2-[(2'S,4aS,8S,8aS)-7-(acetyloxymethyl)-2',4,4,8a-tetramethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid

Details

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Internal ID 796d26e2-89f9-47d5-9a1e-9ca18664ce70
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name 2-[(2'S,4aS,8S,8aS)-7-(acetyloxymethyl)-2',4,4,8a-tetramethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid
SMILES (Canonical) CC(=O)OCC1=CCC2C(CCCC2(C13CCC(O3)(C)CC(=O)O)C)(C)C
SMILES (Isomeric) CC(=O)OCC1=CC[C@@H]2[C@@]([C@@]13CC[C@@](O3)(C)CC(=O)O)(CCCC2(C)C)C
InChI InChI=1S/C22H34O5/c1-15(23)26-14-16-7-8-17-19(2,3)9-6-10-21(17,5)22(16)12-11-20(4,27-22)13-18(24)25/h7,17H,6,8-14H2,1-5H3,(H,24,25)/t17-,20-,21-,22+/m0/s1
InChI Key CUIYYSCXUREZKH-AGOPTVSRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H34O5
Molecular Weight 378.50 g/mol
Exact Mass 378.24062418 g/mol
Topological Polar Surface Area (TPSA) 72.80 Ų
XlogP 3.40
Atomic LogP (AlogP) 4.49
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 2-[(2'S,4aS,8S,8aS)-7-(acetyloxymethyl)-2',4,4,8a-tetramethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9875 98.75%
Caco-2 + 0.6085 60.85%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7857 78.57%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8378 83.78%
OATP1B3 inhibitior + 0.9260 92.60%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.6785 67.85%
P-glycoprotein inhibitior - 0.6214 62.14%
P-glycoprotein substrate - 0.8838 88.38%
CYP3A4 substrate + 0.6177 61.77%
CYP2C9 substrate - 0.6069 60.69%
CYP2D6 substrate - 0.8687 86.87%
CYP3A4 inhibition - 0.6987 69.87%
CYP2C9 inhibition - 0.5796 57.96%
CYP2C19 inhibition - 0.7772 77.72%
CYP2D6 inhibition - 0.9042 90.42%
CYP1A2 inhibition - 0.7491 74.91%
CYP2C8 inhibition + 0.5741 57.41%
CYP inhibitory promiscuity - 0.7026 70.26%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8800 88.00%
Carcinogenicity (trinary) Non-required 0.6000 60.00%
Eye corrosion - 0.9840 98.40%
Eye irritation - 0.8513 85.13%
Skin irritation - 0.6070 60.70%
Skin corrosion - 0.9518 95.18%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6809 68.09%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.6250 62.50%
skin sensitisation - 0.7758 77.58%
Respiratory toxicity - 0.5778 57.78%
Reproductive toxicity + 0.6556 65.56%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.7005 70.05%
Acute Oral Toxicity (c) III 0.5933 59.33%
Estrogen receptor binding + 0.7761 77.61%
Androgen receptor binding + 0.6471 64.71%
Thyroid receptor binding + 0.6600 66.00%
Glucocorticoid receptor binding + 0.7895 78.95%
Aromatase binding + 0.8098 80.98%
PPAR gamma + 0.7024 70.24%
Honey bee toxicity - 0.8807 88.07%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6805 68.05%
Fish aquatic toxicity + 0.9914 99.14%

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 97.54% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.74% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.43% 97.25%
CHEMBL2581 P07339 Cathepsin D 89.67% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.47% 94.45%
CHEMBL340 P08684 Cytochrome P450 3A4 86.88% 91.19%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.96% 86.33%
CHEMBL4040 P28482 MAP kinase ERK2 84.25% 83.82%
CHEMBL221 P23219 Cyclooxygenase-1 82.71% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.91% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 80.44% 94.73%

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.
Chrysoma pauciflosculosa
Grindelia hirsutula

Cross-Links

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PubChem 26452079
LOTUS LTS0193716
wikiData Q104970297