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(10R)-1,4,8,1',8'-pentahydroxy-3,3'-dimethyl-[10,7'-bianthracene]-9,9',10'(10H)-trione

Family: Plantae - Asphodelaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Dimeric Anthracene Derivative

Canonical Smiles	Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)c(cc1)[C@H]1c2cccc(c2C(=O)c2c1c(O)c(C)cc2O)O
InChI	InChI=1S/C30H20O8/c1-11-8-16-22(18(32)9-11)29(37)23-15(27(16)35)7-6-14(28(23)36)20-13-4-3-5-17(31)21(13)30(38)24-19(33)10-12(2)26(34)25(20)24/h3-10,20,31-34,36H,1-2H3/t20-/m1/s1
InChIKey	WABMKKXLXIGLEO-HXUWFJFHSA-N
Formula	C₃₀H₂₀O₈
HBA	8
HBD	5
MW	508.48
Rotatable Bonds	1
TPSA	152.36
LogP	4.33
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	38
Formal Charge	0
Fraction CSP3	0.1
Exact Mass	508.12
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Bulbine abyssinica	Asphodelaceae	Plantae	2511937

Showing of synonyms

Wanjohi JM, Yenesew A, et al. (2005). Three dimeric anthracene derivatives from the fruits of Bulbine abyssinica. Tetrahedron,2005,61(10),2667-2674. [View] [PubMed]

Pubchem: 12182449

No compound-protein relationship available.

SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)C(c(c45)cccc5)c6c(C4=O)cccc6

Level: 1

Mol. Weight: 508.48 g/mol

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

Level: 0

Mol. Weight: 508.48 g/mol

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

Level: 0

Mol. Weight: 508.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.04
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.04
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.22
Plasma Protein Binding: 94.44
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: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.06
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.43
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.01
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.02
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: -1787.05
Rat (Acute): 2.53
Rat (Chronic Oral): 3.88
Fathead Minnow: 10.72
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: 614.45
Hydration Free Energy: -3.15
Log(D) at pH=7.4: 3.42
Log(P): 6.36
Log S: -7.4
Log(Vapor Pressure): -9.24
Melting Point: 290.05
pKa Acid: 6.09
pKa Basic: 4.92

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8869
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8869
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8686
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8686
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8571
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8571
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8370
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8370
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8220
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8220
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8144
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8144
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7663
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7663
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7643
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7643
Glutathione S-transferase A1	P08263	GSTA1_HUMAN	Homo sapiens	2	0.7501
Glutathione S-transferase A1	P08263	GSTA1_HUMAN	Homo sapiens	2	0.7501
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7488
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7488
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7330
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7330
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7319
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7319
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.7318
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.7318
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7316
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7316
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7253
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7253
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7211
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7211
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7012
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7012

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