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5-hydroxyaloin A

Family: Plantae - Asphodelaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthrone

Canonical Smiles	OCc1cc(O)c2c(c1)[C@@H]([C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1c(C2=O)c(O)ccc1O
InChI	InChI=1S/C21H22O10/c22-5-7-3-8-13(11(26)4-7)18(28)16-10(25)2-1-9(24)15(16)14(8)21-20(30)19(29)17(27)12(6-23)31-21/h1-4,12,14,17,19-27,29-30H,5-6H2/t12-,14-,17-,19+,20-,21+/m1/s1
InChIKey	LJCDCYLYUCZUGL-UQBALUMJSA-N
Formula	C₂₁H₂₂O₁₀
HBA	10
HBD	8
MW	434.4
Rotatable Bonds	3
TPSA	188.14
LogP	-1.19
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	434.12
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aloe species	Asphodelaceae	Plantae	117795

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: 11972367

Cas: 138373-23-6

Zinc: ZINC000085508506

Chebi: 196623

Nmrshiftdb2: 60055367

No compound-protein relationship available.

SMILES: O1CCCCC1C(c(c23)cccc3)c4c(C2=O)cccc4

Level: 1

Mol. Weight: 434.4 g/mol

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 434.4 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 434.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.31
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -6.22
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.88

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.56
Plasma Protein Binding: 66.9
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: 11.47
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.18
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.69
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.11
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: -45.99
Rat (Acute): 2.5
Rat (Chronic Oral): 4.43
Fathead Minnow: 3.51
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 620.72
Hydration Free Energy: -8.45
Log(D) at pH=7.4: -1.07
Log(P): 0.03
Log S: -2.67
Log(Vapor Pressure): -12.1
Melting Point: 183.49
pKa Acid: 4.74
pKa Basic: 8.03

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8853
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8853
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8418
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8418
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7941
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7941
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7777
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7777
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7621
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7621
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7598
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7598
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7575
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7575
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7568
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7568
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7559
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7559
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7555
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7555
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7549
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7549
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7258
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7258
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7199
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7199
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7160
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7160
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7019
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7019

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