Natural Product: NPC478233

Natural Product ID:  NPC478233
Common Name:   lecanicillolide
IUPAC Name:  
Synonyms:  
Molecular Formula:   C22H26O7
Standard InCHIKey:  BENLGGSSMMCRCK-AZQKXBOTSA-N
Standard InCHI:  InChI=1S/C22H26O7/c1-7-22(6)19(26)13(8-23)14(15-17(24)9(2)11(4)28-20(15)22)16-18(25)10(3)12(5)29-21(16)27/h13-14,23,25H,7-8H2,1-6H3/t13?,14-,22-/m0/s1
Canonical SMILES:  OCC1[C@H](c2c(=O)oc(c(c2O)C)C)c2c(=O)c(C)c(oc2[C@@](C1=O)(C)CC)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
NPO33702 Lecanicillium sp. PR-M-3 Species Cordycipitaceae Eukaryota isolated from the rhizosphere soil of puer tea at Puer in Yunnan, China 2011-SEP DOI[10.1016/j.tetlet.2017.01.023]

  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 > 100 µM 10.1016/j.tetlet.2017.01.023
NPT2297 Cell Line ASPC1 Homo sapiens IC50 > 100 µM 10.1016/j.tetlet.2017.01.023
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 100 µM 10.1016/j.tetlet.2017.01.023

