NPs Basic Information

Name
Maculosin
Molecular Formula C14H16N2O3
IUPAC Name*
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
SMILES
C1C[C@H]2C(=O)N[C@H](C(=O)N2C1)CC3=CC=C(C=C3)O
InChI
InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1
InChIKey
LSGOTAXPWMCUCK-RYUDHWBXSA-N
Synonyms
Maculosin; Cyclo(L-pro-L-tyr); 4549-02-4; (3s,8as)-3-(4-hydroxybenzyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione; Cyclo(-Pro-Tyr); CYCLO-(L-TYROSINE-L-PROLINE) INHIBITOR; (3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione; CHEBI:6631; (3S,8AR)-3-(4-HYDROXYBENZYL)HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE; (3S,8aS)-Hexahydro-3-[(4-hydroxyphenyl)methyl]pyrrolo[1,2-a]pyrazine-1,4-dione; cyclo(pro-tyr); 1w1y; Cyclo(L-Pro-L-Tyr-); Cyclo-(L-Pro-L-Tyr); Cyclo(L-prolinyl-L-tyrosine); CHEMBL359788; SCHEMBL12035399; DTXSID30196526; HY-P1940; ZINC1629943; MFCD03093467; DB04520; TYP; CS-0064671; Q27089361; Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-3-((4-hydroxyphenyl)methyl)-, (3S,8aS)-; Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-3-((4-hydroxyphenyl)methyl)-, (3S-trans)-
CAS 4549-02-4
PubChem CID 119404
ChEMBL ID CHEMBL359788
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Organic acids and derivat
      • Class: Carboxylic acids and deri
        • Subclass: Amino acids, peptides, an
          • Direct Parent: Alpha amino acids and der

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 260.29 ALogp: 1.0
HBD: 2 HBA: 3
Rotatable Bonds: 2 Lipinski's rule of five: Accepted
Polar Surface Area: 69.6 Aromatic Rings: 3
Heavy Atoms: 19 QED Weighted: 0.827

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.885 MDCK Permeability: 0.00000573
Pgp-inhibitor: 0 Pgp-substrate: 0.004
Human Intestinal Absorption (HIA): 0.026 20% Bioavailability (F20%): 0.794
30% Bioavailability (F30%): 0.599

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.229 Plasma Protein Binding (PPB): 34.03%
Volume Distribution (VD): 0.549 Fu: 60.51%

ADMET: Metabolism

CYP1A2-inhibitor: 0.021 CYP1A2-substrate: 0.111
CYP2C19-inhibitor: 0.217 CYP2C19-substrate: 0.107
CYP2C9-inhibitor: 0.158 CYP2C9-substrate: 0.876
CYP2D6-inhibitor: 0.007 CYP2D6-substrate: 0.554
CYP3A4-inhibitor: 0.11 CYP3A4-substrate: 0.153

ADMET: Excretion

Clearance (CL): 10.215 Half-life (T1/2): 0.82

ADMET: Toxicity

hERG Blockers: 0.02 Human Hepatotoxicity (H-HT): 0.637
Drug-inuced Liver Injury (DILI): 0.14 AMES Toxicity: 0.017
Rat Oral Acute Toxicity: 0.614 Maximum Recommended Daily Dose: 0.383
Skin Sensitization: 0.32 Carcinogencity: 0.315
Eye Corrosion: 0.003 Eye Irritation: 0.016
Respiratory Toxicity: 0.04
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC005408 1.000 D0S2BV 0.477
ENC005092 1.000 D01CRB 0.309
ENC005206 1.000 D0W1RY 0.308
ENC001087 0.683 D0B3QM 0.300
ENC000825 0.683 D0I0DL 0.295
ENC005971 0.683 D0Q5NX 0.289
ENC005484 0.683 D06ZPS 0.271
ENC000975 0.554 D0X9ZC 0.271
ENC004610 0.554 D02DMQ 0.269
ENC003217 0.554 D03UOT 0.267
*Note: the compound similarity was calculated by RDKIT.