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Scrophuloside B5

Family: Plantae - Scrophulariaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Acylated Iridoid Glycoside

Canonical Smiles	OC[C@H]1OC(O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3OC2O[C@@H](C)[C@@H]([C@H]([C@H]2OC(=O)C)OC(=O)/C=C/c2ccc(cc2)OC)OC(=O)/C=C/c2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C42H48O18/c1-21-34(56-28(46)15-11-23-7-5-4-6-8-23)36(57-29(47)16-12-24-9-13-25(51-3)14-10-24)37(54-22(2)45)41(53-21)58-35-26-17-18-52-39(30(26)42(20-44)38(35)60-42)59-40-33(50)32(49)31(48)27(19-43)55-40/h4-18,21,26-27,30-41,43-44,48-50H,19-20H2,1-3H3/b15-11+,16-12+/t21-,26+,27+,30+,31+,32-,33+,34-,35-,36+,37+,38-,39-,40?,41?,42+/m0/s1
InChIKey	FXKHOFVDHKYWJM-ORVRTXMXSA-N
Formula	C₄₂H₄₈O₁₈
HBA	18
HBD	5
MW	840.83
Rotatable Bonds	14
TPSA	247.96
LogP	0.37
Number Rings	7
Number Aromatic Rings	2
Heavy Atom Count	60
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	840.28
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Scrophularia saharae	Scrophulariaceae	Plantae	1357627

Showing of synonyms

Chebaki R, Haba H, et al. (2011). Acylated iridoid glycosides from Scrophularia saharae Batt. & Trab.. Biochemical Systematics and Ecology,2011,39(4-6),902-905. [View]

Pubchem: 162817089

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC2C(OC(=O)C=Cc3ccccc3)COC(C2)OC(C(O4)C45)C6C5C(OC=C6)OC7CCCCO7

Level: 4

Mol. Weight: 840.83 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OC(=O)C=Cc3ccccc3)COC(C2)OC(C(O4)C45)C6C5COC=C6

Level: 3

Mol. Weight: 840.83 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6

Level: 3

Mol. Weight: 840.83 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6

Level: 3

Mol. Weight: 840.83 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(C(O3)C34)C5C4COC=C5

Level: 2

Mol. Weight: 840.83 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(C(O3)C34)C5C4COC=C5

Level: 2

Mol. Weight: 840.83 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(COCC2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 840.83 g/mol

SMILES: O1CCCCC1OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5

Level: 2

Mol. Weight: 840.83 g/mol

SMILES: C1=COCC2C1C(C(O3)C23)OC4CCCCO4

Level: 1

Mol. Weight: 840.83 g/mol

SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4

Level: 1

Mol. Weight: 840.83 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 840.83 g/mol

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 840.83 g/mol

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 840.83 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 840.83 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 840.83 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.5
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 567.18
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 74839.24

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.71
Plasma Protein Binding: 54.38
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: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 5.92
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -1739.59
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.58
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.94
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: -135832990.03
Rat (Acute): 3.32
Rat (Chronic Oral): 4.64
Fathead Minnow: 171467.52
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 15272186.0
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 1.23
Log(P): 2.4
Log S: -3.57
Log(Vapor Pressure): -502829.01
Melting Point: 144.53
pKa Acid: -3597.68
pKa Basic: -8.41

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8411
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8411
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8326
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8326
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8311
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8311
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.8141
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.8141
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7614
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7614
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7533
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7533
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7530
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7530
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7461
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7461
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7431
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7431
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7409
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7409
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7392
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7392
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7390
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7390
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7384
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7384
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7384
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7384
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7370
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7370
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7366
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7366
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7366
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7366
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7365
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7365
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7363
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7363
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7349
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7349
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7340
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7340
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7337
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7337
Histone deacetylase-like amidohydrolase	Q70I53	HDAH_ALCSD	Alcaligenes sp.)	2	0.7332
Histone deacetylase-like amidohydrolase	Q70I53	HDAH_ALCSD	Alcaligenes sp.)	2	0.7332
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7324
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7324
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7319
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7319
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7304
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7304
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7299
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7299
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7295
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7295
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7293
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7293
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7285
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7285
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7248
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7248
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7236
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7236
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7229
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7229
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7223
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7223
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7211
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7211
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7209
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7209
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7208
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7208
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7197
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7197
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7196
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7196
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7195
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7195
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7167
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7167
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7161
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7161
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7160
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7160
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7159
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7159
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7158
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7158
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7155
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7155
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7152
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7152
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7151
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7151
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7146
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7146
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7144
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7144
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7142
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7142
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7129
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7129
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7126
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7126
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7123
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7123
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7113
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7113
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	2	0.7113
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	2	0.7113
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7110
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7110
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7107
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7107
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7102
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7102
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7095
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7095
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7088
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7088
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7080
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7080
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	2	0.7077
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	2	0.7077
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	2	0.7075
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	2	0.7075
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	2	0.7072
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	2	0.7072
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7064
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7064
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	2	0.7058
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	2	0.7058
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7058
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7058
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	2	0.7034
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	2	0.7034

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