Natural Product: NPC72842

Natural Product ID:  NPC72842
Common Name:   1Beta,7Alpha,10Alpha-Trihydroxyeremophil-11(13)-En-12,8Beta-Olide
IUPAC Name:   (3aS,4aR,5S,8R,8aR,9aR)-3a,8,8a-trihydroxy-4a,5-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one
Synonyms:  
Molecular Formula:   C15H22O5
Standard InCHIKey:  VBOVRPFFQYEBGW-CBEDKGEXSA-N
Standard InCHI:  InChI=1S/C15H22O5/c1-8-4-5-10(16)15(19)6-11-14(18,7-13(8,15)3)9(2)12(17)20-11/h8,10-11,16,18-19H,2,4-7H2,1,3H3/t8-,10+,11+,13+,14-,15-/m0/s1
Canonical SMILES:  O=C1O[C@H]2[C@](C1=C)(O)C[C@]1([C@@](C2)(O)[C@H](O)CC[C@@H]1C)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
NPO33420 xylaria sp. bcc 21097 Species Xylariaceae Eukaryota PMID[20155932]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens IC50 = 15000 nM DrugMatrix in vivo data: Pathology
NPT20 Organism Candida albicans Candida albicans IC50 > 177000 nM 19115838
NPT91 Cell Line KB Homo sapiens IC50 = 5000 nM 16933863
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 > 35000 nM 12088425
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC > 177000 nM 12088425
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 7200 nM PubChem BioAssay data set
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 8500 nM 24900628

  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 NPC72842 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
0.9792 High Similarity NPC99510
0.9691 High Similarity NPC283850
0.9388 High Similarity NPC61442
0.9167 High Similarity NPC93245
0.9072 High Similarity NPC473963
0.902 High Similarity NPC37628
0.899 High Similarity NPC308824
0.8969 High Similarity NPC473964
0.8958 High Similarity NPC225474
0.8958 High Similarity NPC24861
0.8958 High Similarity NPC148000
0.8958 High Similarity NPC469596
0.8922 High Similarity NPC284732
0.8922 High Similarity NPC78966
0.8878 High Similarity NPC474395
0.8878 High Similarity NPC136781
0.8866 High Similarity NPC259042
0.8866 High Similarity NPC157686
0.8812 High Similarity NPC156681
0.88 High Similarity NPC475958
0.8725 High Similarity NPC296950
0.8713 High Similarity NPC164551
0.8673 High Similarity NPC90014
0.8614 High Similarity NPC242666
0.8598 High Similarity NPC477126
0.8586 High Similarity NPC284518
0.8544 High Similarity NPC146731
0.8542 High Similarity NPC194642
0.8542 High Similarity NPC116620
0.8515 High Similarity NPC477655
0.8515 High Similarity NPC47024
0.8515 High Similarity NPC477656
0.8505 High Similarity NPC269530
0.8469 Intermediate Similarity NPC147272
0.8454 Intermediate Similarity NPC475776
0.8447 Intermediate Similarity NPC159533
0.8431 Intermediate Similarity NPC111292
0.8416 Intermediate Similarity NPC216478
0.8416 Intermediate Similarity NPC476807
0.8416 Intermediate Similarity NPC476806
0.8411 Intermediate Similarity NPC157476
0.84 Intermediate Similarity NPC165528
0.84 Intermediate Similarity NPC228766
0.8396 Intermediate Similarity NPC474243
0.8381 Intermediate Similarity NPC187435
0.8381 Intermediate Similarity NPC67321
0.8364 Intermediate Similarity NPC58662
0.8333 Intermediate Similarity NPC42658
0.8333 Intermediate Similarity NPC305029
0.8333 Intermediate Similarity NPC181103
0.8333 Intermediate Similarity NPC472002
0.8318 Intermediate Similarity NPC235014
0.8317 Intermediate Similarity NPC474921
0.8302 Intermediate Similarity NPC231278
0.8302 Intermediate Similarity NPC218123
0.8302 Intermediate Similarity NPC208461
0.8302 Intermediate Similarity NPC289702
0.8302 Intermediate Similarity NPC273155
0.8302 Intermediate Similarity NPC112895
0.83 Intermediate Similarity NPC56369
0.8265 Intermediate Similarity NPC153853
0.8252 Intermediate Similarity NPC98225
0.8241 Intermediate Similarity NPC474846
0.8241 Intermediate Similarity NPC469655
0.8241 Intermediate Similarity NPC469656
0.8241 Intermediate Similarity NPC94650
0.8229 Intermediate Similarity NPC9231
0.8229 Intermediate Similarity NPC85698
0.8218 Intermediate Similarity NPC256227
0.8208 Intermediate Similarity NPC166993
0.82 Intermediate Similarity NPC66581
0.8198 Intermediate Similarity NPC470775
0.8198 Intermediate Similarity NPC176513
0.8198 Intermediate Similarity NPC469684
0.8182 Intermediate Similarity NPC117712
0.8163 Intermediate Similarity NPC77001
0.8163 Intermediate Similarity NPC253618
0.8144 Intermediate Similarity NPC175293
0.8131 Intermediate Similarity NPC306265
0.8125 Intermediate Similarity NPC478205
0.8125 Intermediate Similarity NPC478206
0.8125 Intermediate Similarity NPC108581
0.8113 Intermediate Similarity NPC200957
0.8113 Intermediate Similarity NPC138908
0.8095 Intermediate Similarity NPC209298
0.8095 Intermediate Similarity NPC277074
0.8091 Intermediate Similarity NPC478212
0.8087 Intermediate Similarity NPC67251
0.8073 Intermediate Similarity NPC29505
0.8058 Intermediate Similarity NPC124512
0.8058 Intermediate Similarity NPC159763
0.8058 Intermediate Similarity NPC278386
0.8056 Intermediate Similarity NPC102741
0.8056 Intermediate Similarity NPC42662
0.8056 Intermediate Similarity NPC299590
0.8056 Intermediate Similarity NPC154906
0.8053 Intermediate Similarity NPC230513
0.8041 Intermediate Similarity NPC185638
0.8036 Intermediate Similarity NPC13713
0.8036 Intermediate Similarity NPC287343
0.8036 Intermediate Similarity NPC122033
0.8036 Intermediate Similarity NPC478204
0.8036 Intermediate Similarity NPC98249
0.8036 Intermediate Similarity NPC470854
0.8036 Intermediate Similarity NPC474654
0.8036 Intermediate Similarity NPC53396
0.8036 Intermediate Similarity NPC97908
0.8021 Intermediate Similarity NPC97505
0.8021 Intermediate Similarity NPC130966
0.802 Intermediate Similarity NPC473434
0.802 Intermediate Similarity NPC474841
0.802 Intermediate Similarity NPC471446
0.8019 Intermediate Similarity NPC258532
0.8019 Intermediate Similarity NPC301787
0.8019 Intermediate Similarity NPC477127
0.8017 Intermediate Similarity NPC24651
0.8 Intermediate Similarity NPC476081
0.8 Intermediate Similarity NPC295791
0.8 Intermediate Similarity NPC473397
0.7982 Intermediate Similarity NPC100908
0.7982 Intermediate Similarity NPC154491
0.7982 Intermediate Similarity NPC471093
0.7982 Intermediate Similarity NPC112038
0.7982 Intermediate Similarity NPC5103
0.7982 Intermediate Similarity NPC268530
0.7982 Intermediate Similarity NPC85391
0.7982 Intermediate Similarity NPC474567
0.7981 Intermediate Similarity NPC470388
0.7965 Intermediate Similarity NPC470776
0.7965 Intermediate Similarity NPC251310
0.7965 Intermediate Similarity NPC284707
0.7963 Intermediate Similarity NPC94377
0.7963 Intermediate Similarity NPC255082
0.7963 Intermediate Similarity NPC151393
0.7963 Intermediate Similarity NPC473410
0.7963 Intermediate Similarity NPC471094
0.7963 Intermediate Similarity NPC469984
0.7963 Intermediate Similarity NPC63841
0.7961 Intermediate Similarity NPC199099
0.7961 Intermediate Similarity NPC111348
0.7949 Intermediate Similarity NPC293112
0.7946 Intermediate Similarity NPC154363
0.7946 Intermediate Similarity NPC471816
0.7946 Intermediate Similarity NPC270478
0.7946 Intermediate Similarity NPC234858
0.7946 Intermediate Similarity NPC471127
0.7946 Intermediate Similarity NPC207217
0.7946 Intermediate Similarity NPC179626
0.7944 Intermediate Similarity NPC56656
0.7944 Intermediate Similarity NPC472655
0.7944 Intermediate Similarity NPC222833
0.7928 Intermediate Similarity NPC94509
0.7928 Intermediate Similarity NPC471252
0.7928 Intermediate Similarity NPC89018
0.7925 Intermediate Similarity NPC122811
0.7925 Intermediate Similarity NPC474822
0.7925 Intermediate Similarity NPC87927
0.7921 Intermediate Similarity NPC199543
0.7921 Intermediate Similarity NPC110022
0.7917 Intermediate Similarity NPC243347
0.7913 Intermediate Similarity NPC67569
0.7913 Intermediate Similarity NPC4021
0.7913 Intermediate Similarity NPC159456
0.7909 Intermediate Similarity NPC97939
0.7909 Intermediate Similarity NPC247031
0.7909 Intermediate Similarity NPC100329
0.7909 Intermediate Similarity NPC56025
0.7909 Intermediate Similarity NPC213320
0.7909 Intermediate Similarity NPC132790
0.7905 Intermediate Similarity NPC46848
0.7895 Intermediate Similarity NPC470777
0.789 Intermediate Similarity NPC252679
0.789 Intermediate Similarity NPC131903
0.789 Intermediate Similarity NPC118721
0.7885 Intermediate Similarity NPC78427
0.7885 Intermediate Similarity NPC16911
0.7879 Intermediate Similarity NPC471221
0.7879 Intermediate Similarity NPC50847
0.7876 Intermediate Similarity NPC473590
0.7876 Intermediate Similarity NPC473656
0.7876 Intermediate Similarity NPC10721
0.7876 Intermediate Similarity NPC296822
0.7876 Intermediate Similarity NPC27999
0.7876 Intermediate Similarity NPC55296
0.7876 Intermediate Similarity NPC477116
0.7876 Intermediate Similarity NPC473968
0.787 Intermediate Similarity NPC471474
0.787 Intermediate Similarity NPC67745
0.787 Intermediate Similarity NPC230541
0.787 Intermediate Similarity NPC471461
0.787 Intermediate Similarity NPC180744
0.787 Intermediate Similarity NPC143609
0.787 Intermediate Similarity NPC186054
0.787 Intermediate Similarity NPC112780
0.7863 Intermediate Similarity NPC470922
0.7863 Intermediate Similarity NPC81736
0.7863 Intermediate Similarity NPC172154
0.7863 Intermediate Similarity NPC476729
0.7857 Intermediate Similarity NPC226608
0.7857 Intermediate Similarity NPC88867

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC72842 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
0.8302 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.8058 Intermediate Similarity NPD4225 Approved
0.8056 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7565 Intermediate Similarity NPD7115 Discovery
0.7545 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD6921 Approved
0.7248 Intermediate Similarity NPD5344 Discontinued
0.7168 Intermediate Similarity NPD6686 Approved
0.7156 Intermediate Similarity NPD7640 Approved
0.7156 Intermediate Similarity NPD7639 Approved
0.7155 Intermediate Similarity NPD8133 Approved
0.7083 Intermediate Similarity NPD6319 Approved
0.7064 Intermediate Similarity NPD7638 Approved
0.7043 Intermediate Similarity NPD6371 Approved
0.704 Intermediate Similarity NPD7319 Approved
0.6957 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6937 Remote Similarity NPD1700 Approved
0.6875 Remote Similarity NPD7632 Discontinued
0.6864 Remote Similarity NPD4632 Approved
0.686 Remote Similarity NPD7516 Approved
0.6855 Remote Similarity NPD7492 Approved
0.6847 Remote Similarity NPD6648 Approved
0.6833 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6822 Remote Similarity NPD8035 Phase 2
0.6822 Remote Similarity NPD8034 Phase 2
0.6803 Remote Similarity NPD6054 Approved
0.68 Remote Similarity NPD6616 Approved
0.68 Remote Similarity NPD7507 Approved
0.6789 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6783 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6777 Remote Similarity NPD7328 Approved
0.6777 Remote Similarity NPD7327 Approved
0.6748 Remote Similarity NPD8516 Approved
0.6748 Remote Similarity NPD8513 Phase 3
0.6748 Remote Similarity NPD6015 Approved
0.6748 Remote Similarity NPD8515 Approved
0.6748 Remote Similarity NPD8517 Approved
