Natural Product: NPC293136

Natural Product ID:  NPC293136
Common Name:   Squamostatin-D
IUPAC Name:   (2R)-4-[9-[(2R,5S)-5-[(1R,4R)-1,4-dihydroxy-4-[(2S,5S)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]nonyl]-2-methyl-2H-furan-5-one
Synonyms:   Squamostatin-D
Molecular Formula:   C37H66O7
Standard InCHIKey:  VZEPVAAWZDUQLP-JOARZRRZSA-N
Standard InCHI:  InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(38)35-25-26-36(44-35)33(40)23-22-32(39)34-24-21-30(43-34)19-16-13-10-8-9-12-15-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30-,31+,32-,33-,34+,35+,36+/m1/s1
Canonical SMILES:  CCCCCCCCCC[C@@H]([C@@H]1CC[C@H](O1)[C@@H](CC[C@H]([C@@H]1CC[C@H](O1)CCCCCCCCCC1=C[C@H](OC1=O)C)O)O)O
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
NPO2884 Annona squamosa Species Annonaceae Eukaryota seeds PMID[22011319]
NPO2884 Annona squamosa Species Annonaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT165 Cell Line HeLa Homo sapiens IC50 = 38 nM 19285863
NPT2 Others Unspecified IC50 = 54 nM 19285863
NPT515 Cell Line SGC-7901 Homo sapiens IC50 = 180 nM 19285863
NPT83 Cell Line MCF7 Homo sapiens IC50 = 45 nM 19285863
NPT2 Others Unspecified IC50 = 1.4 nM 19285863
NPT81 Cell Line A549 Homo sapiens IC50 = 0.046 ug/ml 22011319
NPT165 Cell Line HeLa Homo sapiens IC50 = 0.1 ug/ml 22011319
NPT83 Cell Line MCF7 Homo sapiens IC50 = 0.11 ug/ml 22011319
NPT65 Cell Line HepG2 Homo sapiens IC50 = 0.56 ug/ml 22011319
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 0.25 ug/ml 22011319
NPT1097 Cell Line MKN-45 Homo sapiens IC50 = 0.87 ug/ml 22011319
NPT81 Cell Line A549 Homo sapiens Ratio IC50 = 7.8 25582602
NPT81 Cell Line A549 Homo sapiens IC50 = 16190 nM 25582602

