Natural Product: NPC309450

Natural Product ID:  NPC309450
Common Name:   Aurantoside F
IUPAC Name:   2-[(2S,4Z)-4-[(2E,4E,6E,8E,10Z,12E,14E,16Z)-11,17-dichloro-1-hydroxyoctadeca-2,4,6,8,10,12,14,16-octaenylidene]-1-[(2R,3R,4S,5R)-3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-[(2S,3S,4R,5R)-4-hydroxy-3-methoxy-5-methyloxolan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]-3,5-dioxopyrrolidin-2-yl]acetamide
Synonyms:   Aurantoside F
Molecular Formula:   C40H50Cl2N2O15
Standard InCHIKey:  PLUSNOWKJZSMMW-QUGWQAMWSA-N
Standard InCHI:  InChI=1S/C40H50Cl2N2O15/c1-21(41)14-10-9-12-16-23(42)15-11-7-5-4-6-8-13-17-25(45)29-31(49)24(18-28(43)47)44(37(29)53)38-35(32(50)26(46)19-55-38)59-39-34(52)33(51)27(20-56-39)58-40-36(54-3)30(48)22(2)57-40/h4-17,22,24,26-27,30,32-36,38-40,45-46,48,50-52H,18-20H2,1-3H3,(H2,43,47)/b5-4+,8-6+,10-9+,11-7+,16-12+,17-13+,21-14-,23-15-,29-25-/t22-,24+,26-,27-,30-,32+,33-,34+,35-,36+,38-,39+,40+/m1/s1
Canonical SMILES:  CO[C@@H]1[C@H](O[C@@H]2CO[C@H]([C@H]([C@@H]2O)O)O[C@@H]2[C@@H](O)[C@H](O)CO[C@H]2N2C(=O)/C(=C(/C=C/C=C/C=C/C=C/C=C(/C=C/C=C/C=C(Cl)/C)Cl)O)/C(=O)[C@@H]2CC(=N)O)O[C@@H]([C@H]1O)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
NPO25388 Siliquariaspongia japonica NA NA NA PMID[10425118]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT168 Cell Line P388 Mus musculus IC50 = 0.05 ug/ml 8904842

