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Gaboroquinone A

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

Canonical Smiles	OCc1cc(O)c2c(c1c1c(O)cc(c(c1OC)C(=O)C)O)C(=O)c1c(C2=O)c(O)ccc1
InChI	InChI=1S/C24H18O9/c1-9(26)16-14(29)7-15(30)20(24(16)33-2)17-10(8-25)6-13(28)19-21(17)22(31)11-4-3-5-12(27)18(11)23(19)32/h3-7,25,27-30H,8H2,1-2H3
InChIKey	KUDYATBIEOTCGT-UHFFFAOYSA-N
Formula	C₂₄H₁₈O₉
HBA	9
HBD	5
MW	450.4
Rotatable Bonds	4
TPSA	161.59
LogP	2.65
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.12
Exact Mass	450.1
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Bulbine frutescens	Asphodelaceae	Plantae	210954

Showing of synonyms

Bringmann G, Mutanyatta-Comar J, et al. (2008). Joziknipholones A and B: the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens. Chemistry: A European Journal,2008,14(5),1420-429. [View] [PubMed]

Pubchem: 10072444

Cas: 455884-21-6

Zinc: ZINC000015249254

Chebi: 65940

Nmrshiftdb2: 60063540

Metabolights: MTBLC65940

Chembl: CHEMBL483822

No compound-protein relationship available.

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4ccccc4

Level: 1

Mol. Weight: 450.4 g/mol

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 450.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 450.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.25
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.08
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.31

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.91
Plasma Protein Binding: 79.13
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-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: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.73
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.14
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.98
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.8
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: -99.39
Rat (Acute): 2.51
Rat (Chronic Oral): 3.99
Fathead Minnow: 4.67
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: 578.15
Hydration Free Energy: -3.58
Log(D) at pH=7.4: 2.32
Log(P): 3.98
Log S: -6.44
Log(Vapor Pressure): -8.65
Melting Point: 232.61
pKa Acid: 9.12
pKa Basic: 3.07

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8834
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8834
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8833
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8833
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8758
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8758
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8630
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8630
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.8547
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.8547
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8419
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8419
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8099
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8099
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7959
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7959
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7936
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7936
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7911
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7911
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7908
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7908
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7844
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7844
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7725
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7725
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7725
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7725
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7715
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7715
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7603
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7603
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7589
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7589
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7577
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7577
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7576
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7576
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7575
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7575
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7572
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7572
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7520
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7520
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7506
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7506
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7380
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7380
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	4	0.7354
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	4	0.7354
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7351
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7351
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7348
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7348
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	4	0.7333
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	4	0.7333
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	4	0.7261
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	4	0.7261
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	4	0.7242
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	4	0.7242
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7225
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7225
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7211
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7211
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7192
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7192
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7180
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7180
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	4	0.7159
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	4	0.7159
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7137
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7137
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	3	0.7121
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	3	0.7121
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7104
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7104
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7086
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7086
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7081
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7081
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7070
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7070
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7068
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7068
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7047
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7047
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7027
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7027
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7026
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7026
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7014
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7014

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