Lychnopholide

Details

• Internal ID: 244cf4d9-632b-46e8-9611-defa5c486633
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(2Z,4R,8R,9S,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradeca-1(13),2-dien-9-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2(C(=O)C=C(O2)C(=CC3C1C(=C)C(=O)O3)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1C[C@@]2(C(=O)C=C(O2)/C(=C\[C@@H]3[C@@H]1C(=C)C(=O)O3)/C)C
• InChI: InChI=1S/C20H22O6/c1-6-10(2)18(22)25-15-9-20(5)16(21)8-13(26-20)11(3)7-14-17(15)12(4)19(23)24-14/h6-8,14-15,17H,4,9H2,1-3,5H3/b10-6-,11-7-/t14-,15+,17+,20-/m1/s1
• InChI Key: QATUWZPYBIHFFR-UVXIKMMUSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.14163842 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• (-)-Lychnopholide
• 77448-64-7
• NSC 669145
• 2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,6,7,11a-octahydro-6,10-dimethyl-3-methylene-2,7-dioxo-6,9-epoxycyclodeca(b)furan-4-yl ester, (3aR-(3aR*,4S*(Z),6R*,10Z,11aR*))-
• NSC669145
• 2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,6,7,11a-octahydro-6,10-dimethyl-3-methylene-2,7-dioxo-6,9-epoxycyclodeca[b]furan-4-yl ester, [3aR-[3aR*,4S*(Z),6R*,10Z,11aR*]]-
• CHEMBL4476580
• DTXSID401317753
• AKOS040752796
• (dimethyl-methylene-dioxo-[?]yl) (Z)-2-methylbut-2-enoate
• [(2Z,4R,8R,9S,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradeca-1(13),2-dien-9-yl] (Z)-2-methylbut-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9871	98.71%
Caco-2	+	0.7130	71.30%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8603	86.03%
OATP1B3 inhibitior	+	0.8450	84.50%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5751	57.51%
P-glycoprotein inhibitior	+	0.6290	62.90%
P-glycoprotein substrate	-	0.6059	60.59%
CYP3A4 substrate	+	0.6594	65.94%
CYP2C9 substrate	-	0.8070	80.70%
CYP2D6 substrate	-	0.8986	89.86%
CYP3A4 inhibition	-	0.5881	58.81%
CYP2C9 inhibition	-	0.9074	90.74%
CYP2C19 inhibition	-	0.8781	87.81%
CYP2D6 inhibition	-	0.9441	94.41%
CYP1A2 inhibition	-	0.7551	75.51%
CYP2C8 inhibition	-	0.6801	68.01%
CYP inhibitory promiscuity	-	0.8600	86.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8643	86.43%
Carcinogenicity (trinary)	Non-required	0.3704	37.04%
Eye corrosion	-	0.9485	94.85%
Eye irritation	-	0.7491	74.91%
Skin irritation	-	0.6637	66.37%
Skin corrosion	-	0.9123	91.23%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7391	73.91%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.6585	65.85%
skin sensitisation	-	0.6009	60.09%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6830	68.30%
Acute Oral Toxicity (c)	III	0.4364	43.64%
Estrogen receptor binding	+	0.7669	76.69%
Androgen receptor binding	+	0.6378	63.78%
Thyroid receptor binding	+	0.6418	64.18%
Glucocorticoid receptor binding	-	0.4768	47.68%
Aromatase binding	-	0.7043	70.43%
PPAR gamma	+	0.6097	60.97%
Honey bee toxicity	-	0.6316	63.16%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9537	95.37%

Targets

Proven Targets:

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	98.34%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.65%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.70%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.91%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.50%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.58%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.63%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.64%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.32%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.26%	95.89%
CHEMBL2581	P07339	Cathepsin D	81.85%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.27%	100.00%

Plants that contains it

• Aucklandia costus
• Crateva magna
• Eremanthus erythropappus
• Lychnophora ericoides
• Lychnophora pohlii
• Lychnophora pseudovillosissima
• Lychnophora rupestris
• Melaleuca cuticularis
• Piptocoma rufescens
• Vachellia pennatula
• Vepris gabonensis

Cross-Links

• PubChem: 49767028
• NPASS: NPC16906
• LOTUS: LTS0060501
• wikiData: Q104250534