Natural Product: NPC322188

Natural Product ID:  NPC322188
Common Name:   Hirsutalin F
IUPAC Name:  
Synonyms:   Hirsutalin F
Molecular Formula:   C28H44O8
Standard InCHIKey:  HURFLECHLMMVAG-SVXRWCJSSA-N
Standard InCHI:  InChI=1S/C28H44O8/c1-7-9-22(31)34-20(8-2)26(32)36-28(6)13-12-21-27(5,33)14-19(30)23-16(3)10-11-18(17(4)15-29)24(23)25(28)35-21/h17-18,20-21,23-25,29,33H,3,7-15H2,1-2,4-6H3/t17-,18+,20?,21+,23+,24+,25+,27+,28+/m0/s1
Canonical SMILES:  CCCC(=O)OC(C(=O)O[C@]1(C)CC[C@H]2O[C@@H]1[C@@H]1[C@H](CCC(=C)[C@@H]1C(=O)C[C@@]2(C)O)[C@H](CO)C)CC
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
NPO16112 Cladiella hirsuta Species Alcyoniidae Eukaryota PMID[20979397]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens IC50 = 29000 nM 20979397
NPT2 Others Unspecified IC50 = 29000 nM 20979397
NPT83 Cell Line MCF7 Homo sapiens IC50 = 32000 nM 20979397

