Structure

Physi-Chem Properties

Molecular Weight:  499.3
Volume:  503.637
LogP:  1.256
LogD:  3.468
LogS:  -1.968
# Rotatable Bonds:  8
TPSA:  123.93
# H-Bond Aceptor:  7
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.398
Synthetic Accessibility Score:  4.532
Fsp3:  0.962
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.493
MDCK Permeability:  2.083531035168562e-05
Pgp-inhibitor:  0.024
Pgp-substrate:  0.083
Human Intestinal Absorption (HIA):  0.934
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.183
Plasma Protein Binding (PPB):  76.8987045288086%
Volume Distribution (VD):  0.512
Pgp-substrate:  9.762907981872559%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.788
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.686
CYP2C9-inhibitor:  0.021
CYP2C9-substrate:  0.065
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.106
CYP3A4-inhibitor:  0.046
CYP3A4-substrate:  0.09

ADMET: Excretion

Clearance (CL):  5.697
Half-life (T1/2):  0.749

ADMET: Toxicity

hERG Blockers:  0.254
Human Hepatotoxicity (H-HT):  0.405
Drug-inuced Liver Injury (DILI):  0.034
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.036
Maximum Recommended Daily Dose:  0.526
Skin Sensitization:  0.962
Carcinogencity:  0.232
Eye Corrosion:  0.022
Eye Irritation:  0.055
Respiratory Toxicity:  0.966

Download Data

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

  Natural Product: NPC247891

Natural Product ID:  NPC247891
Common Name*:   Tauroursodeoxycholate
IUPAC Name:   2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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:   Ursodeoxy Cholic Acid
Standard InCHIKey:  BHTRKEVKTKCXOH-LBSADWJPSA-N
Standard InCHI:  InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1
SMILES:  O[C@@H]1CC[C@]2([C@@H](C1)C[C@@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=NCCS(=O)(=O)O)O)C)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL272427
PubChem CID:   9848818
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001445] Bile acids, alcohols and derivatives
          • [CHEMONTID:0001159] Taurinated bile acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens Ki(app) = 0.005 mole fraction PMID[458578]
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens Activity = 5.0 % PMID[458578]
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens Activity = 15.0 % PMID[458578]
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens Activity = 1.53 % PMID[458578]
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens Activity = 87.2 % PMID[458578]
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens FC = 8.0 n.a. PMID[458578]
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens FC = 1.4 n.a. PMID[458578]
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens Kd = 10000.0 nM PMID[458578]
NPT545 Individual Protein Phospholipase A2 group 1B Homo sapiens Ki(app) = 0.000306 mole fraction PMID[458578]
NPT1028 Individual Protein Multidrug resistance-associated protein 4 Homo sapiens Activity = 26.0 % PMID[458587]
NPT1733 Individual Protein Solute carrier organic anion transporter family member 1A2 Homo sapiens Inhibition = 85.7 % PMID[458590]
NPT1733 Individual Protein Solute carrier organic anion transporter family member 1A2 Homo sapiens Activity = 9.0 % PMID[458591]
NPT305 Individual Protein Solute carrier organic anion transporter family member 1A4 Rattus norvegicus Km = 17000.0 nM PMID[458592]
NPT1733 Individual Protein Solute carrier organic anion transporter family member 1A2 Homo sapiens Km = 19000.0 nM PMID[458591]
NPT1631 Individual Protein Solute carrier organic anion transporter family member 1A5 Rattus norvegicus Km = 6600.0 nM PMID[458584]
NPT4418 Individual Protein Autotaxin Homo sapiens IC50 = 10300.0 nM PMID[458599]
NPT745 Individual Protein G-protein coupled bile acid receptor 1 Homo sapiens EC50 = 30000.0 nM PMID[458577]
NPT745 Individual Protein G-protein coupled bile acid receptor 1 Homo sapiens Efficacy = 97.0 % PMID[458577]
NPT27 Others Unspecified Activity = 1.073 % PMID[458579]
NPT27 Others Unspecified CC50 = 1002000.0 nM PMID[458579]
NPT27 Others Unspecified Activity = 1.049 % PMID[458579]
NPT713 Individual Protein Bile salt export pump Homo sapiens Km = 11900.0 nM PMID[458581]
NPT752 Individual Protein Solute carrier organic anion transporter family member 1A1 Rattus norvegicus Km = 13000.0 nM PMID[458582]
NPT751 Individual Protein Bile acid transporter Rattus norvegicus Km = 14000.0 nM PMID[458583]
NPT748 Individual Protein Bile acid transporter Homo sapiens Activity = 8.0 % PMID[458589]
NPT712 Individual Protein Bile salt export pump Rattus norvegicus Km = 4100.0 nM PMID[458593]
NPT754 Individual Protein Ileal bile acid transporter Homo sapiens Ki = 28000.0 nM PMID[458595]
NPT745 Individual Protein G-protein coupled bile acid receptor 1 Homo sapiens Activity = 39.0 % PMID[458597]
NPT745 Individual Protein G-protein coupled bile acid receptor 1 Homo sapiens EC50 = 105150.0 nM PMID[458597]
NPT745 Individual Protein G-protein coupled bile acid receptor 1 Homo sapiens EC50 = 50500.0 nM PMID[458597]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -21.08 % PMID[458600]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 15.88 % PMID[458601]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.14 % PMID[458602]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[458603]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[458603]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC247891 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 NPC159390
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

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC247891 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

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data