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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:14:25 UTC

Update Date

2021-10-01 18:57:42 UTC

HMDB ID

HMDB0247230

Secondary Accession Numbers

None

Metabolite Identification

Common Name

7-Amino-4-methylcoumarin

Description

7-Amino-4-methylcoumarin, also known as coumarin C440 or 4-methyl-7-aminocoumarin, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Based on a literature review very few articles have been published on 7-Amino-4-methylcoumarin. This compound has been identified in human blood as reported by (PMID: 31557052 ). 7-amino-4-methylcoumarin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 7-Amino-4-methylcoumarin 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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: MCM                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -3.244  -1.966   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.910  -1.196   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.577  -1.966   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.757  -1.196   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.424  -1.196   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.424   0.344   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.091   1.114   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.757   0.344   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.577   1.114   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.910   0.344   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.091   2.654   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.091  -1.966   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.758  -1.966   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    8   12                                                  
CONECT    5    6   12   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    4    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    2    9                                                       
CONECT   11    7                                                            
CONECT   12    4    5                                                       
CONECT   13    5                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Amino-4-methylcoumarin, conjugate monoacid	HMDB
Coumarin C440	HMDB
4-Methyl-7-aminocoumarin	HMDB
Coumarin 120	HMDB
7-amino-4-Methylcoumarin	ChEBI

Chemical Formula

C₁₀H₉NO₂

Average Molecular Weight

175.184

Monoisotopic Molecular Weight

175.063328537

IUPAC Name

7-amino-4-methyl-2H-chromen-2-one

Traditional Name

7-amino-4-methylcoumarin

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)OC2=C1C=CC(N)=C2

InChI Identifier

InChI=1S/C10H9NO2/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5H,11H2,1H3

InChI Key

GLNDAGDHSLMOKX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-aminocoumarins (CHEBI:51771 )

