2-methoxy-3,5-dimethyl-6-((1R,3'S,5'R,6S,8R)-1,3,5-trimethyl-8-(4-nitrophenyl)-4',5'-dihydro-2'H-spiro[bicyclo[4.2.0]octa[2,4]diene-7,3'-furan]-5'-yl)-4H-pyran-4-one

ID: ALA514407

PubChem CID: 9912904

Max Phase: Preclinical

Molecular Formula: C28H31NO6

Molecular Weight: 477.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SNF-4435C | SNF4435C|2-Methoxy-3,5-dimethyl-6-[(1R,2'R,6S,7S,8R)-1,3,5-trimethyl-8-(4-nitrophenyl)spiro[bicyclo[4.2.0]octa-2,4-diene-7,4'-oxolane]-2'-yl]pyran-4-one|CHEMBL514407|SCHEMBL12632512|SNF-4435C|CHEBI:216362

Canonical SMILES:  COc1oc([C@H]2C[C@@]3(CO2)[C@H](c2ccc([N+](=O)[O-])cc2)[C@]2(C)C=C(C)C=C(C)[C@@H]23)c(C)c(=O)c1C

Standard InChI:  InChI=1S/C28H31NO6/c1-15-11-16(2)24-27(5,12-15)25(19-7-9-20(10-8-19)29(31)32)28(24)13-21(34-14-28)23-17(3)22(30)18(4)26(33-6)35-23/h7-12,21,24-25H,13-14H2,1-6H3/t21-,24+,25-,27-,28+/m1/s1

Standard InChI Key:  DXCYJJKWPZZHNZ-PAWAVCGOSA-N

Molfile:  

     RDKit          2D

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  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  1
  6  8  1  0
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  1  6  1  0
  7  8  1  0
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  7 12  1  0
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  7 36  1  6
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA514407

   2-Methoxy-3,5-dimethyl-6-[(1R,2'R,6S,7S,8R)-1,3,5-trimethyl-8-(4-nitrophenyl)spiro[bicyclo[4.2.0]octa-2,4-diene-7,4'-oxolane]-2'-yl]pyran-4-one

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: 477.56

Molecular Weight (Monoisotopic): 477.2151

AlogP: 5.95

#Rotatable Bonds: 4

Polar Surface Area: 91.81

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.04

CX LogD: 5.04

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.40

Np Likeness Score: 0.93

References

1. Wilk W, Waldmann H, Kaiser M..  (2009)  Gamma-pyrone natural products--a privileged compound class provided by nature.,  17  (6): [PMID:19042133] [10.1016/j.bmc.2008.11.001]

Source

Source(1):

• Scientific Literature