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5,7,4′- trihydoxy-8-prenylflavone

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	CC(=CCc1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O)C
InChI	InChI=1S/C20H18O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3
InChIKey	MEHHCBRCXIDGKZ-UHFFFAOYSA-N
Formula	C₂₀H₁₈O₅
HBA	5
HBD	3
MW	338.36
Rotatable Bonds	3
TPSA	90.9
LogP	4.09
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	338.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dorstenia barteri	Moraceae	Plantae	2604977
2	Dorstenia ciliata	Moraceae	Plantae	2604984

Showing of synonyms

Tsopmo A, Tene M, et al. (1999). A new diels-alder-type adduct flavonoid from Dorstenia barteri.. Journal of natural products,1999, 62(10), 1432-1434. [View] [PubMed]
Ngadjui BT, Ngameni B, et al. (2002). Prenylated and geranylated chalcones and flavones from the aerial parts of Dorstenia ciliata. Bulletin of The Chemical Society of Ethiopia, 2002, 16(2), 157-164. [View]

Pubchem: 10246505

Cas: 72357-31-4

Gnps: CCMSLIB00006443296

Zinc: ZINC000000021406

Nmrshiftdb2: 60025911

Chembl: CHEMBL371562

Bindingdb: 50240972

CPRiL: 66992

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 338.36 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 338.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 338.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.87
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.73
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.09

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.12
Plasma Protein Binding: 82.12
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 2.33
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.34
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.93
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.61
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 2.66
Rat (Acute): 2.22
Rat (Chronic Oral): 2.58
Fathead Minnow: 4.96
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 473.68
Hydration Free Energy: -10.9
Log(D) at pH=7.4: 3.77
Log(P): 5.01
Log S: -5.41
Log(Vapor Pressure): -8.96
Melting Point: 246.87
pKa Acid: 9.06
pKa Basic: 7.07

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9414
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9334
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9332
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9226
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.9186
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.9121
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9121
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9023
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9011
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.9008
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8942
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8868
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8765
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8723
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8706
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8702
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8681
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8659
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8576
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8537
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8530
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8524
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8509
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8488
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8475
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8461
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8459
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8392
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8348
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.8344
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8288
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8265
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8265
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8231
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8219
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.8199
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.8177
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8142
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8118
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8050
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7979
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7961
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7913
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7906
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7888
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7885
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7853
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7848
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7843
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7796
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7770
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7765
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7725
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7666
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7644
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7608
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	4	0.7600
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7566
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7563
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7554
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7543
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	4	0.7525
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7504
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7498
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7477
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7469
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7464
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7437
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7435
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7433
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7432
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7430
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7405
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7398
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7383
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7380
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7377
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	6	0.7356
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7343
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	3	0.7337
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7334
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7332
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7331
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7325
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7322
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7321
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7320
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7320
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7298
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7295
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7285
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7285
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7263
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7256
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	3	0.7254
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.7251
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7250
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7247
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7241
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7233
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7230
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7228
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7223
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7209
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7202
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7199
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7196
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7190
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7184
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7179
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7159
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7152
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7146
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7134
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7125
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7112
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7111
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7108
Carbonic anhydrase 4	P22748	CAH4_HUMAN	Homo sapiens	3	0.7101
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7093
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7079
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7069
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7068
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7067
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7066
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7043
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7040
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7021
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7010
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7009
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	4	0.7004
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7002

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