0.6748 Remote Similarity NPD6016 Approved
0.6746 Remote Similarity NPD7078 Approved
0.6731 Remote Similarity NPD1694 Approved
0.6696 Remote Similarity NPD6008 Approved
0.6694 Remote Similarity NPD6370 Approved
0.6694 Remote Similarity NPD5988 Approved
0.6693 Remote Similarity NPD7736 Approved
0.6667 Remote Similarity NPD6059 Approved
0.664 Remote Similarity NPD8328 Phase 3
0.6639 Remote Similarity NPD8297 Approved
0.6638 Remote Similarity NPD5697 Approved
0.6614 Remote Similarity NPD8293 Discontinued
0.661 Remote Similarity NPD4634 Approved
0.6606 Remote Similarity NPD6399 Phase 3
0.6581 Remote Similarity NPD6881 Approved
0.6581 Remote Similarity NPD6899 Approved
0.6574 Remote Similarity NPD46 Approved
0.6574 Remote Similarity NPD6698 Approved
0.6571 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6557 Remote Similarity NPD6009 Approved
0.6555 Remote Similarity NPD6649 Approved
0.6555 Remote Similarity NPD6650 Approved
0.6552 Remote Similarity NPD5739 Approved
0.6552 Remote Similarity NPD6675 Approved
0.6552 Remote Similarity NPD6402 Approved
0.6552 Remote Similarity NPD7128 Approved
0.6525 Remote Similarity NPD6012 Approved
0.6525 Remote Similarity NPD6373 Approved
0.6525 Remote Similarity NPD6013 Approved
0.6525 Remote Similarity NPD6372 Approved
0.6525 Remote Similarity NPD6014 Approved
0.6518 Remote Similarity NPD7902 Approved
0.6514 Remote Similarity NPD7637 Suspended
0.6496 Remote Similarity NPD6412 Phase 2
0.6496 Remote Similarity NPD5701 Approved
0.6484 Remote Similarity NPD8074 Phase 3
0.648 Remote Similarity NPD8380 Approved
0.648 Remote Similarity NPD8296 Approved
0.648 Remote Similarity NPD8033 Approved
0.648 Remote Similarity NPD8379 Approved
0.648 Remote Similarity NPD8335 Approved
0.648 Remote Similarity NPD8378 Approved
0.648 Remote Similarity NPD5983 Phase 2
0.6471 Remote Similarity NPD6883 Approved
0.6471 Remote Similarity NPD7290 Approved
0.6471 Remote Similarity NPD7102 Approved
0.6455 Remote Similarity NPD5778 Approved
0.6455 Remote Similarity NPD5779 Approved
0.6449 Remote Similarity NPD7524 Approved
0.6442 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6441 Remote Similarity NPD6011 Approved
0.6441 Remote Similarity NPD7320 Approved
0.6435 Remote Similarity NPD5211 Phase 2
0.6417 Remote Similarity NPD6847 Approved
0.6417 Remote Similarity NPD8130 Phase 1
0.6417 Remote Similarity NPD6617 Approved
0.6417 Remote Similarity NPD6869 Approved
0.6417 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6415 Remote Similarity NPD1733 Clinical (unspecified phase)
0.64 Remote Similarity NPD8294 Approved
0.64 Remote Similarity NPD8377 Approved
0.6396 Remote Similarity NPD5282 Discontinued
0.6396 Remote Similarity NPD7748 Approved
0.6378 Remote Similarity NPD7604 Phase 2
0.6373 Remote Similarity NPD6114 Approved
0.6373 Remote Similarity NPD6115 Approved
0.6373 Remote Similarity NPD6697 Approved
0.6373 Remote Similarity NPD6118 Approved
0.6364 Remote Similarity NPD7983 Approved
0.6364 Remote Similarity NPD7515 Phase 2
0.6364 Remote Similarity NPD6882 Approved
0.6355 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6355 Remote Similarity NPD3618 Phase 1
0.6349 Remote Similarity NPD7503 Approved
0.633 Remote Similarity NPD1695 Approved
0.6325 Remote Similarity NPD5141 Approved
0.6279 Remote Similarity NPD6336 Discontinued
0.6275 Remote Similarity NPD6116 Phase 1
0.6273 Remote Similarity NPD5785 Approved
0.6261 Remote Similarity NPD5286 Approved
0.6261 Remote Similarity NPD5285 Approved
0.6261 Remote Similarity NPD4696 Approved
0.625 Remote Similarity NPD7900 Approved
0.625 Remote Similarity NPD7901 Clinical (unspecified phase)
0.623 Remote Similarity NPD6053 Discontinued
0.6228 Remote Similarity NPD6083 Phase 2
