Mearnsitrin

Details

• Internal ID: 3b63ed98-9e95-443a-834d-3c6560705f0a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-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=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)OC)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)OC)O)O)O)O
• InChI: InChI=1S/C22H22O12/c1-7-15(27)17(29)18(30)22(32-7)34-21-16(28)14-10(24)5-9(23)6-13(14)33-19(21)8-3-11(25)20(31-2)12(26)4-8/h3-7,15,17-18,22-27,29-30H,1-2H3/t7-,15-,17+,18+,22-/m0/s1
• InChI Key: NAQNISJXKDSYJD-DHWIRCOFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₂
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.11112613 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.50
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• 30484-88-9
• 2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• CHEMBL3109438
• Mearncitrin
• Mearnsetin 3-rhamnoside; Myricetin 4'-methyl ether-3-O-rhamnoside
• MEGxp0_000937
• ACon1_001228
• CHEBI:167827
• DTXSID301318239
• BDBM50446574
• AKOS032962125
• Mearnsitrin, >=95% (LC/MS-ELSD)
• NCGC00169555-01
• BRD-K00587908-001-01-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7980	79.80%
Caco-2	-	0.7885	78.85%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6676	66.76%
OATP2B1 inhibitior	-	0.5503	55.03%
OATP1B1 inhibitior	+	0.9055	90.55%
OATP1B3 inhibitior	+	0.9220	92.20%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7581	75.81%
P-glycoprotein inhibitior	-	0.5053	50.53%
P-glycoprotein substrate	-	0.5936	59.36%
CYP3A4 substrate	+	0.6116	61.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.6056	60.56%
CYP2C9 inhibition	-	0.9236	92.36%
CYP2C19 inhibition	-	0.8201	82.01%
CYP2D6 inhibition	-	0.8906	89.06%
CYP1A2 inhibition	-	0.7268	72.68%
CYP2C8 inhibition	+	0.7406	74.06%
CYP inhibitory promiscuity	-	0.5508	55.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6071	60.71%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.8321	83.21%
Skin irritation	-	0.6906	69.06%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	+	0.5663	56.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5654	56.54%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.5197	51.97%
skin sensitisation	-	0.9206	92.06%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7954	79.54%
Acute Oral Toxicity (c)	III	0.4825	48.25%
Estrogen receptor binding	+	0.7392	73.92%
Androgen receptor binding	+	0.5348	53.48%
Thyroid receptor binding	+	0.5479	54.79%
Glucocorticoid receptor binding	+	0.7339	73.39%
Aromatase binding	-	0.5175	51.75%
PPAR gamma	+	0.6410	64.10%
Honey bee toxicity	-	0.8060	80.60%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9150	91.50%

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	99.20%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.71%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.82%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.81%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.05%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.05%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.19%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.18%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.33%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.87%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.16%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	86.15%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.99%	99.23%
CHEMBL3194	P02766	Transthyretin	83.90%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.80%	97.36%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.35%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.31%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.05%	99.15%

Plants that contains it

• Byrsonima coccolobifolia
• Goniothalamus thwaitesii
• Mentha longifolia
• Myrcia multiflora
• Ribes alpinum
• Syzygium cumini
• Syzygium samarangense

Cross-Links

• PubChem: 6918652
• NPASS: NPC265530
• LOTUS: LTS0080920
• wikiData: Q105176475