Structure

Physi-Chem Properties

Molecular Weight:  174.15
Volume:  185.559
LogP:  -2.024
LogD:  -1.22
LogS:  0.299
# Rotatable Bonds:  2
TPSA:  29.46
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.607
Synthetic Accessibility Score:  4.218
Fsp3:  1.0
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:  -5.567
MDCK Permeability:  0.0003310595056973398
Pgp-inhibitor:  0.0
Pgp-substrate:  0.473
Human Intestinal Absorption (HIA):  0.806
20% Bioavailability (F20%):  0.977
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.209
Plasma Protein Binding (PPB):  12.359308242797852%
Volume Distribution (VD):  0.747
Pgp-substrate:  86.8924789428711%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.675
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.132
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.869
CYP3A4-inhibitor:  0.003
CYP3A4-substrate:  0.064

ADMET: Excretion

Clearance (CL):  4.32
Half-life (T1/2):  0.923

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.221
Drug-inuced Liver Injury (DILI):  0.006
AMES Toxicity:  0.027
Rat Oral Acute Toxicity:  0.437
Maximum Recommended Daily Dose:  0.893
Skin Sensitization:  0.255
Carcinogencity:  0.284
Eye Corrosion:  0.323
Eye Irritation:  0.493
Respiratory Toxicity:  0.917

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

  Natural Product: NPC293551

Natural Product ID:  NPC293551
Common Name*:   Muscarine
IUPAC Name:   [(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium
Synonyms:   L-(+)-muscarine; Muscarin
Standard InCHIKey:  UQOFGTXDASPNLL-XHNCKOQMSA-N
Standard InCHI:  InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1
SMILES:  O[C@@H]1C[C@H](O[C@H]1C)C[N+](C)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL12587
PubChem CID:   9308
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0001540] Monosaccharides
            • [CHEMONTID:0001497] Pentoses

