3-((S)-5-Methyl-9-methylene-4-oxo-tricyclo[6.2.2.0*1,6*]dodec-2-en-5-yl)-propionic acid 2,3-dihydroxy-propyl ester

ID: ALA1773147

PubChem CID: 54581063

Max Phase: Preclinical

Molecular Formula: C20H28O5

Molecular Weight: 348.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Platencinic acid glycerol ester | CHEMBL1773147

Canonical SMILES:  C=C1CC23C=CC(=O)[C@@](C)(CCC(=O)OCC(O)CO)C2CC1CC3

Standard InChI:  InChI=1S/C20H28O5/c1-13-10-20-7-3-14(13)9-16(20)19(2,17(23)4-8-20)6-5-18(24)25-12-15(22)11-21/h4,8,14-16,21-22H,1,3,5-7,9-12H2,2H3/t14?,15?,16?,19-,20?/m0/s1

Standard InChI Key:  FYKIZBPSTADBEK-BTCBHJBXSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    6.4142  -19.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1072  -19.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4124  -18.2081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8020  -19.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5144  -19.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2949  -18.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8867  -19.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2970  -18.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4932  -20.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8799  -20.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1574  -19.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4854  -18.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8028  -20.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2774  -19.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6081  -20.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8535  -20.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6977  -19.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7445  -19.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1502  -21.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013  -19.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853  -19.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2723  -19.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563  -19.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755  -20.2553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5532  -18.1955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
 15 19  2  0
  6  8  2  0
  1 20  1  0
  5  9  1  0
 20 21  1  0
  7 10  2  0
 21 22  1  0
  9 11  1  0
 22 23  1  0
 11 10  1  0
 22 24  1  0
  5 12  1  1
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773147

   PLATENCINIC ACID GLYCEROL ESTER

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: 348.44

Molecular Weight (Monoisotopic): 348.1937

AlogP: 2.17

#Rotatable Bonds: 6

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: 13.62

CX Basic pKa: ┄

CX LogP: 2.04

CX LogD: 2.04

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.57

Np Likeness Score: 3.23

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