Diversonol

ID: ALA1765408

PubChem CID: 11652265

Max Phase: Preclinical

Molecular Formula: C15H18O6

Molecular Weight: 294.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Diversonol | (+)-diversonol|DIVERSONOL|CHEBI:68282|CHEMBL1765408|(1S,4S,4aS,9aR)-1,4,8,9a-tetrahydroxy-4a,6-dimethyl-1,2,3,4-tetrahydroxanthen-9-one|Q27136775

Canonical SMILES:  Cc1cc(O)c2c(c1)O[C@@]1(C)[C@@H](O)CC[C@H](O)[C@]1(O)C2=O

Standard InChI:  InChI=1S/C15H18O6/c1-7-5-8(16)12-9(6-7)21-14(2)10(17)3-4-11(18)15(14,20)13(12)19/h5-6,10-11,16-18,20H,3-4H2,1-2H3/t10-,11-,14-,15-/m0/s1

Standard InChI Key:  GBAMGKOMMOEKIB-GVARAGBVSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -4.1303   -0.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1314   -0.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4211   -1.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227    0.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7119   -0.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7087   -0.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9940   -1.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0004    0.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2810   -0.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2815   -0.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672   -1.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1520   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1525   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5663    0.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8422   -1.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4251    1.0992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0047    1.1113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886    0.7004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5672    1.1145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5687   -2.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -1.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  5  6  1  0
  2  3  1  0
  3  6  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  1  2  2  0
  2 15  1  0
  5  8  1  0
  4 16  1  0
  6  7  1  0
  8 17  2  0
  7 10  1  0
  9 18  1  6
  9  8  1  0
 14 19  1  1
  9 10  1  0
 11 20  1  6
  5  4  2  0
 10 21  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1765408

   DIVERSONOL

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: 294.30

Molecular Weight (Monoisotopic): 294.1103

AlogP: 0.28

#Rotatable Bonds: ┄

Polar Surface Area: 107.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.73

CX Basic pKa: ┄

CX LogP: 1.02

CX LogD: 1.00

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.55

Np Likeness Score: 2.24

References

1. Siddiqui IN, Zahoor A, Hussain H, Ahmed I, Ahmad VU, Padula D, Draeger S, Schulz B, Meier K, Steinert M, Kurtán T, Flörke U, Pescitelli G, Krohn K..  (2011)  Diversonol and blennolide derivatives from the endophytic fungus Microdiplodia sp.: absolute configuration of diversonol.,  74  (3): [PMID:21244021] [10.1021/np100730b]

Source

Source(1):

• Scientific Literature