NORLEVORPHANOL

ID: ALA3989483

Cas Number: 39131-41-4

PubChem CID: 5463854

Max Phase: Phase

Molecular Formula: C16H21NO

Molecular Weight: 243.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: IDS-NN-006 | NIH-7539 | NORLEVORPHANOL|3-Hydroxymorphinan|1531-12-0|(-)-3-Hydroxymorphinan|E4S6LA88PG|(+/-)-3-Hydroxymorphinan|Morphinan-3-ol, (+/-)-|UNII-E4S6LA88PG|IDS-NN-006|IL94262N7K|NIH-7539|39131-41-4|Norlevorfanol|Norlevorphanolum|(-)-3-Morphinanol|Norlevorfanol [INN-Spanish]|Norlevorphanolum [INN-Latin]|UNII-IL94262N7K|Norlevorphanol [INN:BAN:DCF]|EINECS 216-236-4|NORLEVORPHANOL [MI]|NORLEVORPHANOL [INN]|SCHEMBL23822|DEA No. 9634|CHEMBL3989483|IYNWSQDZXMGGGI-NUEKZKHPSA-N|DTXSID301336128Show More⌵

Canonical SMILES:  Oc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3

Standard InChI:  InChI=1S/C16H21NO/c18-12-5-4-11-9-15-13-3-1-2-6-16(13,7-8-17-15)14(11)10-12/h4-5,10,13,15,17-18H,1-3,6-9H2/t13-,15+,16+/m0/s1

Standard InChI Key:  IYNWSQDZXMGGGI-NUEKZKHPSA-N

Molfile:  

     RDKit          2D

 20 23  0  0  0  0  0  0  0  0999 V2000
    0.2063   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -0.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313   -0.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313   -2.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -2.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063   -0.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -0.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4438   -0.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -1.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -0.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6813   -1.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -2.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4438   -2.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438   -3.1084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437    0.4640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7457   -1.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1582    0.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6187    0.4640    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -0.9649    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
 10  1  1  0
  1  2  2  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 10  9  1  0
 14 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  5 15  1  0
  8 16  1  0
 10 17  1  1
 16 18  1  0
 18 17  1  0
  8 19  1  6
  9 20  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3989483

   NORLEVORPHANOL

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 243.35

Molecular Weight (Monoisotopic): 243.1623

AlogP: 2.74

#Rotatable Bonds: ┄

Polar Surface Area: 32.26

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.89

CX Basic pKa: 10.60

CX LogP: 2.36

CX LogD: 0.30

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.73

Np Likeness Score: 1.71

References

1. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

2. Meyer MJ, Neumann VE, Friesacher HR, Zdrazil B, Brockmöller J, Tzvetkov MV..  (2019)  Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.,  62  (21): [PMID:31597043] [10.1021/acs.jmedchem.9b01301]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names