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3-[4-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-N-[1-[[(3S,12R,15Z,18R,21S,24S,25R)-3-(4-aminobutyl)-12-(3-amino-3-oxopropyl)-15-ethylidene-21-[(1S)-1-hydroxyethyl]-18-[(4-hydroxyphenyl)methyl]-7,25-dimethyl-2,5,8,11,14,17,20,23-octaoxo-6-[1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-24-yl]amino]-3-hydroxy-1-oxobutan-2-yl]-2-hydroxyhexadecanamide

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID aa1304ef-fd73-4d7c-ba90-fe5052e15294
Taxonomy Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides > Cyclic glycodepsipeptides
IUPAC Name 3-[4-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-N-[1-[[(3S,12R,15Z,18R,21S,24S,25R)-3-(4-aminobutyl)-12-(3-amino-3-oxopropyl)-15-ethylidene-21-[(1S)-1-hydroxyethyl]-18-[(4-hydroxyphenyl)methyl]-7,25-dimethyl-2,5,8,11,14,17,20,23-octaoxo-6-[1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-24-yl]amino]-3-hydroxy-1-oxobutan-2-yl]-2-hydroxyhexadecanamide
SMILES (Canonical) CCCCCCCCCCCCCC(C(C(=O)NC(C(C)O)C(=O)NC1C(OC(=O)C(NC(=O)C(N(C(=O)CNC(=O)C(NC(=O)C(=CC)NC(=O)C(NC(=O)C(NC1=O)C(C)O)CC2=CC=C(C=C2)O)CCC(=O)N)C)C(C)OC3C(C(C(C(O3)CO)O)O)O)CCCCN)C)O)OC4C(C(C(CO4)O)OC5C(C(C(C(O5)CO)O)O)NC(=O)C)O
SMILES (Isomeric) CCCCCCCCCCCCCC(C(C(=O)NC(C(C)O)C(=O)N[C@H]1[C@H](OC(=O)[C@@H](NC(=O)C(N(C(=O)CNC(=O)[C@H](NC(=O)/C(=C/C)/NC(=O)[C@H](NC(=O)[C@@H](NC1=O)[C@H](C)O)CC2=CC=C(C=C2)O)CCC(=O)N)C)C(C)OC3C(C(C(C(O3)CO)O)O)O)CCCCN)C)O)OC4C(C(C(CO4)O)OC5C(C(C(C(O5)CO)O)O)NC(=O)C)O
InChI InChI=1S/C78H128N12O32/c1-9-11-12-13-14-15-16-17-18-19-20-24-49(119-77-65(106)66(48(97)36-116-77)122-76-57(82-41(7)95)62(103)59(100)50(34-91)120-76)61(102)74(114)88-55(38(4)94)71(111)89-56-39(5)117-75(115)46(23-21-22-31-79)85-73(113)58(40(6)118-78-64(105)63(104)60(101)51(35-92)121-78)90(8)53(99)33-81-67(107)45(29-30-52(80)98)84-68(108)44(10-2)83-69(109)47(32-42-25-27-43(96)28-26-42)86-70(110)54(37(3)93)87-72(56)112/h10,25-28,37-40,45-51,54-66,76-78,91-94,96-97,100-106H,9,11-24,29-36,79H2,1-8H3,(H2,80,98)(H,81,107)(H,82,95)(H,83,109)(H,84,108)(H,85,113)(H,86,110)(H,87,112)(H,88,114)(H,89,111)/b44-10-/t37-,38?,39+,40?,45+,46-,47+,48?,49?,50?,51?,54-,55?,56-,57?,58?,59?,60?,61?,62?,63?,64?,65?,66?,76?,77?,78?/m0/s1
InChI Key CHQQTUZEDAZDBH-UKQIGXNFSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C78H128N12O32
Molecular Weight 1745.90 g/mol
Exact Mass 1744.8757600 g/mol
Topological Polar Surface Area (TPSA) 696.00 Ų
XlogP -2.30
Atomic LogP (AlogP) -8.03
H-Bond Acceptor 33
H-Bond Donor 24
Rotatable Bonds 38

Synonyms

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DTXSID501046985

2D Structure

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2D Structure of 3-[4-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-N-[1-[[(3S,12R,15Z,18R,21S,24S,25R)-3-(4-aminobutyl)-12-(3-amino-3-oxopropyl)-15-ethylidene-21-[(1S)-1-hydroxyethyl]-18-[(4-hydroxyphenyl)methyl]-7,25-dimethyl-2,5,8,11,14,17,20,23-octaoxo-6-[1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-24-yl]amino]-3-hydroxy-1-oxobutan-2-yl]-2-hydroxyhexadecanamide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.7416 74.16%
Caco-2 - 0.8580 85.80%
Blood Brain Barrier - 0.9500 95.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.4243 42.43%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7916 79.16%
OATP1B3 inhibitior + 0.9189 91.89%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.9552 95.52%
P-glycoprotein inhibitior + 0.7417 74.17%
P-glycoprotein substrate + 0.8780 87.80%
CYP3A4 substrate + 0.7623 76.23%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8533 85.33%
CYP3A4 inhibition + 0.5066 50.66%
CYP2C9 inhibition - 0.8211 82.11%
CYP2C19 inhibition - 0.9061 90.61%
CYP2D6 inhibition - 0.8200 82.00%
CYP1A2 inhibition - 0.8897 88.97%
CYP2C8 inhibition + 0.8520 85.20%
CYP inhibitory promiscuity - 0.9493 94.93%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.5685 56.85%
Eye corrosion - 0.9859 98.59%
Eye irritation - 0.8953 89.53%
Skin irritation - 0.7614 76.14%
Skin corrosion - 0.9280 92.80%
Ames mutagenesis - 0.6378 63.78%
Human Ether-a-go-go-Related Gene inhibition + 0.7284 72.84%
Micronuclear + 0.8900 89.00%
Hepatotoxicity - 0.6783 67.83%
skin sensitisation - 0.8693 86.93%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.6826 68.26%
Acute Oral Toxicity (c) III 0.6485 64.85%
Estrogen receptor binding - 0.5263 52.63%
Androgen receptor binding + 0.7520 75.20%
Thyroid receptor binding + 0.7968 79.68%
Glucocorticoid receptor binding + 0.8450 84.50%
Aromatase binding + 0.8100 81.00%
PPAR gamma + 0.7818 78.18%
Honey bee toxicity - 0.6028 60.28%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5848 58.48%
Fish aquatic toxicity + 0.8247 82.47%

Targets

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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
CHEMBL4040 P28482 MAP kinase ERK2 99.98% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.81% 91.11%
CHEMBL2581 P07339 Cathepsin D 99.80% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.65% 96.09%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 99.00% 93.10%
CHEMBL3837 P07711 Cathepsin L 98.97% 96.61%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.76% 94.45%
CHEMBL3038469 P24941 CDK2/Cyclin A 98.33% 91.38%
CHEMBL3060 Q9Y345 Glycine transporter 2 97.41% 99.17%
CHEMBL5103 Q969S8 Histone deacetylase 10 96.52% 90.08%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 95.85% 95.64%
CHEMBL255 P29275 Adenosine A2b receptor 95.41% 98.59%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 95.32% 92.86%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.68% 97.25%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 94.48% 100.00%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 94.05% 89.67%
CHEMBL5608 Q16288 NT-3 growth factor receptor 93.95% 95.89%
CHEMBL2514 O95665 Neurotensin receptor 2 93.87% 100.00%
CHEMBL4588 P22894 Matrix metalloproteinase 8 93.56% 94.66%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 93.36% 96.90%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 92.61% 91.03%
CHEMBL3359 P21462 Formyl peptide receptor 1 92.50% 93.56%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.31% 95.56%
CHEMBL2996 Q05655 Protein kinase C delta 92.01% 97.79%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 91.94% 85.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.59% 89.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 91.13% 95.83%
CHEMBL2094135 Q96BI3 Gamma-secretase 90.61% 98.05%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 90.61% 95.50%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 90.00% 82.38%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 89.92% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.48% 97.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 89.41% 97.14%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 89.24% 90.71%
CHEMBL226 P30542 Adenosine A1 receptor 89.07% 95.93%
CHEMBL3892 Q99500 Sphingosine 1-phosphate receptor Edg-3 89.01% 97.29%
CHEMBL4227 P25090 Lipoxin A4 receptor 88.26% 100.00%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 87.88% 91.24%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 87.62% 94.33%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 87.51% 93.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.65% 86.33%
CHEMBL3392948 Q9NP59 Solute carrier family 40 member 1 86.54% 95.00%
CHEMBL2693 Q9UIQ6 Cystinyl aminopeptidase 86.14% 97.64%
CHEMBL215 P09917 Arachidonate 5-lipoxygenase 86.01% 92.68%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.61% 95.50%
CHEMBL1937 Q92769 Histone deacetylase 2 85.10% 94.75%
CHEMBL5555 O00767 Acyl-CoA desaturase 84.76% 97.50%
CHEMBL3310 Q96DB2 Histone deacetylase 11 84.45% 88.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.16% 85.14%
CHEMBL4581 P52732 Kinesin-like protein 1 84.01% 93.18%
CHEMBL2072 P35499 Sodium channel protein type IV alpha subunit 83.95% 92.32%
CHEMBL2413 P32246 C-C chemokine receptor type 1 83.53% 89.50%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 83.34% 95.17%
CHEMBL299 P17252 Protein kinase C alpha 83.15% 98.03%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 82.63% 92.88%
CHEMBL1255126 O15151 Protein Mdm4 81.95% 90.20%
CHEMBL3401 O75469 Pregnane X receptor 81.69% 94.73%
CHEMBL2492 P36544 Neuronal acetylcholine receptor protein alpha-7 subunit 80.94% 88.42%
CHEMBL4071 P08311 Cathepsin G 80.92% 94.64%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.70% 96.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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Cross-Links

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PubChem 163107865
LOTUS LTS0087089
wikiData Q105102577