Natural Product: NPC471175

Natural Product ID:  NPC471175
Common Name:   11-Epi-Toonacilin
IUPAC Name:   methyl 2-[(1R,2S)-2-[(1aR,3S,3aR,4R,5R,6R,7aS)-4,5-diacetyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate
Synonyms:  
Molecular Formula:   C31H38O9
Standard InCHIKey:  RRBQYKQIAKFGIS-WLFJESJASA-N
Standard InCHI:  InChI=1S/C31H38O9/c1-16-25(29(6)11-9-22(34)28(4,5)21(29)14-24(35)36-8)26(38-17(2)32)27(39-18(3)33)30(7)20(19-10-12-37-15-19)13-23-31(16,30)40-23/h9-12,15,20-21,23,25-27H,1,13-14H2,2-8H3/t20-,21-,23+,25+,26+,27-,29-,30+,31+/m0/s1
Canonical SMILES:  COC(=O)C[C@@H]1[C@](C)(C=CC(=O)C1(C)C)[C@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@]2([C@]3(C1=C)O[C@@H]3C[C@H]2c1cocc1)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
NPO10033 Turraea pubescens Species Meliaceae Eukaryota Twigs Dongfang, Hainan Province, China 2010-MAR PMID[23734701]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 20000 nM 20413315
NPT116 Cell Line HL-60 Homo sapiens IC50 < 10000 nM 8450319

  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 NPC471175 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
0.9932 High Similarity NPC175964
0.9932 High Similarity NPC471169
0.9669 High Similarity NPC5741
0.9463 High Similarity NPC84063
0.9412 High Similarity NPC471166
0.9412 High Similarity NPC471167
0.9351 High Similarity NPC471168
0.9161 High Similarity NPC472668
0.9103 High Similarity NPC472669
0.8924 High Similarity NPC259943
0.891 High Similarity NPC474932
0.8889 High Similarity NPC116717
0.8827 High Similarity NPC469848
0.8797 High Similarity NPC197596
0.8782 High Similarity NPC204663
0.8742 High Similarity NPC34056
0.8726 High Similarity NPC195131
0.8704 High Similarity NPC472650
0.8696 High Similarity NPC472764
0.8696 High Similarity NPC476224
0.8645 High Similarity NPC18135
0.8645 High Similarity NPC291150
0.8642 High Similarity NPC472766
0.8642 High Similarity NPC472765
0.8631 High Similarity NPC242068
0.8631 High Similarity NPC247563
0.8627 High Similarity NPC255414
0.8608 High Similarity NPC470118
0.8608 High Similarity NPC469847
0.8608 High Similarity NPC197137
0.859 High Similarity NPC29695
0.859 High Similarity NPC322546
0.859 High Similarity NPC182427
0.859 High Similarity NPC268905
0.859 High Similarity NPC308205
0.8581 High Similarity NPC5180
0.8562 High Similarity NPC472767
0.8562 High Similarity NPC6326
0.8554 High Similarity NPC478177
0.8545 High Similarity NPC471632
0.8537 High Similarity NPC285227
0.8528 High Similarity NPC327922
0.8528 High Similarity NPC242334
0.8521 High Similarity NPC105395
0.8516 High Similarity NPC471001
0.8516 High Similarity NPC125182
0.8516 High Similarity NPC69647
0.8509 High Similarity NPC165218
0.8509 High Similarity NPC476197
0.8491 Intermediate Similarity NPC167142
0.8481 Intermediate Similarity NPC469850
0.8481 Intermediate Similarity NPC92979
0.8466 Intermediate Similarity NPC173516
0.8462 Intermediate Similarity NPC156189
0.8447 Intermediate Similarity NPC470939
0.8447 Intermediate Similarity NPC96443
0.8447 Intermediate Similarity NPC290400
0.8438 Intermediate Similarity NPC475295
0.8438 Intermediate Similarity NPC473473
0.8434 Intermediate Similarity NPC94763
0.8434 Intermediate Similarity NPC477824
0.8434 Intermediate Similarity NPC236004
0.8415 Intermediate Similarity NPC471397
0.8405 Intermediate Similarity NPC478178
0.8405 Intermediate Similarity NPC149945
0.8397 Intermediate Similarity NPC470790
0.8397 Intermediate Similarity NPC470791
0.8387 Intermediate Similarity NPC221809
0.8375 Intermediate Similarity NPC214495
0.8375 Intermediate Similarity NPC475066
0.8375 Intermediate Similarity NPC470119
0.8375 Intermediate Similarity NPC286722
0.8375 Intermediate Similarity NPC195954
0.8365 Intermediate Similarity NPC476262
0.8365 Intermediate Similarity NPC264943
0.8364 Intermediate Similarity NPC472659
0.8354 Intermediate Similarity NPC472672
0.8354 Intermediate Similarity NPC478179
0.8354 Intermediate Similarity NPC476201
0.8354 Intermediate Similarity NPC476861
0.8354 Intermediate Similarity NPC476850
0.8344 Intermediate Similarity NPC159927
0.8344 Intermediate Similarity NPC476856
0.8344 Intermediate Similarity NPC476858
0.8344 Intermediate Similarity NPC469335
0.8344 Intermediate Similarity NPC476857
0.8333 Intermediate Similarity NPC472771
0.8333 Intermediate Similarity NPC470181
0.8323 Intermediate Similarity NPC237155
0.8323 Intermediate Similarity NPC472671
0.8323 Intermediate Similarity NPC471292
0.8323 Intermediate Similarity NPC470999
0.8323 Intermediate Similarity NPC471437
0.8323 Intermediate Similarity NPC475226
0.8323 Intermediate Similarity NPC469576
0.8313 Intermediate Similarity NPC60973
0.8313 Intermediate Similarity NPC209364
0.8313 Intermediate Similarity NPC159232
0.8312 Intermediate Similarity NPC199044
0.8312 Intermediate Similarity NPC238843
0.8303 Intermediate Similarity NPC160651
0.8303 Intermediate Similarity NPC472673
0.8302 Intermediate Similarity NPC253201
0.8302 Intermediate Similarity NPC302054
0.8301 Intermediate Similarity NPC121158
0.8289 Intermediate Similarity NPC56197
0.8282 Intermediate Similarity NPC663
0.8282 Intermediate Similarity NPC292389
0.8282 Intermediate Similarity NPC472139
0.8282 Intermediate Similarity NPC14499
0.8282 Intermediate Similarity NPC472773
0.8282 Intermediate Similarity NPC224394
0.8282 Intermediate Similarity NPC476035
0.8282 Intermediate Similarity NPC469846
0.8282 Intermediate Similarity NPC469338
0.8282 Intermediate Similarity NPC475039
0.8274 Intermediate Similarity NPC167340
0.8274 Intermediate Similarity NPC469633
0.8272 Intermediate Similarity NPC305016
0.8272 Intermediate Similarity NPC25255
0.8272 Intermediate Similarity NPC191828
0.8269 Intermediate Similarity NPC471174
0.8261 Intermediate Similarity NPC88007
0.8261 Intermediate Similarity NPC299038
0.8261 Intermediate Similarity NPC472283
0.8258 Intermediate Similarity NPC5676
0.8253 Intermediate Similarity NPC470995
0.825 Intermediate Similarity NPC296807
0.825 Intermediate Similarity NPC141538
0.825 Intermediate Similarity NPC155939
0.8247 Intermediate Similarity NPC80635
0.8242 Intermediate Similarity NPC472775
0.8242 Intermediate Similarity NPC476853
0.8242 Intermediate Similarity NPC473766
0.8242 Intermediate Similarity NPC473753
0.8242 Intermediate Similarity NPC472774
0.8239 Intermediate Similarity NPC471002
0.8239 Intermediate Similarity NPC470996
0.8239 Intermediate Similarity NPC75906
0.8239 Intermediate Similarity NPC33938
0.8232 Intermediate Similarity NPC470940
0.8232 Intermediate Similarity NPC469849
0.8232 Intermediate Similarity NPC276551
0.8232 Intermediate Similarity NPC123088
0.8232 Intermediate Similarity NPC476860
0.8228 Intermediate Similarity NPC477404
0.8228 Intermediate Similarity NPC196864
0.8228 Intermediate Similarity NPC470997
0.8228 Intermediate Similarity NPC476122
0.8221 Intermediate Similarity NPC470792
0.8221 Intermediate Similarity NPC149896
0.8221 Intermediate Similarity NPC193798
0.8221 Intermediate Similarity NPC68848
0.8221 Intermediate Similarity NPC117986
0.821 Intermediate Similarity NPC477403
0.8199 Intermediate Similarity NPC263265
0.8199 Intermediate Similarity NPC126723
0.8199 Intermediate Similarity NPC107646
0.8194 Intermediate Similarity NPC251865
0.8187 Intermediate Similarity NPC34421
0.8187 Intermediate Similarity NPC98206
0.8187 Intermediate Similarity NPC57998
0.8187 Intermediate Similarity NPC237259
0.8182 Intermediate Similarity NPC23387
0.8182 Intermediate Similarity NPC470875
0.8176 Intermediate Similarity NPC471000
0.8176 Intermediate Similarity NPC272590
0.8171 Intermediate Similarity NPC51568
0.8171 Intermediate Similarity NPC285567
0.8171 Intermediate Similarity NPC234660
0.8165 Intermediate Similarity NPC234494
0.8165 Intermediate Similarity NPC472654
0.8165 Intermediate Similarity NPC329180
0.816 Intermediate Similarity NPC477402
0.816 Intermediate Similarity NPC472653
0.816 Intermediate Similarity NPC475381
0.816 Intermediate Similarity NPC470789
0.8153 Intermediate Similarity NPC216755
0.8153 Intermediate Similarity NPC71821
0.8148 Intermediate Similarity NPC194499
0.8148 Intermediate Similarity NPC472772
0.8148 Intermediate Similarity NPC187149
0.8148 Intermediate Similarity NPC472777
0.8148 Intermediate Similarity NPC472778
0.8148 Intermediate Similarity NPC472776
0.8137 Intermediate Similarity NPC469336
0.8133 Intermediate Similarity NPC472282
0.8133 Intermediate Similarity NPC270312
0.8129 Intermediate Similarity NPC223415
0.8129 Intermediate Similarity NPC470938
0.8121 Intermediate Similarity NPC27541
0.8121 Intermediate Similarity NPC271657
0.8121 Intermediate Similarity NPC126984
0.8121 Intermediate Similarity NPC62692
0.8121 Intermediate Similarity NPC61967
0.811 Intermediate Similarity NPC200782
0.811 Intermediate Similarity NPC18347
0.811 Intermediate Similarity NPC82851
0.811 Intermediate Similarity NPC69028
0.811 Intermediate Similarity NPC5079

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471175 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
0.8025 Intermediate Similarity NPD5760 Phase 2
0.8025 Intermediate Similarity NPD5761 Phase 2
0.7746 Intermediate Similarity NPD6764 Approved
0.7746 Intermediate Similarity NPD6765 Approved
0.7727 Intermediate Similarity NPD8434 Phase 2
0.7725 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD6785 Approved
0.7571 Intermediate Similarity NPD6784 Approved
0.7073 Intermediate Similarity NPD4628 Phase 3
0.7029 Intermediate Similarity NPD8127 Discontinued
0.6995 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6988 Remote Similarity NPD7236 Approved
0.6964 Remote Similarity NPD6273 Approved
0.6901 Remote Similarity NPD6599 Discontinued
0.6891 Remote Similarity NPD7497 Discontinued
0.6882 Remote Similarity NPD7239 Suspended
0.6879 Remote Similarity NPD7819 Suspended
0.6875 Remote Similarity NPD5494 Approved
0.6868 Remote Similarity NPD7685 Pre-registration
0.6864 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6836 Remote Similarity NPD1247 Approved
0.6833 Remote Similarity NPD7799 Discontinued
0.6824 Remote Similarity NPD920 Approved
0.6818 Remote Similarity NPD919 Approved
0.6807 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6796 Remote Similarity NPD5844 Phase 1
0.6782 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6766 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6761 Remote Similarity NPD7075 Discontinued
0.6706 Remote Similarity NPD642 Clinical (unspecified phase)
0.6687 Remote Similarity NPD6002 Phase 3
0.6687 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6687 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6687 Remote Similarity NPD5763 Approved
0.6687 Remote Similarity NPD6005 Phase 3
0.6687 Remote Similarity NPD6004 Phase 3
0.6687 Remote Similarity NPD5762 Approved
0.6686 Remote Similarity NPD643 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3748 Approved
0.6667 Remote Similarity NPD8032 Phase 2
0.6667 Remote Similarity NPD7411 Suspended
0.665 Remote Similarity NPD8404 Phase 2
0.6648 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6648 Remote Similarity NPD3817 Phase 2
0.6648 Remote Similarity NPD7199 Phase 2
0.6647 Remote Similarity NPD6799 Approved
0.6647 Remote Similarity NPD3226 Approved
0.6629 Remote Similarity NPD6801 Discontinued
0.6628 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6627 Remote Similarity NPD2796 Approved
0.661 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6609 Remote Similarity NPD7028 Phase 2
0.6608 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6595 Remote Similarity NPD6559 Discontinued
0.6593 Remote Similarity NPD7473 Discontinued
0.6587 Remote Similarity NPD1471 Phase 3
0.6587 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6575 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6564 Remote Similarity NPD4107 Approved
0.6557 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6552 Remote Similarity NPD7458 Discontinued
0.6517 Remote Similarity NPD7058 Phase 2
0.6517 Remote Similarity NPD7057 Phase 3
0.6509 Remote Similarity NPD1243 Approved
0.6497 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6485 Remote Similarity NPD6355 Discontinued
0.6481 Remote Similarity NPD6832 Phase 2
0.6471 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6471 Remote Similarity NPD3750 Approved
0.6471 Remote Similarity NPD4110 Phase 3
0.6461 Remote Similarity NPD5402 Approved
0.6458 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6448 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6447 Remote Similarity NPD4482 Phase 3
0.6446 Remote Similarity NPD6653 Approved
0.6441 Remote Similarity NPD1934 Approved
0.6438 Remote Similarity NPD1876 Approved
0.6433 Remote Similarity NPD17 Approved
0.6433 Remote Similarity NPD3887 Approved
0.6429 Remote Similarity NPD6100 Approved
0.6429 Remote Similarity NPD2438 Suspended
0.6429 Remote Similarity NPD6232 Discontinued
0.6429 Remote Similarity NPD6099 Approved
0.6429 Remote Similarity NPD8285 Discontinued
0.6425 Remote Similarity NPD4967 Phase 2
0.6425 Remote Similarity NPD4965 Approved
0.6425 Remote Similarity NPD4966 Approved
0.6424 Remote Similarity NPD4140 Approved
0.642 Remote Similarity NPD4380 Phase 2
0.6416 Remote Similarity NPD2532 Approved
0.6416 Remote Similarity NPD2534 Approved
0.6416 Remote Similarity NPD2533 Approved
0.6415 Remote Similarity NPD3972 Approved
0.6402 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6398 Remote Similarity NPD3266 Approved
0.6398 Remote Similarity NPD3267 Approved
0.6393 Remote Similarity NPD3926 Phase 2
0.6389 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6378 Remote Similarity NPD3818 Discontinued
0.6378 Remote Similarity NPD3751 Discontinued
0.6375 Remote Similarity NPD5327 Phase 3
0.6369 Remote Similarity NPD5353 Approved
0.6369 Remote Similarity NPD2799 Discontinued
0.6359 Remote Similarity NPD2403 Approved
0.6358 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6358 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6354 Remote Similarity NPD6234 Discontinued
0.6354 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6353 Remote Similarity NPD970 Clinical (unspecified phase)
0.6349 Remote Similarity NPD8312 Approved
0.6349 Remote Similarity NPD8313 Approved
0.6348 Remote Similarity NPD37 Approved
0.6343 Remote Similarity NPD5403 Approved
0.6335 Remote Similarity NPD8150 Discontinued
0.6333 Remote Similarity NPD3882 Suspended
0.6331 Remote Similarity NPD1551 Phase 2
0.633 Remote Similarity NPD8368 Discontinued
0.6322 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6322 Remote Similarity NPD5401 Approved
0.6316 Remote Similarity NPD8407 Phase 2
0.6316 Remote Similarity NPD2800 Approved
0.6313 Remote Similarity NPD2801 Approved
0.6312 Remote Similarity NPD1608 Approved
0.631 Remote Similarity NPD7074 Phase 3
0.6303 Remote Similarity NPD3268 Approved
0.6298 Remote Similarity NPD3749 Approved
0.6294 Remote Similarity NPD2346 Discontinued
0.6292 Remote Similarity NPD6385 Approved
0.6292 Remote Similarity NPD6386 Approved
0.6289 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6287 Remote Similarity NPD5735 Approved
0.6284 Remote Similarity NPD6959 Discontinued
0.6277 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6272 Remote Similarity NPD7033 Discontinued
0.6271 Remote Similarity NPD5808 Clinical (unspecified phase)
0.627 Remote Similarity NPD6167 Clinical (unspecified phase)
0.627 Remote Similarity NPD6168 Clinical (unspecified phase)
0.627 Remote Similarity NPD6166 Phase 2
0.6266 Remote Similarity NPD5585 Approved
0.6265 Remote Similarity NPD6663 Approved
0.6258 Remote Similarity NPD5647 Approved
0.6257 Remote Similarity NPD1549 Phase 2
0.6257 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6257 Remote Similarity NPD7054 Approved
0.625 Remote Similarity NPD3787 Discontinued
0.625 Remote Similarity NPD7315 Approved
0.625 Remote Similarity NPD6808 Phase 2
0.625 Remote Similarity NPD6353 Approved
0.6243 Remote Similarity NPD7768 Phase 2
0.6235 Remote Similarity NPD2935 Discontinued
0.6229 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6228 Remote Similarity NPD4307 Phase 2
0.6228 Remote Similarity NPD2979 Phase 3
0.6226 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6223 Remote Similarity NPD7472 Approved
0.6222 Remote Similarity NPD1465 Phase 2
0.6216 Remote Similarity NPD5242 Approved
0.6211 Remote Similarity NPD7507 Approved
0.6211 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6209 Remote Similarity NPD7907 Approved
0.6207 Remote Similarity NPD6652 Clinical (unspecified phase)
0.6203 Remote Similarity NPD7228 Approved
0.62 Remote Similarity NPD6008 Approved
0.6199 Remote Similarity NPD2353 Approved
0.6199 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6199 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6199 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6196 Remote Similarity NPD6362 Approved
0.6196 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6196 Remote Similarity NPD7319 Approved
0.6194 Remote Similarity NPD1241 Discontinued
0.619 Remote Similarity NPD4111 Phase 1
0.619 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6185 Remote Similarity NPD7003 Approved
0.6185 Remote Similarity NPD8166 Discontinued
0.6172 Remote Similarity NPD5980 Discovery
0.617 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6169 Remote Similarity NPD3057 Approved
0.6162 Remote Similarity NPD7229 Phase 3
0.6158 Remote Similarity NPD7251 Discontinued
0.6154 Remote Similarity NPD6651 Approved
0.6149 Remote Similarity NPD6190 Approved
0.6139 Remote Similarity NPD7435 Discontinued
0.6133 Remote Similarity NPD8455 Phase 2
0.6126 Remote Similarity NPD7808 Phase 3
0.6125 Remote Similarity NPD1778 Approved
0.6121 Remote Similarity NPD5736 Approved
0.6118 Remote Similarity NPD7097 Phase 1
0.6114 Remote Similarity NPD4665 Approved
0.6111 Remote Similarity NPD6873 Phase 2
0.6108 Remote Similarity NPD2313 Discontinued
0.6108 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6105 Remote Similarity NPD6797 Phase 2
0.6103 Remote Similarity NPD8435 Approved
0.6103 Remote Similarity NPD8361 Approved
0.6103 Remote Similarity NPD8360 Approved
0.6099 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6095 Remote Similarity NPD447 Suspended
0.6095 Remote Similarity NPD230 Phase 1
0.6095 Remote Similarity NPD1933 Approved

Structure

External Identifiers

PubChem CID   73348892
ChEMBL   CHEMBL2386309
ZINC  

Physicochemical Properties

Molecular Weight:  554.25
ALogP:  0.768
MLogP:  3.88
XLogP:  1.78
# Rotatable Bonds:  16
Polar Surface Area:  117.73
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  40

Download Data

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Biological Activities  
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