Structure

Physi-Chem Properties

Molecular Weight:  178.06
Volume:  180.228
LogP:  2.878
LogD:  1.762
LogS:  -2.299
# Rotatable Bonds:  0
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.612
Synthetic Accessibility Score:  2.692
Fsp3:  0.3
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.537
MDCK Permeability:  2.6948189770337194e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.353

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.495
Plasma Protein Binding (PPB):  91.34319305419922%
Volume Distribution (VD):  1.61
Pgp-substrate:  7.150081634521484%

ADMET: Metabolism

CYP1A2-inhibitor:  0.965
CYP1A2-substrate:  0.277
CYP2C19-inhibitor:  0.601
CYP2C19-substrate:  0.184
CYP2C9-inhibitor:  0.38
CYP2C9-substrate:  0.863
CYP2D6-inhibitor:  0.7
CYP2D6-substrate:  0.566
CYP3A4-inhibitor:  0.295
CYP3A4-substrate:  0.157

ADMET: Excretion

Clearance (CL):  12.03
Half-life (T1/2):  0.591

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.14
Drug-inuced Liver Injury (DILI):  0.63
AMES Toxicity:  0.243
Rat Oral Acute Toxicity:  0.084
Maximum Recommended Daily Dose:  0.304
Skin Sensitization:  0.715
Carcinogencity:  0.932
Eye Corrosion:  0.146
Eye Irritation:  0.977
Respiratory Toxicity:  0.218

Download Data

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

  Natural Product: NPC214702

Natural Product ID:  NPC214702
Common Name*:   (-)-(R)-Mellein
IUPAC Name:   (3R)-8-hydroxy-3-methyl-3,4-dihydroisochromen-1-one
Synonyms:   (R)-Mellein
Standard InCHIKey:  KWILGNNWGSNMPA-ZCFIWIBFSA-N
Standard InCHI:  InChI=1S/C10H10O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h2-4,6,11H,5H2,1H3/t6-/m1/s1
SMILES:  C[C@@H]1Cc2cccc(c2C(=O)O1)O
Synthetic Gene Cluster:   BGC0001244;
ChEMBL Identifier:   CHEMBL499303
PubChem CID:   114679
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003411] 2-benzopyrans

*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
NPO15401 Theobroma cacao Species Malvaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)00169-2]
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[10075773]
NPO33476 microsphaeropsis sp. Species n.a. Eukaryota n.a. n.a. n.a. PMID[10869191]
NPO33476 microsphaeropsis sp. Species n.a. Eukaryota n.a. n.a. n.a. PMID[12027766]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota n.a. fruit n.a. PMID[15128023]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. PMID[16933891]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[18068204]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18464091]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18558747]
NPO2421 Picea glauca Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[18636777]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota stem bark Pangradin village, Jasinga, West Java, Indonesia 2005-AUG PMID[19839614]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20817450]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. pericarp n.a. PMID[24555285]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[24717154]
NPO40491 Fagraea fragrans Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[26905094]
NPO691 Tarchonanthus camphoratus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29244495]
NPO284 Albizia procera Species Fabaceae Eukaryota Bark n.a. n.a. PMID[30520635]
NPO33476 microsphaeropsis sp. Species n.a. Eukaryota n.a. n.a. n.a. PMID[32243151]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota fruit hulls Madras, Tamil Nadu, India 1993-MAR PMID[9213587]
NPO40084 Coniothyrium sp. Species Coniothyriaceae Eukaryota n.a. n.a. n.a. PMID[9917295]
NPO33476 microsphaeropsis sp. Species n.a. Eukaryota n.a. n.a. n.a. PMID[9917295]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota Petiole n.a. n.a. Database[FooDB]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota Testa n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19432 Millettia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16865.1 Prunus serrulata var. spontanea Varieties Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2963 Diospyros glaucifolia Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24931 Myelochroa aurulenta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4064 Halimodendron halodendron Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16885 Phonus arborescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO691 Tarchonanthus camphoratus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4952 Pertusaria amara Species Pertusariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8927 Poria selecta Species Coccinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8354 Aster bellidiastrum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4117 Nauclea rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7464 Uruparia lanosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12600 Trametes cinnabarina Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9717 Wibelia divaricata Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8560 Aplidium tabascum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9741 Actinopyga agassizi Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16865.1 Prunus serrulata var. spontanea Varieties Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3449 Lonicera hypoleuca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15597 Calystegia pubescens Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1539 Artemisia giraldii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3415 Perymenium mendezii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4421 Penicillium cyclopium Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2421 Picea glauca Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29287 Alectoria ochroleuca Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3707 Chromatium okenii Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5981 Achlys triphylla Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19432 Millettia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO855 Elymnias thryallis Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3963 Hortonia floribunda Species Monimiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7616 Melanargia galathea Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10221 Streptomyces alboniger Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO27924 Serpocaulon triseriale Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6844 Bulbophyllum protractum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10056 Nicotiana sylvestris Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15401 Theobroma cacao Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3255 Lampranthus sociorum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3263 Thea sasanqua n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7534 Leptogorgia sarmentosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO284 Albizia procera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25216 Senecio vellereus Species Asteraceae 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
NPO15401 NPC214702 Dried Or Powder n.a. 0.029333333 n.a. n.a. mg/100g Database [PHENOL EXPLORER]

