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(2S,3S,4S,5S,6S)-6-[(1R,2R,4S,5R,8S,10S,13S,14R,17S,18R,21R,22R,23S)-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-21-[(Z)-2-methylbut-2-enoyl]oxy-22-[(Z)-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 19f56fa2-3b21-441d-ae99-0259c71f9b29
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)-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-21-[(Z)-2-methylbut-2-enoyl]oxy-22-[(Z)-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) CC=C(C)C(=O)OC1C(C23C(CC1(C)C)C4(CCC5C6(CCC(C(C6CCC5(C4(CC2O)C)C)(C)C)C7C(C(C(C(O7)C(=O)O)O)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)C)O)O)OC1C(C(C(C(O1)C)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)OC3O)OC(=O)C=CC1=CC=CC=C1
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1[C@@H]([C@]23[C@@H](C[C@]4([C@@]5(CC[C@@H]6[C@@]([C@H]5CC[C@@]4([C@@H]2CC1(C)C)O[C@@H]3O)(CC[C@@H](C6(C)C)[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)C)C)C)O)OC(=O)/C=C\C1=CC=CC=C1
InChI InChI=1S/C74H110O31/c1-12-30(2)62(92)104-59-60(98-41(78)19-18-33-16-14-13-15-17-33)74-39(26-68(59,5)6)73(105-67(74)93)25-22-38-70(9)23-20-34(69(7,8)37(70)21-24-71(38,10)72(73,11)27-40(74)77)53-58(103-64-51(88)47(84)44(81)35(28-75)96-64)54(52(89)55(99-53)61(90)91)100-66-57(49(86)45(82)36(29-76)97-66)102-65-56(48(85)43(80)32(4)95-65)101-63-50(87)46(83)42(79)31(3)94-63/h12-19,31-32,34-40,42-60,63-67,75-77,79-89,93H,20-29H2,1-11H3,(H,90,91)/b19-18-,30-12-/t31-,32-,34+,35+,36+,37-,38+,39-,40+,42-,43-,44-,45-,46+,47-,48+,49-,50+,51+,52-,53-,54-,55-,56+,57+,58-,59-,60-,63-,64-,65-,66-,67-,70-,71+,72-,73-,74+/m0/s1
InChI Key MDKMWDRBFFTMEG-PMSANBETSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C74H110O31
Molecular Weight 1495.60 g/mol
Exact Mass 1494.7031067 g/mol
Topological Polar Surface Area (TPSA) 486.00 Ų
XlogP 2.20
Atomic LogP (AlogP) -1.06
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)-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-21-[(Z)-2-methylbut-2-enoyl]oxy-22-[(Z)-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 + 0.8710 87.10%
Caco-2 - 0.8588 85.88%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.8066 80.66%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7988 79.88%
OATP1B3 inhibitior + 0.9127 91.27%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9734 97.34%
P-glycoprotein inhibitior + 0.7426 74.26%
P-glycoprotein substrate + 0.7069 70.69%
CYP3A4 substrate + 0.7512 75.12%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8770 87.70%
CYP3A4 inhibition - 0.6145 61.45%
CYP2C9 inhibition - 0.7382 73.82%
CYP2C19 inhibition - 0.8487 84.87%
CYP2D6 inhibition - 0.9272 92.72%
CYP1A2 inhibition - 0.8649 86.49%
CYP2C8 inhibition + 0.8422 84.22%
CYP inhibitory promiscuity - 0.9036 90.36%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5788 57.88%
Eye corrosion - 0.9895 98.95%
Eye irritation - 0.8962 89.62%
Skin irritation - 0.6304 63.04%
Skin corrosion - 0.9405 94.05%
Ames mutagenesis - 0.6078 60.78%
Human Ether-a-go-go-Related Gene inhibition + 0.7642 76.42%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.7209 72.09%
skin sensitisation - 0.8946 89.46%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.9370 93.70%
Acute Oral Toxicity (c) I 0.7298 72.98%
Estrogen receptor binding + 0.5962 59.62%
Androgen receptor binding + 0.7652 76.52%
Thyroid receptor binding + 0.7463 74.63%
Glucocorticoid receptor binding + 0.8168 81.68%
Aromatase binding + 0.7355 73.55%
PPAR gamma + 0.8230 82.30%
Honey bee toxicity - 0.6023 60.23%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5245 52.45%
Fish aquatic toxicity + 0.9894 98.94%

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 99.38% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 98.56% 90.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.00% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.76% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.99% 95.56%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 92.99% 94.62%
CHEMBL4302 P08183 P-glycoprotein 1 92.61% 92.98%
CHEMBL2581 P07339 Cathepsin D 92.57% 98.95%
CHEMBL3714130 P46095 G-protein coupled receptor 6 92.44% 97.36%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 92.30% 94.23%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 91.81% 93.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 91.60% 94.08%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 91.33% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.53% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.13% 97.09%
CHEMBL4227 P25090 Lipoxin A4 receptor 85.93% 100.00%
CHEMBL5028 O14672 ADAM10 85.55% 97.50%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.78% 91.07%
CHEMBL3401 O75469 Pregnane X receptor 84.21% 94.73%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.13% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.92% 95.89%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.81% 95.50%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.28% 93.56%
CHEMBL218 P21554 Cannabinoid CB1 receptor 80.04% 96.61%

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 102354528
LOTUS LTS0256836
wikiData Q105161817