Natural Product: NPC81052

Natural Product ID:  NPC81052
Common Name:   Oropheolide
IUPAC Name:   (3R,5S)-3-hexadec-15-en-7,9,11-triynyl-5-(hydroxymethyl)oxolan-2-one
Synonyms:   Oropheolide
Molecular Formula:   C21H26O3
Standard InCHIKey:  PNMPARWIIBHFCP-UXHICEINSA-N
Standard InCHI:  InChI=1S/C21H26O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-17-20(18-22)24-21(19)23/h2,19-20,22H,1,3-4,11-18H2/t19-,20+/m1/s1
Canonical SMILES:  OC[C@@H]1C[C@H](C(=O)O1)CCCCCCC#CC#CC#CCCC=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
NPO10501 Mitrephora glabra Species Annonaceae Eukaryota Stem barks PMID[19874044]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens IC50 = 10000 nM 9644083
NPT395 Cell Line SF-268 Homo sapiens IC50 = 10000 nM 18183025
NPT91 Cell Line KB Homo sapiens IC50 = 10000 nM 18183025
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 10000 nM 12027740
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 250 ug/ml 18591275
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC = 63 ug/ml 18591275
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 31 ug/ml 18591275
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 125 ug/ml 18591275

  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 NPC81052 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
0.9583 High Similarity NPC469495
0.9452 High Similarity NPC209995
0.9324 High Similarity NPC200446
0.8904 High Similarity NPC217725
0.8333 Intermediate Similarity NPC82315
0.8312 Intermediate Similarity NPC11796
0.8312 Intermediate Similarity NPC218817
0.8049 Intermediate Similarity NPC475206
0.7973 Intermediate Similarity NPC28526
0.7838 Intermediate Similarity NPC477980
0.7595 Intermediate Similarity NPC470899
0.7564 Intermediate Similarity NPC472966
0.7532 Intermediate Similarity NPC477983
0.7532 Intermediate Similarity NPC477981
0.75 Intermediate Similarity NPC474780
0.75 Intermediate Similarity NPC151176
0.75 Intermediate Similarity NPC3464
0.75 Intermediate Similarity NPC475963
0.7442 Intermediate Similarity NPC186148
0.7442 Intermediate Similarity NPC179659
0.7439 Intermediate Similarity NPC103634
0.7412 Intermediate Similarity NPC329749
0.7412 Intermediate Similarity NPC21469
0.7368 Intermediate Similarity NPC209327
0.7368 Intermediate Similarity NPC273508
0.7356 Intermediate Similarity NPC58219
0.7356 Intermediate Similarity NPC177629
0.7356 Intermediate Similarity NPC202672
0.7326 Intermediate Similarity NPC474949
0.7326 Intermediate Similarity NPC475019
0.7303 Intermediate Similarity NPC208886
0.7303 Intermediate Similarity NPC12172
0.7303 Intermediate Similarity NPC30515
0.7303 Intermediate Similarity NPC184463
0.7273 Intermediate Similarity NPC307411
0.7273 Intermediate Similarity NPC173926
0.7273 Intermediate Similarity NPC474032
0.7273 Intermediate Similarity NPC92974
0.7273 Intermediate Similarity NPC199557
0.7253 Intermediate Similarity NPC107476
0.7237 Intermediate Similarity NPC271921
0.7237 Intermediate Similarity NPC104537
0.7237 Intermediate Similarity NPC330426
0.7237 Intermediate Similarity NPC127091
0.7237 Intermediate Similarity NPC22101
0.7237 Intermediate Similarity NPC148192
0.7229 Intermediate Similarity NPC233377
0.7222 Intermediate Similarity NPC212486
0.7222 Intermediate Similarity NPC81419
0.7222 Intermediate Similarity NPC475912
0.7222 Intermediate Similarity NPC179746
0.7215 Intermediate Similarity NPC475260
0.7215 Intermediate Similarity NPC51249
0.7215 Intermediate Similarity NPC475232
0.7215 Intermediate Similarity NPC473775
0.7215 Intermediate Similarity NPC474100
0.7215 Intermediate Similarity NPC473699
0.7209 Intermediate Similarity NPC304509
0.7209 Intermediate Similarity NPC149725
0.7209 Intermediate Similarity NPC47958
0.7191 Intermediate Similarity NPC478003
0.7191 Intermediate Similarity NPC474761
0.7191 Intermediate Similarity NPC478004
0.7191 Intermediate Similarity NPC158388
0.7191 Intermediate Similarity NPC51004
0.7191 Intermediate Similarity NPC65359
0.7191 Intermediate Similarity NPC476004
0.7179 Intermediate Similarity NPC42526
0.7143 Intermediate Similarity NPC48218
0.7143 Intermediate Similarity NPC81386
0.7143 Intermediate Similarity NPC473559
0.7143 Intermediate Similarity NPC474035
0.7143 Intermediate Similarity NPC141481
0.7143 Intermediate Similarity NPC324981
0.7126 Intermediate Similarity NPC477993
0.7126 Intermediate Similarity NPC477994
0.7126 Intermediate Similarity NPC476015
0.7126 Intermediate Similarity NPC474762
0.7111 Intermediate Similarity NPC469627
0.7108 Intermediate Similarity NPC470244
0.7108 Intermediate Similarity NPC89128
0.7108 Intermediate Similarity NPC470239
0.7105 Intermediate Similarity NPC477982
0.7093 Intermediate Similarity NPC9868
0.7093 Intermediate Similarity NPC243618
0.7093 Intermediate Similarity NPC70424
0.7093 Intermediate Similarity NPC474776
0.7089 Intermediate Similarity NPC474590
0.7079 Intermediate Similarity NPC474951
0.7079 Intermediate Similarity NPC473564
0.7073 Intermediate Similarity NPC320630
0.7073 Intermediate Similarity NPC116177
0.7073 Intermediate Similarity NPC7563
0.7065 Intermediate Similarity NPC14961
0.7065 Intermediate Similarity NPC36954
0.7065 Intermediate Similarity NPC270013
0.7059 Intermediate Similarity NPC474252
0.7059 Intermediate Similarity NPC474291
0.7051 Intermediate Similarity NPC144511
0.7051 Intermediate Similarity NPC296522
0.7045 Intermediate Similarity NPC190753
0.7045 Intermediate Similarity NPC248602
0.7033 Intermediate Similarity NPC476300
0.7033 Intermediate Similarity NPC295204
0.7033 Intermediate Similarity NPC288240
0.7033 Intermediate Similarity NPC162205
0.7033 Intermediate Similarity NPC273579
0.7027 Intermediate Similarity NPC174560
0.7027 Intermediate Similarity NPC125312
0.7024 Intermediate Similarity NPC472948
0.7024 Intermediate Similarity NPC51507
0.7013 Intermediate Similarity NPC475443
0.7013 Intermediate Similarity NPC473829
0.7013 Intermediate Similarity NPC469925
0.7 Intermediate Similarity NPC206614
0.7 Intermediate Similarity NPC474323
0.7 Intermediate Similarity NPC473619
0.7 Intermediate Similarity NPC313670
0.6988 Remote Similarity NPC267231
0.6986 Remote Similarity NPC470363
0.6977 Remote Similarity NPC250315
0.6977 Remote Similarity NPC11620
0.6966 Remote Similarity NPC153805
0.6966 Remote Similarity NPC281516
0.6966 Remote Similarity NPC53158
0.6962 Remote Similarity NPC472955
0.6962 Remote Similarity NPC476660
0.6957 Remote Similarity NPC190294
0.6957 Remote Similarity NPC18357
0.6951 Remote Similarity NPC476601
0.6951 Remote Similarity NPC279537
0.6941 Remote Similarity NPC191711
0.6941 Remote Similarity NPC126248
0.6941 Remote Similarity NPC207188
0.6941 Remote Similarity NPC470241
0.6923 Remote Similarity NPC70251
0.6923 Remote Similarity NPC475881
0.6923 Remote Similarity NPC473321
0.6905 Remote Similarity NPC19841
0.6897 Remote Similarity NPC472958
0.6897 Remote Similarity NPC472957
0.6897 Remote Similarity NPC72464
0.6889 Remote Similarity NPC77001
0.6889 Remote Similarity NPC295312
0.6889 Remote Similarity NPC253618
0.686 Remote Similarity NPC89555
0.6854 Remote Similarity NPC474765
0.6849 Remote Similarity NPC329819
0.6848 Remote Similarity NPC475788
0.6848 Remote Similarity NPC469692
0.6848 Remote Similarity NPC469645
0.6842 Remote Similarity NPC474213
0.6842 Remote Similarity NPC226592
0.6842 Remote Similarity NPC470320
0.6835 Remote Similarity NPC473772
0.6835 Remote Similarity NPC5714
0.6829 Remote Similarity NPC471491
0.6829 Remote Similarity NPC324762
0.6829 Remote Similarity NPC228411
0.6824 Remote Similarity NPC474981
0.6824 Remote Similarity NPC469920
0.6824 Remote Similarity NPC258965
0.6824 Remote Similarity NPC156658
0.6818 Remote Similarity NPC255307
0.6818 Remote Similarity NPC125290
0.6818 Remote Similarity NPC137033
0.6813 Remote Similarity NPC474232
0.6813 Remote Similarity NPC473448
0.6813 Remote Similarity NPC166554
0.6809 Remote Similarity NPC476315
0.6809 Remote Similarity NPC256227
0.6809 Remote Similarity NPC76862
0.6809 Remote Similarity NPC158416
0.6809 Remote Similarity NPC473859
0.6809 Remote Similarity NPC470883
0.6809 Remote Similarity NPC476009
0.6809 Remote Similarity NPC39859
0.6804 Remote Similarity NPC474747
0.6804 Remote Similarity NPC225353
0.68 Remote Similarity NPC201939
0.6795 Remote Similarity NPC286842
0.679 Remote Similarity NPC472956
0.6786 Remote Similarity NPC108816
0.6786 Remote Similarity NPC192006
0.6786 Remote Similarity NPC471465
0.6786 Remote Similarity NPC196653
0.6786 Remote Similarity NPC93763
0.6786 Remote Similarity NPC3852
0.6786 Remote Similarity NPC475616
0.6782 Remote Similarity NPC111409
0.6782 Remote Similarity NPC52609
0.6782 Remote Similarity NPC239308
0.6782 Remote Similarity NPC253801
0.6782 Remote Similarity NPC128246
0.6782 Remote Similarity NPC470948
0.6782 Remote Similarity NPC1761
0.6778 Remote Similarity NPC473715
0.6778 Remote Similarity NPC476706
0.6778 Remote Similarity NPC87189
0.6778 Remote Similarity NPC476708

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC81052 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
0.7059 Intermediate Similarity NPD6435 Approved
0.6941 Remote Similarity NPD5369 Approved
0.6923 Remote Similarity NPD7983 Approved
0.6842 Remote Similarity NPD3197 Phase 1
0.6824 Remote Similarity NPD5368 Approved
0.6782 Remote Similarity NPD7154 Phase 3
0.6742 Remote Similarity NPD5786 Approved
0.6667 Remote Similarity NPD4270 Approved
0.6667 Remote Similarity NPD4269 Approved
0.663 Remote Similarity NPD46 Approved
0.663 Remote Similarity NPD6698 Approved
0.6629 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6629 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6623 Remote Similarity NPD7909 Approved
0.6591 Remote Similarity NPD5362 Discontinued
0.6591 Remote Similarity NPD5331 Approved
0.6591 Remote Similarity NPD5332 Approved
0.6588 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6444 Remote Similarity NPD5363 Approved
0.6437 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6437 Remote Similarity NPD4252 Approved
0.6377 Remote Similarity NPD622 Approved
0.6374 Remote Similarity NPD4249 Approved
0.6354 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6344 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6344 Remote Similarity NPD6101 Approved
0.6316 Remote Similarity NPD5778 Approved
0.6316 Remote Similarity NPD3198 Approved
0.6316 Remote Similarity NPD5779 Approved
0.6304 Remote Similarity NPD4251 Approved
0.6304 Remote Similarity NPD4250 Approved
0.6301 Remote Similarity NPD3730 Approved
0.6301 Remote Similarity NPD3728 Approved
0.6277 Remote Similarity NPD5785 Approved
0.625 Remote Similarity NPD4822 Approved
0.625 Remote Similarity NPD4820 Approved
0.625 Remote Similarity NPD4821 Approved
0.625 Remote Similarity NPD4819 Approved
0.6211 Remote Similarity NPD6411 Approved
0.6207 Remote Similarity NPD4268 Approved
0.6207 Remote Similarity NPD4271 Approved
0.618 Remote Similarity NPD4790 Discontinued
0.6164 Remote Similarity NPD3172 Approved
0.6132 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6122 Remote Similarity NPD7839 Suspended
0.6105 Remote Similarity NPD7838 Discovery
0.6081 Remote Similarity NPD3195 Phase 2
0.6081 Remote Similarity NPD3194 Approved
0.6081 Remote Similarity NPD3196 Approved
0.6081 Remote Similarity NPD4266 Approved
0.6081 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6058 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6 Remote Similarity NPD5370 Suspended
0.6 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6 Remote Similarity NPD4225 Approved
0.5979 Remote Similarity NPD6399 Phase 3
0.5974 Remote Similarity NPD6109 Phase 1
0.5918 Remote Similarity NPD5282 Discontinued
0.5914 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5914 Remote Similarity NPD1694 Approved
0.5888 Remote Similarity NPD6371 Approved
0.5876 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5876 Remote Similarity NPD8034 Phase 2
0.5876 Remote Similarity NPD8035 Phase 2
0.5862 Remote Similarity NPD8039 Approved
0.5857 Remote Similarity NPD634 Phase 3
0.5854 Remote Similarity NPD7331 Phase 2
0.5851 Remote Similarity NPD6422 Discontinued
0.5849 Remote Similarity NPD6686 Approved
0.5843 Remote Similarity NPD3732 Approved
0.5842 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5833 Remote Similarity NPD1695 Approved
0.5823 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5789 Remote Similarity NPD8517 Approved
0.5789 Remote Similarity NPD8516 Approved
0.5789 Remote Similarity NPD8515 Approved
0.5789 Remote Similarity NPD8513 Phase 3
0.5783 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5761 Remote Similarity NPD3667 Approved
0.5727 Remote Similarity NPD4632 Approved
0.5714 Remote Similarity NPD7637 Suspended
0.5699 Remote Similarity NPD6110 Phase 1
0.5684 Remote Similarity NPD5330 Approved
0.5684 Remote Similarity NPD6684 Approved
0.5684 Remote Similarity NPD7146 Approved
0.5684 Remote Similarity NPD7521 Approved
0.5684 Remote Similarity NPD6409 Approved
0.5684 Remote Similarity NPD7334 Approved
0.5684 Remote Similarity NPD3618 Phase 1
0.5676 Remote Similarity NPD29 Approved
0.5676 Remote Similarity NPD28 Approved
0.5667 Remote Similarity NPD4238 Approved
0.5667 Remote Similarity NPD4802 Phase 2
0.5664 Remote Similarity NPD7641 Discontinued
0.5658 Remote Similarity NPD615 Clinical (unspecified phase)
0.5657 Remote Similarity NPD5781 Clinical (unspecified phase)
0.5644 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5638 Remote Similarity NPD4786 Approved
0.5638 Remote Similarity NPD3666 Approved
0.5638 Remote Similarity NPD3665 Phase 1
0.5638 Remote Similarity NPD3133 Approved
0.5638 Remote Similarity NPD5766 Clinical (unspecified phase)
0.5636 Remote Similarity NPD8297 Approved
0.5625 Remote Similarity NPD1145 Discontinued
0.5616 Remote Similarity NPD3173 Approved
0.5607 Remote Similarity NPD5697 Approved
0.5607 Remote Similarity NPD6412 Phase 2
0.56 Remote Similarity NPD3186 Phase 1
0.56 Remote Similarity NPD7748 Approved

Structure

External Identifiers

PubChem CID   44606075
ChEMBL   CHEMBL1080662
ZINC  

Physicochemical Properties

Molecular Weight:  326.19
ALogP:  1.4834
MLogP:  3.44
XLogP:  5.843
# Rotatable Bonds:  10
Polar Surface Area:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  24

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Similar NPs/Drugs