Natural Product: NPC469586

Natural Product ID:  NPC469586
Common Name:   Khainaoside A
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[5-[(3R,3aS,6R,6aS)-3-(1,3-benzodioxol-5-yl)-3a,6a-dihydroxy-1,3,4,6-tetrahydrofuro[3,4-c]furan-6-yl]-2-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Molecular Formula:   C25H28O13
Standard InCHIKey:  HUVQMIPFAVBQIA-KYBLTUFESA-N
Standard InCHI:  InChI=1S/C25H28O13/c26-7-17-18(28)19(29)20(30)23(38-17)37-15-5-11(1-3-13(15)27)21-24(31)8-34-22(25(24,32)9-33-21)12-2-4-14-16(6-12)36-10-35-14/h1-6,17-23,26-32H,7-10H2/t17-,18-,19+,20-,21-,22-,23-,24+,25+/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](Oc2cc(ccc2O)[C@H]2OC[C@]3([C@]2(O)CO[C@@H]3c2ccc3c(c2)OCO3)O)[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
NPO25391 Vitex glabrata Species Lamiaceae Eukaryota Leaves Chantaburi Province, Thailand 2007-NOV PMID[19943620]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT396 Cell Line T47D Homo sapiens Activity = 3 nM 17190444
NPT396 Cell Line T47D Homo sapiens Activity < 0.1 nM 17060530
NPT83 Cell Line MCF7 Homo sapiens Activity < 0.1 nM 17606681
NPT396 Cell Line T47D Homo sapiens Activity < 0.1 nM PubChem BioAssay data set
NPT83 Cell Line MCF7 Homo sapiens Activity < 0.1 nM PubChem BioAssay data set

