Bovine Metabolome Database: Showing metabocard for Biopterin (BMDB0000468)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:31:10 UTC

Update Date

2020-05-11 20:47:23 UTC

BMDB ID

BMDB0000468

Secondary Accession Numbers

BMDB00468

Metabolite Identification

Common Name

Biopterin

Description

Biopterin, also known as pterin H B2 or orinapterin, belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland. Biopterin, with regard to humans, has been found to be associated with several diseases such as parkinson's disease, pterin-4a carbinolamine dehydratase deficiency, urocanase deficiency, and segawa syndrome; biopterin has also been linked to the inborn metabolic disorder sepiapterin reductase deficiency. Based on a literature review a significant number of articles have been published on Biopterin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Biopterin	ChEBI
(1'r,1's) Biopterin	HMDB
2-Amino-6-(L-erythro-1,2-dihydroxypropyl)-4(3H)-pteridinone	HMDB
6-Biopterin	HMDB
L-Biopterin	HMDB
L-Erythro-biopterin	HMDB
Pterin H b2	HMDB
[S-(R,s)]-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone	HMDB
Orinapterin	HMDB
Dictyopterin	HMDB
2-Amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone	HMDB
Biopterin	MeSH

Chemical Formula

C₉H₁₁N₅O₃

Average Molecular Weight

237.2153

Monoisotopic Molecular Weight

237.086189243

IUPAC Name

2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4,8-dihydropteridin-4-one

Traditional Name

2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-8H-pteridin-4-one

CAS Registry Number

22150-76-1

SMILES

C[C@H](O)[C@H](O)C1=CNC2=NC(N)=NC(=O)C2=N1

InChI Identifier

InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1

InChI Key

LHQIJBMDNUYRAM-DZSWIPIPSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
Aminopyrimidine
Pyrimidone
Pyrazine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
1,2-diol
Secondary alcohol
Azacycle
Organic oxygen compound
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

biopterin (CHEBI:63931 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.7 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.4	ALOGPS
logP	-2.2	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.66 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.81 m³·mol⁻¹	ChemAxon
Polarizability	22.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0aos-1922500000-07177d5a450dbf7c637a	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0aos-1922500000-07177d5a450dbf7c637a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-3910000000-90aa51259ebfb8feb1f5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-044i-5094000000-cf05a1ca25a8f1348f75	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0190000000-cea25aa8258af5c9e837	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-0900000000-32102578ef16c3df8f17	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a5c-5900000000-441b149b7ee5432cdac3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004l-0920000000-6ebd6d01be7b4755e765	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0290000000-b312042f86e0c7f2f21f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-01tc-1940000000-c430f7870641b07714a1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01p9-0090000000-bae0fd7c5247d7cd7961	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0090000000-f4a07c087ef8fff2e2a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-f8f16fa810bd3969420a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0090000000-b4b32605d4abfd33394e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-8900000000-944c0957bfd73e1b3de4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-4900000000-6b39c8f4e23fb16bc1bc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004l-1900000000-da31236bbf093051d962	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9700000000-494f0b4ec95c686ec1a9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00r5-3900000000-f949b0622eaee3ac7b81	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0910000000-2d901c6e9fa821b2d170	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-7cb519f820fc69c6423a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0090000000-8aa892a20d8030a22d50	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0190000000-55344345937d9883d783	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0h91-1920000000-a6b8c5b9d802ce02b0c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-f8e54aa1d030a0c8a29d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0940000000-c3bcfa7320d53b878000	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9800000000-3ab4f0aaf7f070e3ae28	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-50efc32e534ecd957e71	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-0290000000-7aaf4a05ccf0d0bdaaf1	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Brain
Epidermis
Fibroblasts
Liver
Prostate Tissue

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details