Natural Product: NPC178949

Natural Product ID:  NPC178949
Common Name:   Lemnaloside A
IUPAC Name:   [(2R,3R,4S,5R,6S)-6-[[(1S,4S,4aR,8aS)-1,6-dimethyl-4-[(2R)-6-methylhept-5-en-2-yl]-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
Synonyms:  
Molecular Formula:   C28H46O7
Standard InCHIKey:  NUFWENCOYDWSEV-FTWLUMHOSA-N
Standard InCHI:  InChI=1S/C28H46O7/c1-16(2)8-7-9-18(4)20-12-13-28(6,22-11-10-17(3)14-21(20)22)35-27-26(32)25(31)24(30)23(34-27)15-33-19(5)29/h8,14,18,20-27,30-32H,7,9-13,15H2,1-6H3/t18-,20+,21+,22+,23-,24+,25+,26-,27+,28+/m1/s1
Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](O[C@@]2(C)CC[C@H]([C@H]3[C@@H]2CCC(=C3)C)[C@@H](CCC=C(C)C)C)[C@@H]([C@H]([C@H]1O)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
NPO33496 lemnalia sp. Species Nephtheidae Eukaryota PMID[17506585]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT447 Organism Streptomyces Streptomyces IZ = 11 mm DrugMatrix in vivo data: Pathology

