Natural Product: NPC474978

Natural Product ID:  NPC474978
Common Name:   19-Methylmalonyloxy-Ent-Isopimara-8(9),15-Diene
IUPAC Name:   3-O-[(1R,4aR,7R,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthren-1-yl] 1-O-methyl propanedioate
Synonyms:  
Molecular Formula:   C23H34O4
Standard InCHIKey:  LMMOFSFYOMSBHS-OUFMZXHOSA-N
Standard InCHI:  InChI=1S/C23H34O4/c1-6-21(2)13-10-17-16(15-21)8-9-18-22(17,3)11-7-12-23(18,4)27-20(25)14-19(24)26-5/h6,18H,1,7-15H2,2-5H3/t18-,21+,22-,23+/m0/s1
Canonical SMILES:  COC(=O)CC(=O)O[C@]1(C)CCC[C@@]2([C@@H]1CCC1=C2CC[C@@](C1)(C)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
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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 128 ug/ml 21131198
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC > 128 ug/ml 21377877
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 128 ug/ml 11473432
NPT19 Organism Escherichia coli Escherichia coli MIC > 128 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 NPC474978 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
0.9605 High Similarity NPC476101
0.9481 High Similarity NPC474979
0.9114 High Similarity NPC473592
0.8272 Intermediate Similarity NPC269791
0.8 Intermediate Similarity NPC76333
0.7857 Intermediate Similarity NPC286786
0.7805 Intermediate Similarity NPC4827
0.7805 Intermediate Similarity NPC321514
0.7778 Intermediate Similarity NPC899
0.7765 Intermediate Similarity NPC52108
0.7765 Intermediate Similarity NPC474789
0.7765 Intermediate Similarity NPC132386
0.775 Intermediate Similarity NPC166797
0.7738 Intermediate Similarity NPC195334
0.7738 Intermediate Similarity NPC327002
0.7738 Intermediate Similarity NPC476988
0.7738 Intermediate Similarity NPC142163
0.7738 Intermediate Similarity NPC290495
0.7738 Intermediate Similarity NPC474955
0.7717 Intermediate Similarity NPC120708
0.7711 Intermediate Similarity NPC28319
0.7711 Intermediate Similarity NPC100906
0.7701 Intermediate Similarity NPC262085
0.7701 Intermediate Similarity NPC73038
0.7692 Intermediate Similarity NPC23621
0.7692 Intermediate Similarity NPC184006
0.7692 Intermediate Similarity NPC78580
0.7674 Intermediate Similarity NPC120158
0.7674 Intermediate Similarity NPC475193
0.7667 Intermediate Similarity NPC477574
0.7647 Intermediate Similarity NPC15910
0.7647 Intermediate Similarity NPC256112
0.764 Intermediate Similarity NPC471342
0.764 Intermediate Similarity NPC59682
0.764 Intermediate Similarity NPC469866
0.7632 Intermediate Similarity NPC474768
0.7614 Intermediate Similarity NPC245004
0.7614 Intermediate Similarity NPC131329
0.7614 Intermediate Similarity NPC46912
0.7614 Intermediate Similarity NPC171722
0.7614 Intermediate Similarity NPC162107
0.7609 Intermediate Similarity NPC23241
0.7609 Intermediate Similarity NPC473648
0.7609 Intermediate Similarity NPC195715
0.7558 Intermediate Similarity NPC476927
0.7558 Intermediate Similarity NPC476100
0.7556 Intermediate Similarity NPC111585
0.7556 Intermediate Similarity NPC148414
0.7556 Intermediate Similarity NPC175628
