Structure

Physi-Chem Properties

Molecular Weight:  408.14
Volume:  386.18
LogP:  0.991
LogD:  0.536
LogS:  -2.896
# Rotatable Bonds:  4
TPSA:  138.82
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.502
Synthetic Accessibility Score:  4.312
Fsp3:  0.55
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:  -5.557
MDCK Permeability:  3.1552302971249446e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.905
Human Intestinal Absorption (HIA):  0.096
20% Bioavailability (F20%):  0.016
30% Bioavailability (F30%):  0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.143
Plasma Protein Binding (PPB):  74.58535766601562%
Volume Distribution (VD):  0.672
Pgp-substrate:  20.0128231048584%

ADMET: Metabolism

CYP1A2-inhibitor:  0.057
CYP1A2-substrate:  0.115
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.334
CYP2C9-inhibitor:  0.012
CYP2C9-substrate:  0.236
CYP2D6-inhibitor:  0.028
CYP2D6-substrate:  0.466
CYP3A4-inhibitor:  0.006
CYP3A4-substrate:  0.098

ADMET: Excretion

Clearance (CL):  3.209
Half-life (T1/2):  0.515

ADMET: Toxicity

hERG Blockers:  0.15
Human Hepatotoxicity (H-HT):  0.287
Drug-inuced Liver Injury (DILI):  0.572
AMES Toxicity:  0.323
Rat Oral Acute Toxicity:  0.153
Maximum Recommended Daily Dose:  0.395
Skin Sensitization:  0.136
Carcinogencity:  0.853
Eye Corrosion:  0.003
Eye Irritation:  0.048
Respiratory Toxicity:  0.019

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC296377

Natural Product ID:  NPC296377
Common Name*:   Nodakenin
IUPAC Name:   (2R)-2-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-2,3-dihydrofuro[3,2-g]chromen-7-one
Synonyms:   Nodakenin
Standard InCHIKey:  HXCGUCZXPFBNRD-DNLMCPORSA-N
Standard InCHI:  InChI=1S/C20H24O9/c1-20(2,29-19-18(25)17(24)16(23)13(8-21)28-19)14-6-10-5-9-3-4-15(22)27-11(9)7-12(10)26-14/h3-5,7,13-14,16-19,21,23-25H,6,8H2,1-2H3/t13-,14-,16-,17+,18-,19+/m1/s1
SMILES:  CC(C)([C@H]1Cc2cc3ccc(=O)oc3cc2O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL459825
PubChem CID:   73191
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0000358] Furanocoumarins
          • [CHEMONTID:0002569] Linear furanocoumarins
            • [CHEMONTID:0000202] Psoralens

*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
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. DOI[10.5012/bkcs.2003.24.11.1699]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[11374978]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15679317]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[17703773]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. root n.a. PMID[22784551]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24813739]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. root n.a. PMID[25068578]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25333853]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27444348]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota Roots n.a. n.a. PMID[31464439]
NPO4340 Peucedanum praeruptorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4340 Peucedanum praeruptorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4340 Peucedanum praeruptorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4340 Peucedanum praeruptorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2953 Ostericum grosseserratum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2953 Ostericum grosseserratum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15394 Angelica decursiva Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4340 Peucedanum praeruptorum Species Apiaceae 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
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 68000.0 nM PMID[459547]
NPT151 Individual Protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 28183.8 nM PMID[459548]
NPT60 Individual Protein Lysosomal alpha-glucosidase Homo sapiens Potency = 35481.3 nM PMID[459548]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 89125.1 nM PMID[459548]
NPT501 Individual Protein Alpha-galactosidase A Homo sapiens Potency n.a. 44668.4 nM PMID[459548]
NPT156 Individual Protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 25118.9 nM PMID[459548]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 5.8 nM PMID[459548]
NPT105 Individual Protein Muscleblind-like protein 1 Homo sapiens Potency n.a. 2818.4 nM PMID[459548]
NPT791 Individual Protein Cruzipain Trypanosoma cruzi Potency = 25118.9 nM PMID[459548]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 15848.9 nM PMID[459548]
NPT864 Individual Protein Lethal(3)malignant brain tumor-like protein 1 Homo sapiens Potency = 25118.9 nM PMID[459548]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 89125.1 nM PMID[459548]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 79432.8 nM PMID[459548]

☑ 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 NPC296377 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
0.9929 High Similarity NPC169510
0.9856 High Similarity NPC85624
0.9716 High Similarity NPC471764
0.9716 High Similarity NPC87950
0.9568 High Similarity NPC215512
0.9568 High Similarity NPC476442
0.9517 High Similarity NPC470264
0.9357 High Similarity NPC312881
0.9353 High Similarity NPC232246
0.9353 High Similarity NPC153818
0.9291 High Similarity NPC195357
0.9291 High Similarity NPC287286
0.9291 High Similarity NPC152771
0.9286 High Similarity NPC279573
0.9281 High Similarity NPC224543
0.9281 High Similarity NPC78746
0.9281 High Similarity NPC188380
0.9281 High Similarity NPC103409
0.9214 High Similarity NPC225106
0.9214 High Similarity NPC184861
0.9214 High Similarity NPC281014
0.9214 High Similarity NPC212124
0.9214 High Similarity NPC155963
0.9214 High Similarity NPC294456
0.9209 High Similarity NPC33986
0.9209 High Similarity NPC472525
0.9167 High Similarity NPC469701
0.9167 High Similarity NPC226722
0.9149 High Similarity NPC211110
0.9149 High Similarity NPC151946
0.9143 High Similarity NPC26954
0.9143 High Similarity NPC38099
0.9137 High Similarity NPC180716
0.9137 High Similarity NPC253574
0.9137 High Similarity NPC98179
0.9137 High Similarity NPC224475
0.9137 High Similarity NPC62366
0.9137 High Similarity NPC213173
0.9065 High Similarity NPC167111
0.9065 High Similarity NPC318400
0.9065 High Similarity NPC207002
0.9065 High Similarity NPC133956
0.9065 High Similarity NPC296624
0.9065 High Similarity NPC471910
0.9041 High Similarity NPC469700
0.9 High Similarity NPC260265
0.9 High Similarity NPC100986
0.9 High Similarity NPC198381
0.9 High Similarity NPC204353
0.9 High Similarity NPC326600
0.9 High Similarity NPC287182
0.9 High Similarity NPC166672
0.9 High Similarity NPC195343
0.9 High Similarity NPC84894
0.9 High Similarity NPC127888
0.9 High Similarity NPC267412
0.9 High Similarity NPC307412
0.9 High Similarity NPC319859
0.9 High Similarity NPC18804
0.9 High Similarity NPC74655
0.9 High Similarity NPC164269
0.9 High Similarity NPC55149
0.9 High Similarity NPC50896
0.9 High Similarity NPC47163
0.8993 High Similarity NPC14248
0.898 High Similarity NPC96294
0.898 High Similarity NPC93924
0.8966 High Similarity NPC471824
0.8936 High Similarity NPC281241
0.8936 High Similarity NPC472424
0.8936 High Similarity NPC471909
0.8936 High Similarity NPC86892
0.8936 High Similarity NPC471625
0.8933 High Similarity NPC469699
0.8929 High Similarity NPC7526
0.8929 High Similarity NPC31849
0.8929 High Similarity NPC469449
0.8929 High Similarity NPC222036
0.8921 High Similarity NPC29734
0.8912 High Similarity NPC52740
0.8873 High Similarity NPC160727
0.8873 High Similarity NPC283019
0.8873 High Similarity NPC149320
0.8873 High Similarity NPC177281
0.8873 High Similarity NPC476455
0.8873 High Similarity NPC128529
0.8873 High Similarity NPC471630
0.8873 High Similarity NPC55615
0.8867 High Similarity NPC302610
0.8867 High Similarity NPC215060
0.8867 High Similarity NPC476352
0.8867 High Similarity NPC176186
0.8867 High Similarity NPC169404
0.8867 High Similarity NPC53587
0.8859 High Similarity NPC107197
0.8859 High Similarity NPC114740
0.8849 High Similarity NPC113098
0.8849 High Similarity NPC474491
0.8844 High Similarity NPC107120
0.8844 High Similarity NPC74320
0.8808 High Similarity NPC150442
0.88 High Similarity NPC213197
