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Robustaside A

Family: Plantae - Phyllanthaceae-Euphorbiaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenolic Glycoside

Canonical Smiles	O=C(/C=C/c1ccc(cc1)O)OC[C@H]1OC(Oc2ccc(c(c2C)C)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C23H26O9/c1-12-13(2)17(9-8-16(12)25)31-23-22(29)21(28)20(27)18(32-23)11-30-19(26)10-5-14-3-6-15(24)7-4-14/h3-10,18,20-25,27-29H,11H2,1-2H3/b10-5+/t18-,20-,21+,22-,23?/m1/s1
InChIKey	HJSVKCKJGOVSJG-MCQNMBRLSA-N
Formula	C₂₃H₂₆O₉
HBA	9
HBD	5
MW	446.45
Rotatable Bonds	6
TPSA	145.91
LogP	1.16
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	446.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Phyllanthus atropurpureus	Phyllanthaceae-Euphorbiaceae	Plantae	634324
2	Phyllanthus atropurpureus	Phyllanthaceae-Euphorbiaceae	Plantae	634324

Showing of synonyms

Sarg T, Abdel- Ghani A, et al. (2012). Bioactive compounds from Phyllanthus atropurpureus. Journal of Natural Products,2012,5,10-20. [View]
Sarg T, El Sayed A, et al. (2011). Bioactive compounds from Phyllanthus atropurpureus Bojer cultivated in Egypt. Planta Medica,2011,77-PL56. [View]

Pubchem: 162817130

Nmrshiftdb2: 70070121

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 446.45 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 446.45 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 446.45 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 446.45 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 446.45 g/mol

Antimicrobial

Antitumor

Absorption

Caco-2 (logPapp): -6.68
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.94
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.79

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.92
Plasma Protein Binding: 71.95
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: 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: 11.64
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.39
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.75
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.5
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: -56.62
Rat (Acute): 2.14
Rat (Chronic Oral): 3.58
Fathead Minnow: 4.17
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 516.14
Hydration Free Energy: -4.07
Log(D) at pH=7.4: 2.23
Log(P): 2.14
Log S: -3.69
Log(Vapor Pressure): -10.21
Melting Point: 188.69
pKa Acid: 6.79
pKa Basic: 2.87

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.9291
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.9291
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8957
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8957
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8853
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8853
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8747
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8747
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8719
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8719
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	3	0.8701
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	3	0.8701
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8643
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8643
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8352
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8352
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8297
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8297
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8285
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8285
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8279
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8279
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8223
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8223
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8199
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8199
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8038
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8038
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8005
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8005
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.7782
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.7782
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7778
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7778
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7746
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7746
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7729
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7729
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7643
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7643
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7630
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7630
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7611
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7611
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7599
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7599
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	3	0.7582
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7582
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	3	0.7582
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7582
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7510
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7510
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7491
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7491
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7466
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7466
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7425
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7425
Nitroreductase domain-containing protein	Q8DW21	Q8DW21_STRMU	Streptococcus mutans serotype c	3	0.7419
Nitroreductase domain-containing protein	Q8DW21	Q8DW21_STRMU	Streptococcus mutans serotype c	3	0.7419
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7392
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7392
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7391
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7391
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7370
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7370
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7333
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7333
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7316
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7316
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7294
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7294
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7273
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7273
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7260
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7260
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7246
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7246
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7234
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7234
Probable bifunctional SAT/APS kinase	O67174	SATC_AQUAE	Aquifex aeolicus	3	0.7204
Probable bifunctional SAT/APS kinase	O67174	SATC_AQUAE	Aquifex aeolicus	3	0.7204
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7169
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7169
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7149
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7149
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7108
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7108
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7091
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7091
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7089
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7089
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7086
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7086
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7077
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7077
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7067
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7067
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	4	0.7040
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	4	0.7040
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7030
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7030
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7003
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7003

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