  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 NPC309450 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 NPC247776
1.0 High Similarity NPC304299
1.0 High Similarity NPC475266
1.0 High Similarity NPC475278
0.9697 High Similarity NPC71866
0.8769 High Similarity NPC36254
0.8042 Intermediate Similarity NPC315848
0.8042 Intermediate Similarity NPC315210
0.6536 Remote Similarity NPC471256
0.6531 Remote Similarity NPC471255
0.6449 Remote Similarity NPC201128
0.6447 Remote Similarity NPC120335
0.6443 Remote Similarity NPC471263
0.6443 Remote Similarity NPC315058
0.6424 Remote Similarity NPC313962
0.6405 Remote Similarity NPC314361
0.6351 Remote Similarity NPC273185
0.6333 Remote Similarity NPC309525
0.6284 Remote Similarity NPC315188
0.6268 Remote Similarity NPC251122
0.6258 Remote Similarity NPC78189
0.625 Remote Similarity NPC316244
0.6242 Remote Similarity NPC471262
0.6242 Remote Similarity NPC230889
0.6214 Remote Similarity NPC475918
0.6205 Remote Similarity NPC315809
0.6205 Remote Similarity NPC314050
0.62 Remote Similarity NPC314629
0.619 Remote Similarity NPC477398
0.6159 Remote Similarity NPC314451
0.6159 Remote Similarity NPC313333
0.6159 Remote Similarity NPC313342
0.6159 Remote Similarity NPC314512
0.6104 Remote Similarity NPC316205
0.6104 Remote Similarity NPC315387
0.6103 Remote Similarity NPC8098
0.6103 Remote Similarity NPC197294
0.6103 Remote Similarity NPC45313
0.6103 Remote Similarity NPC183449
0.6096 Remote Similarity NPC103391
0.6096 Remote Similarity NPC472536
0.6084 Remote Similarity NPC298484
0.6071 Remote Similarity NPC55336
0.6069 Remote Similarity NPC314306
0.6067 Remote Similarity NPC477462
0.6065 Remote Similarity NPC477988
0.6053 Remote Similarity NPC470653
0.6053 Remote Similarity NPC470654
0.6053 Remote Similarity NPC470650
0.6036 Remote Similarity NPC475342
0.6023 Remote Similarity NPC327517
0.6023 Remote Similarity NPC319334
0.6023 Remote Similarity NPC322372
0.6013 Remote Similarity NPC99864
0.5987 Remote Similarity NPC325750
0.5974 Remote Similarity NPC314282
0.5973 Remote Similarity NPC235625
0.5959 Remote Similarity NPC314550
0.5959 Remote Similarity NPC469865
0.5956 Remote Similarity NPC256570
0.5956 Remote Similarity NPC158445
0.5956 Remote Similarity NPC156782
0.5956 Remote Similarity NPC70323
0.5956 Remote Similarity NPC157353
0.5956 Remote Similarity NPC54961
0.5956 Remote Similarity NPC23454
0.5956 Remote Similarity NPC262312
0.5956 Remote Similarity NPC282088
0.5956 Remote Similarity NPC192066
0.5956 Remote Similarity NPC17290
0.5956 Remote Similarity NPC35269
0.5956 Remote Similarity NPC3568
0.5949 Remote Similarity NPC120420
0.5948 Remote Similarity NPC97580
0.5948 Remote Similarity NPC469494
0.5948 Remote Similarity NPC204639
0.5944 Remote Similarity NPC315426
0.5935 Remote Similarity NPC329919
0.5935 Remote Similarity NPC477793
0.5935 Remote Similarity NPC470651
0.5935 Remote Similarity NPC470655
0.5929 Remote Similarity NPC188785
0.5924 Remote Similarity NPC316401
0.5906 Remote Similarity NPC6531
0.5903 Remote Similarity NPC474099
0.5894 Remote Similarity NPC470652
0.589 Remote Similarity NPC476875
0.5879 Remote Similarity NPC298067
0.5879 Remote Similarity NPC214821
0.5878 Remote Similarity NPC475975
0.5878 Remote Similarity NPC272166
0.5871 Remote Similarity NPC247902
0.5871 Remote Similarity NPC262880
0.5855 Remote Similarity NPC160688
0.5852 Remote Similarity NPC209047
0.5852 Remote Similarity NPC43074
0.5852 Remote Similarity NPC242503
0.5852 Remote Similarity NPC139782
0.5852 Remote Similarity NPC74672
0.585 Remote Similarity NPC478024
0.5845 Remote Similarity NPC476877
0.5844 Remote Similarity NPC469999
0.5839 Remote Similarity NPC30196
0.5838 Remote Similarity NPC297145
0.5838 Remote Similarity NPC321485
0.5838 Remote Similarity NPC197743
0.5838 Remote Similarity NPC317377
0.5833 Remote Similarity NPC471820
0.5833 Remote Similarity NPC471821
0.5818 Remote Similarity NPC193579
0.5818 Remote Similarity NPC298469
0.5809 Remote Similarity NPC111567
0.5809 Remote Similarity NPC473604
0.5809 Remote Similarity NPC475125
0.5809 Remote Similarity NPC475603
0.5809 Remote Similarity NPC61894
0.5809 Remote Similarity NPC309898
0.5809 Remote Similarity NPC186840
0.5809 Remote Similarity NPC263545
0.5809 Remote Similarity NPC473581
0.5809 Remote Similarity NPC282705
0.5809 Remote Similarity NPC182632
0.5809 Remote Similarity NPC473950
0.5809 Remote Similarity NPC15851
0.5808 Remote Similarity NPC61717
0.5808 Remote Similarity NPC244380
0.5806 Remote Similarity NPC477987
0.5806 Remote Similarity NPC329401
0.5801 Remote Similarity NPC471165
0.5799 Remote Similarity NPC2501
0.5793 Remote Similarity NPC207820
0.5793 Remote Similarity NPC475150
0.5789 Remote Similarity NPC122590
0.5789 Remote Similarity NPC473341
0.5783 Remote Similarity NPC52748
0.5782 Remote Similarity NPC181510
0.5782 Remote Similarity NPC47857
0.5782 Remote Similarity NPC168758
0.5779 Remote Similarity NPC293550
0.5779 Remote Similarity NPC16709
0.5779 Remote Similarity NPC477990
0.5779 Remote Similarity NPC50520
0.5779 Remote Similarity NPC323168
0.5779 Remote Similarity NPC477989
0.5779 Remote Similarity NPC111162
0.5779 Remote Similarity NPC315783
0.5775 Remote Similarity NPC474244
0.5769 Remote Similarity NPC473249
0.5767 Remote Similarity NPC180770
0.5764 Remote Similarity NPC476876
0.5762 Remote Similarity NPC17581
0.5762 Remote Similarity NPC476155
0.5759 Remote Similarity NPC41162
0.5753 Remote Similarity NPC473578
0.5752 Remote Similarity NPC469515
0.5745 Remote Similarity NPC233932
0.5743 Remote Similarity NPC60432
0.5743 Remote Similarity NPC1111
0.5743 Remote Similarity NPC261750
0.574 Remote Similarity NPC298005
0.574 Remote Similarity NPC36463
0.5733 Remote Similarity NPC66007
0.5733 Remote Similarity NPC296043
0.5732 Remote Similarity NPC173173
0.5724 Remote Similarity NPC313802
0.5724 Remote Similarity NPC67917
0.5724 Remote Similarity NPC314268
0.5724 Remote Similarity NPC477515
0.5723 Remote Similarity NPC69176
0.5723 Remote Similarity NPC139585
0.5723 Remote Similarity NPC284625
0.5705 Remote Similarity NPC313173
0.5698 Remote Similarity NPC475599
0.5698 Remote Similarity NPC113620
0.5698 Remote Similarity NPC100612
0.5698 Remote Similarity NPC187497
0.5698 Remote Similarity NPC174336
0.5697 Remote Similarity NPC162910
0.5695 Remote Similarity NPC329216
0.5695 Remote Similarity NPC65045
0.5694 Remote Similarity NPC74035
0.5686 Remote Similarity NPC11379
0.5683 Remote Similarity NPC469739
0.5679 Remote Similarity NPC472430
0.5679 Remote Similarity NPC82129
0.5677 Remote Similarity NPC316133
0.5677 Remote Similarity NPC318445
0.5676 Remote Similarity NPC29501
0.5671 Remote Similarity NPC302276
0.5667 Remote Similarity NPC471645
0.5664 Remote Similarity NPC475149
0.5664 Remote Similarity NPC471097
0.5663 Remote Similarity NPC470886
0.5658 Remote Similarity NPC106791
0.5658 Remote Similarity NPC470300
0.5658 Remote Similarity NPC201889
0.5655 Remote Similarity NPC472433
0.5641 Remote Similarity NPC477985
0.5641 Remote Similarity NPC471087
0.5641 Remote Similarity NPC326386

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC309450 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
0.6159 Remote Similarity NPD8342 Approved
0.6159 Remote Similarity NPD8341 Approved
0.6159 Remote Similarity NPD8340 Approved
0.6159 Remote Similarity NPD8299 Approved
0.6081 Remote Similarity NPD7641 Discontinued
0.6076 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6069 Remote Similarity NPD6429 Approved
0.6069 Remote Similarity NPD6430 Approved
0.6065 Remote Similarity NPD8392 Approved
0.6065 Remote Similarity NPD8391 Approved
0.6065 Remote Similarity NPD8390 Approved
0.6013 Remote Similarity NPD8451 Approved
0.6013 Remote Similarity NPD8415 Approved
0.5974 Remote Similarity NPD8448 Approved
0.5921 Remote Similarity NPD6436 Phase 3
0.589 Remote Similarity NPD8384 Approved
0.5878 Remote Similarity NPD1000 Clinical (unspecified phase)
0.5852 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5845 Remote Similarity NPD8045 Clinical (unspecified phase)
0.5845 Remote Similarity NPD1407 Approved
0.5817 Remote Similarity NPD7623 Phase 3
0.5817 Remote Similarity NPD7624 Clinical (unspecified phase)
0.58 Remote Similarity NPD6936 Clinical (unspecified phase)
0.58 Remote Similarity NPD6935 Phase 3
0.5779 Remote Similarity NPD7830 Approved
0.5779 Remote Similarity NPD7829 Approved
0.5769 Remote Similarity NPD7747 Phase 1
0.5769 Remote Similarity NPD7746 Phase 1
0.5733 Remote Similarity NPD4830 Approved
0.5733 Remote Similarity NPD4831 Approved
0.5733 Remote Similarity NPD4832 Approved
0.5714 Remote Similarity NPD8080 Discontinued
0.5705 Remote Similarity NPD8273 Phase 1
0.5695 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5686 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5677 Remote Similarity NPD7642 Approved
0.5649 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5649 Remote Similarity NPD8444 Approved
0.5649 Remote Similarity NPD7739 Clinical (unspecified phase)
0.5643 Remote Similarity NPD6428 Approved
0.5632 Remote Similarity NPD8414 Discontinued
0.5608 Remote Similarity NPD6421 Discontinued
0.5605 Remote Similarity NPD4816 Clinical (unspecified phase)
0.56 Remote Similarity NPD8417 Discontinued
0.56 Remote Similarity NPD3731 Phase 3

Structure

External Identifiers

PubChem CID   54713412
ChEMBL   CHEMBL454029
ZINC  

Physicochemical Properties

Molecular Weight:  868.26
ALogP:  0.4196
MLogP:  3.77
XLogP:  1.627
# Rotatable Bonds:  28
Polar Surface Area:  258.22
# H-Bond Aceptor:  17
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  59

Download Data

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Structure MOL file  
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Biological Activities  
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