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Angustoline
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | CC(c1cncc2c1cc1c3[nH]c4c(c3CCn1c2=O)cccc4)O |
|---|---|
| InChI | InChI=1S/C20H17N3O2/c1-11(24)15-9-21-10-16-14(15)8-18-19-13(6-7-23(18)20(16)25)12-4-2-3-5-17(12)22-19/h2-5,8-11,22,24H,6-7H2,1H3 |
| InChIKey | NDHJXXLIRWAMEN-UHFFFAOYSA-N |
| Formula | C20H17N3O2 |
| HBA | 4 |
| HBD | 2 |
| MW | 331.38 |
| Rotatable Bonds | 1 |
| TPSA | 70.91 |
| LogP | 3.15 |
| Number Rings | 5 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.2 |
| Exact Mass | 331.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Mitragyna inermis | Rubiaceae | Plantae | 170023 |
Showing of synonyms
Angustoline
40041-95-0
19-(1-hydroxyethyl)-3,13,17-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one
Indolo(2',3':3,4)pyrido(1,2-b)(2,7)naphthyridin-5(7H)-one, 8,13-dihydro-1-(1-hydroxyethyl)-, (-)-
19-(1-hydroxyethyl)-3,13,17-triazapentacyclo(11.8.0.02,10.04,9.015,20)henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one
SCHEMBL3130934
ACon1_001552
DTXSID90960503
BRD-A66206989-001-01-4
1-(1-Hydroxyethyl)-8,13-dihydroindolo[2',3':3,4]pyrido[1,2-b][2,7]naphthyridin-5(7H)-one
- 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]
CPRiL:
90919
SMILES: c1cccc2[nH]c(c3c12)c4n(CC3)c(=O)c5c(c4)ccnc5
Level: 0
Mol. Weight: 331.38 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.76
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.61
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.04
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.27
- Plasma Protein Binding
- 67.89
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.12
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.44
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.95
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.06
- 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
- -2.88
- Rat (Acute)
- 3.19
- Rat (Chronic Oral)
- 1.74
- Fathead Minnow
- 4.78
- 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
- 496.07
- Hydration Free Energy
- -8.39
- Log(D) at pH=7.4
- 2.38
- Log(P)
- 2.18
- Log S
- -4.65
- Log(Vapor Pressure)
- -10.51
- Melting Point
- 343.67
- pKa Acid
- 12.09
- pKa Basic
- 6.35
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.8989 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8974 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8932 |
| Cytochrome P450 1A1 | P04798 | CP1A1_HUMAN | Homo sapiens | 3 | 0.8915 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.8750 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8702 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8583 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8575 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8552 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8537 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.8473 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8418 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8329 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.8247 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8188 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 3 | 0.8126 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8122 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 3 | 0.8029 |
| Apoptosis regulator Bcl-2 | P10415 | BCL2_HUMAN | Homo sapiens | 3 | 0.7999 |
| Nitric oxide synthase, inducible | P35228 | NOS2_HUMAN | Homo sapiens | 3 | 0.7999 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7990 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7989 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 3 | 0.7928 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7877 |
| Retinoic acid receptor beta | P10826 | RARB_HUMAN | Homo sapiens | 4 | 0.7867 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.7841 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7834 |
| Retinol-binding protein 1 | P09455 | RET1_HUMAN | Homo sapiens | 3 | 0.7825 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.7825 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 4 | 0.7820 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7809 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 4 | 0.7793 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7789 |
| Caspase-3 | P42574 | CASP3_HUMAN | Homo sapiens | 3 | 0.7776 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.7756 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7746 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7739 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7724 |
| Glutathione S-transferase F2 | P46422 | GSTF2_ARATH | Arabidopsis thaliana | 3 | 0.7696 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7655 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7652 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 2 | 0.7609 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7602 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 4 | 0.7599 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7591 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7570 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7570 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7568 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7566 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7563 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7555 |
| Gastrotropin | P51161 | FABP6_HUMAN | Homo sapiens | 3 | 0.7544 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7543 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7538 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7536 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7528 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7525 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7520 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 5 | 0.7504 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7497 |
| Cellular retinol-binding protein type II | Q8UVG6 | Q8UVG6_DANRE | Danio rerio | 3 | 0.7484 |
| Biphenyl-2,3-diol 1,2-dioxygenase | P17297 | BPHC_PSES1 | Pseudomonas sp | 3 | 0.7482 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7457 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7452 |
| Retinaldehyde-binding protein 1 | P12271 | RLBP1_HUMAN | Homo sapiens | 4 | 0.7448 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7428 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 4 | 0.7416 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7408 |
| Genome polyprotein | C0LMU0 | C0LMU0_9FLAV | dengue virus type 3 | 3 | 0.7389 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 4 | 0.7357 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7356 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7343 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 3 | 0.7329 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7306 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.7251 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7246 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7243 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7212 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7212 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7191 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7182 |
| Sterol 14-alpha demethylase | Q7Z1V1 | CP51_TRYCC | Trypanosoma cruzi | 4 | 0.7172 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7171 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7163 |
| Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 3 | 0.7135 |
| Glycylpeptide N-tetradecanoyltransferase | A5K1A2 | A5K1A2_PLAVS | Plasmodium vivax | 3 | 0.7126 |
| Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 3 | 0.7122 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 4 | 0.7115 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7104 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 2 | 0.7095 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7094 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7093 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7076 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7075 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7061 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7061 |
| Metallo-beta-lactamase type 2 | P25910 | BLAB_BACFG | Bacteroides fragilis | 3 | 0.7050 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7044 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7008 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7006 |
| Mitogen-activated protein kinase 11 | Q15759 | MK11_HUMAN | Homo sapiens | 4 | 0.7002 |