0.7531 Intermediate Similarity NPC306928
0.7531 Intermediate Similarity NPC71152
0.7529 Intermediate Similarity NPC25554
0.7529 Intermediate Similarity NPC108476
0.75 Intermediate Similarity NPC325594
0.75 Intermediate Similarity NPC329943
0.75 Intermediate Similarity NPC474970
0.75 Intermediate Similarity NPC44083
0.75 Intermediate Similarity NPC286153
0.75 Intermediate Similarity NPC153987
0.75 Intermediate Similarity NPC473431
0.75 Intermediate Similarity NPC327674
0.75 Intermediate Similarity NPC91525
0.75 Intermediate Similarity NPC473280
0.75 Intermediate Similarity NPC10005
0.75 Intermediate Similarity NPC471078
0.75 Intermediate Similarity NPC473435
0.75 Intermediate Similarity NPC9892
0.7473 Intermediate Similarity NPC288833
0.7473 Intermediate Similarity NPC282616
0.7473 Intermediate Similarity NPC471588
0.7473 Intermediate Similarity NPC6255
0.7473 Intermediate Similarity NPC324341
0.7473 Intermediate Similarity NPC155120
0.7473 Intermediate Similarity NPC966
0.7473 Intermediate Similarity NPC228784
0.7473 Intermediate Similarity NPC26888
0.7473 Intermediate Similarity NPC36491
0.7471 Intermediate Similarity NPC156981
0.747 Intermediate Similarity NPC472300
0.747 Intermediate Similarity NPC283619
0.7447 Intermediate Similarity NPC26413
0.7444 Intermediate Similarity NPC474570
0.7444 Intermediate Similarity NPC20946
0.7444 Intermediate Similarity NPC474700
0.7444 Intermediate Similarity NPC471222
0.7444 Intermediate Similarity NPC474889
0.7444 Intermediate Similarity NPC475049
0.7444 Intermediate Similarity NPC30522
0.7444 Intermediate Similarity NPC173042
0.7444 Intermediate Similarity NPC16265
0.7442 Intermediate Similarity NPC73882
0.7416 Intermediate Similarity NPC478104
0.7416 Intermediate Similarity NPC166857
0.7416 Intermediate Similarity NPC30421
0.7416 Intermediate Similarity NPC125925
0.7412 Intermediate Similarity NPC104545
0.7412 Intermediate Similarity NPC476265
0.7412 Intermediate Similarity NPC477057
0.7412 Intermediate Similarity NPC37038
0.7412 Intermediate Similarity NPC233332
0.7412 Intermediate Similarity NPC267517
0.7412 Intermediate Similarity NPC274522
0.7396 Intermediate Similarity NPC473514
0.7391 Intermediate Similarity NPC86368
0.7391 Intermediate Similarity NPC79117
0.7386 Intermediate Similarity NPC474013
0.7386 Intermediate Similarity NPC2709
0.7386 Intermediate Similarity NPC476602
0.7386 Intermediate Similarity NPC191965
0.7381 Intermediate Similarity NPC179028
0.7368 Intermediate Similarity NPC164349
0.7363 Intermediate Similarity NPC113989
0.7363 Intermediate Similarity NPC473269
0.7363 Intermediate Similarity NPC86372
0.7363 Intermediate Similarity NPC474728
0.7363 Intermediate Similarity NPC471896
0.7363 Intermediate Similarity NPC120840
0.7363 Intermediate Similarity NPC172361
0.7356 Intermediate Similarity NPC477373
0.7356 Intermediate Similarity NPC139206
0.7349 Intermediate Similarity NPC152754
0.7349 Intermediate Similarity NPC59602
0.7349 Intermediate Similarity NPC476987
0.734 Intermediate Similarity NPC106425
0.734 Intermediate Similarity NPC132824
