Baohuoside I

Details

• Internal ID: ae5e182a-d2e0-4b58-be7f-5d035a6fe701
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C(=CC(=C3C2=O)O)O)CC=C(C)C)C4=CC=C(C=C4)OC)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C(=CC(=C3C2=O)O)O)CC=C(C)C)C4=CC=C(C=C4)OC)O)O)O
• InChI: InChI=1S/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1
• InChI Key: NGMYNFJANBHLKA-LVKFHIPRSA-N
• Popularity: 154 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₀
• Molecular Weight: 514.50 g/mol
• Exact Mass: 514.18389715 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 113558-15-9
• Icariside II
• Icarlin II
• BAOHUOSIDEI
• CHEBI:82619
• 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• CHEMBL560116
• 3,5,7-Trihydroxy-4'-methoxyl-8-prenylflavone-3-O-rhamnopyranoside
• Icariin-II;Icariside-II
• Baohuoside-I
• Icariside-II
• Icariin-II
• AMY496
• SCHEMBL4229321
• GTPL10686
• DTXSID40150457
• 2h44
• EX-A6795
• HY-N0011
• BDBM50503751
• AKOS037514560
• CS-3673
• 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-
• AC-33977
• AS-75062
• anhydroicaritin-3-O-alpha-L-rhamnopyranoside
• Baohuoside I; Anhydroicaritin; Icariside II
• A894345
• Q-100071
• Q27156136
• 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone-3-O-rhamnopyranoside
• 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone-3-O-alpha-L-rhamnopyranoside
• 3,5,7-Trihydroxy-4'-methoxyl-8-prenylflavone-3-O-rhamnopyranoside; 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-; 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranosideohuside I; Icariin II; Icariside II
• 4H-1-Benzopyran-4-one, 3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-
• 5,7-Dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one
• 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9486	94.86%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5770	57.70%
OATP2B1 inhibitior	-	0.5643	56.43%
OATP1B1 inhibitior	+	0.9078	90.78%
OATP1B3 inhibitior	+	0.8170	81.70%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8593	85.93%
P-glycoprotein inhibitior	+	0.7193	71.93%
P-glycoprotein substrate	-	0.5743	57.43%
CYP3A4 substrate	+	0.6261	62.61%
CYP2C9 substrate	-	0.6946	69.46%
CYP2D6 substrate	-	0.8431	84.31%
CYP3A4 inhibition	-	0.8789	87.89%
CYP2C9 inhibition	+	0.5388	53.88%
CYP2C19 inhibition	+	0.6785	67.85%
CYP2D6 inhibition	-	0.7926	79.26%
CYP1A2 inhibition	-	0.8168	81.68%
CYP2C8 inhibition	+	0.6481	64.81%
CYP inhibitory promiscuity	+	0.6630	66.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6053	60.53%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.8982	89.82%
Skin irritation	-	0.7547	75.47%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.5074	50.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.5718	57.18%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.5323	53.23%
skin sensitisation	-	0.8435	84.35%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8346	83.46%
Acute Oral Toxicity (c)	III	0.6149	61.49%
Estrogen receptor binding	+	0.8555	85.55%
Androgen receptor binding	+	0.7638	76.38%
Thyroid receptor binding	+	0.6068	60.68%
Glucocorticoid receptor binding	+	0.7804	78.04%
Aromatase binding	+	0.6318	63.18%
PPAR gamma	+	0.6925	69.25%
Honey bee toxicity	-	0.7810	78.10%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9916	99.16%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1827	O76074	Phosphodiesterase 5A	160 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.81%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.19%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.49%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.42%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.95%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	94.66%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.29%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.26%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.61%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.88%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.93%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.23%	94.45%
CHEMBL4208	P20618	Proteasome component C5	86.08%	90.00%
CHEMBL240	Q12809	HERG	85.49%	89.76%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.10%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.51%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.47%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.73%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.48%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.26%	92.62%

Plants that contains it

• Acer carpinifolium
• Anemarrhena asphodeloides
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium acuminatum
• Epimedium brevicornu
• Epimedium diphyllum
• Epimedium grandiflorum
• Epimedium hunanense
• Epimedium koreanum
• Epimedium pubescens
• Epimedium sagittatum
• Epimedium sempervirens
• Epimedium wushanense
• Galium rubioides
• Helichrysum lepidissimum
• Helleborus multifidus
• Hopea utilis
• Hypericum revolutum
• Leuzea centauroides
• Litsea salicifolia
• Mesembryanthemum expansum
• Osmorhiza aristata
• Psychotria serpens
• Pycnandra acuminata
• Stipa robusta
• Succisa pratensis

Cross-Links

• PubChem: 5488822
• NPASS: NPC278419
• LOTUS: LTS0252690
• wikiData: Q27156136