Natural Product: NPC300657

Natural Product ID:  NPC300657
Common Name:   Gneyulin B
IUPAC Name:   4-[(2R,3R)-3-(3,5-dihydroxyphenyl)-5-[(2R,3R)-3-(3,5-dihydroxyphenyl)-4-hydroxy-6-(6-hydroxy-1-benzofuran-2-yl)-2,3-dihydro-1-benzofuran-2-yl]-6-hydroxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,3-diol
Synonyms:  
Molecular Formula:   C42H30O12
Standard InCHIKey:  HGGUGLARKRGHTC-IASBXJNJSA-N
Standard InCHI:  InChI=1S/C42H30O12/c43-22-3-4-28(31(49)14-22)41-38(20-5-24(45)12-25(46)6-20)30-16-29(32(50)17-36(30)53-41)42-39(21-7-26(47)13-27(48)8-21)40-33(51)9-19(11-37(40)54-42)34-10-18-1-2-23(44)15-35(18)52-34/h1-17,38-39,41-51H/t38-,39-,41+,42+/m1/s1
Canonical SMILES:  Oc1cc(O)cc(c1)[C@H]1[C@@H](Oc2c1c(O)cc(c2)c1oc2c(c1)ccc(c2)O)c1cc2c(cc1O)O[C@H]([C@@H]2c1cc(O)cc(c1)O)c1ccc(cc1O)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
NPO20232 Gnetum gnemonoides Species Gnetaceae Eukaryota bark PMID[20192242]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT640 Individual Protein Sodium/glucose cotransporter 1 Homo sapiens IC50 = 37000 nM 21954912
NPT641 Individual Protein Sodium/glucose cotransporter 2 Homo sapiens IC50 = 18000 nM 21954912

