Showing Compound Deoxycytidine (FDB021871)

Record Information

Version

1.0

Creation date

2011-09-21 00:04:17 UTC

Update date

2020-09-17 15:38:09 UTC

Primary ID

FDB021871

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Deoxycytidine

Description

Deoxycytidine, also known as dC, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxycytidine is an extremely weak basic (essentially neutral) compound (based on its pKa). Deoxycytidine exists in all living species, ranging from bacteria to humans. Within humans, deoxycytidine participates in a number of enzymatic reactions. In particular, deoxycytidine can be biosynthesized from dCMP; which is mediated by the enzyme cytosolic purine 5'-nucleotidase. In addition, deoxycytidine can be converted into dCMP through its interaction with the enzyme uridine-cytidine kinase-like 1. In humans, deoxycytidine is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, Deoxycytidine has been detected, but not quantified in, several different foods, such as common sages, greenthread tea, chinese broccoli, oil palms, and lingonberries. This could make deoxycytidine a potential biomarker for the consumption of these foods. A pyrimidine 2'-deoxyribonucleoside having cytosine as the nucleobase.

CAS Number

951-77-9

Structure

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

Synonyms

Synonym	Source
4-Amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one	ChEBI
dC	ChEBI
DCYD	ChEBI
2'-Deoxycytidine	Kegg
1-(2-Deoxy-b-D-ribofuranosyl)cytosine	HMDB
1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-cytosine	HMDB
1-(2-Deoxy-beta-D-ribofuranosyl)cytosine	HMDB
1-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-cytosine	HMDB
1-(2-Deoxy-beta-delta-ribofuranosyl)cytosine	HMDB
2-Deoxy-cytidine	HMDB
4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone	HMDB
4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone	HMDB
4-Amino-1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2(1H)-pyrimidinone	HMDB
Cytosine deoxyribonucleoside	HMDB
Cytosine deoxyriboside	HMDB
Deoxy-cytidine	HMDB
Deoxyribose cytidine	HMDB
Desoxycytidine	HMDB
Deoxyribonucleoside, cytosine	HMDB
Deoxyriboside, cytosine	HMDB
Deoxycytidine	ChEBI
1-(2-deoxy-beta-D-erythro-pentofuranosyl)-Cytosine	hmdb
1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-Cytosine	hmdb
2-deoxy-Cytidine	hmdb
4-amino-1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one	ChEBI
deoxy-Cytidine	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	15.9 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.9	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	0.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.03 m³·mol⁻¹	ChemAxon
Polarizability	21.65 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

Chemical Formula

C9H13N3O4

IUPAC name

4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

InChI Identifier

InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1

InChI Key

CKTSBUTUHBMZGZ-SHYZEUOFSA-N

Isomeric SMILES

NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](CO)O1

Average Molecular Weight

227.2172

Monoisotopic Molecular Weight

227.090605919

Classification

Description

Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Pyrimidine 2'-deoxyribonucleoside
Aminopyrimidine
Pyrimidone
Hydropyrimidine
Pyrimidine
Imidolactam
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidine 2'-deoxyribonucleoside (CHEBI:15698 )
Deoxyribonucleosides (C00881 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Tissue and substructures:

All tissues

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Deoxycytidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9510000000-43f83823bd8a63669514	Spectrum
Predicted GC-MS	Deoxycytidine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0gb9-4912000000-fef878d78b0000e850bb	Spectrum
Predicted GC-MS	Deoxycytidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Deoxycytidine, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0900000000-27431bdd2327f6f2b886	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-1900000000-0ea85f3f3940843e385b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03dl-9500000000-569e473eba0b700f5b6e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0090000000-5c8c0fde4f2163fbc335	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-9420000000-28279714b575d59761ce	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9200000000-df7c76b755c9fac5267b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9100000000-acbd1d7557be6d716a19	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00kf-9100000000-056ef35d3aa743e0d5cf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03di-0910000000-52e9d173bb94576f7d9e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-03di-0900000000-e06e5a9f19c4162aa24f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-03di-0900000000-551d8ee9679ef3fb65fa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-03di-3900000000-4c62633283ba566dbee0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03di-0900000000-bac3656523b118a2c1bc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03dj-6900000000-dfa8435d3dd8b8981621	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-01t9-0690000000-72302b09c51553dde169	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-03fr-0930000000-f5c80400a73719f6211f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0006-9130000000-c7f95a478d22e3cc83f4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0090000000-af75883dba546c82e7bc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9420000000-562a675c6278a4ae2bc4	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-e9d4ffd1148d792f5132	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-4900000000-b2a5f419f882d45f6ae7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-8900000000-0bbcfd7be44c4f38c4fc	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1890000000-395ff33971fbc8368eca	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0016-4910000000-2dc8aa3aad2b1c83316f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-cc82bf3d145faf0a6ca3	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum