Natural Product: NPC61442

Natural Product ID:  NPC61442
Common Name:   Tithofolinolide
IUPAC Name:   [(3aR,4R,5aR,6R,8S,9S,9aS,9bS)-8-acetyloxy-6,9-dihydroxy-5a,9-dimethyl-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] 2-methylpropanoate
Synonyms:   tithofolinolide
Molecular Formula:   C21H30O8
Standard InCHIKey:  UABMYELNJDXARW-SYUVKRIKSA-N
Standard InCHI:  InChI=1S/C21H30O8/c1-9(2)18(24)28-12-8-20(5)13(23)7-14(27-11(4)22)21(6,26)17(20)16-15(12)10(3)19(25)29-16/h9,12-17,23,26H,3,7-8H2,1-2,4-6H3/t12-,13-,14+,15-,16+,17-,20+,21-/m1/s1
Canonical SMILES:  CC(=O)O[C@H]1C[C@@H](O)[C@]2([C@H]([C@]1(C)O)[C@H]1OC(=O)C(=C)[C@@H]1[C@@H](C2)OC(=O)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
NPO19764 Tithonia diversifolia Species Asteraceae Eukaryota PMID[11975495]
NPO19764 Tithonia diversifolia Species Asteraceae Eukaryota TCMID*

  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 = 37.4 ug/ml 11975495
NPT2 Others Unspecified IC50 = 40.2 ug/ml 11975495
NPT1851 Cell Line Col2 Homo sapiens IC50 > 20 ug/ml 11975495

