10-(1-Hydroxy-ethyl)-1,2,3-trimethoxy-6,7-dihydro-5H-9-oxa-benzo[3,4]cyclohepta[1,2-f]inden-7-ol

ID: ALA4103889

PubChem CID: 137656916

Max Phase: Preclinical

Molecular Formula: C22H24O6

Molecular Weight: 384.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(c(OC)c1OC)-c1cc3cc(C(C)O)oc3cc1C(O)CC2

Standard InChI:  InChI=1S/C22H24O6/c1-11(23)17-9-13-7-15-14(10-18(13)28-17)16(24)6-5-12-8-19(25-2)21(26-3)22(27-4)20(12)15/h7-11,16,23-24H,5-6H2,1-4H3

Standard InChI Key:  OANSUPXVOFHHME-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   19.6153  -20.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6142  -21.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3222  -21.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3204  -20.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0338  -21.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0290  -20.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6700  -20.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4745  -20.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8358  -20.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4868  -21.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6865  -21.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4512  -22.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0492  -22.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8176  -23.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0168  -23.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9571  -24.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7211  -24.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2528  -23.8097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6530  -20.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3225  -22.6405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6150  -23.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9061  -21.8224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1987  -21.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9075  -20.1864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9073  -19.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9168  -25.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3275  -25.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7017  -25.4608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  5  2  0
  6  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  5 11  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  0
 10 11  2  0
 11 12  1  0
 12 15  2  0
 14 13  2  0
 13 10  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  1  0
  9 19  1  0
  3 20  1  0
 20 21  1  0
  2 22  1  0
 22 23  1  0
  1 24  1  0
 24 25  1  0
 17 26  1  0
 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103889

   ---

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: 384.43

Molecular Weight (Monoisotopic): 384.1573

AlogP: 4.16

#Rotatable Bonds: 4

Polar Surface Area: 81.29

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.57

CX Basic pKa: ┄

CX LogP: 2.65

CX LogD: 2.65

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.70

Np Likeness Score: 1.35

References

1. Gracheva IA, Voitovich IV, Faerman VI, Sitnikov NS, Myrsikova EV, Schmalz HG, Svirshevskaya EV, Fedorov AY..  (2017)  Synthesis and cytostatic properties of polyfunctionalized furanoallocolchicinoids.,  126  [PMID:27912174] [10.1016/j.ejmech.2016.11.020]

Source

Source(1):

• Scientific Literature