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Apigenin 7-O-glucosyl-(1→2)-glucosyl-(1→2)-rhamnoside

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]([C@@H](C1O[C@@H]1OC(C)[C@H]([C@@H](C1O)O)O)O)O
InChI	InChI=1S/C33H40O19/c1-11-22(39)25(42)28(45)31(46-11)51-30-27(44)24(41)20(10-35)50-33(30)52-29-26(43)23(40)19(9-34)49-32(29)47-14-6-15(37)21-16(38)8-17(48-18(21)7-14)12-2-4-13(36)5-3-12/h2-8,11,19-20,22-37,39-45H,9-10H2,1H3/t11?,19?,20?,22-,23-,24-,25+,26+,27+,28?,29?,30?,31+,32-,33+/m1/s1
InChIKey	YXANDSLVLGMPMR-DFODMAPCSA-N
Formula	C₃₃H₄₀O₁₉
HBA	19
HBD	11
MW	740.66
Rotatable Bonds	9
TPSA	308.12
LogP	-3.27
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	52
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	740.22
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: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC(OCCC4)C4OC(OCCC5)C5OC6CCCCO6

Level: 4

Mol. Weight: 740.66 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC(OCCC3)C3OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 740.66 g/mol

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

Level: 3

Mol. Weight: 740.66 g/mol

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

Level: 2

Mol. Weight: 740.66 g/mol

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

Level: 2

Mol. Weight: 740.66 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 740.66 g/mol

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

Level: 1

Mol. Weight: 740.66 g/mol

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

Level: 1

Mol. Weight: 740.66 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 740.66 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 740.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 740.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 740.66 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: -0.89
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 708.95

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.81
Plasma Protein Binding: 38.82
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.87
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -14.48
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.68
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.96
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: -1282442.33
Rat (Acute): 2.55
Rat (Chronic Oral): 4.13
Fathead Minnow: 1627.68
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: 137642.93
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.65
Log(P): -0.97
Log S: -4.32
Log(Vapor Pressure): -4508.97
Melting Point: 189.48
pKa Acid: -6.9
pKa Basic: 5.84

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	0.9505
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9474
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9212
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.9000
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8934
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8848
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8835
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8804
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8771
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.8740
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8645
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8607
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8574
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8552
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8445
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8378
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8367
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8345
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8283
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8281
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8206
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8182
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8017
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7993
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7987
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7973
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.7882
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7879
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7860
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7848
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7848
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7838
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7834
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7828
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7824
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7824
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7786
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7762
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7711
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7667
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7652
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7612
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7594
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7589
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7577
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7558
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7554
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7534
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7533
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7495
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7471
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7399
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	Q08AH3	ACS2A_HUMAN	Homo sapiens	2	0.7347
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7326
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7326
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7317
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7307
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7304
Ribosomal protein S6 kinase alpha-3	P51812	KS6A3_HUMAN	Homo sapiens	4	0.7279
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7278
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7277
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7273
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7258
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7248
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7244
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7224
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	3	0.7211
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7199
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7197
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7189
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7179
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7170
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7159
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7156
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7093
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7092
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7089
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7088
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7068
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7065
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7061
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7053
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7048
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7041
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	3	0.7032
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7018
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7005
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7004

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