Natural Product: NPC196771

Natural Product ID:  NPC196771
Common Name:   Justicinol
IUPAC Name:   9-(1,3-benzodioxol-5-yl)-5-hydroxy-4,6,8-trimethoxy-3H-benzo[f][2]benzofuran-1-one
Synonyms:   Justicinol
Molecular Formula:   C22H18O8
Standard InCHIKey:  HVJLXRHXIVYZJS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C22H18O8/c1-25-14-7-15(26-2)20(23)19-18(14)16(10-4-5-12-13(6-10)30-9-29-12)17-11(21(19)27-3)8-28-22(17)24/h4-7,23H,8-9H2,1-3H3
Canonical SMILES:  COc1cc(OC)c2c(c1O)c(OC)c1c(c2c2ccc3c(c2)OCO3)C(=O)OC1
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
NPO20590 Justicia patentiflora Species Acanthaceae Eukaryota Vietnam PMID[15921419]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens IC50 = 300 nM 22559947
NPT83 Cell Line MCF7 Homo sapiens IC50 = 360 nM 22559947

  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 NPC196771 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
0.9693 High Similarity NPC117911
0.9571 High Similarity NPC174734
0.9571 High Similarity NPC474042
0.9387 High Similarity NPC22130
0.9387 High Similarity NPC116838
0.9202 High Similarity NPC474043
0.9152 High Similarity NPC198796
0.9141 High Similarity NPC143328
0.9085 High Similarity NPC125713
0.908 High Similarity NPC239113
0.908 High Similarity NPC115123
0.9048 High Similarity NPC311912
0.903 High Similarity NPC474770
0.9024 High Similarity NPC115281
0.9024 High Similarity NPC181168
0.9024 High Similarity NPC163527
0.9018 High Similarity NPC234730
0.9006 High Similarity NPC193377
0.9 High Similarity NPC312006
0.9 High Similarity NPC474075
0.9 High Similarity NPC20114
0.9 High Similarity NPC114550
0.9 High Similarity NPC471920
0.9 High Similarity NPC292712
0.9 High Similarity NPC129930
0.9 High Similarity NPC471921
0.9 High Similarity NPC471922
0.8994 High Similarity NPC88557
0.8963 High Similarity NPC109765
0.8947 High Similarity NPC184624
0.8935 High Similarity NPC79322
0.8916 High Similarity NPC91634
0.8916 High Similarity NPC78944
0.8916 High Similarity NPC268718
0.8916 High Similarity NPC150943
0.8909 High Similarity NPC202495
0.8909 High Similarity NPC19600
0.8908 High Similarity NPC208797
0.8908 High Similarity NPC53680
0.8889 High Similarity NPC471181
0.8889 High Similarity NPC178737
0.8848 High Similarity NPC473900
0.8844 High Similarity NPC67629
0.8844 High Similarity NPC79736
0.8841 High Similarity NPC103197
0.8841 High Similarity NPC30009
0.8795 High Similarity NPC19947
0.8795 High Similarity NPC207584
0.8795 High Similarity NPC474990
0.8793 High Similarity NPC35266
0.8793 High Similarity NPC267549
0.8779 High Similarity NPC158226
0.8779 High Similarity NPC469506
0.8765 High Similarity NPC471923
0.8765 High Similarity NPC320471
0.8765 High Similarity NPC118162
0.8765 High Similarity NPC83049
0.8757 High Similarity NPC116759
0.8757 High Similarity NPC14294
0.875 High Similarity NPC15212
0.875 High Similarity NPC258322
0.875 High Similarity NPC288149
0.875 High Similarity NPC191352
0.8743 High Similarity NPC275690
0.8743 High Similarity NPC161609
0.8743 High Similarity NPC45846
0.8736 High Similarity NPC472723
0.8735 High Similarity NPC237946
0.8735 High Similarity NPC32373
0.8727 High Similarity NPC273578
0.8721 High Similarity NPC109827
0.8721 High Similarity NPC17219
0.8721 High Similarity NPC124470
0.872 High Similarity NPC118332
0.872 High Similarity NPC104353
0.8713 High Similarity NPC473531
0.8713 High Similarity NPC475453
0.8713 High Similarity NPC471180
0.8708 High Similarity NPC105591
0.8698 High Similarity NPC76687
0.8698 High Similarity NPC474763
0.8693 High Similarity NPC8940
0.869 High Similarity NPC96593
0.8683 High Similarity NPC296044
0.8683 High Similarity NPC167098
0.8678 High Similarity NPC469354
0.8678 High Similarity NPC199533
