Benwamycin C

ID: ALA4471601

PubChem CID: 155535314

Max Phase: Preclinical

Molecular Formula: C19H26O5

Molecular Weight: 334.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OCc1ccc([C@H](C)[C@@H](O)[C@H](C)C(C)=O)c(/C=C/CO)c1

Standard InChI:  InChI=1S/C19H26O5/c1-12(14(3)21)19(23)13(2)18-8-7-16(11-24-15(4)22)10-17(18)6-5-9-20/h5-8,10,12-13,19-20,23H,9,11H2,1-4H3/b6-5+/t12-,13+,19+/m1/s1

Standard InChI Key:  SAFFYRCQDFKPOV-KHGSUAOUSA-N

Molfile:  

 
     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    5.1212  -18.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292  -17.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375  -18.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375  -19.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8318  -19.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212  -19.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2456  -19.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9537  -19.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6618  -19.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3739  -19.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6618  -20.3456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292  -17.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414  -16.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414  -15.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2495  -15.4340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4132  -17.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010  -18.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010  -19.1150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9929  -17.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2848  -18.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5768  -17.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2848  -19.1150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9929  -17.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4132  -17.0684    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
  8  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
  1 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 19 23  1  1
 16 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4471601

   ---

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: 334.41

Molecular Weight (Monoisotopic): 334.1780

AlogP: 2.44

#Rotatable Bonds: 8

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: 2.02

CX LogD: 2.02

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.71

Np Likeness Score: 1.16

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