  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 NPC293136 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 NPC241360
1.0 High Similarity NPC132940
0.9877 High Similarity NPC476583
0.9877 High Similarity NPC258068
0.9877 High Similarity NPC20533
0.9875 High Similarity NPC77871
0.9875 High Similarity NPC475268
0.9875 High Similarity NPC473671
0.9875 High Similarity NPC9678
0.9875 High Similarity NPC292809
0.9875 High Similarity NPC202055
0.9875 High Similarity NPC25764
0.9875 High Similarity NPC39279
0.9875 High Similarity NPC319036
0.9875 High Similarity NPC39167
0.9875 High Similarity NPC470400
0.9875 High Similarity NPC235809
0.9875 High Similarity NPC473156
0.9756 High Similarity NPC172821
0.9756 High Similarity NPC473905
0.9756 High Similarity NPC171135
0.9756 High Similarity NPC191929
0.9756 High Similarity NPC169511
0.9756 High Similarity NPC81045
0.9756 High Similarity NPC287164
0.9756 High Similarity NPC100454
0.9756 High Similarity NPC133730
0.9756 High Similarity NPC234077
0.9756 High Similarity NPC261952
0.9756 High Similarity NPC274446
0.9756 High Similarity NPC320569
0.9756 High Similarity NPC320458
0.9756 High Similarity NPC39754
0.9756 High Similarity NPC151403
0.9756 High Similarity NPC61257
0.9756 High Similarity NPC242364
0.9753 High Similarity NPC219652
0.9753 High Similarity NPC473840
0.9753 High Similarity NPC282815
0.9753 High Similarity NPC25703
0.975 High Similarity NPC156804
0.9639 High Similarity NPC473504
0.9639 High Similarity NPC20621
0.9639 High Similarity NPC42598
0.9639 High Similarity NPC40066
0.9639 High Similarity NPC81778
0.9639 High Similarity NPC93794
0.9639 High Similarity NPC318963
0.9639 High Similarity NPC91067
0.9634 High Similarity NPC473995
0.9634 High Similarity NPC159750
0.9634 High Similarity NPC473649
0.9634 High Similarity NPC470401
0.9634 High Similarity NPC154097
0.963 High Similarity NPC329615
0.963 High Similarity NPC120398
0.963 High Similarity NPC471567
0.963 High Similarity NPC329838
0.963 High Similarity NPC322529
0.9524 High Similarity NPC239517
0.9512 High Similarity NPC231096
0.9512 High Similarity NPC142117
0.9512 High Similarity NPC62118
0.9512 High Similarity NPC107717
0.9512 High Similarity NPC232555
0.9512 High Similarity NPC240695
0.9512 High Similarity NPC114694
0.9512 High Similarity NPC475581
0.9512 High Similarity NPC171174
0.9506 High Similarity NPC163093
0.95 High Similarity NPC65930
0.95 High Similarity NPC94875
0.95 High Similarity NPC473712
0.95 High Similarity NPC73310
0.95 High Similarity NPC131002
0.95 High Similarity NPC11332
0.95 High Similarity NPC473780
0.95 High Similarity NPC475159
0.95 High Similarity NPC329829
0.95 High Similarity NPC180363
0.95 High Similarity NPC473529
0.95 High Similarity NPC145914
0.939 High Similarity NPC477018
0.939 High Similarity NPC100921
0.939 High Similarity NPC477013
0.939 High Similarity NPC231009
0.939 High Similarity NPC223871
0.939 High Similarity NPC477014
0.939 High Similarity NPC132496
0.939 High Similarity NPC110710
0.939 High Similarity NPC1083
0.939 High Similarity NPC103284
0.939 High Similarity NPC82795
0.939 High Similarity NPC473478
0.939 High Similarity NPC473669
0.939 High Similarity NPC283085
0.939 High Similarity NPC286338
0.939 High Similarity NPC107986
0.939 High Similarity NPC66346
0.939 High Similarity NPC473651
0.9383 High Similarity NPC144415
0.9383 High Similarity NPC253801
0.9302 High Similarity NPC473520
0.9286 High Similarity NPC280621
0.9286 High Similarity NPC20339
0.9286 High Similarity NPC233551