  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 NPC322188 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
0.8298 Intermediate Similarity NPC65359
0.8269 Intermediate Similarity NPC157476
0.8211 Intermediate Similarity NPC329952
0.8173 Intermediate Similarity NPC100908
0.8021 Intermediate Similarity NPC469627
0.7961 Intermediate Similarity NPC474101
0.7879 Intermediate Similarity NPC39859
0.7879 Intermediate Similarity NPC76862
0.7879 Intermediate Similarity NPC158416
0.7879 Intermediate Similarity NPC476009
0.7879 Intermediate Similarity NPC470883
0.781 Intermediate Similarity NPC289702
0.781 Intermediate Similarity NPC208461
0.7778 Intermediate Similarity NPC475900
0.7767 Intermediate Similarity NPC277074
0.7767 Intermediate Similarity NPC209298
0.7767 Intermediate Similarity NPC122811
0.7723 Intermediate Similarity NPC17183
0.7714 Intermediate Similarity NPC176949
0.7714 Intermediate Similarity NPC112780
0.7714 Intermediate Similarity NPC201908
0.7714 Intermediate Similarity NPC166993
0.77 Intermediate Similarity NPC469528
0.77 Intermediate Similarity NPC469369
0.77 Intermediate Similarity NPC260223
0.7692 Intermediate Similarity NPC470104
0.7684 Intermediate Similarity NPC321812
0.7684 Intermediate Similarity NPC322922
0.7677 Intermediate Similarity NPC190294
0.7667 Intermediate Similarity NPC474003
0.7664 Intermediate Similarity NPC320383
0.7664 Intermediate Similarity NPC137104
0.7664 Intermediate Similarity NPC474786
0.766 Intermediate Similarity NPC151176
0.766 Intermediate Similarity NPC475963
0.766 Intermediate Similarity NPC3464
0.7658 Intermediate Similarity NPC297179
0.7658 Intermediate Similarity NPC17772
0.7642 Intermediate Similarity NPC151393
0.7642 Intermediate Similarity NPC153587
0.7642 Intermediate Similarity NPC273155
0.7636 Intermediate Similarity NPC40632
0.7636 Intermediate Similarity NPC16081
0.7636 Intermediate Similarity NPC96312
0.7636 Intermediate Similarity NPC251236
0.7636 Intermediate Similarity NPC173686
0.7636 Intermediate Similarity NPC328374
0.7629 Intermediate Similarity NPC173926
0.7629 Intermediate Similarity NPC77001
0.7629 Intermediate Similarity NPC253618
0.7629 Intermediate Similarity NPC474951
0.7624 Intermediate Similarity NPC111348
0.7624 Intermediate Similarity NPC328562
0.7624 Intermediate Similarity NPC323421
0.7619 Intermediate Similarity NPC200957
0.7619 Intermediate Similarity NPC138908
0.7619 Intermediate Similarity NPC292588
0.7615 Intermediate Similarity NPC7921
0.7615 Intermediate Similarity NPC208998
0.7609 Intermediate Similarity NPC103634
0.7596 Intermediate Similarity NPC469985
0.7589 Intermediate Similarity NPC319570
0.7576 Intermediate Similarity NPC199543
0.7573 Intermediate Similarity NPC236585
0.7573 Intermediate Similarity NPC252614
0.757 Intermediate Similarity NPC131903
0.757 Intermediate Similarity NPC16657
0.757 Intermediate Similarity NPC204652
0.757 Intermediate Similarity NPC274827
0.7568 Intermediate Similarity NPC97908
0.7568 Intermediate Similarity NPC122033
0.7568 Intermediate Similarity NPC476713
0.7568 Intermediate Similarity NPC476712
0.7568 Intermediate Similarity NPC470854
0.7568 Intermediate Similarity NPC474654
0.7568 Intermediate Similarity NPC287343
0.7553 Intermediate Similarity NPC239308
0.7549 Intermediate Similarity NPC474793
0.7549 Intermediate Similarity NPC471038
0.7547 Intermediate Similarity NPC186054
0.7547 Intermediate Similarity NPC471474
0.7545 Intermediate Similarity NPC143268
0.7545 Intermediate Similarity NPC45218
0.7545 Intermediate Similarity NPC473798
0.7545 Intermediate Similarity NPC323821
0.7545 Intermediate Similarity NPC268238
0.7526 Intermediate Similarity NPC255176
0.7525 Intermediate Similarity NPC31645
0.7525 Intermediate Similarity NPC256227
0.7525 Intermediate Similarity NPC219353
0.7524 Intermediate Similarity NPC301787
0.7523 Intermediate Similarity NPC474927
0.7523 Intermediate Similarity NPC317687
0.7522 Intermediate Similarity NPC317635
0.7522 Intermediate Similarity NPC329008
0.7521 Intermediate Similarity NPC188291
0.75 Intermediate Similarity NPC475491
0.75 Intermediate Similarity NPC470776
0.75 Intermediate Similarity NPC251310
0.75 Intermediate Similarity NPC85391
0.75 Intermediate Similarity NPC275990
0.75 Intermediate Similarity NPC469626
0.75 Intermediate Similarity NPC286347
0.7478 Intermediate Similarity NPC91693
0.7478 Intermediate Similarity NPC265557
0.7478 Intermediate Similarity NPC18945
0.7478 Intermediate Similarity NPC105926
0.7477 Intermediate Similarity NPC476711
0.7477 Intermediate Similarity NPC476710
0.7477 Intermediate Similarity NPC63841
0.7477 Intermediate Similarity NPC474734
0.7477 Intermediate Similarity NPC473410
0.7477 Intermediate Similarity NPC469984
0.7477 Intermediate Similarity NPC190185
0.7477 Intermediate Similarity NPC134869
0.7477 Intermediate Similarity NPC152199
0.7477 Intermediate Similarity NPC471094
0.7477 Intermediate Similarity NPC235539
0.7477 Intermediate Similarity NPC293850
0.7477 Intermediate Similarity NPC213084
0.7476 Intermediate Similarity NPC293890
0.7476 Intermediate Similarity NPC470388
0.7476 Intermediate Similarity NPC472972
0.7476 Intermediate Similarity NPC267921
0.7475 Intermediate Similarity NPC198054
0.7473 Intermediate Similarity NPC469867
0.7456 Intermediate Similarity NPC470779
0.7456 Intermediate Similarity NPC75417
0.7455 Intermediate Similarity NPC471252
0.7455 Intermediate Similarity NPC49451
0.7455 Intermediate Similarity NPC198539
0.7455 Intermediate Similarity NPC94509
0.7453 Intermediate Similarity NPC56656
0.7453 Intermediate Similarity NPC222833
0.7453 Intermediate Similarity NPC50535
0.7451 Intermediate Similarity NPC124246
0.7451 Intermediate Similarity NPC40812
0.7451 Intermediate Similarity NPC236176
0.7449 Intermediate Similarity NPC92974
0.7434 Intermediate Similarity NPC180550
0.7434 Intermediate Similarity NPC470777
0.7434 Intermediate Similarity NPC475171
0.7434 Intermediate Similarity NPC309780
0.7434 Intermediate Similarity NPC6377
0.7434 Intermediate Similarity NPC469945
0.7434 Intermediate Similarity NPC214484
0.7434 Intermediate Similarity NPC157868
0.7434 Intermediate Similarity NPC35405
0.7434 Intermediate Similarity NPC39211
0.7434 Intermediate Similarity NPC208381
0.7434 Intermediate Similarity NPC11551
0.7434 Intermediate Similarity NPC472949
0.7434 Intermediate Similarity NPC473884
0.7434 Intermediate Similarity NPC114441
0.7431 Intermediate Similarity NPC171888
0.7431 Intermediate Similarity NPC470281
0.7431 Intermediate Similarity NPC472003
0.7431 Intermediate Similarity NPC146945
0.7431 Intermediate Similarity NPC317107
0.7431 Intermediate Similarity NPC213320
0.7431 Intermediate Similarity NPC34315
0.7429 Intermediate Similarity NPC225238
0.7429 Intermediate Similarity NPC96217
0.7426 Intermediate Similarity NPC248574
0.7414 Intermediate Similarity NPC476729
0.7411 Intermediate Similarity NPC224121
0.7411 Intermediate Similarity NPC473590
0.7411 Intermediate Similarity NPC146432
0.7411 Intermediate Similarity NPC470778
0.7411 Intermediate Similarity NPC470775
0.7411 Intermediate Similarity NPC176513
0.7407 Intermediate Similarity NPC42662
0.7407 Intermediate Similarity NPC475922
0.7407 Intermediate Similarity NPC27814
0.7404 Intermediate Similarity NPC97435
0.7404 Intermediate Similarity NPC46848
0.7404 Intermediate Similarity NPC98225
0.74 Intermediate Similarity NPC478036
0.74 Intermediate Similarity NPC478037
0.74 Intermediate Similarity NPC475788
0.7391 Intermediate Similarity NPC476986
0.7391 Intermediate Similarity NPC471965
0.7391 Intermediate Similarity NPC312833
0.7391 Intermediate Similarity NPC470905
0.7391 Intermediate Similarity NPC162574
0.7387 Intermediate Similarity NPC299849
0.7387 Intermediate Similarity NPC18547
0.7387 Intermediate Similarity NPC473898
0.7387 Intermediate Similarity NPC474906
0.7383 Intermediate Similarity NPC202524
0.7383 Intermediate Similarity NPC251824
0.7383 Intermediate Similarity NPC3316
0.7383 Intermediate Similarity NPC86852
0.7383 Intermediate Similarity NPC144854
0.7379 Intermediate Similarity NPC255592
0.7379 Intermediate Similarity NPC83895
0.7379 Intermediate Similarity NPC469565
0.7379 Intermediate Similarity NPC261377
0.7379 Intermediate Similarity NPC26270
0.7379 Intermediate Similarity NPC187761

