(1R,4aS,10aR)-3-chloro-2-hydroxypropyl 7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate

ID: ALA3358317

PubChem CID: 14166443

Max Phase: Preclinical

Molecular Formula: C23H33ClO3

Molecular Weight: 392.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc2c(c1)CC[C@H]1[C@](C)(C(=O)OCC(O)CCl)CCC[C@]21C

Standard InChI:  InChI=1S/C23H33ClO3/c1-15(2)16-6-8-19-17(12-16)7-9-20-22(19,3)10-5-11-23(20,4)21(26)27-14-18(25)13-24/h6,8,12,15,18,20,25H,5,7,9-11,13-14H2,1-4H3/t18?,20-,22-,23-/m1/s1

Standard InChI Key:  GNMQVGMADCLFIC-KUYSTHMBSA-N

Molfile:  

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   20.1279  -13.2239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3448  -12.5099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3108  -13.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9091  -13.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0919  -13.9513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3245  -14.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9228  -15.3588    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.4227  -10.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.8298  -11.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5319  -11.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.9573  -10.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9689   -9.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2623   -8.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5442   -9.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6817   -8.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3842   -9.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6921   -8.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2441  -10.8133    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.8260   -9.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4145  -12.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 27  1  1
 11 28  1  0
 11  1  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3358317

   (3-chloro-2-hydroxypropyl) (1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate

Molecule Features

Natural Product: No

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: 392.97

Molecular Weight (Monoisotopic): 392.2118

AlogP: 4.96

#Rotatable Bonds: 5

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.57

CX Basic pKa: ┄

CX LogP: 5.93

CX LogD: 5.93

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: 1.77

References

1. Wang H, Nguyen TT, Li S, Liang T, Zhang Y, Li J..  (2015)  Quantitative structure-activity relationship of antifungal activity of rosin derivatives.,  25  (2): [PMID:25466709] [10.1016/j.bmcl.2014.11.034]

Source

Source(1):

• Scientific Literature