Natural Product: NPC476829

Natural Product ID:  NPC476829
Common Name:   Halishigamide D
IUPAC Name:   methyl 2-[(1E,16E)-6-[(E)-9-(2-carbamoyl-1,3-oxazol-4-yl)-3-hydroxy-9-methoxy-8-methyl-7-oxonon-5-enoyl]oxy-17-[formyl(methyl)amino]-8,14-dimethoxy-5,9,13-trimethyl-12-oxoheptadeca-1,16-dienyl]-1,3-oxazole-4-carboxylate
Synonyms:   Halishigamide D
Molecular Formula:   C44H64N4O14
Standard InCHIKey:  ZXRAPGWKFNGPQU-JKQLDQSBSA-N
Standard InCHI:  InChI=1S/C44H64N4O14/c1-27(14-10-11-18-39-46-33(25-60-39)44(55)59-9)38(23-37(57-7)28(2)19-20-35(52)29(3)36(56-6)17-13-21-48(5)26-49)62-40(53)22-31(50)15-12-16-34(51)30(4)41(58-8)32-24-61-43(47-32)42(45)54/h11-13,16,18,21,24-31,36-38,41,50H,10,14-15,17,19-20,22-23H2,1-9H3,(H2,45,54)/b16-12+,18-11+,21-13+
Canonical SMILES:  O=CN(/C=C/CC(C(C(=O)CCC(C(CC(C(CC/C=C/c1occ(n1)C(=O)OC)C)OC(=O)CC(C/C=C/C(=O)C(C(c1coc(n1)C(=O)N)OC)C)O)OC)C)C)OC)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
NPO17255 Chondrosia corticata Species Chondrillidae Eukaryota PMID[15568783]
NPO17255 Chondrosia corticata Species Chondrillidae Eukaryota reef slopes on the south side of Cocos Lagoon, Guam PMID[21550239]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT137 Cell Line L1210 Mus musculus IC50 = 1.1 ug/ml 10.1021/np960558d
NPT91 Cell Line KB Homo sapiens IC50 = 1.8 ug/ml 10.1021/np960558d
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC = 6.5 ug/ml 10.1021/np960558d
NPT111 Cell Line K562 Homo sapiens LC50 = 92 ug/ml 15568783
NPT20 Organism Candida albicans Candida albicans MIC > 100 ug/ml 21550239
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC > 100 ug/ml 21550239
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC > 100 ug/ml 21550239
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC > 100 ug/ml 21550239
NPT2 Others Unspecified Activity = 40 % 21550239

  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 NPC476829 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
0.8806 High Similarity NPC476832
0.8473 Intermediate Similarity NPC476826
0.8473 Intermediate Similarity NPC476831
0.8473 Intermediate Similarity NPC476827
0.8431 Intermediate Similarity NPC476830
0.835 Intermediate Similarity NPC476828
0.8164 Intermediate Similarity NPC477219
0.8143 Intermediate Similarity NPC299035
0.8143 Intermediate Similarity NPC177432
0.8125 Intermediate Similarity NPC37924
0.8104 Intermediate Similarity NPC322800
0.8104 Intermediate Similarity NPC477218
0.8104 Intermediate Similarity NPC168135
0.8086 Intermediate Similarity NPC325683
0.788 Intermediate Similarity NPC30527
0.7656 Intermediate Similarity NPC314523
0.7656 Intermediate Similarity NPC58001
0.7476 Intermediate Similarity NPC258022
0.7353 Intermediate Similarity NPC224395
0.7353 Intermediate Similarity NPC208297
0.7234 Intermediate Similarity NPC211555
0.7233 Intermediate Similarity NPC289029
0.7233 Intermediate Similarity NPC48323
0.7181 Intermediate Similarity NPC186452
0.7136 Intermediate Similarity NPC295653
0.7136 Intermediate Similarity NPC107458
0.7108 Intermediate Similarity NPC88938
0.7108 Intermediate Similarity NPC58112
0.7108 Intermediate Similarity NPC306300
0.7031 Intermediate Similarity NPC12660
0.6995 Remote Similarity NPC54983
0.6893 Remote Similarity NPC46313
0.6893 Remote Similarity NPC199461
0.6893 Remote Similarity NPC103452
0.687 Remote Similarity NPC477585
0.687 Remote Similarity NPC477590
0.687 Remote Similarity NPC477588
0.687 Remote Similarity NPC477586
0.6783 Remote Similarity NPC477589
0.6783 Remote Similarity NPC477587
0.6667 Remote Similarity NPC49195
0.6444 Remote Similarity NPC309919
0.6298 Remote Similarity NPC470903
0.6298 Remote Similarity NPC167763
0.6298 Remote Similarity NPC470112
0.6293 Remote Similarity NPC475455
0.6161 Remote Similarity NPC299806
0.6154 Remote Similarity NPC475421
0.5976 Remote Similarity NPC72715
0.5959 Remote Similarity NPC316224
0.5948 Remote Similarity NPC314270
0.5947 Remote Similarity NPC196449
0.5947 Remote Similarity NPC314222
0.5942 Remote Similarity NPC196091
0.5923 Remote Similarity NPC315804
0.5923 Remote Similarity NPC313804
0.5917 Remote Similarity NPC102593
0.5917 Remote Similarity NPC196718
0.5917 Remote Similarity NPC475196
0.5911 Remote Similarity NPC237219
0.5902 Remote Similarity NPC472923
0.59 Remote Similarity NPC50274
0.5866 Remote Similarity NPC472436
0.5858 Remote Similarity NPC315411
0.5819 Remote Similarity NPC66191
0.5819 Remote Similarity NPC316297
0.5819 Remote Similarity NPC314817
0.5808 Remote Similarity NPC14877
0.5808 Remote Similarity NPC145178
0.5808 Remote Similarity NPC475350
0.5798 Remote Similarity NPC120335
0.5789 Remote Similarity NPC316403
0.5781 Remote Similarity NPC473833
0.5748 Remote Similarity NPC472435
0.5733 Remote Similarity NPC251036
0.5714 Remote Similarity NPC128683
0.5714 Remote Similarity NPC165964
0.5714 Remote Similarity NPC315542
0.5714 Remote Similarity NPC164006
0.5701 Remote Similarity NPC165538
0.5699 Remote Similarity NPC315061
0.5686 Remote Similarity NPC326930
0.5686 Remote Similarity NPC475301
0.5685 Remote Similarity NPC186351
0.5676 Remote Similarity NPC471978
0.5667 Remote Similarity NPC256912
0.5661 Remote Similarity NPC194740
0.5646 Remote Similarity NPC254700
0.564 Remote Similarity NPC75179
0.5634 Remote Similarity NPC477462
0.5634 Remote Similarity NPC473704
0.5628 Remote Similarity NPC184680
0.5625 Remote Similarity NPC53255
0.5625 Remote Similarity NPC85879
0.562 Remote Similarity NPC244536
0.5619 Remote Similarity NPC473502
0.5615 Remote Similarity NPC328928
0.5615 Remote Similarity NPC230683
0.5615 Remote Similarity NPC309525
0.5611 Remote Similarity NPC329961
0.5611 Remote Similarity NPC122427
0.5605 Remote Similarity NPC470785
0.5605 Remote Similarity NPC470784
0.5603 Remote Similarity NPC13603
0.56 Remote Similarity NPC135121

