Amorphigenol

ID: ALA4640867

PubChem CID: 71176526

Max Phase: Preclinical

Molecular Formula: C23H24O8

Molecular Weight: 428.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)[C@@H]1C(=O)c3ccc4c(c3O[C@@H]1CO2)C[C@H](C(C)(O)CO)O4

Standard InChI:  InChI=1S/C23H24O8/c1-23(26,10-24)19-7-13-14(30-19)5-4-11-21(25)20-12-6-16(27-2)17(28-3)8-15(12)29-9-18(20)31-22(11)13/h4-6,8,18-20,24,26H,7,9-10H2,1-3H3/t18-,19-,20+,23?/m1/s1

Standard InChI Key:  HCVCUIIDODCONY-FQAFXWPXSA-N

Molfile:  

 
     RDKit          2D

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   31.6340  -17.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3439  -18.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0497  -17.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.9223  -18.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.2165  -17.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6123  -16.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9364  -15.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7420  -15.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9147  -16.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5142  -15.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9229  -14.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5114  -13.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6992  -15.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1066  -14.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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  4 20  1  1
 21  3  2  0
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 26 27  1  0
 27 28  1  0
 28  1  2  0
 24 28  1  0
 26 29  1  1
 30 29  1  0
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 32 29  1  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4640867

   (1S,6R,13S)-6-(1,2-dihydroxypropan-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

Molecule Features

Natural Product: Yes

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: 428.44

Molecular Weight (Monoisotopic): 428.1471

AlogP: 1.87

#Rotatable Bonds: 4

Polar Surface Area: 103.68

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.17

CX Basic pKa: ┄

CX LogP: 1.31

CX LogD: 1.31

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.76

Np Likeness Score: 2.14

References

1. Russell DA, Bridges HR, Serreli R, Kidd SL, Mateu N, Osberger TJ, Sore HF, Hirst J, Spring DR..  (2020)  Hydroxylated Rotenoids Selectively Inhibit the Proliferation of Prostate Cancer Cells.,  83  (6): [PMID:32459967] [10.1021/acs.jnatprod.9b01224]

Source

Source(1):

• Scientific Literature