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC322188 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
0.781 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD8328 Phase 3
0.7257 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD6319 Approved
0.7155 Intermediate Similarity NPD6921 Approved
0.7129 Intermediate Similarity NPD7983 Approved
0.6937 Remote Similarity NPD6373 Approved
0.6937 Remote Similarity NPD6372 Approved
0.6931 Remote Similarity NPD6101 Approved
0.6931 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6903 Remote Similarity NPD8297 Approved
0.6893 Remote Similarity NPD5778 Approved
0.6893 Remote Similarity NPD5779 Approved
0.6863 Remote Similarity NPD6698 Approved
0.6863 Remote Similarity NPD46 Approved
0.6847 Remote Similarity NPD6686 Approved
0.6842 Remote Similarity NPD4632 Approved
0.6833 Remote Similarity NPD7492 Approved
0.6818 Remote Similarity NPD5739 Approved
0.6818 Remote Similarity NPD6402 Approved
0.6818 Remote Similarity NPD6675 Approved
0.6818 Remote Similarity NPD7128 Approved
0.6814 Remote Similarity NPD6650 Approved
0.6814 Remote Similarity NPD6649 Approved
0.6796 Remote Similarity NPD6411 Approved
0.6786 Remote Similarity NPD8132 Clinical (unspecified phase)
0.678 Remote Similarity NPD6054 Approved
0.678 Remote Similarity NPD6059 Approved
0.6777 Remote Similarity NPD6616 Approved
0.6757 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6721 Remote Similarity NPD8293 Discontinued
0.6721 Remote Similarity NPD7078 Approved
0.6696 Remote Similarity NPD7320 Approved
0.6696 Remote Similarity NPD6899 Approved
0.6696 Remote Similarity NPD6881 Approved
0.6696 Remote Similarity NPD8133 Approved
0.6667 Remote Similarity NPD5282 Discontinued
0.6667 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6009 Approved
0.6667 Remote Similarity NPD6370 Approved
0.6667 Remote Similarity NPD7736 Approved
0.6636 Remote Similarity NPD6084 Phase 2
0.6636 Remote Similarity NPD6083 Phase 2
0.6612 Remote Similarity NPD7604 Phase 2
0.6609 Remote Similarity NPD6882 Approved
0.6607 Remote Similarity NPD6412 Phase 2
0.6607 Remote Similarity NPD5697 Approved
0.6607 Remote Similarity NPD5701 Approved
0.6583 Remote Similarity NPD6015 Approved
0.6583 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6583 Remote Similarity NPD6016 Approved
0.6583 Remote Similarity NPD5983 Phase 2
0.6579 Remote Similarity NPD7290 Approved
0.6579 Remote Similarity NPD7102 Approved
0.6579 Remote Similarity NPD6883 Approved
0.6571 Remote Similarity NPD6399 Phase 3
0.6549 Remote Similarity NPD6011 Approved
0.6529 Remote Similarity NPD8080 Discontinued
0.6529 Remote Similarity NPD5988 Approved
0.6522 Remote Similarity NPD6617 Approved
0.6522 Remote Similarity NPD6869 Approved
0.6522 Remote Similarity NPD8130 Phase 1
0.6522 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6522 Remote Similarity NPD6847 Approved
0.6504 Remote Similarity NPD6336 Discontinued
0.6491 Remote Similarity NPD6012 Approved
0.6491 Remote Similarity NPD6014 Approved
0.6491 Remote Similarity NPD6013 Approved
0.648 Remote Similarity NPD7319 Approved
0.6476 Remote Similarity NPD8034 Phase 2
0.6476 Remote Similarity NPD8035 Phase 2
0.6465 Remote Similarity NPD5369 Approved
0.6449 Remote Similarity NPD5695 Phase 3
0.6446 Remote Similarity NPD8515 Approved
0.6446 Remote Similarity NPD8516 Approved
0.6446 Remote Similarity NPD8517 Approved
0.6446 Remote Similarity NPD8513 Phase 3
0.6435 Remote Similarity NPD4634 Approved
0.6435 Remote Similarity NPD6371 Approved
0.6422 Remote Similarity NPD5696 Approved
0.64 Remote Similarity NPD6435 Approved
0.64 Remote Similarity NPD6033 Approved
0.6396 Remote Similarity NPD8086 Approved
0.6396 Remote Similarity NPD8084 Approved
0.6396 Remote Similarity NPD8138 Approved
0.6396 Remote Similarity NPD8083 Approved
0.6396 Remote Similarity NPD8085 Approved
0.6396 Remote Similarity NPD8139 Approved
0.6396 Remote Similarity NPD8082 Approved
0.6389 Remote Similarity NPD7839 Suspended
0.6385 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6371 Remote Similarity NPD7507 Approved
0.6346 Remote Similarity NPD6672 Approved
0.6346 Remote Similarity NPD5737 Approved
0.6339 Remote Similarity NPD8276 Approved
0.6339 Remote Similarity NPD8275 Approved
0.6337 Remote Similarity NPD6110 Phase 1
0.633 Remote Similarity NPD7902 Approved
0.6311 Remote Similarity NPD5786 Approved
0.6306 Remote Similarity NPD1700 Approved
0.6283 Remote Similarity NPD8081 Approved
0.6273 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6273 Remote Similarity NPD4225 Approved
0.625 Remote Similarity NPD7115 Discovery
