Structure

Physi-Chem Properties

Molecular Weight:  208.07
Volume:  212.234
LogP:  1.456
LogD:  1.34
LogS:  -2.296
# Rotatable Bonds:  4
TPSA:  55.76
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.603
Synthetic Accessibility Score:  2.264
Fsp3:  0.182
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.643
MDCK Permeability:  1.5245250324369408e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.035
Human Intestinal Absorption (HIA):  0.045
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.881
Plasma Protein Binding (PPB):  88.65138244628906%
Volume Distribution (VD):  0.745
Pgp-substrate:  10.728351593017578%

ADMET: Metabolism

CYP1A2-inhibitor:  0.852
CYP1A2-substrate:  0.897
CYP2C19-inhibitor:  0.047
CYP2C19-substrate:  0.744
CYP2C9-inhibitor:  0.036
CYP2C9-substrate:  0.743
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.893
CYP3A4-inhibitor:  0.016
CYP3A4-substrate:  0.234

ADMET: Excretion

Clearance (CL):  8.723
Half-life (T1/2):  0.91

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.46
Drug-inuced Liver Injury (DILI):  0.112
AMES Toxicity:  0.417
Rat Oral Acute Toxicity:  0.94
Maximum Recommended Daily Dose:  0.251
Skin Sensitization:  0.956
Carcinogencity:  0.805
Eye Corrosion:  0.213
Eye Irritation:  0.92
Respiratory Toxicity:  0.957

Download Data

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

  Natural Product: NPC271985

Natural Product ID:  NPC271985
Common Name*:   3-(4-Hydroxy-3,5-Dimethoxyphenyl)Acrylaldehyde
IUPAC Name:   (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
Synonyms:  
Standard InCHIKey:  CDICDSOGTRCHMG-ONEGZZNKSA-N
Standard InCHI:  InChI=1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+
SMILES:  COc1cc(/C=C/C=O)cc(c1O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL225067
PubChem CID:   5280802
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0000190] Methoxyphenols

*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
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. root n.a. DOI[10.1016/0031-9422(90)85209-X]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. Caribbean n.a. PMID[10021943]
NPO4562 Lonchocarpus urucu Species Fabaceae Eukaryota n.a. root n.a. PMID[10075742]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. Taiwan n.a. PMID[11277748]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. root n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. bark n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. xylem n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. leaf n.a. PMID[14727919]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[15921424]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[1659613]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota stem bark n.a. n.a. PMID[17918910]
NPO12339 Daphne feddei Species Thymelaeaceae Eukaryota stem bark Kunming, Yunnan Province, China n.a. PMID[18986199]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota Stems; Barks n.a. n.a. PMID[19086868]
NPO26203 Dysidea villosa Species Dysideidae Eukaryota n.a. Hainan, China n.a. PMID[19091557]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[23806071]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. bark n.a. PMID[23823874]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. China n.a. PMID[25115700]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[26666037]
NPO25406 Celastrus monospermus Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[28006915]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[28485933]
NPO9740 Dacrycarpus imbricatus Species Podocarpaceae Eukaryota Twigs n.a. n.a. PMID[32786878]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7798955]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6017 Artemisia arbuscula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13313 Talipariti tiliaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23754 Solanum aculeatissimum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6017 Artemisia arbuscula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9740 Dacrycarpus imbricatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21943 Acer saccharinum Species Aceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25358 Senecio gilliesi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13443 Doris montereyensis Species Dorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26789 Tephrosia bidwilli Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23754 Solanum aculeatissimum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22264 