Nodulisporic acid

ID: ALA443627

PubChem CID: 11421897

Max Phase: Preclinical

Molecular Formula: C38H49NO4

Molecular Weight: 583.81

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Nodulisporic Acid | Nodulisporic acid D|(2E,4E)-5-[(10S,17S,18S,21S,22S,23R,26S)-21-Hydroxy-7,7,9,9,17,18,22-heptamethyl-8-oxa-15-azaheptacyclo[14.11.0.02,14.04,12.05,10.017,26.018,23]heptacosa-1(16),2(14),3,5,12-pentaen-22-yl]-2-methylpenta-2,4-dienoic acid|CHEMBL443627|SCHEMBL3119536|CHEBI:221469

Canonical SMILES:  C/C(=C\C=C\[C@]1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@H]1Cc3c([nH]c4cc5c(cc34)C3=CC(C)(C)OC(C)(C)[C@H]3C5)[C@@]12C)C(=O)O

Standard InChI:  InChI=1S/C38H49NO4/c1-21(33(41)42)10-9-14-36(6)30-12-11-23-18-26-25-19-24-22(16-28-27(24)20-34(2,3)43-35(28,4)5)17-29(25)39-32(26)38(23,8)37(30,7)15-13-31(36)40/h9-10,14,17,19-20,23,28,30-31,39-40H,11-13,15-16,18H2,1-8H3,(H,41,42)/b14-9+,21-10+/t23-,28-,30-,31-,36-,37-,38+/m0/s1

Standard InChI Key:  CQCRWLOGUOKQCD-FOWVSSDISA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA443627

   NODULISPORIC ACID

Molecule Features

Natural Product: No

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: 583.81

Molecular Weight (Monoisotopic): 583.3662

AlogP: 7.91

#Rotatable Bonds: 3

Polar Surface Area: 82.55

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.50

CX Basic pKa: ┄

CX LogP: 7.12

CX LogD: 4.31

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.25

Np Likeness Score: 2.95

References

1. Singh SB, Ondeyka JG, Jayasuriya H, Zink DL, Ha SN, Dahl-Roshak A, Greene J, Kim JA, Smith MM, Shoop W, Tkacz JS..  (2004)  Nodulisporic acids D-F: structure, biological activities, and biogenetic relationships.,  67  (9): [PMID:15387649] [10.1021/np0498455]

Source

Source(1):

• Scientific Literature