Ala-geninthiocin
| Internal ID | bde10595-37f0-44f5-9a95-1e60af7d22e5 |
| Taxonomy | Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Cyclic peptides |
| IUPAC Name | (14S,27S)-N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-17-ethylidene-14-[(1R)-1-hydroxyethyl]-33-methyl-24,30,37,40-tetramethylidene-12,15,22,25,28,35,38-heptaoxo-27-propan-2-yl-19,32,42-trioxa-9-thia-3,13,16,23,26,29,36,39,44,45,46,47-dodecazahexacyclo[39.2.1.18,11.118,21.131,34.02,7]heptatetraconta-1(43),2(7),3,5,8(47),10,18(46),20,31(45),33,41(44)-undecaene-4-carboxamide |
| SMILES (Canonical) | CC=C1C2=NC(=CO2)C(=O)NC(=C)C(=O)NC(C(=O)NC(=C)C3=NC(=C(O3)C)C(=O)NC(=C)C(=O)NC(=C)C4=NC(=CO4)C5=C(C=CC(=N5)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C6=NC(=CS6)C(=O)NC(C(=O)N1)C(C)O)C(C)C |
| SMILES (Isomeric) | CC=C1C2=NC(=CO2)C(=O)NC(=C)C(=O)N[C@H](C(=O)NC(=C)C3=NC(=C(O3)C)C(=O)NC(=C)C(=O)NC(=C)C4=NC(=CO4)C5=C(C=CC(=N5)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C6=NC(=CS6)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)C(C)C |
| InChI | InChI=1S/C50H49N15O14S/c1-12-28-49-61-31(16-78-49)42(72)54-22(7)40(70)63-33(18(2)3)44(74)57-24(9)48-65-35(26(11)79-48)46(76)55-21(6)39(69)56-23(8)47-60-30(15-77-47)36-27(50-62-32(17-80-50)43(73)64-34(25(10)66)45(75)59-28)13-14-29(58-36)41(71)53-20(5)38(68)52-19(4)37(51)67/h12-18,25,33-34,66H,4-9H2,1-3,10-11H3,(H2,51,67)(H,52,68)(H,53,71)(H,54,72)(H,55,76)(H,56,69)(H,57,74)(H,59,75)(H,63,70)(H,64,73)/t25-,33+,34+/m1/s1 |
| InChI Key | BUWWXQACKZTOAC-OCVOMCNHSA-N |
| Popularity | 1 reference in papers |
| Molecular Formula | C50H49N15O14S |
| Molecular Weight | 1116.10 g/mol |
| Exact Mass | 1115.33041247 g/mol |
| Topological Polar Surface Area (TPSA) | 457.00 Ų |
| XlogP | 2.00 |
| Atomic LogP (AlogP) | 0.68 |
| H-Bond Acceptor | 20 |
| H-Bond Donor | 11 |
| Rotatable Bonds | 7 |
| RefChem:110427 |
| (14S,27S)-N-(3-((3-amino-3-oxoprop-1-en-2-yl)amino)-3-oxoprop-1-en-2-yl)-17-ethylidene-14-((1R)-1-hydroxyethyl)-33-methyl-24,30,37,40-tetramethylidene-12,15,22,25,28,35,38-heptaoxo-27-propan-2-yl-19,32,42-trioxa-9-thia-3,13,16,23,26,29,36,39,44,45,46,47-dodecazahexacyclo(39.2.1.18,11.118,21.131,34.02,7)heptatetraconta-1(43),2(7),3,5,8(47),10,18(46),20,31(45),33,41(44)-undecaene-4-carboxamide |
| (14S,27S)-N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-17-ethylidene-14-[(1R)-1-hydroxyethyl]-33-methyl-24,30,37,40-tetramethylidene-12,15,22,25,28,35,38-heptaoxo-27-propan-2-yl-19,32,42-trioxa-9-thia-3,13,16,23,26,29,36,39,44,45,46,47-dodecazahexacyclo[39.2.1.18,11.118,21.131,34.02,7]heptatetraconta-1(43),2(7),3,5,8(47),10,18(46),20,31(45),33,41(44)-undecaene-4-carboxamide |
| 2-(((14S,27S)-17-ethylidene-12,15,22,25,28,35,38-heptahydroxy-14-((1R)-1-hydroxyethyl)-33-methyl-24,30,37,40-tetramethylidene-27-(propan-2-yl)-19,32,42-trioxa-9-thia-3,13,16,23,26,29,36,39,44,45,46,47-dodecaazahexacyclo(39.2.1.1,.1,.1,.0,)heptatetraconta-1(43),2(7),3,5,8(47),10,12,15,18(46),20,22,25,28,31(45),33,35,38,41(44)-octadecaen-4-yl)formamido)-N-(1-(C-hydroxycarbonimidoyl)eth-1-en-1-yl)prop-2-enimidate |
| 2-(((14S,27S)-17-ethylidene-12,15,22,25,28,35,38-heptahydroxy-14-((1R)-1-hydroxyethyl)-33-methyl-24,30,37,40-tetramethylidene-27-propan-2-yl-19,32,42-trioxa-9-thia-3,13,16,23,26,29,36,39,44,45,46,47-dodecazahexacyclo(39.2.1.18,11.118,21.131,34.02,7)heptatetraconta-1(43),2(7),3,5,8(47),10,12,15,18(46),20,22,25,28,31(45),33,35,38,41(44)-octadecaene-4-carbonyl)amino)-N-(3-hydroxy-3-iminoprop-1-en-2-yl)prop-2-enimidic acid |
| 2-[[(14S,27S)-17-ethylidene-12,15,22,25,28,35,38-heptahydroxy-14-[(1R)-1-hydroxyethyl]-33-methyl-24,30,37,40-tetramethylidene-27-propan-2-yl-19,32,42-trioxa-9-thia-3,13,16,23,26,29,36,39,44,45,46,47-dodecazahexacyclo[39.2.1.18,11.118,21.131,34.02,7]heptatetraconta-1(43),2(7),3,5,8(47),10,12,15,18(46),20,22,25,28,31(45),33,35,38,41(44)-octadecaene-4-carbonyl]amino]-N-(3-hydroxy-3-iminoprop-1-en-2-yl)prop-2-enimidic acid |
| 2-{[(14S,27S)-17-ethylidene-12,15,22,25,28,35,38-heptahydroxy-14-[(1R)-1-hydroxyethyl]-33-methyl-24,30,37,40-tetramethylidene-27-(propan-2-yl)-19,32,42-trioxa-9-thia-3,13,16,23,26,29,36,39,44,45,46,47-dodecaazahexacyclo[39.2.1.1,.1,.1,.0,]heptatetraconta-1(43),2(7),3,5,8(47),10,12,15,18(46),20,22,25,28,31(45),33,35,38,41(44)-octadecaen-4-yl]formamido}-N-[1-(C-hydroxycarbonimidoyl)eth-1-en-1-yl]prop-2-enimidate |
| CHEBI:222237 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.7770 | 77.70% |
| Caco-2 | - | 0.8567 | 85.67% |
| Blood Brain Barrier | - | 0.8250 | 82.50% |
| Human oral bioavailability | - | 0.5286 | 52.86% |
| Subcellular localzation | Mitochondria | 0.5349 | 53.49% |
| OATP2B1 inhibitior | - | 0.7136 | 71.36% |
| OATP1B1 inhibitior | + | 0.8345 | 83.45% |
| OATP1B3 inhibitior | + | 0.9365 | 93.65% |
| MATE1 inhibitior | - | 0.8269 | 82.69% |
| OCT2 inhibitior | - | 1.0000 | 100.00% |
| BSEP inhibitior | + | 0.9595 | 95.95% |
| P-glycoprotein inhibitior | + | 0.7435 | 74.35% |
| P-glycoprotein substrate | + | 0.8148 | 81.48% |
| CYP3A4 substrate | + | 0.7307 | 73.07% |
| CYP2C9 substrate | - | 0.6039 | 60.39% |
| CYP2D6 substrate | - | 0.8744 | 87.44% |
| CYP3A4 inhibition | - | 0.8275 | 82.75% |
| CYP2C9 inhibition | - | 0.7229 | 72.29% |
| CYP2C19 inhibition | - | 0.6552 | 65.52% |
| CYP2D6 inhibition | - | 0.9114 | 91.14% |
| CYP1A2 inhibition | - | 0.6363 | 63.63% |
| CYP2C8 inhibition | + | 0.8012 | 80.12% |
| CYP inhibitory promiscuity | - | 0.8486 | 84.86% |
| UGT catelyzed | + | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.8725 | 87.25% |
| Carcinogenicity (trinary) | Non-required | 0.6059 | 60.59% |
| Eye corrosion | - | 0.9860 | 98.60% |
| Eye irritation | - | 0.8971 | 89.71% |
| Skin irritation | - | 0.7823 | 78.23% |
| Skin corrosion | - | 0.9333 | 93.33% |
| Ames mutagenesis | - | 0.5700 | 57.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.6501 | 65.01% |
| Micronuclear | + | 0.9100 | 91.00% |
| Hepatotoxicity | - | 0.5716 | 57.16% |
| skin sensitisation | - | 0.8478 | 84.78% |
| Respiratory toxicity | + | 0.7556 | 75.56% |
| Reproductive toxicity | + | 0.6667 | 66.67% |
| Mitochondrial toxicity | + | 0.7375 | 73.75% |
| Nephrotoxicity | - | 0.6507 | 65.07% |
| Acute Oral Toxicity (c) | III | 0.5813 | 58.13% |
