(1R,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-11a-(hydroxymethyl)-5b,8,8,13a-tetramethyl-3-oxo-1,3,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[2,1-c]furan-1-yl acetate

ID: ALA573400

PubChem CID: 25159223

Max Phase: Preclinical

Molecular Formula: C27H40O5

Molecular Weight: 444.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@H]1OC(=O)C2=CC[C@@H]3[C@](C)(CC[C@H]4[C@@]3(C)CC[C@H]3C(C)(C)CCC[C@@]34CO)[C@H]21

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

Standard InChI Key:  HZNSTAFUGUGFAZ-JMJANOEMSA-N

Molfile:  

     RDKit          2D

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   15.9050   -4.3231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9125   -7.4000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0500   -9.8625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7583   -8.6250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   14.1833   -8.6375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9208  -10.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7458  -10.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 16 25  1  6
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  6 26  1  6
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  9 27  1  6
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  5 28  1  1
  1  2  1  0
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  1  4  1  0
 10 31  1  1
  2  3  1  0
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 15 17  2  0
 18 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA573400

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

CX Basic pKa: ┄

CX LogP: 4.73

CX LogD: 4.73

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.61

Np Likeness Score: 3.04

References

1. 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