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Isoscutellarein-7-O-(6-O-acetyl-beta-D-allopyranosyl-(1→2)-beta-D-glucopyranoside

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	OCC1OC(Oc2cc(O)c3c(c2O)oc(cc3=O)c2ccc(cc2)O)C(C(C1O)O)OC1OC(COC(=O)C)C(C(C1O)O)O
InChI	InChI=1S/C29H32O17/c1-10(31)41-9-18-21(36)23(38)25(40)28(45-18)46-27-24(39)20(35)17(8-30)44-29(27)43-16-7-14(34)19-13(33)6-15(42-26(19)22(16)37)11-2-4-12(32)5-3-11/h2-7,17-18,20-21,23-25,27-30,32,34-40H,8-9H2,1H3
InChIKey	WINFSIMEBFWGGD-UHFFFAOYSA-N
Formula	C₂₉H₃₂O₁₇
HBA	17
HBD	9
MW	652.56
Rotatable Bonds	8
TPSA	275.5
LogP	-1.85
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	46
Formal Charge	0
Fraction CSP3	0.45
Exact Mass	652.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Stachys mialhesi	Lamiaceae	Plantae	53171

Showing of synonyms

Laggoune S, Zeghib A, et al. (2016). Components and antioxidant, anti-inflammatory, anti-ulcer and antinociceptive activities of the endemic species Stachys mialhesi de Noe ́. Arabian Journal of Chemistry, 2016, 9, S191-S197. [View]

Pubchem: 73802680

Nmrshiftdb2: 70020319

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 652.56 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 652.56 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 652.56 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 652.56 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 652.56 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 652.56 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 652.56 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 652.56 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 652.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.61
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.14
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 34.29

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.83
Plasma Protein Binding: -13.68
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: 10.7
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.22
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.98
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.75
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: -58704.28
Rat (Acute): 2.28
Rat (Chronic Oral): 4.05
Fathead Minnow: 92.64
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 749.94
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.41
Log(P): -0.12
Log S: -4.77
Log(Vapor Pressure): -62.45
Melting Point: 195.54
pKa Acid: 3.55
pKa Basic: 5.86

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9501
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9218
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.9075
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8835
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8829
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8806
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8730
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8721
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8659
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8452
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8397
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8367
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8268
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8243
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8214
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8210
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8171
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8165
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8117
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.8028
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8008
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7974
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7954
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7940
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7920
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7917
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7900
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7874
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7853
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7816
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7809
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7766
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7753
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7752
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7713
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7701
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7694
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7665
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7665
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7663
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7649
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7633
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7624
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7592
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7543
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7520
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7509
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7509
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7489
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7460
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7459
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7447
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7411
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7385
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7374
Leucine--tRNA ligase	P07813	SYL_ECOLI	Escherichia coli	4	0.7372
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7347
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7347
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7343
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7300
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7297
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7278
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7273
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7270
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7243
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7239
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7231
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7215
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7215
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7203
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7200
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7193
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7173
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7137
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	3	0.7120
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7117
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7106
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7083
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7056
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7036
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7029
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7020
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7018

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