Tasipeptin A

Details

• Internal ID: 15dd2acc-637e-4b14-b2f5-6c33b1cc6fb1
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2S)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-21-hydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-(butanoylamino)-3-methylbutanamide
• SMILES (Canonical): CCCC(=O)NC(C(C)C)C(=O)NC1C(OC(=O)C(NC(=O)C(N(C(=O)C(N2C(CCC(C2=O)NC(=O)C(NC1=O)CC(C)C)O)CC(C)C)C)CC3=CC=CC=C3)C(C)C)C
• SMILES (Isomeric): CCCC(=O)N[C@@H](C(C)C)C(=O)N[C@H]1[C@H](OC(=O)[C@@H](NC(=O)[C@@H](N(C(=O)[C@@H](N2[C@@H](CC[C@@H](C2=O)NC(=O)[C@@H](NC1=O)CC(C)C)O)CC(C)C)C)CC3=CC=CC=C3)C(C)C)C
• InChI: InChI=1S/C45H71N7O10/c1-12-16-34(53)48-36(26(6)7)41(57)50-38-28(10)62-45(61)37(27(8)9)49-40(56)32(23-29-17-14-13-15-18-29)51(11)44(60)33(22-25(4)5)52-35(54)20-19-30(43(52)59)46-39(55)31(21-24(2)3)47-42(38)58/h13-15,17-18,24-28,30-33,35-38,54H,12,16,19-23H2,1-11H3,(H,46,55)(H,47,58)(H,48,53)(H,49,56)(H,50,57)/t28-,30+,31+,32+,33+,35-,36+,37+,38+/m1/s1
• InChI Key: RUCVBGWUPBXPNT-LHBJIRMKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₁N₇O₁₀
• Molecular Weight: 870.10 g/mol
• Exact Mass: 869.52624149 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 1.94
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 13

Synonyms

• CHEMBL487379
• SCHEMBL1593407
• DTXSID101334045
• (2S)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-21-hydroxy-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2-(butanoylamino)-3-methylbutanamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5879	58.79%
Caco-2	-	0.8615	86.15%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4098	40.98%
OATP2B1 inhibitior	-	0.7068	70.68%
OATP1B1 inhibitior	+	0.8155	81.55%
OATP1B3 inhibitior	+	0.9048	90.48%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8890	88.90%
BSEP inhibitior	+	0.7319	73.19%
P-glycoprotein inhibitior	+	0.7447	74.47%
P-glycoprotein substrate	+	0.8827	88.27%
CYP3A4 substrate	+	0.7113	71.13%
CYP2C9 substrate	-	0.7982	79.82%
CYP2D6 substrate	-	0.8537	85.37%
CYP3A4 inhibition	-	0.6088	60.88%
CYP2C9 inhibition	-	0.8639	86.39%
CYP2C19 inhibition	-	0.8376	83.76%
CYP2D6 inhibition	-	0.8917	89.17%
CYP1A2 inhibition	-	0.9339	93.39%
CYP2C8 inhibition	+	0.6091	60.91%
CYP inhibitory promiscuity	-	0.9687	96.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6349	63.49%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9107	91.07%
Skin irritation	-	0.7889	78.89%
Skin corrosion	-	0.9212	92.12%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4860	48.60%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.5073	50.73%
skin sensitisation	-	0.8898	88.98%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6871	68.71%
Acute Oral Toxicity (c)	III	0.6587	65.87%
Estrogen receptor binding	+	0.8202	82.02%
Androgen receptor binding	+	0.6515	65.15%
Thyroid receptor binding	+	0.5846	58.46%
Glucocorticoid receptor binding	+	0.6919	69.19%
Aromatase binding	+	0.6286	62.86%
PPAR gamma	+	0.7818	78.18%
Honey bee toxicity	-	0.7575	75.75%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.8131	81.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.92%	98.95%
CHEMBL4072	P07858	Cathepsin B	98.17%	93.67%
CHEMBL221	P23219	Cyclooxygenase-1	97.50%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.67%	96.09%
CHEMBL333	P08253	Matrix metalloproteinase-2	96.58%	96.31%
CHEMBL5103	Q969S8	Histone deacetylase 10	95.97%	90.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.05%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.67%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.61%	99.23%
CHEMBL4040	P28482	MAP kinase ERK2	91.85%	83.82%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	91.41%	93.00%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	91.35%	97.64%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.15%	91.11%
CHEMBL1949	P62937	Cyclophilin A	89.93%	98.57%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.56%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.41%	97.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.61%	93.56%
CHEMBL4588	P22894	Matrix metalloproteinase 8	87.00%	94.66%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.67%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.18%	97.25%
CHEMBL3468	P55210	Caspase-7	85.60%	95.68%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	84.74%	88.42%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.45%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.76%	93.03%
CHEMBL255	P29275	Adenosine A2b receptor	83.72%	98.59%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.83%	96.47%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	82.06%	98.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.19%	95.89%
CHEMBL332	P03956	Matrix metalloproteinase-1	80.93%	94.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.45%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10440686
• LOTUS: LTS0251192
• wikiData: Q75066683