Methyl (4aR,10aS)-9-(Butylthio)-5,6-dihydroxy-7-isopropyl-1,1-dimethyl-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylate

ID: ALA4532131

PubChem CID: 155546327

Max Phase: Preclinical

Molecular Formula: C25H38O4S

Molecular Weight: 434.64

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCSC1C[C@H]2C(C)(C)CCC[C@]2(C(=O)OC)c2c1cc(C(C)C)c(O)c2O

Standard InChI:  InChI=1S/C25H38O4S/c1-7-8-12-30-18-14-19-24(4,5)10-9-11-25(19,23(28)29-6)20-17(18)13-16(15(2)3)21(26)22(20)27/h13,15,18-19,26-27H,7-12,14H2,1-6H3/t18?,19-,25+/m0/s1

Standard InChI Key:  ZGXATVQQSWVMBR-HXTXIVFLSA-N

Molfile:  

 
     RDKit          2D

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    4.4314   -3.6289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9436   -4.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444   -3.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7323   -3.1139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523   -3.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523   -2.6744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3633   -4.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6514   -5.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6514   -5.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3636   -6.3557    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0717   -5.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4882   -5.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1996   -6.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9436   -6.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2359   -5.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4480   -6.7359    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5281   -6.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9347   -7.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1153   -7.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163   -5.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163   -5.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5281   -4.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 15 11  2  0
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 24 23  1  0
 24 25  1  6
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  5 31  1  0
 24  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4532131

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 434.64

Molecular Weight (Monoisotopic): 434.2491

AlogP: 6.44

#Rotatable Bonds: 6

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.24

CX Basic pKa: ┄

CX LogP: 6.81

CX LogD: 6.81

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: 1.56

References

1. Han S, Li X, Xia Y, Yu Z, Cai N, Malwal SR, Han X, Oldfield E, Zhang Y..  (2019)  Farnesyl Pyrophosphate Synthase as a Target for Drug Development: Discovery of Natural-Product-Derived Inhibitors and Their Activity in Pancreatic Cancer Cells.,  62  (23): [PMID:31725297] [10.1021/acs.jmedchem.9b01405]

Source

Source(1):

• Scientific Literature