  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 NPC178949 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 NPC96736
0.9333 High Similarity NPC211238
0.914 High Similarity NPC477928
0.9032 High Similarity NPC96597
0.9032 High Similarity NPC309503
0.9032 High Similarity NPC125551
0.9032 High Similarity NPC155319
0.9032 High Similarity NPC239547
0.9032 High Similarity NPC91197
0.8969 High Similarity NPC470763
0.8969 High Similarity NPC470767
0.8913 High Similarity NPC305160
0.8866 High Similarity NPC470768
0.8866 High Similarity NPC31430
0.8866 High Similarity NPC85593
0.8866 High Similarity NPC173583
0.8854 High Similarity NPC470571
0.8776 High Similarity NPC473199
0.875 High Similarity NPC280991
0.8723 High Similarity NPC90583
0.871 High Similarity NPC477927
0.871 High Similarity NPC72817
0.8696 High Similarity NPC302584
0.8687 High Similarity NPC293512
0.866 High Similarity NPC154452
0.8652 High Similarity NPC477747
0.8652 High Similarity NPC477746
0.8617 High Similarity NPC230347
0.8617 High Similarity NPC286612
0.8617 High Similarity NPC275310
0.8602 High Similarity NPC474792
0.8602 High Similarity NPC91654
0.8602 High Similarity NPC67398
0.86 High Similarity NPC472988
0.86 High Similarity NPC38217
0.8557 High Similarity NPC21064
0.8557 High Similarity NPC121072
0.8556 High Similarity NPC470836
0.8542 High Similarity NPC5358
0.8542 High Similarity NPC216260
0.8539 High Similarity NPC166279
0.8515 High Similarity NPC167383
0.8515 High Similarity NPC125361
0.8515 High Similarity NPC57362
0.8515 High Similarity NPC137917
0.8515 High Similarity NPC51925
0.8515 High Similarity NPC204407
0.8515 High Similarity NPC237503
0.8515 High Similarity NPC43976
0.8515 High Similarity NPC296761
0.8515 High Similarity NPC306746
0.8515 High Similarity NPC154085
0.8506 High Similarity NPC100697
0.85 High Similarity NPC283849
0.85 High Similarity NPC234160
0.85 High Similarity NPC472390
0.8485 Intermediate Similarity NPC470060
0.8485 Intermediate Similarity NPC470057
0.8485 Intermediate Similarity NPC470064
0.8485 Intermediate Similarity NPC470061
0.8485 Intermediate Similarity NPC470062
0.8485 Intermediate Similarity NPC470043
0.8485 Intermediate Similarity NPC470058
0.8485 Intermediate Similarity NPC470059
0.8454 Intermediate Similarity NPC64348
0.8447 Intermediate Similarity NPC37739
0.8447 Intermediate Similarity NPC46388
0.8438 Intermediate Similarity NPC240372
0.8431 Intermediate Similarity NPC279554
0.8431 Intermediate Similarity NPC476881
0.8431 Intermediate Similarity NPC59804
0.8431 Intermediate Similarity NPC476886
0.8431 Intermediate Similarity NPC475296
0.8431 Intermediate Similarity NPC129340
0.8431 Intermediate Similarity NPC90856
0.8431 Intermediate Similarity NPC476887
0.8431 Intermediate Similarity NPC7870
0.8431 Intermediate Similarity NPC476880
0.8431 Intermediate Similarity NPC110139
0.8431 Intermediate Similarity NPC127056
0.8431 Intermediate Similarity NPC78046
0.8431 Intermediate Similarity NPC274507
0.8431 Intermediate Similarity NPC101450
0.8431 Intermediate Similarity NPC476882
0.8431 Intermediate Similarity NPC476883
0.8431 Intermediate Similarity NPC75747
0.8431 Intermediate Similarity NPC474589
0.8431 Intermediate Similarity NPC102914
0.8431 Intermediate Similarity NPC270667
0.8431 Intermediate Similarity NPC220984
0.8431 Intermediate Similarity NPC476884
0.8431 Intermediate Similarity NPC56713
0.8431 Intermediate Similarity NPC136877
0.8431 Intermediate Similarity NPC164194
0.8431 Intermediate Similarity NPC199457
0.8431 Intermediate Similarity NPC29069
0.8431 Intermediate Similarity NPC476885
0.8431 Intermediate Similarity NPC269095
0.8431 Intermediate Similarity NPC68419
0.8431 Intermediate Similarity NPC108709
0.8431 Intermediate Similarity NPC174679
0.8416 Intermediate Similarity NPC28198
0.8416 Intermediate Similarity NPC476123
0.8416 Intermediate Similarity NPC284807
