Deferoxamine

Details

• Internal ID: ea6fe47f-8895-4c5e-8dfa-3e31f4891673
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Carboxylic acid derivatives > Hydroxamic acids > Acetohydroxamic acids
• IUPAC Name: N-[5-[[4-[5-[acetyl(hydroxy)amino]pentylamino]-4-oxobutanoyl]-hydroxyamino]pentyl]-N'-(5-aminopentyl)-N'-hydroxybutanediamide
• SMILES (Canonical): CC(=O)N(CCCCCNC(=O)CCC(=O)N(CCCCCNC(=O)CCC(=O)N(CCCCCN)O)O)O
• SMILES (Isomeric): CC(=O)N(CCCCCNC(=O)CCC(=O)N(CCCCCNC(=O)CCC(=O)N(CCCCCN)O)O)O
• InChI: InChI=1S/C25H48N6O8/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34)
• InChI Key: UBQYURCVBFRUQT-UHFFFAOYSA-N
• Popularity: 14,442 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₈N₆O₈
• Molecular Weight: 560.70 g/mol
• Exact Mass: 560.35336251 g/mol
• Topological Polar Surface Area (TPSA): 206.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): 0.92
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 23

Synonyms

• 70-51-9
• Desferrioxamine B
• DESFERRIOXAMINE
• Deferrioxamine
• Deferrioxamine B
• Deferoxamin
• Deferoxamine B
• Deferoxaminum
• Desferin
• DFOM
• Desferan
• Desferex
• Desferral
• Desferrin
• N-Benzoylferrioxamine B
• Deferoxamina
• DFOA
• NSC-527604
• Ferrioxamine B, N-benzoyl-
• Desferoxamine b
• Dfo-b
• J06Y7MXW4D
• NSC527604
• N-[5-[[4-[5-[acetyl(hydroxy)amino]pentylamino]-4-oxobutanoyl]-hydroxyamino]pentyl]-N'-(5-aminopentyl)-N'-hydroxybutanediamide
• 3,9,14,20,25-Pentaazatriacontane-2,10,13,21,24-pentone, 30-amino-3,14,25-trihydroxy-
• 30-Amino-3,14,25-trihydroxy-3,9,14,20,25-pentaazatriacontane-2,10,13,21,24-pentaone
• CHEBI:4356
• Butanediamide, N'-(5-((4-((5-(acetylhydroxyamino)pentyl)amino)-1,4-dioxobutyl)hydroxyamino)pentyl)-N-(5-aminopentyl)-N-hydroxy-
• DTXSID7022887
• 1-Amino-6,17-dihydroxy-7,10,18,21-tetraoxo-27-(N-acetyl hydroxylamino)-6,11,17,22-tetraazaheptaeicosane
• N-(5-(3-((5-Aminopentyl)hydroxycarbamoyl)propionamido)pentyl)-3-((5-(N-hydroxyacetamido)pentyl)carbamoyl)propionohydroxamic acid
• N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide
• Propionohydroxamic acid, N-(5-(3-((5-aminopentyl)hydroxycarbamoyl)propionamido)pentyl)-3-((5-(N-hydroxyacetamido)pentyl)carbamoyl)-
• Butanediamide, N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxy-
• Deferoximine
• Desferioximine
• Desferroxamine
• N-(5-((4-(5-(acetyl(hydroxy)amino)pentylamino)-4-oxobutanoyl)-hydroxyamino)pentyl)-N'-(5-aminopentyl)-N'-hydroxybutanediamide
• N-(5-aminopentyl)-N-hydroxy-N'-(5-(N-hydroxy-3-((5-(N-hydroxyacetamido)pentyl)carbamoyl)propanamido)pentyl)butanediamide
• N-[5-(3-[(5-Aminopentyl)hydroxycarbamoyl]propionamido)pentyl]-3-([5-(N-hydroxyacetamido)pentyl]carbamoyl)propionohydroxamic acid
• N-[5-{3-[(5-Aminopentyl)hydroxycarbamoyl]propionamido}pentyl]-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propionohydroxamic acid
• Propionohydroxamic acid, N-[5-[3-[(5-aminopentyl)hydroxycarbamoyl]propionamido]pentyl]-3-[[5-(N-hydroxyacetamido)pentyl]carbamoyl]-
• RefChem:54943
• DTXCID002887
• 1-amino-6,17-dihydroxy-7,10,18,21-tetraoxo-27-(n-acetylhydroxylamino)-6,11,17,22-tetraazaheptaeicosane
• 200-738-5
• N'-(5-((4-((5-(Acetylhydroxyamino)pentyl)amino)-1,4-dioxobutyl)hydroxyamino)pentyl)-N-(5-aminopentyl)-N-hydroxybutanediamide
• Deferoxamide B
• DF B
• N1-(5-Aminopentyl)-N1-hydroxy-N4-(5-(N-hydroxy-4-((5-(N-hydroxyacetamido)pentyl)amino)-4-oxobutanamido)pentyl)succinamide