Inula salsoloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22890 Eutrochium purpureum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26690 Lactarius subpiperatus Species Lactariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1267 Acronychia laurifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9324 0techis scutatus Species Elapidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21329 Ilyonectria destructans Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26203 Dysidea villosa Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26160 Thielavia terricola Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25802 Agave deserti Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13313 Talipariti tiliaceum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25201 Aglaia pyramidata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25122 Conium maculatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26849 Parmelia zollingeri Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24478 Morinda coreia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8794 Aconitum fauriei Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2622 Cheilanthes mysurensis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3963 Hortonia floribunda Species Monimiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9094 Citrus reshni Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25833 Asclepias subulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25259 Schrebera swietenoides Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15398 Rhizopus stolonifer Species Rhizopodaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6559 Duddingtonia flagrans Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12339 Daphne feddei Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO182 Cylas formicarius Species Brentidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9234 Cynoctonum wilfordii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26162 Botrydium granulatum Species Botrydiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9740 Dacrycarpus imbricatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1477 Egregia menziesii Species Lessoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26298 Zanthoxylum simulans Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO378 Myristica argentea Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26534 Streptomyces clavifer Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6017 Artemisia arbuscula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10211 Pajanelia multijuga n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO790 Cybister confusus Species Dytiscidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25871 Cryptolestes ferrugineus Species Laemophloeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25406 Celastrus monospermus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3005 Passiflora morifolia Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26409 Plakortis simplex Species Plakinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24547 Xanthoria parietina Species Teloschistaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19672 Hosta sieboldiana Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26992 Sophora leachiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24918 Jacobaea cannabifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4562 Lonchocarpus urucu Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28636 Vernonia lilacina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25714 Solanum spirale Species Solanaceae 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
NPO42042 NPC271985 n.a. n.a. 0.00524 n.a. n.a. mg/100mL 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
NPT137 Cell Line L1210 Mus musculus log(1/ID50) = 2.6 n.a. PMID[534587]
NPT137 Cell Line L1210 Mus musculus log(1/ID50) = 4.25 n.a. PMID[534587]
NPT81 Cell Line A549 Homo sapiens IC50 > 100000.0 nM PMID[534588]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 63000.0 nM PMID[534588]
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 = 66000.0 nM PMID[534588]
NPT114 Cell Line LoVo Homo sapiens IC50 = 33000.0 nM PMID[534588]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 56000.0 nM PMID[534588]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 39000.0 nM PMID[534588]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI = 50.0 % PMID[534588]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 2.0 % PMID[534588]

☑ 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 NPC271985 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
0.9664 High Similarity NPC238810
0.9504 High Similarity NPC300326
0.9504 High Similarity NPC58279
0.9431 High Similarity NPC109275
0.9355 High Similarity NPC48315
0.9328 High Similarity NPC229401
0.9237 High Similarity NPC39793
0.9237 High Similarity NPC259638
0.9213 High Similarity NPC36490
0.9174 High Similarity NPC310373
0.9153 High Similarity NPC193067
0.9083 High Similarity NPC20674
0.907 High Similarity NPC274613
0.9032 High Similarity NPC27352
0.9024 High Similarity NPC108545
0.9016 High Similarity NPC49341
0.9008 High Similarity NPC232084
0.9008 High Similarity NPC10932
0.9008 High Similarity NPC247364
0.9008 High Similarity NPC61516
0.8992 High Similarity NPC237330
0.8943 High Similarity NPC71579
0.8943 High Similarity NPC473411
0.8943 High Similarity NPC262253
0.8939 High Similarity NPC267291
0.8926 High Similarity NPC226629
0.8872 High Similarity NPC224876
0.8872 High Similarity NPC83375
0.8871 High Similarity NPC220598
0.8871 High Similarity NPC165375
0.8852 High Similarity NPC202474
0.8852 High Similarity NPC222175
0.8846 High Similarity NPC92830
0.8846 High Similarity NPC111635
0.8843 High Similarity NPC164706
0.8843 High Similarity NPC272471
0.8843 High Similarity NPC107588
0.8843 High Similarity NPC212743
0.8843 High Similarity NPC70744
0.8843 High Similarity NPC137537
0.8806 High Similarity NPC278469
0.8806 High Similarity NPC193722
0.88 High Similarity NPC183446
0.879 High Similarity NPC288238
0.878 High Similarity NPC204466
0.878 High Similarity NPC166759
0.8741 High Similarity NPC299154
0.873 High Similarity NPC233410
0.873 High Similarity NPC299584
0.873 High Similarity NPC117214
0.873 High Similarity NPC203133
0.873 High Similarity NPC472093
0.873 High Similarity NPC82483
0.873 High Similarity NPC193544
0.873 High Similarity NPC208950
0.873 High Similarity NPC298757
0.873 High Similarity NPC116907
0.873 High Similarity NPC221077
0.873 High Similarity NPC57490
0.873 High Similarity NPC251855
0.873 High Similarity NPC17943
0.873 High Similarity NPC265483
0.873 High Similarity NPC475169
0.8722 High Similarity NPC13067
0.872 High Similarity NPC197757
0.872 High Similarity NPC228922
0.871 High Similarity NPC70752
0.871 High Similarity NPC145780
0.8702 High Similarity NPC249791
0.8702 High Similarity NPC237594
0.8702 High Similarity NPC476387
0.8702 High Similarity NPC119060
0.8699 High Similarity NPC177475
0.8699 High Similarity NPC474565
0.8699 High Similarity NPC148615
0.8699 High Similarity NPC35071
0.8692 High Similarity NPC245120
0.8689 High Similarity NPC255675
0.8689 High Similarity NPC63083
0.8678 High Similarity NPC221049
0.8672 High Similarity NPC186843
0.8672 High Similarity NPC470213
0.8672 High Similarity NPC98631
0.8672 High Similarity NPC206615
0.8661 High Similarity NPC28730
0.8661 High Similarity NPC78974
0.8661 High Similarity NPC44748
0.8661 High Similarity NPC214406
0.8661 High Similarity NPC223136
0.8661 High Similarity NPC18924
0.8661 High Similarity NPC103823
0.8651 High Similarity NPC5796
0.8651 High Similarity NPC206487
0.8647 High Similarity NPC95162
0.8647 High Similarity NPC52086
0.8647 High Similarity NPC148835
0.8647 High Similarity NPC20511
0.8647 High Similarity NPC139548
0.8647 High Similarity NPC76336
0.8644 High Similarity NPC179309
0.864 High Similarity NPC41562
0.8636 High Similarity NPC208760
0.8629 High Similarity NPC199023
0.8629 High Similarity NPC60962
0.8629 High Similarity NPC109083
0.8629 High Similarity NPC224814
0.8629 High Similarity NPC189844
0.8629 High Similarity NPC14007
0.8629 High Similarity NPC269843
0.8618 High Similarity NPC181969
0.8618 High Similarity NPC320987
0.8615 High Similarity NPC73738
0.8605 High Similarity NPC476968
0.8605 High Similarity NPC170844
0.8594 High Similarity NPC74817
0.8594 High Similarity NPC324112
0.8594 High Similarity NPC282000
0.8594 High Similarity NPC266555
0.8594 High Similarity NPC293054
0.8594 High Similarity NPC236791
0.8594 High Similarity NPC124452
0.8594 High Similarity NPC246620
0.8594 High Similarity NPC82679
0.8594 High Similarity NPC210355
0.8594 High Similarity NPC127587
0.8594 High Similarity NPC159968
0.8594 High Similarity NPC169474
0.8583 High Similarity NPC234400
0.8583 High Similarity NPC60885
0.8571 High Similarity NPC136319
0.8571 High Similarity NPC78918
0.8571 High Similarity NPC282496
0.8571 High Similarity NPC126682
0.8571 High Similarity NPC84086
0.8571 High Similarity NPC203924
0.8571 High Similarity NPC233526
0.8571 High Similarity NPC139617
0.8571 High Similarity NPC82271
0.8571 High Similarity NPC95168
0.856 High Similarity NPC470804
0.856 High Similarity NPC285289
0.8559 High Similarity NPC246358
0.8559 High Similarity NPC36108
0.8559 High Similarity NPC165386
0.8559 High Similarity NPC7097
0.8559 High Similarity NPC233731
0.855 High Similarity NPC5423
0.8548 High Similarity NPC2058
0.8538 High Similarity NPC472338
0.8527 High Similarity NPC304747
0.8527 High Similarity NPC154866
0.8519 High Similarity NPC144284
0.8519 High Similarity NPC210478
0.8519 High Similarity NPC4796
0.8516 High Similarity NPC127604
0.8516 High Similarity NPC76451
0.8512 High Similarity NPC294941
0.8507 High Similarity NPC25305
0.8507 High Similarity NPC125417
0.8507 High Similarity NPC95679
0.8507 High Similarity NPC112068
0.8507 High Similarity NPC110899
0.8504 High Similarity NPC20443
0.8504 High Similarity NPC246704
0.8504 High Similarity NPC60517
0.8504 High Similarity NPC146886
0.8496 Intermediate Similarity NPC214729
0.8492 Intermediate Similarity NPC286573
0.8492 Intermediate Similarity NPC270326
0.8492 Intermediate Similarity NPC209567
0.848 Intermediate Similarity NPC158949
0.8473 Intermediate Similarity NPC470096
0.8473 Intermediate Similarity NPC472597
0.8473 Intermediate Similarity NPC470095
0.8473 Intermediate Similarity NPC474017
0.8468 Intermediate Similarity NPC135961
0.8462 Intermediate Similarity NPC470633
0.8462 Intermediate Similarity NPC228769
0.8462 Intermediate Similarity NPC212015
0.8462 Intermediate Similarity NPC58164
0.8462 Intermediate Similarity NPC10225
0.845 Intermediate Similarity NPC203719
0.845 Intermediate Similarity NPC117237
0.8438 Intermediate Similarity NPC105925
0.8438 Intermediate Similarity NPC87113
0.8438 Intermediate Similarity NPC289459
0.843 Intermediate Similarity NPC204120
0.8429 Intermediate Similarity NPC473408
0.8425 Intermediate Similarity NPC229084
0.8425 Intermediate Similarity NPC160900
0.8425 Intermediate Similarity NPC18984
0.8425 Intermediate Similarity NPC121115
0.8425 Intermediate Similarity NPC106659
0.8421 Intermediate Similarity NPC135127
0.8417 Intermediate Similarity NPC8547
0.8417 Intermediate Similarity NPC257124
0.8417 Intermediate Similarity NPC173746
0.8417 Intermediate Similarity NPC156840
0.8413 Intermediate Similarity NPC476343
0.8413 Intermediate Similarity NPC75713

