Dethiobiotin

Details

• Internal ID: 0737a162-6c42-47a1-a307-d7f3ac755afb
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Medium-chain fatty acids
• IUPAC Name: 6-[(4R,5S)-5-methyl-2-oxoimidazolidin-4-yl]hexanoic acid
• SMILES (Canonical): CC1C(NC(=O)N1)CCCCCC(=O)O
• SMILES (Isomeric): C[C@H]1[C@H](NC(=O)N1)CCCCCC(=O)O
• InChI: InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)/t7-,8+/m0/s1
• InChI Key: AUTOLBMXDDTRRT-JGVFFNPUSA-N
• Popularity: 133 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₈N₂O₃
• Molecular Weight: 214.26 g/mol
• Exact Mass: 214.13174244 g/mol
• Topological Polar Surface Area (TPSA): 78.40 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 2
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• dethiobiotin
• 533-48-2
• d-Dethiobiotin
• Desthiobiotin
• (+)-Dethiobiotin
• Biotin, dethio-
• 6-[(4R,5S)-5-methyl-2-oxoimidazolidin-4-yl]hexanoic acid
• (4R,5S)-dethiobiotin
• Desthiobiotin, DL-
• (+/-)-Desthiobiotin
• Desthiobiotin, (+/-)-
• dl-Dethiobiotin
• AI3-26390
• 5-Methyl-2-oxo-4-imidazolidinecaproic acid
• 5-Methyl-2-oxo-4-imidazolidinehexanoic acid
• 4-Methyl-5-(omega-carboxyamyl)imidazolidone-2
• 636-20-4
• epsilon-(4-Methyl-5-imidazolidone-2)caproic acid
• NSC-203773
• (4R-cis)-5-Methyl-2-oxoimidazolidine-4-hexanoic acid
• IRON POTASSIUM SULFIDE)
• MLS001066403
• 71U5JB52KS
• 4-Imidazolidinehexanoic acid, 5-methyl-2-oxo-, (4R,5S)-
• 6-((4R,5S)-5-Methyl-2-oxoimidazolidin-4-yl)hexanoic acid
• 6-(5-METHYL-2-OXO-IMIDAZOLIDIN-4-YL)-HEXANOIC ACID
• CHEBI:42280
• I64P0B487B
• (4R,5S)-5-methyl-2-oxo-4-imidazolidinehexanoic acid
• DTB
• 4-Imidazolidinehexanoic acid, 5-methyl-2-oxo-, (4R-cis)-
• 4-Imidazolidinehexanoic acid, 5-methyl-2-oxo-, cis-(+/-)-
• SMR000471877
• 4-Imidazolidinehexanoic acid, 5-methyl-2-oxo-, (4R,5S)-rel-
• 12022-42-3
• (4R-cis)-5-methyl-2-oxo-4-imidazolidinehexanoic acid
• NSC-3085
• 4-Imidazolidinehexanoic acid, 5-methyl-2-oxo-, (4R,5S)- (8CI,9CI)
• UNII-71U5JB52KS
• NSC 3085
• UNII-I64P0B487B
• MFCD00213804
• rac-Desthio Biotin
• (+)-Desthiobiotin
• EINECS 208-566-2
• DESTHIOBIOTIN [MI]
• bmse000314
• D1411_SIGMA
• SCHEMBL143996
• DESTHIOBIOTIN, (+)-
• cid_445027
• CHEMBL1232381
• SCHEMBL20548075
• BDBM66184
• EXPT01280
• DTXSID50876136
• HMS2235J03
• d-Desthiobiotin, >=98% (TLC)
• AKOS030240689
• AT20607
• DB03775
• BS-48946
• HY-128699
• CS-0098609
• EN300-19745876
• Q27094671
• .EPSILON.-(4-METHYL-5-IMIDAZOLIDONE-2)CAPROIC ACID
• 6-((4R,5S)-5-Methyl-2-oxoimidazolidin-4-yl)hexanoicacid
• 6-[(4R,5S)-5-methyl-2-oxo-4-imidazolidinyl]hexanoic acid
• 6-[(4R,5S)-2-keto-5-methyl-imidazolidin-4-yl]hexanoic acid
• F91C55D1-259D-437E-A748-A08C722D274F
• 6-[(4R,5S)-5-methyl-2-oxidanylidene-imidazolidin-4-yl]hexanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9578	95.78%
Caco-2	-	0.6868	68.68%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7805	78.05%
OATP2B1 inhibitior	-	0.8482	84.82%
OATP1B1 inhibitior	+	0.9066	90.66%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9394	93.94%
P-glycoprotein inhibitior	-	0.9650	96.50%
P-glycoprotein substrate	-	0.8060	80.60%
CYP3A4 substrate	-	0.6413	64.13%
CYP2C9 substrate	+	0.6071	60.71%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.9430	94.30%
CYP2C9 inhibition	-	0.9360	93.60%
CYP2C19 inhibition	-	0.9508	95.08%
CYP2D6 inhibition	-	0.9497	94.97%
CYP1A2 inhibition	-	0.9350	93.50%
CYP2C8 inhibition	-	0.9482	94.82%
CYP inhibitory promiscuity	-	0.9870	98.70%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6695	66.95%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.9269	92.69%
Skin irritation	-	0.7804	78.04%
Skin corrosion	-	0.9269	92.69%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7325	73.25%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.5360	53.60%
skin sensitisation	-	0.9029	90.29%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7202	72.02%
Acute Oral Toxicity (c)	III	0.6980	69.80%
Estrogen receptor binding	-	0.7052	70.52%
Androgen receptor binding	-	0.8970	89.70%
Thyroid receptor binding	-	0.6458	64.58%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6765	67.65%
PPAR gamma	-	0.7224	72.24%
Honey bee toxicity	-	0.9830	98.30%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.6446	64.46%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4374	Q9Y5X4	Photoreceptor-specific nuclear receptor	149.12 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.44%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.58%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.69%	91.11%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.18%	93.00%

Plants that contains it

• Scaphyglottis livida

Cross-Links

• PubChem: 445027
• LOTUS: LTS0182015
• wikiData: Q27094671