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3,4-dimethoxy-3',4'-methylenedioxy-7,7'-epoxylignan

Family: Plantae - Myristicaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	COc1cc(ccc1OC)[C@@H]1O[C@H]([C@H]([C@@H]1C)C)c1ccc2c(c1)OCO2
InChI	InChI=1S/C21H24O5/c1-12-13(2)21(15-6-8-17-19(10-15)25-11-24-17)26-20(12)14-5-7-16(22-3)18(9-14)23-4/h5-10,12-13,20-21H,11H2,1-4H3/t12-,13-,20+,21+/m0/s1
InChIKey	HSMDOSKNXLVXIP-SPDQCEQOSA-N
Formula	C₂₁H₂₄O₅
HBA	5
HBD	0
MW	356.42
Rotatable Bonds	4
TPSA	46.15
LogP	4.52
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	356.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pycnanthus angolensis	Myristicaceae	Plantae	224864

Showing of synonyms

Kuete V, Nono EC, et al. (2011). Antimicrobial activities of the CH2Cl2-CH3OH (1:1) extracts and compounds from the roots and fruits of Pycnanthus angolensis (Myristicaceae).. Natural product research,2011, 25(4), 432-443. [View] [PubMed]

Pubchem: 26113494

Zinc: ZINC000014488310

Nmrshiftdb2: 70097741

No compound-protein relationship available.

SMILES: O1COc(c12)ccc(c2)C3CCC(O3)c4ccccc4

Level: 2

Mol. Weight: 356.42 g/mol

SMILES: O1COc(c12)ccc(c2)C3CCCO3

Level: 1

Mol. Weight: 356.42 g/mol

SMILES: O1CCCC1c2ccccc2

Level: 1

Mol. Weight: 356.42 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 356.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 356.42 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 356.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.02
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.560
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.45

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.280
Plasma Protein Binding: 91.98
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 12.080
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.230
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.800
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.790
Micronucleos: Safe
NR-AhR: Safe
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: -5.760
Rat (Acute): 2.270
Rat (Chronic Oral): 1.600
Fathead Minnow: 4.590
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 421.290
Hydration Free Energy: -5.610
Log(D) at pH=7.4: 3.570
Log(P): 4.22
Log S: -5.25
Log(Vapor Pressure): -6.88
Melting Point: 93.2
pKa Acid: 10.46
pKa Basic: 2.38

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9654
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9567
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9022
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8998
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8910
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8884
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8874
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8721
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8626
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8493
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8352
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8329
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8296
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8152
Diamine oxidase [copper-containing]	P19801	AOC1_HUMAN	Homo sapiens	3	0.8143
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8070
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8052
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7974
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7908
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7877
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7733
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7636
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7626
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7623
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7582
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7567
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7520
Serine protease 1	P00760	TRY1_BOVIN	Bos taurus	3	0.7456
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7436
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7429
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7425
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7412
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7387
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7357
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7350
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7332
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7329
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7324
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7297
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7291
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7290
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7280
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7275
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7253
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7234
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7217
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7214
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7149
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7148
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7142
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7115
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7099
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7086
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7086
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7058
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7032
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	2	0.7027
Endoplasmic reticulum aminopeptidase 2	Q6P179	ERAP2_HUMAN	Homo sapiens	2	0.7019
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	2	0.7003

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