Tiglicamide B

Details

• Internal ID: 527e83b3-acc2-47d3-9ea7-4b541534db6c
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: 3-[(3S,6R,9Z,12S,15S,16R)-3-benzyl-9-ethylidene-15-[[(2R)-3-(4-hydroxyphenyl)-2-[[(2S)-3-methyl-2-[[(E)-2-methylbut-2-enoyl]amino]butanoyl]amino]propanoyl]amino]-12,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-6-yl]propanoic acid
• SMILES (Canonical): CC=C1C(=O)NC(C(=O)NC(C(=O)OC(C(C(=O)NC(C(=O)N1)C)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(C(C)C)NC(=O)C(=CC)C)C)CC3=CC=CC=C3)CCC(=O)O
• SMILES (Isomeric): C/C=C\1/C(=O)N[C@@H](C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N[C@H](C(=O)N1)C)NC(=O)[C@@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](C(C)C)NC(=O)/C(=C/C)/C)C)CC3=CC=CC=C3)CCC(=O)O
• InChI: InChI=1S/C44H57N7O12/c1-8-24(5)37(55)50-35(23(3)4)42(60)48-32(21-28-15-17-29(52)18-16-28)41(59)51-36-26(7)63-44(62)33(22-27-13-11-10-12-14-27)49-40(58)31(19-20-34(53)54)47-39(57)30(9-2)46-38(56)25(6)45-43(36)61/h8-18,23,25-26,31-33,35-36,52H,19-22H2,1-7H3,(H,45,61)(H,46,56)(H,47,57)(H,48,60)(H,49,58)(H,50,55)(H,51,59)(H,53,54)/b24-8+,30-9-/t25-,26+,31+,32+,33-,35-,36-/m0/s1
• InChI Key: HTQZRXGEFURKNL-RGQURIAKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₅₇N₇O₁₂
• Molecular Weight: 876.00 g/mol
• Exact Mass: 875.40652028 g/mol
• Topological Polar Surface Area (TPSA): 288.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 0.56
• H-Bond Acceptor: 11
• H-Bond Donor: 9
• Rotatable Bonds: 14

Synonyms

• DTXSID801335270
• 1207162-71-7
• 3-((3S,6R,9Z,12S,15S,16R)-3-benzyl-9-ethylidene-15-(((2R)-3-(4-hydroxyphenyl)-2-(((2S)-3-methyl-2-(((E)-2-methylbut-2-enoyl)amino)butanoyl)amino)propanoyl)amino)-12,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-6-yl)propanoic acid
• 3-[(3S,6R,9Z,12S,15S,16R)-3-benzyl-9-ethylidene-15-[[(2R)-3-(4-hydroxyphenyl)-2-[[(2S)-3-methyl-2-[[(E)-2-methylbut-2-enoyl]amino]butanoyl]amino]propanoyl]amino]-12,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-6-yl]propanoic acid
• RefChem:189993
• DTXCID601765009
• 3-((3S,6R,12S,15S,16R,Z)-3-benzyl-9-ethylidene-15-((R)-3-(4-hydroxyphenyl)-2-((S)-3-methyl-2-((E)-2-methylbut-2-enamido)butanamido)propanamido)-12,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-6-yl)propanoic acid
• 3-((3S,6R,9Z,12S,15S,16R)-9-ethylidene-3-((4-hydroxyphenyl)methyl)-15-(((2R)-3-(4-hydroxyphenyl)-2-(((2S)-3-methyl-2-(((E)-2-methylbut-2-enoyl)amino)butanoyl)amino)propanoyl)amino)-12,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-6-yl)propanoic acid
• SCHEMBL29885640
• CHEBI:207899
• N-[(2E)-2-Methylbut-2-enoyl]-L-valyl-N-[(3S,6R,9Z,12S,15S,16R)-3-benzyl-6-(2-carboxyethyl)-9-ethylidene-12,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl]-D-tyrosinamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7748	77.48%
Caco-2	-	0.8724	87.24%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7335	73.35%
OATP2B1 inhibitior	-	0.5680	56.80%
OATP1B1 inhibitior	+	0.7975	79.75%
OATP1B3 inhibitior	+	0.9240	92.40%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8890	88.90%
BSEP inhibitior	+	0.9267	92.67%
P-glycoprotein inhibitior	+	0.7619	76.19%
P-glycoprotein substrate	+	0.8706	87.06%
CYP3A4 substrate	+	0.7147	71.47%
CYP2C9 substrate	+	0.6148	61.48%
CYP2D6 substrate	-	0.8891	88.91%
CYP3A4 inhibition	-	0.5310	53.10%
CYP2C9 inhibition	-	0.7828	78.28%
CYP2C19 inhibition	-	0.7380	73.80%
CYP2D6 inhibition	-	0.9182	91.82%
CYP1A2 inhibition	-	0.9137	91.37%
CYP2C8 inhibition	+	0.7319	73.19%
CYP inhibitory promiscuity	-	0.6979	69.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8611	86.11%
Carcinogenicity (trinary)	Non-required	0.5312	53.12%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9104	91.04%
Skin irritation	-	0.7951	79.51%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3877	38.77%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8611	86.11%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5245	52.45%
Acute Oral Toxicity (c)	III	0.6237	62.37%
Estrogen receptor binding	+	0.8169	81.69%
Androgen receptor binding	+	0.7581	75.81%
Thyroid receptor binding	+	0.5945	59.45%
Glucocorticoid receptor binding	+	0.6250	62.50%
Aromatase binding	+	0.5792	57.92%
PPAR gamma	+	0.7608	76.08%
Honey bee toxicity	-	0.7113	71.13%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.8902	89.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.72%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.46%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.36%	85.14%
CHEMBL3837	P07711	Cathepsin L	97.35%	96.61%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.34%	99.17%
CHEMBL4072	P07858	Cathepsin B	94.29%	93.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.64%	96.09%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	93.05%	97.64%
CHEMBL1255126	O15151	Protein Mdm4	93.02%	90.20%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.79%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	92.18%	90.08%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	92.02%	93.10%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.87%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	91.44%	90.17%
CHEMBL4040	P28482	MAP kinase ERK2	91.01%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.64%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.04%	97.14%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	89.92%	85.11%
CHEMBL3468	P55210	Caspase-7	88.90%	95.68%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	88.86%	90.93%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.84%	94.23%
CHEMBL236	P41143	Delta opioid receptor	87.53%	99.35%
CHEMBL340	P08684	Cytochrome P450 3A4	86.45%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.22%	93.56%
CHEMBL2514	O95665	Neurotensin receptor 2	85.12%	100.00%
CHEMBL2327	P21452	Neurokinin 2 receptor	84.20%	98.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.02%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.88%	93.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.60%	95.89%
CHEMBL1944	P08473	Neprilysin	81.67%	92.63%
CHEMBL1293287	P14735	Insulin-degrading enzyme	81.32%	88.10%
CHEMBL259	P32245	Melanocortin receptor 4	81.31%	95.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.73%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.72%	99.15%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.52%	91.71%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	80.47%	82.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 44606523
• LOTUS: LTS0246257
• wikiData: Q77489011