Natural Product: NPC469527

Natural Product ID:  NPC469527
Common Name:   Rosavin
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[(E)-3-phenylprop-2-enoxy]-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
Synonyms:   Rosavin
Molecular Formula:   C20H28O10
Standard InCHIKey:  RINHYCZCUGCZAJ-UHAHJPEESA-N
Standard InCHI:  InChI=1S/C20H28O10/c21-12-9-28-19(17(25)14(12)22)29-10-13-15(23)16(24)18(26)20(30-13)27-8-4-7-11-5-2-1-3-6-11/h1-7,12-26H,8-10H2/b7-4+/t12-,13+,14-,15+,16-,17+,18+,19-,20-/m0/s1
Canonical SMILES:  O[C@@H]1[C@@H](O)[C@@H](OC/C=C/c2ccccc2)O[C@@H]([C@H]1O)CO[C@@H]1OC[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
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota Twigs PMID[19555125]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota Twigs PMID[22677314]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 > 50 ug/ml 20718475
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Inhibition = 18.7 % 26295746
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 > 10000000 nM 7714539

  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 NPC469527 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
0.9406 High Similarity NPC474148
0.9406 High Similarity NPC276061
0.9314 High Similarity NPC30563
0.9223 High Similarity NPC470825
0.9118 High Similarity NPC184633
0.901 High Similarity NPC37714
0.901 High Similarity NPC152384
0.8942 High Similarity NPC264784
0.8868 High Similarity NPC474641
0.8788 High Similarity NPC262826
0.8762 High Similarity NPC43584
0.8725 High Similarity NPC47286
0.8716 High Similarity NPC122245
0.8716 High Similarity NPC266389
0.8716 High Similarity NPC216605
0.8611 High Similarity NPC29607
0.8544 High Similarity NPC148060
0.8349 Intermediate Similarity NPC120217
0.8273 Intermediate Similarity NPC313193
0.8261 Intermediate Similarity NPC140561
0.8261 Intermediate Similarity NPC141970
0.8246 Intermediate Similarity NPC229600
0.8125 Intermediate Similarity NPC175771
0.812 Intermediate Similarity NPC162925
0.812 Intermediate Similarity NPC87153
0.812 Intermediate Similarity NPC57607
0.8103 Intermediate Similarity NPC476142
0.8051 Intermediate Similarity NPC77651
0.8051 Intermediate Similarity NPC28069
0.8017 Intermediate Similarity NPC55608
0.7983 Intermediate Similarity NPC290276
0.7983 Intermediate Similarity NPC114096
0.7983 Intermediate Similarity NPC63404
0.7983 Intermediate Similarity NPC198918
0.7983 Intermediate Similarity NPC10121
0.7983 Intermediate Similarity NPC231888
0.7983 Intermediate Similarity NPC92283
0.7983 Intermediate Similarity NPC204214
0.7983 Intermediate Similarity NPC124878
0.7983 Intermediate Similarity NPC35338
0.7983 Intermediate Similarity NPC10883
0.7966 Intermediate Similarity NPC145287
0.7965 Intermediate Similarity NPC148055
0.7949 Intermediate Similarity NPC52097
0.7946 Intermediate Similarity NPC157338
0.7931 Intermediate Similarity NPC469703
0.7931 Intermediate Similarity NPC469412
0.7931 Intermediate Similarity NPC469704
0.7931 Intermediate Similarity NPC160854
0.7931 Intermediate Similarity NPC201402
0.7931 Intermediate Similarity NPC198734
0.7917 Intermediate Similarity NPC148026
0.7917 Intermediate Similarity NPC231627
0.7917 Intermediate Similarity NPC471025
0.7917 Intermediate Similarity NPC106677
0.7913 Intermediate Similarity NPC14950
0.7899 Intermediate Similarity NPC83218
0.7899 Intermediate Similarity NPC126991
0.7863 Intermediate Similarity NPC469686
0.7863 Intermediate Similarity NPC11724
0.7851 Intermediate Similarity NPC237182
0.7851 Intermediate Similarity NPC226101
0.7851 Intermediate Similarity NPC471024
0.7845 Intermediate Similarity NPC282409
0.7845 Intermediate Similarity NPC469708
0.7845 Intermediate Similarity NPC469702
0.7845 Intermediate Similarity NPC60589
