Natural Product: NPC133391

Natural Product ID:  NPC133391
Common Name:   (2R,6R)-6-[(3R,3Ar,5As,6S,7S,9Br)-6-(2-Carboxyethyl)-3A,6,9B-Trimethyl-7-Prop-1-En-2-Yl-1,2,3,4,5,5A,7,8-Octahydrocyclopenta[A]Naphthalen-3-Yl]-2-Methyl-4-Oxoheptanoic Acid
IUPAC Name:   (2R,6R)-6-[(3R,3aR,5aS,6S,7S,9bR)-6-(2-carboxyethyl)-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,5,5a,7,8-octahydrocyclopenta[a]naphthalen-3-yl]-2-methyl-4-oxoheptanoic acid
Synonyms:  
Molecular Formula:   C30H46O5
Standard InCHIKey:  VNTNAZOWHUDJEO-GUGKPHJQSA-N
Standard InCHI:  InChI=1S/C30H46O5/c1-18(2)22-8-9-25-24(28(22,5)13-12-26(32)33)11-15-29(6)23(10-14-30(25,29)7)19(3)16-21(31)17-20(4)27(34)35/h9,19-20,22-24H,1,8,10-17H2,2-7H3,(H,32,33)(H,34,35)/t19-,20-,22+,23-,24-,28+,29-,30+/m1/s1
Canonical SMILES:  O=C(C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@H]1C2=CC[C@H]([C@]1(C)CCC(=O)O)C(=C)C)C)C)C[C@H](C(=O)O)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
NPO23553 Abies sachalinensis Species Pinaceae Eukaryota Barks PMID[12444693]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens Inhibition = 4 % 20409719

  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 NPC133391 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 NPC477371
0.9367 High Similarity NPC477373
0.9359 High Similarity NPC477372
0.9359 High Similarity NPC38350
0.9359 High Similarity NPC201912
0.9359 High Similarity NPC147066
0.9241 High Similarity NPC240302
0.9241 High Similarity NPC260956
0.9125 High Similarity NPC69279
0.9125 High Similarity NPC83569
0.9 High Similarity NPC320514
0.8916 High Similarity NPC136948
0.8916 High Similarity NPC96496
0.8916 High Similarity NPC167877
0.8902 High Similarity NPC11711
0.8902 High Similarity NPC29447
0.8889 High Similarity NPC470015
0.8889 High Similarity NPC168188
0.8861 High Similarity NPC158846
0.8861 High Similarity NPC196827
0.8861 High Similarity NPC274996
0.878 High Similarity NPC165064
0.878 High Similarity NPC209882
0.878 High Similarity NPC164577
0.8734 High Similarity NPC321514
0.8721 High Similarity NPC212301
0.8721 High Similarity NPC154101
0.8721 High Similarity NPC297265
0.8721 High Similarity NPC86266
0.8721 High Similarity NPC110657
0.8718 High Similarity NPC180886
0.8706 High Similarity NPC54689
0.8706 High Similarity NPC474570
0.8706 High Similarity NPC262043
0.869 High Similarity NPC312215
0.8684 High Similarity NPC160817
0.8675 High Similarity NPC94531
0.8675 High Similarity NPC269638
0.8675 High Similarity NPC473038
0.8675 High Similarity NPC311702
0.8675 High Similarity NPC123319
0.8659 High Similarity NPC97913
0.8659 High Similarity NPC310470
0.8659 High Similarity NPC167103
0.8642 High Similarity NPC278459
0.8625 High Similarity NPC215843
0.8621 High Similarity NPC152897
0.8621 High Similarity NPC141497
0.8621 High Similarity NPC107674
0.8621 High Similarity NPC66429
0.8621 High Similarity NPC170220
0.8588 High Similarity NPC294480
0.8571 High Similarity NPC212843
0.8571 High Similarity NPC155011
0.8554 High Similarity NPC472865
0.8554 High Similarity NPC100391
0.8537 High Similarity NPC296367
0.8523 High Similarity NPC49670
0.8523 High Similarity NPC159410
0.8519 High Similarity NPC37038
0.8506 High Similarity NPC204341
0.85 High Similarity NPC179028
0.85 High Similarity NPC74410
0.85 High Similarity NPC260385
0.85 High Similarity NPC110094
0.85 High Similarity NPC280654
0.8488 Intermediate Similarity NPC475921
0.8488 Intermediate Similarity NPC474704
0.8481 Intermediate Similarity NPC20466
0.8481 Intermediate Similarity NPC246445
0.8471 Intermediate Similarity NPC128644
0.8471 Intermediate Similarity NPC159046
0.8471 Intermediate Similarity NPC233836
0.8471 Intermediate Similarity NPC474684
0.8471 Intermediate Similarity NPC187376
0.8471 Intermediate Similarity NPC142361
0.8452 Intermediate Similarity NPC474218
0.8452 Intermediate Similarity NPC142649
0.8452 Intermediate Similarity NPC470223
0.8434 Intermediate Similarity NPC477852
0.8427 Intermediate Similarity NPC469599
0.8427 Intermediate Similarity NPC263347
0.8415 Intermediate Similarity NPC274050
0.8415 Intermediate Similarity NPC267691
0.8415 Intermediate Similarity NPC232625
0.8415 Intermediate Similarity NPC263272
0.8415 Intermediate Similarity NPC162632
0.8415 Intermediate Similarity NPC327002
0.8415 Intermediate Similarity NPC471898
0.8409 Intermediate Similarity NPC470376
0.8409 Intermediate Similarity NPC470375
0.8409 Intermediate Similarity NPC243866
0.8395 Intermediate Similarity NPC231431
0.8395 Intermediate Similarity NPC199595
0.8395 Intermediate Similarity NPC327674
0.8395 Intermediate Similarity NPC192744
0.8391 Intermediate Similarity NPC46281
0.8391 Intermediate Similarity NPC471896
0.8391 Intermediate Similarity NPC111585
0.8391 Intermediate Similarity NPC148414
0.8391 Intermediate Similarity NPC175628
0.8375 Intermediate Similarity NPC107039
0.8375 Intermediate Similarity NPC66105
0.8375 Intermediate Similarity NPC471899
0.8375 Intermediate Similarity NPC165711
