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Apigenin 7-O-glucosyl-(1→2)-glucosyl-(1→6)-glucoside

Family: Plantae - Asparagaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	OCC1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)C([C@H]([C@@H]1O)O)O[C@@H]1OC(CO[C@@H]2OC(CO)[C@H](C([C@@H]2O)O)O)[C@H](C([C@@H]1O)O)O
InChI	InChI=1S/C33H40O20/c34-8-18-22(39)25(42)28(45)31(50-18)47-10-20-24(41)26(43)29(46)32(52-20)53-30-27(44)23(40)19(9-35)51-33(30)48-13-5-14(37)21-15(38)7-16(49-17(21)6-13)11-1-3-12(36)4-2-11/h1-7,18-20,22-37,39-46H,8-10H2/t18?,19?,20?,22-,23-,24-,25?,26?,27+,28+,29+,30?,31-,32+,33-/m1/s1
InChIKey	MFTJHTRMZGZOPK-QNOAQXGQSA-N
Formula	C₃₃H₄₀O₂₀
HBA	20
HBD	12
MW	756.66
Rotatable Bonds	10
TPSA	328.35
LogP	-4.3
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	53
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	756.21
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hyacinthoides lingulata	Asparagaceae	Plantae	81761

Showing of synonyms

Hanfer M, Benramdane Z, et al. (2022). Chemical constituents, in vitro anti-inflammatory, antioxidant and hemostatic activities of the n butanol extract of Hyacinthoides lingulata (Poir.) Rothm. Natural product research, 2022, 36(12), 3124-3128. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)OC3C(OCCC3)Oc(cc4)cc(c45)oc(cc5=O)-c6ccccc6

Level: 4

Mol. Weight: 756.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3C(OCCC3)Oc(cc4)cc(c45)occc5=O

Level: 3

Mol. Weight: 756.66 g/mol

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

Level: 3

Mol. Weight: 756.66 g/mol

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

Level: 2

Mol. Weight: 756.66 g/mol

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

Level: 2

Mol. Weight: 756.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CCCOC3

Level: 2

Mol. Weight: 756.66 g/mol

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

Level: 1

Mol. Weight: 756.66 g/mol

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

Level: 1

Mol. Weight: 756.66 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 756.66 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 756.66 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 756.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 756.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 756.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.59
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 2.49
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1171.82

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.75
Plasma Protein Binding: 29.58
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: 5.53
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -27.39
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.59
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.83
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: -2121677.71
Rat (Acute): 2.67
Rat (Chronic Oral): 4.61
Fathead Minnow: 2686.74
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: 232142.06
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -1.11
Log(P): -1.44
Log S: -3.65
Log(Vapor Pressure): -7595.55
Melting Point: 220.97
pKa Acid: -20.26
pKa Basic: 6.98

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	0.9490
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9272
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9102
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8982
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8939
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8766
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8765
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8704
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8673
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8634
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8578
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8535
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8474
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8471
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8442
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8433
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8350
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8338
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8272
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.8122
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8096
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8082
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8068
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8047
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7976
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7963
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7902
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7875
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7870
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7866
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7864
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7814
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7791
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7769
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7768
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7760
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7710
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7695
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7655
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7644
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7618
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7609
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7567
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7553
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7534
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7521
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7520
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7507
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7496
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7452
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7418
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7404
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7384
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7311
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.7284
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7283
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7266
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7265
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7259
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7249
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7205
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7184
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7181
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	3	0.7181
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7176
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7165
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7153
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7153
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7140
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7112
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7098
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7080
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	3	0.7074
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7044
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7037
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7014

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