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Pulverulentoside I

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-PHTDYJRASA-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: 162949501

Nmrshiftdb2: 70024410

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: 39.76
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: -8.0
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: -842482.89
Rat (Acute): 3.23
Rat (Chronic Oral): 3.97
Fathead Minnow: 1072.75
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: 90021.43
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.34
Log(P): -0.23
Log S: -2.65
Log(Vapor Pressure): -2924.52
Melting Point: 139.82
pKa Acid: -1.75
pKa Basic: -1.35

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8513
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8513
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8495
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8495
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7851
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7851
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.7626
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.7626
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7621
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7621
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7528
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7528
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7469
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7469
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7421
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7421
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7416
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7416
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7404
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7404
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7401
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7401
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7386
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7386
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7385
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7385
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7379
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7379
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7379
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7379
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7377
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7377
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7362
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7362
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7360
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7360
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7360
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7360
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7353
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7353
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7349
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7349
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7348
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7348
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7342
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7342
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7318
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7318
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7309
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7309
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7307
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7307
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7307
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7307
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7298
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7298
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7284
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7284
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7271
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7271
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7256
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7256
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7241
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7241
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7237
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7237
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
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7211
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7211
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7209
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7209
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7204
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7204
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	4	0.7203
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	4	0.7203
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7194
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7194
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7166
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7166
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7160
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7160
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7150
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7150
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7146
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7146
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7133
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7133
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7131
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7131
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7128
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7128
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	0.7110
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7110
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7104
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7104
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	2	0.7098
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	2	0.7098
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	2	0.7090
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	2	0.7090
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7087
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7087
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7086
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7086
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7085
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7085
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7067
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7067
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7063
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7063
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7060
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	2	0.7060
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	2	0.7060
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	2	0.7060
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	2	0.7060
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7060
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7042
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7042
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7032
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7032
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7013
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7013

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