Amentoflavone

Details

• Internal ID: b4a29c1a-a584-49c6-ad58-b4c64f8938c2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O)O
• InChI: InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H
• InChI Key: YUSWMAULDXZHPY-UHFFFAOYSA-N
• Popularity: 724 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₁₈O₁₀
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.08999677 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 5.13
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

• 1617-53-4
• Didemethyl-ginkgetin
• 3',8''-Biapigenin
• Amenthoflavone
• Tridemethylsciadopitysin
• UNII-9I1VC79L77
• MLS000574827
• CHEBI:2631
• 9I1VC79L77
• MFCD00017470
• NSC 295677
• NSC-295677
• 8-[5-(5,7-dihydroxy-4-oxo-chromen-2-yl)-2-hydroxy-phenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMR000156235
• 4H-1-Benzopyran-4-one, 8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
• 8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• 8-(5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• 8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• SR-01000721725
• 4H-1-Benzopyran-4-one, 8-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-
• D06HRX
• AMENTOFLAVONE [INCI]
• BIDD:PXR0028
• I3',II8-BIAPIGENIN
• GINKGETIN, DIDEMETHYL-
• SCHEMBL312563
• MEGxp0_000924
• med.21724, Compound 138
• DTXSID20167225
• Amentoflavone, analytical standard
• YUSWMAULDXZHPY-UHFFFAOYSA-N
• BDBM429466
• HMS2228B12
• HMS3343J17
• HMS3885A08
• -hydroxyphenyl)-5,7-dihydroxy-2-
• BCP13255
• BEA14006
• HY-N0662
• Amentoflavone, >=99.0% (HPLC)
• LMPK12040009
• NSC295677
• s3833
• (4-hydroxyphenyl)-4H-chromen-4-one
• AKOS015896819
• CCG-269950
• CS-4945
• 3',8-Bi[4',5,7-trihydroxyflavone]
• NCGC00247542-01
• NCGC00247542-02
• AC-34718
• BS-15502
• FT-0622262
• A11476
• A810291
• 8-(5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2
• Q-100192
• Q4742425
• SR-01000721725-2
• SR-01000721725-3
• 4',5,7-Trihydroxyflavone(3'->8)-4',5,7-trihydroxyflavone
• 3''',8-BIFLAVONE, 4',4''',5,5'',7,7''-HEXAHYDROXY
• 4',4''',5,5'',7,7''-Hexahydroxy-3''',8-biflavone, 8CI
• 4H-1-Benzopyran-4-one, 8-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)
• 8-[5-(5,7-dihydroxy-4-oxo-chromen-2-yl)-2-hydroxy-phenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one;Amentoflavone
• 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9336	93.36%
Caco-2	-	0.8774	87.74%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8010	80.10%
OATP2B1 inhibitior	+	0.5792	57.92%
OATP1B1 inhibitior	-	0.3196	31.96%
OATP1B3 inhibitior	-	0.2208	22.08%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8589	85.89%
P-glycoprotein inhibitior	-	0.4467	44.67%
P-glycoprotein substrate	-	0.7248	72.48%
CYP3A4 substrate	+	0.5925	59.25%
CYP2C9 substrate	-	0.6443	64.43%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	+	0.6172	61.72%
CYP2C9 inhibition	+	0.8920	89.20%
CYP2C19 inhibition	+	0.6827	68.27%
CYP2D6 inhibition	-	0.9322	93.22%
CYP1A2 inhibition	+	0.6838	68.38%
CYP2C8 inhibition	+	0.8800	88.00%
CYP inhibitory promiscuity	+	0.5157	51.57%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7320	73.20%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.6819	68.19%
Skin irritation	+	0.5256	52.56%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3749	37.49%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8881	88.81%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5927	59.27%
Acute Oral Toxicity (c)	II	0.6295	62.95%
Estrogen receptor binding	+	0.8873	88.73%
Androgen receptor binding	+	0.9422	94.22%
Thyroid receptor binding	+	0.6141	61.41%
Glucocorticoid receptor binding	+	0.7881	78.81%
Aromatase binding	+	0.6084	60.84%
PPAR gamma	+	0.8430	84.30%
Honey bee toxicity	-	0.7521	75.21%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9283	92.83%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL4822	P56817	Beta-secretase 1	1540 nM	IC50	PMID: 20598535
CHEMBL236	P41143	Delta opioid receptor	36.5 nM; 36 nM	Ki; Ki	PMID: 20408551; PMID: 17685652
CHEMBL234	P35462	Dopamine D3 receptor	1241 nM	Ki	PMID: 12824018
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	1634.07 nM	IC50	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM; 7079.5 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3474	P14555	Phospholipase A2 group IIA	23800 nM	IC50	PMID: 16504502
CHEMBL3964	P19174	Phospholipase C-gamma-1	29000 nM	IC50	PMID: 10869194
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	7400 nM	IC50	PMID: 25907369
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	2555 nM	Ki	PMID: 12824018
CHEMBL1075145	P55072	Transitional endoplasmic reticulum ATPase	8984 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL242	Q92731	Estrogen receptor beta	99.46%	98.35%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.06%	91.11%
CHEMBL3194	P02766	Transthyretin	97.48%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.61%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	96.21%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.98%	99.15%
CHEMBL2581	P07339	Cathepsin D	95.49%	98.95%
CHEMBL3038469	P24941	CDK2/Cyclin A	92.80%	91.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.92%	94.00%
CHEMBL308	P06493	Cyclin-dependent kinase 1	90.75%	91.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.34%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.24%	95.56%
CHEMBL1978	P11511	Cytochrome P450 19A1	87.63%	91.76%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	86.78%	89.23%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.18%	91.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.98%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	84.92%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.91%	99.23%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.91%	85.11%
CHEMBL4530	P00488	Coagulation factor XIII	82.08%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.88%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.74%	83.57%
CHEMBL2208	P49137	MAP kinase-activated protein kinase 2	81.54%	95.20%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.61%	95.78%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.49%	97.28%

