Scandenone - Compound Card

Scandenone

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Scandenone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles CC(=CCc1c2OC(C)(C)C=Cc2c(c2c1occ(c2=O)c1ccc(cc1)O)O)C
InChI InChI=1S/C25H24O5/c1-14(2)5-10-18-23-17(11-12-25(3,4)30-23)21(27)20-22(28)19(13-29-24(18)20)15-6-8-16(26)9-7-15/h5-9,11-13,26-27H,10H2,1-4H3
InChIKey HGHOPAZIUPORIN-UHFFFAOYSA-N
Formula C25H24O5
HBA 5
HBD 2
MW 404.46
Rotatable Bonds 3
TPSA 79.9
LogP 5.56
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 404.16
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina mildbraedii Leguminosae/Fabaceae Plantae 2708827
2 Erythrina addisoniae Leguminosae/Fabaceae Plantae 2590682

Showing of synonyms

  • Talla E, Yankep E, et al. (2014). Chemical constituents from root barks of Erythrina mildbraedii and stem barks of Erythrina addisoniae. Bull. Chem. Soc. Ethiop. 2014, 28(1), 155-159. [View]
  • Tchokouaha RF, Alexi X, et al. (2010). Erymildbraedin A and B, two novel cytotoxic dimethylpyrano-isoflavones from the stem bark of Erythrina mildbraedii: evaluation of their activity toward endocrine cancer cells.. Journal of enzyme inhibition and medicinal chemistry,2010, 25(2), 228-233. [View] [PubMed]
Pubchem: 5379679
Nmrshiftdb2: 60024643
CPRiL: 60840
Structure

SMILES: O1CC=Cc(c2)c1cc(c23)occ(c3=O)-c4ccccc4

Level: 1

Mol. Weight: 404.46 g/mol

Structure

SMILES: O=c1ccoc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 404.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 404.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.42
Plasma Protein Binding
77.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.24
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.59
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.77
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.71
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-20.58
Rat (Acute)
2.56
Rat (Chronic Oral)
2.1
Fathead Minnow
5.45
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
502.74
Hydration Free Energy
-5.83
Log(D) at pH=7.4
4.57
Log(P)
6.23
Log S
-6.32
Log(Vapor Pressure)
-9.53
Melting Point
223.87
pKa Acid
8.59
pKa Basic
6.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9731
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9500
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.9096
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.9020
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8978
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8645
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.8607
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8583
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8555
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8466
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8438
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8232
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8094
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8054
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8024
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8014
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7964
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7862
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7828
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7826
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7819
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7805
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7780
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7660
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7650
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7645
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7640
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7598
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7591
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7573
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7542
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7518
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7517
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7506
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7494
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7477
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7470
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7455
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7433
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7416
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7414
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7405
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7403
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7372
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7339
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7330
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7317
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7289
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7287
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7279
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7258
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7219
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7199
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7187
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7183
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7129
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7128
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7128
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7125
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7109
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7108
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7103
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7086
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7058
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7057
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7040

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