☑ 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
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 = 6200.0 nM PMID[555944]
NPT582 Individual Protein Monoamine oxidase B Homo sapiens IC50 = 50000.0 nM PMID[555944]
NPT960 Organism Medicago sativa Medicago sativa GI = 100.0 % PMID[555943]
NPT3130 Organism Lepidium sativum Lepidium sativum GI = 100.0 % PMID[555943]
NPT1234 Organism Chlorella fusca Chlorella fusca IZ = 14.0 mm PMID[555943]
NPT1232 Organism Eurotium repens Eurotium repens IZ = 6.0 mm PMID[555943]
NPT1233 Organism Mycotypha microspora Mycotypha microspora IZ = 0.0 mm PMID[555943]
NPT1230 Organism Bacillus megaterium Bacillus megaterium IZ = 2.0 mm PMID[555943]
NPT19 Organism Escherichia coli Escherichia coli IZ = 2.0 mm PMID[555943]
NPT1231 Organism Microbotryum violaceum Microbotryum violaceum IZ = 8.0 mm PMID[555943]
NPT2 Others Unspecified Ratio IC50 = 8.1 n.a. PMID[555944]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 128.0 ug.mL-1 PMID[555945]
NPT19 Organism Escherichia coli Escherichia coli MIC > 128.0 ug.mL-1 PMID[555945]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC90 > 25.0 ug.mL-1 PMID[555945]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC90 = 100.0 ug.mL-1 PMID[555945]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC90 = 8.0 ug.mL-1 PMID[555945]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC90 = 1.0 ug.mL-1 PMID[555945]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC90 = 0.125 ug.mL-1 PMID[555945]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC90 = 2.5 ug.mL-1 PMID[555945]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC90 = 0.625 ug.mL-1 PMID[555945]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis FC = 16.0 n.a. PMID[555945]

