Structure

Physi-Chem Properties

Molecular Weight:  836.42
Volume:  819.85
LogP:  3.052
LogD:  2.068
LogS:  -3.948
# Rotatable Bonds:  8
TPSA:  256.04
# H-Bond Aceptor:  16
# H-Bond Donor:  7
# Rings:  7
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.144
Synthetic Accessibility Score:  5.961
Fsp3:  0.86
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.345
MDCK Permeability:  4.707600237452425e-05
Pgp-inhibitor:  0.145
Pgp-substrate:  0.117
Human Intestinal Absorption (HIA):  0.913
20% Bioavailability (F20%):  0.496
30% Bioavailability (F30%):  0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.178
Plasma Protein Binding (PPB):  73.11141204833984%
Volume Distribution (VD):  0.459
Pgp-substrate:  12.97737979888916%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.979
CYP2C19-inhibitor:  0.003
CYP2C19-substrate:  0.323
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.014
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.029
CYP3A4-inhibitor:  0.078
CYP3A4-substrate:  0.019

ADMET: Excretion

Clearance (CL):  1.003
Half-life (T1/2):  0.579

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.194
Drug-inuced Liver Injury (DILI):  0.007
AMES Toxicity:  0.125
Rat Oral Acute Toxicity:  0.066
Maximum Recommended Daily Dose:  0.521
Skin Sensitization:  0.014
Carcinogencity:  0.04
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.948

Download Data

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

  Natural Product: NPC262199

Natural Product ID:  NPC262199
Common Name*:   Glycyrrhizic Acid 6''-Methyl Ester
IUPAC Name:   (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxycarbonyloxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:  
Standard InCHIKey:  JENBECQUKVEUTQ-ILVQQCHOSA-N
Standard InCHI:  InChI=1S/C43H64O16/c1-38(2)22-9-12-43(7)32(21(44)17-19-20-18-40(4,37(53)54)14-13-39(20,3)15-16-42(19,43)6)41(22,5)11-10-23(38)56-36-31(27(48)26(47)29(57-36)33(50)51)59-35-28(49)24(45)25(46)30(58-35)34(52)55-8/h17,20,22-32,35-36,45-49H,9-16,18H2,1-8H3,(H,50,51)(H,53,54)/t20-,22-,23-,24-,25-,26-,27-,28+,29-,30-,31+,32+,35-,36+,39+,40-,41-,42+,43+/m0/s1
SMILES:  CC1(C)[C@@H]2CC[C@]3(C)[C@H](C(=O)C=C4[C@@H]5C[C@](C)(CC[C@]5(C)CC[C@@]34C)C(=O)O)[C@@]2(C)CC[C@@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)OC)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL594736
PubChem CID:   46226470
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001580] Triterpene glycosides
            • [CHEMONTID:0002358] Triterpene saponins

*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
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10026 Mitracarpus scaber Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7786 Lentinus tigrinus Species Lentinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ 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
NPT2 Others Unspecified FC = 1.4 n.a. PMID[491472]
NPT2 Others Unspecified FC = 0.9 n.a. PMID[491472]

☑ 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 NPC262199 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 NPC202666
1.0 High Similarity NPC471961
1.0 High Similarity NPC471964
1.0 High Similarity NPC14617
0.9912 High Similarity NPC471965
0.9912 High Similarity NPC247315
0.9912 High Similarity NPC471962
0.9912 High Similarity NPC471963
0.9826 High Similarity NPC285091
0.9737 High Similarity NPC162574
0.9649 High Similarity NPC301449
0.9649 High Similarity NPC64715
0.9649 High Similarity NPC159309
0.9649 High Similarity NPC114484
0.9649 High Similarity NPC86222
0.9649 High Similarity NPC222580
0.9649 High Similarity NPC11242
0.9649 High Similarity NPC171544
0.9649 High Similarity NPC31838
0.9649 High Similarity NPC297263
0.9649 High Similarity NPC223301
0.9649 High Similarity NPC62725
0.9649 High Similarity NPC104372
0.9649 High Similarity NPC22956
0.9646 High Similarity NPC180550
0.9646 High Similarity NPC473884
0.9646 High Similarity NPC475171
0.9646 High Similarity NPC214484
0.9646 High Similarity NPC472949
0.9646 High Similarity NPC208381
0.9646 High Similarity NPC39211
0.9646 High Similarity NPC35405
0.9646 High Similarity NPC6377
0.9646 High Similarity NPC11551
0.9646 High Similarity NPC309780
0.9646 High Similarity NPC114441
0.9646 High Similarity NPC157868
0.9646 High Similarity NPC469945
0.9565 High Similarity NPC475591
0.9565 High Similarity NPC187290
0.9565 High Similarity NPC107966
0.9565 High Similarity NPC21691
0.9565 High Similarity NPC249848
0.9565 High Similarity NPC80986
0.9565 High Similarity NPC10607
0.9565 High Similarity NPC40775
0.9565 High Similarity NPC4749
0.9565 High Similarity NPC235438
0.9565 High Similarity NPC236870
0.9565 High Similarity NPC213952
0.9561 High Similarity NPC236657
0.9561 High Similarity NPC118440
0.9558 High Similarity NPC286347
0.9487 High Similarity NPC181066
0.9487 High Similarity NPC469947
0.9483 High Similarity NPC258617
0.9483 High Similarity NPC30735
0.9483 High Similarity NPC281148
0.9483 High Similarity NPC235405
0.9483 High Similarity NPC200049
0.9483 High Similarity NPC2370
0.9483 High Similarity NPC44716
0.9483 High Similarity NPC283417
0.9483 High Similarity NPC302543
0.9483 High Similarity NPC257211
0.9478 High Similarity NPC31193
0.9478 High Similarity NPC75417
0.9478 High Similarity NPC187618
0.9478 High Similarity NPC242840
0.9478 High Similarity NPC302887
0.9474 High Similarity NPC192791
0.9469 High Similarity NPC224121
0.9412 High Similarity NPC477196
0.9402 High Similarity NPC160452
0.9402 High Similarity NPC470477
0.9402 High Similarity NPC33068
0.9397 High Similarity NPC131469
0.9397 High Similarity NPC313110
0.9391 High Similarity NPC294112
0.9386 High Similarity NPC109588
0.9333 High Similarity NPC477197
0.9328 High Similarity NPC477193
0.9328 High Similarity NPC477192
0.9328 High Similarity NPC477191
0.9328 High Similarity NPC475281
0.9328 High Similarity NPC477075
0.9328 High Similarity NPC477194
0.9328 High Similarity NPC477078
0.9328 High Similarity NPC329923
0.9322 High Similarity NPC470218
0.9322 High Similarity NPC284449
0.9322 High Similarity NPC475368
0.9316 High Similarity NPC478066
0.9304 High Similarity NPC473401
0.9256 High Similarity NPC476776
0.9256 High Similarity NPC477195
0.925 High Similarity NPC470913
0.925 High Similarity NPC88311
0.925 High Similarity NPC472267
0.925 High Similarity NPC477077
0.925 High Similarity NPC477076
0.925 High Similarity NPC273878
0.925 High Similarity NPC244296
0.925 High Similarity NPC269484
0.925 High Similarity NPC252657
0.925 High Similarity NPC305793
0.925 High Similarity NPC47995
0.925 High Similarity NPC470912
0.925 High Similarity NPC11577
0.925 High Similarity NPC82380
0.925 High Similarity NPC141600
0.925 High Similarity NPC1314
0.925 High Similarity NPC470518
0.925 High Similarity NPC9470
0.925 High Similarity NPC115656
0.925 High Similarity NPC107536
0.925 High Similarity NPC252289
0.925 High Similarity NPC280029
0.925 High Similarity NPC97918
0.925 High Similarity NPC265841
0.925 High Similarity NPC477079
0.9237 High Similarity NPC30188
0.9237 High Similarity NPC23275
0.9237 High Similarity NPC177820
0.9231 High Similarity NPC275343
0.9211 High Similarity NPC291903
0.9211 High Similarity NPC37134
0.918 High Similarity NPC476779
0.9174 High Similarity NPC262796
0.9174 High Similarity NPC134914
0.9174 High Similarity NPC476774
0.9174 High Similarity NPC476775
0.9174 High Similarity NPC45346
0.9174 High Similarity NPC25998
0.9174 High Similarity NPC301639
0.9174 High Similarity NPC264566
0.9174 High Similarity NPC476780
0.9174 High Similarity NPC478155
0.9174 High Similarity NPC329993
0.9174 High Similarity NPC478065
0.9174 High Similarity NPC478064
0.9174 High Similarity NPC475377
0.9174 High Similarity NPC172374
0.9174 High Similarity NPC173435
0.9174 High Similarity NPC271610
0.9174 High Similarity NPC475167
0.9174 High Similarity NPC476074
0.9167 High Similarity NPC470475
0.913 High Similarity NPC309433
0.913 High Similarity NPC300419
0.913 High Similarity NPC475119
0.913 High Similarity NPC473824
0.9123 High Similarity NPC475486
0.9123 High Similarity NPC164389
0.9115 High Similarity NPC1046
0.9115 High Similarity NPC80843
0.9115 High Similarity NPC471967
0.9106 High Similarity NPC476778
0.9106 High Similarity NPC476777
0.9098 High Similarity NPC478154
0.9098 High Similarity NPC277212
0.9098 High Similarity NPC178264
0.9098 High Similarity NPC192765
0.9098 High Similarity NPC46823
0.9098 High Similarity NPC478153
0.9098 High Similarity NPC478150
0.9098 High Similarity NPC312650
0.9098 High Similarity NPC30279
0.9098 High Similarity NPC478152
0.9098 High Similarity NPC473918
0.9098 High Similarity NPC71391
0.9076 High Similarity NPC469842
0.9076 High Similarity NPC469841
0.9052 High Similarity NPC105800
0.9052 High Similarity NPC232237
0.9043 High Similarity NPC75287
0.9043 High Similarity NPC476992
0.9043 High Similarity NPC288205
0.9043 High Similarity NPC26626
0.9043 High Similarity NPC305267
0.9043 High Similarity NPC51465
0.9035 High Similarity NPC475208
0.9035 High Similarity NPC238935
0.9035 High Similarity NPC62696
0.9035 High Similarity NPC293038
0.9032 High Similarity NPC110700
0.9032 High Similarity NPC279915
0.9027 High Similarity NPC31839
0.9024 High Similarity NPC225791
0.9024 High Similarity NPC478151
0.9008 High Similarity NPC470476
0.8983 High Similarity NPC194310
0.8983 High Similarity NPC258815
0.8983 High Similarity NPC169727
0.8983 High Similarity NPC131841
0.8983 High Similarity NPC241310
0.8983 High Similarity NPC412
0.8983 High Similarity NPC258789
0.8983 High Similarity NPC47567
0.8974 High Similarity NPC207738

  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 NPC262199 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 NPD8328 Phase 3
0.9298 High Similarity NPD8295 Clinical (unspecified phase)
0.84 Intermediate Similarity NPD7736 Approved
0.8362 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.8175 Intermediate Similarity NPD8293 Discontinued
0.8 Intermediate Similarity NPD6370 Approved
0.7907 Intermediate Similarity NPD7319 Approved
0.7881 Intermediate Similarity NPD6412 Phase 2
0.7874 Intermediate Similarity NPD7492 Approved
0.784 Intermediate Similarity NPD6059 Approved
0.784 Intermediate Similarity NPD6054 Approved
0.784 Intermediate Similarity NPD6319 Approved
0.7812 Intermediate Similarity NPD6616 Approved
0.7812 Intermediate Similarity NPD7507 Approved
0.7807 Intermediate Similarity NPD7902 Approved
0.7787 Intermediate Similarity NPD8133 Approved
0.7752 Intermediate Similarity NPD7078 Approved
0.7705 Intermediate Similarity NPD8297 Approved
0.7705 Intermediate Similarity NPD6882 Approved
0.7699 Intermediate Similarity NPD7748 Approved
0.7667 Intermediate Similarity NPD6686 Approved
0.7638 Intermediate Similarity NPD6015 Approved
0.7638 Intermediate Similarity NPD8516 Approved
0.7638 Intermediate Similarity NPD6016 Approved
0.7638 Intermediate Similarity NPD8517 Approved
0.7638 Intermediate Similarity NPD8515 Approved
0.7638 Intermediate Similarity NPD8513 Phase 3
0.7603 Intermediate Similarity NPD6373 Approved
0.7603 Intermediate Similarity NPD6372 Approved
0.76 Intermediate Similarity NPD6009 Approved
0.7578 Intermediate Similarity NPD5988 Approved
0.7559 Intermediate Similarity NPD8294 Approved
0.7559 Intermediate Similarity NPD8377 Approved
0.7544 Intermediate Similarity NPD7900 Approved
0.7544 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7522 Intermediate Similarity NPD7515 Phase 2
0.7521 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8335 Approved
0.75 Intermediate Similarity NPD8380 Approved
0.75 Intermediate Similarity NPD8379 Approved
0.75 Intermediate Similarity NPD5739 Approved
0.75 Intermediate Similarity NPD8378 Approved
0.75 Intermediate Similarity NPD6402 Approved
0.75 Intermediate Similarity NPD7128 Approved
0.75 Intermediate Similarity NPD6675 Approved
0.75 Intermediate Similarity NPD8033 Approved
0.75 Intermediate Similarity NPD8296 Approved
0.748 Intermediate Similarity NPD6649 Approved
0.748 Intermediate Similarity NPD6650 Approved
0.7377 Intermediate Similarity NPD7320 Approved
0.7377 Intermediate Similarity NPD6881 Approved
0.7377 Intermediate Similarity NPD6899 Approved
0.736 Intermediate Similarity NPD4632 Approved
0.7339 Intermediate Similarity NPD8130 Phase 1
0.7295 Intermediate Similarity NPD5697 Approved
0.7295 Intermediate Similarity NPD5701 Approved
0.7293 Intermediate Similarity NPD6033 Approved
0.7266 Intermediate Similarity NPD7328 Approved
0.7266 Intermediate Similarity NPD7327 Approved
0.7258 Intermediate Similarity NPD7290 Approved
0.7258 Intermediate Similarity NPD6883 Approved
0.7258 Intermediate Similarity NPD7102 Approved
0.7209 Intermediate Similarity NPD7516 Approved
0.72 Intermediate Similarity NPD6617 Approved
0.72 Intermediate Similarity NPD6847 Approved
0.72 Intermediate Similarity NPD6869 Approved
0.7177 Intermediate Similarity NPD6013 Approved
0.7177 Intermediate Similarity NPD6014 Approved
0.7177 Intermediate Similarity NPD6012 Approved
0.7131 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD7604 Phase 2
0.712 Intermediate Similarity NPD4634 Approved
0.7099 Intermediate Similarity NPD5983 Phase 2
0.7099 Intermediate Similarity NPD7503 Approved
0.7097 Intermediate Similarity NPD6011 Approved
0.7063 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD7115 Discovery
0.7015 Intermediate Similarity NPD6336 Discontinued
0.697 Remote Similarity NPD6921 Approved
0.6929 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6917 Remote Similarity NPD6083 Phase 2
0.6917 Remote Similarity NPD4755 Approved
0.6917 Remote Similarity NPD6084 Phase 2
0.6866 Remote Similarity NPD6067 Discontinued
0.686 Remote Similarity NPD7638 Approved
0.6846 Remote Similarity NPD6274 Approved
0.6838 Remote Similarity NPD8074 Phase 3
0.6833 Remote Similarity NPD4697 Phase 3
0.6818 Remote Similarity NPD7101 Approved
0.6818 Remote Similarity NPD7100 Approved
0.6803 Remote Similarity NPD4700 Approved
0.6803 Remote Similarity NPD5286 Approved
0.6803 Remote Similarity NPD4696 Approved
0.6803 Remote Similarity NPD7640 Approved
0.6803 Remote Similarity NPD5285 Approved
0.6803 Remote Similarity NPD7639 Approved
0.68 Remote Similarity NPD6008 Approved
0.6791 Remote Similarity NPD8080 Discontinued
0.678 Remote Similarity NPD8035 Phase 2
0.678 Remote Similarity NPD6411 Approved
0.678 Remote Similarity NPD8034 Phase 2
0.6772 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6752 Remote Similarity NPD5328 Approved
0.6742 Remote Similarity NPD6335 Approved
0.6724 Remote Similarity NPD3573 Approved
0.6723 Remote Similarity NPD6399 Phase 3
0.6721 Remote Similarity NPD5696 Approved
0.6721 Remote Similarity NPD4225 Approved
0.6719 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6718 Remote Similarity NPD6868 Approved
0.6716 Remote Similarity NPD6909 Approved
0.6716 Remote Similarity NPD6908 Approved
0.6694 Remote Similarity NPD5221 Approved
0.6694 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6694 Remote Similarity NPD5225 Approved
0.6694 Remote Similarity NPD5226 Approved
0.6694 Remote Similarity NPD5222 Approved
0.6694 Remote Similarity NPD4633 Approved
0.6694 Remote Similarity NPD5211 Phase 2
0.6694 Remote Similarity NPD5224 Approved
0.6667 Remote Similarity NPD4767 Approved
0.6667 Remote Similarity NPD6317 Approved
0.6667 Remote Similarity NPD5737 Approved
0.6667 Remote Similarity NPD4768 Approved
0.6667 Remote Similarity NPD6672 Approved
0.664 Remote Similarity NPD5175 Approved
0.664 Remote Similarity NPD5174 Approved
0.6639 Remote Similarity NPD6079 Approved
0.6639 Remote Similarity NPD5173 Approved
0.6638 Remote Similarity NPD3618 Phase 1
0.6617 Remote Similarity NPD6314 Approved
0.6617 Remote Similarity NPD6313 Approved
0.6613 Remote Similarity NPD5223 Approved
0.6612 Remote Similarity NPD5695 Phase 3
0.661 Remote Similarity NPD7285 Clinical (unspecified phase)
0.661 Remote Similarity NPD5764 Clinical (unspecified phase)
0.661 Remote Similarity NPD6101 Approved
0.6593 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6587 Remote Similarity NPD5141 Approved
0.6571 Remote Similarity NPD5956 Approved
0.6562 Remote Similarity NPD4729 Approved
0.6562 Remote Similarity NPD4730 Approved
0.6547 Remote Similarity NPD8337 Approved
0.6547 Remote Similarity NPD8336 Approved
0.6525 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6508 Remote Similarity NPD4754 Approved
0.65 Remote Similarity NPD7983 Approved
0.6484 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6463 Remote Similarity NPD7799 Discontinued
0.6462 Remote Similarity NPD5251 Approved
0.6462 Remote Similarity NPD5248 Approved
0.6462 Remote Similarity NPD5250 Approved
0.6462 Remote Similarity NPD5249 Phase 3
0.6462 Remote Similarity NPD5247 Approved
0.646 Remote Similarity NPD7645 Phase 2
0.6458 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6446 Remote Similarity NPD5778 Approved
0.6446 Remote Similarity NPD5779 Approved
0.6434 Remote Similarity NPD5128 Approved
0.6417 Remote Similarity NPD6698 Approved
0.6417 Remote Similarity NPD46 Approved
0.6414 Remote Similarity NPD7966 Clinical (unspecified phase)
0.641 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6408 Remote Similarity NPD7260 Phase 2
0.6393 Remote Similarity NPD5282 Discontinued
0.6389 Remote Similarity NPD8415 Approved
0.6377 Remote Similarity NPD7829 Approved
0.6377 Remote Similarity NPD7830 Approved
0.637 Remote Similarity NPD6334 Approved
0.637 Remote Similarity NPD7641 Discontinued
0.637 Remote Similarity NPD6333 Approved
0.6364 Remote Similarity NPD8338 Approved
0.6357 Remote Similarity NPD8448 Approved
0.6357 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6356 Remote Similarity NPD7334 Approved
0.6356 Remote Similarity NPD6409 Approved
0.6356 Remote Similarity NPD5330 Approved
0.6356 Remote Similarity NPD6684 Approved
0.6356 Remote Similarity NPD7146 Approved
0.6356 Remote Similarity NPD7521 Approved
0.6333 Remote Similarity NPD6080 Approved
0.6333 Remote Similarity NPD6904 Approved
0.6333 Remote Similarity NPD6673 Approved
0.6333 Remote Similarity NPD4753 Phase 2
0.6331 Remote Similarity NPD8299 Approved
0.6331 Remote Similarity NPD8342 Approved
0.6331 Remote Similarity NPD8341 Approved
0.6331 Remote Similarity NPD8340 Approved
0.632 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6311 Remote Similarity NPD4202 Approved
0.6311 Remote Similarity NPD8171 Discontinued
0.6299 Remote Similarity NPD7632 Discontinued
0.6296 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6288 Remote Similarity NPD5215 Approved
0.6288 Remote Similarity NPD5216 Approved
0.6288 Remote Similarity NPD5217 Approved
0.6286 Remote Similarity NPD8451 Approved
0.625 Remote Similarity NPD6903 Approved
0.6232 Remote Similarity NPD8444 Approved

  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