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Aloenin-2''-p-coumaroyl ester

Family: Plantae - Asphodelaceae
Kingdom: Plantae
Class: Coumarin

Canonical Smiles	OC[C@H]1O[C@@H](Oc2cc(O)cc(c2c2cc(OC)cc(=O)o2)C)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(cc1)O
InChI	InChI=1S/C28H28O12/c1-14-9-17(31)10-19(24(14)20-11-18(36-2)12-23(33)37-20)38-28-27(26(35)25(34)21(13-29)39-28)40-22(32)8-5-15-3-6-16(30)7-4-15/h3-12,21,25-31,34-35H,13H2,1-2H3/b8-5+/t21-,25-,26+,27-,28-/m1/s1
InChIKey	AVKZBTISTJWNNL-MKNNQNITSA-N
Formula	C₂₈H₂₈O₁₂
HBA	12
HBD	5
MW	556.52
Rotatable Bonds	8
TPSA	185.35
LogP	1.48
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	556.16
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aloe nyeriensis	Asphodelaceae	Plantae	117806

Showing of synonyms

Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]

Pubchem: 14211227

Cas: 106533-35-1

Zinc: ZINC000136252009

Nmrshiftdb2: 70083165

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(cccc3)c3-c4cccc(=O)o4

Level: 3

Mol. Weight: 556.52 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc3ccccc3

Level: 2

Mol. Weight: 556.52 g/mol

SMILES: O=c(o1)cccc1-c2c(cccc2)OC3CCCCO3

Level: 2

Mol. Weight: 556.52 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 556.52 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 556.52 g/mol

SMILES: c1ccccc1-c2cccc(=O)o2

Level: 1

Mol. Weight: 556.52 g/mol

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 556.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 556.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 556.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.63
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.850
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.9

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.040
Plasma Protein Binding: 78.67
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: 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: 9.820
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.340
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.910
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.860
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: -3199.860
Rat (Acute): 2.290
Rat (Chronic Oral): 3.690
Fathead Minnow: 13.510
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 525.920
Hydration Free Energy: -2.990
Log(D) at pH=7.4: 1.900
Log(P): 2.1
Log S: -4.48
Log(Vapor Pressure): -9.87
Melting Point: 190.11
pKa Acid: 7.12
pKa Basic: 3.22

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9611
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9611
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9258
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9258
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.9204
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.9204
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8945
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8945
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8890
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8890
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	4	0.8869
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	4	0.8869
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8784
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8784
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8762
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8762
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8640
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8640
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8581
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8581
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8543
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8543
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8541
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8541
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8413
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8413
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8393
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8393
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8327
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8327
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8316
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8316
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8265
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8265
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8147
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8147
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8098
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8098
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8079
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8079
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8066
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8066
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8052
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8052
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8032
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8032
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8032
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8032
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.8005
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.8005
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7921
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7921
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7782
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7782
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7769
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7769
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7673
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7673
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	4	0.7663
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	4	0.7663
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7591
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7591
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7574
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7574
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7555
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7555
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7545
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7545
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7494
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7494
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7431
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7431
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7431
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7431
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7428
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7428
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7387
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7387
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7372
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7372
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7341
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7341
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7325
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7325
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7317
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7317
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7306
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7306
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7300
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7300
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7299
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7299
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7259
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7259
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7236
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7236
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7223
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7223
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7203
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7203
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7203
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7203
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7195
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7195
Biphenyl-2,3-diol 1,2-dioxygenase	P47228	BPHC_PARXL	Paraburkholderia xenovorans	4	0.7191
Biphenyl-2,3-diol 1,2-dioxygenase	P47228	BPHC_PARXL	Paraburkholderia xenovorans	4	0.7191
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7184
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7184
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7179
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7179
Myosin heavy chain, striated muscle	P24733	MYS_ARGIR	Argopecten irradians	3	0.7177
Myosin heavy chain, striated muscle	P24733	MYS_ARGIR	Argopecten irradians	3	0.7177
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7137
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7137
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7134
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7134
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7133
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7133
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7104
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7104
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	3	0.7088
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	3	0.7088
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7084
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7084
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7075
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7075
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7075
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7075
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7070
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7070
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	3	0.7055
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	3	0.7055
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.7040
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.7040
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7036
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7036
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7012
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7012
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7009
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7009
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7003
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7003

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