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476829 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
0.7268 Intermediate Similarity NPD7896 Approved
0.6746 Remote Similarity NPD6347 Phase 2
0.6635 Remote Similarity NPD7490 Discontinued
0.6311 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6239 Remote Similarity NPD6169 Phase 1
0.6193 Remote Similarity NPD6857 Phase 3
0.6186 Remote Similarity NPD7031 Phase 1
0.6164 Remote Similarity NPD7547 Clinical (unspecified phase)
0.613 Remote Similarity NPD6974 Phase 3
0.6109 Remote Similarity NPD7853 Phase 2
0.6058 Remote Similarity NPD4394 Clinical (unspecified phase)
0.6043 Remote Similarity NPD5443 Clinical (unspecified phase)
0.6034 Remote Similarity NPD7180 Phase 3
0.5966 Remote Similarity NPD1659 Phase 1
0.5964 Remote Similarity NPD2779 Approved
0.5957 Remote Similarity NPD1638 Discovery
0.59 Remote Similarity NPD4898 Clinical (unspecified phase)
0.5885 Remote Similarity NPD5922 Phase 3
0.5865 Remote Similarity NPD6247 Clinical (unspecified phase)
0.5862 Remote Similarity NPD2433 Clinical (unspecified phase)
0.5854 Remote Similarity NPD7022 Phase 2
0.5844 Remote Similarity NPD3945 Discontinued
0.583 Remote Similarity NPD2778 Approved
0.5815 Remote Similarity NPD4130 Phase 3
0.5809 Remote Similarity NPD7284 Clinical (unspecified phase)
0.5783 Remote Similarity NPD3392 Approved
0.5781 Remote Similarity NPD8356 Approved
0.5771 Remote Similarity NPD5532 Phase 2
0.5769 Remote Similarity NPD7393 Clinical (unspecified phase)
0.5768 Remote Similarity NPD7589 Clinical (unspecified phase)
0.5766 Remote Similarity NPD6495 Clinical (unspecified phase)
0.5763 Remote Similarity NPD8479 Phase 2
0.5752 Remote Similarity NPD6863 Phase 2
0.5738 Remote Similarity NPD2951 Discontinued
0.5733 Remote Similarity NPD5866 Approved
0.5714 Remote Similarity NPD6824 Clinical (unspecified phase)
0.5708 Remote Similarity NPD3263 Phase 3
0.5708 Remote Similarity NPD5640 Discontinued
0.5702 Remote Similarity NPD5924 Discontinued
0.5691 Remote Similarity NPD4368 Phase 2
0.5685 Remote Similarity NPD8430 Approved
0.5669 Remote Similarity NPD5857 Phase 3
0.5647 Remote Similarity NPD2081 Clinical (unspecified phase)
0.5633 Remote Similarity NPD4373 Phase 2
0.563 Remote Similarity NPD5850 Phase 3
0.562 Remote Similarity NPD3801 Clinical (unspecified phase)
0.562 Remote Similarity NPD4086 Phase 1
0.5611 Remote Similarity NPD1986 Approved
0.5605 Remote Similarity NPD3958 Approved

Structure

External Identifiers

PubChem CID   10509868
ChEMBL   CHEMBL450386
ZINC  

Physicochemical Properties

Molecular Weight:  872.44
ALogP:  -0.3279
MLogP:  4.32
XLogP:  1.128
# Rotatable Bonds:  44
Polar Surface Area:  250.12
# H-Bond Aceptor:  16
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  62

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