(E)-5-[(1S,4aR,5S,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid

Details

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Internal ID 1bf43faa-57b1-4879-b393-f9760e7bb6a9
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name (E)-5-[(1S,4aR,5S,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
SMILES (Canonical) CC(=CC(=O)O)CCC1C(=C)CCC2C1(CCCC2(C)CO)C.CC(=CC(=O)O)CCC1C(=C)CCC2C1(CCCC2(C)CO)C
SMILES (Isomeric) C/C(=C\C(=O)O)/CC[C@@H]1[C@@]2([C@H]([C@](CCC2)(CO)C)CCC1=C)C.C/C(=C\C(=O)O)/CC[C@@H]1[C@@]2([C@H]([C@](CCC2)(CO)C)CCC1=C)C
InChI InChI=1S/2C20H32O3/c2*1-14(12-18(22)23)6-8-16-15(2)7-9-17-19(3,13-21)10-5-11-20(16,17)4/h2*12,16-17,21H,2,5-11,13H2,1,3-4H3,(H,22,23)/b2*14-12+/t2*16-,17-,19+,20+/m00/s1
InChI Key HIEHXTQXLQBSMD-YIMFAWMKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C40H64O6
Molecular Weight 640.90 g/mol
Exact Mass 640.47028976 g/mol
Topological Polar Surface Area (TPSA) 115.00 Ų
XlogP 0.00
Atomic LogP (AlogP) 9.14
H-Bond Acceptor 4
H-Bond Donor 4
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (E)-5-[(1S,4aR,5S,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9527 95.27%
Caco-2 - 0.5966 59.66%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7326 73.26%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8119 81.19%
OATP1B3 inhibitior + 0.8131 81.31%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior + 0.5193 51.93%
BSEP inhibitior + 0.8579 85.79%
P-glycoprotein inhibitior - 0.5057 50.57%
P-glycoprotein substrate - 0.7982 79.82%
CYP3A4 substrate + 0.6185 61.85%
CYP2C9 substrate - 0.8008 80.08%
CYP2D6 substrate - 0.9158 91.58%
CYP3A4 inhibition - 0.5704 57.04%
CYP2C9 inhibition - 0.8065 80.65%
CYP2C19 inhibition - 0.8398 83.98%
CYP2D6 inhibition - 0.9046 90.46%
CYP1A2 inhibition - 0.8508 85.08%
CYP2C8 inhibition + 0.4564 45.64%
CYP inhibitory promiscuity - 0.8228 82.28%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9000 90.00%
Carcinogenicity (trinary) Non-required 0.6777 67.77%
Eye corrosion - 0.9808 98.08%
Eye irritation - 0.7462 74.62%
Skin irritation - 0.7131 71.31%
Skin corrosion - 0.9711 97.11%
Ames mutagenesis - 0.8400 84.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8653 86.53%
Micronuclear - 0.8900 89.00%
Hepatotoxicity - 0.7822 78.22%
skin sensitisation - 0.6130 61.30%
Respiratory toxicity - 0.5333 53.33%
Reproductive toxicity + 0.6000 60.00%
Mitochondrial toxicity - 0.5000 50.00%
Nephrotoxicity - 0.7700 77.00%
Acute Oral Toxicity (c) III 0.6194 61.94%
Estrogen receptor binding + 0.7808 78.08%
Androgen receptor binding + 0.7267 72.67%
Thyroid receptor binding + 0.5383 53.83%
Glucocorticoid receptor binding + 0.6807 68.07%
Aromatase binding + 0.7017 70.17%
PPAR gamma + 0.6035 60.35%
Honey bee toxicity - 0.8694 86.94%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6500 65.00%
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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.04% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 93.02% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.44% 97.25%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 87.87% 95.50%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.58% 94.45%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 87.05% 95.50%
CHEMBL2061 P19793 Retinoid X receptor alpha 86.76% 91.67%
CHEMBL2581 P07339 Cathepsin D 85.82% 98.95%
CHEMBL340 P08684 Cytochrome P450 3A4 85.11% 91.19%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.47% 95.56%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 82.59% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.40% 100.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.96% 100.00%
CHEMBL233 P35372 Mu opioid receptor 81.66% 97.93%
CHEMBL221 P23219 Cyclooxygenase-1 80.15% 90.17%

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.
Pinus pumila

Cross-Links

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PubChem 139065784
LOTUS LTS0167960
wikiData Q104396783