(R)-2-(6-(2-methylbut-3-en-2-yl)-7-oxo-3,7-dihydro-2H-furo[3,2-g]chromen-2-yl)propan-2-yl 2-hydroxyethylcarbamate

ID: ALA4098689

PubChem CID: 137659732

Max Phase: Preclinical

Molecular Formula: C22H27NO6

Molecular Weight: 401.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)c1cc2cc3c(cc2oc1=O)O[C@@H](C(C)(C)OC(=O)NCCO)C3

Standard InChI:  InChI=1S/C22H27NO6/c1-6-21(2,3)15-10-13-9-14-11-18(22(4,5)29-20(26)23-7-8-24)27-16(14)12-17(13)28-19(15)25/h6,9-10,12,18,24H,1,7-8,11H2,2-5H3,(H,23,26)/t18-/m1/s1

Standard InChI Key:  RMMSYCFQCRJWEK-GOSISDBHSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   34.3551  -18.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3592  -19.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0648  -19.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9537  -20.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7461  -20.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5358  -19.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5730  -20.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5712  -18.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8650  -20.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8691  -19.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1691  -18.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4606  -19.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4566  -20.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1610  -20.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7555  -18.7965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7415  -21.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4467  -21.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2799  -19.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2846  -20.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0647  -20.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5420  -19.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0569  -18.9512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7720  -20.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5892  -20.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0019  -21.0115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9936  -19.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8191  -21.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2319  -21.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0490  -21.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  9  7  1  0
  7 19  2  0
 18  8  2  0
  8 10  1  0
  9 10  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  2  0
 13  5  1  0
  5 16  1  0
 16 17  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 21  2  1  1
  2 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098689

   ---

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: 401.46

Molecular Weight (Monoisotopic): 401.1838

AlogP: 3.06

#Rotatable Bonds: 6

Polar Surface Area: 98.00

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 14.00

CX Basic pKa: ┄

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.57

Np Likeness Score: 1.51

References

1. Lin Y, Wang Q, Gu Q, Zhang H, Jiang C, Hu J, Wang Y, Yan Y, Xu J..  (2017)  Semisynthesis of (-)-Rutamarin Derivatives and Their Inhibitory Activity on Epstein-Barr Virus Lytic Replication.,  80  (1): [PMID:28093914] [10.1021/acs.jnatprod.6b00415]

Source

Source(1):

• Scientific Literature