Natural Product: NPC476583

Natural Product ID:  NPC476583
Common Name:   Squamostatin-A
IUPAC Name:   (2R)-4-[9-[(2R,5S)-5-[(1R,4R)-4-[(2S,5S)-5-[(1S,5R)-1,5-dihydroxyundecyl]oxolan-2-yl]-1,4-dihydroxybutyl]oxolan-2-yl]nonyl]-2-methyl-2H-furan-5-one
Synonyms:   Squamostatin-A
Molecular Formula:   C37H66O8
Standard InCHIKey:  HKIHGTSLUYNNHM-QYGGFNKRSA-N
Standard InCHI:  InChI=1S/C37H66O8/c1-3-4-5-12-16-29(38)17-14-19-31(39)35-24-25-36(45-35)33(41)22-21-32(40)34-23-20-30(44-34)18-13-10-8-6-7-9-11-15-28-26-27(2)43-37(28)42/h26-27,29-36,38-41H,3-25H2,1-2H3/t27-,29-,30-,31+,32-,33-,34+,35+,36+/m1/s1
Canonical SMILES:  CCCCCC[C@H](CCC[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)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]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens ED50 = 8 ug/ml 12852747
NPT306 Cell Line PC-3 Homo sapiens ED50 > 20 ug/ml 12852747
NPT307 Cell Line HOS Homo sapiens ED50 > 20 ug/ml 12852747
NPT180 Cell Line HCT-8 Homo sapiens ED50 > 20 ug/ml 12852747
NPT308 Cell Line CAKI-1 Homo sapiens ED50 > 20 ug/ml 12852747
NPT81 Cell Line A549 Homo sapiens ED50 > 20 ug/ml 12852747
NPT309 Cell Line 1A9 Homo sapiens ED50 = 0.0087 ug/ml 12852747
NPT310 Cell Line 1A9/ptx-10 Homo sapiens Inhibition = 40 % 12852747
NPT91 Cell Line KB Homo sapiens ED50 > 20 ug/ml 12852747
NPT165 Cell Line HeLa Homo sapiens IC50 = 33 nM 19285863
NPT2 Others Unspecified IC50 = 50 nM 19285863
NPT515 Cell Line SGC-7901 Homo sapiens IC50 = 97 nM 19285863
NPT83 Cell Line MCF7 Homo sapiens IC50 = 970 nM 19285863
NPT2 Others Unspecified IC50 = 2.6 nM 19285863
NPT81 Cell Line A549 Homo sapiens IC50 = 0.21 ug/ml 22011319
NPT165 Cell Line HeLa Homo sapiens IC50 = 0.45 ug/ml 22011319
NPT83 Cell Line MCF7 Homo sapiens IC50 = 0.15 ug/ml 22011319
NPT65 Cell Line HepG2 Homo sapiens IC50 = 0.83 ug/ml 22011319
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 0.49 ug/ml 22011319
NPT1097 Cell Line MKN-45 Homo sapiens IC50 = 0.93 ug/ml 22011319
NPT81 Cell Line A549 Homo sapiens IC50 > 80000 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 NPC476583 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 NPC20533
1.0 High Similarity NPC258068
0.9878 High Similarity NPC473905
0.9878 High Similarity NPC320458
0.9877 High Similarity NPC25703
0.9877 High Similarity NPC282815
0.9877 High Similarity NPC132940
0.9877 High Similarity NPC219652
0.9877 High Similarity NPC241360
0.9877 High Similarity NPC473840
0.9877 High Similarity NPC293136
0.9759 High Similarity NPC91067
0.9759 High Similarity NPC20621
0.9759 High Similarity NPC40066
0.9759 High Similarity NPC473504
0.9759 High Similarity NPC93794
0.9759 High Similarity NPC42598
0.9759 High Similarity NPC81778
0.9759 High Similarity NPC318963
0.9753 High Similarity NPC329838
0.9753 High Similarity NPC39279
0.9753 High Similarity NPC39167
0.9753 High Similarity NPC77871
0.9753 High Similarity NPC25764
0.9753 High Similarity NPC319036
0.9753 High Similarity NPC473156
0.9753 High Similarity NPC9678
0.9753 High Similarity NPC475268
0.9753 High Similarity NPC473671
0.9753 High Similarity NPC235809
0.9753 High Similarity NPC329615
0.9753 High Similarity NPC470400
0.9753 High Similarity NPC292809
0.9753 High Similarity NPC202055
0.9643 High Similarity NPC239517
0.9639 High Similarity NPC61257
0.9639 High Similarity NPC81045
0.9639 High Similarity NPC274446
0.9639 High Similarity NPC169511
0.9639 High Similarity NPC100454
0.9639 High Similarity NPC151403
0.9639 High Similarity NPC39754
0.9639 High Similarity NPC191929
0.9639 High Similarity NPC171135
0.9639 High Similarity NPC234077
0.9639 High Similarity NPC133730
0.9639 High Similarity NPC242364
0.9639 High Similarity NPC172821
0.9639 High Similarity NPC261952
0.9639 High Similarity NPC320569
0.9639 High Similarity NPC287164
0.963 High Similarity NPC156804
0.9518 High Similarity NPC473995
0.9518 High Similarity NPC473649
0.9518 High Similarity NPC159750
0.9518 High Similarity NPC470401
0.9518 High Similarity NPC154097
