14-hydroxyplatensic acid

ID: ALA1773133

PubChem CID: 54581061

Max Phase: Preclinical

Molecular Formula: C17H22O5

Molecular Weight: 306.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 14-Hydroxyplatensic Acid | CHEMBL1773133

Canonical SMILES:  C[C@]12O[C@H]3CC1C[C@@]1(C=CC(=O)[C@@](C)(CCC(=O)O)C31)[C@H]2O

Standard InChI:  InChI=1S/C17H22O5/c1-15(5-4-12(19)20)11(18)3-6-17-8-9-7-10(13(15)17)22-16(9,2)14(17)21/h3,6,9-10,13-14,21H,4-5,7-8H2,1-2H3,(H,19,20)/t9?,10-,13?,14-,15+,16-,17+/m0/s1

Standard InChI Key:  TVMUTJRGKLRTET-WTGTYFDXSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   16.6480    0.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3664    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6468    1.6381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0836    0.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7829    0.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5115    0.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2299    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5101    1.6427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7943   -0.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2252   -0.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5900   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7828    1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9945   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5851   -0.8456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3657   -0.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1271   -0.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9229   -0.7691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5799   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3772    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8797    0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3873    0.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1949    0.0765    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9465    0.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  5 12  1  1
  1  2  1  0
  9 13  1  0
  6  7  1  0
 13 14  1  0
  2  4  1  0
 14 15  1  0
  6  8  2  0
 15 16  1  0
 11 16  1  0
 16 17  1  1
  5  9  1  0
 15 18  1  6
  4  5  1  0
 15 19  1  0
  7 10  2  0
 13 20  1  0
 20 19  1  0
  1  3  2  0
 11 21  1  1
 19 21  1  0
  9 11  1  0
 13 22  1  6
 11 10  1  0
  1 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773133

   3-[(1S,5S,7S,9S,12R)-12-hydroxy-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.17,10.01,6]tridec-2-en-5-yl]propanoic acid

Molecule Features

Natural Product: Yes

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: 306.36

Molecular Weight (Monoisotopic): 306.1467

AlogP: 1.54

#Rotatable Bonds: 3

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.34

CX Basic pKa: ┄

CX LogP: 1.18

CX LogD: -1.75

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: 3.68

References

1. Zhang C, Ondeyka J, Herath K, Jayasuriya H, Guan Z, Zink DL, Dietrich L, Burgess B, Ha SN, Wang J, Singh SB..  (2011)  Platensimycin and platencin congeners from Streptomyces platensis.,  74  (3): [PMID:21214253] [10.1021/np100635f]

Source

Source(1):

• Scientific Literature