Natural Product: NPC474979

Natural Product ID:  NPC474979
Common Name:   19-Malonyloxy-Entisopimara-8(9),15-Diene
IUPAC Name:   3-[[(1R,4aR,7R,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthren-1-yl]oxy]-3-oxopropanoic acid
Synonyms:  
Molecular Formula:   C22H32O4
Standard InCHIKey:  NKRZOAWZBYVTMB-KVJIRVJXSA-N
Standard InCHI:  InChI=1S/C22H32O4/c1-5-20(2)12-9-16-15(14-20)7-8-17-21(16,3)10-6-11-22(17,4)26-19(25)13-18(23)24/h5,17H,1,6-14H2,2-4H3,(H,23,24)/t17-,20+,21-,22+/m0/s1
Canonical SMILES:  C=C[C@]1(C)CCC2=C(C1)CC[C@H]1[C@@]2(C)CCC[C@@]1(C)OC(=O)CC(=O)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
NPO33152 calceolaria pinifolia Species Calceolariaceae Eukaryota Aerial parts 46 km west of Puesto de Gendarmeria in the province of San Juan, Argentina (30°21'S; 69°40'W) 1997-JAN PMID[12608857]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 4 ug/ml 21377877
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 16 ug/ml DrugMatrix in vitro pharmacology data
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 8 ug/ml 12350142
NPT19 Organism Escherichia coli Escherichia coli MIC = 32 ug/ml 23206866

  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 NPC474979 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
0.9615 High Similarity NPC473592
0.9481 High Similarity NPC474978
0.9114 High Similarity NPC476101
0.8235 Intermediate Similarity NPC76333
0.8049 Intermediate Similarity NPC321514
0.8046 Intermediate Similarity NPC171722
0.8 Intermediate Similarity NPC474789
0.8 Intermediate Similarity NPC52108
0.7976 Intermediate Similarity NPC142163
0.7976 Intermediate Similarity NPC327002
0.7952 Intermediate Similarity NPC100906
0.7935 Intermediate Similarity NPC120708
0.7931 Intermediate Similarity NPC262085
0.7931 Intermediate Similarity NPC73038
0.7912 Intermediate Similarity NPC78580
0.7912 Intermediate Similarity NPC184006
0.7912 Intermediate Similarity NPC23621
0.7907 Intermediate Similarity NPC156981
0.7889 Intermediate Similarity NPC477574
0.7882 Intermediate Similarity NPC15910
0.7865 Intermediate Similarity NPC469866
0.7865 Intermediate Similarity NPC471342
0.7865 Intermediate Similarity NPC59682
0.7857 Intermediate Similarity NPC269791
0.7857 Intermediate Similarity NPC37038
0.7841 Intermediate Similarity NPC131329
0.7841 Intermediate Similarity NPC245004
0.7831 Intermediate Similarity NPC179028
0.7826 Intermediate Similarity NPC23241
0.7826 Intermediate Similarity NPC195715
0.7826 Intermediate Similarity NPC473648
0.7791 Intermediate Similarity NPC477373
0.7791 Intermediate Similarity NPC476100
0.7791 Intermediate Similarity NPC476927
0.7778 Intermediate Similarity NPC148414
0.7778 Intermediate Similarity NPC175628
0.7778 Intermediate Similarity NPC71152
0.7778 Intermediate Similarity NPC111585
0.7738 Intermediate Similarity NPC327674
0.7738 Intermediate Similarity NPC231431
0.7727 Intermediate Similarity NPC474970
0.7727 Intermediate Similarity NPC325594
0.7711 Intermediate Similarity NPC132542
0.7711 Intermediate Similarity NPC283619
0.7692 Intermediate Similarity NPC36491
0.7692 Intermediate Similarity NPC471588
0.7692 Intermediate Similarity NPC26888
0.7692 Intermediate Similarity NPC228784
0.7692 Intermediate Similarity NPC6255
0.7692 Intermediate Similarity NPC288833
0.7692 Intermediate Similarity NPC282616
0.7692 Intermediate Similarity NPC155120
0.7692 Intermediate Similarity NPC324341
0.7692 Intermediate Similarity NPC966
0.7683 Intermediate Similarity NPC279666
0.7683 Intermediate Similarity NPC192540
0.7674 Intermediate Similarity NPC256112
0.7674 Intermediate Similarity NPC73882
0.7667 Intermediate Similarity NPC474889
0.7667 Intermediate Similarity NPC30522
0.7667 Intermediate Similarity NPC474700
0.7667 Intermediate Similarity NPC474570
0.7667 Intermediate Similarity NPC20946
0.7667 Intermediate Similarity NPC16265
0.766 Intermediate Similarity NPC26413
0.7647 Intermediate Similarity NPC477057
0.7647 Intermediate Similarity NPC104545
0.7619 Intermediate Similarity NPC280654
0.7619 Intermediate Similarity NPC260385
0.7619 Intermediate Similarity NPC110094
0.7614 Intermediate Similarity NPC476602
0.7614 Intermediate Similarity NPC191965
0.7609 Intermediate Similarity NPC131840
0.7609 Intermediate Similarity NPC86368
0.7604 Intermediate Similarity NPC473514
0.759 Intermediate Similarity NPC69143
0.759 Intermediate Similarity NPC104806
0.759 Intermediate Similarity NPC309399
0.7582 Intermediate Similarity NPC113989
0.7582 Intermediate Similarity NPC473269
0.7582 Intermediate Similarity NPC471896
0.7582 Intermediate Similarity NPC120840
0.7582 Intermediate Similarity NPC86372
0.7582 Intermediate Similarity NPC474728
0.7582 Intermediate Similarity NPC172361
0.7579 Intermediate Similarity NPC164349
0.7561 Intermediate Similarity NPC476046
0.7561 Intermediate Similarity NPC161923
0.7561 Intermediate Similarity NPC103958
0.7561 Intermediate Similarity NPC283908
0.7561 Intermediate Similarity NPC241854
0.7561 Intermediate Similarity NPC251970
0.7561 Intermediate Similarity NPC183503
0.7558 Intermediate Similarity NPC20096
0.7558 Intermediate Similarity NPC48673
0.7558 Intermediate Similarity NPC142244
0.7558 Intermediate Similarity NPC38350
0.7558 Intermediate Similarity NPC201912
0.7558 Intermediate Similarity NPC278459
