Asphodelin - Compound Card

Asphodelin

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Asphodelin

Structure
Zoomed Structure
  • Family: Plantae - Liliaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Bisanthraquinone/Anthrone
Canonical Smiles Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)c(cc1)c1c(C)cc(c2c1C(=O)c1cccc(c1C2=O)O)O
InChI InChI=1S/C30H18O8/c1-11-8-16-22(18(32)9-11)29(37)23-15(26(16)34)7-6-14(27(23)35)20-12(2)10-19(33)24-25(20)28(36)13-4-3-5-17(31)21(13)30(24)38/h3-10,31-33,35H,1-2H3
InChIKey BXWGUDGILDGCGB-UHFFFAOYSA-N
Formula C30H18O8
HBA 8
HBD 4
MW 506.47
Rotatable Bonds 1
TPSA 149.2
LogP 4.34
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 Kniphofia foliosa Asphodelaceae Plantae 214838
2 Aloe secundiflora Asphodelaceae Plantae 1593107
3 Aloe saponaria Asphodelaceae Plantae 1155789
4 Aloe species Liliaceae Plantae 117795

Showing of synonyms

  • Dagne E, Yenesew A, et al. (1994). Anthraquinones, pre-anthraquinones and isoeleutherol in the roots of Aloe species.. Phytochemistry,1994,35(2),401-406. [View] [PubMed]
  • Induli M, Gebru M, et al. (2013). Antiplasmodial Quinones from the Rhizomes of Kniphofia foliosa. Natural Product Communications,2013,8(9),1261-1264. [View] [PubMed]
  • Induli M, Cheloti M, et al. (2012). Naphthoquinones from the roots of Aloe secundiflora. Phytochemistry Letters,2012,5(3),506-509. [View] [PubMed]
  • Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]
Pubchem: 182665
Nmrshiftdb2: 60060455

No compound-protein relationship available.

Structure

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

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.68
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.23
Plasma Protein Binding
88.52
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
7.21
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.74
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
6.18
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
-1776.78
Rat (Acute)
2.58
Rat (Chronic Oral)
3.55
Fathead Minnow
11.55
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
618.48
Hydration Free Energy
-3.11
Log(D) at pH=7.4
3.3
Log(P)
7.1
Log S
-7.89
Log(Vapor Pressure)
-9.94
Melting Point
331.08
pKa Acid
6.55
pKa Basic
3.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9250
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9250
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8839
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8839
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8748
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8748
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8394
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8394
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8350
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8350
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8285
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8285
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8276
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8276
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7844
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7844
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7593
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7593
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7573
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7573
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7572
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7572
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7533
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7533
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7481
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7481
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7447
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7447
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7442
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7442
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7253
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7253
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7248
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7248
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7244
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7244
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7192
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7192
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7139
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7139
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7138
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7138
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7127
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7127
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7120
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7120
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7105
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7105
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7087
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7087
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7040
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7040
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 4 0.7023
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 4 0.7023

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