Natural Product: NPC476374

Natural Product ID:  NPC476374
Common Name:   Quiquelignan E
IUPAC Name:   [(2R,3R)-2,3-dihydroxy-3-[4-[3-(4-hydroxybenzoyl)oxy-1-(3-hydroxy-2,4-dimethoxyphenyl)-1-oxopropan-2-yl]oxy-3,5-dimethoxyphenyl]propyl] 4-hydroxybenzoate
Synonyms:   Quiquelignan E
Molecular Formula:   C36H36O15
Standard InCHIKey:  LMONDGWEAFZUJM-LMTUGHDTSA-N
Standard InCHI:  InChI=1S/C36H36O15/c1-45-26-14-13-24(33(48-4)32(26)42)31(41)29(18-50-36(44)20-7-11-23(38)12-8-20)51-34-27(46-2)15-21(16-28(34)47-3)30(40)25(39)17-49-35(43)19-5-9-22(37)10-6-19/h5-16,25,29-30,37-40,42H,17-18H2,1-4H3/t25-,29?,30-/m1/s1
Canonical SMILES:  COc1cc(cc(c1OC(C(=O)c1ccc(c(c1OC)O)OC)COC(=O)c1ccc(cc1)O)OC)[C@H]([C@@H](COC(=O)c1ccc(cc1)O)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
NPO32697 calamus quiquesetinervius Species NA NA PMID[20056545]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 53800 nM 15646539
NPT2 Others Unspecified IC50 = 6200 nM 21625478

  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 NPC476374 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
0.9938 High Similarity NPC476370
0.9512 High Similarity NPC476365
0.9503 High Similarity NPC476372
0.9503 High Similarity NPC476371
0.9412 High Similarity NPC104910
0.9412 High Similarity NPC474093
0.9379 High Similarity NPC476373
0.9357 High Similarity NPC475179
0.9333 High Similarity NPC280493
0.9294 High Similarity NPC297503
0.9294 High Similarity NPC97119
0.9294 High Similarity NPC135831
0.929 High Similarity NPC471030
0.9281 High Similarity NPC88560
0.9281 High Similarity NPC175230
0.9281 High Similarity NPC172033
0.9244 High Similarity NPC30011
0.9244 High Similarity NPC72554
0.9244 High Similarity NPC97817
0.924 High Similarity NPC21359
0.924 High Similarity NPC470713
0.924 High Similarity NPC25946
0.924 High Similarity NPC460984
0.924 High Similarity NPC470717
0.924 High Similarity NPC470416
0.924 High Similarity NPC470720
0.9231 High Similarity NPC217520
0.9231 High Similarity NPC35167
0.9231 High Similarity NPC477895
0.9231 High Similarity NPC139571
0.9202 High Similarity NPC158188
0.9202 High Similarity NPC112418
0.9198 High Similarity NPC476410
0.9198 High Similarity NPC172202
0.9198 High Similarity NPC284127
0.9186 High Similarity NPC470719
0.9186 High Similarity NPC473554
0.9186 High Similarity NPC295625
0.9181 High Similarity NPC241781
0.9181 High Similarity NPC470718
0.9181 High Similarity NPC36138
0.9181 High Similarity NPC156785
0.9181 High Similarity NPC162394
0.9172 High Similarity NPC154741
0.9172 High Similarity NPC296018
0.9172 High Similarity NPC61904
0.9172 High Similarity NPC144097
0.9167 High Similarity NPC4390
0.9162 High Similarity NPC149011
0.9162 High Similarity NPC204937
0.9157 High Similarity NPC295082
0.9152 High Similarity NPC125039
0.9152 High Similarity NPC58223
0.9152 High Similarity NPC477840
0.9152 High Similarity NPC36916
0.9152 High Similarity NPC7688
0.9152 High Similarity NPC7154
0.9152 High Similarity NPC471788
0.9152 High Similarity NPC72787
0.9152 High Similarity NPC36
0.9146 High Similarity NPC471745
0.9141 High Similarity NPC53889
0.9141 High Similarity NPC471744
0.9141 High Similarity NPC188967
0.9136 High Similarity NPC63454
0.9136 High Similarity NPC183851
0.9133 High Similarity NPC269625
0.9128 High Similarity NPC275977
0.9128 High Similarity NPC249560
0.9128 High Similarity NPC223860
0.9123 High Similarity NPC117668
0.9118 High Similarity NPC196127
0.9118 High Similarity NPC37668
0.9118 High Similarity NPC217387
0.9118 High Similarity NPC476773
0.9118 High Similarity NPC253521
0.9118 High Similarity NPC293626
0.9118 High Similarity NPC258044
0.9118 High Similarity NPC113836
0.9118 High Similarity NPC267680
0.9112 High Similarity NPC214621
0.9112 High Similarity NPC223426
0.9112 High Similarity NPC99591
0.9112 High Similarity NPC34267
0.9112 High Similarity NPC81042
0.9107 High Similarity NPC175107
0.9107 High Similarity NPC190003
0.9107 High Similarity NPC153755
0.9102 High Similarity NPC475212
0.9085 High Similarity NPC113163
0.9085 High Similarity NPC66618
0.9085 High Similarity NPC305987
0.9085 High Similarity NPC288131
0.9085 High Similarity NPC165970
0.9085 High Similarity NPC84324
0.908 High Similarity NPC154304
0.908 High Similarity NPC87317
0.908 High Similarity NPC190487
0.9075 High Similarity NPC33083
0.9074 High Similarity NPC265511
0.9068 High Similarity NPC469888
0.9059 High Similarity NPC472385
0.9059 High Similarity NPC198324
0.9053 High Similarity NPC472993
0.9048 High Similarity NPC469344
0.9048 High Similarity NPC155763
0.9048 High Similarity NPC244776
0.9048 High Similarity NPC235260
0.9048 High Similarity NPC206123
0.9048 High Similarity NPC180768
0.9048 High Similarity NPC116864
0.9048 High Similarity NPC20505
0.9042 High Similarity NPC116745
0.9042 High Similarity NPC243877
0.9042 High Similarity NPC14662
0.9042 High Similarity NPC260266
0.9036 High Similarity NPC280893
0.903 High Similarity NPC477841
0.903 High Similarity NPC476247
0.903 High Similarity NPC219927
0.9024 High Similarity NPC24164
0.9024 High Similarity NPC101731
0.9018 High Similarity NPC160512
0.9018 High Similarity NPC185526
0.9018 High Similarity NPC68324
0.9018 High Similarity NPC471479
0.9018 High Similarity NPC52530
0.9018 High Similarity NPC114179
0.9018 High Similarity NPC471515
0.9018 High Similarity NPC38779
0.9018 High Similarity NPC289322
0.9018 High Similarity NPC156818
0.9017 High Similarity NPC470451
0.9017 High Similarity NPC470455
0.9006 High Similarity NPC173837
0.9 High Similarity NPC43211
0.9 High Similarity NPC264735
0.9 High Similarity NPC135277
0.9 High Similarity NPC477848
0.9 High Similarity NPC101191
0.9 High Similarity NPC49344
0.9 High Similarity NPC115760
0.9 High Similarity NPC237435
0.9 High Similarity NPC210094
0.8994 High Similarity NPC186847
0.8994 High Similarity NPC212038
0.8994 High Similarity NPC472454
0.8994 High Similarity NPC11847
0.8994 High Similarity NPC217822
0.8994 High Similarity NPC221288
0.8994 High Similarity NPC81332
0.8994 High Similarity NPC271848
0.8994 High Similarity NPC257667
0.8994 High Similarity NPC262580
0.8994 High Similarity NPC289396
0.8994 High Similarity NPC101399
0.8988 High Similarity NPC120099
0.8988 High Similarity NPC203050
0.8988 High Similarity NPC223747
0.8988 High Similarity NPC225434
0.8988 High Similarity NPC138927
0.8988 High Similarity NPC219904
0.8982 High Similarity NPC13481
0.8982 High Similarity NPC477517
0.8982 High Similarity NPC471213
0.8982 High Similarity NPC207575
0.8976 High Similarity NPC272064
0.897 High Similarity NPC308992
0.897 High Similarity NPC471499
0.897 High Similarity NPC142252
0.8966 High Similarity NPC112380
0.8963 High Similarity NPC19687
0.8963 High Similarity NPC18607
0.8963 High Similarity NPC105242
0.8963 High Similarity NPC130894
0.8963 High Similarity NPC261004
0.8963 High Similarity NPC300943
0.8963 High Similarity NPC4481
0.8963 High Similarity NPC176300
0.8963 High Similarity NPC253634
0.8963 High Similarity NPC193842
0.8963 High Similarity NPC22472
0.8963 High Similarity NPC288669
0.8963 High Similarity NPC152166
0.8963 High Similarity NPC9609
0.8963 High Similarity NPC115798
0.8963 High Similarity NPC191459
0.8963 High Similarity NPC204854
0.8963 High Similarity NPC143828
0.8963 High Similarity NPC7846
0.8963 High Similarity NPC25495
0.8963 High Similarity NPC18772
0.896 High Similarity NPC470445
0.896 High Similarity NPC199172
0.896 High Similarity NPC35924
0.896 High Similarity NPC470449
0.896 High Similarity NPC470446
0.896 High Similarity NPC470447
0.8957 High Similarity NPC250922
0.8957 High Similarity NPC88803

