4-CDP-2-C-methyl-D-erythritol

Details

• Internal ID: 4470d798-9706-46af-8886-b1b2eff53669
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine ribonucleotides > Pyrimidine ribonucleoside diphosphates
• IUPAC Name: [[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S)-2,3,4-trihydroxy-3-methylbutyl] hydrogen phosphate
• SMILES (Canonical): CC(CO)(C(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=CC(=NC2=O)N)O)O)O)O
• SMILES (Isomeric): C[C@](CO)([C@@H](COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)N)O)O)O)O
• InChI: InChI=1S/C14H25N3O14P2/c1-14(23,6-18)8(19)5-29-33(26,27)31-32(24,25)28-4-7-10(20)11(21)12(30-7)17-3-2-9(15)16-13(17)22/h2-3,7-8,10-12,18-21,23H,4-6H2,1H3,(H,24,25)(H,26,27)(H2,15,16,22)/t7-,8-,10-,11-,12-,14+/m1/s1
• InChI Key: YFAUKWZNPVBCFF-XHIBXCGHSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₅N₃O₁₄P₂
• Molecular Weight: 521.31 g/mol
• Exact Mass: 521.08117648 g/mol
• Topological Polar Surface Area (TPSA): 271.00 Ų
• XlogP: -5.70
• Atomic LogP (AlogP): -3.20
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

• FB44VKC5JD
• CDP-methyl-D-erythritol
• 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(((hydroxy((2R,3S)-2,3,4-trihydroxy-3-methylbutoxy)phosphoryl phosphonato)oxy)methyl)oxolan-2-yl)-4-imino-1,4-dihydropyrimidin-2-olate
• 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[({hydroxy[(2R,3S)-2,3,4-trihydroxy-3-methylbutoxy]phosphoryl phosphonato}oxy)methyl]oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-olate
• RefChem:515763
• 4-CDP-2-C-methyl-D-erythritol
• 4-DIPHOSPHOCYTIDYL-2-C-METHYL-D-ERYTHRITOL
• 263016-94-0
• [[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S)-2,3,4-trihydroxy-3-methylbutyl] hydrogen phosphate
• cytidine 5'-{3-[(2R,3S)-2,3,4-trihydroxy-3-methylbutyl] dihydrogen diphosphate}
• SCHEMBL254288
• CHEMBL1231708
• CHEBI:16578
• DTXSID50332065
• DB03687
• PD059566
• NS00070430
• Q2715091
• Cytidine 5'-(trihydrogen diphosphate), P'-[(2R,3S)-2,3,4-trihydroxy-3-methylbutyl] ester
• {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy(2,3,4-trihydroxy-3-methylbutoxy)phosphoryl]oxy})phosphinic acid
• 5'-O-[(R)-hydroxy{[(S)-hydroxy{[(2R,3S)-2,3,4-trihydroxy-3-methylbutyl]oxy}phosphoryl]oxy}phosphoryl]cytidine
• 5'-O-[Hydroxy({hydroxy[(2R,3S)-2,3,4-trihydroxy-3-methylbutoxy]phosphoryl}oxy)phosphoryl]cytidine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5775	57.75%
Caco-2	-	0.8978	89.78%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.3588	35.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9162	91.62%
OATP1B3 inhibitior	+	0.9413	94.13%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6638	66.38%
P-glycoprotein inhibitior	-	0.5884	58.84%
P-glycoprotein substrate	-	0.6771	67.71%
CYP3A4 substrate	+	0.6220	62.20%
CYP2C9 substrate	-	0.8118	81.18%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.9137	91.37%
CYP2C9 inhibition	-	0.8617	86.17%
CYP2C19 inhibition	-	0.8366	83.66%
CYP2D6 inhibition	-	0.8660	86.60%
CYP1A2 inhibition	-	0.8618	86.18%
CYP2C8 inhibition	-	0.7985	79.85%
CYP inhibitory promiscuity	-	0.9658	96.58%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5178	51.78%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.9636	96.36%
Skin irritation	-	0.7723	77.23%
Skin corrosion	-	0.9241	92.41%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6542	65.42%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	+	0.5211	52.11%
skin sensitisation	-	0.8377	83.77%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6330	63.30%
Acute Oral Toxicity (c)	III	0.5840	58.40%
Estrogen receptor binding	+	0.7714	77.14%
Androgen receptor binding	+	0.8578	85.78%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5433	54.33%
Aromatase binding	+	0.6228	62.28%
PPAR gamma	+	0.6512	65.12%
Honey bee toxicity	-	0.7607	76.07%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.6758	67.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.71%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	96.56%	95.93%
CHEMBL2581	P07339	Cathepsin D	95.88%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.46%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.43%	97.25%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	90.47%	97.29%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	89.44%	80.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.75%	86.33%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	86.53%	100.00%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	86.43%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.78%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.77%	99.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.67%	96.90%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.37%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.27%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.26%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.82%	96.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.78%	93.65%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.92%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.48%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.46%	95.56%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 443199
• LOTUS: LTS0271613
• wikiData: Q2715091