3-[[(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidene-5-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methoxy]-3-oxopropanoic acid

Details

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Internal ID ad86de86-87f7-4c11-a0b3-a5b6141e328a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
IUPAC Name 3-[[(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidene-5-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methoxy]-3-oxopropanoic acid
SMILES (Canonical) CC1(CCCC2(C1CCC34C2CCC(C3)C(=C)C4)C)COC(=O)CC(=O)O
SMILES (Isomeric) C[C@]1(CCC[C@@]2([C@@H]1CC[C@]34[C@H]2CC[C@H](C3)C(=C)C4)C)COC(=O)CC(=O)O
InChI InChI=1S/C23H34O4/c1-15-12-23-10-7-17-21(2,14-27-20(26)11-19(24)25)8-4-9-22(17,3)18(23)6-5-16(15)13-23/h16-18H,1,4-14H2,2-3H3,(H,24,25)/t16-,17-,18+,21+,22-,23-/m1/s1
InChI Key AUBICOWTHQIHSK-FKACYGGOSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H34O4
Molecular Weight 374.50 g/mol
Exact Mass 374.24570956 g/mol
Topological Polar Surface Area (TPSA) 63.60 Ų
XlogP 5.80
Atomic LogP (AlogP) 4.97
H-Bond Acceptor 3
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 3-[[(1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidene-5-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methoxy]-3-oxopropanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9888 98.88%
Caco-2 - 0.5487 54.87%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability + 0.5857 58.57%
Subcellular localzation Mitochondria 0.6348 63.48%
OATP2B1 inhibitior - 0.8657 86.57%
OATP1B1 inhibitior + 0.8914 89.14%
OATP1B3 inhibitior + 0.9422 94.22%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6370 63.70%
BSEP inhibitior + 0.7248 72.48%
P-glycoprotein inhibitior - 0.5664 56.64%
P-glycoprotein substrate - 0.7159 71.59%
CYP3A4 substrate + 0.6385 63.85%
CYP2C9 substrate - 0.5973 59.73%
CYP2D6 substrate - 0.8699 86.99%
CYP3A4 inhibition - 0.7680 76.80%
CYP2C9 inhibition - 0.7835 78.35%
CYP2C19 inhibition - 0.8609 86.09%
CYP2D6 inhibition - 0.9232 92.32%
CYP1A2 inhibition - 0.7919 79.19%
CYP2C8 inhibition + 0.4441 44.41%
CYP inhibitory promiscuity - 0.8841 88.41%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9100 91.00%
Carcinogenicity (trinary) Non-required 0.6324 63.24%
Eye corrosion - 0.9726 97.26%
Eye irritation - 0.8112 81.12%
Skin irritation - 0.5769 57.69%
Skin corrosion - 0.9574 95.74%
Ames mutagenesis - 0.8700 87.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4458 44.58%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.5976 59.76%
skin sensitisation - 0.7145 71.45%
Respiratory toxicity - 0.5333 53.33%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.6936 69.36%
Acute Oral Toxicity (c) III 0.6910 69.10%
Estrogen receptor binding + 0.7092 70.92%
Androgen receptor binding - 0.5164 51.64%
Thyroid receptor binding + 0.6194 61.94%
Glucocorticoid receptor binding + 0.7875 78.75%
Aromatase binding + 0.7514 75.14%
PPAR gamma + 0.6245 62.45%
Honey bee toxicity - 0.8816 88.16%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.6450 64.50%
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
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 95.70% 96.38%
CHEMBL221 P23219 Cyclooxygenase-1 95.42% 90.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.02% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.87% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.59% 97.25%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 90.53% 95.50%
CHEMBL340 P08684 Cytochrome P450 3A4 87.53% 91.19%
CHEMBL5028 O14672 ADAM10 84.40% 97.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.17% 97.09%
CHEMBL2581 P07339 Cathepsin D 84.13% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.39% 95.89%
CHEMBL5255 O00206 Toll-like receptor 4 82.67% 92.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.61% 100.00%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 82.46% 97.50%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 81.30% 82.69%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.84% 94.33%

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.
Calocephalus knappii
Helichrysum aureum

Cross-Links

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PubChem 101614949
LOTUS LTS0053813
wikiData Q104918815