illudinic acid

ID: ALA448170

PubChem CID: 10264679

Max Phase: Preclinical

Molecular Formula: C15H18O4

Molecular Weight: 262.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Illudinic Acid | illudinic acid|CHEMBL448170|(2S,4S)-4-hydroxy-2,4-dimethyl-6-methylidene-7-oxospiro[1,3-dihydroindene-5,1'-cyclopropane]-2-carboxylic acid

Canonical SMILES:  C=C1C(=O)C2=C(C[C@](C)(C(=O)O)C2)[C@](C)(O)C12CC2

Standard InChI:  InChI=1S/C15H18O4/c1-8-11(16)9-6-13(2,12(17)18)7-10(9)14(3,19)15(8)4-5-15/h19H,1,4-7H2,2-3H3,(H,17,18)/t13-,14+/m1/s1

Standard InChI Key:  XVLXBOQONSPNGH-KGLIPLIRSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -4.0942   -2.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6779   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5001   -1.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6779   -0.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648   -1.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648   -0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2471   -0.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2471   -1.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4587   -1.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9714   -0.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -0.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3919   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9659    0.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3851   -2.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7584   -2.5023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3934   -1.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2654   -0.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066   -2.2592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4019   -1.2508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
  4  6  1  0
  4 12  2  0
  2  5  1  0
  6 13  2  0
  5  8  1  0
  5 14  1  1
  7  6  1  0
  5 15  1  0
  7  8  2  0
 10 16  1  1
  3  2  1  0
 10 17  1  0
  4  2  1  0
 16 18  2  0
  1  3  1  0
 16 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA448170

   ILLUDINIC 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: 262.30

Molecular Weight (Monoisotopic): 262.1205

AlogP: 1.84

#Rotatable Bonds: 1

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.32

CX Basic pKa: ┄

CX LogP: 1.66

CX LogD: -1.29

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.71

Np Likeness Score: 2.75

References

1. Dufresne C, Young K, Pelaez F, Gonzalez del Val A, Valentino D, Graham A, Platas G, Bernard A, Zink D..  (1997)  Illudinic acid, a novel illudane sesquiterpene antibiotic.,  60  (2): [PMID:9051915] [10.1021/np960596x]

Source

Source(1):

• Scientific Literature