Sigmoidin C - Compound Card

Sigmoidin C

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Sigmoidin C

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanone
Canonical Smiles Oc1cc2O[C@@H](CC(=O)c2c(c1)O)c1cc(O)c2c(c1)C=CC(O2)(C)C
InChI InChI=1S/C20H18O6/c1-20(2)4-3-10-5-11(6-15(24)19(10)26-20)16-9-14(23)18-13(22)7-12(21)8-17(18)25-16/h3-8,16,21-22,24H,9H2,1-2H3/t16-/m0/s1
InChIKey RFBNSYVWJNUVHE-INIZCTEOSA-N
Formula C20H18O6
HBA 6
HBD 3
MW 354.36
Rotatable Bonds 1
TPSA 96.22
LogP 3.69
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 354.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina abyssinica Leguminosae/Fabaceae Plantae 1237573
2 Erythrina abyssinica Leguminosae/Fabaceae Plantae 1237573
3 Erythrina abyssinica Leguminosae/Fabaceae Plantae 1237573

Showing of synonyms

  • Yenesew A, Induli M, et al. (2004). Anti-plasmodial flavonoids from the stem bark of Erythrina abyssinica.. Phytochemistry,2004,65(22),3029-3032. [View] [PubMed]
  • Cui L, Ndinteh DT, et al. (2007). Isoprenylated flavonoids from the stem bark of Erythrina abyssinica.. Journal of Natural Products,2007,70(6),1039-1042. [View] [PubMed]
  • Ichimaru M, Moriyasu M, et al. (1996). Structural Elucidation of New Flavanones Isolated from Erythrina abyssinica.. Journal of Natural Products,1996,59,1113-1116. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2=O)c(c3)ccc(c34)OCC=C4

Level: 1

Mol. Weight: 354.36 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 354.36 g/mol

Structure

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 354.36 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.98
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.900
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.180
Plasma Protein Binding
78.31
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.520
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.790
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.300
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.830
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
Toxic
T. Pyriformis
0.240
Rat (Acute)
2.290
Rat (Chronic Oral)
2.760
Fathead Minnow
4.370
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
462.090
Hydration Free Energy
-10.350
Log(D) at pH=7.4
3.020
Log(P)
3.96
Log S
-6.13
Log(Vapor Pressure)
-8.36
Melting Point
235.76
pKa Acid
7.38
pKa Basic
4.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8956
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8956
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8931
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8931
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8586
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8586
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8423
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8423
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8179
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8179
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8116
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8116
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8030
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8030
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8028
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8028
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7996
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7996
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7924
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7924
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7906
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7906
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7856
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7856
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7840
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7840
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7825
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7825
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7816
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7816
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7794
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7794
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7791
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7791
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7778
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7778
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7771
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7771
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7767
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7767
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7760
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7760
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7741
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7741
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7717
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7717
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7711
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7711
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7680
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7680
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7647
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7647
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7619
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7619
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7607
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7607
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7602
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7602
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7573
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7573
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7539
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7539
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7518
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7518
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7516
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7516
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7503
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7503
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7492
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7492
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7448
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7448
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7432
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7432
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7429
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7429
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7418
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7418
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7408
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7408
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7364
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7364
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7343
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7343
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7331
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7331
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7323
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7323
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7314
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7314
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7306
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7306
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7305
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7305
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7304
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7304
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7298
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7298
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7277
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7277
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7243
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7243
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7238
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7238
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7236
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7236
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7218
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7218
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7216
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7216
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7208
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7208
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7201
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7201
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7134
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7134
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7130
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7130
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7113
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7113
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7105
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7105
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7101
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7101
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7096
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7096
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7070
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7070
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7070
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7070
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7064
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7064
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7063
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7063
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7052
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7052
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7049
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7049
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7039
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7039
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7019
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7019

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