Natural Product: NPC159390

Natural Product ID:  NPC159390
Common Name:   Taurocholate
IUPAC Name:   2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-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:   Cholaic acid; Cholic acid taurine conjugate; N-Choloyltaurine; Taurocholate
Molecular Formula:   C26H45NO7S
Standard InCHIKey:  WBWWGRHZICKQGZ-HZAMXZRMSA-N
Standard InCHI:  InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1
Canonical SMILES:  O[C@@H]1CC[C@]2([C@@H](C1)C[C@H]([C@@H]1[C@@H]2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=NCCS(=O)(=O)O)O)C)C)O)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
NPO4808 Bovis calculus NA NA NA TCMSP*
NPO1797 Homo sapiens Species Hominidae Eukaryota blood Geigy Scientific Tables, 8th Rev edition. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
NPO1797 Homo sapiens Species Hominidae Eukaryota PMID[11160372]
NPO1797 Homo sapiens Species Hominidae Eukaryota bile PMID[11160372]
NPO1797 Homo sapiens Species Hominidae Eukaryota Faeces PMID[22664055]
NPO1797 Homo sapiens Species Hominidae Eukaryota urine PMID[3944741]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT751 Individual Protein Bile acid transporter Rattus norvegicus IC50 = 6000 nM 15261266
NPT19 Organism Escherichia coli Escherichia coli MIC = 64000 ug/ml 17210767
NPT19 Organism Escherichia coli Escherichia coli MIC = 8000 ug/ml 17210767
NPT19 Organism Escherichia coli Escherichia coli MIC = 4000 ug/ml 17210767
NPT745 Individual Protein G-protein coupled bile acid receptor 1 Homo sapiens EC50 = 4950 nM 18307294
NPT612 Individual Protein Canalicular multispecific organic anion transporter 1 Homo sapiens Activity = 87 % 18457386
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens Activity = 80 % 19102680
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens Activity = 90 % 19102680
NPT19 Organism Escherichia coli Escherichia coli MIC = 8 ug/ml 20038628
NPT19 Organism Escherichia coli Escherichia coli MIC = 4 ug/ml 20038628
NPT19 Organism Escherichia coli Escherichia coli MIC = 32 ug/ml 20038628
NPT19 Organism Escherichia coli Escherichia coli MIC = 16 ug/ml 20038628
NPT746 Organism Pasteurella multocida Pasteurella multocida MIC = 3125 ug/ml 18725450
NPT746 Organism Pasteurella multocida Pasteurella multocida MIC = 1562.5 ug/ml 18725450
NPT746 Organism Pasteurella multocida Pasteurella multocida MIC = 781.25 ug/ml 18725450
NPT746 Organism Pasteurella multocida Pasteurella multocida Ratio = 2 18725450
NPT1739 Individual Protein Canalicular multispecific organic anion transporter 2 Rattus norvegicus Activity = 42 % 12909565
NPT1594 Individual Protein Multidrug resistance-associated protein 1 Homo sapiens Activity = 72 % 9188796
NPT1736 Individual Protein ATP-binding cassette sub-family C member 11 Homo sapiens Activity = 72 % 15537867
NPT1739 Individual Protein Canalicular multispecific organic anion transporter 2 Rattus norvegicus Activity = 19.2 % 10644759
NPT1739 Individual Protein Canalicular multispecific organic anion transporter 2 Rattus norvegicus Activity = 0 % 10644759
NPT752 Individual Protein Solute carrier organic anion transporter family member 1A1 Rattus norvegicus Activity = 11 % 9632674
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Activity = 14 % 10644574
NPT1733 Individual Protein Solute carrier organic anion transporter family member 1A2 Homo sapiens Activity = 14 % 7557095
NPT752 Individual Protein Solute carrier organic anion transporter family member 1A1 Rattus norvegicus Activity = 15 % 9632674
NPT1739 Individual Protein Canalicular multispecific organic anion transporter 2 Rattus norvegicus Activity = 15.8 % 10644759
