Natural Product: NPC236522

Natural Product ID:  NPC236522
Common Name:   (-)-Cubebinin
IUPAC Name:   (3R,4R)-3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol
Synonyms:   (-)-Cubebinin
Molecular Formula:   C24H32O8
Standard InCHIKey:  PIYHDSUVUSVLGU-HSQXHLSASA-N
Standard InCHI:  InChI=1S/C24H32O8/c1-26-18-9-14(10-19(27-2)22(18)30-5)7-16-13-32-24(25)17(16)8-15-11-20(28-3)23(31-6)21(12-15)29-4/h9-12,16-17,24-25H,7-8,13H2,1-6H3/t16-,17+,24?/m0/s1
Canonical SMILES:  COc1c(OC)cc(cc1OC)C[C@H]1C(O)OC[C@@H]1Cc1cc(OC)c(c(c1)OC)OC
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
NPO11169 Piper cubeba Species Piperaceae Eukaryota PMID[15679319]
NPO11169 Piper cubeba Species Piperaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens IC50 = 15000 nM 15679319
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens IC50 > 100000 nM 15679319

  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 NPC236522 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
0.9695 High Similarity NPC283949
0.9549 High Similarity NPC56091
0.9549 High Similarity NPC226547
0.9545 High Similarity NPC185908
0.9542 High Similarity NPC150534
0.9538 High Similarity NPC196937
0.9412 High Similarity NPC472712
0.9412 High Similarity NPC473046
0.9412 High Similarity NPC187774
0.9412 High Similarity NPC118385
0.9412 High Similarity NPC472713
0.9403 High Similarity NPC46591
0.9265 High Similarity NPC472714
0.9265 High Similarity NPC5262
0.9265 High Similarity NPC287124
0.9254 High Similarity NPC474039
0.9209 High Similarity NPC39657
0.9179 High Similarity NPC143895
0.9173 High Similarity NPC326095
0.9173 High Similarity NPC244983
0.9167 High Similarity NPC261812
0.9167 High Similarity NPC65183
0.9167 High Similarity NPC72046
0.9147 High Similarity NPC9891
0.9147 High Similarity NPC88297
0.9147 High Similarity NPC186845
0.9143 High Similarity NPC130449
0.9143 High Similarity NPC270751
0.9143 High Similarity NPC248132
0.913 High Similarity NPC166884
0.913 High Similarity NPC141569
0.913 High Similarity NPC477701
0.9118 High Similarity NPC177868
0.9104 High Similarity NPC25333
0.9104 High Similarity NPC49235
0.9104 High Similarity NPC148893
0.9098 High Similarity NPC266848
0.9098 High Similarity NPC1474
0.9098 High Similarity NPC136750
0.9091 High Similarity NPC192255
0.9078 High Similarity NPC35877
0.9078 High Similarity NPC286235
0.9078 High Similarity NPC55715
0.9078 High Similarity NPC55158
0.9078 High Similarity NPC51328
0.9078 High Similarity NPC95392
0.9058 High Similarity NPC324962
0.9058 High Similarity NPC12728
0.9058 High Similarity NPC185071
0.9051 High Similarity NPC472711
0.9044 High Similarity NPC156376
0.9037 High Similarity NPC197166
0.9037 High Similarity NPC11453
0.9037 High Similarity NPC121651
0.9037 High Similarity NPC172818
0.9037 High Similarity NPC25695
0.903 High Similarity NPC31530
0.903 High Similarity NPC287745
0.9023 High Similarity NPC204215
0.9023 High Similarity NPC175067
0.9015 High Similarity NPC63574
0.9014 High Similarity NPC472710
0.9014 High Similarity NPC472709
0.9008 High Similarity NPC54321
0.9008 High Similarity NPC328682
0.9008 High Similarity NPC281864
0.9 High Similarity NPC50683
0.9 High Similarity NPC285725
0.9 High Similarity NPC212890
0.9 High Similarity NPC112571
0.9 High Similarity NPC206882
0.8986 High Similarity NPC229172
0.8986 High Similarity NPC230538
0.8986 High Similarity NPC103637
0.8986 High Similarity NPC246947
0.8986 High Similarity NPC476356
0.8986 High Similarity NPC36531
0.8963 High Similarity NPC165155
0.8963 High Similarity NPC34103
0.8963 High Similarity NPC189474
0.8963 High Similarity NPC184938
0.8963 High Similarity NPC101624
0.8963 High Similarity NPC24490
0.8963 High Similarity NPC141765
0.8955 High Similarity NPC69513
0.8955 High Similarity NPC58585
0.8955 High Similarity NPC215833
0.8955 High Similarity NPC158331
0.8931 High Similarity NPC473092
0.8931 High Similarity NPC8050
0.8931 High Similarity NPC473093
0.8929 High Similarity NPC477702
0.8929 High Similarity NPC475868
0.8921 High Similarity NPC255566
0.8921 High Similarity NPC474808
0.8921 High Similarity NPC185307
0.8921 High Similarity NPC298317
0.8921 High Similarity NPC470950
0.8921 High Similarity NPC477898
0.8913 High Similarity NPC471908
0.8905 High Similarity NPC30951
0.8905 High Similarity NPC9068
0.8905 High Similarity NPC290714
0.8905 High Similarity NPC6369
0.8905 High Similarity NPC113550
0.8905 High Similarity NPC201404
0.8905 High Similarity NPC53722
0.8889 High Similarity NPC47181
0.8889 High Similarity NPC251981
0.8889 High Similarity NPC302610
0.8889 High Similarity NPC107478
0.8889 High Similarity NPC13745
0.8889 High Similarity NPC48863
0.8881 High Similarity NPC147616
0.8881 High Similarity NPC259742
0.8881 High Similarity NPC104077
0.8881 High Similarity NPC219671
0.8873 High Similarity NPC316676
0.8873 High Similarity NPC325720
0.8872 High Similarity NPC469612
0.8872 High Similarity NPC181079
0.8872 High Similarity NPC470624
0.8872 High Similarity NPC469614
0.8872 High Similarity NPC237169
0.8872 High Similarity NPC173308
0.8864 High Similarity NPC82862
0.8864 High Similarity NPC470084
0.8864 High Similarity NPC222127
0.8857 High Similarity NPC473045
0.8857 High Similarity NPC471063
0.8857 High Similarity NPC79429
0.8857 High Similarity NPC470235
0.8857 High Similarity NPC172171
0.8857 High Similarity NPC471667
0.8857 High Similarity NPC84181
0.8857 High Similarity NPC217635
0.8857 High Similarity NPC25292
0.8857 High Similarity NPC283995
0.8857 High Similarity NPC129417
0.8857 High Similarity NPC239254
0.8855 High Similarity NPC473960
0.8849 High Similarity NPC189115
0.8849 High Similarity NPC469559
0.8841 High Similarity NPC284464
0.8832 High Similarity NPC469981
0.8832 High Similarity NPC195196
0.8832 High Similarity NPC477938
0.8824 High Similarity NPC126409
0.8824 High Similarity NPC99572
0.8824 High Similarity NPC18576
0.8815 High Similarity NPC112237
0.8811 High Similarity NPC477698
0.8806 High Similarity NPC30043
0.8806 High Similarity NPC470095
0.8806 High Similarity NPC470096
0.8806 High Similarity NPC469625
0.8806 High Similarity NPC476345
0.8806 High Similarity NPC469613
0.8806 High Similarity NPC474017
0.8794 High Similarity NPC476301
0.8794 High Similarity NPC279298
0.8794 High Similarity NPC166506
0.8794 High Similarity NPC189239
0.8794 High Similarity NPC180953
0.8794 High Similarity NPC110763
0.8794 High Similarity NPC475096
0.8794 High Similarity NPC22150
0.8794 High Similarity NPC307466
0.8794 High Similarity NPC38041
0.8794 High Similarity NPC197352
0.8794 High Similarity NPC43508
0.8788 High Similarity NPC242032
0.8786 High Similarity NPC473044
0.8786 High Similarity NPC46092
0.8777 High Similarity NPC469661
0.8777 High Similarity NPC312199
0.8777 High Similarity NPC311530
0.876 High Similarity NPC477886
0.8759 High Similarity NPC199459
0.8759 High Similarity NPC177035
0.8759 High Similarity NPC52277
0.875 High Similarity NPC185680
0.875 High Similarity NPC218041
0.875 High Similarity NPC185955
0.875 High Similarity NPC469707
0.875 High Similarity NPC145979
0.875 High Similarity NPC238140
0.875 High Similarity NPC225815
0.875 High Similarity NPC9933
0.875 High Similarity NPC187194
0.875 High Similarity NPC256776
0.875 High Similarity NPC260781
0.875 High Similarity NPC214326
0.875 High Similarity NPC476411
0.875 High Similarity NPC473989
0.875 High Similarity NPC469706
0.875 High Similarity NPC145722
0.875 High Similarity NPC182368
0.8741 High Similarity NPC162093
0.8741 High Similarity NPC304821

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC236522 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
0.8657 High Similarity NPD3027 Phase 3
0.8473 Intermediate Similarity NPD3705 Approved
0.8446 Intermediate Similarity NPD37 Approved
0.84 Intermediate Similarity NPD4965 Approved
0.84 Intermediate Similarity NPD4966 Approved
0.84 Intermediate Similarity NPD4967 Phase 2
0.817 Intermediate Similarity NPD6234 Discontinued
0.8153 Intermediate Similarity NPD7228 Approved
0.8074 Intermediate Similarity NPD2982 Phase 2
0.8074 Intermediate Similarity NPD2983 Phase 2
0.8071 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8071 Intermediate Similarity NPD1613 Approved
0.8065 Intermediate Similarity NPD7199 Phase 2
0.8062 Intermediate Similarity NPD5283 Phase 1
0.8 Intermediate Similarity NPD2981 Phase 2
0.8 Intermediate Similarity NPD6674 Discontinued
0.7971 Intermediate Similarity NPD3018 Phase 2
0.7971 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD7240 Approved
0.7914 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD1357 Approved
0.7786 Intermediate Similarity NPD4908 Phase 1
0.7748 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD7266 Discontinued
0.7702 Intermediate Similarity NPD3818 Discontinued
0.7697 Intermediate Similarity NPD1653 Approved
0.7676 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD1610 Phase 2
0.7651 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD7074 Phase 3
0.7552 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD7054 Approved
0.7537 Intermediate Similarity NPD7157 Approved
0.7536 Intermediate Similarity NPD1091 Approved
0.7532 Intermediate Similarity NPD4005 Discontinued
0.75 Intermediate Similarity NPD1375 Discontinued
0.75 Intermediate Similarity NPD7472 Approved
0.7483 Intermediate Similarity NPD7124 Phase 2
0.7465 Intermediate Similarity NPD2861 Phase 2
0.7448 Intermediate Similarity NPD3620 Phase 2
0.7448 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD7843 Approved
0.7431 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD4749 Approved
0.7415 Intermediate Similarity NPD6111 Discontinued
0.74 Intermediate Similarity NPD4236 Phase 3
0.74 Intermediate Similarity NPD4237 Approved
0.7383 Intermediate Similarity NPD3540 Phase 1
0.7381 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD1548 Phase 1
0.7368 Intermediate Similarity NPD228 Approved
0.7368 Intermediate Similarity NPD5058 Phase 3
0.7365 Intermediate Similarity NPD7808 Phase 3
0.7315 Intermediate Similarity NPD3539 Phase 1
0.7305 Intermediate Similarity NPD7251 Discontinued
0.7296 Intermediate Similarity NPD3817 Phase 2
0.7278 Intermediate Similarity NPD1934 Approved
0.7273 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2684 Approved
0.7261 Intermediate Similarity NPD4675 Approved
0.7261 Intermediate Similarity NPD4678 Approved
0.725 Intermediate Similarity NPD3882 Suspended
0.725 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD4108 Discontinued
0.7246 Intermediate Similarity NPD6797 Phase 2
0.7241 Intermediate Similarity NPD4625 Phase 3
0.7237 Intermediate Similarity NPD4110 Phase 3
0.7237 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD3892 Phase 2
0.7233 Intermediate Similarity NPD2977 Approved
0.7233 Intermediate Similarity NPD2978 Approved
0.7222 Intermediate Similarity NPD5494 Approved
0.7218 Intermediate Similarity NPD3021 Approved
0.7218 Intermediate Similarity NPD3022 Approved
0.7212 Intermediate Similarity NPD7473 Discontinued
0.7211 Intermediate Similarity NPD4060 Phase 1
0.7208 Intermediate Similarity NPD4357 Discontinued
0.7205 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD6559 Discontinued
0.7202 Intermediate Similarity NPD7685 Pre-registration
0.7183 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD5536 Phase 2
0.7171 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD3384 Approved
0.717 Intermediate Similarity NPD3382 Approved
0.717 Intermediate Similarity NPD3383 Approved
0.7162 Intermediate Similarity NPD5735 Approved
0.7162 Intermediate Similarity NPD6355 Discontinued
0.716 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5762 Approved
0.7152 Intermediate Similarity NPD5763 Approved
0.7152 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6166 Phase 2
0.7152 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD6843 Phase 3
0.7151 Intermediate Similarity NPD6842 Approved
0.7151 Intermediate Similarity NPD6841 Approved
0.7143 Intermediate Similarity NPD5126 Approved
0.7143 Intermediate Similarity NPD5125 Phase 3
0.7135 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6232 Discontinued
0.7133 Intermediate Similarity NPD5588 Approved
0.7133 Intermediate Similarity NPD8651 Approved
0.7126 Intermediate Similarity NPD5844 Phase 1
0.7125 Intermediate Similarity NPD2801 Approved
0.7125 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD8455 Phase 2
0.7125 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD6331 Phase 2
0.7123 Intermediate Similarity NPD7095 Approved
0.7115 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD7680 Approved
0.7095 Intermediate Similarity NPD2238 Phase 2
0.7078 Intermediate Similarity NPD2219 Phase 1
0.7075 Intermediate Similarity NPD5109 Approved
0.7075 Intermediate Similarity NPD5110 Phase 2
0.7075 Intermediate Similarity NPD5111 Phase 2
0.7073 Intermediate Similarity NPD8127 Discontinued
0.7067 Intermediate Similarity NPD4538 Approved
0.7067 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD7097 Phase 1
0.7067 Intermediate Similarity NPD4536 Approved
0.7063 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3060 Approved
0.7059 Intermediate Similarity NPD5177 Phase 3
0.7055 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD3657 Discovery
0.7044 Intermediate Similarity NPD7028 Phase 2
0.703 Intermediate Similarity NPD7229 Phase 3
0.7024 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD7819 Suspended
0.7013 Intermediate Similarity NPD7466 Approved
0.7006 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7526 Approved
0.7006 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD52 Approved
0.7 Intermediate Similarity NPD6653 Approved
0.6994 Remote Similarity NPD4055 Discovery
0.6993 Remote Similarity NPD1608 Approved
0.6981 Remote Similarity NPD7261 Clinical (unspecified phase)
0.698 Remote Similarity NPD4140 Approved
0.698 Remote Similarity NPD1558 Phase 1
0.6974 Remote Similarity NPD2161 Phase 2
0.6974 Remote Similarity NPD6100 Approved
0.6974 Remote Similarity NPD6099 Approved
0.6968 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6963 Remote Similarity NPD4750 Phase 3
0.6959 Remote Similarity NPD7549 Discontinued
0.6954 Remote Similarity NPD6896 Approved
0.6954 Remote Similarity NPD6895 Approved
0.6948 Remote Similarity NPD1652 Phase 2
0.6944 Remote Similarity NPD5327 Phase 3
0.6944 Remote Similarity NPD3685 Discontinued
0.6943 Remote Similarity NPD4123 Phase 3
0.6937 Remote Similarity NPD4380 Phase 2
0.6933 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6933 Remote Similarity NPD230 Phase 1
0.6933 Remote Similarity NPD5124 Phase 1
0.6923 Remote Similarity NPD422 Phase 1
0.6923 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6914 Remote Similarity NPD1465 Phase 2
0.6914 Remote Similarity NPD5772 Approved
0.6914 Remote Similarity NPD5773 Approved
0.6913 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6908 Remote Similarity NPD5960 Phase 3
0.6908 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6908 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6906 Remote Similarity NPD6671 Approved
0.6903 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6903 Remote Similarity NPD4628 Phase 3
0.6901 Remote Similarity NPD6516 Phase 2
0.6901 Remote Similarity NPD5846 Approved
0.6899 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6696 Suspended
0.6886 Remote Similarity NPD5242 Approved
0.6886 Remote Similarity NPD3926 Phase 2
0.6883 Remote Similarity NPD970 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1511 Approved
0.6871 Remote Similarity NPD5353 Approved
0.6871 Remote Similarity NPD2560 Approved
0.6871 Remote Similarity NPD2563 Approved
0.687 Remote Similarity NPD1242 Phase 1
0.6863 Remote Similarity NPD2438 Suspended
0.6859 Remote Similarity NPD2677 Approved
0.6859 Remote Similarity NPD6190 Approved
0.6842 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4162 Approved
0.6835 Remote Similarity NPD2534 Approved
0.6835 Remote Similarity NPD2532 Approved
0.6835 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6835 Remote Similarity NPD2533 Approved
0.6835 Remote Similarity NPD7447 Phase 1
0.6831 Remote Similarity NPD5585 Approved
0.6826 Remote Similarity NPD3787 Discontinued

Structure

External Identifiers

PubChem CID   44575401
ChEMBL   CHEMBL480296
ZINC  

Physicochemical Properties

Molecular Weight:  448.21
ALogP:  -0.7512
MLogP:  3.22
XLogP:  2.341
# Rotatable Bonds:  17
Polar Surface Area:  84.84
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  32

Download Data

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