Cannabis Compound Database: Showing Compound Card for Dihydroneopterin triphosphate (CDB005165)

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Record Information

Version

1.0

Created at

2020-04-17 19:15:52 UTC

Updated at

2020-11-18 16:39:27 UTC

CannabisDB ID

CDB005165

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Dihydroneopterin triphosphate

Description

Dihydroneopterin triphosphate 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. Dihydroneopterin triphosphate is a strong basic compound (based on its pKa). Dihydroneopterin triphosphate exists in all living species, ranging from bacteria to humans. Within humans, dihydroneopterin triphosphate participates in a number of enzymatic reactions. In particular, dihydroneopterin triphosphate can be biosynthesized from 2,5-diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine through its interaction with the enzyme GTP cyclohydrolase. In addition, dihydroneopterin triphosphate can be converted into dyspropterin and pppi; which is mediated by the enzyme 6-pyruvoyl tetrahydrobiopterin synthase. In humans, dihydroneopterin triphosphate is involved in the metabolic disorder called hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps). Outside of the human body, Dihydroneopterin triphosphate has been detected, but not quantified in, several different foods, such as roselles, endives, chinese bayberries, garlics, and arrowroots. This could make dihydroneopterin triphosphate a potential biomarker for the consumption of these foods. It is also used in the Queuosine/Archeosine Pathway. 7,8-Dihydroneopterin triphosphate (DHNTP) is an intermediate in tetrahydrobiopterin biosynthesis. It is transformed by 6-pyruvoyltetrahydropterin synthase into 6-pyruvoyl-tetrahydropterin. Dihydroneopterin triphosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate	ChEBI
6-(L-Erythro-1,2-dihydroxy-3-triphosphooxypropyl)-7,8-dihydropterin	ChEBI
6-(L-Erythro-1,2-dihydroxypropyl 3-triphosphate)-7,8-dihydropterin	ChEBI
6-[(1S,2R)-1,2-Dihydroxy-3-triphosphooxypropyl]-7,8-dihydropterin	ChEBI
2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphoric acid	Generator
6-(L-Erythro-1,2-dihydroxypropyl 3-triphosphoric acid)-7,8-dihydropterin	Generator
Dihydroneopterin triphosphoric acid	Generator
2-amino-4-Hydroxy-6-(erythro-1,2,3-trihydroxypropyl) dihydropteridine triphosphate	HMDB
7,8-Dihydroneopterin 3'-triphosphate	HMDB
7,8-Dihydroneopterin triphosphate	HMDB
Dihydroneopterin triphosphate, (S-(r,s))-isomer	MeSH, HMDB
dihydro-Neopterin triphosphate	MeSH, HMDB
Dihydroneopterin triphosphate	HMDB

Chemical Formula

C₉H₁₆N₅O₁₃P₃

Average Molecular Weight

495.17

Monoisotopic Molecular Weight

494.9957

IUPAC Name

{[({[(2R,3S)-3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid

Traditional Name

{[(2R,3S)-3-(2-amino-4-oxo-7,8-dihydro-1H-pteridin-6-yl)-2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxyphosphonic acid

CAS Registry Number

20574-65-6

SMILES

NC1=NC2=C(N=C(CN2)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(=O)N1

InChI Identifier

InChI=1S/C9H16N5O13P3/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-25-29(21,22)27-30(23,24)26-28(18,19)20/h4,6,15-16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H4,10,11,13,14,17)/t4-,6+/m1/s1

InChI Key

DGGUVLXVLHAAGT-XINAWCOVSA-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
Hydroxypyrimidine
Secondary aliphatic/aromatic amine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Heteroaromatic compound
1,2-diol
Ketimine
Secondary alcohol
Secondary amine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Imine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterin phosphate (CHEBI:18372 )
dihydropterin (CHEBI:18372 )
neopterins (CHEBI:18372 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Subcellular:

