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Miquelianin

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

Canonical Smiles	Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
InChIKey	DUBCCGAQYVUYEU-ZUGPOPFOSA-N
Formula	C₂₁H₁₈O₁₃
HBA	12
HBD	8
MW	478.36
Rotatable Bonds	4
TPSA	227.58
LogP	-0.45
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	478.07
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Schinus molle	Anacardiaceae	Plantae	43851
2	Euphorbia sanctae-catharinae	Euphorbiaceae	Plantae	3990
3	Psidium guajava	Myrtaceae	Plantae	120290
4	Pulicaria arabica	Asteraceae	Plantae	119185
5	Ficus exasperata	Moraceae	Plantae	459060
6	Ficus mucuso	Moraceae	Plantae	309328
7	Ficus sur	Moraceae	Plantae	100575
8	Ficus vallis-choudae	Moraceae	Plantae	182131
9	Ficus variifolia	Moraceae	Plantae	425835
10	Euphorbia gaditana	Euphorbiaceae	Plantae	3990
11	Euphorbia retusa	Euphorbiaceae	Plantae	1091645
12	Eucalyptus camaledulensis	Myrtaceae	Plantae	34316
13	Rumex pictus	Polygonaceae	Plantae	1786036
14	Tamarix nilotica	Tamaricaceae	Plantae	189799
15	Vitis vinifera	Vitaceae	Plantae	29760

Showing of synonyms

Badaoui M, Magid A, et al. (2020). Antioxidant activity-guided isolation of constituents from Euphorbia gaditana Coss. and their antioxidant and tyrosinase inhibitory activities. Phytochemistry Letters, 2020, 39, 99-104. [View]
Marzouk MS, Moharram FA, et al. (2006). Antioxidant flavonol glycosides from Schinus molle. Phytotherapy Research,2006,20(3),200-205. [View] [PubMed]
Salib JY, Michael HN (2004). Cytotoxic phenylethanol glycosides from Psidium guaijava seeds. Phytochemistry,2004,65(14),2091-2093. [View] [PubMed]
Nawwar M, Souleman A, et al. (1984). Flavonoids of The Flowers of Tamarix nilotica. Phytochemistry,1984,23(10),2347–2349. [View]
Saleh NAM (1985). Flavonol glycosides of Euphorbia retusa and E. sanctae-catharinae. Phytochemistry,1985,24(2),371-372. [View]
El-negoumy SI, Mansour RMA, et al. (1982). Flavonols of Pulicaria arabica. Phytochemistry,1982,21(4),953-954. [View]
Greenham JR, Grayer RJ, et al. (2007). Intra-and interspecific variations in vacuolar flavonoids among Ficus species from the Budongo Forest, Uganda.. Biochemical systematics and ecology,2007,35(2),81-90. [View] [PubMed]
Singab A-N, Ayoub N, et al. (2011). Phenolic Constituents of Eucalyptus camaldulensis Dehnh, with Potential Antioxidant and Cytotoxic Activities. Records of Natural Products,2011,5(4),271-280. [View]
Elgamal A, El Raey M, et al. (2021). Phytochemical profiling and anti-aging activities of Euphorbia retusa extract: In silico and in vitro studies. Arabian Journal of Chemistry, 2021, 14(6), 103159. [View]
Elraey M, Elgamal A. (2022). Quercetin-3-O-β-D-glucouronide butyl ester from Vitis vinifera leaves of potent antihelicobacter pylori activity and impact of its combination with clarithromycin. Egypt. J. Chem,2022,65(10),609-615. [View]
El-Kashak W.A, Elshamy A.I, et al. (2017). Rumpictuside A: Unusual 9,10-anthraquinone glucoside from Rumex pictus Forssk. Carbohydrate research, 2017, 448, 74-78. [View] [PubMed]

Pubchem: 44259219

Nmrshiftdb2: 60026738

CPRiL: 91893

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 478.36 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 478.36 g/mol

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

Level: 1

Mol. Weight: 478.36 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.36 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.36 g/mol

Antibacterial

Antioxidant

Absorption

Caco-2 (logPapp): -6.82
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.79
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.55

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.94
Plasma Protein Binding: 80.82
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: 12.04
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.57
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.2
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.48
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: -151.43
Rat (Acute): 2.26
Rat (Chronic Oral): 4.25
Fathead Minnow: 3.81
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 677.25
Hydration Free Energy: -4.32
Log(D) at pH=7.4: -1.56
Log(P): 0.75
Log S: -3.8
Log(Vapor Pressure): -12.73
Melting Point: 218.13
pKa Acid: 3.6
pKa Basic: 8.0

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9755
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9755
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8981
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8981
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8940
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8940
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8917
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8917
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8894
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8894
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8845
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8845
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8639
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8639
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8597
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8597
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8408
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8408
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8377
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8377
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8301
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8301
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8298
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8298
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8274
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8274
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8203
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8203
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8061
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8061
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8028
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8028
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8022
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8022
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8022
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8022
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7997
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7997
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7919
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7919
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7910
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7910
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7909
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7909
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7866
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7866
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	3	0.7785
Acidic phospholipase A2 3	P60045	PA2A3_NAJSG	Naja sagittifera	3	0.7785
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7776
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7776
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7770
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7770
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7757
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7757
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.7676
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.7676
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7660
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7660
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7659
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7659
ADP-ribosyl-[dinitrogen reductase] hydrolase	A7XNI2	A7XNI2_AZOBR	Azospirillum brasilense	3	0.7651
ADP-ribosyl-[dinitrogen reductase] hydrolase	A7XNI2	A7XNI2_AZOBR	Azospirillum brasilense	3	0.7651
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7469
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7469
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7466
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7466
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7369
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7369
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7353
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7353
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7353
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7353
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7319
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7319
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7287
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7287
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7286
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7286
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	3	0.7247
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	3	0.7247
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7147
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7147
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7119
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7119
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7116
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7116
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7090
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7090
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7025
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7025
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7006
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7006

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