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6-(1,1-dimethylallyl)naringenin

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

Canonical Smiles	C=CC(c1c(O)cc2c(c1O)C(=O)C[C@H](O2)c1ccc(cc1)O)(C)C
InChI	InChI=1S/C20H20O5/c1-4-20(2,3)18-14(23)10-16-17(19(18)24)13(22)9-15(25-16)11-5-7-12(21)8-6-11/h4-8,10,15,21,23-24H,1,9H2,2-3H3/t15-/m0/s1
InChIKey	GKOWEQNADRJYIA-HNNXBMFYSA-N
Formula	C₂₀H₂₀O₅
HBA	5
HBD	3
MW	340.38
Rotatable Bonds	3
TPSA	86.99
LogP	3.97
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	340.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Monotes kerstingii	Dipterocarpaceae	Plantae	2029430

Showing of synonyms

Fotso GW, Mogue Kamdem L, et al. (2019). Antimicrobial secondary metabolites from the stem barks and leaves of Monotes kerstingii Gilg (Dipterocarpaceae).. Fitoterapia,2019, 137, 104239. [View] [PubMed]

Pubchem: 10759582

Cas: 192572-93-3

Zinc: ZINC000015121029

Nmrshiftdb2: 70009293

Chembl: CHEMBL478765

CPRiL: 290045

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 340.38 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 340.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 340.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.62
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.76
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.31

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.09
Plasma Protein Binding: 78.44
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: 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: 7.44
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.83
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.76
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.11
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 2.1
Rat (Acute): 2.24
Rat (Chronic Oral): 2.73
Fathead Minnow: 4.53
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 434.58
Hydration Free Energy: -9.99
Log(D) at pH=7.4: 3.31
Log(P): 4.04
Log S: -5.52
Log(Vapor Pressure): -8.62
Melting Point: 164.91
pKa Acid: 7.68
pKa Basic: 5.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9469
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9406
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9281
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9218
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9164
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9085
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.9036
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8943
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8855
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8850
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8735
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8733
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8718
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8632
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8622
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8598
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8596
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8581
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.8578
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8576
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8571
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8549
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8517
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8489
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8425
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8361
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8343
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.8338
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	5	0.8324
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.8324
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8297
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8279
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8239
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8119
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.8067
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8046
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8011
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8011
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	4	0.7956
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7943
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7901
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.7824
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7799
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7715
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7714
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7704
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7685
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7679
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7665
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7636
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.7613
AGAP001556-PA	Q7PXT9	Q7PXT9_ANOGA	Anopheles gambiae	3	0.7600
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7574
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7546
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7544
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7541
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7534
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7505
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7487
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7481
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7465
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7452
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7445
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7418
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	4	0.7414
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7414
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.7403
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7402
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7367
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7344
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7339
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7331
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7329
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7323
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7316
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7304
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7303
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7299
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7281
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7274
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7273
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7269
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7264
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7260
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7260
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7250
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7249
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7249
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7245
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7238
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7237
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7237
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7221
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7202
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7192
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7190
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7189
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7179
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7174
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7163
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7162
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7161
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7154
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7153
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7152
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7146
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7145
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7145
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7140
23S rRNA (guanine(745)-N(1))-methyltransferase	P36999	RLMA_ECOLI	Escherichia coli	3	0.7138
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7130
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7126
Myosin-2 heavy chain	P08799	MYS2_DICDI	Dictyostelium discoideum	4	0.7120
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7117
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7112
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7092
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7084
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7081
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7078
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7075
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7064
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7055
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7055
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7041
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7032
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7022
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7015
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7012
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7009
Enoyl-acyl carrier reductase	Q6UCJ9	Q6UCJ9_TOXGO	Toxoplasma gondii	4	0.7001

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