0.8375 Intermediate Similarity NPC471897
0.8375 Intermediate Similarity NPC238227
0.8372 Intermediate Similarity NPC117122
0.8372 Intermediate Similarity NPC183546
0.8372 Intermediate Similarity NPC242864
0.8372 Intermediate Similarity NPC48866
0.8372 Intermediate Similarity NPC247406
0.8354 Intermediate Similarity NPC192540
0.8354 Intermediate Similarity NPC279666
0.8353 Intermediate Similarity NPC28252
0.8353 Intermediate Similarity NPC472869
0.8353 Intermediate Similarity NPC186975
0.8353 Intermediate Similarity NPC55309
0.8333 Intermediate Similarity NPC214043
0.8333 Intermediate Similarity NPC96095
0.8333 Intermediate Similarity NPC221758
0.8333 Intermediate Similarity NPC473246
0.8333 Intermediate Similarity NPC19849
0.8333 Intermediate Similarity NPC476038
0.8333 Intermediate Similarity NPC472864
0.8333 Intermediate Similarity NPC155676
0.8333 Intermediate Similarity NPC85774
0.8333 Intermediate Similarity NPC194937
0.8333 Intermediate Similarity NPC82902
0.8333 Intermediate Similarity NPC59453
0.8313 Intermediate Similarity NPC193347
0.8313 Intermediate Similarity NPC251779
0.8313 Intermediate Similarity NPC321289
0.8313 Intermediate Similarity NPC327969
0.8313 Intermediate Similarity NPC69101
0.8295 Intermediate Similarity NPC107690
0.8295 Intermediate Similarity NPC189520
0.8295 Intermediate Similarity NPC23434
0.8295 Intermediate Similarity NPC26888
0.8293 Intermediate Similarity NPC104545
0.8276 Intermediate Similarity NPC474889
0.8276 Intermediate Similarity NPC84271
0.8276 Intermediate Similarity NPC476733
0.8276 Intermediate Similarity NPC215029
0.8276 Intermediate Similarity NPC477943
0.8276 Intermediate Similarity NPC214387
0.8276 Intermediate Similarity NPC102414
0.8276 Intermediate Similarity NPC155479
0.8276 Intermediate Similarity NPC77168
0.8276 Intermediate Similarity NPC477973
0.8272 Intermediate Similarity NPC321690
0.8261 Intermediate Similarity NPC51370
0.8256 Intermediate Similarity NPC236618
0.8256 Intermediate Similarity NPC317590
0.8256 Intermediate Similarity NPC90652
0.825 Intermediate Similarity NPC69143
0.825 Intermediate Similarity NPC89294
0.825 Intermediate Similarity NPC309399
0.8242 Intermediate Similarity NPC57416
0.8242 Intermediate Similarity NPC475894
0.8242 Intermediate Similarity NPC107243
0.8235 Intermediate Similarity NPC469948
0.8235 Intermediate Similarity NPC471224
0.8235 Intermediate Similarity NPC474083
0.8235 Intermediate Similarity NPC283733
0.8228 Intermediate Similarity NPC241854
0.8228 Intermediate Similarity NPC103958
0.8228 Intermediate Similarity NPC301065
0.8228 Intermediate Similarity NPC183503
0.8228 Intermediate Similarity NPC161923
0.8228 Intermediate Similarity NPC251970
0.8228 Intermediate Similarity NPC283908
0.8228 Intermediate Similarity NPC476046
0.8222 Intermediate Similarity NPC162001
0.8222 Intermediate Similarity NPC222845
0.8222 Intermediate Similarity NPC45324
0.8222 Intermediate Similarity NPC171395
0.8214 Intermediate Similarity NPC469561
0.8214 Intermediate Similarity NPC70834
0.8214 Intermediate Similarity NPC476082
0.8214 Intermediate Similarity NPC271784
0.8214 Intermediate Similarity NPC278648
0.8202 Intermediate Similarity NPC470254
0.8202 Intermediate Similarity NPC470224
0.8202 Intermediate Similarity NPC25750
0.8202 Intermediate Similarity NPC206810
0.8193 Intermediate Similarity NPC142244
0.8193 Intermediate Similarity NPC221647
0.8182 Intermediate Similarity NPC477147
0.8182 Intermediate Similarity NPC477149
0.8182 Intermediate Similarity NPC469400
0.8182 Intermediate Similarity NPC123854
0.8171 Intermediate Similarity NPC16394
0.8161 Intermediate Similarity NPC472870
0.8161 Intermediate Similarity NPC470417
0.8161 Intermediate Similarity NPC28227
0.8148 Intermediate Similarity NPC212661
0.8148 Intermediate Similarity NPC471035
0.8148 Intermediate Similarity NPC97377
0.8148 Intermediate Similarity NPC68828

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC133391 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
0.8837 High Similarity NPD6399 Phase 3
0.8506 High Similarity NPD5284 Approved
0.8506 High Similarity NPD5281 Approved
0.8333 Intermediate Similarity NPD4786 Approved
0.8313 Intermediate Similarity NPD4223 Phase 3
0.8313 Intermediate Similarity NPD4221 Approved
0.8235 Intermediate Similarity NPD5329 Approved
0.8161 Intermediate Similarity NPD6672 Approved
0.8161 Intermediate Similarity NPD5737 Approved
0.814 Intermediate Similarity NPD6098 Approved
0.8118 Intermediate Similarity NPD4197 Approved
0.8095 Intermediate Similarity NPD3667 Approved
0.8068 Intermediate Similarity NPD6080 Approved
0.8068 Intermediate Similarity NPD6904 Approved
0.8068 Intermediate Similarity NPD6673 Approved
0.8043 Intermediate Similarity NPD6083 Phase 2
0.8043 Intermediate Similarity NPD6084 Phase 2
0.8022 Intermediate Similarity NPD5695 Phase 3
0.7957 Intermediate Similarity NPD5696 Approved
0.7931 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD6684 Approved
0.7931 Intermediate Similarity NPD4694 Approved
0.7931 Intermediate Similarity NPD7146 Approved
0.7931 Intermediate Similarity NPD5280 Approved
0.7931 Intermediate Similarity NPD4689 Approved
0.7931 Intermediate Similarity NPD4693 Phase 3
0.7931 Intermediate Similarity NPD5690 Phase 2
0.7931 Intermediate Similarity NPD7521 Approved
0.7931 Intermediate Similarity NPD7334 Approved
0.7931 Intermediate Similarity NPD4138 Approved
0.7931 Intermediate Similarity NPD4690 Approved
0.7931 Intermediate Similarity NPD5205 Approved
0.7931 Intermediate Similarity NPD6409 Approved
0.7931 Intermediate Similarity NPD3618 Phase 1
0.7931 Intermediate Similarity NPD5330 Approved
0.7931 Intermediate Similarity NPD4688 Approved
0.7907 Intermediate Similarity NPD3133 Approved
0.7907 Intermediate Similarity NPD3666 Approved
0.7907 Intermediate Similarity NPD3665 Phase 1
0.7889 Intermediate Similarity NPD6050 Approved
0.7865 Intermediate Similarity NPD5328 Approved
0.7865 Intermediate Similarity NPD4753 Phase 2
0.7831 Intermediate Similarity NPD3617 Approved
0.7826 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD5207 Approved
0.7778 Intermediate Similarity NPD5692 Phase 3
0.7765 Intermediate Similarity NPD4692 Approved
0.7765 Intermediate Similarity NPD4139 Approved
0.7753 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7753 Intermediate Similarity NPD5208 Approved
0.7753 Intermediate Similarity NPD6903 Approved
0.7742 Intermediate Similarity NPD4697 Phase 3
0.7727 Intermediate Similarity NPD5279 Phase 3
0.7701 Intermediate Similarity NPD3668 Phase 3
0.7692 Intermediate Similarity NPD8034 Phase 2
0.7692 Intermediate Similarity NPD6079 Approved
0.7692 Intermediate Similarity NPD5693 Phase 1
0.7692 Intermediate Similarity NPD8035 Phase 2
0.7692 Intermediate Similarity NPD5694 Approved
0.7692 Intermediate Similarity NPD7515 Phase 2
0.7667 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD7902 Approved
0.7647 Intermediate Similarity NPD4695 Discontinued
0.7634 Intermediate Similarity NPD5210 Approved
0.7634 Intermediate Similarity NPD4629 Approved
0.7625 Intermediate Similarity NPD4747 Approved
0.7619 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD6373 Approved
0.76 Intermediate Similarity NPD6372 Approved
0.7561 Intermediate Similarity NPD5733 Approved
0.7531 Intermediate Similarity NPD4243 Approved
0.7531 Intermediate Similarity NPD6081 Approved
0.7529 Intermediate Similarity NPD4195 Approved
0.7527 Intermediate Similarity NPD6001 Approved
0.7527 Intermediate Similarity NPD7748 Approved
0.75 Intermediate Similarity NPD4137 Phase 3
0.7475 Intermediate Similarity NPD5739 Approved
0.7475 Intermediate Similarity NPD6675 Approved
0.7475 Intermediate Similarity NPD7128 Approved
0.7475 Intermediate Similarity NPD6402 Approved
0.7451 Intermediate Similarity NPD6650 Approved
0.7451 Intermediate Similarity NPD6649 Approved
0.7419 Intermediate Similarity NPD4202 Approved
0.7407 Intermediate Similarity NPD4691 Approved
0.7391 Intermediate Similarity NPD4096 Approved
0.7386 Intermediate Similarity NPD4788 Approved
0.7375 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD5222 Approved
0.7368 Intermediate Similarity NPD5221 Approved
0.7349 Intermediate Similarity NPD4785 Approved
0.7349 Intermediate Similarity NPD4784 Approved
0.7349 Intermediate Similarity NPD4687 Approved
0.7342 Intermediate Similarity NPD4224 Phase 2
0.734 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD7900 Approved
0.7333 Intermediate Similarity NPD4519 Discontinued
0.7333 Intermediate Similarity NPD4623 Approved
0.7327 Intermediate Similarity NPD7320 Approved
0.7327 Intermediate Similarity NPD6899 Approved
0.7327 Intermediate Similarity NPD6881 Approved
0.732 Intermediate Similarity NPD6404 Discontinued
0.7317 Intermediate Similarity NPD5276 Approved
0.7292 Intermediate Similarity NPD5173 Approved
0.7292 Intermediate Similarity NPD4755 Approved
0.7273 Intermediate Similarity NPD6052 Approved
0.7263 Intermediate Similarity NPD5654 Approved
0.7262 Intermediate Similarity NPD7339 Approved
0.7262 Intermediate Similarity NPD6942 Approved
0.7234 Intermediate Similarity NPD5133 Approved
0.7228 Intermediate Similarity NPD5701 Approved
0.7228 Intermediate Similarity NPD5697 Approved
0.7188 Intermediate Similarity NPD7614 Phase 1
0.7184 Intermediate Similarity NPD7290 Approved
0.7184 Intermediate Similarity NPD6883 Approved
0.7184 Intermediate Similarity NPD7102 Approved
0.7174 Intermediate Similarity NPD4518 Approved
0.7172 Intermediate Similarity NPD5091 Approved
0.7159 Intermediate Similarity NPD5369 Approved
0.7157 Intermediate Similarity NPD6011 Approved
0.7143 Intermediate Similarity NPD5285 Approved
0.7143 Intermediate Similarity NPD4700 Approved
0.7143 Intermediate Similarity NPD5286 Approved
0.7143 Intermediate Similarity NPD4696 Approved
0.7143 Intermediate Similarity NPD4058 Approved
0.7115 Intermediate Similarity NPD6869 Approved
0.7115 Intermediate Similarity NPD6847 Approved
0.7115 Intermediate Similarity NPD6617 Approved
0.7115 Intermediate Similarity NPD8130 Phase 1
0.7115 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD5959 Approved
0.7087 Intermediate Similarity NPD6014 Approved
0.7087 Intermediate Similarity NPD6013 Approved
0.7087 Intermediate Similarity NPD6012 Approved
0.7079 Intermediate Similarity NPD4270 Approved
0.7079 Intermediate Similarity NPD4269 Approved
0.7079 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD5223 Approved
0.7065 Intermediate Similarity NPD3573 Approved
0.7059 Intermediate Similarity NPD6614 Approved
0.7059 Intermediate Similarity NPD5275 Approved
0.7059 Intermediate Similarity NPD4190 Phase 3
0.7048 Intermediate Similarity NPD6882 Approved
0.7048 Intermediate Similarity NPD8297 Approved
0.7045 Intermediate Similarity NPD5368 Approved
0.7045 Intermediate Similarity NPD7525 Registered
0.7041 Intermediate Similarity NPD7638 Approved
0.7 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5362 Discontinued
0.7 Intermediate Similarity NPD5211 Phase 2
0.7 Intermediate Similarity NPD5226 Approved
0.7 Intermediate Similarity NPD5225 Approved
0.7 Intermediate Similarity NPD4633 Approved
0.7 Intermediate Similarity NPD5224 Approved
0.6977 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6977 Remote Similarity NPD6117 Approved
0.697 Remote Similarity NPD7639 Approved
0.697 Remote Similarity NPD7640 Approved
0.6961 Remote Similarity NPD6008 Approved
0.6957 Remote Similarity NPD5786 Approved
0.6951 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6951 Remote Similarity NPD5360 Phase 3
0.6947 Remote Similarity NPD6411 Approved
0.6944 Remote Similarity NPD7115 Discovery
0.6941 Remote Similarity NPD6926 Approved
0.6941 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6941 Remote Similarity NPD6924 Approved
0.6931 Remote Similarity NPD4754 Approved
0.6931 Remote Similarity NPD5174 Approved
0.6931 Remote Similarity NPD5175 Approved
0.6915 Remote Similarity NPD6051 Approved
0.6914 Remote Similarity NPD7331 Phase 2
0.6897 Remote Similarity NPD6116 Phase 1
0.6893 Remote Similarity NPD6412 Phase 2
0.6889 Remote Similarity NPD6435 Approved
0.6863 Remote Similarity NPD5141 Approved
0.6854 Remote Similarity NPD4252 Approved
0.6852 Remote Similarity NPD6868 Approved
0.6848 Remote Similarity NPD1694 Approved
0.6848 Remote Similarity NPD5363 Approved
0.6842 Remote Similarity NPD5785 Approved
0.6822 Remote Similarity NPD4632 Approved
0.6818 Remote Similarity NPD6118 Approved
0.6818 Remote Similarity NPD6114 Approved
0.6818 Remote Similarity NPD6697 Approved
0.6818 Remote Similarity NPD6115 Approved
0.6796 Remote Similarity NPD4768 Approved
0.6796 Remote Similarity NPD4767 Approved
0.679 Remote Similarity NPD7341 Phase 2
0.6786 Remote Similarity NPD4789 Approved
0.6782 Remote Similarity NPD6933 Approved
0.6771 Remote Similarity NPD7637 Suspended
0.6737 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6737 Remote Similarity NPD6101 Approved
0.6727 Remote Similarity NPD6335 Approved
0.6706 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6706 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6697 Remote Similarity NPD6274 Approved
0.6667 Remote Similarity NPD7100 Approved

Structure

External Identifiers

PubChem CID   11762658
ChEMBL   CHEMBL464896
ZINC  

Physicochemical Properties

Molecular Weight:  486.33
ALogP:  2.4966
MLogP:  4.21
XLogP:  7.771
# Rotatable Bonds:  18
Polar Surface Area:  91.67
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  35

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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