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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:37 UTC

Update Date

2023-02-21 17:16:11 UTC

HMDB ID

HMDB0002128

Secondary Accession Numbers

HMDB02128

Metabolite Identification

Common Name

2,4-Diamino-6-hydroxypyrimidine

Description

2,4-Diamino-6-hydroxypyrimidine (DAHP) is a selective inhibitor of GTP cyclohydrolase I (GTPCH) that restricts the de novo synthesis of tetrahydrobiopterin (BH4) or the BH4 precursor in vascular smooth muscle cells (VSMC). (PMID 12883322 ). 2,4-Diamino-6-hydroxypyrimidine also inhibits nitric oxide (NO) in both Interferon-gamma (IFN-gamma) and antigen (Ag)/IgE (Ag/IgE) systems, increasing Mast cells (MC) degranulation. (PMID 14514683 ). Sepiapterin, a precursor to tetrahydrobiopterin in the salvage pathway, completely reverses the effect of 2,4-diamino-6-hydroxypyrimidine on neuronal NO-synthase (nNOS) ubiquitylation. (PMID 16216381 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4-diamino-6-Pyrimidinone	HMDB
2,6-diamino-4(1H)-Pyrimidinone	HMDB
2,6-diamino-4(3H)-Pyrimidinone	HMDB
2,6-diamino-4-Hydroxypyrimidine	HMDB
2,6-diamino-4-Pyrimidinol	HMDB
2,6-Diaminopyrimidin-4-one	HMDB
6-Aminoisocytosine	HMDB
6-Hydroxy-2,4-pyrimidinediamine	HMDB
2,4-DAHP	MeSH, HMDB
2,4-Diaminohypoxanthine sulfate	MeSH, HMDB
DHAP-2,4	MeSH, HMDB
2,4-Diaminohypoxanthine	MeSH, HMDB
2,4-Diamino-6-hydroxypyrimidine	MeSH

Chemical Formula

C₄H₆N₄O

Average Molecular Weight

126.1166

Monoisotopic Molecular Weight

126.054160834

IUPAC Name

2,6-diamino-1,4-dihydropyrimidin-4-one

Traditional Name

6-aminoisocytosine

CAS Registry Number

56-06-4

SMILES

NC1=CC(=O)N=C(N)N1

InChI Identifier

InChI=1S/C4H6N4O/c5-2-1-3(9)8-4(6)7-2/h1H,(H5,5,6,7,8,9)

InChI Key

SWELIMKTDYHAOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

Aminopyrimidine
Pyrimidone
Hydropyrimidine
Vinylogous amide
Heteroaromatic compound
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0002128)

