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Cupressuflavone

Family: Plantae - Cupressaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Aglycone Flavonoid

Canonical Smiles	Oc1ccc(cc1)c1cc(=O)c2c(o1)c(c(cc2O)O)c1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O
InChI	InChI=1S/C30H18O10/c31-15-5-1-13(2-6-15)23-11-21(37)25-17(33)9-19(35)27(29(25)39-23)28-20(36)10-18(34)26-22(38)12-24(40-30(26)28)14-3-7-16(32)8-4-14/h1-12,31-36H
InChIKey	LADPNODMUXOPRG-UHFFFAOYSA-N
Formula	C₃₀H₁₈O₁₀
HBA	10
HBD	6
MW	538.46
Rotatable Bonds	3
TPSA	181.8
LogP	5.13
Number Rings	6
Number Aromatic Rings	6
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.0
Exact Mass	538.09
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tetraclinis articulata	Cupressaceae	Plantae	13717

Showing of synonyms

Zidane A, Tits M, et al. (2014). Phytochemical analysis of Tetraclinis articula in relation to its vasorelaxant property. Journal of Materials and Environmental Sciences,2014,5(5),1368-1375. [View]

Pubchem: 5281609

Cas: 3952-18-9

Gnps: CCMSLIB00004684986

Zinc: ZINC000004098511

Kegg Ligand: C10034

Chebi: 3960

Nmrshiftdb2: 60022635

Metabolights: MTBLC3960

Chembl: CHEMBL1208973

Comptox: DTXSID80415153

Bindingdb: 50323213

CPRiL: 142232

SMILES: c1ccccc1-c(cc2=O)oc(c23)c(ccc3)-c(ccc4)c(c45)oc(cc5=O)-c6ccccc6

Level: 3

Mol. Weight: 538.46 g/mol

SMILES: O=c1ccoc(c12)c(ccc2)-c(ccc3)c(c34)oc(cc4=O)-c5ccccc5

Level: 2

Mol. Weight: 538.46 g/mol

SMILES: O=c1ccoc(c12)c(ccc2)-c(ccc3)c(c34)occc4=O

Level: 1

Mol. Weight: 538.46 g/mol

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

Level: 1

Mol. Weight: 538.46 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 538.46 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 538.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.93
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.300
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 5.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.290
Plasma Protein Binding: 97.09
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.180
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.780
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.510
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.020
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -5479.090
Rat (Acute): 2.420
Rat (Chronic Oral): 3.310
Fathead Minnow: 20.140
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 641.830
Hydration Free Energy: -3.090
Log(D) at pH=7.4: 3.320
Log(P): 5.93
Log S: -6.88
Log(Vapor Pressure): -9.49
Melting Point: 451.86
pKa Acid: 8.76
pKa Basic: 6.64

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	0.9381
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9381
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8796
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8796
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8576
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8576
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8358
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8358
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8161
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8161
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.8078
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.8078
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8072
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8072
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	4	0.7872
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	4	0.7872
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7808
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7808
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7785
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7785
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7774
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7774
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7645
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7645
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7642
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7642
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7577
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7577
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7481
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7481
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	4	0.7466
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	4	0.7466
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7453
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7453
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7413
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7413
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7343
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7343
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7283
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7283
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7262
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7262
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7250
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7250
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7241
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7241
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7198
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7198
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.7186
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.7186
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7176
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7176
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7137
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7137
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7108
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7108
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7099
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7099
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7080
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7080
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7076
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7076
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7051
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7051
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7038
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7038
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7012
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7012

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