Natural Product: NPC155873

Natural Product ID:  NPC155873
Common Name:   (+)-Miliusane Xvi
IUPAC Name:   [(1R,5R,9S)-1-[(1E)-2,6-dimethyl-5-oxohepta-1,6-dienyl]-3,6-dioxo-2-oxaspiro[4.5]dec-7-en-9-yl] acetate
Synonyms:   (+)-Miliusane XVI
Molecular Formula:   C20H24O6
Standard InCHIKey:  LMLJUECRBQYQEU-BIPLCGTOSA-N
Standard InCHI:  InChI=1S/C20H24O6/c1-12(2)16(22)7-5-13(3)9-18-20(11-19(24)26-18)10-15(25-14(4)21)6-8-17(20)23/h6,8-9,15,18H,1,5,7,10-11H2,2-4H3/b13-9+/t15-,18-,20+/m1/s1
Canonical SMILES:  C/C(=C[C@H]1OC(=O)C[C@@]21C[C@@H](C=CC2=O)OC(=O)C)/CCC(=O)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
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
NPT1034 Cell Line Lu1 Homo sapiens IC50 = 19940 nM DailyMed
NPT91 Cell Line KB Homo sapiens IC50 = 6110 nM 10096871
NPT1851 Cell Line Col2 Homo sapiens IC50 = 3890 nM 17027268
NPT83 Cell Line MCF7 Homo sapiens IC50 = 6390 nM PubChem BioAssay data set
NPT858 Cell Line LNCaP Homo sapiens IC50 = 6110 nM 22264149

  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 NPC155873 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
0.9873 High Similarity NPC163615
0.9873 High Similarity NPC38569
0.9518 High Similarity NPC78008
0.9512 High Similarity NPC473248
0.9405 High Similarity NPC473455
0.9398 High Similarity NPC153570
0.9286 High Similarity NPC87306
0.9012 High Similarity NPC275507
0.8977 High Similarity NPC214694
0.869 High Similarity NPC219966
0.8353 Intermediate Similarity NPC52923
0.8222 Intermediate Similarity NPC233437
0.8222 Intermediate Similarity NPC207641
0.8022 Intermediate Similarity NPC284185
0.7931 Intermediate Similarity NPC318468
0.7912 Intermediate Similarity NPC253144
0.7882 Intermediate Similarity NPC473980
0.7882 Intermediate Similarity NPC473981
0.7872 Intermediate Similarity NPC21302
0.7872 Intermediate Similarity NPC11396
0.7826 Intermediate Similarity NPC70595
0.7826 Intermediate Similarity NPC74103
0.7826 Intermediate Similarity NPC150978
0.7826 Intermediate Similarity NPC123177
0.7826 Intermediate Similarity NPC20713
0.7816 Intermediate Similarity NPC475690
0.7789 Intermediate Similarity NPC134454
0.7789 Intermediate Similarity NPC17326
0.7765 Intermediate Similarity NPC475699
0.7755 Intermediate Similarity NPC110989
0.7717 Intermediate Similarity NPC62815
0.7711 Intermediate Similarity NPC117746
0.7711 Intermediate Similarity NPC294434
0.7711 Intermediate Similarity NPC259599
0.7711 Intermediate Similarity NPC15499
0.7711 Intermediate Similarity NPC476355
0.7677 Intermediate Similarity NPC203659
0.7674 Intermediate Similarity NPC270126
0.7667 Intermediate Similarity NPC284902
0.7667 Intermediate Similarity NPC478112
0.766 Intermediate Similarity NPC476267
0.766 Intermediate Similarity NPC140543
0.7653 Intermediate Similarity NPC225353
0.7647 Intermediate Similarity NPC57744
0.7634 Intermediate Similarity NPC472705
0.7634 Intermediate Similarity NPC221282
0.7609 Intermediate Similarity NPC166919
0.7586 Intermediate Similarity NPC223904
0.7582 Intermediate Similarity NPC231889
0.7582 Intermediate Similarity NPC475703
0.7579 Intermediate Similarity NPC477922
0.7579 Intermediate Similarity NPC471142
0.7558 Intermediate Similarity NPC128276
0.7558 Intermediate Similarity NPC471220
0.7558 Intermediate Similarity NPC253749
0.7556 Intermediate Similarity NPC473353
0.7556 Intermediate Similarity NPC215364
0.7553 Intermediate Similarity NPC475657
0.7531 Intermediate Similarity NPC470256
0.7529 Intermediate Similarity NPC123360
0.7529 Intermediate Similarity NPC27205
0.7528 Intermediate Similarity NPC170286
0.7528 Intermediate Similarity NPC272814
0.7527 Intermediate Similarity NPC144133
0.7527 Intermediate Similarity NPC71533
0.7527 Intermediate Similarity NPC106510
0.7527 Intermediate Similarity NPC473619
0.7527 Intermediate Similarity NPC179394
0.7526 Intermediate Similarity NPC141191
0.7526 Intermediate Similarity NPC54843
0.7526 Intermediate Similarity NPC23364
0.75 Intermediate Similarity NPC469653
0.75 Intermediate Similarity NPC471047
0.75 Intermediate Similarity NPC477921
0.75 Intermediate Similarity NPC469631
0.75 Intermediate Similarity NPC476275
0.75 Intermediate Similarity NPC185553
0.75 Intermediate Similarity NPC469628
0.75 Intermediate Similarity NPC470297
0.75 Intermediate Similarity NPC140287
0.75 Intermediate Similarity NPC17585
0.75 Intermediate Similarity NPC475906
0.75 Intermediate Similarity NPC169843
0.75 Intermediate Similarity NPC42470
0.7475 Intermediate Similarity NPC235369
0.7475 Intermediate Similarity NPC149371
0.7474 Intermediate Similarity NPC471147
0.7473 Intermediate Similarity NPC38576
0.7473 Intermediate Similarity NPC70555
0.7473 Intermediate Similarity NPC70422
0.7473 Intermediate Similarity NPC104961
0.7473 Intermediate Similarity NPC279859
0.7471 Intermediate Similarity NPC471299
0.7471 Intermediate Similarity NPC178277
0.747 Intermediate Similarity NPC163003
0.7449 Intermediate Similarity NPC477512
0.7449 Intermediate Similarity NPC469402
0.7449 Intermediate Similarity NPC476933
0.7447 Intermediate Similarity NPC473321
0.7442 Intermediate Similarity NPC187568
0.7442 Intermediate Similarity NPC41780
0.7442 Intermediate Similarity NPC476028
0.7442 Intermediate Similarity NPC97516
0.7442 Intermediate Similarity NPC171204
0.7442 Intermediate Similarity NPC141789
0.7439 Intermediate Similarity NPC476591
0.7439 Intermediate Similarity NPC88877
0.7423 Intermediate Similarity NPC70145
0.7423 Intermediate Similarity NPC169205
0.7423 Intermediate Similarity NPC91695
0.7419 Intermediate Similarity NPC295312
0.7416 Intermediate Similarity NPC173609
0.7407 Intermediate Similarity NPC194871
0.74 Intermediate Similarity NPC475945
0.74 Intermediate Similarity NPC254202
0.74 Intermediate Similarity NPC475871
0.7396 Intermediate Similarity NPC473369
0.7396 Intermediate Similarity NPC275960
0.7396 Intermediate Similarity NPC475659
0.7396 Intermediate Similarity NPC90121
0.7396 Intermediate Similarity NPC193645
0.7396 Intermediate Similarity NPC48803
0.7396 Intermediate Similarity NPC474947
0.7391 Intermediate Similarity NPC160138
0.7391 Intermediate Similarity NPC478144
0.7386 Intermediate Similarity NPC474510
0.7386 Intermediate Similarity NPC281132
0.7374 Intermediate Similarity NPC474742
0.7374 Intermediate Similarity NPC472753
0.7374 Intermediate Similarity NPC47880
0.7374 Intermediate Similarity NPC171759
0.7368 Intermediate Similarity NPC288240
0.7368 Intermediate Similarity NPC162205
0.7368 Intermediate Similarity NPC273579
0.7368 Intermediate Similarity NPC295204
0.7363 Intermediate Similarity NPC177932
0.7363 Intermediate Similarity NPC21471
0.7363 Intermediate Similarity NPC33570
0.7363 Intermediate Similarity NPC110405
0.7363 Intermediate Similarity NPC470755
0.7363 Intermediate Similarity NPC21469
0.7363 Intermediate Similarity NPC161957
0.7356 Intermediate Similarity NPC93763
0.7356 Intermediate Similarity NPC108816
0.7353 Intermediate Similarity NPC133422
0.7347 Intermediate Similarity NPC471144
0.734 Intermediate Similarity NPC312042
0.734 Intermediate Similarity NPC80875
0.734 Intermediate Similarity NPC329857
0.734 Intermediate Similarity NPC469718
0.734 Intermediate Similarity NPC475855
0.734 Intermediate Similarity NPC475748
0.734 Intermediate Similarity NPC51004
0.7333 Intermediate Similarity NPC475947
0.7333 Intermediate Similarity NPC170377
0.7333 Intermediate Similarity NPC250315
0.7327 Intermediate Similarity NPC474741
0.732 Intermediate Similarity NPC473859
0.7312 Intermediate Similarity NPC475819
0.7312 Intermediate Similarity NPC473715
0.7312 Intermediate Similarity NPC202672
0.7312 Intermediate Similarity NPC475902
0.7312 Intermediate Similarity NPC226863
0.7303 Intermediate Similarity NPC297440
0.7303 Intermediate Similarity NPC301477
0.7303 Intermediate Similarity NPC281949
0.7303 Intermediate Similarity NPC25684
0.7303 Intermediate Similarity NPC474980
0.7303 Intermediate Similarity NPC471325
0.73 Intermediate Similarity NPC474747
0.73 Intermediate Similarity NPC472754
0.7292 Intermediate Similarity NPC473330
0.7292 Intermediate Similarity NPC477130
0.7292 Intermediate Similarity NPC473316
0.7292 Intermediate Similarity NPC470697
0.7292 Intermediate Similarity NPC148463
0.7292 Intermediate Similarity NPC477129
0.7284 Intermediate Similarity NPC248125
0.7283 Intermediate Similarity NPC220478
0.7283 Intermediate Similarity NPC261253
0.7283 Intermediate Similarity NPC50637
0.7283 Intermediate Similarity NPC278283
0.7283 Intermediate Similarity NPC469676
0.7283 Intermediate Similarity NPC474045
0.7282 Intermediate Similarity NPC476802
0.7282 Intermediate Similarity NPC89171
0.7273 Intermediate Similarity NPC469690
0.7273 Intermediate Similarity NPC469620
0.7273 Intermediate Similarity NPC150646
0.7273 Intermediate Similarity NPC54705
0.7273 Intermediate Similarity NPC288876
0.7273 Intermediate Similarity NPC280963
0.7263 Intermediate Similarity NPC30515
0.7263 Intermediate Similarity NPC111114
0.7263 Intermediate Similarity NPC290651
0.7263 Intermediate Similarity NPC191339
0.7263 Intermediate Similarity NPC473944
0.7263 Intermediate Similarity NPC261607
0.7263 Intermediate Similarity NPC300312
0.7263 Intermediate Similarity NPC286341

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC155873 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
0.7614 Intermediate Similarity NPD5209 Approved
0.7396 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD1694 Approved
0.6989 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6979 Remote Similarity NPD5785 Approved
0.6848 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6818 Remote Similarity NPD8039 Approved
0.6768 Remote Similarity NPD5282 Discontinued
0.6667 Remote Similarity NPD6371 Approved
0.6633 Remote Similarity NPD6698 Approved
0.6633 Remote Similarity NPD46 Approved
0.6604 Remote Similarity NPD6008 Approved
0.6566 Remote Similarity NPD7983 Approved
0.6562 Remote Similarity NPD5786 Approved
0.6548 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6542 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6531 Remote Similarity NPD1695 Approved
0.6505 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6505 Remote Similarity NPD4225 Approved
0.65 Remote Similarity NPD5778 Approved
0.65 Remote Similarity NPD5779 Approved
0.6458 Remote Similarity NPD5363 Approved
0.6346 Remote Similarity NPD7638 Approved
0.633 Remote Similarity NPD6686 Approved
0.63 Remote Similarity NPD7838 Discovery
0.6286 Remote Similarity NPD7639 Approved
0.6286 Remote Similarity NPD7640 Approved
0.6277 Remote Similarity NPD4252 Approved
0.6275 Remote Similarity NPD7900 Approved
0.6275 Remote Similarity NPD7901 Clinical (unspecified phase)
0.625 Remote Similarity NPD6110 Phase 1
0.6239 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6238 Remote Similarity NPD7637 Suspended
0.6238 Remote Similarity NPD6411 Approved
0.6237 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6235 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6224 Remote Similarity NPD7521 Approved
0.6224 Remote Similarity NPD7334 Approved
0.6224 Remote Similarity NPD6684 Approved
0.6224 Remote Similarity NPD6409 Approved
0.6224 Remote Similarity NPD7146 Approved
0.6224 Remote Similarity NPD5330 Approved
0.6224 Remote Similarity NPD4249 Approved
0.6186 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6176 Remote Similarity NPD6399 Phase 3
0.6174 Remote Similarity NPD7115 Discovery
0.6162 Remote Similarity NPD4251 Approved
0.6162 Remote Similarity NPD4250 Approved
0.6162 Remote Similarity NPD3573 Approved
0.6161 Remote Similarity NPD6649 Approved
0.6161 Remote Similarity NPD6650 Approved
0.6154 Remote Similarity NPD6319 Approved
0.6154 Remote Similarity NPD7839 Suspended
0.6146 Remote Similarity NPD4269 Approved
0.6146 Remote Similarity NPD4270 Approved
0.6146 Remote Similarity NPD6435 Approved
0.6106 Remote Similarity NPD6053 Discontinued
0.6102 Remote Similarity NPD8513 Phase 3
0.6102 Remote Similarity NPD8515 Approved
0.6102 Remote Similarity NPD8516 Approved
0.6102 Remote Similarity NPD8517 Approved
0.61 Remote Similarity NPD5737 Approved
0.61 Remote Similarity NPD6672 Approved
0.61 Remote Similarity NPD6903 Approved
0.61 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6095 Remote Similarity NPD7902 Approved
0.6091 Remote Similarity NPD5697 Approved
0.6083 Remote Similarity NPD7492 Approved
0.6078 Remote Similarity NPD5693 Phase 1
0.6071 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6053 Remote Similarity NPD4632 Approved
0.6048 Remote Similarity NPD7260 Phase 2
0.6042 Remote Similarity NPD5369 Approved
0.604 Remote Similarity NPD6101 Approved
0.604 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6036 Remote Similarity NPD6011 Approved
0.6036 Remote Similarity NPD6881 Approved
0.6036 Remote Similarity NPD6899 Approved
0.6033 Remote Similarity NPD6616 Approved
0.6023 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6017 Remote Similarity NPD6054 Approved
0.5984 Remote Similarity NPD7078 Approved
0.5982 Remote Similarity NPD6014 Approved
0.5982 Remote Similarity NPD6372 Approved
0.5982 Remote Similarity NPD6012 Approved
0.5982 Remote Similarity NPD6013 Approved
0.5982 Remote Similarity NPD6373 Approved
0.598 Remote Similarity NPD5207 Approved
0.5966 Remote Similarity NPD6016 Approved
0.5966 Remote Similarity NPD6015 Approved
0.596 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5957 Remote Similarity NPD4756 Discovery
0.5938 Remote Similarity NPD5368 Approved
0.5938 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5935 Remote Similarity NPD7736 Approved
0.5929 Remote Similarity NPD7290 Approved
0.5929 Remote Similarity NPD7102 Approved
0.5929 Remote Similarity NPD6883 Approved
0.5922 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5918 Remote Similarity NPD7154 Phase 3
0.5917 Remote Similarity NPD5988 Approved
0.5917 Remote Similarity NPD6370 Approved
0.5909 Remote Similarity NPD7331 Phase 2
0.5905 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5897 Remote Similarity NPD6009 Approved
0.5893 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5882 Remote Similarity NPD5370 Suspended
0.5877 Remote Similarity NPD8130 Phase 1
0.5877 Remote Similarity NPD6847 Approved
0.5877 Remote Similarity NPD6869 Approved
0.5877 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5877 Remote Similarity NPD6617 Approved
0.5868 Remote Similarity NPD7642 Approved
0.5856 Remote Similarity NPD5739 Approved
0.5856 Remote Similarity NPD6402 Approved
0.5856 Remote Similarity NPD7128 Approved
0.5856 Remote Similarity NPD6675 Approved
0.5854 Remote Similarity NPD8074 Phase 3
0.5841 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5983 Phase 2
0.5833 Remote Similarity NPD6648 Approved
0.5826 Remote Similarity NPD6882 Approved
0.5826 Remote Similarity NPD8297 Approved
0.5814 Remote Similarity NPD7966 Clinical (unspecified phase)
0.581 Remote Similarity NPD7748 Approved
0.5804 Remote Similarity NPD5701 Approved
0.5789 Remote Similarity NPD4634 Approved
0.578 Remote Similarity NPD5344 Discontinued
0.5773 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5769 Remote Similarity NPD6079 Approved
0.5769 Remote Similarity NPD5281 Approved
0.5769 Remote Similarity NPD5694 Approved
0.5769 Remote Similarity NPD5284 Approved
0.5763 Remote Similarity NPD7500 Approved
0.576 Remote Similarity NPD7319 Approved
0.5758 Remote Similarity NPD5362 Discontinued
0.5755 Remote Similarity NPD5695 Phase 3
0.5752 Remote Similarity NPD7320 Approved
0.575 Remote Similarity NPD6927 Phase 3
0.575 Remote Similarity NPD6059 Approved
0.5748 Remote Similarity NPD6845 Suspended
0.5741 Remote Similarity NPD5696 Approved
0.5738 Remote Similarity NPD7830 Approved
0.5738 Remote Similarity NPD8328 Phase 3
0.5738 Remote Similarity NPD7829 Approved
0.5738 Remote Similarity NPD7604 Phase 2
0.573 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5729 Remote Similarity NPD4268 Approved
0.5729 Remote Similarity NPD4271 Approved
0.5728 Remote Similarity NPD6051 Approved
0.5728 Remote Similarity NPD6673 Approved
0.5728 Remote Similarity NPD6080 Approved
0.5728 Remote Similarity NPD6904 Approved
0.5727 Remote Similarity NPD7632 Discontinued
0.5727 Remote Similarity NPD5211 Phase 2
0.5726 Remote Similarity NPD8293 Discontinued
0.5714 Remote Similarity NPD5048 Discontinued
0.5702 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5701 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5701 Remote Similarity NPD5221 Approved
0.5701 Remote Similarity NPD5222 Approved
0.5701 Remote Similarity NPD4697 Phase 3
0.5688 Remote Similarity NPD5286 Approved
0.5688 Remote Similarity NPD4696 Approved
0.5688 Remote Similarity NPD5285 Approved
0.5673 Remote Similarity NPD5692 Phase 3
0.5664 Remote Similarity NPD6412 Phase 2
0.566 Remote Similarity NPD6001 Approved
0.5652 Remote Similarity NPD2067 Discontinued
0.5648 Remote Similarity NPD6083 Phase 2
0.5648 Remote Similarity NPD5173 Approved
0.5648 Remote Similarity NPD6084 Phase 2
0.5645 Remote Similarity NPD7507 Approved
0.5645 Remote Similarity NPD6336 Discontinued
0.5636 Remote Similarity NPD5223 Approved
0.5632 Remote Similarity NPD4192 Approved
0.5632 Remote Similarity NPD4194 Approved
0.5632 Remote Similarity NPD4191 Approved
0.5632 Remote Similarity NPD4193 Approved
0.5631 Remote Similarity NPD5208 Approved
0.563 Remote Similarity NPD6317 Approved
0.5625 Remote Similarity NPD5141 Approved
0.5619 Remote Similarity NPD7515 Phase 2
0.5619 Remote Similarity NPD6050 Approved
0.5612 Remote Similarity NPD4820 Approved
0.5612 Remote Similarity NPD4821 Approved
0.5612 Remote Similarity NPD4819 Approved
0.5612 Remote Similarity NPD4822 Approved
0.5603 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5603 Remote Similarity NPD2181 Clinical (unspecified phase)
0.5603 Remote Similarity NPD2204 Approved

Structure

External Identifiers

PubChem CID   11653392
ChEMBL   CHEMBL381737
ZINC  

Physicochemical Properties

Molecular Weight:  360.16
ALogP:  1.4531
MLogP:  3
XLogP:  1.068
# Rotatable Bonds:  10
Polar Surface Area:  86.74
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  26

Download Data

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