Natural Product: NPC198422

Natural Product ID:  NPC198422
Common Name:   Gusanlungionoside A
IUPAC Name:   (4S)-4-[(E,3R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one
Synonyms:   Gusanlungionoside A
Molecular Formula:   C25H40O11
Standard InCHIKey:  HNFRYUMXAKNBBJ-AHXVQEEHSA-N
Standard InCHI:  InChI=1S/C25H40O11/c1-11-8-14(27)9-25(4,5)15(11)7-6-12(2)33-24-22(20(31)18(29)16(10-26)35-24)36-23-21(32)19(30)17(28)13(3)34-23/h6-8,12-13,15-24,26,28-32H,9-10H2,1-5H3/b7-6+/t12-,13+,15-,16-,17+,18-,19-,20+,21-,22-,23+,24-/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@@H](/C=C/[C@@H]2C(=CC(=O)CC2(C)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](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
NPO1338 Arcangelisia gusanlung Species Menispermaceae Eukaryota Stems PMID[21500777]
NPO19018 Senecio provincialis Species Asteraceae Eukaryota UNPD*
NPO4674 Gaillardia powellii Species Asteraceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 = 150000 nM 21500777

  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 NPC198422 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 NPC40182
0.956 High Similarity NPC25701
0.956 High Similarity NPC2003
0.9158 High Similarity NPC307517
0.9158 High Similarity NPC169468
0.9158 High Similarity NPC81483
0.9158 High Similarity NPC61630
0.8958 High Similarity NPC70733
0.8958 High Similarity NPC56071
0.8854 High Similarity NPC474194
0.8788 High Similarity NPC151516
0.875 High Similarity NPC256230
0.8737 High Similarity NPC294293
0.866 High Similarity NPC278506
0.8646 High Similarity NPC108141
0.8586 High Similarity NPC154127
0.8557 High Similarity NPC143446
0.85 High Similarity NPC223834
0.8447 Intermediate Similarity NPC392
0.8447 Intermediate Similarity NPC177524
0.8447 Intermediate Similarity NPC219900
0.8404 Intermediate Similarity NPC471756
0.8404 Intermediate Similarity NPC471755
0.8286 Intermediate Similarity NPC83005
0.8144 Intermediate Similarity NPC477749
0.8137 Intermediate Similarity NPC201191
0.8125 Intermediate Similarity NPC477748
0.8108 Intermediate Similarity NPC48692
0.81 Intermediate Similarity NPC96597
0.81 Intermediate Similarity NPC155319
0.81 Intermediate Similarity NPC309503
0.81 Intermediate Similarity NPC125551
0.81 Intermediate Similarity NPC91197
0.81 Intermediate Similarity NPC239547
0.8095 Intermediate Similarity NPC272576
0.8095 Intermediate Similarity NPC473288
0.8077 Intermediate Similarity NPC82251
0.8061 Intermediate Similarity NPC474792
0.8061 Intermediate Similarity NPC67398
0.8061 Intermediate Similarity NPC91654
0.8061 Intermediate Similarity NPC320552
0.8056 Intermediate Similarity NPC311592
0.8056 Intermediate Similarity NPC75167
0.8041 Intermediate Similarity NPC202886
0.8041 Intermediate Similarity NPC327253
0.8039 Intermediate Similarity NPC280991
0.8039 Intermediate Similarity NPC198992
0.8021 Intermediate Similarity NPC248312
0.8 Intermediate Similarity NPC474483
0.7982 Intermediate Similarity NPC475163
0.7982 Intermediate Similarity NPC181145
0.7979 Intermediate Similarity NPC266718
