8-Methoxycirsilineol

Details

• Internal ID: 4b7d0d6c-7c0c-4ba3-99ba-f63456e7414b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxychromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)O
• InChI: InChI=1S/C19H18O8/c1-23-13-7-9(5-6-10(13)20)12-8-11(21)14-15(22)17(24-2)19(26-4)18(25-3)16(14)27-12/h5-8,20,22H,1-4H3
• InChI Key: UBZBPKARIHPOEC-UHFFFAOYSA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₈
• Molecular Weight: 374.30 g/mol
• Exact Mass: 374.10016753 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 7-Methylsudachitin
• 16520-78-8
• 7-O-Methylsudachietin
• NSC-654971
• NSC654971
• UNII-72Y87O5H1X
• 72Y87O5H1X
• 4',5-Dihydroxy-3',6,7,8-tetramethoxy-flavone
• 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxychromen-4-one
• CHEMBL74272
• 5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-one
• 5,4'-Dihidroxy-6,7,8,3'-tetramethoxyflavone
• 4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxy-
• SCHEMBL10997058
• DTXSID40937048
• BDBM50412268
• LMPK12111475
• AKOS040735618
• NCI60_019001
• XM177967
• LS-193897
• 5,4'-dihydroxy-6,7,8,3'-tetramethoxyflavone
• Q27266108
• 5-Hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-6,7,8-trimethoxy-chromen-4-one
• 5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	+	0.7092	70.92%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7936	79.36%
OATP2B1 inhibitior	-	0.7197	71.97%
OATP1B1 inhibitior	+	0.9225	92.25%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5706	57.06%
P-glycoprotein inhibitior	+	0.7293	72.93%
P-glycoprotein substrate	-	0.8831	88.31%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.7237	72.37%
CYP2C9 inhibition	-	0.6863	68.63%
CYP2C19 inhibition	+	0.6566	65.66%
CYP2D6 inhibition	-	0.8329	83.29%
CYP1A2 inhibition	+	0.8642	86.42%
CYP2C8 inhibition	+	0.7557	75.57%
CYP inhibitory promiscuity	+	0.7231	72.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5851	58.51%
Eye corrosion	-	0.9825	98.25%
Eye irritation	+	0.5286	52.86%
Skin irritation	-	0.7275	72.75%
Skin corrosion	-	0.9759	97.59%
Ames mutagenesis	-	0.5792	57.92%
Human Ether-a-go-go-Related Gene inhibition	-	0.8281	82.81%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.9511	95.11%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8032	80.32%
Acute Oral Toxicity (c)	III	0.4741	47.41%
Estrogen receptor binding	+	0.9002	90.02%
Androgen receptor binding	+	0.8143	81.43%
Thyroid receptor binding	+	0.6899	68.99%
Glucocorticoid receptor binding	+	0.7856	78.56%
Aromatase binding	+	0.6390	63.90%
PPAR gamma	+	0.7464	74.64%
Honey bee toxicity	-	0.8498	84.98%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6049	60.49%
Fish aquatic toxicity	+	0.8969	89.69%

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	98.41%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.18%	94.00%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	95.39%	98.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.93%	99.15%
CHEMBL2581	P07339	Cathepsin D	92.37%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.34%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.13%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.66%	95.56%
CHEMBL3194	P02766	Transthyretin	88.79%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.41%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.57%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	83.85%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.57%	85.14%

Plants that contains it

• Agnorhiza bolanderi
• Anaxagorea crassipetala
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Baccharis quitensis
• Baccharis tola subsp. tola
• Bellardia trixago
• Beyeria sulcata var. brevipes
• Bursaria spinosa
• Calycadenia multiglandulosa
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Citrus × aurantium
• Citrus medica
• Cleome droserifolia
• Craibia grandiflora
• Dendrosenecio kilimanjari
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Ficus formosana
• Gardenia fosbergii
• Ilex affinis
• Isodon umbrosus
• Kaempferia pulchra
• Litogyne gariepina
• Mentha pulegium
• Mentha spicata
• Odixia angusta
• Prosopis glandulosa
• Prunus laurocerasus
• Psiadia ceylanica
• Pteris plumieri
• Quercus cerris
• Salvia officinalis
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Sideritis × angustifolia
• Sideritis leucantha
• Sideritis maura
• Simira eliezeriana
• Sorbus pallescens
• Stachys aegyptiaca
• Stenostomum lucidum
• Taxodium huegelii
• Thymus herba-barona
• Thymus saturejoides
• Thymus vulgaris
• Vitex madiensis
• Ziziphora clinopodioides

Cross-Links

• PubChem: 181092
• NPASS: NPC227325
• ChEMBL: CHEMBL74272
• LOTUS: LTS0128792
• wikiData: Q27266108