Rhuscholide A

Details

Top
Internal ID 0f51750b-60b4-429b-abd0-ad90754eddbd
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name 5-hydroxy-3-propan-2-ylidene-7-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]-1-benzofuran-2-one
SMILES (Canonical) CC(=CCCC(=CCCC(=CCCC(=CCC1=C2C(=CC(=C1)O)C(=C(C)C)C(=O)O2)C)C)C)C
SMILES (Isomeric) CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CC1=C2C(=CC(=C1)O)C(=C(C)C)C(=O)O2)/C)/C)/C)C
InChI InChI=1S/C31H42O3/c1-21(2)11-8-12-23(5)13-9-14-24(6)15-10-16-25(7)17-18-26-19-27(32)20-28-29(22(3)4)31(33)34-30(26)28/h11,13,15,17,19-20,32H,8-10,12,14,16,18H2,1-7H3/b23-13+,24-15+,25-17+
InChI Key LPJLAXYRFCLYIG-HBKYZHKXSA-N
Popularity 2 references in papers

Physical and Chemical Properties

Top
Molecular Formula C31H42O3
Molecular Weight 462.70 g/mol
Exact Mass 462.31339520 g/mol
Topological Polar Surface Area (TPSA) 46.50 Ų
XlogP 10.00
Atomic LogP (AlogP) 8.79
H-Bond Acceptor 3
H-Bond Donor 1
Rotatable Bonds 11

Synonyms

Top
944804-58-4
5-hydroxy-3-propan-2-ylidene-7-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]-1-benzofuran-2-one
5-hydroxy-3-(propan-2-ylidene)-7-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-1-benzofuran-2(3H)-one
5-hydroxy-3-(propan-2-ylidene)-7-[3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-2(3H)-benzofuranone
CHEBI:66306
AKOS040762282
Q27134849
2(3H)-Benzofuranone, 5-hydroxy-3-(1-methylethylidene)-7-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-
5-hydroxy-3-isopropylidene-7-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]benzofuran-2-one

2D Structure

Top
2D Structure of Rhuscholide A

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9961 99.61%
Caco-2 - 0.5370 53.70%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7371 73.71%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8461 84.61%
OATP1B3 inhibitior + 0.9320 93.20%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.9320 93.20%
P-glycoprotein inhibitior + 0.9165 91.65%
P-glycoprotein substrate - 0.8957 89.57%
CYP3A4 substrate + 0.5272 52.72%
CYP2C9 substrate + 0.5918 59.18%
CYP2D6 substrate - 0.8481 84.81%
CYP3A4 inhibition + 0.5915 59.15%
CYP2C9 inhibition + 0.5288 52.88%
CYP2C19 inhibition + 0.6575 65.75%
CYP2D6 inhibition - 0.7913 79.13%
CYP1A2 inhibition + 0.9110 91.10%
CYP2C8 inhibition - 0.6794 67.94%
CYP inhibitory promiscuity + 0.7276 72.76%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9000 90.00%
Carcinogenicity (trinary) Non-required 0.6311 63.11%
Eye corrosion - 0.9863 98.63%
Eye irritation - 0.8927 89.27%
Skin irritation - 0.6447 64.47%
Skin corrosion - 0.9251 92.51%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8434 84.34%
Micronuclear - 0.8500 85.00%
Hepatotoxicity + 0.5052 50.52%
skin sensitisation - 0.5845 58.45%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.5778 57.78%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity + 0.6054 60.54%
Acute Oral Toxicity (c) III 0.4154 41.54%
Estrogen receptor binding + 0.7807 78.07%
Androgen receptor binding + 0.5604 56.04%
Thyroid receptor binding + 0.5966 59.66%
Glucocorticoid receptor binding + 0.7610 76.10%
Aromatase binding + 0.6611 66.11%
PPAR gamma + 0.7127 71.27%
Honey bee toxicity - 0.8774 87.74%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

Top

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 97.94% 91.11%
CHEMBL4769 O95749 Geranylgeranyl pyrophosphate synthetase 97.94% 92.08%
CHEMBL2581 P07339 Cathepsin D 97.82% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 96.44% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.34% 95.56%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 89.87% 93.10%
CHEMBL3060 Q9Y345 Glycine transporter 2 89.81% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.27% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.76% 96.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.44% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.94% 89.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.52% 90.71%

Plants that contains it

Top
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.
Chrysojasminum humile
Coccinia grandis
Euonymus atropurpureus
Festuca versuta
Neolitsea zeylanica
Rhus chinensis

Cross-Links

Top
PubChem 16655065
NPASS NPC138613
LOTUS LTS0047028
wikiData Q27134849