Natural Product: NPC279722

Natural Product ID:  NPC279722
Common Name:   Pestalofone A
IUPAC Name:   (1S,2S,4E,6S)-2-hydroxy-6-(3-methylbut-2-enyl)-4-(3-methylbut-2-enylidene)-7-oxabicyclo[4.1.0]heptan-5-one
Synonyms:  
Molecular Formula:   C16H22O3
Standard InCHIKey:  XPTXPZUFXASXPQ-KHCQGZIYSA-N
Standard InCHI:  InChI=1S/C16H22O3/c1-10(2)5-6-12-9-13(17)15-16(19-15,14(12)18)8-7-11(3)4/h5-7,13,15,17H,8-9H2,1-4H3/b12-6+/t13-,15-,16+/m0/s1
Canonical SMILES:  CC(=C/C=C/1C[C@H](O)[C@H]2[C@](C1=O)(CC=C(C)C)O2)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
NPO22690 Pestalotiopsis fici Species Sporocadaceae Eukaryota PMID[19101157]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1452 Cell Line C8166 Homo sapiens CC50 > 200000 nM 21493075
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 90400 nM 20583752

  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 NPC279722 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
0.8646 High Similarity NPC236176
0.8544 High Similarity NPC476023
0.8222 Intermediate Similarity NPC67254
0.8039 Intermediate Similarity NPC469980
0.8039 Intermediate Similarity NPC104161
0.8039 Intermediate Similarity NPC118902
0.7981 Intermediate Similarity NPC266514
0.7979 Intermediate Similarity NPC262026
0.7963 Intermediate Similarity NPC80650
0.7941 Intermediate Similarity NPC39996
0.7835 Intermediate Similarity NPC477684
0.781 Intermediate Similarity NPC474716
0.7767 Intermediate Similarity NPC478176
0.7706 Intermediate Similarity NPC477266
0.7685 Intermediate Similarity NPC474229
0.7677 Intermediate Similarity NPC61275
0.767 Intermediate Similarity NPC476270
0.7629 Intermediate Similarity NPC476706
0.7629 Intermediate Similarity NPC476707
0.7604 Intermediate Similarity NPC196381
0.7586 Intermediate Similarity NPC471939
0.7576 Intermediate Similarity NPC146852
0.7573 Intermediate Similarity NPC469551
0.7521 Intermediate Similarity NPC471940
0.75 Intermediate Similarity NPC38154
0.75 Intermediate Similarity NPC474339
0.75 Intermediate Similarity NPC87335
0.75 Intermediate Similarity NPC477116
0.75 Intermediate Similarity NPC164598
0.75 Intermediate Similarity NPC27999
0.75 Intermediate Similarity NPC201718
0.7477 Intermediate Similarity NPC477513
0.7477 Intermediate Similarity NPC469558
0.7476 Intermediate Similarity NPC306908
0.7456 Intermediate Similarity NPC478051
0.7453 Intermediate Similarity NPC474741
0.7449 Intermediate Similarity NPC476708
0.7436 Intermediate Similarity NPC225049
0.7434 Intermediate Similarity NPC17772
0.7431 Intermediate Similarity NPC89408
0.7429 Intermediate Similarity NPC474747
0.7414 Intermediate Similarity NPC473802
0.7411 Intermediate Similarity NPC207217
0.7404 Intermediate Similarity NPC475949
0.74 Intermediate Similarity NPC476705
0.7396 Intermediate Similarity NPC469809
0.7396 Intermediate Similarity NPC136114
0.7391 Intermediate Similarity NPC102822
0.7391 Intermediate Similarity NPC477046
0.7387 Intermediate Similarity NPC7921
0.7387 Intermediate Similarity NPC208998
0.7383 Intermediate Similarity NPC128828
