Natural Product: NPC51978

Natural Product ID:  NPC51978
Common Name:   Ailanthone
IUPAC Name:  
Synonyms:   Ailanthone
Molecular Formula:   C20H24O7
Standard InCHIKey:  WBBVXGHSWZIJST-RLQYZCPESA-N
Standard InCHI:  InChI=1S/C20H24O7/c1-8-4-12(21)16(24)18(3)10(8)5-13-19-7-26-20(25,17(18)19)15(23)9(2)11(19)6-14(22)27-13/h4,10-11,13,15-17,23-25H,2,5-7H2,1,3H3/t10-,11-,13+,15+,16+,17+,18+,19+,20-/m0/s1
Canonical SMILES:  O=C1O[C@@H]2C[C@H]3C(=CC(=O)[C@H]([C@@]3([C@@H]3[C@@]42[C@@H](C1)C(=C)[C@H]([C@@]3(OC4)O)O)C)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
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota PMID[23290052]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota stem barks PMID[25666824]
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota PMID[19299148]
NPO6884 Ailanthi cortex NA NA NA TCMSP*
NPO15443 Ailanthus altissima Species Simaroubaceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.003 ug/ml 19299148
NPT992 Organism Entamoeba histolytica Entamoeba histolytica IC50 = 0.14 ug/ml 10.1007/s00044-011-9767-1
NPT65 Cell Line HepG2 Homo sapiens IC50 = 10650 nM 23290052
NPT2 Others Unspecified IC50 = 480 nM 23290052
NPT65 Cell Line HepG2 Homo sapiens IC50 = 240 nM 23290052
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 5180 nM 25666824

  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 NPC51978 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
0.9808 High Similarity NPC201992
0.9714 High Similarity NPC11252
0.9714 High Similarity NPC289312
0.9533 High Similarity NPC18547
0.9533 High Similarity NPC474906
0.9528 High Similarity NPC302146
0.9455 High Similarity NPC112038
0.9444 High Similarity NPC152199
0.9444 High Similarity NPC134869
0.9444 High Similarity NPC235539
0.9429 High Similarity NPC143706
0.9429 High Similarity NPC472534
0.9364 High Similarity NPC475775
0.9364 High Similarity NPC476529
0.9352 High Similarity NPC469877
0.9352 High Similarity NPC470919
0.9333 High Similarity NPC293850
0.9279 High Similarity NPC109607
0.9279 High Similarity NPC107338
0.9273 High Similarity NPC204552
0.9273 High Similarity NPC188667
0.9273 High Similarity NPC297179
0.9266 High Similarity NPC474046
0.9266 High Similarity NPC259306
0.9266 High Similarity NPC470628
0.9259 High Similarity NPC49451
0.9238 High Similarity NPC3316
0.9238 High Similarity NPC144854
0.9182 High Similarity NPC473968
0.9151 High Similarity NPC154608
0.9151 High Similarity NPC192813
0.9151 High Similarity NPC277017
0.9123 High Similarity NPC470922
0.9091 High Similarity NPC328374
0.9091 High Similarity NPC40632
0.9091 High Similarity NPC96312
0.9091 High Similarity NPC251236
0.9065 High Similarity NPC141350
0.9027 High Similarity NPC102822
0.9027 High Similarity NPC477046
0.9018 High Similarity NPC469488
0.9009 High Similarity NPC470854
0.9009 High Similarity NPC287343
0.9009 High Similarity NPC309433
0.9009 High Similarity NPC97908
0.9009 High Similarity NPC474654
0.9009 High Similarity NPC122033
0.9 High Similarity NPC473798
0.8991 High Similarity NPC474516
0.8962 High Similarity NPC102352
0.8929 High Similarity NPC17772
0.8929 High Similarity NPC251310
0.8919 High Similarity NPC474734
0.8909 High Similarity NPC7921
0.8909 High Similarity NPC208998
0.8899 High Similarity NPC171888
0.8899 High Similarity NPC146945
0.8879 High Similarity NPC230541
0.8839 High Similarity NPC470775
0.8839 High Similarity NPC176513
0.8829 High Similarity NPC243354
0.8818 High Similarity NPC472002
0.8807 High Similarity NPC210005
0.8785 High Similarity NPC181357
0.8761 High Similarity NPC470776
0.875 High Similarity NPC207217
0.875 High Similarity NPC179626
0.8739 High Similarity NPC194273
0.8739 High Similarity NPC194100
0.8727 High Similarity NPC188738
0.8727 High Similarity NPC471243
0.8707 High Similarity NPC67251
0.8684 High Similarity NPC470777
0.8684 High Similarity NPC122971
0.8673 High Similarity NPC473590
0.8632 High Similarity NPC24651
0.8632 High Similarity NPC476729
0.8621 High Similarity NPC312833
0.8598 High Similarity NPC275583
0.8571 High Similarity NPC255017
0.8547 High Similarity NPC91693
0.8547 High Similarity NPC265557
0.8547 High Similarity NPC18945
0.8547 High Similarity NPC105926
0.8545 High Similarity NPC27814
0.8534 High Similarity NPC202051
0.8522 High Similarity NPC268958
0.8509 High Similarity NPC477116
0.8509 High Similarity NPC218970
0.8509 High Similarity NPC27999
0.8509 High Similarity NPC470171
0.8496 Intermediate Similarity NPC268238
0.8496 Intermediate Similarity NPC117712
0.8496 Intermediate Similarity NPC102088
0.8496 Intermediate Similarity NPC45218
0.8496 Intermediate Similarity NPC143268
0.8496 Intermediate Similarity NPC323821
0.8496 Intermediate Similarity NPC472274
0.8491 Intermediate Similarity NPC472972
0.8468 Intermediate Similarity NPC474567
0.8468 Intermediate Similarity NPC5103
0.8462 Intermediate Similarity NPC222688
0.8421 Intermediate Similarity NPC16081
0.8421 Intermediate Similarity NPC173686
0.8421 Intermediate Similarity NPC478216
0.8407 Intermediate Similarity NPC320118
0.8407 Intermediate Similarity NPC293038