  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 NPC478233 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
0.8265 Intermediate Similarity NPC476797
0.8105 Intermediate Similarity NPC143025
0.7959 Intermediate Similarity NPC271652
0.7895 Intermediate Similarity NPC229717
0.785 Intermediate Similarity NPC478209
0.7843 Intermediate Similarity NPC54705
0.7822 Intermediate Similarity NPC53844
0.7822 Intermediate Similarity NPC208094
0.781 Intermediate Similarity NPC478208
0.7802 Intermediate Similarity NPC315765
0.78 Intermediate Similarity NPC209355
0.7767 Intermediate Similarity NPC244456
0.7767 Intermediate Similarity NPC469657
0.7755 Intermediate Similarity NPC476369
0.7755 Intermediate Similarity NPC476437
0.7755 Intermediate Similarity NPC51486
0.77 Intermediate Similarity NPC53685
0.7692 Intermediate Similarity NPC469606
0.7692 Intermediate Similarity NPC31058
0.7692 Intermediate Similarity NPC273005
0.7692 Intermediate Similarity NPC235369
0.7685 Intermediate Similarity NPC478211
0.7677 Intermediate Similarity NPC472705
0.7664 Intermediate Similarity NPC220155
0.7653 Intermediate Similarity NPC5509
0.7647 Intermediate Similarity NPC121339
0.7642 Intermediate Similarity NPC469607
0.7636 Intermediate Similarity NPC478212
0.7624 Intermediate Similarity NPC295347
0.7619 Intermediate Similarity NPC320154
0.7619 Intermediate Similarity NPC291154
0.7615 Intermediate Similarity NPC247031
0.7615 Intermediate Similarity NPC100329
0.7615 Intermediate Similarity NPC132790
0.7615 Intermediate Similarity NPC97939
0.76 Intermediate Similarity NPC115021
0.7593 Intermediate Similarity NPC228477
0.7593 Intermediate Similarity NPC137911
0.7593 Intermediate Similarity NPC478210
0.7576 Intermediate Similarity NPC213636
0.7576 Intermediate Similarity NPC113393
0.7576 Intermediate Similarity NPC253177
0.7576 Intermediate Similarity NPC280592
0.7553 Intermediate Similarity NPC282293
0.7551 Intermediate Similarity NPC307298
0.7551 Intermediate Similarity NPC472302
0.7551 Intermediate Similarity NPC72397
0.7551 Intermediate Similarity NPC476796
0.7549 Intermediate Similarity NPC17578
0.7549 Intermediate Similarity NPC240673
0.7549 Intermediate Similarity NPC202833
0.7549 Intermediate Similarity NPC3772
0.7547 Intermediate Similarity NPC121099
0.7525 Intermediate Similarity NPC476415
0.7525 Intermediate Similarity NPC184870
0.7525 Intermediate Similarity NPC474555
0.7524 Intermediate Similarity NPC80781
0.7522 Intermediate Similarity NPC108581
0.7522 Intermediate Similarity NPC478205
0.7522 Intermediate Similarity NPC478206
0.75 Intermediate Similarity NPC472814
0.75 Intermediate Similarity NPC307954
0.75 Intermediate Similarity NPC478216
0.75 Intermediate Similarity NPC177037
0.75 Intermediate Similarity NPC471329
0.75 Intermediate Similarity NPC476299
0.75 Intermediate Similarity NPC476767
0.75 Intermediate Similarity NPC117685
0.75 Intermediate Similarity NPC198880
0.75 Intermediate Similarity NPC296114
0.75 Intermediate Similarity NPC474012
0.7477 Intermediate Similarity NPC266570
0.7477 Intermediate Similarity NPC472935
0.7477 Intermediate Similarity NPC475966
0.7476 Intermediate Similarity NPC106557
0.7475 Intermediate Similarity NPC280833
0.7475 Intermediate Similarity NPC284561
0.7455 Intermediate Similarity NPC324683
0.7455 Intermediate Similarity NPC474315
0.7453 Intermediate Similarity NPC159533
0.7453 Intermediate Similarity NPC95899
0.7451 Intermediate Similarity NPC37646
0.7449 Intermediate Similarity NPC125925
0.7449 Intermediate Similarity NPC220930
0.7449 Intermediate Similarity NPC113370
0.7449 Intermediate Similarity NPC312561
0.7449 Intermediate Similarity NPC476079
0.7449 Intermediate Similarity NPC272039
0.7449 Intermediate Similarity NPC103743
0.7449 Intermediate Similarity NPC476409
0.7434 Intermediate Similarity NPC478204
0.7431 Intermediate Similarity NPC23497
0.7429 Intermediate Similarity NPC471075
0.7426 Intermediate Similarity NPC476416
0.7426 Intermediate Similarity NPC131840
0.7423 Intermediate Similarity NPC307112
0.7407 Intermediate Similarity NPC91034
0.7404 Intermediate Similarity NPC316598
0.7404 Intermediate Similarity NPC23364
