Chrysalodin - Compound Card

Chrysalodin

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Chrysalodin

Structure
Zoomed Structure
  • Family: Plantae - Liliaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Bisanthraquinone
Canonical Smiles OCc1cc(O)c2c(c1)C(O)(c1ccc3c(c1O)C(=O)c1c(C3=O)cc(cc1O)C)c1c(C2=O)c(O)ccc1
InChI InChI=1S/C30H20O9/c1-12-7-15-22(20(33)8-12)28(37)23-14(26(15)35)5-6-17(27(23)36)30(39)16-3-2-4-19(32)24(16)29(38)25-18(30)9-13(11-31)10-21(25)34/h2-10,31-34,36,39H,11H2,1H3
InChIKey DLKFSQPERBZZAT-UHFFFAOYSA-N
Formula C30H20O9
HBA 9
HBD 6
MW 524.48
Rotatable Bonds 2
TPSA 172.59
LogP 2.91
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.1
Exact Mass 524.11
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Kniphofia species Asphodelaceae Plantae 49723
2 Kniphofia species Liliaceae Plantae 49723

Showing of synonyms

  • Yenesew A, Wondimu A, et al. (1988). A comparative study of anthraquinones in rhizomes of Kniphofia species.. Biochemical systematics and ecology,1988,16(2),157-159. [View] [PubMed]
  • Dagne E, Berhanu E, et al. (1987). New bianthraquinone pigments from Kniphofia species. Bulletin of the Chemical Society of Ethiopia,1987,1(1),32-35. [View] [PubMed]
Pubchem: 13940829
Nmrshiftdb2: 70124544

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 524.48 g/mol

Structure

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

Level: 0

Mol. Weight: 524.48 g/mol

Structure

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

Level: 0

Mol. Weight: 524.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.23
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.02
Plasma Protein Binding
80.34
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
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
8.92
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.13
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.82
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.11
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
-2891.5
Rat (Acute)
2.47
Rat (Chronic Oral)
4.55
Fathead Minnow
14.3
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
586.67
Hydration Free Energy
-3.13
Log(D) at pH=7.4
2.57
Log(P)
5.41
Log S
-5.38
Log(Vapor Pressure)
-8.2
Melting Point
242.3
pKa Acid
8.9
pKa Basic
2.57
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 0.8733
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8733
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8671
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8671
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8573
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8573
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8563
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8563
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8246
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8246
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8229
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8229
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8182
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8182
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8180
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8180
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7950
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7950
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7767
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7767
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7625
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7625
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7502
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7502
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7468
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7468
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7436
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7436
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7435
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7435
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7423
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7423
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7304
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7304
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7231
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7231
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7123
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7123
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7039
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7039

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