☑ 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 NPC214702 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 NPC470831
0.9688 High Similarity NPC27407
0.9688 High Similarity NPC142027
0.9612 High Similarity NPC291454
0.9466 High Similarity NPC126739
0.9466 High Similarity NPC197666
0.9462 High Similarity NPC235115
0.9389 High Similarity NPC301915
0.9389 High Similarity NPC261292
0.9318 High Similarity NPC221104
0.9297 High Similarity NPC473271
0.9254 High Similarity NPC470842
0.9231 High Similarity NPC153783
0.9179 High Similarity NPC155205
0.9173 High Similarity NPC472602
0.9173 High Similarity NPC478200
0.9173 High Similarity NPC33144
0.9127 High Similarity NPC265910
0.9127 High Similarity NPC91475
0.9111 High Similarity NPC53649
0.9111 High Similarity NPC158634
0.9104 High Similarity NPC32360
0.9104 High Similarity NPC88269
0.9104 High Similarity NPC268052
0.9098 High Similarity NPC70380
0.9084 High Similarity NPC43627
0.9077 High Similarity NPC189823
0.9077 High Similarity NPC219892
0.9051 High Similarity NPC151607
0.9051 High Similarity NPC42540
0.9037 High Similarity NPC158472
0.9037 High Similarity NPC472601
0.9037 High Similarity NPC472600
0.903 High Similarity NPC191835
0.903 High Similarity NPC212693
0.903 High Similarity NPC94248
0.9015 High Similarity NPC175943
0.9015 High Similarity NPC474097
0.8978 High Similarity NPC478202
0.8978 High Similarity NPC159721
0.8978 High Similarity NPC469542
0.8971 High Similarity NPC478217
0.8971 High Similarity NPC472605
0.8971 High Similarity NPC472035
0.8971 High Similarity NPC313123
0.8971 High Similarity NPC478201
0.8971 High Similarity NPC472604
0.8971 High Similarity NPC149533
0.8971 High Similarity NPC472603
0.8963 High Similarity NPC139634
0.8963 High Similarity NPC105456
0.8963 High Similarity NPC52358
0.8955 High Similarity NPC71256
0.8955 High Similarity NPC135837
0.8947 High Similarity NPC470844
0.8931 High Similarity NPC7012
0.8915 High Similarity NPC181715
0.8905 High Similarity NPC474385
0.8841 High Similarity NPC472610
0.8841 High Similarity NPC471731
0.8832 High Similarity NPC475730
0.8832 High Similarity NPC67650
0.8832 High Similarity NPC1704
0.8832 High Similarity NPC130485
0.8832 High Similarity NPC244923
0.8824 High Similarity NPC92655
0.8824 High Similarity NPC247409
0.8806 High Similarity NPC180905
0.8806 High Similarity NPC182496
0.879 High Similarity NPC125252
0.8786 High Similarity NPC473023
0.8777 High Similarity NPC210425
0.8777 High Similarity NPC210966
0.8777 High Similarity NPC126882
0.8777 High Similarity NPC478203
0.8777 High Similarity NPC277426
0.8777 High Similarity NPC280404
0.8777 High Similarity NPC86373
0.8768 High Similarity NPC469579
0.8768 High Similarity NPC471733
0.875 High Similarity NPC177307
0.875 High Similarity NPC61590
0.875 High Similarity NPC9121
0.8741 High Similarity NPC50455
0.8741 High Similarity NPC158481
0.8723 High Similarity NPC476463
0.8722 High Similarity NPC476389
0.872 High Similarity NPC94637
0.8714 High Similarity NPC257558
0.8714 High Similarity NPC472034
0.8714 High Similarity NPC83272
0.8705 High Similarity NPC51106
0.8705 High Similarity NPC472006
0.8696 High Similarity NPC37530
0.8696 High Similarity NPC90411
0.8686 High Similarity NPC295339
0.8686 High Similarity NPC275356
0.8676 High Similarity NPC474771
0.8676 High Similarity NPC178467
0.8676 High Similarity NPC149372
0.8676 High Similarity NPC194579
