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7-O-beta-apiofuranosyl-(1→6)-O-beta-glucopyranosyl benzyl alcohol

Family: Plantae - Acanthaceae
Kingdom: Plantae
Class: Glycoside
- Subclass: Benzyl Alcohol Glycoside

Canonical Smiles	OCC1(O)COC([C@@H]1O)(O)OCC1O[C@@](O)(O[C@H](c2ccccc2)O)[C@H](C([C@@H]1O)O)O
InChI	InChI=1S/C18H26O13/c19-7-16(25)8-29-18(27,15(16)24)28-6-10-11(20)12(21)13(22)17(26,30-10)31-14(23)9-4-2-1-3-5-9/h1-5,10-15,19-27H,6-8H2/t10?,11-,12?,13+,14-,15-,16?,17-,18?/m1/s1
InChIKey	RWYAXCQHFDRUHP-WNUOMJQQSA-N
Formula	C₁₈H₂₆O₁₃
HBA	13
HBD	9
MW	450.39
Rotatable Bonds	7
TPSA	218.99
LogP	-4.4
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.67
Exact Mass	450.14
Number of Lipinski Rule Violations	2

#	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: 162817640

Nmrshiftdb2: 70060458

No compound-protein relationship available.

SMILES: c1ccccc1COC(O2)CCCC2COC3CCCO3

Level: 2

Mol. Weight: 450.39 g/mol

SMILES: c1ccccc1COC2CCCCO2

Level: 1

Mol. Weight: 450.39 g/mol

SMILES: O1CCCCC1COC2CCCO2

Level: 1

Mol. Weight: 450.39 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 450.39 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 450.39 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 450.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.28
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.65
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.69
Plasma Protein Binding: 41.38
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 3.95
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.55
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.27
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.99
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: Safe
T. Pyriformis: -35.34
Rat (Acute): 1.97
Rat (Chronic Oral): 3.87
Fathead Minnow: 2.37
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: 514.3
Hydration Free Energy: -9.31
Log(D) at pH=7.4: -2.23
Log(P): -2.98
Log S: -1.08
Log(Vapor Pressure): -17.52
Melting Point: 156.71
pKa Acid: 1.62
pKa Basic: 7.77

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.9010
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.9010
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8624
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8624
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8393
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8393
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8367
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8367
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8348
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8348
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8182
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8182
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8036
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8036
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7909
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7909
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7785
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7785
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7760
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7760
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7616
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7616
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7600
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7600
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7445
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7445
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7418
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7418
Nitric oxide synthase, inducible	P35228	NOS2_HUMAN	Homo sapiens	3	0.7386
Nitric oxide synthase, inducible	P35228	NOS2_HUMAN	Homo sapiens	3	0.7386
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7385
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7385
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7373
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7373
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7318
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7318
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7300
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7300
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7284
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7284
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7266
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7266
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7249
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7249
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7234
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7234
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7229
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7229
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7209
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7209
Tissue factor	P13726	TF_HUMAN	Homo sapiens	3	0.7207
Tissue factor	P13726	TF_HUMAN	Homo sapiens	3	0.7207
Acetylglutamate kinase	Q0ASS9	Q0ASS9_MARMM	Maricaulis maris	3	0.7192
Acetylglutamate kinase	Q0ASS9	Q0ASS9_MARMM	Maricaulis maris	3	0.7192
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7186
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7186
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7165
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7165
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7163
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7163
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7112
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7112
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7108
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7108
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7080
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7080
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7077
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7077
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7074
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7074
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	2	0.7067
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	2	0.7067
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	2	0.7035
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	2	0.7035
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7020
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7020
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7015
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7015
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7014
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7014
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7011
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7011
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7006
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7006
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7005
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7005

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