Cytosine

Details

• Internal ID: 5f8d0502-0fa4-4b27-b88d-a7df8f99c937
• Taxonomy: Organoheterocyclic compounds > Diazines > Pyrimidines and pyrimidine derivatives > Pyrimidones
• IUPAC Name: 6-amino-1H-pyrimidin-2-one
• SMILES (Canonical): C1=C(NC(=O)N=C1)N
• SMILES (Isomeric): C1=C(NC(=O)N=C1)N
• InChI: InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)
• InChI Key: OPTASPLRGRRNAP-UHFFFAOYSA-N
• Popularity: 41,479 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄H₅N₃O
• Molecular Weight: 111.10 g/mol
• Exact Mass: 111.043261792 g/mol
• Topological Polar Surface Area (TPSA): 67.50 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -0.65
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 71-30-7
• 4-Amino-2-hydroxypyrimidine
• 4-aminopyrimidin-2(1H)-one
• Cytosinimine
• 2(1H)-Pyrimidinone, 4-amino-
• 4-Amino-2(1H)-pyrimidinone
• 6-amino-1H-pyrimidin-2-one
• DTXSID4044456
• CHEBI:16040
• NSC-27787
• 8J337D1HZY
• 4-amino-3h-pyrimidin-2-one
• DTXCID2024456
• NSC27787
• 6-amino-1,2-dihydropyrimidin-2-one
• RefChem:5728
• 200-749-5
• 4-Aminouracil
• 6-Aminopyrimidin-2(1h)-One
• MFCD00006034
• 4-aminopyrimidin-2-ol
• Cytosin
• 2(1H)-pyrimidinone, 6-amino-
• Cyt
• 4-amino-2-oxo-1,2-dihydropyrimidine
• 4-amino-2-pyrimidinol
• Zytosin
• AI3-52281
• 107646-83-3
• 134434-40-5
• 107646-84-4
• 134434-39-2
• 2(1H)-Pyrimidinone, 3,4-dihydro-4-imino-, (E)- (9CI)
• 4-Aminopyrimidin-2-(1H)-one
• 2(1H)-Pyrimidinone, 3,4-dihydro-4-imino-, (Z)- (9CI)
• 4-Aminopyrimidin-2(1H)-one (Cytosine)
• Cytosine-5,6-d2
• 6-amino-3-hydropyrimidin-2-one
• pyrimidine, 4-amino-2-hydroxy-
• SMR000857094
• 4-Amino-1H-pyrimidin-2-one
• EINECS 200-749-5
• Lamivudine EP Impurity E
• NSC 27787
• 2-Pyrimidinol, 1,4-dihydro-4-imino-
• aminopyrimidone
• UNII-8J337D1HZY
• iminopyrimidinone
• 3h-cytosine
• 66460-18-2
• 66460-21-7
• Cytosine (8CI)
• 4-amino-1,2-dihydropyrimidin-2-one
• Cytosine (Standard)
• Lamivudine impurity c
• 2-Pyrimidinol, 1,4-dihydro-4-imino-, (Z)- (9CI)
• Gemcitabine impurity A
• Cytosine, >=99%
• 2(1H)-Pyrimidinone, 4-amino- (9CI)
• Lamivudine impurity c rs
• CYTOSINE [MI]
• 4-amino-pyrimidin-2-ol
• 4-Amino-2-oxypyrimidine
• 2(1H)-Pyrimidinone, 3,4-dihydro-4-imino-
• bmse000180
• CYTOSINE [USP-RS]
• CYTOSINE [WHO-DD]
• Epitope ID:167475
• 4-Amino-2(1H)pyrimidone
• EC 200-749-5
• SCHEMBL4059
• SCHEMBL8618
• 4-Amino-2(1H)-pyrimidone
• 2-Hydroxy-6-amino-pyrimidin
• MLS001332635
• MLS001332636
• CHEMBL15913
• SCHEMBL308339
• SCHEMBL437958
• SCHEMBL437959
• SCHEMBL655341
• 2-Pyrimidinol, 1,6-dihydro-6-imino-, (E)- (9CI)
• GTPL8490
• orb1302527
• SCHEMBL4818561
• SCHEMBL6547006
• SCHEMBL8921275
• SCHEMBL10402537
• HY-I0626R
• MSK6920
• HMS2233N21
• HMS3369N05
• HMS5083D22
• Cytosine, >=99.0% (HPLC)
• ALBB-021996
• BCP22793
• HY-I0626
• STR01426
• Tox21_302139
• s4893
• SBB071711
• STK366767
• STL455080
• AKOS000120336
• AKOS005443393
• AKOS015896942
• AC-2489
• BCP9000005
• CCG-266052
• CS-W020703
• FC03781
• 2-Pyrimidinol, 1,6-dihydro-6-imino-
• CAS-71-30-7
• CID 5274263
• SRI-2354-05
• NCGC00247019-01
• NCGC00255926-01
• 66398-98-9
• 66460-19-3
• BP-20183
• Cytosine, Vetec(TM) reagent grade, 99%
• NCI60_012445
• SY001643
• 4-imino-3,4-dihydropyrimidin-2(1H)-one
• DB-029615
• DB-268893
• DB-268963
• DB-271170
• DB-271171
• DB-295125
• LAMIVUDINE IMPURITY E [EP IMPURITY]
• LAMIVUDINE IMPURITY C [USP IMPURITY]
• NS00006844
• ST45026865
• EN300-21504
• 71C307
• C00380
• 006C034
• 2-Pyrimidinol,1,6-dihydro-6-imino-,(E)-(9ci)
• F036359
• Q178425
• 2(1H)-Pyrimidinone,3,4-dihydro-4-imino-,(E)-(9ci)
• CBA1D098-C5AB-46CE-AAC6-754572886EB2
• Z203045338
• Cytosine, United States Pharmacopeia (USP) Reference Standard
• Cytosine, Pharmaceutical Secondary Standard; Certified Reference Material
• Gemcitabine impurity A, European Pharmacopoeia (EP) Reference Standard
• 66460-16-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	-	0.7069	70.69%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.8714	87.14%
Subcellular localzation	Nucleus	0.4083	40.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9852	98.52%
OATP1B3 inhibitior	+	0.9512	95.12%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9381	93.81%
P-glycoprotein inhibitior	-	0.9889	98.89%
P-glycoprotein substrate	-	0.9023	90.23%
CYP3A4 substrate	-	0.7444	74.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.9888	98.88%
CYP2C9 inhibition	-	0.9668	96.68%
CYP2C19 inhibition	-	0.9551	95.51%
CYP2D6 inhibition	-	0.9879	98.79%
CYP1A2 inhibition	-	0.9168	91.68%
CYP2C8 inhibition	-	0.9695	96.95%
CYP inhibitory promiscuity	-	0.9856	98.56%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8623	86.23%
Carcinogenicity (trinary)	Non-required	0.5436	54.36%
Eye corrosion	-	0.9888	98.88%
Eye irritation	+	0.9754	97.54%
Skin irritation	-	0.7715	77.15%
Skin corrosion	-	0.9701	97.01%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8119	81.19%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5984	59.84%
Acute Oral Toxicity (c)	III	0.6327	63.27%
Estrogen receptor binding	-	0.9689	96.89%
Androgen receptor binding	-	0.8352	83.52%
Thyroid receptor binding	-	0.7654	76.54%
Glucocorticoid receptor binding	-	0.8870	88.70%
Aromatase binding	-	0.8267	82.67%
PPAR gamma	-	0.8864	88.64%
Honey bee toxicity	-	0.9708	97.08%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	-	0.9383	93.83%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.29%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.92%	96.09%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	87.66%	85.30%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.77%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	83.29%	94.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.15%	94.00%

Plants that contains it

• Euryale ferox
• Gastrodia elata
• Maackia amurensis

Cross-Links

• PubChem: 597
• NPASS: NPC212436
• LOTUS: LTS0122344
• wikiData: Q178425