Natural Product: NPC469495

Natural Product ID:  NPC469495
Common Name:   9,10-Dihydrooropheolide
IUPAC Name:   (3R,5S)-3-[(5E)-hexadeca-5,15-dien-7,9,11-triynyl]-5-(hydroxymethyl)oxolan-2-one
Synonyms:   9,10-Dihydrooropheolide
Molecular Formula:   C21H24O3
Standard InCHIKey:  SIHBCONZMCURTQ-UBGMWTFPSA-N
Standard InCHI:  InChI=1S/C21H24O3/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/h2,11-12,19-20,22H,1,3-4,13-18H2/b12-11+/t19-,20+/m1/s1
Canonical SMILES:  OC[C@@H]1C[C@H](C(=O)O1)CCCC/C=C/C#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 16759086
NPT91 Cell Line KB Homo sapiens IC50 = 10000 nM 16759086
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC = 12 ug/ml PubChem BioAssay data set
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 12 ug/ml PubChem BioAssay data set
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 10000 nM 17536856
NPT395 Cell Line SF-268 Homo sapiens IC50 = 10000 nM 17067147
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 12 ug/ml 18591275
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 50 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 NPC469495 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
0.9863 High Similarity NPC209995
0.973 High Similarity NPC200446
0.9583 High Similarity NPC81052
0.8701 High Similarity NPC11796
0.8701 High Similarity NPC218817
0.8553 High Similarity NPC217725
0.8415 Intermediate Similarity NPC475206
0.8 Intermediate Similarity NPC82315
0.7975 Intermediate Similarity NPC470899
0.7949 Intermediate Similarity NPC472966
0.7922 Intermediate Similarity NPC477981
0.7922 Intermediate Similarity NPC477983
0.7805 Intermediate Similarity NPC103634
0.7791 Intermediate Similarity NPC179659
0.7765 Intermediate Similarity NPC21469
0.7763 Intermediate Similarity NPC273508
0.7763 Intermediate Similarity NPC209327
0.7701 Intermediate Similarity NPC202672
0.7662 Intermediate Similarity NPC28526
0.7662 Intermediate Similarity NPC199557
0.764 Intermediate Similarity NPC184463
0.764 Intermediate Similarity NPC208886
0.764 Intermediate Similarity NPC30515
0.764 Intermediate Similarity NPC12172
0.7632 Intermediate Similarity NPC104537
0.7632 Intermediate Similarity NPC148192
0.7632 Intermediate Similarity NPC127091
0.7632 Intermediate Similarity NPC271921
0.7632 Intermediate Similarity NPC22101
0.7632 Intermediate Similarity NPC330426
0.7614 Intermediate Similarity NPC474032
0.7614 Intermediate Similarity NPC307411
0.759 Intermediate Similarity NPC233377
0.7582 Intermediate Similarity NPC107476
0.7564 Intermediate Similarity NPC42526
0.7556 Intermediate Similarity NPC475912
0.7556 Intermediate Similarity NPC179746
0.7556 Intermediate Similarity NPC81419
0.7556 Intermediate Similarity NPC212486
0.7532 Intermediate Similarity NPC473559
0.7532 Intermediate Similarity NPC141481
0.7532 Intermediate Similarity NPC477980
0.7532 Intermediate Similarity NPC324981
0.7532 Intermediate Similarity NPC48218
0.7528 Intermediate Similarity NPC474761
0.7528 Intermediate Similarity NPC158388
0.7528 Intermediate Similarity NPC51004
0.7528 Intermediate Similarity NPC478003
0.7528 Intermediate Similarity NPC478004
0.7528 Intermediate Similarity NPC476004
0.75 Intermediate Similarity NPC477982
0.7473 Intermediate Similarity NPC474035
0.7473 Intermediate Similarity NPC81386
0.7471 Intermediate Similarity NPC477993
0.7471 Intermediate Similarity NPC477994
0.747 Intermediate Similarity NPC89128
0.747 Intermediate Similarity NPC470244
0.747 Intermediate Similarity NPC470239
0.7442 Intermediate Similarity NPC243618
0.7442 Intermediate Similarity NPC9868
0.7442 Intermediate Similarity NPC474776
0.7442 Intermediate Similarity NPC70424
0.7439 Intermediate Similarity NPC116177
0.7439 Intermediate Similarity NPC7563
0.7439 Intermediate Similarity NPC320630
0.7436 Intermediate Similarity NPC144511
0.7436 Intermediate Similarity NPC296522
0.7432 Intermediate Similarity NPC125312
0.7432 Intermediate Similarity NPC174560
0.7416 Intermediate Similarity NPC473564
0.7412 Intermediate Similarity NPC474252
0.7412 Intermediate Similarity NPC474291
0.7403 Intermediate Similarity NPC473829
0.7403 Intermediate Similarity NPC475443
0.7391 Intermediate Similarity NPC14961
0.7391 Intermediate Similarity NPC36954
0.7391 Intermediate Similarity NPC270013
0.7386 Intermediate Similarity NPC248602
0.7381 Intermediate Similarity NPC472948
0.7363 Intermediate Similarity NPC288240
0.7363 Intermediate Similarity NPC273579
0.7363 Intermediate Similarity NPC162205
0.7363 Intermediate Similarity NPC476300
0.7363 Intermediate Similarity NPC295204
0.7349 Intermediate Similarity NPC267231
0.7342 Intermediate Similarity NPC472955
0.7342 Intermediate Similarity NPC476660
0.7333 Intermediate Similarity NPC313670
0.7333 Intermediate Similarity NPC473619
0.7326 Intermediate Similarity NPC11620
0.7326 Intermediate Similarity NPC250315
0.7317 Intermediate Similarity NPC279537
0.7303 Intermediate Similarity NPC281516
0.7303 Intermediate Similarity NPC153805
0.7294 Intermediate Similarity NPC470241
0.7294 Intermediate Similarity NPC191711
0.7294 Intermediate Similarity NPC207188
0.726 Intermediate Similarity NPC329819
0.7253 Intermediate Similarity NPC473321
0.7241 Intermediate Similarity NPC151176
0.7241 Intermediate Similarity NPC475963
0.7241 Intermediate Similarity NPC474780
0.7241 Intermediate Similarity NPC472957
0.7241 Intermediate Similarity NPC72464
0.7241 Intermediate Similarity NPC472958
0.7241 Intermediate Similarity NPC3464
0.7237 Intermediate Similarity NPC226592
0.7237 Intermediate Similarity NPC470320
0.7222 Intermediate Similarity NPC295312
0.7215 Intermediate Similarity NPC473772
0.7209 Intermediate Similarity NPC89555
0.72 Intermediate Similarity NPC201939
0.7195 Intermediate Similarity NPC324762
0.7191 Intermediate Similarity NPC186148
0.7191 Intermediate Similarity NPC474765
0.7176 Intermediate Similarity NPC469920
0.7174 Intermediate Similarity NPC469692
0.7174 Intermediate Similarity NPC469645
0.716 Intermediate Similarity NPC472956
0.7159 Intermediate Similarity NPC329749
0.7159 Intermediate Similarity NPC255307
0.7159 Intermediate Similarity NPC125290
0.7159 Intermediate Similarity NPC137033
0.7143 Intermediate Similarity NPC93763
0.7143 Intermediate Similarity NPC108816
0.7143 Intermediate Similarity NPC473448
0.7143 Intermediate Similarity NPC474232
0.7143 Intermediate Similarity NPC471465
0.7143 Intermediate Similarity NPC3852
0.7143 Intermediate Similarity NPC196653
0.7143 Intermediate Similarity NPC192006
0.7143 Intermediate Similarity NPC166554
0.7128 Intermediate Similarity NPC473859
0.7128 Intermediate Similarity NPC476315
0.7126 Intermediate Similarity NPC253801
0.7126 Intermediate Similarity NPC1761
0.7126 Intermediate Similarity NPC52609
0.7126 Intermediate Similarity NPC470948
0.7113 Intermediate Similarity NPC225353
0.7113 Intermediate Similarity NPC474747
0.7111 Intermediate Similarity NPC58219
0.7111 Intermediate Similarity NPC87189
0.7111 Intermediate Similarity NPC227379
0.7111 Intermediate Similarity NPC473715
0.7111 Intermediate Similarity NPC476707
0.7111 Intermediate Similarity NPC177629
0.7111 Intermediate Similarity NPC474471
0.7111 Intermediate Similarity NPC476803
0.7111 Intermediate Similarity NPC228415
0.7111 Intermediate Similarity NPC476706
0.7111 Intermediate Similarity NPC476708
0.7111 Intermediate Similarity NPC476704
0.7108 Intermediate Similarity NPC12740
0.7108 Intermediate Similarity NPC266159
0.7108 Intermediate Similarity NPC472959
0.7108 Intermediate Similarity NPC110461
0.7108 Intermediate Similarity NPC61863
0.7108 Intermediate Similarity NPC472967
0.7097 Intermediate Similarity NPC121825
0.7097 Intermediate Similarity NPC303942
0.7097 Intermediate Similarity NPC71589
0.7097 Intermediate Similarity NPC57405
0.7093 Intermediate Similarity NPC52861
0.7093 Intermediate Similarity NPC47031
0.7089 Intermediate Similarity NPC476614
0.7083 Intermediate Similarity NPC54766
0.7079 Intermediate Similarity NPC474949
0.7079 Intermediate Similarity NPC469910
0.7079 Intermediate Similarity NPC469483
0.7079 Intermediate Similarity NPC475753
0.7079 Intermediate Similarity NPC279267
0.7079 Intermediate Similarity NPC475019
0.7079 Intermediate Similarity NPC69082
0.7079 Intermediate Similarity NPC164393
0.7079 Intermediate Similarity NPC150755
0.7079 Intermediate Similarity NPC112685
0.7079 Intermediate Similarity NPC309211
0.7079 Intermediate Similarity NPC305475
0.7079 Intermediate Similarity NPC475461
0.7073 Intermediate Similarity NPC474321
0.7067 Intermediate Similarity NPC243532
0.7059 Intermediate Similarity NPC167881
0.7059 Intermediate Similarity NPC98557
0.7059 Intermediate Similarity NPC475210
0.7053 Intermediate Similarity NPC40812
0.7053 Intermediate Similarity NPC17326
0.7053 Intermediate Similarity NPC134454
0.7045 Intermediate Similarity NPC114979
0.7045 Intermediate Similarity NPC191476
0.7045 Intermediate Similarity NPC96259
0.7045 Intermediate Similarity NPC141193
0.7045 Intermediate Similarity NPC476804
0.7045 Intermediate Similarity NPC295799
0.7045 Intermediate Similarity NPC165287
0.7041 Intermediate Similarity NPC475945
0.7041 Intermediate Similarity NPC110989
0.7041 Intermediate Similarity NPC475871
0.7037 Intermediate Similarity NPC129665
0.7037 Intermediate Similarity NPC163003
0.7033 Intermediate Similarity NPC52198

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469495 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
0.7412 Intermediate Similarity NPD6435 Approved
0.7294 Intermediate Similarity NPD5369 Approved
0.7253 Intermediate Similarity NPD7983 Approved
0.7237 Intermediate Similarity NPD3197 Phase 1
0.7176 Intermediate Similarity NPD5368 Approved
0.7126 Intermediate Similarity NPD7154 Phase 3
0.7079 Intermediate Similarity NPD5786 Approved
0.7011 Intermediate Similarity NPD4270 Approved
0.7011 Intermediate Similarity NPD4269 Approved
0.6966 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6957 Remote Similarity NPD46 Approved
0.6957 Remote Similarity NPD6698 Approved
0.6941 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6932 Remote Similarity NPD5362 Discontinued
0.6932 Remote Similarity NPD5332 Approved
0.6932 Remote Similarity NPD5331 Approved
0.6782 Remote Similarity NPD4252 Approved
0.6782 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6778 Remote Similarity NPD5363 Approved
0.6703 Remote Similarity NPD4249 Approved
0.6667 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6101 Approved
0.6667 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6632 Remote Similarity NPD5778 Approved
0.6632 Remote Similarity NPD5779 Approved
0.663 Remote Similarity NPD4250 Approved
0.663 Remote Similarity NPD4251 Approved
0.6596 Remote Similarity NPD5785 Approved
0.6591 Remote Similarity NPD4822 Approved
0.6591 Remote Similarity NPD4819 Approved
0.6591 Remote Similarity NPD4821 Approved
0.6591 Remote Similarity NPD4820 Approved
0.6575 Remote Similarity NPD3172 Approved
0.6552 Remote Similarity NPD4271 Approved
0.6552 Remote Similarity NPD4268 Approved
0.6526 Remote Similarity NPD6411 Approved
0.6517 Remote Similarity NPD4790 Discontinued
0.6486 Remote Similarity NPD3195 Phase 2
0.6486 Remote Similarity NPD3196 Approved
0.6486 Remote Similarity NPD4266 Approved
0.6486 Remote Similarity NPD3194 Approved
0.6429 Remote Similarity NPD7839 Suspended
0.6421 Remote Similarity NPD7838 Discovery
0.6415 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6375 Remote Similarity NPD7909 Approved
0.6364 Remote Similarity NPD6109 Phase 1
0.6346 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6316 Remote Similarity NPD5370 Suspended
0.63 Remote Similarity NPD4225 Approved
0.6289 Remote Similarity NPD6399 Phase 3
0.6237 Remote Similarity NPD1694 Approved
0.6224 Remote Similarity NPD5282 Discontinued
0.622 Remote Similarity NPD7331 Phase 2
0.6207 Remote Similarity NPD8039 Approved
0.6203 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6186 Remote Similarity NPD4810 Clinical (unspecified phase)
0.618 Remote Similarity NPD3732 Approved
0.617 Remote Similarity NPD6422 Discontinued
0.6168 Remote Similarity NPD6371 Approved
0.6146 Remote Similarity NPD1695 Approved
0.6145 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6139 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6132 Remote Similarity NPD6686 Approved
0.6111 Remote Similarity NPD622 Approved
0.6087 Remote Similarity NPD3667 Approved
0.6081 Remote Similarity NPD29 Approved
0.6081 Remote Similarity NPD28 Approved
0.6076 Remote Similarity NPD3198 Approved
0.6053 Remote Similarity NPD8515 Approved
0.6053 Remote Similarity NPD3728 Approved
0.6053 Remote Similarity NPD8517 Approved
0.6053 Remote Similarity NPD8516 Approved
0.6053 Remote Similarity NPD3730 Approved
0.6053 Remote Similarity NPD8513 Phase 3
0.6027 Remote Similarity NPD3173 Approved
0.6022 Remote Similarity NPD6110 Phase 1
0.602 Remote Similarity NPD7637 Suspended
0.6 Remote Similarity NPD5330 Approved
0.6 Remote Similarity NPD3618 Phase 1
0.6 Remote Similarity NPD4632 Approved
0.6 Remote Similarity NPD6409 Approved
0.6 Remote Similarity NPD7334 Approved
0.6 Remote Similarity NPD7146 Approved
0.6 Remote Similarity NPD6684 Approved
0.6 Remote Similarity NPD7521 Approved
0.596 Remote Similarity NPD5781 Clinical (unspecified phase)
0.5957 Remote Similarity NPD3666 Approved
0.5957 Remote Similarity NPD5766 Clinical (unspecified phase)
0.5957 Remote Similarity NPD3133 Approved
0.5957 Remote Similarity NPD3665 Phase 1
0.5957 Remote Similarity NPD4786 Approved
0.5941 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5929 Remote Similarity NPD7641 Discontinued
0.5914 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5909 Remote Similarity NPD8297 Approved
0.5904 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5904 Remote Similarity NPD7341 Phase 2
0.59 Remote Similarity NPD7748 Approved
0.5888 Remote Similarity NPD6412 Phase 2
0.5888 Remote Similarity NPD5697 Approved
0.5882 Remote Similarity NPD6084 Phase 2
0.5882 Remote Similarity NPD6083 Phase 2
0.5882 Remote Similarity NPD7902 Approved
0.5876 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5876 Remote Similarity NPD6903 Approved
0.5876 Remote Similarity NPD5208 Approved
0.5859 Remote Similarity NPD6079 Approved
0.5859 Remote Similarity NPD7515 Phase 2
0.5844 Remote Similarity NPD3729 Clinical (unspecified phase)
0.5842 Remote Similarity NPD5695 Phase 3
0.5841 Remote Similarity NPD7115 Discovery
0.5833 Remote Similarity NPD6011 Approved
0.5833 Remote Similarity NPD6881 Approved
0.5833 Remote Similarity NPD6899 Approved
0.5833 Remote Similarity NPD4519 Discontinued
0.5833 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5279 Phase 3
0.5833 Remote Similarity NPD4623 Approved
0.5826 Remote Similarity NPD6319 Approved
0.5825 Remote Similarity NPD7638 Approved
0.5825 Remote Similarity NPD5696 Approved
0.5818 Remote Similarity NPD6649 Approved
0.5818 Remote Similarity NPD6650 Approved
0.5816 Remote Similarity NPD5328 Approved
0.5798 Remote Similarity NPD8074 Phase 3
0.5794 Remote Similarity NPD6675 Approved
0.5794 Remote Similarity NPD7128 Approved
0.5794 Remote Similarity NPD5739 Approved
0.5794 Remote Similarity NPD6402 Approved
0.5784 Remote Similarity NPD4792 Clinical (unspecified phase)
0.578 Remote Similarity NPD6372 Approved
0.578 Remote Similarity NPD6373 Approved
0.578 Remote Similarity NPD6012 Approved
0.578 Remote Similarity NPD6013 Approved
0.578 Remote Similarity NPD6014 Approved
0.5769 Remote Similarity NPD7640 Approved
0.5769 Remote Similarity NPD7639 Approved
0.5758 Remote Similarity NPD5207 Approved
0.5745 Remote Similarity NPD5209 Approved
0.5741 Remote Similarity NPD5701 Approved
0.5729 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5727 Remote Similarity NPD7102 Approved
0.5727 Remote Similarity NPD7290 Approved
0.5727 Remote Similarity NPD6883 Approved
0.5727 Remote Similarity NPD6421 Discontinued
0.5714 Remote Similarity NPD4518 Approved
0.5714 Remote Similarity NPD5344 Discontinued
0.5714 Remote Similarity NPD5737 Approved
0.5714 Remote Similarity NPD6672 Approved
0.5702 Remote Similarity NPD6009 Approved
0.57 Remote Similarity NPD5284 Approved
0.57 Remote Similarity NPD5281 Approved
0.57 Remote Similarity NPD8034 Phase 2
0.57 Remote Similarity NPD8035 Phase 2
0.5688 Remote Similarity NPD7320 Approved
0.5676 Remote Similarity NPD6869 Approved
0.5676 Remote Similarity NPD6847 Approved
0.5676 Remote Similarity NPD6617 Approved
0.5676 Remote Similarity NPD1719 Phase 1
0.5676 Remote Similarity NPD8130 Phase 1
0.5676 Remote Similarity NPD5343 Approved
0.567 Remote Similarity NPD5205 Approved
0.567 Remote Similarity NPD4688 Approved
0.567 Remote Similarity NPD4689 Approved
0.567 Remote Similarity NPD4138 Approved
0.567 Remote Similarity NPD4693 Phase 3
0.567 Remote Similarity NPD4690 Approved
0.5648 Remote Similarity NPD6008 Approved
0.5641 Remote Similarity NPD8444 Approved
0.5641 Remote Similarity NPD5983 Phase 2
0.5638 Remote Similarity NPD857 Phase 3
0.5636 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5636 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5631 Remote Similarity NPD5221 Approved
0.5631 Remote Similarity NPD5222 Approved
0.5631 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5631 Remote Similarity NPD4697 Phase 3
0.563 Remote Similarity NPD8342 Approved
0.563 Remote Similarity NPD7492 Approved
0.563 Remote Similarity NPD8340 Approved
0.563 Remote Similarity NPD8299 Approved
0.563 Remote Similarity NPD8341 Approved
0.5625 Remote Similarity NPD6882 Approved
0.5625 Remote Similarity NPD6053 Discontinued
0.5616 Remote Similarity NPD3174 Discontinued
0.5616 Remote Similarity NPD634 Phase 3
0.5616 Remote Similarity NPD4222 Approved
0.5614 Remote Similarity NPD2629 Approved
0.5612 Remote Similarity NPD3573 Approved
0.5612 Remote Similarity NPD7750 Discontinued
0.5612 Remote Similarity NPD7524 Approved
0.5604 Remote Similarity NPD6933 Approved

Structure

External Identifiers

PubChem CID   46879782
ChEMBL   CHEMBL1080835
ZINC  

Physicochemical Properties

Molecular Weight:  324.17
ALogP:  2.7204
MLogP:  3.44
XLogP:  5.729
# Rotatable Bonds:  9
Polar Surface Area:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  24

Download Data

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