| Estrogen receptor binding | + | 0.6860 | 68.60% |
| Androgen receptor binding | + | 0.7686 | 76.86% |
| Thyroid receptor binding | + | 0.6908 | 69.08% |
| Glucocorticoid receptor binding | + | 0.6797 | 67.97% |
| Aromatase binding | + | 0.7518 | 75.18% |
| PPAR gamma | + | 0.7358 | 73.58% |
| Honey bee toxicity | - | 0.6384 | 63.84% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | - | 0.6300 | 63.00% |
| Fish aquatic toxicity | + | 0.8873 | 88.73% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| No proven targets yet! | |||||
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL1907600 | Q00535 | Cyclin-dependent kinase 5/CDK5 activator 1 | 97.85% | 93.03% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 97.37% | 91.11% |
| CHEMBL4040 | P28482 | MAP kinase ERK2 | 96.21% | 83.82% |
| CHEMBL3267 | P48736 | PI3-kinase p110-gamma subunit | 94.86% | 95.71% |
| CHEMBL5845 | P23415 | Glycine receptor subunit alpha-1 | 94.14% | 90.71% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 93.46% | 99.23% |
| CHEMBL1293294 | P51151 | Ras-related protein Rab-9A | 92.76% | 87.67% |
| CHEMBL2492 | P36544 | Neuronal acetylcholine receptor protein alpha-7 subunit | 92.61% | 88.42% |
| CHEMBL4685 | P14902 | Indoleamine 2,3-dioxygenase | 92.44% | 96.38% |
| CHEMBL1293267 | Q9HC97 | G-protein coupled receptor 35 | 92.17% | 89.34% |
| CHEMBL3038469 | P24941 | CDK2/Cyclin A | 91.99% | 91.38% |
| CHEMBL2581 | P07339 | Cathepsin D | 91.29% | 98.95% |
| CHEMBL3830 | Q2M2I8 | Adaptor-associated kinase | 90.21% | 83.10% |
| CHEMBL2243 | O00519 | Anandamide amidohydrolase | 89.23% | 97.53% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 88.30% | 94.73% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 88.06% | 95.56% |
| CHEMBL3384 | Q16512 | Protein kinase N1 | 87.99% | 80.71% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 87.84% | 85.14% |
| CHEMBL3880 | P07900 | Heat shock protein HSP 90-alpha | 87.80% | 96.21% |
| CHEMBL213 | P08588 | Beta-1 adrenergic receptor | 87.77% | 95.56% |
| CHEMBL1907602 | P06493 | Cyclin-dependent kinase 1/cyclin B1 | 87.25% | 91.24% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 87.25% | 96.09% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 86.89% | 94.00% |
| CHEMBL3130 | O00329 | PI3-kinase p110-delta subunit | 85.34% | 96.47% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 85.18% | 94.45% |
| CHEMBL2335 | P42785 | Lysosomal Pro-X carboxypeptidase | 83.68% | 100.00% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 82.72% | 89.00% |
| CHEMBL1628481 | P35414 | Apelin receptor | 82.38% | 97.89% |
| CHEMBL4530 | P00488 | Coagulation factor XIII | 81.66% | 96.00% |
| CHEMBL5163 | Q9NY46 | Sodium channel protein type III alpha subunit | 81.30% | 96.90% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 81.27% | 95.50% |
| CHEMBL3976 | Q9UHL4 | Dipeptidyl peptidase II | 80.14% | 92.29% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 80.06% | 90.17% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 145720674 |
| LOTUS | LTS0046816 |
| wikiData | Q104946373 |