rac-5,6,7-Trimethoxy-3-(3'-hydroxy-4'-methoxybenzyl)-chromane

ID: ALA4532031

PubChem CID: 155546532

Max Phase: Preclinical

Molecular Formula: C20H24O6

Molecular Weight: 360.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(CC2COc3cc(OC)c(OC)c(OC)c3C2)cc1O

Standard InChI:  InChI=1S/C20H24O6/c1-22-16-6-5-12(9-15(16)21)7-13-8-14-17(26-11-13)10-18(23-2)20(25-4)19(14)24-3/h5-6,9-10,13,21H,7-8,11H2,1-4H3

Standard InChI Key:  RACFGZBMVCDIDQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   16.3713  -28.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5112  -27.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5100  -28.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2248  -28.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2230  -27.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9384  -27.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9373  -28.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6502  -28.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3701  -27.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6526  -27.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7966  -27.0711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2266  -29.5488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0843  -28.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8002  -28.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5116  -28.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2271  -28.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2304  -27.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5123  -27.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7999  -27.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9458  -27.0894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7952  -28.7228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0810  -28.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9400  -28.7415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7964  -26.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5129  -29.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9475  -26.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  6 10  1  0
  7  8  1  0
  8  1  1  0
  1  9  1  0
  9 10  1  0
  2 11  1  0
  4 12  1  0
  1 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
  3 21  1  0
 21 22  1  0
 16 23  1  0
 11 24  1  0
 12 25  1  0
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4532031

   ---

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: 360.41

Molecular Weight (Monoisotopic): 360.1573

AlogP: 3.22

#Rotatable Bonds: 6

Polar Surface Area: 66.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.04

CX Basic pKa: ┄

CX LogP: 3.31

CX LogD: 3.31

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: 1.13

References

1. Schwikkard S, Whitmore H, Sishtla K, Sulaiman RS, Shetty T, Basavarajappa HD, Waller C, Alqahtani A, Frankemoelle L, Chapman A, Crouch N, Wetschnig W, Knirsch W, Andriantiana J, Mas-Claret E, Langat MK, Mulholland D, Corson TW..  (2019)  The Antiangiogenic Activity of Naturally Occurring and Synthetic Homoisoflavonoids from the Hyacinthaceae ( sensu APGII).,  82  (5): [PMID:30951308] [10.1021/acs.jnatprod.8b00989]

Source

Source(1):

• Scientific Literature