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(2E,4E,6R)-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-[(2S,3S,4R,5S,6S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methylhepta-2,4-dienoic acid

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 9e32b5dd-3d29-44cf-9768-de5bc21918cd
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name (2E,4E,6R)-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-[(2S,3S,4R,5S,6S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methylhepta-2,4-dienoic acid
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC56CC57CCC8(C(CCC8(C7CCC6C4(C)C)C)C(C)C=CC=C(C)C(=O)O)C)CO)O)OC9C(C(C(C(O9)CO)O)O)O)COC1C(C(C(C(O1)CO)O)O)O)O)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3[C@@H]([C@H]([C@@H](O[C@@H]3O[C@H]4CC[C@]56C[C@]57CC[C@@]8([C@H](CC[C@]8([C@@H]7CC[C@H]6C4(C)C)C)[C@H](C)/C=C/C=C(\C)/C(=O)O)C)CO)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)CO[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O)O)O)O)O)O)O)O
InChI InChI=1S/C60H96O27/c1-24(9-8-10-25(2)50(76)77)27-13-15-58(7)33-12-11-32-56(4,5)34(14-16-59(32)23-60(33,59)18-17-57(27,58)6)84-55-49(47(39(68)30(21-63)82-55)85-53-46(75)42(71)37(66)29(20-62)81-53)87-54-48(86-52-45(74)40(69)35(64)26(3)79-52)43(72)38(67)31(83-54)22-78-51-44(73)41(70)36(65)28(19-61)80-51/h8-10,24,26-49,51-55,61-75H,11-23H2,1-7H3,(H,76,77)/b9-8+,25-10+/t24-,26+,27-,28+,29-,30+,31-,32+,33+,34+,35+,36+,37-,38-,39+,40-,41-,42+,43+,44+,45-,46-,47-,48-,49+,51+,52+,53+,54+,55-,57-,58+,59-,60+/m1/s1
InChI Key PKFILTNFIVXAID-MEEYSNSNSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C60H96O27
Molecular Weight 1249.40 g/mol
Exact Mass 1248.61389778 g/mol
Topological Polar Surface Area (TPSA) 433.00 Ų
XlogP 0.10
Atomic LogP (AlogP) -2.84
H-Bond Acceptor 26
H-Bond Donor 16
Rotatable Bonds 18

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2E,4E,6R)-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-[(2S,3S,4R,5S,6S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methylhepta-2,4-dienoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7433 74.33%
Caco-2 - 0.8710 87.10%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.8041 80.41%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8074 80.74%
OATP1B3 inhibitior + 0.8110 81.10%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6776 67.76%
BSEP inhibitior + 0.9053 90.53%
P-glycoprotein inhibitior + 0.7456 74.56%
P-glycoprotein substrate + 0.5570 55.70%
CYP3A4 substrate + 0.7268 72.68%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8878 88.78%
CYP3A4 inhibition - 0.9657 96.57%
CYP2C9 inhibition - 0.7286 72.86%
CYP2C19 inhibition - 0.8573 85.73%
CYP2D6 inhibition - 0.9338 93.38%
CYP1A2 inhibition - 0.8475 84.75%
CYP2C8 inhibition + 0.7011 70.11%
CYP inhibitory promiscuity - 0.9057 90.57%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6787 67.87%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.8996 89.96%
Skin irritation - 0.6410 64.10%
Skin corrosion - 0.9426 94.26%
Ames mutagenesis - 0.7008 70.08%
Human Ether-a-go-go-Related Gene inhibition + 0.7981 79.81%
Micronuclear - 0.8000 80.00%
Hepatotoxicity - 0.8100 81.00%
skin sensitisation - 0.8811 88.11%
Respiratory toxicity + 0.5333 53.33%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity - 0.5500 55.00%
Nephrotoxicity - 0.7553 75.53%
Acute Oral Toxicity (c) I 0.4306 43.06%
Estrogen receptor binding + 0.7777 77.77%
Androgen receptor binding + 0.7511 75.11%
Thyroid receptor binding + 0.5795 57.95%
Glucocorticoid receptor binding + 0.7677 76.77%
Aromatase binding + 0.6530 65.30%
PPAR gamma + 0.8000 80.00%
Honey bee toxicity - 0.6195 61.95%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5755 57.55%
Fish aquatic toxicity + 0.9650 96.50%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.46% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.90% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.79% 96.09%
CHEMBL2581 P07339 Cathepsin D 93.62% 98.95%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 93.36% 98.75%
CHEMBL218 P21554 Cannabinoid CB1 receptor 91.49% 96.61%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 90.90% 95.58%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 90.41% 96.21%
CHEMBL4005 P42336 PI3-kinase p110-alpha subunit 88.49% 97.47%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 87.79% 93.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.32% 86.33%
CHEMBL5255 O00206 Toll-like receptor 4 87.11% 92.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 86.56% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.13% 97.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.04% 99.17%
CHEMBL4618 P09960 Leukotriene A4 hydrolase 85.81% 97.86%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.69% 89.00%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 85.61% 96.47%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 84.91% 96.38%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 84.56% 100.00%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 84.38% 95.71%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.08% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.15% 95.89%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.99% 93.56%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 82.95% 95.50%
CHEMBL340 P08684 Cytochrome P450 3A4 82.61% 91.19%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.55% 95.89%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.54% 96.77%
CHEMBL3714130 P46095 G-protein coupled receptor 6 82.13% 97.36%
CHEMBL4683 Q12884 Fibroblast activation protein alpha 81.90% 93.07%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.53% 93.04%
CHEMBL220 P22303 Acetylcholinesterase 81.03% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 80.81% 90.17%
CHEMBL3286 P00749 Urokinase-type plasminogen activator 80.38% 97.88%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Mussaenda macrophylla

Cross-Links

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PubChem 73355976
LOTUS LTS0165631
wikiData Q105210389