Natural Product: NPC185253

Natural Product ID:  NPC185253
Common Name:   Chaetomugilin I
IUPAC Name:   (7S,8S)-5-chloro-7-hydroxy-3-[(E,3R,4R)-4-hydroxy-3-methylpent-1-enyl]-7-methyl-8-[(E)-3-methyl-2-oxopent-3-enyl]-8H-isochromen-6-one
Synonyms:   Chaetomugilin I
Molecular Formula:   C22H27ClO5
Standard InCHIKey:  BYFBAJVBSPNIFS-YJTDBNEFSA-N
Standard InCHI:  InChI=1S/C22H27ClO5/c1-6-12(2)19(25)10-18-17-11-28-15(8-7-13(3)14(4)24)9-16(17)20(23)21(26)22(18,5)27/h6-9,11,13-14,18,24,27H,10H2,1-5H3/b8-7+,12-6+/t13-,14-,18+,22+/m1/s1
Canonical SMILES:  C/C=C(/C(=O)C[C@H]1C2=COC(=CC2=C(C(=O)[C@@]1(C)O)Cl)/C=C/[C@H]([C@H](O)C)C)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
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota PMID[21640594]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota PMID[26343828]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT71 Cell Line HEK293 Homo sapiens Survival = 59.2 % 24852121
NPT113 Cell Line RAW264.7 Mus musculus Survival = 37.1 % 18044832
NPT91 Cell Line KB Homo sapiens IC50 = 0.0023 nM 10.1016/S0305-1978(03)00160-1
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 300 nM 9784152
NPT137 Cell Line L1210 Mus musculus IC50 = 0.0019 nM 20541427
NPT116 Cell Line HL-60 Homo sapiens IC50 = 0.0011 nM 19167886
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 1500 nM 20303767
NPT168 Cell Line P388 Mus musculus IC50 = 0.0011 nM 25397992
NPT2 Others Unspecified Inhibition = 99.9 % 15646539
NPT2 Others Unspecified IC50 = 900 nM 9157194
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 99.9 % 9748375

