Sigmoidin A - Compound Card

Sigmoidin A

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Sigmoidin A

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanone
Canonical Smiles CC(=CCc1c(cc(c(c1O)O)CC=C(C)C)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O)C
InChI InChI=1S/C25H28O6/c1-13(2)5-7-15-9-18(17(8-6-14(3)4)25(30)24(15)29)21-12-20(28)23-19(27)10-16(26)11-22(23)31-21/h5-6,9-11,21,26-27,29-30H,7-8,12H2,1-4H3/t21-/m0/s1
InChIKey BVHLNRAYBCPKOY-NRFANRHFSA-N
Formula C25H28O6
HBA 6
HBD 4
MW 424.49
Rotatable Bonds 5
TPSA 107.22
LogP 5.23
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 424.19
Number of Lipinski Rule Violations 1
# 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]
Pubchem: 73204
Chebi: 66482
Nmrshiftdb2: 60072966
Metabolights: MTBLC66482
Bindingdb: 50212392

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 424.49 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 424.49 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 424.49 g/mol

Anti-inflammatory
Anti-plasmodial
Antimicrobial
Antioxidant

Absorption

Caco-2 (logPapp)
-5.76
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.96
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.0
Plasma Protein Binding
84.18
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.4
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.03
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.66
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.72
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
Toxic
T. Pyriformis
-23.73
Rat (Acute)
2.01
Rat (Chronic Oral)
3.11
Fathead Minnow
5.15
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
507.98
Hydration Free Energy
-6.27
Log(D) at pH=7.4
3.06
Log(P)
5.53
Log S
-6.52
Log(Vapor Pressure)
-9.21
Melting Point
199.14
pKa Acid
7.15
pKa Basic
6.97
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 0.8982
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8982
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8965
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8965
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8963
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8963
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8819
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8819
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8696
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8696
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8577
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8577
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8492
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8492
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8439
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8439
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8435
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8435
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8423
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8423
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8335
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8335
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8325
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8325
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8168
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8168
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8135
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8135
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7936
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7936
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7919
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7919
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7896
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7896
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7880
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7880
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7865
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7865
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7825
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7825
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7804
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7804
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7784
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7784
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7738
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7738
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7667
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7667
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7628
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7628
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7614
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7614
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7609
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7609
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7548
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7548
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7541
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7541
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7535
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7535
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7533
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7533
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7521
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7521
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7510
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7510
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7470
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7470
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7440
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7440
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7390
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7390
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7375
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7375
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7371
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7371
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7332
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7332
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7304
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7304
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7288
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7288
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7256
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7256
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7251
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7251
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7245
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7245
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7244
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7244
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7239
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7239
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7224
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7224
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7189
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7189
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7164
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7164
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7151
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7151
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7131
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 6 0.7131
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7128
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7128
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7122
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7122
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7117
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7117
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7115
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7115
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7109
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7109
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7103
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7103
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7100
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7100
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7098
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7098
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7095
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7095
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7075
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7075
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7063
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7063
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7046
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7046
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7041
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7041
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7036
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7036
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7033
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7033
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7018
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7018
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7017
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7017
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7008
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7008
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7004
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7004

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