Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:44:29 UTC

Update Date

2022-11-24 00:09:12 UTC

HMDB ID

HMDB0255164

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Isopropylaniline

Description

N-ISOPROPYLANILINE belongs to the class of organic compounds known as phenylisopropylamines. These are organic aromatic compounds containing a 1-phenylpropan-2-amine moiety. N-ISOPROPYLANILINE is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). N-isopropylaniline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Isopropylaniline is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-Isopropylaniline hydrochloride	MeSH
N-Isopropylaniline	MeSH

Chemical Formula

C₉H₁₃N

Average Molecular Weight

135.21

Monoisotopic Molecular Weight

135.104799423

IUPAC Name

N-(propan-2-yl)aniline

Traditional Name

N-isopropylaniline

CAS Registry Number

Not Available

SMILES

CC(C)NC1=CC=CC=C1

InChI Identifier

InChI=1S/C9H13N/c1-8(2)10-9-6-4-3-5-7-9/h3-8,10H,1-2H3

InChI Key

FRCFWPVMFJMNDP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylisopropylamines. These are organic aromatic compounds containing a 1-phenylpropan-2-amine moiety.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Phenylisopropylamines

Alternative Parents

Substituents

Phenylisopropylamine
Aniline or substituted anilines
Secondary aliphatic/aromatic amine
Benzenoid
Monocyclic benzene moiety
Secondary amine
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.56	ALOGPS
logP	2.22	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	5.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.42 m³·mol⁻¹	ChemAxon
Polarizability	16.31 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	132.505	30932474
DeepCCS	[M-H]-	128.932	30932474
DeepCCS	[M-2H]-	166.329	30932474
DeepCCS	[M+Na]+	141.526	30932474
AllCCS	[M+H]+	130.2	32859911
AllCCS	[M+H-H2O]+	125.6	32859911
AllCCS	[M+NH4]+	134.4	32859911
AllCCS	[M+Na]+	135.6	32859911
AllCCS	[M-H]-	130.0	32859911
AllCCS	[M+Na-2H]-	131.9	32859911
AllCCS	[M+HCOO]-	134.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	13.0582 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.27 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1791.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	436.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	252.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	435.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	600.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1057.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	390.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	941.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	374.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	223.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	25.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-ISOPROPYLANILINE	CC(C)NC1=CC=CC=C1	1631.2	Standard polar	33892256
N-ISOPROPYLANILINE	CC(C)NC1=CC=CC=C1	1133.2	Standard non polar	33892256
N-ISOPROPYLANILINE	CC(C)NC1=CC=CC=C1	1156.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-ISOPROPYLANILINE,1TMS,isomer #1	CC(C)N(C1=CC=CC=C1)[Si](C)(C)C	1248.3	Semi standard non polar	33892256
N-ISOPROPYLANILINE,1TMS,isomer #1	CC(C)N(C1=CC=CC=C1)[Si](C)(C)C	1297.3	Standard non polar	33892256
N-ISOPROPYLANILINE,1TMS,isomer #1	CC(C)N(C1=CC=CC=C1)[Si](C)(C)C	1473.9	Standard polar	33892256
N-ISOPROPYLANILINE,1TBDMS,isomer #1	CC(C)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1454.3	Semi standard non polar	33892256
N-ISOPROPYLANILINE,1TBDMS,isomer #1	CC(C)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1494.1	Standard non polar	33892256
N-ISOPROPYLANILINE,1TBDMS,isomer #1	CC(C)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1637.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Isopropylaniline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9600000000-859f1a30435c477fb55d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Isopropylaniline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isopropylaniline 10V, Positive-QTOF	splash10-000i-1900000000-f3d5e9c0822338a18b4a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isopropylaniline 20V, Positive-QTOF	splash10-000l-9800000000-4dbaa2b84839e5cd3d0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isopropylaniline 40V, Positive-QTOF	splash10-00kf-9100000000-b4f35d871673fe1b52c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isopropylaniline 10V, Negative-QTOF	splash10-001i-0900000000-da3fa9dfd3f8c628cf83	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isopropylaniline 20V, Negative-QTOF	splash10-001i-2900000000-906295b7f7a0b6650fc4	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isopropylaniline 40V, Negative-QTOF	splash10-0006-9300000000-2570f501252a1c20cec5	2016-08-04	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

13032

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for N-Isopropylaniline (HMDB0255164)

MOL for HMDB0255164 (N-Isopropylaniline)

3D MOL for HMDB0255164 (N-Isopropylaniline)

3D SDF for HMDB0255164 (N-Isopropylaniline)

3D-SDF for HMDB0255164 (N-Isopropylaniline)

PDB for HMDB0255164 (N-Isopropylaniline)

3D PDB for HMDB0255164 (N-Isopropylaniline)

SMILES for HMDB0255164 (N-Isopropylaniline)

INCHI for HMDB0255164 (N-Isopropylaniline)

Structure for HMDB0255164 (N-Isopropylaniline)

3D Structure for HMDB0255164 (N-Isopropylaniline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra