Benwamycin G

ID: ALA4460955

PubChem CID: 155528181

Max Phase: Preclinical

Molecular Formula: C20H26O4

Molecular Weight: 330.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC1=CC(=O)[C@@H](C)[C@@H]([C@@H](C)c2ccc(CO)cc2/C=C/CO)O1

Standard InChI:  InChI=1S/C20H26O4/c1-4-17-11-19(23)14(3)20(24-17)13(2)18-8-7-15(12-22)10-16(18)6-5-9-21/h5-8,10-11,13-14,20-22H,4,9,12H2,1-3H3/b6-5+/t13-,14+,20+/m0/s1

Standard InChI Key:  QQUATXMTFHAAFC-FZVHOESVSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   28.2690  -15.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9808  -14.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6886  -15.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6886  -16.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9808  -16.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2690  -16.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9808  -17.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2693  -17.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3960  -14.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3960  -14.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1034  -15.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8152  -14.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5191  -15.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5191  -16.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8137  -16.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1034  -16.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2307  -16.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9381  -16.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8152  -14.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5227  -13.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5227  -12.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2301  -12.4003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6886  -14.4448    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.9808  -14.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5615  -14.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  3  4  1  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  5  7  1  0
  7  8  1  0
  3  9  1  0
  9 10  1  1
  9 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 11 16  1  0
 14 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
  3 23  1  6
  2 24  1  1
  1 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4460955

   ---

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: 330.42

Molecular Weight (Monoisotopic): 330.1831

AlogP: 3.19

#Rotatable Bonds: 6

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.97

CX LogD: 2.97

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: 1.53

References

1. Yang FX, Huang JP, Liu Z, Wang Z, Yang J, Tang J, Yu Z, Yan Y, Kai G, Huang SX..  (2020)  Benwamycins A-G, Trialkyl-Substituted Benzene Derivatives from a Soil-Derived Streptomyces.,  83  (1): [PMID:31904958] [10.1021/acs.jnatprod.9b00903]

Source

Source(1):

• Scientific Literature