Natural Product: NPC320478

Natural Product ID:  NPC320478
Common Name:   Taurolithocholic Acid
IUPAC Name:   2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
Synonyms:   Taurolithocholate; Tauroursodeoxycholic acid
Molecular Formula:   C26H45NO5S
Standard InCHIKey:  QBYUNVOYXHFVKC-GBURMNQMSA-N
Standard InCHI:  InChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1
Canonical SMILES:  O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=NCCS(=O)(=O)O)O)C)C)C
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
NPO1797 Homo sapiens Species Hominidae Eukaryota blood PMID[16182619]
NPO1797 Homo sapiens Species Hominidae Eukaryota bile PMID[16548228]
NPO1797 Homo sapiens Species Hominidae Eukaryota Faeces PMID[22664055]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT745 Individual Protein G-protein coupled bile acid receptor 1 Homo sapiens EC50 = 290 nM 18307294
NPT612 Individual Protein Canalicular multispecific organic anion transporter 1 Homo sapiens Activity = 27 % 18457386
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens Activity = 40 % 19102680
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens Activity = 70 % 19102680
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens Activity = 5.29 % 19102680
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens Activity = 98.4 % 19102680
NPT2614 Individual Protein Multidrug resistance protein 1a Rattus norvegicus Activity = 16 % 7912687
NPT1422 Individual Protein ATP-binding cassette sub-family G member 2 Homo sapiens Activity = 20 % 12920197
NPT748 Individual Protein Bile acid transporter Homo sapiens Activity = 33 % 8132774
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 40 % 7912687
NPT1594 Individual Protein Multidrug resistance-associated protein 1 Homo sapiens Activity = 56 % 9188796
NPT713 Individual Protein Bile salt export pump Homo sapiens IC50 = 189200 nM 12739759
NPT1028 Individual Protein Multidrug resistance-associated protein 4 Homo sapiens IC50 = 20000 nM 12523936
NPT622 Individual Protein Solute carrier organic anion transporter family member 2B1 Homo sapiens Inhibition = 94.6 % 22541068
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 89.8 % 22541068
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 97.8 % 22541068
NPT198 Individual Protein Vitamin D receptor Homo sapiens EC50 > 150000 nM 26774929
NPT198 Individual Protein Vitamin D receptor Homo sapiens IC50 = 14500 nM 26774929
NPT198 Individual Protein Vitamin D receptor Homo sapiens IC50 > 50000 nM 26774929
NPT2 Others Unspecified LD50 > 0.15 nM 26774929

