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Echinulin
- Family: Plantae - Combretaceae
- Kingdom: Fungi, Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | C=CC(c1[nH]c2c(c1C[C@@H]1NC(=O)[C@@H](NC1=O)C)cc(cc2CC=C(C)C)CC=C(C)C)(C)C |
|---|---|
| InChI | InChI=1S/C29H39N3O2/c1-9-29(7,8)26-23(16-24-28(34)30-19(6)27(33)31-24)22-15-20(12-10-17(2)3)14-21(25(22)32-26)13-11-18(4)5/h9-11,14-15,19,24,32H,1,12-13,16H2,2-8H3,(H,30,34)(H,31,33)/t19-,24-/m0/s1 |
| InChIKey | DIKMWTRJIZQJMY-CYFREDJKSA-N |
| Formula | C29H39N3O2 |
| HBA | 2 |
| HBD | 3 |
| MW | 461.65 |
| Rotatable Bonds | 8 |
| TPSA | 73.99 |
| LogP | 5.19 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.45 |
| Exact Mass | 461.3 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus amstelodami | Trichocomaceae | Fungi | 5054 |
| 2 | Combretum dolichopetalum | Combretaceae | Plantae | 99434 |
Showing of synonyms
Echinulin
Echinuline
1859-87-6
3DP19VPN8U
CHEMBL251450
D-Gluconic acid, 2-(acetylamino)-2-deoxy-, delta-lactone
(3S,6S)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]piperazine-2,5-dione
2,5-Piperazinedione, 3-((2-(1,1-dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl)methyl)-6-methyl-, (3S,6S)-
(3s,6s)-3-methyl-6-{[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}piperazine-2,5-dione
UNII-3DP19VPN8U
2,5-Piperazinedione, 3-[[2-(1,1-dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl]methyl]-6-methyl-, (3S,6S)-
ECHINULINE [MI]
CHEBI:68193
HY-N3796
BDBM50223401
AKOS030213189
AT43222
NCGC00386111-01
CS-0024238
Q27257084
D-Gluconic acid, 2-(acetylamino)-2-deoxy-, |A-lactone
(3S,6S)-3-[[2-(1,1-dimethyl-2-propen-1-yl)-5,7-bis(3-methyl-2-buten-1-yl)-1H-indol-3-yl]methyl]-6-methyl-2,5-piperazinedione
(3S,6S)-3-[[2-(1,1-dimethylallyl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]-6-methyl-piperazine-2,5-dione
3-((2-(1,1-Dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl)methyl)-6-methyl-2,5-piperazinedione
- Elsbaey M, Sallam A, et al. (2019). Melanogenesis Inhibitors from the Endophytic Fungus Aspergillus amstelodami. Chem Biodivers,2019,16(8),e1900237. [View] [PubMed]
- Uzor PF, Ebrahim W, et al. (2015). Metabolites from Combretum dolichopetalum and its endophytic fungus Nigrospora oryzae — evidence for a associated metabolic partnership. Fitoterapia,2015,105,147-150. [View]
Pubchem:
115252
Cas:
1859-87-6
Gnps:
CCMSLIB00000839192
Zinc:
ZINC000015149223
Chebi:
68193
Nmrshiftdb2:
60026693
Metabolights:
MTBLC68193
Chembl:
CHEMBL251450
Bindingdb:
50223401
No compound-protein relationship available.
SMILES: N1CC(=O)NC(C1=O)Cc2c[nH]c(c23)cccc3
Level: 1
Mol. Weight: 461.65 g/mol
SMILES: c1c[nH]c(c12)cccc2
Level: 0
Mol. Weight: 461.65 g/mol
SMILES: O=C1CNC(=O)CN1
Level: 0
Mol. Weight: 461.65 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.87
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.12
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.5
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.44
- Plasma Protein Binding
- 75.12
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.54
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.16
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.47
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.09
- 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
- -126.53
- Rat (Acute)
- 2.56
- Rat (Chronic Oral)
- 2.55
- Fathead Minnow
- 5.27
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 506.95
- Hydration Free Energy
- -3.18
- Log(D) at pH=7.4
- 4.23
- Log(P)
- 6.71
- Log S
- -4.83
- Log(Vapor Pressure)
- -9.95
- Melting Point
- 189.53
- pKa Acid
- 10.27
- pKa Basic
- 5.97
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 3 | 0.8586 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8539 |
| cAMP-dependent protein kinase type II-beta regulatory subunit | P12369 | KAP3_RAT | Rattus norvegicus | 3 | 0.8423 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8305 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8184 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8077 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7968 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7910 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.7819 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 4 | 0.7807 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7799 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7665 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7658 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7632 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7612 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7577 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7541 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 3 | 0.7499 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7331 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7268 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7262 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7177 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7161 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7148 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.7136 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 4 | 0.7121 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7056 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7054 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7048 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7033 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.7029 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7013 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 2 | 0.7011 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7003 |