12-hydroxyplatencinic acid methyl ester

ID: ALA1773148

PubChem CID: 54584046

Max Phase: Preclinical

Molecular Formula: C18H24O4

Molecular Weight: 304.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 12-Hydroxyplatencinic Acid Methyl Ester | 12-Hydroxyplatencinic Acid Methyl Ester|CHEMBL1773148

Canonical SMILES:  C=C1CC23C=CC(=O)[C@@](C)(CCC(=O)OC)C2CC1[C@@H](O)C3

Standard InChI:  InChI=1S/C18H24O4/c1-11-9-18-7-4-15(20)17(2,6-5-16(21)22-3)14(18)8-12(11)13(19)10-18/h4,7,12-14,19H,1,5-6,8-10H2,2-3H3/t12?,13-,14?,17-,18?/m0/s1

Standard InChI Key:  YNZQBHPCQCEONI-PZYMKTKKSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   12.9650  -19.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6781  -19.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9631  -18.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3933  -19.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1264  -19.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9297  -18.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5386  -19.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9317  -18.1109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1045  -20.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5316  -20.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7881  -20.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0965  -18.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3940  -20.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8533  -20.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1937  -20.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4753  -20.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2858  -19.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3631  -19.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2313  -19.5501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4944  -19.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7224  -21.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0655  -18.8595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  1  0
 11 10  1  0
  5 12  1  1
  9 13  1  0
  1  2  1  0
 13 14  1  0
  1  3  2  0
 14 15  1  0
  2  4  1  0
 15 16  1  0
 11 16  1  0
  4  5  1  0
 14 17  1  0
  5  6  1  0
 17 18  1  0
 11 18  1  0
  6  7  1  0
  1 19  1  0
  6  8  2  0
 19 20  1  0
  5  9  1  0
 15 21  2  0
  7 10  2  0
 17 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1773148

   methyl 3-[(5S,9S)-9-hydroxy-5-methyl-12-methylidene-4-oxo-5-tricyclo[6.2.2.01,6]dodec-2-enyl]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: 304.39

Molecular Weight (Monoisotopic): 304.1675

AlogP: 2.42

#Rotatable Bonds: 3

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: 2.05

CX LogD: 2.05

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: 3.47

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