  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 NPC300657 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
0.9333 High Similarity NPC286230
0.9333 High Similarity NPC253730
0.9329 High Similarity NPC169471
0.9152 High Similarity NPC38591
0.9146 High Similarity NPC301256
0.9146 High Similarity NPC312273
0.9136 High Similarity NPC137100
0.9091 High Similarity NPC473012
0.9036 High Similarity NPC159508
0.9036 High Similarity NPC473009
0.9024 High Similarity NPC40583
0.9006 High Similarity NPC101991
0.9 High Similarity NPC24748
0.9 High Similarity NPC59491
0.8982 High Similarity NPC474591
0.8982 High Similarity NPC473010
0.8976 High Similarity NPC473011
0.8971 High Similarity NPC47905
0.8971 High Similarity NPC139683
0.8971 High Similarity NPC73929
0.897 High Similarity NPC292863
0.897 High Similarity NPC184326
0.8935 High Similarity NPC53252
0.8929 High Similarity NPC251336
0.8916 High Similarity NPC137232
0.8916 High Similarity NPC18380
0.8914 High Similarity NPC304322
0.8909 High Similarity NPC195167
0.8909 High Similarity NPC105584
0.8909 High Similarity NPC472877
0.8909 High Similarity NPC51760
0.8902 High Similarity NPC69531
0.8902 High Similarity NPC121888
0.8902 High Similarity NPC32867
0.8869 High Similarity NPC469664
0.8862 High Similarity NPC15374
0.8855 High Similarity NPC472052
0.8855 High Similarity NPC98023
0.8855 High Similarity NPC470342
0.8855 High Similarity NPC472060
0.8855 High Similarity NPC226462
0.8855 High Similarity NPC195136
0.8848 High Similarity NPC246647
0.8848 High Similarity NPC212967
0.8848 High Similarity NPC164110
0.8848 High Similarity NPC96342
0.8841 High Similarity NPC66441
0.8841 High Similarity NPC134171
0.8841 High Similarity NPC300668
0.8841 High Similarity NPC182555
0.8817 High Similarity NPC82330
0.881 High Similarity NPC290160
0.8802 High Similarity NPC90822
0.8802 High Similarity NPC189552
0.8802 High Similarity NPC273467
0.8795 High Similarity NPC15815
0.8795 High Similarity NPC295090
0.8788 High Similarity NPC309648
0.8788 High Similarity NPC180924
0.878 High Similarity NPC121568
0.878 High Similarity NPC213608
0.878 High Similarity NPC1477
0.8773 High Similarity NPC170169
0.875 High Similarity NPC261896
0.8743 High Similarity NPC304839
0.8743 High Similarity NPC220582
0.8743 High Similarity NPC312993
0.8743 High Similarity NPC42965
0.8743 High Similarity NPC186325
0.8736 High Similarity NPC478000
0.8735 High Similarity NPC257166
0.8735 High Similarity NPC65504
0.8735 High Similarity NPC271741
0.8735 High Similarity NPC208258
0.8735 High Similarity NPC287789
0.8735 High Similarity NPC1796
0.8735 High Similarity NPC475184
0.8727 High Similarity NPC100049
0.8727 High Similarity NPC14606
0.8727 High Similarity NPC205026
0.8727 High Similarity NPC258474
0.8727 High Similarity NPC150908
0.8727 High Similarity NPC79375
0.8727 High Similarity NPC201227
0.8727 High Similarity NPC265624
0.8727 High Similarity NPC158027
0.8727 High Similarity NPC198490
0.8727 High Similarity NPC186227
0.8727 High Similarity NPC52611
0.8727 High Similarity NPC148938
0.8727 High Similarity NPC215203
0.8727 High Similarity NPC159707
0.8727 High Similarity NPC37253
0.8727 High Similarity NPC121649
0.8727 High Similarity NPC248739
0.8721 High Similarity NPC477529
0.8721 High Similarity NPC477836
0.872 High Similarity NPC115601
0.872 High Similarity NPC78324
0.872 High Similarity NPC208011
0.872 High Similarity NPC174086
0.872 High Similarity NPC5871
0.872 High Similarity NPC39154
0.8712 High Similarity NPC78335
0.8712 High Similarity NPC230713
0.8712 High Similarity NPC167576
0.8706 High Similarity NPC53640
0.8706 High Similarity NPC477835
0.8706 High Similarity NPC171985
0.8706 High Similarity NPC320741
0.8706 High Similarity NPC224851
0.8698 High Similarity NPC109180
0.869 High Similarity NPC304387
0.8683 High Similarity NPC55443
0.8683 High Similarity NPC226287
0.8683 High Similarity NPC51247
0.8683 High Similarity NPC324736
0.8683 High Similarity NPC18699
0.8683 High Similarity NPC177650
0.8675 High Similarity NPC56049
0.8675 High Similarity NPC61112
0.8675 High Similarity NPC198489
0.8675 High Similarity NPC54830
0.8667 High Similarity NPC472462
0.8667 High Similarity NPC194593
0.8667 High Similarity NPC290830
0.8667 High Similarity NPC71061
0.8667 High Similarity NPC72425
0.8667 High Similarity NPC235333
0.8667 High Similarity NPC303485
0.8667 High Similarity NPC72370
0.8667 High Similarity NPC183874
0.8659 High Similarity NPC111112
0.8659 High Similarity NPC67322
0.8659 High Similarity NPC138299
0.8659 High Similarity NPC222713
0.8655 High Similarity NPC476459
0.865 High Similarity NPC226644
0.865 High Similarity NPC178202
0.865 High Similarity NPC37226
0.8639 High Similarity NPC477239
0.8639 High Similarity NPC3448
0.8631 High Similarity NPC121647
0.8629 High Similarity NPC475783
0.8623 High Similarity NPC324358
0.8623 High Similarity NPC268360
0.8623 High Similarity NPC318527
0.8623 High Similarity NPC323627
0.8623 High Similarity NPC322459
0.8614 High Similarity NPC254351
0.8614 High Similarity NPC226656
0.8614 High Similarity NPC66508
0.8614 High Similarity NPC297531
0.8614 High Similarity NPC213936
0.8613 High Similarity NPC174700
0.8613 High Similarity NPC28589
0.8613 High Similarity NPC248593
0.8613 High Similarity NPC478002
0.8606 High Similarity NPC207624
0.8606 High Similarity NPC43345
0.8605 High Similarity NPC300307
0.8605 High Similarity NPC107627
0.8589 High Similarity NPC135325
0.8589 High Similarity NPC122894
0.8588 High Similarity NPC63438
0.858 High Similarity NPC472261
0.858 High Similarity NPC74854
0.858 High Similarity NPC45124
0.858 High Similarity NPC30655
0.8571 High Similarity NPC324220
0.8571 High Similarity NPC312630
0.8571 High Similarity NPC476350
0.8571 High Similarity NPC476349
0.8563 High Similarity NPC65885
0.8563 High Similarity NPC160015
0.8563 High Similarity NPC247677
0.8555 High Similarity NPC477571
0.8555 High Similarity NPC477572
0.8555 High Similarity NPC477573
0.8554 High Similarity NPC122365
0.8554 High Similarity NPC324447
0.8547 High Similarity NPC50394
0.8547 High Similarity NPC324522
0.8547 High Similarity NPC472058
0.8547 High Similarity NPC470341
0.8547 High Similarity NPC105414
0.8547 High Similarity NPC234497
0.8545 High Similarity NPC178484
0.8545 High Similarity NPC476553
0.8545 High Similarity NPC58668
0.8545 High Similarity NPC476552
0.8545 High Similarity NPC193976
0.8545 High Similarity NPC115324
0.8545 High Similarity NPC106372
0.8545 High Similarity NPC476551
0.8545 High Similarity NPC23668
0.8539 High Similarity NPC154527
0.8538 High Similarity NPC136641
0.8537 High Similarity NPC288840
0.8537 High Similarity NPC317492

