ANPDB

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Scropolioside B

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

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2OC(=O)C)OC(=O)/C=C/c2ccccc2)OC(=O)/C=C/c2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C41H46O17/c1-21-33(54-27(45)15-13-23-9-5-3-6-10-23)35(55-28(46)16-14-24-11-7-4-8-12-24)36(52-22(2)44)40(51-21)56-34-25-17-18-50-38(29(25)41(20-43)37(34)58-41)57-39-32(49)31(48)30(47)26(19-42)53-39/h3-18,21,25-26,29-40,42-43,47-49H,19-20H2,1-2H3/b15-13+,16-14+/t21-,25+,26+,29+,30+,31-,32+,33-,34-,35+,36+,37-,38-,39-,40-,41+/m0/s1
InChIKey	PCHWYSGBVKSPAM-VNWDAGECSA-N
Formula	C₄₁H₄₆O₁₇
HBA	17
HBD	5
MW	810.8
Rotatable Bonds	13
TPSA	238.73
LogP	0.36
Number Rings	7
Number Aromatic Rings	2
Heavy Atom Count	58
Formal Charge	0
Fraction CSP3	0.49
Exact Mass	810.27
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Scrophularia saharae	Scrophulariaceae	Plantae	1357627
2	Verbascum ballii	Scrophulariaceae	Plantae	39257

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]
Arrif S, Benkhaled M, et al. (2006). Glycosylated iridoids and a triterpene saponin from Verbascum ballii (Batt.) M. Qaiser. Biochemical Systematics and Ecology,2006,34(3),259-262. [View]

Pubchem: 45360375

Cas: 116084-90-3

Gnps: CCMSLIB00000851616

Zinc: ZINC000253389528

Nmrshiftdb2: 70020665

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: 810.8 g/mol

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

Level: 3

Mol. Weight: 810.8 g/mol

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

Level: 3

Mol. Weight: 810.8 g/mol

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

Level: 3

Mol. Weight: 810.8 g/mol

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

Level: 2

Mol. Weight: 810.8 g/mol

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

Level: 2

Mol. Weight: 810.8 g/mol

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

Level: 2

Mol. Weight: 810.8 g/mol

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

Level: 2

Mol. Weight: 810.8 g/mol

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

Level: 1

Mol. Weight: 810.8 g/mol

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

Level: 1

Mol. Weight: 810.8 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 810.8 g/mol

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 810.8 g/mol

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 810.8 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 810.8 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 810.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.46
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 229.870
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 30739.64

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.710
Plasma Protein Binding: 58.29
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: Inhibitor

Excretion

Clearance: 6.630
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -713.790
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.620
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.860
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: -55794485.950
Rat (Acute): 3.340
Rat (Chronic Oral): 4.570
Fathead Minnow: 70435.190
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: 6270219.660
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 1.570
Log(P): 1.98
Log S: -3.5
Log(Vapor Pressure): -206394.23
Melting Point: 136.04
pKa Acid: -1442.23
pKa Basic: -4.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.9818
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.9818
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8908
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8908
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8046
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8046
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8015
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8015
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7948
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7948
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7899
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7899
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7885
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7885
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7867
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7867
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	2	0.7854
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	2	0.7854
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7782
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7782
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7781
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7781
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7737
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7737
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7697
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7697
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7680
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7680
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7639
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7639
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7572
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7572
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7571
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7571
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7569
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7569
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7471
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7471
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7442
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7442
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7361
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7361
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7301
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7301
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7268
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7268
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7244
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7244
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7240
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7240
Ribosomal protein S6 kinase beta-1	P23443	KS6B1_HUMAN	Homo sapiens	2	0.7227
Ribosomal protein S6 kinase beta-1	P23443	KS6B1_HUMAN	Homo sapiens	2	0.7227
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7184
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7184
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7139
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7139
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7126
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7126
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7083
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7083

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