Lipoamide

Details

• Internal ID: d2ad99d4-d2b6-43e5-9fca-63fef67a0c29
• Taxonomy: Organoheterocyclic compounds > Dithiolanes > Lipoamides
• IUPAC Name: 5-(dithiolan-3-yl)pentanamide
• InChI: InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
• InChI Key: FCCDDURTIIUXBY-UHFFFAOYSA-N
• Popularity: 566 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₅NOS₂
• Molecular Weight: 205.30 g/mol
• Exact Mass: 205.05950645 g/mol
• Topological Polar Surface Area (TPSA): 93.70 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• Thioctamide
• 940-69-2
• 5-(1,2-Dithiolan-3-yl)pentanamide
• thioctic acid amide
• 3206-73-3
• dl-6,8-Thioctamide
• Lipoacin
• DL-lipoamide
• Vitamin N
• Lipamide
• Lipoamid
• Lipoicin
• Pathoclon
• 1,2-Dithiolane-3-pentanamide
• Lipozyme
• (+/-)-alpha-Lipoamide
• alpha-Lipoic acid amide
• DL-5-(1,2-Dithiolan-3-yl)valeramide
• dl-alpha-Lipoamide
• Thioctamid
• Lypoaran
• Thioami
• Thiotomin
• Ticolin
• 5-(dithiolan-3-yl)pentanamide
• alpha-Lipoamide
• 5-(1,2-Dithiolan-3-yl)valeramide
• .alpha.-Lipamide
• dl-6-Thioctic amide
• 1,2-DITHIOLANE-3-VALERAMIDE
• Lipoamide, alpha-
• NSC-90787
• NSC-759236
• Thioctic acid amide (JAN)
• Dl-.alpha.-lipoic acid amide
• DTXSID2046541
• CHEBI:17460
• Q1GT04827L
• NSC90787
• NCGC00166104-01
• 1,2-Dithiolane-3-pentanamide, (.+/-.)-
• DTXCID0026541
• THIOCTIC ACID AMIDE [JAN]
• thioctic amide
• CAS-940-69-2
• 5-(Dithiolan-3-yl)valeramide
• 5-(1,2)Dithiolan-3-yl-pentanoic acid amide
• 5-[1,2]Dithiolan-3-yl-pentanoic acid amide
• dl-thioctic acid amide
• EINECS 213-375-2
• dl-alpha-lipoic acid amide
• (+/-)-alpha-Lipoamide;DL-Lipoamide;DL-6,8-Thioctamide
• (+-)-Thioctic acid amide
• BRN 0122470
• DL-6,8-Epidithiooctanamide
• alpha-Lipamide
• Alpha-lipoate
• UNII-Q1GT04827L
• 5-(1,2-dithiolan-3-yl)-pentanamide
• D,L-Lipoamide
• (S)-Lipoamide
• .alpha.-Lipoamide
• (+-)-1,2-Dithiolane-3-valeramide
• NSC 90787
• (+-)-1,2-Dithiolane-3-pentanamide
• Tioctan (Salt/Mix)
• 6-Thioctic acid amide
• (+/-)-?-Lipoamide
• Maybridge4_001874
• .alpha.-Lipoic acid amide
• bmse000769
• NCIOpen2_006211
• SCHEMBL50599
• (+/-)- alpha -Lipoamide
• THIOCTAMIDE [WHO-DD]
• 5-19-07-00238 (Beilstein Handbook Reference)
• 1,2-Dithiolane-3-pentanamide-
• 1,2-Dithiolane-3-valeroylamide
• CHEMBL1403899
• BDBM16435
• FCCDDURTIIUXBY-UHFFFAOYSA-
• HMS1526F04
• HMS3264F08
• Pharmakon1600-01505740
• HY-B1142
• (+/-)-THIOCTIC ACID AMIDE
• Tox21_112317
• CCG-42144
• LMFA08010006
• MFCD00005475
• NSC759236
• s6178
• AKOS015897492
• Tox21_112317_1
• AC-8132
• CS-4705
• 5-(1,2-Dithiolan-3-yl)pentanamide #
• NCGC00166104-02
• NCGC00166104-04
• BS-23283
• SBI-0207048.P001
• (+/-)-alpha-Lipoamide, analytical standard
• A5770
• FT-0625517
• T0818
• (+/-)-1,2-DITHIOLANE-3-VALERAMIDE
• (+/-)-1,2-DITHIOLANE-3-PENTANAMIDE
• C00248
• D00048
• D92402
• ()--Lipoamide;DL-Lipoamide;DL-6,8-Thioctamide
• AB01563370_01
• EN300-7407229
• SR-01000632164
• SR-01000632164-1
• SR-01000632164-2
• W-100216
• BRD-A14440173-001-01-8
• Z101185540
• 4BFBE47A-76FD-447C-883B-E049423E6511
• InChI=1/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	-	0.6353	63.53%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4939	49.39%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9673	96.73%
OATP1B3 inhibitior	+	0.9455	94.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8622	86.22%
P-glycoprotein inhibitior	-	0.9726	97.26%
P-glycoprotein substrate	-	0.8725	87.25%
CYP3A4 substrate	-	0.6131	61.31%
CYP2C9 substrate	-	0.6171	61.71%
CYP2D6 substrate	-	0.8339	83.39%
CYP3A4 inhibition	-	0.8909	89.09%
CYP2C9 inhibition	-	0.8341	83.41%
CYP2C19 inhibition	-	0.5469	54.69%
CYP2D6 inhibition	-	0.8363	83.63%
CYP1A2 inhibition	-	0.5970	59.70%
CYP2C8 inhibition	-	0.9406	94.06%
CYP inhibitory promiscuity	-	0.6619	66.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7500	75.00%
Carcinogenicity (trinary)	Non-required	0.5780	57.80%
Eye corrosion	-	0.8957	89.57%
Eye irritation	+	0.8093	80.93%
Skin irritation	-	0.6858	68.58%
Skin corrosion	-	0.8309	83.09%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6716	67.16%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8794	87.94%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6918	69.18%
Acute Oral Toxicity (c)	III	0.7840	78.40%
Estrogen receptor binding	-	0.5676	56.76%
Androgen receptor binding	-	0.8786	87.86%
Thyroid receptor binding	-	0.7335	73.35%
Glucocorticoid receptor binding	-	0.8044	80.44%
Aromatase binding	-	0.7172	71.72%
PPAR gamma	-	0.5066	50.66%
Honey bee toxicity	-	0.9553	95.53%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.7075	70.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.62%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.87%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.46%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.98%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.42%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.85%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.42%	93.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.19%	96.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.97%	95.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.27%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.34%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	81.83%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.54%	82.69%
CHEMBL2581	P07339	Cathepsin D	80.97%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	80.19%	90.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 863
• LOTUS: LTS0093322
• wikiData: Q63611085