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Terrelumamide A
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
- Class: Amide
| Canonical Smiles | COC(=O)c1ccccc1NC(=O)[C@H]([C@H](O)C)NC(=O)c1cnc2c(n1)c(=O)[nH]c(=O)n2C |
|---|---|
| InChI | InChI=1S/C20H20N6O7/c1-9(27)13(17(29)23-11-7-5-4-6-10(11)19(31)33-3)24-16(28)12-8-21-15-14(22-12)18(30)25-20(32)26(15)2/h4-9,13,27H,1-3H3,(H,23,29)(H,24,28)(H,25,30,32)/t9-,13+/m1/s1 |
| InChIKey | YVUJATOOBNWJDN-RNCFNFMXSA-N |
| Formula | C20H20N6O7 |
| HBA | 10 |
| HBD | 4 |
| MW | 456.42 |
| Rotatable Bonds | 6 |
| TPSA | 185.37 |
| LogP | -1.08 |
| Number Rings | 3 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 456.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus terreus | Trichocomaceae | Fungi | 33178 |
| 2 | Aspergillus terreus | Trichocomaceae | Fungi | 33178 |
Showing of synonyms
Terrelumamide A
Methyl 2-[[(2S,3R)-3-hydroxy-2-[(1-methyl-2,4-dioxopteridine-6-carbonyl)amino]butanoyl]amino]benzoate
(2S,3R)-3-Hydroxy-2-((hydroxy(4-hydroxy-1-methyl-2-oxo-1,2-dihydropteridin-6-yl)methylidene)amino)-N-(2-(methoxycarbonyl)phenyl)butanimidate
(2S,3R)-3-Hydroxy-2-{[hydroxy(4-hydroxy-1-methyl-2-oxo-1,2-dihydropteridin-6-yl)methylidene]amino}-N-[2-(methoxycarbonyl)phenyl]butanimidate
Methyl 2-(((2S,3R)-3-hydroxy-2-((1-methyl-2,4-dioxopteridine-6-carbonyl)amino)butanoyl)amino)benzoate
CHEMBL4474465
CHEBI:226139
HY-N6181
BDBM50519515
CS-0032666
- Shaaban M, El-Metwally M.M, et al. (2018). Terretonin M: A new meroterpenoid from the thermophilic Aspergillus terreus TM8 and revision of the absolute configuration of penisimplicins. Nat Prod Res,2018,32(20),2437-2446. [View] [PubMed]
- Hamed A, Abdel-Razek A.S, et al. (2020). Terretonin O: a new meroterpenoid from Aspergillus terreus. Nat Prod Res,2020,34(7),965-974. [View] [PubMed]
No compound-protein relationship available.
SMILES: c1ccccc1NC(=O)CNC(=O)c(n2)cnc(c23)[nH]c(=O)[nH]c3=O
Level: 1
Mol. Weight: 456.42 g/mol
SMILES: n1ccnc(c12)[nH]c(=O)[nH]c2=O
Level: 0
Mol. Weight: 456.42 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 456.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.77
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.320
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.5
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.040
- Plasma Protein Binding
- 62.0
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-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
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.250
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.740
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.390
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.870
- 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
- -91.260
- Rat (Acute)
- 1.680
- Rat (Chronic Oral)
- 2.830
- Fathead Minnow
- 4.160
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 607.810
- Hydration Free Energy
- -3.790
- Log(D) at pH=7.4
- 0.350
- Log(P)
- 0.12
- Log S
- -4.34
- Log(Vapor Pressure)
- -10.86
- Melting Point
- 226.39
- pKa Acid
- 7.29
- pKa Basic
- 5.29
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.9491 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.9105 |
| Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 3 | 0.8852 |
| Dipeptidyl peptidase 4 | P14740 | DPP4_RAT | Rattus norvegicus | 3 | 0.8655 |
| Bifunctional protein GlmU | P43889 | GLMU_HAEIN | Haemophilus influenzae | 3 | 0.8613 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8510 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8507 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8506 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 3 | 0.8491 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.8474 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8444 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8285 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.8231 |
| Tubulin alpha-1B chain | P81947 | TBA1B_BOVIN | Bos taurus | 3 | 0.8201 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8135 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8060 |
| Carnitine O-palmitoyltransferase 2, mitochondrial | P18886 | CPT2_RAT | Rattus norvegicus | 3 | 0.8042 |
| Orf1a polyprotein | Q692E5 | Q692E5_CVHSA | SARS coronavirus TJF | 3 | 0.8024 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.7996 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.7921 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7882 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7807 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7755 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7652 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7634 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7617 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7600 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.7564 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 2 | 0.7488 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7481 |
| Uridine phosphorylase | P0A1F6 | UDP_SALTY | Salmonella typhimurium | 4 | 0.7468 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7431 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7426 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 4 | 0.7418 |
| Sodium-dependent dopamine transporter | Q7K4Y6 | DAT_DROME | Drosophila melanogaster | 2 | 0.7398 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7393 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.7386 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7374 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 3 | 0.7366 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7357 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7333 |
| Metallo-beta-lactamase type 2 | P26918 | BLAB_AERHY | Aeromonas hydrophila | 2 | 0.7332 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7310 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7310 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7299 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7296 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7287 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.7276 |
| Stimulator of interferon genes protein | Q86WV6 | STING_HUMAN | Homo sapiens | 3 | 0.7269 |
| Genome polyprotein | Q99AU2 | Q99AU2_9HEPC | Hepatitis C virus subtype 1b | 3 | 0.7265 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7253 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7237 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7230 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7223 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 4 | 0.7189 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7186 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7185 |
| Microcin C7 self-immunity protein MccF | Q47511 | MCCF_ECOLX | Escherichia coli | 3 | 0.7150 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.7142 |
| Annexin A5 | P08758 | ANXA5_HUMAN | Homo sapiens | 2 | 0.7142 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.7137 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7129 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7104 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7097 |
| Chalcone synthase 2 | P30074 | CHS2_MEDSA | Medicago sativa | 2 | 0.7083 |
| Dicamba O-demethylase, oxygenase component | Q5S3I3 | DDMC_STEMA | Stenotrophomonas maltophilia | 3 | 0.7051 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.7050 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7043 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 2 | 0.7039 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7039 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7033 |
| Pol protein | Q000H7 | Q000H7_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7018 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 2 | 0.7010 |