Pentostatin

Details

• Internal ID: 244411e0-bc0e-4123-9491-a5f13730a20b
• Taxonomy: Organoheterocyclic compounds > Imidazodiazepines
• IUPAC Name: (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-8-ol
• SMILES (Canonical): C1C(C(OC1N2C=NC3=C2NC=NCC3O)CO)O
• SMILES (Isomeric): C1[C@@H]([C@H](O[C@H]1N2C=NC3=C2NC=NC[C@H]3O)CO)O
• InChI: InChI=1S/C11H16N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h4-9,16-18H,1-3H2,(H,12,13)/t6-,7+,8+,9+/m0/s1
• InChI Key: FPVKHBSQESCIEP-JQCXWYLXSA-N
• Popularity: 2,274 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₆N₄O₄
• Molecular Weight: 268.27 g/mol
• Exact Mass: 268.11715500 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -0.99
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• Deoxycoformycin
• 53910-25-1
• Nipent
• 2'-Deoxycoformycin
• Covidarabine
• CO-Vidarabine
• CI-825
• Vidarbine
• NSC-218321
• 2'-Dexoycoformycin
• YK-176
• Pentostatina
• Pentostatine
• Pentostatinum
• Coforin
• Oncopent
• 2'-DCF
• Co-V
• Nipent (TN)
• PD 81565
• PD-81565
• PD-ADI
• Vira A deaminase inhibitor
• Pentostatin (JAN/USAN/INN)
• (R)-2'-Deoxycoformycin
• DTXSID2023436
• UNII-395575MZO7
• (R)-Deoxycoformycin
• 395575MZO7
• (8R)-3-(2-Deoxy-beta-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
• (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol
• NCGC00182045-01
• 8R-2'-Deoxycoformycin
• Deaminase inhibitor (PD)
• NSC218321
• CL-67310465
• dCF
• NSC 218321
• Pentostatine [INN-French]
• Pentostatinum [INN-Latin]
• Pentostatina [INN-Spanish]
• (R)-3-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
• (R)-3-(2-Deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo(4,5-d)(1,3)diazepin-8-ol
• HSDB 6547
• Pentostatin [USAN:INN:BAN:JAN]
• BRN 1223097
• (8R)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
• (R)-3-(2-Deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo(4,5-d)(1,3)diazepin-8-ol
• Imidazo[4,5-d][1,3]diazepin-8-ol, 3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydro-, (8R)-
• CI-825;Deoxycoformycin
• CL 67310465
• Deaminase, inhibitor for adenosine arabinoside
• Pentostatn
• Pentostatin [USAN:BAN:INN:JAN]
• C11-H16-N4-O4
• (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-8-ol
• (R)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
• Pentostatin (PTN)
• PENTOSTATIN [MI]
• PENTOSTATIN [INN]
• PENTOSTATIN [JAN]
• PENTOSTATIN [HSDB]
• PENTOSTATIN [USAN]
• D0T3AD
• PENTOSTATIN [VANDF]
• Pentostatin(Deoxycoformycin)
• SCHEMBL2817
• CHEMBL1580
• PENTOSTATIN [MART.]
• PENTOSTATIN [WHO-DD]
• BIDD:GT0136
• DTXCID403436
• GTPL4805
• BDBM22925
• Pentostatin, >=95% (HPLC)
• PENTOSTATIN [ORANGE BOOK]
• FPVKHBSQESCIEP-JQCXWYLXSA-N
• BDBM223291
• (8R)-3-(2-Deoxy-beta-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]-diazepin-8-ol
• (R)-3-((2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
• AMY10324
• HY-A0006
• Imidazo(4,5-d)(1,3)diazepin-8-ol, 3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydro-, (R)-
• Imidazo(4,5-d)(1,3)diazepin-8-ol, 3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydro-, (R)-
• Imidazo[4,5-d][1,3]diazepin-8-ol, 3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydro-, (R)-
• Tox21_113417
• MFCD00078802
• s9521
• AKOS024456918
• AKOS032949742
• CS-0374
• DB00552
• NCGC00388420-02
• CAS-53910-25-1
• C02267
• D00155
• EN300-222177
• A829822
• Q425470
• SR-01000883935
• J-523899
• SR-01000883935-1
• Adenosine Deaminase Inhibitor, DCF - CAS 53910-25-1
• Z2204459563
• (8R)-3-(2-Deoxy-?-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
• (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,4H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol
• (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-8-ol
• (R,Z)-3-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9461	94.61%
Caco-2	-	0.8296	82.96%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Nucleus	0.6414	64.14%
OATP2B1 inhibitior	-	0.8606	86.06%
OATP1B1 inhibitior	+	0.9222	92.22%
OATP1B3 inhibitior	+	0.9405	94.05%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9537	95.37%
P-glycoprotein inhibitior	-	0.9381	93.81%
P-glycoprotein substrate	-	0.7652	76.52%
CYP3A4 substrate	+	0.5131	51.31%
CYP2C9 substrate	-	0.8031	80.31%
CYP2D6 substrate	-	0.8349	83.49%
CYP3A4 inhibition	-	0.9262	92.62%
CYP2C9 inhibition	-	0.8863	88.63%
CYP2C19 inhibition	-	0.8898	88.98%
CYP2D6 inhibition	-	0.9122	91.22%
CYP1A2 inhibition	-	0.8677	86.77%
CYP2C8 inhibition	-	0.7513	75.13%
CYP inhibitory promiscuity	-	0.9214	92.14%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6215	62.15%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9719	97.19%
Skin irritation	-	0.7489	74.89%
Skin corrosion	-	0.9226	92.26%
Ames mutagenesis	-	0.6707	67.07%
Human Ether-a-go-go-Related Gene inhibition	-	0.6603	66.03%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	+	0.9064	90.64%
skin sensitisation	-	0.8451	84.51%
Respiratory toxicity	+	0.9667	96.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8736	87.36%
Acute Oral Toxicity (c)	III	0.5686	56.86%
Estrogen receptor binding	-	0.5761	57.61%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	+	0.6169	61.69%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6194	61.94%
PPAR gamma	-	0.5884	58.84%
Honey bee toxicity	-	0.8101	81.01%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.8093	80.93%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1910	P00813	Adenosine deaminase	0.033 nM; 0.0001 nM; 0.0025 nM	Ki; Ki; Ki	PMID: 12643924; PMID: 23084905; PMID: 6604819

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.14%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.84%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.31%	97.09%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	89.19%	98.46%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.94%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.08%	94.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.75%	95.83%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.04%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.95%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.32%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.56%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.94%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	81.54%	95.93%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	80.61%	96.67%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	80.05%	80.33%

Plants that contains it

• Allium ampeloprasum
• Artemisia gmelinii
• Drimia altissima
• Helenium amarum
• Scutellaria viscidula
• Senecio retrorsus
• Taxus wallichiana

Cross-Links

• PubChem: 439693
• NPASS: NPC74306
• ChEMBL: CHEMBL1580
• LOTUS: LTS0069464
• wikiData: Q425470