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(3S)-3-[(3S,3aS,5aR,6R,7S,9R,9aR)-9-acetyloxy-3a,6,9a-trimethyl-3-[(3S,5S)-5-(2-methylprop-1-enyl)oxolan-3-yl]-7-prop-1-en-2-yl-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]-3-acetyloxypropanoic 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 fbf9af42-4337-4533-9048-5366cb24124e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
IUPAC Name (3S)-3-[(3S,3aS,5aR,6R,7S,9R,9aR)-9-acetyloxy-3a,6,9a-trimethyl-3-[(3S,5S)-5-(2-methylprop-1-enyl)oxolan-3-yl]-7-prop-1-en-2-yl-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]-3-acetyloxypropanoic acid
SMILES (Canonical) CC(=CC1CC(CO1)C2CC=C3C2(CCC4C3(C(CC(C4(C)C(CC(=O)O)OC(=O)C)C(=C)C)OC(=O)C)C)C)C
SMILES (Isomeric) CC(=C[C@@H]1C[C@H](CO1)[C@@H]2CC=C3[C@]2(CC[C@H]4[C@]3([C@@H](C[C@H]([C@@]4(C)[C@H](CC(=O)O)OC(=O)C)C(=C)C)OC(=O)C)C)C)C
InChI InChI=1S/C34H50O7/c1-19(2)14-24-15-23(18-39-24)25-10-11-27-32(25,7)13-12-28-33(8,30(17-31(37)38)41-22(6)36)26(20(3)4)16-29(34(27,28)9)40-21(5)35/h11,14,23-26,28-30H,3,10,12-13,15-18H2,1-2,4-9H3,(H,37,38)/t23-,24-,25+,26+,28-,29-,30+,32+,33-,34+/m1/s1
InChI Key JHUWVMXELQZRFA-MMWJASJTSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C34H50O7
Molecular Weight 570.80 g/mol
Exact Mass 570.35565393 g/mol
Topological Polar Surface Area (TPSA) 99.10 Ų
XlogP 6.70
Atomic LogP (AlogP) 6.67
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3S)-3-[(3S,3aS,5aR,6R,7S,9R,9aR)-9-acetyloxy-3a,6,9a-trimethyl-3-[(3S,5S)-5-(2-methylprop-1-enyl)oxolan-3-yl]-7-prop-1-en-2-yl-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]-3-acetyloxypropanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9943 99.43%
Caco-2 - 0.7518 75.18%
Blood Brain Barrier + 0.8500 85.00%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.8279 82.79%
OATP2B1 inhibitior - 0.8612 86.12%
OATP1B1 inhibitior + 0.8435 84.35%
OATP1B3 inhibitior + 0.7885 78.85%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior + 0.9572 95.72%
P-glycoprotein inhibitior + 0.7828 78.28%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7233 72.33%
CYP2C9 substrate - 0.6027 60.27%
CYP2D6 substrate - 0.8768 87.68%
CYP3A4 inhibition - 0.5630 56.30%
CYP2C9 inhibition - 0.6120 61.20%
CYP2C19 inhibition - 0.8626 86.26%
CYP2D6 inhibition - 0.9463 94.63%
CYP1A2 inhibition - 0.7988 79.88%
CYP2C8 inhibition + 0.6793 67.93%
CYP inhibitory promiscuity - 0.8646 86.46%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.5681 56.81%
Eye corrosion - 0.9879 98.79%
Eye irritation - 0.9120 91.20%
Skin irritation + 0.5255 52.55%
Skin corrosion - 0.9348 93.48%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6060 60.60%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.6321 63.21%
skin sensitisation - 0.8480 84.80%
Respiratory toxicity + 0.5333 53.33%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.5699 56.99%
Acute Oral Toxicity (c) I 0.5211 52.11%
Estrogen receptor binding + 0.7793 77.93%
Androgen receptor binding + 0.6989 69.89%
Thyroid receptor binding + 0.5448 54.48%
Glucocorticoid receptor binding + 0.7960 79.60%
Aromatase binding + 0.6795 67.95%
PPAR gamma + 0.7079 70.79%
Honey bee toxicity - 0.5935 59.35%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5155 51.55%
Fish aquatic toxicity + 1.0000 100.00%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.68% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.93% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.03% 94.45%
CHEMBL4040 P28482 MAP kinase ERK2 95.15% 83.82%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 91.85% 97.21%
CHEMBL340 P08684 Cytochrome P450 3A4 90.49% 91.19%
CHEMBL2581 P07339 Cathepsin D 90.00% 98.95%
CHEMBL221 P23219 Cyclooxygenase-1 89.19% 90.17%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.91% 97.25%
CHEMBL5028 O14672 ADAM10 88.83% 97.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.51% 100.00%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 88.06% 89.05%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.23% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.22% 97.09%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 86.07% 94.62%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 86.02% 94.08%
CHEMBL1907598 P05106 Integrin alpha-V/beta-3 85.32% 95.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.71% 95.56%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 82.64% 94.97%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.54% 86.33%
CHEMBL3359 P21462 Formyl peptide receptor 1 81.92% 93.56%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.58% 96.95%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.00% 91.07%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.57% 100.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.50% 93.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.27% 95.50%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.20% 82.69%

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.
Aglaia argentea

Cross-Links

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PubChem 163104556
LOTUS LTS0270689
wikiData Q105128360