Phenentada - Compound Card

Phenentada

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Phenentada

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Phenanthrene
Canonical Smiles OCOc1cc2ccc3c(c2cc1O)cc(c(c3)OC)OC
InChI InChI=1S/C17H16O5/c1-20-16-6-11-4-3-10-5-15(22-9-18)14(19)7-12(10)13(11)8-17(16)21-2/h3-8,18-19H,9H2,1-2H3
InChIKey MNXCMELMJHBXRR-UHFFFAOYSA-N
Formula C17H16O5
HBA 5
HBD 2
MW 300.31
Rotatable Bonds 4
TPSA 68.15
LogP 3.04
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 300.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Entada abyssinica Leguminosae/Fabaceae Plantae 204973

Showing of synonyms

  • Magnibou L, Leutcha P, et al. (2022). A new phenanthrene derivative from Entada abyssinica with antimicrobial and antioxidant properties. Zeitschrift für Naturforschung B. 2022, 77(1), 1-7. [View]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)ccc2cccc3

Level: 0

Mol. Weight: 300.31 g/mol

Antimicrobial
Antioxidant

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.49
Plasma Protein Binding
67.29
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
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.76
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.94
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.45
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.12
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
2.96
Rat (Acute)
2.35
Rat (Chronic Oral)
2.67
Fathead Minnow
4.8
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
422.06
Hydration Free Energy
-9.31
Log(D) at pH=7.4
2.21
Log(P)
2.24
Log S
-4.91
Log(Vapor Pressure)
-6.82
Melting Point
148.31
pKa Acid
8.62
pKa Basic
1.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9725
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9546
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9462
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9428
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9392
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9370
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.9290
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9203
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9157
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9077
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8991
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8980
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8877
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8866
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8858
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8723
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8722
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8719
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8706
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8700
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8664
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8663
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8658
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 4 0.8621
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8589
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8579
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8576
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8557
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8532
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8514
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8514
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8462
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8382
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8361
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8333
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8332
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8309
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8278
Reaction center protein L chain P0C0Y8 RCEL_RHOSH Rhodobacter sphaeroides 3 0.8232
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8220
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8140
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8118
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8067
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8048
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8046
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8040
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8036
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8023
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8004
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7992
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7989
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7984
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7968
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7935
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7930
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7913
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7875
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7875
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7831
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7796
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7788
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7761
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7744
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7742
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7714
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7699
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7683
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7671
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7667
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7666
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7653
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7646
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7634
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7632
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7629
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7622
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7583
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7574
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7559
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7558
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7553
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7549
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7538
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7532
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7530
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7496
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7488
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7475
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7474
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7460
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7445
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7429
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7423
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7403
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7380
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7351
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7349
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7348
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7347
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7345
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7344
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7343
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7327
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7325
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7308
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7306
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7296
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7291
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7280
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7257
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 3 0.7256
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7253
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7229
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7224
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7212
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7202
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7181
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7175
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7160
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7145
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7144
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7137
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7135
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7107
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7103
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7091
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7082
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7082
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7072
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7064
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7058
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7036
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7027
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7021
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7013
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7001
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7001

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