Natural Product: NPC473248

Natural Product ID:  NPC473248
Common Name:   (+)-Miliusane Xx
IUPAC Name:   2-[(1S,5R,6R)-6-[(1E)-2,6-dimethylhepta-1,5-dienyl]-4-oxo-7-oxabicyclo[3.2.1]oct-2-en-5-yl]acetic acid
Synonyms:   (+)-Miliusane XX
Molecular Formula:   C18H24O4
Standard InCHIKey:  WAUSUAIPUGCTAF-FWDDYHNSSA-N
Standard InCHI:  InChI=1S/C18H24O4/c1-12(2)5-4-6-13(3)9-16-18(11-17(20)21)10-14(22-16)7-8-15(18)19/h5,7-9,14,16H,4,6,10-11H2,1-3H3,(H,20,21)/b13-9+/t14-,16-,18+/m1/s1
Canonical SMILES:  OC(=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 > 59000 nM PubChem BioAssay data set
NPT1034 Cell Line Lu1 Homo sapiens IC50 > 59000 nM PubChem BioAssay data set
NPT1851 Cell Line Col2 Homo sapiens IC50 > 59000 nM 17027268
NPT116 Cell Line HL-60 Homo sapiens IC50 = 57010 nM 12027740
NPT858 Cell Line LNCaP Homo sapiens IC50 > 59000 nM 22694318
NPT83 Cell Line MCF7 Homo sapiens IC50 > 59000 nM PubChem BioAssay data set

  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 NPC473248 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
0.9759 High Similarity NPC87306
0.9643 High Similarity NPC473455
0.9639 High Similarity NPC153570
0.963 High Similarity NPC163615
0.963 High Similarity NPC38569
0.9512 High Similarity NPC155873
0.9205 High Similarity NPC214694
0.9157 High Similarity NPC219966
0.907 High Similarity NPC78008
0.881 High Similarity NPC52923
0.8795 High Similarity NPC275507
0.8085 Intermediate Similarity NPC11396
0.8085 Intermediate Similarity NPC21302
0.8 Intermediate Similarity NPC134454
0.8 Intermediate Similarity NPC17326
0.7959 Intermediate Similarity NPC110989
0.7889 Intermediate Similarity NPC478112
0.7879 Intermediate Similarity NPC203659
0.7857 Intermediate Similarity NPC225353
0.7849 Intermediate Similarity NPC207641
0.7849 Intermediate Similarity NPC233437
0.7849 Intermediate Similarity NPC472705
0.7789 Intermediate Similarity NPC471142
0.7789 Intermediate Similarity NPC477922
0.7742 Intermediate Similarity NPC71533
0.7742 Intermediate Similarity NPC473619
0.7742 Intermediate Similarity NPC179394
0.7742 Intermediate Similarity NPC106510
0.7742 Intermediate Similarity NPC144133
0.7732 Intermediate Similarity NPC23364
0.7732 Intermediate Similarity NPC141191
0.7727 Intermediate Similarity NPC297440
0.7727 Intermediate Similarity NPC474980
0.7708 Intermediate Similarity NPC477921
0.7708 Intermediate Similarity NPC185553
0.7692 Intermediate Similarity NPC278283
0.7677 Intermediate Similarity NPC149371
0.7677 Intermediate Similarity NPC235369
0.766 Intermediate Similarity NPC284185
0.766 Intermediate Similarity NPC473321
0.7634 Intermediate Similarity NPC295312
0.7629 Intermediate Similarity NPC70145
0.7629 Intermediate Similarity NPC91695
0.7629 Intermediate Similarity NPC169205
0.7609 Intermediate Similarity NPC160138
0.7604 Intermediate Similarity NPC475659
0.7604 Intermediate Similarity NPC48803
0.7604 Intermediate Similarity NPC193645
0.7604 Intermediate Similarity NPC90121
0.7604 Intermediate Similarity NPC275960
0.76 Intermediate Similarity NPC475871
0.76 Intermediate Similarity NPC475945
0.7586 Intermediate Similarity NPC93763
0.7586 Intermediate Similarity NPC108816
0.7582 Intermediate Similarity NPC470755
0.7582 Intermediate Similarity NPC21469
0.7579 Intermediate Similarity NPC295204
0.7579 Intermediate Similarity NPC162205
0.7579 Intermediate Similarity NPC273579
0.7579 Intermediate Similarity NPC288240
0.7576 Intermediate Similarity NPC171759
0.7576 Intermediate Similarity NPC474742
0.7576 Intermediate Similarity NPC47880
0.7576 Intermediate Similarity NPC472753
0.7556 Intermediate Similarity NPC318468
0.7556 Intermediate Similarity NPC250315
0.7553 Intermediate Similarity NPC253144
0.7553 Intermediate Similarity NPC475855
0.7553 Intermediate Similarity NPC51004
0.7551 Intermediate Similarity NPC471144
0.7527 Intermediate Similarity NPC119740
0.7527 Intermediate Similarity NPC150063
0.7527 Intermediate Similarity NPC202672
0.7527 Intermediate Similarity NPC475819
0.7527 Intermediate Similarity NPC473715
0.7526 Intermediate Similarity NPC473859
0.7525 Intermediate Similarity NPC474741
0.75 Intermediate Similarity NPC472754
0.75 Intermediate Similarity NPC473980
0.75 Intermediate Similarity NPC474747
0.75 Intermediate Similarity NPC284902
0.75 Intermediate Similarity NPC475927
0.75 Intermediate Similarity NPC475832
0.75 Intermediate Similarity NPC473981
0.7476 Intermediate Similarity NPC89171
0.7476 Intermediate Similarity NPC476802
0.7475 Intermediate Similarity NPC288876
0.7475 Intermediate Similarity NPC280963
0.7475 Intermediate Similarity NPC54705
0.7474 Intermediate Similarity NPC261607
0.7474 Intermediate Similarity NPC30515
0.7474 Intermediate Similarity NPC111114
0.7474 Intermediate Similarity NPC300312
0.7474 Intermediate Similarity NPC20713
0.7474 Intermediate Similarity NPC123177
0.7474 Intermediate Similarity NPC150978
0.7474 Intermediate Similarity NPC74103
0.7474 Intermediate Similarity NPC70595
0.7473 Intermediate Similarity NPC474251
0.7473 Intermediate Similarity NPC32676
0.7473 Intermediate Similarity NPC472957
0.7473 Intermediate Similarity NPC472958
0.7473 Intermediate Similarity NPC158756
0.7449 Intermediate Similarity NPC471462
0.7449 Intermediate Similarity NPC108475
0.7449 Intermediate Similarity NPC170143
0.7449 Intermediate Similarity NPC213947
0.7449 Intermediate Similarity NPC40812
0.7449 Intermediate Similarity NPC245521
0.7447 Intermediate Similarity NPC474032
0.7447 Intermediate Similarity NPC307411
0.7444 Intermediate Similarity NPC475690
0.7426 Intermediate Similarity NPC475873
0.7426 Intermediate Similarity NPC472755
0.7419 Intermediate Similarity NPC72513
0.74 Intermediate Similarity NPC475099
0.7396 Intermediate Similarity NPC135776
0.7396 Intermediate Similarity NPC475912
0.7396 Intermediate Similarity NPC179746
0.7396 Intermediate Similarity NPC81419
0.7396 Intermediate Similarity NPC476300
0.7391 Intermediate Similarity NPC215364
0.7391 Intermediate Similarity NPC125290
0.7386 Intermediate Similarity NPC475699
0.7386 Intermediate Similarity NPC267231
0.7386 Intermediate Similarity NPC127526
0.7374 Intermediate Similarity NPC83895
0.7374 Intermediate Similarity NPC255592
0.7374 Intermediate Similarity NPC261377
0.7374 Intermediate Similarity NPC187761
0.7374 Intermediate Similarity NPC308567
0.7368 Intermediate Similarity NPC62815
0.7363 Intermediate Similarity NPC116543
0.7363 Intermediate Similarity NPC169575
0.7363 Intermediate Similarity NPC16488
0.7363 Intermediate Similarity NPC40746
0.7353 Intermediate Similarity NPC146731
0.7353 Intermediate Similarity NPC100487
0.7353 Intermediate Similarity NPC472756
0.7347 Intermediate Similarity NPC230800
0.7347 Intermediate Similarity NPC126156
0.734 Intermediate Similarity NPC476805
0.7333 Intermediate Similarity NPC5103
0.7333 Intermediate Similarity NPC41551
0.7326 Intermediate Similarity NPC15499
0.7326 Intermediate Similarity NPC114727
0.7326 Intermediate Similarity NPC476355
0.7326 Intermediate Similarity NPC294434
0.7326 Intermediate Similarity NPC259599
0.7326 Intermediate Similarity NPC117746
0.7326 Intermediate Similarity NPC476590
0.732 Intermediate Similarity NPC476415
0.732 Intermediate Similarity NPC469632
0.732 Intermediate Similarity NPC476267
0.732 Intermediate Similarity NPC167219
0.732 Intermediate Similarity NPC81386
0.732 Intermediate Similarity NPC474035
0.732 Intermediate Similarity NPC140543
0.7312 Intermediate Similarity NPC469483
0.7312 Intermediate Similarity NPC309211
0.7312 Intermediate Similarity NPC122502
0.7312 Intermediate Similarity NPC261721
0.7312 Intermediate Similarity NPC469910
0.7312 Intermediate Similarity NPC477010
0.7312 Intermediate Similarity NPC112685
0.7308 Intermediate Similarity NPC275539
0.7308 Intermediate Similarity NPC189075
0.7303 Intermediate Similarity NPC270126
0.73 Intermediate Similarity NPC306856
0.73 Intermediate Similarity NPC174314
0.73 Intermediate Similarity NPC475949
0.7292 Intermediate Similarity NPC184463
0.7292 Intermediate Similarity NPC12172
0.7292 Intermediate Similarity NPC208886
0.7292 Intermediate Similarity NPC221282
0.7283 Intermediate Similarity NPC31086
0.7283 Intermediate Similarity NPC212363
0.7282 Intermediate Similarity NPC469607
0.7273 Intermediate Similarity NPC7563
0.7273 Intermediate Similarity NPC57744
0.7273 Intermediate Similarity NPC266842
0.7273 Intermediate Similarity NPC474343
0.7273 Intermediate Similarity NPC320630
0.7273 Intermediate Similarity NPC116177
0.7264 Intermediate Similarity NPC474750
0.7264 Intermediate Similarity NPC179798
0.7264 Intermediate Similarity NPC304180
0.7263 Intermediate Similarity NPC52198
0.7263 Intermediate Similarity NPC117405
0.7263 Intermediate Similarity NPC14901
0.7263 Intermediate Similarity NPC477017
0.7263 Intermediate Similarity NPC477011
0.7263 Intermediate Similarity NPC280612
0.7263 Intermediate Similarity NPC166919
0.7263 Intermediate Similarity NPC477016
0.7263 Intermediate Similarity NPC130359
0.7262 Intermediate Similarity NPC476591
0.7262 Intermediate Similarity NPC88877
0.7255 Intermediate Similarity NPC474581
0.7255 Intermediate Similarity NPC475321

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC473248 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
0.7604 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD5209 Approved
0.7188 Intermediate Similarity NPD5785 Approved
0.7021 Intermediate Similarity NPD1694 Approved
0.697 Remote Similarity NPD5282 Discontinued
0.6852 Remote Similarity NPD6371 Approved
0.6837 Remote Similarity NPD46 Approved
0.6837 Remote Similarity NPD6698 Approved
0.6771 Remote Similarity NPD5786 Approved
0.6768 Remote Similarity NPD7983 Approved
0.6729 Remote Similarity NPD7899 Clinical (unspecified phase)
0.67 Remote Similarity NPD5778 Approved
0.67 Remote Similarity NPD5779 Approved
0.6699 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6699 Remote Similarity NPD4225 Approved
0.6667 Remote Similarity NPD5363 Approved
0.6667 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6632 Remote Similarity NPD6110 Phase 1
0.6538 Remote Similarity NPD7638 Approved
0.6526 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6514 Remote Similarity NPD6686 Approved
0.65 Remote Similarity NPD7838 Discovery
0.6489 Remote Similarity NPD4252 Approved
0.6484 Remote Similarity NPD8039 Approved
0.6476 Remote Similarity NPD7639 Approved
0.6476 Remote Similarity NPD7640 Approved
0.6452 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6437 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6436 Remote Similarity NPD7637 Suspended
0.6436 Remote Similarity NPD6411 Approved
0.6429 Remote Similarity NPD4249 Approved
0.6392 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6399 Phase 3
0.6364 Remote Similarity NPD4250 Approved
0.6364 Remote Similarity NPD4251 Approved
0.6354 Remote Similarity NPD4270 Approved
0.6354 Remote Similarity NPD6435 Approved
0.6354 Remote Similarity NPD4269 Approved
0.6348 Remote Similarity NPD7115 Discovery
0.6346 Remote Similarity NPD7839 Suspended
0.6339 Remote Similarity NPD6650 Approved
0.6339 Remote Similarity NPD6649 Approved
0.633 Remote Similarity NPD6008 Approved
0.6325 Remote Similarity NPD6319 Approved
0.6286 Remote Similarity NPD7902 Approved
0.6283 Remote Similarity NPD6053 Discontinued
0.6273 Remote Similarity NPD5697 Approved
0.6271 Remote Similarity NPD8513 Phase 3
0.6271 Remote Similarity NPD8517 Approved
0.6271 Remote Similarity NPD8515 Approved
0.6271 Remote Similarity NPD8516 Approved
0.625 Remote Similarity NPD5955 Clinical (unspecified phase)
0.625 Remote Similarity NPD5369 Approved
0.625 Remote Similarity NPD7492 Approved
0.6238 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6238 Remote Similarity NPD6101 Approved
0.6238 Remote Similarity NPD1695 Approved
0.6228 Remote Similarity NPD4632 Approved
0.6216 Remote Similarity NPD6881 Approved
0.6216 Remote Similarity NPD6899 Approved
0.6216 Remote Similarity NPD6011 Approved
0.621 Remote Similarity NPD7260 Phase 2
0.6207 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6198 Remote Similarity NPD6616 Approved
0.6186 Remote Similarity NPD6054 Approved
0.617 Remote Similarity NPD4756 Discovery
0.6162 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6161 Remote Similarity NPD6373 Approved
0.6161 Remote Similarity NPD6014 Approved
0.6161 Remote Similarity NPD6012 Approved
0.6161 Remote Similarity NPD6372 Approved
0.6161 Remote Similarity NPD6013 Approved
0.6148 Remote Similarity NPD7078 Approved
0.6146 Remote Similarity NPD5368 Approved
0.6146 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6136 Remote Similarity NPD7331 Phase 2
0.6134 Remote Similarity NPD6015 Approved
0.6134 Remote Similarity NPD6016 Approved
0.6122 Remote Similarity NPD7154 Phase 3
0.6117 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6106 Remote Similarity NPD7290 Approved
0.6106 Remote Similarity NPD6883 Approved
0.6106 Remote Similarity NPD7102 Approved
0.6098 Remote Similarity NPD7736 Approved
0.6083 Remote Similarity NPD5988 Approved
0.6083 Remote Similarity NPD6370 Approved
0.6078 Remote Similarity NPD5370 Suspended
0.6071 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6068 Remote Similarity NPD6009 Approved
0.6053 Remote Similarity NPD6847 Approved
0.6053 Remote Similarity NPD6869 Approved
0.6053 Remote Similarity NPD6617 Approved
0.6053 Remote Similarity NPD8130 Phase 1
0.6053 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6036 Remote Similarity NPD6402 Approved
0.6036 Remote Similarity NPD7128 Approved
0.6036 Remote Similarity NPD5739 Approved
0.6036 Remote Similarity NPD6675 Approved
0.6033 Remote Similarity NPD7642 Approved
0.6018 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6016 Remote Similarity NPD8074 Phase 3
0.6 Remote Similarity NPD7900 Approved
0.6 Remote Similarity NPD6882 Approved
0.6 Remote Similarity NPD7748 Approved
0.6 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6 Remote Similarity NPD5983 Phase 2
0.6 Remote Similarity NPD8297 Approved
0.5982 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5982 Remote Similarity NPD5701 Approved
0.5979 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5969 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5965 Remote Similarity NPD4634 Approved
0.5963 Remote Similarity NPD5344 Discontinued
0.5962 Remote Similarity NPD5281 Approved
0.5962 Remote Similarity NPD6079 Approved
0.5962 Remote Similarity NPD5284 Approved
0.596 Remote Similarity NPD5362 Discontinued
0.5943 Remote Similarity NPD5695 Phase 3
0.5941 Remote Similarity NPD7334 Approved
0.5941 Remote Similarity NPD5330 Approved
0.5941 Remote Similarity NPD6684 Approved
0.5941 Remote Similarity NPD7521 Approved
0.5941 Remote Similarity NPD7146 Approved
0.5941 Remote Similarity NPD6409 Approved
0.5938 Remote Similarity NPD4268 Approved
0.5938 Remote Similarity NPD4271 Approved
0.5932 Remote Similarity NPD7500 Approved
0.5929 Remote Similarity NPD7320 Approved
0.5926 Remote Similarity NPD5696 Approved
0.592 Remote Similarity NPD7319 Approved
0.5917 Remote Similarity NPD6059 Approved
0.5913 Remote Similarity NPD2204 Approved
0.5909 Remote Similarity NPD5211 Phase 2
0.5909 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5909 Remote Similarity NPD7632 Discontinued
0.5906 Remote Similarity NPD6845 Suspended
0.5902 Remote Similarity NPD7604 Phase 2
0.5902 Remote Similarity NPD8328 Phase 3
0.5902 Remote Similarity NPD7830 Approved
0.5902 Remote Similarity NPD7829 Approved
0.5893 Remote Similarity NPD5048 Discontinued
0.5888 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5888 Remote Similarity NPD4697 Phase 3
0.5888 Remote Similarity NPD5221 Approved
0.5888 Remote Similarity NPD5222 Approved
0.5887 Remote Similarity NPD8293 Discontinued
0.5882 Remote Similarity NPD3573 Approved
0.5872 Remote Similarity NPD6648 Approved
0.5872 Remote Similarity NPD5286 Approved
0.5872 Remote Similarity NPD4696 Approved
0.5872 Remote Similarity NPD5285 Approved
0.5868 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5841 Remote Similarity NPD6412 Phase 2
0.5833 Remote Similarity NPD6083 Phase 2
0.5833 Remote Similarity NPD5173 Approved
0.5833 Remote Similarity NPD6084 Phase 2
0.5825 Remote Similarity NPD5737 Approved
0.5825 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5825 Remote Similarity NPD6903 Approved
0.5825 Remote Similarity NPD6672 Approved
0.5818 Remote Similarity NPD5223 Approved
0.5816 Remote Similarity NPD4822 Approved
0.5816 Remote Similarity NPD4821 Approved
0.5816 Remote Similarity NPD4820 Approved
0.5816 Remote Similarity NPD4819 Approved
0.581 Remote Similarity NPD5693 Phase 1
0.581 Remote Similarity NPD7515 Phase 2
0.5806 Remote Similarity NPD6336 Discontinued
0.5806 Remote Similarity NPD7507 Approved
0.5804 Remote Similarity NPD5141 Approved
0.5798 Remote Similarity NPD6317 Approved
0.5784 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5784 Remote Similarity NPD3618 Phase 1
0.5776 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5769 Remote Similarity NPD5328 Approved
0.5766 Remote Similarity NPD5225 Approved
0.5766 Remote Similarity NPD4633 Approved
0.5766 Remote Similarity NPD5226 Approved
0.5766 Remote Similarity NPD5224 Approved
0.5763 Remote Similarity NPD6010 Discontinued
0.575 Remote Similarity NPD6314 Approved
0.575 Remote Similarity NPD7641 Discontinued
0.575 Remote Similarity NPD6335 Approved
0.575 Remote Similarity NPD6313 Approved
0.5747 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5743 Remote Similarity NPD3666 Approved
0.5743 Remote Similarity NPD3133 Approved
0.5743 Remote Similarity NPD3665 Phase 1
0.5738 Remote Similarity NPD8444 Approved
0.5714 Remote Similarity NPD6274 Approved
0.5714 Remote Similarity NPD6647 Phase 2
0.5714 Remote Similarity NPD5175 Approved
0.5714 Remote Similarity NPD5174 Approved
0.5714 Remote Similarity NPD5207 Approved
0.5714 Remote Similarity NPD6868 Approved
0.5702 Remote Similarity NPD7100 Approved
0.5702 Remote Similarity NPD7101 Approved
0.57 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5688 Remote Similarity NPD4755 Approved
0.5686 Remote Similarity NPD1696 Phase 3

Structure

External Identifiers

PubChem CID   44406793
ChEMBL   CHEMBL383494
ZINC  

Physicochemical Properties

Molecular Weight:  304.17
ALogP:  2.1184
MLogP:  3
XLogP:  2.454
# Rotatable Bonds:  10
Polar Surface Area:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  22

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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