Benwamycin D

ID: ALA4589064

PubChem CID: 155567424

Max Phase: Preclinical

Molecular Formula: C20H28O5

Molecular Weight: 348.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(=O)O[C@@H]([C@H](C)C(C)=O)[C@@H](C)c1ccc(CO)cc1/C=C/CO

Standard InChI:  InChI=1S/C20H28O5/c1-5-19(24)25-20(13(2)15(4)23)14(3)18-9-8-16(12-22)11-17(18)7-6-10-21/h6-9,11,13-14,20-22H,5,10,12H2,1-4H3/b7-6+/t13-,14+,20+/m1/s1

Standard InChI Key:  KXWCDNGXRAPJLE-XSMXVWRTSA-N

Molfile:  

 
     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   17.0598   -6.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7678   -5.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4761   -6.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4761   -6.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7704   -7.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0598   -6.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1842   -7.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8923   -6.9772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7678   -4.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4800   -4.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4800   -3.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881   -3.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3517   -5.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6437   -6.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6437   -6.9778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2304   -7.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6324   -8.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2191   -9.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4109   -7.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9315   -5.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2234   -6.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5153   -5.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2234   -6.9778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9315   -4.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3517   -4.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  7  8  1  0
  2  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
  1 13  1  0
 13 14  1  0
 14 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  1
 13 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4589064

   ---

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: 348.44

Molecular Weight (Monoisotopic): 348.1937

AlogP: 2.83

#Rotatable Bonds: 9

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.72

CX LogD: 2.72

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: 1.12

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