  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 NPC271985 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
0.8605 High Similarity NPD3027 Phase 3
0.845 Intermediate Similarity NPD9494 Approved
0.8425 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8417 Intermediate Similarity NPD228 Approved
0.8134 Intermediate Similarity NPD1613 Approved
0.8134 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8106 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8074 Intermediate Similarity NPD230 Phase 1
0.803 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD2983 Phase 2
0.8 Intermediate Similarity NPD2982 Phase 2
0.7986 Intermediate Similarity NPD1653 Approved
0.7923 Intermediate Similarity NPD2981 Phase 2
0.7874 Intermediate Similarity NPD5536 Phase 2
0.7832 Intermediate Similarity NPD4357 Discontinued
0.777 Intermediate Similarity NPD1934 Approved
0.7761 Intermediate Similarity NPD3018 Phase 2
0.7733 Intermediate Similarity NPD3882 Suspended
0.771 Intermediate Similarity NPD422 Phase 1
0.7642 Intermediate Similarity NPD1358 Approved
0.7615 Intermediate Similarity NPD1357 Approved
0.76 Intermediate Similarity NPD2801 Approved
0.7586 Intermediate Similarity NPD1511 Approved
0.7538 Intermediate Similarity NPD1548 Phase 1
0.7483 Intermediate Similarity NPD1512 Approved
0.7483 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD9296 Approved
0.7448 Intermediate Similarity NPD2219 Phase 1
0.7444 Intermediate Similarity NPD1610 Phase 2
0.7438 Intermediate Similarity NPD1242 Phase 1
0.7422 Intermediate Similarity NPD5283 Phase 1
0.7413 Intermediate Similarity NPD7266 Discontinued
0.7394 Intermediate Similarity NPD1510 Phase 2
0.7388 Intermediate Similarity NPD9269 Phase 2
0.7386 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD1558 Phase 1
0.7357 Intermediate Similarity NPD1240 Approved
0.7347 Intermediate Similarity NPD5297 Approved
0.7343 Intermediate Similarity NPD1551 Phase 2
0.7319 Intermediate Similarity NPD4908 Phase 1
0.7313 Intermediate Similarity NPD3705 Approved
0.7305 Intermediate Similarity NPD447 Suspended
0.728 Intermediate Similarity NPD3134 Approved
0.7278 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD6166 Phase 2
0.7278 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD1607 Approved
0.7241 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD291 Approved
0.7234 Intermediate Similarity NPD943 Approved
0.7222 Intermediate Similarity NPD290 Approved
0.7214 Intermediate Similarity NPD3144 Approved
0.7214 Intermediate Similarity NPD3145 Approved
0.7214 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD6190 Approved
0.7208 Intermediate Similarity NPD3817 Phase 2
0.72 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD1652 Phase 2
0.7188 Intermediate Similarity NPD3818 Discontinued
0.7179 Intermediate Similarity NPD6234 Discontinued
0.7172 Intermediate Similarity NPD3540 Phase 1
0.7165 Intermediate Similarity NPD2684 Approved
0.7163 Intermediate Similarity NPD2674 Phase 3
0.7143 Intermediate Similarity NPD7054 Approved
0.7143 Intermediate Similarity NPD9545 Approved
0.7143 Intermediate Similarity NPD1465 Phase 2
0.7124 Intermediate Similarity NPD5090 Approved
0.7124 Intermediate Similarity NPD5089 Approved
0.7123 Intermediate Similarity NPD1549 Phase 2
0.7114 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD3620 Phase 2
0.7113 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD3022 Approved
0.7109 Intermediate Similarity NPD3021 Approved
0.7103 Intermediate Similarity NPD3539 Phase 1
0.7099 Intermediate Similarity NPD7472 Approved
0.7099 Intermediate Similarity NPD7074 Phase 3
0.7097 Intermediate Similarity NPD846 Approved
0.7097 Intermediate Similarity NPD940 Approved
0.7092 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD9268 Approved
0.708 Intermediate Similarity NPD4749 Approved
0.7078 Intermediate Similarity NPD37 Approved
0.7077 Intermediate Similarity NPD7843 Approved
0.707 Intermediate Similarity NPD919 Approved
0.7059 Intermediate Similarity NPD4675 Approved
0.7059 Intermediate Similarity NPD4678 Approved
0.7059 Intermediate Similarity NPD4380 Phase 2
0.7059 Intermediate Similarity NPD1091 Approved
0.7055 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD7157 Approved
0.7044 Intermediate Similarity NPD6232 Discontinued
0.7037 Intermediate Similarity NPD4626 Approved
0.7034 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6799 Approved
0.6993 Remote Similarity NPD4060 Phase 1
0.6985 Remote Similarity NPD3496 Discontinued
0.6981 Remote Similarity NPD1247 Approved
