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Isofoliosone

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

Canonical Smiles	COc1c(C(=O)C)c(O)cc(c1C1(O)c2cccc(c2C(=O)c2c1cc(C)cc2O)O)O
InChI	InChI=1S/C24H20O8/c1-10-7-13-20(15(27)8-10)22(30)19-12(5-4-6-14(19)26)24(13,31)21-17(29)9-16(28)18(11(2)25)23(21)32-3/h4-9,26-29,31H,1-3H3
InChIKey	YYRWFFHWAITJEB-UHFFFAOYSA-N
Formula	C₂₄H₂₀O₈
HBA	8
HBD	5
MW	436.42
Rotatable Bonds	3
TPSA	144.52
LogP	2.86
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.17
Exact Mass	436.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Kniphofia foliosa	Asphodelaceae	Plantae	214838

Showing of synonyms

Yenesew A, Dagne E, et al. (1994). An anthrone, an anthraquinone and two oxanthrones from Kniphofia foliosa. Phytochemistry,1994,37(2),525-528. [View] [PubMed]

Pubchem: 101674078

No compound-protein relationship available.

SMILES: c1ccccc1C(c(c23)cccc3)c4c(C2=O)cccc4

Level: 1

Mol. Weight: 436.42 g/mol

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

Level: 0

Mol. Weight: 436.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 436.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.13
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.210
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.26

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.980
Plasma Protein Binding: 79.34
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.190
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.090
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.930
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.540
Micronucleos: Toxic
NR-AhR: Toxic
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: -51.490
Rat (Acute): 2.430
Rat (Chronic Oral): 4.070
Fathead Minnow: 4.380
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 523.840
Hydration Free Energy: -5.290
Log(D) at pH=7.4: 2.910
Log(P): 4.58
Log S: -5.79
Log(Vapor Pressure): -7.87
Melting Point: 228.21
pKa Acid: 11.27
pKa Basic: 3.83

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8957
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8957
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8912
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8912
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8434
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8434
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8309
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8309
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	3	0.8255
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	3	0.8255
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8098
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8098
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7693
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7693
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	4	0.7589
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	4	0.7589
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7414
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7414
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7330
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7330
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7320
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7320
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7308
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7308
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7217
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7217
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7160
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7160
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7142
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7142
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7058
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7058

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