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Apigenin-8-C-glucoside

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Flavonoid

Canonical Smiles	OCC1OC(C(C(C1O)O)O)c1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O
InChI	InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2
InChIKey	SGEWCQFRYRRZDC-UHFFFAOYSA-N
Formula	C₂₁H₂₀O₁₀
HBA	10
HBD	7
MW	432.38
Rotatable Bonds	3
TPSA	181.05
LogP	0.09
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	432.11
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Citrus nobilis x Citrus deliciosa	Rutaceae	Plantae	558547

Showing of synonyms

El-Hawary S.S, Issa M.Y, et al. (2022). Potential of (Citrus nobilis Lour x Citrus deliciosa Tenora) metabolites on COVID-19 virus main protease supported by in silico analysis. Natural product research, 2022, 36(11), 2843-2847. [View] [PubMed]

Pubchem: 5378180

Chebi: 192299

Nmrshiftdb2: 60024502

CPRiL: 54730

SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 432.38 g/mol

SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3

Level: 1

Mol. Weight: 432.38 g/mol

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

Level: 1

Mol. Weight: 432.38 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 432.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 432.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 432.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.52
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.75
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.39

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.79
Plasma Protein Binding: 27.44
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: 12.34
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.43
Biodegradation: Safe
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: 5.26
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: -44.3
Rat (Acute): 2.47
Rat (Chronic Oral): 4.29
Fathead Minnow: 3.9
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 617.74
Hydration Free Energy: -6.99
Log(D) at pH=7.4: 0.26
Log(P): 1.23
Log S: -3.73
Log(Vapor Pressure): -12.01
Melting Point: 222.54
pKa Acid: 4.73
pKa Basic: 8.24

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	0.9366
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9198
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8934
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8926
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8866
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8687
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8568
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8540
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8430
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8417
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8399
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8350
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8179
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8168
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8046
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8037
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7910
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7853
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7845
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7839
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7796
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7755
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7739
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7498
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7481
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7468
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7428
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7406
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7342
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7321
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7306
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7266
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7257
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7243
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7238
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7232
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7178
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7157
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7125
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7106
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7102
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7095
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7052
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7041
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7037
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7027
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7019
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7011
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7010

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