  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 NPC185253 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
1.0 High Similarity NPC215253
0.9891 High Similarity NPC166770
0.9783 High Similarity NPC134083
0.9479 High Similarity NPC473144
0.9479 High Similarity NPC297281
0.8298 Intermediate Similarity NPC203795
0.8198 Intermediate Similarity NPC476815
0.8198 Intermediate Similarity NPC31641
0.8137 Intermediate Similarity NPC224172
0.8108 Intermediate Similarity NPC245320
0.8077 Intermediate Similarity NPC272528
0.8036 Intermediate Similarity NPC473145
0.7959 Intermediate Similarity NPC224270
0.7768 Intermediate Similarity NPC243298
0.7757 Intermediate Similarity NPC232969
0.7757 Intermediate Similarity NPC199107
0.7647 Intermediate Similarity NPC12727
0.7642 Intermediate Similarity NPC320294
0.7549 Intermediate Similarity NPC143210
0.7525 Intermediate Similarity NPC32552
0.75 Intermediate Similarity NPC471694
0.7477 Intermediate Similarity NPC25666
0.7477 Intermediate Similarity NPC271059
0.7453 Intermediate Similarity NPC469851
0.7431 Intermediate Similarity NPC469853
0.7339 Intermediate Similarity NPC469852
0.7333 Intermediate Similarity NPC208094
0.7308 Intermediate Similarity NPC295347
0.7297 Intermediate Similarity NPC137911
0.7297 Intermediate Similarity NPC228477
0.729 Intermediate Similarity NPC472637
0.7273 Intermediate Similarity NPC32037
0.7263 Intermediate Similarity NPC478122
0.7228 Intermediate Similarity NPC60765
0.7184 Intermediate Similarity NPC166110
0.7184 Intermediate Similarity NPC32944
0.7184 Intermediate Similarity NPC193396
0.7182 Intermediate Similarity NPC478052
0.7182 Intermediate Similarity NPC32006
0.7182 Intermediate Similarity NPC85529
0.7158 Intermediate Similarity NPC97173
0.7157 Intermediate Similarity NPC210216
0.7157 Intermediate Similarity NPC51358
0.7157 Intermediate Similarity NPC307092
0.7143 Intermediate Similarity NPC31021
0.7115 Intermediate Similarity NPC242637
0.7115 Intermediate Similarity NPC248193
0.7105 Intermediate Similarity NPC66108
0.71 Intermediate Similarity NPC187529
0.7087 Intermediate Similarity NPC131864
0.7083 Intermediate Similarity NPC231739
0.7071 Intermediate Similarity NPC16488
0.7071 Intermediate Similarity NPC288281
0.7059 Intermediate Similarity NPC26078
0.7059 Intermediate Similarity NPC473658
0.7043 Intermediate Similarity NPC321496
0.7043 Intermediate Similarity NPC326264
0.703 Intermediate Similarity NPC315395
0.703 Intermediate Similarity NPC94666
0.703 Intermediate Similarity NPC316426
0.7027 Intermediate Similarity NPC477125
0.7027 Intermediate Similarity NPC266570
0.7027 Intermediate Similarity NPC189863
0.701 Intermediate Similarity NPC19900
0.7 Intermediate Similarity NPC473624
0.6991 Remote Similarity NPC23497
0.699 Remote Similarity NPC118011
0.699 Remote Similarity NPC142159
0.699 Remote Similarity NPC95364
0.699 Remote Similarity NPC36668
0.699 Remote Similarity NPC212598
0.6981 Remote Similarity NPC476245
0.6981 Remote Similarity NPC91408
0.6979 Remote Similarity NPC82666
0.6972 Remote Similarity NPC244456
0.6972 Remote Similarity NPC469657
0.6972 Remote Similarity NPC471699
0.6972 Remote Similarity NPC115862
0.6964 Remote Similarity NPC185
0.6961 Remote Similarity NPC476079
0.6961 Remote Similarity NPC103743
0.6961 Remote Similarity NPC113370
0.6949 Remote Similarity NPC146786
0.6944 Remote Similarity NPC57079
0.6944 Remote Similarity NPC108368
0.6944 Remote Similarity NPC35717
0.6931 Remote Similarity NPC6185
0.6931 Remote Similarity NPC307112
0.6931 Remote Similarity NPC8518
0.6931 Remote Similarity NPC263997
0.6931 Remote Similarity NPC132228
0.6931 Remote Similarity NPC241512
0.6923 Remote Similarity NPC475823
0.6923 Remote Similarity NPC474209
