Narcissin

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	6cd34671-41e7-4c58-82d4-60df4f9b12d5
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
IUPAC Name	5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
SMILES (Canonical)	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O
SMILES (Isomeric)	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O
InChI	InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16+,18-,19+,21+,22-,23+,24+,27+,28-/m0/s1
InChI Key	UIDGLYUNOUKLBM-GEBJFKNCSA-N
Popularity	274 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₈H₃₂O₁₆
Molecular Weight	624.50 g/mol
Exact Mass	624.16903493 g/mol
Topological Polar Surface Area (TPSA)	255.00 Å²
XlogP	-1.00
Atomic LogP (AlogP)	-1.38
H-Bond Acceptor	16
H-Bond Donor	9
Rotatable Bonds	7

Synonyms

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604-80-8

Narcissin

Narcissin Flavonol

Isorhamnetin 3-rhamnoglucoside

N4AX11L1TF

DTXSID00209157

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl)oxan-2-yl)oxychromen-4-one

RefChem:42644

DTXCID20131648

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	-	0.4777	47.77%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6902	69.02%
OATP2B1 inhibitior	-	0.5772	57.72%
OATP1B1 inhibitior	+	0.8990	89.90%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6263	62.63%
P-glycoprotein inhibitior	-	0.5762	57.62%
P-glycoprotein substrate	+	0.5892	58.92%
CYP3A4 substrate	+	0.6383	63.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.8619	86.19%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.8713	87.13%
CYP inhibitory promiscuity	-	0.6670	66.70%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6995	69.95%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9056	90.56%
Skin irritation	-	0.8249	82.49%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.6328	63.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4684	46.84%
Micronuclear	+	0.7492	74.92%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9436	94.36%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.9093	90.93%
Acute Oral Toxicity (c)	III	0.6904	69.04%
Estrogen receptor binding	+	0.8205	82.05%
Androgen receptor binding	+	0.5477	54.77%
Thyroid receptor binding	+	0.5215	52.15%
Glucocorticoid receptor binding	+	0.6600	66.00%
Aromatase binding	+	0.6062	60.62%
PPAR gamma	+	0.7100	71.00%
Honey bee toxicity	-	0.7729	77.29%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.8477	84.77%

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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.25%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.34%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.80%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.58%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.92%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.40%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.55%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.30%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	90.01%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.53%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	88.31%	91.49%
CHEMBL3194	P02766	Transthyretin	87.04%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.67%	95.64%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.18%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.25%	85.14%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.73%	95.78%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.43%	96.00%
CHEMBL4208	P20618	Proteasome component C5	82.11%	90.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.16%	94.03%

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.

Anaxagorea dolichocarpa

Aristolochia kaempferi

Artocarpus altilis

Astragalus dasyanthus

Astragalus icmadophilus

Astragalus sevangensis

Baccharis sagittalis