Nodakenin

Details

• Internal ID: d38dfeb6-5f58-442c-b05f-b60846c15c09
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: (2R)-2-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-2,3-dihydrofuro[3,2-g]chromen-7-one
• SMILES (Canonical): CC(C)(C1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): CC(C)([C@H]1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C20H24O9/c1-20(2,29-19-18(25)17(24)16(23)13(8-21)28-19)14-6-10-5-9-3-4-15(22)27-11(9)7-12(10)26-14/h3-5,7,13-14,16-19,21,23-25H,6,8H2,1-2H3/t13-,14-,16-,17+,18-,19+/m1/s1
• InChI Key: HXCGUCZXPFBNRD-DNLMCPORSA-N
• Popularity: 37 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₉
• Molecular Weight: 408.40 g/mol
• Exact Mass: 408.14203234 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.31
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• 495-31-8
• (+)-Marmesinin
• UNII-S2KTH28M3N
• S2KTH28M3N
• MLS000563463
• CHEBI:7607
• CHEMBL459825
• Nodakenetin, beta-D-glucopyranoside
• (2R)-2-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-2,3-dihydrofuro[3,2-g]chromen-7-one
• (2R)-2-[1-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-ethyl]-2,3-dihydrofuro[3,2-g]chromen-7-one
• AC1L2JF8
• nodakenetin glucoside
• NODAKENIN [MI]
• NODAKENIN, (+)-
• cid_73191
• MEGxp0_001251
• SCHEMBL22099973
• DTXSID601318602
• HMS2208A17
• HMS3886P20
• HY-N0825
• BDBM50242388
• MFCD09953919
• s9260
• ZB1883
• AKOS000276878
• Nodakenetin, .beta.-D-glucopyranoside
• CCG-268741
• NCGC00247564-01
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 2-(1-(beta-D-glucopyranosyloxy)-1-methylethyl)-2,3-dihydro-, (2R)-
• AC-35081
• AS-56095
• SMR000232306
• CS-0009857
• C09279
• Q-100554
• Q27107539
• (R)-2-(2-(((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propan-2-yl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one
• (R)-2-(2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propan-2-yl)-2H-furo[3,2-g]chromen-7(3H)-one
• 2-(1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1-METHYLETHYL)-2,3-DIHYDRO-7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE
• 2-[1-(beta-D-Glucopyranosyloxy)-1-methylethyl]-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one
• 7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 2-(1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1-METHYLETHYL)-2,3-DIHYDRO-, (2R)-
• 7H-Furo[3,2-g][1]benzopyran-7-one, 2-[1-(.beta.-D-glucopyranosyloxy)-1- methylethyl]-2,3-dihydro-, (2R)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7702	77.02%
Caco-2	-	0.7529	75.29%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7568	75.68%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.9046	90.46%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5133	51.33%
P-glycoprotein inhibitior	-	0.6397	63.97%
P-glycoprotein substrate	-	0.7829	78.29%
CYP3A4 substrate	+	0.5629	56.29%
CYP2C9 substrate	-	0.8241	82.41%
CYP2D6 substrate	-	0.8455	84.55%
CYP3A4 inhibition	-	0.8892	88.92%
CYP2C9 inhibition	-	0.8680	86.80%
CYP2C19 inhibition	-	0.8343	83.43%
CYP2D6 inhibition	-	0.9033	90.33%
CYP1A2 inhibition	-	0.6932	69.32%
CYP2C8 inhibition	-	0.7395	73.95%
CYP inhibitory promiscuity	-	0.7011	70.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6246	62.46%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9618	96.18%
Skin irritation	-	0.7972	79.72%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6552	65.52%
Micronuclear	-	0.5467	54.67%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8244	82.44%
Acute Oral Toxicity (c)	III	0.6592	65.92%
Estrogen receptor binding	+	0.8182	81.82%
Androgen receptor binding	+	0.6119	61.19%
Thyroid receptor binding	+	0.7055	70.55%
Glucocorticoid receptor binding	+	0.6390	63.90%
Aromatase binding	+	0.7632	76.32%
PPAR gamma	+	0.7670	76.70%
Honey bee toxicity	-	0.8404	84.04%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5352	53.52%
Fish aquatic toxicity	+	0.9463	94.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	15848.9 nM	Potency	via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	25118.9 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	35481.3 nM; 35481.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.80%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.53%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.17%	97.25%
CHEMBL220	P22303	Acetylcholinesterase	94.98%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	94.67%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.32%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.42%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.60%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.01%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.48%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.75%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.42%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.90%	95.83%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.76%	97.36%

Plants that contains it

• Angelica acutiloba
• Angelica capitellata
• Angelica dahurica
• Angelica decursiva
• Angelica gigas
• Angelica pubescens
• Angelica sinensis
• Apium graveolens
• Cicuta virosa
• Glehnia littoralis
• Hansenia forbesii
• Hansenia weberbaueriana
• Kitagawia praeruptora
• Rhodiola rosea
• Saposhnikovia divaricata

Cross-Links

• PubChem: 73191
• NPASS: NPC296377
• ChEMBL: CHEMBL459825
• LOTUS: LTS0251242
• wikiData: Q27107539