Skimmin

Details

• Internal ID: ce61d5ca-04cd-42f4-9cf8-dee3e013a46c
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): C1=CC(=CC2=C1C=CC(=O)O2)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=CC(=CC2=C1C=CC(=O)O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C15H16O8/c16-6-10-12(18)13(19)14(20)15(23-10)21-8-3-1-7-2-4-11(17)22-9(7)5-8/h1-5,10,12-16,18-20H,6H2/t10-,12-,13+,14-,15-/m1/s1
• InChI Key: VPAOSFFTKWUGAD-TVKJYDDYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₈
• Molecular Weight: 324.28 g/mol
• Exact Mass: 324.08451746 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.03
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 93-39-0
• 7-Hydroxycoumarin glucoside
• Skimmine
• UMBELLIFERONE GLUCOSIDE
• UNII-H072F03PQN
• H072F03PQN
• 7-Hydroxycoumarin-7-glucoside
• Umbelliferone, beta-D-glucopyranoside
• 7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• NSC 267696
• Glucopyranoside, umbelliferone, beta-D-
• Coumarin, 7-(beta-D-glucopyranosyloxy)-
• C15H16O8
• 7-(glucosyloxy)coumarin
• C15-H16-O8
• NSC-267696
• SKIMIN
• SKIMMIN [MI]
• 7-(beta-D-Glucopyranosyloxy)-2H-1-benzopyran-2-one
• 2H-1-Benzopyran-2-one, 7-(.beta.-D-glucopyranosyloxy)-
• SKIMMIN, (-)-
• CHEMBL526377
• SCHEMBL1944336
• CHEBI:177698
• DTXSID201018989
• HY-N2263
• Skimmin, >=90% (LC/MS-UV)
• MFCD00017710
• s9254
• AKOS000277094
• CCG-267743
• COUMARIN 7-O-.BETA.-D-GLUCOSIDE
• AC-35014
• AS-83344
• CS-0019592
• A859802
• UMBELLIFERONE 7-O-.BETA.-D-GLUCOPYRANOSIDE
• Q-100893
• Q15114711
• 2H-1-Benzopyran-2-one, 7-(beta-D-glucopyranosyloxy)-
• 7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
• 7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2H-chromen-2-one
• 7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2H-chromen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6367	63.67%
Caco-2	-	0.8035	80.35%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5792	57.92%
OATP2B1 inhibitior	-	0.8491	84.91%
OATP1B1 inhibitior	+	0.8640	86.40%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8582	85.82%
P-glycoprotein inhibitior	-	0.9316	93.16%
P-glycoprotein substrate	-	0.9556	95.56%
CYP3A4 substrate	-	0.5387	53.87%
CYP2C9 substrate	-	0.8219	82.19%
CYP2D6 substrate	-	0.8584	85.84%
CYP3A4 inhibition	-	0.9271	92.71%
CYP2C9 inhibition	-	0.9542	95.42%
CYP2C19 inhibition	-	0.9292	92.92%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	-	0.9202	92.02%
CYP2C8 inhibition	-	0.8373	83.73%
CYP inhibitory promiscuity	-	0.8566	85.66%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6617	66.17%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.7912	79.12%
Skin irritation	-	0.8079	80.79%
Skin corrosion	-	0.9743	97.43%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.9024	90.24%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7455	74.55%
Acute Oral Toxicity (c)	III	0.4845	48.45%
Estrogen receptor binding	-	0.5825	58.25%
Androgen receptor binding	+	0.5498	54.98%
Thyroid receptor binding	-	0.5772	57.72%
Glucocorticoid receptor binding	+	0.6314	63.14%
Aromatase binding	+	0.6065	60.65%
PPAR gamma	+	0.6153	61.53%
Honey bee toxicity	-	0.8261	82.61%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6950	69.50%
Fish aquatic toxicity	+	0.7264	72.64%

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	98.26%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	93.95%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.79%	94.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.54%	83.57%
CHEMBL2581	P07339	Cathepsin D	89.89%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.88%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.84%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.99%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.14%	94.73%
CHEMBL4208	P20618	Proteasome component C5	83.86%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.65%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	82.12%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.89%	96.00%

Plants that contains it

• Aframomum daniellii
• Alchornea cordifolia
• Angelica dahurica
• Artemisia ordosica
• Astragalus brachycarpus
• Atalantia wightii
• Balanophora japonica
• Corydalis persica
• Corynanthe pachyceras
• Cota tinctoria
• Cynoglossum amabile
• Daphne feddei
• Eucalyptus viminalis
• Glehnia littoralis
• Glycosmis pseudoracemosa
• Hydrangea macrophylla
• Iphiona grantioides
• Ipomoea nil
• Juniperus horizontalis
• Juniperus phoenicea
• Kitagawia praeruptora
• Lathyrus tingitanus
• Morus alba
• Phellodendron amurense
• Picea neoveitchii
• Plectranthus caninus
• Rauvolfia salicifolia
• Rhodiola heterodonta
• Saussurea hieracioides
• Skimmia japonica
• Skimmia reevesiana
• Solanum aculeatissimum
• Stellera chamaejasme
• Strychnos spinosa
• Tetradium glabrifolium

Cross-Links

• PubChem: 99693
• NPASS: NPC103409
• LOTUS: LTS0063676
• wikiData: Q15114711