• Deferoxamine (USAN)
• DEFEROXAMINE [USAN]
• Deferoxamine B; Deferriferrioxamine B; Deferrioxamine
• Desferriferrioxamin B
• MLS002702118
• Deferoxamine [USAN:INN]
• Deferoxaminum [INN-Latin]
• Deferoxamina [INN-Spanish]
• HSDB 3311
• SMR000058548
• EINECS 200-738-5
• Ba 33112
• UNII-J06Y7MXW4D
• BRN 2514118
• Cordaneurin
• Desferrioxamin
• Perineurin
• Desferioxamine B
• desferrioxamine-B
• N1-(5-Aminopentyl)-N1-hydroxy-N4-[5-[N-hydroxy-4-[[5-(N-hydroxyacetamido)pentyl]amino]-4-oxobutanamido]pentyl]succinamide
• deferoxamine-mesylate
• Desferal (Salt/Mix)
• Spectrum_000892
• Deferoxamine (Standard)
• Prestwick0_000725
• Prestwick1_000725
• Prestwick2_000725
• Prestwick3_000725
• Spectrum2_001155
• Spectrum3_000376
• Spectrum4_000311
• Spectrum5_000827
• DEFEROXAMINE [MI]
• DEFEROXAMINE [INN]
• CHEMBL556
• DEFEROXAMINE [HSDB]
• EC 200-738-5
• DEFEROXAMINE [VANDF]
• SCHEMBL34571
• BSPBio_000650
• BSPBio_002131
• KBioGR_000922
• KBioGR_002429
• KBioSS_001372
• KBioSS_002435
• cid_62881
• N'-(5-((4-((5-(Acetylhydroxamino)pentyl)amino)-1,4-dioxobutyl) hydroxyamino)pentyl)-N-(5-aminopentyl)-N-hydroxybutanediamide
• DEFEROXAMINE [WHO-DD]
• DivK1c_000082
• Ba 29837 (Salt/Mix)
• SPBio_001109
• SPBio_002589
• BPBio1_000716
• CGH-749B
• ICL-749B
• orb1992268
• BDBM47715
• HY-B1625R
• KBio1_000082
• KBio2_001372
• KBio2_002429
• KBio2_003940
• KBio2_004997
• KBio2_006508
• KBio2_007565
• KBio3_001351
• KBio3_002908
• cMAP_000047
• NINDS_000082
• HMS3604E17
• HY-B1625
• EBC-27321
• LMFA08020169
• MFCD00242585
• WLN: Z5NQV/2VM5NQV/ 21
• DEFEROXAMINE, Deferoxamine Mesylate
• AKOS016004824
• DB00746
• FD46531
• IDI1_000082
• SMP2_000121
• NCGC00178802-01
• NCGC00178802-02
• NCGC00178802-03
• DA-72630
• MS-30181
• NCI60_002181
• SMR001550278
• SY237696
• SBI-0051332.P003
• AB00053447
• CS-0013559
• NS00007870
• C06940
• D03670
• F11488
• AB00053447_14
• 070D519
• EN300-19748908
• Q419618
• BRD-K09821361-066-05-0
• BRD-K09821361-066-06-8
• BRD-K09821361-066-08-4
• BRD-K09821361-066-13-4
• BRD-K09821361-066-15-9
• BRD-K09821361-066-16-7
• BRD-K09821361-066-23-3
• BRD-K09821361-066-24-1
• BRD-K09821361-066-25-8
• 3,14,20,25-Pentaazatriacontane-2,10,13,21,24-pentone, 30-amino-3,14,25-trihydroxy-
• 30-Amino-3,25-trihydroxy-3,9,14,20,25-pentaazatriacontane-2,10,13,21,24-pentaone
• Butanediamide,4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxy-
• N''''-(5-azanylpentyl)-N-[5-[[4-[5-[ethanoyl(oxidanyl)amino]pentylamino]-4-oxidanylidene-butanoyl]-oxidanyl-amino]pentyl]-N''''-oxidanyl-butanediamide;methanesulfonic acid
• N'-[5-(acetyl-hydroxy-amino)pentyl]-N-[5-[3-(5-aminopentyl-hydroxy-carbamoyl)propanoylamino]pentyl]-N-hydroxy-butane diamide
• N'-{5-[acetyl(hydroxy)amino]pentyl}-N-(5-{4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanamido}pentyl)-N-hydroxybutanediamide
• N'-{5-[acetyl(hydroxy)amino]pentyl}-N-[5-({4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanoyl}amino)pentyl]-N-hydroxybutanediamide
• N-[5-[[4-[5-[acetyl(hydroxy)amino]pentylamino]-1,4-dioxobutyl]-hydroxyamino]pentyl]-N''''-(5-aminopentyl)-N''''-hydroxybutanediamide;methanesulfonic acid
• N-[5-[[4-[5-[acetyl(hydroxy)amino]pentylamino]-4-keto-butanoyl]-hydroxy-amino]pentyl]-N''-(5-aminopentyl)-N''-hydroxy-succinamide;mesylic acid