Plants that contains it

• Aglaia forbesii
• Albizia julibrissin
• Apocynum venetum
• Araucaria cunninghamii
• Biophytum sensitivum
• Brassica oleracea
• Breonia chinensis
• Broussonetia papyrifera
• Calocedrus decurrens
• Calocedrus formosana
• Calophyllum brasiliense
• Calophyllum calaba
• Calophyllum inophyllum
• Calophyllum pinetorum
• Calophyllum venulosum
• Campylospermum flavum
• Campylospermum glaucum
• Campylospermum sulcatum
• Campylotropis hirtella
• Canarium schweinfurthii
• Casearia clarkei
• Cephalotaxus fortunei
• Ceropegia dichotoma
• Chamaecyparis formosensis
• Chrozophora tinctoria
• Cremastra appendiculata
• Crinum moorei
• Crotalaria candicans
• Cryptomeria japonica
• Cunninghamia lanceolata
• Cupressus nootkatensis
• Cupressus sempervirens
• Cycas beddomei
• Cycas revoluta
• Dendrobium chrysotoxum
• Dendrobium loddigesii
• Distephanus angulifolius
• Elateriospermum tapos
• Erucastrum gallicum
• Etlingera elatior
• Eucalyptus apodophylla
• Eurybia divaricata
• Garcinia intermedia
• Garcinia kola
• Garcinia livingstonei
• Garcinia prainiana
• Garcinia xanthochymus
• Ginkgo biloba
• Glycosmis macrophylla
• Gypsophila perfoliata
• Haplopteris anguste-elongata
• Hippobromus pauciflorus
• Hydnocarpus hainanensis
• Hypericum elegans
• Hypericum montanum
• Hypericum perforatum
• Hypericum polyanthemum
• Hypericum thasium
• Isophysis tasmanica
• Juniperus communis
• Juniperus drupacea
• Juniperus occidentalis
• Juniperus sabina var. sabina
• Juniperus virginiana
• Lanaria lanata
• Leycesteria formosa
• Lophostemon confertus
• Luxemburgia nobilis
• Mammea siamensis
• Mangifera indica
• Manihot esculenta
• Mentha × gentilis
• Metasequoia glyptostroboides
• Microbiota decussata
• Nageia nagi
• Nandina domestica
• Nanuza plicata
• Ononis spinosa
• Orbivestus karaguensis
• Orthopterygium huaucui
• Ouratea castaneifolia
• Ouratea multiflora
• Ouratea semiserrata
• Panax stipuleanatus
• Patersonia glabrata
• Pentaclethra macrophylla
• Periploca sepium
• Phyllosma capensis
• Physocarpus capitatus
• Picea smithiana
• Pinalia japonica
• Pinus palustris
• Piranhea mexicana
• Platycladus orientalis
• Plectranthus hereroensis
• Pleione bulbocodioides
• Pleione yunnanensis
• Podocarpus fasciculus
• Podocarpus macrophyllus
• Podocarpus nivalis
• Proustia ilicifolia
• Pterocaulon virgatum
• Quercus canariensis
• Quercus infectoria
• Retrophyllum rospigliosii
• Rhodiola semenovii
• Rhus coriaria
• Rhus punjabensis
• Salvia sessei
• Schinus areira
• Schinus terebinthifolia
• Schnabelia tetradonta
• Sciadotenia toxifera
• Selaginella delicatula
• Selaginella denticulata
• Selaginella doederleinii
• Selaginella kraussiana
• Selaginella labordei
• Selaginella moellendorffii
• Selaginella pulvinata
• Selaginella selaginoides
• Selaginella tamariscina
• Selaginella uncinata
• Selaginella willdenowii
• Sequoiadendron giganteum
• Sonneratia caseolaris
• Soulamea pancheri
• Stephania zippeliana
• Struthiola argentea
• Taiwania cryptomerioides
• Taxodium distichum
• Taxodium huegelii
• Taxus baccata
• Taxus wallichiana
• Tetraclinis articulata
• Tilia tomentosa
• Tmesipteris lanceolata
• Torreya fargesii var. yunnanensis
• Torreya grandis
• Torreya nucifera
• Toxicodendron succedaneum
• Valeriana microphylla
• Veronica polita
• Viburnum coriaceum
• Viburnum cotinifolium
• Viburnum davidii
• Viburnum jucundum
• Viburnum pichinchense

Cross-Links

• PubChem: 5281600
• NPASS: NPC138299
• ChEMBL: CHEMBL63354
• LOTUS: LTS0063796
• wikiData: Q4742425