14-hydroxyplatensic acid methyl ester

ID: ALA1773134

PubChem CID: 54585948

Max Phase: Preclinical

Molecular Formula: C18H24O5

Molecular Weight: 320.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 14-Hydroxyplatensic Acid Methyl Ester | CHEMBL1773134

Canonical SMILES:  COC(=O)CC[C@]1(C)C(=O)C=C[C@]23CC4C[C@H](O[C@]4(C)[C@@H]2O)C13

Standard InChI:  InChI=1S/C18H24O5/c1-16(6-5-13(20)22-3)12(19)4-7-18-9-10-8-11(14(16)18)23-17(10,2)15(18)21/h4,7,10-11,14-15,21H,5-6,8-9H2,1-3H3/t10?,11-,14?,15-,16+,17-,18+/m0/s1

Standard InChI Key:  FBBBYTFYYNYGMH-MDHIWDTMSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   22.6895    1.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4080    0.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6882    1.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1252    1.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8244    0.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5530    1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2715    0.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5517    1.8838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8357   -0.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2668   -0.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6316    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8243    1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0361    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6267   -0.6045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4073   -0.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1686   -0.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9645   -0.5280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6215   -1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4187    0.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9213    0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4289    0.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2365    0.3175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.9880    0.6418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9898   -0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  5  6  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773134

   methyl 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]propanoate

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: 320.39

Molecular Weight (Monoisotopic): 320.1624

AlogP: 1.63

#Rotatable Bonds: 3

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.54

CX Basic pKa: ┄

CX LogP: 1.33

CX LogD: 1.33

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.80

Np Likeness Score: 3.48

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