0.9286 High Similarity NPC40376
0.9286 High Similarity NPC48338
0.9286 High Similarity NPC89001
0.9286 High Similarity NPC21208
0.9277 High Similarity NPC134807
0.9277 High Similarity NPC134865
0.9277 High Similarity NPC309211
0.9277 High Similarity NPC69082
0.9277 High Similarity NPC210218
0.9277 High Similarity NPC134885
0.9277 High Similarity NPC477010
0.9277 High Similarity NPC204686
0.9277 High Similarity NPC473687
0.9277 High Similarity NPC308412
0.9277 High Similarity NPC477015
0.9277 High Similarity NPC279267
0.9277 High Similarity NPC219498
0.9277 High Similarity NPC103523
0.9176 High Similarity NPC477011
0.9176 High Similarity NPC477017
0.9176 High Similarity NPC477016
0.9167 High Similarity NPC178215
0.907 High Similarity NPC473904
0.9048 High Similarity NPC47937
0.9048 High Similarity NPC112685
0.8953 High Similarity NPC139418
0.8953 High Similarity NPC14901
0.8953 High Similarity NPC130359
0.8953 High Similarity NPC280612
0.8941 High Similarity NPC477012
0.8929 High Similarity NPC182383
0.8864 High Similarity NPC473723
0.8864 High Similarity NPC475173
0.8864 High Similarity NPC473561
0.8864 High Similarity NPC473663
0.875 High Similarity NPC473707
0.8652 High Similarity NPC11456
0.8242 Intermediate Similarity NPC81419
0.8242 Intermediate Similarity NPC179746
0.8132 Intermediate Similarity NPC12172
0.8132 Intermediate Similarity NPC208886
0.8132 Intermediate Similarity NPC30515
0.8025 Intermediate Similarity NPC84038
0.8022 Intermediate Similarity NPC473619
0.8022 Intermediate Similarity NPC476004
0.8022 Intermediate Similarity NPC474761
0.8022 Intermediate Similarity NPC473448
0.8022 Intermediate Similarity NPC51004
0.8 Intermediate Similarity NPC187268
0.7976 Intermediate Similarity NPC475711
0.7938 Intermediate Similarity NPC86077
0.7935 Intermediate Similarity NPC473321
0.7935 Intermediate Similarity NPC184463
0.7927 Intermediate Similarity NPC474705
0.7912 Intermediate Similarity NPC307411
0.7912 Intermediate Similarity NPC295312
0.7872 Intermediate Similarity NPC36954
0.7865 Intermediate Similarity NPC21469
0.7849 Intermediate Similarity NPC476300
0.7849 Intermediate Similarity NPC475912
0.7849 Intermediate Similarity NPC162205
0.7849 Intermediate Similarity NPC295204
0.7849 Intermediate Similarity NPC288240
0.7849 Intermediate Similarity NPC273579
0.7812 Intermediate Similarity NPC473326
0.7802 Intermediate Similarity NPC58219
0.7802 Intermediate Similarity NPC177629
0.7802 Intermediate Similarity NPC202672
0.7791 Intermediate Similarity NPC470149
0.7791 Intermediate Similarity NPC470148
0.7778 Intermediate Similarity NPC469483
0.7778 Intermediate Similarity NPC164393
0.7766 Intermediate Similarity NPC81386
0.7766 Intermediate Similarity NPC474035
0.7753 Intermediate Similarity NPC288471
0.7717 Intermediate Similarity NPC92974
0.7717 Intermediate Similarity NPC473564
0.7717 Intermediate Similarity NPC474032
0.7701 Intermediate Similarity NPC470147
0.7701 Intermediate Similarity NPC133226
0.7701 Intermediate Similarity NPC47653
0.7692 Intermediate Similarity NPC160138
0.7692 Intermediate Similarity NPC186148
0.7692 Intermediate Similarity NPC248602
0.7684 Intermediate Similarity NPC14961
0.7684 Intermediate Similarity NPC270013
0.7674 Intermediate Similarity NPC3852
0.7674 Intermediate Similarity NPC248775
0.7667 Intermediate Similarity NPC137033
0.766 Intermediate Similarity NPC212486
0.7654 Intermediate Similarity NPC218477
0.764 Intermediate Similarity NPC475947
0.764 Intermediate Similarity NPC286770
0.764 Intermediate Similarity NPC284472

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC293136 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
0.7826 Intermediate Similarity NPD6698 Approved
0.7826 Intermediate Similarity NPD46 Approved
0.7451 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD7838 Discovery
0.7212 Intermediate Similarity NPD6686 Approved
0.7188 Intermediate Similarity NPD7983 Approved
0.6931 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6916 Remote Similarity NPD6371 Approved
0.6771 Remote Similarity NPD4251 Approved
0.6771 Remote Similarity NPD4250 Approved
0.6747 Remote Similarity NPD3197 Phase 1
0.6737 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6697 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4249 Approved
0.6634 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6566 Remote Similarity NPD5785 Approved
0.6562 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6526 Remote Similarity NPD7154 Phase 3
0.6526 Remote Similarity NPD5362 Discontinued
0.6476 Remote Similarity NPD5344 Discontinued
0.6465 Remote Similarity NPD1695 Approved
0.6442 Remote Similarity NPD4225 Approved
0.6442 Remote Similarity NPD7638 Approved
0.6421 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6413 Remote Similarity NPD4756 Discovery
0.6392 Remote Similarity NPD5363 Approved
0.6383 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6381 Remote Similarity NPD7640 Approved
0.6381 Remote Similarity NPD7639 Approved
0.6364 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6339 Remote Similarity NPD6053 Discontinued
0.6322 Remote Similarity NPD4247 Clinical (unspecified phase)
0.625 Remote Similarity NPD7507 Approved
0.625 Remote Similarity NPD6435 Approved
0.6196 Remote Similarity NPD8039 Approved
0.619 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6186 Remote Similarity NPD8513 Phase 3
0.6186 Remote Similarity NPD8515 Approved
0.6186 Remote Similarity NPD8516 Approved
0.6186 Remote Similarity NPD6110 Phase 1
0.6186 Remote Similarity NPD8517 Approved
0.617 Remote Similarity NPD4271 Approved
0.617 Remote Similarity NPD4268 Approved
0.617 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6146 Remote Similarity NPD4790 Discontinued
0.6122 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6117 Remote Similarity NPD5779 Approved
0.6117 Remote Similarity NPD5778 Approved
0.6098 Remote Similarity NPD7319 Approved
0.6095 Remote Similarity NPD7839 Suspended
0.6092 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6083 Remote Similarity NPD7829 Approved
0.6083 Remote Similarity NPD7830 Approved
0.6082 Remote Similarity NPD4270 Approved
0.6082 Remote Similarity NPD5209 Approved
0.6082 Remote Similarity NPD4269 Approved
0.6075 Remote Similarity NPD6648 Approved
0.6061 Remote Similarity NPD1694 Approved
0.6058 Remote Similarity NPD5282 Discontinued
0.6049 Remote Similarity NPD4266 Approved
0.6049 Remote Similarity NPD3194 Approved
0.6049 Remote Similarity NPD3728 Approved
0.6049 Remote Similarity NPD3195 Phase 2
0.6049 Remote Similarity NPD3730 Approved
0.6049 Remote Similarity NPD3196 Approved
0.6042 Remote Similarity NPD4821 Approved
0.6042 Remote Similarity NPD4820 Approved
0.6042 Remote Similarity NPD4819 Approved
0.6042 Remote Similarity NPD4822 Approved
0.6042 Remote Similarity NPD5368 Approved
0.6042 Remote Similarity NPD4252 Approved
0.6036 Remote Similarity NPD6412 Phase 2
0.602 Remote Similarity NPD5332 Approved
0.602 Remote Similarity NPD5331 Approved
0.6018 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6 Remote Similarity NPD5786 Approved
0.5983 Remote Similarity NPD7115 Discovery
0.5979 Remote Similarity NPD5369 Approved
0.5966 Remote Similarity NPD8294 Approved
0.5966 Remote Similarity NPD8377 Approved
0.5952 Remote Similarity NPD6109 Phase 1
0.5935 Remote Similarity NPD8074 Phase 3
0.5932 Remote Similarity NPD7327 Approved
0.5932 Remote Similarity NPD7328 Approved
0.5926 Remote Similarity NPD3172 Approved
0.5917 Remote Similarity NPD8335 Approved
0.5917 Remote Similarity NPD8378 Approved
0.5917 Remote Similarity NPD8380 Approved
0.5917 Remote Similarity NPD8033 Approved
0.5917 Remote Similarity NPD8379 Approved
0.5917 Remote Similarity NPD8296 Approved
0.5891 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5882 Remote Similarity NPD7516 Approved
0.5875 Remote Similarity NPD6927 Phase 3
0.5862 Remote Similarity NPD4632 Approved
0.5862 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5843 Remote Similarity NPD3704 Approved
0.582 Remote Similarity NPD7642 Approved
0.5818 Remote Similarity NPD7632 Discontinued
0.5806 Remote Similarity NPD7078 Approved
0.5798 Remote Similarity NPD7641 Discontinued
0.5785 Remote Similarity NPD8444 Approved
0.5776 Remote Similarity NPD8297 Approved
0.5772 Remote Similarity NPD7492 Approved
0.5765 Remote Similarity NPD9119 Approved
0.5765 Remote Similarity NPD69 Approved
0.576 Remote Similarity NPD7736 Approved
0.5755 Remote Similarity NPD7748 Approved
0.5752 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5741 Remote Similarity NPD7902 Approved
0.5739 Remote Similarity NPD6421 Discontinued
0.5726 Remote Similarity NPD8133 Approved
0.5726 Remote Similarity NPD6616 Approved
0.5726 Remote Similarity NPD8273 Phase 1
0.5714 Remote Similarity NPD7637 Suspended
0.5714 Remote Similarity NPD7500 Approved
0.5702 Remote Similarity NPD6319 Approved
0.5702 Remote Similarity NPD6054 Approved
0.569 Remote Similarity NPD7116 Clinical (unspecified phase)
0.569 Remote Similarity NPD2204 Approved
0.568 Remote Similarity NPD8293 Discontinued
0.5679 Remote Similarity NPD29 Approved
0.5679 Remote Similarity NPD28 Approved
0.5673 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5673 Remote Similarity NPD5370 Suspended
0.5673 Remote Similarity NPD6101 Approved
0.5667 Remote Similarity NPD7331 Phase 2
0.5667 Remote Similarity NPD6108 Clinical (unspecified phase)
0.566 Remote Similarity NPD6399 Phase 3
0.5656 Remote Similarity NPD7503 Approved
0.5648 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5647 Remote Similarity NPD9118 Approved
0.5625 Remote Similarity NPD7260 Phase 2
0.5625 Remote Similarity NPD6647 Phase 2
0.561 Remote Similarity NPD6370 Approved
0.5603 Remote Similarity NPD2067 Discontinued
0.56 Remote Similarity NPD8451 Approved

Structure

External Identifiers

PubChem CID   44591855
ChEMBL   CHEMBL448616
ZINC  

Physicochemical Properties

Molecular Weight:  622.48
ALogP:  -8.3702
MLogP:  4.76
XLogP:  9.788
# Rotatable Bonds:  30
Polar Surface Area:  105.45
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  44

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Structure MOL file  
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Biological Activities  
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