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Aloenin

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)O
InChI	InChI=1S/C19H22O10/c1-8-3-9(21)4-11(15(8)12-5-10(26-2)6-14(22)27-12)28-19-18(25)17(24)16(23)13(7-20)29-19/h3-6,13,16-21,23-25H,7H2,1-2H3/t13-,16-,17+,18-,19-/m1/s1
InChIKey	KFJNVVJUICKJEQ-LQDZTQBFSA-N
Formula	C₁₉H₂₂O₁₀
HBA	10
HBD	5
MW	410.38
Rotatable Bonds	5
TPSA	159.05
LogP	-0.49
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	410.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aloe nyeriensis	Asphodelaceae	Plantae	117806
2	Aloe arborescens	Asphodelaceae	Plantae	45385

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: 162305

Cas: 38412-46-3

Gnps: CCMSLIB00006408290

Zinc: ZINC000006070013

Chebi: 176869

Nmrshiftdb2: 60028057

Comptox: DTXSID10191751

CPRiL: 113685

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

Level: 2

Mol. Weight: 410.38 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 410.38 g/mol

SMILES: c1ccccc1-c2cccc(=O)o2

Level: 1

Mol. Weight: 410.38 g/mol

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 410.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 410.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 410.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.03
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.160
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.55

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.950
Plasma Protein Binding: 74.55
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: 7.290
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.270
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.010
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.500
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: -13.630
Rat (Acute): 2.280
Rat (Chronic Oral): 3.530
Fathead Minnow: 4.120
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: 534.800
Hydration Free Energy: -12.250
Log(D) at pH=7.4: 0.320
Log(P): -0.42
Log S: -3.0
Log(Vapor Pressure): -11.35
Melting Point: 178.72
pKa Acid: 5.37
pKa Basic: 6.07

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	0.9640
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9640
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.9052
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.9052
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.9044
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.9044
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8932
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8932
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8740
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8740
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8627
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8627
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8569
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8569
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.8367
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.8367
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8272
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8272
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8217
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8217
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8200
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8200
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8103
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8103
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7956
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7956
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7921
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7921
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.7808
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.7808
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7797
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7797
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7781
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7781
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7757
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7757
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7709
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7709
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7707
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7707
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7695
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7695
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7668
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7668
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7628
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7628
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7598
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7598
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7548
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7548
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7531
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7531
Biphenyl-2,3-diol 1,2-dioxygenase	P47228	BPHC_PARXL	Paraburkholderia xenovorans	4	0.7504
Biphenyl-2,3-diol 1,2-dioxygenase	P47228	BPHC_PARXL	Paraburkholderia xenovorans	4	0.7504
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7503
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7503
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7487
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7487
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7442
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7442
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7420
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7420
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7414
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7414
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7352
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7352
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7352
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7352
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7336
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7336
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7318
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7318
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7318
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7318
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7294
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7294
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7290
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7290
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7287
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7287
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7277
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7277
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	3	0.7235
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	3	0.7235
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7234
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7234
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7221
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7221
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7190
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7190
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7184
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7184
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7175
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7175
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7175
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7175
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7165
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7165
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7148
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7148
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7144
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7144
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7080
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7080
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7076
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7076
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7072
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7072
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7057
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7057
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7036
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7036

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