6aR,11aR-1-hydroxy-4-isoprenyl-maackiain

ID: ALA4090778

PubChem CID: 137644292

Max Phase: Preclinical

Molecular Formula: C21H20O6

Molecular Weight: 368.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCc1c(O)cc(O)c2c1OC[C@H]1c3cc4c(cc3O[C@@H]21)OCO4

Standard InChI:  InChI=1S/C21H20O6/c1-10(2)3-4-11-14(22)6-15(23)19-20(11)24-8-13-12-5-17-18(26-9-25-17)7-16(12)27-21(13)19/h3,5-7,13,21-23H,4,8-9H2,1-2H3/t13-,21+/m0/s1

Standard InChI Key:  HDSKERZFYMZNDJ-YEJXKQKISA-N

Molfile:  

     RDKit          2D

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    3.9136   -4.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9160   -4.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6213   -5.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186   -3.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3207   -4.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3259   -4.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7422   -4.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0275   -3.7169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7473   -4.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0347   -5.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2072   -6.1644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3562   -5.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0221   -6.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5011   -6.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1708   -5.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6487   -6.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3209   -6.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9357   -7.3662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6435   -6.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4675   -6.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2086   -3.7283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6192   -6.1731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6150   -2.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9083   -2.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046   -1.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2020   -1.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6117   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4564   -4.5398    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3256   -5.7700    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 17  2  0
 16 15  2  0
 15 12  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
  9 28  1  6
 10 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4090778

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 368.39

Molecular Weight (Monoisotopic): 368.1260

AlogP: 3.94

#Rotatable Bonds: 2

Polar Surface Area: 77.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.84

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.70

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: 2.39

References

1. Yang X, Deng S, Huang M, Wang J, Chen L, Xiong M, Yang J, Zheng S, Ma X, Zhao P, Feng Y..  (2017)  Chemical constituents from Sophora tonkinensis and their glucose transporter 4 translocation activities.,  27  (6): [PMID:28236591] [10.1016/j.bmcl.2017.01.078]

Source

Source(1):

• Scientific Literature