0.7368 Intermediate Similarity NPC470777
0.7364 Intermediate Similarity NPC317107
0.7364 Intermediate Similarity NPC146945
0.7364 Intermediate Similarity NPC171888
0.7358 Intermediate Similarity NPC320294
0.7358 Intermediate Similarity NPC475871
0.7358 Intermediate Similarity NPC475945
0.735 Intermediate Similarity NPC473919
0.735 Intermediate Similarity NPC473709
0.7345 Intermediate Similarity NPC53396
0.7345 Intermediate Similarity NPC122033
0.7345 Intermediate Similarity NPC98249
0.7345 Intermediate Similarity NPC474654
0.7345 Intermediate Similarity NPC97908
0.7345 Intermediate Similarity NPC287343
0.7345 Intermediate Similarity NPC470854
0.734 Intermediate Similarity NPC472948
0.7333 Intermediate Similarity NPC475606
0.7333 Intermediate Similarity NPC47880
0.7333 Intermediate Similarity NPC251564
0.7333 Intermediate Similarity NPC475314
0.7333 Intermediate Similarity NPC112613
0.7333 Intermediate Similarity NPC477189
0.7333 Intermediate Similarity NPC474742
0.7327 Intermediate Similarity NPC212486
0.732 Intermediate Similarity NPC187529
0.732 Intermediate Similarity NPC79573
0.7308 Intermediate Similarity NPC471144
0.7308 Intermediate Similarity NPC161855
0.7308 Intermediate Similarity NPC300584
0.73 Intermediate Similarity NPC65359
0.73 Intermediate Similarity NPC469464
0.7297 Intermediate Similarity NPC317687
0.7288 Intermediate Similarity NPC217901
0.7282 Intermediate Similarity NPC94337
0.7282 Intermediate Similarity NPC473291
0.7281 Intermediate Similarity NPC284707
0.7281 Intermediate Similarity NPC251310
0.7273 Intermediate Similarity NPC210005
0.7273 Intermediate Similarity NPC201046
0.7273 Intermediate Similarity NPC474508
0.7273 Intermediate Similarity NPC476704
0.7273 Intermediate Similarity NPC473485
0.7264 Intermediate Similarity NPC471148
0.7264 Intermediate Similarity NPC149371
0.7263 Intermediate Similarity NPC286229
0.7257 Intermediate Similarity NPC477509
0.7257 Intermediate Similarity NPC328374
0.7257 Intermediate Similarity NPC96312
0.7257 Intermediate Similarity NPC270478
0.7257 Intermediate Similarity NPC251236
0.7257 Intermediate Similarity NPC40632
0.7248 Intermediate Similarity NPC102843
0.7248 Intermediate Similarity NPC29827
0.7241 Intermediate Similarity NPC472401
0.7238 Intermediate Similarity NPC324667
0.7238 Intermediate Similarity NPC475053
0.7238 Intermediate Similarity NPC288876
0.7232 Intermediate Similarity NPC49451
0.7232 Intermediate Similarity NPC198539
0.7228 Intermediate Similarity NPC142838
0.7228 Intermediate Similarity NPC469627
0.7228 Intermediate Similarity NPC475441
0.7227 Intermediate Similarity NPC475273
0.7227 Intermediate Similarity NPC168849
0.7222 Intermediate Similarity NPC474101
0.7212 Intermediate Similarity NPC473574
0.7212 Intermediate Similarity NPC20066
0.7212 Intermediate Similarity NPC20078
0.7207 Intermediate Similarity NPC207689
0.7203 Intermediate Similarity NPC24651
0.7196 Intermediate Similarity NPC472755
0.7196 Intermediate Similarity NPC475873
0.7193 Intermediate Similarity NPC476713