Process

Not Available

Role

Industrial application

Drug (HMDB: HMDB0002128)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	286 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	858500 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.3 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.6	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	15.84	ChemAxon
pKa (Strongest Basic)	1.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	93.5 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.88 m³·mol⁻¹	ChemAxon
Polarizability	11.37 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	124.54	31661259
DarkChem	[M-H]-	120.427	31661259
DeepCCS	[M+H]+	127.636	30932474
DeepCCS	[M-H]-	125.256	30932474
DeepCCS	[M-2H]-	161.6	30932474
DeepCCS	[M+Na]+	136.493	30932474
AllCCS	[M+H]+	127.6	32859911
AllCCS	[M+H-H2O]+	122.8	32859911
AllCCS	[M+NH4]+	132.1	32859911
AllCCS	[M+Na]+	133.3	32859911
AllCCS	[M-H]-	120.0	32859911
AllCCS	[M+Na-2H]-	122.1	32859911
AllCCS	[M+HCOO]-	124.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4-Diamino-6-hydroxypyrimidine	NC1=CC(=O)N=C(N)N1	2744.2	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine	NC1=CC(=O)N=C(N)N1	1554.3	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine	NC1=CC(=O)N=C(N)N1	1818.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,4-Diamino-6-hydroxypyrimidine,1TMS,isomer #1	C[Si](C)(C)NC1=CC(=O)N=C(N)[NH]1	1732.9	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TMS,isomer #1	C[Si](C)(C)NC1=CC(=O)N=C(N)[NH]1	1863.7	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TMS,isomer #1	C[Si](C)(C)NC1=CC(=O)N=C(N)[NH]1	2600.3	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C=C(N)[NH]1	1739.1	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C=C(N)[NH]1	1818.3	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C=C(N)[NH]1	2639.8	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TMS,isomer #3	C[Si](C)(C)N1C(N)=CC(=O)N=C1N	1764.1	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TMS,isomer #3	C[Si](C)(C)N1C(N)=CC(=O)N=C1N	1751.2	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TMS,isomer #3	C[Si](C)(C)N1C(N)=CC(=O)N=C1N	2699.5	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #1	C[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C)[NH]1	1762.3	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #1	C[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C)[NH]1	1982.7	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #1	C[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C)[NH]1	2536.9	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #2	C[Si](C)(C)N(C1=CC(=O)N=C(N)[NH]1)[Si](C)(C)C	1739.7	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #2	C[Si](C)(C)N(C1=CC(=O)N=C(N)[NH]1)[Si](C)(C)C	1925.7	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #2	C[Si](C)(C)N(C1=CC(=O)N=C(N)[NH]1)[Si](C)(C)C	2492.3	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #3	C[Si](C)(C)NC1=CC(=O)N=C(N)N1[Si](C)(C)C	1791.0	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #3	C[Si](C)(C)NC1=CC(=O)N=C(N)N1[Si](C)(C)C	1885.5	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #3	C[Si](C)(C)NC1=CC(=O)N=C(N)N1[Si](C)(C)C	2418.4	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #4	C[Si](C)(C)N(C1=NC(=O)C=C(N)[NH]1)[Si](C)(C)C	1744.1	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #4	C[Si](C)(C)N(C1=NC(=O)C=C(N)[NH]1)[Si](C)(C)C	1904.5	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #4	C[Si](C)(C)N(C1=NC(=O)C=C(N)[NH]1)[Si](C)(C)C	2475.1	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #5	C[Si](C)(C)NC1=NC(=O)C=C(N)N1[Si](C)(C)C	1781.0	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #5	C[Si](C)(C)NC1=NC(=O)C=C(N)N1[Si](C)(C)C	1886.9	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TMS,isomer #5	C[Si](C)(C)NC1=NC(=O)C=C(N)N1[Si](C)(C)C	2486.6	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]1	1774.3	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]1	1919.3	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]1	2365.7	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #2	C[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]1	1786.1	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #2	C[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]1	1964.0	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #2	C[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]1	2220.4	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #3	C[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C)N1[Si](C)(C)C	1846.0	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #3	C[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C)N1[Si](C)(C)C	1972.1	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #3	C[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C)N1[Si](C)(C)C	2280.2	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #4	C[Si](C)(C)N(C1=CC(=O)N=C(N)N1[Si](C)(C)C)[Si](C)(C)C	1795.7	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #4	C[Si](C)(C)N(C1=CC(=O)N=C(N)N1[Si](C)(C)C)[Si](C)(C)C	1926.7	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #4	C[Si](C)(C)N(C1=CC(=O)N=C(N)N1[Si](C)(C)C)[Si](C)(C)C	2361.6	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #5	C[Si](C)(C)N(C1=NC(=O)C=C(N)N1[Si](C)(C)C)[Si](C)(C)C	1782.2	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #5	C[Si](C)(C)N(C1=NC(=O)C=C(N)N1[Si](C)(C)C)[Si](C)(C)C	1945.0	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TMS,isomer #5	C[Si](C)(C)N(C1=NC(=O)C=C(N)N1[Si](C)(C)C)[Si](C)(C)C	2332.5	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TMS,isomer #1	C[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]1)[Si](C)(C)C	1833.9	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TMS,isomer #1	C[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]1)[Si](C)(C)C	1983.2	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TMS,isomer #1	C[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]1)[Si](C)(C)C	2060.5	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C	1880.8	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C	1988.7	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TMS,isomer #2	C[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C	2142.9	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TMS,isomer #3	C[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C	1920.2	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TMS,isomer #3	C[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C	2008.2	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TMS,isomer #3	C[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C	2039.2	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,5TMS,isomer #1	C[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C	1961.9	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,5TMS,isomer #1	C[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C	2088.8	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,5TMS,isomer #1	C[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C)[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C	1923.9	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N)[NH]1	1987.5	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N)[NH]1	2067.4	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N)[NH]1	2699.5	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N)[NH]1	1990.8	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N)[NH]1	2029.7	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N)[NH]1	2734.4	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(N)=CC(=O)N=C1N	2012.3	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(N)=CC(=O)N=C1N	1952.5	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(N)=CC(=O)N=C1N	2746.5	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]1	2252.8	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]1	2343.0	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C(C)(C)C)[NH]1	2616.7	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N)[NH]1)[Si](C)(C)C(C)(C)C	2172.4	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N)[NH]1)[Si](C)(C)C(C)(C)C	2295.4	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N)[NH]1)[Si](C)(C)C(C)(C)C	2535.1	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N)N1[Si](C)(C)C(C)(C)C	2250.1	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N)N1[Si](C)(C)C(C)(C)C	2296.6	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N)N1[Si](C)(C)C(C)(C)C	2501.9	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C=C(N)[NH]1)[Si](C)(C)C(C)(C)C	2144.4	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C=C(N)[NH]1)[Si](C)(C)C(C)(C)C	2315.0	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C=C(N)[NH]1)[Si](C)(C)C(C)(C)C	2497.5	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N)N1[Si](C)(C)C(C)(C)C	2219.2	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N)N1[Si](C)(C)C(C)(C)C	2292.1	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N)N1[Si](C)(C)C(C)(C)C	2552.5	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1	2382.1	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1	2512.0	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1	2557.7	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1	2389.8	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1	2541.5	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1	2451.1	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2479.3	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2558.3	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2492.7	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2418.7	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2531.2	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2540.4	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C=C(N)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2386.6	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C=C(N)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2554.7	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C=C(N)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2511.8	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C	2571.6	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C	2761.6	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C	2446.1	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2660.6	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2769.8	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=O)C=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2518.8	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2662.6	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2789.8	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2451.5	Standard polar	33892256
2,4-Diamino-6-hydroxypyrimidine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2885.1	Semi standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2976.2	Standard non polar	33892256
2,4-Diamino-6-hydroxypyrimidine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC(=O)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2449.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-4900000000-1e063b05226e8896a663	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 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 - 2,4-Diamino-6-hydroxypyrimidine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-0900000000-00f9b9f5ce4b5cad43b0	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014i-9000000000-40b3a1d8e972f237c69e	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014i-9000000000-bedf37ced21617434775	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 10V, Positive-QTOF	splash10-004i-0900000000-5e3c38e0a0a648095bbd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 20V, Positive-QTOF	splash10-004i-2900000000-b08fbf010a25872f527e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 40V, Positive-QTOF	splash10-000f-9000000000-37474e4ea02c53c6dbbf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 10V, Negative-QTOF	splash10-004i-2900000000-33f401e4d08da16fa38f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 20V, Negative-QTOF	splash10-004i-3900000000-d44c471a63adfa036032	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 40V, Negative-QTOF	splash10-000x-9000000000-515cef0906e879cd3b67	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 10V, Positive-QTOF	splash10-004i-0900000000-17e49b273de10b22c70b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 20V, Positive-QTOF	splash10-002f-9200000000-f64008e5d2bac657c5a4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 40V, Positive-QTOF	splash10-00kf-9000000000-8fe725f865981c7d648f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 10V, Negative-QTOF	splash10-004i-7900000000-8ac5ea6d8dbacebc0edf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 20V, Negative-QTOF	splash10-0006-9000000000-76ada99b8a779fab63d8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Diamino-6-hydroxypyrimidine 40V, Negative-QTOF	splash10-00kf-9000000000-9c42190a2a1ee0031cf7	2021-09-24	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
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB022857

