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

ID: ALA4101164

PubChem CID: 137659147

Max Phase: Preclinical

Molecular Formula: C26H33NO6

Molecular Weight: 455.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)c1cc2cc3c(cc2oc1=O)O[C@@H](C(C)(C)OC(=O)CNCC1CCCO1)C3

Standard InChI:  InChI=1S/C26H33NO6/c1-6-25(2,3)19-11-16-10-17-12-22(31-20(17)13-21(16)32-24(19)29)26(4,5)33-23(28)15-27-14-18-8-7-9-30-18/h6,10-11,13,18,22,27H,1,7-9,12,14-15H2,2-5H3/t18?,22-/m1/s1

Standard InChI Key:  HANZUUDWDMVPSF-LMNIDFBRSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   19.5878  -11.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5920  -12.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2976  -12.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1865  -13.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9789  -13.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7686  -12.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8058  -13.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8040  -11.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0978  -12.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1018  -12.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4019  -11.7668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6934  -12.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6893  -12.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3937  -13.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9883  -11.7555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9743  -14.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6795  -14.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5126  -12.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5174  -12.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2975  -13.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7748  -12.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2897  -11.9101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0048  -13.2700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8219  -13.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2347  -13.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2263  -12.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0519  -13.9656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4646  -14.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2818  -14.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7677  -15.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5434  -15.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5386  -14.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7599  -14.0008    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
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101164

   ---

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: 455.55

Molecular Weight (Monoisotopic): 455.2308

AlogP: 3.65

#Rotatable Bonds: 8

Polar Surface Area: 87.00

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.09

CX LogP: 3.67

CX LogD: 3.65

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: 1.36

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