0.7193 Intermediate Similarity NPC474518
0.7193 Intermediate Similarity NPC476712
0.7193 Intermediate Similarity NPC478204
0.7193 Intermediate Similarity NPC156252
0.7188 Intermediate Similarity NPC253364
0.7184 Intermediate Similarity NPC14961
0.7184 Intermediate Similarity NPC270013
0.7182 Intermediate Similarity NPC471400
0.7182 Intermediate Similarity NPC77089
0.7179 Intermediate Similarity NPC19464
0.7172 Intermediate Similarity NPC471738
0.717 Intermediate Similarity NPC84042
0.717 Intermediate Similarity NPC133907
0.717 Intermediate Similarity NPC207885
0.717 Intermediate Similarity NPC46998
0.717 Intermediate Similarity NPC305085
0.717 Intermediate Similarity NPC472753
0.717 Intermediate Similarity NPC110443
0.717 Intermediate Similarity NPC185141
0.717 Intermediate Similarity NPC128733
0.717 Intermediate Similarity NPC181645
0.7168 Intermediate Similarity NPC473798
0.7167 Intermediate Similarity NPC236999
0.7156 Intermediate Similarity NPC144854
0.7156 Intermediate Similarity NPC3316
0.7154 Intermediate Similarity NPC475500
0.7154 Intermediate Similarity NPC473548
0.7154 Intermediate Similarity NPC182266
0.7154 Intermediate Similarity NPC100017
0.7154 Intermediate Similarity NPC475154
0.7154 Intermediate Similarity NPC471136
0.7154 Intermediate Similarity NPC471137
0.7154 Intermediate Similarity NPC223356
0.7143 Intermediate Similarity NPC298595
0.7143 Intermediate Similarity NPC35717
0.7143 Intermediate Similarity NPC473877
0.7143 Intermediate Similarity NPC278008
0.7143 Intermediate Similarity NPC474516
0.713 Intermediate Similarity NPC477510
0.713 Intermediate Similarity NPC297179
0.713 Intermediate Similarity NPC478206
0.713 Intermediate Similarity NPC108581
0.713 Intermediate Similarity NPC471143
0.713 Intermediate Similarity NPC478205
0.713 Intermediate Similarity NPC204552
0.713 Intermediate Similarity NPC106644
0.713 Intermediate Similarity NPC188667
0.7119 Intermediate Similarity NPC472399
0.7119 Intermediate Similarity NPC280498
0.7119 Intermediate Similarity NPC11895
0.7117 Intermediate Similarity NPC100908
0.7115 Intermediate Similarity NPC17585
0.7115 Intermediate Similarity NPC8803
0.7115 Intermediate Similarity NPC135576
0.7115 Intermediate Similarity NPC93271
0.7115 Intermediate Similarity NPC473859
0.7113 Intermediate Similarity NPC477786
0.7113 Intermediate Similarity NPC477784
0.7113 Intermediate Similarity NPC477785
0.7107 Intermediate Similarity NPC162495
0.7105 Intermediate Similarity NPC476710
0.7105 Intermediate Similarity NPC476711
0.7103 Intermediate Similarity NPC472754
0.71 Intermediate Similarity NPC281516
0.71 Intermediate Similarity NPC472008
0.7091 Intermediate Similarity NPC192813
0.7091 Intermediate Similarity NPC277017
0.7091 Intermediate Similarity NPC322903
0.7091 Intermediate Similarity NPC293850
0.7091 Intermediate Similarity NPC264819
0.7091 Intermediate Similarity NPC154608
0.7087 Intermediate Similarity NPC258674
0.7087 Intermediate Similarity NPC474035
0.7087 Intermediate Similarity NPC121825

