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3-[(3S,3aS,5aR,6S,7R,9R,9aR)-9-[(Z,2R)-2-hydroxy-3-methylpent-3-enoyl]oxy-7-(2-hydroxypropan-2-yl)-3a,6,9a-trimethyl-3-[(3S,5S)-5-(2-methylprop-1-enyl)oxolan-3-yl]-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]propanoic 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 ac26d906-2f6c-4f78-bc30-fba9cf91ee3c
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
IUPAC Name 3-[(3S,3aS,5aR,6S,7R,9R,9aR)-9-[(Z,2R)-2-hydroxy-3-methylpent-3-enoyl]oxy-7-(2-hydroxypropan-2-yl)-3a,6,9a-trimethyl-3-[(3S,5S)-5-(2-methylprop-1-enyl)oxolan-3-yl]-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
SMILES (Canonical) CC=C(C)C(C(=O)OC1CC(C(C2C1(C3=CCC(C3(CC2)C)C4CC(OC4)C=C(C)C)C)(C)CCC(=O)O)C(C)(C)O)O
SMILES (Isomeric) C/C=C(/C)\[C@H](C(=O)O[C@@H]1C[C@H]([C@@]([C@@H]2[C@@]1(C3=CC[C@H]([C@@]3(CC2)C)[C@@H]4C[C@H](OC4)C=C(C)C)C)(C)CCC(=O)O)C(C)(C)O)O
InChI InChI=1S/C36H56O7/c1-10-22(4)31(39)32(40)43-29-19-28(33(5,6)41)35(8,16-14-30(37)38)27-13-15-34(7)25(11-12-26(34)36(27,29)9)23-18-24(42-20-23)17-21(2)3/h10,12,17,23-25,27-29,31,39,41H,11,13-16,18-20H2,1-9H3,(H,37,38)/b22-10-/t23-,24-,25+,27-,28+,29-,31-,34+,35+,36+/m1/s1
InChI Key WMWGSTONTQJHTQ-COXIXVMXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C36H56O7
Molecular Weight 600.80 g/mol
Exact Mass 600.40260412 g/mol
Topological Polar Surface Area (TPSA) 113.00 Ų
XlogP 6.80
Atomic LogP (AlogP) 6.63
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3-[(3S,3aS,5aR,6S,7R,9R,9aR)-9-[(Z,2R)-2-hydroxy-3-methylpent-3-enoyl]oxy-7-(2-hydroxypropan-2-yl)-3a,6,9a-trimethyl-3-[(3S,5S)-5-(2-methylprop-1-enyl)oxolan-3-yl]-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9920 99.20%
Caco-2 - 0.7871 78.71%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.9054 90.54%
OATP2B1 inhibitior - 0.8599 85.99%
OATP1B1 inhibitior + 0.8416 84.16%
OATP1B3 inhibitior + 0.9261 92.61%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7157 71.57%
BSEP inhibitior + 0.9171 91.71%
P-glycoprotein inhibitior + 0.7360 73.60%
P-glycoprotein substrate + 0.6078 60.78%
CYP3A4 substrate + 0.7363 73.63%
CYP2C9 substrate - 0.8125 81.25%
CYP2D6 substrate - 0.8700 87.00%
CYP3A4 inhibition + 0.5093 50.93%
CYP2C9 inhibition - 0.6697 66.97%
CYP2C19 inhibition - 0.8793 87.93%
CYP2D6 inhibition - 0.9203 92.03%
CYP1A2 inhibition - 0.8676 86.76%
CYP2C8 inhibition + 0.7413 74.13%
CYP inhibitory promiscuity - 0.7509 75.09%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5355 53.55%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.9273 92.73%
Skin irritation + 0.5483 54.83%
Skin corrosion - 0.9437 94.37%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6449 64.49%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.5226 52.26%
skin sensitisation - 0.9021 90.21%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.8540 85.40%
Acute Oral Toxicity (c) III 0.5101 51.01%
Estrogen receptor binding + 0.7646 76.46%
Androgen receptor binding + 0.7061 70.61%
Thyroid receptor binding - 0.4946 49.46%
Glucocorticoid receptor binding + 0.7945 79.45%
Aromatase binding + 0.7476 74.76%
PPAR gamma + 0.6562 65.62%
Honey bee toxicity - 0.5995 59.95%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.9958 99.58%

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
CHEMBL4040 P28482 MAP kinase ERK2 99.98% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.56% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.61% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.13% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.09% 91.11%
CHEMBL2581 P07339 Cathepsin D 94.33% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.58% 97.09%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 92.44% 97.21%
CHEMBL340 P08684 Cytochrome P450 3A4 90.53% 91.19%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 90.43% 89.05%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.60% 89.00%
CHEMBL5028 O14672 ADAM10 89.32% 97.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 88.67% 100.00%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 88.21% 94.23%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.62% 91.07%
CHEMBL3359 P21462 Formyl peptide receptor 1 85.01% 93.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.98% 99.17%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.86% 97.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.56% 86.33%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 83.89% 94.97%
CHEMBL2179 P04062 Beta-glucocerebrosidase 83.87% 85.31%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.13% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.06% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 80.48% 90.17%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.33% 95.89%

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
Aristolochia triangularis
Macaranga tanarius

Cross-Links

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PubChem 163106434
LOTUS LTS0090619
wikiData Q105161964