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(2R,4aR,6aS,6aR,6bS,8aS,10R,12aS,14bS)-10-[(2S,3S,4R,5R,6S)-3-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylic 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 a285e72a-960a-42c5-8959-af6489822db2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2R,4aR,6aS,6aR,6bS,8aS,10R,12aS,14bS)-10-[(2S,3S,4R,5R,6S)-3-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylic acid
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC5(C(C4(C)C)CCC6(C5CC=C7C6(CCC8(C7CC(CC8)(C)C(=O)O)C(=O)O)C)C)C)CO)O)O)CO)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@@]5([C@@H](C4(C)C)CC[C@]6([C@H]5CC=C7[C@@]6(CC[C@@]8([C@H]7C[C@](CC8)(C)C(=O)O)C(=O)O)C)C)C)CO)O)O)CO)O)O)O)O)O
InChI InChI=1S/C48H76O19/c1-21-29(51)32(54)35(57)38(62-21)66-37-34(56)31(53)25(20-50)64-40(37)67-36-33(55)30(52)24(19-49)63-39(36)65-28-11-12-45(5)26(43(28,2)3)10-13-47(7)27(45)9-8-22-23-18-44(4,41(58)59)14-16-48(23,42(60)61)17-15-46(22,47)6/h8,21,23-40,49-57H,9-20H2,1-7H3,(H,58,59)(H,60,61)/t21-,23-,24-,25-,26+,27-,28+,29-,30-,31-,32+,33+,34+,35-,36-,37-,38+,39+,40+,44+,45+,46-,47-,48-/m0/s1
InChI Key UPPXMONNNGGKMB-LDEVSCRGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C48H76O19
Molecular Weight 957.10 g/mol
Exact Mass 956.49808019 g/mol
Topological Polar Surface Area (TPSA) 312.00 Ų
XlogP 1.50
Atomic LogP (AlogP) 0.80
H-Bond Acceptor 17
H-Bond Donor 11
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,4aR,6aS,6aR,6bS,8aS,10R,12aS,14bS)-10-[(2S,3S,4R,5R,6S)-3-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7181 71.81%
Caco-2 - 0.8908 89.08%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.8914 89.14%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior - 0.3231 32.31%
OATP1B3 inhibitior - 0.5187 51.87%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior + 0.5974 59.74%
BSEP inhibitior + 0.6963 69.63%
P-glycoprotein inhibitior + 0.7523 75.23%
P-glycoprotein substrate - 0.7882 78.82%
CYP3A4 substrate + 0.7103 71.03%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8798 87.98%
CYP3A4 inhibition - 0.9061 90.61%
CYP2C9 inhibition - 0.8653 86.53%
CYP2C19 inhibition - 0.9130 91.30%
CYP2D6 inhibition - 0.9498 94.98%
CYP1A2 inhibition - 0.8749 87.49%
CYP2C8 inhibition + 0.6663 66.63%
CYP inhibitory promiscuity - 0.9549 95.49%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6115 61.15%
Eye corrosion - 0.9892 98.92%
Eye irritation - 0.9058 90.58%
Skin irritation - 0.6295 62.95%
Skin corrosion - 0.9453 94.53%
Ames mutagenesis - 0.8970 89.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7089 70.89%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.9000 90.00%
skin sensitisation - 0.9028 90.28%
Respiratory toxicity - 0.5667 56.67%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity - 0.6250 62.50%
Nephrotoxicity - 0.7363 73.63%
Acute Oral Toxicity (c) III 0.7689 76.89%
Estrogen receptor binding + 0.7687 76.87%
Androgen receptor binding + 0.7281 72.81%
Thyroid receptor binding - 0.5657 56.57%
Glucocorticoid receptor binding + 0.6915 69.15%
Aromatase binding + 0.6256 62.56%
PPAR gamma + 0.7738 77.38%
Honey bee toxicity - 0.6658 66.58%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6105 61.05%
Fish aquatic toxicity + 0.9722 97.22%

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 96.82% 91.11%
CHEMBL3714130 P46095 G-protein coupled receptor 6 96.41% 97.36%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.08% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.17% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.50% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.46% 95.56%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 86.95% 96.21%
CHEMBL2581 P07339 Cathepsin D 84.75% 98.95%
CHEMBL5255 O00206 Toll-like receptor 4 83.54% 92.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.26% 99.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.04% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.33% 89.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.52% 96.77%

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.
Phytolacca icosandra

Cross-Links

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PubChem 163077393
LOTUS LTS0175629
wikiData Q105276939