Cannabis Compound Database: Showing Compound Card for UDP-D-apiose (CDB005032)

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Record Information

Version

1.0

Created at

2020-04-17 19:02:23 UTC

Updated at

2020-11-18 16:39:14 UTC

CannabisDB ID

CDB005032

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

UDP-D-apiose

Description

UDP-D-apiose, also known as UDP-apiose, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. UDP-D-apiose is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, UDP-D-apiose has been detected, but not quantified in, several different foods, such as spelts, bilberries, gingers, japanese chestnuts, and bitter gourds. This could make UDP-D-apiose a potential biomarker for the consumption of these foods. UDP-D-apiose is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
UDP-Apiose	MeSH
Uridine 5'-(alpha-D-apio-D-furanosyl pyrophosphate)	MeSH
[({[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinate	Generator

Chemical Formula

C₁₄H₂₂N₂O₁₆P₂

Average Molecular Weight

536.28

Monoisotopic Molecular Weight

536.0445

IUPAC Name

[({[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid

Traditional Name

{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy(hydroxy)phosphoryl}oxy([(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphinic acid

CAS Registry Number

20230-91-5

SMILES

OC[C@@]1(O)CO[C@@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@@H]1O

InChI Identifier

InChI=1S/C14H22N2O16P2/c17-4-14(23)5-28-12(10(14)21)31-34(26,27)32-33(24,25)29-3-6-8(19)9(20)11(30-6)16-2-1-7(18)15-13(16)22/h1-2,6,8-12,17,19-21,23H,3-5H2,(H,24,25)(H,26,27)(H,15,18,22)/t6-,8-,9-,10+,11-,12+,14-/m1/s1

InChI Key

SYVORCSTSYHSPN-VPPDZDBCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine ribonucleotides

Direct Parent

Pyrimidine ribonucleoside diphosphates

Alternative Parents

Substituents

Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Vinylogous amide
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Lactam
Urea
Azacycle
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

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	-0.7	ALOGPS
logP	-4.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	274.8 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	101.03 m³·mol⁻¹	ChemAxon
Polarizability	43.57 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	UDP-D-apiose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-7644590000-9057d8ed31f50e9a99c6	Spectrum
Predicted GC-MS	UDP-D-apiose, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01b9-8001209000-465c481e28d06373cfa5	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	UDP-D-apiose, TMS_2_16, 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	splash10-03di-0901110000-f76d25f46131ce59ad0e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3910000000-9030d650ff99164a047c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-4900000000-156bb85e162785682af7	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01p6-4411790000-097298b9bde8b801e092	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-9753210000-7b8a1d2f0a08bfa57674	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06r6-4900000000-ddd397cf6a1ccecec79e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0000960000-ed43e7655a9965e52127	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bvu-1893860000-4b4f9d53fc899ec8189c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2922000000-49c3b52de84d534d8693	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000090000-ea6246f6d98035ff4c44	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bwi-8816960000-cb8f4173981f38279af2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053u-3629000000-160d619e4a84b5569870	2021-09-22	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0012301

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028924

KNApSAcK ID

Not Available

Chemspider ID

35032431

KEGG Compound ID

C01623

BioCyc ID

UDP-APIOSE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25202307

PDB ID

Not Available

ChEBI ID

15933

References

General References

Not Available

Showing Compound Card for UDP-D-apiose (CDB005032)

Structure for CDB005032 (UDP-D-apiose)