Stachysoside A

Details

• Internal ID: 26af7edc-c580-44cc-8517-f5845f0002ca
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides
• IUPAC Name: [(2R,3R,4R,5R,6R)-4-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)OC5C(C(C(CO5)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)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O[C@H]5[C@@H]([C@H]([C@H](CO5)O)O)O)O)O
• InChI: InChI=1S/C34H44O19/c1-14-24(42)26(44)31(53-32-27(45)25(43)21(40)13-48-32)34(49-14)52-30-28(46)33(47-9-8-16-3-6-18(37)20(39)11-16)50-22(12-35)29(30)51-23(41)7-4-15-2-5-17(36)19(38)10-15/h2-7,10-11,14,21-22,24-40,42-46H,8-9,12-13H2,1H3/b7-4+/t14-,21-,22+,24-,25-,26+,27+,28+,29+,30+,31+,32-,33+,34-/m0/s1
• InChI Key: UDHCHDJLZGYDDM-LVDCRSFESA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₄O₁₉
• Molecular Weight: 756.70 g/mol
• Exact Mass: 756.24767917 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.55
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 12

Synonyms

• lavandulifolioside
• [(2R,3R,4R,5R,6R)-4-[(2S,3R,4R,5R,6S)-4,5-Dihydroxy-6-methyl-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CHEBI:169606

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7025	70.25%
Caco-2	-	0.8992	89.92%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7309	73.09%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.8745	87.45%
OATP1B3 inhibitior	+	0.9547	95.47%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8347	83.47%
P-glycoprotein inhibitior	-	0.4663	46.63%
P-glycoprotein substrate	+	0.5298	52.98%
CYP3A4 substrate	+	0.6887	68.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9168	91.68%
CYP2C9 inhibition	-	0.8684	86.84%
CYP2C19 inhibition	-	0.9206	92.06%
CYP2D6 inhibition	-	0.9026	90.26%
CYP1A2 inhibition	-	0.8912	89.12%
CYP2C8 inhibition	+	0.6921	69.21%
CYP inhibitory promiscuity	-	0.8468	84.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6875	68.75%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9125	91.25%
Skin irritation	-	0.8244	82.44%
Skin corrosion	-	0.9526	95.26%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7793	77.93%
Micronuclear	-	0.6567	65.67%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8397	83.97%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9842	98.42%
Acute Oral Toxicity (c)	III	0.7951	79.51%
Estrogen receptor binding	+	0.8017	80.17%
Androgen receptor binding	-	0.7674	76.74%
Thyroid receptor binding	+	0.5293	52.93%
Glucocorticoid receptor binding	+	0.5781	57.81%
Aromatase binding	+	0.5324	53.24%
PPAR gamma	+	0.7250	72.50%
Honey bee toxicity	-	0.6602	66.02%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.7225	72.25%

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	99.85%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.15%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.10%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.59%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.26%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.26%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.89%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.60%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	91.02%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.78%	97.36%
CHEMBL3194	P02766	Transthyretin	90.12%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.95%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	88.91%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.26%	97.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.43%	80.78%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	84.27%	96.37%
CHEMBL4208	P20618	Proteasome component C5	84.13%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.15%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.94%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.08%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.87%	91.71%

Plants that contains it

• Ajuga salicifolia
• Asystasia gangetica subsp. micrantha
• Ballota nigra
• Campylanthus glaber
• Leonotis nepetifolia
• Leonurus cardiaca
• Leonurus glaucescens
• Leonurus japonicus
• Marrubium velutinum
• Plantago lanceolata
• Scrophularia buergeriana
• Scrophularia ningpoensis
• Sideritis lyciae
• Sideritis perfoliata
• Stachys byzantina
• Stachys lavandulifolia
• Stachys riederi
• Veronica persica

Cross-Links

• PubChem: 14034195
• NPASS: NPC207306
• LOTUS: LTS0001896
• wikiData: Q104667393