Uasdlabdane A

ID: ALA4526976

PubChem CID: 155544577

Max Phase: Preclinical

Molecular Formula: C20H30O4

Molecular Weight: 334.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)O[C@@H]1C[C@@H]1[C@@H](C)C(=O)C[C@@H]2C(C)(C)[C@@H](O)CC[C@@]12C

Standard InChI:  InChI=1S/C20H30O4/c1-11-8-18(23)24-15(11)9-13-12(2)14(21)10-16-19(3,4)17(22)6-7-20(13,16)5/h8,12-13,15-17,22H,6-7,9-10H2,1-5H3/t12-,13-,15-,16-,17+,20+/m1/s1

Standard InChI Key:  DGVPZQBBQYONCU-OTXCGIJESA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    1.2918   -3.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918   -4.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971   -5.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971   -3.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7024   -3.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034   -4.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4077   -5.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1155   -4.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -3.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057   -3.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -5.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6992   -5.5140    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6951   -3.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788   -5.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2039   -5.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8221   -3.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8232   -5.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4035   -2.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101   -2.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8577   -2.5759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4029   -1.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -1.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849   -0.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2158   -2.0504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3967   -1.8325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  1
  6 12  1  1
  5 13  1  6
  3 14  1  0
  3 15  1  0
  9 16  1  1
  8 17  2  0
 10 18  1  6
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
 23 24  1  0
 21 25  2  0
 19 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4526976

   ---

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: 334.46

Molecular Weight (Monoisotopic): 334.2144

AlogP: 3.28

#Rotatable Bonds: 2

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: 10.49

CX Basic pKa: ┄

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: 2.80

References

1. Castillo QA, Triana J, Eiroa JL, Calcul L, Rivera E, Wojtas L, Padrón JM, Padrón JM, Boberieth L, Keramane M, Abel-Santos E, Báez LA, Germosén EA..  (2016)  ent-Labdane Diterpenoids from the Aerial Parts of Eupatorium obtusissmum.,  79  (4): [PMID:27023255] [10.1021/acs.jnatprod.5b00954]

Source

Source(1):

• Scientific Literature