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Agathisflavone-4’,7,7”-trimethyl ether

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

Canonical Smiles	COc1cc2oc(cc(=O)c2c(c1c1c(OC)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O)O)c1ccc(cc1)OC
InChI	InChI=1S/C33H24O10/c1-39-19-10-6-17(7-11-19)23-13-22(37)29-27(42-23)15-26(41-3)30(32(29)38)31-25(40-2)14-21(36)28-20(35)12-24(43-33(28)31)16-4-8-18(34)9-5-16/h4-15,34,36,38H,1-3H3
InChIKey	OOLIVNGGWCSOMN-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: 13888658

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)c(ccc3)-c(c4)ccc(c45)oc(cc5=O)-c6ccccc6

Level: 3

Mol. Weight: 580.55 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)c(ccc3)-c(c4)ccc(c45)occc5=O

Level: 2

Mol. Weight: 580.55 g/mol

SMILES: O=c1ccoc(c12)c(ccc2)-c(c3)ccc(c34)oc(cc4=O)-c5ccccc5

Level: 2

Mol. Weight: 580.55 g/mol

SMILES: O=c1ccoc(c12)c(ccc2)-c(c3)ccc(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): -5.57
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.840
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 16.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 2.020
Plasma Protein Binding: 87.18
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: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.790
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.150
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.760
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.950
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: Safe
T. Pyriformis: -28107.710
Rat (Acute): 2.810
Rat (Chronic Oral): 3.020
Fathead Minnow: 58.800
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: 399.640
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 5.220
Log(P): 6.04
Log S: -8.55
Log(Vapor Pressure): -15.34
Melting Point: 329.52
pKa Acid: 11.51
pKa Basic: 1.15

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9851
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9618
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9537
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9376
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.9276
Metallo-beta-lactamase type 2	P25910	BLAB_BACFG	Bacteroides fragilis	4	0.9264
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9135
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8985
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8973
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8900
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8804
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.8746
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8641
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8639
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8497
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8445
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8233
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8223
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8122
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.8078
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8076
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.8062
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7905
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7836
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7824
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7769
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7765
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7697
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7688
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.7680
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7665
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7650
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7629
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7625
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7620
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7551
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7537
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7525
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7488
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7482
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	4	0.7423
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7416
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7405
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7393
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7383
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7374
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7370
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7325
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7312
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7307
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7306
Oxidized purine nucleoside triphosphate hydrolase	P36639	8ODP_HUMAN	Homo sapiens	4	0.7299
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7297
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7296
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7291
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7289
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7258
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	4	0.7254
Neutrophil collagenase	P22894	MMP8_HUMAN	Homo sapiens	3	0.7214
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7177
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7162
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7156
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7142
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.7125
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7090
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7078
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7068
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7064
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7061
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7055
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7042
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7038
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.7011
Nucleoside diphosphate kinase	Q5HFV4	NDK_STAAC	Staphylococcus aureus	2	0.7011

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