0.8794 High Similarity NPC163557
0.8786 High Similarity NPC272650
0.8786 High Similarity NPC267336
0.8784 High Similarity NPC41844
0.8777 High Similarity NPC295970
0.8776 High Similarity NPC476450
0.8766 High Similarity NPC241600
0.8766 High Similarity NPC173726
0.8759 High Similarity NPC108674
0.8758 High Similarity NPC17521
0.8741 High Similarity NPC283331
0.8741 High Similarity NPC166180
0.8723 High Similarity NPC194277
0.8705 High Similarity NPC185066
0.8699 High Similarity NPC472353
0.8671 High Similarity NPC469675
0.8671 High Similarity NPC185778
0.8667 High Similarity NPC206264
0.8667 High Similarity NPC212670
0.8667 High Similarity NPC313334
0.8645 High Similarity NPC470607
0.8643 High Similarity NPC168710
0.863 High Similarity NPC5155
0.8609 High Similarity NPC100818
0.8609 High Similarity NPC88886
0.8609 High Similarity NPC103116
0.8609 High Similarity NPC104172
0.86 High Similarity NPC270751
0.8591 High Similarity NPC205361
0.8582 High Similarity NPC80170
0.8581 High Similarity NPC470606
0.8581 High Similarity NPC476457
0.8581 High Similarity NPC471763
0.8571 High Similarity NPC230718
0.8571 High Similarity NPC49542
0.8571 High Similarity NPC146540
0.8571 High Similarity NPC84207
0.8571 High Similarity NPC5253
0.8571 High Similarity NPC139976
0.8571 High Similarity NPC128337
0.8571 High Similarity NPC145319
0.8561 High Similarity NPC471826
0.8561 High Similarity NPC188327
0.8561 High Similarity NPC234109
0.8552 High Similarity NPC87777
0.8552 High Similarity NPC471068
0.8552 High Similarity NPC471069
0.8552 High Similarity NPC124149
0.8552 High Similarity NPC262328
0.8543 High Similarity NPC106138
0.8533 High Similarity NPC15577
0.8531 High Similarity NPC291551
0.8531 High Similarity NPC215037
0.8531 High Similarity NPC469965
0.8531 High Similarity NPC141822
0.8531 High Similarity NPC205797
0.8531 High Similarity NPC241165
0.8531 High Similarity NPC1220
0.8531 High Similarity NPC142563
0.8528 High Similarity NPC325176
0.8526 High Similarity NPC43761
0.8523 High Similarity NPC108994
0.8523 High Similarity NPC106126
0.8516 High Similarity NPC284810
0.8514 High Similarity NPC183646
0.8514 High Similarity NPC116922
0.8514 High Similarity NPC119640
0.8503 High Similarity NPC300611
0.8503 High Similarity NPC279851
0.8503 High Similarity NPC472520
0.8503 High Similarity NPC210192
0.85 High Similarity NPC258567
0.85 High Similarity NPC121740
0.85 High Similarity NPC473993
0.85 High Similarity NPC224774
0.8497 Intermediate Similarity NPC23253
0.8493 Intermediate Similarity NPC144512
0.8493 Intermediate Similarity NPC137262
0.8493 Intermediate Similarity NPC47040
0.8493 Intermediate Similarity NPC35501
0.8493 Intermediate Similarity NPC471070
0.8493 Intermediate Similarity NPC37428
0.8493 Intermediate Similarity NPC278600
0.8493 Intermediate Similarity NPC471072
0.8493 Intermediate Similarity NPC471071
0.8483 Intermediate Similarity NPC20829
0.8483 Intermediate Similarity NPC262585
0.8483 Intermediate Similarity NPC18189
0.8477 Intermediate Similarity NPC476348
0.8477 Intermediate Similarity NPC187398
0.8472 Intermediate Similarity NPC131950
0.8472 Intermediate Similarity NPC124085
0.8472 Intermediate Similarity NPC117048
0.8467 Intermediate Similarity NPC199928
0.8467 Intermediate Similarity NPC474044
0.8466 Intermediate Similarity NPC314213
0.8456 Intermediate Similarity NPC292443
0.8456 Intermediate Similarity NPC225445

