Natural Product: NPC55793

Natural Product ID:  NPC55793
Common Name:   Princepin
IUPAC Name:   4-[(3S,3aR,6S,6aR)-6-[(2S,3S)-3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]benzene-1,2-diol
Synonyms:   Princepin
Molecular Formula:   C27H26O9
Standard InCHIKey:  RRXDUTVDPLTNBK-FFFFCZNISA-N
Standard InCHI:  InChI=1S/C27H26O9/c28-10-24-27(14-2-5-19(30)21(32)8-14)36-23-9-15(3-6-22(23)35-24)26-17-12-33-25(16(17)11-34-26)13-1-4-18(29)20(31)7-13/h1-9,16-17,24-32H,10-12H2/t16-,17-,24-,25+,26+,27-/m0/s1
Canonical SMILES:  OC[C@@H]1Oc2ccc(cc2O[C@H]1c1ccc(c(c1)O)O)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc(c(c1)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
NPO18521 Capparis flavicans Species Capparaceae Eukaryota Aerial parts Khon Kaen Province, Thailand 2006-AUG PMID[19943620]
NPO6662 Joannesia princeps Species Euphorbiaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens Activity = 0.3 nM 19943620
NPT83 Cell Line MCF7 Homo sapiens Activity = 0.004 nM 19943620
NPT83 Cell Line MCF7 Homo sapiens Activity = 0.007 nM 19943620
NPT396 Cell Line T47D Homo sapiens Activity = 0.4 nM 19943620
NPT396 Cell Line T47D Homo sapiens Activity = 0.001 nM 19943620
NPT396 Cell Line T47D Homo sapiens Activity = 0.006 nM 19943620

  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 NPC55793 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
0.9478 High Similarity NPC77861
0.942 High Similarity NPC114119
0.942 High Similarity NPC471415
0.942 High Similarity NPC470097
0.9343 High Similarity NPC470372
0.9286 High Similarity NPC317053
0.9286 High Similarity NPC324492
0.9259 High Similarity NPC93783
0.9248 High Similarity NPC40432
0.9248 High Similarity NPC228346
0.9248 High Similarity NPC158079
0.9248 High Similarity NPC161557
0.9248 High Similarity NPC7171
0.9248 High Similarity NPC27843
0.9248 High Similarity NPC115207
0.9225 High Similarity NPC470098
0.9225 High Similarity NPC473266
0.9225 High Similarity NPC470826
0.922 High Similarity NPC320671
0.922 High Similarity NPC327412
0.922 High Similarity NPC320970
0.922 High Similarity NPC328567
0.9214 High Similarity NPC22150
0.9214 High Similarity NPC279298
0.9214 High Similarity NPC38041
0.9203 High Similarity NPC178054
0.9197 High Similarity NPC260842
0.9179 High Similarity NPC181049
0.9179 High Similarity NPC207400
0.9179 High Similarity NPC4940
0.9173 High Similarity NPC153739
0.9173 High Similarity NPC92164
0.9173 High Similarity NPC257582
0.9173 High Similarity NPC242807
0.9173 High Similarity NPC64201
0.9173 High Similarity NPC241522
0.9173 High Similarity NPC187998
0.9173 High Similarity NPC77040
0.9173 High Similarity NPC145305
0.9173 High Similarity NPC174495
0.9173 High Similarity NPC42300
0.9167 High Similarity NPC72529
0.9155 High Similarity NPC304048
0.9155 High Similarity NPC226153
0.9149 High Similarity NPC112861
0.9137 High Similarity NPC476356
0.9137 High Similarity NPC302506
0.913 High Similarity NPC266197
0.913 High Similarity NPC291101
0.9104 High Similarity NPC277804
0.9098 High Similarity NPC475875
0.9098 High Similarity NPC5851
0.9098 High Similarity NPC86030
0.9097 High Similarity NPC324517
0.9097 High Similarity NPC321972
0.9097 High Similarity NPC329343
0.9078 High Similarity NPC18979
0.9078 High Similarity NPC469586
0.9071 High Similarity NPC185307
0.9071 High Similarity NPC477898
0.9071 High Similarity NPC470950
0.9058 High Similarity NPC22517
0.9051 High Similarity NPC29799
0.9051 High Similarity NPC209985
0.9051 High Similarity NPC177160
0.9051 High Similarity NPC10737
0.9051 High Similarity NPC54743
0.9051 High Similarity NPC263367
0.9051 High Similarity NPC156502
0.9051 High Similarity NPC477939
0.9044 High Similarity NPC478085
0.9028 High Similarity NPC475224
0.9023 High Similarity NPC252307
0.9023 High Similarity NPC129570
0.9023 High Similarity NPC45774
0.9023 High Similarity NPC474178
0.9023 High Similarity NPC470084
0.9023 High Similarity NPC21867
0.9023 High Similarity NPC282703
0.9023 High Similarity NPC11258
0.9023 High Similarity NPC184733
0.9023 High Similarity NPC128208
0.9023 High Similarity NPC245826
0.9021 High Similarity NPC227516
0.9021 High Similarity NPC20757
0.9014 High Similarity NPC241846
0.9014 High Similarity NPC260397
0.9014 High Similarity NPC93610
0.9007 High Similarity NPC470235
0.9007 High Similarity NPC129417
0.9007 High Similarity NPC179521
0.9007 High Similarity NPC84181
0.9007 High Similarity NPC283995
0.9 High Similarity NPC246947
0.8993 High Similarity NPC309124
0.8993 High Similarity NPC262189
0.8993 High Similarity NPC184797
0.8986 High Similarity NPC474390
0.8978 High Similarity NPC99572
0.8978 High Similarity NPC141765
0.8978 High Similarity NPC24490
0.8978 High Similarity NPC126409
0.8978 High Similarity NPC165155
0.8978 High Similarity NPC34103
0.8958 High Similarity NPC55158
0.8958 High Similarity NPC51328
0.8958 High Similarity NPC286235
0.8947 High Similarity NPC41706
0.8947 High Similarity NPC111247
0.8947 High Similarity NPC147821
0.8947 High Similarity NPC292056
0.8947 High Similarity NPC319625
0.8947 High Similarity NPC165045
0.8947 High Similarity NPC118533
0.8947 High Similarity NPC183181
0.8947 High Similarity NPC118787
0.8947 High Similarity NPC163332
0.8936 High Similarity NPC46092
0.8929 High Similarity NPC472711
0.8921 High Similarity NPC473739
0.8921 High Similarity NPC232164
0.8921 High Similarity NPC156376
0.8921 High Similarity NPC236306
0.8919 High Similarity NPC11411
0.8905 High Similarity NPC326095
0.8905 High Similarity NPC187616
0.8905 High Similarity NPC287745
0.8905 High Similarity NPC170694
0.8905 High Similarity NPC471942
0.8905 High Similarity NPC244983
0.8905 High Similarity NPC193026
0.8905 High Similarity NPC49603
0.8897 High Similarity NPC98624
0.8889 High Similarity NPC248132
0.8889 High Similarity NPC329836
0.8889 High Similarity NPC130449
0.8881 High Similarity NPC276753
0.8881 High Similarity NPC205796
0.8873 High Similarity NPC28440
0.8873 High Similarity NPC15659
0.8873 High Similarity NPC304894
0.8873 High Similarity NPC171932
0.8872 High Similarity NPC206882
0.8872 High Similarity NPC178284
0.8872 High Similarity NPC58607
0.8872 High Similarity NPC191037
0.8865 High Similarity NPC107161
0.8865 High Similarity NPC67467
0.8864 High Similarity NPC146355
0.8864 High Similarity NPC257682
0.8864 High Similarity NPC131747
0.8857 High Similarity NPC106944
0.8841 High Similarity NPC142547
0.8841 High Similarity NPC135777
0.8832 High Similarity NPC26394
0.8832 High Similarity NPC158331
0.8828 High Similarity NPC211561
0.8819 High Similarity NPC236202
0.8819 High Similarity NPC204770
0.8819 High Similarity NPC31325
0.8819 High Similarity NPC82917
0.8819 High Similarity NPC39657
0.8819 High Similarity NPC108811
0.8819 High Similarity NPC58190
0.8819 High Similarity NPC202742
0.8819 High Similarity NPC114505
0.8819 High Similarity NPC275284
0.8819 High Similarity NPC18185
0.8819 High Similarity NPC70409
0.8819 High Similarity NPC262911
0.8819 High Similarity NPC294558
0.8819 High Similarity NPC213074
0.8819 High Similarity NPC99183
0.8819 High Similarity NPC15956
0.8819 High Similarity NPC263940
0.8819 High Similarity NPC193473
0.8819 High Similarity NPC224674
0.8819 High Similarity NPC170103
0.8811 High Similarity NPC181615
0.8806 High Similarity NPC5428
0.8803 High Similarity NPC173203
0.8803 High Similarity NPC163508
0.8797 High Similarity NPC194519
0.8797 High Similarity NPC148627
0.8794 High Similarity NPC263261
0.8794 High Similarity NPC87725
0.8794 High Similarity NPC471908
0.8794 High Similarity NPC471389
0.8794 High Similarity NPC247291
0.8794 High Similarity NPC471414
0.8794 High Similarity NPC311530
0.8788 High Similarity NPC473451
0.8786 High Similarity NPC193666
0.8786 High Similarity NPC88640
0.8786 High Similarity NPC123526
0.8784 High Similarity NPC157333
0.8777 High Similarity NPC471988
0.8777 High Similarity NPC269091
0.8777 High Similarity NPC248727
0.8777 High Similarity NPC265433

