sagequinone methide A

ID: ALA1081337

Cas Number: 194472-90-7

PubChem CID: 44254444

Max Phase: Preclinical

Molecular Formula: C20H24O4

Molecular Weight: 328.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C1=CC2=C[C@H]3OC(=O)[C@@]4(CCCC(C)(C)[C@H]34)C2=C(O)C1=O

Standard InChI:  InChI=1S/C20H24O4/c1-10(2)12-8-11-9-13-17-19(3,4)6-5-7-20(17,18(23)24-13)14(11)16(22)15(12)21/h8-10,13,17,22H,5-7H2,1-4H3/t13-,17+,20+/m1/s1

Standard InChI Key:  CYJLXXSGOZGYMC-VOWSPCBNSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    3.6669   -7.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6669   -7.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768   -8.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768   -6.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0910   -7.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921   -7.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8052   -8.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5177   -7.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8031   -6.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5155   -7.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2329   -6.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2349   -5.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5133   -5.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8033   -5.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9562   -9.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858   -9.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0877   -8.7589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0835   -6.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4965   -5.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8024   -7.5210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0862   -5.4624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5119   -4.6358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9518   -5.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6640   -5.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9522   -4.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982   -9.1885    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
 12 13  1  0
  1  4  1  0
 13 14  1  0
 14  9  2  0
  2  3  1  0
  3 15  1  0
  5  9  1  0
  3 16  1  0
  6  7  1  0
  6 17  1  6
  7  8  1  0
  5 18  1  1
  8 10  2  0
 18 19  2  0
  3  6  1  0
 20 18  1  0
  5  4  1  0
 14 21  1  0
  9 10  1  0
 13 22  2  0
  5  6  1  0
 12 23  1  0
 10 11  1  0
 23 24  1  0
 23 25  1  0
 20  7  1  0
 11 12  2  0
  7 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1081337

   SAGEQUINONE METHIDE A

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: 3.64

#Rotatable Bonds: 1

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.39

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: 3.04

References

1. Marrero JG, Moujir L, Andrés LS, Montaño NP, Araujo L, Luis JG..  (2009)  Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone.,  72  (8): [PMID:19711987] [10.1021/np900047p]

Source

Source(1):

• Scientific Literature