(1S,4aR,10aS)-methyl 1-formyl-5-hydroxy-7-isopropyl-6-methoxy-1-methyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylate

ID: ALA4572137

PubChem CID: 155563247

Max Phase: Preclinical

Molecular Formula: C22H30O5

Molecular Weight: 374.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]12CCC[C@](C)(C=O)[C@@H]1CCc1cc(C(C)C)c(OC)c(O)c12

Standard InChI:  InChI=1S/C22H30O5/c1-13(2)15-11-14-7-8-16-21(3,12-23)9-6-10-22(16,20(25)27-5)17(14)18(24)19(15)26-4/h11-13,16,24H,6-10H2,1-5H3/t16-,21+,22+/m0/s1

Standard InChI Key:  QFEJDDXYLXDDGI-KNXBSLHKSA-N

Molfile:  

 
     RDKit          2D

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   13.7684  -12.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0668  -13.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4783  -12.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7684  -11.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1841  -11.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1717  -12.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4783  -11.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3610  -14.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7726  -14.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9483  -14.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4783  -13.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8981  -11.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3652  -12.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4783  -10.3717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6429  -13.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6429  -12.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9022  -10.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6038  -11.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1205  -14.4577    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7655  -14.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7788   -9.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1309  -14.7526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6500  -12.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0624  -11.4075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8289  -12.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4203  -11.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3598  -10.8835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  2  0
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  6  8  1  0
  7  4  1  0
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  9  3  1  0
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 13  6  1  0
 14  1  1  0
 15  8  1  0
 16 17  1  0
 17 14  1  0
 18 13  1  0
 19 13  1  0
  3 20  1  6
  9 16  1  0
  4 12  1  0
  7  6  2  0
  9 21  1  6
 15 22  1  0
 11 23  2  0
  1 24  1  1
 24 25  2  0
 24 26  1  0
 26 27  1  0
  5 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4572137

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 374.48

Molecular Weight (Monoisotopic): 374.2093

AlogP: 3.89

#Rotatable Bonds: 4

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.86

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 4.46

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: 2.27

References

1. Bustos-Brito C, Joseph-Nathan P, Burgueño-Tapia E, Martínez-Otero D, Nieto-Camacho A, Calzada F, Yépez-Mulia L, Esquivel B, Quijano L..  (2019)  Structure and Absolute Configuration of Abietane Diterpenoids from Salvia clinopodioides: Antioxidant, Antiprotozoal, and Antipropulsive Activities.,  82  (5): [PMID:31063376] [10.1021/acs.jnatprod.8b00952]

Source

Source(1):

• Scientific Literature