Benwamycin H

ID: ALA4547130

PubChem CID: 38354501

Max Phase: Preclinical

Molecular Formula: C20H28O4

Molecular Weight: 332.44

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H28O4/c1-6-19(23)24-20(14(3)16(5)22)15(4)18-10-9-13(2)12-17(18)8-7-11-21/h7-10,12,14-15,20-21H,6,11H2,1-5H3/b8-7+/t14-,15+,20+/m1/s1

Standard InChI Key:  MIXMRTZVGMGBIC-PHYBXGOISA-N

Molfile:  

 
     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    5.0991   -6.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8112   -6.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5154   -6.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5154   -7.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137   -8.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0991   -7.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2234   -8.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8112   -5.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5193   -5.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5193   -4.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2273   -4.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910   -6.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -6.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -7.7459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0906   -8.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -9.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0906   -9.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100   -8.4540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748   -6.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -6.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5546   -6.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -7.7459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748   -5.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910   -5.6993    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
  2  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  1 12  1  0
 12 13  1  0
 13 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 13 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 19 23  1  1
 12 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4547130

   [(2S,3R,4S)-2-[2-[(E)-3-hydroxyprop-1-enyl]-4-methylphenyl]-4-methyl-5-oxohexan-3-yl] propanoate

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: 332.44

Molecular Weight (Monoisotopic): 332.1988

AlogP: 3.65

#Rotatable Bonds: 8

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: 0.91

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