0.7961 Intermediate Similarity NPC222062
0.7928 Intermediate Similarity NPC473828
0.7928 Intermediate Similarity NPC473617
0.7928 Intermediate Similarity NPC234522
0.7905 Intermediate Similarity NPC476740
0.7905 Intermediate Similarity NPC476738
0.7905 Intermediate Similarity NPC239961
0.79 Intermediate Similarity NPC469543
0.789 Intermediate Similarity NPC293658
0.789 Intermediate Similarity NPC474410
0.789 Intermediate Similarity NPC473159
0.7885 Intermediate Similarity NPC118761
0.7885 Intermediate Similarity NPC309398
0.7885 Intermediate Similarity NPC267869
0.7885 Intermediate Similarity NPC197541
0.7885 Intermediate Similarity NPC284929
0.7885 Intermediate Similarity NPC234304
0.7879 Intermediate Similarity NPC61201
0.7876 Intermediate Similarity NPC476204
0.7876 Intermediate Similarity NPC170084
0.785 Intermediate Similarity NPC246205
0.7838 Intermediate Similarity NPC473405
0.7822 Intermediate Similarity NPC54731
0.7818 Intermediate Similarity NPC165439
0.7798 Intermediate Similarity NPC471967
0.7798 Intermediate Similarity NPC174836
0.7788 Intermediate Similarity NPC476150
0.7788 Intermediate Similarity NPC473130
0.7788 Intermediate Similarity NPC476127
0.7788 Intermediate Similarity NPC121423
0.7778 Intermediate Similarity NPC472125
0.7778 Intermediate Similarity NPC119550
0.7778 Intermediate Similarity NPC472124
0.7778 Intermediate Similarity NPC472126
0.7778 Intermediate Similarity NPC302584
0.7768 Intermediate Similarity NPC471548
0.7768 Intermediate Similarity NPC45475
0.7766 Intermediate Similarity NPC20072
0.7759 Intermediate Similarity NPC297950
0.7757 Intermediate Similarity NPC48548
0.7757 Intermediate Similarity NPC217921
0.7757 Intermediate Similarity NPC135015
0.7757 Intermediate Similarity NPC128795
0.7755 Intermediate Similarity NPC309310
0.7745 Intermediate Similarity NPC240372
0.7727 Intermediate Similarity NPC62696
0.7727 Intermediate Similarity NPC477944
0.7727 Intermediate Similarity NPC260665
0.7727 Intermediate Similarity NPC264153
0.7727 Intermediate Similarity NPC293038
0.7714 Intermediate Similarity NPC474581
0.7714 Intermediate Similarity NPC475367
0.7714 Intermediate Similarity NPC473816
0.7708 Intermediate Similarity NPC477746
0.7708 Intermediate Similarity NPC477747
0.77 Intermediate Similarity NPC474835
0.77 Intermediate Similarity NPC320089
0.77 Intermediate Similarity NPC472195
0.77 Intermediate Similarity NPC472196
0.77 Intermediate Similarity NPC238090
0.7699 Intermediate Similarity NPC122971
0.7692 Intermediate Similarity NPC476611
0.7692 Intermediate Similarity NPC285231
0.7692 Intermediate Similarity NPC470516
0.7692 Intermediate Similarity NPC21568
0.7685 Intermediate Similarity NPC40728
0.7685 Intermediate Similarity NPC316974
0.7679 Intermediate Similarity NPC309433
0.7677 Intermediate Similarity NPC270908
0.7677 Intermediate Similarity NPC120021
0.7677 Intermediate Similarity NPC470573
0.7677 Intermediate Similarity NPC231710
0.7677 Intermediate Similarity NPC303451
0.7677 Intermediate Similarity NPC307699
0.7677 Intermediate Similarity NPC6414
0.7677 Intermediate Similarity NPC216826
0.7677 Intermediate Similarity NPC65665
0.7672 Intermediate Similarity NPC318135
0.767 Intermediate Similarity NPC472015
0.7664 Intermediate Similarity NPC125423
0.7664 Intermediate Similarity NPC293512
0.7664 Intermediate Similarity NPC184512
0.7664 Intermediate Similarity NPC88013
0.7658 Intermediate Similarity NPC102088
0.7658 Intermediate Similarity NPC74727
0.7647 Intermediate Similarity NPC306041
0.7642 Intermediate Similarity NPC110656
0.7642 Intermediate Similarity NPC121566
0.7642 Intermediate Similarity NPC470768
0.7642 Intermediate Similarity NPC203354
0.7642 Intermediate Similarity NPC473127
0.7642 Intermediate Similarity NPC100955
0.7636 Intermediate Similarity NPC210420
0.7636 Intermediate Similarity NPC474265
0.7632 Intermediate Similarity NPC470312
0.7627 Intermediate Similarity NPC112492
0.7627 Intermediate Similarity NPC472270
0.7627 Intermediate Similarity NPC23020
0.7627 Intermediate Similarity NPC220838
0.7627 Intermediate Similarity NPC245094
0.7627 Intermediate Similarity NPC472268
0.7627 Intermediate Similarity NPC45606
0.7627 Intermediate Similarity NPC472269
0.7624 Intermediate Similarity NPC159698
0.7619 Intermediate Similarity NPC150463
0.7619 Intermediate Similarity NPC214277
0.7619 Intermediate Similarity NPC13171
0.7619 Intermediate Similarity NPC195510
0.7615 Intermediate Similarity NPC59804
0.7615 Intermediate Similarity NPC270667
0.7615 Intermediate Similarity NPC78046
0.7615 Intermediate Similarity NPC46407
0.7615 Intermediate Similarity NPC154856
0.7615 Intermediate Similarity NPC475296
0.7615 Intermediate Similarity NPC136877
0.7615 Intermediate Similarity NPC56713
0.7615 Intermediate Similarity NPC29069
0.7615 Intermediate Similarity NPC90856
0.7615 Intermediate Similarity NPC174679
0.7615 Intermediate Similarity NPC52241
0.7615 Intermediate Similarity NPC475317
0.7615 Intermediate Similarity NPC269095
0.7615 Intermediate Similarity NPC127056
0.7615 Intermediate Similarity NPC164194
0.7615 Intermediate Similarity NPC474589
0.7615 Intermediate Similarity NPC279554
0.7611 Intermediate Similarity NPC291564
0.7611 Intermediate Similarity NPC470515
0.7611 Intermediate Similarity NPC13710
0.7604 Intermediate Similarity NPC475035
0.76 Intermediate Similarity NPC472197
0.7596 Intermediate Similarity NPC255677
0.7596 Intermediate Similarity NPC64348
0.7596 Intermediate Similarity NPC306344
0.7596 Intermediate Similarity NPC22149
0.7593 Intermediate Similarity NPC193765
0.7593 Intermediate Similarity NPC473807
0.7593 Intermediate Similarity NPC311223
0.7589 Intermediate Similarity NPC473126
0.7589 Intermediate Similarity NPC207637
0.7589 Intermediate Similarity NPC31797
0.7576 Intermediate Similarity NPC285588
0.7573 Intermediate Similarity NPC266842
0.7573 Intermediate Similarity NPC476613
0.7573 Intermediate Similarity NPC476612
0.7573 Intermediate Similarity NPC472290
0.757 Intermediate Similarity NPC470763
0.757 Intermediate Similarity NPC63023

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC198422 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
0.8447 Intermediate Similarity NPD6686 Approved
0.8 Intermediate Similarity NPD6412 Phase 2
0.75 Intermediate Similarity NPD46 Approved
0.75 Intermediate Similarity NPD6698 Approved
0.7333 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD7507 Approved
0.7288 Intermediate Similarity NPD8328 Phase 3
0.7265 Intermediate Similarity NPD7503 Approved
0.7207 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD8294 Approved
0.7179 Intermediate Similarity NPD8377 Approved
0.7155 Intermediate Similarity NPD7328 Approved
0.7155 Intermediate Similarity NPD7327 Approved
0.7131 Intermediate Similarity NPD7319 Approved
0.7119 Intermediate Similarity NPD8033 Approved
0.7119 Intermediate Similarity NPD8516 Approved
0.7119 Intermediate Similarity NPD8296 Approved
0.7119 Intermediate Similarity NPD8517 Approved
0.7119 Intermediate Similarity NPD8513 Phase 3
0.7119 Intermediate Similarity NPD8380 Approved
0.7119 Intermediate Similarity NPD8335 Approved
0.7119 Intermediate Similarity NPD8515 Approved
0.7119 Intermediate Similarity NPD8379 Approved
0.7119 Intermediate Similarity NPD8378 Approved
0.7105 Intermediate Similarity NPD8133 Approved
0.7094 Intermediate Similarity NPD7516 Approved
0.708 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.6917 Remote Similarity NPD6370 Approved
0.69 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6852 Remote Similarity NPD7638 Approved
0.6827 Remote Similarity NPD7838 Discovery
0.68 Remote Similarity NPD6110 Phase 1
0.6789 Remote Similarity NPD7639 Approved
0.6789 Remote Similarity NPD7640 Approved
0.678 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6754 Remote Similarity NPD4061 Clinical (unspecified phase)
0.675 Remote Similarity NPD6054 Approved
0.6721 Remote Similarity NPD7830 Approved
0.6721 Remote Similarity NPD7829 Approved
0.664 Remote Similarity NPD7736 Approved
0.6639 Remote Similarity NPD7115 Discovery
0.6612 Remote Similarity NPD6059 Approved
0.6604 Remote Similarity NPD7983 Approved
0.6585 Remote Similarity NPD6067 Discontinued
0.6581 Remote Similarity NPD6882 Approved
0.656 Remote Similarity NPD8293 Discontinued
0.656 Remote Similarity NPD8074 Phase 3
0.6557 Remote Similarity NPD6016 Approved
0.6557 Remote Similarity NPD6015 Approved
0.6552 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6552 Remote Similarity NPD6371 Approved
0.6545 Remote Similarity NPD4225 Approved
0.6532 Remote Similarity NPD7492 Approved
0.6522 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6504 Remote Similarity NPD5988 Approved
0.65 Remote Similarity NPD6009 Approved
0.648 Remote Similarity NPD6616 Approved
0.6475 Remote Similarity NPD6319 Approved
0.6452 Remote Similarity NPD7642 Approved
0.6449 Remote Similarity NPD6411 Approved
0.6446 Remote Similarity NPD7641 Discontinued
0.6441 Remote Similarity NPD8297 Approved
0.6441 Remote Similarity NPD6053 Discontinued
0.6429 Remote Similarity NPD7078 Approved
0.6429 Remote Similarity NPD5344 Discontinued
0.6423 Remote Similarity NPD8444 Approved
0.6389 Remote Similarity NPD5779 Approved
0.6389 Remote Similarity NPD5778 Approved
0.6387 Remote Similarity NPD4632 Approved
0.6357 Remote Similarity NPD7260 Phase 2
0.6349 Remote Similarity NPD8451 Approved
0.633 Remote Similarity NPD7748 Approved
0.633 Remote Similarity NPD5282 Discontinued
0.6306 Remote Similarity NPD7902 Approved
0.6306 Remote Similarity NPD6083 Phase 2
0.6306 Remote Similarity NPD6084 Phase 2
0.6299 Remote Similarity NPD8448 Approved
0.6296 Remote Similarity NPD7637 Suspended
0.6296 Remote Similarity NPD7515 Phase 2
0.6293 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6293 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6279 Remote Similarity NPD8391 Approved
0.6279 Remote Similarity NPD8390 Approved
0.6279 Remote Similarity NPD8392 Approved
0.6262 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6262 Remote Similarity NPD6101 Approved
0.625 Remote Similarity NPD3666 Approved
0.625 Remote Similarity NPD3133 Approved
0.625 Remote Similarity NPD3665 Phase 1
0.6239 Remote Similarity NPD6399 Phase 3
0.6239 Remote Similarity NPD6881 Approved
0.6239 Remote Similarity NPD6899 Approved
0.6228 Remote Similarity NPD7632 Discontinued
0.6218 Remote Similarity NPD6649 Approved
0.6218 Remote Similarity NPD6650 Approved
0.6216 Remote Similarity NPD7839 Suspended
0.6214 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6207 Remote Similarity NPD6675 Approved
0.6207 Remote Similarity NPD7128 Approved
0.6207 Remote Similarity NPD5739 Approved
0.6207 Remote Similarity NPD6402 Approved
0.6204 Remote Similarity NPD5785 Approved
0.6186 Remote Similarity NPD6372 Approved
0.6186 Remote Similarity NPD6373 Approved
0.6176 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6914 Discontinued
0.6154 Remote Similarity NPD5956 Approved
0.6154 Remote Similarity NPD5697 Approved
0.6147 Remote Similarity NPD6079 Approved
0.6142 Remote Similarity NPD8340 Approved
0.6142 Remote Similarity NPD8342 Approved
0.6142 Remote Similarity NPD8341 Approved
0.6142 Remote Similarity NPD8299 Approved
0.6139 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6134 Remote Similarity NPD7102 Approved
0.6134 Remote Similarity NPD7290 Approved
0.6134 Remote Similarity NPD4634 Approved
0.6134 Remote Similarity NPD6883 Approved
0.6132 Remote Similarity NPD7521 Approved
0.6132 Remote Similarity NPD5330 Approved
0.6132 Remote Similarity NPD6684 Approved
0.6132 Remote Similarity NPD7334 Approved
0.6132 Remote Similarity NPD6409 Approved
0.6132 Remote Similarity NPD7146 Approved
0.6132 Remote Similarity NPD5279 Phase 3
0.6132 Remote Similarity NPD3618 Phase 1
0.6126 Remote Similarity NPD5695 Phase 3
0.6126 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6124 Remote Similarity NPD8336 Approved
0.6124 Remote Similarity NPD6033 Approved
0.6124 Remote Similarity NPD8337 Approved
0.6121 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6111 Remote Similarity NPD5328 Approved
0.6111 Remote Similarity NPD4753 Phase 2
0.6102 Remote Similarity NPD7320 Approved
0.6098 Remote Similarity NPD7500 Approved
0.6095 Remote Similarity NPD4786 Approved
0.6087 Remote Similarity NPD5211 Phase 2
0.6083 Remote Similarity NPD6617 Approved
0.6083 Remote Similarity NPD6847 Approved
0.6083 Remote Similarity NPD6869 Approved
0.6083 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6083 Remote Similarity NPD8130 Phase 1
0.6075 Remote Similarity NPD4250 Approved
0.6075 Remote Similarity NPD4251 Approved
0.6063 Remote Similarity NPD7604 Phase 2
0.6058 Remote Similarity NPD5209 Approved
0.6058 Remote Similarity NPD3667 Approved
0.6053 Remote Similarity NPD5286 Approved
0.6053 Remote Similarity NPD6648 Approved
0.6053 Remote Similarity NPD5285 Approved
0.6053 Remote Similarity NPD4696 Approved
0.605 Remote Similarity NPD6013 Approved
0.605 Remote Similarity NPD6014 Approved
0.605 Remote Similarity NPD6012 Approved
0.6038 Remote Similarity NPD1694 Approved
0.6036 Remote Similarity NPD7900 Approved
0.6036 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6032 Remote Similarity NPD5983 Phase 2
0.6032 Remote Similarity NPD6921 Approved
0.6019 Remote Similarity NPD6903 Approved
0.6019 Remote Similarity NPD4695 Discontinued
0.6019 Remote Similarity NPD5737 Approved
0.6019 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6672 Approved
0.6019 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6018 Remote Similarity NPD4755 Approved
0.6017 Remote Similarity NPD5701 Approved
0.6 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6 Remote Similarity NPD8039 Approved
0.5984 Remote Similarity NPD8080 Discontinued
0.5983 Remote Similarity NPD5141 Approved
0.5982 Remote Similarity NPD5210 Approved
0.5982 Remote Similarity NPD4629 Approved
0.5981 Remote Similarity NPD4519 Discontinued
0.5981 Remote Similarity NPD4249 Approved
0.5981 Remote Similarity NPD4623 Approved
0.5969 Remote Similarity NPD6336 Discontinued
0.5966 Remote Similarity NPD6011 Approved
0.5965 Remote Similarity NPD5696 Approved
0.5948 Remote Similarity NPD4633 Approved
0.5948 Remote Similarity NPD5224 Approved
0.5948 Remote Similarity NPD5226 Approved
0.5948 Remote Similarity NPD5225 Approved
0.5946 Remote Similarity NPD4202 Approved
0.594 Remote Similarity NPD6845 Suspended
0.5929 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5929 Remote Similarity NPD5222 Approved
0.5929 Remote Similarity NPD5221 Approved
0.5926 Remote Similarity NPD7524 Approved
0.5913 Remote Similarity NPD4700 Approved
0.5909 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5905 Remote Similarity NPD6435 Approved
0.5897 Remote Similarity NPD5175 Approved
0.5897 Remote Similarity NPD5174 Approved
0.5877 Remote Similarity NPD5173 Approved
0.5868 Remote Similarity NPD6421 Discontinued
0.5862 Remote Similarity NPD5223 Approved
0.5856 Remote Similarity NPD5284 Approved
0.5856 Remote Similarity NPD5281 Approved

Structure

External Identifiers

PubChem CID   53355015
ChEMBL   CHEMBL1813013
ZINC  

Physicochemical Properties

Molecular Weight:  516.26
ALogP:  -1.4942
MLogP:  3
XLogP:  0.237
# Rotatable Bonds:  18
Polar Surface Area:  175.37
# H-Bond Aceptor:  11
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  36

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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