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Denudatin A

Family: Plantae - Magnoliaceae
Kingdom: Plantae
Class: Lignan
- Subclass: Benzofuran Flavonoid

Canonical Smiles	C=CCC1=C[C@]2(OC)C(=CC1=O)O[C@@H]([C@H]2C)c1ccc2c(c1)OCO2
InChI	InChI=1S/C20H20O5/c1-4-5-14-10-20(22-3)12(2)19(25-18(20)9-15(14)21)13-6-7-16-17(8-13)24-11-23-16/h4,6-10,12,19H,1,5,11H2,2-3H3/t12-,19+,20-/m1/s1
InChIKey	GGRIWHJBFXFKGS-OITMNORJSA-N
Formula	C₂₀H₂₀O₅
HBA	5
HBD	0
MW	340.38
Rotatable Bonds	4
TPSA	53.99
LogP	3.48
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	340.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Magnolia saulangiana	Magnoliaceae	Plantae	3402

Showing of synonyms

Abdallah O. (1993). Lignans in flower buds of Magnolia saulangiana. Phytochemistry, 1993, 34(4), 1185-1187. [View]

Pubchem: 13336517

Cas: 87402-87-7

Zinc: ZINC000013434857

Nmrshiftdb2: 60070279

Chembl: CHEMBL606463

No compound-protein relationship available.

SMILES: O1COc(c12)ccc(c2)C(O3)CC(C3=4)C=CC(=O)C4

Level: 1

Mol. Weight: 340.38 g/mol

SMILES: O1CCC(C1=2)C=CC(=O)C2

Level: 0

Mol. Weight: 340.38 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 340.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.3
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.9

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.09
Plasma Protein Binding: 78.24
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: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.75
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.21
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.22
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.47
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: Safe
T. Pyriformis: -2.69
Rat (Acute): 2.46
Rat (Chronic Oral): 1.74
Fathead Minnow: 4.5
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 406.1
Hydration Free Energy: -6.35
Log(D) at pH=7.4: 3.43
Log(P): 3.44
Log S: -4.4
Log(Vapor Pressure): -7.16
Melting Point: 90.38
pKa Acid: 8.47
pKa Basic: 3.28

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	0.9257
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9221
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9156
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9144
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9016
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8894
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8835
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8822
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8796
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.8771
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8758
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8736
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8729
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8725
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8702
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8695
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8588
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.8578
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8520
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8517
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8314
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.8219
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8095
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8064
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8058
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.8043
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.8008
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7993
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7987
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7985
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7980
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7956
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7954
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7933
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7929
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7917
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7875
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7857
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7852
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7828
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7828
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7822
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7819
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7782
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7767
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7724
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7712
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7706
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7683
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7620
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7558
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7539
Phosphoenolpyruvate carboxykinase [GTP]	P9WIH3	PCKG_MYCTU	Mycobacterium tuberculosis	3	0.7535
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7534
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7517
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7515
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7512
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7496
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7489
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7487
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7464
Probable esterase KAI2	Q9SZU7	KAI2_ARATH	Arabidopsis thaliana	3	0.7460
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	2	0.7452
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7446
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	4	0.7445
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7439
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7439
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7428
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7427
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7393
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7382
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7374
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7366
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7357
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7350
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7337
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7320
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7313
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7305
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7303
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7293
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7269
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7262
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7244
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7230
Phosphoenolpyruvate carboxykinase [GTP]	A5TYT6	PCKG_MYCTA	Mycobacterium tuberculosis	3	0.7228
Phytohormone-binding protein	G7J032	PHBP_MEDTR	Medicago truncatula	4	0.7225
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7218
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.7203
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7196
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	2	0.7173
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7171
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7167
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7152
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7148
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7124
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.7108
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7101
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	2	0.7101
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7075
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7071
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7071
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7066
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7062
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7061
Aspartokinase 1, chloroplastic	Q9LYU8	AK1_ARATH	Arabidopsis thaliana	3	0.7061
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7051
Phosphoenolpyruvate carboxykinase [GTP]	A5TYT6	PCKG_MYCTA	Mycobacterium tuberculosis	3	0.7038
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7021
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7019
Prostaglandin G/H synthase 1	P05979	PGH1_SHEEP	Ovis aries	2	0.7016
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7016
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7016

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