0.698 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6111 Discontinued
0.6959 Remote Similarity NPD3060 Approved
0.6951 Remote Similarity NPD6797 Phase 2
0.6949 Remote Similarity NPD9094 Approved
0.6944 Remote Similarity NPD5124 Phase 1
0.6944 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6943 Remote Similarity NPD4965 Approved
0.6943 Remote Similarity NPD4967 Phase 2
0.6943 Remote Similarity NPD4966 Approved
0.6933 Remote Similarity NPD5844 Phase 1
0.6923 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6914 Remote Similarity NPD7473 Discontinued
0.6913 Remote Similarity NPD3750 Approved
0.6913 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6913 Remote Similarity NPD4628 Phase 3
0.6912 Remote Similarity NPD1778 Approved
0.6909 Remote Similarity NPD7251 Discontinued
0.6901 Remote Similarity NPD4625 Phase 3
0.6899 Remote Similarity NPD7075 Discontinued
0.6894 Remote Similarity NPD1241 Discontinued
0.6883 Remote Similarity NPD824 Approved
0.6883 Remote Similarity NPD4005 Discontinued
0.6879 Remote Similarity NPD5353 Approved
0.6875 Remote Similarity NPD7199 Phase 2
0.6875 Remote Similarity NPD968 Approved
0.6871 Remote Similarity NPD2935 Discontinued
0.6871 Remote Similarity NPD7228 Approved
0.6867 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6867 Remote Similarity NPD7808 Phase 3
0.6848 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6846 Remote Similarity NPD4237 Approved
0.6846 Remote Similarity NPD4236 Phase 3
0.6842 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6838 Remote Similarity NPD5691 Approved
0.6831 Remote Similarity NPD1008 Clinical (unspecified phase)
0.6828 Remote Similarity NPD4340 Discontinued
0.6824 Remote Similarity NPD1375 Discontinued
0.6821 Remote Similarity NPD7124 Phase 2
0.6818 Remote Similarity NPD3686 Approved
0.6818 Remote Similarity NPD3687 Approved
0.6815 Remote Similarity NPD4585 Approved
0.6815 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6813 Remote Similarity NPD5494 Approved
0.6807 Remote Similarity NPD6559 Discontinued
0.6806 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6797 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4381 Clinical (unspecified phase)
0.679 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6788 Remote Similarity NPD9384 Approved
0.6788 Remote Similarity NPD9381 Approved
0.6766 Remote Similarity NPD7549 Discontinued
0.6763 Remote Similarity NPD9717 Approved
0.6761 Remote Similarity NPD2861 Phase 2
0.6757 Remote Similarity NPD2796 Approved
0.6741 Remote Similarity NPD9493 Approved
0.6732 Remote Similarity NPD4123 Phase 3
0.6732 Remote Similarity NPD2532 Approved
0.6732 Remote Similarity NPD2534 Approved
0.6732 Remote Similarity NPD2533 Approved
0.6731 Remote Similarity NPD6599 Discontinued
0.6718 Remote Similarity NPD4750 Phase 3
0.6718 Remote Similarity NPD556 Approved
0.6714 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6714 Remote Similarity NPD9622 Approved
0.6709 Remote Similarity NPD7819 Suspended
0.6707 Remote Similarity NPD7685 Pre-registration
0.6695 Remote Similarity NPD111 Approved
0.6692 Remote Similarity NPD9377 Approved
0.6692 Remote Similarity NPD821 Approved
0.6692 Remote Similarity NPD9379 Approved
0.6691 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6689 Remote Similarity NPD8166 Discontinued
0.6689 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6689 Remote Similarity NPD4110 Phase 3
0.6687 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6687 Remote Similarity NPD5242 Approved
0.6667 Remote Similarity NPD3866 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2492 Phase 1
0.6667 Remote Similarity NPD2424 Discontinued
0.6667 Remote Similarity NPD7095 Approved
0.6667 Remote Similarity NPD3225 Approved
0.6667 Remote Similarity NPD5402 Approved
0.6667 Remote Similarity NPD8651 Approved
0.6667 Remote Similarity NPD6671 Approved
0.6667 Remote Similarity NPD6653 Approved
0.6647 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6646 Remote Similarity NPD6801 Discontinued
0.6645 Remote Similarity NPD5403 Approved
0.6644 Remote Similarity NPD6100 Approved
0.6644 Remote Similarity NPD6099 Approved
0.6643 Remote Similarity NPD1608 Approved
0.6642 Remote Similarity NPD7533 Approved
0.6642 Remote Similarity NPD7534 Approved
0.6639 Remote Similarity NPD9365 Approved
0.6625 Remote Similarity NPD7768 Phase 2
0.6623 Remote Similarity NPD1424 Approved
0.6623 Remote Similarity NPD7410 Clinical (unspecified phase)

  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