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[(E)-5-[(1S,2S,4aR,8aR)-2-[(2R,3S,4R,5S)-4-acetyloxy-3,5-dihydroxyoxan-2-yl]oxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enyl] 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 5f69aed1-940b-4c4b-b832-fca58ba5cbe0
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name [(E)-5-[(1S,2S,4aR,8aR)-2-[(2R,3S,4R,5S)-4-acetyloxy-3,5-dihydroxyoxan-2-yl]oxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enyl] acetate
SMILES (Canonical) CC(=CCOC(=O)C)CCC1C2(CCCC(C2CCC1(C)OC3C(C(C(CO3)O)OC(=O)C)O)(C)C)C
SMILES (Isomeric) C/C(=C\COC(=O)C)/CC[C@H]1[C@@]2(CCCC([C@H]2CC[C@]1(C)O[C@@H]3[C@H]([C@@H]([C@H](CO3)O)OC(=O)C)O)(C)C)C
InChI InChI=1S/C29H48O8/c1-18(12-16-34-19(2)30)9-10-23-28(6)14-8-13-27(4,5)22(28)11-15-29(23,7)37-26-24(33)25(36-20(3)31)21(32)17-35-26/h12,21-26,32-33H,8-11,13-17H2,1-7H3/b18-12+/t21-,22+,23-,24-,25+,26+,28+,29-/m0/s1
InChI Key BNOSBXHEAQNSDQ-NARDSLQPSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C29H48O8
Molecular Weight 524.70 g/mol
Exact Mass 524.33491849 g/mol
Topological Polar Surface Area (TPSA) 112.00 Ų
XlogP 4.70
Atomic LogP (AlogP) 4.30
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(E)-5-[(1S,2S,4aR,8aR)-2-[(2R,3S,4R,5S)-4-acetyloxy-3,5-dihydroxyoxan-2-yl]oxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enyl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8326 83.26%
Caco-2 - 0.7528 75.28%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8246 82.46%
OATP2B1 inhibitior - 0.5689 56.89%
OATP1B1 inhibitior + 0.8240 82.40%
OATP1B3 inhibitior + 0.9092 90.92%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior + 0.8812 88.12%
P-glycoprotein inhibitior + 0.6402 64.02%
P-glycoprotein substrate - 0.6633 66.33%
CYP3A4 substrate + 0.7055 70.55%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8805 88.05%
CYP3A4 inhibition - 0.8497 84.97%
CYP2C9 inhibition - 0.8758 87.58%
CYP2C19 inhibition - 0.8632 86.32%
CYP2D6 inhibition - 0.9344 93.44%
CYP1A2 inhibition - 0.8339 83.39%
CYP2C8 inhibition + 0.5627 56.27%
CYP inhibitory promiscuity - 0.9262 92.62%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6721 67.21%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.9232 92.32%
Skin irritation - 0.5508 55.08%
Skin corrosion - 0.9498 94.98%
Ames mutagenesis - 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear - 0.7600 76.00%
Hepatotoxicity - 0.7077 70.77%
skin sensitisation - 0.8601 86.01%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity - 0.6870 68.70%
Acute Oral Toxicity (c) III 0.7150 71.50%
Estrogen receptor binding + 0.6429 64.29%
Androgen receptor binding + 0.6061 60.61%
Thyroid receptor binding - 0.4940 49.40%
Glucocorticoid receptor binding + 0.6733 67.33%
Aromatase binding + 0.7530 75.30%
PPAR gamma + 0.6434 64.34%
Honey bee toxicity - 0.7134 71.34%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5955 59.55%
Fish aquatic toxicity + 0.9713 97.13%

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 98.01% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.17% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.96% 91.11%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 89.61% 95.50%
CHEMBL325 Q13547 Histone deacetylase 1 89.40% 95.92%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 88.73% 82.69%
CHEMBL5255 O00206 Toll-like receptor 4 88.56% 92.50%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.38% 94.45%
CHEMBL340 P08684 Cytochrome P450 3A4 86.88% 91.19%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.81% 91.07%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.12% 92.62%
CHEMBL2581 P07339 Cathepsin D 84.00% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.16% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.09% 89.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.95% 94.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.81% 95.89%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 81.76% 91.24%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.76% 97.09%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.65% 100.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.49% 93.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 162963391
LOTUS LTS0047493
wikiData Q104938946