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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2020-11-01 17:55:20 UTC

Update Date

2022-03-07 03:18:21 UTC

HMDB ID

HMDB0240713

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9-Methyladenine

Description

9-Methyladenine belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 9-Methyladenine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 9-Methyladenine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N9-Methyladenine	ChEBI

Chemical Formula

C₆H₇N₅

Average Molecular Weight

149.1533

Monoisotopic Molecular Weight

149.070145249

IUPAC Name

9-methyl-9H-purin-6-amine

Traditional Name

9H-purin-6-amine, 9-methyl-

CAS Registry Number

Not Available

SMILES

CN1C=NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C6H7N5/c1-11-3-10-4-5(7)8-2-9-6(4)11/h2-3H,1H3,(H2,7,8,9)

InChI Key

WRXCXOUDSPTXNX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-aminopurines

Alternative Parents

Substituents

6-aminopurine
Aminopyrimidine
N-substituted imidazole
Pyrimidine
Imidolactam
Azole
Imidazole
Heteroaromatic compound
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Primary amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyladenine (CHEBI:40526 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0240713)

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	-0.12	ALOGPS
logP	-0.31	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	18.6	ChemAxon
pKa (Strongest Basic)	5.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.62 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.5 m³·mol⁻¹	ChemAxon
Polarizability	14.51 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	163.792	30932474
DeepCCS	[M+Na]+	138.909	30932474
AllCCS	[M+H]+	134.8	32859911
AllCCS	[M+H-H2O]+	130.3	32859911
AllCCS	[M+NH4]+	139.0	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	128.3	32859911
AllCCS	[M+Na-2H]-	129.4	32859911
AllCCS	[M+HCOO]-	130.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.62 minutes	32390414
Predicted by Siyang on May 30, 2022	8.3642 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.92 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1108.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	297.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	76.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	197.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	65.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	274.0 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	268.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	172.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	571.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	100.1 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	658.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	165.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	210.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	424.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	273.0 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	90.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-Methyladenine	CN1C=NC2=C(N)N=CN=C12	2145.1	Standard polar	33892256
9-Methyladenine	CN1C=NC2=C(N)N=CN=C12	1736.4	Standard non polar	33892256
9-Methyladenine	CN1C=NC2=C(N)N=CN=C12	1671.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9-Methyladenine,1TMS,isomer #1	CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21	1870.9	Semi standard non polar	33892256
9-Methyladenine,1TMS,isomer #1	CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21	1812.1	Standard non polar	33892256
9-Methyladenine,1TMS,isomer #1	CN1C=NC2=C(N[Si](C)(C)C)N=CN=C21	2927.9	Standard polar	33892256
9-Methyladenine,2TMS,isomer #1	CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	1867.8	Semi standard non polar	33892256
9-Methyladenine,2TMS,isomer #1	CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	1881.2	Standard non polar	33892256
9-Methyladenine,2TMS,isomer #1	CN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	2529.5	Standard polar	33892256
9-Methyladenine,1TBDMS,isomer #1	CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21	2108.8	Semi standard non polar	33892256
9-Methyladenine,1TBDMS,isomer #1	CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21	1967.7	Standard non polar	33892256
9-Methyladenine,1TBDMS,isomer #1	CN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21	2981.9	Standard polar	33892256
9-Methyladenine,2TBDMS,isomer #1	CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	2269.6	Semi standard non polar	33892256
9-Methyladenine,2TBDMS,isomer #1	CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	2297.8	Standard non polar	33892256
9-Methyladenine,2TBDMS,isomer #1	CN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	2601.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Methyladenine 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 - 9-Methyladenine 10V, Positive-QTOF	splash10-0udi-0900000000-b0b2c7bd9b2ad50b0a19	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 20V, Positive-QTOF	splash10-0udi-0900000000-ed6925b823a5ec2cd365	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 40V, Positive-QTOF	splash10-053r-9800000000-3f3e266848c7c3da19e8	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 10V, Negative-QTOF	splash10-0002-0900000000-3b97b7c952c5cd775434	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 20V, Negative-QTOF	splash10-0002-0900000000-726eb83f3fc5ea5b06d9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 40V, Negative-QTOF	splash10-001i-4900000000-b0daeafed920d578990b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 10V, Negative-QTOF	splash10-0002-0900000000-0fdae69660ea9759916e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 20V, Negative-QTOF	splash10-0002-0900000000-6a42bd65616f33500067	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 40V, Negative-QTOF	splash10-00lr-7900000000-05cce3ef4dd6286886be	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 10V, Positive-QTOF	splash10-0udi-0900000000-18eefbc35459f26a6570	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 20V, Positive-QTOF	splash10-0udi-0900000000-a10052ac285350478228	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Methyladenine 40V, Positive-QTOF	splash10-0ac4-9300000000-b35797cba8329437783e	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

62890

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

69689

PDB ID

Not Available

ChEBI ID

40526

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

Not Available

Showing metabocard for 9-Methyladenine (HMDB0240713)

MOL for HMDB0240713 (9-Methyladenine)

3D MOL for HMDB0240713 (9-Methyladenine)

3D SDF for HMDB0240713 (9-Methyladenine)

3D-SDF for HMDB0240713 (9-Methyladenine)

PDB for HMDB0240713 (9-Methyladenine)

3D PDB for HMDB0240713 (9-Methyladenine)

SMILES for HMDB0240713 (9-Methyladenine)

INCHI for HMDB0240713 (9-Methyladenine)

Structure for HMDB0240713 (9-Methyladenine)

3D Structure for HMDB0240713 (9-Methyladenine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra