight (Monoisotopic): 722.4183

AlogP: 9.47

#Rotatable Bonds: 10

Polar Surface Area: 99.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.52

CX Basic pKa: ┄

CX LogP: 9.55

CX LogD: 9.55

Aromatic Rings: 2

Heavy Atoms: 53

QED Weighted: 0.15

Np Likeness Score: 2.54

References

1. Singh SB, Ondeyka JG, Schleif WA, Felock P, Hazuda DJ..  (2003)  Chemistry and structure-activity relationship of HIV-1 integrase inhibitor integracide B and related natural products.,  66  (10): [PMID:14575434] [10.1021/np030211s]

Source

Source(1):

• Scientific Literature