Kazusamycin A

ID: ALA207141

Cas Number: 92090-94-3

PubChem CID: 11272917

Product Number: K102385, Order Now?

Max Phase: Preclinical

Molecular Formula: C33H48O7

Molecular Weight: 556.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=C/[C@H](C)C/C=C/C(C)=C/[C@@H](CO)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C/C(C)=C/C(=O)O)/C=C/[C@@H]1OC(=O)C=C[C@@H]1C

Standard InChI:  InChI=1S/C33H48O7/c1-8-27(13-14-29-24(5)12-15-31(37)40-29)17-21(2)10-9-11-22(3)18-28(20-34)33(39)26(7)32(38)25(6)16-23(4)19-30(35)36/h9,11-15,17-19,21,24-26,28-29,32,34,38H,8,10,16,20H2,1-7H3,(H,35,36)/b11-9+,14-13+,22-18+,23-19+,27-17-/t21-,24+,25+,26+,28+,29+,32-/m1/s1

Standard InChI Key:  KZMHNEBMQDBQND-LBNZKSCFSA-N

Molfile:  

     RDKit          2D

 40 40  0  0  1  0  0  0  0  0999 V2000
   -3.4174    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7035    2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9896    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2757    2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5618    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521    2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800    2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2939    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0078    2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7217    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4356    2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1495    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8635    2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2913    2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0052    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7191    2.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1342    2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4163    1.0143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9896    1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5618    1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521    3.0820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661    1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800    3.0820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2939    1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101    0.6008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7217    1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774    1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4359    1.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0052    1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7215    0.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7215   -0.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0020   -0.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0001   -1.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7144   -1.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4326   -1.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4362   -0.6351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2875   -0.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1473   -1.8807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3 21  1  0
 10 11  2  0
  5 22  1  1
  5  6  1  0
  6 23  1  1
 11 12  1  0
  7 24  1  1
  1  2  1  0
  8 25  2  0
 12 13  2  0
  9 26  1  1
  6  7  1  0
 26 27  1  0
 13 14  1  0
 11 28  1  0
  3  4  1  0
 15 29  1  6
 14 15  1  0
 18 30  1  0
  7  8  1  0
 17 31  1  0
 15 16  1  0
 31 32  2  0
 33 32  1  6
 33 34  1  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
  4  5  1  0
  1 19  1  0
 33 38  1  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
  9 10  1  0
 34 39  1  6
  1 20  2  0
 37 40  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA207141

   KAZUSAMYCIN A

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 556.74

Molecular Weight (Monoisotopic): 556.3400

AlogP: 5.76

#Rotatable Bonds: 16

Polar Surface Area: 121.13

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.38

CX Basic pKa: ┄

CX LogP: 6.29

CX LogD: 3.39

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.13

Np Likeness Score: 2.31

References

1. Ando R, Amano Y, Nakamura H, Arai N, Kuwajima I..  (2006)  Design, synthesis, and evaluation of novel kazusamycin A derivatives as potent antitumor agents.,  16  (12): [PMID:16617017] [10.1016/j.bmcl.2006.03.056]

Source

Source(1):

• Scientific Literature