Baohuoside II

Details

• Internal ID: ca6d41ff-544a-4c53-95d9-69e2e1f35f49
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-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)O)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)O)O)O)O
• InChI: InChI=1S/C26H28O10/c1-11(2)4-9-15-16(28)10-17(29)18-20(31)25(36-26-22(33)21(32)19(30)12(3)34-26)23(35-24(15)18)13-5-7-14(27)8-6-13/h4-8,10,12,19,21-22,26-30,32-33H,9H2,1-3H3/t12-,19-,21+,22+,26-/m0/s1
• InChI Key: RPLMLWBOUPDPQF-GULSFEPBSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₀
• Molecular Weight: 500.50 g/mol
• Exact Mass: 500.16824709 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• Ikarisoside A
• 55395-07-8
• C26H28O10
• MLS000697625
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMR000470956
• 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mennopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-
• CHEMBL1728934
• BDBM78941
• cid_5481982
• DTXSID70203945
• HMS2271C12
• HY-N0875
• AKOS037514893
• CS-3692
• NCGC00247526-01
• MS-29289
• 2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-5,7-bis(oxidanyl)chromen-4-one
• 5,7-Dihydroxy-2-(4-hydroxyphenyl)-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-hydroxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromone
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-3-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-2-oxanyl]oxy]-1-benzopyran-4-one
• 8-((2E)-3-Methylbut-2-enyl)-3-((2S,6S,3R,4R,5R)-3,4,5-trihydroxy-6-methylperhydropyran-2-yloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9516	95.16%
Caco-2	-	0.8930	89.30%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6451	64.51%
OATP2B1 inhibitior	+	0.5799	57.99%
OATP1B1 inhibitior	+	0.9011	90.11%
OATP1B3 inhibitior	+	0.8008	80.08%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8670	86.70%
P-glycoprotein inhibitior	+	0.6786	67.86%
P-glycoprotein substrate	-	0.5536	55.36%
CYP3A4 substrate	+	0.6113	61.13%
CYP2C9 substrate	-	0.6645	66.45%
CYP2D6 substrate	-	0.8507	85.07%
CYP3A4 inhibition	-	0.8852	88.52%
CYP2C9 inhibition	+	0.6270	62.70%
CYP2C19 inhibition	+	0.6621	66.21%
CYP2D6 inhibition	-	0.8466	84.66%
CYP1A2 inhibition	-	0.7942	79.42%
CYP2C8 inhibition	+	0.7358	73.58%
CYP inhibitory promiscuity	+	0.7001	70.01%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6253	62.53%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.8749	87.49%
Skin irritation	-	0.7462	74.62%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.5174	51.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.6089	60.89%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8107	81.07%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7417	74.17%
Acute Oral Toxicity (c)	III	0.6000	60.00%
Estrogen receptor binding	+	0.8231	82.31%
Androgen receptor binding	+	0.7642	76.42%
Thyroid receptor binding	+	0.5567	55.67%
Glucocorticoid receptor binding	+	0.7537	75.37%
Aromatase binding	+	0.6364	63.64%
PPAR gamma	+	0.7143	71.43%
Honey bee toxicity	-	0.7459	74.59%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9958	99.58%

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	99.61%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.64%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.42%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.06%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	96.04%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.36%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.51%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.67%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.07%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.39%	94.45%
CHEMBL3038469	P24941	CDK2/Cyclin A	87.57%	91.38%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.89%	91.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.70%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.62%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.99%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.52%	95.89%

Plants that contains it

• Acer carpinifolium
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium brevicornu
• Epimedium diphyllum
• Epimedium grandiflorum
• 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: 5481982
• NPASS: NPC66087
• LOTUS: LTS0011650
• wikiData: Q72444771