Natural Product: NPC474518

Natural Product ID:  NPC474518
Common Name:   3-O-Deacetyl-22,23-Dihydro-24,28-Dehydroluffasterol B
IUPAC Name:   2-[(1R,2R,5R)-2-[(1aS,4aS,7S,8aR)-7-hydroxy-4a-methyl-4-oxo-5,6,7,8-tetrahydro-1aH-naphtho[1,8a-b]oxiren-3-yl]-1-methyl-5-[(E,2R)-6-methyl-5-methylidenehept-3-en-2-yl]cyclopentyl]acetaldehyde
Synonyms:  
Molecular Formula:   C28H40O4
Standard InCHIKey:  AUSQYKJYXFAPGL-DOILQICDSA-N
Standard InCHI:  InChI=1S/C28H40O4/c1-17(2)18(3)7-8-19(4)22-9-10-23(26(22,5)13-14-29)21-15-24-28(32-24)16-20(30)11-12-27(28,6)25(21)31/h7-8,14-15,17,19-20,22-24,30H,3,9-13,16H2,1-2,4-6H3/b8-7+/t19-,20+,22-,23+,24+,26-,27-,28+/m1/s1
Canonical SMILES:  O=CC[C@]1(C)[C@H](CC[C@H]1C1=C[C@@H]2O[C@@]32[C@](C1=O)(C)CC[C@@H](C3)O)[C@@H](/C=C/C(=C)C(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
NPO25507 Spongia agaricina Species Spongiidae Eukaryota PMID[9548857]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 = 1 ug/ml 18816139
NPT139 Cell Line HT-29 Homo sapiens IC50 = 1 ug/ml 19029333
NPT81 Cell Line A549 Homo sapiens IC50 = 1 ug/ml 19029333
NPT168 Cell Line P388 Mus musculus IC50 = 1 ug/ml 19029333

  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 NPC474518 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
0.9813 High Similarity NPC238667
0.8655 High Similarity NPC293112
0.8644 High Similarity NPC469789
0.8644 High Similarity NPC11895
0.8621 High Similarity NPC476960
0.8559 High Similarity NPC170538
0.8559 High Similarity NPC476802
0.8559 High Similarity NPC89171
0.8547 High Similarity NPC476962
0.85 High Similarity NPC473635
0.8475 Intermediate Similarity NPC67569
0.8448 Intermediate Similarity NPC476959
0.8417 Intermediate Similarity NPC81736
0.8417 Intermediate Similarity NPC172154
0.8417 Intermediate Similarity NPC8369
0.8403 Intermediate Similarity NPC470265
0.8403 Intermediate Similarity NPC23786
0.8376 Intermediate Similarity NPC284707
0.8362 Intermediate Similarity NPC476963
0.8348 Intermediate Similarity NPC122056
0.8333 Intermediate Similarity NPC55602
0.8333 Intermediate Similarity NPC204812
0.8333 Intermediate Similarity NPC474229
0.8333 Intermediate Similarity NPC207689
0.8319 Intermediate Similarity NPC310511
0.8291 Intermediate Similarity NPC53396
0.8291 Intermediate Similarity NPC98249
0.8291 Intermediate Similarity NPC469684
0.8288 Intermediate Similarity NPC470297
0.8279 Intermediate Similarity NPC287423
0.8276 Intermediate Similarity NPC470953
0.8264 Intermediate Similarity NPC241456
0.8264 Intermediate Similarity NPC32868
0.8261 Intermediate Similarity NPC476801
0.8257 Intermediate Similarity NPC112167
0.8241 Intermediate Similarity NPC111187
0.8241 Intermediate Similarity NPC190080
0.8235 Intermediate Similarity NPC476961
0.8235 Intermediate Similarity NPC184555
0.823 Intermediate Similarity NPC177064
0.822 Intermediate Similarity NPC709
0.822 Intermediate Similarity NPC470420
0.822 Intermediate Similarity NPC50774
0.8214 Intermediate Similarity NPC128828
0.8211 Intermediate Similarity NPC473620
0.8205 Intermediate Similarity NPC469794
0.8205 Intermediate Similarity NPC72772
0.8198 Intermediate Similarity NPC476848
0.819 Intermediate Similarity NPC317210
0.8174 Intermediate Similarity NPC474315
0.8167 Intermediate Similarity NPC46570
0.8158 Intermediate Similarity NPC474243
0.8151 Intermediate Similarity NPC472667
0.8151 Intermediate Similarity NPC156745
0.8151 Intermediate Similarity NPC475520
0.8151 Intermediate Similarity NPC236918
0.8145 Intermediate Similarity NPC221414
0.8145 Intermediate Similarity NPC231529
0.8136 Intermediate Similarity NPC167606
0.8136 Intermediate Similarity NPC286528
0.8136 Intermediate Similarity NPC20302
0.8136 Intermediate Similarity NPC140055
0.8136 Intermediate Similarity NPC239273
0.813 Intermediate Similarity NPC42399
0.8115 Intermediate Similarity NPC8374
0.8103 Intermediate Similarity NPC475970
0.8103 Intermediate Similarity NPC277769
0.8099 Intermediate Similarity NPC107493
0.8095 Intermediate Similarity NPC469674
0.8087 Intermediate Similarity NPC76084
0.8083 Intermediate Similarity NPC268530
0.8083 Intermediate Similarity NPC154491
0.8083 Intermediate Similarity NPC472759
0.8083 Intermediate Similarity NPC251226
0.8083 Intermediate Similarity NPC474370
0.8083 Intermediate Similarity NPC475885
0.8083 Intermediate Similarity NPC329080
0.807 Intermediate Similarity NPC65941
0.807 Intermediate Similarity NPC102843
0.807 Intermediate Similarity NPC322903
0.8067 Intermediate Similarity NPC473720
0.8065 Intermediate Similarity NPC236999
0.8053 Intermediate Similarity NPC469607
0.8051 Intermediate Similarity NPC270929
0.8051 Intermediate Similarity NPC270478
0.8049 Intermediate Similarity NPC471939
0.8036 Intermediate Similarity NPC473624
0.8036 Intermediate Similarity NPC247957
0.8036 Intermediate Similarity NPC249187
0.8036 Intermediate Similarity NPC120321
0.8034 Intermediate Similarity NPC469454
0.8034 Intermediate Similarity NPC56448
0.8034 Intermediate Similarity NPC469463
0.8034 Intermediate Similarity NPC25909
0.8034 Intermediate Similarity NPC469496
0.8034 Intermediate Similarity NPC471204
0.8033 Intermediate Similarity NPC120724
0.8031 Intermediate Similarity NPC248703
0.8018 Intermediate Similarity NPC476240
0.8018 Intermediate Similarity NPC207885
0.8018 Intermediate Similarity NPC112613
0.8018 Intermediate Similarity NPC476223
0.8018 Intermediate Similarity NPC472637
0.8018 Intermediate Similarity NPC224720
0.8017 Intermediate Similarity NPC159456
0.8017 Intermediate Similarity NPC4021
0.8017 Intermediate Similarity NPC470960
0.8 Intermediate Similarity NPC61520
0.8 Intermediate Similarity NPC270850
0.8 Intermediate Similarity NPC472933
0.8 Intermediate Similarity NPC470186
0.8 Intermediate Similarity NPC103051
0.8 Intermediate Similarity NPC285298
0.8 Intermediate Similarity NPC305260
0.8 Intermediate Similarity NPC473274
0.8 Intermediate Similarity NPC257082
0.8 Intermediate Similarity NPC473593
0.8 Intermediate Similarity NPC475065
0.8 Intermediate Similarity NPC264954
0.7984 Intermediate Similarity NPC471940
0.7984 Intermediate Similarity NPC473253
0.7983 Intermediate Similarity NPC312824
0.7983 Intermediate Similarity NPC243065
0.7983 Intermediate Similarity NPC470492
0.7983 Intermediate Similarity NPC476965
0.7983 Intermediate Similarity NPC473656
0.7983 Intermediate Similarity NPC470493
0.7983 Intermediate Similarity NPC183580
0.7983 Intermediate Similarity NPC470959
0.7982 Intermediate Similarity NPC329048
0.7982 Intermediate Similarity NPC78473
0.7982 Intermediate Similarity NPC330011
0.7982 Intermediate Similarity NPC263729
0.7982 Intermediate Similarity NPC179380
0.7966 Intermediate Similarity NPC147912
0.7966 Intermediate Similarity NPC67259
0.7965 Intermediate Similarity NPC72255
0.7965 Intermediate Similarity NPC294259
0.7965 Intermediate Similarity NPC96268
0.7951 Intermediate Similarity NPC269642
0.7951 Intermediate Similarity NPC153700
0.7951 Intermediate Similarity NPC88326
0.7949 Intermediate Similarity NPC4573
0.7949 Intermediate Similarity NPC69291
0.7949 Intermediate Similarity NPC476163
0.7949 Intermediate Similarity NPC90952
0.7949 Intermediate Similarity NPC269530
0.7949 Intermediate Similarity NPC476964
0.7946 Intermediate Similarity NPC476081
0.7946 Intermediate Similarity NPC155332
0.7946 Intermediate Similarity NPC32577
0.7946 Intermediate Similarity NPC114540
0.7937 Intermediate Similarity NPC475606
0.7937 Intermediate Similarity NPC251564
0.7937 Intermediate Similarity NPC477189
0.7937 Intermediate Similarity NPC475314
0.7934 Intermediate Similarity NPC185876
0.7934 Intermediate Similarity NPC19336
0.7934 Intermediate Similarity NPC79579
0.7934 Intermediate Similarity NPC143755
0.7931 Intermediate Similarity NPC472214
0.7931 Intermediate Similarity NPC478209
0.7931 Intermediate Similarity NPC472215
0.7931 Intermediate Similarity NPC253906
0.7928 Intermediate Similarity NPC35751
0.7928 Intermediate Similarity NPC476274
0.7917 Intermediate Similarity NPC186525
0.7917 Intermediate Similarity NPC472760
0.7917 Intermediate Similarity NPC153440
0.7917 Intermediate Similarity NPC21326
0.7917 Intermediate Similarity NPC124676
0.7917 Intermediate Similarity NPC146280
0.7917 Intermediate Similarity NPC329736
0.7913 Intermediate Similarity NPC473482
0.7913 Intermediate Similarity NPC476479
0.7913 Intermediate Similarity NPC475418
0.7913 Intermediate Similarity NPC318363
0.7913 Intermediate Similarity NPC220155
0.7913 Intermediate Similarity NPC275539
0.7913 Intermediate Similarity NPC189075
0.7909 Intermediate Similarity NPC126815
0.7909 Intermediate Similarity NPC291634
0.7903 Intermediate Similarity NPC159499
0.7899 Intermediate Similarity NPC234858
0.7899 Intermediate Similarity NPC154363
0.7899 Intermediate Similarity NPC148458
0.7899 Intermediate Similarity NPC477509
0.7899 Intermediate Similarity NPC471127
0.7899 Intermediate Similarity NPC298278
0.7899 Intermediate Similarity NPC190286
0.7895 Intermediate Similarity NPC34768
0.7895 Intermediate Similarity NPC1679
0.7895 Intermediate Similarity NPC103088
0.7895 Intermediate Similarity NPC470979
0.7895 Intermediate Similarity NPC470975
0.7895 Intermediate Similarity NPC60681
0.7895 Intermediate Similarity NPC478052
0.7895 Intermediate Similarity NPC257353
0.7891 Intermediate Similarity NPC478072
0.789 Intermediate Similarity NPC316215

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC474518 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
0.8136 Intermediate Similarity NPD7115 Discovery
0.7642 Intermediate Similarity NPD6054 Approved
0.7632 Intermediate Similarity NPD5211 Phase 2
0.7627 Intermediate Similarity NPD4634 Approved
0.7615 Intermediate Similarity NPD6079 Approved
0.7611 Intermediate Similarity NPD5285 Approved
0.7611 Intermediate Similarity NPD4696 Approved
0.7611 Intermediate Similarity NPD5286 Approved
0.7607 Intermediate Similarity NPD6899 Approved
0.7607 Intermediate Similarity NPD6881 Approved
0.7586 Intermediate Similarity NPD6008 Approved
0.7578 Intermediate Similarity NPD7319 Approved
0.7563 Intermediate Similarity NPD6649 Approved
0.7563 Intermediate Similarity NPD6650 Approved
0.7521 Intermediate Similarity NPD5697 Approved
0.752 Intermediate Similarity NPD6370 Approved
0.75 Intermediate Similarity NPD6319 Approved
0.75 Intermediate Similarity NPD4697 Phase 3
0.75 Intermediate Similarity NPD5141 Approved
0.7479 Intermediate Similarity NPD6883 Approved
0.7479 Intermediate Similarity NPD7290 Approved
0.7479 Intermediate Similarity NPD7102 Approved
0.7478 Intermediate Similarity NPD5226 Approved
0.7478 Intermediate Similarity NPD5224 Approved
0.7478 Intermediate Similarity NPD4633 Approved
0.7478 Intermediate Similarity NPD5225 Approved
0.744 Intermediate Similarity NPD6015 Approved
0.744 Intermediate Similarity NPD6016 Approved
0.7436 Intermediate Similarity NPD6402 Approved
0.7436 Intermediate Similarity NPD5739 Approved
0.7436 Intermediate Similarity NPD7128 Approved
0.7436 Intermediate Similarity NPD6675 Approved
0.7434 Intermediate Similarity NPD4755 Approved
0.7431 Intermediate Similarity NPD5328 Approved
0.7417 Intermediate Similarity NPD8130 Phase 1
0.7417 Intermediate Similarity NPD6617 Approved
0.7417 Intermediate Similarity NPD6869 Approved
0.7417 Intermediate Similarity NPD6847 Approved
0.7414 Intermediate Similarity NPD5175 Approved
0.7414 Intermediate Similarity NPD5174 Approved
0.7402 Intermediate Similarity NPD7492 Approved
0.7395 Intermediate Similarity NPD6373 Approved
0.7395 Intermediate Similarity NPD6012 Approved
0.7395 Intermediate Similarity NPD6014 Approved
0.7395 Intermediate Similarity NPD6372 Approved
0.7395 Intermediate Similarity NPD6013 Approved
0.7391 Intermediate Similarity NPD5223 Approved
0.7381 Intermediate Similarity NPD5988 Approved
0.7368 Intermediate Similarity NPD7638 Approved
0.736 Intermediate Similarity NPD6059 Approved
0.7355 Intermediate Similarity NPD6882 Approved
0.7355 Intermediate Similarity NPD8297 Approved
0.7345 Intermediate Similarity NPD5221 Approved
0.7345 Intermediate Similarity NPD5222 Approved
0.7345 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD7507 Approved
0.7344 Intermediate Similarity NPD6616 Approved
0.7311 Intermediate Similarity NPD7320 Approved
0.7311 Intermediate Similarity NPD6011 Approved
0.7304 Intermediate Similarity NPD4700 Approved
0.7304 Intermediate Similarity NPD7640 Approved
0.7304 Intermediate Similarity NPD7639 Approved
0.7295 Intermediate Similarity NPD4632 Approved
0.7287 Intermediate Similarity NPD7078 Approved
0.7281 Intermediate Similarity NPD5173 Approved
0.725 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD5778 Approved
0.7232 Intermediate Similarity NPD5779 Approved
0.7231 Intermediate Similarity NPD7736 Approved
0.7227 Intermediate Similarity NPD5701 Approved
0.7213 Intermediate Similarity NPD6053 Discontinued
0.719 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD7604 Phase 2
0.7167 Intermediate Similarity NPD4729 Approved
0.7167 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD4730 Approved
0.7156 Intermediate Similarity NPD3618 Phase 1
0.7143 Intermediate Similarity NPD7637 Suspended
0.712 Intermediate Similarity NPD6009 Approved
0.708 Intermediate Similarity NPD4202 Approved
0.708 Intermediate Similarity NPD6399 Phase 3
0.7069 Intermediate Similarity NPD4225 Approved
0.7049 Intermediate Similarity NPD5247 Approved
0.7049 Intermediate Similarity NPD5248 Approved
0.7049 Intermediate Similarity NPD6371 Approved
0.7049 Intermediate Similarity NPD5249 Phase 3
0.7049 Intermediate Similarity NPD5250 Approved
0.7049 Intermediate Similarity NPD5251 Approved
0.7031 Intermediate Similarity NPD5983 Phase 2
0.7025 Intermediate Similarity NPD5128 Approved
0.7023 Intermediate Similarity NPD8293 Discontinued
0.7009 Intermediate Similarity NPD6648 Approved
0.7008 Intermediate Similarity NPD7101 Approved
0.7008 Intermediate Similarity NPD7100 Approved
0.7 Intermediate Similarity NPD4768 Approved
0.7 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4767 Approved
0.6992 Remote Similarity NPD5215 Approved
0.6992 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6992 Remote Similarity NPD5216 Approved
0.6992 Remote Similarity NPD5217 Approved
0.6991 Remote Similarity NPD6411 Approved
0.6975 Remote Similarity NPD4754 Approved
0.6972 Remote Similarity NPD4786 Approved
0.6972 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6957 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5210 Approved
0.6957 Remote Similarity NPD4629 Approved
0.6949 Remote Similarity NPD5344 Discontinued
0.6947 Remote Similarity NPD6336 Discontinued
0.6942 Remote Similarity NPD5954 Clinical (unspecified phase)
0.694 Remote Similarity NPD7260 Phase 2
0.6929 Remote Similarity NPD6335 Approved
0.6911 Remote Similarity NPD5169 Approved
0.6911 Remote Similarity NPD5135 Approved
0.6911 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6905 Remote Similarity NPD6274 Approved
0.6903 Remote Similarity NPD5785 Approved
0.6899 Remote Similarity NPD8513 Phase 3
0.6899 Remote Similarity NPD8515 Approved
0.6899 Remote Similarity NPD8517 Approved
0.6899 Remote Similarity NPD8516 Approved
0.6899 Remote Similarity NPD7503 Approved
0.6881 Remote Similarity NPD6695 Phase 3
0.687 Remote Similarity NPD5282 Discontinued
0.6855 Remote Similarity NPD5127 Approved
0.685 Remote Similarity NPD6317 Approved
0.6847 Remote Similarity NPD5279 Phase 3
0.6842 Remote Similarity NPD6033 Approved
0.6842 Remote Similarity NPD5284 Approved
0.6842 Remote Similarity NPD5281 Approved
0.6838 Remote Similarity NPD6084 Phase 2
0.6838 Remote Similarity NPD6083 Phase 2
0.6814 Remote Similarity NPD4753 Phase 2
0.6814 Remote Similarity NPD6101 Approved
0.6814 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6803 Remote Similarity NPD6412 Phase 2
0.6797 Remote Similarity NPD6313 Approved
0.6797 Remote Similarity NPD6314 Approved
0.6789 Remote Similarity NPD3667 Approved
0.6772 Remote Similarity NPD6868 Approved
0.6769 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6757 Remote Similarity NPD1694 Approved
0.675 Remote Similarity NPD7632 Discontinued
0.6748 Remote Similarity NPD5168 Approved
0.6748 Remote Similarity NPD6686 Approved
0.6695 Remote Similarity NPD7902 Approved
0.6693 Remote Similarity NPD5167 Approved
0.6667 Remote Similarity NPD3133 Approved
0.6667 Remote Similarity NPD5695 Phase 3
0.6667 Remote Similarity NPD3666 Approved
0.6667 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3665 Phase 1
0.6667 Remote Similarity NPD7328 Approved
0.6667 Remote Similarity NPD8328 Phase 3
0.6667 Remote Similarity NPD7327 Approved
0.6645 Remote Similarity NPD5761 Phase 2
0.6645 Remote Similarity NPD5760 Phase 2
0.6642 Remote Similarity NPD8074 Phase 3
0.6641 Remote Similarity NPD6909 Approved
0.6641 Remote Similarity NPD6908 Approved
0.6639 Remote Similarity NPD5696 Approved
0.6637 Remote Similarity NPD7524 Approved
0.6637 Remote Similarity NPD7750 Discontinued
0.6615 Remote Similarity NPD7516 Approved
0.6609 Remote Similarity NPD7838 Discovery
0.6609 Remote Similarity NPD46 Approved
0.6609 Remote Similarity NPD6698 Approved
0.6607 Remote Similarity NPD1696 Phase 3
0.6606 Remote Similarity NPD6931 Approved
0.6606 Remote Similarity NPD6930 Phase 2
0.6606 Remote Similarity NPD7514 Phase 3
0.6581 Remote Similarity NPD7748 Approved
0.6552 Remote Similarity NPD7515 Phase 2
0.6552 Remote Similarity NPD7983 Approved
0.6549 Remote Similarity NPD5280 Approved
0.6549 Remote Similarity NPD5690 Phase 2
0.6549 Remote Similarity NPD4694 Approved
0.6545 Remote Similarity NPD6902 Approved
0.6532 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6531 Remote Similarity NPD7236 Approved
0.6522 Remote Similarity NPD6845 Suspended
0.6515 Remote Similarity NPD8380 Approved
0.6515 Remote Similarity NPD6921 Approved
0.6515 Remote Similarity NPD8335 Approved
0.6515 Remote Similarity NPD8033 Approved
0.6515 Remote Similarity NPD8379 Approved
0.6515 Remote Similarity NPD8378 Approved
0.6515 Remote Similarity NPD8296 Approved
0.6514 Remote Similarity NPD6929 Approved
0.6491 Remote Similarity NPD3573 Approved
0.6489 Remote Similarity NPD4522 Approved
0.6486 Remote Similarity NPD4223 Phase 3
0.6486 Remote Similarity NPD4221 Approved
0.6481 Remote Similarity NPD6932 Approved
0.6466 Remote Similarity NPD5207 Approved
0.646 Remote Similarity NPD5363 Approved
0.646 Remote Similarity NPD5329 Approved
0.6455 Remote Similarity NPD7525 Registered
0.6455 Remote Similarity NPD7332 Phase 2

Structure

External Identifiers

PubChem CID   44575442
ChEMBL   CHEMBL470552
ZINC  

Physicochemical Properties

Molecular Weight:  440.29
ALogP:  1.4571
MLogP:  4.1
XLogP:  6.084
# Rotatable Bonds:  13
Polar Surface Area:  66.9
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  32

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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