0.8678 High Similarity NPC470454
0.8678 High Similarity NPC469438
0.8674 High Similarity NPC476358
0.8671 High Similarity NPC260263
0.8663 High Similarity NPC165979
0.8663 High Similarity NPC99613
0.8663 High Similarity NPC49487
0.8663 High Similarity NPC163130
0.8663 High Similarity NPC211309
0.8655 High Similarity NPC472452
0.8647 High Similarity NPC270837
0.8647 High Similarity NPC475865
0.8639 High Similarity NPC311740
0.8639 High Similarity NPC295009
0.8639 High Similarity NPC239890
0.8639 High Similarity NPC209411
0.8639 High Similarity NPC260640
0.8636 High Similarity NPC470091
0.8636 High Similarity NPC329161
0.8636 High Similarity NPC240887
0.8636 High Similarity NPC183843
0.8636 High Similarity NPC212290
0.8629 High Similarity NPC473713
0.8629 High Similarity NPC297574
0.8621 High Similarity NPC477881
0.8621 High Similarity NPC316539
0.8614 High Similarity NPC54179
0.8613 High Similarity NPC180768
0.8613 High Similarity NPC477572
0.8613 High Similarity NPC52598
0.8613 High Similarity NPC477573
0.8613 High Similarity NPC477571
0.8606 High Similarity NPC78505
0.8605 High Similarity NPC234331
0.8605 High Similarity NPC185498
0.8603 High Similarity NPC174486
0.8598 High Similarity NPC475722
0.8598 High Similarity NPC24425
0.8598 High Similarity NPC261322
0.8598 High Similarity NPC149505
0.8596 High Similarity NPC114120
0.8596 High Similarity NPC167045
0.8596 High Similarity NPC474301
0.8596 High Similarity NPC327652
0.8596 High Similarity NPC26386
0.8596 High Similarity NPC326520
0.8596 High Similarity NPC477884
0.8588 High Similarity NPC473445
0.8588 High Similarity NPC188217
0.8588 High Similarity NPC265795
0.8588 High Similarity NPC144843
0.8588 High Similarity NPC291957
0.8588 High Similarity NPC14030
0.8588 High Similarity NPC42797
0.8588 High Similarity NPC294965
0.858 High Similarity NPC297807
0.858 High Similarity NPC285973
0.858 High Similarity NPC24627
0.858 High Similarity NPC53889
0.858 High Similarity NPC84571
0.858 High Similarity NPC225624
0.858 High Similarity NPC260300
0.858 High Similarity NPC119910
0.8571 High Similarity NPC35598
0.8571 High Similarity NPC227906
0.8571 High Similarity NPC139350
0.8571 High Similarity NPC472607
0.8571 High Similarity NPC222689
0.8571 High Similarity NPC472860
0.8563 High Similarity NPC223375
0.8563 High Similarity NPC473697
0.8563 High Similarity NPC472835
0.8563 High Similarity NPC476642
0.8563 High Similarity NPC475825
0.8555 High Similarity NPC476279
0.8555 High Similarity NPC471287
0.8554 High Similarity NPC178574
0.8554 High Similarity NPC65591
0.8554 High Similarity NPC245948
0.8547 High Similarity NPC261623
0.8547 High Similarity NPC329119
0.8547 High Similarity NPC20216
0.8547 High Similarity NPC111490
0.8547 High Similarity NPC29160
0.8547 High Similarity NPC43065
0.8547 High Similarity NPC170245
0.8545 High Similarity NPC477700
0.8545 High Similarity NPC13985
0.8545 High Similarity NPC210642
0.8545 High Similarity NPC32079
0.8538 High Similarity NPC474350
0.8538 High Similarity NPC156082
0.8538 High Similarity NPC197168
0.8538 High Similarity NPC291977
0.8538 High Similarity NPC470898
0.8538 High Similarity NPC67959
0.8538 High Similarity NPC236132
0.8538 High Similarity NPC470178
0.8538 High Similarity NPC477689
0.8537 High Similarity NPC668
0.8537 High Similarity NPC174512
0.8537 High Similarity NPC293757
0.8537 High Similarity NPC216223
0.8537 High Similarity NPC145569
0.8537 High Similarity NPC127827
0.8537 High Similarity NPC474965
0.8537 High Similarity NPC477695
0.8531 High Similarity NPC80956
0.8531 High Similarity NPC84494
0.8531 High Similarity NPC113446
0.8531 High Similarity NPC245059
0.8529 High Similarity NPC311803
0.8529 High Similarity NPC25389

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC196771 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
0.897 High Similarity NPD6234 Discontinued
0.8922 High Similarity NPD6232 Discontinued
0.8772 High Similarity NPD5844 Phase 1
0.8765 High Similarity NPD7473 Discontinued
0.8735 High Similarity NPD4966 Approved
0.8735 High Similarity NPD4967 Phase 2
0.8735 High Similarity NPD4965 Approved
0.8605 High Similarity NPD7228 Approved
0.8554 High Similarity NPD37 Approved
0.8529 High Similarity NPD7199 Phase 2
0.8492 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.843 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8402 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8391 Intermediate Similarity NPD3818 Discontinued
0.8364 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8324 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.8258 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8202 Intermediate Similarity NPD6559 Discontinued
0.8176 Intermediate Similarity NPD1465 Phase 2
0.8176 Intermediate Similarity NPD2801 Approved
0.8133 Intermediate Similarity NPD2534 Approved
0.8133 Intermediate Similarity NPD2533 Approved
0.8133 Intermediate Similarity NPD2532 Approved
0.8101 Intermediate Similarity NPD7240 Approved
0.8098 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.809 Intermediate Similarity NPD7074 Phase 3
0.807 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8034 Intermediate Similarity NPD7054 Approved
0.8012 Intermediate Similarity NPD1934 Approved
0.7989 Intermediate Similarity NPD7472 Approved
0.7977 Intermediate Similarity NPD3882 Suspended
0.7967 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7966 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7966 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7966 Intermediate Similarity NPD6166 Phase 2
0.7943 Intermediate Similarity NPD5494 Approved
0.7919 Intermediate Similarity NPD3817 Phase 2
0.7898 Intermediate Similarity NPD6959 Discontinued
0.7861 Intermediate Similarity NPD7819 Suspended
0.7845 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7845 Intermediate Similarity NPD6797 Phase 2
0.7802 Intermediate Similarity NPD7251 Discontinued
0.7772 Intermediate Similarity NPD7680 Approved
0.776 Intermediate Similarity NPD7808 Phase 3
0.7755 Intermediate Similarity NPD8151 Discontinued
0.7749 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD7075 Discontinued
0.7727 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD8312 Approved
0.7717 Intermediate Similarity NPD8313 Approved
0.7705 Intermediate Similarity NPD7685 Pre-registration
0.7688 Intermediate Similarity NPD4380 Phase 2
0.768 Intermediate Similarity NPD7435 Discontinued
0.7677 Intermediate Similarity NPD7783 Phase 2
0.7677 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD1653 Approved
0.7654 Intermediate Similarity NPD7229 Phase 3
0.7647 Intermediate Similarity NPD1511 Approved
0.7644 Intermediate Similarity NPD7411 Suspended
0.7637 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD7458 Discontinued
0.7627 Intermediate Similarity NPD3749 Approved
0.7622 Intermediate Similarity NPD230 Phase 1
0.7617 Intermediate Similarity NPD6776 Approved
0.7617 Intermediate Similarity NPD6781 Approved
0.7617 Intermediate Similarity NPD6782 Approved
0.7617 Intermediate Similarity NPD6780 Approved
0.7617 Intermediate Similarity NPD6779 Approved
0.7617 Intermediate Similarity NPD6778 Approved
0.7617 Intermediate Similarity NPD6777 Approved
0.7571 Intermediate Similarity NPD7768 Phase 2
0.7569 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD1512 Approved
0.7557 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD5711 Approved
0.7556 Intermediate Similarity NPD5710 Approved
0.7545 Intermediate Similarity NPD2935 Discontinued
0.7529 Intermediate Similarity NPD3226 Approved
0.7529 Intermediate Similarity NPD6190 Approved
0.7515 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1247 Approved
0.75 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6801 Discontinued
0.7486 Intermediate Similarity NPD919 Approved
0.7486 Intermediate Similarity NPD6599 Discontinued
0.7471 Intermediate Similarity NPD4628 Phase 3
0.7471 Intermediate Similarity NPD3750 Approved
0.7462 Intermediate Similarity NPD7870 Phase 2
0.7462 Intermediate Similarity NPD7871 Phase 2
0.7458 Intermediate Similarity NPD8455 Phase 2
0.745 Intermediate Similarity NPD7874 Approved
0.745 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD7390 Discontinued
0.7429 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7418 Intermediate Similarity NPD3926 Phase 2
0.7416 Intermediate Similarity NPD5402 Approved
0.7411 Intermediate Similarity NPD7698 Approved
0.7411 Intermediate Similarity NPD7696 Phase 3
0.7411 Intermediate Similarity NPD7697 Approved
0.7399 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD3751 Discontinued
0.7368 Intermediate Similarity NPD7003 Approved
0.7363 Intermediate Similarity NPD3787 Discontinued
0.736 Intermediate Similarity NPD6823 Phase 2
0.7358 Intermediate Similarity NPD6535 Approved
0.7358 Intermediate Similarity NPD6534 Approved
0.735 Intermediate Similarity NPD7701 Phase 2
0.7341 Intermediate Similarity NPD6799 Approved
0.7333 Intermediate Similarity NPD3764 Approved
0.7316 Intermediate Similarity NPD8150 Discontinued
0.7278 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD1510 Phase 2
0.7273 Intermediate Similarity NPD5006 Approved
0.7273 Intermediate Similarity NPD3027 Phase 3
0.7273 Intermediate Similarity NPD5005 Approved
0.7262 Intermediate Similarity NPD1607 Approved
0.7245 Intermediate Similarity NPD7699 Phase 2
0.7245 Intermediate Similarity NPD7700 Phase 2
0.7241 Intermediate Similarity NPD7801 Approved
0.7235 Intermediate Similarity NPD5405 Approved
0.7235 Intermediate Similarity NPD5406 Approved
0.7235 Intermediate Similarity NPD5408 Approved
0.7235 Intermediate Similarity NPD5404 Approved
0.7229 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD5242 Approved
0.7225 Intermediate Similarity NPD8434 Phase 2
0.7216 Intermediate Similarity NPD920 Approved
0.7209 Intermediate Similarity NPD6674 Discontinued
0.7204 Intermediate Similarity NPD7177 Discontinued
0.7193 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD2346 Discontinued
0.7193 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD7266 Discontinued
0.7177 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD3748 Approved
0.7169 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD7999 Approved
0.7157 Intermediate Similarity NPD4420 Approved
0.7151 Intermediate Similarity NPD1549 Phase 2
0.7143 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD943 Approved
0.7143 Intermediate Similarity NPD1613 Approved
0.7143 Intermediate Similarity NPD1240 Approved
0.7136 Intermediate Similarity NPD7930 Approved
0.7135 Intermediate Similarity NPD1551 Phase 2
0.7135 Intermediate Similarity NPD2438 Suspended
0.7128 Intermediate Similarity NPD6212 Phase 3
0.7128 Intermediate Similarity NPD6213 Phase 3
0.7128 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD7827 Phase 1
0.712 Intermediate Similarity NPD8127 Discontinued
0.7114 Intermediate Similarity NPD8320 Phase 1
0.7114 Intermediate Similarity NPD8319 Approved
0.711 Intermediate Similarity NPD2800 Approved
0.7108 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD7028 Phase 2
0.7085 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1283 Approved
0.7066 Intermediate Similarity NPD4625 Phase 3
0.7048 Intermediate Similarity NPD9494 Approved
0.7048 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD2979 Phase 3
0.7041 Intermediate Similarity NPD4060 Phase 1
0.7035 Intermediate Similarity NPD6100 Approved
0.7035 Intermediate Similarity NPD2796 Approved
0.7035 Intermediate Similarity NPD6099 Approved
0.7024 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD5403 Approved
0.7011 Intermediate Similarity NPD1243 Approved
0.7 Intermediate Similarity NPD5953 Discontinued
0.7 Intermediate Similarity NPD447 Suspended
0.7 Intermediate Similarity NPD1933 Approved
0.6994 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6994 Remote Similarity NPD3705 Approved
0.6989 Remote Similarity NPD643 Clinical (unspecified phase)
0.6982 Remote Similarity NPD6233 Phase 2
0.6977 Remote Similarity NPD651 Clinical (unspecified phase)
0.6973 Remote Similarity NPD6746 Phase 2
0.6971 Remote Similarity NPD8166 Discontinued
0.6966 Remote Similarity NPD6273 Approved
0.6961 Remote Similarity NPD6386 Approved
0.6961 Remote Similarity NPD6385 Approved
0.6951 Remote Similarity NPD9269 Phase 2
0.694 Remote Similarity NPD5353 Approved
0.6927 Remote Similarity NPD7549 Discontinued
0.6923 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6798 Discontinued
0.6912 Remote Similarity NPD7211 Clinical (unspecified phase)
0.691 Remote Similarity NPD5401 Approved
0.6905 Remote Similarity NPD4908 Phase 1
0.6897 Remote Similarity NPD2344 Approved
0.6895 Remote Similarity NPD7286 Phase 2

Structure

External Identifiers

PubChem CID   11373226
ChEMBL   CHEMBL518690
ZINC  

Physicochemical Properties

Molecular Weight:  410.10
ALogP:  -0.9979
MLogP:  3
XLogP:  1.573
# Rotatable Bonds:  8
Polar Surface Area:  92.68
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  30

Download Data

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