Cynarascoloside C

Details

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Internal ID fbdcdb86-a705-4536-baf8-70e97b989de5
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name (3S,3aR,4S,6aR,9S,9aR,9bR)-3,9-dimethyl-6-methylidene-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione
SMILES (Canonical) CC1C2C(CC1=O)C(=C)CC(C3C2OC(=O)C3C)OC4C(C(C(C(O4)CO)O)O)O
SMILES (Isomeric) C[C@H]1[C@H]2[C@@H](CC1=O)C(=C)C[C@@H]([C@@H]3[C@@H]2OC(=O)[C@H]3C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
InChI InChI=1S/C21H30O9/c1-7-4-12(28-21-18(26)17(25)16(24)13(6-22)29-21)15-9(3)20(27)30-19(15)14-8(2)11(23)5-10(7)14/h8-10,12-19,21-22,24-26H,1,4-6H2,2-3H3/t8-,9+,10+,12+,13-,14+,15-,16-,17+,18-,19-,21-/m1/s1
InChI Key HGFWSEPBYRBDOL-JVEAFJHYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H30O9
Molecular Weight 426.50 g/mol
Exact Mass 426.18898253 g/mol
Topological Polar Surface Area (TPSA) 143.00 Ų
XlogP -0.70
Atomic LogP (AlogP) -0.85
H-Bond Acceptor 9
H-Bond Donor 4
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of Cynarascoloside C

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6660 66.60%
Caco-2 - 0.7965 79.65%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.7392 73.92%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8412 84.12%
OATP1B3 inhibitior + 0.9598 95.98%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.5309 53.09%
P-glycoprotein inhibitior - 0.7494 74.94%
P-glycoprotein substrate - 0.7973 79.73%
CYP3A4 substrate + 0.6082 60.82%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8900 89.00%
CYP3A4 inhibition - 0.7739 77.39%
CYP2C9 inhibition - 0.8695 86.95%
CYP2C19 inhibition - 0.8579 85.79%
CYP2D6 inhibition - 0.9303 93.03%
CYP1A2 inhibition - 0.8443 84.43%
CYP2C8 inhibition - 0.8670 86.70%
CYP inhibitory promiscuity - 0.8860 88.60%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.7282 72.82%
Eye corrosion - 0.9848 98.48%
Eye irritation - 0.9338 93.38%
Skin irritation - 0.7138 71.38%
Skin corrosion - 0.9321 93.21%
Ames mutagenesis - 0.6354 63.54%
Human Ether-a-go-go-Related Gene inhibition - 0.4528 45.28%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.6625 66.25%
skin sensitisation - 0.8573 85.73%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity + 0.5053 50.53%
Acute Oral Toxicity (c) III 0.5078 50.78%
Estrogen receptor binding + 0.5862 58.62%
Androgen receptor binding - 0.5072 50.72%
Thyroid receptor binding + 0.5669 56.69%
Glucocorticoid receptor binding - 0.5967 59.67%
Aromatase binding - 0.5478 54.78%
PPAR gamma - 0.6055 60.55%
Honey bee toxicity - 0.7483 74.83%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.6450 64.50%
Fish aquatic toxicity + 0.9502 95.02%

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 96.07% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.00% 96.09%
CHEMBL2581 P07339 Cathepsin D 90.14% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.98% 97.09%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 87.71% 86.92%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.17% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.35% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.03% 94.00%
CHEMBL220 P22303 Acetylcholinesterase 81.58% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.98% 99.17%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.90% 97.25%

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.
Colchicum soboliferum
Cynara cardunculus
Psorothamnus spinosus
Trachelospermum asiaticum

Cross-Links

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PubChem 101156886
NPASS NPC163665
LOTUS LTS0057869
wikiData Q105027719