NPT1739 Individual Protein Canalicular multispecific organic anion transporter 2 Rattus norvegicus Activity = 19 % 12909565
NPT1739 Individual Protein Canalicular multispecific organic anion transporter 2 Rattus norvegicus Activity = 20.3 % 10644759
NPT2850 Individual Protein Multidrug resistance associated protein Homo sapiens Activity = 21.7 % 11585759
NPT752 Individual Protein Solute carrier organic anion transporter family member 1A1 Rattus norvegicus Activity = 28 % 8786566
NPT877 Individual Protein Solute carrier family 22 member 8 Mus musculus Activity = 19.5 % 14762099
NPT1023 Individual Protein Solute carrier organic anion transporter family member 3A1 Homo sapiens Activity = 40 % 14631946
NPT957 Individual Protein Multidrug resistance-associated protein 7 Homo sapiens Activity = 44.5 % 12527806
NPT2613 Individual Protein Bile salt export pump Mus musculus Activity = 46 % 10607905
NPT1733 Individual Protein Solute carrier organic anion transporter family member 1A2 Homo sapiens Activity = 48 % 7557095
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Activity = 50 % 12906759
NPT1733 Individual Protein Solute carrier organic anion transporter family member 1A2 Homo sapiens Activity = 53 % 7557095
NPT2850 Individual Protein Multidrug resistance associated protein Homo sapiens Activity = 55 % 12220224
NPT748 Individual Protein Bile acid transporter Homo sapiens Activity = 57 % 8132774
NPT1028 Individual Protein Multidrug resistance-associated protein 4 Homo sapiens Activity = 64 % 12883481
NPT1422 Individual Protein ATP-binding cassette sub-family G member 2 Homo sapiens Activity = 70 % 12920197
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 88 % 7912687
NPT305 Individual Protein Solute carrier organic anion transporter family member 1A4 Rattus norvegicus IC50 = 1480000 nM 11561088
NPT1028 Individual Protein Multidrug resistance-associated protein 4 Homo sapiens IC50 = 250000 nM 14643890
NPT1028 Individual Protein Multidrug resistance-associated protein 4 Homo sapiens IC50 = 350000 nM 12523936
NPT2850 Individual Protein Multidrug resistance associated protein Homo sapiens IC50 = 40000 nM 12924948
NPT748 Individual Protein Bile acid transporter Homo sapiens IC50 = 5300 nM 10565843
NPT752 Individual Protein Solute carrier organic anion transporter family member 1A1 Rattus norvegicus Ki = 10800 nM 11408557
NPT1744 Individual Protein Solute carrier organic anion transporter family member 1C1 Mus musculus Ki = 109000 nM 15166123
NPT305 Individual Protein Solute carrier organic anion transporter family member 1A4 Rattus norvegicus Ki = 156000 nM 11792694
NPT750 Individual Protein Solute carrier organic anion transporter family member 1A3 Rattus norvegicus Ki = 183000 nM 10869408
NPT666 Individual Protein Solute carrier family 22 member 6 Rattus norvegicus Ki = 2770000 nM 11408557
NPT752 Individual Protein Solute carrier organic anion transporter family member 1A1 Rattus norvegicus Ki = 32000 nM 9794920
NPT305 Individual Protein Solute carrier organic anion transporter family member 1A4 Rattus norvegicus Ki = 39400 nM 11408557
NPT754 Individual Protein Ileal bile acid transporter Homo sapiens Ki = 41500 nM 9458785
NPT667 Individual Protein Solute carrier family 22 member 8 Rattus norvegicus Ki = 790000 nM 11408557
NPT622 Individual Protein Solute carrier organic anion transporter family member 2B1 Homo sapiens Inhibition = 96.2 % 22541068
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 95.5 % 22541068
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 93 % 22541068

  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 NPC159390 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 NPC247891
1.0 High Similarity NPC133995
0.9762 High Similarity NPC283751
0.9643 High Similarity NPC320478
0.9302 High Similarity NPC317363
0.8571 High Similarity NPC478053
0.8022 Intermediate Similarity NPC270957
0.8022 Intermediate Similarity NPC119633
0.8022 Intermediate Similarity NPC171698
0.8022 Intermediate Similarity NPC321340
0.8022 Intermediate Similarity NPC323958
0.7802 Intermediate Similarity NPC175419
0.7692 Intermediate Similarity NPC323180
0.7473 Intermediate Similarity NPC192456
0.7303 Intermediate Similarity NPC473916
0.7303 Intermediate Similarity NPC477601
0.7303 Intermediate Similarity NPC477602
0.7241 Intermediate Similarity NPC478103
0.7209 Intermediate Similarity NPC66407
0.7126 Intermediate Similarity NPC251201
0.7126 Intermediate Similarity NPC63588
0.7126 Intermediate Similarity NPC232925
0.7126 Intermediate Similarity NPC192192
0.7119 Intermediate Similarity NPC473549
0.7079 Intermediate Similarity NPC478130
0.7045 Intermediate Similarity NPC187471
0.7045 Intermediate Similarity NPC470071
0.7045 Intermediate Similarity NPC127094
0.7045 Intermediate Similarity NPC252182
0.7045 Intermediate Similarity NPC1340
0.7011 Intermediate Similarity NPC129829
0.7011 Intermediate Similarity NPC477820
0.7011 Intermediate Similarity NPC254037
0.6966 Remote Similarity NPC153719
0.6966 Remote Similarity NPC470610
0.6923 Remote Similarity NPC201712
0.6915 Remote Similarity NPC109533
0.6905 Remote Similarity NPC114891
0.6889 Remote Similarity NPC304499
0.6889 Remote Similarity NPC48795
0.686 Remote Similarity NPC142712
0.6854 Remote Similarity NPC473552
0.6854 Remote Similarity NPC477821
0.6854 Remote Similarity NPC477822
0.6854 Remote Similarity NPC323900
0.6854 Remote Similarity NPC477823
0.6854 Remote Similarity NPC324984
0.6818 Remote Similarity NPC107919
0.6813 Remote Similarity NPC243027
0.6813 Remote Similarity NPC317242
0.6813 Remote Similarity NPC196136
0.6813 Remote Similarity NPC158208
0.6786 Remote Similarity NPC218585
0.6786 Remote Similarity NPC148174
0.6786 Remote Similarity NPC71460
0.6782 Remote Similarity NPC475884
0.6782 Remote Similarity NPC48079
0.6782 Remote Similarity NPC473230
0.6771 Remote Similarity NPC246956
0.6771 Remote Similarity NPC478054
0.6744 Remote Similarity NPC477603
0.6744 Remote Similarity NPC41577
0.6744 Remote Similarity NPC473276
0.6744 Remote Similarity NPC474380
0.6739 Remote Similarity NPC163597
0.6731 Remote Similarity NPC473537
0.6705 Remote Similarity NPC472741
0.6703 Remote Similarity NPC228994
0.6703 Remote Similarity NPC192501
0.6703 Remote Similarity NPC10476
0.6701 Remote Similarity NPC320824
0.6667 Remote Similarity NPC185915
0.6667 Remote Similarity NPC475249
0.6667 Remote Similarity NPC157422
0.6667 Remote Similarity NPC252564
0.6667 Remote Similarity NPC128951
0.6667 Remote Similarity NPC474574
0.6667 Remote Similarity NPC44122
0.6667 Remote Similarity NPC192046
0.6667 Remote Similarity NPC100586
0.6667 Remote Similarity NPC133596
0.6667 Remote Similarity NPC302578
0.6667 Remote Similarity NPC109457
0.6667 Remote Similarity NPC105208
0.6667 Remote Similarity NPC11907
0.6667 Remote Similarity NPC477227
0.6667 Remote Similarity NPC64081
0.663 Remote Similarity NPC91387
0.663 Remote Similarity NPC231680
0.663 Remote Similarity NPC270306
0.6629 Remote Similarity NPC299948
0.6629 Remote Similarity NPC241085
0.6629 Remote Similarity NPC470830
0.6628 Remote Similarity NPC281540
0.6628 Remote Similarity NPC69149
0.6628 Remote Similarity NPC159654
0.6628 Remote Similarity NPC118937
0.6628 Remote Similarity NPC167995
0.6596 Remote Similarity NPC80089
0.6596 Remote Similarity NPC324700
0.6596 Remote Similarity NPC329117
0.6596 Remote Similarity NPC171426
0.6596 Remote Similarity NPC224802
0.6596 Remote Similarity NPC18857
0.6596 Remote Similarity NPC147993
0.6596 Remote Similarity NPC34046
0.6596 Remote Similarity NPC67657
0.6591 Remote Similarity NPC475172
0.6556 Remote Similarity NPC231945
0.6556 Remote Similarity NPC282454
0.6542 Remote Similarity NPC475518
0.6526 Remote Similarity NPC220379
0.6526 Remote Similarity NPC201276
0.6526 Remote Similarity NPC477282
0.6526 Remote Similarity NPC80891
0.6526 Remote Similarity NPC287452
0.6526 Remote Similarity NPC81074
0.6522 Remote Similarity NPC472503
0.6522 Remote Similarity NPC308440
0.6517 Remote Similarity NPC474756
0.6512 Remote Similarity NPC209686
0.6512 Remote Similarity NPC249078
0.6512 Remote Similarity NPC236099
0.65 Remote Similarity NPC477600
0.6495 Remote Similarity NPC477599
0.6489 Remote Similarity NPC212453
0.6489 Remote Similarity NPC202540
0.6489 Remote Similarity NPC476233
0.6484 Remote Similarity NPC195530
0.6484 Remote Similarity NPC473279
0.6484 Remote Similarity NPC157777
0.6484 Remote Similarity NPC131506
0.6458 Remote Similarity NPC78545
0.6458 Remote Similarity NPC71535
0.6452 Remote Similarity NPC103822
0.6444 Remote Similarity NPC470833
0.6429 Remote Similarity NPC476735
0.6421 Remote Similarity NPC471045
0.6421 Remote Similarity NPC471769
0.6421 Remote Similarity NPC477817
0.6421 Remote Similarity NPC477819
0.6421 Remote Similarity NPC31828
0.6413 Remote Similarity NPC232112
0.6413 Remote Similarity NPC473238
0.6413 Remote Similarity NPC472341
0.6404 Remote Similarity NPC63190
0.6392 Remote Similarity NPC73515
0.6392 Remote Similarity NPC469745
0.6383 Remote Similarity NPC4209
0.6354 Remote Similarity NPC476176
0.6354 Remote Similarity NPC116119
0.6354 Remote Similarity NPC80297
0.6354 Remote Similarity NPC472742
0.6354 Remote Similarity NPC475727
0.6344 Remote Similarity NPC477508
0.6344 Remote Similarity NPC475458
0.6333 Remote Similarity NPC469987
0.6327 Remote Similarity NPC296734
0.6327 Remote Similarity NPC268040
0.6327 Remote Similarity NPC470611
0.6327 Remote Similarity NPC121121
0.6327 Remote Similarity NPC202688
0.6327 Remote Similarity NPC154043
0.6327 Remote Similarity NPC475388
0.6327 Remote Similarity NPC60018
0.6316 Remote Similarity NPC317913
0.6316 Remote Similarity NPC207010
0.6304 Remote Similarity NPC58057
0.6304 Remote Similarity NPC156277
0.6304 Remote Similarity NPC126642
0.6304 Remote Similarity NPC320549
0.6304 Remote Similarity NPC111234
0.6304 Remote Similarity NPC151018
0.6289 Remote Similarity NPC470609
0.6289 Remote Similarity NPC16449
0.6289 Remote Similarity NPC475679
0.6286 Remote Similarity NPC243985
0.6286 Remote Similarity NPC280710
0.6277 Remote Similarity NPC3403
0.6277 Remote Similarity NPC231256
0.6277 Remote Similarity NPC104387
0.6277 Remote Similarity NPC212879
0.6277 Remote Similarity NPC240235
0.6277 Remote Similarity NPC159789
0.6277 Remote Similarity NPC185536
0.6277 Remote Similarity NPC195155
0.6277 Remote Similarity NPC273366
0.6277 Remote Similarity NPC212733
0.6277 Remote Similarity NPC70982
0.6277 Remote Similarity NPC97534
0.6277 Remote Similarity NPC178383
0.6277 Remote Similarity NPC478105
0.6277 Remote Similarity NPC230704
0.6277 Remote Similarity NPC174964
0.6264 Remote Similarity NPC99264
0.6263 Remote Similarity NPC216420
0.6263 Remote Similarity NPC110778
0.6263 Remote Similarity NPC85095
0.6263 Remote Similarity NPC211135
0.6263 Remote Similarity NPC470070

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC159390 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
1.0 High Similarity NPD6700 Approved
1.0 High Similarity NPD6701 Clinical (unspecified phase)
0.9651 High Similarity NPD6702 Approved
0.9651 High Similarity NPD6703 Approved
0.7087 Intermediate Similarity NPD8418 Phase 2
0.6818 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6731 Remote Similarity NPD7920 Phase 3
0.6731 Remote Similarity NPD7919 Phase 3
0.6705 Remote Similarity NPD6705 Phase 1
0.6667 Remote Similarity NPD8088 Phase 1
0.6596 Remote Similarity NPD6118 Approved
0.6596 Remote Similarity NPD6697 Approved
0.6596 Remote Similarity NPD6115 Approved
0.6596 Remote Similarity NPD5364 Discontinued
0.6596 Remote Similarity NPD6114 Approved
0.6383 Remote Similarity NPD6117 Approved
0.6374 Remote Similarity NPD4787 Phase 1
0.6316 Remote Similarity NPD6116 Phase 1
0.6304 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6304 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6277 Remote Similarity NPD3703 Phase 2
0.6238 Remote Similarity NPD8308 Discontinued
0.6226 Remote Similarity NPD7991 Discontinued
0.6207 Remote Similarity NPD8298 Phase 2
0.617 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6122 Remote Similarity NPD7525 Registered
0.6122 Remote Similarity NPD6928 Phase 2
0.6087 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6087 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6053 Remote Similarity NPD8174 Phase 2
0.5851 Remote Similarity NPD4789 Approved
0.5851 Remote Similarity NPD4245 Approved
0.5851 Remote Similarity NPD4244 Approved
0.5806 Remote Similarity NPD5360 Phase 3
0.5806 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5745 Remote Similarity NPD3698 Phase 2
0.5701 Remote Similarity NPD7136 Phase 2
0.57 Remote Similarity NPD5354 Approved
0.5673 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5652 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5612 Remote Similarity NPD6942 Approved
0.5612 Remote Similarity NPD7339 Approved
0.5603 Remote Similarity NPD6920 Discontinued
0.56 Remote Similarity NPD3671 Phase 1

Structure

External Identifiers

PubChem CID   6675
ChEMBL   CHEMBL224867
ZINC  

Physicochemical Properties

Molecular Weight:  515.29
ALogP:  -1.0507
MLogP:  3.33
XLogP:  3.189
# Rotatable Bonds:  15
Polar Surface Area:  156.03
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  35

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs