Clitorin

Details

• Internal ID: 86821b9e-498e-477a-97ff-28cbb4354c8e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-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)OC6C(C(C(C(O6)C)O)O)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)O[C@H]6[C@@H]([C@@H]([C@H]([C@@H](O6)C)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C33H40O19/c1-10-19(37)23(41)26(44)31(47-10)46-9-17-21(39)25(43)30(52-32-27(45)24(42)20(38)11(2)48-32)33(50-17)51-29-22(40)18-15(36)7-14(35)8-16(18)49-28(29)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-27,30-39,41-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21+,23+,24+,25-,26+,27+,30+,31+,32-,33-/m0/s1
• InChI Key: WRXVPTMENPZUIZ-QEZWUOJGSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₉
• Molecular Weight: 740.70 g/mol
• Exact Mass: 740.21637904 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.54
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 8

Synonyms

• 55804-74-5
• 3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SCHEMBL18167030
• HY-N7005
• AKOS040760340
• MS-31285
• CS-0027865

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4659	46.59%
Caco-2	-	0.9147	91.47%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7552	75.52%
OATP2B1 inhibitior	-	0.7109	71.09%
OATP1B1 inhibitior	+	0.8773	87.73%
OATP1B3 inhibitior	+	0.9107	91.07%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8185	81.85%
P-glycoprotein inhibitior	-	0.5475	54.75%
P-glycoprotein substrate	+	0.5973	59.73%
CYP3A4 substrate	+	0.6598	65.98%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.8904	89.04%
CYP2C9 inhibition	-	0.9134	91.34%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.8713	87.13%
CYP2C8 inhibition	+	0.8284	82.84%
CYP inhibitory promiscuity	-	0.6602	66.02%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7067	70.67%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9113	91.13%
Skin irritation	-	0.8277	82.77%
Skin corrosion	-	0.9610	96.10%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6452	64.52%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.9381	93.81%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.9021	90.21%
Acute Oral Toxicity (c)	III	0.6245	62.45%
Estrogen receptor binding	+	0.8180	81.80%
Androgen receptor binding	+	0.6465	64.65%
Thyroid receptor binding	+	0.5491	54.91%
Glucocorticoid receptor binding	+	0.5541	55.41%
Aromatase binding	+	0.5933	59.33%
PPAR gamma	+	0.7325	73.25%
Honey bee toxicity	-	0.7412	74.12%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5050	50.50%
Fish aquatic toxicity	+	0.9179	91.79%

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	99.39%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.24%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.80%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.63%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.39%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.23%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.15%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	94.25%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.60%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.58%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.67%	95.56%
CHEMBL3194	P02766	Transthyretin	85.61%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.00%	97.36%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.38%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.26%	95.78%
CHEMBL242	Q92731	Estrogen receptor beta	82.41%	98.35%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.23%	95.89%
CHEMBL4208	P20618	Proteasome component C5	81.08%	90.00%

Plants that contains it

• Acalypha indica
• Alangium platanifolium
• Albizia altissima
• Albizia inundata
• Anthocleista grandiflora
• Artocarpus altilis
• Centaurea solstitialis
• Chamaemelum nobile
• Chenopodium album
• Clitoria ternatea
• Cosmos diversifolius
• Cryptocarya oblata
• Curcuma caesia
• Diospyros rhombifolia
• Erythrina pallida
• Eucalyptus radiata subsp. radiata
• Garrya elliptica
• Glinus lotoides
• Helleborus orientalis
• Hypoestes serpens
• Inga velutina
• Lactuca serriola
• Lagochilus leiacanthus
• Lespedeza homoloba
• Lolium perenne
• Nassauvia cumingii
• Ocimum africanum
• Onobrychis cyri
• Onobrychis viciifolia
• Oxalis purpurea
• Phelline lucida
• Picradeniopsis multiflora
• Piptostigma fugax
• Primula farinosa
• Rhododendron mucronatum
• Saxifraga cuneifolia
• Strychnos tricalysioides
• Tipuana tipu
• Trichodesma incanum
• Urochloa eminii
• Xanthorrhoea resinosa

Cross-Links

• PubChem: 11592917
• NPASS: NPC12323
• LOTUS: LTS0188568
• wikiData: Q104399482