Natural Product: NPC475038

Natural Product ID:  NPC475038
Common Name:   ((1R,4R,4Ar,5S,6R,8S,8Ar)-8-Acetoxy-8A-(Acetoxymethyl)-5-((S)-2-Hydroxy-2-(5-Oxo-2,5-Dihydrofuran-3-Yl)Ethyl)-5,6-Dimethyloctahydro-2H-Spiro[Naphthalene-1,2'-Oxirane]-4-Yl) 2-Methylbut-2-Enoate
IUPAC Name:   [(1R,4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-8-[(2S)-2-hydroxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (Z)-2-methylbut-2-enoate
Synonyms:  
Molecular Formula:   C29H40O10
Standard InCHIKey:  HZPBAEMQRBYDPW-ZERDVMLBSA-N
Standard InCHI:  InChI=1S/C29H40O10/c1-7-16(2)26(34)39-22-8-9-28(14-37-28)29(15-36-18(4)30)23(38-19(5)31)10-17(3)27(6,25(22)29)12-21(32)20-11-24(33)35-13-20/h7,11,17,21-23,25,32H,8-10,12-15H2,1-6H3/b16-7-/t17-,21+,22-,23+,25-,27+,28+,29-/m1/s1
Canonical SMILES:  C/C=C(C(=O)O[C@@H]1CC[C@@]2([C@]3([C@H]1[C@@](C)(C[C@@H](C1=CC(=O)OC1)O)[C@H](C)C[C@@H]3OC(=O)C)COC(=O)C)CO2)/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
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota flowering whole plant PMID[10425119]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT80 Cell Line Raji Homo sapiens Activity > 80 % 7931367
NPT80 Cell Line Raji Homo sapiens Activity = 50 % 25238284
NPT2 Others Unspecified Activity = 0 % 22834923
NPT2 Others Unspecified Activity = 100 % 9090874
NPT2 Others Unspecified Activity = 55.8 % 10560729
NPT2 Others Unspecified Activity = 76.3 % 10560729
NPT80 Cell Line Raji Homo sapiens Activity > 80 % 10924160
NPT80 Cell Line Raji Homo sapiens Activity > 80 % Open TG-GATES in vivo data: Biochemistry

  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 NPC475038 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 NPC109195
0.9468 High Similarity NPC475380
0.9468 High Similarity NPC209297
0.9368 High Similarity NPC311241
0.9368 High Similarity NPC475446
0.9271 High Similarity NPC107806
0.9271 High Similarity NPC72647
0.9255 High Similarity NPC105490
0.9255 High Similarity NPC140277
0.9175 High Similarity NPC16601
0.9167 High Similarity NPC100912
0.9149 High Similarity NPC7349
0.9091 High Similarity NPC471938
0.9082 High Similarity NPC11974
0.9062 High Similarity NPC194132
0.902 High Similarity NPC322912
0.9 High Similarity NPC471937
0.899 High Similarity NPC471914
0.898 High Similarity NPC324841
0.8958 High Similarity NPC276110
0.8922 High Similarity NPC181994
0.8824 High Similarity NPC319438
0.8824 High Similarity NPC471205
0.88 High Similarity NPC162973
0.8788 High Similarity NPC38855
0.8763 High Similarity NPC471915
0.8763 High Similarity NPC111273
0.8737 High Similarity NPC78973
0.8723 High Similarity NPC93411
0.87 High Similarity NPC471412
0.8687 High Similarity NPC325229
0.8687 High Similarity NPC275086
0.8687 High Similarity NPC278673
0.8673 High Similarity NPC134072
0.8673 High Similarity NPC234993
0.866 High Similarity NPC161998
0.8646 High Similarity NPC78594
0.8641 High Similarity NPC216636
0.8614 High Similarity NPC472552
0.8614 High Similarity NPC476081
0.86 High Similarity NPC471413
0.8586 High Similarity NPC51499
0.8571 High Similarity NPC472441
0.8557 High Similarity NPC472641
0.8557 High Similarity NPC472640
0.8544 High Similarity NPC51719
0.8544 High Similarity NPC218158
0.8529 High Similarity NPC160583
0.8529 High Similarity NPC474822
0.8515 High Similarity NPC472554
0.8511 High Similarity NPC131813
0.85 High Similarity NPC218107
0.8485 Intermediate Similarity NPC165632
0.8476 Intermediate Similarity NPC475586
0.8469 Intermediate Similarity NPC57117
0.8462 Intermediate Similarity NPC187435
0.8462 Intermediate Similarity NPC67321
0.8462 Intermediate Similarity NPC122816
0.8454 Intermediate Similarity NPC473675
0.8421 Intermediate Similarity NPC166857
0.8416 Intermediate Similarity NPC251680
0.84 Intermediate Similarity NPC205143
0.8381 Intermediate Similarity NPC38948
0.8367 Intermediate Similarity NPC205034
0.8367 Intermediate Similarity NPC53555
0.8367 Intermediate Similarity NPC139692
0.8367 Intermediate Similarity NPC152778
0.8367 Intermediate Similarity NPC110022
0.8367 Intermediate Similarity NPC162615
0.8365 Intermediate Similarity NPC81630
0.8365 Intermediate Similarity NPC471206
0.8365 Intermediate Similarity NPC119855
0.8365 Intermediate Similarity NPC220217
0.8365 Intermediate Similarity NPC34768
0.8351 Intermediate Similarity NPC472642
0.835 Intermediate Similarity NPC45897
0.835 Intermediate Similarity NPC189588
0.835 Intermediate Similarity NPC10232
0.835 Intermediate Similarity NPC187302
0.835 Intermediate Similarity NPC120009
0.835 Intermediate Similarity NPC120321
0.835 Intermediate Similarity NPC473523
0.835 Intermediate Similarity NPC97487
0.835 Intermediate Similarity NPC196471
0.835 Intermediate Similarity NPC281378
0.8349 Intermediate Similarity NPC470075
0.8333 Intermediate Similarity NPC268829
0.8333 Intermediate Similarity NPC222875
0.8333 Intermediate Similarity NPC295110
0.8333 Intermediate Similarity NPC247701
0.8333 Intermediate Similarity NPC291665
0.8333 Intermediate Similarity NPC25177
0.8318 Intermediate Similarity NPC470076
0.8302 Intermediate Similarity NPC206618
0.83 Intermediate Similarity NPC472995
0.83 Intermediate Similarity NPC16967
0.83 Intermediate Similarity NPC29952
0.83 Intermediate Similarity NPC242848
0.8298 Intermediate Similarity NPC32223
0.8298 Intermediate Similarity NPC306951
0.8298 Intermediate Similarity NPC102048
0.8286 Intermediate Similarity NPC475074
0.8283 Intermediate Similarity NPC119562
0.8283 Intermediate Similarity NPC279410
0.8269 Intermediate Similarity NPC473543
0.8265 Intermediate Similarity NPC329842
0.8265 Intermediate Similarity NPC72845
0.8265 Intermediate Similarity NPC124374
0.8257 Intermediate Similarity NPC216665
0.8252 Intermediate Similarity NPC472815
0.8247 Intermediate Similarity NPC170633
0.8247 Intermediate Similarity NPC314727
0.8235 Intermediate Similarity NPC47024
0.8235 Intermediate Similarity NPC470074
0.8224 Intermediate Similarity NPC177047
0.8218 Intermediate Similarity NPC287668
0.8218 Intermediate Similarity NPC472998
0.8218 Intermediate Similarity NPC473244
0.8208 Intermediate Similarity NPC475263
0.8208 Intermediate Similarity NPC306265
0.8208 Intermediate Similarity NPC470024
0.8208 Intermediate Similarity NPC88701
0.8208 Intermediate Similarity NPC50124
0.82 Intermediate Similarity NPC469583
0.8191 Intermediate Similarity NPC476927
0.8191 Intermediate Similarity NPC311070
0.8182 Intermediate Similarity NPC471816
0.8182 Intermediate Similarity NPC99653
0.8182 Intermediate Similarity NPC472812
0.8173 Intermediate Similarity NPC112009
0.8173 Intermediate Similarity NPC478057
0.8173 Intermediate Similarity NPC297617
0.8173 Intermediate Similarity NPC23584
0.8173 Intermediate Similarity NPC472821
0.8165 Intermediate Similarity NPC171126
0.8165 Intermediate Similarity NPC25909
0.8163 Intermediate Similarity NPC220216
0.8163 Intermediate Similarity NPC310479
0.8163 Intermediate Similarity NPC182136
0.8155 Intermediate Similarity NPC477717
0.8144 Intermediate Similarity NPC106332
0.8131 Intermediate Similarity NPC299590
0.8125 Intermediate Similarity NPC471219
0.8119 Intermediate Similarity NPC284194
0.8119 Intermediate Similarity NPC472997
0.8119 Intermediate Similarity NPC471765
0.8119 Intermediate Similarity NPC221801
0.8119 Intermediate Similarity NPC211810
0.8119 Intermediate Similarity NPC473153
0.8119 Intermediate Similarity NPC472996
0.8119 Intermediate Similarity NPC202833
0.8113 Intermediate Similarity NPC302788
0.8113 Intermediate Similarity NPC109376
0.8113 Intermediate Similarity NPC475781
0.8113 Intermediate Similarity NPC179380
0.8113 Intermediate Similarity NPC473586
0.81 Intermediate Similarity NPC472416
0.81 Intermediate Similarity NPC191521
0.81 Intermediate Similarity NPC472360
0.8091 Intermediate Similarity NPC474872
0.8091 Intermediate Similarity NPC43213
0.8085 Intermediate Similarity NPC2524
0.8081 Intermediate Similarity NPC472811
0.8077 Intermediate Similarity NPC121423
0.8077 Intermediate Similarity NPC475344
0.8077 Intermediate Similarity NPC165250
0.8077 Intermediate Similarity NPC11956
0.8077 Intermediate Similarity NPC476471
0.8077 Intermediate Similarity NPC470972
0.8073 Intermediate Similarity NPC90952
0.8073 Intermediate Similarity NPC42658
0.8073 Intermediate Similarity NPC470063
0.807 Intermediate Similarity NPC23786
0.807 Intermediate Similarity NPC470265
0.8061 Intermediate Similarity NPC246028
0.8061 Intermediate Similarity NPC50488
0.8061 Intermediate Similarity NPC174342
0.8061 Intermediate Similarity NPC261320
0.8061 Intermediate Similarity NPC474396
0.8058 Intermediate Similarity NPC476767
0.8058 Intermediate Similarity NPC272223
0.8058 Intermediate Similarity NPC477721
0.8058 Intermediate Similarity NPC79303
0.8058 Intermediate Similarity NPC477716
0.8056 Intermediate Similarity NPC103491
0.8041 Intermediate Similarity NPC471796
0.8039 Intermediate Similarity NPC473963
0.8039 Intermediate Similarity NPC73911
0.8039 Intermediate Similarity NPC99726
0.8039 Intermediate Similarity NPC136781
0.8039 Intermediate Similarity NPC477718
0.8039 Intermediate Similarity NPC477719
0.8039 Intermediate Similarity NPC199099
0.8037 Intermediate Similarity NPC322903
0.8037 Intermediate Similarity NPC275539
0.8037 Intermediate Similarity NPC189075
0.8037 Intermediate Similarity NPC102843
0.8037 Intermediate Similarity NPC224660
0.8034 Intermediate Similarity NPC476859
0.8021 Intermediate Similarity NPC474013

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC475038 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
0.8416 Intermediate Similarity NPD7639 Approved
0.8416 Intermediate Similarity NPD7640 Approved
0.8317 Intermediate Similarity NPD7638 Approved
0.8155 Intermediate Similarity NPD5344 Discontinued
0.8131 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.8056 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD4225 Approved
0.7885 Intermediate Similarity NPD6648 Approved
0.7876 Intermediate Similarity NPD7328 Approved
0.7876 Intermediate Similarity NPD7327 Approved
0.787 Intermediate Similarity NPD6686 Approved
0.7807 Intermediate Similarity NPD7516 Approved
0.7778 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD7632 Discontinued
0.7632 Intermediate Similarity NPD7115 Discovery
0.7586 Intermediate Similarity NPD8377 Approved
0.7586 Intermediate Similarity NPD8294 Approved
0.7521 Intermediate Similarity NPD8378 Approved
0.7521 Intermediate Similarity NPD8379 Approved
0.7521 Intermediate Similarity NPD8296 Approved
0.7521 Intermediate Similarity NPD8033 Approved
0.7521 Intermediate Similarity NPD8380 Approved
0.7521 Intermediate Similarity NPD8335 Approved
0.7451 Intermediate Similarity NPD7838 Discovery
0.7417 Intermediate Similarity NPD7507 Approved
0.7373 Intermediate Similarity NPD7503 Approved
0.7347 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD46 Approved
0.7282 Intermediate Similarity NPD6698 Approved
0.7236 Intermediate Similarity NPD7319 Approved
0.7232 Intermediate Similarity NPD6881 Approved
0.7232 Intermediate Similarity NPD6899 Approved
0.7207 Intermediate Similarity NPD7128 Approved
0.7207 Intermediate Similarity NPD5739 Approved
0.7207 Intermediate Similarity NPD6675 Approved
0.7207 Intermediate Similarity NPD6402 Approved
0.7193 Intermediate Similarity NPD6649 Approved
0.7193 Intermediate Similarity NPD6650 Approved
0.7168 Intermediate Similarity NPD6373 Approved
0.7168 Intermediate Similarity NPD6372 Approved
0.7143 Intermediate Similarity NPD5697 Approved
0.713 Intermediate Similarity NPD8297 Approved
0.713 Intermediate Similarity NPD6882 Approved
0.7105 Intermediate Similarity NPD6883 Approved
0.7105 Intermediate Similarity NPD7290 Approved
0.7105 Intermediate Similarity NPD7102 Approved
0.708 Intermediate Similarity NPD7320 Approved
0.7075 Intermediate Similarity NPD7748 Approved
0.7054 Intermediate Similarity NPD6008 Approved
0.7048 Intermediate Similarity NPD7515 Phase 2
0.7048 Intermediate Similarity NPD7637 Suspended
0.7043 Intermediate Similarity NPD6869 Approved
0.7043 Intermediate Similarity NPD6847 Approved
0.7043 Intermediate Similarity NPD8130 Phase 1
0.7043 Intermediate Similarity NPD6617 Approved
0.7037 Intermediate Similarity NPD7902 Approved
0.703 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD6012 Approved
0.7018 Intermediate Similarity NPD6013 Approved
0.7018 Intermediate Similarity NPD6014 Approved
0.7 Intermediate Similarity NPD6319 Approved
0.6991 Remote Similarity NPD5701 Approved
0.6972 Remote Similarity NPD8029 Clinical (unspecified phase)
0.697 Remote Similarity NPD7525 Registered
0.6957 Remote Similarity NPD6371 Approved
0.6937 Remote Similarity NPD5211 Phase 2
0.6931 Remote Similarity NPD6695 Phase 3
0.693 Remote Similarity NPD6011 Approved
0.693 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4632 Approved
0.6881 Remote Similarity NPD6083 Phase 2
0.6881 Remote Similarity NPD6084 Phase 2
0.6857 Remote Similarity NPD6051 Approved
0.6838 Remote Similarity NPD6053 Discontinued
0.6829 Remote Similarity NPD7604 Phase 2
0.6822 Remote Similarity NPD6399 Phase 3
0.6814 Remote Similarity NPD5141 Approved
0.6796 Remote Similarity NPD1694 Approved
0.678 Remote Similarity NPD8133 Approved
0.6774 Remote Similarity NPD7492 Approved
0.6759 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6759 Remote Similarity NPD7900 Approved
0.6757 Remote Similarity NPD5286 Approved
0.6757 Remote Similarity NPD4696 Approved
0.6757 Remote Similarity NPD5285 Approved
0.6752 Remote Similarity NPD6401 Clinical (unspecified phase)
0.675 Remote Similarity NPD6009 Approved
0.6731 Remote Similarity NPD3618 Phase 1
0.6729 Remote Similarity NPD6079 Approved
0.6727 Remote Similarity NPD4755 Approved
0.6721 Remote Similarity NPD6054 Approved
0.672 Remote Similarity NPD6616 Approved
0.67 Remote Similarity NPD7645 Phase 2
0.6698 Remote Similarity NPD5328 Approved
0.6696 Remote Similarity NPD6412 Phase 2
0.6667 Remote Similarity NPD4202 Approved
0.6667 Remote Similarity NPD7078 Approved
0.6667 Remote Similarity NPD7524 Approved
0.6667 Remote Similarity NPD5778 Approved
0.6667 Remote Similarity NPD5983 Phase 2
0.6667 Remote Similarity NPD6274 Approved
0.6667 Remote Similarity NPD7750 Discontinued
0.6667 Remote Similarity NPD5779 Approved
0.6639 Remote Similarity NPD7101 Approved
0.6639 Remote Similarity NPD7100 Approved
0.6637 Remote Similarity NPD4633 Approved
0.6637 Remote Similarity NPD5224 Approved
0.6637 Remote Similarity NPD5226 Approved
0.6637 Remote Similarity NPD5225 Approved
0.6634 Remote Similarity NPD6931 Approved
0.6634 Remote Similarity NPD6930 Phase 2
0.6614 Remote Similarity NPD7736 Approved
0.6613 Remote Similarity NPD6370 Approved
0.6607 Remote Similarity NPD4700 Approved
0.6587 Remote Similarity NPD6336 Discontinued
0.6585 Remote Similarity NPD6059 Approved
0.6581 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6579 Remote Similarity NPD5174 Approved
0.6579 Remote Similarity NPD5175 Approved
0.6574 Remote Similarity NPD8035 Phase 2
0.6574 Remote Similarity NPD8034 Phase 2
0.6571 Remote Similarity NPD6684 Approved
0.6571 Remote Similarity NPD7334 Approved
0.6571 Remote Similarity NPD6409 Approved
0.6571 Remote Similarity NPD7146 Approved
0.6571 Remote Similarity NPD5330 Approved
0.6571 Remote Similarity NPD7521 Approved
0.656 Remote Similarity NPD8328 Phase 3
0.6557 Remote Similarity NPD6335 Approved
0.6552 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6549 Remote Similarity NPD5223 Approved
0.6545 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6545 Remote Similarity NPD5695 Phase 3
0.6535 Remote Similarity NPD8293 Discontinued
0.6535 Remote Similarity NPD6929 Approved
0.6532 Remote Similarity NPD6016 Approved
0.6532 Remote Similarity NPD6015 Approved
0.6525 Remote Similarity NPD4634 Approved
0.6518 Remote Similarity NPD5696 Approved
0.6509 Remote Similarity NPD3573 Approved
0.6509 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6496 Remote Similarity NPD4730 Approved
0.6496 Remote Similarity NPD4729 Approved
0.6486 Remote Similarity NPD5222 Approved
0.6486 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6486 Remote Similarity NPD5221 Approved
0.6481 Remote Similarity NPD5785 Approved
0.648 Remote Similarity NPD5988 Approved
0.6476 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6475 Remote Similarity NPD6317 Approved
0.6471 Remote Similarity NPD7332 Phase 2
0.6471 Remote Similarity NPD7514 Phase 3
0.6466 Remote Similarity NPD4767 Approved
0.6466 Remote Similarity NPD4768 Approved
0.6449 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6449 Remote Similarity NPD6672 Approved
0.6449 Remote Similarity NPD6903 Approved
0.6449 Remote Similarity NPD5737 Approved
0.6429 Remote Similarity NPD5173 Approved
0.6423 Remote Similarity NPD6313 Approved
0.6423 Remote Similarity NPD6314 Approved
0.6422 Remote Similarity NPD7087 Discontinued
0.6422 Remote Similarity NPD5693 Phase 1
0.6408 Remote Similarity NPD6902 Approved
0.64 Remote Similarity NPD6921 Approved
0.64 Remote Similarity NPD8513 Phase 3
0.64 Remote Similarity NPD6909 Approved
0.64 Remote Similarity NPD6908 Approved
0.64 Remote Similarity NPD8515 Approved
0.64 Remote Similarity NPD8517 Approved
0.64 Remote Similarity NPD8516 Approved
0.6396 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6393 Remote Similarity NPD6868 Approved
0.6389 Remote Similarity NPD4753 Phase 2
0.6389 Remote Similarity NPD1695 Approved
0.6387 Remote Similarity NPD5249 Phase 3
0.6387 Remote Similarity NPD5247 Approved
0.6387 Remote Similarity NPD5248 Approved
0.6387 Remote Similarity NPD5250 Approved
0.6387 Remote Similarity NPD5251 Approved
0.6383 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6381 Remote Similarity NPD3666 Approved
0.6381 Remote Similarity NPD3133 Approved
0.6381 Remote Similarity NPD3665 Phase 1
0.6381 Remote Similarity NPD4786 Approved
0.6356 Remote Similarity NPD5128 Approved
0.6355 Remote Similarity NPD4251 Approved
0.6355 Remote Similarity NPD4250 Approved
0.6346 Remote Similarity NPD3667 Approved
0.6339 Remote Similarity NPD4697 Phase 3
0.6337 Remote Similarity NPD6925 Approved
0.6337 Remote Similarity NPD5776 Phase 2
0.6333 Remote Similarity NPD8413 Clinical (unspecified phase)
0.633 Remote Similarity NPD3168 Discontinued
0.6321 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6321 Remote Similarity NPD1696 Phase 3
0.6321 Remote Similarity NPD6893 Approved
0.6311 Remote Similarity NPD4820 Approved
0.6311 Remote Similarity NPD4821 Approved

Structure

External Identifiers

PubChem CID   44566360
ChEMBL   CHEMBL493852
ZINC  

Physicochemical Properties

Molecular Weight:  548.26
ALogP:  0.3494
MLogP:  3.55
XLogP:  3.172
# Rotatable Bonds:  18
Polar Surface Area:  137.96
# H-Bond Aceptor:  10
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  39

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs