Natural Product: NPC133698

Natural Product ID:  NPC133698
Common Name:   Cumambrin A
IUPAC Name:   [(3aR,4S,6R,6aR,9aR,9bR)-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] acetate
Synonyms:  
Molecular Formula:   C17H22O5
Standard InCHIKey:  XMJROHDIQQOWTO-NRPXGKOBSA-N
Standard InCHI:  InChI=1S/C17H22O5/c1-8-5-6-11-13(8)15-14(9(2)16(19)22-15)12(21-10(3)18)7-17(11,4)20/h5,11-15,20H,2,6-7H2,1,3-4H3/t11-,12+,13+,14-,15-,17-/m1/s1
Canonical SMILES:  CC(=O)O[C@H]1C[C@@](C)(O)[C@H]2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)C(=CC2)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
NPO24213 Strophanthus thollonii Species Apocynaceae Eukaryota UNPD*
NPO17263 Mimosa diplotricha Species Fabaceae Eukaryota UNPD*
NPO23451 Polytrichum commune Species Polytrichaceae Eukaryota UNPD*
NPO23687 Delphinium hybridum Species Ranunculaceae Eukaryota UNPD*
NPO21202 Galeopsis pubescens Species Lamiaceae Eukaryota UNPD*
NPO22967 Maytenus blepharodes Species Celastraceae Eukaryota UNPD*
NPO18699 Baccharis articulata Species Asteraceae Eukaryota UNPD*
NPO20909 Astragalus amarus Species Fabaceae Eukaryota UNPD*
NPO26367 Muriceopsis flavida Species Plexauridae Eukaryota UNPD*
NPO24326 Adenocalymma alliaceum Species Bignoniaceae Eukaryota UNPD*
NPO26758 Forsythia x intermedia Species Oleaceae Eukaryota UNPD*
NPO18436 Agave ghiesbreghtii Species Asparagaceae Eukaryota UNPD*
NPO23093 Blumea obliqua Species Asteraceae Eukaryota UNPD*
NPO29592 Chrysanthemi indici flos NA NA NA TCMSP*
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota TCMID*
NPO21955 Salvia deserta Species Lamiaceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT983 Protein Complex Nuclear factor NF-kappa-B complex Homo sapiens IC100 = 0.02 nM 15537359
NPT721 Individual Protein Nuclear factor NF-kappa-B p65 subunit Homo sapiens IC100 = 0.02 nM 16570920

  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 NPC133698 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
0.977 High Similarity NPC477131
0.977 High Similarity NPC198853
0.9767 High Similarity NPC131209
0.9545 High Similarity NPC470010
0.9545 High Similarity NPC262133
0.9545 High Similarity NPC470013
0.9545 High Similarity NPC323008
0.9419 High Similarity NPC91248
0.9222 High Similarity NPC67584
0.9222 High Similarity NPC304886
0.9121 High Similarity NPC213078
0.9091 High Similarity NPC4986
0.9043 High Similarity NPC86077
0.9022 High Similarity NPC161493
0.9011 High Similarity NPC52044
0.9 High Similarity NPC135776
0.8977 High Similarity NPC79549
0.8901 High Similarity NPC127019
0.8876 High Similarity NPC215556
0.8804 High Similarity NPC213698
0.8778 High Similarity NPC216284
0.8778 High Similarity NPC37607
0.8778 High Similarity NPC301969
0.8764 High Similarity NPC207114
0.8764 High Similarity NPC178875
0.8764 High Similarity NPC217983
0.8763 High Similarity NPC223450
0.8763 High Similarity NPC243998
0.8763 High Similarity NPC166115
0.875 High Similarity NPC67493
0.8723 High Similarity NPC221615
0.8706 High Similarity NPC276356
0.8681 High Similarity NPC155215
0.8681 High Similarity NPC475925
0.8681 High Similarity NPC184063
0.8667 High Similarity NPC32922
0.8652 High Similarity NPC118601
0.8636 High Similarity NPC204105
0.8636 High Similarity NPC284534
0.8636 High Similarity NPC235792
0.8636 High Similarity NPC300082
0.8602 High Similarity NPC163228
0.8602 High Similarity NPC472873
0.8602 High Similarity NPC170120
0.8587 High Similarity NPC258216
0.8571 High Similarity NPC54065
0.8571 High Similarity NPC297474
0.8571 High Similarity NPC19087
0.8556 High Similarity NPC202672
0.8542 High Similarity NPC150923
0.8539 High Similarity NPC64153
0.8539 High Similarity NPC187661
0.8539 High Similarity NPC107787
0.8523 High Similarity NPC156485
0.8523 High Similarity NPC115786
0.8511 High Similarity NPC18019
0.8511 High Similarity NPC24956
0.8506 High Similarity NPC246076
0.8495 Intermediate Similarity NPC474338
0.8485 Intermediate Similarity NPC26617
0.8478 Intermediate Similarity NPC12172
0.8478 Intermediate Similarity NPC35959
0.8478 Intermediate Similarity NPC293001
0.8478 Intermediate Similarity NPC184463
0.8478 Intermediate Similarity NPC171360
0.8478 Intermediate Similarity NPC208886
0.8478 Intermediate Similarity NPC133888
0.8478 Intermediate Similarity NPC63193
0.8478 Intermediate Similarity NPC29821
0.8478 Intermediate Similarity NPC57304
0.8462 Intermediate Similarity NPC38392
0.8462 Intermediate Similarity NPC155935
0.8462 Intermediate Similarity NPC472872
0.8462 Intermediate Similarity NPC307411
0.8444 Intermediate Similarity NPC160138
0.8427 Intermediate Similarity NPC78089
0.8421 Intermediate Similarity NPC213947
0.8421 Intermediate Similarity NPC170143
0.8421 Intermediate Similarity NPC108475
0.8416 Intermediate Similarity NPC471884
0.8409 Intermediate Similarity NPC245665
0.8409 Intermediate Similarity NPC250315
0.8404 Intermediate Similarity NPC476053
0.8387 Intermediate Similarity NPC228451
0.8387 Intermediate Similarity NPC473273
0.8387 Intermediate Similarity NPC476300
0.8387 Intermediate Similarity NPC475912
0.8387 Intermediate Similarity NPC308656
0.8387 Intermediate Similarity NPC473234
0.8387 Intermediate Similarity NPC475838
0.8387 Intermediate Similarity NPC179746
0.8387 Intermediate Similarity NPC473263
0.8387 Intermediate Similarity NPC81419
0.8387 Intermediate Similarity NPC212486
0.8387 Intermediate Similarity NPC125674
0.8387 Intermediate Similarity NPC60386
0.837 Intermediate Similarity NPC35809
0.837 Intermediate Similarity NPC129419
0.837 Intermediate Similarity NPC51004
0.837 Intermediate Similarity NPC144133
0.837 Intermediate Similarity NPC179394
0.837 Intermediate Similarity NPC475855
0.8367 Intermediate Similarity NPC124881
0.8352 Intermediate Similarity NPC224652
