Structure

Physi-Chem Properties

Molecular Weight:  716.14
Volume:  681.617
LogP:  0.408
LogD:  -0.692
LogS:  -4.362
# Rotatable Bonds:  13
TPSA:  297.86
# H-Bond Aceptor:  16
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.049
Synthetic Accessibility Score:  4.742
Fsp3:  0.139
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.79
MDCK Permeability:  4.843084298045142e-06
Pgp-inhibitor:  0.032
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.995
20% Bioavailability (F20%):  0.685
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.017
Plasma Protein Binding (PPB):  91.17076873779297%
Volume Distribution (VD):  0.316
Pgp-substrate:  5.660836219787598%

ADMET: Metabolism

CYP1A2-inhibitor:  0.194
CYP1A2-substrate:  0.006
CYP2C19-inhibitor:  0.037
CYP2C19-substrate:  0.024
CYP2C9-inhibitor:  0.599
CYP2C9-substrate:  0.16
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.106
CYP3A4-inhibitor:  0.072
CYP3A4-substrate:  0.006

ADMET: Excretion

Clearance (CL):  4.164
Half-life (T1/2):  0.95

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.499
Drug-inuced Liver Injury (DILI):  0.983
AMES Toxicity:  0.693
Rat Oral Acute Toxicity:  0.061
Maximum Recommended Daily Dose:  0.82
Skin Sensitization:  0.97
Carcinogencity:  0.079
Eye Corrosion:  0.003
Eye Irritation:  0.916
Respiratory Toxicity:  0.009

Download Data

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

  Natural Product: NPC473544

Natural Product ID:  NPC473544
Common Name*:   Dipotassium;(2R)-2-[(1R)-3-[(1R)-1-Carboxylato-2-(3,4-Dihydroxyphenyl)Ethoxy]Carbonyl-1-(3,4-Dihydroxyphenyl)-6,7-Dihydroxy-1,2-Dihydronaphthalene-2-Carbonyl]Oxy-3-(3,4-Dihydroxyphenyl)Propanoate
IUPAC Name:   dipotassium;(2R)-2-[(1R)-3-[(1R)-1-carboxylato-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoate
Synonyms:  
Standard InCHIKey:  YYHRLIRLQRUSRG-CFHFNVEYSA-L
Standard InCHI:  InChI=1S/C36H30O16.2K/c37-21-4-1-15(7-24(21)40)9-29(33(45)46)51-35(49)20-11-18-13-27(43)28(44)14-19(18)31(17-3-6-23(39)26(42)12-17)32(20)36(50)52-30(34(47)48)10-16-2-5-22(38)25(41)8-16;;/h1-8,11-14,29-32,37-44H,9-10H2,(H,45,46)(H,47,48);;/q;2*+1/p-2/t29-,30-,31-,32?;;/m1../s1
SMILES:  C1=CC(=C(C=C1CC(C(=O)[O-])OC(=O)C2C(C3=CC(=C(C=C3C=C2C(=O)OC(CC4=CC(=C(C=C4)O)O)C(=O)[O-])O)O)C5=CC(=C(C=C5)O)O)O)O.[K+].[K+]
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL445198
PubChem CID:   5316937
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[12502328]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[7775984]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11421 Arnebia euchroma Species Boraginaceae 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
NPT759 Cell Line H9 Homo sapiens IC50 = 50.0 ug.mL-1 PMID[478622]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 16.0 ug.mL-1 PMID[478622]
NPT27 Others Unspecified Ratio IC50/EC50 = 3.1 n.a. PMID[478622]

☑ 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 NPC473544 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 NPC475216
1.0 High Similarity NPC475162
1.0 High Similarity NPC83663
1.0 High Similarity NPC475595
1.0 High Similarity NPC266084
1.0 High Similarity NPC475145
0.9536 High Similarity NPC471750
0.9054 High Similarity NPC228940
0.8951 High Similarity NPC473630
0.8912 High Similarity NPC38473
0.8824 High Similarity NPC477334
0.8675 High Similarity NPC53520
0.8675 High Similarity NPC477333
0.8621 High Similarity NPC18074
0.8621 High Similarity NPC61
0.8621 High Similarity NPC5419
0.8621 High Similarity NPC25581
0.8591 High Similarity NPC179505
0.8591 High Similarity NPC156709
0.8589 High Similarity NPC471870
0.8589 High Similarity NPC41494
0.8589 High Similarity NPC186100
0.8589 High Similarity NPC216403
0.8562 High Similarity NPC155209
0.8562 High Similarity NPC168799
0.8552 High Similarity NPC198388
0.8543 High Similarity NPC477873
0.8543 High Similarity NPC469447
0.8526 High Similarity NPC270268
0.8456 Intermediate Similarity NPC279676
0.8456 Intermediate Similarity NPC67349
0.8434 Intermediate Similarity NPC471871
0.8428 Intermediate Similarity NPC134925
0.8421 Intermediate Similarity NPC37331
0.8421 Intermediate Similarity NPC319628
0.8421 Intermediate Similarity NPC303090
0.8421 Intermediate Similarity NPC220664
0.8421 Intermediate Similarity NPC284948
0.8366 Intermediate Similarity NPC160378
0.8366 Intermediate Similarity NPC25491
0.8355 Intermediate Similarity NPC477335
0.8355 Intermediate Similarity NPC206095
0.8355 Intermediate Similarity NPC471027
0.8355 Intermediate Similarity NPC224389
0.8355 Intermediate Similarity NPC13818
0.8355 Intermediate Similarity NPC35702
0.8355 Intermediate Similarity NPC297517
0.8354 Intermediate Similarity NPC471874
0.8344 Intermediate Similarity NPC471875
0.8333 Intermediate Similarity NPC471152
0.8323 Intermediate Similarity NPC322660
0.8323 Intermediate Similarity NPC229264
0.8313 Intermediate Similarity NPC470896
0.8313 Intermediate Similarity NPC473275
0.8311 Intermediate Similarity NPC471749
0.8303 Intermediate Similarity NPC217781
0.8301 Intermediate Similarity NPC43158
0.8301 Intermediate Similarity NPC472016
0.8301 Intermediate Similarity NPC192831
0.8301 Intermediate Similarity NPC277315
0.8301 Intermediate Similarity NPC258469
0.8301 Intermediate Similarity NPC285550
0.8293 Intermediate Similarity NPC162169
0.8293 Intermediate Similarity NPC166851
0.8289 Intermediate Similarity NPC304110
0.8289 Intermediate Similarity NPC9218
0.8289 Intermediate Similarity NPC477279
0.8289 Intermediate Similarity NPC27518
0.8282 Intermediate Similarity NPC471873
0.8282 Intermediate Similarity NPC144557
0.828 Intermediate Similarity NPC221091
0.828 Intermediate Similarity NPC327962
0.828 Intermediate Similarity NPC259576
0.8269 Intermediate Similarity NPC155910
0.8269 Intermediate Similarity NPC17042
0.8269 Intermediate Similarity NPC192568
0.8269 Intermediate Similarity NPC471076
0.8258 Intermediate Similarity NPC8102
0.8258 Intermediate Similarity NPC66894
0.8247 Intermediate Similarity NPC183824
0.8242 Intermediate Similarity NPC26536
0.8242 Intermediate Similarity NPC175793
0.8242 Intermediate Similarity NPC317671
0.8242 Intermediate Similarity NPC49983
0.8242 Intermediate Similarity NPC142707
0.8235 Intermediate Similarity NPC477278
0.8235 Intermediate Similarity NPC477277
0.8232 Intermediate Similarity NPC134047
0.8232 Intermediate Similarity NPC272750
0.8232 Intermediate Similarity NPC223006
0.8232 Intermediate Similarity NPC173729
0.8228 Intermediate Similarity NPC252979
0.8228 Intermediate Similarity NPC118033
0.8228 Intermediate Similarity NPC300329
0.8224 Intermediate Similarity NPC289690
0.8224 Intermediate Similarity NPC288452
0.8221 Intermediate Similarity NPC266365
0.8221 Intermediate Similarity NPC216916
0.8221 Intermediate Similarity NPC471869
0.8217 Intermediate Similarity NPC473719
0.8205 Intermediate Similarity NPC299090
0.8205 Intermediate Similarity NPC143892
0.8205 Intermediate Similarity NPC283081
0.8205 Intermediate Similarity NPC221383
0.8193 Intermediate Similarity NPC190204
0.8193 Intermediate Similarity NPC311389
0.8193 Intermediate Similarity NPC470271
0.8193 Intermediate Similarity NPC261411
0.8193 Intermediate Similarity NPC43918
0.8176 Intermediate Similarity NPC473773
0.8176 Intermediate Similarity NPC318799
0.8176 Intermediate Similarity NPC475579
0.8176 Intermediate Similarity NPC476434
0.8165 Intermediate Similarity NPC32197
0.8158 Intermediate Similarity NPC219428
0.8158 Intermediate Similarity NPC302857
0.8158 Intermediate Similarity NPC37250
0.8158 Intermediate Similarity NPC152942
0.8158 Intermediate Similarity NPC283560
0.8158 Intermediate Similarity NPC278068
0.8158 Intermediate Similarity NPC24295
0.8158 Intermediate Similarity NPC142703
0.8158 Intermediate Similarity NPC182249
0.8153 Intermediate Similarity NPC1580
0.8153 Intermediate Similarity NPC473138
0.8153 Intermediate Similarity NPC28776
0.8144 Intermediate Similarity NPC266545
0.8144 Intermediate Similarity NPC202428
0.8137 Intermediate Similarity NPC203757
0.8133 Intermediate Similarity NPC106406
0.8129 Intermediate Similarity NPC26045
0.8129 Intermediate Similarity NPC470130
0.8129 Intermediate Similarity NPC198902
0.8125 Intermediate Similarity NPC87403
0.8121 Intermediate Similarity NPC45943
0.8113 Intermediate Similarity NPC473680
0.8113 Intermediate Similarity NPC475311
0.8113 Intermediate Similarity NPC473579
0.8113 Intermediate Similarity NPC475454
0.8108 Intermediate Similarity NPC32626
0.8108 Intermediate Similarity NPC329344
0.8108 Intermediate Similarity NPC237506
0.8108 Intermediate Similarity NPC217052
0.8107 Intermediate Similarity NPC98583
0.8105 Intermediate Similarity NPC274891
0.8105 Intermediate Similarity NPC473591
0.8105 Intermediate Similarity NPC106055
0.8105 Intermediate Similarity NPC26241
0.8105 Intermediate Similarity NPC303683
0.8105 Intermediate Similarity NPC476819
0.8105 Intermediate Similarity NPC205751
0.8105 Intermediate Similarity NPC155192
0.8105 Intermediate Similarity NPC474875
0.8105 Intermediate Similarity NPC110699
0.8105 Intermediate Similarity NPC295492
0.8105 Intermediate Similarity NPC271494
0.8105 Intermediate Similarity NPC476820
0.8095 Intermediate Similarity NPC470272
0.8095 Intermediate Similarity NPC47521
0.8086 Intermediate Similarity NPC239019
0.8086 Intermediate Similarity NPC247629
0.8086 Intermediate Similarity NPC471968
0.8084 Intermediate Similarity NPC177362
0.8084 Intermediate Similarity NPC31034
0.8079 Intermediate Similarity NPC477874
0.8079 Intermediate Similarity NPC43353
0.8079 Intermediate Similarity NPC173569
0.8077 Intermediate Similarity NPC53884
0.8077 Intermediate Similarity NPC258671
0.8075 Intermediate Similarity NPC281703
0.8075 Intermediate Similarity NPC125487
0.8075 Intermediate Similarity NPC469888
0.8065 Intermediate Similarity NPC235557
0.8063 Intermediate Similarity NPC246566
0.8063 Intermediate Similarity NPC267091
0.8063 Intermediate Similarity NPC106818
0.8063 Intermediate Similarity NPC95498
0.8061 Intermediate Similarity NPC322982
0.8061 Intermediate Similarity NPC149389
0.8054 Intermediate Similarity NPC108553
0.8052 Intermediate Similarity NPC172311
0.8052 Intermediate Similarity NPC29599
0.8049 Intermediate Similarity NPC301089
0.8047 Intermediate Similarity NPC65333
0.8047 Intermediate Similarity NPC469775
0.8047 Intermediate Similarity NPC469772
0.8047 Intermediate Similarity NPC295941
0.8047 Intermediate Similarity NPC100251
0.8047 Intermediate Similarity NPC469776
0.8047 Intermediate Similarity NPC135334
0.8047 Intermediate Similarity NPC469773
0.8047 Intermediate Similarity NPC469778
0.8047 Intermediate Similarity NPC469777
0.8047 Intermediate Similarity NPC469774
0.8047 Intermediate Similarity NPC32723
0.8047 Intermediate Similarity NPC100925
0.8038 Intermediate Similarity NPC142528
0.8037 Intermediate Similarity NPC172419
0.8037 Intermediate Similarity NPC238419
0.8026 Intermediate Similarity NPC249817

  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 NPC473544 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
0.8477 Intermediate Similarity NPD8166 Discontinued
0.8421 Intermediate Similarity NPD6190 Approved
0.7989 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7941 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD6234 Discontinued
0.7758 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD8312 Approved
0.7701 Intermediate Similarity NPD8313 Approved
0.7692 Intermediate Similarity NPD7266 Discontinued
0.7661 Intermediate Similarity NPD7228 Approved
0.7632 Intermediate Similarity NPD3764 Approved
0.7576 Intermediate Similarity NPD37 Approved
0.7574 Intermediate Similarity NPD8127 Discontinued
0.7571 Intermediate Similarity NPD8150 Discontinued
0.7545 Intermediate Similarity NPD4965 Approved
0.7545 Intermediate Similarity NPD4966 Approved
0.7545 Intermediate Similarity NPD4967 Phase 2
0.7529 Intermediate Similarity NPD6232 Discontinued
0.75 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7473 Discontinued
0.7425 Intermediate Similarity NPD8455 Phase 2
0.7414 Intermediate Similarity NPD5844 Phase 1
0.7405 Intermediate Similarity NPD5408 Approved
0.7405 Intermediate Similarity NPD5404 Approved
0.7405 Intermediate Similarity NPD5405 Approved
0.7405 Intermediate Similarity NPD5406 Approved
0.7341 Intermediate Similarity NPD6166 Phase 2
0.7341 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD4060 Phase 1
0.7301 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6798 Discontinued
0.7288 Intermediate Similarity NPD7240 Approved
0.7283 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD230 Phase 1
0.7257 Intermediate Similarity NPD3751 Discontinued
0.7244 Intermediate Similarity NPD6663 Approved
0.7244 Intermediate Similarity NPD6233 Phase 2
0.7222 Intermediate Similarity NPD7003 Approved
0.7222 Intermediate Similarity NPD4628 Phase 3
0.7219 Intermediate Similarity NPD1465 Phase 2
0.7212 Intermediate Similarity NPD6273 Approved
0.7208 Intermediate Similarity NPD5736 Approved
0.7191 Intermediate Similarity NPD7685 Pre-registration
0.7182 Intermediate Similarity NPD8434 Phase 2
0.7158 Intermediate Similarity NPD8320 Phase 1
0.7158 Intermediate Similarity NPD8319 Approved
0.7152 Intermediate Similarity NPD6355 Discontinued
0.7151 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6797 Phase 2
0.7095 Intermediate Similarity NPD7251 Discontinued
0.7093 Intermediate Similarity NPD7075 Discontinued
0.7083 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD3226 Approved
0.7078 Intermediate Similarity NPD1470 Approved
0.7076 Intermediate Similarity NPD3817 Phase 2
0.7076 Intermediate Similarity NPD5402 Approved
0.7069 Intermediate Similarity NPD7199 Phase 2
0.7069 Intermediate Similarity NPD6959 Discontinued
0.7063 Intermediate Similarity NPD7097 Phase 1
0.7056 Intermediate Similarity NPD7808 Phase 3
0.7048 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD3882 Suspended
0.7035 Intermediate Similarity NPD7768 Phase 2
0.7029 Intermediate Similarity NPD3787 Discontinued
0.7018 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD7680 Approved
0.7016 Intermediate Similarity NPD7435 Discontinued
0.7012 Intermediate Similarity NPD3750 Approved
0.7006 Intermediate Similarity NPD7095 Approved
0.6988 Remote Similarity NPD7390 Discontinued
0.6982 Remote Similarity NPD7458 Discontinued
0.6982 Remote Similarity NPD3455 Phase 2
0.6975 Remote Similarity NPD2438 Suspended
0.6966 Remote Similarity NPD3818 Discontinued
0.6959 Remote Similarity NPD1934 Approved
0.6952 Remote Similarity NPD6534 Approved
0.6952 Remote Similarity NPD6535 Approved
0.6951 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6949 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6948 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6946 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6946 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6941 Remote Similarity NPD4380 Phase 2
0.6933 Remote Similarity NPD5763 Approved
0.6933 Remote Similarity NPD5762 Approved
0.6931 Remote Similarity NPD7700 Phase 2
0.6931 Remote Similarity NPD7699 Phase 2
0.6923 Remote Similarity NPD8151 Discontinued
0.6919 Remote Similarity NPD7819 Suspended
0.6919 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6914 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6909 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6909 Remote Similarity NPD4110 Phase 3
0.6908 Remote Similarity NPD3019 Approved
0.6908 Remote Similarity NPD2932 Approved
0.6903 Remote Similarity NPD1283 Approved
0.6899 Remote Similarity NPD3027 Phase 3
0.6895 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6889 Remote Similarity NPD7472 Approved
0.6889 Remote Similarity NPD7074 Phase 3
0.6888 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6888 Remote Similarity NPD7874 Approved
0.6885 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6875 Remote Similarity NPD2979 Phase 3
0.6875 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3620 Phase 2
0.6864 Remote Similarity NPD5403 Approved
0.6864 Remote Similarity NPD6980 Clinical (unspecified phase)
0.686 Remote Similarity NPD6801 Discontinued
0.6859 Remote Similarity NPD6780 Approved
0.6859 Remote Similarity NPD6782 Approved
0.6859 Remote Similarity NPD6779 Approved
0.6859 Remote Similarity NPD6777 Approved
0.6859 Remote Similarity NPD6778 Approved
0.6859 Remote Similarity NPD6781 Approved
0.6859 Remote Similarity NPD6776 Approved
0.6849 Remote Similarity NPD3021 Approved
0.6849 Remote Similarity NPD3022 Approved
0.6833 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6833 Remote Similarity NPD7054 Approved
0.6829 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6826 Remote Similarity NPD3300 Phase 2
0.6821 Remote Similarity NPD2801 Approved
0.6818 Remote Similarity NPD1201 Approved
0.6813 Remote Similarity NPD4062 Phase 3
0.681 Remote Similarity NPD651 Clinical (unspecified phase)
0.6807 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6805 Remote Similarity NPD1512 Approved
0.6804 Remote Similarity NPD7871 Phase 2
0.6804 Remote Similarity NPD7870 Phase 2
0.6792 Remote Similarity NPD7008 Discontinued
0.6792 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6788 Remote Similarity NPD5958 Discontinued
0.6782 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6778 Remote Similarity NPD7177 Discontinued
0.6776 Remote Similarity NPD9545 Approved
0.6774 Remote Similarity NPD9269 Phase 2
0.677 Remote Similarity NPD7966 Clinical (unspecified phase)
0.677 Remote Similarity NPD1612 Clinical (unspecified phase)
0.677 Remote Similarity NPD1613 Approved
0.677 Remote Similarity NPD943 Approved
0.6768 Remote Similarity NPD2935 Discontinued
0.6753 Remote Similarity NPD7697 Approved
0.6753 Remote Similarity NPD7698 Approved
0.6753 Remote Similarity NPD7696 Phase 3
0.6752 Remote Similarity NPD3094 Phase 2
0.6746 Remote Similarity NPD5401 Approved
0.6744 Remote Similarity NPD7028 Phase 2
0.6744 Remote Similarity NPD6599 Discontinued
0.6739 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6733 Remote Similarity NPD2629 Approved
0.6728 Remote Similarity NPD4340 Discontinued
0.6727 Remote Similarity NPD2346 Discontinued
0.6726 Remote Similarity NPD7236 Approved
0.6725 Remote Similarity NPD1653 Approved
0.6723 Remote Similarity NPD5494 Approved
0.6721 Remote Similarity NPD6559 Discontinued
0.6721 Remote Similarity NPD7038 Approved
0.6721 Remote Similarity NPD7039 Approved
0.671 Remote Similarity NPD1281 Approved
0.671 Remote Similarity NPD3092 Approved
0.6708 Remote Similarity NPD8032 Phase 2
0.6707 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6707 Remote Similarity NPD3748 Approved
0.6705 Remote Similarity NPD7411 Suspended
0.6705 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6705 Remote Similarity NPD3749 Approved
0.6702 Remote Similarity NPD8485 Approved
0.6701 Remote Similarity NPD7701 Phase 2
0.6689 Remote Similarity NPD4198 Discontinued
0.6687 Remote Similarity NPD4534 Discontinued
0.6686 Remote Similarity NPD6799 Approved
0.6686 Remote Similarity NPD1511 Approved
0.6683 Remote Similarity NPD7801 Approved
0.6667 Remote Similarity NPD1608 Approved
0.6667 Remote Similarity NPD4140 Approved
0.6667 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6667 Remote Similarity NPD826 Approved
0.6667 Remote Similarity NPD825 Approved
0.6667 Remote Similarity NPD9494 Approved
0.6648 Remote Similarity NPD7229 Phase 3
0.6647 Remote Similarity NPD6674 Discontinued
0.6647 Remote Similarity NPD2534 Approved
0.6647 Remote Similarity NPD2532 Approved
0.6647 Remote Similarity NPD2533 Approved
0.6634 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6632 Remote Similarity NPD6212 Phase 3
0.6632 Remote Similarity NPD6213 Phase 3
0.6632 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6631 Remote Similarity NPD8424 Clinical (unspecified phase)
0.663 Remote Similarity NPD8368 Discontinued
0.6628 Remote Similarity NPD7239 Suspended
0.6625 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6614 Remote Similarity NPD2488 Approved
0.6614 Remote Similarity NPD2490 Approved
0.6609 Remote Similarity NPD6386 Approved
0.6609 Remote Similarity NPD6385 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