  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 NPC296377 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
0.8667 High Similarity NPD1653 Approved
0.8531 High Similarity NPD5124 Phase 1
0.8531 High Similarity NPD5123 Clinical (unspecified phase)
0.8378 Intermediate Similarity NPD1652 Phase 2
0.8228 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD6559 Discontinued
0.8071 Intermediate Similarity NPD1091 Approved
0.8 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD422 Phase 1
0.7939 Intermediate Similarity NPD3818 Discontinued
0.7925 Intermediate Similarity NPD8455 Phase 2
0.7925 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD7075 Discontinued
0.7862 Intermediate Similarity NPD6801 Discontinued
0.7857 Intermediate Similarity NPD5058 Phase 3
0.7848 Intermediate Similarity NPD4380 Phase 2
0.7829 Intermediate Similarity NPD2424 Discontinued
0.7763 Intermediate Similarity NPD7266 Discontinued
0.775 Intermediate Similarity NPD37 Approved
0.7744 Intermediate Similarity NPD7199 Phase 2
0.7718 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD1613 Approved
0.7716 Intermediate Similarity NPD4966 Approved
0.7716 Intermediate Similarity NPD4967 Phase 2
0.7716 Intermediate Similarity NPD4965 Approved
0.7703 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD7097 Phase 1
0.7679 Intermediate Similarity NPD7054 Approved
0.7633 Intermediate Similarity NPD7472 Approved
0.7633 Intermediate Similarity NPD7074 Phase 3
0.7622 Intermediate Similarity NPD6234 Discontinued
0.7619 Intermediate Similarity NPD7228 Approved
0.7607 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD7819 Suspended
0.7588 Intermediate Similarity NPD6797 Phase 2
0.7584 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD7411 Suspended
0.7574 Intermediate Similarity NPD5844 Phase 1
0.7568 Intermediate Similarity NPD4908 Phase 1
0.7548 Intermediate Similarity NPD6674 Discontinued
0.7547 Intermediate Similarity NPD5403 Approved
0.7545 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD7251 Discontinued
0.7532 Intermediate Similarity NPD5401 Approved
0.75 Intermediate Similarity NPD7808 Phase 3
0.75 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD6799 Approved
0.745 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD1610 Phase 2
0.7442 Intermediate Similarity NPD7240 Approved
0.7439 Intermediate Similarity NPD3817 Phase 2
0.7439 Intermediate Similarity NPD5402 Approved
0.7438 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD920 Approved
0.7421 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD8651 Approved
0.7413 Intermediate Similarity NPD1548 Phase 1
0.7405 Intermediate Similarity NPD7583 Approved
0.7403 Intermediate Similarity NPD7033 Discontinued
0.7403 Intermediate Similarity NPD5588 Approved
0.74 Intermediate Similarity NPD3027 Phase 3
0.7389 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD3750 Approved
0.7389 Intermediate Similarity NPD4628 Phase 3
0.7383 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4060 Phase 1
0.7366 Intermediate Similarity NPD7585 Approved
0.7362 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD2796 Approved
0.7351 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD6798 Discontinued
0.7338 Intermediate Similarity NPD4536 Approved
0.7338 Intermediate Similarity NPD4538 Approved
0.7338 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2415 Discontinued
0.7325 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD1243 Approved
0.732 Intermediate Similarity NPD6355 Discontinued
0.7317 Intermediate Similarity NPD1934 Approved
0.7312 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD6002 Phase 3
0.7308 Intermediate Similarity NPD6004 Phase 3
0.7308 Intermediate Similarity NPD5763 Approved
0.7308 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5762 Approved
0.7308 Intermediate Similarity NPD6005 Phase 3
0.7308 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD6599 Discontinued
0.7296 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD3748 Approved
0.7289 Intermediate Similarity NPD7768 Phase 2
0.7285 Intermediate Similarity NPD4625 Phase 3
0.7263 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD5494 Approved
0.7261 Intermediate Similarity NPD1549 Phase 2
0.7257 Intermediate Similarity NPD8312 Approved
0.7257 Intermediate Similarity NPD8313 Approved
0.725 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD2797 Approved
0.7237 Intermediate Similarity NPD1296 Phase 2
0.7234 Intermediate Similarity NPD7843 Approved
0.723 Intermediate Similarity NPD4749 Approved
0.7229 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD4340 Discontinued
0.7203 Intermediate Similarity NPD7157 Approved
0.7202 Intermediate Similarity NPD919 Approved
0.72 Intermediate Similarity NPD7549 Discontinued
0.7197 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD2684 Approved
0.7193 Intermediate Similarity NPD6166 Phase 2
0.7193 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD5126 Approved
0.7192 Intermediate Similarity NPD5125 Phase 3
0.7191 Intermediate Similarity NPD6842 Approved
0.7191 Intermediate Similarity NPD6841 Approved
0.7191 Intermediate Similarity NPD6843 Phase 3
0.719 Intermediate Similarity NPD6233 Phase 2
0.7184 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD3225 Approved
0.7179 Intermediate Similarity NPD5960 Phase 3
0.7175 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD2861 Phase 2
0.7143 Intermediate Similarity NPD4140 Approved
0.7143 Intermediate Similarity NPD3749 Approved
0.7143 Intermediate Similarity NPD7685 Pre-registration
0.7143 Intermediate Similarity NPD3496 Discontinued
0.7128 Intermediate Similarity NPD7584 Approved
0.7124 Intermediate Similarity NPD3268 Approved
0.7123 Intermediate Similarity NPD5691 Approved
0.7122 Intermediate Similarity NPD290 Approved
0.7122 Intermediate Similarity NPD1358 Approved
0.7118 Intermediate Similarity NPD8127 Discontinued
0.7113 Intermediate Similarity NPD5535 Approved
0.711 Intermediate Similarity NPD3751 Discontinued
0.7108 Intermediate Similarity NPD4433 Discontinued
0.7099 Intermediate Similarity NPD2532 Approved
0.7099 Intermediate Similarity NPD2533 Approved
0.7099 Intermediate Similarity NPD2534 Approved
0.7095 Intermediate Similarity NPD3705 Approved
0.7083 Intermediate Similarity NPD3882 Suspended
0.7076 Intermediate Similarity NPD3787 Discontinued
0.7076 Intermediate Similarity NPD7229 Phase 3
0.7075 Intermediate Similarity NPD4626 Approved
0.707 Intermediate Similarity NPD4308 Phase 3
0.707 Intermediate Similarity NPD1510 Phase 2
0.7066 Intermediate Similarity NPD1465 Phase 2
0.7066 Intermediate Similarity NPD2801 Approved
0.7063 Intermediate Similarity NPD7982 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7095 Approved
0.703 Intermediate Similarity NPD7458 Discontinued
0.703 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD2935 Discontinued
0.7025 Intermediate Similarity NPD1551 Phase 2
0.7013 Intermediate Similarity NPD2313 Discontinued
0.7006 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6993 Remote Similarity NPD6832 Phase 2
0.6987 Remote Similarity NPD1933 Approved
0.6978 Remote Similarity NPD9697 Approved
0.6977 Remote Similarity NPD6232 Discontinued
0.6975 Remote Similarity NPD6667 Approved
0.6975 Remote Similarity NPD6666 Approved
0.6962 Remote Similarity NPD2799 Discontinued
0.6943 Remote Similarity NPD6653 Approved
0.6937 Remote Similarity NPD970 Clinical (unspecified phase)
0.6933 Remote Similarity NPD7213 Phase 3
0.6933 Remote Similarity NPD1511 Approved
0.6933 Remote Similarity NPD7212 Phase 2
0.6929 Remote Similarity NPD3134 Approved
0.6928 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6923 Remote Similarity NPD969 Suspended
0.6923 Remote Similarity NPD4307 Phase 2
0.6919 Remote Similarity NPD6959 Discontinued
0.6914 Remote Similarity NPD6190 Approved
0.6908 Remote Similarity NPD3266 Approved
0.6908 Remote Similarity NPD3267 Approved
0.6903 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7985 Registered
0.6894 Remote Similarity NPD2800 Approved
0.6892 Remote Similarity NPD1357 Approved
0.6891 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6891 Remote Similarity NPD7783 Phase 2
0.689 Remote Similarity NPD7447 Phase 1
0.6878 Remote Similarity NPD7435 Discontinued
0.6875 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6863 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6859 Remote Similarity NPD4062 Phase 3
0.6857 Remote Similarity NPD7473 Discontinued
0.6852 Remote Similarity NPD4535 Phase 3
0.6852 Remote Similarity NPD7466 Approved
0.6851 Remote Similarity NPD8434 Phase 2

  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