KNApSAcK ID

Not Available

Chemspider ID

2840

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6500

PubChem Compound

2944

PDB ID

Not Available

ChEBI ID

804916

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1163371

References

Synthesis Reference

Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Kamada Y, Jenkins GJ, Lau M, Dunbar AY, Lowe ER, Osawa Y: Tetrahydrobiopterin depletion and ubiquitylation of neuronal nitric oxide synthase. Brain Res Mol Brain Res. 2005 Dec 7;142(1):19-27. Epub 2005 Oct 10. [PubMed:16216381 ]
Yoshida M, Nakanishi N, Wang X, Hattori Y: Exogenous biopterins requirement for iNOS function in vascular smooth muscle cells. J Cardiovasc Pharmacol. 2003 Aug;42(2):197-203. [PubMed:12883322 ]
Gilchrist M, Hesslinger C, Befus AD: Tetrahydrobiopterin, a critical factor in the production and role of nitric oxide in mast cells. J Biol Chem. 2003 Dec 12;278(50):50607-14. Epub 2003 Sep 26. [PubMed:14514683 ]

Showing metabocard for 2,4-Diamino-6-hydroxypyrimidine (HMDB0002128)

MOL for HMDB0002128 (2,4-Diamino-6-hydroxypyrimidine)

3D MOL for HMDB0002128 (2,4-Diamino-6-hydroxypyrimidine)

3D SDF for HMDB0002128 (2,4-Diamino-6-hydroxypyrimidine)

3D-SDF for HMDB0002128 (2,4-Diamino-6-hydroxypyrimidine)

PDB for HMDB0002128 (2,4-Diamino-6-hydroxypyrimidine)

3D PDB for HMDB0002128 (2,4-Diamino-6-hydroxypyrimidine)

SMILES for HMDB0002128 (2,4-Diamino-6-hydroxypyrimidine)

INCHI for HMDB0002128 (2,4-Diamino-6-hydroxypyrimidine)

Structure for HMDB0002128 (2,4-Diamino-6-hydroxypyrimidine)

3D Structure for HMDB0002128 (2,4-Diamino-6-hydroxypyrimidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra