Natural Product: NPC38569

Natural Product ID:  NPC38569
Common Name:   (-)-Miliusane Xix
IUPAC Name:   methyl 2-[(1S,5R,6R)-6-[(1E)-2,6-dimethylhepta-1,5-dienyl]-4-oxo-7-oxabicyclo[3.2.1]oct-2-en-5-yl]acetate
Synonyms:   (-)-Miliusane Xix
Molecular Formula:   C19H26O4
Standard InCHIKey:  MOGLHHCTNHEXAL-OROLVADBSA-N
Standard InCHI:  InChI=1S/C19H26O4/c1-13(2)6-5-7-14(3)10-17-19(12-18(21)22-4)11-15(23-17)8-9-16(19)20/h6,8-10,15,17H,5,7,11-12H2,1-4H3/b14-10+/t15-,17-,19+/m1/s1
Canonical SMILES:  COC(=O)C[C@]12C[C@H](O[C@@H]1/C=C(/CCC=C(C)C)C)C=CC2=O
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
NPO22093 Miliusa sinensis Species Annonaceae Eukaryota dried leaves, twigs, and flowers Vietnam PMID[16420055]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens IC50 = 2610 nM DrugMatrix in vitro pharmacology data
NPT1034 Cell Line Lu1 Homo sapiens IC50 = 1820 nM 22676269
NPT1851 Cell Line Col2 Homo sapiens IC50 = 2010 nM 25237727
NPT858 Cell Line LNCaP Homo sapiens IC50 = 1730 nM 15711537
NPT83 Cell Line MCF7 Homo sapiens IC50 = 2260 nM 3373220

  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 NPC38569 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
1.0 High Similarity NPC163615
0.9873 High Similarity NPC155873
0.963 High Similarity NPC473248
0.9512 High Similarity NPC153570
0.9398 High Similarity NPC78008
0.9398 High Similarity NPC87306
0.9286 High Similarity NPC473455
0.9125 High Similarity NPC275507
0.8864 High Similarity NPC214694
0.8795 High Similarity NPC219966
0.8452 Intermediate Similarity NPC52923
0.8111 Intermediate Similarity NPC233437
0.8111 Intermediate Similarity NPC207641
0.7912 Intermediate Similarity NPC284185
0.7816 Intermediate Similarity NPC318468
0.7802 Intermediate Similarity NPC253144
0.7766 Intermediate Similarity NPC11396
0.7766 Intermediate Similarity NPC21302
0.7765 Intermediate Similarity NPC473980
0.7765 Intermediate Similarity NPC473981
0.7717 Intermediate Similarity NPC123177
0.7717 Intermediate Similarity NPC150978
0.7717 Intermediate Similarity NPC74103
0.7717 Intermediate Similarity NPC20713
0.7717 Intermediate Similarity NPC70595
0.7701 Intermediate Similarity NPC475690
0.7684 Intermediate Similarity NPC134454
0.7684 Intermediate Similarity NPC17326
0.7653 Intermediate Similarity NPC110989
0.7647 Intermediate Similarity NPC475699
0.7609 Intermediate Similarity NPC62815
0.759 Intermediate Similarity NPC476355
0.759 Intermediate Similarity NPC117746
0.759 Intermediate Similarity NPC259599
0.759 Intermediate Similarity NPC15499
0.759 Intermediate Similarity NPC294434
0.7576 Intermediate Similarity NPC203659
0.7558 Intermediate Similarity NPC270126
0.7556 Intermediate Similarity NPC284902
0.7556 Intermediate Similarity NPC478112
0.7553 Intermediate Similarity NPC140543
0.7553 Intermediate Similarity NPC476267
0.7551 Intermediate Similarity NPC225353
0.7531 Intermediate Similarity NPC476591
0.7531 Intermediate Similarity NPC88877
0.7529 Intermediate Similarity NPC57744
0.7527 Intermediate Similarity NPC221282
0.7527 Intermediate Similarity NPC472705
0.75 Intermediate Similarity NPC166919
0.7474 Intermediate Similarity NPC477922
0.7474 Intermediate Similarity NPC471142
0.7473 Intermediate Similarity NPC475703
0.7473 Intermediate Similarity NPC231889
0.7471 Intermediate Similarity NPC223904
0.7447 Intermediate Similarity NPC475657
0.7444 Intermediate Similarity NPC473353
0.7444 Intermediate Similarity NPC215364
0.7442 Intermediate Similarity NPC128276
0.7442 Intermediate Similarity NPC471220
0.7442 Intermediate Similarity NPC253749
0.7423 Intermediate Similarity NPC54843
0.7423 Intermediate Similarity NPC23364
0.7423 Intermediate Similarity NPC141191
0.7419 Intermediate Similarity NPC179394
0.7419 Intermediate Similarity NPC71533
0.7419 Intermediate Similarity NPC144133
0.7419 Intermediate Similarity NPC106510
0.7419 Intermediate Similarity NPC473619
0.7416 Intermediate Similarity NPC170286
0.7416 Intermediate Similarity NPC272814
0.7412 Intermediate Similarity NPC27205
0.7412 Intermediate Similarity NPC123360
0.7407 Intermediate Similarity NPC470256
0.74 Intermediate Similarity NPC169843
0.74 Intermediate Similarity NPC470297
0.7396 Intermediate Similarity NPC477921
0.7396 Intermediate Similarity NPC17585
0.7396 Intermediate Similarity NPC476275
0.7396 Intermediate Similarity NPC185553
0.7391 Intermediate Similarity NPC469653
0.7391 Intermediate Similarity NPC471047
0.7391 Intermediate Similarity NPC469628
0.7391 Intermediate Similarity NPC475906
0.7391 Intermediate Similarity NPC469631
0.7386 Intermediate Similarity NPC297440
0.7386 Intermediate Similarity NPC474980
0.7386 Intermediate Similarity NPC42470
0.7381 Intermediate Similarity NPC140287
0.7374 Intermediate Similarity NPC149371
0.7374 Intermediate Similarity NPC235369
0.7368 Intermediate Similarity NPC471147
0.7363 Intermediate Similarity NPC278283
0.7363 Intermediate Similarity NPC104961
0.7363 Intermediate Similarity NPC279859
0.7363 Intermediate Similarity NPC70422
0.7363 Intermediate Similarity NPC38576
0.7363 Intermediate Similarity NPC70555
0.7356 Intermediate Similarity NPC471299
0.7356 Intermediate Similarity NPC178277
0.7349 Intermediate Similarity NPC163003
0.7347 Intermediate Similarity NPC469402
0.7347 Intermediate Similarity NPC476933
0.7347 Intermediate Similarity NPC477512
0.734 Intermediate Similarity NPC473321
0.7326 Intermediate Similarity NPC476028
0.7326 Intermediate Similarity NPC141789
0.7326 Intermediate Similarity NPC171204
0.7326 Intermediate Similarity NPC41780
0.7326 Intermediate Similarity NPC187568
0.7326 Intermediate Similarity NPC97516
0.732 Intermediate Similarity NPC169205
0.732 Intermediate Similarity NPC70145
0.732 Intermediate Similarity NPC91695
0.7312 Intermediate Similarity NPC295312
0.7303 Intermediate Similarity NPC173609
0.73 Intermediate Similarity NPC475945
0.73 Intermediate Similarity NPC254202
0.73 Intermediate Similarity NPC475871
0.7292 Intermediate Similarity NPC473369
0.7292 Intermediate Similarity NPC475659
0.7292 Intermediate Similarity NPC275960
0.7292 Intermediate Similarity NPC90121
0.7292 Intermediate Similarity NPC474947
0.7292 Intermediate Similarity NPC48803
0.7292 Intermediate Similarity NPC193645
0.7284 Intermediate Similarity NPC203335
0.7284 Intermediate Similarity NPC194871
0.7283 Intermediate Similarity NPC478144
0.7283 Intermediate Similarity NPC160138
0.7273 Intermediate Similarity NPC474510
0.7273 Intermediate Similarity NPC281132
0.7273 Intermediate Similarity NPC47880
0.7273 Intermediate Similarity NPC474742
0.7273 Intermediate Similarity NPC472753
0.7273 Intermediate Similarity NPC171759
0.7263 Intermediate Similarity NPC288240
0.7263 Intermediate Similarity NPC162205
0.7263 Intermediate Similarity NPC295204
0.7263 Intermediate Similarity NPC273579