0.6923 Remote Similarity NPC469372
0.6923 Remote Similarity NPC265856
0.6923 Remote Similarity NPC212369
0.6923 Remote Similarity NPC38952
0.6916 Remote Similarity NPC318082
0.6909 Remote Similarity NPC469606
0.6909 Remote Similarity NPC273005
0.6909 Remote Similarity NPC31058
0.6907 Remote Similarity NPC475994
0.69 Remote Similarity NPC477785
0.69 Remote Similarity NPC477784
0.69 Remote Similarity NPC477786
0.6897 Remote Similarity NPC474271
0.6893 Remote Similarity NPC7280
0.6893 Remote Similarity NPC307298
0.6893 Remote Similarity NPC53454
0.6893 Remote Similarity NPC229612
0.6887 Remote Similarity NPC474882
0.6887 Remote Similarity NPC299100
0.6887 Remote Similarity NPC78159
0.6887 Remote Similarity NPC38830
0.6881 Remote Similarity NPC46761
0.687 Remote Similarity NPC474315
0.6863 Remote Similarity NPC291712
0.6863 Remote Similarity NPC234038
0.6863 Remote Similarity NPC472974
0.6857 Remote Similarity NPC45579
0.6857 Remote Similarity NPC303697
0.6857 Remote Similarity NPC472975
0.6852 Remote Similarity NPC202705
0.6852 Remote Similarity NPC239895
0.6852 Remote Similarity NPC473161
0.6852 Remote Similarity NPC20066
0.6847 Remote Similarity NPC111323
0.6847 Remote Similarity NPC476848
0.6837 Remote Similarity NPC27817
0.6837 Remote Similarity NPC475681
0.6827 Remote Similarity NPC474918
0.6827 Remote Similarity NPC471054
0.6827 Remote Similarity NPC5509
0.6822 Remote Similarity NPC471698
0.6822 Remote Similarity NPC279313
0.6822 Remote Similarity NPC180950
0.6822 Remote Similarity NPC209355
0.6822 Remote Similarity NPC280725
0.6822 Remote Similarity NPC183012
0.6818 Remote Similarity NPC207885
0.6814 Remote Similarity NPC475294
0.681 Remote Similarity NPC221144
0.6804 Remote Similarity NPC471061
0.68 Remote Similarity NPC158411
0.68 Remote Similarity NPC279186
0.68 Remote Similarity NPC38796
0.68 Remote Similarity NPC103486
0.6796 Remote Similarity NPC181327
0.6792 Remote Similarity NPC282644
0.6792 Remote Similarity NPC29798
0.6792 Remote Similarity NPC476049
0.6792 Remote Similarity NPC134826
0.6789 Remote Similarity NPC222011
0.6789 Remote Similarity NPC316598
0.6789 Remote Similarity NPC306908
0.6786 Remote Similarity NPC118911
0.6774 Remote Similarity NPC474060
0.6768 Remote Similarity NPC74086
0.6765 Remote Similarity NPC255174
0.6765 Remote Similarity NPC476426
0.6765 Remote Similarity NPC281172
0.6765 Remote Similarity NPC471060
0.6765 Remote Similarity NPC28887
0.6762 Remote Similarity NPC253177
0.6762 Remote Similarity NPC469464
0.6762 Remote Similarity NPC220454
0.6762 Remote Similarity NPC469595
0.6762 Remote Similarity NPC213636
0.6762 Remote Similarity NPC113393
0.6762 Remote Similarity NPC280592
0.6762 Remote Similarity NPC476369
0.6762 Remote Similarity NPC212679
0.6762 Remote Similarity NPC476437
0.6759 Remote Similarity NPC78473
0.6757 Remote Similarity NPC87351
0.6757 Remote Similarity NPC235369
0.6757 Remote Similarity NPC303653
0.6757 Remote Similarity NPC189609
0.6757 Remote Similarity NPC140591
0.6757 Remote Similarity NPC291500
0.6757 Remote Similarity NPC114540
0.6757 Remote Similarity NPC32577
0.6757 Remote Similarity NPC155332
0.6757 Remote Similarity NPC197835
0.6754 Remote Similarity NPC327106
0.6754 Remote Similarity NPC220155
0.6752 Remote Similarity NPC469463
0.6752 Remote Similarity NPC469454
0.6752 Remote Similarity NPC469496
0.6733 Remote Similarity NPC475083
0.6733 Remote Similarity NPC297398
0.6731 Remote Similarity NPC477302
0.6731 Remote Similarity NPC106051
0.6729 Remote Similarity NPC477130
0.6729 Remote Similarity NPC477241
0.6729 Remote Similarity NPC217624
0.6729 Remote Similarity NPC191521
0.6729 Remote Similarity NPC474328
0.6729 Remote Similarity NPC474690

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC185253 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
0.6909 Remote Similarity NPD5091 Approved
0.6822 Remote Similarity NPD4629 Approved
0.6822 Remote Similarity NPD5210 Approved
0.6783 Remote Similarity NPD5169 Approved
0.6768 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6724 Remote Similarity NPD5127 Approved
0.6633 Remote Similarity NPD4756 Discovery
0.6609 Remote Similarity NPD5168 Approved
0.6609 Remote Similarity NPD5128 Approved
0.6602 Remote Similarity NPD1696 Phase 3
0.66 Remote Similarity NPD4695 Discontinued
0.6581 Remote Similarity NPD5217 Approved
0.6581 Remote Similarity NPD5215 Approved
0.6581 Remote Similarity NPD5216 Approved
0.6555 Remote Similarity NPD5167 Approved
0.6538 Remote Similarity NPD5279 Phase 3
0.6529 Remote Similarity NPD6314 Approved
0.6529 Remote Similarity NPD6313 Approved
0.6529 Remote Similarity NPD6335 Approved
0.6481 Remote Similarity NPD5133 Approved
0.646 Remote Similarity NPD5211 Phase 2
0.6455 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6455 Remote Similarity NPD5221 Approved
0.6455 Remote Similarity NPD5222 Approved
0.6449 Remote Similarity NPD5785 Approved
0.6446 Remote Similarity NPD7115 Discovery
0.6429 Remote Similarity NPD5285 Approved
0.6429 Remote Similarity NPD5286 Approved
0.6429 Remote Similarity NPD4696 Approved
0.6422 Remote Similarity NPD5282 Discontinued
0.6408 Remote Similarity NPD6110 Phase 1
0.6396 Remote Similarity NPD5173 Approved
0.6381 Remote Similarity NPD3618 Phase 1
0.6379 Remote Similarity NPD6614 Approved
0.6372 Remote Similarity NPD5223 Approved
0.6364 Remote Similarity NPD6868 Approved
0.6355 Remote Similarity NPD4753 Phase 2
0.6348 Remote Similarity NPD5141 Approved
0.6341 Remote Similarity NPD7100 Approved
0.6341 Remote Similarity NPD7101 Approved
0.6339 Remote Similarity NPD5696 Approved
0.6316 Remote Similarity NPD5226 Approved
0.6316 Remote Similarity NPD5225 Approved
0.6316 Remote Similarity NPD5224 Approved
0.6316 Remote Similarity NPD4633 Approved
0.6311 Remote Similarity NPD3667 Approved
0.6306 Remote Similarity NPD4697 Phase 3
0.6286 Remote Similarity NPD1694 Approved
0.6286 Remote Similarity NPD5363 Approved
0.6277 Remote Similarity NPD3704 Approved
0.6261 Remote Similarity NPD5175 Approved
0.6261 Remote Similarity NPD5174 Approved
0.625 Remote Similarity NPD6053 Discontinued
0.625 Remote Similarity NPD4755 Approved
0.6239 Remote Similarity NPD6079 Approved
0.6239 Remote Similarity NPD5697 Approved
0.6226 Remote Similarity NPD4694 Approved
0.6226 Remote Similarity NPD5280 Approved
0.6226 Remote Similarity NPD5690 Phase 2
0.6216 Remote Similarity NPD5654 Approved
0.6204 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6198 Remote Similarity NPD4632 Approved
0.6195 Remote Similarity NPD8029 Clinical (unspecified phase)
0.619 Remote Similarity NPD4786 Approved
0.619 Remote Similarity NPD3665 Phase 1
0.619 Remote Similarity NPD3133 Approved
0.619 Remote Similarity NPD3666 Approved
0.6186 Remote Similarity NPD6899 Approved
0.6186 Remote Similarity NPD6881 Approved
0.6186 Remote Similarity NPD6011 Approved
0.6183 Remote Similarity NPD7260 Phase 2
0.6182 Remote Similarity NPD5779 Approved
0.6182 Remote Similarity NPD5778 Approved
0.6167 Remote Similarity NPD6649 Approved
0.6167 Remote Similarity NPD6650 Approved
0.614 Remote Similarity NPD4700 Approved
0.6134 Remote Similarity NPD6014 Approved
0.6134 Remote Similarity NPD6012 Approved
0.6134 Remote Similarity NPD6013 Approved
0.6129 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6111 Remote Similarity NPD5983 Phase 2
0.6106 Remote Similarity NPD5959 Approved
0.6106 Remote Similarity NPD6084 Phase 2
0.6106 Remote Similarity NPD6083 Phase 2
0.6105 Remote Similarity NPD6108 Clinical (unspecified phase)
0.61 Remote Similarity NPD8264 Approved
0.6095 Remote Similarity NPD7154 Phase 3
0.6091 Remote Similarity NPD5284 Approved
0.6091 Remote Similarity NPD5281 Approved
0.6091 Remote Similarity NPD7515 Phase 2
0.6083 Remote Similarity NPD7102 Approved
0.6083 Remote Similarity NPD6883 Approved
0.6083 Remote Similarity NPD7290 Approved
0.608 Remote Similarity NPD4522 Approved
0.6075 Remote Similarity NPD4623 Approved
0.6075 Remote Similarity NPD4519 Discontinued
0.6071 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5695 Phase 3
0.6058 Remote Similarity NPD5369 Approved
0.6055 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6055 Remote Similarity NPD6101 Approved
0.6055 Remote Similarity NPD5328 Approved
0.6053 Remote Similarity NPD4225 Approved
0.605 Remote Similarity NPD4729 Approved
0.605 Remote Similarity NPD4730 Approved
0.6048 Remote Similarity NPD6009 Approved
0.6047 Remote Similarity NPD6336 Discontinued
0.6038 Remote Similarity NPD4197 Approved
0.6036 Remote Similarity NPD6399 Phase 3
0.6036 Remote Similarity NPD4202 Approved
0.6033 Remote Similarity NPD6847 Approved
0.6033 Remote Similarity NPD6617 Approved
0.6033 Remote Similarity NPD8130 Phase 1
0.6033 Remote Similarity NPD6869 Approved
0.6032 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6017 Remote Similarity NPD5739 Approved
0.6017 Remote Similarity NPD6675 Approved
0.6017 Remote Similarity NPD7128 Approved
0.6017 Remote Similarity NPD6402 Approved
0.6 Remote Similarity NPD6698 Approved
0.6 Remote Similarity NPD6372 Approved
0.6 Remote Similarity NPD4269 Approved
0.6 Remote Similarity NPD4270 Approved
0.6 Remote Similarity NPD5209 Approved
0.6 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6 Remote Similarity NPD46 Approved
0.6 Remote Similarity NPD6373 Approved
0.5984 Remote Similarity NPD6882 Approved
0.5984 Remote Similarity NPD8297 Approved
0.5983 Remote Similarity NPD4754 Approved
0.5982 Remote Similarity NPD7748 Approved
0.5981 Remote Similarity NPD5329 Approved
0.5966 Remote Similarity NPD5701 Approved
0.5965 Remote Similarity NPD7902 Approved
0.5962 Remote Similarity NPD4252 Approved
0.595 Remote Similarity NPD5251 Approved
0.595 Remote Similarity NPD5134 Clinical (unspecified phase)
0.595 Remote Similarity NPD5250 Approved
0.595 Remote Similarity NPD5247 Approved
0.595 Remote Similarity NPD5248 Approved
0.595 Remote Similarity NPD5135 Approved
0.595 Remote Similarity NPD4634 Approved
0.595 Remote Similarity NPD5249 Phase 3
0.5946 Remote Similarity NPD5693 Phase 1
0.5946 Remote Similarity NPD6411 Approved
0.5946 Remote Similarity NPD5694 Approved
0.5943 Remote Similarity NPD5362 Discontinued
0.5938 Remote Similarity NPD7331 Phase 2
0.5926 Remote Similarity NPD5786 Approved
0.5926 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5922 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5922 Remote Similarity NPD3617 Approved
0.5917 Remote Similarity NPD7320 Approved
0.5913 Remote Similarity NPD7638 Approved
0.5902 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5888 Remote Similarity NPD3668 Phase 3
0.5882 Remote Similarity NPD4767 Approved
0.5882 Remote Similarity NPD4768 Approved
0.5862 Remote Similarity NPD7640 Approved
0.5862 Remote Similarity NPD7639 Approved
0.5859 Remote Similarity NPD8513 Phase 3
0.5856 Remote Similarity NPD7838 Discovery
0.5856 Remote Similarity NPD5692 Phase 3
0.5849 Remote Similarity NPD4223 Phase 3
0.5849 Remote Similarity NPD4221 Approved
0.5842 Remote Similarity NPD4058 Approved
0.5833 Remote Similarity NPD6033 Approved
0.5833 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5818 Remote Similarity NPD6672 Approved
0.5818 Remote Similarity NPD4518 Approved
0.5818 Remote Similarity NPD5737 Approved
0.5804 Remote Similarity NPD6050 Approved
0.5794 Remote Similarity NPD6317 Approved
0.5784 Remote Similarity NPD8039 Approved
0.5778 Remote Similarity NPD6845 Suspended
0.5772 Remote Similarity NPD4141 Clinical (unspecified phase)
0.5772 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5772 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5746 Remote Similarity NPD5956 Approved
0.5741 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5739 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5736 Remote Similarity NPD8515 Approved
0.5736 Remote Similarity NPD8516 Approved
0.5736 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5736 Remote Similarity NPD8517 Approved
0.5727 Remote Similarity NPD3573 Approved
0.5714 Remote Similarity NPD5207 Approved
0.5714 Remote Similarity NPD6274 Approved
0.5702 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5702 Remote Similarity NPD7900 Approved
0.5701 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5691 Remote Similarity NPD6371 Approved
0.5686 Remote Similarity NPD4687 Approved
0.5684 Remote Similarity NPD368 Approved
0.567 Remote Similarity NPD7341 Phase 2
0.5664 Remote Similarity NPD7637 Suspended
0.5664 Remote Similarity NPD7983 Approved
0.566 Remote Similarity NPD4822 Approved
0.566 Remote Similarity NPD4819 Approved
0.566 Remote Similarity NPD4820 Approved

Structure

External Identifiers

PubChem CID   44250025
ChEMBL   CHEMBL1797233
ZINC  

Physicochemical Properties

Molecular Weight:  406.15
ALogP:  0.9217
MLogP:  3.22
XLogP:  2.143
# Rotatable Bonds:  14
Polar Surface Area:  83.83
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  28

Download Data

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