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Kelampayoside A

Family: Plantae - Sterculiaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenolic Glycoside

Canonical Smiles	COc1cc(O[C@@H]2O[C@H](CO[C@@H]3OC[C@]([C@H]3O)(O)CO)[C@H]([C@@H]([C@H]2O)O)O)cc(c1OC)OC
InChI	InChI=1S/C20H30O13/c1-27-10-4-9(5-11(28-2)16(10)29-3)32-18-15(24)14(23)13(22)12(33-18)6-30-19-17(25)20(26,7-21)8-31-19/h4-5,12-15,17-19,21-26H,6-8H2,1-3H3/t12-,13-,14+,15-,17+,18-,19-,20-/m1/s1
InChIKey	CKGKQISENBKOCA-FHXQZXMCSA-N
Formula	C₂₀H₃₀O₁₃
HBA	13
HBD	6
MW	478.45
Rotatable Bonds	9
TPSA	185.99
LogP	-2.64
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.7
Exact Mass	478.17
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Strychnos cocculoides	Loganiaceae	Plantae	1040870
2	Sterculia setigera	Sterculiaceae	Plantae	66667

Showing of synonyms

Andima M, Coghi P, et al. (2021). Chemical constituents and biological activities of African medicinal tree Sterculia setigera Delile stem bark. South African Journal of Botany, 2021, 143, 274-281. [View]
Sunghwa F, Koketsu M. (2009). Phenolic and bis-iridoid glycosides from Strychnos cocculoides.. Natural Product Research,2009,23(15),1408-4015. [View] [PubMed]

Pubchem: 10552637

Cas: 87562-76-3

Zinc: ZINC000038322012

Chebi: 68963

Nmrshiftdb2: 60026056

Metabolights: MTBLC68963

Chembl: CHEMBL1923077

No compound-protein relationship available.

SMILES: O1CCCC1OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 478.45 g/mol

SMILES: O1CCCCC1COC2CCCO2

Level: 1

Mol. Weight: 478.45 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 478.45 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.45 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.45 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 478.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.07
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.210
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.740
Plasma Protein Binding: 63.95
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: 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: 5.750
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.940
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.060
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.800
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: -110.730
Rat (Acute): 2.170
Rat (Chronic Oral): 3.880
Fathead Minnow: 3.490
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: 502.790
Hydration Free Energy: -3.850
Log(D) at pH=7.4: -0.680
Log(P): -1.72
Log S: -2.29
Log(Vapor Pressure): -13.75
Melting Point: 165.66
pKa Acid: 5.85
pKa Basic: 2.14

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8901
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8901
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8755
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8755
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8519
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8519
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8467
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8467
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8420
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8420
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8250
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8250
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8186
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8186
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7870
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7870
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7780
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7780
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7533
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7533
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7467
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7467
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7457
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7457
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7447
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7447
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7432
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7432
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7401
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7401
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7387
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7387
GMP synthase [glutamine-hydrolyzing]	Q8IJR9	Q8IJR9_PLAF7	Plasmodium falciparum	5	0.7382
GMP synthase [glutamine-hydrolyzing]	Q8IJR9	Q8IJR9_PLAF7	Plasmodium falciparum	5	0.7382
16S rRNA (guanine(1405)-N(7))-methyltransferase	Q763K9	Q763K9_ECOLX	Escherichia coli	3	0.7353
16S rRNA (guanine(1405)-N(7))-methyltransferase	Q763K9	Q763K9_ECOLX	Escherichia coli	3	0.7353
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7306
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7306
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7279
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7279
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7269
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7269
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7269
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7269
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7228
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7228
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7222
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7222
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7190
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7190
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7189
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7189
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7174
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7174
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7128
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7128
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7097
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7097
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7084
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7084
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7074
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7074
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7063
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7063
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7018
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7018
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7008
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7008

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