Shanzhiside-methylester

Details

• Internal ID: 4c2d9c5a-cc92-4e79-88c5-82d1bf183c0c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,5R,7S)-5,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@]1(C[C@H](C2C1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
• InChI: InChI=1S/C17H26O11/c1-17(24)3-7(19)9-6(14(23)25-2)5-26-15(10(9)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5,7-13,15-16,18-22,24H,3-4H2,1-2H3/t7-,8-,9?,10?,11-,12+,13-,15+,16+,17+/m1/s1
• InChI Key: KKSYAZCUYVRKML-QDXNKOLPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₁₁
• Molecular Weight: 406.40 g/mol
• Exact Mass: 406.14751164 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -3.04
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• Shanziside methyl ester
• Shanzhizide methyl ester
• Shanzhiside-methylester
• DTXSID20982995
• Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5,7-dihydroxy-7-methyl-, methyl ester, (1S-(1alpha,4aalpha,5alpha,7alpha,7aalpha))-
• Methyl 1-(hexopyranosyloxy)-5,7-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6977	69.77%
Caco-2	-	0.8519	85.19%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6306	63.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7842	78.42%
OATP1B3 inhibitior	+	0.9420	94.20%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9301	93.01%
P-glycoprotein inhibitior	-	0.8548	85.48%
P-glycoprotein substrate	-	0.7689	76.89%
CYP3A4 substrate	+	0.6459	64.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8720	87.20%
CYP3A4 inhibition	-	0.9033	90.33%
CYP2C9 inhibition	-	0.9185	91.85%
CYP2C19 inhibition	-	0.8937	89.37%
CYP2D6 inhibition	-	0.9031	90.31%
CYP1A2 inhibition	-	0.9074	90.74%
CYP2C8 inhibition	-	0.7395	73.95%
CYP inhibitory promiscuity	-	0.8673	86.73%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6463	64.63%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9693	96.93%
Skin irritation	-	0.7188	71.88%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	+	0.5063	50.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5880	58.80%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.8223	82.23%
skin sensitisation	-	0.8584	85.84%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5813	58.13%
Acute Oral Toxicity (c)	III	0.4318	43.18%
Estrogen receptor binding	+	0.5663	56.63%
Androgen receptor binding	-	0.5360	53.60%
Thyroid receptor binding	-	0.5762	57.62%
Glucocorticoid receptor binding	-	0.6303	63.03%
Aromatase binding	-	0.5377	53.77%
PPAR gamma	-	0.5595	55.95%
Honey bee toxicity	-	0.8211	82.11%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.4512	45.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.20%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.02%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.99%	85.14%
CHEMBL4208	P20618	Proteasome component C5	91.90%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.82%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.18%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	83.89%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.97%	96.61%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.59%	96.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.30%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.17%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	81.25%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.22%	89.00%

Plants that contains it

• Barleria lupulina
• Barleria prionitis
• Castilleja integra
• Castilleja miniata
• Castilleja purpurea
• Castilleja sulphurea
• Cordiera macrophylla
• Gardenia jasminoides
• Lamium amplexicaule
• Lamium purpureum
• Lippia alba
• Mussaenda pubescens
• Mussaenda shikokiana
• Odontites vernus
• Parentucellia viscosa
• Pedicularis artselaeri
• Pedicularis condensata
• Pedicularis grayi
• Pedicularis palustris
• Pedicularis spicata
• Pedicularis torta
• Phlomis rigida
• Phlomis spinidens
• Phlomoides betonicoides
• Phlomoides rotata
• Phlomoides tuberosa
• Phlomoides umbrosa
• Phlomoides younghusbandii
• Psydrax subcordatus
• Salvia digitaloides
• Sesamum alatum
• Veronica anagallis-aquatica

Cross-Links

• PubChem: 3085296
• NPASS: NPC110822
• LOTUS: LTS0218420
• wikiData: Q72507460