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476374 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
0.9152 High Similarity NPD6168 Clinical (unspecified phase)
0.9152 High Similarity NPD6167 Clinical (unspecified phase)
0.9152 High Similarity NPD6166 Phase 2
0.9107 High Similarity NPD7993 Clinical (unspecified phase)
0.9012 High Similarity NPD3817 Phase 2
0.9 High Similarity NPD4338 Clinical (unspecified phase)
0.8957 High Similarity NPD4868 Clinical (unspecified phase)
0.8957 High Similarity NPD3882 Suspended
0.8889 High Similarity NPD7808 Phase 3
0.883 High Similarity NPD7251 Discontinued
0.8788 High Similarity NPD7075 Discontinued
0.8773 High Similarity NPD1934 Approved
0.8772 High Similarity NPD6797 Phase 2
0.8765 High Similarity NPD7054 Approved
0.872 High Similarity NPD2801 Approved
0.8713 High Similarity NPD7074 Phase 3
0.8713 High Similarity NPD7472 Approved
0.8706 High Similarity NPD3818 Discontinued
0.8667 High Similarity NPD5402 Approved
0.8606 High Similarity NPD7096 Clinical (unspecified phase)
0.8606 High Similarity NPD2393 Clinical (unspecified phase)
0.8545 High Similarity NPD6801 Discontinued
0.8519 High Similarity NPD1512 Approved
0.8509 High Similarity NPD6799 Approved
0.8466 Intermediate Similarity NPD5403 Approved
0.8439 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.843 Intermediate Similarity NPD7473 Discontinued
0.8395 Intermediate Similarity NPD1511 Approved
0.8363 Intermediate Similarity NPD6232 Discontinued
0.8344 Intermediate Similarity NPD5401 Approved
0.8343 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD5844 Phase 1
0.8313 Intermediate Similarity NPD4380 Phase 2
0.8284 Intermediate Similarity NPD7768 Phase 2
0.8278 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8274 Intermediate Similarity NPD7819 Suspended
0.8266 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD7411 Suspended
0.8225 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD6599 Discontinued
0.8187 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8166 Intermediate Similarity NPD1465 Phase 2
0.816 Intermediate Similarity NPD6190 Approved
0.814 Intermediate Similarity NPD5494 Approved
0.8121 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD6959 Discontinued
0.8012 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD8312 Approved
0.8 Intermediate Similarity NPD8313 Approved
0.7989 Intermediate Similarity NPD6559 Discontinued
0.7977 Intermediate Similarity NPD919 Approved
0.7975 Intermediate Similarity NPD1549 Phase 2
0.7919 Intermediate Similarity NPD3749 Approved
0.7917 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD3926 Phase 2
0.7865 Intermediate Similarity NPD3751 Discontinued
0.7853 Intermediate Similarity NPD2796 Approved
0.7841 Intermediate Similarity NPD3787 Discontinued
0.7826 Intermediate Similarity NPD230 Phase 1
0.7791 Intermediate Similarity NPD1510 Phase 2
0.779 Intermediate Similarity NPD7685 Pre-registration
0.7784 Intermediate Similarity NPD1247 Approved
0.7784 Intermediate Similarity NPD7199 Phase 2
0.7716 Intermediate Similarity NPD447 Suspended
0.7711 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD8150 Discontinued
0.7676 Intermediate Similarity NPD8434 Phase 2
0.767 Intermediate Similarity NPD6234 Discontinued
0.7668 Intermediate Similarity NPD7435 Discontinued
0.7667 Intermediate Similarity NPD7228 Approved
0.7665 Intermediate Similarity NPD3750 Approved
0.7665 Intermediate Similarity NPD4628 Phase 3
0.7661 Intermediate Similarity NPD1653 Approved
0.7654 Intermediate Similarity NPD1240 Approved
0.7654 Intermediate Similarity NPD943 Approved
0.7653 Intermediate Similarity NPD8151 Discontinued
0.7651 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD1551 Phase 2
0.7586 Intermediate Similarity NPD37 Approved
0.7561 Intermediate Similarity NPD1607 Approved
0.756 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD4967 Phase 2
0.7557 Intermediate Similarity NPD4965 Approved
0.7557 Intermediate Similarity NPD4966 Approved
0.7556 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD1613 Approved
0.7546 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD8455 Phase 2
0.7531 Intermediate Similarity NPD6798 Discontinued
0.753 Intermediate Similarity NPD2935 Discontinued
0.7529 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD7874 Approved
0.7514 Intermediate Similarity NPD3226 Approved
0.7486 Intermediate Similarity NPD8127 Discontinued
0.7485 Intermediate Similarity NPD2532 Approved
0.7485 Intermediate Similarity NPD2533 Approved
0.7485 Intermediate Similarity NPD2534 Approved
0.7485 Intermediate Similarity NPD6233 Phase 2
0.747 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD3027 Phase 3
0.7449 Intermediate Similarity NPD7870 Phase 2
0.7449 Intermediate Similarity NPD7871 Phase 2
0.7446 Intermediate Similarity NPD5953 Discontinued
0.7432 Intermediate Similarity NPD7286 Phase 2
0.7423 Intermediate Similarity NPD6781 Approved
0.7423 Intermediate Similarity NPD6777 Approved
0.7423 Intermediate Similarity NPD6776 Approved
0.7423 Intermediate Similarity NPD6780 Approved
0.7423 Intermediate Similarity NPD6778 Approved
0.7423 Intermediate Similarity NPD6779 Approved
0.7423 Intermediate Similarity NPD6782 Approved
0.7407 Intermediate Similarity NPD6832 Phase 2
0.7399 Intermediate Similarity NPD920 Approved
0.7398 Intermediate Similarity NPD7696 Phase 3
0.7398 Intermediate Similarity NPD7698 Approved
0.7398 Intermediate Similarity NPD7697 Approved
0.7394 Intermediate Similarity NPD1933 Approved
0.7384 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7266 Discontinued
0.7365 Intermediate Similarity NPD3748 Approved
0.736 Intermediate Similarity NPD8320 Phase 1
0.736 Intermediate Similarity NPD8319 Approved
0.7337 Intermediate Similarity NPD7701 Phase 2
0.7333 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7390 Discontinued
0.7313 Intermediate Similarity NPD7783 Phase 2
0.7313 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD5353 Approved
0.7301 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD6355 Discontinued
0.7283 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD2799 Discontinued
0.7246 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD9494 Approved
0.7232 Intermediate Similarity NPD6386 Approved
0.7232 Intermediate Similarity NPD6385 Approved
0.7231 Intermediate Similarity NPD7700 Phase 2
0.7231 Intermediate Similarity NPD7699 Phase 2
0.7228 Intermediate Similarity NPD7801 Approved
0.7222 Intermediate Similarity NPD1203 Approved
0.7219 Intermediate Similarity NPD7240 Approved
0.7219 Intermediate Similarity NPD7038 Approved
0.7219 Intermediate Similarity NPD7039 Approved
0.7216 Intermediate Similarity NPD7458 Discontinued
0.7216 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD5242 Approved
0.7212 Intermediate Similarity NPD2313 Discontinued
0.7193 Intermediate Similarity NPD1243 Approved
0.7193 Intermediate Similarity NPD2800 Approved
0.7186 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD2344 Approved
0.7176 Intermediate Similarity NPD2346 Discontinued
0.7168 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD6534 Approved
0.7165 Intermediate Similarity NPD6535 Approved
0.716 Intermediate Similarity NPD7033 Discontinued
0.7158 Intermediate Similarity NPD7229 Phase 3
0.7151 Intermediate Similarity NPD8166 Discontinued
0.7151 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD9269 Phase 2
0.7118 Intermediate Similarity NPD5404 Approved
0.7118 Intermediate Similarity NPD5406 Approved
0.7118 Intermediate Similarity NPD5405 Approved
0.7118 Intermediate Similarity NPD5408 Approved
0.7114 Intermediate Similarity NPD7584 Approved
0.7099 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD6844 Discontinued
0.7091 Intermediate Similarity NPD4908 Phase 1
0.7085 Intermediate Similarity NPD6823 Phase 2
0.7059 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD7680 Approved
0.7048 Intermediate Similarity NPD7095 Approved
0.7047 Intermediate Similarity NPD4287 Approved
0.7045 Intermediate Similarity NPD6273 Approved
0.7041 Intermediate Similarity NPD6651 Approved
0.7039 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD9717 Approved
0.7024 Intermediate Similarity NPD4060 Phase 1
0.7018 Intermediate Similarity NPD6099 Approved
0.7018 Intermediate Similarity NPD6100 Approved
0.7011 Intermediate Similarity NPD2354 Approved
0.7011 Intermediate Similarity NPD3887 Approved
0.7011 Intermediate Similarity NPD2309 Approved
0.7006 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD7177 Discontinued
0.7005 Intermediate Similarity NPD2163 Approved
0.7 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7549 Discontinued
0.7 Intermediate Similarity NPD7907 Approved
0.6994 Remote Similarity NPD1652 Phase 2
0.6973 Remote Similarity NPD5710 Approved

Structure

External Identifiers

PubChem CID   46232299
ChEMBL   CHEMBL590248
ZINC  

Physicochemical Properties

Molecular Weight:  708.21
ALogP:  -3.3435
MLogP:  3.77
XLogP:  2.183
# Rotatable Bonds:  27
Polar Surface Area:  216.97
# H-Bond Aceptor:  7
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  51

Download Data

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