isoneorautenol

ID: ALA1098729

PubChem CID: 821442

Max Phase: Preclinical

Molecular Formula: C20H18O4

Molecular Weight: 322.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isoneorautenol | CHEMBL1098729|BDBM50317433|(1R,13R)-7,7-Dimethyl-8,12,20-trioxapentacyclo[11.8.0.02,11.04,9.014,19]henicosa-2(11),3,5,9,14(19),15,17-heptaen-17-ol

Canonical SMILES:  CC1(C)C=Cc2cc3c(cc2O1)O[C@H]1c2ccc(O)cc2OC[C@@H]31

Standard InChI:  InChI=1S/C20H18O4/c1-20(2)6-5-11-7-14-15-10-22-17-8-12(21)3-4-13(17)19(15)23-18(14)9-16(11)24-20/h3-9,15,19,21H,10H2,1-2H3/t15-,19-/m0/s1

Standard InChI Key:  WTKJOOHYNMPGLE-KXBFYZLASA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
   13.4137    3.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4125    2.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1248    2.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1230    3.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8359    3.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8347    2.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2704    3.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5514    3.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2692    2.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5482    2.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7160    1.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8824    1.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5402    1.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0207    0.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7007    2.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9775    2.9147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8309    1.6816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7016    3.7367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1833    1.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8420    0.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3218   -0.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1453    0.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4867    0.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0045    1.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9289   -0.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7261   -0.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
 14 20  2  0
  1  2  2  0
 19 15  2  0
 15 12  1  0
  5  8  1  0
  9 16  1  6
  6 10  1  0
 10 17  1  6
  9  7  1  0
  1 18  1  0
 19 20  1  0
  7  8  1  0
  9 10  1  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
 10 11  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 11 13  1  0
 22 25  1  0
  9 12  1  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098729

   ISONEORAUTENOL

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: 322.36

Molecular Weight (Monoisotopic): 322.1205

AlogP: 4.19

#Rotatable Bonds: ┄

Polar Surface Area: 47.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.42

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 3.56

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: 2.88

References

1. Nguyen PH, Nguyen TN, Kang KW, Ndinteh DT, Mbafor JT, Kim YR, Oh WK..  (2010)  Prenylated pterocarpans as bacterial neuraminidase inhibitors.,  18  (9): [PMID:20363636] [10.1016/j.bmc.2010.03.005]

2. Rueda DC, De Mieri M, Hering S, Hamburger M..  (2014)  HPLC-based activity profiling for GABAA receptor modulators in Adenocarpus cincinnatus.,  77  (3): [PMID:24571311] [10.1021/np500016z]

Source

Source(1):

• Scientific Literature