Negundoside

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	29be9f99-7954-4129-bae0-fc9a35bb3fd6
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name	(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical)	CC1(CCC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)OC(=O)C4=CC=C(C=C4)O)O
SMILES (Isomeric)	C[C@@]1(CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)C4=CC=C(C=C4)O)O
InChI	InChI=1S/C23H28O12/c1-23(31)7-6-12-13(19(28)29)9-32-21(15(12)23)35-22-18(17(27)16(26)14(8-24)33-22)34-20(30)10-2-4-11(25)5-3-10/h2-5,9,12,14-18,21-22,24-27,31H,6-8H2,1H3,(H,28,29)/t12-,14-,15-,16-,17+,18-,21+,22+,23+/m1/s1
InChI Key	RFCSGMIUBXUYSE-KLZCBZFCSA-N
Popularity	5 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₃H₂₈O₁₂
Molecular Weight	496.50 g/mol
Exact Mass	496.15807632 g/mol
Topological Polar Surface Area (TPSA)	192.00 Å²
XlogP	-0.10
Atomic LogP (AlogP)	-0.52
H-Bond Acceptor	11
H-Bond Donor	6
Rotatable Bonds	6

Synonyms

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82451-20-5

78XBW51XWI

UNII-78XBW51XWI

NEGUNDOSIDE (USP-RS)

NEGUNDOSIDE [USP-RS]

(1S,4aS,7S,7aS)-1,4a,5,6,7,7a-Hexahydro-7-hydroxy-1-((2-O-(4-hydroxybenzoyl)-beta-D-glucopyranosyl)oxy)-7-methylcyclopenta(C)pyran-4-carboxylic acid

(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Cyclopenta(C)pyran-4-carboxylic acid, 1,4a,5,6,7,7a-hexahydro-7-hydroxy-1-((2-O-(4-hydroxybenzoyl)-beta-D-glucopyranosyl)oxy)-7-methyl-, (1S,4aS,7S,7aS)-

Cyclopenta(C)pyran-4-carboxylic acid, 1,4a,5,6,7,7a-hexahydro-7-hydroxy-1-((2-O-(4-hydroxybenzoyl)-beta-D-glucopyranosyl)oxy)-7-methyl-, (1S-(1alpha,4aalpha,7alpha,7aalpha))-

SCHEMBL381311

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8275	82.75%
Caco-2	-	0.8807	88.07%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7306	73.06%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	-	0.3359	33.59%
OATP1B3 inhibitior	+	0.9205	92.05%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7651	76.51%
BSEP inhibitior	-	0.7487	74.87%
P-glycoprotein inhibitior	-	0.6075	60.75%
P-glycoprotein substrate	-	0.6883	68.83%
CYP3A4 substrate	+	0.6705	67.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8794	87.94%
CYP3A4 inhibition	-	0.8426	84.26%
CYP2C9 inhibition	-	0.8157	81.57%
CYP2C19 inhibition	-	0.8532	85.32%
CYP2D6 inhibition	-	0.9025	90.25%
CYP1A2 inhibition	-	0.7887	78.87%
CYP2C8 inhibition	+	0.7481	74.81%
CYP inhibitory promiscuity	-	0.8459	84.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5793	57.93%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9317	93.17%
Skin irritation	-	0.6258	62.58%
Skin corrosion	-	0.9276	92.76%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4809	48.09%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7690	76.90%
skin sensitisation	-	0.8732	87.32%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.5572	55.72%
Acute Oral Toxicity (c)	I	0.4504	45.04%
Estrogen receptor binding	+	0.8194	81.94%
Androgen receptor binding	+	0.6312	63.12%
Thyroid receptor binding	+	0.6077	60.77%
Glucocorticoid receptor binding	+	0.6730	67.30%
Aromatase binding	+	0.5997	59.97%
PPAR gamma	+	0.6457	64.57%
Honey bee toxicity	-	0.8543	85.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6950	69.50%
Fish aquatic toxicity	+	0.9345	93.45%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	96.90%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.81%	97.09%
CHEMBL4208	P20618	Proteasome component C5	93.16%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.95%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	92.44%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.93%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.84%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.05%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	89.09%	91.49%
CHEMBL5255	O00206	Toll-like receptor 4	88.81%	92.50%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	88.17%	94.97%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.76%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.16%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.47%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.81%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.08%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.46%	99.17%
CHEMBL3194	P02766	Transthyretin	81.96%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.51%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.27%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.98%	91.19%
CHEMBL242	Q92731	Estrogen receptor beta	80.66%	98.35%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.41%	94.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.40%	95.83%
CHEMBL226	P30542	Adenosine A1 receptor	80.39%	95.93%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Delphinium campylocentrum

Disepalum plagioneurum

Eremophila serrulata

Grindelia hirsutula

Hakea salicifolia