Natural Product: NPC469549

Natural Product ID:  NPC469549
Common Name:   1-[(2R)-4-(4-Hydroxyphenyl)-2-Butanol-2-O-B-Dglucopyranosyl]-3-Hydroxyl-3-Methylglutaric Acid
IUPAC Name:   (3S)-3-hydroxy-3-methyl-5-oxo-5-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]oxyoxan-2-yl]methoxy]pentanoic acid
Synonyms:  
Molecular Formula:   C22H32O11
Standard InCHIKey:  SBAYJWHOFRCVDL-LBQWKFMXSA-N
Standard InCHI:  InChI=1S/C22H32O11/c1-12(3-4-13-5-7-14(23)8-6-13)32-21-20(29)19(28)18(27)15(33-21)11-31-17(26)10-22(2,30)9-16(24)25/h5-8,12,15,18-21,23,27-30H,3-4,9-11H2,1-2H3,(H,24,25)/t12-,15-,18-,19+,20-,21+,22+/m1/s1
Canonical SMILES:  C[C@@H](O[C@H]1O[C@H](COC(=O)C[C@](CC(=O)O)(O)C)[C@H]([C@@H]([C@H]1O)O)O)CCc1ccc(cc1)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
NPO4138 Betula platyphylla Species Betulaceae Eukaryota bark PMID[20363129]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT521 Cell Line RBL-2H3 Rattus norvegicus Inhibition = 20 % 19191549
NPT521 Cell Line RBL-2H3 Rattus norvegicus Inhibition = 26.6 % DrugMatrix in vitro pharmacology data

  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 NPC469549 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
0.9154 High Similarity NPC169398
0.9008 High Similarity NPC471029
0.8992 High Similarity NPC470122
0.8992 High Similarity NPC17968
0.8992 High Similarity NPC469705
0.8952 High Similarity NPC476448
0.8952 High Similarity NPC476445
0.8952 High Similarity NPC469548
0.8947 High Similarity NPC101686
0.8947 High Similarity NPC469364
0.8947 High Similarity NPC65262
0.8931 High Similarity NPC164172
0.8923 High Similarity NPC281798
0.8898 High Similarity NPC123704
0.8871 High Similarity NPC282409
0.8871 High Similarity NPC469702
0.8855 High Similarity NPC471066
0.8855 High Similarity NPC471095
0.8852 High Similarity NPC148055
0.8837 High Similarity NPC158673
0.876 High Similarity NPC106677
0.8731 High Similarity NPC472132
0.873 High Similarity NPC55608
0.8705 High Similarity NPC212808
0.8689 High Similarity NPC157338
0.8686 High Similarity NPC469623
0.8686 High Similarity NPC296643
0.8686 High Similarity NPC148080
0.8667 High Similarity NPC469696
0.8661 High Similarity NPC52097
0.8651 High Similarity NPC469704
0.8651 High Similarity NPC160854
0.8651 High Similarity NPC201402
0.8651 High Similarity NPC469703
0.8636 High Similarity NPC478255
0.8636 High Similarity NPC476407
0.8636 High Similarity NPC235294
0.8636 High Similarity NPC46137
0.8615 High Similarity NPC173150
0.8615 High Similarity NPC45224
0.8615 High Similarity NPC288416
0.8615 High Similarity NPC35288
0.8615 High Similarity NPC471881
0.8615 High Similarity NPC156692
0.8615 High Similarity NPC471882
0.8594 High Similarity NPC178449
0.8594 High Similarity NPC470907
0.8594 High Similarity NPC232454
0.8583 High Similarity NPC469686
0.8583 High Similarity NPC11724
0.8571 High Similarity NPC143246
0.8571 High Similarity NPC475539
0.8571 High Similarity NPC119773
0.8571 High Similarity NPC474268
0.8561 High Similarity NPC63304
0.8538 High Similarity NPC252114
0.8538 High Similarity NPC61181
0.8538 High Similarity NPC471157
0.8529 High Similarity NPC310252
0.8529 High Similarity NPC84789
0.8529 High Similarity NPC302583
0.8529 High Similarity NPC100558
0.8519 High Similarity NPC123988
0.8516 High Similarity NPC469927
0.8516 High Similarity NPC471067
0.8507 High Similarity NPC114116
0.8504 High Similarity NPC476872
0.85 High Similarity NPC475528
0.8496 Intermediate Similarity NPC138777
0.8496 Intermediate Similarity NPC225384
0.8496 Intermediate Similarity NPC246869
0.8489 Intermediate Similarity NPC478250
0.8473 Intermediate Similarity NPC103533
0.8467 Intermediate Similarity NPC220942
0.8462 Intermediate Similarity NPC126991
0.8462 Intermediate Similarity NPC83218
0.8456 Intermediate Similarity NPC471345
0.845 Intermediate Similarity NPC236981
0.8429 Intermediate Similarity NPC296659
0.8429 Intermediate Similarity NPC202391
0.8409 Intermediate Similarity NPC225307
0.84 Intermediate Similarity NPC175771
0.8387 Intermediate Similarity NPC29607
0.8387 Intermediate Similarity NPC313193
0.8382 Intermediate Similarity NPC263829
0.8382 Intermediate Similarity NPC180171
0.8382 Intermediate Similarity NPC158325
0.8382 Intermediate Similarity NPC103398
0.8357 Intermediate Similarity NPC469367
0.8357 Intermediate Similarity NPC186296
0.8333 Intermediate Similarity NPC469687
0.8333 Intermediate Similarity NPC324262
0.8333 Intermediate Similarity NPC31745
0.8333 Intermediate Similarity NPC220936
0.8333 Intermediate Similarity NPC62800
0.8322 Intermediate Similarity NPC23677
0.8321 Intermediate Similarity NPC90318
0.8321 Intermediate Similarity NPC470572
0.8309 Intermediate Similarity NPC34456
0.8298 Intermediate Similarity NPC184464
0.8298 Intermediate Similarity NPC251062
0.8295 Intermediate Similarity NPC266045
0.8276 Intermediate Similarity NPC474620
0.8235 Intermediate Similarity NPC215484
0.8235 Intermediate Similarity NPC254398
0.8227 Intermediate Similarity NPC293154
0.8219 Intermediate Similarity NPC106818
0.8214 Intermediate Similarity NPC159387
0.8214 Intermediate Similarity NPC7518
0.8214 Intermediate Similarity NPC137501
0.8214 Intermediate Similarity NPC154262
0.8209 Intermediate Similarity NPC229784
0.8209 Intermediate Similarity NPC253595
0.8209 Intermediate Similarity NPC477294
0.8209 Intermediate Similarity NPC477293
0.8207 Intermediate Similarity NPC117346
0.8207 Intermediate Similarity NPC240592
0.8201 Intermediate Similarity NPC328273
0.8201 Intermediate Similarity NPC81515
0.8201 Intermediate Similarity NPC321184
0.8201 Intermediate Similarity NPC476383
0.8201 Intermediate Similarity NPC64141
0.8201 Intermediate Similarity NPC171134
0.8201 Intermediate Similarity NPC68092
0.8201 Intermediate Similarity NPC472350
0.8201 Intermediate Similarity NPC321638
0.8201 Intermediate Similarity NPC197316
0.8201 Intermediate Similarity NPC89105
0.8195 Intermediate Similarity NPC264900
0.8195 Intermediate Similarity NPC79715
0.8195 Intermediate Similarity NPC108659
0.8195 Intermediate Similarity NPC231607
0.8182 Intermediate Similarity NPC473147
0.8175 Intermediate Similarity NPC287597
0.8175 Intermediate Similarity NPC34293
0.8175 Intermediate Similarity NPC886
0.8175 Intermediate Similarity NPC471883
0.8169 Intermediate Similarity NPC194938
0.8163 Intermediate Similarity NPC87403
0.8162 Intermediate Similarity NPC269421
0.8162 Intermediate Similarity NPC473924
0.8162 Intermediate Similarity NPC473285
0.8138 Intermediate Similarity NPC478242
0.8138 Intermediate Similarity NPC96599
0.8134 Intermediate Similarity NPC232880
0.8129 Intermediate Similarity NPC476376
0.8129 Intermediate Similarity NPC260425
0.8125 Intermediate Similarity NPC470330
0.812 Intermediate Similarity NPC94179
0.8112 Intermediate Similarity NPC210330
0.8102 Intermediate Similarity NPC28637
0.8099 Intermediate Similarity NPC475213
0.8099 Intermediate Similarity NPC152796
0.8092 Intermediate Similarity NPC476142
0.8088 Intermediate Similarity NPC254819
0.8088 Intermediate Similarity NPC219677
0.8085 Intermediate Similarity NPC476385
0.8085 Intermediate Similarity NPC476377
0.8085 Intermediate Similarity NPC134405
0.8085 Intermediate Similarity NPC47471
0.8082 Intermediate Similarity NPC35097
0.8074 Intermediate Similarity NPC295970
0.8074 Intermediate Similarity NPC184092
0.8071 Intermediate Similarity NPC205195
0.8071 Intermediate Similarity NPC49597
0.8069 Intermediate Similarity NPC28776
0.8069 Intermediate Similarity NPC473138
0.806 Intermediate Similarity NPC476873
0.8056 Intermediate Similarity NPC473867
0.8056 Intermediate Similarity NPC291153
0.8042 Intermediate Similarity NPC141455
0.8042 Intermediate Similarity NPC473281
0.8042 Intermediate Similarity NPC296954
0.8042 Intermediate Similarity NPC77922
0.8042 Intermediate Similarity NPC196063
0.8042 Intermediate Similarity NPC300894
0.803 Intermediate Similarity NPC212176
0.803 Intermediate Similarity NPC138798
0.8028 Intermediate Similarity NPC222433
0.8028 Intermediate Similarity NPC265648
0.8027 Intermediate Similarity NPC475407
0.8027 Intermediate Similarity NPC158546
0.8027 Intermediate Similarity NPC289021
0.8014 Intermediate Similarity NPC478234
0.8014 Intermediate Similarity NPC473799
0.8014 Intermediate Similarity NPC475530
0.8013 Intermediate Similarity NPC469384
0.8 Intermediate Similarity NPC148982
0.8 Intermediate Similarity NPC10945
0.8 Intermediate Similarity NPC475378
0.8 Intermediate Similarity NPC78363
0.7987 Intermediate Similarity NPC160882
0.7986 Intermediate Similarity NPC233350
0.7986 Intermediate Similarity NPC182217
0.7986 Intermediate Similarity NPC70680
0.7972 Intermediate Similarity NPC96795
0.7972 Intermediate Similarity NPC476384
0.7972 Intermediate Similarity NPC76406
0.7972 Intermediate Similarity NPC269141
0.7972 Intermediate Similarity NPC105005

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469549 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
0.8201 Intermediate Similarity NPD7266 Discontinued
0.7612 Intermediate Similarity NPD1091 Approved
0.7484 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6190 Approved
0.7403 Intermediate Similarity NPD8455 Phase 2
0.7394 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD7097 Phase 1
0.7333 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD9545 Approved
0.731 Intermediate Similarity NPD7033 Discontinued
0.7284 Intermediate Similarity NPD7054 Approved
0.7284 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD5048 Discontinued
0.7239 Intermediate Similarity NPD7074 Phase 3
0.7239 Intermediate Similarity NPD7472 Approved
0.7203 Intermediate Similarity NPD6233 Phase 2
0.719 Intermediate Similarity NPD1653 Approved
0.7181 Intermediate Similarity NPD4628 Phase 3
0.7152 Intermediate Similarity NPD7251 Discontinued
0.7152 Intermediate Similarity NPD7685 Pre-registration
0.7152 Intermediate Similarity NPD7075 Discontinued
0.7117 Intermediate Similarity NPD7228 Approved
0.7108 Intermediate Similarity NPD7808 Phase 3
0.7108 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4380 Phase 2
0.7091 Intermediate Similarity NPD6797 Phase 2
0.7055 Intermediate Similarity NPD6653 Approved
0.7048 Intermediate Similarity NPD6559 Discontinued
0.7042 Intermediate Similarity NPD5736 Approved
0.7039 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD6798 Discontinued
0.7012 Intermediate Similarity NPD3818 Discontinued
0.7006 Intermediate Similarity NPD37 Approved
0.7 Intermediate Similarity NPD6234 Discontinued
0.6992 Remote Similarity NPD7843 Approved
0.6986 Remote Similarity NPD230 Phase 1
0.6986 Remote Similarity NPD6355 Discontinued
0.6981 Remote Similarity NPD4967 Phase 2
0.6981 Remote Similarity NPD4966 Approved
0.6981 Remote Similarity NPD4965 Approved
0.6977 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6972 Remote Similarity NPD5647 Approved
0.6966 Remote Similarity NPD4062 Phase 3
0.6962 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6954 Remote Similarity NPD3400 Discontinued
0.6954 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6944 Remote Similarity NPD3027 Phase 3
0.6935 Remote Similarity NPD2933 Approved
0.6935 Remote Similarity NPD2934 Approved
0.6928 Remote Similarity NPD6799 Approved
0.6917 Remote Similarity NPD969 Suspended
0.6913 Remote Similarity NPD9570 Approved
0.6899 Remote Similarity NPD6801 Discontinued
0.6889 Remote Similarity NPD2629 Approved
0.6887 Remote Similarity NPD1652 Phase 2
0.688 Remote Similarity NPD2859 Approved
0.688 Remote Similarity NPD2860 Approved
0.687 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6867 Remote Similarity NPD7978 Discontinued
0.6864 Remote Similarity NPD8312 Approved
0.6864 Remote Similarity NPD8313 Approved
0.6863 Remote Similarity NPD5058 Phase 3
0.6849 Remote Similarity NPD6663 Approved
0.6838 Remote Similarity NPD7157 Approved
0.6835 Remote Similarity NPD5125 Phase 3
0.6835 Remote Similarity NPD5126 Approved
0.6835 Remote Similarity NPD7411 Suspended
0.6828 Remote Similarity NPD7095 Approved
0.6818 Remote Similarity NPD2684 Approved
0.681 Remote Similarity NPD7199 Phase 2
0.6795 Remote Similarity NPD5403 Approved
0.6792 Remote Similarity NPD1934 Approved
0.6788 Remote Similarity NPD9493 Approved
0.6786 Remote Similarity NPD3847 Discontinued
0.6784 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6783 Remote Similarity NPD6362 Approved
0.6781 Remote Similarity NPD3764 Approved
0.6776 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6772 Remote Similarity NPD9495 Approved
0.677 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6768 Remote Similarity NPD3787 Discontinued
0.6757 Remote Similarity NPD5124 Phase 1
0.6757 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6755 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6755 Remote Similarity NPD1550 Clinical (unspecified phase)
0.675 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6746 Remote Similarity NPD7240 Approved
0.6744 Remote Similarity NPD846 Approved
0.6744 Remote Similarity NPD940 Approved
0.6742 Remote Similarity NPD1358 Approved
0.6738 Remote Similarity NPD1535 Discovery
0.6738 Remote Similarity NPD3705 Approved
0.6738 Remote Similarity NPD422 Phase 1
0.6732 Remote Similarity NPD2575 Approved
0.6719 Remote Similarity NPD3020 Approved
0.6714 Remote Similarity NPD1778 Approved
0.6713 Remote Similarity NPD3225 Approved
0.6712 Remote Similarity NPD3136 Phase 2
0.6711 Remote Similarity NPD970 Clinical (unspecified phase)
0.6711 Remote Similarity NPD2424 Discontinued
0.6711 Remote Similarity NPD1549 Phase 2
0.6708 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6708 Remote Similarity NPD3817 Phase 2
0.6692 Remote Similarity NPD6647 Phase 2
0.6692 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6691 Remote Similarity NPD1894 Discontinued
0.669 Remote Similarity NPD1481 Phase 2
0.6689 Remote Similarity NPD826 Approved
0.6689 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6689 Remote Similarity NPD4060 Phase 1
0.6689 Remote Similarity NPD1613 Approved
0.6689 Remote Similarity NPD825 Approved
0.6689 Remote Similarity NPD2935 Discontinued
0.6687 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6687 Remote Similarity NPD6166 Phase 2
0.6687 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6674 Discontinued
0.6667 Remote Similarity NPD3094 Phase 2
0.6667 Remote Similarity NPD5401 Approved
0.6667 Remote Similarity NPD6685 Approved
0.6667 Remote Similarity NPD6599 Discontinued
0.6646 Remote Similarity NPD7972 Discontinued
0.6646 Remote Similarity NPD7819 Suspended
0.6645 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6645 Remote Similarity NPD6004 Phase 3
0.6645 Remote Similarity NPD6005 Phase 3
0.6645 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6645 Remote Similarity NPD6002 Phase 3
0.6644 Remote Similarity NPD4340 Discontinued
0.6644 Remote Similarity NPD6832 Phase 2
0.6643 Remote Similarity NPD1357 Approved
0.6642 Remote Similarity NPD3022 Approved
0.6642 Remote Similarity NPD3021 Approved
0.6627 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6625 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6623 Remote Similarity NPD8166 Discontinued
0.6621 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6617 Remote Similarity NPD290 Approved
0.6607 Remote Similarity NPD3751 Discontinued
0.6605 Remote Similarity NPD5402 Approved
0.6604 Remote Similarity NPD7458 Discontinued
0.6596 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6594 Remote Similarity NPD255 Approved
0.6594 Remote Similarity NPD256 Approved
0.6594 Remote Similarity NPD4198 Discontinued
0.6593 Remote Similarity NPD7435 Discontinued
0.6582 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6579 Remote Similarity NPD2240 Approved
0.6579 Remote Similarity NPD2239 Approved
0.6577 Remote Similarity NPD1240 Approved
0.6573 Remote Similarity NPD1608 Approved
0.6573 Remote Similarity NPD9269 Phase 2
0.6571 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6567 Remote Similarity NPD9266 Approved
0.6567 Remote Similarity NPD74 Approved
0.6561 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6561 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6561 Remote Similarity NPD3536 Discontinued
0.6557 Remote Similarity NPD8319 Approved
0.6557 Remote Similarity NPD8320 Phase 1
0.6556 Remote Similarity NPD4536 Approved
0.6556 Remote Similarity NPD4538 Approved
0.6556 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6554 Remote Similarity NPD3268 Approved
0.6552 Remote Similarity NPD8150 Discontinued
0.6543 Remote Similarity NPD2801 Approved
0.6541 Remote Similarity NPD3134 Approved
0.6536 Remote Similarity NPD5763 Approved
0.6536 Remote Similarity NPD5762 Approved
0.6535 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6533 Remote Similarity NPD555 Phase 2
0.6533 Remote Similarity NPD1933 Approved
0.6531 Remote Similarity NPD4908 Phase 1
0.6528 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6519 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6517 Remote Similarity NPD6534 Approved
0.6517 Remote Similarity NPD6535 Approved
0.6516 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6513 Remote Similarity NPD1510 Phase 2
0.651 Remote Similarity NPD5729 Clinical (unspecified phase)
0.651 Remote Similarity NPD520 Approved
0.6503 Remote Similarity NPD3092 Approved
0.6503 Remote Similarity NPD4806 Approved
0.6503 Remote Similarity NPD4807 Approved
0.65 Remote Similarity NPD7700 Phase 2
0.65 Remote Similarity NPD7699 Phase 2
0.6496 Remote Similarity NPD5535 Approved
0.6494 Remote Similarity NPD4534 Discontinued
0.6493 Remote Similarity NPD9267 Approved
0.6493 Remote Similarity NPD9264 Approved
0.6493 Remote Similarity NPD9263 Approved
0.649 Remote Similarity NPD1607 Approved
0.6488 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6483 Remote Similarity NPD8651 Approved
0.6479 Remote Similarity NPD5305 Approved
0.6479 Remote Similarity NPD5306 Approved
0.6475 Remote Similarity NPD6671 Approved
0.6475 Remote Similarity NPD111 Approved

Structure

External Identifiers

PubChem CID   46889079
ChEMBL   CHEMBL1086949
ZINC  

Physicochemical Properties

Molecular Weight:  472.19
ALogP:  -2.9989
MLogP:  2.67
XLogP:  0.518
# Rotatable Bonds:  20
Polar Surface Area:  183.21
# H-Bond Aceptor:  10
# H-Bond Donor:  6
# Rings:  2
# Heavy Atoms:  33

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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