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC279722 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
0.6923 Remote Similarity NPD5282 Discontinued
0.6893 Remote Similarity NPD7983 Approved
0.6864 Remote Similarity NPD6319 Approved
0.6796 Remote Similarity NPD6698 Approved
0.6796 Remote Similarity NPD46 Approved
0.6768 Remote Similarity NPD6110 Phase 1
0.6723 Remote Similarity NPD6054 Approved
0.6697 Remote Similarity NPD5344 Discontinued
0.6667 Remote Similarity NPD4634 Approved
0.6667 Remote Similarity NPD6016 Approved
0.6667 Remote Similarity NPD5779 Approved
0.6667 Remote Similarity NPD6015 Approved
0.6667 Remote Similarity NPD5778 Approved
0.6637 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6635 Remote Similarity NPD7838 Discovery
0.6634 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6612 Remote Similarity NPD6370 Approved
0.6612 Remote Similarity NPD5988 Approved
0.6606 Remote Similarity NPD6648 Approved
0.6583 Remote Similarity NPD6059 Approved
0.6557 Remote Similarity NPD8328 Phase 3
0.6549 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6538 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6538 Remote Similarity NPD6101 Approved
0.6522 Remote Similarity NPD6371 Approved
0.6504 Remote Similarity NPD7492 Approved
0.6496 Remote Similarity NPD4632 Approved
0.6471 Remote Similarity NPD7115 Discovery
0.6452 Remote Similarity NPD6616 Approved
0.6415 Remote Similarity NPD6411 Approved
0.641 Remote Similarity NPD8297 Approved
0.6404 Remote Similarity NPD5697 Approved
0.64 Remote Similarity NPD7078 Approved
0.6364 Remote Similarity NPD4225 Approved
0.6349 Remote Similarity NPD7736 Approved
0.6348 Remote Similarity NPD6899 Approved
0.6348 Remote Similarity NPD6881 Approved
0.6333 Remote Similarity NPD6009 Approved
0.6325 Remote Similarity NPD6649 Approved
0.6325 Remote Similarity NPD6650 Approved
0.6316 Remote Similarity NPD6675 Approved
0.6316 Remote Similarity NPD5739 Approved
0.6316 Remote Similarity NPD6402 Approved
0.6316 Remote Similarity NPD7128 Approved
0.6306 Remote Similarity NPD5286 Approved
0.6306 Remote Similarity NPD5285 Approved
0.6306 Remote Similarity NPD4696 Approved
0.6304 Remote Similarity NPD7331 Phase 2
0.6293 Remote Similarity NPD6372 Approved
0.6293 Remote Similarity NPD6014 Approved
0.6293 Remote Similarity NPD6013 Approved
0.6293 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6293 Remote Similarity NPD6373 Approved
0.6293 Remote Similarity NPD6012 Approved
0.629 Remote Similarity NPD7604 Phase 2
0.6273 Remote Similarity NPD4755 Approved
0.627 Remote Similarity NPD8293 Discontinued
0.6261 Remote Similarity NPD5701 Approved
0.626 Remote Similarity NPD5983 Phase 2
0.625 Remote Similarity NPD5279 Phase 3
0.6239 Remote Similarity NPD6883 Approved
0.6239 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6239 Remote Similarity NPD7102 Approved
0.6239 Remote Similarity NPD7290 Approved
0.6207 Remote Similarity NPD7320 Approved
0.6207 Remote Similarity NPD6011 Approved
0.6198 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6195 Remote Similarity NPD5211 Phase 2
0.6195 Remote Similarity NPD5226 Approved
0.6195 Remote Similarity NPD5225 Approved
0.6195 Remote Similarity NPD5224 Approved
0.6195 Remote Similarity NPD4633 Approved
0.619 Remote Similarity NPD7524 Approved
0.6186 Remote Similarity NPD6617 Approved
0.6186 Remote Similarity NPD6847 Approved
0.6186 Remote Similarity NPD6869 Approved
0.6186 Remote Similarity NPD8130 Phase 1
0.6182 Remote Similarity NPD7839 Suspended
0.6182 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6182 Remote Similarity NPD5222 Approved
0.6182 Remote Similarity NPD4697 Phase 3
0.6182 Remote Similarity NPD5221 Approved
0.6174 Remote Similarity NPD6008 Approved
0.6162 Remote Similarity NPD4756 Discovery
0.6161 Remote Similarity NPD4700 Approved
0.6154 Remote Similarity NPD1696 Phase 3
0.6148 Remote Similarity NPD7641 Discontinued
0.614 Remote Similarity NPD5175 Approved
0.614 Remote Similarity NPD5174 Approved
0.6139 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6134 Remote Similarity NPD6882 Approved
0.6129 Remote Similarity NPD8516 Approved
0.6129 Remote Similarity NPD8517 Approved
0.6129 Remote Similarity NPD8515 Approved
0.6129 Remote Similarity NPD3704 Approved
0.6129 Remote Similarity NPD8513 Phase 3
0.6126 Remote Similarity NPD5173 Approved
0.6111 Remote Similarity NPD6079 Approved
0.6106 Remote Similarity NPD5223 Approved
0.6102 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6095 Remote Similarity NPD3618 Phase 1
0.6094 Remote Similarity NPD6033 Approved
0.609 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6087 Remote Similarity NPD5141 Approved
0.6075 Remote Similarity NPD5328 Approved
0.6071 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6063 Remote Similarity NPD6336 Discontinued
0.6032 Remote Similarity NPD7829 Approved
0.6032 Remote Similarity NPD7642 Approved
0.6032 Remote Similarity NPD7830 Approved
0.6022 Remote Similarity NPD7341 Phase 2
0.6019 Remote Similarity NPD3168 Discontinued
0.6019 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6 Remote Similarity NPD6921 Approved
0.5984 Remote Similarity NPD6274 Approved
0.5983 Remote Similarity NPD6412 Phase 2
0.5982 Remote Similarity NPD6084 Phase 2
0.5982 Remote Similarity NPD6083 Phase 2
0.598 Remote Similarity NPD4695 Discontinued
0.5978 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5957 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5952 Remote Similarity NPD8080 Discontinued
0.5946 Remote Similarity NPD5695 Phase 3
0.5946 Remote Similarity NPD5210 Approved
0.5946 Remote Similarity NPD4629 Approved
0.5943 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5932 Remote Similarity NPD4729 Approved
0.5932 Remote Similarity NPD4730 Approved
0.5932 Remote Similarity NPD6686 Approved
0.5932 Remote Similarity NPD5128 Approved
0.5929 Remote Similarity NPD5696 Approved
0.5926 Remote Similarity NPD1695 Approved
0.5926 Remote Similarity NPD4753 Phase 2
0.5923 Remote Similarity NPD7319 Approved
0.5922 Remote Similarity NPD5369 Approved
0.5917 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5917 Remote Similarity NPD6401 Clinical (unspecified phase)
0.59 Remote Similarity NPD818 Approved
0.59 Remote Similarity NPD819 Approved
0.5897 Remote Similarity NPD4768 Approved
0.5897 Remote Similarity NPD4767 Approved
0.5891 Remote Similarity NPD8074 Phase 3
0.5862 Remote Similarity NPD4754 Approved
0.5849 Remote Similarity NPD5363 Approved
0.5847 Remote Similarity NPD5954 Clinical (unspecified phase)
0.584 Remote Similarity NPD7100 Approved
0.584 Remote Similarity NPD7101 Approved
0.5833 Remote Similarity NPD5249 Phase 3
0.5833 Remote Similarity NPD5251 Approved
0.5833 Remote Similarity NPD5248 Approved
0.5833 Remote Similarity NPD5247 Approved
0.5833 Remote Similarity NPD5250 Approved
0.5826 Remote Similarity NPD1700 Approved
0.5818 Remote Similarity NPD7637 Suspended
0.581 Remote Similarity NPD6695 Phase 3
0.5806 Remote Similarity NPD6317 Approved
0.5794 Remote Similarity NPD4694 Approved
0.5794 Remote Similarity NPD5786 Approved
0.5794 Remote Similarity NPD5280 Approved
0.5785 Remote Similarity NPD5217 Approved
0.5785 Remote Similarity NPD5216 Approved
0.5785 Remote Similarity NPD5215 Approved
0.5785 Remote Similarity NPD7601 Clinical (unspecified phase)
0.5766 Remote Similarity NPD4202 Approved
0.576 Remote Similarity NPD6314 Approved
0.576 Remote Similarity NPD6335 Approved
0.576 Remote Similarity NPD6313 Approved
0.5758 Remote Similarity NPD5956 Approved
0.5755 Remote Similarity NPD3665 Phase 1
0.5755 Remote Similarity NPD3666 Approved
0.5755 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5755 Remote Similarity NPD3133 Approved
0.575 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5748 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5745 Remote Similarity NPD3197 Phase 1
0.5741 Remote Similarity NPD3573 Approved
0.5736 Remote Similarity NPD8299 Approved
0.5736 Remote Similarity NPD8340 Approved
0.5736 Remote Similarity NPD8342 Approved
0.5736 Remote Similarity NPD8341 Approved
0.5727 Remote Similarity NPD5785 Approved
0.5726 Remote Similarity NPD6868 Approved
0.5714 Remote Similarity NPD7748 Approved
0.5714 Remote Similarity NPD7260 Phase 2
0.5714 Remote Similarity NPD4522 Approved
0.5714 Remote Similarity NPD6435 Approved
0.5714 Remote Similarity NPD3667 Approved
0.5702 Remote Similarity NPD7902 Approved
0.5702 Remote Similarity NPD5135 Approved
0.5702 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5702 Remote Similarity NPD5169 Approved
0.5701 Remote Similarity NPD1694 Approved
0.5692 Remote Similarity NPD7507 Approved
0.5692 Remote Similarity NPD8273 Phase 1
0.5692 Remote Similarity NPD8451 Approved
0.5676 Remote Similarity NPD7515 Phase 2
0.5673 Remote Similarity NPD6930 Phase 2
0.5673 Remote Similarity NPD6931 Approved
0.5667 Remote Similarity NPD5168 Approved
0.5664 Remote Similarity NPD6190 Approved

Structure

External Identifiers

PubChem CID   42609854
ChEMBL   CHEMBL522607
ZINC  

Physicochemical Properties

Molecular Weight:  262.16
ALogP:  2.2455
MLogP:  2.89
XLogP:  1.552
# Rotatable Bonds:  8
Polar Surface Area:  49.83
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  19

Download Data

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