Natural Product: NPC188555

Natural Product ID:  NPC188555
Common Name:   Lysidiside M
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R)-4,5-dihydroxy-2-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:   lysidiside M
Molecular Formula:   C25H30O12
Standard InCHIKey:  KTSPZJPSJGQOIQ-YKULTYPDSA-N
Standard InCHI:  InChI=1S/C25H30O12/c26-10-18-20(31)21(32)22(33)24(36-18)37-23-19(30)17(29)11-34-25(23)35-16-8-13(7-15(28)9-16)2-1-12-3-5-14(27)6-4-12/h1-9,17-33H,10-11H2/b2-1+/t17-,18-,19+,20-,21+,22-,23-,24+,25+/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC[C@H]([C@@H]2O)O)Oc2cc(O)cc(c2)/C=C/c2ccc(cc2)O)[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
NPO33047 lysidice brevicalyx wei Species NA Eukaryota Barks PMID[18847246]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Activity = 5 % 22394155
NPT2 Others Unspecified Activity = 29 % 24211635

  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 NPC188555 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 NPC130496
0.9922 High Similarity NPC238243
0.9845 High Similarity NPC40664
0.9845 High Similarity NPC197723
0.9845 High Similarity NPC165482
0.9845 High Similarity NPC138350
0.9845 High Similarity NPC3293
0.9843 High Similarity NPC303422
0.9843 High Similarity NPC26080
0.9843 High Similarity NPC85799
0.9843 High Similarity NPC165686
0.9766 High Similarity NPC294166
0.9766 High Similarity NPC115022
0.9764 High Similarity NPC121376
0.9606 High Similarity NPC218003
0.9549 High Similarity NPC257095
0.9549 High Similarity NPC89686
0.9549 High Similarity NPC273932
0.9542 High Similarity NPC203230
0.9542 High Similarity NPC242028
0.947 High Similarity NPC124149
0.947 High Similarity NPC59324
0.947 High Similarity NPC65530
0.9398 High Similarity NPC212770
0.9398 High Similarity NPC98777
0.9338 High Similarity NPC76176
0.9338 High Similarity NPC138227
0.9338 High Similarity NPC469313
0.9338 High Similarity NPC168579
0.9323 High Similarity NPC87777
0.9323 High Similarity NPC262328
0.9265 High Similarity NPC37793
0.9259 High Similarity NPC210192
0.9259 High Similarity NPC469661
0.9248 High Similarity NPC164857
0.9203 High Similarity NPC125755
0.9191 High Similarity NPC189115
0.9191 High Similarity NPC475084
0.9191 High Similarity NPC469559
0.9191 High Similarity NPC472353
0.9173 High Similarity NPC470236
0.9167 High Similarity NPC49074
0.916 High Similarity NPC475067
0.9141 High Similarity NPC12308
0.9137 High Similarity NPC473480
0.9137 High Similarity NPC15538
0.913 High Similarity NPC161700
0.913 High Similarity NPC277867
0.9124 High Similarity NPC473044
0.9124 High Similarity NPC252169
0.9091 High Similarity NPC162093
0.9071 High Similarity NPC280945
0.9058 High Similarity NPC473045
0.9058 High Similarity NPC25292
0.9051 High Similarity NPC139976
0.9051 High Similarity NPC49542
0.9051 High Similarity NPC84207
0.9051 High Similarity NPC230718
0.9051 High Similarity NPC128337
0.9051 High Similarity NPC5253
0.9044 High Similarity NPC106944
0.9037 High Similarity NPC134260
0.9023 High Similarity NPC132895
0.8993 High Similarity NPC475096
0.8978 High Similarity NPC108674
0.8955 High Similarity NPC13745
0.8955 High Similarity NPC251981
0.8955 High Similarity NPC48863
0.8947 High Similarity NPC299144
0.8939 High Similarity NPC262606
0.8929 High Similarity NPC190714
0.8929 High Similarity NPC99515
0.8921 High Similarity NPC225445
0.8897 High Similarity NPC470413
0.8897 High Similarity NPC138738
0.8889 High Similarity NPC185778
0.8881 High Similarity NPC473621
0.8881 High Similarity NPC69513
0.8881 High Similarity NPC215833
0.8872 High Similarity NPC473412
0.8872 High Similarity NPC9912
0.8872 High Similarity NPC469698
0.8865 High Similarity NPC227902
0.8865 High Similarity NPC39657
0.8864 High Similarity NPC248355
0.8849 High Similarity NPC116922
0.8824 High Similarity NPC172818
0.8824 High Similarity NPC25695
0.8815 High Similarity NPC170694
0.8815 High Similarity NPC476411
0.8815 High Similarity NPC187194
0.8815 High Similarity NPC87696
0.8815 High Similarity NPC107478
0.8806 High Similarity NPC470270
0.8803 High Similarity NPC478237
0.8803 High Similarity NPC175976
0.8794 High Similarity NPC74320
0.8794 High Similarity NPC107120
0.8788 High Similarity NPC302378
0.8788 High Similarity NPC40377
0.8786 High Similarity NPC177597
0.8786 High Similarity NPC476867
0.8777 High Similarity NPC5262
0.8777 High Similarity NPC145319
0.8777 High Similarity NPC472714
0.8759 High Similarity NPC195196
0.875 High Similarity NPC79957
0.875 High Similarity NPC269242
0.875 High Similarity NPC469412
0.875 High Similarity NPC198734
0.8741 High Similarity NPC51328
0.8741 High Similarity NPC286235
0.8741 High Similarity NPC106138
0.8741 High Similarity NPC55158
0.8723 High Similarity NPC476869
0.8723 High Similarity NPC476866
0.8723 High Similarity NPC226722
0.8723 High Similarity NPC476868
0.8723 High Similarity NPC476864
0.8722 High Similarity NPC166040
0.8722 High Similarity NPC307110
0.8705 High Similarity NPC186406
0.8696 High Similarity NPC292487
0.869 High Similarity NPC233467
0.869 High Similarity NPC169404
0.869 High Similarity NPC21902
0.869 High Similarity NPC53587
0.869 High Similarity NPC59692
0.869 High Similarity NPC176186
0.8686 High Similarity NPC177035
0.8686 High Similarity NPC166180
0.8686 High Similarity NPC104167
0.8686 High Similarity NPC199459
0.8686 High Similarity NPC52277
0.8681 High Similarity NPC238140
0.8676 High Similarity NPC35731
0.8672 High Similarity NPC469708
0.8672 High Similarity NPC60589
0.8671 High Similarity NPC130449
0.8671 High Similarity NPC248132
0.8667 High Similarity NPC7903
0.8667 High Similarity NPC16208
0.8667 High Similarity NPC35932
0.8667 High Similarity NPC184447
0.8667 High Similarity NPC160991
0.8667 High Similarity NPC254275
0.8662 High Similarity NPC155564
0.8662 High Similarity NPC248053
0.8662 High Similarity NPC476865
0.8662 High Similarity NPC102280
0.8657 High Similarity NPC80600
0.8657 High Similarity NPC472024
0.8652 High Similarity NPC472713
0.8652 High Similarity NPC187774
0.8652 High Similarity NPC292443
0.8652 High Similarity NPC118385
0.8652 High Similarity NPC473046
0.8652 High Similarity NPC472712
0.8643 High Similarity NPC157816
0.8633 High Similarity NPC210478
0.8633 High Similarity NPC202700
0.863 High Similarity NPC78809
0.863 High Similarity NPC150442
0.8626 High Similarity NPC287429
0.8623 High Similarity NPC211549
0.8621 High Similarity NPC259707
0.8615 High Similarity NPC476142
0.8613 High Similarity NPC61946
0.8613 High Similarity NPC164787
0.8611 High Similarity NPC35877
0.8611 High Similarity NPC95392
0.8611 High Similarity NPC55715
0.8603 High Similarity NPC215037
0.8603 High Similarity NPC25821
0.8601 High Similarity NPC52740
0.8593 High Similarity NPC469625
0.8593 High Similarity NPC65942
0.8593 High Similarity NPC166168
0.8593 High Similarity NPC469613
0.8593 High Similarity NPC248307
0.8593 High Similarity NPC472597
0.8593 High Similarity NPC103799
0.8593 High Similarity NPC30043
0.8592 High Similarity NPC23807
0.8582 High Similarity NPC273295
0.8582 High Similarity NPC81638
0.8582 High Similarity NPC185307
0.8582 High Similarity NPC97326
0.8582 High Similarity NPC478239
0.8582 High Similarity NPC470950
0.8582 High Similarity NPC46092
0.8582 High Similarity NPC190629
0.8582 High Similarity NPC218856
0.8582 High Similarity NPC202582
0.8582 High Similarity NPC285339
0.8582 High Similarity NPC226788
0.8582 High Similarity NPC270849
0.8582 High Similarity NPC26653
0.8582 High Similarity NPC470258
0.8582 High Similarity NPC210623

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC188555 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
0.8538 High Similarity NPD1091 Approved
0.8529 High Similarity NPD1613 Approved
0.8529 High Similarity NPD1612 Clinical (unspecified phase)
0.8356 Intermediate Similarity NPD1653 Approved
0.8309 Intermediate Similarity NPD3027 Phase 3
0.8235 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8169 Intermediate Similarity NPD7266 Discontinued
0.8162 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8158 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8102 Intermediate Similarity NPD4908 Phase 1
0.8038 Intermediate Similarity NPD7054 Approved
0.7987 Intermediate Similarity NPD7472 Approved
0.7987 Intermediate Similarity NPD7074 Phase 3
0.7986 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7985 Intermediate Similarity NPD1610 Phase 2
0.7955 Intermediate Similarity NPD1548 Phase 1
0.7937 Intermediate Similarity NPD6797 Phase 2
0.7888 Intermediate Similarity NPD7251 Discontinued
0.784 Intermediate Similarity NPD7808 Phase 3
0.7812 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD2861 Phase 2
0.775 Intermediate Similarity NPD3818 Discontinued
0.775 Intermediate Similarity NPD7228 Approved
0.773 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD8455 Phase 2
0.7687 Intermediate Similarity NPD6674 Discontinued
0.7669 Intermediate Similarity NPD6559 Discontinued
0.7651 Intermediate Similarity NPD5058 Phase 3
0.7628 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD2983 Phase 2
0.7609 Intermediate Similarity NPD2982 Phase 2
0.7548 Intermediate Similarity NPD37 Approved
0.7536 Intermediate Similarity NPD2981 Phase 2
0.7535 Intermediate Similarity NPD4625 Phase 3
0.7532 Intermediate Similarity NPD4380 Phase 2
0.7532 Intermediate Similarity NPD6234 Discontinued
0.7516 Intermediate Similarity NPD6166 Phase 2
0.7516 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD4967 Phase 2
0.7516 Intermediate Similarity NPD4965 Approved
0.7516 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD1357 Approved
0.7483 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD4749 Approved
0.7466 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD4538 Approved
0.7466 Intermediate Similarity NPD4536 Approved
0.745 Intermediate Similarity NPD1652 Phase 2
0.745 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD7199 Phase 2
0.7436 Intermediate Similarity NPD1934 Approved
0.7415 Intermediate Similarity NPD5960 Phase 3
0.7415 Intermediate Similarity NPD5588 Approved
0.7394 Intermediate Similarity NPD3018 Phase 2
0.7391 Intermediate Similarity NPD3787 Discontinued
0.7389 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7843 Approved
0.7361 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD7240 Approved
0.7342 Intermediate Similarity NPD5402 Approved
0.7338 Intermediate Similarity NPD3705 Approved
0.7333 Intermediate Similarity NPD7157 Approved
0.7329 Intermediate Similarity NPD5124 Phase 1
0.7329 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD2684 Approved
0.7323 Intermediate Similarity NPD1242 Phase 1
0.7308 Intermediate Similarity NPD968 Approved
0.7289 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD4060 Phase 1
0.7255 Intermediate Similarity NPD7212 Phase 2
0.7255 Intermediate Similarity NPD7213 Phase 3
0.7252 Intermediate Similarity NPD290 Approved
0.725 Intermediate Similarity NPD7075 Discontinued
0.7239 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD7097 Phase 1
0.7226 Intermediate Similarity NPD5403 Approved
0.7214 Intermediate Similarity NPD422 Phase 1
0.7212 Intermediate Similarity NPD3751 Discontinued
0.7208 Intermediate Similarity NPD7447 Phase 1
0.72 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD6516 Phase 2
0.7194 Intermediate Similarity NPD5846 Approved
0.7192 Intermediate Similarity NPD6233 Phase 2
0.717 Intermediate Similarity NPD2801 Approved
0.716 Intermediate Similarity NPD8313 Approved
0.716 Intermediate Similarity NPD8312 Approved
0.7152 Intermediate Similarity NPD1549 Phase 2
0.7143 Intermediate Similarity NPD7685 Pre-registration
0.7143 Intermediate Similarity NPD1511 Approved
0.7125 Intermediate Similarity NPD3817 Phase 2
0.7124 Intermediate Similarity NPD6190 Approved
0.7113 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD5401 Approved
0.7097 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD4340 Discontinued
0.7089 Intermediate Similarity NPD4678 Approved
0.7089 Intermediate Similarity NPD4675 Approved
0.7083 Intermediate Similarity NPD6584 Phase 3
0.708 Intermediate Similarity NPD6671 Approved
0.7071 Intermediate Similarity NPD5125 Phase 3
0.7071 Intermediate Similarity NPD5126 Approved
0.7067 Intermediate Similarity NPD4108 Discontinued
0.7066 Intermediate Similarity NPD5844 Phase 1
0.7063 Intermediate Similarity NPD1465 Phase 2
0.7063 Intermediate Similarity NPD8651 Approved
0.7063 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD4628 Phase 3
0.7059 Intermediate Similarity NPD3750 Approved
0.7055 Intermediate Similarity NPD7095 Approved
0.7051 Intermediate Similarity NPD1512 Approved
0.7042 Intermediate Similarity NPD2231 Phase 2
0.7042 Intermediate Similarity NPD2235 Phase 2
0.7037 Intermediate Similarity NPD228 Approved
0.7037 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD6959 Discontinued
0.7007 Intermediate Similarity NPD6798 Discontinued
0.7006 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6801 Discontinued
0.6987 Remote Similarity NPD4378 Clinical (unspecified phase)
0.698 Remote Similarity NPD5735 Approved
0.6975 Remote Similarity NPD3882 Suspended
0.6966 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6957 Remote Similarity NPD2977 Approved
0.6957 Remote Similarity NPD2978 Approved
0.6957 Remote Similarity NPD7819 Suspended
0.6948 Remote Similarity NPD4535 Phase 3
0.6948 Remote Similarity NPD3892 Phase 2
0.6944 Remote Similarity NPD3225 Approved
0.6937 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6937 Remote Similarity NPD7411 Suspended
0.6934 Remote Similarity NPD5283 Phase 1
0.6933 Remote Similarity NPD6653 Approved
0.6927 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6799 Approved
0.6914 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6913 Remote Similarity NPD1558 Phase 1
0.6908 Remote Similarity NPD1551 Phase 2
0.6908 Remote Similarity NPD6100 Approved
0.6908 Remote Similarity NPD6099 Approved
0.6903 Remote Similarity NPD2677 Approved
0.6875 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6582 Phase 2
0.6875 Remote Similarity NPD3685 Discontinued
0.6875 Remote Similarity NPD6583 Phase 3
0.6868 Remote Similarity NPD7680 Approved
0.6867 Remote Similarity NPD6355 Discontinued
0.6863 Remote Similarity NPD5763 Approved
0.6863 Remote Similarity NPD5762 Approved
0.6863 Remote Similarity NPD3540 Phase 1
0.6861 Remote Similarity NPD5535 Approved
0.6852 Remote Similarity NPD7089 Clinical (unspecified phase)
0.6848 Remote Similarity NPD5494 Approved
0.6846 Remote Similarity NPD4062 Phase 3
0.6842 Remote Similarity NPD1510 Phase 2
0.6842 Remote Similarity NPD7033 Discontinued
0.6839 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6824 Remote Similarity NPD3179 Approved
0.6824 Remote Similarity NPD3180 Approved
0.6818 Remote Similarity NPD2424 Discontinued
0.6815 Remote Similarity NPD4357 Discontinued
0.6813 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6809 Remote Similarity NPD1182 Approved
0.68 Remote Similarity NPD2238 Phase 2
0.68 Remote Similarity NPD4140 Approved
0.68 Remote Similarity NPD6841 Approved
0.68 Remote Similarity NPD5837 Clinical (unspecified phase)
0.68 Remote Similarity NPD3619 Clinical (unspecified phase)
0.68 Remote Similarity NPD3620 Phase 2
0.68 Remote Similarity NPD6843 Phase 3
0.68 Remote Similarity NPD6842 Approved
0.6797 Remote Similarity NPD3454 Phase 3
0.6797 Remote Similarity NPD3539 Phase 1
0.6797 Remote Similarity NPD2796 Approved
0.6795 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6792 Remote Similarity NPD2122 Discontinued
0.6783 Remote Similarity NPD3496 Discontinued
0.6782 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6774 Remote Similarity NPD5061 Approved
0.6774 Remote Similarity NPD5062 Approved
0.6774 Remote Similarity NPD3060 Approved
0.6772 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6772 Remote Similarity NPD3536 Discontinued
0.6772 Remote Similarity NPD4123 Phase 3
0.6768 Remote Similarity NPD7768 Phase 2
0.6761 Remote Similarity NPD5585 Approved
0.6759 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6755 Remote Similarity NPD230 Phase 1
0.6753 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6753 Remote Similarity NPD1375 Discontinued
0.6742 Remote Similarity NPD291 Approved
0.6741 Remote Similarity NPD1358 Approved
0.6738 Remote Similarity NPD5536 Phase 2
0.6736 Remote Similarity NPD1535 Discovery
0.6732 Remote Similarity NPD3748 Approved
0.6731 Remote Similarity NPD7466 Approved

Structure

External Identifiers

PubChem CID   25155595
ChEMBL   CHEMBL573408
ZINC  

Physicochemical Properties

Molecular Weight:  522.17
ALogP:  -3.8962
MLogP:  2.89
XLogP:  1.034
# Rotatable Bonds:  15
Polar Surface Area:  198.76
# H-Bond Aceptor:  9
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  37

Download Data

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