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6'-O-acetylverbascoside

Family: Plantae - Bignoniaceae
Kingdom: Plantae
Class: Glycoside
- Subclass: Phenylpropanoid Glycoside

Canonical Smiles	CC(=O)OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
InChI	InChI=1S/C31H38O16/c1-14-24(38)25(39)26(40)31(44-14)47-29-27(41)30(42-10-9-17-4-7-19(34)21(36)12-17)45-22(13-43-15(2)32)28(29)46-23(37)8-5-16-3-6-18(33)20(35)11-16/h3-8,11-12,14,22,24-31,33-36,38-41H,9-10,13H2,1-2H3/b8-5+/t14-,22+,24-,25+,26+,27+,28+,29+,30+,31-/m0/s1
InChIKey	JBGBPOYDCGQCJC-MWKLXWFVSA-N
Formula	C₃₁H₃₈O₁₆
HBA	16
HBD	8
MW	666.63
Rotatable Bonds	11
TPSA	251.36
LogP	-0.45
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	47
Formal Charge	0
Fraction CSP3	0.48
Exact Mass	666.22
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tecoma mollis	Bignoniaceae	Plantae	2822953

Showing of synonyms

Abdel-Mageed WM, Backheet EY, et al. (2012). Antiparasitic antioxidant phenylpropanoids and iridoid glycosides from Tecoma mollis. Fitoterapia,2012,83(3),500-507. [View] [PubMed]

Pubchem: 10462068

Cas: 441769-43-3

Zinc: ZINC000095909238

Nmrshiftdb2: 60076071

Chembl: CHEMBL4473793

Bindingdb: 50528376

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC(C2OC3CCCCO3)COC(C2)OCCc4ccccc4

Level: 3

Mol. Weight: 666.63 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OCCc3ccccc3

Level: 2

Mol. Weight: 666.63 g/mol

SMILES: c1ccccc1C=CC(=O)OC(COCC2)C2OC3CCCCO3

Level: 2

Mol. Weight: 666.63 g/mol

SMILES: c1ccccc1CCOC(OCC2)CC2OC3CCCCO3

Level: 2

Mol. Weight: 666.63 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 666.63 g/mol

SMILES: c1ccccc1CCOC2CCCCO2

Level: 1

Mol. Weight: 666.63 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 666.63 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 666.63 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 666.63 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.76
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.97
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 37.73

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.75
Plasma Protein Binding: 61.92
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.08
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.11
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.84
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.85
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: -70163.33
Rat (Acute): 2.23
Rat (Chronic Oral): 4.61
Fathead Minnow: 105.95
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: 1650.74
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 0.54
Log(P): 0.41
Log S: -4.2
Log(Vapor Pressure): -99.2
Melting Point: 194.95
pKa Acid: 5.5
pKa Basic: 1.53

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9363
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9363
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9168
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9168
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8812
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8812
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8677
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8677
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8646
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8646
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8589
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8589
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8568
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8568
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8388
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8388
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8380
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8380
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8339
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8339
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8308
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8308
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8209
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8209
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7949
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7949
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7878
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7878
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7864
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7864
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7851
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7851
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7818
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7818
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7730
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7730
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7603
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7603
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7556
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7556
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7501
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7501
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7497
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7497
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7492
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7492
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7413
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7413
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7411
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7411
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7409
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7409
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7322
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7322
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7259
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7259
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7198
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7198
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7193
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7193
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7191
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7191
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7173
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7173
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7173
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7173
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7164
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7164
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7163
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7163
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7160
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7160
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7146
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7146
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7144
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7144
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7129
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7129
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7123
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7123
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7080
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7080
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7078
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7078
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7058
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7058
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7043
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7043
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7037
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7037
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7036
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7036
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7013
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7013

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