0.74 Intermediate Similarity NPC212679
0.74 Intermediate Similarity NPC145666
0.74 Intermediate Similarity NPC469595
0.74 Intermediate Similarity NPC220454
0.74 Intermediate Similarity NPC281942
0.74 Intermediate Similarity NPC232426
0.7396 Intermediate Similarity NPC258985
0.7396 Intermediate Similarity NPC102197
0.7387 Intermediate Similarity NPC285956
0.7379 Intermediate Similarity NPC242848
0.7379 Intermediate Similarity NPC243525
0.7379 Intermediate Similarity NPC40765
0.7379 Intermediate Similarity NPC7124
0.7374 Intermediate Similarity NPC53454
0.7374 Intermediate Similarity NPC24816
0.7364 Intermediate Similarity NPC470496
0.7364 Intermediate Similarity NPC206595
0.7358 Intermediate Similarity NPC475320
0.7358 Intermediate Similarity NPC295791
0.7358 Intermediate Similarity NPC476890
0.7358 Intermediate Similarity NPC137430
0.7358 Intermediate Similarity NPC281702
0.7353 Intermediate Similarity NPC474554
0.7353 Intermediate Similarity NPC84893
0.7347 Intermediate Similarity NPC477478
0.7347 Intermediate Similarity NPC322159
0.7347 Intermediate Similarity NPC474062
0.7347 Intermediate Similarity NPC477479
0.7339 Intermediate Similarity NPC151393
0.7339 Intermediate Similarity NPC89171
0.7339 Intermediate Similarity NPC476765
0.7339 Intermediate Similarity NPC476802
0.7333 Intermediate Similarity NPC306856
0.7333 Intermediate Similarity NPC299971
0.7333 Intermediate Similarity NPC144660
0.7327 Intermediate Similarity NPC141831
0.7321 Intermediate Similarity NPC321496
0.732 Intermediate Similarity NPC149869
0.7315 Intermediate Similarity NPC189863
0.7312 Intermediate Similarity NPC316324
0.7308 Intermediate Similarity NPC474343
0.7308 Intermediate Similarity NPC287668
0.7308 Intermediate Similarity NPC253826
0.7308 Intermediate Similarity NPC122294
0.7308 Intermediate Similarity NPC475709
0.73 Intermediate Similarity NPC118011
0.73 Intermediate Similarity NPC36668
0.729 Intermediate Similarity NPC8196
0.729 Intermediate Similarity NPC99266
0.729 Intermediate Similarity NPC271059
0.729 Intermediate Similarity NPC476889
0.729 Intermediate Similarity NPC25666
0.7281 Intermediate Similarity NPC98249
0.7281 Intermediate Similarity NPC53396
0.7273 Intermediate Similarity NPC286174
0.7273 Intermediate Similarity NPC31522
0.7273 Intermediate Similarity NPC77947
0.7273 Intermediate Similarity NPC477228
0.7265 Intermediate Similarity NPC287236
0.7264 Intermediate Similarity NPC323441
0.7264 Intermediate Similarity NPC476888
0.7264 Intermediate Similarity NPC472924
0.7264 Intermediate Similarity NPC472637
0.7264 Intermediate Similarity NPC93744
0.7264 Intermediate Similarity NPC475099
0.7255 Intermediate Similarity NPC476049
0.7248 Intermediate Similarity NPC112780
0.7248 Intermediate Similarity NPC202524
0.7248 Intermediate Similarity NPC473037
0.7245 Intermediate Similarity NPC86316
0.7245 Intermediate Similarity NPC106416
0.7245 Intermediate Similarity NPC65661
0.7245 Intermediate Similarity NPC189311
0.7245 Intermediate Similarity NPC76333
0.7241 Intermediate Similarity NPC476962
0.7238 Intermediate Similarity NPC16021
0.7238 Intermediate Similarity NPC471717
0.7232 Intermediate Similarity NPC90952
0.7232 Intermediate Similarity NPC66108
0.7228 Intermediate Similarity NPC477147
0.7228 Intermediate Similarity NPC232202
0.7228 Intermediate Similarity NPC469372
0.7228 Intermediate Similarity NPC472307
0.7228 Intermediate Similarity NPC477782
0.7228 Intermediate Similarity NPC477149
0.7222 Intermediate Similarity NPC296950
0.7222 Intermediate Similarity NPC239162
0.7222 Intermediate Similarity NPC325769
0.7222 Intermediate Similarity NPC146731
0.7217 Intermediate Similarity NPC284707
0.7216 Intermediate Similarity NPC475083
0.7216 Intermediate Similarity NPC49019
0.7212 Intermediate Similarity NPC328371
0.7212 Intermediate Similarity NPC184065
0.7212 Intermediate Similarity NPC472941
0.7212 Intermediate Similarity NPC456
0.7212 Intermediate Similarity NPC234993
0.7212 Intermediate Similarity NPC134072
0.7207 Intermediate Similarity NPC29133
0.7207 Intermediate Similarity NPC129689
0.7207 Intermediate Similarity NPC286880

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC478233 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
0.7255 Intermediate Similarity NPD5779 Approved
0.7255 Intermediate Similarity NPD5778 Approved
0.7157 Intermediate Similarity NPD6411 Approved
0.708 Intermediate Similarity NPD6053 Discontinued
0.7009 Intermediate Similarity NPD7640 Approved
0.7009 Intermediate Similarity NPD7639 Approved
0.6961 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6961 Remote Similarity NPD6101 Approved
0.6939 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6916 Remote Similarity NPD7638 Approved
0.6881 Remote Similarity NPD7632 Discontinued
0.6838 Remote Similarity NPD7115 Discovery
0.6814 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6796 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6759 Remote Similarity NPD4225 Approved
0.6759 Remote Similarity NPD5696 Approved
0.6731 Remote Similarity NPD5785 Approved
0.6726 Remote Similarity NPD6686 Approved
0.6698 Remote Similarity NPD7748 Approved
0.6667 Remote Similarity NPD5279 Phase 3
0.6667 Remote Similarity NPD6083 Phase 2
0.6667 Remote Similarity NPD6084 Phase 2
0.6667 Remote Similarity NPD7515 Phase 2
0.6636 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6636 Remote Similarity NPD5695 Phase 3
0.6609 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6569 Remote Similarity NPD1694 Approved
0.6566 Remote Similarity NPD4695 Discontinued
0.6562 Remote Similarity NPD8039 Approved
0.6538 Remote Similarity NPD5737 Approved
0.6538 Remote Similarity NPD6672 Approved
0.6535 Remote Similarity NPD7260 Phase 2
0.6531 Remote Similarity NPD3617 Approved
0.6514 Remote Similarity NPD7902 Approved
0.6509 Remote Similarity NPD5281 Approved
0.6509 Remote Similarity NPD7983 Approved
0.6509 Remote Similarity NPD5284 Approved
0.6509 Remote Similarity NPD7637 Suspended
0.6509 Remote Similarity NPD5693 Phase 1
0.6505 Remote Similarity NPD7146 Approved
0.6505 Remote Similarity NPD6409 Approved
0.6505 Remote Similarity NPD7334 Approved
0.6505 Remote Similarity NPD7521 Approved
0.6505 Remote Similarity NPD5330 Approved
0.6505 Remote Similarity NPD6684 Approved
0.6484 Remote Similarity NPD6845 Suspended
0.6471 Remote Similarity NPD3133 Approved
0.6471 Remote Similarity NPD3665 Phase 1
0.6471 Remote Similarity NPD3666 Approved
0.6466 Remote Similarity NPD6371 Approved
0.6449 Remote Similarity NPD6399 Phase 3
0.6436 Remote Similarity NPD5209 Approved
0.6429 Remote Similarity NPD4756 Discovery
0.6422 Remote Similarity NPD7614 Phase 1
0.6415 Remote Similarity NPD6698 Approved
0.6415 Remote Similarity NPD46 Approved
0.6415 Remote Similarity NPD5692 Phase 3
0.6404 Remote Similarity NPD6402 Approved
0.6404 Remote Similarity NPD7128 Approved
0.6404 Remote Similarity NPD5739 Approved
0.6404 Remote Similarity NPD6675 Approved
0.6389 Remote Similarity NPD5282 Discontinued
0.6381 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6381 Remote Similarity NPD6903 Approved
0.6355 Remote Similarity NPD6050 Approved
0.6355 Remote Similarity NPD5694 Approved
0.6348 Remote Similarity NPD5701 Approved
0.6348 Remote Similarity NPD5697 Approved
0.6348 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6346 Remote Similarity NPD3618 Phase 1
0.6346 Remote Similarity NPD4519 Discontinued
0.6346 Remote Similarity NPD4623 Approved
0.6346 Remote Similarity NPD3574 Clinical (unspecified phase)
0.633 Remote Similarity NPD5210 Approved
0.633 Remote Similarity NPD4629 Approved
0.6321 Remote Similarity NPD4753 Phase 2
0.6321 Remote Similarity NPD5328 Approved
0.6311 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6293 Remote Similarity NPD7320 Approved
0.6293 Remote Similarity NPD6899 Approved
0.6293 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6293 Remote Similarity NPD6011 Approved
0.6293 Remote Similarity NPD6881 Approved
0.6286 Remote Similarity NPD3573 Approved
0.6275 Remote Similarity NPD3667 Approved
0.6273 Remote Similarity NPD7839 Suspended
0.6273 Remote Similarity NPD7732 Phase 3
0.6262 Remote Similarity NPD5207 Approved
0.626 Remote Similarity NPD6319 Approved
0.625 Remote Similarity NPD1696 Phase 3
0.625 Remote Similarity NPD5363 Approved
0.6239 Remote Similarity NPD6012 Approved
0.6239 Remote Similarity NPD6014 Approved
0.6239 Remote Similarity NPD6373 Approved
0.6239 Remote Similarity NPD7900 Approved
0.6239 Remote Similarity NPD6372 Approved
0.6239 Remote Similarity NPD6013 Approved
0.6239 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6214 Remote Similarity NPD7154 Phase 3
0.621 Remote Similarity NPD8513 Phase 3
0.621 Remote Similarity NPD7503 Approved
0.6207 Remote Similarity NPD6412 Phase 2