0.6228 Remote Similarity NPD4755 Approved
0.6228 Remote Similarity NPD6084 Phase 2
0.6216 Remote Similarity NPD6411 Approved
0.621 Remote Similarity NPD6274 Approved
0.6183 Remote Similarity NPD6033 Approved
0.6176 Remote Similarity NPD6117 Approved
0.6174 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6174 Remote Similarity NPD5696 Approved
0.6168 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6161 Remote Similarity NPD4202 Approved
0.6154 Remote Similarity NPD5225 Approved
0.6154 Remote Similarity NPD5226 Approved
0.6154 Remote Similarity NPD5224 Approved
0.6154 Remote Similarity NPD4633 Approved
0.6148 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6132 Remote Similarity NPD3667 Approved
0.6126 Remote Similarity NPD7838 Discovery
0.6121 Remote Similarity NPD4700 Approved
0.6102 Remote Similarity NPD5174 Approved
0.6102 Remote Similarity NPD5175 Approved
0.6094 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6075 Remote Similarity NPD6695 Phase 3
0.6075 Remote Similarity NPD4788 Approved
0.6071 Remote Similarity NPD6079 Approved
0.6068 Remote Similarity NPD4159 Approved
0.6068 Remote Similarity NPD5223 Approved
0.6063 Remote Similarity NPD7100 Approved
0.6063 Remote Similarity NPD7101 Approved
0.6053 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6053 Remote Similarity NPD5695 Phase 3
0.6042 Remote Similarity NPD371 Approved
0.6036 Remote Similarity NPD6101 Approved
0.6036 Remote Similarity NPD5328 Approved
0.6036 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6032 Remote Similarity NPD6317 Approved
0.6019 Remote Similarity NPD4786 Approved
0.6 Remote Similarity NPD6067 Discontinued
0.6 Remote Similarity NPD6845 Suspended
0.6 Remote Similarity NPD5222 Approved
0.6 Remote Similarity NPD4697 Phase 3
0.6 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6 Remote Similarity NPD3573 Approved
0.6 Remote Similarity NPD5221 Approved
0.5984 Remote Similarity NPD6314 Approved
0.5984 Remote Similarity NPD6335 Approved
0.5984 Remote Similarity NPD6313 Approved
0.598 Remote Similarity NPD6113 Clinical (unspecified phase)
0.597 Remote Similarity NPD5956 Approved
0.5948 Remote Similarity NPD5173 Approved
0.5929 Remote Similarity NPD5693 Phase 1
0.5926 Remote Similarity NPD7260 Phase 2
0.5922 Remote Similarity NPD3703 Phase 2
0.5917 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5913 Remote Similarity NPD4629 Approved
0.5913 Remote Similarity NPD5210 Approved
0.5909 Remote Similarity NPD5330 Approved
0.5909 Remote Similarity NPD7521 Approved
0.5909 Remote Similarity NPD6409 Approved
0.5909 Remote Similarity NPD7146 Approved
0.5909 Remote Similarity NPD7334 Approved
0.5909 Remote Similarity NPD6684 Approved
0.5902 Remote Similarity NPD4729 Approved
0.5902 Remote Similarity NPD5128 Approved
0.5902 Remote Similarity NPD4730 Approved
0.5893 Remote Similarity NPD4753 Phase 2
0.5888 Remote Similarity NPD1780 Approved
0.5888 Remote Similarity NPD1779 Approved
0.5872 Remote Similarity NPD3666 Approved
0.5872 Remote Similarity NPD3665 Phase 1
0.5872 Remote Similarity NPD3133 Approved
0.5868 Remote Similarity NPD4768 Approved
0.5868 Remote Similarity NPD4767 Approved
0.5856 Remote Similarity NPD7750 Discontinued
0.5846 Remote Similarity NPD6909 Approved
0.5846 Remote Similarity NPD6908 Approved
0.5842 Remote Similarity NPD7532 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   46211045
ChEMBL   CHEMBL1099249
ZINC  

Physicochemical Properties

Molecular Weight:  282.15
ALogP:  -0.6807
MLogP:  2.56
XLogP:  0.878
# Rotatable Bonds:  5
Polar Surface Area:  86.99
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  20

Download Data

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