Piperolactam D - Compound Card

Piperolactam D

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Piperolactam D

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Aristolactam Alkaloid
Canonical Smiles COc1c(O)c2c3ccccc3cc3c2c(c1OC)c(=O)[nH]3
InChI InChI=1S/C17H13NO4/c1-21-15-13-12-10(18-17(13)20)7-8-5-3-4-6-9(8)11(12)14(19)16(15)22-2/h3-7,19H,1-2H3,(H,18,20)
InChIKey PHKYZFGDNGACRM-UHFFFAOYSA-N
Formula C17H13NO4
HBA 4
HBD 2
MW 295.29
Rotatable Bonds 2
TPSA 67.79
LogP 3.28
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 295.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Anonidium mannii Annonaceae Plantae 2109291

Showing of synonyms

  • Matchi JLT, Noungoue DT, et al. (2021). Manniindole, an indole derivative from the roots of Anonidium mannii and combined antischistosomal and enzymatic activities. Natural product research,2021, 35(24), 5665-5673. [View] [PubMed]
Pubchem: 14039008
Chebi: 174802
Nmrshiftdb2: 70007156

No compound-protein relationship available.

Structure

SMILES: c12c3cccc2c4c(cc1NC3=O)cccc4

Level: 0

Mol. Weight: 295.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.590
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.600
Plasma Protein Binding
77.6
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.440
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.880
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.280
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.020
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
2.760
Rat (Acute)
2.230
Rat (Chronic Oral)
2.970
Fathead Minnow
4.750
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
448.720
Hydration Free Energy
-8.980
Log(D) at pH=7.4
2.120
Log(P)
2.46
Log S
-4.88
Log(Vapor Pressure)
-7.21
Melting Point
233.51
pKa Acid
7.73
pKa Basic
2.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9590
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9345
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.9343
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9306
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9185
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9020
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9008
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8989
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8976
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8965
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8908
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8860
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8801
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8780
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8775
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8673
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8642
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8620
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8576
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8576
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8575
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.8543
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8537
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8520
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8516
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8515
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8481
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8436
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8396
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 3 0.8372
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8368
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.8330
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8309
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8259
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8255
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8237
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8227
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8223
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8197
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8172
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8166
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8142
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8126
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.8116
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8084
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8079
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8067
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8061
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 4 0.8058
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8051
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8023
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8010
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8005
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8001
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 4 0.7997
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7996
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7992
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7983
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7967
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7964
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7932
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7927
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7913
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7901
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7901
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7880
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7810
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7777
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7775
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7774
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7755
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7741
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7706
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7704
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7703
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7696
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7693
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7663
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7648
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7639
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7627
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7623
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7613
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7590
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7590
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7576
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7554
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7538
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7524
Prothrombin P00734 THRB_HUMAN Homo sapiens 4 0.7517
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7505
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7490
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7489
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7488
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7478
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7467
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7465
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7426
Mucosa-associated lymphoid tissue lymphoma translocation protein 1 Q9UDY8 MALT1_HUMAN Homo sapiens 3 0.7425
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7413
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7410
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7406
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7405
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7401
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7395
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7384
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7379
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7379
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7378
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7364
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7361
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7357
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7352
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7348
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7324
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7321
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7321
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7304
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7294
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7283
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7278
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7278
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7277
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7274
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7268
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7263
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7262
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7250
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7230
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7222
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 2 0.7221
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7215
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7212
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7183
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7181
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7178
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7173
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7170
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7156
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7152
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7147
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7132
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7116
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7097
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7096
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7081
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7075
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7074
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7058
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7017
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7015
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7013
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7012

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