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[(3R,4S,5S,6R)-6-[2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-yloxy]-4-acetyloxy-5-hydroxyoxan-3-yl] acetate

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 63cfbac6-490e-4923-9159-5e147c97230a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
IUPAC Name [(3R,4S,5S,6R)-6-[2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-yloxy]-4-acetyloxy-5-hydroxyoxan-3-yl] acetate
SMILES (Canonical) CC(=O)OC1COC(C(C1OC(=O)C)O)OC(C)(C)C2CCC3(CCCC(=C)C3C2)C
SMILES (Isomeric) CC(=O)O[C@@H]1CO[C@@H]([C@H]([C@@H]1OC(=O)C)O)OC(C)(C)[C@@H]2CC[C@]3(CCCC(=C)[C@@H]3C2)C
InChI InChI=1S/C24H38O7/c1-14-8-7-10-24(6)11-9-17(12-18(14)24)23(4,5)31-22-20(27)21(30-16(3)26)19(13-28-22)29-15(2)25/h17-22,27H,1,7-13H2,2-6H3/t17-,18+,19-,20+,21-,22-,24-/m1/s1
InChI Key QVYFDGJADKQNBV-NKERXSTMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C24H38O7
Molecular Weight 438.60 g/mol
Exact Mass 438.26175355 g/mol
Topological Polar Surface Area (TPSA) 91.30 Ų
XlogP 3.40
Atomic LogP (AlogP) 3.52
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3R,4S,5S,6R)-6-[2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-yloxy]-4-acetyloxy-5-hydroxyoxan-3-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9425 94.25%
Caco-2 - 0.6364 63.64%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.8439 84.39%
OATP2B1 inhibitior - 0.7146 71.46%
OATP1B1 inhibitior + 0.8741 87.41%
OATP1B3 inhibitior + 0.8781 87.81%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5000 50.00%
BSEP inhibitior - 0.4896 48.96%
P-glycoprotein inhibitior + 0.6153 61.53%
P-glycoprotein substrate - 0.7022 70.22%
CYP3A4 substrate + 0.7194 71.94%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8805 88.05%
CYP3A4 inhibition - 0.7508 75.08%
CYP2C9 inhibition - 0.7943 79.43%
CYP2C19 inhibition - 0.7875 78.75%
CYP2D6 inhibition - 0.9450 94.50%
CYP1A2 inhibition + 0.5160 51.60%
CYP2C8 inhibition + 0.5447 54.47%
CYP inhibitory promiscuity - 0.9388 93.88%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6677 66.77%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.8983 89.83%
Skin irritation + 0.5000 50.00%
Skin corrosion - 0.9416 94.16%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4007 40.07%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.5851 58.51%
skin sensitisation - 0.8027 80.27%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.8035 80.35%
Acute Oral Toxicity (c) III 0.6983 69.83%
Estrogen receptor binding + 0.6483 64.83%
Androgen receptor binding + 0.5781 57.81%
Thyroid receptor binding + 0.5537 55.37%
Glucocorticoid receptor binding + 0.6252 62.52%
Aromatase binding + 0.6121 61.21%
PPAR gamma + 0.5195 51.95%
Honey bee toxicity - 0.6568 65.68%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity + 0.5900 59.00%
Fish aquatic toxicity + 0.9933 99.33%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.92% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.01% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.92% 94.45%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 93.27% 96.77%
CHEMBL1951 P21397 Monoamine oxidase A 91.68% 91.49%
CHEMBL241 Q14432 Phosphodiesterase 3A 90.69% 92.94%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.62% 89.00%
CHEMBL2581 P07339 Cathepsin D 90.44% 98.95%
CHEMBL1871 P10275 Androgen Receptor 88.76% 96.43%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.10% 96.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.04% 99.23%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.97% 100.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.58% 92.62%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 86.45% 91.07%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.32% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.16% 95.89%
CHEMBL259 P32245 Melanocortin receptor 4 85.17% 95.38%
CHEMBL5255 O00206 Toll-like receptor 4 83.33% 92.50%
CHEMBL340 P08684 Cytochrome P450 3A4 83.32% 91.19%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.25% 95.56%
CHEMBL5028 O14672 ADAM10 82.30% 97.50%
CHEMBL3922 P50579 Methionine aminopeptidase 2 81.22% 97.28%
CHEMBL2413 P32246 C-C chemokine receptor type 1 80.94% 89.50%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 80.57% 83.00%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 80.44% 82.50%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.26% 94.33%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.12% 97.14%

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.
Lessingia glandulifera

Cross-Links

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PubChem 14138820
LOTUS LTS0255060
wikiData Q105228999