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22alpha-acetyl-16alpha,21beta-dihydroxyoleanane-13beta:28-olide 3-O-[beta-glucopyranosyl-(1'''→6')][6''-O-coumaroylglucopyranosyl-(1''→2')]-beta-glucopyranoside

Family: Plantae - Myrsinaceae
Kingdom: Plantae
Class: Terpenoid

Canonical Smiles	OC[C@H]1OC(OC[C@H]2OC(O[C@H]3CC[C@]4(C(C3(C)C)CC[C@@]3(C4CC[C@]45[C@@]3(C)CC([C@@]3(C5CC(C)(C)[C@H]([C@@H]3OC(=O)C)O)C(=O)O4)O)C)C)[C@@H]([C@H]([C@@H]2O)O)OC2O[C@H](COC(=O)/C=C/c3ccc(cc3)O)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C59H86O24/c1-26(61)77-48-47(73)53(2,3)21-34-58-20-16-33-55(6)18-17-36(54(4,5)32(55)15-19-56(33,7)57(58,8)22-35(63)59(34,48)52(74)83-58)81-51-46(43(70)40(67)31(80-51)25-76-49-44(71)41(68)38(65)29(23-60)78-49)82-50-45(72)42(69)39(66)30(79-50)24-75-37(64)14-11-27-9-12-28(62)13-10-27/h9-14,29-36,38-51,60,62-63,65-73H,15-25H2,1-8H3/b14-11+/t29-,30-,31-,32?,33?,34?,35?,36+,38-,39-,40-,41+,42+,43+,44-,45-,46-,47+,48+,49?,50?,51?,55+,56-,57+,58+,59-/m1/s1
InChIKey	FVETWVZIZYYQDT-AJBOBDSLSA-N
Formula	C₅₉H₈₆O₂₄
HBA	24
HBD	12
MW	1179.31
Rotatable Bonds	13
TPSA	377.04
LogP	-0.17
Number Rings	10
Number Aromatic Rings	1
Heavy Atom Count	83
Formal Charge	0
Fraction CSP3	0.81
Exact Mass	1178.55
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Maesa lanceolata	Myrsinaceae	Plantae	992730

Showing of synonyms

Manguro LO, Midiwo JO, et al. (2011). Triterpene saponins of Maesa lanceolata leaves.. Arkivoc,2011,ii,172-198. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC(CCC3COC4CCCCO4)C(O3)OC(CC5)CC(CC6)C5C(CC7)C6C(CC8)C7(OC9=O)C(C189)CCCC1

Level: 4

Mol. Weight: 1179.31 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC3C(OCCC3)OC(CC4)CC(CC5)C4C(CC6)C5C(CC7)C6(OC8=O)C(C789)CCCC9

Level: 3

Mol. Weight: 1179.31 g/mol

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)OC(CC4)CC(CC5)C4C(CC6)C5C(CC7)C6(OC8=O)C(C789)CCCC9

Level: 3

Mol. Weight: 1179.31 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC(CO3)CCC3COC4CCCCO4

Level: 3

Mol. Weight: 1179.31 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC(CC3)CC(CC4)C3C(CC5)C4C(CC6)C5(OC7=O)C(C678)CCCC8

Level: 2

Mol. Weight: 1179.31 g/mol

SMILES: C1CCCC(C123)C4(OC2=O)C(CC3)C5C(CC4)C6C(CC5)CC(CC6)OC(OCCC7)C7OC8CCCCO8

Level: 2

Mol. Weight: 1179.31 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC3CCCOC3

Level: 2

Mol. Weight: 1179.31 g/mol

SMILES: O1CCCCC1OCC2CCC(CO2)OC3CCCCO3

Level: 2

Mol. Weight: 1179.31 g/mol

SMILES: C1CCCC(C123)C4(OC2=O)C(CC3)C5C(CC4)C6C(CC5)CC(CC6)OC7CCCCO7

Level: 1

Mol. Weight: 1179.31 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 1179.31 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 1179.31 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 1179.31 g/mol

SMILES: C1CCCC(C123)C4(OC2=O)C(CC3)C5C(CC4)C6C(CC5)CCCC6

Level: 0

Mol. Weight: 1179.31 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1179.31 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1179.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.38
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 6290938751.84
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 822151346501.78

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.54
Plasma Protein Binding: 68.0
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: Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 2.48
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -19121377952.67
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -7807.89
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -1492165058039299.5
Rat (Acute): 4.29
Rat (Chronic Oral): 3200564.09
Fathead Minnow: 1883540734717.88
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 167827221664862.9
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -93295174.34
Log(P): -10859.1
Log S: -3.53
Log(Vapor Pressure): -5526464999961.38
Melting Point: -1675794.14
pKa Acid: -40269029773.37
pKa Basic: -323962996.08

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.9177
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.9177
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8166
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8166
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7853
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7853
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7795
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7795
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7523
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7523
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7513
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7513
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7400
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7400
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7372
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7372
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7311
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7311
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7295
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7295
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7276
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7276
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7254
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7254
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7254
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7254
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7244
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7244
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7232
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7232
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7206
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7206
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7206
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7206
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7195
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7195
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7153
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7153
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7114
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7114
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7112
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7112
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7097
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7097
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7093
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7093
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7084
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7084
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7084
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7084
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7079
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7079
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7050
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7050
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7049
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7049
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7047
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7047
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7044
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7044
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7031
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7031
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7031
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7031
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7030
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7030
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7024
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7024
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7022
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7022
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7013
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7013
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7011
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7011
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7010
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7010
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7009
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7009
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7006
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7006

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