0.8676 High Similarity NPC474849
0.8676 High Similarity NPC65837
0.8672 High Similarity NPC217756
0.8652 High Similarity NPC472033
0.8651 High Similarity NPC328459
0.8651 High Similarity NPC90522
0.8633 High Similarity NPC82913
0.8633 High Similarity NPC250755
0.8623 High Similarity NPC99441
0.8623 High Similarity NPC168471
0.8615 High Similarity NPC240744
0.8615 High Similarity NPC167055
0.8615 High Similarity NPC262671
0.8615 High Similarity NPC201728
0.8613 High Similarity NPC475974
0.8613 High Similarity NPC472403
0.8611 High Similarity NPC70016
0.8611 High Similarity NPC215921
0.8601 High Similarity NPC77325
0.8601 High Similarity NPC237440
0.8601 High Similarity NPC476684
0.8601 High Similarity NPC270160
0.8601 High Similarity NPC4423
0.8592 High Similarity NPC471734
0.8592 High Similarity NPC210320
0.8592 High Similarity NPC472036
0.8583 High Similarity NPC72977
0.8583 High Similarity NPC233282
0.8582 High Similarity NPC473692
0.8582 High Similarity NPC477406
0.8582 High Similarity NPC470160
0.8561 High Similarity NPC220106
0.8561 High Similarity NPC257003
0.856 High Similarity NPC128825
0.8552 High Similarity NPC295646
0.8551 High Similarity NPC256463
0.8551 High Similarity NPC29771
0.8551 High Similarity NPC471819
0.8551 High Similarity NPC216312
0.8551 High Similarity NPC474655
0.8551 High Similarity NPC299405
0.8551 High Similarity NPC111422
0.8551 High Similarity NPC471602
0.8551 High Similarity NPC306835
0.8551 High Similarity NPC476477
0.855 High Similarity NPC95309
0.8542 High Similarity NPC472891
0.854 High Similarity NPC245058
0.8531 High Similarity NPC471641
0.8531 High Similarity NPC240253
0.8531 High Similarity NPC471642
0.8531 High Similarity NPC221352
0.8531 High Similarity NPC73411
0.8531 High Similarity NPC240622
0.8531 High Similarity NPC215711
0.8527 High Similarity NPC46634
0.8521 High Similarity NPC107625
0.8521 High Similarity NPC471735
0.8521 High Similarity NPC267509
0.8516 High Similarity NPC272454
0.8516 High Similarity NPC35856
0.8516 High Similarity NPC179092
0.8516 High Similarity NPC26433
0.8516 High Similarity NPC292665
0.8516 High Similarity NPC159760
0.8516 High Similarity NPC222876
0.8516 High Similarity NPC301987
0.8516 High Similarity NPC115188
0.8516 High Similarity NPC244994
0.8516 High Similarity NPC178395
0.8511 High Similarity NPC66404
0.8511 High Similarity NPC95123
0.8504 High Similarity NPC233165
0.8504 High Similarity NPC184579
0.85 High Similarity NPC105648
0.85 High Similarity NPC322112
0.8489 Intermediate Similarity NPC327916
0.8489 Intermediate Similarity NPC165172
0.8489 Intermediate Similarity NPC241349
0.8489 Intermediate Similarity NPC42262
0.8489 Intermediate Similarity NPC220496
0.8489 Intermediate Similarity NPC32749
0.8489 Intermediate Similarity NPC147542
0.8489 Intermediate Similarity NPC37992
0.8472 Intermediate Similarity NPC84142
0.8467 Intermediate Similarity NPC472599
0.8467 Intermediate Similarity NPC156967
0.8467 Intermediate Similarity NPC242712
0.8462 Intermediate Similarity NPC166583
0.8462 Intermediate Similarity NPC53362
0.8451 Intermediate Similarity NPC32470
0.8451 Intermediate Similarity NPC312789
0.8451 Intermediate Similarity NPC134621
0.845 Intermediate Similarity NPC198336
0.844 Intermediate Similarity NPC21873
0.844 Intermediate Similarity NPC476473
0.8433 Intermediate Similarity NPC17840
0.8433 Intermediate Similarity NPC247477
0.8433 Intermediate Similarity NPC12694

  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 NPC214702 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
0.8824 High Similarity NPD970 Clinical (unspecified phase)
0.856 High Similarity NPD9493 Approved
0.8425 Intermediate Similarity NPD9545 Approved
0.8121 Intermediate Similarity NPD7819 Suspended
0.8085 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8085 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8069 Intermediate Similarity NPD2532 Approved
0.8069 Intermediate Similarity NPD2534 Approved
0.8069 Intermediate Similarity NPD2533 Approved
0.8043 Intermediate Similarity NPD1240 Approved
0.803 Intermediate Similarity NPD1201 Approved
0.8028 Intermediate Similarity NPD1549 Phase 2
0.8014 Intermediate Similarity NPD1551 Phase 2
0.7986 Intermediate Similarity NPD230 Phase 1
0.7984 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.797 Intermediate Similarity NPD9717 Approved
0.7943 Intermediate Similarity NPD1510 Phase 2
0.7929 Intermediate Similarity NPD1607 Approved
0.7926 Intermediate Similarity NPD1203 Approved
0.792 Intermediate Similarity NPD9266 Approved
0.792 Intermediate Similarity NPD74 Approved
0.7917 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD2935 Discontinued
0.784 Intermediate Similarity NPD9263 Approved
0.784 Intermediate Similarity NPD9264 Approved
0.784 Intermediate Similarity NPD9267 Approved
0.7836 Intermediate Similarity NPD1608 Approved
0.7815 Intermediate Similarity NPD1934 Approved
0.7794 Intermediate Similarity NPD1470 Approved
0.777 Intermediate Similarity NPD3764 Approved
0.777 Intermediate Similarity NPD411 Approved
0.7763 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD3226 Approved
0.773 Intermediate Similarity NPD447 Suspended
0.7727 Intermediate Similarity NPD7075 Discontinued
0.7708 Intermediate Similarity NPD2346 Discontinued
0.7692 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD3750 Approved
0.7664 Intermediate Similarity NPD1164 Approved
0.7647 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD6232 Discontinued
0.7639 Intermediate Similarity NPD2796 Approved
0.7639 Intermediate Similarity NPD5406 Approved
0.7639 Intermediate Similarity NPD5405 Approved
0.7639 Intermediate Similarity NPD5404 Approved
0.7639 Intermediate Similarity NPD5408 Approved
0.7635 Intermediate Similarity NPD6799 Approved
0.7635 Intermediate Similarity NPD1511 Approved
0.7632 Intermediate Similarity NPD7411 Suspended
0.7626 Intermediate Similarity NPD6832 Phase 2
0.7613 Intermediate Similarity NPD3749 Approved
0.7612 Intermediate Similarity NPD17 Approved
0.7606 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD520 Approved
0.7584 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD6959 Discontinued
0.7569 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD4380 Phase 2
0.7559 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD4628 Phase 3
0.7535 Intermediate Similarity NPD943 Approved
0.7533 Intermediate Similarity NPD1512 Approved
0.7532 Intermediate Similarity NPD5710 Approved
0.7532 Intermediate Similarity NPD5711 Approved
0.752 Intermediate Similarity NPD9261 Approved
0.7518 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7473 Discontinued
0.75 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3817 Phase 2
0.7483 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD1019 Discontinued
0.7481 Intermediate Similarity NPD1778 Approved
0.747 Intermediate Similarity NPD8150 Discontinued
0.7451 Intermediate Similarity NPD6599 Discontinued
0.7448 Intermediate Similarity NPD7033 Discontinued
0.7438 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7768 Phase 2
0.7436 Intermediate Similarity NPD3882 Suspended
0.7432 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD9281 Approved
0.7419 Intermediate Similarity NPD2801 Approved
0.741 Intermediate Similarity NPD2797 Approved
0.7407 Intermediate Similarity NPD5844 Phase 1
0.7397 Intermediate Similarity NPD6100 Approved
0.7397 Intermediate Similarity NPD6099 Approved
0.7389 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD5402 Approved
0.7372 Intermediate Similarity NPD422 Phase 1
0.7368 Intermediate Similarity NPD5403 Approved
0.7365 Intermediate Similarity NPD1243 Approved
0.7357 Intermediate Similarity NPD2798 Approved
0.7355 Intermediate Similarity NPD6801 Discontinued
0.7351 Intermediate Similarity NPD5401 Approved
0.7347 Intermediate Similarity NPD2344 Approved
0.7338 Intermediate Similarity NPD1283 Approved
0.7333 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6166 Phase 2
0.7329 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD2799 Discontinued
0.7329 Intermediate Similarity NPD3748 Approved
0.7329 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD1465 Phase 2
0.7301 Intermediate Similarity NPD7054 Approved
0.7294 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD7390 Discontinued
0.7273 Intermediate Similarity NPD3268 Approved
0.7273 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2313 Discontinued
0.7256 Intermediate Similarity NPD7074 Phase 3
0.7256 Intermediate Similarity NPD7472 Approved
0.7255 Intermediate Similarity NPD920 Approved
0.7252 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD2800 Approved
0.7241 Intermediate Similarity NPD1933 Approved
0.7237 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD4626 Approved
0.7214 Intermediate Similarity NPD3225 Approved
0.7212 Intermediate Similarity NPD6797 Phase 2
0.7211 Intermediate Similarity NPD4308 Phase 3
0.7194 Intermediate Similarity NPD9269 Phase 2
0.7186 Intermediate Similarity NPD8313 Approved
0.7186 Intermediate Similarity NPD8312 Approved
0.7183 Intermediate Similarity NPD9494 Approved
0.7169 Intermediate Similarity NPD7251 Discontinued
0.7153 Intermediate Similarity NPD5691 Approved
0.7153 Intermediate Similarity NPD9268 Approved
0.7152 Intermediate Similarity NPD2309 Approved
0.7152 Intermediate Similarity NPD6190 Approved
0.7134 Intermediate Similarity NPD3818 Discontinued
0.7126 Intermediate Similarity NPD7808 Phase 3
0.7125 Intermediate Similarity NPD919 Approved
0.7122 Intermediate Similarity NPD1281 Approved
0.7103 Intermediate Similarity NPD6663 Approved
0.7099 Intermediate Similarity NPD2182 Approved
0.7091 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD7003 Approved
0.7081 Intermediate Similarity NPD5494 Approved
0.7078 Intermediate Similarity NPD6273 Approved
0.7075 Intermediate Similarity NPD6651 Approved
0.7066 Intermediate Similarity NPD6559 Discontinued
0.7063 Intermediate Similarity NPD5736 Approved
0.7059 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD164 Approved
0.705 Intermediate Similarity NPD3496 Discontinued
0.7042 Intermediate Similarity NPD3266 Approved
0.7042 Intermediate Similarity NPD3267 Approved
0.703 Intermediate Similarity NPD3751 Discontinued
0.703 Intermediate Similarity NPD7177 Discontinued
0.7027 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD1238 Approved
0.7006 Intermediate Similarity NPD5953 Discontinued
0.7 Intermediate Similarity NPD6002 Phase 3
0.7 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6004 Phase 3
0.7 Intermediate Similarity NPD1610 Phase 2
0.7 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6005 Phase 3
0.6977 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4625 Phase 3
0.6963 Remote Similarity NPD1241 Discontinued
0.694 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6939 Remote Similarity NPD4060 Phase 1
0.6939 Remote Similarity NPD4307 Phase 2
0.6933 Remote Similarity NPD4477 Approved
0.6933 Remote Similarity NPD4476 Approved
0.6914 Remote Similarity NPD6534 Approved
0.6914 Remote Similarity NPD6535 Approved
0.6906 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6905 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6901 Remote Similarity NPD4749 Approved
0.6892 Remote Similarity NPD6355 Discontinued
0.689 Remote Similarity NPD3787 Discontinued
0.6889 Remote Similarity NPD7435 Discontinued
0.6887 Remote Similarity NPD1471 Phase 3
0.6887 Remote Similarity NPD7266 Discontinued
0.6886 Remote Similarity NPD7286 Phase 2
0.6883 Remote Similarity NPD3300 Phase 2
0.6875 Remote Similarity NPD6007 Clinical (unspecified phase)
0.687 Remote Similarity NPD5048 Discontinued
0.6863 Remote Similarity NPD8166 Discontinued
0.6857 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6857 Remote Similarity NPD6212 Phase 3
0.6857 Remote Similarity NPD6213 Phase 3
0.6853 Remote Similarity NPD1876 Approved
0.6851 Remote Similarity NPD8320 Phase 1
0.6851 Remote Similarity NPD8319 Approved
0.6849 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6849 Remote Similarity NPD7008 Discontinued
0.6835 Remote Similarity NPD3455 Phase 2
0.6835 Remote Similarity NPD1548 Phase 1
0.6835 Remote Similarity NPD7458 Discontinued
0.6835 Remote Similarity NPD1894 Discontinued

  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