0.7556 Intermediate Similarity NPC72397
0.7556 Intermediate Similarity NPC24816
0.7553 Intermediate Similarity NPC98874
0.7553 Intermediate Similarity NPC132824
0.7553 Intermediate Similarity NPC269492
0.7553 Intermediate Similarity NPC327788
0.7531 Intermediate Similarity NPC160817
0.7531 Intermediate Similarity NPC110799
0.7529 Intermediate Similarity NPC199595
0.7528 Intermediate Similarity NPC476104
0.7528 Intermediate Similarity NPC137306
0.7528 Intermediate Similarity NPC475181
0.7528 Intermediate Similarity NPC324063
0.7528 Intermediate Similarity NPC475753
0.7528 Intermediate Similarity NPC84121
0.7527 Intermediate Similarity NPC80365
0.7527 Intermediate Similarity NPC222047
0.7527 Intermediate Similarity NPC148964
0.7526 Intermediate Similarity NPC473788
0.7526 Intermediate Similarity NPC475558
0.75 Intermediate Similarity NPC107039
0.75 Intermediate Similarity NPC470590
0.75 Intermediate Similarity NPC297265
0.75 Intermediate Similarity NPC471899
0.75 Intermediate Similarity NPC60755
0.75 Intermediate Similarity NPC77099
0.75 Intermediate Similarity NPC471897
0.75 Intermediate Similarity NPC475156
0.75 Intermediate Similarity NPC285184
0.75 Intermediate Similarity NPC473576
0.75 Intermediate Similarity NPC476417
0.7474 Intermediate Similarity NPC21728
0.7474 Intermediate Similarity NPC473456
0.7474 Intermediate Similarity NPC89225
0.7473 Intermediate Similarity NPC270768
0.7473 Intermediate Similarity NPC234346
0.7473 Intermediate Similarity NPC59263
0.7473 Intermediate Similarity NPC61543
0.7473 Intermediate Similarity NPC97577
0.7473 Intermediate Similarity NPC475921
0.7473 Intermediate Similarity NPC121798
0.7473 Intermediate Similarity NPC263393
0.7473 Intermediate Similarity NPC127689
0.7473 Intermediate Similarity NPC225585
0.7473 Intermediate Similarity NPC474704
0.7473 Intermediate Similarity NPC130520
0.7473 Intermediate Similarity NPC293048
0.7471 Intermediate Similarity NPC260956
0.7471 Intermediate Similarity NPC2524
0.7471 Intermediate Similarity NPC286786
0.7447 Intermediate Similarity NPC148523
0.7447 Intermediate Similarity NPC777
0.7447 Intermediate Similarity NPC171395
0.7444 Intermediate Similarity NPC187376
0.7444 Intermediate Similarity NPC158141
0.7444 Intermediate Similarity NPC159046
0.7444 Intermediate Similarity NPC96496
0.7444 Intermediate Similarity NPC233836
0.7444 Intermediate Similarity NPC231599
0.7444 Intermediate Similarity NPC173089
0.7444 Intermediate Similarity NPC166857
0.7442 Intermediate Similarity NPC26139
0.7436 Intermediate Similarity NPC474768
0.7423 Intermediate Similarity NPC323441
0.7423 Intermediate Similarity NPC476888
0.7423 Intermediate Similarity NPC93744
0.7419 Intermediate Similarity NPC118490
0.7419 Intermediate Similarity NPC38232
0.7419 Intermediate Similarity NPC298554
0.7416 Intermediate Similarity NPC471344
0.7416 Intermediate Similarity NPC474537
0.7416 Intermediate Similarity NPC164424
0.7412 Intermediate Similarity NPC74410
0.7412 Intermediate Similarity NPC4827
0.7396 Intermediate Similarity NPC174663
0.7391 Intermediate Similarity NPC469400
0.7391 Intermediate Similarity NPC111110
0.7391 Intermediate Similarity NPC470589
0.7391 Intermediate Similarity NPC130278
0.7391 Intermediate Similarity NPC126369
0.7386 Intermediate Similarity NPC200752
0.7386 Intermediate Similarity NPC69279
0.7386 Intermediate Similarity NPC23748
0.7386 Intermediate Similarity NPC132386
0.7386 Intermediate Similarity NPC49208
0.7386 Intermediate Similarity NPC83569
0.7381 Intermediate Similarity NPC89294
0.7381 Intermediate Similarity NPC899
0.7381 Intermediate Similarity NPC180886
0.7375 Intermediate Similarity NPC94192
0.7368 Intermediate Similarity NPC327179
0.7368 Intermediate Similarity NPC167193
0.7368 Intermediate Similarity NPC469528
0.7368 Intermediate Similarity NPC472806
0.7368 Intermediate Similarity NPC201657
0.7368 Intermediate Similarity NPC471153
0.7368 Intermediate Similarity NPC469369
0.7363 Intermediate Similarity NPC242864
0.7363 Intermediate Similarity NPC1753
0.7363 Intermediate Similarity NPC474511
0.7363 Intermediate Similarity NPC246708

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC474979 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
0.7692 Intermediate Similarity NPD6411 Approved
0.7473 Intermediate Similarity NPD6101 Approved
0.7473 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD7748 Approved
0.7333 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD5695 Phase 3
0.7253 Intermediate Similarity NPD3573 Approved
0.7128 Intermediate Similarity NPD5284 Approved
0.7128 Intermediate Similarity NPD5281 Approved
0.7128 Intermediate Similarity NPD7515 Phase 2
0.7126 Intermediate Similarity NPD7645 Phase 2
0.7113 Intermediate Similarity NPD6083 Phase 2
0.7113 Intermediate Similarity NPD7902 Approved
0.7113 Intermediate Similarity NPD6084 Phase 2
0.7097 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD5779 Approved
0.7053 Intermediate Similarity NPD6399 Phase 3
0.7053 Intermediate Similarity NPD5778 Approved
0.699 Remote Similarity NPD6881 Approved
0.699 Remote Similarity NPD6899 Approved
0.6961 Remote Similarity NPD5739 Approved
0.6961 Remote Similarity NPD7128 Approved
0.6961 Remote Similarity NPD6675 Approved
0.6961 Remote Similarity NPD6402 Approved
0.6957 Remote Similarity NPD6098 Approved
0.6947 Remote Similarity NPD6050 Approved
0.6947 Remote Similarity NPD5694 Approved
0.6941 Remote Similarity NPD4785 Approved
0.6941 Remote Similarity NPD4784 Approved
0.6932 Remote Similarity NPD4195 Approved
0.6915 Remote Similarity NPD6673 Approved
0.6915 Remote Similarity NPD6904 Approved
0.6915 Remote Similarity NPD6080 Approved
0.6907 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4243 Approved
0.6893 Remote Similarity NPD5697 Approved
0.6869 Remote Similarity NPD5696 Approved
0.6869 Remote Similarity NPD7638 Approved
0.6869 Remote Similarity NPD4225 Approved
0.6857 Remote Similarity NPD6883 Approved
0.6857 Remote Similarity NPD7290 Approved
0.6857 Remote Similarity NPD7102 Approved
0.6854 Remote Similarity NPD7525 Registered
0.6842 Remote Similarity NPD5692 Phase 3
0.6842 Remote Similarity NPD5207 Approved
0.6827 Remote Similarity NPD7320 Approved
0.6809 Remote Similarity NPD6672 Approved
0.6809 Remote Similarity NPD5737 Approved
0.6804 Remote Similarity NPD7900 Approved
0.6804 Remote Similarity NPD7901 Clinical (unspecified phase)
0.68 Remote Similarity NPD7640 Approved
0.68 Remote Similarity NPD7639 Approved
0.6792 Remote Similarity NPD6650 Approved
0.6792 Remote Similarity NPD6617 Approved
0.6792 Remote Similarity NPD6847 Approved
0.6792 Remote Similarity NPD6869 Approved
0.6792 Remote Similarity NPD8130 Phase 1
0.6792 Remote Similarity NPD6649 Approved
0.6789 Remote Similarity NPD7115 Discovery
0.6774 Remote Similarity NPD5690 Phase 2
0.6774 Remote Similarity NPD6409 Approved
0.6774 Remote Similarity NPD6684 Approved
0.6774 Remote Similarity NPD5330 Approved
0.6774 Remote Similarity NPD7521 Approved
0.6774 Remote Similarity NPD7146 Approved
0.6774 Remote Similarity NPD7334 Approved
0.6771 Remote Similarity NPD7637 Suspended
0.6762 Remote Similarity NPD6373 Approved
0.6762 Remote Similarity NPD6372 Approved
0.6762 Remote Similarity NPD6013 Approved
0.6762 Remote Similarity NPD6014 Approved
0.6762 Remote Similarity NPD6012 Approved
0.6737 Remote Similarity NPD6051 Approved
0.6731 Remote Similarity NPD5701 Approved
0.6729 Remote Similarity NPD8297 Approved
0.6729 Remote Similarity NPD6882 Approved
0.6703 Remote Similarity NPD4221 Approved
0.6703 Remote Similarity NPD4223 Phase 3
0.6667 Remote Similarity NPD4695 Discontinued
0.6667 Remote Similarity NPD7614 Phase 1
0.6667 Remote Similarity NPD5329 Approved
0.6667 Remote Similarity NPD6011 Approved
0.6633 Remote Similarity NPD6001 Approved
0.6632 Remote Similarity NPD6903 Approved
0.6632 Remote Similarity NPD5208 Approved
0.6632 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6598 Remote Similarity NPD6079 Approved
0.6598 Remote Similarity NPD8034 Phase 2
0.6598 Remote Similarity NPD5693 Phase 1
0.6598 Remote Similarity NPD8035 Phase 2
0.6596 Remote Similarity NPD4623 Approved
0.6596 Remote Similarity NPD4694 Approved
0.6596 Remote Similarity NPD5280 Approved
0.6596 Remote Similarity NPD3618 Phase 1
0.6596 Remote Similarity NPD4519 Discontinued
0.6593 Remote Similarity NPD4139 Approved
0.6593 Remote Similarity NPD4692 Approved
0.6566 Remote Similarity NPD5654 Approved
0.6562 Remote Similarity NPD5328 Approved
0.6562 Remote Similarity NPD4753 Phase 2
0.6559 Remote Similarity NPD4197 Approved
0.6559 Remote Similarity NPD4786 Approved
0.6522 Remote Similarity NPD3667 Approved
0.6509 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6489 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6489 Remote Similarity NPD1694 Approved
0.6481 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6477 Remote Similarity NPD5275 Approved
0.6477 Remote Similarity NPD7339 Approved
0.6477 Remote Similarity NPD6942 Approved
0.6477 Remote Similarity NPD4190 Phase 3
0.6471 Remote Similarity NPD5285 Approved
0.6471 Remote Similarity NPD5286 Approved
0.6471 Remote Similarity NPD4696 Approved
0.646 Remote Similarity NPD6319 Approved
0.6449 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6444 Remote Similarity NPD3617 Approved
0.6436 Remote Similarity NPD4755 Approved
0.6436 Remote Similarity NPD5959 Approved
0.6421 Remote Similarity NPD4689 Approved
0.6421 Remote Similarity NPD4693 Phase 3
0.6421 Remote Similarity NPD4688 Approved
0.6421 Remote Similarity NPD5205 Approved
0.6421 Remote Similarity NPD4690 Approved
0.6421 Remote Similarity NPD4138 Approved
0.6404 Remote Similarity NPD3701 Clinical (unspecified phase)
0.64 Remote Similarity NPD5210 Approved
0.64 Remote Similarity NPD4629 Approved
0.6383 Remote Similarity NPD3666 Approved
0.6383 Remote Similarity NPD3133 Approved
0.6383 Remote Similarity NPD3665 Phase 1
0.6379 Remote Similarity NPD7492 Approved
0.6372 Remote Similarity NPD7100 Approved
0.6372 Remote Similarity NPD7101 Approved
0.6364 Remote Similarity NPD4202 Approved
0.6346 Remote Similarity NPD7632 Discontinued
0.6346 Remote Similarity NPD4633 Approved
0.6346 Remote Similarity NPD5224 Approved
0.6346 Remote Similarity NPD5211 Phase 2
0.6346 Remote Similarity NPD5225 Approved
0.6346 Remote Similarity NPD5226 Approved
0.6344 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5222 Approved
0.6337 Remote Similarity NPD5221 Approved
0.6337 Remote Similarity NPD7732 Phase 3
0.6325 Remote Similarity NPD6616 Approved
0.6316 Remote Similarity NPD6054 Approved
0.6311 Remote Similarity NPD4700 Approved
0.6304 Remote Similarity NPD4748 Discontinued
0.63 Remote Similarity NPD5707 Approved
0.6296 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6292 Remote Similarity NPD8264 Approved
0.6286 Remote Similarity NPD5175 Approved
0.6286 Remote Similarity NPD5174 Approved
0.6283 Remote Similarity NPD6335 Approved
0.6277 Remote Similarity NPD6695 Phase 3
0.6275 Remote Similarity NPD5173 Approved
0.6271 Remote Similarity NPD7078 Approved
0.625 Remote Similarity NPD5223 Approved
0.625 Remote Similarity NPD5279 Phase 3
0.625 Remote Similarity NPD6274 Approved
0.625 Remote Similarity NPD6868 Approved
0.6239 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6239 Remote Similarity NPD4634 Approved
0.6237 Remote Similarity NPD5369 Approved
0.6226 Remote Similarity NPD5141 Approved
0.6218 Remote Similarity NPD7736 Approved
0.6216 Remote Similarity NPD4632 Approved
0.6211 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6211 Remote Similarity NPD3668 Phase 3
0.6207 Remote Similarity NPD6370 Approved
0.62 Remote Similarity NPD5133 Approved
0.6195 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6195 Remote Similarity NPD6317 Approved
0.618 Remote Similarity NPD6926 Approved
0.618 Remote Similarity NPD6924 Approved
0.6176 Remote Similarity NPD4697 Phase 3
0.6174 Remote Similarity NPD6059 Approved
0.6168 Remote Similarity NPD6008 Approved
0.6162 Remote Similarity NPD4096 Approved
0.6154 Remote Similarity NPD6404 Discontinued
0.6154 Remote Similarity NPD8328 Phase 3
0.614 Remote Similarity NPD6313 Approved
0.614 Remote Similarity NPD6314 Approved
0.6134 Remote Similarity NPD8293 Discontinued
0.6132 Remote Similarity NPD6052 Approved
0.6122 Remote Similarity NPD4518 Approved
0.6121 Remote Similarity NPD6908 Approved
0.6121 Remote Similarity NPD6015 Approved
0.6121 Remote Similarity NPD6909 Approved
0.6121 Remote Similarity NPD7503 Approved
0.6121 Remote Similarity NPD6016 Approved
0.6111 Remote Similarity NPD6412 Phase 2
0.6111 Remote Similarity NPD6614 Approved
0.6111 Remote Similarity NPD8039 Approved
0.6095 Remote Similarity NPD5344 Discontinued
0.6068 Remote Similarity NPD5988 Approved
0.6055 Remote Similarity NPD4729 Approved
0.6055 Remote Similarity NPD4730 Approved

Structure

External Identifiers

PubChem CID   44566221
ChEMBL   CHEMBL490701
ZINC  

Physicochemical Properties

Molecular Weight:  360.23
ALogP:  2.0817
MLogP:  3.44
XLogP:  5.593
# Rotatable Bonds:  9
Polar Surface Area:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  26

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs