Natural Product: NPC118159

Natural Product ID:  NPC118159
Common Name:   3-Angeloyloxy-8-Acetoxy-10(14)-Oplopen-4-One
IUPAC Name:   [(2S,3R,3aR,4S,5R,7aR)-3-acetyl-5-acetyloxy-7-methylidene-4-propan-2-yl-1,2,3,3a,4,5,6,7a-octahydroinden-2-yl] (Z)-2-methylbut-2-enoate
Synonyms:  
Molecular Formula:   C22H32O5
Standard InCHIKey:  FDFXUUAZUMJPNJ-OZWCXVTBSA-N
Standard InCHI:  InChI=1S/C22H32O5/c1-8-12(4)22(25)27-18-10-16-13(5)9-17(26-15(7)24)19(11(2)3)21(16)20(18)14(6)23/h8,11,16-21H,5,9-10H2,1-4,6-7H3/b12-8-/t16-,17+,18-,19+,20-,21+/m0/s1
Canonical SMILES:  C/C=C(C(=O)O[C@H]1C[C@@H]2[C@@H]([C@H]1C(=O)C)[C@H](C(C)C)[C@@H](CC2=C)OC(=O)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
NPO16686 Robinsonecio gerberifolius Species Asteraceae Eukaryota PMID[12608854]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT148 Cell Line HCT-15 Homo sapiens IC50 = 43600 nM PubChem BioAssay data set
NPT83 Cell Line MCF7 Homo sapiens IC50 = 33900 nM PubChem BioAssay data set
NPT111 Cell Line K562 Homo sapiens IC50 = 13000 nM 24900585
NPT306 Cell Line PC-3 Homo sapiens IC50 = 78700 nM 17958396
NPT380 Cell Line U-251 Homo sapiens IC50 = 13000 nM DrugMatrix in vivo data: Pathology

  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 NPC118159 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
0.9468 High Similarity NPC475750
0.9149 High Similarity NPC471932
0.8632 High Similarity NPC470978
0.8632 High Similarity NPC470974
0.86 High Similarity NPC470975
0.86 High Similarity NPC103088
0.86 High Similarity NPC470979
0.8511 High Similarity NPC221282
0.8462 Intermediate Similarity NPC471933
0.8384 Intermediate Similarity NPC475099
0.835 Intermediate Similarity NPC471934
0.8298 Intermediate Similarity NPC288699
0.8269 Intermediate Similarity NPC179642
0.8241 Intermediate Similarity NPC470420
0.8125 Intermediate Similarity NPC470230
0.8 Intermediate Similarity NPC176845
0.7961 Intermediate Similarity NPC470297
0.7938 Intermediate Similarity NPC290651
0.7938 Intermediate Similarity NPC472953
0.7938 Intermediate Similarity NPC473944
0.7921 Intermediate Similarity NPC471413
0.7921 Intermediate Similarity NPC306856
0.7917 Intermediate Similarity NPC471043
0.79 Intermediate Similarity NPC2049
0.789 Intermediate Similarity NPC469794
0.789 Intermediate Similarity NPC190286
0.789 Intermediate Similarity NPC72772
0.7879 Intermediate Similarity NPC470229
0.7876 Intermediate Similarity NPC204812
0.787 Intermediate Similarity NPC472926
0.787 Intermediate Similarity NPC470120
0.7864 Intermediate Similarity NPC254202
0.7857 Intermediate Similarity NPC46570
0.7843 Intermediate Similarity NPC471412
0.7843 Intermediate Similarity NPC52899
0.7843 Intermediate Similarity NPC163963
0.7843 Intermediate Similarity NPC289148
0.7843 Intermediate Similarity NPC171759
0.7838 Intermediate Similarity NPC475520
0.7835 Intermediate Similarity NPC161638
0.783 Intermediate Similarity NPC475941
0.783 Intermediate Similarity NPC474901
0.7822 Intermediate Similarity NPC469986
0.7822 Intermediate Similarity NPC252295
0.7822 Intermediate Similarity NPC222011
0.7818 Intermediate Similarity NPC239273
0.781 Intermediate Similarity NPC472925
0.7807 Intermediate Similarity NPC241456
0.7807 Intermediate Similarity NPC32868
0.78 Intermediate Similarity NPC329910
0.7798 Intermediate Similarity NPC470953
0.7789 Intermediate Similarity NPC64153
0.7788 Intermediate Similarity NPC189616
0.7788 Intermediate Similarity NPC269642
0.7788 Intermediate Similarity NPC96268
0.7788 Intermediate Similarity NPC107493
0.7778 Intermediate Similarity NPC470697
0.7778 Intermediate Similarity NPC475118
0.7778 Intermediate Similarity NPC148463
0.7767 Intermediate Similarity NPC148628
0.7767 Intermediate Similarity NPC214946
0.7767 Intermediate Similarity NPC88203
0.7767 Intermediate Similarity NPC162973
0.7767 Intermediate Similarity NPC76866
0.7767 Intermediate Similarity NPC246736
0.7767 Intermediate Similarity NPC304832
0.7767 Intermediate Similarity NPC286519
0.7757 Intermediate Similarity NPC197428
0.7755 Intermediate Similarity NPC191339
0.7755 Intermediate Similarity NPC286341
0.7748 Intermediate Similarity NPC473720
0.7748 Intermediate Similarity NPC153440
0.7748 Intermediate Similarity NPC475372
0.7745 Intermediate Similarity NPC287676
0.7745 Intermediate Similarity NPC469551
0.7745 Intermediate Similarity NPC476933
0.7736 Intermediate Similarity NPC476802
0.7736 Intermediate Similarity NPC89171
0.7732 Intermediate Similarity NPC474679
0.7723 Intermediate Similarity NPC69385
0.7723 Intermediate Similarity NPC108475
0.7723 Intermediate Similarity NPC110937
0.7723 Intermediate Similarity NPC170143
0.7723 Intermediate Similarity NPC213947
0.7719 Intermediate Similarity NPC472768
0.7714 Intermediate Similarity NPC295366
0.7708 Intermediate Similarity NPC175293
0.77 Intermediate Similarity NPC470232
0.7692 Intermediate Similarity NPC36321
0.7692 Intermediate Similarity NPC87927
0.7692 Intermediate Similarity NPC159442
0.7685 Intermediate Similarity NPC470960
0.7679 Intermediate Similarity NPC5292
0.7679 Intermediate Similarity NPC312536
0.7679 Intermediate Similarity NPC472667
0.7679 Intermediate Similarity NPC476960
0.7679 Intermediate Similarity NPC475041
0.7672 Intermediate Similarity NPC287423
0.767 Intermediate Similarity NPC310981
0.767 Intermediate Similarity NPC472924
0.7664 Intermediate Similarity NPC474243
0.7658 Intermediate Similarity NPC472927
0.7658 Intermediate Similarity NPC476959
0.7653 Intermediate Similarity NPC152467
0.7647 Intermediate Similarity NPC78427
0.7647 Intermediate Similarity NPC474793
0.7647 Intermediate Similarity NPC471038
0.7647 Intermediate Similarity NPC16911
0.7636 Intermediate Similarity NPC238667
0.7632 Intermediate Similarity NPC170538
0.7624 Intermediate Similarity NPC111684
0.7624 Intermediate Similarity NPC29952
0.7624 Intermediate Similarity NPC58052
0.7624 Intermediate Similarity NPC307164
0.7619 Intermediate Similarity NPC98603
0.7615 Intermediate Similarity NPC475970
0.7611 Intermediate Similarity NPC4548
0.7611 Intermediate Similarity NPC476962
0.7611 Intermediate Similarity NPC474585
0.7611 Intermediate Similarity NPC476961
0.7611 Intermediate Similarity NPC79579
0.7604 Intermediate Similarity NPC469676
0.7604 Intermediate Similarity NPC474045
0.7604 Intermediate Similarity NPC261253
0.7604 Intermediate Similarity NPC220478
0.76 Intermediate Similarity NPC470385
0.76 Intermediate Similarity NPC47853
0.76 Intermediate Similarity NPC224410
0.76 Intermediate Similarity NPC474841
0.76 Intermediate Similarity NPC100257
0.76 Intermediate Similarity NPC473434
0.76 Intermediate Similarity NPC470386
0.76 Intermediate Similarity NPC471446
0.7596 Intermediate Similarity NPC22388
0.7596 Intermediate Similarity NPC170615
0.7589 Intermediate Similarity NPC113448
0.7579 Intermediate Similarity NPC30486
0.7576 Intermediate Similarity NPC165180
0.7573 Intermediate Similarity NPC470906
0.7573 Intermediate Similarity NPC471041
0.7573 Intermediate Similarity NPC117685
0.7573 Intermediate Similarity NPC476274
0.7573 Intermediate Similarity NPC47024
0.7573 Intermediate Similarity NPC251680
0.757 Intermediate Similarity NPC275539
0.757 Intermediate Similarity NPC189075
0.757 Intermediate Similarity NPC211224
0.757 Intermediate Similarity NPC61411
0.7568 Intermediate Similarity NPC148458
0.7568 Intermediate Similarity NPC176840
0.7568 Intermediate Similarity NPC470793
0.7568 Intermediate Similarity NPC196931
0.7568 Intermediate Similarity NPC476963
0.7565 Intermediate Similarity NPC55602
0.7565 Intermediate Similarity NPC11895
0.7565 Intermediate Similarity NPC469789
0.7549 Intermediate Similarity NPC96839
0.7549 Intermediate Similarity NPC38530
0.7549 Intermediate Similarity NPC474343
0.7549 Intermediate Similarity NPC47834
0.7549 Intermediate Similarity NPC253826
0.7549 Intermediate Similarity NPC84335
0.7547 Intermediate Similarity NPC37600
0.7547 Intermediate Similarity NPC278628
0.7547 Intermediate Similarity NPC470980
0.7547 Intermediate Similarity NPC231530
0.7547 Intermediate Similarity NPC469874
0.7547 Intermediate Similarity NPC475571
0.7545 Intermediate Similarity NPC962
0.7545 Intermediate Similarity NPC52634
0.7544 Intermediate Similarity NPC310511
0.7542 Intermediate Similarity NPC231529
0.7542 Intermediate Similarity NPC221414
0.7542 Intermediate Similarity NPC472770
0.7525 Intermediate Similarity NPC281134
0.7525 Intermediate Similarity NPC33473
0.7524 Intermediate Similarity NPC475526
0.7524 Intermediate Similarity NPC329345
0.7524 Intermediate Similarity NPC470310
0.7524 Intermediate Similarity NPC470954
0.7524 Intermediate Similarity NPC473283
0.7524 Intermediate Similarity NPC474775
0.7524 Intermediate Similarity NPC216114
0.7524 Intermediate Similarity NPC469985
0.7524 Intermediate Similarity NPC95899
0.7523 Intermediate Similarity NPC174471
0.7523 Intermediate Similarity NPC474871
0.7523 Intermediate Similarity NPC260786
0.7523 Intermediate Similarity NPC96739
0.7523 Intermediate Similarity NPC94650
0.7523 Intermediate Similarity NPC475495
0.7523 Intermediate Similarity NPC470281
0.7523 Intermediate Similarity NPC472928
0.7522 Intermediate Similarity NPC472933
0.7522 Intermediate Similarity NPC270850
0.7522 Intermediate Similarity NPC305260
0.75 Intermediate Similarity NPC475657
0.75 Intermediate Similarity NPC79117
0.75 Intermediate Similarity NPC112457
0.75 Intermediate Similarity NPC476223

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC118159 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
0.7714 Intermediate Similarity NPD6008 Approved
0.7647 Intermediate Similarity NPD7638 Approved
0.7573 Intermediate Similarity NPD7639 Approved
0.7573 Intermediate Similarity NPD7640 Approved
0.73 Intermediate Similarity NPD5785 Approved
0.7297 Intermediate Similarity NPD6053 Discontinued
0.7248 Intermediate Similarity NPD6881 Approved
0.7248 Intermediate Similarity NPD6899 Approved
0.7245 Intermediate Similarity NPD5330 Approved
0.7245 Intermediate Similarity NPD7521 Approved
0.7245 Intermediate Similarity NPD7334 Approved
0.7245 Intermediate Similarity NPD6684 Approved
0.7245 Intermediate Similarity NPD7146 Approved
0.7245 Intermediate Similarity NPD6409 Approved
0.7222 Intermediate Similarity NPD5739 Approved
0.7222 Intermediate Similarity NPD6402 Approved
0.7222 Intermediate Similarity NPD7128 Approved
0.7222 Intermediate Similarity NPD6675 Approved
0.7193 Intermediate Similarity NPD7115 Discovery
0.7188 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD5697 Approved
0.7155 Intermediate Similarity NPD6319 Approved
0.7143 Intermediate Similarity NPD5363 Approved
0.7117 Intermediate Similarity NPD7290 Approved
0.7117 Intermediate Similarity NPD6883 Approved
0.7117 Intermediate Similarity NPD7102 Approved
0.7107 Intermediate Similarity NPD7319 Approved
0.71 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD6903 Approved
0.7091 Intermediate Similarity NPD7320 Approved
0.7091 Intermediate Similarity NPD6011 Approved
0.708 Intermediate Similarity NPD4632 Approved
0.7071 Intermediate Similarity NPD5786 Approved
0.7059 Intermediate Similarity NPD5693 Phase 1
0.7059 Intermediate Similarity NPD7492 Approved
0.7054 Intermediate Similarity NPD6847 Approved
0.7054 Intermediate Similarity NPD6649 Approved
0.7054 Intermediate Similarity NPD6650 Approved
0.7054 Intermediate Similarity NPD8130 Phase 1
0.7054 Intermediate Similarity NPD6617 Approved
0.7054 Intermediate Similarity NPD6869 Approved
0.7027 Intermediate Similarity NPD6012 Approved
0.7027 Intermediate Similarity NPD6373 Approved
0.7027 Intermediate Similarity NPD6014 Approved
0.7027 Intermediate Similarity NPD6013 Approved
0.7027 Intermediate Similarity NPD6372 Approved
0.7019 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6054 Approved
0.7 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7507 Approved
0.7 Intermediate Similarity NPD5701 Approved
0.7 Intermediate Similarity NPD6616 Approved
0.6991 Remote Similarity NPD8297 Approved
0.6991 Remote Similarity NPD6882 Approved
0.699 Remote Similarity NPD5778 Approved
0.699 Remote Similarity NPD5779 Approved
0.6981 Remote Similarity NPD4225 Approved
0.697 Remote Similarity NPD1694 Approved
0.6964 Remote Similarity NPD6371 Approved
0.6944 Remote Similarity NPD7632 Discontinued
0.6942 Remote Similarity NPD7078 Approved
0.6931 Remote Similarity NPD6672 Approved
0.6931 Remote Similarity NPD5737 Approved
0.6903 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6009 Approved
0.6893 Remote Similarity NPD6079 Approved
0.6891 Remote Similarity NPD6370 Approved
0.6885 Remote Similarity NPD7736 Approved
0.6864 Remote Similarity NPD6059 Approved
0.6863 Remote Similarity NPD1695 Approved
0.6863 Remote Similarity NPD6673 Approved
0.6863 Remote Similarity NPD6080 Approved
0.6863 Remote Similarity NPD5328 Approved
0.6863 Remote Similarity NPD6904 Approved
0.6837 Remote Similarity NPD4270 Approved
0.6837 Remote Similarity NPD4269 Approved
0.6833 Remote Similarity NPD7604 Phase 2
0.6827 Remote Similarity NPD6399 Phase 3
0.6814 Remote Similarity NPD4634 Approved
0.6807 Remote Similarity NPD5983 Phase 2
0.6807 Remote Similarity NPD6016 Approved
0.6807 Remote Similarity NPD6015 Approved
0.6803 Remote Similarity NPD8293 Discontinued
0.6789 Remote Similarity NPD5211 Phase 2
0.6768 Remote Similarity NPD5362 Discontinued
0.6759 Remote Similarity NPD5286 Approved
0.6759 Remote Similarity NPD5285 Approved
0.6759 Remote Similarity NPD4696 Approved
0.675 Remote Similarity NPD5988 Approved
0.6735 Remote Similarity NPD5369 Approved
0.6731 Remote Similarity NPD6050 Approved
0.6729 Remote Similarity NPD6084 Phase 2
0.6729 Remote Similarity NPD4755 Approved
0.6729 Remote Similarity NPD6083 Phase 2
0.6721 Remote Similarity NPD6336 Discontinued
0.6699 Remote Similarity NPD6051 Approved
0.6698 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6698 Remote Similarity NPD5695 Phase 3
0.6697 Remote Similarity NPD5223 Approved
0.6695 Remote Similarity NPD6335 Approved
0.6667 Remote Similarity NPD6274 Approved
0.6667 Remote Similarity NPD6435 Approved
0.6667 Remote Similarity NPD5141 Approved
0.6667 Remote Similarity NPD3573 Approved
0.6667 Remote Similarity NPD5209 Approved
0.6639 Remote Similarity NPD7101 Approved
0.6639 Remote Similarity NPD7100 Approved
0.6637 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6637 Remote Similarity NPD6686 Approved
0.6636 Remote Similarity NPD5221 Approved
0.6636 Remote Similarity NPD5224 Approved
0.6636 Remote Similarity NPD5226 Approved
0.6636 Remote Similarity NPD5222 Approved
0.6636 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6636 Remote Similarity NPD5225 Approved
0.6636 Remote Similarity NPD4633 Approved
0.6635 Remote Similarity NPD6698 Approved
0.6635 Remote Similarity NPD46 Approved
0.6635 Remote Similarity NPD5692 Phase 3
0.6634 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6633 Remote Similarity NPD4252 Approved
0.661 Remote Similarity NPD6317 Approved
0.6606 Remote Similarity NPD4700 Approved
0.6606 Remote Similarity NPD6648 Approved
0.6604 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6604 Remote Similarity NPD6001 Approved
0.6604 Remote Similarity NPD7900 Approved
0.6604 Remote Similarity NPD7748 Approved
0.6602 Remote Similarity NPD5208 Approved
0.6577 Remote Similarity NPD5175 Approved
0.6577 Remote Similarity NPD5174 Approved
0.6574 Remote Similarity NPD5173 Approved
0.6571 Remote Similarity NPD8034 Phase 2
0.6571 Remote Similarity NPD5694 Approved
0.6571 Remote Similarity NPD8035 Phase 2
0.6571 Remote Similarity NPD7637 Suspended
0.6569 Remote Similarity NPD6098 Approved
0.6555 Remote Similarity NPD6313 Approved
0.6555 Remote Similarity NPD6314 Approved
0.6545 Remote Similarity NPD5344 Discontinued
0.6538 Remote Similarity NPD6101 Approved
0.6538 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6868 Approved
0.6514 Remote Similarity NPD5696 Approved
0.6509 Remote Similarity NPD4202 Approved
0.6481 Remote Similarity NPD4697 Phase 3
0.648 Remote Similarity NPD6033 Approved
0.6476 Remote Similarity NPD5207 Approved
0.6471 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6465 Remote Similarity NPD5368 Approved
0.6429 Remote Similarity NPD4754 Approved
0.6422 Remote Similarity NPD7902 Approved
0.6417 Remote Similarity NPD7328 Approved
0.6417 Remote Similarity NPD7327 Approved
0.6415 Remote Similarity NPD7515 Phase 2
0.6415 Remote Similarity NPD6411 Approved
0.6415 Remote Similarity NPD7983 Approved
0.6408 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6408 Remote Similarity NPD3618 Phase 1
0.6404 Remote Similarity NPD6412 Phase 2
0.6404 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6393 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6393 Remote Similarity NPD6908 Approved
0.6393 Remote Similarity NPD6909 Approved
0.6393 Remote Similarity NPD8033 Approved
0.6373 Remote Similarity NPD3133 Approved
0.6373 Remote Similarity NPD3665 Phase 1
0.6373 Remote Similarity NPD4786 Approved
0.6373 Remote Similarity NPD3666 Approved
0.6364 Remote Similarity NPD7516 Approved
0.6348 Remote Similarity NPD4730 Approved
0.6348 Remote Similarity NPD4729 Approved
0.6348 Remote Similarity NPD5128 Approved
0.6346 Remote Similarity NPD4251 Approved
0.6346 Remote Similarity NPD4250 Approved
0.6328 Remote Similarity NPD7260 Phase 2
0.6316 Remote Similarity NPD4767 Approved
0.6316 Remote Similarity NPD4768 Approved
0.6311 Remote Similarity NPD8294 Approved
0.6311 Remote Similarity NPD8377 Approved
0.63 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6293 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6288 Remote Similarity NPD6333 Approved
0.6288 Remote Similarity NPD6334 Approved
0.6275 Remote Similarity NPD5331 Approved
0.6275 Remote Similarity NPD5332 Approved
0.6275 Remote Similarity NPD4788 Approved
0.6275 Remote Similarity NPD7154 Phase 3
0.6263 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6262 Remote Similarity NPD5281 Approved
0.6262 Remote Similarity NPD5284 Approved
0.626 Remote Similarity NPD7503 Approved
0.626 Remote Similarity NPD8380 Approved
0.626 Remote Similarity NPD8378 Approved
0.626 Remote Similarity NPD8296 Approved
0.626 Remote Similarity NPD8335 Approved
0.626 Remote Similarity NPD8379 Approved
0.625 Remote Similarity NPD4249 Approved
0.6239 Remote Similarity NPD5248 Approved

Structure

External Identifiers

PubChem CID   643686
ChEMBL   CHEMBL514283
ZINC  

Physicochemical Properties

Molecular Weight:  376.22
ALogP:  1.7101
MLogP:  3.33
XLogP:  3.455
# Rotatable Bonds:  13
Polar Surface Area:  69.67
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  27

Download Data

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