(1S,4S,5aS,5bR,7aS,11aS,11bR,13aS,13bR)-4-hydroxy-5b,8,8,11a,13a-pentamethyl-1,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[2,1-c]furan-1-yl acetate

ID: ALA572476

PubChem CID: 25158708

Max Phase: Preclinical

Molecular Formula: C27H42O4

Molecular Weight: 430.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@H]1OC=C2[C@H]1[C@@]1(C)CC[C@H]3[C@@](C)(CC[C@H]4C(C)(C)CCC[C@]34C)[C@@H]1C[C@@H]2O

Standard InChI:  InChI=1S/C27H42O4/c1-16(28)31-23-22-17(15-30-23)18(29)14-21-26(5)12-8-19-24(2,3)10-7-11-25(19,4)20(26)9-13-27(21,22)6/h15,18-23,29H,7-14H2,1-6H3/t18-,19-,20+,21-,22+,23-,25-,26+,27-/m0/s1

Standard InChI Key:  FQJRSISTDYPNPR-ARCYHYOLSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   -4.5250  -14.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5250  -15.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8130  -16.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8130  -14.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010  -14.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0999  -15.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3889  -16.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743  -15.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3910  -14.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6757  -14.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6678  -13.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9526  -13.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628  -14.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539  -14.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697  -14.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2335  -13.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774  -13.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043  -13.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7807  -12.2621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462  -12.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725  -11.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0740  -10.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005  -10.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508  -10.8897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2417  -13.9667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042  -16.4292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3958  -15.1917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083  -13.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3976  -13.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6833  -13.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583  -12.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708  -15.2042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333  -16.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083  -16.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791  -14.8180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 17  1  0
 16 17  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 16 20  1  0
  3  6  1  0
 20 21  1  6
  5  4  1  0
 21 22  1  0
  5  6  1  0
 22 23  1  0
  9 29  1  0
 22 24  2  0
 10 13  1  0
 16 25  1  6
 12 11  1  0
  6 26  1  6
 11 29  1  0
  9 27  1  6
 12 13  1  0
  5 28  1  1
  1  2  1  0
 10 30  1  1
  1  4  1  0
 12 31  1  1
  2  3  1  0
 13 32  1  6
 12 16  1  0
  3 33  1  0
 13 14  1  0
  3 34  1  0
 14 15  1  0
 15 35  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA572476

   [(1S,4S,5aS,5bR,7aS,11aS,11bR,13aS,13bR)-4-hydroxy-5b,8,8,11a,13a-pentamethyl-1,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[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: 430.63

Molecular Weight (Monoisotopic): 430.3083

AlogP: 5.84

#Rotatable Bonds: 1

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.79

CX LogD: 4.79

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: 2.90

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