Structure

Physi-Chem Properties

Molecular Weight:  192.08
Volume:  197.524
LogP:  3.51
LogD:  2.404
LogS:  -3.114
# 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:  0.637
Synthetic Accessibility Score:  2.875
Fsp3:  0.364
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.546
MDCK Permeability:  2.6998832254321314e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.473
Plasma Protein Binding (PPB):  93.46070098876953%
Volume Distribution (VD):  0.746
Pgp-substrate:  5.313899517059326%

ADMET: Metabolism

CYP1A2-inhibitor:  0.971
CYP1A2-substrate:  0.717
CYP2C19-inhibitor:  0.642
CYP2C19-substrate:  0.272
CYP2C9-inhibitor:  0.542
CYP2C9-substrate:  0.905
CYP2D6-inhibitor:  0.746
CYP2D6-substrate:  0.66
CYP3A4-inhibitor:  0.405
CYP3A4-substrate:  0.18

ADMET: Excretion

Clearance (CL):  12.658
Half-life (T1/2):  0.489

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.155
Drug-inuced Liver Injury (DILI):  0.513
AMES Toxicity:  0.331
Rat Oral Acute Toxicity:  0.11
Maximum Recommended Daily Dose:  0.285
Skin Sensitization:  0.731
Carcinogencity:  0.939
Eye Corrosion:  0.18
Eye Irritation:  0.963
Respiratory Toxicity:  0.334

Download Data

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC291454

Natural Product ID:  NPC291454
Common Name*:   (-)-5-Methylmellein
IUPAC Name:   (3R)-8-hydroxy-3,5-dimethyl-3,4-dihydroisochromen-1-one
Synonyms:  
Standard InCHIKey:  YETSBBYQOFXYGV-SSDOTTSWSA-N
Standard InCHI:  InChI=1S/C11H12O3/c1-6-3-4-9(12)10-8(6)5-7(2)14-11(10)13/h3-4,7,12H,5H2,1-2H3/t7-/m1/s1
SMILES:  Cc1ccc(c2c1C[C@@H](C)OC2=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL461985
PubChem CID:   14807789
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
NPO2421 Picea glauca Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[18636777]
NPO33230 Phomopsis sp. BCC 9789 Species Valsaceae Eukaryota n.a. n.a. n.a. PMID[20038128]
NPO6850 Typha domingensis Species Typhaceae Eukaryota n.a. aerial part n.a. PMID[21417376]
NPO7622 Monanchora pulchra Species Crambeidae Eukaryota n.a. n.a. n.a. PMID[21848268]
NPO7622 Monanchora pulchra Species Crambeidae Eukaryota n.a. Urup Island (4557,9 N; 15044,9 E; depth 66 m) 2008-AUG PMID[21848268]
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]
NPO17226 Burkholderia pyrrocinia Species Burkholderiaceae Bacteria n.a. n.a. n.a. PMID[4955234]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19663 Cliona celata Species Clionaidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7916 Vanilla planifolia Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3124 Gloiopeltis furcata Species Endocladiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7770 Lactuca laciniata Species Asteraceae 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]
NPO3124 Gloiopeltis furcata Species Endocladiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19663 Cliona celata Species Clionaidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7916 Vanilla planifolia Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3124 Gloiopeltis furcata Species Endocladiaceae 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]
NPO10870 Trichilia hirta Species Meliaceae 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]
NPO6302 Licaria armeniaca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3255 Lampranthus sociorum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO99 Artemisia porrecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7916 Vanilla planifolia Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5981 Achlys triphylla Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25775 Dasystenella acanthina Species Primnoidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO691 Tarchonanthus camphoratus 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]
NPO19114 Rabdosia forrestii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO115 Eutreptia viridis Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO855 Elymnias thryallis Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2963 Diospyros glaucifolia Species Ebenaceae 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]
NPO1897 Ephedra aphylla Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO284 Albizia procera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7770 Lactuca laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6130 Mammillaria magnimamma Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19333 Byssothecium obiones Species Massarinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20432 Pseudocinchona mayumbensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4816 Cycas armstrongii Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5588 Bursera tonkinensis Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19663 Cliona celata Species Clionaidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17226 Burkholderia pyrrocinia Species Burkholderiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4117 Nauclea rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7155 Cypripedium calceolus Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3756 Munronia delavayi Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2421 Picea glauca Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2609 Neonectria candida Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3419 Quercus suber Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15597 Calystegia pubescens Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3124 Gloiopeltis furcata Species Endocladiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21095 Prostanthera melissifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4952 Pertusaria amara Species Pertusariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18420 Meniscium simplex Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18463 Plectocephalus chilensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3415 Perymenium mendezii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7622 Monanchora pulchra Species Crambeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29287 Alectoria ochroleuca Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6850 Typha domingensis Species Typhaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19432 Millettia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20504 Siphonaria virgulata Species Chytriomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1539 Artemisia giraldii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO291 Suillus bovinus Species Suillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7616 Melanargia galathea Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2968 Anthopleura xanthogrammica Species Actiniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4293 Allium neapolitanum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6844 Bulbophyllum protractum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3259 Streptomyces showdoensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4421 Penicillium cyclopium Species Aspergillaceae 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
NPT91 Cell Line KB Homo sapiens IC50 > 104000.0 nM PMID[458328]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 > 104000.0 nM PMID[458328]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 260000.0 nM PMID[458328]
NPT582 Individual Protein Monoamine oxidase B Homo sapiens IC50 = 38500.0 nM PMID[458329]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 = 4600.0 nM PMID[458329]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 104000.0 nM PMID[458328]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC > 260000.0 nM PMID[458328]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 MIC > 260000.0 nM PMID[458328]
NPT23336 PROTEIN FAMILY Monoamine oxidase Mus musculus IC50 = 1060.0 nM PMID[458329]
NPT2 Others Unspecified Ratio IC50 = 8.3 n.a. PMID[458329]

☑ 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 NPC291454 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
0.9697 High Similarity NPC221104
0.9627 High Similarity NPC470842
0.9612 High Similarity NPC470831
0.9612 High Similarity NPC214702
0.9478 High Similarity NPC88269
0.9474 High Similarity NPC301915
0.9474 High Similarity NPC261292
0.947 High Similarity NPC142027
0.947 High Similarity NPC27407
0.9416 High Similarity NPC42540
0.9416 High Similarity NPC151607
0.9407 High Similarity NPC472601
0.9407 High Similarity NPC472600
0.9398 High Similarity NPC235115
0.9343 High Similarity NPC159721
0.9338 High Similarity NPC472603
0.9338 High Similarity NPC472605
0.9338 High Similarity NPC472604
0.9323 High Similarity NPC470844
0.9265 High Similarity NPC155205
0.9259 High Similarity NPC472602
0.9203 High Similarity NPC472610
0.9203 High Similarity NPC471731
0.9197 High Similarity NPC53649
0.9185 High Similarity NPC70380
0.9173 High Similarity NPC153783
0.9143 High Similarity NPC473023
0.913 High Similarity NPC471733
0.9118 High Similarity NPC94248
0.9118 High Similarity NPC191835
0.9118 High Similarity NPC212693
0.9118 High Similarity NPC126739
0.9118 High Similarity NPC478200
0.9118 High Similarity NPC33144
0.9118 High Similarity NPC197666
0.9111 High Similarity NPC158481
0.9111 High Similarity NPC50455
0.9065 High Similarity NPC478202
0.9065 High Similarity NPC469542
0.9058 High Similarity NPC37530
0.9058 High Similarity NPC313123
0.9058 High Similarity NPC158634
0.9058 High Similarity NPC478217
0.9058 High Similarity NPC149533
0.9051 High Similarity NPC268052
0.9051 High Similarity NPC275356
0.9051 High Similarity NPC32360
0.9051 High Similarity NPC105456
0.9051 High Similarity NPC139634
0.9044 High Similarity NPC194579
0.9044 High Similarity NPC71256
0.9023 High Similarity NPC219892
0.9023 High Similarity NPC189823
0.8993 High Similarity NPC82913
0.8986 High Similarity NPC99441
0.8986 High Similarity NPC168471
0.8986 High Similarity NPC158472
0.8963 High Similarity NPC175943
0.8947 High Similarity NPC473271
0.8944 High Similarity NPC471734
0.8936 High Similarity NPC473692
0.8921 High Similarity NPC478201
0.8921 High Similarity NPC1704
0.8921 High Similarity NPC67650
0.8921 High Similarity NPC472035
0.8913 High Similarity NPC52358
0.8905 High Similarity NPC135837
0.8905 High Similarity NPC245058
0.8873 High Similarity NPC471735
0.8857 High Similarity NPC469579
0.8857 High Similarity NPC322112
0.8857 High Similarity NPC474385
0.8849 High Similarity NPC165172
0.8832 High Similarity NPC156967
0.8832 High Similarity NPC472599
0.8815 High Similarity NPC476389
0.8811 High Similarity NPC476463
0.8811 High Similarity NPC166583
0.8811 High Similarity NPC53362
0.8803 High Similarity NPC83272
0.8794 High Similarity NPC472006
0.8794 High Similarity NPC51106
0.8786 High Similarity NPC244923
0.8786 High Similarity NPC475730
0.8779 High Similarity NPC91475
0.8779 High Similarity NPC265910
0.8779 High Similarity NPC184219
0.8777 High Similarity NPC92655
0.8777 High Similarity NPC247409
0.8768 High Similarity NPC474849
0.8768 High Similarity NPC178467
0.8768 High Similarity NPC149372
0.8768 High Similarity NPC65837
0.8768 High Similarity NPC474771
0.8759 High Similarity NPC182496
0.8759 High Similarity NPC180905
0.875 High Similarity NPC43627
0.8741 High Similarity NPC260946
0.8741 High Similarity NPC7012
0.8741 High Similarity NPC163846
0.8741 High Similarity NPC225173
0.8732 High Similarity NPC210966
0.8732 High Similarity NPC210425
0.8732 High Similarity NPC478203
0.8732 High Similarity NPC277426
0.8732 High Similarity NPC126882
0.8732 High Similarity NPC86373
0.8732 High Similarity NPC280404
0.8723 High Similarity NPC250755
0.8714 High Similarity NPC64664
0.8705 High Similarity NPC61590
0.8705 High Similarity NPC9121
0.8705 High Similarity NPC177307
0.8705 High Similarity NPC475974
0.8699 High Similarity NPC215921
0.8699 High Similarity NPC70016
0.869 High Similarity NPC237440
0.869 High Similarity NPC4423
0.869 High Similarity NPC270160
0.869 High Similarity NPC77325
0.8686 High Similarity NPC474097
0.8686 High Similarity NPC475645
0.8681 High Similarity NPC125801
0.8671 High Similarity NPC472034
0.8671 High Similarity NPC257558
0.8667 High Similarity NPC296158
0.8657 High Similarity NPC473744
0.8652 High Similarity NPC130485
0.8652 High Similarity NPC90411
0.8643 High Similarity NPC295339
0.8643 High Similarity NPC474655
0.8639 High Similarity NPC295646
0.8639 High Similarity NPC271681
0.863 High Similarity NPC119929
0.8626 High Similarity NPC67300
0.8623 High Similarity NPC278375
0.8621 High Similarity NPC37139
0.8621 High Similarity NPC221352
0.8611 High Similarity NPC267509
0.8611 High Similarity NPC472033
0.8611 High Similarity NPC107625
0.8592 High Similarity NPC314271
0.8582 High Similarity NPC181715
0.8581 High Similarity NPC472799
0.8571 High Similarity NPC262671
0.8571 High Similarity NPC472403
0.8571 High Similarity NPC201728
0.8562 High Similarity NPC233267
0.8562 High Similarity NPC476684
0.8562 High Similarity NPC291049
0.8562 High Similarity NPC247219
0.8561 High Similarity NPC118919
0.8552 High Similarity NPC210320
0.8552 High Similarity NPC472036
0.8552 High Similarity NPC119767
0.8551 High Similarity NPC474394
0.8542 High Similarity NPC32470
0.8542 High Similarity NPC134621
0.8531 High Similarity NPC66593
0.8529 High Similarity NPC62219
0.8529 High Similarity NPC17840
0.8529 High Similarity NPC247477
0.8521 High Similarity NPC220106
0.8521 High Similarity NPC257003
0.8514 High Similarity NPC115249
0.8514 High Similarity NPC273483
0.8514 High Similarity NPC167903
0.8511 High Similarity NPC476477
0.8511 High Similarity NPC471819
0.8511 High Similarity NPC299405
0.8511 High Similarity NPC111422
0.8511 High Similarity NPC216312
0.8511 High Similarity NPC306835
0.8511 High Similarity NPC29771
0.8511 High Similarity NPC471602
0.8511 High Similarity NPC256463
0.8507 High Similarity NPC95309
0.8503 High Similarity NPC469619
0.8503 High Similarity NPC469670
0.8503 High Similarity NPC470107
0.8503 High Similarity NPC179178
0.8503 High Similarity NPC56204
0.8503 High Similarity NPC150928
0.8503 High Similarity NPC472891
0.8503 High Similarity NPC205766
0.8503 High Similarity NPC158866
0.8493 Intermediate Similarity NPC153417
0.8493 Intermediate Similarity NPC240253
0.8493 Intermediate Similarity NPC215711
0.8493 Intermediate Similarity NPC73411
0.8493 Intermediate Similarity NPC240622
0.8493 Intermediate Similarity NPC471641
0.8493 Intermediate Similarity NPC105415
0.8493 Intermediate Similarity NPC471642
0.8489 Intermediate Similarity NPC290803
0.8485 Intermediate Similarity NPC283514
0.8483 Intermediate Similarity NPC51513
0.8483 Intermediate Similarity NPC202112
0.8483 Intermediate Similarity NPC237208
0.8483 Intermediate Similarity NPC470570

  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 NPC291454 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
0.8777 High Similarity NPD970 Clinical (unspecified phase)
0.8456 Intermediate Similarity NPD7819 Suspended
0.8414 Intermediate Similarity NPD2534 Approved
0.8414 Intermediate Similarity NPD2532 Approved
0.8414 Intermediate Similarity NPD2533 Approved
0.8385 Intermediate Similarity NPD9545 Approved
0.8239 Intermediate Similarity NPD2935 Discontinued
0.8231 Intermediate Similarity NPD9493 Approved
0.8182 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8143 Intermediate Similarity NPD1240 Approved
0.8125 Intermediate Similarity NPD1549 Phase 2
0.8092 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8052 Intermediate Similarity NPD7075 Discontinued
0.8042 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8042 Intermediate Similarity NPD1510 Phase 2
0.8029 Intermediate Similarity NPD1164 Approved
0.8028 Intermediate Similarity NPD1607 Approved
0.8 Intermediate Similarity NPD1201 Approved
0.7986 Intermediate Similarity NPD5404 Approved
0.7986 Intermediate Similarity NPD5408 Approved
0.7986 Intermediate Similarity NPD5405 Approved
0.7986 Intermediate Similarity NPD5406 Approved
0.7974 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD6232 Discontinued
0.7961 Intermediate Similarity NPD7411 Suspended
0.7958 Intermediate Similarity NPD230 Phase 1
0.7922 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD1934 Approved
0.7898 Intermediate Similarity NPD6959 Discontinued
0.7895 Intermediate Similarity NPD4380 Phase 2
0.7872 Intermediate Similarity NPD3764 Approved
0.7848 Intermediate Similarity NPD5710 Approved
0.7848 Intermediate Similarity NPD5711 Approved
0.7829 Intermediate Similarity NPD3226 Approved
0.7823 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD7473 Discontinued
0.7808 Intermediate Similarity NPD2346 Discontinued
0.777 Intermediate Similarity NPD3750 Approved
0.777 Intermediate Similarity NPD1470 Approved
0.7756 Intermediate Similarity NPD7768 Phase 2
0.775 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD2796 Approved
0.774 Intermediate Similarity NPD1551 Phase 2
0.7716 Intermediate Similarity NPD5844 Phase 1
0.7707 Intermediate Similarity NPD3749 Approved
0.7703 Intermediate Similarity NPD1243 Approved
0.7698 Intermediate Similarity NPD1283 Approved
0.7687 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD9717 Approved
0.7681 Intermediate Similarity NPD1608 Approved
0.7677 Intermediate Similarity NPD6801 Discontinued
0.7671 Intermediate Similarity NPD2799 Discontinued
0.7667 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD4628 Phase 3
0.7643 Intermediate Similarity NPD1203 Approved
0.7639 Intermediate Similarity NPD943 Approved
0.7616 Intermediate Similarity NPD7390 Discontinued
0.7616 Intermediate Similarity NPD1511 Approved
0.7616 Intermediate Similarity NPD6799 Approved
0.7615 Intermediate Similarity NPD9266 Approved
0.7615 Intermediate Similarity NPD74 Approved
0.7597 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD4626 Approved
0.7584 Intermediate Similarity NPD2800 Approved
0.7582 Intermediate Similarity NPD920 Approved
0.7566 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD8150 Discontinued
0.7551 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD6599 Discontinued
0.7538 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD9264 Approved
0.7538 Intermediate Similarity NPD9263 Approved
0.7538 Intermediate Similarity NPD9267 Approved
0.7532 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD5691 Approved
0.7516 Intermediate Similarity NPD1512 Approved
0.75 Intermediate Similarity NPD411 Approved
0.75 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD1281 Approved
0.7468 Intermediate Similarity NPD3817 Phase 2
0.7466 Intermediate Similarity NPD447 Suspended
0.7464 Intermediate Similarity NPD17 Approved
0.7451 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD2344 Approved
0.7438 Intermediate Similarity NPD919 Approved
0.7432 Intermediate Similarity NPD3748 Approved
0.7423 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD6166 Phase 2
0.7423 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD3882 Suspended
0.7417 Intermediate Similarity NPD7003 Approved
0.7417 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD6651 Approved
0.7405 Intermediate Similarity NPD1465 Phase 2
0.7405 Intermediate Similarity NPD2801 Approved
0.7394 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD5494 Approved
0.7379 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD2313 Discontinued
0.7365 Intermediate Similarity NPD6559 Discontinued
0.7361 Intermediate Similarity NPD6832 Phase 2
0.7357 Intermediate Similarity NPD422 Phase 1
0.7357 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD7074 Phase 3
0.7347 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6663 Approved
0.7329 Intermediate Similarity NPD520 Approved
0.7315 Intermediate Similarity NPD7033 Discontinued
0.7305 Intermediate Similarity NPD5953 Discontinued
0.7292 Intermediate Similarity NPD5736 Approved
0.729 Intermediate Similarity NPD6273 Approved
0.7289 Intermediate Similarity NPD7054 Approved
0.7279 Intermediate Similarity NPD4060 Phase 1
0.7278 Intermediate Similarity NPD8312 Approved
0.7278 Intermediate Similarity NPD8313 Approved
0.7273 Intermediate Similarity NPD2797 Approved
0.7267 Intermediate Similarity NPD4476 Approved
0.7267 Intermediate Similarity NPD4477 Approved
0.7267 Intermediate Similarity NPD6100 Approved
0.7267 Intermediate Similarity NPD6099 Approved
0.7267 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD2309 Approved
0.7246 Intermediate Similarity NPD7472 Approved
0.7231 Intermediate Similarity NPD9261 Approved
0.7229 Intermediate Similarity NPD3818 Discontinued
0.7226 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD2798 Approved
0.7222 Intermediate Similarity NPD1019 Discontinued
0.7219 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD1778 Approved
0.7202 Intermediate Similarity NPD6797 Phase 2
0.7186 Intermediate Similarity NPD7286 Phase 2
0.7183 Intermediate Similarity NPD9269 Phase 2
0.7172 Intermediate Similarity NPD9494 Approved
0.7162 Intermediate Similarity NPD2979 Phase 3
0.7161 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7251 Discontinued
0.7153 Intermediate Similarity NPD9281 Approved
0.7152 Intermediate Similarity NPD2438 Suspended
0.7152 Intermediate Similarity NPD7458 Discontinued
0.7143 Intermediate Similarity NPD9268 Approved
0.7143 Intermediate Similarity NPD6190 Approved
0.7143 Intermediate Similarity NPD5402 Approved
0.7143 Intermediate Similarity NPD3268 Approved
0.7143 Intermediate Similarity NPD1651 Approved
0.7134 Intermediate Similarity NPD5403 Approved
0.7126 Intermediate Similarity NPD7177 Discontinued
0.7118 Intermediate Similarity NPD7808 Phase 3
0.7115 Intermediate Similarity NPD5401 Approved
0.7114 Intermediate Similarity NPD5124 Phase 1
0.7114 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD1610 Phase 2
0.7111 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD6004 Phase 3
0.7105 Intermediate Similarity NPD6005 Phase 3
0.7105 Intermediate Similarity NPD6002 Phase 3
0.7102 Intermediate Similarity NPD6535 Approved
0.7102 Intermediate Similarity NPD6534 Approved
0.7091 Intermediate Similarity NPD7229 Phase 3
0.7086 Intermediate Similarity NPD4308 Phase 3
0.7078 Intermediate Similarity NPD8166 Discontinued
0.7075 Intermediate Similarity NPD4625 Phase 3
0.7072 Intermediate Similarity NPD7435 Discontinued
0.7033 Intermediate Similarity NPD8320 Phase 1
0.7033 Intermediate Similarity NPD8319 Approved
0.703 Intermediate Similarity NPD1247 Approved
0.7027 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD37 Approved
0.7018 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD6234 Discontinued
0.7 Intermediate Similarity NPD6780 Approved
0.7 Intermediate Similarity NPD6779 Approved
0.7 Intermediate Similarity NPD6782 Approved
0.7 Intermediate Similarity NPD6778 Approved
0.7 Intermediate Similarity NPD6777 Approved
0.7 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1933 Approved
0.7 Intermediate Similarity NPD6776 Approved
0.7 Intermediate Similarity NPD6355 Discontinued
0.7 Intermediate Similarity NPD6781 Approved
0.6994 Remote Similarity NPD4966 Approved
0.6994 Remote Similarity NPD4967 Phase 2
0.6994 Remote Similarity NPD4965 Approved
0.6993 Remote Similarity NPD1471 Phase 3
0.6986 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7699 Phase 2
0.6983 Remote Similarity NPD7700 Phase 2
0.6972 Remote Similarity NPD3019 Approved
0.6972 Remote Similarity NPD2932 Approved
0.6968 Remote Similarity NPD3400 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