3-((1R,3R,4aR,4bS,10aS,12aS)-1-acetoxy-4b,7,7,10a-tetramethylhexadecahydro-1H-naphtho[2,1-f]isochromen-3-yl)-5-oxo-2,5-dihydrofuran-2-yl acetate

ID: ALA514471

Chembl Id: CHEMBL514471

PubChem CID: 44575492

Max Phase: Preclinical

Molecular Formula: C29H42O7

Molecular Weight: 502.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC1OC(=O)C=C1[C@H]1C[C@@H]2[C@H](CCC3[C@@]4(C)CCCC(C)(C)C4CC[C@]32C)[C@@H](OC(C)=O)O1

Standard InChI:  InChI=1S/C29H42O7/c1-16(30)33-25-18-8-9-23-28(5,13-10-22-27(3,4)11-7-12-29(22,23)6)20(18)15-21(35-25)19-14-24(32)36-26(19)34-17(2)31/h14,18,20-23,25-26H,7-13,15H2,1-6H3/t18-,20+,21+,22?,23?,25-,26?,28-,29-/m0/s1

Standard InChI Key:  MZXCAKUNUVJPJS-RYYLEPEISA-N

Alternative Forms

1. Parent:

   

   ALA514471

   [(1R,3R,4aR,4bS,10aS,12aS)-3-(2-acetyloxy-5-oxo-2H-furan-3-yl)-4b,7,7,10a-tetramethyl-1,3,4,4a,5,6,6a,8,9,10,10b,11,12,12a-tetradecahydronaphtho[2,1-f]isochromen-1-yl] acetate

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: 502.65

Molecular Weight (Monoisotopic): 502.2931

AlogP: 5.31

#Rotatable Bonds: 3

Polar Surface Area: 88.13

Molecular Species: ACID

HBA: 7

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.82

CX Basic pKa: ┄

CX LogP: 5.36

CX LogD: 1.88

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.48

Np Likeness Score: 2.96

References

1. Randazzo A, Debitus C, Minale L, García Pastor P, Alcaraz MJ, Payá M, Gomez-Paloma L..  (1998)  Petrosaspongiolides M-R: new potent and selective phospholipase A2 inhibitors from the New Caledonian marine sponge Petrosaspongia nigra.,  61  (5): [PMID:9599251] [10.1021/np9704922]

Source

Source(1):

• Scientific Literature