Natural Product: ENC000975

NPs Basic Information

Download MOL File
Name
Brevianamide F
Molecular Formula C16H17N3O2
IUPAC Name*
(3S,8aS)-3-(1H-indol-3-ylmethyl)-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=CNC4=CC=CC=C43
InChI
InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1
InChIKey
RYFZBPVMVYTEKZ-KBPBESRZSA-N
Synonyms
Brevianamide F; 38136-70-8; Cyclo-L-Trp-L-Pro; L-prolyl-L-tryptophan anhydride; cyclo-(Trp-Pro); Cyclo(L-Pro-L-Trp); Cyclo-L-tryptophyl-L-proline; (3s,8as)-3-(1h-Indol-3-Ylmethyl)hexahydropyrrolo[1,2-A]pyrazine-1,4-Dione; cyclo-L-tryptophanyl-L-proline; 76XZ426FPP; CHEBI:64530; tryptophan-proline diketopiperazine; (3S,8aS)-3-((1H-Indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione; L-tryptophyl-L-proline cyclic anhydride; (3S,8aS)-3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione; BrevianamideF; cyclo-L-Prolyl-L-tryptophanyl; (3S,8AS)-HEXAHYDRO-3-(1H-INDOL-3-YLMETHYL)PYRROLO(1,2-A)PYRAZINE-1,4-DIONE; (3S,8aS)-Hexahydro-3-(1H-indol-3-ylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione; QRP; Cyclo(L-Trp-L-Pro); cyclo-(L-Trp-L-Pro); UNII-76XZ426FPP; cyclo-L-proline-L-pryptophan; cyclo-L-pryptophan-L-proline; CHEMBL563557; SCHEMBL2018181; DTXSID10959075; ZINC1582158; Brevianamide F; cyclo-L-Trp-L-Pro; MFCD29917326; s6751; CS-5688; AC-35169; AS-60483; HY-100385; C20563; A873918; Q25323862; (3S,8aS)-3-[(1H-indol-3-yl)methyl]-octahydropyrrolo[1,2-a]piperazine-1,4-dione; (3S,8aS)-3-[(1H-indol-3-yl)methyl]-octahydropyrrolo[1,2-a]pyrazine-1,4-dione; 1-Hydroxy-3-[(1H-indol-3-yl)methyl]-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazin-4(3H)-one
CAS 38136-70-8
PubChem CID 181567
ChEMBL ID CHEMBL563557
*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

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NPs Physi-Chem Properties

Molecular Weight: 283.32 ALogp: 1.5
HBD: 2 HBA: 2
Rotatable Bonds: 2 Lipinski's rule of five: Accepted
Polar Surface Area: 65.2 Aromatic Rings: 4
Heavy Atoms: 21 QED Weighted: 0.88

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.631 MDCK Permeability: 0.00000959
Pgp-inhibitor: 0.001 Pgp-substrate: 0.006
Human Intestinal Absorption (HIA): 0.009 20% Bioavailability (F20%): 0.019
30% Bioavailability (F30%): 0.637

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.668 Plasma Protein Binding (PPB): 51.39%
Volume Distribution (VD): 0.742 Fu: 38.70%

ADMET: Metabolism

CYP1A2-inhibitor: 0.075 CYP1A2-substrate: 0.479
CYP2C19-inhibitor: 0.556 CYP2C19-substrate: 0.18
CYP2C9-inhibitor: 0.191 CYP2C9-substrate: 0.895
CYP2D6-inhibitor: 0.027 CYP2D6-substrate: 0.694
CYP3A4-inhibitor: 0.566 CYP3A4-substrate: 0.182

ADMET: Excretion

Clearance (CL): 5.954 Half-life (T1/2): 0.795

ADMET: Toxicity

hERG Blockers: 0.025 Human Hepatotoxicity (H-HT): 0.796
Drug-inuced Liver Injury (DILI): 0.202 AMES Toxicity: 0.019
Rat Oral Acute Toxicity: 0.779 Maximum Recommended Daily Dose: 0.815
Skin Sensitization: 0.377 Carcinogencity: 0.162
Eye Corrosion: 0.003 Eye Irritation: 0.014
Respiratory Toxicity: 0.135
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

*Note: the compound similarity was calculated by RDKIT.