NP-MRD: Showing NP-Card for trans-3'-hydroxycotinine (NP0339598)

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Record Information

Version

2.0

Created at

2024-09-11 22:38:22 UTC

Updated at

2024-09-11 22:38:23 UTC

NP-MRD ID

NP0339598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-3'-hydroxycotinine

Description

Trans-3'-hydroxycotinine belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. trans-3'-hydroxycotinine was first documented in 2024 (PMID: 39270062). Based on a literature review very few articles have been published on trans-3'-hydroxycotinine (PMID: 39125048) (PMID: 38463008).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05272301102D          

 14 15  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3381   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7358   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5642   -1.7646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339598

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(CC(O)C1=O)C1=CC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3

> <INCHI_KEY>
XOKCJXZZNAUIQN-UHFFFAOYNA-N

> <FORMULA>
C10H12N2O2

> <MOLECULAR_WEIGHT>
192.218

> <EXACT_MASS>
192.089877634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.41124908340461

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

> <JCHEM_LOGP>
-0.7332253989999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.107323140437016

> <JCHEM_PKA_STRONGEST_BASIC>
4.788748646548031

> <JCHEM_POLAR_SURFACE_AREA>
53.43000000000001

> <JCHEM_REFRACTIVITY>
50.7291

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.342  -5.926   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.377  -2.739   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.044  -2.739   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.364  -1.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.829  -0.757   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.973  -1.788   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.653  -3.294   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.189  -3.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    2    8                                                  
CONECT    8    7                                                            
CONECT    9    3   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₂N₂O₂

Average Mass

192.2180 Da

Monoisotopic Mass

192.08988 Da

IUPAC Name

3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

Traditional Name

3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

CAS Registry Number

Not Available

SMILES

CN1C(CC(O)C1=O)C1=CC=CN=C1

InChI Identifier

InChI=1/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3

InChI Key

XOKCJXZZNAUIQN-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as pyrrolidinylpyridines. These are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyrrolidinylpyridines

Direct Parent

Pyrrolidinylpyridines

Alternative Parents

Substituents

Pyrrolidinylpyridine
Alkaloid or derivatives
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Carboxamide group
Lactam
Secondary alcohol
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a secondary metabolite (CPD-2750 )

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
logP	-0.73	ChemAxon
pKa (Strongest Acidic)	13.11	ChemAxon
pKa (Strongest Basic)	4.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	53.43 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	50.73 m³·mol⁻¹	ChemAxon
Polarizability	19.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tang Y, Bryant MS, Li M, Min S, Pellar G, Wu Q, Yang DJ, Kang HK, Sepehr E, He X, McLellen F, Lewis SM, Greenhaw J, Fisher J, Yang X, Chemerynski S, Yee SB, Rosenfeldt H, Yeager RP, Howard PC, Hu SC, Roque P, Goel R, Kc P, Yi J: Pharmacokinetic Analysis of Nicotine and Its Metabolites (Cotinine and trans-3'-Hydroxycotinine) in Male Sprague-Dawley Rats Following Nose-Only Inhalation, Oral Gavage, and Intravenous Infusion of Nicotine. Toxicol Sci. 2024 Sep 12:kfae120. doi: 10.1093/toxsci/kfae120. [PubMed:39270062 ]
Szumska M, Mroczek P, Tyrpien-Golder K, Pastuszka B, Janoszka B: Determination of Cotinine, 3'-Hydroxycotinine and Nicotine 1'-Oxide in Urine of Passive and Active Young Smokers by LC-Orbitrap-MS/MS Technique. Molecules. 2024 Aug 1;29(15):3643. doi: 10.3390/molecules29153643. [PubMed:39125048 ]
Dai HD, Michaud T, Guenzel N, Morgan M, Cohen SM: Biomarker Assessment of Nicotine Exposure Among Adolescent E-Cigarette Users: 2018-2019. Pediatrics. 2024 Apr 1;153(4):e2023062424. doi: 10.1542/peds.2023-062424. [PubMed:38463008 ]

Showing NP-Card for trans-3'-hydroxycotinine (NP0339598)

MOL for NP0339598 (trans-3'-hydroxycotinine)

3D MOL for NP0339598 (trans-3'-hydroxycotinine)

3D SDF for NP0339598 (trans-3'-hydroxycotinine)

3D-SDF for NP0339598 (trans-3'-hydroxycotinine)

PDB for NP0339598 (trans-3'-hydroxycotinine)

3D PDB for NP0339598 (trans-3'-hydroxycotinine)

SMILES for NP0339598 (trans-3'-hydroxycotinine)

INCHI for NP0339598 (trans-3'-hydroxycotinine)

Structure for NP0339598 (trans-3'-hydroxycotinine)

3D Structure for NP0339598 (trans-3'-hydroxycotinine)