0.8407 Intermediate Similarity NPC62696
0.8403 Intermediate Similarity NPC285091
0.8403 Intermediate Similarity NPC225049
0.839 Intermediate Similarity NPC227397
0.8378 Intermediate Similarity NPC310546
0.8376 Intermediate Similarity NPC470779
0.8364 Intermediate Similarity NPC293512
0.8362 Intermediate Similarity NPC127530
0.8362 Intermediate Similarity NPC475041
0.8362 Intermediate Similarity NPC19028
0.8362 Intermediate Similarity NPC473920
0.8362 Intermediate Similarity NPC473401
0.8362 Intermediate Similarity NPC9674
0.8361 Intermediate Similarity NPC102316
0.8361 Intermediate Similarity NPC471855
0.8349 Intermediate Similarity NPC258532
0.8348 Intermediate Similarity NPC13713
0.8333 Intermediate Similarity NPC295791
0.8333 Intermediate Similarity NPC470882
0.8333 Intermediate Similarity NPC475633
0.8333 Intermediate Similarity NPC470780
0.8319 Intermediate Similarity NPC174836
0.8319 Intermediate Similarity NPC194951
0.8319 Intermediate Similarity NPC12046
0.8319 Intermediate Similarity NPC269530
0.8319 Intermediate Similarity NPC205534
0.8319 Intermediate Similarity NPC471967
0.8305 Intermediate Similarity NPC471965
0.8305 Intermediate Similarity NPC28532
0.8304 Intermediate Similarity NPC471093
0.8293 Intermediate Similarity NPC168879
0.8291 Intermediate Similarity NPC472257
0.8291 Intermediate Similarity NPC109973
0.8291 Intermediate Similarity NPC471406
0.8288 Intermediate Similarity NPC469984
0.8288 Intermediate Similarity NPC63841
0.8288 Intermediate Similarity NPC189075
0.8288 Intermediate Similarity NPC275539
0.8288 Intermediate Similarity NPC471094
0.8288 Intermediate Similarity NPC473410
0.8288 Intermediate Similarity NPC272576
0.8279 Intermediate Similarity NPC476074
0.8279 Intermediate Similarity NPC329993
0.8279 Intermediate Similarity NPC134914
0.8279 Intermediate Similarity NPC478065
0.8279 Intermediate Similarity NPC45346
0.8279 Intermediate Similarity NPC475377
0.8279 Intermediate Similarity NPC301639
0.8279 Intermediate Similarity NPC478064
0.8279 Intermediate Similarity NPC475167
0.8279 Intermediate Similarity NPC173435
0.8279 Intermediate Similarity NPC264566
0.8279 Intermediate Similarity NPC262796
0.8279 Intermediate Similarity NPC172374
0.8273 Intermediate Similarity NPC127609
0.8264 Intermediate Similarity NPC473888
0.8264 Intermediate Similarity NPC188291
0.8261 Intermediate Similarity NPC49492
0.8261 Intermediate Similarity NPC138372
0.8261 Intermediate Similarity NPC266728
0.8261 Intermediate Similarity NPC106228
0.825 Intermediate Similarity NPC47113
0.825 Intermediate Similarity NPC174367
0.8246 Intermediate Similarity NPC25909
0.8246 Intermediate Similarity NPC469496
0.8246 Intermediate Similarity NPC962
0.8246 Intermediate Similarity NPC157441
0.8246 Intermediate Similarity NPC469463
0.8246 Intermediate Similarity NPC250109
0.8246 Intermediate Similarity NPC178981
0.8246 Intermediate Similarity NPC469454
0.824 Intermediate Similarity NPC251998
0.824 Intermediate Similarity NPC243014
0.8235 Intermediate Similarity NPC471964
0.8235 Intermediate Similarity NPC262199
0.8235 Intermediate Similarity NPC471961
0.8235 Intermediate Similarity NPC478066
0.8235 Intermediate Similarity NPC202666
0.8235 Intermediate Similarity NPC14617
0.823 Intermediate Similarity NPC304180
0.823 Intermediate Similarity NPC132790
0.823 Intermediate Similarity NPC213320
0.823 Intermediate Similarity NPC29505
0.823 Intermediate Similarity NPC179798
0.823 Intermediate Similarity NPC263827
0.823 Intermediate Similarity NPC97939
0.823 Intermediate Similarity NPC469655
0.823 Intermediate Similarity NPC250481
0.823 Intermediate Similarity NPC100329
0.823 Intermediate Similarity NPC469656
0.823 Intermediate Similarity NPC247031
0.823 Intermediate Similarity NPC285410
0.823 Intermediate Similarity NPC56025

