Peregrinone - Compound Card

Peregrinone

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Peregrinone

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Ketone
Canonical Smiles O=C1CC[C@]2([C@@H]3[C@@]1(C)C(=O)O[C@@H]3C[C@H]([C@]2(O)CCc1ccoc1)C)C
InChI InChI=1S/C20H26O5/c1-12-10-14-16-18(2,7-5-15(21)19(16,3)17(22)25-14)20(12,23)8-4-13-6-9-24-11-13/h6,9,11-12,14,16,23H,4-5,7-8,10H2,1-3H3/t12-,14-,16-,18+,19+,20-/m1/s1
InChIKey NMTGXAKMAWZRIF-YCXIAQJUSA-N
Formula C20H26O5
HBA 5
HBD 1
MW 346.42
Rotatable Bonds 3
TPSA 76.74
LogP 2.9
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 346.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Leucas neufliseana Lamiaceae Plantae 2511971

Showing of synonyms

  • Ele S, G/Yesus T, et al. (2007). Chemical studies of Leucas martinicensis. M.Sc. Thesis, Addis Ababa University, Ethiopia,2007. [View] [PubMed]
Pubchem: 7091745
Nmrshiftdb2: 60072501

No compound-protein relationship available.

Structure

SMILES: c1occc1CCC(C2CCC3=O)CCC(C2C34)OC4=O

Level: 1

Mol. Weight: 346.42 g/mol

Structure

SMILES: O=C1OC(C2C13)CCCC2CCC3=O

Level: 0

Mol. Weight: 346.42 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 346.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.690
Plasma Protein Binding
66.18
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.960
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.260
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.720
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.350
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
-3.110
Rat (Acute)
4.440
Rat (Chronic Oral)
1.800
Fathead Minnow
3.920
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
378.960
Hydration Free Energy
-6.530
Log(D) at pH=7.4
2.090
Log(P)
1.77
Log S
-3.64
Log(Vapor Pressure)
-7.33
Melting Point
170.01
pKa Acid
7.39
pKa Basic
4.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9133
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9133
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8842
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8842
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8622
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8622
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8555
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8555
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8235
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8235
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8215
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8215
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.8140
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.8140
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7997
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7997
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7877
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7877
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7861
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7861
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7818
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7818
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7771
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7771
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7693
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7693
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7663
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7663
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7660
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7660
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7619
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7619
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7616
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7616
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7604
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7604
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7589
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7589
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7562
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7562
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7561
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7561
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7551
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7551
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7542
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7542
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7494
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7494
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7470
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7470
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7466
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7466
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7455
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7455
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7440
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7440
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7434
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7434
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7428
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7428
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7428
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7428
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7419
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7419
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7417
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7417
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7410
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7410
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7408
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7408
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7394
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7394
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7381
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7381
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7364
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7364
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7341
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7341
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7311
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7311
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7292
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7292
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7289
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7289
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7285
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7285
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7271
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7271
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7248
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7248
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7248
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7248
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7245
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7245
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7224
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7224
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7191
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7191
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7180
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7180
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7175
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7175
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7169
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7169
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7167
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7167
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7143
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7143
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7141
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7141
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7127
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7127
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7114
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7114
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7114
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7114
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7110
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7110
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7098
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7098
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7055
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7055
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7045
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7045
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7039
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7039
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7029
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7029
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 2 0.7022
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 2 0.7022
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7014
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7014
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7014
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7014

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