[(1S,2R,4R,5R,6S,9R,10R,13S)-2,6-dihydroxy-5,9-dimethyl-14-methylidene-5-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methyl acetate

Details

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Internal ID 93a8f649-9ced-4b6c-9afc-f0f98167e56e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
IUPAC Name [(1S,2R,4R,5R,6S,9R,10R,13S)-2,6-dihydroxy-5,9-dimethyl-14-methylidene-5-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methyl acetate
SMILES (Canonical) CC(=O)OCC1(C(CCC2(C1CC(C34C2CCC(C3)C(=C)C4)O)C)O)C
SMILES (Isomeric) CC(=O)OC[C@@]1([C@H](CC[C@]2([C@H]1C[C@H]([C@@]34[C@@H]2CC[C@@H](C3)C(=C)C4)O)C)O)C
InChI InChI=1S/C22H34O4/c1-13-10-22-11-15(13)5-6-16(22)20(3)8-7-18(24)21(4,12-26-14(2)23)17(20)9-19(22)25/h15-19,24-25H,1,5-12H2,2-4H3/t15-,16+,17+,18-,19+,20+,21-,22+/m0/s1
InChI Key FOSUPIBQARPELG-DQSBVALTSA-N
Popularity 4 references in papers

Physical and Chemical Properties

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Molecular Formula C22H34O4
Molecular Weight 362.50 g/mol
Exact Mass 362.24570956 g/mol
Topological Polar Surface Area (TPSA) 66.80 Ų
XlogP 3.20
Atomic LogP (AlogP) 3.46
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2R,4R,5R,6S,9R,10R,13S)-2,6-dihydroxy-5,9-dimethyl-14-methylidene-5-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9904 99.04%
Caco-2 + 0.5433 54.33%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.7426 74.26%
OATP2B1 inhibitior - 0.8662 86.62%
OATP1B1 inhibitior + 0.9118 91.18%
OATP1B3 inhibitior + 0.8921 89.21%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6411 64.11%
BSEP inhibitior + 0.6283 62.83%
P-glycoprotein inhibitior - 0.7368 73.68%
P-glycoprotein substrate - 0.6441 64.41%
CYP3A4 substrate + 0.6794 67.94%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8407 84.07%
CYP3A4 inhibition - 0.8428 84.28%
CYP2C9 inhibition - 0.7254 72.54%
CYP2C19 inhibition - 0.8318 83.18%
CYP2D6 inhibition - 0.9525 95.25%
CYP1A2 inhibition - 0.8087 80.87%
CYP2C8 inhibition - 0.6037 60.37%
CYP inhibitory promiscuity - 0.8761 87.61%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6453 64.53%
Eye corrosion - 0.9934 99.34%
Eye irritation - 0.7473 74.73%
Skin irritation + 0.6039 60.39%
Skin corrosion - 0.9590 95.90%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5695 56.95%
Micronuclear - 0.8900 89.00%
Hepatotoxicity - 0.7351 73.51%
skin sensitisation - 0.8711 87.11%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.6186 61.86%
Acute Oral Toxicity (c) III 0.3257 32.57%
Estrogen receptor binding + 0.7907 79.07%
Androgen receptor binding + 0.5562 55.62%
Thyroid receptor binding + 0.5789 57.89%
Glucocorticoid receptor binding + 0.8043 80.43%
Aromatase binding + 0.7305 73.05%
PPAR gamma - 0.5317 53.17%
Honey bee toxicity - 0.7661 76.61%
Biodegradation - 0.6000 60.00%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9974 99.74%

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 96.53% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.10% 94.45%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 93.02% 82.69%
CHEMBL221 P23219 Cyclooxygenase-1 91.90% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.54% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.19% 96.09%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 87.32% 95.50%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 85.20% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.69% 100.00%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 84.33% 96.38%
CHEMBL2581 P07339 Cathepsin D 83.84% 98.95%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 82.85% 93.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.52% 95.89%
CHEMBL340 P08684 Cytochrome P450 3A4 81.02% 91.19%
CHEMBL5028 O14672 ADAM10 80.03% 97.50%

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.
Piper nigrum
Sideritis argyrea
Sideritis huber-morathii
Sideritis perfoliata subsp. athoa
Sideritis pusilla
Sideritis rubriflora
Sideritis sipylea
Sideritis tragoriganum

Cross-Links

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PubChem 133550451
LOTUS LTS0167519
wikiData Q105210145