Leucosceptoside A

Details

• Internal ID: 184e9ce6-6bf0-4424-a881-b97abdfcf830
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)OC)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)OC)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C30H38O15/c1-14-23(36)24(37)25(38)30(42-14)45-28-26(39)29(41-10-9-16-3-6-17(32)19(34)11-16)43-21(13-31)27(28)44-22(35)8-5-15-4-7-18(33)20(12-15)40-2/h3-8,11-12,14,21,23-34,36-39H,9-10,13H2,1-2H3/b8-5+/t14-,21+,23-,24+,25+,26+,27+,28+,29+,30-/m0/s1
• InChI Key: ZMYQRHSOVRDQDL-CPPDSBOHSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₅
• Molecular Weight: 638.60 g/mol
• Exact Mass: 638.22107050 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.71
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

• CHEMBL450121
• SCHEMBL2157078
• HY-N8018
• BDBM50250350
• AKOS040761981
• CS-0138982
• E88783
• 3,4-Dihydroxyphenethyl 3-O-(alpha-L-rhamnopyranosyl)-4-O-[3-(3-methoxy-4-hydroxyphenyl)acryloyl]-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7808	78.08%
Caco-2	-	0.9077	90.77%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7406	74.06%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8764	87.64%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8058	80.58%
P-glycoprotein inhibitior	-	0.5289	52.89%
P-glycoprotein substrate	-	0.5221	52.21%
CYP3A4 substrate	+	0.6683	66.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.8552	85.52%
CYP2C9 inhibition	-	0.7968	79.68%
CYP2C19 inhibition	-	0.8381	83.81%
CYP2D6 inhibition	-	0.8929	89.29%
CYP1A2 inhibition	-	0.8885	88.85%
CYP2C8 inhibition	+	0.7934	79.34%
CYP inhibitory promiscuity	-	0.6452	64.52%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7121	71.21%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9254	92.54%
Skin irritation	-	0.8430	84.30%
Skin corrosion	-	0.9583	95.83%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6574	65.74%
Micronuclear	-	0.6367	63.67%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8413	84.13%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.9640	96.40%
Acute Oral Toxicity (c)	III	0.7950	79.50%
Estrogen receptor binding	+	0.8294	82.94%
Androgen receptor binding	-	0.6773	67.73%
Thyroid receptor binding	+	0.5326	53.26%
Glucocorticoid receptor binding	+	0.6412	64.12%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7008	70.08%
Honey bee toxicity	-	0.6531	65.31%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.6850	68.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL299	P17252	Protein kinase C alpha	19000 nM	IC50	PMID: 9834166

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.76%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.01%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.49%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.82%	96.00%
CHEMBL3194	P02766	Transthyretin	94.75%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.59%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.57%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.10%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.37%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	89.18%	94.73%
CHEMBL2581	P07339	Cathepsin D	86.13%	98.95%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.64%	80.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.01%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	83.73%	91.49%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.32%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.90%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.18%	92.62%
CHEMBL4208	P20618	Proteasome component C5	81.18%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.10%	94.45%

Plants that contains it

• Acanthus ebracteatus
• Acanthus montanus
• Allium stipitatum
• Alstonia longifolia
• Angiopteris evecta
• Artemisia argentea
• Asphodeline damascena
• Brodiaea californica
• Buddleja davidii
• Campsis grandiflora
• Cyathula tomentosa
• Digitalis purpurea
• Echinostephia aculeata
• Eucalyptus kitsoniana
• Euphorbia antiquorum
• Exochorda racemosa subsp. giraldii
• Fernandoa adenophylla
• Firmiana simplex
• Hemionitis lemmonii
• Himantoglossum hircinum
• Kopsia arborea
• Lamium purpureum
• Lantana trifolia
• Leonurus persicus
• Lepidophorum repandum
• Marrubium alysson
• Marrubium velutinum
• Myristica malabarica
• Odontites vernus
• Pedicularis artselaeri
• Penstemon centranthifolius
• Penstemon crandallii
• Penstemon linarioides
• Phlomis armeniaca
• Plagiomnium cuspidatum
• Plantago asiatica
• Plantago depressa
• Plantago lanceolata
• Plectranthus lanuginosus
• Populus yunnanensis
• Rehmannia glutinosa
• Rhodanthe maryonii
• Rhododendron campylocarpum
• Sagina japonica
• Santisukia kerrii
• Scabiosa comosa
• Scapania aequiloba
• Scutellaria baicalensis
• Sideritis ozturkii
• Solanum dulcamara
• Spartium junceum
• Stachys lavandulifolia
• Toddalia asiatica
• Tynanthus panurensis
• Vachellia lasiopetala
• Verbena brasiliensis
• Volkameria inermis

Cross-Links

• PubChem: 10394343
• NPASS: NPC100998
• ChEMBL: CHEMBL450121
• LOTUS: LTS0138388
• wikiData: Q105379836