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4-O-beta-glucopyranosyl dehydrodiconiferyl alcohol

Family: Plantae - Acanthaceae
Kingdom: Plantae
Class: Glycoside
- Subclass: Neolignan Glycoside

Canonical Smiles	OC/C=C/c1cc(OC)c2c(c1)[C@H](CO)[C@H](O2)c1ccc(c(c1)OC)O[C@@H]1OC(CO)[C@H](C([C@@H]1O)O)O
InChI	InChI=1S/C26H32O11/c1-33-18-10-14(5-6-17(18)35-26-23(32)22(31)21(30)20(12-29)36-26)24-16(11-28)15-8-13(4-3-7-27)9-19(34-2)25(15)37-24/h3-6,8-10,16,20-24,26-32H,7,11-12H2,1-2H3/b4-3+/t16-,20?,21+,22?,23-,24+,26+/m0/s1
InChIKey	SPWHQAUMLDQOFU-VNVWMUPHSA-N
Formula	C₂₆H₃₂O₁₁
HBA	11
HBD	6
MW	520.53
Rotatable Bonds	9
TPSA	167.53
LogP	0.1
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	37
Formal Charge	0
Fraction CSP3	0.46
Exact Mass	520.19
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Sanchezia nobilis	Acanthaceae	Plantae	71612

Showing of synonyms

Abd Ellah AE, Mohamed KM, et al. (2014). Cinnamyl alcohol, benzyl alcohol, and flavonoid glycosides from Sanchezia nobilis. Chemistry of Natural Compounds,2014,50(5),823-826. [View]

Pubchem: 162984205

Nmrshiftdb2: 70060454

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(C2)c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 520.53 g/mol

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 520.53 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 520.53 g/mol

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 520.53 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 520.53 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 520.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.3
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.94
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.68

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.02
Plasma Protein Binding: 79.75
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.37
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.62
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.63
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.87
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: -1216.97
Rat (Acute): 2.59
Rat (Chronic Oral): 3.93
Fathead Minnow: 5.8
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: 540.29
Hydration Free Energy: -2.97
Log(D) at pH=7.4: 1.03
Log(P): -0.61
Log S: -3.61
Log(Vapor Pressure): -10.91
Melting Point: 195.54
pKa Acid: 6.92
pKa Basic: 1.66

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.9269
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.9269
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9013
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9013
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8701
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8701
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	4	0.8633
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	4	0.8633
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8598
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8598
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8547
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8547
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8367
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8367
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8217
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8217
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8161
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8161
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8102
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8102
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.8023
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.8023
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.8015
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.8015
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7992
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7992
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7970
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7970
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7753
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7753
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7727
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7727
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7673
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7673
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7665
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7665
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7644
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7644
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7544
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7544
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7541
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7541
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7540
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7540
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7521
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7521
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7461
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7461
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7379
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7379
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7344
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7344
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7340
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7340
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7336
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7336
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7332
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7332
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7325
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7325
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7287
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7287
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7285
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7285
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7275
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7275
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7263
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7263
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7217
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7217
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7207
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7207
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7204
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7204
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7200
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7200
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7176
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7176
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7173
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7173
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7170
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7170
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7166
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7166
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7159
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7159
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7152
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7152
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7138
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7138
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7137
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7137
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7088
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7088
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7048
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7048
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7048
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7048
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7040
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7040
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7038
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7038
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7012
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7012
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Q9Y3Z3	SAMH1_HUMAN	Homo sapiens	3	0.7008
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Q9Y3Z3	SAMH1_HUMAN	Homo sapiens	3	0.7008
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	2	0.7006
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	2	0.7006

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