Natural Product: NPC263266

Natural Product ID:  NPC263266
Common Name:   Vermelhotin
IUPAC Name:   (3Z)-3-[6-[(E)-prop-1-enyl]pyran-2-ylidene]pyrrolidine-2,4-dione
Synonyms:  
Molecular Formula:   C12H11NO3
Standard InCHIKey:  AGPWDHWZOCXKTC-ZSLCMEJMSA-N
Standard InCHI:  InChI=1S/C12H11NO3/c1-2-4-8-5-3-6-10(16-8)11-9(14)7-13-12(11)15/h2-6H,7H2,1H3,(H,13,15)/b4-2+,11-10-
Canonical SMILES:  C/C=C/C1=CC=C/C(=C/2C(=O)CN=C2O)/O1
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO32874 unidentified marine-derived fungus cri247-01 Species NA NA Phytochemistry,2008,69: 2621-2626

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 6.2 ug/ml 21676619
NPT113 Cell Line RAW264.7 Mus musculus Inhibition >= 80 % DrugMatrix in vivo data: Pathology
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 3.1 ug/ml 23819871
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 6.2 ug/ml 22365879
NPT113 Cell Line RAW264.7 Mus musculus FC = 203.39 17107790
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 3.1 ug/ml 10.6019/CHEMBL1201861
NPT171 Cell Line MRC5 Homo sapiens IC50 = 6.97 ug/ml 10.6019/CHEMBL1201861
NPT113 Cell Line RAW264.7 Mus musculus Inhibition > 95 % 20608716
NPT113 Cell Line RAW264.7 Mus musculus FC = 144.02 23684893
NPT113 Cell Line RAW264.7 Mus musculus FC = 13.72 12502317
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 5350 nM PubChem BioAssay data set
NPT115 Organism Mycobacterium tuberculosis H37Ra Mycobacterium tuberculosis H37Ra MIC = 3.1 ug/ml 23964704
NPT113 Cell Line RAW264.7 Mus musculus Survival > 80 % 10514307

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC263266 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.7527 Intermediate Similarity NPC313234
0.734 Intermediate Similarity NPC175531
0.7215 Intermediate Similarity NPC469836
0.7037 Intermediate Similarity NPC469835
0.6875 Remote Similarity NPC4706
0.6832 Remote Similarity NPC24389
0.6622 Remote Similarity NPC245650
0.6438 Remote Similarity NPC218486
0.6404 Remote Similarity NPC469838
0.6404 Remote Similarity NPC469833
0.6329 Remote Similarity NPC475618
0.6316 Remote Similarity NPC189700
0.625 Remote Similarity NPC471565
0.625 Remote Similarity NPC471566
0.6154 Remote Similarity NPC6795
0.6154 Remote Similarity NPC130953
0.6145 Remote Similarity NPC471022
0.6053 Remote Similarity NPC150717
0.6053 Remote Similarity NPC221763
0.6049 Remote Similarity NPC471556
0.6026 Remote Similarity NPC133600
0.6022 Remote Similarity NPC185928
0.6 Remote Similarity NPC2328
0.6 Remote Similarity NPC77891
0.5949 Remote Similarity NPC98519
0.5946 Remote Similarity NPC191643
0.593 Remote Similarity NPC326126
0.5921 Remote Similarity NPC173157
0.5921 Remote Similarity NPC25038
0.5904 Remote Similarity NPC470442
0.59 Remote Similarity NPC175614
0.5875 Remote Similarity NPC273614
0.5854 Remote Similarity NPC476589
0.5802 Remote Similarity NPC473737
0.5789 Remote Similarity NPC14234
0.5789 Remote Similarity NPC184014
0.5789 Remote Similarity NPC132669
0.5789 Remote Similarity NPC269800
0.5789 Remote Similarity NPC246519
0.5789 Remote Similarity NPC44193
0.5783 Remote Similarity NPC187315
0.5783 Remote Similarity NPC315115
0.5769 Remote Similarity NPC469598
0.5769 Remote Similarity NPC474825
0.5765 Remote Similarity NPC473277
0.5753 Remote Similarity NPC234084
0.5753 Remote Similarity NPC126184
0.5739 Remote Similarity NPC469515
0.573 Remote Similarity NPC470705
0.5714 Remote Similarity NPC313911
0.5714 Remote Similarity NPC314854
0.57 Remote Similarity NPC116930
0.5698 Remote Similarity NPC59558
0.5698 Remote Similarity NPC315597
0.5686 Remote Similarity NPC167380
0.5686 Remote Similarity NPC265662
0.5684 Remote Similarity NPC296589
0.5676 Remote Similarity NPC307435
0.5676 Remote Similarity NPC267692
0.5664 Remote Similarity NPC476190
0.5647 Remote Similarity NPC313444
0.5647 Remote Similarity NPC249713
0.5647 Remote Similarity NPC287705
0.5647 Remote Similarity NPC477117
0.5641 Remote Similarity NPC51846
0.5638 Remote Similarity NPC475083
0.5636 Remote Similarity NPC170375
0.5616 Remote Similarity NPC128520
0.561 Remote Similarity NPC475073
0.561 Remote Similarity NPC471023
0.56 Remote Similarity NPC267340
0.56 Remote Similarity NPC304223
0.56 Remote Similarity NPC145032
0.56 Remote Similarity NPC54542
0.56 Remote Similarity NPC243539

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC263266 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.5806 Remote Similarity NPD205 Approved
0.5636 Remote Similarity NPD7601 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   73349254
ChEMBL   CHEMBL2426307
ZINC  

Physicochemical Properties

Molecular Weight:  217.07
ALogP:  0.5202
MLogP:  2.34
XLogP:  0.78
# Rotatable Bonds:  3
Polar Surface Area:  58.89
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  16

Download Data

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Biological Activities  
Similar NPs/Drugs