  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 NPC320478 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
0.9878 High Similarity NPC283751
0.9643 High Similarity NPC159390
0.9643 High Similarity NPC133995
0.9643 High Similarity NPC247891
0.9639 High Similarity NPC317363
0.8295 Intermediate Similarity NPC323958
0.8265 Intermediate Similarity NPC478053
0.7955 Intermediate Similarity NPC323180
0.7865 Intermediate Similarity NPC175419
0.7727 Intermediate Similarity NPC192456
0.7692 Intermediate Similarity NPC171698
0.7692 Intermediate Similarity NPC321340
0.7692 Intermediate Similarity NPC119633
0.7692 Intermediate Similarity NPC270957
0.7294 Intermediate Similarity NPC478103
0.716 Intermediate Similarity NPC114891
0.7126 Intermediate Similarity NPC478130
0.7037 Intermediate Similarity NPC218585
0.7037 Intermediate Similarity NPC148174
0.7037 Intermediate Similarity NPC71460
0.6988 Remote Similarity NPC477603
0.6966 Remote Similarity NPC477602
0.6966 Remote Similarity NPC477601
0.6966 Remote Similarity NPC473916
0.6957 Remote Similarity NPC109533
0.6905 Remote Similarity NPC142712
0.6867 Remote Similarity NPC159654
0.6867 Remote Similarity NPC69149
0.6867 Remote Similarity NPC167995
0.6867 Remote Similarity NPC281540
0.6867 Remote Similarity NPC118937
0.6864 Remote Similarity NPC473549
0.686 Remote Similarity NPC107919
0.686 Remote Similarity NPC66407
0.6824 Remote Similarity NPC473230
0.6824 Remote Similarity NPC475172
0.6824 Remote Similarity NPC48079
0.6824 Remote Similarity NPC475884
0.6813 Remote Similarity NPC329117
0.6809 Remote Similarity NPC246956
0.6786 Remote Similarity NPC474380
0.6786 Remote Similarity NPC473276
0.6786 Remote Similarity NPC41577
0.6782 Remote Similarity NPC63588
0.6782 Remote Similarity NPC251201
0.6782 Remote Similarity NPC192192
0.6782 Remote Similarity NPC232925
0.6765 Remote Similarity NPC473537
0.6744 Remote Similarity NPC472741
0.6706 Remote Similarity NPC44122
0.6705 Remote Similarity NPC127094
0.6705 Remote Similarity NPC100586
0.6705 Remote Similarity NPC157422
0.6705 Remote Similarity NPC252182
0.6705 Remote Similarity NPC109457
0.6705 Remote Similarity NPC1340
0.6705 Remote Similarity NPC187471
0.6705 Remote Similarity NPC470071
0.6699 Remote Similarity NPC252564
0.6699 Remote Similarity NPC475249
0.6667 Remote Similarity NPC129829
0.6667 Remote Similarity NPC299948
0.6667 Remote Similarity NPC254037
0.6667 Remote Similarity NPC477820
0.6667 Remote Similarity NPC476735
0.6667 Remote Similarity NPC241085
0.6667 Remote Similarity NPC470830
0.6635 Remote Similarity NPC201712
0.6629 Remote Similarity NPC470610
0.6629 Remote Similarity NPC153719
0.6591 Remote Similarity NPC231945
0.6591 Remote Similarity NPC282454
0.6571 Remote Similarity NPC475518
0.6556 Remote Similarity NPC48795
0.6556 Remote Similarity NPC304499
0.6526 Remote Similarity NPC477599
0.6517 Remote Similarity NPC131506
0.6517 Remote Similarity NPC324984
0.6517 Remote Similarity NPC323900
0.6517 Remote Similarity NPC156277
0.6517 Remote Similarity NPC126642
0.6517 Remote Similarity NPC151018
0.6517 Remote Similarity NPC157777
0.6517 Remote Similarity NPC477823
0.6517 Remote Similarity NPC477821
0.6517 Remote Similarity NPC195530
0.6517 Remote Similarity NPC473279
0.6517 Remote Similarity NPC58057
0.6517 Remote Similarity NPC473552
0.6517 Remote Similarity NPC477822
0.6517 Remote Similarity NPC320549
0.6484 Remote Similarity NPC243027
0.6484 Remote Similarity NPC158208
0.6484 Remote Similarity NPC196136
0.6484 Remote Similarity NPC317242
0.6477 Remote Similarity NPC99264
0.6471 Remote Similarity NPC280710
0.6471 Remote Similarity NPC243985
0.6458 Remote Similarity NPC478054
0.6444 Remote Similarity NPC232112
0.6444 Remote Similarity NPC473238
0.6444 Remote Similarity NPC472341
0.6442 Remote Similarity NPC240650
0.6437 Remote Similarity NPC63190
0.6413 Remote Similarity NPC4209
0.6413 Remote Similarity NPC163597
0.6395 Remote Similarity NPC243469
0.6395 Remote Similarity NPC190827
0.6395 Remote Similarity NPC475943
0.6395 Remote Similarity NPC472946
0.6392 Remote Similarity NPC320824
0.6383 Remote Similarity NPC52951
0.6383 Remote Similarity NPC474132
0.6374 Remote Similarity NPC280026
0.6374 Remote Similarity NPC10476
0.6374 Remote Similarity NPC167702
0.6374 Remote Similarity NPC477508
0.6374 Remote Similarity NPC192501
0.6374 Remote Similarity NPC228994
0.6374 Remote Similarity NPC254340
0.6344 Remote Similarity NPC302578
0.6344 Remote Similarity NPC185915
0.6344 Remote Similarity NPC105208
0.6344 Remote Similarity NPC11907
0.6344 Remote Similarity NPC317913
0.6344 Remote Similarity NPC477227
0.6344 Remote Similarity NPC64081
0.6344 Remote Similarity NPC207010
0.6344 Remote Similarity NPC128951
0.6344 Remote Similarity NPC192046
0.6344 Remote Similarity NPC474574
0.6344 Remote Similarity NPC133596
0.6337 Remote Similarity NPC312637
0.6333 Remote Similarity NPC111234
0.6304 Remote Similarity NPC231680
0.6304 Remote Similarity NPC230704
0.6304 Remote Similarity NPC231256
0.6304 Remote Similarity NPC3403
0.6304 Remote Similarity NPC212879
0.6304 Remote Similarity NPC104387
0.6304 Remote Similarity NPC91387
0.6304 Remote Similarity NPC273366
0.6304 Remote Similarity NPC70982
0.6304 Remote Similarity NPC195155
0.6304 Remote Similarity NPC478105
0.6304 Remote Similarity NPC185536
0.6304 Remote Similarity NPC270306
0.6304 Remote Similarity NPC103822
0.6304 Remote Similarity NPC178383
0.6304 Remote Similarity NPC97534
0.6304 Remote Similarity NPC212733
0.6304 Remote Similarity NPC174964
0.6304 Remote Similarity NPC240235
0.63 Remote Similarity NPC324405
0.6296 Remote Similarity NPC45365
0.6296 Remote Similarity NPC293299
0.6292 Remote Similarity NPC6120
0.6292 Remote Similarity NPC213178
0.6292 Remote Similarity NPC327728
0.6292 Remote Similarity NPC131892
0.6277 Remote Similarity NPC324700
0.6277 Remote Similarity NPC224802
0.6277 Remote Similarity NPC301707
0.6277 Remote Similarity NPC18857
0.6277 Remote Similarity NPC67657
0.6277 Remote Similarity NPC80089
0.6277 Remote Similarity NPC147993
0.6277 Remote Similarity NPC185465
0.6277 Remote Similarity NPC171426
0.6277 Remote Similarity NPC34046
0.6264 Remote Similarity NPC195489
0.6237 Remote Similarity NPC278091
0.6237 Remote Similarity NPC93662
0.6237 Remote Similarity NPC5767
0.6237 Remote Similarity NPC78067
0.6237 Remote Similarity NPC472486
0.6237 Remote Similarity NPC86305
0.6237 Remote Similarity NPC472487
0.6237 Remote Similarity NPC475742
0.6237 Remote Similarity NPC470145
0.6237 Remote Similarity NPC91573
0.6237 Remote Similarity NPC14112
0.6224 Remote Similarity NPC478102
0.6222 Remote Similarity NPC45296
0.6211 Remote Similarity NPC320144
0.6211 Remote Similarity NPC220379
0.6211 Remote Similarity NPC477282
0.6211 Remote Similarity NPC287452
0.6211 Remote Similarity NPC201276
0.6211 Remote Similarity NPC81074
0.6211 Remote Similarity NPC80891
0.6207 Remote Similarity NPC260116
0.6207 Remote Similarity NPC80463
0.62 Remote Similarity NPC477600
0.6196 Remote Similarity NPC49168
0.6196 Remote Similarity NPC62657
0.6196 Remote Similarity NPC254509
0.6196 Remote Similarity NPC145552
0.6196 Remote Similarity NPC196358
0.6196 Remote Similarity NPC192638

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC320478 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
0.9643 High Similarity NPD6701 Clinical (unspecified phase)
0.9643 High Similarity NPD6700 Approved
0.9302 High Similarity NPD6703 Approved
0.9302 High Similarity NPD6702 Approved
0.6941 Remote Similarity NPD6705 Phase 1
0.686 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6813 Remote Similarity NPD5364 Discontinued
0.6796 Remote Similarity NPD8418 Phase 2
0.6765 Remote Similarity NPD7920 Phase 3
0.6765 Remote Similarity NPD7919 Phase 3
0.6699 Remote Similarity NPD8088 Phase 1
0.6591 Remote Similarity NPD4787 Phase 1
0.6517 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6517 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6413 Remote Similarity NPD6117 Approved
0.6374 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6344 Remote Similarity NPD6116 Phase 1
0.6292 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6292 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6277 Remote Similarity NPD6118 Approved
0.6277 Remote Similarity NPD6114 Approved
0.6277 Remote Similarity NPD6697 Approved
0.6277 Remote Similarity NPD6115 Approved
0.6146 Remote Similarity NPD7525 Registered
0.6095 Remote Similarity NPD7991 Discontinued
0.6087 Remote Similarity NPD8298 Phase 2
0.6044 Remote Similarity NPD4245 Approved
0.6044 Remote Similarity NPD4244 Approved
0.6044 Remote Similarity NPD4789 Approved
0.6 Remote Similarity NPD5360 Phase 3
0.6 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5979 Remote Similarity NPD6928 Phase 2
0.5957 Remote Similarity NPD3703 Phase 2
0.5941 Remote Similarity NPD8308 Discontinued
0.5934 Remote Similarity NPD3698 Phase 2
0.5929 Remote Similarity NPD8174 Phase 2
0.5843 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6942 Approved
0.5789 Remote Similarity NPD7339 Approved
0.5773 Remote Similarity NPD3671 Phase 1
0.5752 Remote Similarity NPD6920 Discontinued
0.5714 Remote Similarity NPD5354 Approved
0.5701 Remote Similarity NPD5771 Approved
0.5686 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5638 Remote Similarity NPD3187 Discontinued
0.5638 Remote Similarity NPD4758 Discontinued
0.5638 Remote Similarity NPD6081 Approved

Structure

External Identifiers

PubChem CID   439763
ChEMBL   CHEMBL408701
ZINC  

Physicochemical Properties

Molecular Weight:  483.30
ALogP:  0.2887
MLogP:  3.55
XLogP:  7.359
# Rotatable Bonds:  13
Polar Surface Area:  115.57
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  33

Download Data

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Structure MOL file  
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