Fraxidin

Details

• Internal ID: d65be928-64d1-4f8b-98b7-e8c4d48797d1
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins
• IUPAC Name: 8-hydroxy-6,7-dimethoxychromen-2-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)C=CC(=O)O2)O)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)C=CC(=O)O2)O)OC
• InChI: InChI=1S/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)9(13)11(7)15-2/h3-5,13H,1-2H3
• InChI Key: QNFBKOHHLAWWTC-UHFFFAOYSA-N
• Popularity: 65 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀O₅
• Molecular Weight: 222.19 g/mol
• Exact Mass: 222.05282342 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 525-21-3
• 2H-1-Benzopyran-2-one, 8-hydroxy-6,7-dimethoxy-
• 8-hydroxy-6,7-dimethoxychromen-2-one
• EINECS 208-370-7
• 8-Hydroxy-6,7-dimethoxy-2-benzopyrone
• CHEMBL2334351
• CHEBI:81120
• 8-Hydroxy-6,7-dimethoxycoumarin
• 8-hydroxy-6,7-dimethoxy-2H-chromen-2-one
• SCHEMBL3190311
• DTXSID70200499
• QNFBKOHHLAWWTC-UHFFFAOYSA-N
• HY-N3907
• BDBM50428430
• MFCD00017492
• AKOS000278008
• MS-23240
• PD164908
• CS-0024435
• FT-0603449
• C17479
• 8-Hydroxy-6,7-dimethoxy-2H-1-benzopyran-2-one
• Q27155076
• 2-[(4S)-2,2-DIMETHYL-5-OXO-1,3-DIOXOLAN-4-YL]ACETICACID
• InChI=1/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)9(13)11(7)15-2/h3-5,13H,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9643	96.43%
Caco-2	+	0.6898	68.98%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6686	66.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9355	93.55%
OATP1B3 inhibitior	+	0.9746	97.46%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6770	67.70%
P-glycoprotein inhibitior	-	0.8455	84.55%
P-glycoprotein substrate	-	0.9616	96.16%
CYP3A4 substrate	-	0.6300	63.00%
CYP2C9 substrate	-	0.8431	84.31%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	-	0.7395	73.95%
CYP2C9 inhibition	-	0.9291	92.91%
CYP2C19 inhibition	-	0.7830	78.30%
CYP2D6 inhibition	-	0.8714	87.14%
CYP1A2 inhibition	+	0.8253	82.53%
CYP2C8 inhibition	-	0.5697	56.97%
CYP inhibitory promiscuity	-	0.6635	66.35%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6010	60.10%
Eye corrosion	-	0.9585	95.85%
Eye irritation	+	0.8343	83.43%
Skin irritation	-	0.6008	60.08%
Skin corrosion	-	0.9837	98.37%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6711	67.11%
Micronuclear	+	0.9059	90.59%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8224	82.24%
Acute Oral Toxicity (c)	II	0.6201	62.01%
Estrogen receptor binding	+	0.8623	86.23%
Androgen receptor binding	+	0.5293	52.93%
Thyroid receptor binding	-	0.6890	68.90%
Glucocorticoid receptor binding	+	0.6250	62.50%
Aromatase binding	+	0.8487	84.87%
PPAR gamma	+	0.6454	64.54%
Honey bee toxicity	-	0.9517	95.17%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	+	0.9128	91.28%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	9890 nM	Ki	PMID: 22892213
CHEMBL3594	Q16790	Carbonic anhydrase IX	850 nM; 850 nM	Ki; Ki	PMID: 22892213; via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	5560 nM	Ki	PMID: 22892213
CHEMBL3242	O43570	Carbonic anhydrase XII	7840 nM	Ki	PMID: 22892213

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.68%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.29%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.38%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.14%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.16%	86.33%
CHEMBL2581	P07339	Cathepsin D	84.45%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.27%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.22%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.02%	80.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.25%	94.45%
CHEMBL4208	P20618	Proteasome component C5	81.15%	90.00%

Plants that contains it

• Aconitum gigas
• Aralidium pinnatifidum
• Artemisia abrotanum
• Artemisia keiskeana
• Artemisia mesatlantica
• Artemisia minor
• Bersama swinnyi
• Blainvillea acmella
• Bulbophyllum crabro
• Ceanothus sanguineus
• Dioscorea gracillima
• Durio kutejensis
• Echium rubrum
• Entada africana
• Entada polystachya
• Euphorbia resinifera
• Eurycoma longifolia
• Fraxinus chinensis
• Fraxinus chinensis subsp. chinensis
• Fraxinus chinensis subsp. rhynchophylla
• Fraxinus ornus
• Fraxinus stylosa
• Fumaria indica
• Geigeria schinzii
• Goniothalamus undulatus
• Gymnospermium kiangnanensis
• Helichrysum sutherlandii
• Hemionitis marantae
• Iberis sempervirens
• Jatropha multifida
• Lophocereus marginatus
• Lycium barbarum
• Lycium chinense
• Moquiniastrum argentinum
• Nectandra gardneri
• Nemuaron vieillardii
• Ophryosporus charua
• Oreomecon radicata
• Pachycereus pringlei
• Picea laxa
• Plectranthus verticillatus
• Pontederia crassipes
• Prosopis kuntzei
• Pseuduvaria trimera
• Pteris leptophylla
• Pteris spinescens
• Reseda luteola
• Roemeria carica
• Salsola laricifolia
• Saposhnikovia divaricata
• Sarcandra glabra
• Schumanniophyton magnificum
• Seriphidium scotinum
• Stenocereus thurberi
• Teramnus labialis
• Trifolium pratense
• Vitex limonifolia
• Vitex negundo

Cross-Links

• PubChem: 3083616
• NPASS: NPC148835
• ChEMBL: CHEMBL2334351
• LOTUS: LTS0182118
• wikiData: Q27155076