NP-MRD: Showing NP-Card for norlevorphanol (NP0287900)

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Record Information

Version

2.0

Created at

2022-09-09 17:22:56 UTC

Updated at

2022-09-09 17:22:56 UTC

NP-MRD ID

NP0287900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

norlevorphanol

Description

3-Hydroxymorphinan, also known as norlevorphanol, belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. norlevorphanol is found in Papaver somniferum. norlevorphanol was first documented in 2011 (PMID: 21606622). Based on a literature review a significant number of articles have been published on 3-Hydroxymorphinan (PMID: 34487960) (PMID: 32393072) (PMID: 32269947) (PMID: 31504591) (PMID: 30783196) (PMID: 29565959).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    3.8637   -2.7714   -0.3846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1145   -1.6761    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7101   -0.7353    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744    0.3467    1.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    0.4878    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642   -0.4632    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7960   -1.5582   -0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3553   -0.2748   -0.3626 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9716   -1.6058   -0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483   -1.4697   -0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0876   -0.9536    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5251    0.3901    0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384    0.3652    0.8118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4821    1.7424    1.0074 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9596    1.7026    1.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525    2.5623   -0.1782 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1252    1.9886   -1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300    0.6227   -1.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4169   -2.7869   -1.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7416   -0.8854    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4552    1.0798    1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097   -2.2716   -1.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7782   -2.3925    0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438   -1.8739   -1.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7648   -0.8330   -1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8954   -2.4784   -1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1718   -0.8453    0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9785   -1.7118    1.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968    0.5812    1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9295    1.1758    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -0.2349    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723    2.2555    1.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639    1.7125    2.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4874    2.6349    1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347    2.6405   -0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611    2.6351   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1941    1.9839   -1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507    0.1412   -2.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116    0.7734   -1.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 15  1  0
 15 14  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
  8 18  1  6
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  8  6  1  0
  6  7  2  0
  7  2  1  0
  6  5  1  0
 13 14  1  0
 13  8  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
 15 33  1  0
 15 34  1  0
 14 32  1  1
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  1
  7 22  1  0
M  END


  Mrv1652309092219222D          

 18 21  0  0  0  0            999 V2000
    4.7791    1.5503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1170    1.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2121    0.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -0.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8196   -0.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976    0.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    1.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0508    1.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    1.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4790    1.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4525    0.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251    0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0243    0.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -0.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2804   -0.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8142   -0.1556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    0.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313    1.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2CC3NCCC4(CCCCC34)C2=C1

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
IYNWSQDZXMGGGI-UHFFFAOYSA-N

> <FORMULA>
C16H21NO

> <MOLECULAR_WEIGHT>
243.35

> <EXACT_MASS>
243.1623143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.64125356188321

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6-trien-4-ol

> <JCHEM_LOGP>
2.3568481969773263

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.889250675428489

> <JCHEM_PKA_STRONGEST_BASIC>
10.595354464074981

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
72.7862

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6-trien-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0       8.921   2.894   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.685   1.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.863   0.446   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.627  -0.473   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.263  -0.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.035   1.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.839   2.536   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.828   2.624   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.186   3.351   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.494   2.538   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.445   0.999   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.087   0.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.779   1.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.727  -1.247   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.257  -1.069   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.520  -0.290   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       1.342   1.239   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.299   2.446   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   13   18                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    5                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    8                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
Norlevorphanol hydrobromide	HMDB
Norlevorphanol, 9alpha,13alpha,14alpha-isomer	HMDB
Norlevorphanol	MeSH

Chemical Formula

C₁₆H₂₁NO

Average Mass

243.3500 Da

Monoisotopic Mass

243.16231 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=CC=C2CC3NCCC4(CCCCC34)C2=C1

InChI Identifier

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

InChI Key

IYNWSQDZXMGGGI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Papaver somniferum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
Phenanthrene
Benzazocine
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Secondary amine
Amine
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

HMDB0255744

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

452801

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Hydroxymorphinan

METLIN ID

Not Available

PubChem Compound

519103

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jung TW, Hwang EJ, Pyun DH, Kim TJ, Lee HJ, Abd El-Aty AM, Bang JS, Kim HC, Jeong JH: 3-hydroxymorphinan enhances mitochondrial biogenesis and adipocyte browning through AMPK-dependent pathway. Biochem Biophys Res Commun. 2021 Nov 5;577:17-23. doi: 10.1016/j.bbrc.2021.08.083. Epub 2021 Aug 30. [PubMed:34487960 ]
Silva AR, Dinis-Oliveira RJ: Pharmacokinetics and pharmacodynamics of dextromethorphan: clinical and forensic aspects. Drug Metab Rev. 2020 May;52(2):258-282. doi: 10.1080/03602532.2020.1758712. Epub 2020 May 12. [PubMed:32393072 ]
Su WL, Weng YY, Huang WH, Shui HA, Chou TC: Mechanisms of the antiplatelet and analgesic effects of dextromethorphan and its metabolites. Ci Ji Yi Xue Za Zhi. 2019 Sep 5;32(2):154-161. doi: 10.4103/tcmj.tcmj_48_19. eCollection 2020 Apr-Jun. [PubMed:32269947 ]
Cornthwaite HM, McDonald CS, Watterson JH: Analysis of Dextromethorphan and Three Metabolites in Decomposed Skeletal Tissues by UPLC-QToF-MS: Comparison of Acute and Repeated Drug Exposures. J Anal Toxicol. 2019 Oct 17;43(9):726-733. doi: 10.1093/jat/bkz074. [PubMed:31504591 ]
Li Z, Bao X, Bai X, Zhang G, Wang J, Zhu M, Wang Y, Shang J, Sheng C, Zhang D, Wang Y: Design, Synthesis, and Biological Evaluation of Phenol Bioisosteric Analogues of 3-Hydroxymorphinan. Sci Rep. 2019 Feb 19;9(1):2247. doi: 10.1038/s41598-019-38911-1. [PubMed:30783196 ]
Watson AR, Roberts A: Identifying Levorphanol Ingestion Using Urine Biomarkers in Health Care Patients. Pain Physician. 2018 Mar;21(2):E167-E171. [PubMed:29565959 ]
Song JH, Yeh JZ: Dextromethorphan inhibition of voltage-gated proton currents in BV2 microglial cells. Neurosci Lett. 2012 May 10;516(1):94-8. doi: 10.1016/j.neulet.2012.03.065. Epub 2012 Apr 1. [PubMed:22487729 ]
Lutz JD, Isoherranen N: Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole. Drug Metab Dispos. 2012 Jan;40(1):159-68. doi: 10.1124/dmd.111.042200. Epub 2011 Oct 18. [PubMed:22010218 ]
Shin EJ, Bach JH, Lee SY, Kim JM, Lee J, Hong JS, Nabeshima T, Kim HC: Neuropsychotoxic and neuroprotective potentials of dextromethorphan and its analogs. J Pharmacol Sci. 2011;116(2):137-48. doi: 10.1254/jphs.11r02cr. Epub 2011 May 21. [PubMed:21606622 ]
Loos WJ, de Graan AJ, de Bruijn P, van Schaik RH, van Fessem MA, Lam MH, Mathijssen RH, Wiemer EA: Simultaneous quantification of dextromethorphan and its metabolites dextrorphan, 3-methoxymorphinan and 3-hydroxymorphinan in human plasma by ultra performance liquid chromatography/tandem triple-quadrupole mass spectrometry. J Pharm Biomed Anal. 2011 Jan 25;54(2):387-94. doi: 10.1016/j.jpba.2010.08.033. Epub 2010 Sep 21. [PubMed:20926215 ]
LOTUS database [Link]

Showing NP-Card for norlevorphanol (NP0287900)

MOL for NP0287900 (norlevorphanol)

3D MOL for NP0287900 (norlevorphanol)

3D SDF for NP0287900 (norlevorphanol)

3D-SDF for NP0287900 (norlevorphanol)

PDB for NP0287900 (norlevorphanol)

3D PDB for NP0287900 (norlevorphanol)

SMILES for NP0287900 (norlevorphanol)

INCHI for NP0287900 (norlevorphanol)

Structure for NP0287900 (norlevorphanol)

3D Structure for NP0287900 (norlevorphanol)