0.8333 Intermediate Similarity NPC162071
0.8333 Intermediate Similarity NPC50637
0.8333 Intermediate Similarity NPC304558
0.8333 Intermediate Similarity NPC470242
0.8333 Intermediate Similarity NPC236692
0.8333 Intermediate Similarity NPC309757
0.8315 Intermediate Similarity NPC165287
0.8315 Intermediate Similarity NPC224386
0.8315 Intermediate Similarity NPC194859
0.8298 Intermediate Similarity NPC474247
0.8298 Intermediate Similarity NPC167219
0.8295 Intermediate Similarity NPC89555
0.8283 Intermediate Similarity NPC203659
0.8283 Intermediate Similarity NPC100487
0.828 Intermediate Similarity NPC30515
0.8276 Intermediate Similarity NPC69271
0.8276 Intermediate Similarity NPC74673
0.8265 Intermediate Similarity NPC474747
0.8265 Intermediate Similarity NPC225353
0.8261 Intermediate Similarity NPC268298
0.8261 Intermediate Similarity NPC295312
0.8252 Intermediate Similarity NPC258711
0.8252 Intermediate Similarity NPC95290
0.8252 Intermediate Similarity NPC35069
0.8252 Intermediate Similarity NPC189338
0.8247 Intermediate Similarity NPC70865
0.8247 Intermediate Similarity NPC186861
0.8242 Intermediate Similarity NPC190753
0.8242 Intermediate Similarity NPC24728
0.8229 Intermediate Similarity NPC471150
0.8229 Intermediate Similarity NPC474313
0.8229 Intermediate Similarity NPC169205
0.8229 Intermediate Similarity NPC181151
0.8222 Intermediate Similarity NPC255307
0.8222 Intermediate Similarity NPC215364
0.8222 Intermediate Similarity NPC165162
0.8211 Intermediate Similarity NPC224689
0.8211 Intermediate Similarity NPC48803
0.8211 Intermediate Similarity NPC90121
0.8211 Intermediate Similarity NPC270013
0.8211 Intermediate Similarity NPC14961
0.8211 Intermediate Similarity NPC193645
0.8211 Intermediate Similarity NPC275960
0.8211 Intermediate Similarity NPC36954
0.8202 Intermediate Similarity NPC272814
0.8202 Intermediate Similarity NPC128246
0.8202 Intermediate Similarity NPC111409
0.82 Intermediate Similarity NPC475217
0.82 Intermediate Similarity NPC54737
0.8191 Intermediate Similarity NPC472874
0.8191 Intermediate Similarity NPC153590
0.8182 Intermediate Similarity NPC301477
0.8182 Intermediate Similarity NPC25684
0.8182 Intermediate Similarity NPC110989
0.8182 Intermediate Similarity NPC475945
0.8182 Intermediate Similarity NPC39411
0.8182 Intermediate Similarity NPC255580
0.8182 Intermediate Similarity NPC475871
0.8182 Intermediate Similarity NPC141810
0.8182 Intermediate Similarity NPC281949
0.8173 Intermediate Similarity NPC209058
0.8172 Intermediate Similarity NPC62815
0.8163 Intermediate Similarity NPC474742
0.8163 Intermediate Similarity NPC171759
0.8161 Intermediate Similarity NPC617
0.8161 Intermediate Similarity NPC470239
0.8161 Intermediate Similarity NPC182550
0.8161 Intermediate Similarity NPC470244
0.8152 Intermediate Similarity NPC471149
0.8144 Intermediate Similarity NPC45125
0.8144 Intermediate Similarity NPC187268
0.8144 Intermediate Similarity NPC141191
0.814 Intermediate Similarity NPC470240
0.814 Intermediate Similarity NPC476794
0.8132 Intermediate Similarity NPC475461
0.8132 Intermediate Similarity NPC56593
0.8132 Intermediate Similarity NPC150755
0.8132 Intermediate Similarity NPC305475
0.8132 Intermediate Similarity NPC284902
0.8125 Intermediate Similarity NPC230800
0.8125 Intermediate Similarity NPC142529
0.8125 Intermediate Similarity NPC279621
0.8125 Intermediate Similarity NPC476315
0.8125 Intermediate Similarity NPC91771
0.8125 Intermediate Similarity NPC185553
0.8111 Intermediate Similarity NPC191476
0.8111 Intermediate Similarity NPC114979
0.8111 Intermediate Similarity NPC476804
0.8105 Intermediate Similarity NPC81386
0.8105 Intermediate Similarity NPC474035
0.81 Intermediate Similarity NPC474741
0.8085 Intermediate Similarity NPC111114
0.8085 Intermediate Similarity NPC261607
0.8085 Intermediate Similarity NPC74103
0.8085 Intermediate Similarity NPC300312
0.8085 Intermediate Similarity NPC123177

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC133698 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
0.9091 High Similarity NPD1695 Approved
0.8485 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.8211 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD6371 Approved
0.7634 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD5282 Discontinued
0.7423 Intermediate Similarity NPD6698 Approved
0.7423 Intermediate Similarity NPD46 Approved
0.7419 Intermediate Similarity NPD5362 Discontinued
0.7407 Intermediate Similarity NPD6053 Discontinued
0.7368 Intermediate Similarity NPD4249 Approved
0.7292 Intermediate Similarity NPD4251 Approved
0.7292 Intermediate Similarity NPD4250 Approved
0.7263 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD7154 Phase 3
0.7071 Intermediate Similarity NPD5785 Approved
0.7071 Intermediate Similarity NPD7838 Discovery
0.7021 Intermediate Similarity NPD5369 Approved
0.6947 Remote Similarity NPD6435 Approved
0.6931 Remote Similarity NPD6399 Phase 3
0.6915 Remote Similarity NPD4820 Approved
0.6915 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6915 Remote Similarity NPD4822 Approved
0.6915 Remote Similarity NPD4819 Approved
0.6915 Remote Similarity NPD4821 Approved
0.6907 Remote Similarity NPD5363 Approved
0.6881 Remote Similarity NPD6686 Approved
0.6852 Remote Similarity NPD6008 Approved
0.6847 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6832 Remote Similarity NPD7983 Approved
0.6771 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6771 Remote Similarity NPD4270 Approved
0.6771 Remote Similarity NPD4269 Approved
0.6765 Remote Similarity NPD5778 Approved
0.6765 Remote Similarity NPD5779 Approved
0.6762 Remote Similarity NPD4225 Approved
0.6762 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6762 Remote Similarity NPD7638 Approved
0.6737 Remote Similarity NPD5368 Approved
0.6735 Remote Similarity NPD1694 Approved
0.6702 Remote Similarity NPD4268 Approved
0.6702 Remote Similarity NPD4271 Approved
0.6702 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6701 Remote Similarity NPD5331 Approved
0.6701 Remote Similarity NPD5332 Approved
0.6698 Remote Similarity NPD7640 Approved
0.6698 Remote Similarity NPD7639 Approved
0.6667 Remote Similarity NPD4790 Discontinued
0.6667 Remote Similarity NPD5786 Approved
0.6636 Remote Similarity NPD5344 Discontinued
0.6635 Remote Similarity NPD5695 Phase 3
0.6604 Remote Similarity NPD5696 Approved
0.6562 Remote Similarity NPD4252 Approved
0.6552 Remote Similarity NPD7115 Discovery
0.6542 Remote Similarity NPD6648 Approved
0.6509 Remote Similarity NPD6083 Phase 2
0.6509 Remote Similarity NPD6084 Phase 2
0.6505 Remote Similarity NPD7637 Suspended
0.6486 Remote Similarity NPD5697 Approved
0.6471 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6101 Approved
0.6465 Remote Similarity NPD7338 Clinical (unspecified phase)
0.646 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7320 Approved
0.6429 Remote Similarity NPD6881 Approved
0.6429 Remote Similarity NPD6899 Approved
0.6429 Remote Similarity NPD5209 Approved
0.6404 Remote Similarity NPD6649 Approved
0.6404 Remote Similarity NPD6650 Approved
0.6396 Remote Similarity NPD6402 Approved
0.6396 Remote Similarity NPD5739 Approved
0.6396 Remote Similarity NPD6675 Approved
0.6396 Remote Similarity NPD7128 Approved
0.6393 Remote Similarity NPD7507 Approved
0.6372 Remote Similarity NPD6014 Approved
0.6372 Remote Similarity NPD6373 Approved
0.6372 Remote Similarity NPD6012 Approved
0.6372 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6372 Remote Similarity NPD6372 Approved
0.6372 Remote Similarity NPD6013 Approved
0.6364 Remote Similarity NPD6695 Phase 3
0.6346 Remote Similarity NPD5281 Approved
0.6346 Remote Similarity NPD5693 Phase 1
0.6346 Remote Similarity NPD6411 Approved
0.6346 Remote Similarity NPD5284 Approved
0.6339 Remote Similarity NPD5701 Approved
0.6333 Remote Similarity NPD8515 Approved
0.6333 Remote Similarity NPD8516 Approved
0.6333 Remote Similarity NPD8513 Phase 3
0.6333 Remote Similarity NPD8517 Approved
0.6321 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7102 Approved
0.6316 Remote Similarity NPD7290 Approved
0.6316 Remote Similarity NPD6883 Approved
0.6311 Remote Similarity NPD7492 Approved
0.6293 Remote Similarity NPD4632 Approved
0.6292 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6283 Remote Similarity NPD6011 Approved
0.6262 Remote Similarity NPD7839 Suspended
0.6261 Remote Similarity NPD8130 Phase 1
0.6261 Remote Similarity NPD6847 Approved
0.6261 Remote Similarity NPD6869 Approved
0.6261 Remote Similarity NPD6617 Approved
0.626 Remote Similarity NPD6616 Approved
0.625 Remote Similarity NPD6054 Approved
0.625 Remote Similarity NPD5207 Approved
0.625 Remote Similarity NPD6319 Approved
0.624 Remote Similarity NPD7319 Approved
0.6214 Remote Similarity NPD6672 Approved
0.6214 Remote Similarity NPD6903 Approved
0.6214 Remote Similarity NPD5737 Approved
0.621 Remote Similarity NPD7078 Approved
0.6207 Remote Similarity NPD6882 Approved
0.6207 Remote Similarity NPD8297 Approved
0.6204 Remote Similarity NPD7902 Approved
0.6198 Remote Similarity NPD6016 Approved
0.6198 Remote Similarity NPD6015 Approved
0.6195 Remote Similarity NPD6412 Phase 2
0.6195 Remote Similarity NPD5954 Clinical (unspecified phase)
0.619 Remote Similarity NPD8035 Phase 2
0.619 Remote Similarity NPD8034 Phase 2
0.6176 Remote Similarity NPD5330 Approved
0.6176 Remote Similarity NPD6684 Approved
0.6176 Remote Similarity NPD7521 Approved
0.6176 Remote Similarity NPD7334 Approved
0.6176 Remote Similarity NPD6409 Approved
0.6176 Remote Similarity NPD7146 Approved
0.6168 Remote Similarity NPD5210 Approved
0.6168 Remote Similarity NPD4629 Approved
0.616 Remote Similarity NPD7736 Approved
0.6154 Remote Similarity NPD4753 Phase 2
0.6148 Remote Similarity NPD5988 Approved
0.6148 Remote Similarity NPD6370 Approved
0.6139 Remote Similarity NPD4786 Approved
0.6134 Remote Similarity NPD6009 Approved
0.6126 Remote Similarity NPD5211 Phase 2
0.6126 Remote Similarity NPD7632 Discontinued
0.6117 Remote Similarity NPD7524 Approved
0.6117 Remote Similarity NPD7750 Discontinued
0.6116 Remote Similarity NPD6059 Approved
0.61 Remote Similarity NPD3667 Approved
0.6091 Remote Similarity NPD4696 Approved
0.6091 Remote Similarity NPD5285 Approved
0.6091 Remote Similarity NPD5286 Approved
0.6083 Remote Similarity NPD7328 Approved
0.6083 Remote Similarity NPD7327 Approved
0.608 Remote Similarity NPD8293 Discontinued
0.608 Remote Similarity NPD8074 Phase 3
0.6075 Remote Similarity NPD6001 Approved
0.6075 Remote Similarity NPD7748 Approved
0.6066 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6066 Remote Similarity NPD5983 Phase 2
0.6066 Remote Similarity NPD8033 Approved
0.6061 Remote Similarity NPD6930 Phase 2
0.6061 Remote Similarity NPD6931 Approved
0.6058 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6055 Remote Similarity NPD4755 Approved
0.605 Remote Similarity NPD6274 Approved
0.6042 Remote Similarity NPD8039 Approved
0.6033 Remote Similarity NPD7516 Approved
0.6019 Remote Similarity NPD3618 Phase 1
0.6019 Remote Similarity NPD5279 Phase 3
0.6018 Remote Similarity NPD5141 Approved
0.6017 Remote Similarity NPD8133 Approved
0.6016 Remote Similarity NPD7260 Phase 2
0.6 Remote Similarity NPD6673 Approved
0.6 Remote Similarity NPD6080 Approved
0.6 Remote Similarity NPD6051 Approved
0.6 Remote Similarity NPD6904 Approved
0.6 Remote Similarity NPD8273 Phase 1
0.6 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5984 Remote Similarity NPD8377 Approved
0.5984 Remote Similarity NPD8294 Approved
0.5983 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5983 Remote Similarity NPD2204 Approved
0.5982 Remote Similarity NPD4633 Approved
0.5982 Remote Similarity NPD5224 Approved
0.5982 Remote Similarity NPD5225 Approved
0.5982 Remote Similarity NPD5226 Approved
0.5981 Remote Similarity NPD4202 Approved
0.598 Remote Similarity NPD3665 Phase 1
0.598 Remote Similarity NPD6400 Clinical (unspecified phase)
0.598 Remote Similarity NPD3133 Approved
0.598 Remote Similarity NPD3666 Approved
0.5969 Remote Similarity NPD6845 Suspended
0.5968 Remote Similarity NPD7604 Phase 2
0.596 Remote Similarity NPD6929 Approved
0.5946 Remote Similarity NPD4700 Approved
0.5943 Remote Similarity NPD5692 Phase 3
0.5941 Remote Similarity NPD4221 Approved
0.5941 Remote Similarity NPD4223 Phase 3
0.5941 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5935 Remote Similarity NPD8296 Approved
0.5935 Remote Similarity NPD7503 Approved
0.5935 Remote Similarity NPD8379 Approved
0.5935 Remote Similarity NPD8380 Approved
0.5935 Remote Similarity NPD8335 Approved
0.5935 Remote Similarity NPD8378 Approved
0.5929 Remote Similarity NPD5174 Approved
0.5929 Remote Similarity NPD5175 Approved

Structure

External Identifiers

PubChem CID   174867
ChEMBL   CHEMBL190755
ZINC  

Physicochemical Properties

Molecular Weight:  306.15
ALogP:  0.5188
MLogP:  2.78
XLogP:  1.283
# Rotatable Bonds:  6
Polar Surface Area:  72.83
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  22

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
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