  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 NPC61442 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
0.9474 High Similarity NPC473963
0.9388 High Similarity NPC72842
0.9388 High Similarity NPC99510
0.9368 High Similarity NPC93245
0.9368 High Similarity NPC473964
0.9263 High Similarity NPC157686
0.9263 High Similarity NPC259042
0.9158 High Similarity NPC148000
0.9158 High Similarity NPC469596
0.9158 High Similarity NPC225474
0.91 High Similarity NPC283850
0.9072 High Similarity NPC136781
0.902 High Similarity NPC37628
0.899 High Similarity NPC475958
0.8958 High Similarity NPC24861
0.8922 High Similarity NPC78966
0.8922 High Similarity NPC284732
0.8889 High Similarity NPC47024
0.8878 High Similarity NPC474395
0.8842 High Similarity NPC475776
0.88 High Similarity NPC308824
0.8788 High Similarity NPC476806
0.8788 High Similarity NPC476807
0.8776 High Similarity NPC284518
0.8774 High Similarity NPC477126
0.8737 High Similarity NPC116620
0.8687 High Similarity NPC474921
0.8673 High Similarity NPC90014
0.8627 High Similarity NPC156681
0.86 High Similarity NPC216478
0.8586 High Similarity NPC228766
0.8586 High Similarity NPC256227
0.8586 High Similarity NPC165528
0.8558 High Similarity NPC187435
0.8558 High Similarity NPC67321
0.8544 High Similarity NPC301787
0.8542 High Similarity NPC194642
0.8529 High Similarity NPC164551
0.8526 High Similarity NPC175293
0.8526 High Similarity NPC305029
0.8515 High Similarity NPC477655
0.8515 High Similarity NPC477656
0.8485 Intermediate Similarity NPC56369
0.8476 Intermediate Similarity NPC273155
0.8469 Intermediate Similarity NPC147272
0.8462 Intermediate Similarity NPC222833
0.8431 Intermediate Similarity NPC98225
0.8431 Intermediate Similarity NPC111292
0.8431 Intermediate Similarity NPC242666
0.8421 Intermediate Similarity NPC9231
0.8421 Intermediate Similarity NPC185638
0.8421 Intermediate Similarity NPC85698
0.8411 Intermediate Similarity NPC474846
0.8411 Intermediate Similarity NPC469656
0.8411 Intermediate Similarity NPC469655
0.8411 Intermediate Similarity NPC157476
0.8396 Intermediate Similarity NPC474243
0.8384 Intermediate Similarity NPC473434
0.8384 Intermediate Similarity NPC66581
0.8384 Intermediate Similarity NPC471446
0.8384 Intermediate Similarity NPC474841
0.8381 Intermediate Similarity NPC166993
0.8367 Intermediate Similarity NPC122057
0.8365 Intermediate Similarity NPC477127
0.8364 Intermediate Similarity NPC473590
0.835 Intermediate Similarity NPC476081
0.8333 Intermediate Similarity NPC181103
0.8333 Intermediate Similarity NPC472002
0.8317 Intermediate Similarity NPC111348
0.8302 Intermediate Similarity NPC231278
0.8302 Intermediate Similarity NPC218123
0.8302 Intermediate Similarity NPC112895
0.8302 Intermediate Similarity NPC306265
0.8302 Intermediate Similarity NPC255082
0.8286 Intermediate Similarity NPC138908
0.8286 Intermediate Similarity NPC200957
0.8273 Intermediate Similarity NPC471816
0.8265 Intermediate Similarity NPC153853
0.8257 Intermediate Similarity NPC49451
0.8252 Intermediate Similarity NPC252614
0.8247 Intermediate Similarity NPC50847
0.8241 Intermediate Similarity NPC94650
0.8224 Intermediate Similarity NPC42662
0.8224 Intermediate Similarity NPC299590
0.8224 Intermediate Similarity NPC154906
0.8211 Intermediate Similarity NPC97505
0.8208 Intermediate Similarity NPC143609
0.8198 Intermediate Similarity NPC13713
0.8198 Intermediate Similarity NPC287343
0.8198 Intermediate Similarity NPC97908
0.8198 Intermediate Similarity NPC474654
0.8198 Intermediate Similarity NPC470775
0.8198 Intermediate Similarity NPC58662
0.8198 Intermediate Similarity NPC473968
0.8198 Intermediate Similarity NPC176513
0.8198 Intermediate Similarity NPC122033
0.8198 Intermediate Similarity NPC470854
0.819 Intermediate Similarity NPC146731
0.819 Intermediate Similarity NPC296950
0.8174 Intermediate Similarity NPC24651
0.8173 Intermediate Similarity NPC472552
0.8165 Intermediate Similarity NPC269530
0.8165 Intermediate Similarity NPC473397
0.8165 Intermediate Similarity NPC474516
0.8163 Intermediate Similarity NPC77001
0.8163 Intermediate Similarity NPC253618
0.8155 Intermediate Similarity NPC188968
0.8148 Intermediate Similarity NPC475134
0.8148 Intermediate Similarity NPC100908
0.8148 Intermediate Similarity NPC85391
0.8148 Intermediate Similarity NPC253906
0.8148 Intermediate Similarity NPC475563
0.8148 Intermediate Similarity NPC5103
0.8144 Intermediate Similarity NPC470012
0.8137 Intermediate Similarity NPC472998
0.8137 Intermediate Similarity NPC274793
0.8131 Intermediate Similarity NPC208461
0.8131 Intermediate Similarity NPC469916
0.8131 Intermediate Similarity NPC181994
0.8131 Intermediate Similarity NPC472439
0.8131 Intermediate Similarity NPC94377
0.8131 Intermediate Similarity NPC289702
0.8125 Intermediate Similarity NPC124676
0.8125 Intermediate Similarity NPC146280
0.8113 Intermediate Similarity NPC111952
0.8113 Intermediate Similarity NPC102352
0.8108 Intermediate Similarity NPC471127
0.8108 Intermediate Similarity NPC234858
0.8108 Intermediate Similarity NPC96312
0.8108 Intermediate Similarity NPC179626
0.8108 Intermediate Similarity NPC474734
0.8108 Intermediate Similarity NPC40632
0.8108 Intermediate Similarity NPC328374
0.8108 Intermediate Similarity NPC154363
0.8108 Intermediate Similarity NPC251236
0.8095 Intermediate Similarity NPC120321
0.8095 Intermediate Similarity NPC209298
0.8095 Intermediate Similarity NPC225238
0.8095 Intermediate Similarity NPC159533
0.8095 Intermediate Similarity NPC122811
0.8095 Intermediate Similarity NPC277074
0.8091 Intermediate Similarity NPC89018
0.8091 Intermediate Similarity NPC471252
0.8091 Intermediate Similarity NPC94509
0.8087 Intermediate Similarity NPC67251
0.8081 Intermediate Similarity NPC471378
0.8081 Intermediate Similarity NPC312471
0.8077 Intermediate Similarity NPC49532
0.8077 Intermediate Similarity NPC472554
0.8073 Intermediate Similarity NPC213320
0.8073 Intermediate Similarity NPC475668
0.8073 Intermediate Similarity NPC473921
0.8073 Intermediate Similarity NPC475480
0.8073 Intermediate Similarity NPC29505
0.8058 Intermediate Similarity NPC89099
0.8058 Intermediate Similarity NPC20479
0.8058 Intermediate Similarity NPC28864
0.8058 Intermediate Similarity NPC38296
0.8058 Intermediate Similarity NPC38471
0.8058 Intermediate Similarity NPC98837
0.8058 Intermediate Similarity NPC162459
0.8056 Intermediate Similarity NPC102741
0.8056 Intermediate Similarity NPC472216
0.8056 Intermediate Similarity NPC284828
0.8056 Intermediate Similarity NPC131903
0.8056 Intermediate Similarity NPC173905
0.8056 Intermediate Similarity NPC5475
0.8053 Intermediate Similarity NPC475775
0.8053 Intermediate Similarity NPC476529
0.8053 Intermediate Similarity NPC469380
0.8041 Intermediate Similarity NPC477920
0.8037 Intermediate Similarity NPC144854
0.8037 Intermediate Similarity NPC3316
0.8037 Intermediate Similarity NPC230541
0.8037 Intermediate Similarity NPC180744
0.8036 Intermediate Similarity NPC469684
0.8036 Intermediate Similarity NPC98249
0.8036 Intermediate Similarity NPC10721
0.8036 Intermediate Similarity NPC53396
0.8036 Intermediate Similarity NPC296822
0.8021 Intermediate Similarity NPC130966
0.8019 Intermediate Similarity NPC65523
0.8019 Intermediate Similarity NPC258532
0.8018 Intermediate Similarity NPC88867
0.8018 Intermediate Similarity NPC299849
0.8018 Intermediate Similarity NPC117712
0.8018 Intermediate Similarity NPC226608
0.8018 Intermediate Similarity NPC472400
0.8018 Intermediate Similarity NPC73314
0.8018 Intermediate Similarity NPC473798
0.8 Intermediate Similarity NPC470063
0.8 Intermediate Similarity NPC295791
0.8 Intermediate Similarity NPC474927
0.8 Intermediate Similarity NPC162009
0.8 Intermediate Similarity NPC226988
0.8 Intermediate Similarity NPC162973
0.8 Intermediate Similarity NPC42658
0.8 Intermediate Similarity NPC275990
0.8 Intermediate Similarity NPC186363
0.8 Intermediate Similarity NPC312805

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC61442 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
0.8224 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.8131 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD4225 Approved
0.787 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD6686 Approved
0.7611 Intermediate Similarity NPD8133 Approved
0.7458 Intermediate Similarity NPD6921 Approved
0.7414 Intermediate Similarity NPD7115 Discovery
0.7407 Intermediate Similarity NPD5344 Discontinued
0.7383 Intermediate Similarity NPD7638 Approved
0.7315 Intermediate Similarity NPD7639 Approved
0.7315 Intermediate Similarity NPD7640 Approved
0.7288 Intermediate Similarity NPD7516 Approved
0.7257 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD6319 Approved
0.7213 Intermediate Similarity NPD7507 Approved
0.7203 Intermediate Similarity NPD7327 Approved
0.7203 Intermediate Similarity NPD7328 Approved
0.7177 Intermediate Similarity NPD7319 Approved
0.7155 Intermediate Similarity NPD4632 Approved
0.7143 Intermediate Similarity NPD8034 Phase 2
0.7143 Intermediate Similarity NPD8035 Phase 2
0.7069 Intermediate Similarity NPD8297 Approved
0.7048 Intermediate Similarity NPD6698 Approved
0.7048 Intermediate Similarity NPD46 Approved
0.7 Intermediate Similarity NPD6648 Approved
0.6991 Remote Similarity NPD6008 Approved
0.6983 Remote Similarity NPD6649 Approved
0.6983 Remote Similarity NPD6650 Approved
0.6957 Remote Similarity NPD6372 Approved
0.6957 Remote Similarity NPD6373 Approved
0.693 Remote Similarity NPD5697 Approved
0.693 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6916 Remote Similarity NPD6399 Phase 3
0.6897 Remote Similarity NPD6371 Approved
0.6893 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6885 Remote Similarity NPD8296 Approved
0.6885 Remote Similarity NPD8335 Approved
0.6885 Remote Similarity NPD8380 Approved
0.6885 Remote Similarity NPD8378 Approved
0.6885 Remote Similarity NPD8033 Approved
0.6885 Remote Similarity NPD8379 Approved
0.6875 Remote Similarity NPD7632 Discontinued
0.687 Remote Similarity NPD6899 Approved
0.687 Remote Similarity NPD6881 Approved
0.6855 Remote Similarity NPD7492 Approved
0.6842 Remote Similarity NPD6402 Approved
0.6842 Remote Similarity NPD7128 Approved
0.6842 Remote Similarity NPD5739 Approved
0.6842 Remote Similarity NPD6675 Approved
0.6833 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6833 Remote Similarity NPD6009 Approved
0.6818 Remote Similarity NPD7902 Approved
0.681 Remote Similarity NPD6014 Approved
0.681 Remote Similarity NPD6012 Approved
0.681 Remote Similarity NPD6013 Approved
0.6803 Remote Similarity NPD6054 Approved
0.6803 Remote Similarity NPD8377 Approved
0.6803 Remote Similarity NPD8294 Approved
0.68 Remote Similarity NPD6616 Approved
0.6783 Remote Similarity NPD5701 Approved
0.6783 Remote Similarity NPD6412 Phase 2
0.678 Remote Similarity NPD6882 Approved
0.6774 Remote Similarity NPD8328 Phase 3
0.6765 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6752 Remote Similarity NPD7290 Approved
0.6752 Remote Similarity NPD6883 Approved
0.6752 Remote Similarity NPD7102 Approved
0.6748 Remote Similarity NPD8515 Approved
0.6748 Remote Similarity NPD8517 Approved
0.6748 Remote Similarity NPD8513 Phase 3
0.6748 Remote Similarity NPD8516 Approved
0.6748 Remote Similarity NPD5983 Phase 2
0.6748 Remote Similarity NPD6016 Approved
0.6748 Remote Similarity NPD7503 Approved
0.6748 Remote Similarity NPD6015 Approved
0.6746 Remote Similarity NPD7078 Approved
0.6731 Remote Similarity NPD1694 Approved
0.6724 Remote Similarity NPD6011 Approved
0.6724 Remote Similarity NPD7320 Approved
0.6697 Remote Similarity NPD7748 Approved
0.6695 Remote Similarity NPD6847 Approved
0.6695 Remote Similarity NPD6617 Approved
0.6695 Remote Similarity NPD6869 Approved
0.6695 Remote Similarity NPD8130 Phase 1
0.6695 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6694 Remote Similarity NPD6370 Approved
0.6694 Remote Similarity NPD5988 Approved
0.6693 Remote Similarity NPD7736 Approved
0.6667 Remote Similarity NPD3618 Phase 1
0.6667 Remote Similarity NPD6059 Approved
0.6667 Remote Similarity NPD7515 Phase 2
0.664 Remote Similarity NPD7604 Phase 2
0.6637 Remote Similarity NPD1700 Approved
0.6636 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6614 Remote Similarity NPD8293 Discontinued
0.661 Remote Similarity NPD4634 Approved
0.6604 Remote Similarity NPD7524 Approved
0.6579 Remote Similarity NPD5211 Phase 2
0.6574 Remote Similarity NPD7838 Discovery
0.6571 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6549 Remote Similarity NPD5286 Approved
0.6549 Remote Similarity NPD4696 Approved
0.6549 Remote Similarity NPD5285 Approved
0.6545 Remote Similarity NPD7900 Approved
0.6545 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6535 Remote Similarity NPD6697 Approved
0.6535 Remote Similarity NPD6115 Approved
0.6535 Remote Similarity NPD6336 Discontinued
0.6535 Remote Similarity NPD6114 Approved
0.6535 Remote Similarity NPD6118 Approved
0.6518 Remote Similarity NPD6083 Phase 2
0.6518 Remote Similarity NPD6084 Phase 2
0.6518 Remote Similarity NPD4755 Approved
0.65 Remote Similarity NPD6053 Discontinued
0.6484 Remote Similarity NPD8074 Phase 3
0.6481 Remote Similarity NPD1695 Approved
0.6475 Remote Similarity NPD6274 Approved
0.6466 Remote Similarity NPD5141 Approved
0.646 Remote Similarity NPD8029 Clinical (unspecified phase)
0.646 Remote Similarity NPD5696 Approved
0.6455 Remote Similarity NPD4202 Approved
0.6442 Remote Similarity NPD3667 Approved
0.6436 Remote Similarity NPD6116 Phase 1
0.6435 Remote Similarity NPD5224 Approved
0.6435 Remote Similarity NPD5226 Approved
0.6435 Remote Similarity NPD5225 Approved
0.6435 Remote Similarity NPD4633 Approved
0.6417 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6404 Remote Similarity NPD4700 Approved
0.6396 Remote Similarity NPD5282 Discontinued
0.6381 Remote Similarity NPD4788 Approved
0.6379 Remote Similarity NPD5175 Approved
0.6379 Remote Similarity NPD5174 Approved
0.6364 Remote Similarity NPD7637 Suspended
0.6364 Remote Similarity NPD7983 Approved
0.6364 Remote Similarity NPD6079 Approved
0.6349 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6348 Remote Similarity NPD5223 Approved
0.6339 Remote Similarity NPD5695 Phase 3
0.6339 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6337 Remote Similarity NPD6117 Approved
0.633 Remote Similarity NPD5328 Approved
0.6321 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6321 Remote Similarity NPD4786 Approved
0.632 Remote Similarity NPD7100 Approved
0.632 Remote Similarity NPD7101 Approved
0.6306 Remote Similarity NPD5778 Approved
0.6306 Remote Similarity NPD5779 Approved
0.6303 Remote Similarity NPD4729 Approved
0.6303 Remote Similarity NPD4730 Approved
0.6296 Remote Similarity NPD3573 Approved
0.629 Remote Similarity NPD6317 Approved
0.6288 Remote Similarity NPD7260 Phase 2
0.6283 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6283 Remote Similarity NPD5221 Approved
0.6283 Remote Similarity NPD4697 Phase 3
0.6283 Remote Similarity NPD5222 Approved
0.6271 Remote Similarity NPD4768 Approved
0.6271 Remote Similarity NPD4767 Approved
0.625 Remote Similarity NPD6067 Discontinued
0.6241 Remote Similarity NPD6845 Suspended
0.624 Remote Similarity NPD6335 Approved
0.624 Remote Similarity NPD6314 Approved
0.624 Remote Similarity NPD6313 Approved
0.6228 Remote Similarity NPD5173 Approved
0.6226 Remote Similarity NPD6695 Phase 3
0.6216 Remote Similarity NPD6411 Approved
0.6216 Remote Similarity NPD5693 Phase 1
0.6207 Remote Similarity NPD4159 Approved
0.6204 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6204 Remote Similarity NPD5330 Approved
0.6204 Remote Similarity NPD6409 Approved
0.6204 Remote Similarity NPD7146 Approved
0.6204 Remote Similarity NPD6684 Approved
0.6204 Remote Similarity NPD7521 Approved
0.6204 Remote Similarity NPD7334 Approved
0.6198 Remote Similarity NPD5248 Approved
0.6198 Remote Similarity NPD5249 Phase 3
0.6198 Remote Similarity NPD5247 Approved
0.6198 Remote Similarity NPD5250 Approved
0.6198 Remote Similarity NPD5251 Approved
0.6195 Remote Similarity NPD5210 Approved
0.6195 Remote Similarity NPD4629 Approved
0.6186 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6183 Remote Similarity NPD6033 Approved
0.6182 Remote Similarity NPD4753 Phase 2
0.6168 Remote Similarity NPD3666 Approved
0.6168 Remote Similarity NPD3665 Phase 1
0.6168 Remote Similarity NPD3133 Approved
0.6167 Remote Similarity NPD5128 Approved
0.6162 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6139 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6126 Remote Similarity NPD5785 Approved
0.6126 Remote Similarity NPD3168 Discontinued
0.6106 Remote Similarity NPD6001 Approved
0.6102 Remote Similarity NPD4754 Approved
0.6095 Remote Similarity NPD7525 Registered
0.6094 Remote Similarity NPD6909 Approved

Structure

External Identifiers

PubChem CID   10938482
ChEMBL   CHEMBL464698
ZINC  

Physicochemical Properties

Molecular Weight:  410.19
ALogP:  -0.2786
MLogP:  2.89
XLogP:  1.151
# Rotatable Bonds:  12
Polar Surface Area:  119.36
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  29

Download Data

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General Info & Identifiers & Properties  
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Biological Activities  
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