Natural Product: NPC135951

Natural Product ID:  NPC135951
Common Name:   Lehualide A
IUPAC Name:   4-hydroxy-3-methoxy-5-methyl-6-[(2E,6Z,9E)-3,7,9-trimethyl-11-phenylundeca-2,6,9-trienyl]pyran-2-one
Synonyms:  
Molecular Formula:   C27H34O4
Standard InCHIKey:  RVGXYJCOGNMRGK-XAFHVSQGSA-N
Standard InCHI:  InChI=1S/C27H34O4/c1-19(15-17-24-22(4)25(28)26(30-5)27(29)31-24)10-9-11-20(2)18-21(3)14-16-23-12-7-6-8-13-23/h6-8,11-15,28H,9-10,16-18H2,1-5H3/b19-15+,20-11-,21-14+
Canonical SMILES:  COc1c(=O)oc(c(c1O)C)C/C=C(/CC/C=C(C/C(=C/Cc1ccccc1)/C)/C)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
NPO31509 Plakortis Genus Plakinidae Eukaryota Hawaiian PMID[16180823]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT140 Organism Artemia Artemia LD50 = 50 ug/ml 19691309

  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 NPC135951 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
0.9891 High Similarity NPC80115
0.9783 High Similarity NPC154517
0.8478 Intermediate Similarity NPC53299
0.8454 Intermediate Similarity NPC473347
0.8352 Intermediate Similarity NPC99240
0.835 Intermediate Similarity NPC477251
0.8333 Intermediate Similarity NPC472319
0.8302 Intermediate Similarity NPC477250
0.8105 Intermediate Similarity NPC96625
0.8105 Intermediate Similarity NPC286608
0.8105 Intermediate Similarity NPC169050
0.8043 Intermediate Similarity NPC71795
0.8041 Intermediate Similarity NPC108026
0.8 Intermediate Similarity NPC136962
0.798 Intermediate Similarity NPC23453
0.7872 Intermediate Similarity NPC127491
0.7872 Intermediate Similarity NPC308619
0.7872 Intermediate Similarity NPC324835
0.787 Intermediate Similarity NPC477247
0.785 Intermediate Similarity NPC281604
0.783 Intermediate Similarity NPC474376
0.783 Intermediate Similarity NPC475203
0.783 Intermediate Similarity NPC472316
0.783 Intermediate Similarity NPC472315
0.781 Intermediate Similarity NPC280616
0.781 Intermediate Similarity NPC171831
0.781 Intermediate Similarity NPC242913
0.7757 Intermediate Similarity NPC156648
0.7736 Intermediate Similarity NPC127676
0.7714 Intermediate Similarity NPC91820
0.7714 Intermediate Similarity NPC82426
0.77 Intermediate Similarity NPC77273
0.7684 Intermediate Similarity NPC208183
0.7684 Intermediate Similarity NPC243289
0.7664 Intermediate Similarity NPC37115
0.766 Intermediate Similarity NPC303245
0.766 Intermediate Similarity NPC89950
0.7647 Intermediate Similarity NPC30361
0.7636 Intermediate Similarity NPC234376
0.7634 Intermediate Similarity NPC78517
0.7634 Intermediate Similarity NPC167577
0.7609 Intermediate Similarity NPC287790
0.7609 Intermediate Similarity NPC3672
0.7568 Intermediate Similarity NPC265002
0.7527 Intermediate Similarity NPC176228
0.75 Intermediate Similarity NPC240108
0.75 Intermediate Similarity NPC213156
0.75 Intermediate Similarity NPC175393
0.7431 Intermediate Similarity NPC20485
0.7431 Intermediate Similarity NPC277788
0.7429 Intermediate Similarity NPC474308
0.7411 Intermediate Similarity NPC477245
0.7411 Intermediate Similarity NPC477246
0.7395 Intermediate Similarity NPC14141
0.7395 Intermediate Similarity NPC471466
0.7391 Intermediate Similarity NPC32203
0.7391 Intermediate Similarity NPC206800
0.7387 Intermediate Similarity NPC323007
0.7387 Intermediate Similarity NPC183700
0.7383 Intermediate Similarity NPC234305
0.7373 Intermediate Similarity NPC475328
0.7364 Intermediate Similarity NPC182549
0.7364 Intermediate Similarity NPC114741
0.734 Intermediate Similarity NPC50192
0.7333 Intermediate Similarity NPC179411
0.7321 Intermediate Similarity NPC139946
0.7315 Intermediate Similarity NPC85977
0.7315 Intermediate Similarity NPC269644
0.7297 Intermediate Similarity NPC79543
0.7281 Intermediate Similarity NPC469509
0.7273 Intermediate Similarity NPC475465
0.7273 Intermediate Similarity NPC260952
0.7273 Intermediate Similarity NPC47536
0.7273 Intermediate Similarity NPC472314
0.7264 Intermediate Similarity NPC98911
0.7264 Intermediate Similarity NPC472318
0.7263 Intermediate Similarity NPC469894
0.7248 Intermediate Similarity NPC472919
0.7245 Intermediate Similarity NPC44546
0.7222 Intermediate Similarity NPC304638
0.7222 Intermediate Similarity NPC160382
0.7217 Intermediate Similarity NPC296526
0.7217 Intermediate Similarity NPC476476
0.7212 Intermediate Similarity NPC5472
0.7207 Intermediate Similarity NPC184633
0.7207 Intermediate Similarity NPC40178
0.7203 Intermediate Similarity NPC474223
0.7203 Intermediate Similarity NPC243059
0.7203 Intermediate Similarity NPC475827
0.7203 Intermediate Similarity NPC31314
0.7203 Intermediate Similarity NPC280827
0.7196 Intermediate Similarity NPC253746
0.7182 Intermediate Similarity NPC51174
0.7179 Intermediate Similarity NPC203124
0.7172 Intermediate Similarity NPC123476
0.717 Intermediate Similarity NPC476120
0.7168 Intermediate Similarity NPC474689
0.7168 Intermediate Similarity NPC470825
0.7157 Intermediate Similarity NPC110420
0.7157 Intermediate Similarity NPC26224
0.7157 Intermediate Similarity NPC303967
0.7157 Intermediate Similarity NPC67585
0.7156 Intermediate Similarity NPC109637
0.7155 Intermediate Similarity NPC108532
0.7143 Intermediate Similarity NPC273837
0.713 Intermediate Similarity NPC94343
0.7129 Intermediate Similarity NPC304760
0.7119 Intermediate Similarity NPC204784
0.7105 Intermediate Similarity NPC131530
0.7105 Intermediate Similarity NPC272524
0.7103 Intermediate Similarity NPC171843
0.7097 Intermediate Similarity NPC217431
0.7097 Intermediate Similarity NPC110313
0.7094 Intermediate Similarity NPC122117
0.7087 Intermediate Similarity NPC119631
0.708 Intermediate Similarity NPC43584
0.7075 Intermediate Similarity NPC133135
0.7075 Intermediate Similarity NPC278228
0.7075 Intermediate Similarity NPC103048
0.7075 Intermediate Similarity NPC251579
0.7069 Intermediate Similarity NPC216387
0.7065 Intermediate Similarity NPC155429
0.7059 Intermediate Similarity NPC2058
0.7059 Intermediate Similarity NPC193193
0.7059 Intermediate Similarity NPC173443
0.7054 Intermediate Similarity NPC206341
0.7054 Intermediate Similarity NPC469511
0.7054 Intermediate Similarity NPC474364
0.7049 Intermediate Similarity NPC146886
0.7049 Intermediate Similarity NPC60517
0.7049 Intermediate Similarity NPC20443
0.7043 Intermediate Similarity NPC474641
0.7043 Intermediate Similarity NPC87069
0.704 Intermediate Similarity NPC253595
0.7034 Intermediate Similarity NPC471033
0.7034 Intermediate Similarity NPC309434
0.7034 Intermediate Similarity NPC311091
0.7025 Intermediate Similarity NPC474159
0.7025 Intermediate Similarity NPC474254
0.7018 Intermediate Similarity NPC474314
0.7018 Intermediate Similarity NPC158282
0.7018 Intermediate Similarity NPC470355
0.7009 Intermediate Similarity NPC470820
0.7009 Intermediate Similarity NPC33717
0.7009 Intermediate Similarity NPC281277
0.7009 Intermediate Similarity NPC145052
0.7008 Intermediate Similarity NPC323379
0.7008 Intermediate Similarity NPC327204
0.7 Intermediate Similarity NPC470849
0.7 Intermediate Similarity NPC475710
0.7 Intermediate Similarity NPC58616
0.7 Intermediate Similarity NPC2518
0.7 Intermediate Similarity NPC470848
0.6991 Remote Similarity NPC75272
0.6991 Remote Similarity NPC471954
0.6984 Remote Similarity NPC319995
0.6984 Remote Similarity NPC289415
0.6984 Remote Similarity NPC17567
0.6983 Remote Similarity NPC33749
0.6983 Remote Similarity NPC261453
0.6983 Remote Similarity NPC328593
0.6983 Remote Similarity NPC210092
0.6975 Remote Similarity NPC241634
0.6975 Remote Similarity NPC141791
0.6975 Remote Similarity NPC263386
0.6967 Remote Similarity NPC472373
0.696 Remote Similarity NPC93632
0.6957 Remote Similarity NPC266116
0.6957 Remote Similarity NPC48525
0.6957 Remote Similarity NPC161611
0.6953 Remote Similarity NPC477281
0.6953 Remote Similarity NPC477280
0.6953 Remote Similarity NPC19719
0.6949 Remote Similarity NPC183154
0.6949 Remote Similarity NPC263754
0.6937 Remote Similarity NPC269457
0.6937 Remote Similarity NPC288760
0.6937 Remote Similarity NPC209632
0.6937 Remote Similarity NPC227255
0.6935 Remote Similarity NPC213552
0.6935 Remote Similarity NPC267733
0.6935 Remote Similarity NPC276047
0.6935 Remote Similarity NPC120225
0.693 Remote Similarity NPC476003
0.693 Remote Similarity NPC474157
0.693 Remote Similarity NPC63345
0.6923 Remote Similarity NPC473507
0.6923 Remote Similarity NPC474967
0.6923 Remote Similarity NPC476484
0.6923 Remote Similarity NPC233669
0.6923 Remote Similarity NPC471616
0.6917 Remote Similarity NPC474222
0.6917 Remote Similarity NPC475804
0.6917 Remote Similarity NPC474874
0.6916 Remote Similarity NPC270654
0.6911 Remote Similarity NPC57607
0.6911 Remote Similarity NPC145287
0.6911 Remote Similarity NPC246704
0.6909 Remote Similarity NPC301943
0.6909 Remote Similarity NPC474365

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC135951 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
0.8105 Intermediate Similarity NPD1282 Approved
0.7778 Intermediate Similarity NPD2067 Discontinued
0.7684 Intermediate Similarity NPD3971 Phase 1
0.7642 Intermediate Similarity NPD5909 Discontinued
0.7576 Intermediate Similarity NPD689 Discontinued
0.7526 Intermediate Similarity NPD5734 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD9716 Approved
0.7383 Intermediate Similarity NPD6647 Phase 2
0.7368 Intermediate Similarity NPD4198 Discontinued
0.7168 Intermediate Similarity NPD969 Suspended
0.7155 Intermediate Similarity NPD694 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD1358 Approved
0.7048 Intermediate Similarity NPD6049 Phase 2
0.7048 Intermediate Similarity NPD6048 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD5926 Approved
0.6983 Remote Similarity NPD2629 Approved
0.6952 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3134 Approved
0.6852 Remote Similarity NPD9495 Approved
0.6822 Remote Similarity NPD4340 Discontinued
0.6786 Remote Similarity NPD5048 Discontinued
0.6772 Remote Similarity NPD7095 Approved
0.6757 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6754 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6744 Remote Similarity NPD4060 Phase 1
0.6721 Remote Similarity NPD3496 Discontinued
0.6719 Remote Similarity NPD6798 Discontinued
0.6692 Remote Similarity NPD6355 Discontinued
0.6667 Remote Similarity NPD4807 Approved
0.6667 Remote Similarity NPD4806 Approved
0.6667 Remote Similarity NPD5979 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6233 Phase 2
0.6667 Remote Similarity NPD4062 Phase 3
0.6639 Remote Similarity NPD5305 Approved
0.6639 Remote Similarity NPD5306 Approved
0.6636 Remote Similarity NPD7798 Approved
0.6636 Remote Similarity NPD2066 Phase 3
0.6615 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6609 Remote Similarity NPD2182 Approved
0.6587 Remote Similarity NPD2797 Approved
0.6585 Remote Similarity NPD4106 Approved
0.6585 Remote Similarity NPD4136 Approved
0.6585 Remote Similarity NPD4135 Approved
0.6571 Remote Similarity NPD5346 Phase 2
0.6571 Remote Similarity NPD5347 Phase 2
0.6557 Remote Similarity NPD4102 Approved
0.6557 Remote Similarity NPD4105 Approved
0.6538 Remote Similarity NPD4793 Discontinued
0.6532 Remote Similarity NPD422 Phase 1
0.6525 Remote Similarity NPD7843 Approved
0.6525 Remote Similarity NPD5535 Approved
0.6512 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6504 Remote Similarity NPD4626 Approved
0.6496 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6491 Remote Similarity NPD9697 Approved
0.6486 Remote Similarity NPD1238 Approved
0.6471 Remote Similarity NPD9491 Approved
0.6471 Remote Similarity NPD6010 Discontinued
0.6466 Remote Similarity NPD2684 Approved
0.6462 Remote Similarity NPD3268 Approved
0.6462 Remote Similarity NPD1048 Approved
0.6452 Remote Similarity NPD3847 Discontinued
0.6444 Remote Similarity NPD5762 Approved
0.6444 Remote Similarity NPD5763 Approved
0.6436 Remote Similarity NPD226 Approved
0.6435 Remote Similarity NPD6685 Approved
0.6429 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6422 Remote Similarity NPD2933 Approved
0.6422 Remote Similarity NPD2934 Approved
0.6415 Remote Similarity NPD800 Approved
0.6404 Remote Similarity NPD164 Approved
0.6404 Remote Similarity NPD1237 Approved
0.6378 Remote Similarity NPD3225 Approved
0.6364 Remote Similarity NPD2859 Approved
0.6364 Remote Similarity NPD2860 Approved
0.6364 Remote Similarity NPD1989 Approved
0.6364 Remote Similarity NPD7157 Approved
0.6355 Remote Similarity NPD1089 Approved
0.6355 Remote Similarity NPD3672 Approved
0.6355 Remote Similarity NPD3673 Approved
0.6355 Remote Similarity NPD9258 Approved
0.6355 Remote Similarity NPD1090 Approved
0.6355 Remote Similarity NPD9256 Approved
0.6355 Remote Similarity NPD1086 Approved
0.6341 Remote Similarity NPD9545 Approved
0.6341 Remote Similarity NPD1894 Discontinued
0.6328 Remote Similarity NPD2625 Approved
0.6328 Remote Similarity NPD2626 Approved
0.6328 Remote Similarity NPD2628 Approved
0.6328 Remote Similarity NPD987 Approved
0.6328 Remote Similarity NPD2160 Approved
0.6328 Remote Similarity NPD2627 Approved
0.6328 Remote Similarity NPD2159 Approved
0.6324 Remote Similarity NPD7266 Discontinued
0.6316 Remote Similarity NPD1929 Approved
0.6316 Remote Similarity NPD1930 Approved
0.6316 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6311 Remote Similarity NPD9493 Approved
0.629 Remote Similarity NPD5691 Approved
0.6288 Remote Similarity NPD4248 Discontinued
0.6279 Remote Similarity NPD5647 Approved
0.6279 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6273 Remote Similarity NPD1693 Approved
0.6271 Remote Similarity NPD5235 Approved
0.6271 Remote Similarity NPD5237 Approved
0.6271 Remote Similarity NPD5240 Approved
0.6271 Remote Similarity NPD5236 Approved
0.6271 Remote Similarity NPD5239 Approved
0.6269 Remote Similarity NPD6653 Approved
0.626 Remote Similarity NPD5536 Phase 2
0.625 Remote Similarity NPD5667 Approved
0.6239 Remote Similarity NPD290 Approved
0.6239 Remote Similarity NPD1088 Approved
0.6231 Remote Similarity NPD5204 Approved
0.623 Remote Similarity NPD6671 Approved
0.6222 Remote Similarity NPD7097 Phase 1
0.622 Remote Similarity NPD9717 Approved
0.622 Remote Similarity NPD6637 Approved
0.622 Remote Similarity NPD1877 Discontinued
0.6218 Remote Similarity NPD2201 Approved
0.6212 Remote Similarity NPD6859 Clinical (unspecified phase)
0.62 Remote Similarity NPD9294 Approved
0.6195 Remote Similarity NPD3020 Approved
0.6194 Remote Similarity NPD5124 Phase 1
0.6194 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6187 Remote Similarity NPD4628 Phase 3
0.6183 Remote Similarity NPD4620 Approved
0.6183 Remote Similarity NPD5201 Approved
0.6183 Remote Similarity NPD4617 Approved
0.6183 Remote Similarity NPD5203 Approved
0.6183 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6183 Remote Similarity NPD6832 Phase 2
0.6182 Remote Similarity NPD1202 Approved
0.6182 Remote Similarity NPD1066 Discontinued
0.6174 Remote Similarity NPD5765 Approved
0.617 Remote Similarity NPD6799 Approved
0.6167 Remote Similarity NPD228 Approved
0.6167 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6159 Remote Similarity NPD4534 Discontinued
0.6154 Remote Similarity NPD968 Approved
0.6154 Remote Similarity NPD5403 Approved
0.6148 Remote Similarity NPD5951 Approved
0.6147 Remote Similarity NPD7609 Phase 3
0.6147 Remote Similarity NPD1239 Approved
0.6143 Remote Similarity NPD2354 Approved
0.6143 Remote Similarity NPD6190 Approved
0.6142 Remote Similarity NPD6287 Discontinued
0.6142 Remote Similarity NPD4480 Approved
0.6142 Remote Similarity NPD1535 Discovery
0.6139 Remote Similarity NPD227 Approved
0.6139 Remote Similarity NPD225 Approved
0.6136 Remote Similarity NPD5454 Clinical (unspecified phase)
0.6129 Remote Similarity NPD2347 Approved
0.6127 Remote Similarity NPD3536 Discontinued
0.6115 Remote Similarity NPD1652 Phase 2
0.6111 Remote Similarity NPD5126 Approved
0.6111 Remote Similarity NPD5125 Phase 3
0.6111 Remote Similarity NPD1778 Approved
0.6107 Remote Similarity NPD3661 Approved
0.6107 Remote Similarity NPD3662 Phase 3
0.6107 Remote Similarity NPD3663 Approved
0.6107 Remote Similarity NPD3664 Approved
0.6094 Remote Similarity NPD1481 Phase 2
0.6091 Remote Similarity NPD7631 Approved
0.609 Remote Similarity NPD4619 Approved
0.609 Remote Similarity NPD2313 Discontinued
0.609 Remote Similarity NPD4621 Approved
0.6087 Remote Similarity NPD1932 Approved
0.6084 Remote Similarity NPD5049 Phase 3
0.608 Remote Similarity NPD7741 Discontinued
0.6078 Remote Similarity NPD9490 Approved
0.6077 Remote Similarity NPD1203 Approved
0.6077 Remote Similarity NPD6362 Approved
0.6077 Remote Similarity NPD3266 Approved
0.6077 Remote Similarity NPD3267 Approved
0.6075 Remote Similarity NPD1087 Approved
0.6071 Remote Similarity NPD7835 Discontinued
0.6071 Remote Similarity NPD5206 Clinical (unspecified phase)
0.6071 Remote Similarity NPD8166 Discontinued
0.6066 Remote Similarity NPD1241 Discontinued
0.6066 Remote Similarity NPD5283 Phase 1
0.6058 Remote Similarity NPD7033 Discontinued
0.6058 Remote Similarity NPD4308 Phase 3
0.6056 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6048 Remote Similarity NPD4431 Clinical (unspecified phase)
0.6048 Remote Similarity NPD5292 Approved
0.6048 Remote Similarity NPD5291 Approved
0.6043 Remote Similarity NPD5958 Discontinued
0.6043 Remote Similarity NPD2030 Discontinued
0.6038 Remote Similarity NPD111 Approved
0.6036 Remote Similarity NPD845 Approved
0.6033 Remote Similarity NPD6912 Phase 3
0.6032 Remote Similarity NPD5585 Approved
0.6031 Remote Similarity NPD2788 Approved
0.6031 Remote Similarity NPD6085 Phase 2
0.6031 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6028 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6028 Remote Similarity NPD3887 Approved
0.6019 Remote Similarity NPD1507 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   54710737
ChEMBL   CHEMBL464741
ZINC  

Physicochemical Properties

Molecular Weight:  422.25
ALogP:  3.6828
MLogP:  3.99
XLogP:  8.86
# Rotatable Bonds:  16
Polar Surface Area:  55.76
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  31

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
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