(3R,4R)-8-hydroxy-3-((S)-2-hydroxypentyl)-4,6,7-trimethoxyisochroman-1-one

ID: ALA4873636

PubChem CID: 164622493

Max Phase: Preclinical

Molecular Formula: C17H24O7

Molecular Weight: 340.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC[C@H](O)C[C@H]1OC(=O)c2c(cc(OC)c(OC)c2O)[C@H]1OC

Standard InChI:  InChI=1S/C17H24O7/c1-5-6-9(18)7-12-15(22-3)10-8-11(21-2)16(23-4)14(19)13(10)17(20)24-12/h8-9,12,15,18-19H,5-7H2,1-4H3/t9-,12+,15+/m0/s1

Standard InChI Key:  BHPZFTLUYCMBBI-TURKWSHLSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   29.7149   -2.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7137   -3.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4286   -4.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4268   -2.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1421   -2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1409   -3.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5816   -2.8442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8602   -2.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5805   -3.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8610   -4.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8602   -1.5993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4242   -1.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0004   -2.4334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9990   -4.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2860   -2.8461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9984   -4.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8603   -4.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2935   -4.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1455   -5.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0094   -3.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7224   -4.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4383   -3.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1513   -4.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0124   -2.8574    0.0000 O   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
  8 11  2  0
  4 12  1  0
  1 13  1  0
  2 14  1  0
 13 15  1  0
 14 16  1  0
 10 17  1  6
  9 18  1  6
 17 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4873636

   ---

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: 340.37

Molecular Weight (Monoisotopic): 340.1522

AlogP: 2.19

#Rotatable Bonds: 7

Polar Surface Area: 94.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.10

CX Basic pKa: ┄

CX LogP: 2.39

CX LogD: 2.38

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: 2.13

References

1. Coronado L, Zhang XQ, Dorta D, Escala N, Pineda LM, Ng MG, Del Olmo E, Wang CY, Gu YC, Shao CL, Spadafora C..  (2021)  Semisynthesis, Antiplasmodial Activity, and Mechanism of Action Studies of Isocoumarin Derivatives.,  84  (5.0): [PMID:33979168] [10.1021/acs.jnatprod.0c01032]

Source

Source(1):

• Scientific Literature