Senegalensin - Compound Card

Senegalensin

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Senegalensin

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles CC(=CCc1c2O[C@@H](CC(=O)c2c(c(c1O)CC=C(C)C)O)c1ccc(cc1)O)C
InChI InChI=1S/C25H28O5/c1-14(2)5-11-18-23(28)19(12-6-15(3)4)25-22(24(18)29)20(27)13-21(30-25)16-7-9-17(26)10-8-16/h5-10,21,26,28-29H,11-13H2,1-4H3/t21-/m0/s1
InChIKey HCNLDGTUMBOHKT-NRFANRHFSA-N
Formula C25H28O5
HBA 5
HBD 3
MW 408.49
Rotatable Bonds 5
TPSA 86.99
LogP 5.53
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 408.19
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Macaranga hurifolia Euphorbiaceae Plantae 396461

Showing of synonyms

  • Pagna JI M, Awazi T, et al. (2022). Antibacterial flavonoids from the fruits of Macaranga hurifolia.. Journal of Asian natural products research,2022, 24(11), 1041-1051. [View] [PubMed]
Pubchem: 124035
Kegg Ligand: C09724
Chebi: 2156
Nmrshiftdb2: 60025267
Metabolights: MTBLC2156
CPRiL: 123180
Structure

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

Level: 1

Mol. Weight: 408.49 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 408.49 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 408.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.89
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.79
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.03
Plasma Protein Binding
78.58
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
4.83
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.49
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.52
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.03
Micronucleos
Toxic
NR-AhR
Safe
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
Safe
T. Pyriformis
-16.44
Rat (Acute)
1.94
Rat (Chronic Oral)
2.73
Fathead Minnow
5.14
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
474.23
Hydration Free Energy
-6.21
Log(D) at pH=7.4
3.95
Log(P)
6.58
Log S
-5.8
Log(Vapor Pressure)
-9.32
Melting Point
163.48
pKa Acid
7.97
pKa Basic
6.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9330
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9297
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9231
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9034
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8931
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8797
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8701
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8643
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8507
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8467
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8450
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8390
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8365
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8350
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8305
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8298
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8284
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8249
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8237
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8200
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8189
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8161
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8122
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8084
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8035
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7829
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7796
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7775
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7744
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7735
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7735
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7722
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7680
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7673
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7666
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7620
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7580
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7570
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7557
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7534
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7514
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7511
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7494
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7490
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7486
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7478
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7474
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7442
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7441
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7426
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 4 0.7406
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7392
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7385
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7384
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7368
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7357
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7344
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7320
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7308
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7297
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7254
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7239
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7239
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7215
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7211
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7207
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7201
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7179
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7167
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7157
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7137
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7129
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7113
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7096
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7093
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7092
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7078
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7066
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7048
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7046
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7045
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7040
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7040
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7027
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7025
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7015

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