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	1.59	ALOGPS
logP	1.25	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	3.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.53 m³·mol⁻¹	ChemAxon
Polarizability	17.93 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	139.274	30932474
DeepCCS	[M-H]-	136.718	30932474
DeepCCS	[M-2H]-	172.2	30932474
DeepCCS	[M+Na]+	147.392	30932474
AllCCS	[M+H]+	135.3	32859911
AllCCS	[M+H-H2O]+	130.7	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.8	32859911
AllCCS	[M-H]-	135.8	32859911
AllCCS	[M+Na-2H]-	136.2	32859911
AllCCS	[M+HCOO]-	136.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Amino-4-methylcoumarin	CC1=CC(=O)OC2=C1C=CC(N)=C2	2968.9	Standard polar	33892256
7-Amino-4-methylcoumarin	CC1=CC(=O)OC2=C1C=CC(N)=C2	1966.3	Standard non polar	33892256
7-Amino-4-methylcoumarin	CC1=CC(=O)OC2=C1C=CC(N)=C2	2080.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Amino-4-methylcoumarin,1TMS,isomer #1	CC1=CC(=O)OC2=CC(N[Si](C)(C)C)=CC=C12	2124.4	Semi standard non polar	33892256
7-Amino-4-methylcoumarin,1TMS,isomer #1	CC1=CC(=O)OC2=CC(N[Si](C)(C)C)=CC=C12	2119.4	Standard non polar	33892256
7-Amino-4-methylcoumarin,1TMS,isomer #1	CC1=CC(=O)OC2=CC(N[Si](C)(C)C)=CC=C12	2372.2	Standard polar	33892256
7-Amino-4-methylcoumarin,2TMS,isomer #1	CC1=CC(=O)OC2=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C12	2166.0	Semi standard non polar	33892256
7-Amino-4-methylcoumarin,2TMS,isomer #1	CC1=CC(=O)OC2=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C12	2145.5	Standard non polar	33892256
7-Amino-4-methylcoumarin,2TMS,isomer #1	CC1=CC(=O)OC2=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C12	2261.6	Standard polar	33892256
7-Amino-4-methylcoumarin,1TBDMS,isomer #1	CC1=CC(=O)OC2=CC(N[Si](C)(C)C(C)(C)C)=CC=C12	2384.9	Semi standard non polar	33892256
7-Amino-4-methylcoumarin,1TBDMS,isomer #1	CC1=CC(=O)OC2=CC(N[Si](C)(C)C(C)(C)C)=CC=C12	2278.2	Standard non polar	33892256
7-Amino-4-methylcoumarin,1TBDMS,isomer #1	CC1=CC(=O)OC2=CC(N[Si](C)(C)C(C)(C)C)=CC=C12	2476.4	Standard polar	33892256
7-Amino-4-methylcoumarin,2TBDMS,isomer #1	CC1=CC(=O)OC2=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C12	2573.7	Semi standard non polar	33892256
7-Amino-4-methylcoumarin,2TBDMS,isomer #1	CC1=CC(=O)OC2=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C12	2561.6	Standard non polar	33892256
7-Amino-4-methylcoumarin,2TBDMS,isomer #1	CC1=CC(=O)OC2=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C12	2437.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Amino-4-methylcoumarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-057i-1900000000-739a5c8861e4e7d36e6b	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Amino-4-methylcoumarin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin LC-ESI-QFT , positive-QTOF	splash10-004i-0900000000-9498ceb31167ba961666	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 30V, Positive-QTOF	splash10-00e9-0900000000-54d5a105a032e1569940	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 20V, Positive-QTOF	splash10-004i-0900000000-5da5961059c378baab41	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 10V, Positive-QTOF	splash10-004i-0900000000-b955a735a0efcce169f8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 50V, Positive-QTOF	splash10-004i-0900000000-217b917b80cff8ddd71c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 35V, Positive-QTOF	splash10-004i-0900000000-eb56672dedd6a32373df	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 10V, Positive-QTOF	splash10-004i-0900000000-51a0a7b3c3d144f49bf9	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 20V, Positive-QTOF	splash10-004i-0900000000-4121150358adb32edf42	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 40V, Positive-QTOF	splash10-017l-4900000000-a673e4c8df42395b11bf	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 10V, Negative-QTOF	splash10-00di-0900000000-c034b95e4529cb744721	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 20V, Negative-QTOF	splash10-00di-0900000000-4971f851527d003b146c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 40V, Negative-QTOF	splash10-008c-3900000000-f27e680aa20885f2cd8e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 10V, Positive-QTOF	splash10-004i-0900000000-d07827f54b9762c6f46c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 20V, Positive-QTOF	splash10-004i-0900000000-20fc8962b8a29b40c962	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 40V, Positive-QTOF	splash10-0159-3900000000-7c62d29da94ab30fc53a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 10V, Negative-QTOF	splash10-00di-0900000000-e1e7a7636061f9624da0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 20V, Negative-QTOF	splash10-00di-0900000000-e1e7a7636061f9624da0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Amino-4-methylcoumarin 40V, Negative-QTOF	splash10-0aos-4900000000-feaeec57a0c2f2009cc9	2021-10-12	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

DB08168

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00048593

Chemspider ID

83285

KEGG Compound ID

C01386

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92249

PDB ID

Not Available

ChEBI ID

51771

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 ]

Enzymes

Enzyme Details

1. Subtilisin-like serine protease Pen c 1

General function:: Not Available
Specific function:: Serine protease (PubMed:10103041, PubMed:7763554). Hydrolyzes azocasein (PubMed:10103041). Cleaves peptide bonds of the oxidized insulin B chain preferably at 15-Leu-|-Tyr-16, but also at 4-Gln-|-His-5 and 24-Phe-|-Phe-25, and to a lesser extent at 5-His-|-Leu-6 and 25-Phe-|-Tyr-26. Hydrolyzes amide bonds between amino acids and 7-amino-4-methylcoumarin (AMC) in vitro (PubMed:7763554).
Gene Name:: Not Available
Uniprot ID:: Q9Y749
Molecular weight:: 40383.44

Showing metabocard for 7-Amino-4-methylcoumarin (HMDB0247230)

MOL for HMDB0247230 (7-Amino-4-methylcoumarin)

3D MOL for HMDB0247230 (7-Amino-4-methylcoumarin)

3D SDF for HMDB0247230 (7-Amino-4-methylcoumarin)

3D-SDF for HMDB0247230 (7-Amino-4-methylcoumarin)

PDB for HMDB0247230 (7-Amino-4-methylcoumarin)

3D PDB for HMDB0247230 (7-Amino-4-methylcoumarin)

SMILES for HMDB0247230 (7-Amino-4-methylcoumarin)

INCHI for HMDB0247230 (7-Amino-4-methylcoumarin)

Structure for HMDB0247230 (7-Amino-4-methylcoumarin)

3D Structure for HMDB0247230 (7-Amino-4-methylcoumarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes