3-{3-[(1R,5S,7S,9S)-3,12-dihydroxy-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.1^{7,10}.0^{1,6}]tridec-2-en-5-yl]propanamido}-2,4-dihydroxybenzoic acid

ID: ALA1773150

PubChem CID: 54580075

Max Phase: Preclinical

Molecular Formula: C24H27NO9

Molecular Weight: 473.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12O[C@H]3CC1C[C@@]1(C=C(O)C(=O)[C@@](C)(CCC(=O)Nc4c(O)ccc(C(=O)O)c4O)C31)C2O

Standard InChI:  InChI=1S/C24H27NO9/c1-22(6-5-15(28)25-16-12(26)4-3-11(17(16)29)20(31)32)18-14-7-10-8-24(18,9-13(27)19(22)30)21(33)23(10,2)34-14/h3-4,9-10,14,18,21,26-27,29,33H,5-8H2,1-2H3,(H,25,28)(H,31,32)/t10?,14-,18?,21?,22-,23-,24-/m0/s1

Standard InChI Key:  YFIXEYMGWRRNJF-ZSVIGFJHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1773150

   3-[3-[(1R,5S,7S,9S)-3,12-dihydroxy-5,9-dimethyl-4-oxo-8-oxatetracyclo[7.2.1.17,10.01,6]tridec-2-en-5-yl]propanoylamino]-2,4-dihydroxybenzoic 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: 473.48

Molecular Weight (Monoisotopic): 473.1686

AlogP: 2.09

#Rotatable Bonds: 5

Polar Surface Area: 173.62

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.96

CX Basic pKa: ┄

CX LogP: 1.80

CX LogD: -1.71

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.35

Np Likeness Score: 2.34

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