Boesenmaxane A

ID: ALA4871158

PubChem CID: 164619410

Max Phase: Preclinical

Molecular Formula: C20H26O3

Molecular Weight: 314.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)CCC[C@]2(C)C3=C(C[C@H](C4=CCOC4=O)C3)C(=O)C[C@@H]12

Standard InChI:  InChI=1S/C20H26O3/c1-19(2)6-4-7-20(3)15-10-12(13-5-8-23-18(13)22)9-14(15)16(21)11-17(19)20/h5,12,17H,4,6-11H2,1-3H3/t12-,17-,20+/m0/s1

Standard InChI Key:  HOFGDYNGISNEHI-CYFODOTGSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    6.3816   -8.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9720   -8.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5579   -8.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2616   -6.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2616   -7.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9758   -6.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6898   -6.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6864   -7.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3972   -8.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1163   -7.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4043   -6.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1172   -6.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7323   -6.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3997   -5.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5789   -5.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8161   -4.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6372   -4.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8123   -3.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0972   -3.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4803   -4.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1873   -5.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8312   -8.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6783   -8.5087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6824   -6.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  6  1  0
  5  2  1  0
  2  8  1  0
  7  6  1  0
  7  8  1  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 14 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  2  0
 17 21  2  0
 10 22  2  0
  8 23  1  6
  7 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4871158

   ---

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: 314.43

Molecular Weight (Monoisotopic): 314.1882

AlogP: 3.98

#Rotatable Bonds: 1

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.36

CX Basic pKa: ┄

CX LogP: 3.86

CX LogD: 3.86

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: 3.01

References

1. Moe TS, Chaturonrutsamee S, Bunteang S, Kuhakarn C, Prabpai S, Surawatanawong P, Chairoungdua A, Suksen K, Akkarawongsapat R, Limthongkul J, Napaswad C, Nuntasaen N, Reutrakul V..  (2021)  Boesenmaxane Diterpenoids from Boesenbergia maxwellii.,  84  (2.0): [PMID:33372792] [10.1021/acs.jnatprod.0c00629]

Source

Source(1):

• Scientific Literature