Natural Product: NPC118385

Natural Product ID:  NPC118385
Common Name:   Ligraminol B
IUPAC Name:   (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R)-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:   ligraminol B
Molecular Formula:   C28H38O14
Standard InCHIKey:  FHFLZYGQOCDSKY-FCEOPEINSA-N
Standard InCHI:  InChI=1S/C28H38O14/c1-36-16-5-12(6-17(37-2)21(16)31)26-14(9-29)15(11-40-28-25(35)24(34)23(33)20(10-30)41-28)27(42-26)13-7-18(38-3)22(32)19(8-13)39-4/h5-8,14-15,20,23-35H,9-11H2,1-4H3/t14-,15-,20-,23-,24+,25-,26+,27+,28-/m1/s1
Canonical SMILES:  OC[C@H]1[C@@H](O[C@H]([C@@H]1CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1cc(OC)c(c(c1)OC)O)c1cc(OC)c(c(c1)OC)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
NPO5681 Acorus gramineus Species Acoraceae Eukaryota Rhizomes PMID[21936523]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell Line A549 Homo sapiens IC50 > 10000 nM 21936523
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 10000 nM 21936523
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 > 10000 nM 21936523
NPT34 Cell Line BV-2 Mus musculus IC50 = 22960 nM 21936523
NPT34 Cell Line BV-2 Mus musculus Activity = 84.4 % 21936523

  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 NPC118385 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
1.0 High Similarity NPC472712
1.0 High Similarity NPC472713
1.0 High Similarity NPC473046
1.0 High Similarity NPC187774
0.9853 High Similarity NPC5262
0.9853 High Similarity NPC472714
0.9784 High Similarity NPC39657
0.9714 High Similarity NPC248132
0.9714 High Similarity NPC130449
0.9645 High Similarity NPC55158
0.9645 High Similarity NPC51328
0.9645 High Similarity NPC286235
0.9635 High Similarity NPC472711
0.9577 High Similarity NPC472709
0.9577 High Similarity NPC472710
0.9559 High Similarity NPC474039
0.9496 High Similarity NPC185307
0.9496 High Similarity NPC477898
0.9496 High Similarity NPC470950
0.9429 High Similarity NPC25292
0.9429 High Similarity NPC84181
0.9429 High Similarity NPC129417
0.9429 High Similarity NPC283995
0.9429 High Similarity NPC470235
0.9429 High Similarity NPC473045
0.9424 High Similarity NPC469559
0.9424 High Similarity NPC476356
0.9424 High Similarity NPC189115
0.942 High Similarity NPC177868
0.9412 High Similarity NPC236522
0.9362 High Similarity NPC279298
0.9362 High Similarity NPC38041
0.9362 High Similarity NPC475096
0.9362 High Similarity NPC22150
0.9357 High Similarity NPC473044
0.9357 High Similarity NPC185071
0.9357 High Similarity NPC12728
0.9357 High Similarity NPC46092
0.9353 High Similarity NPC469661
0.9343 High Similarity NPC199459
0.9343 High Similarity NPC52277
0.9343 High Similarity NPC177035
0.9338 High Similarity NPC244983
0.9338 High Similarity NPC107478
0.9338 High Similarity NPC326095
0.9306 High Similarity NPC218041
0.9306 High Similarity NPC225815
0.9306 High Similarity NPC260781
0.9306 High Similarity NPC469707
0.9306 High Similarity NPC185955
0.9306 High Similarity NPC9933
0.9306 High Similarity NPC214326
0.9306 High Similarity NPC145979
0.9306 High Similarity NPC469706
0.9306 High Similarity NPC182368
0.9301 High Similarity NPC270751
0.9296 High Similarity NPC112861
0.9296 High Similarity NPC99515
0.9296 High Similarity NPC190714
0.9296 High Similarity NPC212890
0.9275 High Similarity NPC195196
0.9275 High Similarity NPC283949
0.927 High Similarity NPC184938
0.927 High Similarity NPC101624
0.9236 High Similarity NPC35877
0.9236 High Similarity NPC55715
0.9236 High Similarity NPC95392
0.9231 High Similarity NPC275284
0.9231 High Similarity NPC15956
0.9231 High Similarity NPC193473
0.9231 High Similarity NPC31325
0.9231 High Similarity NPC114505
0.9231 High Similarity NPC213074
0.9231 High Similarity NPC227902
0.9231 High Similarity NPC224674
0.9225 High Similarity NPC18979
0.9225 High Similarity NPC307466
0.9225 High Similarity NPC161700
0.9225 High Similarity NPC477702
0.9225 High Similarity NPC277867
0.922 High Similarity NPC255566
0.922 High Similarity NPC298317
0.922 High Similarity NPC278961
0.922 High Similarity NPC113680
0.9209 High Similarity NPC212770
0.9209 High Similarity NPC98777
0.9209 High Similarity NPC156376
0.9197 High Similarity NPC287745
0.9191 High Similarity NPC175067
0.9191 High Similarity NPC204215
0.9191 High Similarity NPC470270
0.9167 High Similarity NPC175976
0.9161 High Similarity NPC125755
0.9149 High Similarity NPC246947
0.9149 High Similarity NPC475084
0.9143 High Similarity NPC226547
0.9143 High Similarity NPC56091
0.9143 High Similarity NPC46591
0.9137 High Similarity NPC65530
0.9137 High Similarity NPC304152
0.9137 High Similarity NPC138738
0.9137 High Similarity NPC470413
0.9137 High Similarity NPC185908
0.9137 High Similarity NPC59324
0.913 High Similarity NPC24490
0.913 High Similarity NPC150534
0.913 High Similarity NPC141765
0.913 High Similarity NPC34103
0.913 High Similarity NPC165155
0.9124 High Similarity NPC158331
0.9124 High Similarity NPC196937
0.9124 High Similarity NPC132895
0.9091 High Similarity NPC43508
0.9091 High Similarity NPC166506
0.9091 High Similarity NPC286245
0.9091 High Similarity NPC110763
0.9091 High Similarity NPC272619
0.9091 High Similarity NPC197352
0.9091 High Similarity NPC189239
0.9091 High Similarity NPC476301
0.9085 High Similarity NPC37793
0.9085 High Similarity NPC81638
0.9078 High Similarity NPC471908
0.9071 High Similarity NPC30951
0.9071 High Similarity NPC6369
0.9065 High Similarity NPC172818
0.9065 High Similarity NPC25695
0.9065 High Similarity NPC203230
0.9065 High Similarity NPC242028
0.9058 High Similarity NPC48863
0.9058 High Similarity NPC470881
0.9058 High Similarity NPC13745
0.9058 High Similarity NPC251981
0.9058 High Similarity NPC35731
0.9051 High Similarity NPC106739
0.9051 High Similarity NPC253105
0.9051 High Similarity NPC201587
0.9051 High Similarity NPC471505
0.9048 High Similarity NPC302610
0.9041 High Similarity NPC98624
0.9041 High Similarity NPC475224
0.9034 High Similarity NPC301961
0.9034 High Similarity NPC166584
0.9028 High Similarity NPC226540
0.9021 High Similarity NPC471415
0.9021 High Similarity NPC469313
0.9021 High Similarity NPC76176
0.9021 High Similarity NPC121661
0.9021 High Similarity NPC471667
0.9021 High Similarity NPC470097
0.9021 High Similarity NPC217635
0.9021 High Similarity NPC114119
0.9021 High Similarity NPC253015
0.9021 High Similarity NPC471065
0.9021 High Similarity NPC168579
0.9021 High Similarity NPC79429
0.9021 High Similarity NPC471063
0.9021 High Similarity NPC138227
0.9021 High Similarity NPC73467
0.9014 High Similarity NPC41782
0.9014 High Similarity NPC48309
0.9014 High Similarity NPC287124
0.9007 High Similarity NPC309124
0.9007 High Similarity NPC291101
0.9007 High Similarity NPC266197
0.9007 High Similarity NPC106944
0.9007 High Similarity NPC184797
0.9007 High Similarity NPC284464
0.8993 High Similarity NPC142547
0.8993 High Similarity NPC126409
0.8993 High Similarity NPC135777
0.8993 High Similarity NPC99572
0.8986 High Similarity NPC215833
0.8986 High Similarity NPC6836
0.8986 High Similarity NPC69513
0.8978 High Similarity NPC476345
0.8978 High Similarity NPC65942
0.8978 High Similarity NPC470096
0.8978 High Similarity NPC474017
0.8978 High Similarity NPC475067
0.8978 High Similarity NPC248307
0.8978 High Similarity NPC470095
0.8973 High Similarity NPC90896
0.8973 High Similarity NPC283839
0.8973 High Similarity NPC106138
0.8966 High Similarity NPC473480
0.8966 High Similarity NPC15538
0.8958 High Similarity NPC469586
0.8951 High Similarity NPC324962
0.8951 High Similarity NPC252169
0.8951 High Similarity NPC474808
0.8944 High Similarity NPC247291
0.8944 High Similarity NPC311530
0.8936 High Similarity NPC236306
0.8936 High Similarity NPC193666
0.8936 High Similarity NPC292487
0.8936 High Similarity NPC123526
0.8936 High Similarity NPC473739
0.8936 High Similarity NPC88640
0.8936 High Similarity NPC232164

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC118385 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
0.8832 High Similarity NPD3027 Phase 3
0.8662 High Similarity NPD7228 Approved
0.8571 High Similarity NPD6234 Discontinued
0.8511 High Similarity NPD1612 Clinical (unspecified phase)
0.8511 High Similarity NPD1613 Approved
0.8487 Intermediate Similarity NPD37 Approved
0.8442 Intermediate Similarity NPD4967 Phase 2
0.8442 Intermediate Similarity NPD4965 Approved
0.8442 Intermediate Similarity NPD4966 Approved
0.8288 Intermediate Similarity NPD7266 Discontinued
0.8286 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8227 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8224 Intermediate Similarity NPD1653 Approved
0.8176 Intermediate Similarity NPD6674 Discontinued
0.8116 Intermediate Similarity NPD3705 Approved
0.811 Intermediate Similarity NPD7240 Approved
0.8098 Intermediate Similarity NPD7074 Phase 3
0.8086 Intermediate Similarity NPD3818 Discontinued
0.8037 Intermediate Similarity NPD7054 Approved
0.8 Intermediate Similarity NPD7199 Phase 2
0.7988 Intermediate Similarity NPD7472 Approved
0.7847 Intermediate Similarity NPD4908 Phase 1
0.7791 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD7251 Discontinued
0.777 Intermediate Similarity NPD1357 Approved
0.7755 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD3620 Phase 2
0.774 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD7808 Phase 3
0.773 Intermediate Similarity NPD1610 Phase 2
0.773 Intermediate Similarity NPD1091 Approved
0.7727 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD6797 Phase 2
0.7679 Intermediate Similarity NPD7685 Pre-registration
0.7673 Intermediate Similarity NPD1934 Approved
0.7655 Intermediate Similarity NPD2861 Phase 2
0.7647 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD2983 Phase 2
0.7622 Intermediate Similarity NPD2982 Phase 2
0.7619 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD5283 Phase 1
0.758 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD6559 Discontinued
0.7556 Intermediate Similarity NPD7680 Approved
0.7552 Intermediate Similarity NPD2981 Phase 2
0.7548 Intermediate Similarity NPD5058 Phase 3
0.7534 Intermediate Similarity NPD3018 Phase 2
0.753 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD6166 Phase 2
0.753 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2978 Approved
0.7516 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2977 Approved
0.75 Intermediate Similarity NPD4749 Approved
0.7469 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7445 Intermediate Similarity NPD228 Approved
0.7396 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD5125 Phase 3
0.7343 Intermediate Similarity NPD5126 Approved
0.7324 Intermediate Similarity NPD1548 Phase 1
0.7317 Intermediate Similarity NPD3882 Suspended
0.7315 Intermediate Similarity NPD4625 Phase 3
0.7301 Intermediate Similarity NPD2801 Approved
0.7301 Intermediate Similarity NPD8455 Phase 2
0.7299 Intermediate Similarity NPD3021 Approved
0.7299 Intermediate Similarity NPD3022 Approved
0.7267 Intermediate Similarity NPD4005 Discontinued
0.7261 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD7157 Approved
0.7222 Intermediate Similarity NPD4380 Phase 2
0.7216 Intermediate Similarity NPD6841 Approved
0.7216 Intermediate Similarity NPD6842 Approved
0.7216 Intermediate Similarity NPD6843 Phase 3
0.7209 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD4108 Discontinued
0.7208 Intermediate Similarity NPD5588 Approved
0.7195 Intermediate Similarity NPD1465 Phase 2
0.7193 Intermediate Similarity NPD5844 Phase 1
0.7186 Intermediate Similarity NPD5494 Approved
0.7176 Intermediate Similarity NPD7473 Discontinued
0.7171 Intermediate Similarity NPD4060 Phase 1
0.7152 Intermediate Similarity NPD6190 Approved
0.7152 Intermediate Similarity NPD3817 Phase 2
0.7143 Intermediate Similarity NPD4536 Approved
0.7143 Intermediate Similarity NPD4538 Approved
0.7143 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7843 Approved
0.7134 Intermediate Similarity NPD4236 Phase 3
0.7134 Intermediate Similarity NPD4237 Approved
0.7134 Intermediate Similarity NPD3384 Approved
0.7134 Intermediate Similarity NPD3382 Approved
0.7134 Intermediate Similarity NPD5177 Phase 3
0.7134 Intermediate Similarity NPD3383 Approved
0.7124 Intermediate Similarity NPD5735 Approved
0.7115 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD1375 Discontinued
0.7107 Intermediate Similarity NPD7124 Phase 2
0.7101 Intermediate Similarity NPD6232 Discontinued
0.7066 Intermediate Similarity NPD7075 Discontinued
0.7063 Intermediate Similarity NPD1511 Approved
0.7059 Intermediate Similarity NPD1558 Phase 1
0.7051 Intermediate Similarity NPD6099 Approved
0.7051 Intermediate Similarity NPD6100 Approved
0.7039 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD7097 Phase 1
0.7032 Intermediate Similarity NPD6111 Discontinued
0.7025 Intermediate Similarity NPD1652 Phase 2
0.7025 Intermediate Similarity NPD3060 Approved
0.7013 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD230 Phase 1
0.7013 Intermediate Similarity NPD6355 Discontinued
0.7013 Intermediate Similarity NPD5124 Phase 1
0.7012 Intermediate Similarity NPD4675 Approved
0.7012 Intermediate Similarity NPD4678 Approved
0.7006 Intermediate Similarity NPD3540 Phase 1
0.7006 Intermediate Similarity NPD5763 Approved
0.7006 Intermediate Similarity NPD5762 Approved
0.7 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3787 Discontinued
0.6987 Remote Similarity NPD5960 Phase 3
0.6981 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6331 Phase 2
0.6981 Remote Similarity NPD4110 Phase 3
0.698 Remote Similarity NPD8651 Approved
0.6978 Remote Similarity NPD2684 Approved
0.6975 Remote Similarity NPD1512 Approved
0.6974 Remote Similarity NPD7095 Approved
0.6968 Remote Similarity NPD6653 Approved
0.6957 Remote Similarity NPD4357 Discontinued
0.6948 Remote Similarity NPD2238 Phase 2
0.6946 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6943 Remote Similarity NPD3539 Phase 1
0.6941 Remote Similarity NPD8127 Discontinued
0.6933 Remote Similarity NPD3094 Phase 2
0.6932 Remote Similarity NPD7549 Discontinued
0.6928 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6927 Remote Similarity NPD7906 Approved
0.6923 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6919 Remote Similarity NPD27 Approved
0.6919 Remote Similarity NPD2489 Approved
0.6914 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6914 Remote Similarity NPD7447 Phase 1
0.6913 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6909 Remote Similarity NPD7028 Phase 2
0.6906 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6903 Remote Similarity NPD3657 Discovery
0.6893 Remote Similarity NPD7313 Approved
0.6893 Remote Similarity NPD7312 Approved
0.6893 Remote Similarity NPD8312 Approved
0.6893 Remote Similarity NPD7311 Approved
0.6893 Remote Similarity NPD7310 Approved
0.6893 Remote Similarity NPD8313 Approved
0.6889 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6886 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6886 Remote Similarity NPD7819 Suspended
0.6886 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6886 Remote Similarity NPD5773 Approved
0.6886 Remote Similarity NPD5772 Approved
0.6886 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3892 Phase 2
0.6875 Remote Similarity NPD7466 Approved
0.6875 Remote Similarity NPD4628 Phase 3
0.6875 Remote Similarity NPD6671 Approved
0.6872 Remote Similarity NPD4663 Approved
0.6867 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6864 Remote Similarity NPD5604 Discontinued
0.686 Remote Similarity NPD2970 Approved
0.686 Remote Similarity NPD2969 Approved
0.6854 Remote Similarity NPD8054 Approved
0.6854 Remote Similarity NPD7309 Approved
0.6854 Remote Similarity NPD8053 Approved
0.6852 Remote Similarity NPD7212 Phase 2
0.6852 Remote Similarity NPD7213 Phase 3
0.6839 Remote Similarity NPD3751 Discontinued
0.6839 Remote Similarity NPD4140 Approved
0.6833 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6832 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6832 Remote Similarity NPD2219 Phase 1
0.681 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6809 Remote Similarity NPD4750 Phase 3
0.6802 Remote Similarity NPD3051 Approved
0.6802 Remote Similarity NPD6071 Discontinued
0.6802 Remote Similarity NPD7229 Phase 3
0.68 Remote Similarity NPD5327 Phase 3
0.6798 Remote Similarity NPD4578 Approved
0.6798 Remote Similarity NPD4577 Approved
0.6792 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6792 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6788 Remote Similarity NPD7827 Phase 1

Structure

External Identifiers

PubChem CID   56600271
ChEMBL   CHEMBL1928002
ZINC  

Physicochemical Properties

Molecular Weight:  598.23
ALogP:  -4.6392
MLogP:  3
XLogP:  -1.33
# Rotatable Bonds:  22
Polar Surface Area:  206.22
# H-Bond Aceptor:  8
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  42

Download Data

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