0.734 Intermediate Similarity NPC151725
0.734 Intermediate Similarity NPC98874
0.734 Intermediate Similarity NPC122324
0.734 Intermediate Similarity NPC327788
0.734 Intermediate Similarity NPC269492
0.7333 Intermediate Similarity NPC224145
0.7333 Intermediate Similarity NPC24816
0.7333 Intermediate Similarity NPC477128
0.7333 Intermediate Similarity NPC474845
0.7333 Intermediate Similarity NPC80335
0.7333 Intermediate Similarity NPC93411
0.7326 Intermediate Similarity NPC170303
0.732 Intermediate Similarity NPC473788
0.732 Intermediate Similarity NPC475558
0.7312 Intermediate Similarity NPC222047
0.7312 Intermediate Similarity NPC80365
0.7312 Intermediate Similarity NPC470697
0.7312 Intermediate Similarity NPC148964
0.7303 Intermediate Similarity NPC84121
0.7303 Intermediate Similarity NPC476104
0.7303 Intermediate Similarity NPC137306
0.7303 Intermediate Similarity NPC475753
0.7303 Intermediate Similarity NPC475181
0.7303 Intermediate Similarity NPC324063
0.7303 Intermediate Similarity NPC264127
0.7294 Intermediate Similarity NPC242767
0.7294 Intermediate Similarity NPC231431
0.7292 Intermediate Similarity NPC475385
0.7292 Intermediate Similarity NPC475156
0.7292 Intermediate Similarity NPC475392
0.7292 Intermediate Similarity NPC475202
0.7292 Intermediate Similarity NPC473576
0.7284 Intermediate Similarity NPC110799
0.7283 Intermediate Similarity NPC470590
0.7283 Intermediate Similarity NPC60755
0.7283 Intermediate Similarity NPC177641
0.7283 Intermediate Similarity NPC476417
0.7283 Intermediate Similarity NPC77099
0.7283 Intermediate Similarity NPC297265
0.7283 Intermediate Similarity NPC285184
0.7273 Intermediate Similarity NPC469407
0.7273 Intermediate Similarity NPC312660
0.7273 Intermediate Similarity NPC306951
0.7273 Intermediate Similarity NPC100391
0.7263 Intermediate Similarity NPC2049
0.7263 Intermediate Similarity NPC89225
0.7263 Intermediate Similarity NPC21728
0.7263 Intermediate Similarity NPC473456
0.7262 Intermediate Similarity NPC132542
0.7253 Intermediate Similarity NPC234346
0.7253 Intermediate Similarity NPC474704
0.7253 Intermediate Similarity NPC59263
0.7253 Intermediate Similarity NPC127689
0.7253 Intermediate Similarity NPC225585
0.7253 Intermediate Similarity NPC130520
0.7253 Intermediate Similarity NPC263393
0.7253 Intermediate Similarity NPC177141
0.7253 Intermediate Similarity NPC270768
0.7253 Intermediate Similarity NPC475921
0.7253 Intermediate Similarity NPC121798
0.7253 Intermediate Similarity NPC293048
0.7253 Intermediate Similarity NPC97577
0.7253 Intermediate Similarity NPC61543
0.7245 Intermediate Similarity NPC470954
0.7241 Intermediate Similarity NPC100297
0.7241 Intermediate Similarity NPC240302
0.7241 Intermediate Similarity NPC321289
0.7241 Intermediate Similarity NPC471218
0.7241 Intermediate Similarity NPC327969
0.7241 Intermediate Similarity NPC2524
0.7234 Intermediate Similarity NPC476519
0.7234 Intermediate Similarity NPC777
0.7234 Intermediate Similarity NPC148523
0.7234 Intermediate Similarity NPC474909
0.7229 Intermediate Similarity NPC279666