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC55793 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
0.8623 High Similarity NPD1613 Approved
0.8623 High Similarity NPD1612 Clinical (unspecified phase)
0.854 High Similarity NPD3027 Phase 3
0.8333 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD2861 Phase 2
0.8201 Intermediate Similarity NPD4908 Phase 1
0.8085 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7972 Intermediate Similarity NPD3620 Phase 2
0.7972 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD6234 Discontinued
0.795 Intermediate Similarity NPD7228 Approved
0.7905 Intermediate Similarity NPD6674 Discontinued
0.7834 Intermediate Similarity NPD4967 Phase 2
0.7834 Intermediate Similarity NPD4965 Approved
0.7834 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD4966 Approved
0.7826 Intermediate Similarity NPD6166 Phase 2
0.7826 Intermediate Similarity NPD1610 Phase 2
0.7826 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.782 Intermediate Similarity NPD5283 Phase 1
0.777 Intermediate Similarity NPD7266 Discontinued
0.7755 Intermediate Similarity NPD5588 Approved
0.775 Intermediate Similarity NPD7199 Phase 2
0.7671 Intermediate Similarity NPD5735 Approved
0.7669 Intermediate Similarity NPD228 Approved
0.7667 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD37 Approved
0.7643 Intermediate Similarity NPD1934 Approved
0.7613 Intermediate Similarity NPD1653 Approved
0.7582 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD7157 Approved
0.7571 Intermediate Similarity NPD3705 Approved
0.7568 Intermediate Similarity NPD4538 Approved
0.7568 Intermediate Similarity NPD4536 Approved
0.7568 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD6516 Phase 2
0.7554 Intermediate Similarity NPD5846 Approved
0.7546 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD3022 Approved
0.7519 Intermediate Similarity NPD3021 Approved
0.7517 Intermediate Similarity NPD5960 Phase 3
0.7516 Intermediate Similarity NPD5058 Phase 3
0.7515 Intermediate Similarity NPD3818 Discontinued
0.7484 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD4060 Phase 1
0.7483 Intermediate Similarity NPD1558 Phase 1
0.7481 Intermediate Similarity NPD7843 Approved
0.7471 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD1091 Approved
0.7444 Intermediate Similarity NPD2684 Approved
0.744 Intermediate Similarity NPD7240 Approved
0.7431 Intermediate Similarity NPD6584 Phase 3
0.7427 Intermediate Similarity NPD4663 Approved
0.7425 Intermediate Similarity NPD7074 Phase 3
0.7417 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD1548 Phase 1
0.7394 Intermediate Similarity NPD2489 Approved
0.7394 Intermediate Similarity NPD27 Approved
0.7386 Intermediate Similarity NPD6331 Phase 2
0.7381 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD3051 Approved
0.7375 Intermediate Similarity NPD8455 Phase 2
0.7368 Intermediate Similarity NPD7037 Approved
0.7365 Intermediate Similarity NPD7054 Approved
0.7365 Intermediate Similarity NPD5844 Phase 1
0.7357 Intermediate Similarity NPD1357 Approved
0.7353 Intermediate Similarity NPD4578 Approved
0.7353 Intermediate Similarity NPD4577 Approved
0.7347 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD4749 Approved
0.7343 Intermediate Similarity NPD2983 Phase 2
0.7343 Intermediate Similarity NPD2982 Phase 2
0.7338 Intermediate Similarity NPD6190 Approved
0.7333 Intermediate Similarity NPD2969 Approved
0.7333 Intermediate Similarity NPD2970 Approved
0.7321 Intermediate Similarity NPD7472 Approved
0.732 Intermediate Similarity NPD4236 Phase 3
0.732 Intermediate Similarity NPD4237 Approved
0.7317 Intermediate Similarity NPD8127 Discontinued
0.7308 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6233 Phase 2
0.7292 Intermediate Similarity NPD8651 Approved
0.7285 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD3882 Suspended
0.7283 Intermediate Similarity NPD7906 Approved
0.7279 Intermediate Similarity NPD7095 Approved
0.7279 Intermediate Similarity NPD4625 Phase 3
0.7273 Intermediate Similarity NPD4110 Phase 3
0.7273 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2981 Phase 2
0.7267 Intermediate Similarity NPD2801 Approved
0.7267 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD3018 Phase 2
0.7256 Intermediate Similarity NPD5494 Approved
0.7251 Intermediate Similarity NPD7310 Approved
0.7251 Intermediate Similarity NPD7312 Approved
0.7251 Intermediate Similarity NPD7311 Approved
0.7251 Intermediate Similarity NPD7313 Approved
0.7248 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD4140 Approved
0.7241 Intermediate Similarity NPD3094 Phase 2
0.7237 Intermediate Similarity NPD2161 Phase 2
0.7235 Intermediate Similarity NPD7685 Pre-registration
0.723 Intermediate Similarity NPD6798 Discontinued
0.7222 Intermediate Similarity NPD6582 Phase 2
0.7222 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6583 Phase 3
0.7222 Intermediate Similarity NPD5327 Phase 3
0.7219 Intermediate Similarity NPD7097 Phase 1
0.7209 Intermediate Similarity NPD7309 Approved
0.7208 Intermediate Similarity NPD5177 Phase 3
0.7208 Intermediate Similarity NPD3060 Approved
0.72 Intermediate Similarity NPD6355 Discontinued
0.7194 Intermediate Similarity NPD6671 Approved
0.7193 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD5763 Approved
0.719 Intermediate Similarity NPD1375 Discontinued
0.719 Intermediate Similarity NPD5762 Approved
0.7188 Intermediate Similarity NPD4380 Phase 2
0.7176 Intermediate Similarity NPD6797 Phase 2
0.7164 Intermediate Similarity NPD968 Approved
0.7161 Intermediate Similarity NPD4628 Phase 3
0.716 Intermediate Similarity NPD1465 Phase 2
0.716 Intermediate Similarity NPD5773 Approved
0.716 Intermediate Similarity NPD2978 Approved
0.716 Intermediate Similarity NPD2977 Approved
0.716 Intermediate Similarity NPD5772 Approved
0.7153 Intermediate Similarity NPD2231 Phase 2
0.7153 Intermediate Similarity NPD2235 Phase 2
0.7152 Intermediate Similarity NPD6653 Approved
0.7152 Intermediate Similarity NPD6353 Approved
0.7143 Intermediate Similarity NPD7680 Approved
0.7135 Intermediate Similarity NPD7251 Discontinued
0.7134 Intermediate Similarity NPD7213 Phase 3
0.7134 Intermediate Similarity NPD7212 Phase 2
0.7134 Intermediate Similarity NPD1511 Approved
0.7134 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD2560 Approved
0.7117 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD2563 Approved
0.7115 Intermediate Similarity NPD2677 Approved
0.7111 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD290 Approved
0.7107 Intermediate Similarity NPD2122 Discontinued
0.7103 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4162 Approved
0.7093 Intermediate Similarity NPD7808 Phase 3
0.7093 Intermediate Similarity NPD7549 Discontinued
0.7089 Intermediate Similarity NPD4123 Phase 3
0.7089 Intermediate Similarity NPD7447 Phase 1
0.7086 Intermediate Similarity NPD3657 Discovery
0.7083 Intermediate Similarity NPD3092 Approved
0.707 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6071 Discontinued
0.7063 Intermediate Similarity NPD5126 Approved
0.7063 Intermediate Similarity NPD5125 Phase 3
0.7051 Intermediate Similarity NPD4535 Phase 3
0.7051 Intermediate Similarity NPD7466 Approved
0.7044 Intermediate Similarity NPD7526 Approved
0.7044 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD1512 Approved
0.7044 Intermediate Similarity NPD52 Approved
0.7044 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6559 Discontinued
0.703 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD7833 Phase 2
0.703 Intermediate Similarity NPD7831 Phase 2
0.7025 Intermediate Similarity NPD7041 Phase 2
0.7025 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD2238 Phase 2
0.7012 Intermediate Similarity NPD3817 Phase 2
0.7011 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD8053 Approved
0.7011 Intermediate Similarity NPD8054 Approved
0.7006 Intermediate Similarity NPD5241 Discontinued
0.7006 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.6992 Remote Similarity NPD291 Approved
0.6981 Remote Similarity NPD1754 Clinical (unspecified phase)
0.698 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6978 Remote Similarity NPD5535 Approved
0.6975 Remote Similarity NPD4675 Approved
0.6975 Remote Similarity NPD4678 Approved
0.6974 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6974 Remote Similarity NPD4340 Discontinued
0.6974 Remote Similarity NPD5124 Phase 1
0.6972 Remote Similarity NPD5536 Phase 2
0.6968 Remote Similarity NPD6002 Phase 3
0.6968 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6004 Phase 3
0.6968 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6005 Phase 3
0.6964 Remote Similarity NPD6232 Discontinued
0.6964 Remote Similarity NPD3787 Discontinued

Structure

External Identifiers

PubChem CID   46186848
ChEMBL   CHEMBL1086906
ZINC  

Physicochemical Properties

Molecular Weight:  494.16
ALogP:  -3.6969
MLogP:  3.44
XLogP:  2.046
# Rotatable Bonds:  9
Polar Surface Area:  138.07
# H-Bond Aceptor:  3
# H-Bond Donor:  5
# Rings:  6
# Heavy Atoms:  36

Download Data

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