Natural Product: NPC186933

Natural Product ID:  NPC186933
Common Name:   1Alpha-Hydroxy-4Alphah-1,2,3,4-Tetrahydrocadalen-15-Oic Acid
IUPAC Name:   (5R,8S)-5-hydroxy-5-methyl-8-propan-2-yl-7,8-dihydro-6H-naphthalene-2-carboxylic acid
Synonyms:  
Molecular Formula:   C15H20O3
Standard InCHIKey:  WOURYSLHFFSMAH-XHDPSFHLSA-N
Standard InCHI:  InChI=1S/C15H20O3/c1-9(2)11-6-7-15(3,18)13-5-4-10(14(16)17)8-12(11)13/h4-5,8-9,11,18H,6-7H2,1-3H3,(H,16,17)/t11-,15+/m0/s1
Canonical SMILES:  CC([C@@H]1CC[C@@](c2c1cc(cc2)C(=O)O)(C)O)C
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
NPO25769 Heterotheca inuloides Species Asteraceae Eukaryota PMID[11473412]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT32 Organism Mus musculus Mus musculus Inhibition = 24.6 % 12880316

  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 NPC186933 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
0.9352 High Similarity NPC66208
0.9083 High Similarity NPC474057
0.9074 High Similarity NPC318327
0.8879 High Similarity NPC472222
0.8879 High Similarity NPC472221
0.8868 High Similarity NPC304873
0.8803 High Similarity NPC167323
0.8803 High Similarity NPC269923
0.8796 High Similarity NPC105899
0.8785 High Similarity NPC255676
0.8739 High Similarity NPC133308
0.8739 High Similarity NPC95126
0.8739 High Similarity NPC475002
0.8692 High Similarity NPC25458
0.8679 High Similarity NPC217621
0.8655 High Similarity NPC85511
0.8655 High Similarity NPC275145
0.8609 High Similarity NPC158157
0.8596 High Similarity NPC476357
0.8585 High Similarity NPC229242
0.8559 High Similarity NPC472981
0.8491 Intermediate Similarity NPC253423
0.8468 Intermediate Similarity NPC249811
0.844 Intermediate Similarity NPC329556
0.844 Intermediate Similarity NPC247976
0.8435 Intermediate Similarity NPC93181
0.8435 Intermediate Similarity NPC274839
0.8378 Intermediate Similarity NPC37914
0.8374 Intermediate Similarity NPC51448
0.8374 Intermediate Similarity NPC115797
0.8361 Intermediate Similarity NPC470765
0.8348 Intermediate Similarity NPC471721
0.8348 Intermediate Similarity NPC196673
0.8333 Intermediate Similarity NPC369
0.8333 Intermediate Similarity NPC293831
0.8319 Intermediate Similarity NPC133389
0.8319 Intermediate Similarity NPC183339
0.8319 Intermediate Similarity NPC234337
0.8305 Intermediate Similarity NPC328694
0.8304 Intermediate Similarity NPC211439
0.8293 Intermediate Similarity NPC473220
0.8293 Intermediate Similarity NPC470753
0.8291 Intermediate Similarity NPC212891
0.8279 Intermediate Similarity NPC236189
0.8276 Intermediate Similarity NPC221275
0.8264 Intermediate Similarity NPC282577
0.8261 Intermediate Similarity NPC93287
0.8261 Intermediate Similarity NPC128368
0.8257 Intermediate Similarity NPC225079
0.825 Intermediate Similarity NPC241001
0.8224 Intermediate Similarity NPC61944
0.822 Intermediate Similarity NPC160199
0.8214 Intermediate Similarity NPC100767
0.8211 Intermediate Similarity NPC123506
0.8211 Intermediate Similarity NPC275576
