Natural Product: NPC327373

Natural Product ID:  NPC327373
Common Name:   Lonijaposide L
IUPAC Name:   (2S,3R,4S)-4-[(E)-2-[1-(2-carboxyethyl)pyridin-1-ium-3-yl]ethenyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
Synonyms:   Lonijaposide L
Molecular Formula:   C24H29NO11
Standard InCHIKey:  ONSYQRQUUDJRLS-IRTUFKDUSA-N
Standard InCHI:  InChI=1S/C24H29NO11/c1-2-14-15(6-5-13-4-3-8-25(10-13)9-7-18(27)28)16(22(32)33)12-34-23(14)36-24-21(31)20(30)19(29)17(11-26)35-24/h2-6,8,10,12,14-15,17,19-21,23-24,26,29-31H,1,7,9,11H2,(H-,27,28,32,33)/b6-5+/t14-,15+,17-,19-,20+,21-,23+,24+/m1/s1
Canonical SMILES:  C=C[C@H]1[C@@H](OC=C([C@H]1/C=C/c1ccc[n+](c1)CCC(=O)O)C(=O)[O-])O[C@@H]1O[C@H](CO)[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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds PMID[21942812]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Inhibition < 30 % 21942812

  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 NPC327373 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
0.9756 High Similarity NPC322043
0.9756 High Similarity NPC325093
0.9639 High Similarity NPC318020
0.9524 High Similarity NPC325775
0.9524 High Similarity NPC328798
0.9467 High Similarity NPC182814
0.9357 High Similarity NPC127647
0.8989 High Similarity NPC50997
0.8989 High Similarity NPC160127
0.8983 High Similarity NPC329024
0.8977 High Similarity NPC20593
0.8933 High Similarity NPC324245
0.8933 High Similarity NPC59033
0.8933 High Similarity NPC317672
0.8933 High Similarity NPC320748
0.8833 High Similarity NPC79223
0.8785 High Similarity NPC32451
0.8681 High Similarity NPC328559
0.8641 High Similarity NPC25442
0.8641 High Similarity NPC12944
0.8548 High Similarity NPC156044
0.8325 Intermediate Similarity NPC111732
0.8105 Intermediate Similarity NPC309498
0.7692 Intermediate Similarity NPC317010
0.7677 Intermediate Similarity NPC292517
0.7629 Intermediate Similarity NPC476115
0.7614 Intermediate Similarity NPC472752
0.7612 Intermediate Similarity NPC162812
0.7571 Intermediate Similarity NPC474217
0.7562 Intermediate Similarity NPC30570
0.7514 Intermediate Similarity NPC71079
0.7513 Intermediate Similarity NPC474905
0.7475 Intermediate Similarity NPC476114
0.7475 Intermediate Similarity NPC477910
0.743 Intermediate Similarity NPC85918
0.7424 Intermediate Similarity NPC475835
0.7413 Intermediate Similarity NPC472553
0.7413 Intermediate Similarity NPC476467
0.7402 Intermediate Similarity NPC82070
0.7389 Intermediate Similarity NPC127730
0.7389 Intermediate Similarity NPC278366
0.7387 Intermediate Similarity NPC63041
0.7353 Intermediate Similarity NPC475408
0.7353 Intermediate Similarity NPC471014
0.735 Intermediate Similarity NPC472550
0.735 Intermediate Similarity NPC304179
0.735 Intermediate Similarity NPC48042
0.7317 Intermediate Similarity NPC144779
0.7317 Intermediate Similarity NPC294579
0.7304 Intermediate Similarity NPC470306
0.7282 Intermediate Similarity NPC472555
0.7282 Intermediate Similarity NPC52254
0.7268 Intermediate Similarity NPC6981
0.7268 Intermediate Similarity NPC471016
0.726 Intermediate Similarity NPC477911
0.7255 Intermediate Similarity NPC319128
0.7255 Intermediate Similarity NPC228331
0.7247 Intermediate Similarity NPC138018
0.7233 Intermediate Similarity NPC174788
0.7233 Intermediate Similarity NPC62367
0.7232 Intermediate Similarity NPC263455
0.7225 Intermediate Similarity NPC475271
0.7212 Intermediate Similarity NPC477912
0.7204 Intermediate Similarity NPC124029
0.7204 Intermediate Similarity NPC211920
0.7198 Intermediate Similarity NPC216428
0.7198 Intermediate Similarity NPC301368
0.7198 Intermediate Similarity NPC84815
0.719 Intermediate Similarity NPC233727
0.719 Intermediate Similarity NPC477902
0.7186 Intermediate Similarity NPC322488
0.7184 Intermediate Similarity NPC477908
0.7184 Intermediate Similarity NPC206343
0.7156 Intermediate Similarity NPC148860
0.7143 Intermediate Similarity NPC471980
0.7143 Intermediate Similarity NPC477975
0.7136 Intermediate Similarity NPC42678
0.7136 Intermediate Similarity NPC477907
0.7136 Intermediate Similarity NPC477909
0.7122 Intermediate Similarity NPC165837
0.7114 Intermediate Similarity NPC238457
0.7111 Intermediate Similarity NPC472435
0.7109 Intermediate Similarity NPC475137
0.7109 Intermediate Similarity NPC475498
0.7109 Intermediate Similarity NPC473850
0.7109 Intermediate Similarity NPC328154
0.7103 Intermediate Similarity NPC477906
0.7095 Intermediate Similarity NPC127026
0.7095 Intermediate Similarity NPC127720
0.7094 Intermediate Similarity NPC477548
0.7087 Intermediate Similarity NPC264674
0.7075 Intermediate Similarity NPC473506
0.7073 Intermediate Similarity NPC323551
0.7073 Intermediate Similarity NPC280473
0.7068 Intermediate Similarity NPC62510
0.7065 Intermediate Similarity NPC319456
0.7062 Intermediate Similarity NPC250807
0.7062 Intermediate Similarity NPC57797
0.7062 Intermediate Similarity NPC76565
0.7053 Intermediate Similarity NPC207531
0.7042 Intermediate Similarity NPC475601
0.7039 Intermediate Similarity NPC41724
0.7039 Intermediate Similarity NPC51008
0.7037 Intermediate Similarity NPC471997
0.7024 Intermediate Similarity NPC40919
0.7024 Intermediate Similarity NPC470189
0.7023 Intermediate Similarity NPC150698
0.7023 Intermediate Similarity NPC96801
0.702 Intermediate Similarity NPC149708
0.7018 Intermediate Similarity NPC472436
0.7009 Intermediate Similarity NPC475644
0.7009 Intermediate Similarity NPC475362
0.7009 Intermediate Similarity NPC471190
0.7009 Intermediate Similarity NPC470486
0.7009 Intermediate Similarity NPC471977
0.7005 Intermediate Similarity NPC313640
0.7005 Intermediate Similarity NPC170751
0.7005 Intermediate Similarity NPC4421
0.6991 Remote Similarity NPC469748
0.699 Remote Similarity NPC244856
0.6989 Remote Similarity NPC249614
0.6986 Remote Similarity NPC319556
0.6983 Remote Similarity NPC312860
0.6983 Remote Similarity NPC107287
0.698 Remote Similarity NPC289086
0.6971 Remote Similarity NPC193361
0.6971 Remote Similarity NPC62844
0.6963 Remote Similarity NPC87152
0.6963 Remote Similarity NPC328186
0.6963 Remote Similarity NPC228377
0.6963 Remote Similarity NPC146824
0.6963 Remote Similarity NPC475631
0.6963 Remote Similarity NPC122968
0.6963 Remote Similarity NPC477787
0.6963 Remote Similarity NPC475600
0.6963 Remote Similarity NPC476110
0.6961 Remote Similarity NPC470190
0.6957 Remote Similarity NPC306644
0.6957 Remote Similarity NPC236424
0.6932 Remote Similarity NPC167400
0.6923 Remote Similarity NPC274842
0.6923 Remote Similarity NPC99891
0.6919 Remote Similarity NPC109922
0.6912 Remote Similarity NPC30456
0.6906 Remote Similarity NPC472434
0.6906 Remote Similarity NPC476090
0.6905 Remote Similarity NPC158020
0.6905 Remote Similarity NPC212768
0.6905 Remote Similarity NPC187494
0.6905 Remote Similarity NPC473115
0.6905 Remote Similarity NPC75600
0.6905 Remote Similarity NPC473089
0.6905 Remote Similarity NPC6576
0.6904 Remote Similarity NPC103230
0.69 Remote Similarity NPC474767
0.6891 Remote Similarity NPC133591
0.6888 Remote Similarity NPC114974
0.6887 Remote Similarity NPC477903
0.6881 Remote Similarity NPC237702
0.6875 Remote Similarity NPC230085
0.6875 Remote Similarity NPC471323
0.6875 Remote Similarity NPC221100
0.6875 Remote Similarity NPC234078
0.6875 Remote Similarity NPC159630
0.6872 Remote Similarity NPC75544
0.6869 Remote Similarity NPC26881
0.6866 Remote Similarity NPC316841
0.6866 Remote Similarity NPC292416
0.6866 Remote Similarity NPC473689
0.6866 Remote Similarity NPC475596
0.6866 Remote Similarity NPC475303
0.686 Remote Similarity NPC29702
0.6856 Remote Similarity NPC38823
0.6856 Remote Similarity NPC207033
0.6856 Remote Similarity NPC291759
0.6854 Remote Similarity NPC235364
0.6849 Remote Similarity NPC35208
0.6849 Remote Similarity NPC475426
0.6849 Remote Similarity NPC327769
0.684 Remote Similarity NPC477901
0.6839 Remote Similarity NPC207851
0.6835 Remote Similarity NPC320324
0.6835 Remote Similarity NPC319880
0.6835 Remote Similarity NPC244839
0.6831 Remote Similarity NPC113812
0.6821 Remote Similarity NPC114310
0.6806 Remote Similarity NPC14116
0.6806 Remote Similarity NPC285411
0.6804 Remote Similarity NPC238278
0.6802 Remote Similarity NPC472097
0.6791 Remote Similarity NPC477899
0.6791 Remote Similarity NPC477900
0.6776 Remote Similarity NPC477788
0.6774 Remote Similarity NPC311196
0.6774 Remote Similarity NPC134384
0.6773 Remote Similarity NPC475406
0.6772 Remote Similarity NPC477976
0.676 Remote Similarity NPC112741
0.6745 Remote Similarity NPC314270
0.6743 Remote Similarity NPC91125

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC327373 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
0.768 Intermediate Similarity NPD7396 Approved
0.7612 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7612 Intermediate Similarity NPD8326 Phase 3
0.7612 Intermediate Similarity NPD8325 Phase 3
0.7571 Intermediate Similarity NPD5088 Discontinued
0.7381 Intermediate Similarity NPD2896 Discontinued
0.7258 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD2544 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD8372 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD2511 Approved
0.7151 Intermediate Similarity NPD820 Phase 3
0.7135 Intermediate Similarity NPD2809 Approved
0.7052 Intermediate Similarity NPD4805 Approved
0.705 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD8468 Phase 2
0.7018 Intermediate Similarity NPD8409 Suspended
0.7005 Intermediate Similarity NPD5322 Clinical (unspecified phase)
0.6995 Remote Similarity NPD6635 Approved
0.6984 Remote Similarity NPD8037 Clinical (unspecified phase)
0.6984 Remote Similarity NPD8036 Clinical (unspecified phase)
0.6977 Remote Similarity NPD203 Clinical (unspecified phase)
0.6971 Remote Similarity NPD751 Clinical (unspecified phase)
0.6959 Remote Similarity NPD7234 Approved
0.6959 Remote Similarity NPD7233 Approved
0.6954 Remote Similarity NPD4427 Phase 2
0.6936 Remote Similarity NPD4804 Approved
0.6932 Remote Similarity NPD9075 Approved
0.6932 Remote Similarity NPD9074 Approved
0.6927 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6927 Remote Similarity NPD6529 Discontinued
0.6898 Remote Similarity NPD485 Clinical (unspecified phase)
0.6887 Remote Similarity NPD6298 Discontinued
0.6879 Remote Similarity NPD1380 Discovery
0.6875 Remote Similarity NPD3794 Approved
0.6875 Remote Similarity NPD3795 Approved
0.684 Remote Similarity NPD8479 Phase 2
0.6834 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6828 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6818 Remote Similarity NPD4526 Approved
0.6818 Remote Similarity NPD4529 Approved
0.6818 Remote Similarity NPD4528 Approved
0.6813 Remote Similarity NPD6026 Approved
0.6809 Remote Similarity NPD6739 Clinical (unspecified phase)
0.6802 Remote Similarity NPD1977 Clinical (unspecified phase)
0.68 Remote Similarity NPD107 Approved
0.6778 Remote Similarity NPD7913 Clinical (unspecified phase)
0.6772 Remote Similarity NPD43 Approved
0.6772 Remote Similarity NPD6183 Clinical (unspecified phase)
0.6772 Remote Similarity NPD6182 Approved
0.6771 Remote Similarity NPD5897 Approved
0.6771 Remote Similarity NPD5899 Approved
0.6771 Remote Similarity NPD5898 Approved
0.6769 Remote Similarity NPD8370 Discontinued
0.6761 Remote Similarity NPD1382 Phase 2
0.6761 Remote Similarity NPD1383 Phase 3
0.676 Remote Similarity NPD9271 Approved
0.6757 Remote Similarity NPD4239 Clinical (unspecified phase)
0.6751 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6728 Remote Similarity NPD4086 Phase 1
0.6726 Remote Similarity NPD8375 Approved
0.6723 Remote Similarity NPD1427 Clinical (unspecified phase)
0.6702 Remote Similarity NPD5862 Discovery
0.67 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6686 Remote Similarity NPD1627 Clinical (unspecified phase)
0.6682 Remote Similarity NPD3280 Approved
0.6667 Remote Similarity NPD8063 Discontinued
0.6667 Remote Similarity NPD9206 Approved
0.6667 Remote Similarity NPD8371 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9207 Approved
0.665 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6649 Remote Similarity NPD8408 Discontinued
0.6648 Remote Similarity NPD510 Phase 1
0.6633 Remote Similarity NPD2336 Approved
0.6629 Remote Similarity NPD9506 Approved
0.6618 Remote Similarity NPD4500 Approved
0.6618 Remote Similarity NPD4501 Approved
0.6618 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6616 Remote Similarity NPD4021 Phase 2
0.6606 Remote Similarity NPD5640 Discontinued
0.6604 Remote Similarity NPD5149 Phase 2
0.6604 Remote Similarity NPD5148 Clinical (unspecified phase)
0.6601 Remote Similarity NPD7778 Approved
0.6601 Remote Similarity NPD7777 Approved
0.6601 Remote Similarity NPD53 Approved
0.6592 Remote Similarity NPD3813 Approved
0.6588 Remote Similarity NPD7069 Discontinued
0.6587 Remote Similarity NPD7562 Approved
0.6585 Remote Similarity NPD3911 Approved
0.6583 Remote Similarity NPD3321 Discontinued
0.658 Remote Similarity NPD6641 Approved
0.658 Remote Similarity NPD6642 Approved
0.6579 Remote Similarity NPD8291 Clinical (unspecified phase)
0.6575 Remote Similarity NPD4702 Approved
0.6575 Remote Similarity NPD4703 Approved
0.657 Remote Similarity NPD2831 Approved
0.6567 Remote Similarity NPD8373 Clinical (unspecified phase)
0.6566 Remote Similarity NPD8020 Approved
0.6566 Remote Similarity NPD8021 Approved
0.6564 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6559 Remote Similarity NPD5255 Approved
0.6553 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6552 Remote Similarity NPD6206 Phase 1
0.6548 Remote Similarity NPD4889 Approved
0.6542 Remote Similarity NPD4989 Phase 2
0.6535 Remote Similarity NPD5975 Clinical (unspecified phase)
0.6533 Remote Similarity NPD4334 Discontinued
0.6519 Remote Similarity NPD6148 Clinical (unspecified phase)
0.6517 Remote Similarity NPD4376 Phase 3
0.6517 Remote Similarity NPD5505 Discontinued
0.6517 Remote Similarity NPD1649 Discontinued
0.6517 Remote Similarity NPD6665 Discontinued
0.6516 Remote Similarity NPD8374 Phase 3
0.6515 Remote Similarity NPD4375 Approved
0.6512 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6505 Remote Similarity NPD2581 Approved
0.6505 Remote Similarity NPD2582 Approved
0.6502 Remote Similarity NPD2307 Discontinued
0.6497 Remote Similarity NPD6178 Phase 3
0.6495 Remote Similarity NPD8123 Approved
0.6495 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6495 Remote Similarity NPD8122 Approved
0.6491 Remote Similarity NPD9284 Approved
0.6486 Remote Similarity NPD2061 Approved
0.6485 Remote Similarity NPD6361 Phase 2
0.6484 Remote Similarity NPD1270 Approved
0.6474 Remote Similarity NPD5611 Phase 2
0.6473 Remote Similarity NPD8329 Phase 3
0.6468 Remote Similarity NPD3785 Clinical (unspecified phase)
0.6456 Remote Similarity NPD6479 Discontinued
0.645 Remote Similarity NPD6068 Discontinued
0.6447 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6444 Remote Similarity NPD3717 Discontinued
0.644 Remote Similarity NPD4639 Approved
0.644 Remote Similarity NPD4640 Approved
0.644 Remote Similarity NPD4638 Approved
0.6436 Remote Similarity NPD6569 Phase 2
0.6432 Remote Similarity NPD180 Clinical (unspecified phase)
0.6422 Remote Similarity NPD6226 Phase 3
0.642 Remote Similarity NPD272 Approved
0.6419 Remote Similarity NPD3393 Approved
0.6419 Remote Similarity NPD3389 Approved
0.6419 Remote Similarity NPD3394 Approved
0.6415 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6414 Remote Similarity NPD1096 Discontinued
0.6411 Remote Similarity NPD4038 Approved
0.6411 Remote Similarity NPD4036 Approved
0.6411 Remote Similarity NPD4122 Approved
0.6411 Remote Similarity NPD4037 Approved
0.6411 Remote Similarity NPD4034 Approved
0.6411 Remote Similarity NPD4039 Approved
0.6411 Remote Similarity NPD32 Approved
0.6411 Remote Similarity NPD4033 Approved
0.6411 Remote Similarity NPD31 Approved
0.6411 Remote Similarity NPD4035 Approved
0.64 Remote Similarity NPD6257 Clinical (unspecified phase)
0.6398 Remote Similarity NPD2510 Approved
0.6398 Remote Similarity NPD2509 Approved
0.6396 Remote Similarity NPD3386 Phase 2
0.6395 Remote Similarity NPD9080 Approved
0.6394 Remote Similarity NPD7561 Approved
0.6393 Remote Similarity NPD8356 Approved
0.6382 Remote Similarity NPD5555 Phase 1
0.6378 Remote Similarity NPD1620 Clinical (unspecified phase)
0.6378 Remote Similarity NPD3262 Approved
0.6373 Remote Similarity NPD7944 Discontinued
0.6364 Remote Similarity NPD5213 Clinical (unspecified phase)
0.6364 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6364 Remote Similarity NPD8072 Approved
0.6364 Remote Similarity NPD5487 Phase 1
0.6359 Remote Similarity NPD6261 Phase 3
0.6355 Remote Similarity NPD4315 Phase 2
0.6354 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6354 Remote Similarity NPD2781 Approved
0.6347 Remote Similarity NPD4301 Approved
0.6345 Remote Similarity NPD1618 Phase 2
0.6338 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6338 Remote Similarity NPD8321 Discontinued
0.6337 Remote Similarity NPD6281 Approved
0.6335 Remote Similarity NPD2782 Approved
0.6335 Remote Similarity NPD2780 Approved
0.6333 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6332 Remote Similarity NPD3569 Discontinued
0.6329 Remote Similarity NPD6249 Phase 2
0.6329 Remote Similarity NPD6248 Phase 2
0.6321 Remote Similarity NPD1573 Approved
0.6321 Remote Similarity NPD1575 Approved
0.6319 Remote Similarity NPD1352 Discontinued
0.6313 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6306 Remote Similarity NPD7426 Phase 1
0.6303 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6303 Remote Similarity NPD7957 Phase 1
0.6303 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6303 Remote Similarity NPD7010 Phase 3
0.6301 Remote Similarity NPD2118 Approved
0.6301 Remote Similarity NPD2119 Approved
0.63 Remote Similarity NPD3082 Discontinued
0.6298 Remote Similarity NPD5228 Phase 3
0.6298 Remote Similarity NPD5020 Approved
0.6288 Remote Similarity NPD7886 Phase 2
0.6288 Remote Similarity NPD7885 Phase 2

Structure

External Identifiers

PubChem CID   56599872
ChEMBL   CHEMBL1928050
ZINC  

Physicochemical Properties

Molecular Weight:  507.17
ALogP:  -4.2945
MLogP:  2.78
XLogP:  0.03
# Rotatable Bonds:  16
Polar Surface Area:  189.92
# H-Bond Aceptor:  11
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  36

Download Data

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Biological Activities  
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