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Gaboroquinone B

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

Canonical Smiles	OCc1cc(O)c2c(c1c1c(O)cc(c(c1O)C(=O)C)OC)C(=O)c1c(C2=O)c(O)ccc1
InChI	InChI=1S/C24H18O9/c1-9(26)16-15(33-2)7-14(29)19(23(16)31)17-10(8-25)6-13(28)20-21(17)22(30)11-4-3-5-12(27)18(11)24(20)32/h3-7,25,27-29,31H,8H2,1-2H3
InChIKey	XBZFXAYXSQAPPD-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: 636652

Cas: 455884-25-0

Zinc: ZINC000015249257

Nmrshiftdb2: 2432

Chembl: CHEMBL484021

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): -6.34
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: 0.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.91
Plasma Protein Binding: 79.96
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: 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: 10.58
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.06
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.0
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.15
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: -101.04
Rat (Acute): 2.54
Rat (Chronic Oral): 4.06
Fathead Minnow: 4.63
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: 578.79
Hydration Free Energy: -3.45
Log(D) at pH=7.4: 2.16
Log(P): 3.95
Log S: -6.5
Log(Vapor Pressure): -8.81
Melting Point: 230.45
pKa Acid: 8.01
pKa Basic: 3.18

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.9369
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.9369
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8905
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8905
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8544
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8544
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8297
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8297
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7996
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7996
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7937
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7937
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7831
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7831
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	4	0.7706
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	4	0.7706
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7704
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7704
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7660
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7660
L-malyl-CoA/beta-methylmalyl-CoA lyase	Q3J5L6	MCAL_RHOS4	Cereibacter sphaeroides	4	0.7651
L-malyl-CoA/beta-methylmalyl-CoA lyase	Q3J5L6	MCAL_RHOS4	Cereibacter sphaeroides	4	0.7651
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7636
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7636
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7623
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7623
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7609
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7609
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7572
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7572
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7431
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7431
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	4	0.7413
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	4	0.7413
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7375
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7375
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7362
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7362
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7344
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7344
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7324
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7324
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7235
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7235
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7217
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7217
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7186
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7186
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.7169
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.7169
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	2	0.7093
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	2	0.7093
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7076
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7076
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7025
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7025
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7007
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7007

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