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Cupressuflavone-4',7,7"-trimethyl ether

Family: Plantae - Araucariaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Bisflavonoid

Canonical Smiles	COc1cc(O)c2c(c1c1c(OC)cc(c3c1oc(cc3=O)c1ccc(cc1)O)O)oc(cc2=O)c1ccc(cc1)OC
InChI	InChI=1S/C33H24O10/c1-39-19-10-6-17(7-11-19)25-13-21(36)29-23(38)15-27(41-3)31(33(29)43-25)30-26(40-2)14-22(37)28-20(35)12-24(42-32(28)30)16-4-8-18(34)9-5-16/h4-15,34,37-38H,1-3H3
InChIKey	MQOXLMURYUCRGW-UHFFFAOYSA-N
Formula	C₃₃H₂₄O₁₀
HBA	10
HBD	3
MW	580.55
Rotatable Bonds	6
TPSA	148.8
LogP	6.04
Number Rings	6
Number Aromatic Rings	6
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.09
Exact Mass	580.14
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Araucaria bidwillii	Araucariaceae	Plantae	56993

Showing of synonyms

Ebada S, Talaat A, et al. (2017). Cytotoxic labdane diterpenes and bisflavonoid atropisomers from leaves of Araucaria bidwillii. Tetrahedron, 2017, 73(21), 3048-3055. [View]

Pubchem: 13888659

Nmrshiftdb2: 70050857

Chembl: CHEMBL4513568

Bindingdb: 50522696

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 580.55 g/mol

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

Level: 2

Mol. Weight: 580.55 g/mol

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

Level: 1

Mol. Weight: 580.55 g/mol

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

Level: 1

Mol. Weight: 580.55 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 580.55 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 580.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.51
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.810
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 16.39

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 2.010
Plasma Protein Binding: 85.98
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: 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: 4.670
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.180
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.820
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.680
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -28036.730
Rat (Acute): 2.830
Rat (Chronic Oral): 2.990
Fathead Minnow: 59.100
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 414.800
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 5.030
Log(P): 5.94
Log S: -8.6
Log(Vapor Pressure): -15.37
Melting Point: 350.85
pKa Acid: 10.96
pKa Basic: 1.11

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	0.9357
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.9265
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9135
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9102
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8899
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8868
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8825
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8709
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8587
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8359
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8195
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.8119
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7884
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7779
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7744
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.7734
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7708
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7686
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	4	0.7633
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7633
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7626
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7597
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7592
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7565
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7564
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7492
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7481
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7451
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7389
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.7379
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7370
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7367
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	4	0.7344
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7324
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7319
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7298
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7273
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7273
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7239
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7189
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7188
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7158
Myosin heavy chain, striated muscle	P24733	MYS_ARGIR	Argopecten irradians	3	0.7105
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7078
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7045
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7044
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7027
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7012
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7011

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