0.7833 Intermediate Similarity NPC471157
0.7833 Intermediate Similarity NPC267733
0.7833 Intermediate Similarity NPC276047
0.7833 Intermediate Similarity NPC252114
0.7815 Intermediate Similarity NPC287429
0.7797 Intermediate Similarity NPC471067
0.7778 Intermediate Similarity NPC476445
0.7778 Intermediate Similarity NPC476448
0.7778 Intermediate Similarity NPC269242
0.7778 Intermediate Similarity NPC476872
0.7778 Intermediate Similarity NPC469548
0.7769 Intermediate Similarity NPC288416
0.7769 Intermediate Similarity NPC175333
0.7759 Intermediate Similarity NPC476096
0.775 Intermediate Similarity NPC470510
0.7731 Intermediate Similarity NPC178449
0.7731 Intermediate Similarity NPC232454
0.7731 Intermediate Similarity NPC470907
0.7724 Intermediate Similarity NPC319995
0.7724 Intermediate Similarity NPC289415
0.7712 Intermediate Similarity NPC226712
0.7705 Intermediate Similarity NPC301857
0.7705 Intermediate Similarity NPC225307
0.7686 Intermediate Similarity NPC147032
0.7667 Intermediate Similarity NPC244454
0.7661 Intermediate Similarity NPC138777
0.7661 Intermediate Similarity NPC225384
0.7661 Intermediate Similarity NPC9912
0.7661 Intermediate Similarity NPC246869
0.7661 Intermediate Similarity NPC46137
0.7661 Intermediate Similarity NPC235294
0.7642 Intermediate Similarity NPC253595
0.7642 Intermediate Similarity NPC295970
0.7623 Intermediate Similarity NPC471882
0.7623 Intermediate Similarity NPC45224
0.7623 Intermediate Similarity NPC35288
0.7623 Intermediate Similarity NPC156692
0.7623 Intermediate Similarity NPC173150
0.7623 Intermediate Similarity NPC471881
0.76 Intermediate Similarity NPC473285
0.76 Intermediate Similarity NPC254275
0.7583 Intermediate Similarity NPC212176
0.7581 Intermediate Similarity NPC17567
0.7563 Intermediate Similarity NPC266045
0.7561 Intermediate Similarity NPC302378
0.7521 Intermediate Similarity NPC228907
0.752 Intermediate Similarity NPC254819
0.752 Intermediate Similarity NPC475067
0.752 Intermediate Similarity NPC478255
0.75 Intermediate Similarity NPC301651
0.75 Intermediate Similarity NPC27712
0.75 Intermediate Similarity NPC248355
0.75 Intermediate Similarity NPC477294
0.75 Intermediate Similarity NPC473556
0.75 Intermediate Similarity NPC477293
0.75 Intermediate Similarity NPC307110
0.75 Intermediate Similarity NPC229784
0.75 Intermediate Similarity NPC184092
0.75 Intermediate Similarity NPC218003
0.748 Intermediate Similarity NPC231607
0.748 Intermediate Similarity NPC188555
0.748 Intermediate Similarity NPC108659
0.748 Intermediate Similarity NPC87696
0.748 Intermediate Similarity NPC264900
0.748 Intermediate Similarity NPC130496
0.748 Intermediate Similarity NPC469687
0.748 Intermediate Similarity NPC79715
0.748 Intermediate Similarity NPC35731
0.746 Intermediate Similarity NPC26080
0.746 Intermediate Similarity NPC303422
0.746 Intermediate Similarity NPC165686
0.746 Intermediate Similarity NPC85799
0.7459 Intermediate Similarity NPC90318
0.744 Intermediate Similarity NPC80600
0.744 Intermediate Similarity NPC472024
0.7438 Intermediate Similarity NPC138798
0.7438 Intermediate Similarity NPC473881
0.7422 Intermediate Similarity NPC470236
0.7422 Intermediate Similarity NPC263829
0.7422 Intermediate Similarity NPC238243
0.7419 Intermediate Similarity NPC40377
0.7419 Intermediate Similarity NPC232880
0.7419 Intermediate Similarity NPC146540
0.7419 Intermediate Similarity NPC148982
0.7402 Intermediate Similarity NPC28637
0.7402 Intermediate Similarity NPC322503
0.7402 Intermediate Similarity NPC294166
0.7402 Intermediate Similarity NPC115022
0.7402 Intermediate Similarity NPC470143
0.7398 Intermediate Similarity NPC61181
0.7398 Intermediate Similarity NPC94179
0.7398 Intermediate Similarity NPC471026
0.7381 Intermediate Similarity NPC65942
0.7381 Intermediate Similarity NPC219677
0.7381 Intermediate Similarity NPC248307
0.7381 Intermediate Similarity NPC121376
0.7381 Intermediate Similarity NPC281798
0.7368 Intermediate Similarity NPC234376
0.7364 Intermediate Similarity NPC3293
0.7364 Intermediate Similarity NPC164857
0.7364 Intermediate Similarity NPC197723
0.7364 Intermediate Similarity NPC165482
0.7364 Intermediate Similarity NPC469383
0.7364 Intermediate Similarity NPC472132
0.7364 Intermediate Similarity NPC138350
0.7364 Intermediate Similarity NPC40664
0.736 Intermediate Similarity NPC97326
0.736 Intermediate Similarity NPC270849
0.736 Intermediate Similarity NPC11025
0.736 Intermediate Similarity NPC26653
0.736 Intermediate Similarity NPC166040
0.7344 Intermediate Similarity NPC187194
0.7344 Intermediate Similarity NPC287597
0.7344 Intermediate Similarity NPC169398
0.7344 Intermediate Similarity NPC476411
0.7344 Intermediate Similarity NPC886
0.7344 Intermediate Similarity NPC34293
0.7339 Intermediate Similarity NPC103533
0.7339 Intermediate Similarity NPC198798
0.7339 Intermediate Similarity NPC476873
0.7323 Intermediate Similarity NPC162093
0.7323 Intermediate Similarity NPC473924
0.7323 Intermediate Similarity NPC252833
0.7317 Intermediate Similarity NPC12308
0.7317 Intermediate Similarity NPC123704
0.7308 Intermediate Similarity NPC65262
0.7308 Intermediate Similarity NPC476376
0.7308 Intermediate Similarity NPC260425
0.7308 Intermediate Similarity NPC78363
0.7308 Intermediate Similarity NPC469364
0.7308 Intermediate Similarity NPC262328
0.7308 Intermediate Similarity NPC87777
0.7308 Intermediate Similarity NPC304152

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469527 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
0.7845 Intermediate Similarity NPD5126 Approved
0.7845 Intermediate Similarity NPD5125 Phase 3
0.7712 Intermediate Similarity NPD1091 Approved
0.7368 Intermediate Similarity NPD969 Suspended
0.7252 Intermediate Similarity NPD7266 Discontinued
0.7054 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.6991 Remote Similarity NPD5048 Discontinued
0.6952 Remote Similarity NPD689 Discontinued
0.6884 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6010 Discontinued
0.6667 Remote Similarity NPD7741 Discontinued
0.6638 Remote Similarity NPD6685 Approved
0.6604 Remote Similarity NPD1282 Approved
0.6581 Remote Similarity NPD290 Approved
0.6557 Remote Similarity NPD4198 Discontinued
0.6549 Remote Similarity NPD7798 Approved
0.6522 Remote Similarity NPD5765 Approved
0.6522 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6522 Remote Similarity NPD6647 Phase 2
0.6519 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6507 Remote Similarity NPD8455 Phase 2
0.6503 Remote Similarity NPD1653 Approved
0.65 Remote Similarity NPD5058 Phase 3
0.65 Remote Similarity NPD6912 Phase 3
0.6484 Remote Similarity NPD7876 Discontinued
0.6466 Remote Similarity NPD4404 Approved
0.6446 Remote Similarity NPD7843 Approved
0.6441 Remote Similarity NPD9532 Phase 3
0.6436 Remote Similarity NPD9294 Approved
0.6403 Remote Similarity NPD6674 Discontinued
0.6389 Remote Similarity NPD531 Approved
0.6387 Remote Similarity NPD2684 Approved
0.6371 Remote Similarity NPD694 Clinical (unspecified phase)
0.6349 Remote Similarity NPD1357 Approved
0.6341 Remote Similarity NPD2629 Approved
0.6333 Remote Similarity NPD2067 Discontinued
0.6328 Remote Similarity NPD3705 Approved
0.6316 Remote Similarity NPD9495 Approved
0.6316 Remote Similarity NPD3027 Phase 3
0.6299 Remote Similarity NPD5723 Approved
0.6296 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6296 Remote Similarity NPD1613 Approved
0.629 Remote Similarity NPD7157 Approved
0.6277 Remote Similarity NPD41 Approved
0.6277 Remote Similarity NPD5886 Approved
0.6277 Remote Similarity NPD4538 Approved
0.6277 Remote Similarity NPD4536 Approved
0.6277 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6267 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6232 Remote Similarity NPD5588 Approved
0.6232 Remote Similarity NPD5960 Phase 3
0.6197 Remote Similarity NPD6190 Approved
0.6186 Remote Similarity NPD5909 Discontinued
0.6174 Remote Similarity NPD5926 Approved
0.617 Remote Similarity NPD1652 Phase 2
0.6167 Remote Similarity NPD6406 Approved
0.6159 Remote Similarity NPD7097 Phase 1
0.6129 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6103 Remote Similarity NPD6233 Phase 2
0.609 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6083 Remote Similarity NPD3526 Approved
0.6083 Remote Similarity NPD968 Approved
0.6083 Remote Similarity NPD3524 Approved
0.6074 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6068 Remote Similarity NPD2558 Approved
0.6068 Remote Similarity NPD2553 Approved
0.6068 Remote Similarity NPD2555 Approved
0.6068 Remote Similarity NPD2550 Approved
0.6068 Remote Similarity NPD2552 Approved
0.6068 Remote Similarity NPD2549 Approved
0.6066 Remote Similarity NPD9713 Approved
0.6061 Remote Similarity NPD8651 Approved
0.6056 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6047 Remote Similarity NPD6516 Phase 2
0.6047 Remote Similarity NPD5846 Approved
0.6045 Remote Similarity NPD2861 Phase 2
0.6034 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6033 Remote Similarity NPD4095 Clinical (unspecified phase)
0.6033 Remote Similarity NPD1358 Approved
0.6017 Remote Similarity NPD291 Approved
0.6017 Remote Similarity NPD4189 Approved
0.6017 Remote Similarity NPD4188 Approved
0.6016 Remote Similarity NPD1548 Phase 1
0.6013 Remote Similarity NPD7054 Approved
0.6013 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6 Remote Similarity NPD4908 Phase 1
0.6 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6 Remote Similarity NPD794 Clinical (unspecified phase)
0.5985 Remote Similarity NPD3685 Discontinued
0.5984 Remote Similarity NPD5291 Approved
0.5984 Remote Similarity NPD5292 Approved
0.5975 Remote Similarity NPD7074 Phase 3
0.5975 Remote Similarity NPD7472 Approved
0.5972 Remote Similarity NPD7274 Clinical (unspecified phase)
0.5966 Remote Similarity NPD5700 Clinical (unspecified phase)
0.5965 Remote Similarity NPD3718 Approved
0.5965 Remote Similarity NPD5122 Clinical (unspecified phase)
0.5965 Remote Similarity NPD3719 Approved
0.5956 Remote Similarity NPD3179 Approved
0.5956 Remote Similarity NPD3180 Approved
0.5954 Remote Similarity NPD1610 Phase 2
0.5949 Remote Similarity NPD7228 Approved
0.5938 Remote Similarity NPD6797 Phase 2
0.5935 Remote Similarity NPD556 Approved
0.5931 Remote Similarity NPD3122 Phase 3
0.5929 Remote Similarity NPD9365 Approved
0.5926 Remote Similarity NPD3971 Phase 1
0.5926 Remote Similarity NPD1530 Clinical (unspecified phase)
0.5922 Remote Similarity NPD9716 Approved
0.5917 Remote Similarity NPD3046 Approved
0.5917 Remote Similarity NPD3047 Approved
0.5917 Remote Similarity NPD3048 Approved
0.5913 Remote Similarity NPD2934 Approved
0.5913 Remote Similarity NPD2933 Approved
0.5912 Remote Similarity NPD6798 Discontinued
0.5912 Remote Similarity NPD8470 Clinical (unspecified phase)
0.5912 Remote Similarity NPD4907 Clinical (unspecified phase)
0.5906 Remote Similarity NPD7508 Discontinued
0.5903 Remote Similarity NPD2575 Approved
0.5902 Remote Similarity NPD5979 Clinical (unspecified phase)
0.5902 Remote Similarity NPD6686 Approved
0.5901 Remote Similarity NPD7251 Discontinued
0.5899 Remote Similarity NPD4340 Discontinued
0.5899 Remote Similarity NPD5123 Clinical (unspecified phase)
0.5899 Remote Similarity NPD5124 Phase 1
0.5896 Remote Similarity NPD2159 Approved
0.5896 Remote Similarity NPD2625 Approved
0.5896 Remote Similarity NPD2627 Approved
0.5896 Remote Similarity NPD3094 Phase 2
0.5896 Remote Similarity NPD2160 Approved
0.5896 Remote Similarity NPD2628 Approved
0.5896 Remote Similarity NPD2626 Approved
0.5894 Remote Similarity NPD37 Approved
0.5888 Remote Similarity NPD226 Approved
0.5887 Remote Similarity NPD7033 Discontinued
0.5887 Remote Similarity NPD4025 Clinical (unspecified phase)
0.5887 Remote Similarity NPD4141 Clinical (unspecified phase)
0.5887 Remote Similarity NPD4108 Discontinued
0.5882 Remote Similarity NPD4967 Phase 2
0.5882 Remote Similarity NPD4966 Approved
0.5882 Remote Similarity NPD2613 Approved
0.5882 Remote Similarity NPD4965 Approved
0.5867 Remote Similarity NPD4380 Phase 2
0.5865 Remote Similarity NPD2982 Phase 2
0.5865 Remote Similarity NPD2983 Phase 2
0.5864 Remote Similarity NPD7808 Phase 3
0.5862 Remote Similarity NPD2860 Approved
0.5862 Remote Similarity NPD2859 Approved
0.5857 Remote Similarity NPD6653 Approved
0.5856 Remote Similarity NPD4793 Discontinued
0.5854 Remote Similarity NPD2182 Approved
0.5852 Remote Similarity NPD7247 Discontinued
0.5849 Remote Similarity NPD3818 Discontinued
0.5847 Remote Similarity NPD1238 Approved
0.5841 Remote Similarity NPD3673 Approved
0.5841 Remote Similarity NPD3672 Approved
0.584 Remote Similarity NPD4573 Approved
0.584 Remote Similarity NPD4572 Approved
0.584 Remote Similarity NPD4571 Approved
0.5833 Remote Similarity NPD744 Clinical (unspecified phase)
0.5828 Remote Similarity NPD8313 Approved
0.5828 Remote Similarity NPD8312 Approved
0.5822 Remote Similarity NPD5756 Phase 2
0.582 Remote Similarity NPD2551 Approved
0.582 Remote Similarity NPD3134 Approved
0.582 Remote Similarity NPD811 Approved
0.582 Remote Similarity NPD2559 Approved
0.582 Remote Similarity NPD812 Approved
0.582 Remote Similarity NPD810 Approved
0.5806 Remote Similarity NPD6234 Discontinued
0.5804 Remote Similarity NPD521 Clinical (unspecified phase)
0.5804 Remote Similarity NPD5763 Approved
0.5804 Remote Similarity NPD2029 Clinical (unspecified phase)
0.5804 Remote Similarity NPD5762 Approved
0.5802 Remote Similarity NPD5305 Approved
0.5802 Remote Similarity NPD5238 Clinical (unspecified phase)
0.5802 Remote Similarity NPD7685 Pre-registration
0.5802 Remote Similarity NPD7240 Approved
0.5802 Remote Similarity NPD5306 Approved
0.5802 Remote Similarity NPD6559 Discontinued
0.5798 Remote Similarity NPD1242 Phase 1
0.5797 Remote Similarity NPD6410 Clinical (unspecified phase)
0.5797 Remote Similarity NPD6859 Clinical (unspecified phase)
0.5796 Remote Similarity NPD3787 Discontinued
0.5794 Remote Similarity NPD1138 Approved
0.5793 Remote Similarity NPD4535 Phase 3
0.5793 Remote Similarity NPD4628 Phase 3
0.5789 Remote Similarity NPD2981 Phase 2
0.5789 Remote Similarity NPD7249 Approved
0.5789 Remote Similarity NPD7250 Approved
0.5789 Remote Similarity NPD2235 Phase 2
0.5789 Remote Similarity NPD2231 Phase 2
0.5785 Remote Similarity NPD1237 Approved
0.5782 Remote Similarity NPD6143 Clinical (unspecified phase)
0.5781 Remote Similarity NPD6671 Approved
0.578 Remote Similarity NPD9491 Approved
0.5776 Remote Similarity NPD4814 Discontinued
0.5772 Remote Similarity NPD5403 Approved
0.5769 Remote Similarity NPD9545 Approved
0.5767 Remote Similarity NPD4338 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   6440755
ChEMBL   CHEMBL1083511
ZINC  

Physicochemical Properties

Molecular Weight:  428.17
ALogP:  -2.964
MLogP:  2.56
XLogP:  1.406
# Rotatable Bonds:  13
Polar Surface Area:  158.3
# H-Bond Aceptor:  10
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  30

Download Data

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