Comazaphilone D

ID: ALA1689198

PubChem CID: 51041753

Max Phase: Preclinical

Molecular Formula: C21H22O7

Molecular Weight: 386.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Comazaphilone D | Comazaphilone D|CHEBI:70013|MLS005941364|CHEMBL1689198|SMR004614078|Q27138354|(6R,7R)-7-Hydroxy-7-methyl-8-oxo-3-[prop-1-en-1-yl]-5,6,7,8-tetrahydro-1H-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate|[(6R,7R)-7-hydroxy-7-methyl-8-oxo-3-[(E)-prop-1-enyl]-5,6-dihydro-1H-isochromen-6-yl] 2,4-dihydroxy-6-methyl-benzoate|rel-(6R,7R)-7-hydroxy-7-methyl-8-oxo-3-[(1E)-prop-1-en-1-yl]-5,6,7,8-tetrahydro-1H-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate

Canonical SMILES:  C/C=C/C1=CC2=C(CO1)C(=O)[C@](C)(O)[C@H](OC(=O)c1c(C)cc(O)cc1O)C2

Standard InChI:  InChI=1S/C21H22O7/c1-4-5-14-7-12-8-17(21(3,26)19(24)15(12)10-27-14)28-20(25)18-11(2)6-13(22)9-16(18)23/h4-7,9,17,22-23,26H,8,10H2,1-3H3/b5-4+/t17-,21-/m1/s1

Standard InChI Key:  GIROBNCADSJPIJ-OQBWYENPSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   10.1694   -4.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1682   -3.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8831   -2.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5995   -3.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5966   -4.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8813   -4.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8788   -5.4586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3096   -4.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4534   -2.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0256   -4.2299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3064   -5.4647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7385   -4.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4571   -4.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4531   -5.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7361   -5.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1690   -5.4673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1666   -4.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8764   -4.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5933   -4.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5957   -5.4631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8813   -5.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3146   -2.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4528   -6.7043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3060   -4.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0222   -4.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7349   -4.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5167   -6.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9333   -5.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 12 15  1  0
 13 17  1  0
 16 14  1  0
 14 15  1  0
 16 17  2  0
  3  4  2  0
  5  8  1  0
  2  9  1  0
  4  5  1  0
  8 10  1  0
 16 21  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  2  3  1  0
  4 22  1  0
  8 11  2  0
 14 23  2  0
  5  6  2  0
 19 24  1  0
 12 10  1  6
 24 25  2  0
 12 13  1  0
 25 26  1  0
  6  1  1  0
 15 27  1  1
  1  2  2  0
 15 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1689198

   COMAZAPHILONE D

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: 386.40

Molecular Weight (Monoisotopic): 386.1366

AlogP: 2.44

#Rotatable Bonds: 3

Polar Surface Area: 113.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.70

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: 3.38

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: 2.33

References

1. Gao SS, Li XM, Zhang Y, Li CS, Cui CM, Wang BG..  (2011)  Comazaphilones A-F, azaphilone derivatives from the marine sediment-derived fungus Penicillium commune QSD-17.,  74  (2): [PMID:21226488] [10.1021/np100788h]

Source

Source(1):

• Scientific Literature