Natural Product: NPC268052

Natural Product ID:  NPC268052
Common Name:   (-)-Citreoisocoumarin
IUPAC Name:   6,8-dihydroxy-3-[(2S)-2-hydroxy-4-oxopentyl]isochromen-1-one
Synonyms:  
Molecular Formula:   C14H14O6
Standard InCHIKey:  OSPHTXUUCFLMQA-SECBINFHSA-N
Standard InCHI:  InChI=1S/C14H14O6/c1-7(15)2-9(16)5-11-4-8-3-10(17)6-12(18)13(8)14(19)20-11/h3-4,6,9,16-18H,2,5H2,1H3/t9-/m1/s1
Canonical SMILES:  CC(=O)C[C@H](Cc1oc(=O)c2c(c1)cc(cc2O)O)O
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
NPO25042 Fusarium tricinctum Species Nectriaceae Eukaryota PMID[24175613]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 64 ug/ml 23219856
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 64 ug/ml 16297615
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 64 ug/ml 26034885
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae MIC > 64 ug/ml 26034885
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC > 64 ug/ml 26034885
NPT19 Organism Escherichia coli Escherichia coli MIC > 64 ug/ml 26034885
NPT2709 Organism Bacillus subtilis subsp. subtilis str. 168 Bacillus subtilis subsp. subtilis str. 168 MIC > 64 ug/ml 26034885

  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 NPC268052 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
0.985 High Similarity NPC32360
0.9704 High Similarity NPC158634
0.9624 High Similarity NPC235115
0.9621 High Similarity NPC175943
0.9556 High Similarity NPC92655
0.9556 High Similarity NPC247409
0.9545 High Similarity NPC153783
0.9481 High Similarity NPC478200
0.9481 High Similarity NPC33144
0.9481 High Similarity NPC94248
0.9481 High Similarity NPC191835
0.9481 High Similarity NPC212693
0.942 High Similarity NPC478202
0.942 High Similarity NPC469542
0.9416 High Similarity NPC244923
0.9412 High Similarity NPC139634
0.9412 High Similarity NPC105456
0.9407 High Similarity NPC70380
0.9407 High Similarity NPC135837
0.9394 High Similarity NPC219892
0.9394 High Similarity NPC189823
0.9362 High Similarity NPC471641
0.9362 High Similarity NPC240253
0.9362 High Similarity NPC471642
0.9362 High Similarity NPC240622
0.9348 High Similarity NPC82913
0.9348 High Similarity NPC474385
0.9343 High Similarity NPC158472
0.9338 High Similarity NPC472602
0.9333 High Similarity NPC50455
0.9281 High Similarity NPC51106
0.9281 High Similarity NPC472006
0.9275 High Similarity NPC472605
0.9275 High Similarity NPC53649
0.9275 High Similarity NPC478217
0.9275 High Similarity NPC67650
0.9275 High Similarity NPC472604
0.9275 High Similarity NPC472035
0.9275 High Similarity NPC472603
0.9275 High Similarity NPC313123
0.9275 High Similarity NPC478201
0.9275 High Similarity NPC1704
0.927 High Similarity NPC88269
0.927 High Similarity NPC52358
0.9259 High Similarity NPC180905
0.9259 High Similarity NPC182496
0.9225 High Similarity NPC153417
0.9214 High Similarity NPC280404
0.9214 High Similarity NPC210425
0.9214 High Similarity NPC277426
0.9214 High Similarity NPC86373
0.9209 High Similarity NPC469579
0.9203 High Similarity NPC472601
0.9203 High Similarity NPC472600
0.9203 High Similarity NPC155205
0.9197 High Similarity NPC475974
0.9161 High Similarity NPC4423
0.9161 High Similarity NPC77325
0.9155 High Similarity NPC210320
0.9155 High Similarity NPC472036
0.9149 High Similarity NPC312789
0.9149 High Similarity NPC257558
0.9149 High Similarity NPC472034
0.9143 High Similarity NPC471731
0.9143 High Similarity NPC159721
0.9137 High Similarity NPC475730
0.9137 High Similarity NPC90411
0.913 High Similarity NPC474655
0.9124 High Similarity NPC474771
0.9124 High Similarity NPC71256
0.9124 High Similarity NPC65837
0.9124 High Similarity NPC149372
0.9124 High Similarity NPC474849
0.9124 High Similarity NPC178467
0.9118 High Similarity NPC142027
0.9118 High Similarity NPC27407
0.9104 High Similarity NPC214702
0.9104 High Similarity NPC470831
0.9103 High Similarity NPC478224
0.9097 High Similarity NPC472891
0.9091 High Similarity NPC73411
0.9091 High Similarity NPC215711
0.9085 High Similarity NPC107625
0.9085 High Similarity NPC472033
0.9085 High Similarity NPC473023
0.9078 High Similarity NPC478203
0.9078 High Similarity NPC42540
0.9078 High Similarity NPC210966
0.9078 High Similarity NPC126882
0.9078 High Similarity NPC151607
0.9071 High Similarity NPC471733
0.9065 High Similarity NPC156872
0.9058 High Similarity NPC472403
0.9058 High Similarity NPC9121
0.9058 High Similarity NPC177307
0.9051 High Similarity NPC291454
0.9051 High Similarity NPC242712
0.9051 High Similarity NPC158481
0.9034 High Similarity NPC91809
0.9028 High Similarity NPC270160
0.9028 High Similarity NPC237440
0.9028 High Similarity NPC84142
0.9028 High Similarity NPC476684
0.9021 High Similarity NPC14098
0.9014 High Similarity NPC473692
0.9014 High Similarity NPC83272
0.9007 High Similarity NPC472610
0.9 High Similarity NPC220106
0.9 High Similarity NPC37530
0.8993 High Similarity NPC57380
0.8993 High Similarity NPC275356
0.8986 High Similarity NPC301915
0.8986 High Similarity NPC194579
0.8986 High Similarity NPC261292
0.898 High Similarity NPC208173
0.898 High Similarity NPC170189
0.898 High Similarity NPC69043
0.898 High Similarity NPC478230
0.8973 High Similarity NPC115249
0.8973 High Similarity NPC184284
0.8973 High Similarity NPC76041
0.8966 High Similarity NPC164762
0.8958 High Similarity NPC221352
0.8944 High Similarity NPC66404
0.8944 High Similarity NPC95123
0.8939 High Similarity NPC201728
0.8939 High Similarity NPC262671
0.8936 High Similarity NPC471644
0.8936 High Similarity NPC250755
0.8936 High Similarity NPC105648
0.8936 High Similarity NPC471640
0.8929 High Similarity NPC99441
0.8929 High Similarity NPC165172
0.8921 High Similarity NPC126739
0.8921 High Similarity NPC221104
0.8921 High Similarity NPC197666
0.8912 High Similarity NPC478231
0.8912 High Similarity NPC137301
0.8905 High Similarity NPC223457
0.8904 High Similarity NPC70016
0.8904 High Similarity NPC215921
0.8897 High Similarity NPC476389
0.8889 High Similarity NPC166583
0.8889 High Similarity NPC471734
0.8889 High Similarity NPC53362
0.8889 High Similarity NPC147757
0.8881 High Similarity NPC41263
0.8881 High Similarity NPC134621
0.8865 High Similarity NPC149533
0.8865 High Similarity NPC470842
0.8859 High Similarity NPC472889
0.8859 High Similarity NPC246466
0.8857 High Similarity NPC471819
0.8851 High Similarity NPC478221
0.8851 High Similarity NPC472890
0.8844 High Similarity NPC167903
0.8836 High Similarity NPC295036
0.8836 High Similarity NPC469619
0.8836 High Similarity NPC56204
0.8836 High Similarity NPC469670
0.8819 High Similarity NPC471735
0.8819 High Similarity NPC237208
0.8819 High Similarity NPC267509
0.8811 High Similarity NPC257025
0.8811 High Similarity NPC475201
0.8803 High Similarity NPC322112
0.8803 High Similarity NPC297985
0.8784 High Similarity NPC281477
0.8776 High Similarity NPC200773
0.8776 High Similarity NPC240768
0.8768 High Similarity NPC474097
0.8759 High Similarity NPC478190
0.8759 High Similarity NPC476463
0.8759 High Similarity NPC475589
0.8759 High Similarity NPC31872
0.8759 High Similarity NPC473584
0.875 High Similarity NPC29577
0.875 High Similarity NPC32470
0.8741 High Similarity NPC354984
0.8741 High Similarity NPC310340
0.8741 High Similarity NPC293453
0.8741 High Similarity NPC471643
0.8741 High Similarity NPC471639
0.8733 High Similarity NPC478225
0.8733 High Similarity NPC478226
0.8732 High Similarity NPC275734
0.8732 High Similarity NPC130485
0.8731 High Similarity NPC95309
0.8725 High Similarity NPC99381
0.8725 High Similarity NPC317585
0.8725 High Similarity NPC82592
0.8725 High Similarity NPC16082
0.8722 High Similarity NPC91475
0.8722 High Similarity NPC265910
0.8716 High Similarity NPC271681
0.8716 High Similarity NPC273483
0.8714 High Similarity NPC193792
0.8714 High Similarity NPC245058
0.8707 High Similarity NPC96501
0.8707 High Similarity NPC60413

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC268052 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
0.9412 High Similarity NPD970 Clinical (unspecified phase)
0.8511 High Similarity NPD1510 Phase 2
0.8493 Intermediate Similarity NPD2532 Approved
0.8493 Intermediate Similarity NPD2533 Approved
0.8493 Intermediate Similarity NPD2534 Approved
0.8411 Intermediate Similarity NPD7819 Suspended
0.8392 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8392 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8357 Intermediate Similarity NPD1240 Approved
0.8345 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1549 Phase 2
0.8298 Intermediate Similarity NPD230 Phase 1
0.8239 Intermediate Similarity NPD1607 Approved
0.8219 Intermediate Similarity NPD3750 Approved
0.8176 Intermediate Similarity NPD1511 Approved
0.8125 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD1934 Approved
0.8092 Intermediate Similarity NPD4380 Phase 2
0.8069 Intermediate Similarity NPD1551 Phase 2
0.8069 Intermediate Similarity NPD2796 Approved
0.8067 Intermediate Similarity NPD1512 Approved
0.806 Intermediate Similarity NPD9545 Approved
0.8054 Intermediate Similarity NPD6799 Approved
0.8052 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD7075 Discontinued
0.8 Intermediate Similarity NPD3817 Phase 2
0.7987 Intermediate Similarity NPD6801 Discontinued
0.7975 Intermediate Similarity NPD6959 Discontinued
0.7935 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD2801 Approved
0.7925 Intermediate Similarity NPD6232 Discontinued
0.7922 Intermediate Similarity NPD7411 Suspended
0.791 Intermediate Similarity NPD9493 Approved
0.7905 Intermediate Similarity NPD1243 Approved
0.7898 Intermediate Similarity NPD3749 Approved
0.7898 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD7473 Discontinued
0.7885 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD3748 Approved
0.7857 Intermediate Similarity NPD6599 Discontinued
0.7847 Intermediate Similarity NPD943 Approved
0.7834 Intermediate Similarity NPD3882 Suspended
0.7832 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD2935 Discontinued
0.7812 Intermediate Similarity NPD5710 Approved
0.7812 Intermediate Similarity NPD5711 Approved
0.7791 Intermediate Similarity NPD7054 Approved
0.7785 Intermediate Similarity NPD2800 Approved
0.7778 Intermediate Similarity NPD920 Approved
0.7778 Intermediate Similarity NPD5403 Approved
0.7771 Intermediate Similarity NPD5402 Approved
0.7763 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD5401 Approved
0.7748 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD7472 Approved
0.773 Intermediate Similarity NPD3818 Discontinued
0.7722 Intermediate Similarity NPD7768 Phase 2
0.7722 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD6166 Phase 2
0.7716 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7698 Intermediate Similarity NPD422 Phase 1
0.7697 Intermediate Similarity NPD6797 Phase 2
0.7697 Intermediate Similarity NPD7390 Discontinued
0.7683 Intermediate Similarity NPD5844 Phase 1
0.7651 Intermediate Similarity NPD7251 Discontinued
0.7647 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD9717 Approved
0.7636 Intermediate Similarity NPD7074 Phase 3
0.7625 Intermediate Similarity NPD919 Approved
0.7619 Intermediate Similarity NPD6651 Approved
0.7616 Intermediate Similarity NPD4628 Phase 3
0.7606 Intermediate Similarity NPD1203 Approved
0.7605 Intermediate Similarity NPD7808 Phase 3
0.7595 Intermediate Similarity NPD1465 Phase 2
0.7586 Intermediate Similarity NPD3764 Approved
0.7576 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD1201 Approved
0.7564 Intermediate Similarity NPD3226 Approved
0.755 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD9269 Phase 2
0.75 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD1470 Approved
0.7482 Intermediate Similarity NPD9268 Approved
0.7467 Intermediate Similarity NPD5405 Approved
0.7467 Intermediate Similarity NPD6100 Approved
0.7467 Intermediate Similarity NPD5406 Approved
0.7467 Intermediate Similarity NPD5404 Approved
0.7467 Intermediate Similarity NPD6099 Approved
0.7467 Intermediate Similarity NPD5408 Approved
0.7466 Intermediate Similarity NPD411 Approved
0.744 Intermediate Similarity NPD6559 Discontinued
0.7432 Intermediate Similarity NPD447 Suspended
0.7417 Intermediate Similarity NPD2346 Discontinued
0.74 Intermediate Similarity NPD2799 Discontinued
0.74 Intermediate Similarity NPD7033 Discontinued
0.7394 Intermediate Similarity NPD1608 Approved
0.7381 Intermediate Similarity NPD5953 Discontinued
0.7381 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD5494 Approved
0.7361 Intermediate Similarity NPD1164 Approved
0.7356 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6832 Phase 2
0.732 Intermediate Similarity NPD2654 Approved
0.7315 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD9266 Approved
0.7313 Intermediate Similarity NPD74 Approved
0.7312 Intermediate Similarity NPD37 Approved
0.7308 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD2344 Approved
0.7294 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD4966 Approved
0.7284 Intermediate Similarity NPD4965 Approved
0.7284 Intermediate Similarity NPD4967 Phase 2
0.7262 Intermediate Similarity NPD7286 Phase 2
0.7239 Intermediate Similarity NPD9263 Approved
0.7239 Intermediate Similarity NPD9264 Approved
0.7239 Intermediate Similarity NPD9267 Approved
0.7239 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD1296 Phase 2
0.723 Intermediate Similarity NPD3268 Approved
0.723 Intermediate Similarity NPD2313 Discontinued
0.7226 Intermediate Similarity NPD6190 Approved
0.7225 Intermediate Similarity NPD8150 Discontinued
0.7222 Intermediate Similarity NPD4288 Approved
0.7215 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD1247 Approved
0.7212 Intermediate Similarity NPD7199 Phase 2
0.7202 Intermediate Similarity NPD3751 Discontinued
0.72 Intermediate Similarity NPD5124 Phase 1
0.72 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD6234 Discontinued
0.7192 Intermediate Similarity NPD2798 Approved
0.7192 Intermediate Similarity NPD1019 Discontinued
0.7183 Intermediate Similarity NPD17 Approved
0.7172 Intermediate Similarity NPD1283 Approved
0.7163 Intermediate Similarity NPD1548 Phase 1
0.7123 Intermediate Similarity NPD2797 Approved
0.7115 Intermediate Similarity NPD2309 Approved
0.7114 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1652 Phase 2
0.7083 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD1610 Phase 2
0.7067 Intermediate Similarity NPD520 Approved
0.7066 Intermediate Similarity NPD3787 Discontinued
0.7066 Intermediate Similarity NPD7229 Phase 3
0.7063 Intermediate Similarity NPD4626 Approved
0.7063 Intermediate Similarity NPD1778 Approved
0.7063 Intermediate Similarity NPD1653 Approved
0.7059 Intermediate Similarity NPD4308 Phase 3
0.7055 Intermediate Similarity NPD3225 Approved
0.7052 Intermediate Similarity NPD8313 Approved
0.7052 Intermediate Similarity NPD8312 Approved
0.7045 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6273 Approved
0.7043 Intermediate Similarity NPD8151 Discontinued
0.7027 Intermediate Similarity NPD9494 Approved
0.7025 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD3926 Phase 2
0.702 Intermediate Similarity NPD1613 Approved
0.702 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD5353 Approved
0.7007 Intermediate Similarity NPD3266 Approved
0.7007 Intermediate Similarity NPD3267 Approved
0.7 Intermediate Similarity NPD7228 Approved
0.7 Intermediate Similarity NPD9281 Approved
0.7 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.6993 Remote Similarity NPD5691 Approved
0.6983 Remote Similarity NPD4360 Phase 2
0.6983 Remote Similarity NPD4363 Phase 3
0.698 Remote Similarity NPD4908 Phase 1
0.698 Remote Similarity NPD1008 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1281 Approved
0.6959 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7435 Discontinued
0.6949 Remote Similarity NPD4287 Approved
0.6943 Remote Similarity NPD7003 Approved
0.694 Remote Similarity NPD9261 Approved
0.6933 Remote Similarity NPD3027 Phase 3
0.6929 Remote Similarity NPD1241 Discontinued
0.6914 Remote Similarity NPD7458 Discontinued
0.6908 Remote Similarity NPD4060 Phase 1
0.6889 Remote Similarity NPD6535 Approved
0.6889 Remote Similarity NPD6534 Approved
0.6887 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6887 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6885 Remote Similarity NPD6780 Approved
0.6885 Remote Similarity NPD6776 Approved
0.6885 Remote Similarity NPD6781 Approved
0.6885 Remote Similarity NPD6778 Approved
0.6885 Remote Similarity NPD6777 Approved
0.6885 Remote Similarity NPD6779 Approved
0.6885 Remote Similarity NPD6782 Approved

Structure

External Identifiers

PubChem CID   15071544
ChEMBL   CHEMBL3086840
ZINC  

Physicochemical Properties

Molecular Weight:  278.08
ALogP:  -1.4649
MLogP:  2.34
XLogP:  0.264
# Rotatable Bonds:  8
Polar Surface Area:  104.06
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  20

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs