platensimycin A5 methyl ester

ID: ALA1773141

PubChem CID: 54586932

Max Phase: Preclinical

Molecular Formula: C25H31NO8

Molecular Weight: 473.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Platensimycin A5 Methyl Ester | Platensimycin A5 Methyl Ester|CHEBI:68264|CHEMBL1773141|Q27136757|methyl 2,4-dihydroxy-3-({3-[(1S)-6-hydroxy-6-(hydroxymethyl)-1-methyl-2-oxo-1,2,5,6,7,8,9,9a-octahydro-4a,7-methanobenzo[7]annulen-1-yl]propanoyl}amino)benzoate

Canonical SMILES:  COC(=O)c1ccc(O)c(NC(=O)CC[C@]2(C)C(=O)C=CC34CC(CCC32)C(O)(CO)C4)c1O

Standard InChI:  InChI=1S/C25H31NO8/c1-23(9-8-19(30)26-20-16(28)5-4-15(21(20)31)22(32)34-2)17-6-3-14-11-24(17,10-7-18(23)29)12-25(14,33)13-27/h4-5,7,10,14,17,27-28,31,33H,3,6,8-9,11-13H2,1-2H3,(H,26,30)/t14?,17?,23-,24?,25?/m0/s1

Standard InChI Key:  LNVBATHWLFVZRW-HURMGZDQSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
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   22.4768   -9.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1927   -9.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9101   -9.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.7604   -9.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0522   -9.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7597  -10.6093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6192   -9.7839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   25.3334   -8.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   27.4759  -10.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9034  -10.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2698  -10.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4644   -8.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6780  -10.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2696  -11.0201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0483  -10.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8079  -11.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2620  -11.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0598  -10.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5635   -9.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0675   -9.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0439  -11.7859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0557   -8.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 18  1  0
  2  9  1  0
 18 19  1  0
  4  5  1  0
 18 20  2  0
  9 10  1  0
 17 21  1  0
  2  3  1  0
 19 22  2  0
  9 11  2  0
 21 23  1  0
 23 22  1  0
  5  6  2  0
 17 24  1  1
  4 12  1  0
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  6  1  1  0
 12 13  1  0
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  1  2  2  0
 27 28  1  0
 23 28  1  0
 13 14  1  0
 27 29  1  0
  5  7  1  0
 27 30  1  0
 13 15  2  0
 25 31  1  0
 31 30  1  0
  3  4  2  0
 23 32  1  0
 30 32  1  0
 14 16  1  0
 29 33  1  0
  3  8  1  0
 10 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1773141

   PLATENSIMYCIN A5 METHYL 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: 473.52

Molecular Weight (Monoisotopic): 473.2050

AlogP: 2.28

#Rotatable Bonds: 6

Polar Surface Area: 153.39

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.96

CX Basic pKa: ┄

CX LogP: 2.68

CX LogD: 2.58

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.31

Np Likeness Score: 2.33

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