  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 NPC469586 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
0.9712 High Similarity NPC18979
0.9643 High Similarity NPC112861
0.9571 High Similarity NPC22150
0.9571 High Similarity NPC38041
0.9571 High Similarity NPC279298
0.9568 High Similarity NPC46092
0.95 High Similarity NPC283995
0.95 High Similarity NPC470235
0.95 High Similarity NPC129417
0.95 High Similarity NPC84181
0.9429 High Similarity NPC477898
0.9429 High Similarity NPC185307
0.9429 High Similarity NPC470950
0.9424 High Similarity NPC471908
0.9375 High Similarity NPC98624
0.9375 High Similarity NPC475224
0.9357 High Similarity NPC476356
0.9357 High Similarity NPC246947
0.9306 High Similarity NPC51328
0.9306 High Similarity NPC55158
0.9306 High Similarity NPC286235
0.9286 High Similarity NPC472711
0.9281 High Similarity NPC156376
0.9281 High Similarity NPC193666
0.9281 High Similarity NPC123526
0.9281 High Similarity NPC88640
0.9236 High Similarity NPC248132
0.9236 High Similarity NPC130449
0.9225 High Similarity NPC179521
0.9214 High Similarity NPC106944
0.9209 High Similarity NPC138738
0.9209 High Similarity NPC470413
0.9203 High Similarity NPC18576
0.9167 High Similarity NPC275284
0.9167 High Similarity NPC114505
0.9167 High Similarity NPC15956
0.9167 High Similarity NPC31325
0.9167 High Similarity NPC213074
0.9167 High Similarity NPC224674
0.9167 High Similarity NPC193473
0.9167 High Similarity NPC39657
0.9149 High Similarity NPC469661
0.9137 High Similarity NPC199459
0.9137 High Similarity NPC52277
0.9137 High Similarity NPC177035
0.913 High Similarity NPC47181
0.913 High Similarity NPC470881
0.913 High Similarity NPC476411
0.9097 High Similarity NPC276753
0.9097 High Similarity NPC205796
0.9091 High Similarity NPC25292
0.9091 High Similarity NPC473045
0.9085 High Similarity NPC302506
0.9085 High Similarity NPC189115
0.9078 High Similarity NPC55793
0.9071 High Similarity NPC101807
0.9071 High Similarity NPC304152
0.9071 High Similarity NPC469981
0.9065 High Similarity NPC142547
0.9065 High Similarity NPC101624
0.9065 High Similarity NPC135777
0.9065 High Similarity NPC184938
0.9058 High Similarity NPC25821
0.9058 High Similarity NPC6836
0.9028 High Similarity NPC43508
0.9028 High Similarity NPC476301
0.9021 High Similarity NPC298317
0.9021 High Similarity NPC185071
0.9021 High Similarity NPC12728
0.9021 High Similarity NPC473044
0.9021 High Similarity NPC265154
0.9021 High Similarity NPC255566
0.8993 High Similarity NPC187194
0.8986 High Similarity NPC4940
0.8986 High Similarity NPC252833
0.8973 High Similarity NPC226153
0.8973 High Similarity NPC304048
0.8966 High Similarity NPC99515
0.8966 High Similarity NPC190714
0.8958 High Similarity NPC472712
0.8958 High Similarity NPC187774
0.8958 High Similarity NPC217635
0.8958 High Similarity NPC471063
0.8958 High Similarity NPC472713
0.8958 High Similarity NPC79429
0.8958 High Similarity NPC118385
0.8958 High Similarity NPC473046
0.8958 High Similarity NPC471667
0.8951 High Similarity NPC253878
0.8951 High Similarity NPC60249
0.8951 High Similarity NPC48309
0.8951 High Similarity NPC469559
0.8936 High Similarity NPC477798
0.8936 High Similarity NPC477797
0.8936 High Similarity NPC59324
0.8936 High Similarity NPC65530
0.8921 High Similarity NPC169973
0.8913 High Similarity NPC248307
0.8913 High Similarity NPC65942
0.8913 High Similarity NPC9912
0.8912 High Similarity NPC44452
0.8897 High Similarity NPC475096
0.8889 High Similarity NPC81638
0.8889 High Similarity NPC113680
0.8889 High Similarity NPC278961
0.8881 High Similarity NPC76871
0.8881 High Similarity NPC471414
0.8874 High Similarity NPC478055
0.8874 High Similarity NPC11411
0.8873 High Similarity NPC98777
0.8873 High Similarity NPC212770
0.8865 High Similarity NPC203230
0.8865 High Similarity NPC242028
0.8857 High Similarity NPC35731
0.8851 High Similarity NPC238140
0.8851 High Similarity NPC472710
0.8851 High Similarity NPC472709
0.8849 High Similarity NPC259742
0.8849 High Similarity NPC104077
0.8849 High Similarity NPC219671
0.8849 High Similarity NPC181049
0.8849 High Similarity NPC147616
0.8849 High Similarity NPC471505
0.8849 High Similarity NPC207400
0.8849 High Similarity NPC106739
0.8844 High Similarity NPC301961
0.8844 High Similarity NPC166584
0.8844 High Similarity NPC175976
0.8841 High Similarity NPC472024
0.8841 High Similarity NPC171550
0.8841 High Similarity NPC80600
0.8841 High Similarity NPC134764
0.8836 High Similarity NPC93610
0.8836 High Similarity NPC226540
0.8836 High Similarity NPC241846
0.8836 High Similarity NPC125755
0.8836 High Similarity NPC162193
0.8832 High Similarity NPC72529
0.8828 High Similarity NPC76176
0.8828 High Similarity NPC469313
0.8828 High Similarity NPC168579
0.8828 High Similarity NPC138227
0.8819 High Similarity NPC475084
0.8819 High Similarity NPC5262
0.8819 High Similarity NPC472714
0.8811 High Similarity NPC226547
0.8811 High Similarity NPC56091
0.8811 High Similarity NPC177868
0.8811 High Similarity NPC46591
0.8808 High Similarity NPC186316
0.88 High Similarity NPC299706
0.88 High Similarity NPC61604
0.88 High Similarity NPC115466
0.88 High Similarity NPC245615
0.8794 High Similarity NPC174191
0.8784 High Similarity NPC95392
0.8784 High Similarity NPC55715
0.8784 High Similarity NPC240521
0.8784 High Similarity NPC35877
0.8777 High Similarity NPC158079
0.8777 High Similarity NPC228346
0.8777 High Similarity NPC40432
0.8777 High Similarity NPC161557
0.8777 High Similarity NPC82111
0.8777 High Similarity NPC277804
0.8777 High Similarity NPC27843
0.8777 High Similarity NPC115207
0.8777 High Similarity NPC227160
0.8777 High Similarity NPC7171
0.8776 High Similarity NPC227902
0.8768 High Similarity NPC86030
0.8768 High Similarity NPC307110
0.8768 High Similarity NPC26653
0.8768 High Similarity NPC5851
0.8768 High Similarity NPC248355
0.8768 High Similarity NPC166040
0.8768 High Similarity NPC270849
0.8767 High Similarity NPC11422
0.8767 High Similarity NPC178014
0.8767 High Similarity NPC286245
0.8767 High Similarity NPC277867
0.8767 High Similarity NPC272619
0.8767 High Similarity NPC474749
0.8767 High Similarity NPC161700
0.8767 High Similarity NPC42716
0.8759 High Similarity NPC478239
0.8759 High Similarity NPC37793
0.8759 High Similarity NPC252169
0.875 High Similarity NPC186406
0.875 High Similarity NPC163635
0.8742 High Similarity NPC159922
0.8741 High Similarity NPC292487
0.8741 High Similarity NPC183781
0.8732 High Similarity NPC77861
0.8732 High Similarity NPC25695
0.8732 High Similarity NPC172818
0.8723 High Similarity NPC87696
0.8716 High Similarity NPC270751
0.8716 High Similarity NPC116229
0.8714 High Similarity NPC158526

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469586 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
0.8322 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD1613 Approved
0.8239 Intermediate Similarity NPD3027 Phase 3
0.8108 Intermediate Similarity NPD7266 Discontinued
0.8052 Intermediate Similarity NPD1653 Approved
0.805 Intermediate Similarity NPD6234 Discontinued
0.8042 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD7228 Approved
0.8 Intermediate Similarity NPD6674 Discontinued
0.7972 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD3705 Approved
0.7929 Intermediate Similarity NPD1091 Approved
0.7927 Intermediate Similarity NPD3818 Discontinued
0.7925 Intermediate Similarity NPD4966 Approved
0.7925 Intermediate Similarity NPD4967 Phase 2
0.7925 Intermediate Similarity NPD4965 Approved
0.7847 Intermediate Similarity NPD2861 Phase 2
0.7843 Intermediate Similarity NPD5058 Phase 3
0.7736 Intermediate Similarity NPD37 Approved
0.773 Intermediate Similarity NPD7199 Phase 2
0.7725 Intermediate Similarity NPD7074 Phase 3
0.7714 Intermediate Similarity NPD1357 Approved
0.7677 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD7054 Approved
0.7619 Intermediate Similarity NPD7472 Approved
0.753 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7240 Approved
0.7529 Intermediate Similarity NPD7685 Pre-registration
0.75 Intermediate Similarity NPD5588 Approved
0.7485 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD6797 Phase 2
0.7469 Intermediate Similarity NPD2977 Approved
0.7469 Intermediate Similarity NPD2978 Approved
0.7469 Intermediate Similarity NPD8455 Phase 2
0.7467 Intermediate Similarity NPD3620 Phase 2
0.7467 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD4908 Phase 1
0.7431 Intermediate Similarity NPD1610 Phase 2
0.7427 Intermediate Similarity NPD7251 Discontinued
0.7419 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD5283 Phase 1
0.7407 Intermediate Similarity NPD1934 Approved
0.7403 Intermediate Similarity NPD1375 Discontinued
0.7391 Intermediate Similarity NPD228 Approved
0.7384 Intermediate Similarity NPD7808 Phase 3
0.7378 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD6559 Discontinued
0.7322 Intermediate Similarity NPD7680 Approved
0.732 Intermediate Similarity NPD4538 Approved
0.732 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD4536 Approved
0.7305 Intermediate Similarity NPD7157 Approved
0.7292 Intermediate Similarity NPD5125 Phase 3
0.7292 Intermediate Similarity NPD5126 Approved
0.7278 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD6166 Phase 2
0.7278 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5960 Phase 3
0.7256 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD4060 Phase 1
0.7237 Intermediate Similarity NPD1558 Phase 1
0.7215 Intermediate Similarity NPD6190 Approved
0.7214 Intermediate Similarity NPD7843 Approved
0.7211 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD5735 Approved
0.7179 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD2684 Approved
0.7153 Intermediate Similarity NPD1548 Phase 1
0.7152 Intermediate Similarity NPD4625 Phase 3
0.7152 Intermediate Similarity NPD7095 Approved
0.7122 Intermediate Similarity NPD3021 Approved
0.7122 Intermediate Similarity NPD3022 Approved
0.7105 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD7097 Phase 1
0.7095 Intermediate Similarity NPD2982 Phase 2
0.7095 Intermediate Similarity NPD4749 Approved
0.7095 Intermediate Similarity NPD2983 Phase 2
0.7089 Intermediate Similarity NPD4237 Approved
0.7089 Intermediate Similarity NPD4236 Phase 3
0.7066 Intermediate Similarity NPD3882 Suspended
0.7063 Intermediate Similarity NPD6671 Approved
0.7063 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3787 Discontinued
0.7055 Intermediate Similarity NPD6516 Phase 2
0.7055 Intermediate Similarity NPD5846 Approved
0.7052 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD4108 Discontinued
0.7048 Intermediate Similarity NPD2801 Approved
0.7047 Intermediate Similarity NPD8651 Approved
0.7044 Intermediate Similarity NPD4628 Phase 3
0.7044 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6331 Phase 2
0.7044 Intermediate Similarity NPD4110 Phase 3
0.7027 Intermediate Similarity NPD2981 Phase 2
0.7024 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD4663 Approved
0.702 Intermediate Similarity NPD3018 Phase 2
0.7006 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7906 Approved
0.6981 Remote Similarity NPD3060 Approved
0.6977 Remote Similarity NPD2489 Approved
0.6977 Remote Similarity NPD27 Approved
0.6975 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6971 Remote Similarity NPD7993 Clinical (unspecified phase)
0.697 Remote Similarity NPD7028 Phase 2
0.6968 Remote Similarity NPD6355 Discontinued
0.6962 Remote Similarity NPD5762 Approved
0.6962 Remote Similarity NPD5763 Approved
0.6954 Remote Similarity NPD6584 Phase 3
0.6954 Remote Similarity NPD5844 Phase 1
0.6949 Remote Similarity NPD7312 Approved
0.6949 Remote Similarity NPD7311 Approved
0.6949 Remote Similarity NPD8313 Approved
0.6949 Remote Similarity NPD4577 Approved
0.6949 Remote Similarity NPD7310 Approved
0.6949 Remote Similarity NPD7313 Approved
0.6949 Remote Similarity NPD8312 Approved
0.6949 Remote Similarity NPD4578 Approved
0.6948 Remote Similarity NPD6233 Phase 2
0.6946 Remote Similarity NPD5772 Approved
0.6946 Remote Similarity NPD1465 Phase 2
0.6946 Remote Similarity NPD5773 Approved
0.6943 Remote Similarity NPD7033 Discontinued
0.6923 Remote Similarity NPD6653 Approved
0.6919 Remote Similarity NPD2970 Approved
0.6919 Remote Similarity NPD2969 Approved
0.6914 Remote Similarity NPD1511 Approved
0.691 Remote Similarity NPD7309 Approved
0.6909 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6906 Remote Similarity NPD968 Approved
0.6905 Remote Similarity NPD2560 Approved
0.6905 Remote Similarity NPD3817 Phase 2
0.6905 Remote Similarity NPD2563 Approved
0.6903 Remote Similarity NPD4140 Approved
0.6901 Remote Similarity NPD8127 Discontinued
0.6899 Remote Similarity NPD2161 Phase 2
0.6897 Remote Similarity NPD3751 Discontinued
0.6894 Remote Similarity NPD2677 Approved
0.6886 Remote Similarity NPD3382 Approved
0.6886 Remote Similarity NPD3384 Approved
0.6886 Remote Similarity NPD3383 Approved
0.6883 Remote Similarity NPD6798 Discontinued
0.6875 Remote Similarity NPD5177 Phase 3
0.6875 Remote Similarity NPD4162 Approved
0.6871 Remote Similarity NPD4123 Phase 3
0.6867 Remote Similarity NPD4380 Phase 2
0.686 Remote Similarity NPD6071 Discontinued
0.686 Remote Similarity NPD3051 Approved
0.6859 Remote Similarity NPD4340 Discontinued
0.6857 Remote Similarity NPD290 Approved
0.6848 Remote Similarity NPD4210 Discontinued
0.6848 Remote Similarity NPD3687 Approved
0.6848 Remote Similarity NPD3686 Approved
0.6842 Remote Similarity NPD5494 Approved
0.6839 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6835 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6835 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6832 Remote Similarity NPD4535 Phase 3
0.6829 Remote Similarity NPD1512 Approved
0.6829 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5604 Discontinued
0.6821 Remote Similarity NPD6696 Suspended
0.6815 Remote Similarity NPD6353 Approved
0.6813 Remote Similarity NPD2424 Discontinued
0.68 Remote Similarity NPD2231 Phase 2
0.68 Remote Similarity NPD2235 Phase 2
0.6796 Remote Similarity NPD6842 Approved
0.6796 Remote Similarity NPD6841 Approved
0.6796 Remote Similarity NPD6843 Phase 3
0.6795 Remote Similarity NPD2238 Phase 2
0.6795 Remote Similarity NPD5837 Clinical (unspecified phase)
0.679 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7945 Clinical (unspecified phase)
0.678 Remote Similarity NPD7007 Discovery
0.6776 Remote Similarity NPD3094 Phase 2
0.6772 Remote Similarity NPD4978 Clinical (unspecified phase)
0.677 Remote Similarity NPD1652 Phase 2
0.6768 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6766 Remote Similarity NPD4678 Approved
0.6766 Remote Similarity NPD4675 Approved
0.6758 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6757 Remote Similarity NPD5582 Discontinued
0.6755 Remote Similarity NPD6582 Phase 2
0.6755 Remote Similarity NPD5327 Phase 3
0.6755 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6755 Remote Similarity NPD3685 Discontinued
0.6755 Remote Similarity NPD6583 Phase 3
0.6753 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6752 Remote Similarity NPD5124 Phase 1
0.6752 Remote Similarity NPD5123 Clinical (unspecified phase)
0.675 Remote Similarity NPD6002 Phase 3
0.675 Remote Similarity NPD6005 Phase 3

Structure

External Identifiers

PubChem CID   44606078
ChEMBL   CHEMBL1089049
ZINC  

Physicochemical Properties

Molecular Weight:  536.15
ALogP:  -4.8464
MLogP:  2.78
XLogP:  -0.888
# Rotatable Bonds:  12
Polar Surface Area:  196.99
# H-Bond Aceptor:  9
# H-Bond Donor:  7
# Rings:  6
# Heavy Atoms:  38

Download Data

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