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC474978 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
0.7473 Intermediate Similarity NPD6411 Approved
0.7416 Intermediate Similarity NPD3573 Approved
0.7253 Intermediate Similarity NPD6101 Approved
0.7253 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5737 Approved
0.7143 Intermediate Similarity NPD6672 Approved
0.7128 Intermediate Similarity NPD7900 Approved
0.7128 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD7748 Approved
0.7111 Intermediate Similarity NPD7146 Approved
0.7111 Intermediate Similarity NPD6684 Approved
0.7111 Intermediate Similarity NPD5330 Approved
0.7111 Intermediate Similarity NPD6409 Approved
0.7111 Intermediate Similarity NPD6098 Approved
0.7111 Intermediate Similarity NPD7521 Approved
0.7111 Intermediate Similarity NPD7334 Approved
0.7097 Intermediate Similarity NPD5694 Approved
0.7097 Intermediate Similarity NPD6050 Approved
0.7065 Intermediate Similarity NPD6051 Approved
0.7065 Intermediate Similarity NPD6080 Approved
0.7065 Intermediate Similarity NPD6904 Approved
0.7065 Intermediate Similarity NPD6673 Approved
0.7053 Intermediate Similarity NPD5695 Phase 3
0.6989 Remote Similarity NPD5692 Phase 3
0.6989 Remote Similarity NPD5207 Approved
0.6957 Remote Similarity NPD6903 Approved
0.6957 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6915 Remote Similarity NPD7515 Phase 2
0.6907 Remote Similarity NPD6084 Phase 2
0.6907 Remote Similarity NPD6083 Phase 2
0.6907 Remote Similarity NPD7902 Approved
0.6897 Remote Similarity NPD7645 Phase 2
0.6842 Remote Similarity NPD5779 Approved
0.6842 Remote Similarity NPD6399 Phase 3
0.6842 Remote Similarity NPD5778 Approved
0.6813 Remote Similarity NPD1694 Approved
0.6796 Remote Similarity NPD6881 Approved
0.6796 Remote Similarity NPD6899 Approved
0.6774 Remote Similarity NPD5208 Approved
0.6771 Remote Similarity NPD6001 Approved
0.6765 Remote Similarity NPD5739 Approved
0.6765 Remote Similarity NPD6675 Approved
0.6765 Remote Similarity NPD6402 Approved
0.6765 Remote Similarity NPD7128 Approved
0.6737 Remote Similarity NPD5693 Phase 1
0.6737 Remote Similarity NPD5284 Approved
0.6737 Remote Similarity NPD5281 Approved
0.6702 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6701 Remote Similarity NPD5654 Approved
0.6699 Remote Similarity NPD5697 Approved
0.6667 Remote Similarity NPD5696 Approved
0.6667 Remote Similarity NPD6883 Approved
0.6667 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7290 Approved
0.6667 Remote Similarity NPD4225 Approved
0.6667 Remote Similarity NPD7102 Approved
0.6667 Remote Similarity NPD7638 Approved
0.6635 Remote Similarity NPD7320 Approved
0.6633 Remote Similarity NPD7732 Phase 3
0.6629 Remote Similarity NPD7525 Registered
0.6606 Remote Similarity NPD7115 Discovery
0.6604 Remote Similarity NPD6847 Approved
0.6604 Remote Similarity NPD6617 Approved
0.6604 Remote Similarity NPD6869 Approved
0.6604 Remote Similarity NPD6650 Approved
0.6604 Remote Similarity NPD8130 Phase 1
0.6604 Remote Similarity NPD6649 Approved
0.66 Remote Similarity NPD7639 Approved
0.66 Remote Similarity NPD7640 Approved
0.6571 Remote Similarity NPD6013 Approved
0.6571 Remote Similarity NPD6372 Approved
0.6571 Remote Similarity NPD6012 Approved
0.6571 Remote Similarity NPD6014 Approved
0.6571 Remote Similarity NPD6373 Approved
0.6566 Remote Similarity NPD5959 Approved
0.6562 Remote Similarity NPD7637 Suspended
0.6542 Remote Similarity NPD8297 Approved
0.6542 Remote Similarity NPD6882 Approved
0.6538 Remote Similarity NPD5701 Approved
0.6517 Remote Similarity NPD4195 Approved
0.6512 Remote Similarity NPD4784 Approved
0.6512 Remote Similarity NPD4785 Approved
0.6476 Remote Similarity NPD6011 Approved
0.6471 Remote Similarity NPD4243 Approved
0.6442 Remote Similarity NPD6008 Approved
0.6437 Remote Similarity NPD8039 Approved
0.6392 Remote Similarity NPD8034 Phase 2
0.6392 Remote Similarity NPD6079 Approved
0.6392 Remote Similarity NPD8035 Phase 2
0.6383 Remote Similarity NPD5690 Phase 2
0.6383 Remote Similarity NPD3618 Phase 1
0.6354 Remote Similarity NPD4753 Phase 2
0.6354 Remote Similarity NPD5328 Approved
0.6344 Remote Similarity NPD4786 Approved
0.6344 Remote Similarity NPD3668 Phase 3
0.6321 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6304 Remote Similarity NPD4223 Phase 3
0.6304 Remote Similarity NPD4221 Approved
0.6304 Remote Similarity NPD3667 Approved
0.63 Remote Similarity NPD7614 Phase 1
0.6296 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6283 Remote Similarity NPD6319 Approved
