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Atrisemibaccatoside A

Family: Plantae - Chenopodiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Triglycoside

Canonical Smiles	OC[C@H]1OC([C@@H]([C@H]1O)O)O[C@@H]1[C@H](O)C(OC[C@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(c(c3)OC)O)[C@@H]([C@H]([C@@H]2O)O)O)O[C@@H]([C@H]1O)C
InChI	InChI=1S/C33H40O20/c1-10-20(38)29(52-32-25(43)21(39)17(8-34)50-32)27(45)31(48-10)47-9-18-22(40)24(42)26(44)33(51-18)53-30-23(41)19-14(37)6-12(35)7-16(19)49-28(30)11-3-4-13(36)15(5-11)46-2/h3-7,10,17-18,20-22,24-27,29,31-40,42-45H,8-9H2,1-2H3/t10-,17-,18-,20-,21+,22-,24+,25-,26-,27+,29+,31?,32?,33+/m1/s1
InChIKey	HXCBAFYNILFOMA-FRLZAUQLSA-N
Formula	C₃₃H₄₀O₂₀
HBA	20
HBD	11
MW	756.66
Rotatable Bonds	10
TPSA	317.35
LogP	-2.92
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	Atriplex semibaccata	Chenopodiaceae	Plantae	417609

Showing of synonyms

Elshamy A, Mohamed T, et al. (2019). New phenolics, cytotoxicity and chemosystematic significance of Atriplex semibaccata. Phytochemistry Letters, 2019, 34, 74-78. [View]

No compound-protein relationship available.

SMILES: O1CCCC1OC2CC(OCC2)OCC3CCCC(O3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 756.66 g/mol

SMILES: O1CCCC1OC2CC(OCC2)OCC3CCCC(O3)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 756.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 756.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 756.66 g/mol

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

Level: 2

Mol. Weight: 756.66 g/mol

SMILES: O1CCCCC1COC(OCC2)CC2OC3CCCO3

Level: 2

Mol. Weight: 756.66 g/mol

SMILES: c1cccc(c12)occ(c2=O)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: O1CCCC1OC2CCOCC2

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

SMILES: C1CCOC1

Level: 0

Mol. Weight: 756.66 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: 2.620
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 1172.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.750
Plasma Protein Binding: 50.18
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: 9.430
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -26.420
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.680
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.790
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: -2123722.430
Rat (Acute): 2.390
Rat (Chronic Oral): 4.680
Fathead Minnow: 2687.950
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: 232071.920
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -0.800
Log(P): -1.09
Log S: -4.9
Log(Vapor Pressure): -7610.35
Melting Point: 214.73
pKa Acid: -22.48
pKa Basic: 4.9

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9599
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9110
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9085
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9075
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8884
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8834
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8791
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8581
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8433
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8415
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8358
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8173
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8150
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8043
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8038
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8021
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7900
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7900
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7894
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7885
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7883
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7850
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7794
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7751
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7741
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7737
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7729
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7669
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7627
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7577
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7503
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7499
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7431
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7396
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7250
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7247
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7219
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7193
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7163
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7147
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7137
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7114
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7089
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7040
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7021
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7010
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7004
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7004

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