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(2E,4E,6E,8E)-12-[[(1S,3R,7R,8R,8aS)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy]-10-hydroxy-5,9,11-trimethyl-12-oxo-dodeca-2,4,6,8-tetraenoic 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 f2376dfb-4aee-4ed2-968d-c6846a8b25e8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
IUPAC Name (2E,4E,6E,8E)-12-[[(1S,3R,7R,8R,8aS)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy]-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid
SMILES (Canonical) CC1CC(C2C(=C1)C=CC(C2(C)C(=O)CCO)(C)O)OC(=O)C(C)C(C(=CC=CC(=CC=CC(=O)O)C)C)O
SMILES (Isomeric) C[C@@H]1C[C@@H]([C@H]2C(=C1)C=C[C@@]([C@]2(C)C(=O)CCO)(C)O)OC(=O)C(C)C(/C(=C/C=C/C(=C/C=C/C(=O)O)/C)/C)O
InChI InChI=1S/C31H42O8/c1-19(10-8-12-26(34)35)9-7-11-21(3)28(36)22(4)29(37)39-24-18-20(2)17-23-13-15-30(5,38)31(6,27(23)24)25(33)14-16-32/h7-13,15,17,20,22,24,27-28,32,36,38H,14,16,18H2,1-6H3,(H,34,35)/b9-7+,12-8+,19-10+,21-11+/t20-,22?,24-,27+,28?,30+,31+/m0/s1
InChI Key VBTJSQZQYFMROV-UXPBUBJASA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C31H42O8
Molecular Weight 542.70 g/mol
Exact Mass 542.28796829 g/mol
Topological Polar Surface Area (TPSA) 141.00 Ų
XlogP 4.00
Atomic LogP (AlogP) 3.85
H-Bond Acceptor 7
H-Bond Donor 4
Rotatable Bonds 11

Synonyms

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(1R,2R,6R,8S,8aR)-3-Hydroxy-2,4,8-trimethyldodeca-4(E),6(E),8(E),10(E)-tetraenedioic acid 1-[2-hydroxy-1-(3-hydroxypropanoyl)-1,2,6-trimethyl-1,2,6,7,8,8a-hexahydronaphth-8-yl]monoester
(2E,4E,6E,8E)-12-[[(1S,3R,7R,8R,8aS)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy]-10-hydroxy-5,9,11-trimethyl-12-oxo-dodeca-2,4,6,8-tetraenoic acid

2D Structure

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2D Structure of (2E,4E,6E,8E)-12-[[(1S,3R,7R,8R,8aS)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy]-10-hydroxy-5,9,11-trimethyl-12-oxo-dodeca-2,4,6,8-tetraenoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9837 98.37%
Caco-2 - 0.7752 77.52%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7974 79.74%
OATP2B1 inhibitior - 0.7179 71.79%
OATP1B1 inhibitior + 0.8308 83.08%
OATP1B3 inhibitior + 0.8540 85.40%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5864 58.64%
BSEP inhibitior + 0.9723 97.23%
P-glycoprotein inhibitior + 0.7750 77.50%
P-glycoprotein substrate + 0.6846 68.46%
CYP3A4 substrate + 0.6984 69.84%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9174 91.74%
CYP3A4 inhibition - 0.6661 66.61%
CYP2C9 inhibition - 0.8657 86.57%
CYP2C19 inhibition - 0.9212 92.12%
CYP2D6 inhibition - 0.9101 91.01%
CYP1A2 inhibition - 0.6430 64.30%
CYP2C8 inhibition + 0.6189 61.89%
CYP inhibitory promiscuity - 0.8329 83.29%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.6283 62.83%
Eye corrosion - 0.9914 99.14%
Eye irritation - 0.9363 93.63%
Skin irritation + 0.6000 60.00%
Skin corrosion - 0.9448 94.48%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4474 44.74%
Micronuclear - 0.7200 72.00%
Hepatotoxicity + 0.6033 60.33%
skin sensitisation - 0.8552 85.52%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity - 0.7949 79.49%
Acute Oral Toxicity (c) III 0.8422 84.22%
Estrogen receptor binding + 0.7541 75.41%
Androgen receptor binding + 0.6287 62.87%
Thyroid receptor binding + 0.6107 61.07%
Glucocorticoid receptor binding + 0.8052 80.52%
Aromatase binding + 0.6662 66.62%
PPAR gamma + 0.6946 69.46%
Honey bee toxicity - 0.7034 70.34%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.7200 72.00%
Fish aquatic toxicity + 0.9607 96.07%

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 97.62% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 95.99% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.12% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 93.79% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.43% 97.25%
CHEMBL1937 Q92769 Histone deacetylase 2 92.45% 94.75%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.40% 94.45%
CHEMBL2996 Q05655 Protein kinase C delta 88.73% 97.79%
CHEMBL2581 P07339 Cathepsin D 87.79% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.73% 97.09%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.66% 91.07%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.65% 86.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.32% 95.89%
CHEMBL299 P17252 Protein kinase C alpha 85.45% 98.03%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.32% 95.56%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 84.93% 94.23%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.59% 99.17%
CHEMBL2061 P19793 Retinoid X receptor alpha 82.53% 91.67%
CHEMBL340 P08684 Cytochrome P450 3A4 82.14% 91.19%
CHEMBL4208 P20618 Proteasome component C5 81.66% 90.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.63% 100.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.50% 96.00%

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.
Kopsia griffithii
Tabernaemontana cymosa

Cross-Links

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PubChem 6474046
LOTUS LTS0242906
wikiData Q105351404