Spinosin

Details

• Internal ID: b0b9efac-aa0c-443e-a2b5-8f28d1e9d25d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C28H32O15/c1-39-14-7-15-18(12(32)6-13(40-15)10-2-4-11(31)5-3-10)22(35)19(14)26-27(24(37)21(34)16(8-29)41-26)43-28-25(38)23(36)20(33)17(9-30)42-28/h2-7,16-17,20-21,23-31,33-38H,8-9H2,1H3/t16-,17-,20-,21-,23+,24+,25-,26+,27-,28+/m1/s1
• InChI Key: VGGSULWDCMWZPO-ODEMIOGVSA-N
• Popularity: 40 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₅
• Molecular Weight: 608.50 g/mol
• Exact Mass: 608.17412031 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.78
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

• 72063-39-9
• flavoayamenin
• 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• 6-(2-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
• 2''-O-glycosylswertisin
• SCHEMBL2980651
• CHEBI:81360
• DTXSID50222396
• HMS3886F18
• HY-N0651
• MFCD09754430
• s9134
• AKOS015897169
• CCG-270216
• AC-31296
• BS-17968
• LS-193896
• CS-0009676
• P2887
• C17834
• A866326
• Q-100793
• Q27155298
• (1S)-1,5-anhydro-2-O-beta-D-glucopyranosyl-1-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-6-yl]-D-glucitol
• 4H-1-Benzopyran-4-one, 6-(2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-
• 6-((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.9105	91.05%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.5745	57.45%
OATP1B1 inhibitior	+	0.7928	79.28%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6250	62.50%
P-glycoprotein inhibitior	-	0.6497	64.97%
P-glycoprotein substrate	-	0.5544	55.44%
CYP3A4 substrate	+	0.6532	65.32%
CYP2C9 substrate	-	0.8389	83.89%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.7515	75.15%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9208	92.08%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5199	51.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.4308	43.08%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8980	89.80%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8085	80.85%
Androgen receptor binding	+	0.7813	78.13%
Thyroid receptor binding	+	0.5461	54.61%
Glucocorticoid receptor binding	+	0.6084	60.84%
Aromatase binding	+	0.6401	64.01%
PPAR gamma	+	0.7592	75.92%
Honey bee toxicity	-	0.6944	69.44%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.6698	66.98%

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	99.42%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.29%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.09%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.91%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.90%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.09%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.63%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.28%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.05%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	84.79%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.68%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.10%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.91%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.15%	96.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.08%	83.57%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.50%	97.14%
CHEMBL220	P22303	Acetylcholinesterase	80.45%	94.45%

Plants that contains it

• Clutia abyssinica
• Desmodium tortuosum
• Galipea trifoliata
• Wilbrandia ebracteata
• Ziziphus jujuba
• Ziziphus jujuba var. spinosa

Cross-Links

• PubChem: 155692
• NPASS: NPC34995
• LOTUS: LTS0075106
• wikiData: Q27155298