0.8198 Intermediate Similarity NPC329282
0.8182 Intermediate Similarity NPC284477
0.8182 Intermediate Similarity NPC25168
0.8174 Intermediate Similarity NPC292834
0.8167 Intermediate Similarity NPC478121
0.816 Intermediate Similarity NPC96024
0.8145 Intermediate Similarity NPC169913
0.813 Intermediate Similarity NPC199273
0.8115 Intermediate Similarity NPC121168
0.8099 Intermediate Similarity NPC165197
0.8095 Intermediate Similarity NPC117899
0.8091 Intermediate Similarity NPC282895
0.808 Intermediate Similarity NPC84672
0.808 Intermediate Similarity NPC72667
0.808 Intermediate Similarity NPC78364
0.808 Intermediate Similarity NPC176130
0.808 Intermediate Similarity NPC69424
0.8067 Intermediate Similarity NPC45794
0.8033 Intermediate Similarity NPC249340
0.8033 Intermediate Similarity NPC162935
0.8031 Intermediate Similarity NPC108129
0.8017 Intermediate Similarity NPC471188
0.8016 Intermediate Similarity NPC3009
0.8016 Intermediate Similarity NPC193203
0.8016 Intermediate Similarity NPC229894
0.8 Intermediate Similarity NPC253681
0.8 Intermediate Similarity NPC254492
0.8 Intermediate Similarity NPC474106
0.8 Intermediate Similarity NPC228435
0.7984 Intermediate Similarity NPC142956
0.7984 Intermediate Similarity NPC117794
0.7969 Intermediate Similarity NPC18798
0.7967 Intermediate Similarity NPC297193
0.7967 Intermediate Similarity NPC307174
0.7966 Intermediate Similarity NPC474095
0.7966 Intermediate Similarity NPC306740
0.7965 Intermediate Similarity NPC172483
0.7963 Intermediate Similarity NPC172925
0.7953 Intermediate Similarity NPC262819
0.7953 Intermediate Similarity NPC276238
0.7953 Intermediate Similarity NPC303910
0.7953 Intermediate Similarity NPC171460
0.7951 Intermediate Similarity NPC164852
0.7949 Intermediate Similarity NPC143768
0.7934 Intermediate Similarity NPC42657
0.7934 Intermediate Similarity NPC476645
0.7931 Intermediate Similarity NPC210089
0.7931 Intermediate Similarity NPC265513
0.7928 Intermediate Similarity NPC469481
0.7928 Intermediate Similarity NPC136810
0.7928 Intermediate Similarity NPC128248
0.7928 Intermediate Similarity NPC133809
0.7925 Intermediate Similarity NPC62765
0.7925 Intermediate Similarity NPC70940
0.7925 Intermediate Similarity NPC274455
0.7925 Intermediate Similarity NPC86670
0.792 Intermediate Similarity NPC472592
0.7913 Intermediate Similarity NPC85493
0.7903 Intermediate Similarity NPC273683
0.7895 Intermediate Similarity NPC94751
0.7895 Intermediate Similarity NPC83409
0.7895 Intermediate Similarity NPC185763
0.7895 Intermediate Similarity NPC142326
0.7891 Intermediate Similarity NPC31539
0.7886 Intermediate Similarity NPC154696
0.7881 Intermediate Similarity NPC153053
0.7874 Intermediate Similarity NPC48248
0.7869 Intermediate Similarity NPC232958
0.7863 Intermediate Similarity NPC321852
0.7863 Intermediate Similarity NPC280789
0.7851 Intermediate Similarity NPC161943
0.7851 Intermediate Similarity NPC273282
0.7851 Intermediate Similarity NPC474890
0.784 Intermediate Similarity NPC173978
0.7833 Intermediate Similarity NPC105141
0.7833 Intermediate Similarity NPC242764
0.7833 Intermediate Similarity NPC83718
0.7829 Intermediate Similarity NPC471851
0.7826 Intermediate Similarity NPC472980
0.7826 Intermediate Similarity NPC472979
0.7826 Intermediate Similarity NPC27252
0.7823 Intermediate Similarity NPC244351
0.7823 Intermediate Similarity NPC283514
0.7812 Intermediate Similarity NPC131684
0.7807 Intermediate Similarity NPC134120
0.7807 Intermediate Similarity NPC209632
0.7805 Intermediate Similarity NPC178395
0.7805 Intermediate Similarity NPC301987
0.7805 Intermediate Similarity NPC259703
0.7805 Intermediate Similarity NPC35856
0.7805 Intermediate Similarity NPC159760
0.7805 Intermediate Similarity NPC32322
0.7805 Intermediate Similarity NPC244994
0.7805 Intermediate Similarity NPC222876
0.7805 Intermediate Similarity NPC272454
0.7805 Intermediate Similarity NPC115188
0.7805 Intermediate Similarity NPC179092
0.7805 Intermediate Similarity NPC292665
0.7805 Intermediate Similarity NPC26433
0.7803 Intermediate Similarity NPC118919
0.7797 Intermediate Similarity NPC470253
0.7797 Intermediate Similarity NPC272524
0.7788 Intermediate Similarity NPC274443
0.7787 Intermediate Similarity NPC184579
0.7787 Intermediate Similarity NPC202015
0.7787 Intermediate Similarity NPC472708
0.7787 Intermediate Similarity NPC233165
0.7786 Intermediate Similarity NPC202225
0.7786 Intermediate Similarity NPC477594
0.7778 Intermediate Similarity NPC260818
0.7769 Intermediate Similarity NPC228318
0.7769 Intermediate Similarity NPC125252
0.7769 Intermediate Similarity NPC58685
0.776 Intermediate Similarity NPC174991
0.776 Intermediate Similarity NPC328107
0.776 Intermediate Similarity NPC228739
0.776 Intermediate Similarity NPC318067
0.776 Intermediate Similarity NPC77691
0.7757 Intermediate Similarity NPC26224
0.7752 Intermediate Similarity NPC72915
0.775 Intermediate Similarity NPC322197
0.7744 Intermediate Similarity NPC62272
0.7742 Intermediate Similarity NPC198336
0.7742 Intermediate Similarity NPC120545
0.7736 Intermediate Similarity NPC329064
0.7734 Intermediate Similarity NPC282923
0.7731 Intermediate Similarity NPC211421
0.7731 Intermediate Similarity NPC242136
0.7727 Intermediate Similarity NPC161632
0.7727 Intermediate Similarity NPC472372
0.7727 Intermediate Similarity NPC472374
0.7727 Intermediate Similarity NPC472551
0.7727 Intermediate Similarity NPC477596
0.7727 Intermediate Similarity NPC472545
0.7727 Intermediate Similarity NPC290803
0.7724 Intermediate Similarity NPC206778
0.7724 Intermediate Similarity NPC473243
0.7724 Intermediate Similarity NPC133302
0.7724 Intermediate Similarity NPC285829
0.7719 Intermediate Similarity NPC249067
0.7719 Intermediate Similarity NPC114594
0.7717 Intermediate Similarity NPC51292
0.7717 Intermediate Similarity NPC160499
0.7717 Intermediate Similarity NPC3224
0.7712 Intermediate Similarity NPC186128

