Natural Product: NPC8389

Natural Product ID:  NPC8389
Common Name:   6Beta-Cinnamoyloxy-7Beta-Acetoxyvouacapen-5Alpha-Ol
IUPAC Name:   [(4aR,5R,6R,6aS,7R,11aS,11bR)-6-acetyloxy-4a-hydroxy-4,4,7,11b-tetramethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-5-yl] (E)-3-phenylprop-2-enoate
Synonyms:  
Molecular Formula:   C31H38O6
Standard InCHIKey:  NQXXHQFQXKHFLH-JLTDNTAYSA-N
Standard InCHI:  InChI=1S/C31H38O6/c1-19-22-14-17-35-24(22)18-23-26(19)27(36-20(2)32)28(31(34)29(3,4)15-9-16-30(23,31)5)37-25(33)13-12-21-10-7-6-8-11-21/h6-8,10-14,17,19,23,26-28,34H,9,15-16,18H2,1-5H3/b13-12+/t19-,23-,26-,27+,28+,30+,31+/m0/s1
Canonical SMILES:  O=C(O[C@@H]1[C@H](OC(=O)C)[C@H]2[C@@H](C)c3ccoc3C[C@@H]2[C@@]2([C@]1(O)C(C)(C)CCC2)C)/C=C/c1ccccc1
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
NPO32590 caesalpinia sp. Species Fabaceae Eukaryota PMID[20356735]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT116 Cell Line HL-60 Homo sapiens IC50 = 17370 nM 8133298
NPT165 Cell Line HeLa Homo sapiens IC50 = 33410 nM 20666364

  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 NPC8389 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
0.9934 High Similarity NPC79571
0.9867 High Similarity NPC7059
0.974 High Similarity NPC277618
0.9615 High Similarity NPC296558
0.9605 High Similarity NPC194499
0.9605 High Similarity NPC88007
0.9477 High Similarity NPC195954
0.947 High Similarity NPC121615
0.947 High Similarity NPC294511
0.9467 High Similarity NPC228842
0.9467 High Similarity NPC212257
0.9419 High Similarity NPC68848
0.9295 High Similarity NPC18986
0.9295 High Similarity NPC188649
0.9267 High Similarity NPC71821
0.9236 High Similarity NPC88841
0.9236 High Similarity NPC285567
0.9236 High Similarity NPC283209
0.9236 High Similarity NPC288602
0.9182 High Similarity NPC310572
0.9182 High Similarity NPC41689
0.9167 High Similarity NPC474611
0.9161 High Similarity NPC41880
0.9119 High Similarity NPC121995
0.9108 High Similarity NPC287559
0.9038 High Similarity NPC104736
0.902 High Similarity NPC69647
0.902 High Similarity NPC125182
0.9013 High Similarity NPC255414
0.9006 High Similarity NPC255787
0.9006 High Similarity NPC291742
0.9 High Similarity NPC308156
0.8994 High Similarity NPC14499
0.8994 High Similarity NPC475039
0.8994 High Similarity NPC476035
0.8981 High Similarity NPC304692
0.8963 High Similarity NPC56953
0.8963 High Similarity NPC176413
0.8951 High Similarity NPC118086
0.8944 High Similarity NPC270312
0.8938 High Similarity NPC56358
0.8933 High Similarity NPC263337
0.8931 High Similarity NPC471003
0.8924 High Similarity NPC123153
0.8896 High Similarity NPC294512
0.8896 High Similarity NPC475641
0.8896 High Similarity NPC475237
0.8861 High Similarity NPC81405
0.882 High Similarity NPC61967
0.882 High Similarity NPC62692
0.882 High Similarity NPC126984
0.882 High Similarity NPC27541
0.8805 High Similarity NPC140952
0.8774 High Similarity NPC211625
0.8765 High Similarity NPC86800
0.8758 High Similarity NPC5676
0.8743 High Similarity NPC11062
0.8733 High Similarity NPC202260
0.8726 High Similarity NPC268905
0.872 High Similarity NPC88593
0.872 High Similarity NPC302392
0.8704 High Similarity NPC276735
0.8696 High Similarity NPC82851
0.8696 High Similarity NPC200782
0.8688 High Similarity NPC84349
0.8684 High Similarity NPC121158
0.8671 High Similarity NPC253201
0.8671 High Similarity NPC302054
0.8671 High Similarity NPC98206
0.8671 High Similarity NPC34421
0.8671 High Similarity NPC237259
0.8659 High Similarity NPC160651
0.865 High Similarity NPC475779
0.8645 High Similarity NPC286038
0.8645 High Similarity NPC216755
0.8642 High Similarity NPC469338
0.8642 High Similarity NPC472773
0.8642 High Similarity NPC292389
0.8634 High Similarity NPC472299
0.8625 High Similarity NPC299038
0.8616 High Similarity NPC155939
0.8616 High Similarity NPC296807
0.8616 High Similarity NPC141538
0.8608 High Similarity NPC48671
0.8608 High Similarity NPC246164
0.8608 High Similarity NPC472672
0.8608 High Similarity NPC476201
0.86 High Similarity NPC307401
0.8598 High Similarity NPC173516
0.859 High Similarity NPC66991
0.8589 High Similarity NPC469849
0.8589 High Similarity NPC276551
0.8589 High Similarity NPC470182
0.8589 High Similarity NPC470940
0.858 High Similarity NPC470792
0.858 High Similarity NPC472771
0.8571 High Similarity NPC475967
0.8571 High Similarity NPC472665
0.8553 High Similarity NPC114880
0.8553 High Similarity NPC282445
0.8545 High Similarity NPC271235
0.8545 High Similarity NPC471397
0.8537 High Similarity NPC470875
0.8535 High Similarity NPC234494
0.8528 High Similarity NPC302369
0.8528 High Similarity NPC134254
0.8528 High Similarity NPC39986
0.8528 High Similarity NPC477405
0.8526 High Similarity NPC471174
0.8519 High Similarity NPC335761
0.8509 High Similarity NPC249021
0.8509 High Similarity NPC472776
0.8509 High Similarity NPC472777
0.8509 High Similarity NPC472778
0.8506 High Similarity NPC241951
0.8506 High Similarity NPC57628
0.8506 High Similarity NPC470152
0.8506 High Similarity NPC188865
0.8506 High Similarity NPC95265
0.8506 High Similarity NPC472570
0.8506 High Similarity NPC475122
0.8506 High Similarity NPC472573
0.8506 High Similarity NPC11685
0.8506 High Similarity NPC95810
0.8506 High Similarity NPC475759
0.8506 High Similarity NPC243577
0.8506 High Similarity NPC472569
0.8506 High Similarity NPC70716
0.8506 High Similarity NPC125106
0.8506 High Similarity NPC25768
0.8506 High Similarity NPC476974
0.8506 High Similarity NPC163719
0.85 High Similarity NPC25351
0.85 High Similarity NPC264943
0.85 High Similarity NPC92979
0.85 High Similarity NPC476262
0.8494 Intermediate Similarity NPC470995
0.8491 Intermediate Similarity NPC33938
0.8491 Intermediate Similarity NPC469503
0.8485 Intermediate Similarity NPC472774
0.8485 Intermediate Similarity NPC472282
0.8485 Intermediate Similarity NPC472775
0.8485 Intermediate Similarity NPC473766
0.8485 Intermediate Similarity NPC473753
0.8481 Intermediate Similarity NPC470997
0.8471 Intermediate Similarity NPC19747
0.8466 Intermediate Similarity NPC18347
0.8466 Intermediate Similarity NPC149896
0.8466 Intermediate Similarity NPC329938
0.8466 Intermediate Similarity NPC5079
0.8466 Intermediate Similarity NPC69028
0.8466 Intermediate Similarity NPC263432
0.8462 Intermediate Similarity NPC62799
0.8457 Intermediate Similarity NPC307383
0.8457 Intermediate Similarity NPC472671
0.8452 Intermediate Similarity NPC470159
0.8452 Intermediate Similarity NPC174982
0.8452 Intermediate Similarity NPC158663
0.8452 Intermediate Similarity NPC171525
0.8452 Intermediate Similarity NPC476973
0.8452 Intermediate Similarity NPC177940
0.8452 Intermediate Similarity NPC469349
0.8452 Intermediate Similarity NPC148185
0.8452 Intermediate Similarity NPC251865
0.8452 Intermediate Similarity NPC29704
0.8452 Intermediate Similarity NPC471104
0.8452 Intermediate Similarity NPC70403
0.8452 Intermediate Similarity NPC184817
0.8452 Intermediate Similarity NPC472568
0.8452 Intermediate Similarity NPC473088
0.8452 Intermediate Similarity NPC472571
0.8452 Intermediate Similarity NPC200471
0.8452 Intermediate Similarity NPC472572
0.8452 Intermediate Similarity NPC96903
0.8452 Intermediate Similarity NPC472575
0.8452 Intermediate Similarity NPC470157
0.8447 Intermediate Similarity NPC107646
0.8442 Intermediate Similarity NPC163087
0.8438 Intermediate Similarity NPC30222
0.8438 Intermediate Similarity NPC178932
0.8431 Intermediate Similarity NPC148374
0.8431 Intermediate Similarity NPC224491
0.8431 Intermediate Similarity NPC67003
0.8428 Intermediate Similarity NPC119252
0.8424 Intermediate Similarity NPC97574
0.8424 Intermediate Similarity NPC93172
0.8424 Intermediate Similarity NPC472141
0.8418 Intermediate Similarity NPC471001
0.8415 Intermediate Similarity NPC51568
0.8415 Intermediate Similarity NPC234660
0.8415 Intermediate Similarity NPC469889
0.8415 Intermediate Similarity NPC476197
0.8408 Intermediate Similarity NPC473215
0.8405 Intermediate Similarity NPC472653
0.8397 Intermediate Similarity NPC41182
0.8395 Intermediate Similarity NPC472772
0.8395 Intermediate Similarity NPC475066
0.8395 Intermediate Similarity NPC470119
0.8395 Intermediate Similarity NPC470118
0.8395 Intermediate Similarity NPC214495

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC8389 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
0.8698 High Similarity NPD8434 Phase 2
0.8323 Intermediate Similarity NPD4628 Phase 3
0.8063 Intermediate Similarity NPD6273 Approved
0.8049 Intermediate Similarity NPD5760 Phase 2
0.8049 Intermediate Similarity NPD5761 Phase 2
0.8049 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD7458 Discontinued
0.7977 Intermediate Similarity NPD6764 Approved
0.7977 Intermediate Similarity NPD6765 Approved
0.7975 Intermediate Similarity NPD6599 Discontinued
0.7939 Intermediate Similarity NPD7819 Suspended
0.7911 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD5844 Phase 1
0.7904 Intermediate Similarity NPD7075 Discontinued
0.7898 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD8127 Discontinued
0.7844 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD3749 Approved
0.7797 Intermediate Similarity NPD6784 Approved
0.7797 Intermediate Similarity NPD6785 Approved
0.7785 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD6559 Discontinued
0.7716 Intermediate Similarity NPD6799 Approved
0.7711 Intermediate Similarity NPD7411 Suspended
0.7706 Intermediate Similarity NPD5494 Approved
0.7679 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD6801 Discontinued
0.7647 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD919 Approved
0.764 Intermediate Similarity NPD3750 Approved
0.764 Intermediate Similarity NPD7003 Approved
0.764 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD7768 Phase 2
0.7619 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD7473 Discontinued
0.7584 Intermediate Similarity NPD8312 Approved
0.7584 Intermediate Similarity NPD8313 Approved
0.7582 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD6355 Discontinued
0.7576 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD920 Approved
0.7574 Intermediate Similarity NPD3817 Phase 2
0.756 Intermediate Similarity NPD1934 Approved
0.7558 Intermediate Similarity NPD7199 Phase 2
0.7547 Intermediate Similarity NPD3748 Approved
0.7546 Intermediate Similarity NPD7236 Approved
0.7546 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD4380 Phase 2
0.7538 Intermediate Similarity NPD8404 Phase 2
0.7531 Intermediate Similarity NPD8166 Discontinued
0.7529 Intermediate Similarity NPD3882 Suspended
0.7529 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2796 Approved
0.75 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6100 Approved
0.75 Intermediate Similarity NPD6099 Approved
0.7485 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD3226 Approved
0.7471 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD5403 Approved
0.746 Intermediate Similarity NPD7497 Discontinued
0.7457 Intermediate Similarity NPD6959 Discontinued
0.7456 Intermediate Similarity NPD37 Approved
0.7455 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD5401 Approved
0.7443 Intermediate Similarity NPD3818 Discontinued
0.7442 Intermediate Similarity NPD6234 Discontinued
0.7438 Intermediate Similarity NPD2799 Discontinued
0.7436 Intermediate Similarity NPD7095 Approved
0.7434 Intermediate Similarity NPD1608 Approved
0.7429 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD6166 Phase 2
0.7429 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD4965 Approved
0.7427 Intermediate Similarity NPD4966 Approved
0.7427 Intermediate Similarity NPD4967 Phase 2
0.7414 Intermediate Similarity NPD6232 Discontinued
0.7412 Intermediate Similarity NPD8455 Phase 2
0.7407 Intermediate Similarity NPD1549 Phase 2
0.7391 Intermediate Similarity NPD1551 Phase 2
0.7389 Intermediate Similarity NPD6798 Discontinued
0.7389 Intermediate Similarity NPD3764 Approved
0.7377 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD5402 Approved
0.7362 Intermediate Similarity NPD1243 Approved
0.736 Intermediate Similarity NPD7074 Phase 3
0.7349 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD1471 Phase 3
0.7346 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD2346 Discontinued
0.7345 Intermediate Similarity NPD7177 Discontinued
0.7345 Intermediate Similarity NPD7228 Approved
0.7342 Intermediate Similarity NPD8032 Phase 2
0.7329 Intermediate Similarity NPD7033 Discontinued
0.7325 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD7239 Suspended
0.7317 Intermediate Similarity NPD4110 Phase 3
0.7317 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD7229 Phase 3
0.7314 Intermediate Similarity NPD3787 Discontinued
0.731 Intermediate Similarity NPD2801 Approved
0.731 Intermediate Similarity NPD1465 Phase 2
0.7303 Intermediate Similarity NPD7054 Approved
0.7303 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7685 Pre-registration
0.7278 Intermediate Similarity NPD3268 Approved
0.7268 Intermediate Similarity NPD8150 Discontinued
0.7267 Intermediate Similarity NPD7097 Phase 1
0.7263 Intermediate Similarity NPD7472 Approved
0.7257 Intermediate Similarity NPD1247 Approved
0.7247 Intermediate Similarity NPD7799 Discontinued
0.7247 Intermediate Similarity NPD3751 Discontinued
0.7247 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD2532 Approved
0.7246 Intermediate Similarity NPD2533 Approved
0.7246 Intermediate Similarity NPD2534 Approved
0.7239 Intermediate Similarity NPD2344 Approved
0.7239 Intermediate Similarity NPD5763 Approved
0.7239 Intermediate Similarity NPD5762 Approved
0.7237 Intermediate Similarity NPD17 Approved
0.7233 Intermediate Similarity NPD6233 Phase 2
0.7222 Intermediate Similarity NPD4308 Phase 3
0.7222 Intermediate Similarity NPD1510 Phase 2
0.7208 Intermediate Similarity NPD3972 Approved
0.7195 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD4140 Approved
0.7188 Intermediate Similarity NPD7435 Discontinued
0.7186 Intermediate Similarity NPD1511 Approved
0.7182 Intermediate Similarity NPD7240 Approved
0.7182 Intermediate Similarity NPD7251 Discontinued
0.7179 Intermediate Similarity NPD2797 Approved
0.7175 Intermediate Similarity NPD3926 Phase 2
0.717 Intermediate Similarity NPD2313 Discontinued
0.7169 Intermediate Similarity NPD3887 Approved
0.7169 Intermediate Similarity NPD2354 Approved
0.7169 Intermediate Similarity NPD6190 Approved
0.7168 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6832 Phase 2
0.7143 Intermediate Similarity NPD7808 Phase 3
0.7143 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7028 Phase 2
0.7127 Intermediate Similarity NPD6797 Phase 2
0.712 Intermediate Similarity NPD4107 Approved
0.7101 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD1512 Approved
0.7099 Intermediate Similarity NPD1607 Approved
0.7093 Intermediate Similarity NPD6677 Suspended
0.7081 Intermediate Similarity NPD4307 Phase 2
0.7081 Intermediate Similarity NPD4060 Phase 1
0.7081 Intermediate Similarity NPD1240 Approved
0.7073 Intermediate Similarity NPD2438 Suspended
0.7073 Intermediate Similarity NPD2935 Discontinued
0.707 Intermediate Similarity NPD3266 Approved
0.707 Intermediate Similarity NPD3267 Approved
0.7066 Intermediate Similarity NPD2309 Approved
0.7065 Intermediate Similarity NPD8407 Phase 2
0.7048 Intermediate Similarity NPD2800 Approved
0.7047 Intermediate Similarity NPD3057 Approved
0.7041 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD5735 Approved
0.7031 Intermediate Similarity NPD6776 Approved
0.7031 Intermediate Similarity NPD6780 Approved
0.7031 Intermediate Similarity NPD6777 Approved
0.7031 Intermediate Similarity NPD6779 Approved
0.7031 Intermediate Similarity NPD6781 Approved
0.7031 Intermediate Similarity NPD6778 Approved
0.7031 Intermediate Similarity NPD6782 Approved
0.703 Intermediate Similarity NPD6005 Phase 3
0.703 Intermediate Similarity NPD6004 Phase 3
0.703 Intermediate Similarity NPD6002 Phase 3
0.703 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD2798 Approved
0.7013 Intermediate Similarity NPD1778 Approved
0.7006 Intermediate Similarity NPD1283 Approved
0.7005 Intermediate Similarity NPD8435 Approved
0.7005 Intermediate Similarity NPD8360 Approved
0.7005 Intermediate Similarity NPD8361 Approved
0.7 Intermediate Similarity NPD7008 Discontinued
0.7 Intermediate Similarity NPD5049 Phase 3
0.6995 Remote Similarity NPD8368 Discontinued
0.6995 Remote Similarity NPD4482 Phase 3
0.6989 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6988 Remote Similarity NPD4534 Discontinued
0.697 Remote Similarity NPD7874 Approved
0.697 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6965 Remote Similarity NPD7047 Phase 3
0.6963 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6959 Remote Similarity NPD2972 Approved
0.6959 Remote Similarity NPD3533 Approved
0.6957 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7577 Discontinued
0.6937 Remote Similarity NPD4908 Phase 1

Structure

External Identifiers

PubChem CID   46861633
ChEMBL   CHEMBL1097166
ZINC  

Physicochemical Properties

Molecular Weight:  506.27
ALogP:  0.0673
MLogP:  4.21
XLogP:  8.243
# Rotatable Bonds:  12
Polar Surface Area:  85.97
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  37

Download Data

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