0.7262 Intermediate Similarity NPC287878
0.7255 Intermediate Similarity NPC133422
0.7253 Intermediate Similarity NPC161957
0.7253 Intermediate Similarity NPC177932
0.7253 Intermediate Similarity NPC33570
0.7253 Intermediate Similarity NPC21471
0.7253 Intermediate Similarity NPC470755
0.7253 Intermediate Similarity NPC110405
0.7253 Intermediate Similarity NPC21469
0.7245 Intermediate Similarity NPC471144
0.7241 Intermediate Similarity NPC93763
0.7241 Intermediate Similarity NPC108816
0.7234 Intermediate Similarity NPC80875
0.7234 Intermediate Similarity NPC475748
0.7234 Intermediate Similarity NPC475855
0.7234 Intermediate Similarity NPC51004
0.7234 Intermediate Similarity NPC312042
0.7234 Intermediate Similarity NPC469718
0.7234 Intermediate Similarity NPC329857
0.7228 Intermediate Similarity NPC474741
0.7222 Intermediate Similarity NPC250315
0.7222 Intermediate Similarity NPC475947
0.7222 Intermediate Similarity NPC170377
0.7216 Intermediate Similarity NPC473859
0.7204 Intermediate Similarity NPC473715
0.7204 Intermediate Similarity NPC202672
0.7204 Intermediate Similarity NPC150063
0.7204 Intermediate Similarity NPC226863
0.7204 Intermediate Similarity NPC119740
0.7204 Intermediate Similarity NPC475902
0.7204 Intermediate Similarity NPC475819
0.72 Intermediate Similarity NPC474747
0.72 Intermediate Similarity NPC472754
0.7191 Intermediate Similarity NPC471325
0.7191 Intermediate Similarity NPC25684
0.7191 Intermediate Similarity NPC281949
0.7191 Intermediate Similarity NPC301477
0.7188 Intermediate Similarity NPC477129
0.7188 Intermediate Similarity NPC473330
0.7188 Intermediate Similarity NPC475927
0.7188 Intermediate Similarity NPC148463
0.7188 Intermediate Similarity NPC470697
0.7188 Intermediate Similarity NPC473316
0.7188 Intermediate Similarity NPC477130
0.7188 Intermediate Similarity NPC475832
0.7184 Intermediate Similarity NPC89171
0.7184 Intermediate Similarity NPC476802
0.7174 Intermediate Similarity NPC261253
0.7174 Intermediate Similarity NPC220478
0.7174 Intermediate Similarity NPC474045
0.7174 Intermediate Similarity NPC50637
0.7174 Intermediate Similarity NPC469676
0.7172 Intermediate Similarity NPC54705
0.7172 Intermediate Similarity NPC288876
0.7172 Intermediate Similarity NPC280963
0.716 Intermediate Similarity NPC248125
0.7159 Intermediate Similarity NPC150646
0.7159 Intermediate Similarity NPC469690
0.7159 Intermediate Similarity NPC469620
0.7158 Intermediate Similarity NPC261607
0.7158 Intermediate Similarity NPC473944

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC38569 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
0.75 Intermediate Similarity NPD5209 Approved
0.7292 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD1694 Approved
0.6882 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5785 Approved
0.6739 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6705 Remote Similarity NPD8039 Approved
0.6667 Remote Similarity NPD5282 Discontinued
0.6574 Remote Similarity NPD6371 Approved
0.6531 Remote Similarity NPD6698 Approved
0.6531 Remote Similarity NPD46 Approved
0.6509 Remote Similarity NPD6008 Approved
0.6465 Remote Similarity NPD7983 Approved
0.6458 Remote Similarity NPD5786 Approved
0.6449 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6429 Remote Similarity NPD1695 Approved
0.6429 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6408 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6408 Remote Similarity NPD4225 Approved
0.64 Remote Similarity NPD5778 Approved
0.64 Remote Similarity NPD5779 Approved
0.6354 Remote Similarity NPD5363 Approved
0.6316 Remote Similarity NPD6110 Phase 1
0.625 Remote Similarity NPD7638 Approved
0.6239 Remote Similarity NPD6686 Approved
0.62 Remote Similarity NPD7838 Discovery
0.619 Remote Similarity NPD7640 Approved
0.619 Remote Similarity NPD7639 Approved
0.6176 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6176 Remote Similarity NPD7900 Approved
0.617 Remote Similarity NPD4252 Approved
0.6147 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6139 Remote Similarity NPD7637 Suspended
0.6139 Remote Similarity NPD6411 Approved
0.6129 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6122 Remote Similarity NPD7521 Approved
0.6122 Remote Similarity NPD5330 Approved
0.6122 Remote Similarity NPD7146 Approved
0.6122 Remote Similarity NPD7334 Approved
0.6122 Remote Similarity NPD6409 Approved
0.6122 Remote Similarity NPD4249 Approved
0.6122 Remote Similarity NPD6684 Approved
0.6118 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6092 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6087 Remote Similarity NPD7115 Discovery
0.6082 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6078 Remote Similarity NPD6399 Phase 3
0.6071 Remote Similarity NPD6650 Approved
0.6071 Remote Similarity NPD6649 Approved
0.6068 Remote Similarity NPD6319 Approved
0.6061 Remote Similarity NPD3573 Approved
0.6061 Remote Similarity NPD4251 Approved
0.6061 Remote Similarity NPD4250 Approved
0.6058 Remote Similarity NPD7839 Suspended
0.6042 Remote Similarity NPD4269 Approved
0.6042 Remote Similarity NPD6435 Approved
0.6042 Remote Similarity NPD4270 Approved
0.6018 Remote Similarity NPD6053 Discontinued
0.6017 Remote Similarity NPD8517 Approved
0.6017 Remote Similarity NPD8513 Phase 3
0.6017 Remote Similarity NPD8515 Approved
0.6017 Remote Similarity NPD8516 Approved
0.6 Remote Similarity NPD7492 Approved
0.6 Remote Similarity NPD5737 Approved
0.6 Remote Similarity NPD5697 Approved
0.6 Remote Similarity NPD6903 Approved
0.6 Remote Similarity NPD6672 Approved
0.6 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6 Remote Similarity NPD7902 Approved
0.5982 Remote Similarity NPD5955 Clinical (unspecified phase)
0.598 Remote Similarity NPD5693 Phase 1
0.5968 Remote Similarity NPD7260 Phase 2
0.5965 Remote Similarity NPD4632 Approved
0.595 Remote Similarity NPD6616 Approved
0.5946 Remote Similarity NPD6011 Approved
0.5946 Remote Similarity NPD6899 Approved
0.5946 Remote Similarity NPD6881 Approved
0.5941 Remote Similarity NPD6101 Approved
0.5941 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5938 Remote Similarity NPD5369 Approved
0.5932 Remote Similarity NPD6054 Approved
0.5902 Remote Similarity NPD7078 Approved
0.5893 Remote Similarity NPD6373 Approved
0.5893 Remote Similarity NPD6013 Approved
0.5893 Remote Similarity NPD6012 Approved
0.5893 Remote Similarity NPD6014 Approved
0.5893 Remote Similarity NPD6372 Approved
0.5882 Remote Similarity NPD5207 Approved
0.5882 Remote Similarity NPD6016 Approved
0.5882 Remote Similarity NPD6015 Approved
0.5859 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5854 Remote Similarity NPD7736 Approved
0.5851 Remote Similarity NPD4756 Discovery
0.5841 Remote Similarity NPD6883 Approved
0.5841 Remote Similarity NPD7102 Approved
0.5841 Remote Similarity NPD7290 Approved
0.5833 Remote Similarity NPD6370 Approved
0.5833 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5368 Approved
0.5833 Remote Similarity NPD5988 Approved
0.5825 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5823 Remote Similarity NPD6927 Phase 3
0.5816 Remote Similarity NPD7154 Phase 3
0.5812 Remote Similarity NPD6009 Approved
0.581 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5804 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5795 Remote Similarity NPD7331 Phase 2
0.5789 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6847 Approved
0.5789 Remote Similarity NPD8130 Phase 1
0.5789 Remote Similarity NPD6617 Approved
0.5789 Remote Similarity NPD6869 Approved
0.5785 Remote Similarity NPD7642 Approved
0.5784 Remote Similarity NPD5370 Suspended
0.5772 Remote Similarity NPD8074 Phase 3
0.5766 Remote Similarity NPD5739 Approved
0.5766 Remote Similarity NPD7128 Approved
0.5766 Remote Similarity NPD6402 Approved
0.5766 Remote Similarity NPD6675 Approved
0.5752 Remote Similarity NPD4061 Clinical (unspecified phase)
0.575 Remote Similarity NPD5983 Phase 2
0.5741 Remote Similarity NPD6648 Approved
0.5739 Remote Similarity NPD6882 Approved
0.5739 Remote Similarity NPD8297 Approved
0.5736 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7748 Approved
0.5714 Remote Similarity NPD5701 Approved
0.5702 Remote Similarity NPD4634 Approved
0.5688 Remote Similarity NPD5344 Discontinued
0.568 Remote Similarity NPD7319 Approved
0.5678 Remote Similarity NPD7500 Approved
0.5673 Remote Similarity NPD6079 Approved
0.5673 Remote Similarity NPD5281 Approved
0.5673 Remote Similarity NPD5284 Approved
0.5673 Remote Similarity NPD5694 Approved
0.567 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5669 Remote Similarity NPD6845 Suspended
0.5667 Remote Similarity NPD6059 Approved
0.5664 Remote Similarity NPD7320 Approved
0.566 Remote Similarity NPD5695 Phase 3
0.5657 Remote Similarity NPD5362 Discontinued
0.5656 Remote Similarity NPD7830 Approved
0.5656 Remote Similarity NPD7604 Phase 2
0.5656 Remote Similarity NPD7829 Approved
0.5656 Remote Similarity NPD8328 Phase 3
0.5652 Remote Similarity NPD2204 Approved
0.5648 Remote Similarity NPD5696 Approved
0.5645 Remote Similarity NPD8293 Discontinued
0.5636 Remote Similarity NPD7632 Discontinued
0.5636 Remote Similarity NPD5211 Phase 2
0.5631 Remote Similarity NPD6904 Approved
0.5631 Remote Similarity NPD6051 Approved
0.5631 Remote Similarity NPD6673 Approved
0.5631 Remote Similarity NPD6080 Approved
0.5625 Remote Similarity NPD5048 Discontinued
0.5625 Remote Similarity NPD4271 Approved
0.5625 Remote Similarity NPD4268 Approved
0.562 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5618 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5607 Remote Similarity NPD4697 Phase 3
0.5607 Remote Similarity NPD5221 Approved
0.5607 Remote Similarity NPD5222 Approved
0.5607 Remote Similarity NPD5220 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   11602160
ChEMBL   CHEMBL203140
ZINC  

Physicochemical Properties

Molecular Weight:  318.18
ALogP:  2.3694
MLogP:  3.11
XLogP:  2.775
# Rotatable Bonds:  11
Polar Surface Area:  52.6
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  23

Download Data

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