12-Deacetoxy-23-acetoxyscalarin

ID: ALA573356

PubChem CID: 11443149

Max Phase: Preclinical

Molecular Formula: C29H42O6

Molecular Weight: 486.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@]12CCCC(C)(C)[C@@H]1CC[C@@]1(C)[C@@H]3CC=C4C(=O)O[C@@H](OC(C)=O)[C@@H]4[C@@]3(C)CC[C@@H]12

Standard InChI:  InChI=1S/C29H42O6/c1-17(30)33-16-29-13-7-12-26(3,4)20(29)10-14-27(5)21-9-8-19-23(28(21,6)15-11-22(27)29)25(34-18(2)31)35-24(19)32/h8,20-23,25H,7,9-16H2,1-6H3/t20-,21-,22-,23+,25+,27-,28-,29+/m0/s1

Standard InChI Key:  HTBVRXFAQQUUQL-OFFJBMDCSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA573356

   [(1R,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-1-acetyloxy-5b,8,8,13a-tetramethyl-3-oxo-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-11a-yl]methyl 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: 486.65

Molecular Weight (Monoisotopic): 486.2981

AlogP: 5.59

#Rotatable Bonds: 3

Polar Surface Area: 78.90

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.18

CX LogD: 5.18

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.48

Np Likeness Score: 2.84

References

1. Rho JR, Lee HS, Shin HJ, Ahn JW, Kim JY, Sim CJ, Shin J..  (2004)  New sesterterpenes from the sponge Smenospongia sp.,  67  (10): [PMID:15497955] [10.1021/np040103l]

2. Song J, Jeong W, Wang N, Lee HS, Sim CJ, Oh KB, Shin J..  (2008)  Scalarane sesterterpenes from the sponge Smenospongia sp.,  71  (11): [PMID:18973387] [10.1021/np8003694]

Source

Source(1):

• Scientific Literature