(8S,11bS)-7,11-dihydroxy-4,4,8,11b-tetramethyl-1,3,4,4a,5,8,9,11b-octahydrophenanthro[3,2-b]furan-6(2H)-one

ID: ALA5203169

PubChem CID: 168292929

Max Phase: Preclinical

Molecular Formula: C20H26O4

Molecular Weight: 330.42

Names and Identifiers

Canonical SMILES:  C[C@@H]1COc2c(O)c3c(c(O)c21)C(=O)CC1C(C)(C)CCC[C@]31C

Standard InChI:  InChI=1S/C20H26O4/c1-10-9-24-18-13(10)16(22)14-11(21)8-12-19(2,3)6-5-7-20(12,4)15(14)17(18)23/h10,12,22-23H,5-9H2,1-4H3/t10-,12?,20+/m1/s1

Standard InChI Key:  AFKBIJLWRQCMOW-BXUBMEQVSA-N

Molfile:  

 
     RDKit          2D

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   -1.7727    0.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0581   -0.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0581   -1.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7727   -1.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4872   -1.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435   -1.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -1.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -0.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435    0.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3434    0.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3710    1.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0856    0.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0855    0.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8003   -0.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6900    1.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578    2.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    2.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4872    1.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583    1.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0857   -1.5372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0581    0.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861   -2.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3607   -2.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  2  0
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  9 14  1  0
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 16 19  1  1
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  3 22  1  1
  5 23  1  0
  5 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5203169

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 330.42

Molecular Weight (Monoisotopic): 330.1831

AlogP: 4.26

#Rotatable Bonds: ┄

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.32

CX Basic pKa: ┄

CX LogP: 4.46

CX LogD: 4.45

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.70

Np Likeness Score: 2.89

References

1. Peng X, Tan Q, Wu L, Wu D, Xu J, Zhou H, Gu Q..  (2022)  Ferroptosis Inhibitory Aromatic Abietane Diterpenoids from Ajuga decumbens and Structural Revision of Two 3,4-Epoxy Group-Containing Abietanes.,  85  (7.0): [PMID:35796002] [10.1021/acs.jnatprod.2c00352]

Source

Source(1):

• Scientific Literature