Natural Product: NPC277784

Natural Product ID:  NPC277784
Common Name:   Gnetulin
IUPAC Name:   (1E,2S,3S)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol
Synonyms:   Gnetulin
Molecular Formula:   C30H26O8
Standard InCHIKey:  YUGHGAXRXHODHK-MGOPEXEZSA-N
Standard InCHI:  InChI=1S/C30H26O8/c1-37-26-8-15(3-5-23(26)34)7-21-22-13-20(33)14-25(36)30(22)29(16-4-6-24(35)27(11-16)38-2)28(21)17-9-18(31)12-19(32)10-17/h3-14,28-29,31-36H,1-2H3/b21-7-/t28-,29+/m0/s1
Canonical SMILES:  COc1cc(ccc1O)/C=C1/c2cc(O)cc(c2[C@@H]([C@H]1c1cc(O)cc(c1)O)c1ccc(c(c1)OC)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
NPO2820 Artocarpus venenosa Species Moraceae Eukaryota UNPD*
NPO39 Actaea asiatica Species Ranunculaceae Eukaryota UNPD*
NPO1888 Nodularia harveyana Species Aphanizomenonaceae Bacteria UNPD*
NPO5631 Taraktogenos heterophylla NA NA NA UNPD*
NPO3783 Geodia lindgreni Species Geodiidae Eukaryota UNPD*
NPO6593 Mollisia ventosa Species Dermateaceae Eukaryota UNPD*
NPO4697 Gnetum ula Species Gnetaceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 70160 nM 21839642

  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 NPC277784 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
0.9416 High Similarity NPC472091
0.9416 High Similarity NPC472090
0.9416 High Similarity NPC472092
0.9281 High Similarity NPC472087
0.9281 High Similarity NPC472088
0.9209 High Similarity NPC472089
0.9143 High Similarity NPC183709
0.9124 High Similarity NPC313081
0.9065 High Similarity NPC55947
0.9037 High Similarity NPC126836
0.9014 High Similarity NPC15659
0.9014 High Similarity NPC304894
0.8986 High Similarity NPC69029
0.8986 High Similarity NPC10314
0.8986 High Similarity NPC294884
0.8986 High Similarity NPC200557
0.8986 High Similarity NPC158142
0.8986 High Similarity NPC108198
0.8966 High Similarity NPC476969
0.8963 High Similarity NPC471518
0.8963 High Similarity NPC471519
0.8958 High Similarity NPC262297
0.8944 High Similarity NPC173203
0.8944 High Similarity NPC163508
0.8929 High Similarity NPC230124
0.8929 High Similarity NPC6300
0.8929 High Similarity NPC275061
0.8929 High Similarity NPC184613
0.8929 High Similarity NPC132804
0.8929 High Similarity NPC220344
0.8929 High Similarity NPC114171
0.8929 High Similarity NPC243996
0.8921 High Similarity NPC143139
0.8921 High Similarity NPC202846
0.8913 High Similarity NPC66840
0.8913 High Similarity NPC209199
0.8913 High Similarity NPC256307
0.8913 High Similarity NPC125649
0.8905 High Similarity NPC161958
0.8905 High Similarity NPC14224
0.8897 High Similarity NPC329836
0.8889 High Similarity NPC211758
0.8889 High Similarity NPC126291
0.8889 High Similarity NPC87794
0.8865 High Similarity NPC12668
0.8865 High Similarity NPC22317
0.8865 High Similarity NPC308768
0.8857 High Similarity NPC242715
0.8857 High Similarity NPC22902
0.8857 High Similarity NPC56329
0.8857 High Similarity NPC230919
0.8857 High Similarity NPC200935
0.8857 High Similarity NPC266453
0.8857 High Similarity NPC94994
0.8849 High Similarity NPC241241
0.8841 High Similarity NPC32778
0.8832 High Similarity NPC238168
0.8832 High Similarity NPC473309
0.8832 High Similarity NPC232275
0.8832 High Similarity NPC237424
0.8815 High Similarity NPC236791
0.8815 High Similarity NPC127587
0.8815 High Similarity NPC324112
0.8815 High Similarity NPC82679
0.8815 High Similarity NPC246620
0.8815 High Similarity NPC74817
0.8815 High Similarity NPC124452
0.8815 High Similarity NPC293054
0.8815 High Similarity NPC159968
0.8815 High Similarity NPC282000
0.8815 High Similarity NPC169474
0.8811 High Similarity NPC469630
0.8794 High Similarity NPC105847
0.8794 High Similarity NPC243759
0.8794 High Similarity NPC29868
0.8794 High Similarity NPC79622
0.8794 High Similarity NPC212942
0.8794 High Similarity NPC218131
0.8786 High Similarity NPC300846
0.8786 High Similarity NPC114155
0.8786 High Similarity NPC30632
0.8786 High Similarity NPC476639
0.8777 High Similarity NPC56764
0.8777 High Similarity NPC289258
0.8777 High Similarity NPC276026
0.8777 High Similarity NPC469659
0.8777 High Similarity NPC555
0.8777 High Similarity NPC7515
0.8777 High Similarity NPC160697
0.8777 High Similarity NPC206737
0.8777 High Similarity NPC188378
0.8768 High Similarity NPC6451
0.8768 High Similarity NPC474134
0.8768 High Similarity NPC131128
0.8759 High Similarity NPC254000
0.875 High Similarity NPC317237
0.875 High Similarity NPC44530
0.875 High Similarity NPC154866
0.875 High Similarity NPC277951
0.8741 High Similarity NPC76451
0.8741 High Similarity NPC28730
0.8741 High Similarity NPC470917
0.8741 High Similarity NPC175838
0.8741 High Similarity NPC191231
0.8741 High Similarity NPC18924
0.8741 High Similarity NPC78974
0.8741 High Similarity NPC44748
0.8741 High Similarity NPC214406
0.8741 High Similarity NPC223136
0.8741 High Similarity NPC103823
0.8723 High Similarity NPC151656
0.8723 High Similarity NPC6262
0.8723 High Similarity NPC201145
0.8723 High Similarity NPC272157
0.8723 High Similarity NPC266006
0.8723 High Similarity NPC90615
0.8723 High Similarity NPC73535
0.8723 High Similarity NPC25111
0.8716 High Similarity NPC321972
0.8716 High Similarity NPC324517
0.8716 High Similarity NPC329343
0.8714 High Similarity NPC180602
0.8714 High Similarity NPC214853
0.8714 High Similarity NPC240279
0.8714 High Similarity NPC55239
0.8707 High Similarity NPC318373
0.8707 High Similarity NPC321657
0.8707 High Similarity NPC211561
0.8696 High Similarity NPC45715
0.8696 High Similarity NPC474356
0.8696 High Similarity NPC15543
0.8696 High Similarity NPC12275
0.8686 High Similarity NPC212015
0.8681 High Similarity NPC155392
0.8681 High Similarity NPC274721
0.8681 High Similarity NPC135767
0.8676 High Similarity NPC252131
0.8676 High Similarity NPC266555
0.8671 High Similarity NPC178054
0.8667 High Similarity NPC113495
0.8667 High Similarity NPC299584
0.8667 High Similarity NPC105925
0.8667 High Similarity NPC472093
0.8667 High Similarity NPC234400
0.8667 High Similarity NPC17943
0.8667 High Similarity NPC265483
0.8667 High Similarity NPC251855
0.8667 High Similarity NPC60885
0.8667 High Similarity NPC82483
0.8667 High Similarity NPC116907
0.8667 High Similarity NPC233410
0.8667 High Similarity NPC298757
0.8667 High Similarity NPC221077
0.8667 High Similarity NPC157333
0.8667 High Similarity NPC57490
0.8667 High Similarity NPC117214
0.8667 High Similarity NPC208950
0.8667 High Similarity NPC203133
0.8667 High Similarity NPC193544
0.8667 High Similarity NPC475169
0.8657 High Similarity NPC197757
0.8657 High Similarity NPC228922
0.8657 High Similarity NPC121115
0.8652 High Similarity NPC265433
0.8652 High Similarity NPC205442
0.8652 High Similarity NPC248727
0.8652 High Similarity NPC162659
0.8652 High Similarity NPC270456
0.8652 High Similarity NPC133025
0.8649 High Similarity NPC477612
0.8643 High Similarity NPC317380
0.8643 High Similarity NPC141023
0.8639 High Similarity NPC227516
0.8639 High Similarity NPC20757
0.8633 High Similarity NPC303144
0.863 High Similarity NPC317053
0.863 High Similarity NPC260397
0.863 High Similarity NPC324492
0.8623 High Similarity NPC299221
0.8623 High Similarity NPC192687
0.8623 High Similarity NPC311680
0.8623 High Similarity NPC224157
0.8623 High Similarity NPC234488
0.8623 High Similarity NPC51840
0.8621 High Similarity NPC28440
0.8621 High Similarity NPC171932
0.8621 High Similarity NPC473108
0.8613 High Similarity NPC28765
0.8609 High Similarity NPC202104
0.8603 High Similarity NPC223953
0.8601 High Similarity NPC34431
0.8601 High Similarity NPC262189
0.8601 High Similarity NPC184797
0.8601 High Similarity NPC73505
0.8601 High Similarity NPC295719
0.8601 High Similarity NPC266197
0.8601 High Similarity NPC309124
0.8601 High Similarity NPC291101
0.8601 High Similarity NPC165026
0.8592 High Similarity NPC301765

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC277784 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
0.8417 Intermediate Similarity NPD3027 Phase 3
0.8214 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD4908 Phase 1
0.8143 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8112 Intermediate Similarity NPD3620 Phase 2
0.8112 Intermediate Similarity NPD1613 Approved
0.8112 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.8112 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8101 Intermediate Similarity NPD7199 Phase 2
0.8099 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD3018 Phase 2
0.7862 Intermediate Similarity NPD6234 Discontinued
0.7836 Intermediate Similarity NPD5283 Phase 1
0.7771 Intermediate Similarity NPD37 Approved
0.773 Intermediate Similarity NPD2982 Phase 2
0.773 Intermediate Similarity NPD2983 Phase 2
0.7714 Intermediate Similarity NPD1610 Phase 2
0.7687 Intermediate Similarity NPD228 Approved
0.766 Intermediate Similarity NPD2981 Phase 2
0.7655 Intermediate Similarity NPD4625 Phase 3
0.7639 Intermediate Similarity NPD2861 Phase 2
0.7636 Intermediate Similarity NPD7228 Approved
0.7625 Intermediate Similarity NPD4966 Approved
0.7625 Intermediate Similarity NPD4967 Phase 2
0.7625 Intermediate Similarity NPD4965 Approved
0.7607 Intermediate Similarity NPD6232 Discontinued
0.7606 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD7473 Discontinued
0.7537 Intermediate Similarity NPD3021 Approved
0.7537 Intermediate Similarity NPD3022 Approved
0.7529 Intermediate Similarity NPD8054 Approved
0.7529 Intermediate Similarity NPD8053 Approved
0.7516 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6166 Phase 2
0.7515 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4060 Phase 1
0.7483 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD4749 Approved
0.7448 Intermediate Similarity NPD4624 Approved
0.7438 Intermediate Similarity NPD1934 Approved
0.7429 Intermediate Similarity NPD1548 Phase 1
0.7403 Intermediate Similarity NPD3892 Phase 2
0.7391 Intermediate Similarity NPD2801 Approved
0.7338 Intermediate Similarity NPD6674 Discontinued
0.7333 Intermediate Similarity NPD3657 Discovery
0.7333 Intermediate Similarity NPD5735 Approved
0.7329 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD5763 Approved
0.732 Intermediate Similarity NPD5762 Approved
0.732 Intermediate Similarity NPD3540 Phase 1
0.7301 Intermediate Similarity NPD3882 Suspended
0.7285 Intermediate Similarity NPD4097 Suspended
0.7284 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD1465 Phase 2
0.7278 Intermediate Similarity NPD5844 Phase 1
0.726 Intermediate Similarity NPD3094 Phase 2
0.7256 Intermediate Similarity NPD7831 Phase 2
0.7256 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD7833 Phase 2
0.7255 Intermediate Similarity NPD3539 Phase 1
0.725 Intermediate Similarity NPD4005 Discontinued
0.7248 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD8127 Discontinued
0.7222 Intermediate Similarity NPD3092 Approved
0.7222 Intermediate Similarity NPD3705 Approved
0.7193 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD1653 Approved
0.7153 Intermediate Similarity NPD4750 Phase 3
0.7152 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1511 Approved
0.7152 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7041 Phase 2
0.7152 Intermediate Similarity NPD4055 Discovery
0.7151 Intermediate Similarity NPD7240 Approved
0.7135 Intermediate Similarity NPD7074 Phase 3
0.7133 Intermediate Similarity NPD5109 Approved
0.7133 Intermediate Similarity NPD5111 Phase 2
0.7133 Intermediate Similarity NPD5110 Phase 2
0.7126 Intermediate Similarity NPD6959 Discontinued
0.7123 Intermediate Similarity NPD5327 Phase 3
0.7118 Intermediate Similarity NPD8252 Approved
0.7118 Intermediate Similarity NPD3818 Discontinued
0.7118 Intermediate Similarity NPD8251 Approved
0.7118 Intermediate Similarity NPD8099 Discontinued
0.7115 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD7447 Phase 1
0.7097 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD7124 Phase 2
0.7086 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7054 Approved
0.7076 Intermediate Similarity NPD8156 Discontinued
0.707 Intermediate Similarity NPD3750 Approved
0.7063 Intermediate Similarity NPD3091 Approved
0.7063 Intermediate Similarity NPD1512 Approved
0.7059 Intermediate Similarity NPD6353 Approved
0.7051 Intermediate Similarity NPD7037 Approved
0.7048 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD4357 Discontinued
0.7044 Intermediate Similarity NPD7213 Phase 3
0.7044 Intermediate Similarity NPD7212 Phase 2
0.7039 Intermediate Similarity NPD4140 Approved
0.7039 Intermediate Similarity NPD1558 Phase 1
0.7035 Intermediate Similarity NPD7472 Approved
0.7032 Intermediate Similarity NPD6099 Approved
0.7032 Intermediate Similarity NPD6100 Approved
0.703 Intermediate Similarity NPD3817 Phase 2
0.703 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD940 Approved
0.7015 Intermediate Similarity NPD846 Approved
0.7011 Intermediate Similarity NPD7549 Discontinued
0.7006 Intermediate Similarity NPD5177 Phase 3
0.7 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2489 Approved
0.7 Intermediate Similarity NPD27 Approved
0.6994 Remote Similarity NPD7028 Phase 2
0.6994 Remote Similarity NPD4380 Phase 2
0.6993 Remote Similarity NPD6355 Discontinued
0.6993 Remote Similarity NPD5536 Phase 2
0.6988 Remote Similarity NPD7768 Phase 2
0.6987 Remote Similarity NPD7266 Discontinued
0.698 Remote Similarity NPD6584 Phase 3
0.6972 Remote Similarity NPD7157 Approved
0.6968 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4626 Approved
0.6966 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4059 Approved
0.6964 Remote Similarity NPD5494 Approved
0.6962 Remote Similarity NPD7466 Approved
0.6962 Remote Similarity NPD6331 Phase 2
0.6957 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7095 Approved
0.6943 Remote Similarity NPD970 Clinical (unspecified phase)
0.694 Remote Similarity NPD1242 Phase 1
0.6937 Remote Similarity NPD7390 Discontinued
0.6933 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2238 Phase 2
0.6918 Remote Similarity NPD5241 Discontinued
0.6918 Remote Similarity NPD5084 Clinical (unspecified phase)
0.691 Remote Similarity NPD7906 Approved
0.6908 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6908 Remote Similarity NPD6798 Discontinued
0.6906 Remote Similarity NPD5451 Approved
0.6903 Remote Similarity NPD6111 Discontinued
0.6899 Remote Similarity NPD3060 Approved
0.6897 Remote Similarity NPD1357 Approved
0.6897 Remote Similarity NPD6797 Phase 2
0.6894 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6894 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6886 Remote Similarity NPD6788 Approved
0.6882 Remote Similarity NPD7229 Phase 3
0.6882 Remote Similarity NPD7680 Approved
0.6882 Remote Similarity NPD3051 Approved
0.6879 Remote Similarity NPD7843 Approved
0.6875 Remote Similarity NPD4577 Approved
0.6875 Remote Similarity NPD4578 Approved
0.6871 Remote Similarity NPD422 Phase 1
0.6867 Remote Similarity NPD7819 Suspended
0.6866 Remote Similarity NPD3020 Approved
0.6863 Remote Similarity NPD2674 Phase 3
0.6859 Remote Similarity NPD1510 Phase 2
0.6857 Remote Similarity NPD7251 Discontinued
0.6857 Remote Similarity NPD7685 Pre-registration
0.6855 Remote Similarity NPD7003 Approved
0.6855 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6855 Remote Similarity NPD4110 Phase 3
0.6855 Remote Similarity NPD8166 Discontinued
0.6854 Remote Similarity NPD4663 Approved
0.6853 Remote Similarity NPD6671 Approved
0.6849 Remote Similarity NPD5846 Approved
0.6849 Remote Similarity NPD3019 Approved
0.6849 Remote Similarity NPD6516 Phase 2
0.6849 Remote Similarity NPD3095 Discontinued
0.6848 Remote Similarity NPD5090 Approved
0.6848 Remote Similarity NPD5089 Approved
0.6848 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6846 Remote Similarity NPD8651 Approved
0.6845 Remote Similarity NPD3749 Approved
0.6842 Remote Similarity NPD2970 Approved
0.6842 Remote Similarity NPD2969 Approved
0.6839 Remote Similarity NPD2157 Approved
0.6835 Remote Similarity NPD2684 Approved
0.6824 Remote Similarity NPD2230 Approved
0.6824 Remote Similarity NPD2233 Approved
0.6824 Remote Similarity NPD2232 Approved
0.6818 Remote Similarity NPD943 Approved
0.6818 Remote Similarity NPD8453 Clinical (unspecified phase)
0.6818 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6818 Remote Similarity NPD1240 Approved
0.6818 Remote Similarity NPD7808 Phase 3
0.6802 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6802 Remote Similarity NPD2898 Approved
0.68 Remote Similarity NPD4339 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   56673069
ChEMBL   CHEMBL1818263
ZINC  

Physicochemical Properties

Molecular Weight:  514.16
ALogP:  -2.5962
MLogP:  3.88
XLogP:  3.471
# Rotatable Bonds:  13
Polar Surface Area:  139.84
# H-Bond Aceptor:  0
# H-Bond Donor:  6
# Rings:  5
# Heavy Atoms:  38

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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