(P)-8,9,1',8'-tetrahydroxy-3,3'-dimethyl[10,7'-bianthracene]-1,4,9',10'-tetraone - Compound Card

(P)-8,9,1',8'-tetrahydroxy-3,3'-dimethyl[10,7'-bianthracene]-1,4,9',10'-tetraone

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(P)-8,9,1',8'-tetrahydroxy-3,3'-dimethyl[10,7'-bianthracene]-1,4,9',10'-tetraone

Structure
Zoomed Structure
  • 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)c1c2C(=O)C(=CC(=O)c2c(c2c1cccc2O)O)C
InChI InChI=1S/C30H18O8/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/h3-10,31-32,36,38H,1-2H3
InChIKey MFTDXOCBTJZGKK-UHFFFAOYSA-N
Formula C30H18O8
HBA 8
HBD 4
MW 506.47
Rotatable Bonds 1
TPSA 149.2
LogP 4.74
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 506.1
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: 12182448
Nmrshiftdb2: 70090283

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(=O)c(c12)cc3c(cccc3)c2-c(c4)ccc(c45)C(=O)c6c(C5=O)cccc6

Level: 1

Mol. Weight: 506.47 g/mol

Structure

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

Level: 0

Mol. Weight: 506.47 g/mol

Structure

SMILES: O=C1C=CC(=O)c(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 506.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.57
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.88
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.26
Plasma Protein Binding
86.33
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
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
6.44
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.8
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.42
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
-1785.37
Rat (Acute)
2.63
Rat (Chronic Oral)
3.81
Fathead Minnow
11.64
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
618.16
Hydration Free Energy
-3.14
Log(D) at pH=7.4
3.48
Log(P)
6.23
Log S
-8.38
Log(Vapor Pressure)
-9.72
Melting Point
313.71
pKa Acid
5.54
pKa Basic
3.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9294
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9294
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9064
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9064
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9033
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9033
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8906
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8906
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8903
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8903
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8680
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8680
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8547
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8547
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8156
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8156
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8037
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8037
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7948
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7948
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7839
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7839
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7820
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7820
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7793
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7793
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7733
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7733
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7671
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7671
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7490
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7490
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7407
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7407
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7226
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7226
Serine/threonine-protein kinase VRK1 Q99986 VRK1_HUMAN Homo sapiens 4 0.7141
Serine/threonine-protein kinase VRK1 Q99986 VRK1_HUMAN Homo sapiens 4 0.7141
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7084
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7084
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7070
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7070

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