isoguaiacin

ID: ALA482239

Cas Number: 78341-26-1

PubChem CID: 10314441

Max Phase: Preclinical

Molecular Formula: C20H24O4

Molecular Weight: 328.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isoguaiacin | isoguaiacin|(-)-isoguaiacin|F803X9JE3W|78341-26-1|UNII-F803X9JE3W|CHEBI:68174|(6R,7R,8R)-5,6,7,8-Tetrahydro-8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-2-naphthalenol|(6R,7R,8R)-8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol|2-Naphthalenol, 5,6,7,8-tetrahydro-8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-, (6R-(6alpha,7alpha,8beta))-|CHEMBL482239|HY-N11935|CS-0890030|Q27136666|2-NAPHTHALENOL, 5,6,7,8-TETRAHYDRO-8-(4-HYDROXY-3-Show More⌵

Canonical SMILES:  COc1cc([C@@H]2c3cc(O)c(OC)cc3C[C@@H](C)[C@H]2C)ccc1O

Standard InChI:  InChI=1S/C20H24O4/c1-11-7-14-9-19(24-4)17(22)10-15(14)20(12(11)2)13-5-6-16(21)18(8-13)23-3/h5-6,8-12,20-22H,7H2,1-4H3/t11-,12-,20-/m1/s1

Standard InChI Key:  TZAAYUCUPIYQBR-FKANQGBASA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.5820  -11.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832  -12.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8703  -12.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723  -10.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1541  -11.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1530  -12.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4371  -12.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2782  -12.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2731  -11.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4433  -10.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9849  -10.9105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8761  -10.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1653   -9.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1688   -8.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8857   -8.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006   -8.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5936   -9.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8907   -7.6289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4561   -8.4482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2601   -8.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944  -12.5676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9979  -13.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983  -12.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2968  -10.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  4 12  1  6
  5  6  1  0
 12 13  2  0
  3  6  1  0
 13 14  1  0
  6  7  2  0
 14 15  2  0
  1  2  1  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 12  1  0
  5  4  1  0
 15 18  1  0
  8  9  2  0
 14 19  1  0
  4  1  1  0
 19 20  1  0
  9 10  1  0
  8 21  1  0
 10  5  2  0
 21 22  1  0
  2 23  1  1
  9 11  1  0
  1 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA482239

   ISOGUAIACIN

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: 328.41

Molecular Weight (Monoisotopic): 328.1675

AlogP: 4.08

#Rotatable Bonds: 3

Polar Surface Area: 58.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.85

CX Basic pKa: ┄

CX LogP: 4.50

CX LogD: 4.50

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.89

Np Likeness Score: 1.60

References

1. Lobo-Echeverri T, Rivero-Cruz JF, Su BN, Chai HB, Cordell GA, Pezzuto JM, Swanson SM, Soejarto DD, Kinghorn AD..  (2005)  Constituents of the leaves and twigs of Calyptranthes pallens collected from an experimental plot in Southern Florida.,  68  (4): [PMID:15844953] [10.1021/np0496688]

Source

Source(1):

• Scientific Literature