• N-[5-[[4-[5-[acetyl(hydroxy)amino]pentylamino]-4-oxobutanoyl]-hydroxyamino]pentyl]-N''''-(5-aminopentyl)-N''''-hydroxybutanediamide;methanesulfonic acid
• N~1~-(5-(Acetyl(hydroxy)amino)pentyl)-N~4~-(5-((4-((5-aminopentyl)(hydroxy)amino)-4-oxobutanoyl)amino)pentyl)-N~4~-hydroxysuccinamide
• N~1~-(5-Aminopentyl)-N~1~-hydroxy-N~4~-[5-(N-hydroxy-4-{[5-(N-hydroxyacetamido)pentyl]amino}-4-oxobutanamido)pentyl]butanediamide
• N~4~-{5-[acetyl(hydroxy)amino]pentyl}-N~1~-[5-({4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanoyl}amino)pentyl]-N~1~-hydroxybutanediamide
• Propionohydroxamic acid, N-[5-(3-[(5-aminopentyl)hydroxycarbamoyl]propionamido)phentyl]-3-([5-(N-hydroxyacetamido)pentyl]carbamoyl)-
• Propionohydroxamic acid, N-[5-[3-[(5-aminopentyl)hydroxycarbamoyl]propionamido]pentyl]-3-[(5-N-hydroxyacetamido)pentyl]carbamoyl]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6546	65.46%
Caco-2	-	0.8717	87.17%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5531	55.31%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.9444	94.44%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	+	0.6561	65.61%
P-glycoprotein substrate	-	0.5144	51.44%
CYP3A4 substrate	+	0.5445	54.45%
CYP2C9 substrate	-	0.8227	82.27%
CYP2D6 substrate	-	0.7645	76.45%
CYP3A4 inhibition	-	0.7574	75.74%
CYP2C9 inhibition	-	0.8442	84.42%
CYP2C19 inhibition	-	0.8236	82.36%
CYP2D6 inhibition	-	0.9103	91.03%
CYP1A2 inhibition	-	0.8767	87.67%
CYP2C8 inhibition	-	0.9517	95.17%
CYP inhibitory promiscuity	-	0.9786	97.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	+	0.5100	51.00%
Carcinogenicity (trinary)	Non-required	0.4850	48.50%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8512	85.12%
Skin irritation	-	0.7592	75.92%
Skin corrosion	-	0.9159	91.59%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6001	60.01%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.7783	77.83%
skin sensitisation	-	0.8559	85.59%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7839	78.39%
Acute Oral Toxicity (c)	III	0.6170	61.70%
Estrogen receptor binding	+	0.6563	65.63%
Androgen receptor binding	+	0.5781	57.81%
Thyroid receptor binding	+	0.5868	58.68%
Glucocorticoid receptor binding	+	0.5676	56.76%
Aromatase binding	+	0.6157	61.57%
PPAR gamma	+	0.6638	66.38%
Honey bee toxicity	-	0.9127	91.27%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.7196	71.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3492	P49721	Proteasome Macropain subunit	95.92%	90.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.96%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.86%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.62%	99.17%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	91.52%	93.10%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.39%	91.11%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.06%	97.29%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.81%	97.21%
CHEMBL2664	P23526	Adenosylhomocysteinase	85.56%	86.67%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.45%	94.33%
CHEMBL221	P23219	Cyclooxygenase-1	84.15%	90.17%
CHEMBL2514	O95665	Neurotensin receptor 2	83.37%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	83.20%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.62%	89.34%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.98%	96.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 2973
• LOTUS: LTS0267339
• wikiData: Q419618