0.9512 High Similarity NPC471567
0.9512 High Similarity NPC477013
0.9512 High Similarity NPC120398
0.9512 High Similarity NPC322529
0.9512 High Similarity NPC477014
0.9405 High Similarity NPC280621
0.9405 High Similarity NPC233551
0.9405 High Similarity NPC40376
0.9405 High Similarity NPC20339
0.9405 High Similarity NPC21208
0.9405 High Similarity NPC89001
0.9405 High Similarity NPC48338
0.9398 High Similarity NPC475581
0.9398 High Similarity NPC107717
0.9398 High Similarity NPC240695
0.9398 High Similarity NPC171174
0.9398 High Similarity NPC231096
0.9398 High Similarity NPC114694
0.9398 High Similarity NPC134865
0.9398 High Similarity NPC232555
0.9398 High Similarity NPC142117
0.9398 High Similarity NPC62118
0.9398 High Similarity NPC103523
0.9398 High Similarity NPC477015
0.939 High Similarity NPC163093
0.9383 High Similarity NPC11332
0.9383 High Similarity NPC131002
0.9383 High Similarity NPC145914
0.9383 High Similarity NPC73310
0.9383 High Similarity NPC180363
0.9383 High Similarity NPC473780
0.9383 High Similarity NPC473712
0.9383 High Similarity NPC475159
0.9383 High Similarity NPC329829
0.9383 High Similarity NPC94875
0.9383 High Similarity NPC65930
0.9383 High Similarity NPC473529
0.9294 High Similarity NPC477011
0.9294 High Similarity NPC477016
0.9294 High Similarity NPC477017
0.9286 High Similarity NPC178215
0.9277 High Similarity NPC477018
0.9277 High Similarity NPC100921
0.9277 High Similarity NPC82795
0.9277 High Similarity NPC103284
0.9277 High Similarity NPC132496
0.9277 High Similarity NPC283085
0.9277 High Similarity NPC107986
0.9277 High Similarity NPC223871
0.9277 High Similarity NPC286338
0.9277 High Similarity NPC473478
0.9277 High Similarity NPC473669
0.9277 High Similarity NPC1083
0.9277 High Similarity NPC231009
0.9277 High Similarity NPC473651
0.9277 High Similarity NPC66346
0.9277 High Similarity NPC110710
0.9268 High Similarity NPC144415
0.9268 High Similarity NPC253801
0.9195 High Similarity NPC473520
0.9186 High Similarity NPC473904
0.9167 High Similarity NPC473687
0.9167 High Similarity NPC477010
0.9167 High Similarity NPC308412
0.9167 High Similarity NPC219498
0.9167 High Similarity NPC210218
0.9167 High Similarity NPC279267
0.9167 High Similarity NPC204686
0.9167 High Similarity NPC134807
0.9167 High Similarity NPC309211
0.9167 High Similarity NPC69082
0.9167 High Similarity NPC134885
0.907 High Similarity NPC139418
0.907 High Similarity NPC14901
0.907 High Similarity NPC280612
0.907 High Similarity NPC130359
0.9059 High Similarity NPC477012
0.8941 High Similarity NPC112685
0.8941 High Similarity NPC47937
0.8824 High Similarity NPC182383
0.8764 High Similarity NPC475173
0.8764 High Similarity NPC473561
0.8764 High Similarity NPC473723
0.8764 High Similarity NPC473663
0.8764 High Similarity NPC11456
0.8652 High Similarity NPC473707
0.8152 Intermediate Similarity NPC81419
0.8152 Intermediate Similarity NPC179746
0.8043 Intermediate Similarity NPC30515
0.8043 Intermediate Similarity NPC12172
0.8043 Intermediate Similarity NPC208886
0.7979 Intermediate Similarity NPC36954
0.7957 Intermediate Similarity NPC476300
0.7935 Intermediate Similarity NPC476004
0.7935 Intermediate Similarity NPC51004
0.7935 Intermediate Similarity NPC473619
0.7935 Intermediate Similarity NPC473448
0.7935 Intermediate Similarity NPC474761
0.7927 Intermediate Similarity NPC84038
0.7917 Intermediate Similarity NPC187268
0.7889 Intermediate Similarity NPC469483
0.7882 Intermediate Similarity NPC475711
0.7865 Intermediate Similarity NPC288471
0.7857 Intermediate Similarity NPC86077
0.7849 Intermediate Similarity NPC184463
0.7849 Intermediate Similarity NPC473321
0.7831 Intermediate Similarity NPC474705
0.7826 Intermediate Similarity NPC307411
0.7826 Intermediate Similarity NPC295312
0.7826 Intermediate Similarity NPC92974
0.7816 Intermediate Similarity NPC470147
0.7816 Intermediate Similarity NPC133226
0.7778 Intermediate Similarity NPC21469
0.7766 Intermediate Similarity NPC475912
0.7766 Intermediate Similarity NPC295204
0.7766 Intermediate Similarity NPC273579
0.7766 Intermediate Similarity NPC288240
0.7766 Intermediate Similarity NPC162205
0.7742 Intermediate Similarity NPC478003
0.7742 Intermediate Similarity NPC478004
0.7742 Intermediate Similarity NPC158388
0.7732 Intermediate Similarity NPC161855
0.7732 Intermediate Similarity NPC473326
0.7717 Intermediate Similarity NPC58219
0.7717 Intermediate Similarity NPC202672
0.7717 Intermediate Similarity NPC177629
0.7708 Intermediate Similarity NPC279621
0.7708 Intermediate Similarity NPC476315
0.7701 Intermediate Similarity NPC180725
0.7701 Intermediate Similarity NPC470148
0.7701 Intermediate Similarity NPC470149
0.7692 Intermediate Similarity NPC164393
0.7684 Intermediate Similarity NPC474035
0.7684 Intermediate Similarity NPC81386
0.7674 Intermediate Similarity NPC474026
0.7634 Intermediate Similarity NPC473564
0.7634 Intermediate Similarity NPC474032
0.7614 Intermediate Similarity NPC47653
0.7609 Intermediate Similarity NPC186148
0.7609 Intermediate Similarity NPC160138
0.7609 Intermediate Similarity NPC248602
0.7604 Intermediate Similarity NPC471141
0.7604 Intermediate Similarity NPC270013

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476583 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
0.7935 Intermediate Similarity NPD46 Approved
0.7935 Intermediate Similarity NPD6698 Approved
0.7553 Intermediate Similarity NPD7838 Discovery
0.7549 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD6686 Approved
0.7292 Intermediate Similarity NPD7983 Approved
0.703 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.6852 Remote Similarity NPD6371 Approved
0.6789 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6701 Remote Similarity NPD4250 Approved
0.6701 Remote Similarity NPD4251 Approved
0.6667 Remote Similarity NPD3197 Phase 1
0.6667 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6598 Remote Similarity NPD4249 Approved
0.6569 Remote Similarity NPD1698 Clinical (unspecified phase)
0.65 Remote Similarity NPD5785 Approved
0.6495 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6458 Remote Similarity NPD5362 Discontinued
0.6458 Remote Similarity NPD7154 Phase 3
0.6415 Remote Similarity NPD5344 Discontinued
0.64 Remote Similarity NPD1695 Approved
0.6381 Remote Similarity NPD4225 Approved
0.6381 Remote Similarity NPD7638 Approved
0.6354 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6344 Remote Similarity NPD4756 Discovery
0.6333 Remote Similarity NPD7507 Approved
0.6327 Remote Similarity NPD5363 Approved
0.6321 Remote Similarity NPD7640 Approved
0.6321 Remote Similarity NPD7639 Approved
0.6316 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6306 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6283 Remote Similarity NPD6053 Discontinued
0.6271 Remote Similarity NPD8515 Approved
0.6271 Remote Similarity NPD8513 Phase 3
0.6271 Remote Similarity NPD8517 Approved
0.6271 Remote Similarity NPD8516 Approved
0.625 Remote Similarity NPD4247 Clinical (unspecified phase)
0.619 Remote Similarity NPD7839 Suspended
0.6186 Remote Similarity NPD6435 Approved
0.6179 Remote Similarity NPD7319 Approved
0.6167 Remote Similarity NPD7830 Approved
0.6167 Remote Similarity NPD7829 Approved
0.6129 Remote Similarity NPD8039 Approved
0.6122 Remote Similarity NPD6110 Phase 1
0.6118 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6106 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6105 Remote Similarity NPD4268 Approved
0.6105 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6105 Remote Similarity NPD4271 Approved
0.6082 Remote Similarity NPD4790 Discontinued
0.6061 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6058 Remote Similarity NPD5778 Approved
0.6058 Remote Similarity NPD5779 Approved
0.605 Remote Similarity NPD8294 Approved
0.605 Remote Similarity NPD8377 Approved
0.6023 Remote Similarity NPD2685 Clinical (unspecified phase)
0.602 Remote Similarity NPD4270 Approved
0.602 Remote Similarity NPD5209 Approved
0.602 Remote Similarity NPD4269 Approved
0.6019 Remote Similarity NPD6648 Approved
0.6017 Remote Similarity NPD7328 Approved
0.6017 Remote Similarity NPD7327 Approved
0.6016 Remote Similarity NPD8074 Phase 3
0.6 Remote Similarity NPD8296 Approved
0.6 Remote Similarity NPD8378 Approved
0.6 Remote Similarity NPD8379 Approved
0.6 Remote Similarity NPD8335 Approved
0.6 Remote Similarity NPD8033 Approved
0.6 Remote Similarity NPD1694 Approved
0.6 Remote Similarity NPD5282 Discontinued
0.6 Remote Similarity NPD8380 Approved
0.5982 Remote Similarity NPD6412 Phase 2
0.5979 Remote Similarity NPD5368 Approved
0.5979 Remote Similarity NPD4821 Approved
0.5979 Remote Similarity NPD4822 Approved
0.5979 Remote Similarity NPD4819 Approved
0.5979 Remote Similarity NPD4820 Approved
0.5979 Remote Similarity NPD4252 Approved
0.5976 Remote Similarity NPD3195 Phase 2
0.5976 Remote Similarity NPD3730 Approved
0.5976 Remote Similarity NPD4266 Approved
0.5976 Remote Similarity NPD3196 Approved
0.5976 Remote Similarity NPD3728 Approved
0.5976 Remote Similarity NPD3194 Approved
0.5969 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5966 Remote Similarity NPD7516 Approved
0.596 Remote Similarity NPD5331 Approved
0.596 Remote Similarity NPD5332 Approved
0.5941 Remote Similarity NPD5786 Approved
0.5932 Remote Similarity NPD7115 Discovery
0.5918 Remote Similarity NPD5369 Approved
0.5902 Remote Similarity NPD7642 Approved
0.5882 Remote Similarity NPD6109 Phase 1
0.5882 Remote Similarity NPD7641 Discontinued
0.5868 Remote Similarity NPD8444 Approved
0.5862 Remote Similarity NPD8297 Approved
0.5854 Remote Similarity NPD3172 Approved
0.5841 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5826 Remote Similarity NPD6421 Discontinued
0.5812 Remote Similarity NPD8133 Approved
0.5812 Remote Similarity NPD4632 Approved
0.5806 Remote Similarity NPD8273 Phase 1
0.5802 Remote Similarity NPD6927 Phase 3
0.5798 Remote Similarity NPD7500 Approved
0.5795 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5785 Remote Similarity NPD6319 Approved
0.5778 Remote Similarity NPD3704 Approved
0.5776 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5766 Remote Similarity NPD7632 Discontinued
0.576 Remote Similarity NPD7078 Approved
0.5738 Remote Similarity NPD7503 Approved
0.5726 Remote Similarity NPD7492 Approved
0.5714 Remote Similarity NPD7736 Approved
0.5703 Remote Similarity NPD7260 Phase 2
0.5701 Remote Similarity NPD7748 Approved
0.5698 Remote Similarity NPD9119 Approved
0.5698 Remote Similarity NPD69 Approved
0.5688 Remote Similarity NPD7902 Approved
0.568 Remote Similarity NPD8451 Approved
0.568 Remote Similarity NPD6616 Approved
0.5667 Remote Similarity NPD7505 Discontinued
0.566 Remote Similarity NPD7637 Suspended
0.5659 Remote Similarity NPD6845 Suspended
0.5656 Remote Similarity NPD6054 Approved
0.5645 Remote Similarity NPD8328 Phase 3
0.5641 Remote Similarity NPD2204 Approved
0.5635 Remote Similarity NPD8448 Approved
0.5635 Remote Similarity NPD8293 Discontinued
0.5619 Remote Similarity NPD5370 Suspended
0.5619 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5619 Remote Similarity NPD6101 Approved
0.561 Remote Similarity NPD8267 Approved
0.561 Remote Similarity NPD29 Approved
0.561 Remote Similarity NPD28 Approved
0.561 Remote Similarity NPD8269 Approved
0.561 Remote Similarity NPD8266 Approved
0.561 Remote Similarity NPD8268 Approved
0.5607 Remote Similarity NPD6399 Phase 3
0.5604 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5604 Remote Similarity NPD7331 Phase 2
0.5603 Remote Similarity NPD8132 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   44591858
ChEMBL   CHEMBL447119
ZINC  

Physicochemical Properties

Molecular Weight:  638.48
ALogP:  -8.5929
MLogP:  4.65
XLogP:  7.914
# Rotatable Bonds:  31
Polar Surface Area:  125.68
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  45

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Biological Activities  
Similar NPs/Drugs