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC51978 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
0.8235 Intermediate Similarity NPD8328 Phase 3
0.8087 Intermediate Similarity NPD4632 Approved
0.8036 Intermediate Similarity NPD6412 Phase 2
0.8034 Intermediate Similarity NPD6009 Approved
0.8017 Intermediate Similarity NPD7492 Approved
0.7983 Intermediate Similarity NPD6059 Approved
0.7983 Intermediate Similarity NPD6319 Approved
0.7983 Intermediate Similarity NPD6054 Approved
0.7967 Intermediate Similarity NPD7736 Approved
0.7951 Intermediate Similarity NPD6616 Approved
0.7946 Intermediate Similarity NPD6675 Approved
0.7946 Intermediate Similarity NPD6402 Approved
0.7946 Intermediate Similarity NPD7128 Approved
0.7946 Intermediate Similarity NPD5739 Approved
0.7917 Intermediate Similarity NPD6016 Approved
0.7917 Intermediate Similarity NPD6015 Approved
0.7895 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7886 Intermediate Similarity NPD7078 Approved
0.7886 Intermediate Similarity NPD8293 Discontinued
0.7881 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7876 Intermediate Similarity NPD5701 Approved
0.7876 Intermediate Similarity NPD5697 Approved
0.7851 Intermediate Similarity NPD5988 Approved
0.7851 Intermediate Similarity NPD6370 Approved
0.7845 Intermediate Similarity NPD6882 Approved
0.7845 Intermediate Similarity NPD8297 Approved
0.7807 Intermediate Similarity NPD7320 Approved
0.7807 Intermediate Similarity NPD6881 Approved
0.7807 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7807 Intermediate Similarity NPD6899 Approved
0.7807 Intermediate Similarity NPD6686 Approved
0.7805 Intermediate Similarity NPD7507 Approved
0.7739 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7739 Intermediate Similarity NPD6012 Approved
0.7739 Intermediate Similarity NPD6372 Approved
0.7739 Intermediate Similarity NPD6014 Approved
0.7739 Intermediate Similarity NPD6013 Approved
0.7739 Intermediate Similarity NPD6373 Approved
0.7679 Intermediate Similarity NPD5211 Phase 2
0.7672 Intermediate Similarity NPD7102 Approved
0.7672 Intermediate Similarity NPD6883 Approved
0.7672 Intermediate Similarity NPD7290 Approved
0.7652 Intermediate Similarity NPD6011 Approved
0.7636 Intermediate Similarity NPD4755 Approved
0.7632 Intermediate Similarity NPD6008 Approved
0.7623 Intermediate Similarity NPD5983 Phase 2
0.7619 Intermediate Similarity NPD7319 Approved
0.7607 Intermediate Similarity NPD6650 Approved
0.7607 Intermediate Similarity NPD8130 Phase 1
0.7607 Intermediate Similarity NPD6617 Approved
0.7607 Intermediate Similarity NPD6869 Approved
0.7607 Intermediate Similarity NPD6649 Approved
0.7607 Intermediate Similarity NPD6847 Approved
0.7583 Intermediate Similarity NPD7115 Discovery
0.7568 Intermediate Similarity NPD4225 Approved
0.7544 Intermediate Similarity NPD5141 Approved
0.7523 Intermediate Similarity NPD7748 Approved
0.7521 Intermediate Similarity NPD4634 Approved
0.75 Intermediate Similarity NPD5286 Approved
0.75 Intermediate Similarity NPD7515 Phase 2
0.75 Intermediate Similarity NPD4700 Approved
0.75 Intermediate Similarity NPD4696 Approved
0.75 Intermediate Similarity NPD7640 Approved
0.75 Intermediate Similarity NPD7604 Phase 2
0.75 Intermediate Similarity NPD5285 Approved
0.75 Intermediate Similarity NPD7639 Approved
0.7477 Intermediate Similarity NPD7902 Approved
0.7458 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD7638 Approved
0.7402 Intermediate Similarity NPD6033 Approved
0.7387 Intermediate Similarity NPD4697 Phase 3
0.7387 Intermediate Similarity NPD5221 Approved
0.7387 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7387 Intermediate Similarity NPD5222 Approved
0.7381 Intermediate Similarity NPD6336 Discontinued
0.7373 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD5224 Approved
0.7368 Intermediate Similarity NPD5225 Approved
0.7368 Intermediate Similarity NPD4633 Approved
0.7368 Intermediate Similarity NPD5226 Approved
0.7355 Intermediate Similarity NPD6274 Approved
0.7339 Intermediate Similarity NPD8515 Approved
0.7339 Intermediate Similarity NPD8517 Approved
0.7339 Intermediate Similarity NPD8516 Approved
0.7339 Intermediate Similarity NPD8513 Phase 3
0.7321 Intermediate Similarity NPD6084 Phase 2
0.7321 Intermediate Similarity NPD6083 Phase 2
0.7321 Intermediate Similarity NPD5173 Approved
0.7317 Intermediate Similarity NPD7516 Approved
0.7315 Intermediate Similarity NPD5328 Approved
0.7304 Intermediate Similarity NPD5175 Approved
0.7304 Intermediate Similarity NPD5174 Approved
0.729 Intermediate Similarity NPD3573 Approved
0.7281 Intermediate Similarity NPD5223 Approved
0.7273 Intermediate Similarity NPD6399 Phase 3
0.7236 Intermediate Similarity NPD7327 Approved
0.7236 Intermediate Similarity NPD7328 Approved
0.7207 Intermediate Similarity NPD7900 Approved
0.7207 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD8033 Approved
0.7196 Intermediate Similarity NPD3618 Phase 1
0.719 Intermediate Similarity NPD8133 Approved
0.7182 Intermediate Similarity NPD6079 Approved
0.7179 Intermediate Similarity NPD4767 Approved
0.7179 Intermediate Similarity NPD4768 Approved
0.7177 Intermediate Similarity NPD7100 Approved
0.7177 Intermediate Similarity NPD7101 Approved
0.7167 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD4754 Approved
0.7154 Intermediate Similarity NPD6317 Approved
0.7143 Intermediate Similarity NPD5695 Phase 3
0.712 Intermediate Similarity NPD8377 Approved
0.712 Intermediate Similarity NPD8294 Approved
0.7119 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD5696 Approved
0.7097 Intermediate Similarity NPD6335 Approved
0.7097 Intermediate Similarity NPD6313 Approved
0.7097 Intermediate Similarity NPD6314 Approved
0.7087 Intermediate Similarity NPD6067 Discontinued
0.7073 Intermediate Similarity NPD6868 Approved
0.7064 Intermediate Similarity NPD5737 Approved
0.7064 Intermediate Similarity NPD6672 Approved
0.7063 Intermediate Similarity NPD7503 Approved
0.7063 Intermediate Similarity NPD8380 Approved
0.7063 Intermediate Similarity NPD8335 Approved
0.7063 Intermediate Similarity NPD6921 Approved
0.7063 Intermediate Similarity NPD6909 Approved
0.7063 Intermediate Similarity NPD8378 Approved
0.7063 Intermediate Similarity NPD8379 Approved
0.7063 Intermediate Similarity NPD8296 Approved
0.7063 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6908 Approved
0.7059 Intermediate Similarity NPD4729 Approved
0.7059 Intermediate Similarity NPD4730 Approved
0.7059 Intermediate Similarity NPD5128 Approved
0.7027 Intermediate Similarity NPD6411 Approved
0.7 Intermediate Similarity NPD4753 Phase 2
0.6981 Remote Similarity NPD3667 Approved
0.6964 Remote Similarity NPD5778 Approved
0.6964 Remote Similarity NPD5779 Approved
0.6964 Remote Similarity NPD4202 Approved
0.6942 Remote Similarity NPD5250 Approved
0.6942 Remote Similarity NPD5251 Approved
0.6942 Remote Similarity NPD5249 Phase 3
0.6942 Remote Similarity NPD5247 Approved
0.6942 Remote Similarity NPD5248 Approved
0.6937 Remote Similarity NPD46 Approved
0.6937 Remote Similarity NPD6698 Approved
0.6923 Remote Similarity NPD7632 Discontinued
0.6923 Remote Similarity NPD8074 Phase 3
0.6909 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6903 Remote Similarity NPD5282 Discontinued
0.6885 Remote Similarity NPD5215 Approved
0.6885 Remote Similarity NPD5216 Approved
0.6885 Remote Similarity NPD5217 Approved
0.6881 Remote Similarity NPD6684 Approved
0.6881 Remote Similarity NPD7521 Approved
0.6881 Remote Similarity NPD5330 Approved
0.6881 Remote Similarity NPD7146 Approved
0.6881 Remote Similarity NPD6409 Approved
0.6881 Remote Similarity NPD7334 Approved
0.6852 Remote Similarity NPD3665 Phase 1
0.6852 Remote Similarity NPD4786 Approved
0.6852 Remote Similarity NPD3666 Approved
0.6852 Remote Similarity NPD3133 Approved
0.6847 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6847 Remote Similarity NPD6101 Approved
0.6847 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7260 Phase 2
0.6838 Remote Similarity NPD5344 Discontinued
0.6829 Remote Similarity NPD6053 Discontinued
0.6803 Remote Similarity NPD5135 Approved
0.6803 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6803 Remote Similarity NPD5169 Approved
0.6792 Remote Similarity NPD4695 Discontinued
0.6777 Remote Similarity NPD5168 Approved
0.6767 Remote Similarity NPD5956 Approved
0.6757 Remote Similarity NPD6903 Approved
0.6748 Remote Similarity NPD5127 Approved
0.6727 Remote Similarity NPD5279 Phase 3
0.6726 Remote Similarity NPD7983 Approved
0.6726 Remote Similarity NPD8034 Phase 2
0.6726 Remote Similarity NPD5693 Phase 1
0.6726 Remote Similarity NPD8035 Phase 2
0.6696 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6080 Approved
0.6696 Remote Similarity NPD5210 Approved
0.6696 Remote Similarity NPD6673 Approved
0.6696 Remote Similarity NPD6904 Approved
0.6696 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6696 Remote Similarity NPD4629 Approved
0.6667 Remote Similarity NPD6845 Suspended
0.6667 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6371 Approved
0.6636 Remote Similarity NPD1694 Approved
0.6636 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6587 Remote Similarity NPD5167 Approved
0.6557 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6547 Remote Similarity NPD6333 Approved
0.6547 Remote Similarity NPD6334 Approved

Structure

External Identifiers

PubChem CID   72965
ChEMBL   CHEMBL161015
ZINC  

Physicochemical Properties

Molecular Weight:  376.15
ALogP:  -0.9967
MLogP:  2.89
XLogP:  -0.429
# Rotatable Bonds:  5
Polar Surface Area:  113.29
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  27

Download Data

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Biological Activities  
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