0.8416 Intermediate Similarity NPC177246
0.8404 Intermediate Similarity NPC474835
0.8387 Intermediate Similarity NPC202886
0.8367 Intermediate Similarity NPC309425
0.8367 Intermediate Similarity NPC88000
0.8367 Intermediate Similarity NPC470054
0.8367 Intermediate Similarity NPC117714
0.8367 Intermediate Similarity NPC129372
0.8367 Intermediate Similarity NPC472023
0.8367 Intermediate Similarity NPC160734
0.8367 Intermediate Similarity NPC4831
0.8367 Intermediate Similarity NPC263756
0.8367 Intermediate Similarity NPC47566
0.8365 Intermediate Similarity NPC47063
0.8365 Intermediate Similarity NPC138334
0.8365 Intermediate Similarity NPC271138
0.8365 Intermediate Similarity NPC269315
0.8365 Intermediate Similarity NPC204458
0.8365 Intermediate Similarity NPC189884
0.8351 Intermediate Similarity NPC477875
0.8351 Intermediate Similarity NPC234287
0.8351 Intermediate Similarity NPC280825
0.8351 Intermediate Similarity NPC477876
0.835 Intermediate Similarity NPC263827
0.835 Intermediate Similarity NPC179434
0.835 Intermediate Similarity NPC65167
0.835 Intermediate Similarity NPC297208
0.835 Intermediate Similarity NPC250481
0.835 Intermediate Similarity NPC114188
0.835 Intermediate Similarity NPC31839
0.835 Intermediate Similarity NPC191763
0.835 Intermediate Similarity NPC285410
0.835 Intermediate Similarity NPC30397
0.835 Intermediate Similarity NPC235841
0.835 Intermediate Similarity NPC211798
0.835 Intermediate Similarity NPC164419
0.835 Intermediate Similarity NPC473481
0.835 Intermediate Similarity NPC108748
0.8333 Intermediate Similarity NPC265655
0.8333 Intermediate Similarity NPC127853
0.8317 Intermediate Similarity NPC473538
0.8315 Intermediate Similarity NPC20072
0.83 Intermediate Similarity NPC470885
0.83 Intermediate Similarity NPC187400
0.83 Intermediate Similarity NPC221562
0.8283 Intermediate Similarity NPC470053
0.8283 Intermediate Similarity NPC30289
0.8283 Intermediate Similarity NPC76497
0.8283 Intermediate Similarity NPC136816
0.8283 Intermediate Similarity NPC256133
0.8283 Intermediate Similarity NPC213674
0.828 Intermediate Similarity NPC473058
0.828 Intermediate Similarity NPC477748
0.8269 Intermediate Similarity NPC116794
0.8269 Intermediate Similarity NPC104400
0.8269 Intermediate Similarity NPC79718
0.8269 Intermediate Similarity NPC139044
0.8269 Intermediate Similarity NPC475504
0.8269 Intermediate Similarity NPC109079
0.8269 Intermediate Similarity NPC10320
0.8269 Intermediate Similarity NPC104071
0.8269 Intermediate Similarity NPC292677
0.8269 Intermediate Similarity NPC174836
0.8269 Intermediate Similarity NPC276093
0.8269 Intermediate Similarity NPC139894
0.8269 Intermediate Similarity NPC471967
0.8269 Intermediate Similarity NPC473125
0.8269 Intermediate Similarity NPC475516
0.8269 Intermediate Similarity NPC257468
0.8269 Intermediate Similarity NPC128925
0.8269 Intermediate Similarity NPC1046
0.8269 Intermediate Similarity NPC48249
0.8269 Intermediate Similarity NPC102439
0.8269 Intermediate Similarity NPC469946
0.8269 Intermediate Similarity NPC473373
0.8269 Intermediate Similarity NPC80843
0.8269 Intermediate Similarity NPC256798
0.8269 Intermediate Similarity NPC473383
0.8269 Intermediate Similarity NPC471383
0.8269 Intermediate Similarity NPC101744
0.8269 Intermediate Similarity NPC324875
0.8265 Intermediate Similarity NPC324598
0.8265 Intermediate Similarity NPC473200
0.8265 Intermediate Similarity NPC317019
0.8265 Intermediate Similarity NPC7341
0.8252 Intermediate Similarity NPC242611
0.8247 Intermediate Similarity NPC471770
0.8247 Intermediate Similarity NPC278939
0.8247 Intermediate Similarity NPC243728
0.8247 Intermediate Similarity NPC473555
0.8247 Intermediate Similarity NPC473890
0.8235 Intermediate Similarity NPC135015
0.8235 Intermediate Similarity NPC295980
0.8235 Intermediate Similarity NPC295389
0.8235 Intermediate Similarity NPC195708
0.8235 Intermediate Similarity NPC48548

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC178949 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
0.7981 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.789 Intermediate Similarity NPD7328 Approved
0.789 Intermediate Similarity NPD7327 Approved
0.7818 Intermediate Similarity NPD7516 Approved
0.7788 Intermediate Similarity NPD6412 Phase 2
0.7748 Intermediate Similarity NPD8294 Approved
0.7748 Intermediate Similarity NPD8377 Approved
0.7714 Intermediate Similarity NPD6686 Approved
0.7679 Intermediate Similarity NPD8033 Approved
0.7679 Intermediate Similarity NPD8379 Approved
0.7679 Intermediate Similarity NPD8378 Approved
0.7679 Intermediate Similarity NPD8296 Approved
0.7679 Intermediate Similarity NPD8335 Approved
0.7679 Intermediate Similarity NPD8380 Approved
0.7679 Intermediate Similarity NPD7503 Approved
0.7544 Intermediate Similarity NPD8328 Phase 3
0.7477 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD7507 Approved
0.7364 Intermediate Similarity NPD8133 Approved
0.7308 Intermediate Similarity NPD5344 Discontinued
0.7227 Intermediate Similarity NPD7319 Approved
0.7217 Intermediate Similarity NPD8517 Approved
0.7217 Intermediate Similarity NPD8516 Approved
0.7217 Intermediate Similarity NPD8513 Phase 3
0.7217 Intermediate Similarity NPD8515 Approved
0.7203 Intermediate Similarity NPD8293 Discontinued
0.7155 Intermediate Similarity NPD6370 Approved
0.7143 Intermediate Similarity NPD7736 Approved
0.7115 Intermediate Similarity NPD7638 Approved
0.7083 Intermediate Similarity NPD3669 Approved
0.7083 Intermediate Similarity NPD3670 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7639 Approved
0.7048 Intermediate Similarity NPD7640 Approved
0.7034 Intermediate Similarity NPD7492 Approved
0.7033 Intermediate Similarity NPD1811 Approved
0.7033 Intermediate Similarity NPD1810 Approved
0.7021 Intermediate Similarity NPD7645 Phase 2
0.7018 Intermediate Similarity NPD6009 Approved
0.7 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.6983 Remote Similarity NPD6054 Approved
0.6983 Remote Similarity NPD6059 Approved
0.6975 Remote Similarity NPD6616 Approved
0.6964 Remote Similarity NPD6882 Approved
0.6947 Remote Similarity NPD7525 Registered
0.6931 Remote Similarity NPD3168 Discontinued
0.6917 Remote Similarity NPD7078 Approved
0.6909 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6903 Remote Similarity NPD4632 Approved
0.6893 Remote Similarity NPD7748 Approved
0.6887 Remote Similarity NPD6648 Approved
0.6881 Remote Similarity NPD6402 Approved
0.6881 Remote Similarity NPD5739 Approved
0.6881 Remote Similarity NPD7128 Approved
0.6881 Remote Similarity NPD6675 Approved
0.6863 Remote Similarity NPD7515 Phase 2
0.6857 Remote Similarity NPD7902 Approved
0.6838 Remote Similarity NPD6319 Approved
0.6832 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6832 Remote Similarity NPD6101 Approved
0.6814 Remote Similarity NPD8297 Approved
0.6807 Remote Similarity NPD6067 Discontinued
0.6796 Remote Similarity NPD6399 Phase 3
0.6792 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4225 Approved
0.678 Remote Similarity NPD6015 Approved
0.678 Remote Similarity NPD6016 Approved
0.6765 Remote Similarity NPD46 Approved
0.6765 Remote Similarity NPD6698 Approved
0.6757 Remote Similarity NPD6899 Approved
0.6757 Remote Similarity NPD7320 Approved
0.6757 Remote Similarity NPD6881 Approved
0.6726 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6723 Remote Similarity NPD5988 Approved
0.6703 Remote Similarity NPD2254 Approved
0.6703 Remote Similarity NPD2687 Approved
0.6703 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6703 Remote Similarity NPD2686 Approved
0.6699 Remote Similarity NPD6411 Approved
0.6696 Remote Similarity NPD6373 Approved
0.6696 Remote Similarity NPD6372 Approved
0.6667 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD5697 Approved
0.6639 Remote Similarity NPD8074 Phase 3
0.6637 Remote Similarity NPD7102 Approved
0.6637 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6637 Remote Similarity NPD6883 Approved
0.6637 Remote Similarity NPD7290 Approved
0.6635 Remote Similarity NPD5779 Approved
0.6635 Remote Similarity NPD5778 Approved
0.6634 Remote Similarity NPD7524 Approved
0.6602 Remote Similarity NPD7838 Discovery
0.6581 Remote Similarity NPD7115 Discovery
0.6579 Remote Similarity NPD6869 Approved
0.6579 Remote Similarity NPD6847 Approved
0.6579 Remote Similarity NPD6649 Approved
0.6579 Remote Similarity NPD8130 Phase 1
0.6579 Remote Similarity NPD6650 Approved
0.6579 Remote Similarity NPD6617 Approved
0.6571 Remote Similarity NPD7900 Approved
0.6571 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6549 Remote Similarity NPD6014 Approved
0.6549 Remote Similarity NPD6012 Approved
0.6549 Remote Similarity NPD6013 Approved
0.6542 Remote Similarity NPD6083 Phase 2
0.6542 Remote Similarity NPD6084 Phase 2
0.6531 Remote Similarity NPD1779 Approved
0.6531 Remote Similarity NPD1780 Approved
0.6529 Remote Similarity NPD7604 Phase 2
0.65 Remote Similarity NPD7338 Clinical (unspecified phase)
0.65 Remote Similarity NPD5983 Phase 2
0.65 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6476 Remote Similarity NPD8171 Discontinued
0.646 Remote Similarity NPD6011 Approved
0.6455 Remote Similarity NPD7632 Discontinued
0.6452 Remote Similarity NPD6033 Approved
0.6435 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6429 Remote Similarity NPD5357 Phase 1
0.6429 Remote Similarity NPD6008 Approved
0.6423 Remote Similarity NPD6336 Discontinued
0.6421 Remote Similarity NPD6942 Approved
0.6421 Remote Similarity NPD7339 Approved
0.6404 Remote Similarity NPD371 Approved
0.64 Remote Similarity NPD6695 Phase 3
0.6389 Remote Similarity NPD4755 Approved
0.6381 Remote Similarity NPD8035 Phase 2
0.6381 Remote Similarity NPD8034 Phase 2
0.6381 Remote Similarity NPD7983 Approved
0.6379 Remote Similarity NPD6053 Discontinued
0.6373 Remote Similarity NPD3618 Phase 1
0.6372 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6355 Remote Similarity NPD5695 Phase 3
0.6354 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6348 Remote Similarity NPD4634 Approved
0.6346 Remote Similarity NPD5328 Approved
0.6346 Remote Similarity NPD6051 Approved
0.6337 Remote Similarity NPD4786 Approved
0.6321 Remote Similarity NPD4202 Approved
0.6311 Remote Similarity NPD3573 Approved
0.6306 Remote Similarity NPD3653 Clinical (unspecified phase)
0.63 Remote Similarity NPD3667 Approved
0.6275 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6273 Remote Similarity NPD5285 Approved
0.6273 Remote Similarity NPD5286 Approved
0.6273 Remote Similarity NPD4700 Approved
0.6273 Remote Similarity NPD4696 Approved
0.625 Remote Similarity NPD8449 Approved
0.625 Remote Similarity NPD7625 Phase 1
0.623 Remote Similarity NPD6921 Approved
0.6226 Remote Similarity NPD7637 Suspended
0.6226 Remote Similarity NPD6079 Approved
0.6218 Remote Similarity NPD6274 Approved
0.6214 Remote Similarity NPD7334 Approved
0.6214 Remote Similarity NPD5330 Approved
0.6214 Remote Similarity NPD7146 Approved
0.6214 Remote Similarity NPD6409 Approved
0.6214 Remote Similarity NPD7521 Approved
0.6214 Remote Similarity NPD6684 Approved
0.6202 Remote Similarity NPD8450 Suspended
0.6198 Remote Similarity NPD7100 Approved
0.6198 Remote Similarity NPD7101 Approved
0.6195 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6186 Remote Similarity NPD6933 Approved
0.6182 Remote Similarity NPD5696 Approved
0.6167 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6161 Remote Similarity NPD5226 Approved
0.6161 Remote Similarity NPD4633 Approved
0.6161 Remote Similarity NPD5224 Approved
0.6161 Remote Similarity NPD5211 Phase 2
0.6161 Remote Similarity NPD5225 Approved
0.6154 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6154 Remote Similarity NPD7750 Discontinued
0.6116 Remote Similarity NPD7641 Discontinued
0.6116 Remote Similarity NPD6335 Approved
0.6106 Remote Similarity NPD5175 Approved
0.6106 Remote Similarity NPD5174 Approved
0.61 Remote Similarity NPD6931 Approved
0.61 Remote Similarity NPD6928 Phase 2
0.61 Remote Similarity NPD6930 Phase 2
0.6098 Remote Similarity NPD6908 Approved
0.6098 Remote Similarity NPD6909 Approved
0.6095 Remote Similarity NPD6672 Approved
0.6095 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6095 Remote Similarity NPD6903 Approved
0.6095 Remote Similarity NPD5737 Approved
0.608 Remote Similarity NPD8341 Approved
0.608 Remote Similarity NPD8340 Approved
0.608 Remote Similarity NPD8342 Approved
0.608 Remote Similarity NPD8299 Approved
0.6071 Remote Similarity NPD5223 Approved
0.6067 Remote Similarity NPD1145 Discontinued
0.6063 Remote Similarity NPD8337 Approved
0.6063 Remote Similarity NPD8336 Approved
0.6055 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6053 Remote Similarity NPD5141 Approved
0.6038 Remote Similarity NPD4753 Phase 2
0.6033 Remote Similarity NPD6317 Approved
0.6032 Remote Similarity NPD8451 Approved
0.6019 Remote Similarity NPD3666 Approved
0.6019 Remote Similarity NPD3133 Approved
0.6019 Remote Similarity NPD3665 Phase 1

Structure

External Identifiers

PubChem CID   16737221
ChEMBL   CHEMBL226094
ZINC  

Physicochemical Properties

Molecular Weight:  494.32
ALogP:  1.6242
MLogP:  3.77
XLogP:  5.606
# Rotatable Bonds:  18
Polar Surface Area:  105.45
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  35

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs