Natural Product: NPC476301

Natural Product ID:  NPC476301
Common Name:   4-O-Rhamnosyl-7S,8R-7',8'-Erythro-Sismbrifolin
IUPAC Name:   (2S,3R,4R,5R,6S)-2-[4-[(2S,3R)-3-(hydroxymethyl)-7-methoxy-5-[(1R,2S)-1,2,3-trihydroxypropyl]-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]-6-methyloxane-3,4,5-triol
Synonyms:  
Molecular Formula:   C26H34O12
Standard InCHIKey:  NQHFIYPUIVKCLI-KNJWWJHHSA-N
Standard InCHI:  InChI=1S/C26H34O12/c1-11-20(30)22(32)23(33)26(36-11)37-17-5-4-12(7-18(17)34-2)24-15(9-27)14-6-13(21(31)16(29)10-28)8-19(35-3)25(14)38-24/h4-8,11,15-16,20-24,26-33H,9-10H2,1-3H3/t11-,15-,16-,20-,21+,22+,23+,24+,26-/m0/s1
Canonical SMILES:  OC[C@@H]([C@@H](c1cc2[C@H](CO)[C@H](Oc2c(c1)OC)c1ccc(c(c1)OC)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)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
NPO28152 Jacaranda caucana Species Bignoniaceae Eukaryota PMID[19361168]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Ratio = 1.84 23454511
NPT2 Others Unspecified EC50 = 9070 nM 23978047

  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 NPC476301 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 NPC43508
0.9927 High Similarity NPC217635
0.9927 High Similarity NPC79429
0.9927 High Similarity NPC471667
0.9856 High Similarity NPC213074
0.9856 High Similarity NPC275284
0.9856 High Similarity NPC193473
0.9856 High Similarity NPC224674
0.9856 High Similarity NPC15956
0.9856 High Similarity NPC114505
0.9856 High Similarity NPC31325
0.9648 High Similarity NPC98624
0.9645 High Similarity NPC270751
0.9568 High Similarity NPC470950
0.9568 High Similarity NPC185307
0.951 High Similarity NPC472709
0.951 High Similarity NPC472710
0.95 High Similarity NPC283995
0.95 High Similarity NPC470235
0.95 High Similarity NPC129417
0.9496 High Similarity NPC246947
0.9496 High Similarity NPC253878
0.9496 High Similarity NPC476356
0.9433 High Similarity NPC22150
0.9433 High Similarity NPC38041
0.9433 High Similarity NPC279298
0.9429 High Similarity NPC46092
0.9424 High Similarity NPC471414
0.9424 High Similarity NPC472711
0.9379 High Similarity NPC302610
0.9366 High Similarity NPC112861
0.9362 High Similarity NPC471063
0.9301 High Similarity NPC39657
0.9296 High Similarity NPC18979
0.9291 High Similarity NPC477898
0.9281 High Similarity NPC156376
0.927 High Similarity NPC476411
0.927 High Similarity NPC187194
0.9257 High Similarity NPC228357
0.9247 High Similarity NPC474442
0.9231 High Similarity NPC205796
0.9231 High Similarity NPC276753
0.9225 High Similarity NPC84181
0.922 High Similarity NPC302506
0.9209 High Similarity NPC138738
0.9209 High Similarity NPC470413
0.9197 High Similarity NPC26394
0.9172 High Similarity NPC286235
0.9172 High Similarity NPC44452
0.9172 High Similarity NPC51328
0.9172 High Similarity NPC55158
0.9161 High Similarity NPC475096
0.9149 High Similarity NPC471908
0.9137 High Similarity NPC209985
0.9137 High Similarity NPC263367
0.9137 High Similarity NPC29799
0.9137 High Similarity NPC199459
0.9137 High Similarity NPC52277
0.9137 High Similarity NPC156502
0.9137 High Similarity NPC54743
0.9137 High Similarity NPC477939
0.9137 High Similarity NPC10737
0.9137 High Similarity NPC177160
0.9137 High Similarity NPC177035
0.9133 High Similarity NPC478269
0.9124 High Similarity NPC230219
0.911 High Similarity NPC475224
0.9103 High Similarity NPC130449
0.9103 High Similarity NPC248132
0.9097 High Similarity NPC99515
0.9097 High Similarity NPC190714
0.9091 High Similarity NPC472712
0.9091 High Similarity NPC179521
0.9091 High Similarity NPC164183
0.9091 High Similarity NPC473046
0.9091 High Similarity NPC118385
0.9091 High Similarity NPC187774
0.9091 High Similarity NPC472713
0.9085 High Similarity NPC60249
0.9078 High Similarity NPC106944
0.9065 High Similarity NPC79957
0.9065 High Similarity NPC101624
0.9065 High Similarity NPC184938
0.9058 High Similarity NPC25821
0.9034 High Similarity NPC227902
0.9028 High Similarity NPC272619
0.9028 High Similarity NPC469586
0.9028 High Similarity NPC286245
0.9028 High Similarity NPC180953
0.9028 High Similarity NPC181615
0.9021 High Similarity NPC278961
0.9021 High Similarity NPC113680
0.9014 High Similarity NPC76871
0.9013 High Similarity NPC478267
0.9007 High Similarity NPC241600
0.9007 High Similarity NPC173726
0.8993 High Similarity NPC193026
0.8993 High Similarity NPC90083
0.8993 High Similarity NPC170779
0.8993 High Similarity NPC49603
0.8993 High Similarity NPC187616
0.8986 High Similarity NPC18842
0.898 High Similarity NPC229882
0.898 High Similarity NPC183380
0.898 High Similarity NPC158635
0.898 High Similarity NPC238140
0.8978 High Similarity NPC80600
0.8978 High Similarity NPC472024
0.8973 High Similarity NPC175976
0.8973 High Similarity NPC71726
0.8966 High Similarity NPC241846
0.8966 High Similarity NPC260397
0.8966 High Similarity NPC93610
0.8966 High Similarity NPC125755
0.8958 High Similarity NPC473045
0.8958 High Similarity NPC25292
0.8958 High Similarity NPC253015
0.8958 High Similarity NPC471065
0.8951 High Similarity NPC131971
0.8951 High Similarity NPC189115
0.8951 High Similarity NPC469559
0.8951 High Similarity NPC5262
0.8951 High Similarity NPC475084
0.8951 High Similarity NPC472714
0.8936 High Similarity NPC304152
0.8936 High Similarity NPC477938
0.8929 High Similarity NPC93783
0.8926 High Similarity NPC115466
0.8926 High Similarity NPC245615
0.8926 High Similarity NPC61604
0.8926 High Similarity NPC299706
0.8913 High Similarity NPC9912
0.8912 High Similarity NPC35877
0.8912 High Similarity NPC240521
0.8912 High Similarity NPC95392
0.8912 High Similarity NPC55715
0.8905 High Similarity NPC26653
0.8905 High Similarity NPC248355
0.8905 High Similarity NPC270849
0.8905 High Similarity NPC166040
0.8904 High Similarity NPC99183
0.8897 High Similarity NPC161700
0.8897 High Similarity NPC307466
0.8897 High Similarity NPC277867
0.8889 High Similarity NPC473044
0.8889 High Similarity NPC81638
0.8881 High Similarity NPC263261
0.8881 High Similarity NPC87725
0.8881 High Similarity NPC108674
0.8881 High Similarity NPC469661
0.8873 High Similarity NPC292487
0.8867 High Similarity NPC159922
0.8865 High Similarity NPC77861
0.8865 High Similarity NPC172818
0.8865 High Similarity NPC25695
0.8859 High Similarity NPC59692
0.8859 High Similarity NPC21902
0.8857 High Similarity NPC35731
0.8857 High Similarity NPC470881
0.8857 High Similarity NPC16485
0.8857 High Similarity NPC478085
0.8851 High Similarity NPC469707
0.8851 High Similarity NPC185955
0.8851 High Similarity NPC225815
0.8851 High Similarity NPC469706
0.8851 High Similarity NPC218041
0.8851 High Similarity NPC214326
0.8851 High Similarity NPC260781
0.8851 High Similarity NPC9933
0.8851 High Similarity NPC182368
0.8851 High Similarity NPC145979
0.8849 High Similarity NPC259742
0.8849 High Similarity NPC104077
0.8849 High Similarity NPC219671
0.8849 High Similarity NPC147616
0.8849 High Similarity NPC471505
0.8849 High Similarity NPC106739
0.8844 High Similarity NPC159697
0.8844 High Similarity NPC304048
0.8844 High Similarity NPC303013
0.8844 High Similarity NPC301961
0.8844 High Similarity NPC166584
0.8844 High Similarity NPC130959
0.8844 High Similarity NPC474795
0.8844 High Similarity NPC226153
0.8844 High Similarity NPC474940
0.8836 High Similarity NPC162193
0.8832 High Similarity NPC470084
0.8832 High Similarity NPC302378
0.8828 High Similarity NPC76176
0.8828 High Similarity NPC168579
0.8828 High Similarity NPC12641
0.8828 High Similarity NPC63879
0.8828 High Similarity NPC280092
0.8828 High Similarity NPC469313
0.8828 High Similarity NPC93323
0.8828 High Similarity NPC133251
0.8828 High Similarity NPC45257
0.8828 High Similarity NPC138227
0.8819 High Similarity NPC41782

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476301 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
0.8881 High Similarity NPD6674 Discontinued
0.8322 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD1613 Approved
0.8194 Intermediate Similarity NPD37 Approved
0.8188 Intermediate Similarity NPD1091 Approved
0.8153 Intermediate Similarity NPD4965 Approved
0.8153 Intermediate Similarity NPD4967 Phase 2
0.8153 Intermediate Similarity NPD4966 Approved
0.8148 Intermediate Similarity NPD7228 Approved
0.8112 Intermediate Similarity NPD3027 Phase 3
0.8108 Intermediate Similarity NPD7266 Discontinued
0.8099 Intermediate Similarity NPD2861 Phase 2
0.8079 Intermediate Similarity NPD5058 Phase 3
0.8063 Intermediate Similarity NPD7199 Phase 2
0.8058 Intermediate Similarity NPD3705 Approved
0.8052 Intermediate Similarity NPD1653 Approved
0.805 Intermediate Similarity NPD6234 Discontinued
0.8042 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD8455 Phase 2
0.8 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7972 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD7074 Phase 3
0.7931 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7927 Intermediate Similarity NPD3818 Discontinued
0.7879 Intermediate Similarity NPD7054 Approved
0.7853 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD7240 Approved
0.7842 Intermediate Similarity NPD1357 Approved
0.7831 Intermediate Similarity NPD7472 Approved
0.7823 Intermediate Similarity NPD4060 Phase 1
0.7793 Intermediate Similarity NPD4908 Phase 1
0.7762 Intermediate Similarity NPD8651 Approved
0.7738 Intermediate Similarity NPD6559 Discontinued
0.7733 Intermediate Similarity NPD5588 Approved
0.7692 Intermediate Similarity NPD7808 Phase 3
0.7677 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD1610 Phase 2
0.7667 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD4538 Approved
0.7667 Intermediate Similarity NPD4536 Approved
0.7664 Intermediate Similarity NPD5283 Phase 1
0.766 Intermediate Similarity NPD5125 Phase 3
0.766 Intermediate Similarity NPD5126 Approved
0.7633 Intermediate Similarity NPD7251 Discontinued
0.7632 Intermediate Similarity NPD5762 Approved
0.7632 Intermediate Similarity NPD5763 Approved
0.7584 Intermediate Similarity NPD3620 Phase 2
0.7584 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD6797 Phase 2
0.7568 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD7157 Approved
0.755 Intermediate Similarity NPD7097 Phase 1
0.7546 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7533 Intermediate Similarity NPD6355 Discontinued
0.7533 Intermediate Similarity NPD5735 Approved
0.7529 Intermediate Similarity NPD7685 Pre-registration
0.7516 Intermediate Similarity NPD1934 Approved
0.75 Intermediate Similarity NPD4625 Phase 3
0.75 Intermediate Similarity NPD5960 Phase 3
0.75 Intermediate Similarity NPD4108 Discontinued
0.7485 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6331 Phase 2
0.7464 Intermediate Similarity NPD7843 Approved
0.7456 Intermediate Similarity NPD5844 Phase 1
0.7455 Intermediate Similarity NPD5494 Approved
0.7442 Intermediate Similarity NPD8313 Approved
0.7442 Intermediate Similarity NPD8312 Approved
0.7439 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD2970 Approved
0.7425 Intermediate Similarity NPD2969 Approved
0.741 Intermediate Similarity NPD8127 Discontinued
0.7403 Intermediate Similarity NPD1375 Discontinued
0.7381 Intermediate Similarity NPD6166 Phase 2
0.7381 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD3018 Phase 2
0.7365 Intermediate Similarity NPD3051 Approved
0.7362 Intermediate Similarity NPD2978 Approved
0.7362 Intermediate Similarity NPD2977 Approved
0.7329 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD4749 Approved
0.7308 Intermediate Similarity NPD5177 Phase 3
0.7305 Intermediate Similarity NPD6671 Approved
0.7303 Intermediate Similarity NPD5124 Phase 1
0.7303 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD2684 Approved
0.7296 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6004 Phase 3
0.729 Intermediate Similarity NPD6005 Phase 3
0.729 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6002 Phase 3
0.7279 Intermediate Similarity NPD6696 Suspended
0.7278 Intermediate Similarity NPD2489 Approved
0.7278 Intermediate Similarity NPD27 Approved
0.7273 Intermediate Similarity NPD1548 Phase 1
0.7273 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD7095 Approved
0.7266 Intermediate Similarity NPD228 Approved
0.7262 Intermediate Similarity NPD6071 Discontinued
0.7261 Intermediate Similarity NPD4110 Phase 3
0.7261 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD6653 Approved
0.7244 Intermediate Similarity NPD2424 Discontinued
0.7241 Intermediate Similarity NPD7311 Approved
0.7241 Intermediate Similarity NPD7310 Approved
0.7241 Intermediate Similarity NPD7312 Approved
0.7241 Intermediate Similarity NPD7313 Approved
0.7237 Intermediate Similarity NPD4140 Approved
0.7229 Intermediate Similarity NPD7075 Discontinued
0.7228 Intermediate Similarity NPD7680 Approved
0.7226 Intermediate Similarity NPD290 Approved
0.7219 Intermediate Similarity NPD6798 Discontinued
0.7215 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD2677 Approved
0.7212 Intermediate Similarity NPD2563 Approved
0.7212 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD2560 Approved
0.7212 Intermediate Similarity NPD3817 Phase 2
0.7211 Intermediate Similarity NPD5327 Phase 3
0.7211 Intermediate Similarity NPD2983 Phase 2
0.7211 Intermediate Similarity NPD2982 Phase 2
0.7205 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7309 Approved
0.7197 Intermediate Similarity NPD4236 Phase 3
0.7197 Intermediate Similarity NPD4237 Approved
0.7181 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD4380 Phase 2
0.7175 Intermediate Similarity NPD7906 Approved
0.7175 Intermediate Similarity NPD6841 Approved
0.7175 Intermediate Similarity NPD6843 Phase 3
0.7175 Intermediate Similarity NPD6842 Approved
0.717 Intermediate Similarity NPD6667 Approved
0.717 Intermediate Similarity NPD6666 Approved
0.7169 Intermediate Similarity NPD3882 Suspended
0.7161 Intermediate Similarity NPD7033 Discontinued
0.716 Intermediate Similarity NPD3787 Discontinued
0.7152 Intermediate Similarity NPD7819 Suspended
0.7152 Intermediate Similarity NPD2801 Approved
0.7152 Intermediate Similarity NPD4628 Phase 3
0.7152 Intermediate Similarity NPD4535 Phase 3
0.7152 Intermediate Similarity NPD5773 Approved
0.7152 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5772 Approved
0.7143 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2981 Phase 2
0.7135 Intermediate Similarity NPD7473 Discontinued
0.7135 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD1558 Phase 1
0.7122 Intermediate Similarity NPD3021 Approved
0.7122 Intermediate Similarity NPD3022 Approved
0.7119 Intermediate Similarity NPD4663 Approved
0.7117 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1652 Phase 2
0.7079 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD7028 Phase 2
0.7063 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6232 Discontinued
0.7059 Intermediate Similarity NPD6233 Phase 2
0.7059 Intermediate Similarity NPD7229 Phase 3
0.7056 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD6516 Phase 2
0.7055 Intermediate Similarity NPD5846 Approved
0.7045 Intermediate Similarity NPD4578 Approved
0.7045 Intermediate Similarity NPD4577 Approved
0.7037 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7526 Approved
0.7037 Intermediate Similarity NPD52 Approved
0.7032 Intermediate Similarity NPD6353 Approved
0.703 Intermediate Similarity NPD6072 Discontinued
0.7019 Intermediate Similarity NPD7041 Phase 2
0.7019 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1774 Approved
0.7013 Intermediate Similarity NPD2238 Phase 2
0.7012 Intermediate Similarity NPD7458 Discontinued
0.7006 Intermediate Similarity NPD2161 Phase 2
0.7 Intermediate Similarity NPD3094 Phase 2
0.6994 Remote Similarity NPD3751 Discontinued
0.6989 Remote Similarity NPD7549 Discontinued
0.6988 Remote Similarity NPD6801 Discontinued
0.6988 Remote Similarity NPD3383 Approved
0.6988 Remote Similarity NPD3382 Approved
0.6988 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6988 Remote Similarity NPD3384 Approved
0.6987 Remote Similarity NPD7119 Phase 2
0.6987 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6981 Remote Similarity NPD4162 Approved
0.6981 Remote Similarity NPD3060 Approved

Structure

External Identifiers

PubChem CID   45272229
ChEMBL   CHEMBL562877
ZINC  

Physicochemical Properties

Molecular Weight:  538.21
ALogP:  -4.2402
MLogP:  3
XLogP:  -0.954
# Rotatable Bonds:  19
Polar Surface Area:  187.76
# H-Bond Aceptor:  8
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  38

Download Data

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