Nodulisporic Acid F

ID: ALA458267

PubChem CID: 11281984

Max Phase: Preclinical

Molecular Formula: C28H37NO3

Molecular Weight: 435.61

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Nodulisporic Acid F | Nodulisporic Acid F|(E)-5-[(1S,12S,15R,16S,17S,20S)-17-hydroxy-1,16,20-trimethyl-3-azapentacyclo[10.8.0.02,10.04,9.015,20]icosa-2(10),4,6,8-tetraen-16-yl]-2-methylpent-2-enoic acid|CHEMBL458267|SCHEMBL20855299|CHEBI:207670

Canonical SMILES:  C/C(=C\CC[C@]1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@H]1Cc3c([nH]c4ccccc34)[C@@]12C)C(=O)O

Standard InChI:  InChI=1S/C28H37NO3/c1-17(25(31)32)8-7-14-26(2)22-12-11-18-16-20-19-9-5-6-10-21(19)29-24(20)28(18,4)27(22,3)15-13-23(26)30/h5-6,8-10,18,22-23,29-30H,7,11-16H2,1-4H3,(H,31,32)/b17-8+/t18-,22-,23-,26-,27-,28+/m0/s1

Standard InChI Key:  FYZYVTHTMPXJHJ-UOOBVZAFSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    8.0611  -17.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0599  -18.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7747  -18.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7729  -16.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4883  -17.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4931  -18.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2806  -18.3819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7643  -17.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7527  -16.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5408  -16.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5456  -17.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9669  -16.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2492  -16.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5333  -15.7917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   13.6854  -18.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6851  -17.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2542  -17.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9667  -18.2583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6792  -17.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4005  -19.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4792  -17.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0657  -18.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8614  -17.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4479  -18.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2437  -18.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2387  -19.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8333  -18.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4560  -17.5516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 15  1  1
  7  9  1  0
 12 16  1  6
 17 18  1  0
  8  5  1  0
  8  9  2  0
  1  2  2  0
  5  4  2  0
  4  1  1  0
  9 12  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 11 10  1  0
 18 23  1  1
 10  8  1  0
 17 24  1  6
 11 12  1  0
 22 25  1  1
  5  6  1  0
 21 26  1  1
 22 27  1  0
  2  3  1  0
 27 28  1  0
  3  6  2  0
 28 29  1  0
 11 14  1  0
 29 30  2  0
 12 18  1  0
 30 31  1  0
 17 13  1  0
 30 32  1  0
 13 14  1  0
  6  7  1  0
 31 33  1  0
 31 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA458267

   NODULISPORIC ACID F

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: 435.61

Molecular Weight (Monoisotopic): 435.2773

AlogP: 5.99

#Rotatable Bonds: 4

Polar Surface Area: 73.32

Molecular Species: ACID

HBA: 2

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.58

CX Basic pKa: ┄

CX LogP: 5.81

CX LogD: 3.06

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: 2.67

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