Naucleactonin D - Compound Card

Naucleactonin D

Select a section from the left sidebar

Naucleactonin D

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles O=Cc1c(C)oc2c1cc1c3[nH]c4c(c3CCn1c2=O)cccc4
InChI InChI=1S/C19H14N2O3/c1-10-14(9-22)13-8-16-17-12(11-4-2-3-5-15(11)20-17)6-7-21(16)19(23)18(13)24-10/h2-5,8-9,20H,6-7H2,1H3
InChIKey UYYNFGDCEFXZGB-UHFFFAOYSA-N
Formula C19H14N2O3
HBA 4
HBD 1
MW 318.33
Rotatable Bonds 1
TPSA 68.0
LogP 3.42
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.16
Exact Mass 318.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Mitragyna inermis Rubiaceae Plantae 170023

Showing of synonyms

  • Donfack E, Lenta B, et al. (2012). Naucleactonin D, an Indole Alkaloid and other Chemical Constituents from Roots and Fruits of Mitragyna inermis. Zeitschrift für Naturforschung B. 2012, 67(11), 1159-1165. [View]
Pubchem: 71545910

No compound-protein relationship available.

Structure

SMILES: c1cccc2[nH]c(c3c12)c4n(CC3)c(=O)c5c(c4)cco5

Level: 0

Mol. Weight: 318.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.05
Plasma Protein Binding
55.4
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
Substrate
CYP 2C9 Inhibitor
Non-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
5.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.43
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.0
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.32
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
Safe
T. Pyriformis
0.37
Rat (Acute)
3.07
Rat (Chronic Oral)
1.45
Fathead Minnow
4.83
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
487.31
Hydration Free Energy
-9.41
Log(D) at pH=7.4
2.34
Log(P)
3.32
Log S
-5.65
Log(Vapor Pressure)
-11.39
Melting Point
362.49
pKa Acid
9.46
pKa Basic
5.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9900
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9626
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.9532
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9325
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9250
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.9139
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.9092
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.9073
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.9051
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9033
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9020
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8989
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8986
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8975
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8748
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8739
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8721
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8648
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8636
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8511
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8360
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8284
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8193
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8133
Bcl-2-like protein 1 Q07817 B2CL1_HUMAN Homo sapiens 3 0.8112
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8099
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8099
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8084
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8048
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.8033
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8016
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7927
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7916
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7864
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7820
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7800
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7800
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7792
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7771
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7759
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7756
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7733
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7731
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7717
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7701
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7700
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7685
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7661
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7655
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7634
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7633
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7626
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7598
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 4 0.7592
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7590
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7587
Sterol 14-alpha demethylase Q7Z1V1 CP51_TRYCC Trypanosoma cruzi 4 0.7581
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7565
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7549
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7549
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7548
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7539
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7534
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7517
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7495
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7495
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7485
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 4 0.7482
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7476
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7473
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7429
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7416
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7415
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7415
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7406
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7399
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7397
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7387
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7387
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7387
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7380
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7377
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7372
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7367
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7353
Toll-like receptor 8 Q9NR97 TLR8_HUMAN Homo sapiens 3 0.7353
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7345
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7342
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7336
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7332
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7327
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7326
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7320
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7317
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7316
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7313
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7294
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7287
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7285
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7284
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7282
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7280
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7272
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7269
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7262
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7260
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7257
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7255
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7255
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 4 0.7252
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7246
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7239
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7229
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7224
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7224
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7223
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7216
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7209
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 4 0.7207
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7204
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 4 0.7199
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7188
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7176
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7158
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7146
Isoliquiritigenin 2'-O-methyltransferase P93324 CHOMT_MEDSA Medicago sativa 3 0.7141
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7137
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7118
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7107
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7104
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7097
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7095
Genome polyprotein P03303 POLG_HRV14 Human rhinovirus 14 3 0.7092
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7085
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7080
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7079
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7069
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7053
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7047
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7041
Genome polyprotein Q9WMX2 POLG_HCVCO Hepatitis C virus genotype 1b 4 0.7040
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7040
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7038
Mitogen-activated protein kinase 11 Q15759 MK11_HUMAN Homo sapiens 4 0.7034
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 4 0.7029
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7024
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7016
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7015

Download SDF