Natural Product: ENC002520

NPs Basic Information

Download MOL File
Name
6-methoxyspirotryprostatin B
Molecular Formula C22H23N3O4
IUPAC Name*
(5S,6S,9S)-6'-methoxy-6-(2-methylprop-1-enyl)spiro[1,7-diazatricyclo[7.3.0.03,7]dodec-3-ene-5,3'-1H-indole]-2,2',8-trione
SMILES
CC(=C[C@H]1[C@]2(C=C3N1C(=O)[C@@H]4CCCN4C3=O)C5=C(C=C(C=C5)OC)NC2=O)C
InChI
InChI=1S/C22H23N3O4/c1-12(2)9-18-22(14-7-6-13(29-3)10-15(14)23-21(22)28)11-17-19(26)24-8-4-5-16(24)20(27)25(17)18/h6-7,9-11,16,18H,4-5,8H2,1-3H3,(H,23,28)/t16-,18-,22-/m0/s1
InChIKey
UHQKDPCPFNXIDU-ZJBJCVSYSA-N
Synonyms
6-methoxyspirotryprostatin B; CHEBI:66707; (2S,3S,5aS)-5a,6,7,8-Tetrahydro-6'-methoxy-3-(2-methyl-1-propen-1-yl)spiro[5H,10H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),3'-[3H]indole]-2',5,10(1'H)-trione; (2S,3S,5aS)-6'-methoxy-3-(2-methylprop-1-en-1-yl)-5a,6,7,8-tetrahydro-5H,10H-spiro[dipyrrolo[1,2-a:1',2'-d]pyrazine-2,3'-indole]-2',5,10(1'H)-trione; CHEMBL488302; Q27135329; (5S,6S,9S)-6'-methoxy-6-(2-methylprop-1-enyl)spiro[1,7-diazatricyclo[7.3.0.03,7]dodec-3-ene-5,3'-1H-indole]-2,2',8-trione
CAS NA
PubChem CID 24900164
ChEMBL ID CHEMBL488302
*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 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

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NPs Physi-Chem Properties

Molecular Weight: 393.4 ALogp: 1.8
HBD: 1 HBA: 4
Rotatable Bonds: 2 Lipinski's rule of five: Accepted
Polar Surface Area: 79.0 Aromatic Rings: 5
Heavy Atoms: 29 QED Weighted: 0.784

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -5.043 MDCK Permeability: 0.00001820
Pgp-inhibitor: 0.668 Pgp-substrate: 0.665
Human Intestinal Absorption (HIA): 0.007 20% Bioavailability (F20%): 0.239
30% Bioavailability (F30%): 0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.948 Plasma Protein Binding (PPB): 85.81%
Volume Distribution (VD): 1.036 Fu: 16.75%

ADMET: Metabolism

CYP1A2-inhibitor: 0.019 CYP1A2-substrate: 0.642
CYP2C19-inhibitor: 0.489 CYP2C19-substrate: 0.878
CYP2C9-inhibitor: 0.257 CYP2C9-substrate: 0.695
CYP2D6-inhibitor: 0.022 CYP2D6-substrate: 0.199
CYP3A4-inhibitor: 0.454 CYP3A4-substrate: 0.926

ADMET: Excretion

Clearance (CL): 7.943 Half-life (T1/2): 0.128

ADMET: Toxicity

hERG Blockers: 0.026 Human Hepatotoxicity (H-HT): 0.951
Drug-inuced Liver Injury (DILI): 0.883 AMES Toxicity: 0.065
Rat Oral Acute Toxicity: 0.727 Maximum Recommended Daily Dose: 0.593
Skin Sensitization: 0.745 Carcinogencity: 0.692
Eye Corrosion: 0.003 Eye Irritation: 0.007
Respiratory Toxicity: 0.529
*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.