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(+)-dehydrodiconiferyl alcohol

Family: Plantae - Cruciferae-Brassicaceea
Kingdom: Plantae
Class: Lignan
- Subclass: Neolignan

Canonical Smiles	OC/C=C/c1cc2c(c(c1)OC)O[C@@H]([C@H]2CO)c1ccc(c(c1)OC)O
InChI	InChI=1S/C20H22O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h3-6,8-10,15,19,21-23H,7,11H2,1-2H3/b4-3+/t15-,19+/m0/s1
InChIKey	KUSXBOZNRPQEON-LNFBDUAVSA-N
Formula	C₂₀H₂₂O₆
HBA	6
HBD	3
MW	358.39
Rotatable Bonds	6
TPSA	88.38
LogP	2.62
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	358.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Anastatica hierochuntica	Cruciferae-Brassicaceea	Plantae	663965

Showing of synonyms

Nakashima S, Matsuda H, et al. (2010). Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells. Bioorganic and Medicinal Chemistry,2010,18(6),2337-2345. [View] [PubMed]

Pubchem: 11824478

Cas: 97465-82-2

Zinc: ZINC000029064393

Chebi: 143256

Nmrshiftdb2: 60026974

Metabolights: MTBLC143256

Chembl: CHEMBL406378

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 358.39 g/mol

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 358.39 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 358.39 g/mol

Anticancer

Absorption

Caco-2 (logPapp): -4.49
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.79
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.39

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.15
Plasma Protein Binding: 77.53
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: 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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.44
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.4
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.82
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.16
Micronucleos: Toxic
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: Safe
T. Pyriformis: -3.55
Rat (Acute): 2.05
Rat (Chronic Oral): 2.94
Fathead Minnow: 4.69
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 444.42
Hydration Free Energy: -8.0
Log(D) at pH=7.4: 2.44
Log(P): 1.16
Log S: -4.19
Log(Vapor Pressure): -7.97
Melting Point: 155.23
pKa Acid: 8.51
pKa Basic: 1.62

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9153
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9153
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8765
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8765
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8760
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8760
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	4	0.8691
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	4	0.8691
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8638
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8638
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8584
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8584
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8535
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8535
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8461
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8461
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8442
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8442
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8441
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8441
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8250
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8250
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8241
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8241
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8199
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8199
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8178
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8178
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8028
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8028
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8023
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8023
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7994
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7994
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7965
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7965
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7939
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7939
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7924
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7924
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7906
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7906
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7904
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7904
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7730
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7730
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7709
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7709
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7701
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7701
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7670
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7670
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7649
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7649
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7618
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7618
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7613
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7613
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7572
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7572
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7562
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7562
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7560
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7560
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7552
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7552
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7536
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7536
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7525
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7525
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7436
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7436
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7427
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7427
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7424
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7424
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7375
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7375
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7322
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7322
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7318
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7318
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7294
Lethal factor	P15917	LEF_BACAN	Bacillus anthracis	3	0.7294
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7279
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7279
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7273
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7273
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7259
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7259
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7250
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7250
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7236
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7236
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7224
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7224
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7220
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7220
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7192
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7192
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7163
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7163
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7157
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7157
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	2	0.7154
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	2	0.7154
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7143
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7143
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7120
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7120
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7112
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7112
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7101
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7101
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7100
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7100
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7099
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7099
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7082
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7082
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7079
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7079
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7066
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7066
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7063
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7063
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7062
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7062
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7055
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7055
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7053
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7053
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7052
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7052
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7048
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7048
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7044
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7044
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7043
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7043
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7031
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7031
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	4	0.7020
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	4	0.7020
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7018
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7018
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7016
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7016
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7015
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7015
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7015
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7015
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7008
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7008
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7001
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7001

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