0.6204 Remote Similarity NPD6079 Approved
0.62 Remote Similarity NPD5784 Clinical (unspecified phase)
0.619 Remote Similarity NPD5280 Approved
0.619 Remote Similarity NPD4694 Approved
0.619 Remote Similarity NPD5786 Approved
0.6186 Remote Similarity NPD7290 Approved
0.6186 Remote Similarity NPD7102 Approved
0.6186 Remote Similarity NPD6883 Approved
0.6182 Remote Similarity NPD5654 Approved
0.6168 Remote Similarity NPD6080 Approved
0.6168 Remote Similarity NPD6904 Approved
0.6168 Remote Similarity NPD6673 Approved
0.6167 Remote Similarity NPD4632 Approved
0.6161 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4786 Approved
0.614 Remote Similarity NPD5211 Phase 2
0.6134 Remote Similarity NPD6650 Approved
0.6134 Remote Similarity NPD6617 Approved
0.6134 Remote Similarity NPD8130 Phase 1
0.6134 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6134 Remote Similarity NPD6847 Approved
0.6134 Remote Similarity NPD6649 Approved
0.6134 Remote Similarity NPD6869 Approved
0.6129 Remote Similarity NPD7341 Phase 2
0.6126 Remote Similarity NPD4697 Phase 3
0.6126 Remote Similarity NPD5221 Approved
0.6126 Remote Similarity NPD5222 Approved
0.6126 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6124 Remote Similarity NPD7319 Approved
0.6121 Remote Similarity NPD6008 Approved
0.6117 Remote Similarity NPD4221 Approved
0.6117 Remote Similarity NPD4269 Approved
0.6117 Remote Similarity NPD4223 Phase 3
0.6117 Remote Similarity NPD4270 Approved
0.6111 Remote Similarity NPD8328 Phase 3
0.6111 Remote Similarity NPD7838 Discovery
0.6106 Remote Similarity NPD6404 Discontinued
0.6102 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6083 Remote Similarity NPD6882 Approved
0.6083 Remote Similarity NPD8297 Approved
0.608 Remote Similarity NPD8516 Approved
0.608 Remote Similarity NPD8515 Approved
0.608 Remote Similarity NPD8517 Approved
0.6075 Remote Similarity NPD5208 Approved
0.6071 Remote Similarity NPD4755 Approved
0.6071 Remote Similarity NPD5959 Approved
0.6071 Remote Similarity NPD5173 Approved
0.6064 Remote Similarity NPD3704 Approved
0.6063 Remote Similarity NPD7492 Approved
0.6058 Remote Similarity NPD6110 Phase 1
0.6036 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6034 Remote Similarity NPD5141 Approved
0.6034 Remote Similarity NPD5909 Discontinued
0.6032 Remote Similarity NPD2838 Clinical (unspecified phase)
0.6016 Remote Similarity NPD6009 Approved
0.6016 Remote Similarity NPD7507 Approved
0.6016 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6016 Remote Similarity NPD6616 Approved
0.6 Remote Similarity NPD4202 Approved
0.6 Remote Similarity NPD6059 Approved
0.6 Remote Similarity NPD6054 Approved
0.6 Remote Similarity NPD4197 Approved
0.5969 Remote Similarity NPD8293 Discontinued
0.5969 Remote Similarity NPD7078 Approved
0.5965 Remote Similarity NPD4700 Approved
0.5965 Remote Similarity NPD5286 Approved
0.5965 Remote Similarity NPD4696 Approved
0.5965 Remote Similarity NPD5285 Approved
0.5963 Remote Similarity NPD4096 Approved
0.5962 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5954 Remote Similarity NPD6914 Discontinued
0.5952 Remote Similarity NPD5983 Phase 2
0.5952 Remote Similarity NPD6016 Approved
0.5952 Remote Similarity NPD6015 Approved
0.5943 Remote Similarity NPD5329 Approved
0.5935 Remote Similarity NPD6868 Approved
0.5935 Remote Similarity NPD6274 Approved
0.5932 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5926 Remote Similarity NPD4518 Approved
0.5923 Remote Similarity NPD7736 Approved
0.5922 Remote Similarity NPD4252 Approved
0.5922 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5917 Remote Similarity NPD4634 Approved
0.5913 Remote Similarity NPD5223 Approved
0.5906 Remote Similarity NPD5988 Approved
0.5906 Remote Similarity NPD6370 Approved
0.5905 Remote Similarity NPD5362 Discontinued
0.5905 Remote Similarity NPD4788 Approved
0.5888 Remote Similarity NPD5690 Phase 2
0.5888 Remote Similarity NPD4689 Approved
0.5888 Remote Similarity NPD4688 Approved
0.5888 Remote Similarity NPD4693 Phase 3
0.5888 Remote Similarity NPD4138 Approved
0.5888 Remote Similarity NPD4249 Approved
0.5888 Remote Similarity NPD4690 Approved
0.5888 Remote Similarity NPD5205 Approved
0.5888 Remote Similarity NPD6098 Approved
0.5887 Remote Similarity NPD6317 Approved

Structure

External Identifiers

PubChem CID  
ChEMBL  
ZINC  

Physicochemical Properties

Molecular Weight:  402.17
ALogP:  0.5597
MLogP:  3.11
XLogP:  1.333
# Rotatable Bonds:  11
Polar Surface Area:  110.13
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  29

Download Data

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