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC186933 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
0.8929 High Similarity NPD5951 Approved
0.8475 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.844 Intermediate Similarity NPD1930 Approved
0.844 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.844 Intermediate Similarity NPD1929 Approved
0.8393 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD2066 Phase 3
0.7963 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7953 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7953 Intermediate Similarity NPD7008 Discontinued
0.7931 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7925 Intermediate Similarity NPD1086 Approved
0.7925 Intermediate Similarity NPD1089 Approved
0.7925 Intermediate Similarity NPD9258 Approved
0.7925 Intermediate Similarity NPD9256 Approved
0.7925 Intermediate Similarity NPD1090 Approved
0.7857 Intermediate Similarity NPD1932 Approved
0.783 Intermediate Similarity NPD800 Approved
0.7798 Intermediate Similarity NPD1693 Approved
0.7778 Intermediate Similarity NPD1088 Approved
0.776 Intermediate Similarity NPD182 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD2329 Discontinued
0.7744 Intermediate Similarity NPD5404 Approved
0.7744 Intermediate Similarity NPD5406 Approved
0.7744 Intermediate Similarity NPD5408 Approved
0.7744 Intermediate Similarity NPD5405 Approved
0.7719 Intermediate Similarity NPD1237 Approved
0.7706 Intermediate Similarity NPD1202 Approved
0.7698 Intermediate Similarity NPD1283 Approved
0.7685 Intermediate Similarity NPD1239 Approved
0.7667 Intermediate Similarity NPD2629 Approved
0.7658 Intermediate Similarity NPD1565 Approved
0.7658 Intermediate Similarity NPD1566 Phase 3
0.7658 Intermediate Similarity NPD1564 Approved
0.7647 Intermediate Similarity NPD7003 Approved
0.7642 Intermediate Similarity NPD1087 Approved
0.7638 Intermediate Similarity NPD1164 Approved
0.7627 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7623 Intermediate Similarity NPD7610 Discontinued
0.76 Intermediate Similarity NPD1201 Approved
0.7565 Intermediate Similarity NPD164 Approved
0.7547 Intermediate Similarity NPD9257 Approved
0.7547 Intermediate Similarity NPD9259 Approved
0.7545 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3495 Discontinued
0.75 Intermediate Similarity NPD1470 Approved
0.746 Intermediate Similarity NPD1281 Approved
0.7458 Intermediate Similarity NPD2182 Approved
0.7442 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD2932 Approved
0.744 Intermediate Similarity NPD3019 Approved
0.744 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD2346 Discontinued
0.7417 Intermediate Similarity NPD9508 Approved
0.7417 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD5909 Discontinued
0.7405 Intermediate Similarity NPD6966 Discovery
0.7402 Intermediate Similarity NPD4878 Approved
0.7398 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD1317 Discontinued
0.7387 Intermediate Similarity NPD1563 Approved
0.7368 Intermediate Similarity NPD1238 Approved
0.736 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD3764 Approved
0.7328 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD6049 Phase 2
0.7321 Intermediate Similarity NPD6048 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD4626 Approved
0.7302 Intermediate Similarity NPD2345 Approved
0.7297 Intermediate Similarity NPD7631 Approved
0.7286 Intermediate Similarity NPD7236 Approved
0.7281 Intermediate Similarity NPD9495 Approved
0.728 Intermediate Similarity NPD7009 Phase 2
0.7279 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD2799 Discontinued
0.7264 Intermediate Similarity NPD9491 Approved
0.7257 Intermediate Similarity NPD1989 Approved
0.7236 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD9264 Approved
0.7227 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD9267 Approved
0.7227 Intermediate Similarity NPD9263 Approved
0.7226 Intermediate Similarity NPD2935 Discontinued
0.7213 Intermediate Similarity NPD7635 Approved
0.7213 Intermediate Similarity NPD5277 Phase 2
0.7207 Intermediate Similarity NPD7609 Phase 3
0.7188 Intermediate Similarity NPD6287 Discontinued
0.7167 Intermediate Similarity NPD9266 Approved
0.7167 Intermediate Similarity NPD74 Approved
0.7165 Intermediate Similarity NPD1362 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD5306 Approved
0.7165 Intermediate Similarity NPD5305 Approved
0.7164 Intermediate Similarity NPD7961 Discontinued
0.7164 Intermediate Similarity NPD6663 Approved
0.7156 Intermediate Similarity NPD650 Approved
0.7153 Intermediate Similarity NPD7239 Suspended
0.7121 Intermediate Similarity NPD5736 Approved
0.712 Intermediate Similarity NPD9493 Approved
0.7103 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD3971 Phase 1
0.7087 Intermediate Similarity NPD1651 Approved
0.7087 Intermediate Similarity NPD4105 Approved
0.7087 Intermediate Similarity NPD4102 Approved
0.7075 Intermediate Similarity NPD226 Approved
0.7054 Intermediate Similarity NPD4807 Approved
0.7054 Intermediate Similarity NPD4806 Approved
0.7045 Intermediate Similarity NPD4980 Approved
0.7045 Intermediate Similarity NPD2798 Approved
0.704 Intermediate Similarity NPD4198 Discontinued
0.704 Intermediate Similarity NPD3317 Approved
0.7034 Intermediate Similarity NPD6647 Phase 2
0.7029 Intermediate Similarity NPD4308 Phase 3
0.7027 Intermediate Similarity NPD5346 Phase 2
0.7027 Intermediate Similarity NPD5347 Phase 2
0.7018 Intermediate Similarity NPD9260 Approved
0.7016 Intermediate Similarity NPD4869 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD6273 Approved
0.7008 Intermediate Similarity NPD9545 Approved
0.7007 Intermediate Similarity NPD3528 Clinical (unspecified phase)
0.6986 Remote Similarity NPD3226 Approved
0.6986 Remote Similarity NPD7458 Discontinued
0.6985 Remote Similarity NPD2979 Phase 3
0.6977 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6977 Remote Similarity NPD4106 Approved
0.6977 Remote Similarity NPD3026 Approved
0.6977 Remote Similarity NPD4136 Approved
0.6977 Remote Similarity NPD4135 Approved
0.6977 Remote Similarity NPD4879 Approved
0.6977 Remote Similarity NPD3023 Approved
0.697 Remote Similarity NPD2797 Approved
0.6963 Remote Similarity NPD2313 Discontinued
0.6953 Remote Similarity NPD5691 Approved
0.6953 Remote Similarity NPD1245 Approved
0.6953 Remote Similarity NPD3025 Approved
0.6953 Remote Similarity NPD3024 Approved
0.6944 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6942 Remote Similarity NPD2342 Discontinued
0.693 Remote Similarity NPD845 Approved
0.6929 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3020 Approved
0.6912 Remote Similarity NPD7714 Approved
0.6912 Remote Similarity NPD7715 Approved
0.6906 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6901 Remote Similarity NPD8166 Discontinued
0.6901 Remote Similarity NPD4628 Phase 3
0.6897 Remote Similarity NPD288 Approved
0.6894 Remote Similarity NPD1888 Phase 1
0.6894 Remote Similarity NPD1876 Approved
0.6891 Remote Similarity NPD9261 Approved
0.6887 Remote Similarity NPD9490 Approved
0.6875 Remote Similarity NPD7390 Discontinued
0.6871 Remote Similarity NPD6591 Clinical (unspecified phase)
0.687 Remote Similarity NPD1608 Approved
0.687 Remote Similarity NPD3972 Approved
0.6847 Remote Similarity NPD4793 Discontinued
0.6842 Remote Similarity NPD1508 Approved
0.6831 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6825 Remote Similarity NPD1246 Approved
0.6825 Remote Similarity NPD9281 Approved
0.6818 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5157 Phase 1
0.6818 Remote Similarity NPD5159 Phase 2
0.681 Remote Similarity NPD844 Approved
0.6806 Remote Similarity NPD3300 Phase 2
0.68 Remote Similarity NPD7094 Approved
0.68 Remote Similarity NPD6858 Approved
0.6792 Remote Similarity NPD227 Approved
0.6792 Remote Similarity NPD225 Approved
0.6783 Remote Similarity NPD3750 Approved
0.6783 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6769 Remote Similarity NPD1104 Approved
0.6761 Remote Similarity NPD970 Clinical (unspecified phase)
0.6759 Remote Similarity NPD942 Approved
0.6742 Remote Similarity NPD9717 Approved
0.6739 Remote Similarity NPD4307 Phase 2
0.6738 Remote Similarity NPD2531 Phase 2
0.6738 Remote Similarity NPD4477 Approved
0.6738 Remote Similarity NPD4476 Approved
0.6738 Remote Similarity NPD2438 Suspended
0.6723 Remote Similarity NPD1616 Discontinued
0.6719 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6716 Remote Similarity NPD1203 Approved
0.6715 Remote Similarity NPD3268 Approved
0.6715 Remote Similarity NPD411 Approved
0.6712 Remote Similarity NPD2533 Approved
0.6712 Remote Similarity NPD2534 Approved
0.6712 Remote Similarity NPD2532 Approved
0.6711 Remote Similarity NPD7057 Phase 3
0.6711 Remote Similarity NPD7058 Phase 2
0.669 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6689 Remote Similarity NPD7819 Suspended
0.6667 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2859 Approved
0.6667 Remote Similarity NPD1843 Approved
0.6667 Remote Similarity NPD2860 Approved
0.6667 Remote Similarity NPD3673 Approved
0.6667 Remote Similarity NPD6085 Phase 2
0.6667 Remote Similarity NPD3672 Approved
0.6667 Remote Similarity NPD5618 Discontinued

Structure

External Identifiers

PubChem CID   21592236
ChEMBL   CHEMBL459412
ZINC  

Physicochemical Properties

Molecular Weight:  248.14
ALogP:  0.5043
MLogP:  2.78
XLogP:  3.816
# Rotatable Bonds:  7
Polar Surface Area:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  18

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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