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.71	ALOGPS
logP	-4.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	0.9	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	292.15 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	102.28 m³·mol⁻¹	ChemAxon
Polarizability	37.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Dihydroneopterin triphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kdm-5895400000-c878c84180ac32db5d6e	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fs-7239235000-209a5180925a00469a6f	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydroneopterin triphosphate, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-1344900000-749ef2751d4c02be068c	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ds-3966200000-7b11e054b0d9f45b441d	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-1920000000-db4d3283e1adc21eb602	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0430900000-3810f529876f3b2a139c	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-005c-9550100000-5ca0214d149cdaf8e715	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9610000000-4ef866d42ea41abade0f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000900000-c66663d87526f1b932c8	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ks-0049600000-b0bd4a1239d964cfabc2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000b-0931000000-e97653fab66aeb2aeb35	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0100900000-44d989804f7de0829af1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-8501900000-f10d33df2b148966d71f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-e1f5b79920ef4f1ff109	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Pterine Biosynthesis
Dopa-responsive dystonia		Not Available
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiency		Not Available
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)		Not Available
Hyperphenylalaninemia due to dhpr-deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alkaline phosphatase, placental type	ALPP	2q37	P05187	details
Intestinal-type alkaline phosphatase	ALPI	2q37.1	P09923	details
Alkaline phosphatase, tissue-nonspecific isozyme	ALPL	1p36.12	P05186	details
Alkaline phosphatase, placental-like	ALPPL2	2q37	P10696	details
6-pyruvoyl tetrahydrobiopterin synthase	PTS	11q22.3	Q03393	details
GTP cyclohydrolase 1	GCH1	14q22.1-q22.2	P30793	details
RuvB-like 2	RUVBL2	19q13.3	Q9Y230	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alkaline phosphatase, placental type	ALPP	2q37	P05187	details
Intestinal-type alkaline phosphatase	ALPI	2q37.1	P09923	details
Alkaline phosphatase, tissue-nonspecific isozyme	ALPL	1p36.12	P05186	details
Alkaline phosphatase, placental-like	ALPPL2	2q37	P10696	details
6-pyruvoyl tetrahydrobiopterin synthase	PTS	11q22.3	Q03393	details

Receptors

Not Available

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
RuvB-like 2	RUVBL2	19q13.3	Q9Y230	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000980

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

7,8-Dihydroneopterin triphosphate

METLIN ID

5917

PubChem Compound

121885

PDB ID

Not Available

ChEBI ID

18372

References

General References

Not Available

Only showing the first 10 proteins. There are 13 proteins in total.

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Enzymes

Enzyme Details

1. Alkaline phosphatase, placental type

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: ALPP
Uniprot ID:: P05187
Molecular weight:: 57953.31

Enzyme Details

2. Intestinal-type alkaline phosphatase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: ALPI
Uniprot ID:: P09923
Molecular weight:: 56811.695

Enzyme Details

3. Alkaline phosphatase, tissue-nonspecific isozyme

General function:: Involved in catalytic activity
Specific function:: This isozyme may play a role in skeletal mineralization.
Gene Name:: ALPL
Uniprot ID:: P05186
Molecular weight:: 57304.435

Enzyme Details

4. Alkaline phosphatase, placental-like

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: ALPPL2
Uniprot ID:: P10696
Molecular weight:: 57376.515

Enzyme Details

5. 6-pyruvoyl tetrahydrobiopterin synthase

General function:: Involved in 6-pyruvoyltetrahydropterin synthase activity
Specific function:: Involved in the biosynthesis of tetrahydrobiopterin, an essential cofactor of aromatic amino acid hydroxylases. Catalyzes the transformation of 7,8-dihydroneopterin triphosphate into 6-pyruvoyl tetrahydropterin.
Gene Name:: PTS
Uniprot ID:: Q03393
Molecular weight:: 16385.63

Enzyme Details

6. GTP cyclohydrolase 1

General function:: Involved in GTP cyclohydrolase I activity
Specific function:: Positively regulates nitric oxide synthesis in umbilical vein endothelial cells (HUVECs). May be involved in dopamine synthesis. May modify pain sensitivity and persistence. Isoform GCH-1 is the functional enzyme, the potential function of the enzymatically inactive isoforms remains unknown.
Gene Name:: GCH1
Uniprot ID:: P30793
Molecular weight:: 27902.855

Enzyme Details

7. RuvB-like 2

General function:: Involved in nucleotide binding
Specific function:: Possesses single-stranded DNA-stimulated ATPase and ATP-dependent DNA helicase (5' to 3') activity; hexamerization is thought to be critical for ATP hydrolysis and adjacent subunits in the ring-like structure contribute to the ATPase activity. Component of the NuA4 histone acetyltransferase complex which is involved in transcriptional activation of select genes principally by acetylation of nucleosomal histones H4 and H2A. This modification may both alter nucleosome - DNA interactions and promote interaction of the modified histones with other proteins which positively regulate transcription. This complex may be required for the activation of transcriptional programs associated with oncogene and proto-oncogene mediated growth induction, tumor suppressor mediated growth arrest and replicative senescence, apoptosis, and DNA repair. The NuA4 complex ATPase and helicase activities seem to be, at least in part, contributed by the association of RUVBL1 and RUVBL2 with EP400. NuA4 may also play a direct role in DNA repair when recruited to sites of DNA damage. Proposed core component of the chromatin remodeling INO80 complex which is involved in transcriptional regulation, DNA replication and probably DNA repair. Plays an essential role in oncogenic transformation by MYC and also modulates transcriptional activation by the LEF1/TCF1-CTNNB1 complex. May also inhibit the transcriptional activity of ATF2.
Gene Name:: RUVBL2
Uniprot ID:: Q9Y230
Molecular weight:: 51156.08

Only showing the first 10 proteins. There are 13 proteins in total.

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Showing Compound Card for Dihydroneopterin triphosphate (CDB005165)

Structure for CDB005165 (Dihydroneopterin triphosphate)

Enzymes