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC300657 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
0.8802 High Similarity NPD6959 Discontinued
0.8503 High Similarity NPD8443 Clinical (unspecified phase)
0.843 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8294 Intermediate Similarity NPD3749 Approved
0.8249 Intermediate Similarity NPD6559 Discontinued
0.8235 Intermediate Similarity NPD7768 Phase 2
0.8182 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD4380 Phase 2
0.8121 Intermediate Similarity NPD7390 Discontinued
0.8118 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8118 Intermediate Similarity NPD7819 Suspended
0.8107 Intermediate Similarity NPD7411 Suspended
0.8092 Intermediate Similarity NPD5494 Approved
0.8072 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8068 Intermediate Similarity NPD7473 Discontinued
0.8056 Intermediate Similarity NPD8313 Approved
0.8056 Intermediate Similarity NPD8312 Approved
0.8037 Intermediate Similarity NPD1549 Phase 2
0.8011 Intermediate Similarity NPD6166 Phase 2
0.8011 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6232 Discontinued
0.7975 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD3818 Discontinued
0.7919 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7889 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD5844 Phase 1
0.7874 Intermediate Similarity NPD7075 Discontinued
0.7874 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD2533 Approved
0.7857 Intermediate Similarity NPD2534 Approved
0.7857 Intermediate Similarity NPD2532 Approved
0.7853 Intermediate Similarity NPD1510 Phase 2
0.7849 Intermediate Similarity NPD1934 Approved
0.7838 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD3882 Suspended
0.7805 Intermediate Similarity NPD2796 Approved
0.7778 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD920 Approved
0.7758 Intermediate Similarity NPD2344 Approved
0.7751 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD1607 Approved
0.7701 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD2801 Approved
0.7692 Intermediate Similarity NPD1511 Approved
0.7674 Intermediate Similarity NPD3226 Approved
0.7665 Intermediate Similarity NPD2800 Approved
0.766 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD3926 Phase 2
0.7647 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD6801 Discontinued
0.7637 Intermediate Similarity NPD7074 Phase 3
0.7633 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD1240 Approved
0.7602 Intermediate Similarity NPD1512 Approved
0.7582 Intermediate Similarity NPD7054 Approved
0.7574 Intermediate Similarity NPD2309 Approved
0.7572 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD1243 Approved
0.756 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD5402 Approved
0.7542 Intermediate Similarity NPD1247 Approved
0.7541 Intermediate Similarity NPD7472 Approved
0.753 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6599 Discontinued
0.7525 Intermediate Similarity NPD8151 Discontinued
0.7515 Intermediate Similarity NPD3750 Approved
0.7514 Intermediate Similarity NPD7808 Phase 3
0.75 Intermediate Similarity NPD6797 Phase 2
0.7485 Intermediate Similarity NPD5404 Approved
0.7485 Intermediate Similarity NPD1551 Phase 2
0.7485 Intermediate Similarity NPD5408 Approved
0.7485 Intermediate Similarity NPD5406 Approved
0.7485 Intermediate Similarity NPD5405 Approved
0.7459 Intermediate Similarity NPD7251 Discontinued
0.7458 Intermediate Similarity NPD3817 Phase 2
0.7432 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.743 Intermediate Similarity NPD919 Approved
0.7419 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD7003 Approved
0.7411 Intermediate Similarity NPD7871 Phase 2
0.7411 Intermediate Similarity NPD7870 Phase 2
0.7403 Intermediate Similarity NPD7229 Phase 3
0.7401 Intermediate Similarity NPD5761 Phase 2
0.7401 Intermediate Similarity NPD5760 Phase 2
0.7396 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD6799 Approved
0.7381 Intermediate Similarity NPD2935 Discontinued
0.7378 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7458 Discontinued
0.7368 Intermediate Similarity NPD4287 Approved
0.7356 Intermediate Similarity NPD5403 Approved
0.7354 Intermediate Similarity NPD8434 Phase 2
0.7341 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD2346 Discontinued
0.7337 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6234 Discontinued
0.7321 Intermediate Similarity NPD2799 Discontinued
0.7318 Intermediate Similarity NPD4966 Approved
0.7318 Intermediate Similarity NPD4967 Phase 2
0.7318 Intermediate Similarity NPD4965 Approved
0.7312 Intermediate Similarity NPD5953 Discontinued
0.7308 Intermediate Similarity NPD5710 Approved
0.7308 Intermediate Similarity NPD5711 Approved
0.7303 Intermediate Similarity NPD8455 Phase 2
0.7303 Intermediate Similarity NPD1465 Phase 2
0.7302 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD6781 Approved
0.7296 Intermediate Similarity NPD6777 Approved
0.7296 Intermediate Similarity NPD6782 Approved
0.7296 Intermediate Similarity NPD6776 Approved
0.7296 Intermediate Similarity NPD6778 Approved
0.7296 Intermediate Similarity NPD6779 Approved
0.7296 Intermediate Similarity NPD6780 Approved
0.7278 Intermediate Similarity NPD6099 Approved
0.7278 Intermediate Similarity NPD6100 Approved
0.7273 Intermediate Similarity NPD7697 Approved
0.7273 Intermediate Similarity NPD7698 Approved
0.7273 Intermediate Similarity NPD7696 Phase 3
0.7263 Intermediate Similarity NPD8150 Discontinued
0.7256 Intermediate Similarity NPD4908 Phase 1
0.7243 Intermediate Similarity NPD7177 Discontinued
0.7243 Intermediate Similarity NPD3751 Discontinued
0.7243 Intermediate Similarity NPD7228 Approved
0.7241 Intermediate Similarity NPD5401 Approved
0.7219 Intermediate Similarity NPD3748 Approved
0.7213 Intermediate Similarity NPD3787 Discontinued
0.7209 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD4628 Phase 3
0.7204 Intermediate Similarity NPD7286 Phase 2
0.7202 Intermediate Similarity NPD6651 Approved
0.7192 Intermediate Similarity NPD7783 Phase 2
0.7192 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7435 Discontinued
0.7169 Intermediate Similarity NPD2313 Discontinued
0.7159 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD7199 Phase 2
0.7151 Intermediate Similarity NPD37 Approved
0.7143 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD7701 Phase 2
0.7128 Intermediate Similarity NPD4360 Phase 2
0.7128 Intermediate Similarity NPD4363 Phase 3
0.7108 Intermediate Similarity NPD7801 Approved
0.7102 Intermediate Similarity NPD6273 Approved
0.7083 Intermediate Similarity NPD943 Approved
0.7081 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD2296 Approved
0.7066 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7874 Approved
0.705 Intermediate Similarity NPD6823 Phase 2
0.7041 Intermediate Similarity NPD6535 Approved
0.7041 Intermediate Similarity NPD6534 Approved
0.7035 Intermediate Similarity NPD1471 Phase 3
0.702 Intermediate Similarity NPD7700 Phase 2
0.702 Intermediate Similarity NPD7699 Phase 2
0.7011 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD4625 Phase 3
0.7005 Intermediate Similarity NPD4361 Phase 2
0.7005 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.698 Remote Similarity NPD8320 Phase 1
0.698 Remote Similarity NPD8319 Approved
0.697 Remote Similarity NPD1470 Approved
0.6964 Remote Similarity NPD3764 Approved
0.6961 Remote Similarity NPD6280 Approved
0.6961 Remote Similarity NPD6279 Approved
0.695 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6935 Remote Similarity NPD6808 Phase 2
0.6933 Remote Similarity NPD1610 Phase 2
0.6933 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6931 Remote Similarity NPD7680 Approved
0.6911 Remote Similarity NPD7240 Approved
0.6906 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6895 Remote Similarity NPD1729 Discontinued
0.6893 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6887 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6886 Remote Similarity NPD2861 Phase 2
0.6885 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6882 Remote Similarity NPD8127 Discontinued
0.6867 Remote Similarity NPD1203 Approved
0.6865 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6852 Remote Similarity NPD7654 Discontinued
0.6845 Remote Similarity NPD6832 Phase 2
0.6829 Remote Similarity NPD1201 Approved
0.6826 Remote Similarity NPD2798 Approved
0.6821 Remote Similarity NPD7033 Discontinued
0.6818 Remote Similarity NPD6213 Phase 3
0.6818 Remote Similarity NPD6212 Phase 3
0.6818 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6816 Remote Similarity NPD8285 Discontinued
0.6784 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6784 Remote Similarity NPD1613 Approved
0.6776 Remote Similarity NPD6844 Discontinued
0.6765 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6765 Remote Similarity NPD3268 Approved
0.6748 Remote Similarity NPD7584 Approved
0.6747 Remote Similarity NPD4749 Approved
0.6744 Remote Similarity NPD1899 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   46210600
ChEMBL   CHEMBL1097908
ZINC  

Physicochemical Properties

Molecular Weight:  726.17
ALogP:  -4.9676
MLogP:  4.76
XLogP:  3.825
# Rotatable Bonds:  14
Polar Surface Area:  213.67
# H-Bond Aceptor:  0
# H-Bond Donor:  9
# Rings:  9
# Heavy Atoms:  54

Download Data

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