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6-O-[(2''-O-p-methoxy-trans-cinnamoyl-3''-O-acetyl)-alpha-L-rhamnopyranosyl]-catalpol

Family: Plantae - Scrophulariaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: 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=C\c2ccc(cc2)OC)OC(=O)C)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C33H42O17/c1-14-22(38)27(45-15(2)36)28(47-20(37)9-6-16-4-7-17(42-3)8-5-16)32(44-14)48-26-18-10-11-43-30(21(18)33(13-35)29(26)50-33)49-31-25(41)24(40)23(39)19(12-34)46-31/h4-11,14,18-19,21-32,34-35,38-41H,12-13H2,1-3H3/b9-6-/t14-,18+,19+,21+,22-,23+,24-,25+,26-,27+,28+,29-,30-,31?,32?,33+/m0/s1
InChIKey	AUVKOEQGZIDTGI-CAKPALOOSA-N
Formula	C₃₃H₄₂O₁₇
HBA	17
HBD	6
MW	710.68
Rotatable Bonds	11
TPSA	241.89
LogP	-1.89
Number Rings	6
Number Aromatic Rings	1
Heavy Atom Count	50
Formal Charge	0
Fraction CSP3	0.64
Exact Mass	710.24
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Verbascum dentifolium	Scrophulariaceae	Plantae	512637

Showing of synonyms

Arrif S, Lavaud C, et al. (2008). Iridoids from Verbascum dentifolium. Biochemical Systematics and Ecology,2008,36(8),669-673. [View]

Pubchem: 162949503

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6

Level: 3

Mol. Weight: 710.68 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)OC(C(O3)C34)C5C4COC=C5

Level: 2

Mol. Weight: 710.68 g/mol

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

Level: 2

Mol. Weight: 710.68 g/mol

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

Level: 1

Mol. Weight: 710.68 g/mol

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

Level: 1

Mol. Weight: 710.68 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 710.68 g/mol

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 710.68 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 710.68 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 710.68 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.75
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -1.88
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 462.52

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.68
Plasma Protein Binding: 39.82
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: 7.16
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -8.05
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.74
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.53
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: -842484.57
Rat (Acute): 3.23
Rat (Chronic Oral): 3.96
Fathead Minnow: 1072.6
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 90015.42
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.39
Log(P): -0.24
Log S: -2.65
Log(Vapor Pressure): -2922.42
Melting Point: 133.28
pKa Acid: -1.74
pKa Basic: -1.36

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7617
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7617
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7576
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7576
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7558
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7558
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7350
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7350
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7330
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7330
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7302
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7302
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7288
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7288
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7263
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7263
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7259
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7259
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7240
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7240
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7239
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7239
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7238
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7238
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7228
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7228
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	2	0.7227
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	2	0.7227
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7200
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7200
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7188
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7188
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7120
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7120
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7106
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7106
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7078
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7078
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	2	0.7062
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	2	0.7062
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7048
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7048
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7040
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7040
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7012
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7012
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	2	0.7005
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	2	0.7005

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