Natural Product: NPC109510

Natural Product ID:  NPC109510
Common Name:   Trisnor-Gamma-Lactone
IUPAC Name:   [(1R,3R,4R,4aS,8aS)-3,4a,8,8-tetramethyl-5'-oxospiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxolane]-1-yl] acetate
Synonyms:   Trisnor-Gamma-Lactone
Molecular Formula:   C19H30O4
Standard InCHIKey:  HXILYTQMWOYCAT-IONYDWJHSA-N
Standard InCHI:  InChI=1S/C19H30O4/c1-12-11-14(22-13(2)20)16-17(3,4)8-6-9-18(16,5)19(12)10-7-15(21)23-19/h12,14,16H,6-11H2,1-5H3/t12-,14-,16+,18+,19-/m1/s1
Canonical SMILES:  CC(=O)O[C@@H]1C[C@@H](C)[C@@]2([C@@]3([C@@H]1C(C)(C)CCC3)C)CCC(=O)O2
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
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota fruits PMID[11975496]
NPO29705 Viticis fructus Species Curculionidae Eukaryota TCMSP*
NPO15454 Vitex rotundifolia Species Lamiaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT681 Cell Line PC-12 Rattus norvegicus GI50 > 5 ug/ml 11975496
NPT393 Cell Line HCT-116 Homo sapiens GI50 > 5 ug/ml 11975496

  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 NPC109510 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
0.9286 High Similarity NPC55508
0.9167 High Similarity NPC307865
0.9104 High Similarity NPC84562
0.9054 High Similarity NPC125366
0.9054 High Similarity NPC134227
0.8873 High Similarity NPC474755
0.8667 High Similarity NPC73013
0.859 High Similarity NPC65133
0.8507 High Similarity NPC306750
0.8421 Intermediate Similarity NPC474754
0.84 Intermediate Similarity NPC143250
0.8358 Intermediate Similarity NPC478126
0.8333 Intermediate Similarity NPC13494
0.8267 Intermediate Similarity NPC471046
0.8267 Intermediate Similarity NPC92489
0.8205 Intermediate Similarity NPC280781
0.8205 Intermediate Similarity NPC475743
0.8205 Intermediate Similarity NPC48756
0.8205 Intermediate Similarity NPC58631
0.8171 Intermediate Similarity NPC471221
0.8169 Intermediate Similarity NPC41542
0.8158 Intermediate Similarity NPC471151
0.8148 Intermediate Similarity NPC477441
0.8125 Intermediate Similarity NPC473299
0.8088 Intermediate Similarity NPC204173
0.8025 Intermediate Similarity NPC477445
0.8 Intermediate Similarity NPC15091
0.7975 Intermediate Similarity NPC271572
0.7975 Intermediate Similarity NPC475951
0.7975 Intermediate Similarity NPC474870
0.7952 Intermediate Similarity NPC221993
0.7945 Intermediate Similarity NPC295788
0.7922 Intermediate Similarity NPC207010
0.7922 Intermediate Similarity NPC317913
0.7917 Intermediate Similarity NPC476928
0.7901 Intermediate Similarity NPC79308
0.7901 Intermediate Similarity NPC477434
0.7887 Intermediate Similarity NPC230047
0.7887 Intermediate Similarity NPC19311
0.7882 Intermediate Similarity NPC216137
0.7857 Intermediate Similarity NPC472234
0.7857 Intermediate Similarity NPC477440
0.7857 Intermediate Similarity NPC477443
0.7857 Intermediate Similarity NPC472233
0.7848 Intermediate Similarity NPC261616
0.7821 Intermediate Similarity NPC31031
0.7821 Intermediate Similarity NPC472608
0.7821 Intermediate Similarity NPC243594
0.7805 Intermediate Similarity NPC62572
0.7792 Intermediate Similarity NPC4209
0.7765 Intermediate Similarity NPC477444
0.7765 Intermediate Similarity NPC477442
0.7765 Intermediate Similarity NPC477433
0.775 Intermediate Similarity NPC209318
0.775 Intermediate Similarity NPC223330
0.7733 Intermediate Similarity NPC197701
0.7722 Intermediate Similarity NPC80891
0.7722 Intermediate Similarity NPC201276
0.7703 Intermediate Similarity NPC178541
0.7683 Intermediate Similarity NPC34984
0.7683 Intermediate Similarity NPC25037
0.7662 Intermediate Similarity NPC212733
0.7654 Intermediate Similarity NPC289486
0.7654 Intermediate Similarity NPC61107
0.7654 Intermediate Similarity NPC226988
0.7647 Intermediate Similarity NPC67653
0.7647 Intermediate Similarity NPC471459
0.7632 Intermediate Similarity NPC475230
0.7625 Intermediate Similarity NPC170038
0.7625 Intermediate Similarity NPC1882
0.7619 Intermediate Similarity NPC175293
0.7595 Intermediate Similarity NPC80089
0.7595 Intermediate Similarity NPC34046
0.7595 Intermediate Similarity NPC224802
0.7595 Intermediate Similarity NPC171426
0.7595 Intermediate Similarity NPC324700
0.7586 Intermediate Similarity NPC472232
0.7586 Intermediate Similarity NPC147272
0.7586 Intermediate Similarity NPC472231
0.7558 Intermediate Similarity NPC470114
0.7558 Intermediate Similarity NPC475776
0.7558 Intermediate Similarity NPC185529
0.7558 Intermediate Similarity NPC472146
0.7532 Intermediate Similarity NPC96759
0.7532 Intermediate Similarity NPC167702
0.7532 Intermediate Similarity NPC280026
0.7531 Intermediate Similarity NPC328639
0.7531 Intermediate Similarity NPC470154
0.7531 Intermediate Similarity NPC12933
0.7531 Intermediate Similarity NPC329490
0.7531 Intermediate Similarity NPC470156
0.7531 Intermediate Similarity NPC50658
0.7531 Intermediate Similarity NPC71541
0.7529 Intermediate Similarity NPC476379
0.7529 Intermediate Similarity NPC476435
0.7528 Intermediate Similarity NPC473964
0.75 Intermediate Similarity NPC478227
0.75 Intermediate Similarity NPC118987
0.75 Intermediate Similarity NPC469940
0.75 Intermediate Similarity NPC320144
0.75 Intermediate Similarity NPC248216
0.75 Intermediate Similarity NPC477495
0.75 Intermediate Similarity NPC89310
0.75 Intermediate Similarity NPC309127
0.75 Intermediate Similarity NPC247877
0.75 Intermediate Similarity NPC477287
0.75 Intermediate Similarity NPC470424
0.75 Intermediate Similarity NPC120395
0.7471 Intermediate Similarity NPC475878
0.747 Intermediate Similarity NPC319909
0.747 Intermediate Similarity NPC9060
0.747 Intermediate Similarity NPC473336
0.747 Intermediate Similarity NPC97505
0.747 Intermediate Similarity NPC470011
0.747 Intermediate Similarity NPC139566
0.747 Intermediate Similarity NPC471044
0.747 Intermediate Similarity NPC181871
0.7468 Intermediate Similarity NPC143133
0.7468 Intermediate Similarity NPC474404
0.7468 Intermediate Similarity NPC298168
0.7467 Intermediate Similarity NPC196197
0.7444 Intermediate Similarity NPC266417
0.7444 Intermediate Similarity NPC473963
0.7444 Intermediate Similarity NPC474921
0.7442 Intermediate Similarity NPC253618
0.7442 Intermediate Similarity NPC200580
0.7442 Intermediate Similarity NPC194642
0.7442 Intermediate Similarity NPC77001
0.7439 Intermediate Similarity NPC477446
0.7439 Intermediate Similarity NPC164289
0.7439 Intermediate Similarity NPC470155
0.7439 Intermediate Similarity NPC121121
0.7439 Intermediate Similarity NPC242771
0.7439 Intermediate Similarity NPC311642
0.7439 Intermediate Similarity NPC102156
0.7439 Intermediate Similarity NPC148740
0.7439 Intermediate Similarity NPC100366
0.7439 Intermediate Similarity NPC477447
0.7436 Intermediate Similarity NPC179858
0.7436 Intermediate Similarity NPC478105
0.7412 Intermediate Similarity NPC305029
0.7412 Intermediate Similarity NPC239938
0.7407 Intermediate Similarity NPC471217
0.7407 Intermediate Similarity NPC472943
0.7407 Intermediate Similarity NPC471216
0.7407 Intermediate Similarity NPC472951
0.7407 Intermediate Similarity NPC60568
0.7403 Intermediate Similarity NPC123122
0.7386 Intermediate Similarity NPC472147
0.7386 Intermediate Similarity NPC474379
0.7386 Intermediate Similarity NPC472148
0.7381 Intermediate Similarity NPC473350
0.7381 Intermediate Similarity NPC98270
0.7381 Intermediate Similarity NPC474572
0.7375 Intermediate Similarity NPC475725
0.7375 Intermediate Similarity NPC185465
0.7375 Intermediate Similarity NPC329117
0.7356 Intermediate Similarity NPC50443
0.7356 Intermediate Similarity NPC18536
0.7349 Intermediate Similarity NPC471037
0.7349 Intermediate Similarity NPC472847
0.7349 Intermediate Similarity NPC243347
0.7349 Intermediate Similarity NPC476721
0.7342 Intermediate Similarity NPC474020
0.7333 Intermediate Similarity NPC119838
0.7333 Intermediate Similarity NPC235109
0.7333 Intermediate Similarity NPC116683
0.7333 Intermediate Similarity NPC93245
0.7326 Intermediate Similarity NPC477128
0.7326 Intermediate Similarity NPC236459
0.7317 Intermediate Similarity NPC472229
0.7317 Intermediate Similarity NPC472230
0.7317 Intermediate Similarity NPC476071
0.7308 Intermediate Similarity NPC74639
0.7308 Intermediate Similarity NPC272359
0.7294 Intermediate Similarity NPC476717
0.7294 Intermediate Similarity NPC6979
0.7294 Intermediate Similarity NPC474008
0.7294 Intermediate Similarity NPC185638
0.7294 Intermediate Similarity NPC471042
0.7294 Intermediate Similarity NPC9231
0.7294 Intermediate Similarity NPC472272
0.7294 Intermediate Similarity NPC92139
0.7294 Intermediate Similarity NPC85698
0.7284 Intermediate Similarity NPC476176
0.7273 Intermediate Similarity NPC49420
0.7273 Intermediate Similarity NPC474065
0.7273 Intermediate Similarity NPC126642
0.7273 Intermediate Similarity NPC160506
0.7262 Intermediate Similarity NPC219011
0.7262 Intermediate Similarity NPC219535
0.7262 Intermediate Similarity NPC105895
0.7262 Intermediate Similarity NPC237938
0.7262 Intermediate Similarity NPC475509
0.7253 Intermediate Similarity NPC136781
0.725 Intermediate Similarity NPC212453
0.725 Intermediate Similarity NPC477918
0.725 Intermediate Similarity NPC475031
0.725 Intermediate Similarity NPC23884
0.725 Intermediate Similarity NPC474433

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC109510 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
0.7922 Intermediate Similarity NPD6116 Phase 1
0.7792 Intermediate Similarity NPD6117 Approved
0.7733 Intermediate Similarity NPD5777 Approved
0.7595 Intermediate Similarity NPD6114 Approved
0.7595 Intermediate Similarity NPD6697 Approved
0.7595 Intermediate Similarity NPD6118 Approved
0.7595 Intermediate Similarity NPD6115 Approved
0.7532 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD3702 Approved
0.7333 Intermediate Similarity NPD229 Approved
0.7273 Intermediate Similarity NPD8035 Phase 2
0.7273 Intermediate Similarity NPD8034 Phase 2
0.7237 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD4224 Phase 2
0.7051 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3703 Phase 2
0.6933 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6933 Remote Similarity NPD9496 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7900 Approved
0.6905 Remote Similarity NPD1780 Approved
0.6905 Remote Similarity NPD1779 Approved
0.6883 Remote Similarity NPD5360 Phase 3
0.6883 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6835 Remote Similarity NPD6081 Approved
0.6813 Remote Similarity NPD6399 Phase 3
0.6795 Remote Similarity NPD3698 Phase 2
0.6782 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6735 Remote Similarity NPD6008 Approved
0.6709 Remote Similarity NPD4244 Approved
0.6709 Remote Similarity NPD4245 Approved
0.6702 Remote Similarity NPD7902 Approved
0.6667 Remote Similarity NPD1700 Approved
0.6667 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6625 Remote Similarity NPD4758 Discontinued
0.6591 Remote Similarity NPD1694 Approved
0.6559 Remote Similarity NPD7748 Approved
0.6548 Remote Similarity NPD3671 Phase 1
0.6517 Remote Similarity NPD6409 Approved
0.6517 Remote Similarity NPD5330 Approved
0.6517 Remote Similarity NPD7334 Approved
0.6517 Remote Similarity NPD7146 Approved
0.6517 Remote Similarity NPD7521 Approved
0.6517 Remote Similarity NPD6684 Approved
0.65 Remote Similarity NPD4789 Approved
0.6471 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6444 Remote Similarity NPD3573 Approved
0.6437 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6436 Remote Similarity NPD5345 Clinical (unspecified phase)
0.64 Remote Similarity NPD5739 Approved
0.64 Remote Similarity NPD6402 Approved
0.64 Remote Similarity NPD7128 Approved
0.64 Remote Similarity NPD6675 Approved
0.6383 Remote Similarity NPD6001 Approved
0.6375 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6375 Remote Similarity NPD3726 Approved
0.6375 Remote Similarity NPD3725 Approved
0.6374 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6374 Remote Similarity NPD6672 Approved
0.6374 Remote Similarity NPD5737 Approved
0.6374 Remote Similarity NPD6903 Approved
0.6373 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6373 Approved
0.6373 Remote Similarity NPD6372 Approved
0.6364 Remote Similarity NPD3669 Approved
0.6364 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6353 Remote Similarity NPD5364 Discontinued
0.6344 Remote Similarity NPD7515 Phase 2
0.6337 Remote Similarity NPD5701 Approved
0.6337 Remote Similarity NPD5697 Approved
0.6333 Remote Similarity NPD3618 Phase 1
0.6275 Remote Similarity NPD7320 Approved
0.6275 Remote Similarity NPD6881 Approved
0.6275 Remote Similarity NPD6899 Approved
0.6275 Remote Similarity NPD6011 Approved
0.625 Remote Similarity NPD6649 Approved
0.625 Remote Similarity NPD615 Clinical (unspecified phase)
0.625 Remote Similarity NPD3729 Clinical (unspecified phase)
0.625 Remote Similarity NPD6650 Approved
0.6214 Remote Similarity NPD6013 Approved
0.6214 Remote Similarity NPD6014 Approved
0.6214 Remote Similarity NPD6012 Approved
0.6154 Remote Similarity NPD6098 Approved
0.6154 Remote Similarity NPD7102 Approved
0.6154 Remote Similarity NPD7290 Approved
0.6154 Remote Similarity NPD6883 Approved
0.6129 Remote Similarity NPD6904 Approved
0.6129 Remote Similarity NPD6080 Approved
0.6129 Remote Similarity NPD6673 Approved
0.6122 Remote Similarity NPD5696 Approved
0.6122 Remote Similarity NPD7638 Approved
0.6122 Remote Similarity NPD4225 Approved
0.6111 Remote Similarity NPD3668 Phase 3
0.6105 Remote Similarity NPD4202 Approved
0.6095 Remote Similarity NPD6617 Approved
0.6095 Remote Similarity NPD8130 Phase 1
0.6095 Remote Similarity NPD6869 Approved
0.6095 Remote Similarity NPD6847 Approved
0.6095 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6067 Remote Similarity NPD3667 Approved
0.6064 Remote Similarity NPD5207 Approved
0.6061 Remote Similarity NPD8418 Phase 2
0.6061 Remote Similarity NPD7639 Approved
0.6061 Remote Similarity NPD7640 Approved
0.6058 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6053 Remote Similarity NPD3198 Approved
0.6038 Remote Similarity NPD6882 Approved
0.6038 Remote Similarity NPD8297 Approved
0.6023 Remote Similarity NPD6928 Phase 2
0.6022 Remote Similarity NPD5208 Approved
0.602 Remote Similarity NPD6084 Phase 2
0.602 Remote Similarity NPD4755 Approved
0.602 Remote Similarity NPD6083 Phase 2
0.6 Remote Similarity NPD5693 Phase 1
0.598 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5979 Remote Similarity NPD5695 Phase 3
0.5978 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5977 Remote Similarity NPD4802 Phase 2
0.5977 Remote Similarity NPD4238 Approved
0.5957 Remote Similarity NPD5328 Approved
0.5941 Remote Similarity NPD7632 Discontinued
0.5934 Remote Similarity NPD4786 Approved
0.5918 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5918 Remote Similarity NPD4697 Phase 3
0.5904 Remote Similarity NPD2687 Approved
0.5904 Remote Similarity NPD2686 Approved
0.5904 Remote Similarity NPD2254 Approved
0.5904 Remote Similarity NPD4787 Phase 1
0.59 Remote Similarity NPD4700 Approved
0.59 Remote Similarity NPD5285 Approved
0.59 Remote Similarity NPD4696 Approved
0.59 Remote Similarity NPD5286 Approved
0.5895 Remote Similarity NPD5692 Phase 3
0.5893 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5882 Remote Similarity NPD2699 Approved
0.5872 Remote Similarity NPD6274 Approved
0.5862 Remote Similarity NPD8143 Approved
0.5862 Remote Similarity NPD8144 Approved
0.5857 Remote Similarity NPD2266 Phase 2
0.5843 Remote Similarity NPD7525 Registered
0.5842 Remote Similarity NPD5223 Approved
0.5833 Remote Similarity NPD5284 Approved
0.5833 Remote Similarity NPD8133 Approved
0.5833 Remote Similarity NPD5281 Approved
0.5833 Remote Similarity NPD4632 Approved
0.5833 Remote Similarity NPD5694 Approved
0.5833 Remote Similarity NPD6079 Approved
0.5833 Remote Similarity NPD6050 Approved
0.5824 Remote Similarity NPD4788 Approved
0.5821 Remote Similarity NPD387 Clinical (unspecified phase)
0.5818 Remote Similarity NPD7115 Discovery
0.5818 Remote Similarity NPD6317 Approved
0.5789 Remote Similarity NPD6051 Approved
0.5784 Remote Similarity NPD4633 Approved
0.5784 Remote Similarity NPD5224 Approved
0.5784 Remote Similarity NPD5225 Approved
0.5784 Remote Similarity NPD5211 Phase 2
0.5784 Remote Similarity NPD5226 Approved
0.5766 Remote Similarity NPD6314 Approved
0.5766 Remote Similarity NPD6313 Approved
0.5766 Remote Similarity NPD6335 Approved
0.5761 Remote Similarity NPD3666 Approved
0.5761 Remote Similarity NPD3133 Approved
0.5761 Remote Similarity NPD3665 Phase 1
0.5758 Remote Similarity NPD5222 Approved
0.5758 Remote Similarity NPD5221 Approved
0.5758 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5752 Remote Similarity NPD6921 Approved
0.575 Remote Similarity NPD7909 Approved
0.575 Remote Similarity NPD371 Approved
0.5728 Remote Similarity NPD5174 Approved
0.5728 Remote Similarity NPD4754 Approved
0.5728 Remote Similarity NPD5175 Approved
0.5728 Remote Similarity NPD6052 Approved
0.5714 Remote Similarity NPD7101 Approved
0.5714 Remote Similarity NPD7100 Approved
0.57 Remote Similarity NPD5173 Approved
0.5676 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5676 Remote Similarity NPD6009 Approved
0.5673 Remote Similarity NPD5141 Approved
0.567 Remote Similarity NPD6411 Approved
0.5664 Remote Similarity NPD6319 Approved
0.5657 Remote Similarity NPD5654 Approved
0.5634 Remote Similarity NPD6125 Clinical (unspecified phase)
0.5632 Remote Similarity NPD2257 Approved
0.5625 Remote Similarity NPD4753 Phase 2
0.5619 Remote Similarity NPD4768 Approved
0.5619 Remote Similarity NPD4767 Approved
0.5619 Remote Similarity NPD6920 Discontinued
0.5618 Remote Similarity NPD3617 Approved
0.5614 Remote Similarity NPD5983 Phase 2
0.5614 Remote Similarity NPD6909 Approved
0.5614 Remote Similarity NPD6908 Approved
0.5603 Remote Similarity NPD7492 Approved

Structure

External Identifiers

PubChem CID   21668661
ChEMBL   CHEMBL464481
ZINC  

Physicochemical Properties

Molecular Weight:  322.21
ALogP:  1.0641
MLogP:  3.11
XLogP:  4.738
# Rotatable Bonds:  7
Polar Surface Area:  52.6
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  23

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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