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(2S,3S,4S,5S,6S)-6-[(1R,2R,4S,5R,8S,10S,13S,14R,17S,18R,21R,22R,23S)-21-benzoyloxy-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-22-[(E)-3-phenylprop-2-enoyl]oxy-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl]-4-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic 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 7facd2d3-3839-4f34-85f5-a711cb5bde55
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3S,4S,5S,6S)-6-[(1R,2R,4S,5R,8S,10S,13S,14R,17S,18R,21R,22R,23S)-21-benzoyloxy-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-22-[(E)-3-phenylprop-2-enoyl]oxy-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl]-4-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4C(C(OC(C4OC5C(C(C(C(O5)CO)O)O)O)C6CCC7(C(C6(C)C)CCC8(C7CCC91C8(CC(C2(C9CC(C(C2OC(=O)C=CC2=CC=CC=C2)OC(=O)C2=CC=CC=C2)(C)C)C(O1)O)O)C)C)C)C(=O)O)O)CO)O)O)C)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]4[C@@H]([C@H](O[C@H]([C@@H]4O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)[C@H]6CC[C@@]7([C@H]8CC[C@]91[C@@H]2CC([C@H]([C@@H]([C@@]2([C@@H](C[C@]9([C@@]8(CC[C@H]7C6(C)C)C)C)O)[C@H](O1)O)OC(=O)/C=C/C1=CC=CC=C1)OC(=O)C1=CC=CC=C1)(C)C)C)C(=O)O)O)CO)O)O)C)O)O)O)O)O
InChI InChI=1S/C76H108O31/c1-32-44(81)48(85)52(89)65(96-32)103-58-50(87)45(82)33(2)97-67(58)104-59-51(88)47(84)38(31-78)99-68(59)102-56-54(91)57(63(92)93)101-55(60(56)105-66-53(90)49(86)46(83)37(30-77)98-66)36-22-25-72(7)39(71(36,5)6)23-26-73(8)40(72)24-27-75-41-28-70(3,4)61(106-64(94)35-18-14-11-15-19-35)62(100-43(80)21-20-34-16-12-10-13-17-34)76(41,69(95)107-75)42(79)29-74(73,75)9/h10-21,32-33,36-42,44-62,65-69,77-79,81-91,95H,22-31H2,1-9H3,(H,92,93)/b21-20+/t32-,33-,36+,37+,38+,39-,40+,41-,42+,44-,45-,46-,47-,48+,49-,50+,51-,52+,53+,54-,55-,56-,57-,58+,59+,60-,61-,62-,65-,66-,67-,68-,69-,72-,73+,74-,75-,76+/m0/s1
InChI Key LHLWERNEXPTXMR-AVSAADINSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C76H108O31
Molecular Weight 1517.60 g/mol
Exact Mass 1516.6874566 g/mol
Topological Polar Surface Area (TPSA) 486.00 Ų
XlogP 2.70
Atomic LogP (AlogP) -0.72
H-Bond Acceptor 30
H-Bond Donor 16
Rotatable Bonds 17

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3S,4S,5S,6S)-6-[(1R,2R,4S,5R,8S,10S,13S,14R,17S,18R,21R,22R,23S)-21-benzoyloxy-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-22-[(E)-3-phenylprop-2-enoyl]oxy-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl]-4-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7911 79.11%
Caco-2 - 0.8584 85.84%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.7928 79.28%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8014 80.14%
OATP1B3 inhibitior + 0.9107 91.07%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7787 77.87%
BSEP inhibitior + 0.9708 97.08%
P-glycoprotein inhibitior + 0.7425 74.25%
P-glycoprotein substrate + 0.7044 70.44%
CYP3A4 substrate + 0.7501 75.01%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8733 87.33%
CYP3A4 inhibition - 0.6129 61.29%
CYP2C9 inhibition - 0.8242 82.42%
CYP2C19 inhibition - 0.8618 86.18%
CYP2D6 inhibition - 0.9436 94.36%
CYP1A2 inhibition - 0.9072 90.72%
CYP2C8 inhibition + 0.8567 85.67%
CYP inhibitory promiscuity - 0.9343 93.43%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6047 60.47%
Eye corrosion - 0.9898 98.98%
Eye irritation - 0.8961 89.61%
Skin irritation - 0.7044 70.44%
Skin corrosion - 0.9395 93.95%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7569 75.69%
Micronuclear - 0.7000 70.00%
Hepatotoxicity - 0.6834 68.34%
skin sensitisation - 0.9106 91.06%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.9674 96.74%
Acute Oral Toxicity (c) I 0.6886 68.86%
Estrogen receptor binding + 0.5875 58.75%
Androgen receptor binding + 0.7646 76.46%
Thyroid receptor binding + 0.7571 75.71%
Glucocorticoid receptor binding + 0.8200 82.00%
Aromatase binding + 0.7299 72.99%
PPAR gamma + 0.8238 82.38%
Honey bee toxicity - 0.6210 62.10%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5445 54.45%
Fish aquatic toxicity + 0.9925 99.25%

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
CHEMBL221 P23219 Cyclooxygenase-1 99.03% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 98.55% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.73% 91.11%
CHEMBL4302 P08183 P-glycoprotein 1 97.53% 92.98%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.46% 96.09%
CHEMBL1951 P21397 Monoamine oxidase A 95.92% 91.49%
CHEMBL2581 P07339 Cathepsin D 93.84% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.31% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.67% 97.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.63% 96.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 90.19% 94.08%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 89.95% 94.23%
CHEMBL5028 O14672 ADAM10 87.98% 97.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.62% 89.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 87.02% 97.36%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.25% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 86.17% 91.07%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 84.85% 93.00%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 84.50% 81.11%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.92% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.70% 95.89%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 83.61% 87.67%
CHEMBL226 P30542 Adenosine A1 receptor 83.53% 95.93%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 83.14% 95.83%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.93% 99.17%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 80.93% 94.62%
CHEMBL218 P21554 Cannabinoid CB1 receptor 80.75% 96.61%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 80.55% 83.00%
CHEMBL3401 O75469 Pregnane X receptor 80.31% 94.73%

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.
Maesa balansae

Cross-Links

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PubChem 102354529
LOTUS LTS0268973
wikiData Q105151838