0.6277 Remote Similarity NPD5329 Approved
0.6277 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6275 Remote Similarity NPD5285 Approved
0.6275 Remote Similarity NPD5286 Approved
0.6275 Remote Similarity NPD4696 Approved
0.6264 Remote Similarity NPD4695 Discontinued
0.6263 Remote Similarity NPD5707 Approved
0.6262 Remote Similarity NPD8132 Clinical (unspecified phase)
0.625 Remote Similarity NPD7339 Approved
0.625 Remote Similarity NPD6052 Approved
0.625 Remote Similarity NPD6942 Approved
0.6238 Remote Similarity NPD4755 Approved
0.6226 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6226 Remote Similarity NPD6614 Approved
0.622 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6211 Remote Similarity NPD4623 Approved
0.6211 Remote Similarity NPD4694 Approved
0.6211 Remote Similarity NPD5280 Approved
0.6211 Remote Similarity NPD4519 Discontinued
0.6207 Remote Similarity NPD7492 Approved
0.62 Remote Similarity NPD4629 Approved
0.62 Remote Similarity NPD5210 Approved
0.6196 Remote Similarity NPD4692 Approved
0.6196 Remote Similarity NPD4139 Approved
0.6195 Remote Similarity NPD7101 Approved
0.6195 Remote Similarity NPD7100 Approved
0.618 Remote Similarity NPD3701 Clinical (unspecified phase)
0.617 Remote Similarity NPD3666 Approved
0.617 Remote Similarity NPD4197 Approved
0.617 Remote Similarity NPD3133 Approved
0.617 Remote Similarity NPD3665 Phase 1
0.6162 Remote Similarity NPD4202 Approved
0.6154 Remote Similarity NPD6616 Approved
0.6154 Remote Similarity NPD5225 Approved
0.6154 Remote Similarity NPD5226 Approved
0.6154 Remote Similarity NPD5224 Approved
0.6154 Remote Similarity NPD5211 Phase 2
0.6154 Remote Similarity NPD4633 Approved
0.6154 Remote Similarity NPD7632 Discontinued
0.614 Remote Similarity NPD6054 Approved
0.6139 Remote Similarity NPD5222 Approved
0.6139 Remote Similarity NPD5221 Approved
0.6139 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6136 Remote Similarity NPD4687 Approved
0.6136 Remote Similarity NPD5733 Approved
0.6117 Remote Similarity NPD4700 Approved
0.6111 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6106 Remote Similarity NPD6335 Approved
0.6102 Remote Similarity NPD7078 Approved
0.6095 Remote Similarity NPD5175 Approved
0.6095 Remote Similarity NPD5174 Approved
0.6087 Remote Similarity NPD4748 Discontinued
0.6078 Remote Similarity NPD5173 Approved
0.6071 Remote Similarity NPD6274 Approved
0.6071 Remote Similarity NPD6868 Approved
0.6067 Remote Similarity NPD4190 Phase 3
0.6067 Remote Similarity NPD8264 Approved
0.6067 Remote Similarity NPD5275 Approved
0.6064 Remote Similarity NPD6695 Phase 3
0.6058 Remote Similarity NPD5223 Approved
0.6055 Remote Similarity NPD4634 Approved
0.6055 Remote Similarity NPD5955 Clinical (unspecified phase)
0.605 Remote Similarity NPD7736 Approved
0.6047 Remote Similarity NPD4137 Phase 3
0.6044 Remote Similarity NPD3617 Approved
0.6042 Remote Similarity NPD4138 Approved
0.6042 Remote Similarity NPD4693 Phase 3
0.6042 Remote Similarity NPD4689 Approved
0.6042 Remote Similarity NPD4688 Approved
0.6042 Remote Similarity NPD5205 Approved
0.6042 Remote Similarity NPD5279 Phase 3
0.6042 Remote Similarity NPD4690 Approved
0.6038 Remote Similarity NPD5141 Approved
0.6036 Remote Similarity NPD4632 Approved
0.6034 Remote Similarity NPD6370 Approved
0.6022 Remote Similarity NPD5369 Approved
0.6018 Remote Similarity NPD6317 Approved
0.6018 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6 Remote Similarity NPD6059 Approved
0.5983 Remote Similarity NPD8328 Phase 3
0.598 Remote Similarity NPD5349 Clinical (unspecified phase)
0.598 Remote Similarity NPD4697 Phase 3
0.5977 Remote Similarity NPD4691 Approved
0.5977 Remote Similarity NPD4747 Approved
0.5966 Remote Similarity NPD8293 Discontinued
0.5965 Remote Similarity NPD6314 Approved
0.5965 Remote Similarity NPD6313 Approved
0.5962 Remote Similarity NPD6648 Approved
0.5957 Remote Similarity NPD5209 Approved
0.5955 Remote Similarity NPD6924 Approved
0.5955 Remote Similarity NPD6926 Approved
0.5955 Remote Similarity NPD4058 Approved
0.5948 Remote Similarity NPD6908 Approved
0.5948 Remote Similarity NPD7503 Approved
0.5948 Remote Similarity NPD6016 Approved

Structure

External Identifiers

PubChem CID   44566220
ChEMBL   CHEMBL490700
ZINC  

Physicochemical Properties

Molecular Weight:  374.25
ALogP:  2.3327
MLogP:  3.55
XLogP:  5.914
# Rotatable Bonds:  10
Polar Surface Area:  52.6
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  27

Download Data

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