0.625 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6228 Remote Similarity NPD6008 Approved
0.6228 Remote Similarity NPD8393 Approved
0.6214 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6207 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6204 Remote Similarity NPD7748 Approved
0.62 Remote Similarity NPD5368 Approved
0.6198 Remote Similarity NPD6335 Approved
0.619 Remote Similarity NPD8074 Phase 3
0.6186 Remote Similarity NPD6053 Discontinued
0.6183 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6182 Remote Similarity NPD4755 Approved
0.6176 Remote Similarity NPD3669 Approved
0.6176 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6168 Remote Similarity NPD7515 Phase 2
0.6167 Remote Similarity NPD6274 Approved
0.6162 Remote Similarity NPD4802 Phase 2
0.6162 Remote Similarity NPD4238 Approved
0.616 Remote Similarity NPD8340 Approved
0.616 Remote Similarity NPD8341 Approved
0.616 Remote Similarity NPD8299 Approved
0.616 Remote Similarity NPD8342 Approved
0.6154 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6154 Remote Similarity NPD7909 Approved
0.6154 Remote Similarity NPD6098 Approved
0.6148 Remote Similarity NPD7100 Approved
0.6148 Remote Similarity NPD7101 Approved
0.6147 Remote Similarity NPD1698 Clinical (unspecified phase)
0.614 Remote Similarity NPD4056 Clinical (unspecified phase)
0.614 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6139 Remote Similarity NPD1780 Approved
0.6139 Remote Similarity NPD1779 Approved
0.6132 Remote Similarity NPD6904 Approved
0.6132 Remote Similarity NPD6673 Approved
0.6132 Remote Similarity NPD6080 Approved
0.6126 Remote Similarity NPD7638 Approved
0.6124 Remote Similarity NPD7260 Phase 2
0.6116 Remote Similarity NPD6317 Approved
0.6111 Remote Similarity NPD8451 Approved
0.6107 Remote Similarity NPD8415 Approved
0.61 Remote Similarity NPD7329 Approved
0.6091 Remote Similarity NPD4697 Phase 3
0.6078 Remote Similarity NPD4270 Approved
0.6078 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6078 Remote Similarity NPD4269 Approved
0.6075 Remote Similarity NPD7838 Discovery
0.6071 Remote Similarity NPD7639 Approved
0.6071 Remote Similarity NPD5286 Approved
0.6071 Remote Similarity NPD4700 Approved
0.6071 Remote Similarity NPD4696 Approved
0.6071 Remote Similarity NPD7640 Approved
0.6071 Remote Similarity NPD5285 Approved
0.6066 Remote Similarity NPD6314 Approved
0.6066 Remote Similarity NPD7641 Discontinued
0.6066 Remote Similarity NPD6313 Approved
0.6063 Remote Similarity NPD8448 Approved
0.6055 Remote Similarity NPD7900 Approved
0.6055 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6048 Remote Similarity NPD6908 Approved
0.6048 Remote Similarity NPD6909 Approved
0.6048 Remote Similarity NPD8269 Approved
0.6048 Remote Similarity NPD8267 Approved
0.6048 Remote Similarity NPD8268 Approved
0.6048 Remote Similarity NPD8266 Approved
0.6033 Remote Similarity NPD6868 Approved
0.6019 Remote Similarity NPD6050 Approved
0.6019 Remote Similarity NPD7637 Suspended
0.6019 Remote Similarity NPD4788 Approved
0.6018 Remote Similarity NPD5344 Discontinued
0.6018 Remote Similarity NPD5223 Approved
0.6 Remote Similarity NPD5279 Phase 3
0.6 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6 Remote Similarity NPD7334 Approved
0.6 Remote Similarity NPD7146 Approved
0.6 Remote Similarity NPD5330 Approved
0.6 Remote Similarity NPD6684 Approved
0.6 Remote Similarity NPD7521 Approved
0.6 Remote Similarity NPD6409 Approved
0.6 Remote Similarity NPD6422 Discontinued
0.5981 Remote Similarity NPD5328 Approved
0.5981 Remote Similarity NPD4753 Phase 2
0.5965 Remote Similarity NPD8301 Approved
0.5965 Remote Similarity NPD5225 Approved
0.5965 Remote Similarity NPD5211 Phase 2
0.5965 Remote Similarity NPD4633 Approved
0.5965 Remote Similarity NPD8300 Approved
0.5965 Remote Similarity NPD5226 Approved
0.5965 Remote Similarity NPD5224 Approved
0.5962 Remote Similarity NPD4786 Approved
0.5957 Remote Similarity NPD898 Approved
0.5957 Remote Similarity NPD897 Approved
0.5957 Remote Similarity NPD896 Approved
0.5954 Remote Similarity NPD6845 Suspended
0.5952 Remote Similarity NPD7642 Approved
0.5948 Remote Similarity NPD4768 Approved
0.5948 Remote Similarity NPD4767 Approved

Structure

External Identifiers

PubChem CID   50900139
ChEMBL   CHEMBL1631452
ZINC  

Physicochemical Properties

Molecular Weight:  508.30
ALogP:  -1.6876
MLogP:  3.66
XLogP:  2.931
# Rotatable Bonds:  17
Polar Surface Area:  119.36
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  36

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