12-Deacetoxy-23-acetoxy-19-O-acetylscalarin

ID: ALA576346

PubChem CID: 11166698

Max Phase: Preclinical

Molecular Formula: C27H40O5

Molecular Weight: 444.61

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](O)[C@@H]4[C@@]3(C)CC[C@@H]12

Standard InChI:  InChI=1S/C27H40O5/c1-16(28)31-15-27-12-6-11-24(2,3)18(27)9-13-25(4)19-8-7-17-21(23(30)32-22(17)29)26(19,5)14-10-20(25)27/h7,18-21,23,30H,6,8-15H2,1-5H3/t18-,19-,20-,21+,23+,25-,26-,27+/m0/s1

Standard InChI Key:  NQUDADRZXBXFOV-JMJANOEMSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA576346

   [(1R,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-1-hydroxy-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: 444.61

Molecular Weight (Monoisotopic): 444.2876

AlogP: 5.02

#Rotatable Bonds: 2

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.93

CX Basic pKa: ┄

CX LogP: 4.73

CX LogD: 4.73

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.61

Np Likeness Score: 2.95

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]

3. Hahn D, Won DH, Mun B, Kim H, Han C, Wang W, Chun T, Park S, Yoon D, Choi H, Nam SJ, Ekins M, Chin J, Kang H..  (2013)  Cytotoxic scalarane sesterterpenes from a Korean marine sponge Psammocinia sp.,  23  (8): [PMID:23489626] [10.1016/j.bmcl.2013.02.061]

Source

Source(1):

• Scientific Literature