Clinopodiolide D; 6,7,11,14-tetrahydro-14-deoxy-12-O-methylicetexone

ID: ALA4518135

PubChem CID: 155541200

Max Phase: Preclinical

Molecular Formula: C21H28O4

Molecular Weight: 344.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c(C(C)C)cc2c(c1O)C[C@]13CCC[C@](C)(C(=O)O1)[C@@H]3CC2

Standard InChI:  InChI=1S/C21H28O4/c1-12(2)14-10-13-6-7-16-20(3)8-5-9-21(16,25-19(20)23)11-15(13)17(22)18(14)24-4/h10,12,16,22H,5-9,11H2,1-4H3/t16-,20-,21-/m0/s1

Standard InChI Key:  ALFZLIORNLXGRD-NDXORKPFSA-N

Molfile:  

 
     RDKit          2D

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    3.9085  -11.6223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5164  -13.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9056  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5205  -12.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726  -13.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726  -12.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2015  -13.8675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085  -14.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701  -14.7629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542  -13.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1520  -12.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7301  -11.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378  -13.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4618  -13.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4507  -12.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7767  -12.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167  -12.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9273  -12.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5966  -11.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8577  -11.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5300  -10.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0064  -10.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7512  -10.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6689  -12.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9969  -12.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0783  -11.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  1
  2 10  1  0
  3  2  1  0
  4 11  1  0
  5  6  1  0
  6  4  1  0
 10  7  1  6
  2  5  1  0
  3  1  1  0
  2  8  1  6
  3  9  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 12 15  1  0
 13 14  1  0
 14 16  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 18 24  1  0
 24 25  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4518135

   ---

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: 344.45

Molecular Weight (Monoisotopic): 344.1988

AlogP: 4.11

#Rotatable Bonds: 2

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.98

CX Basic pKa: ┄

CX LogP: 4.86

CX LogD: 4.86

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: 2.10

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