*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
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np50031a011]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18303850]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18681481]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[19344127]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. aerial part n.a. PMID[21902175]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[26000707]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[32880179]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7513 Cannabis sativa Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7513 Cannabis sativa Species Cannabaceae 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
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus pD2 = 6.8 n.a. PMID[549494]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus Efficiency = 100.0 % PMID[549494]
NPT262 Individual Protein Muscarinic acetylcholine receptor M1 Homo sapiens Inhibition = 2.0 % PMID[549495]
NPT262 Individual Protein Muscarinic acetylcholine receptor M1 Homo sapiens Ki = 56.0 nM PMID[549495]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Ki = 25.0 nM PMID[549495]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Ki = 72.0 nM PMID[549495]
NPT264 Individual Protein Muscarinic acetylcholine receptor M3 Homo sapiens Inhibition = 28.0 % PMID[549495]
NPT265 Individual Protein Muscarinic acetylcholine receptor M4 Homo sapiens Ki = 1400.0 nM PMID[549495]
NPT265 Individual Protein Muscarinic acetylcholine receptor M4 Homo sapiens Ki = 23.0 nM PMID[549495]
NPT1301 Individual Protein Muscarinic acetylcholine receptor M2 Rattus norvegicus K app = 2.3 uM PMID[549497]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens PD2 = 6.69 n.a. PMID[549498]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Intrinsic activity = 1.0 n.a. PMID[549498]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus PD2 = 7.1 n.a. PMID[549498]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus Intrinsic activity = 1.0 n.a. PMID[549498]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus PD2 = 5.69 n.a. PMID[549498]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens ED50 = 0.0037 mg.kg-1 PMID[549498]
NPT262 Individual Protein Muscarinic acetylcholine receptor M1 Homo sapiens ED50 = 0.0025 mg.kg-1 PMID[549498]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens -Log ED50 = 6.42 n.a. PMID[549498]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens -Log KD = 4.61 n.a. PMID[549498]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens -Log KD = 4.7 n.a. PMID[549498]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus -Log KD = 5.95 n.a. PMID[549498]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus -Log KD = 4.62 n.a. PMID[549498]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Relative affinity = 1.0 n.a. PMID[549498]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus Relative affinity = 1.0 n.a. PMID[549498]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Receptor occupied = 1.52 % PMID[549498]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Receptor occupied = 1.01 % PMID[549498]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus Receptor occupied = 6.62 % PMID[549498]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus Receptor occupied = 7.85 % PMID[549498]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens pD2 = 6.69 n.a. PMID[549500]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Intrinsic activity = 1.0 n.a. PMID[549500]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus pD2 = 7.1 n.a. PMID[549500]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus Intrinsic activity = 1.0 n.a. PMID[549500]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus pD2 = 5.69 n.a. PMID[549500]
NPT1301 Individual Protein Muscarinic acetylcholine receptor M2 Rattus norvegicus ED50 = 0.0037 mg.kg-1 PMID[549500]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens -Log ED50 = 6.42 n.a. PMID[549500]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Relative efficacy = 1.0 n.a. PMID[549500]
NPT420 Individual Protein Muscarinic acetylcholine receptor M3 Cavia porcellus Relative efficacy = 1.0 n.a. PMID[549500]
NPT1301 Individual Protein Muscarinic acetylcholine receptor M2 Rattus norvegicus Ki = 75.0 nM PMID[549502]
NPT1303 Individual Protein Muscarinic acetylcholine receptor M3 Rattus norvegicus Inhibition = 28.0 % PMID[549502]
NPT432 Individual Protein Muscarinic acetylcholine receptor M4 Rattus norvegicus Ki = 1400.0 nM PMID[549502]
NPT1301 Individual Protein Muscarinic acetylcholine receptor M2 Rattus norvegicus IC50 = 490.0 nM PMID[549502]
NPT1301 Individual Protein Muscarinic acetylcholine receptor M2 Rattus norvegicus IC50 = 3900.0 nM PMID[549502]
NPT432 Individual Protein Muscarinic acetylcholine receptor M4 Rattus norvegicus IC50 = 470.0 nM PMID[549502]
NPT1303 Individual Protein Muscarinic acetylcholine receptor M3 Rattus norvegicus EC50 = 130.0 nM PMID[549502]
NPT262 Individual Protein Muscarinic acetylcholine receptor M1 Homo sapiens Inhibition = 15.0 % PMID[549503]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Ki = 75.0 nM PMID[549503]
NPT265 Individual Protein Muscarinic acetylcholine receptor M4 Homo sapiens Ki = 28000.0 nM PMID[549503]
NPT265 Individual Protein Muscarinic acetylcholine receptor M4 Homo sapiens Inhibition = 1.4 % PMID[549503]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens IC50 = 449.0 nM PMID[549503]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens IC50 = 3900.0 nM PMID[549503]
NPT262 Individual Protein Muscarinic acetylcholine receptor M1 Homo sapiens Ki = 18197.01 nM PMID[549505]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Ki = 489.78 nM PMID[549505]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 7943.3 nM PMID[549506]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 92.0 nM PMID[549507]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 15848.9 nM PMID[549507]
NPT104 Individual Protein Cerebroside-sulfatase Homo sapiens Potency n.a. 16944.1 nM PMID[549507]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus pD2 = 7.4 n.a. PMID[549494]
NPT422 Protein Family Muscarinic acetylcholine receptor Rattus norvegicus Efficiency = 100.0 % PMID[549494]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus pD2 = 5.9 n.a. PMID[549494]
NPT422 Protein Family Muscarinic acetylcholine receptor Rattus norvegicus IC50 = 12.0 nM PMID[549494]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus IC50 = 5680.0 nM PMID[549494]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Ratio = 473.0 n.a. PMID[549494]
NPT422 Protein Family Muscarinic acetylcholine receptor Rattus norvegicus Inhibition = 3.0 % PMID[549495]
NPT422 Protein Family Muscarinic acetylcholine receptor Rattus norvegicus Ki = 14.0 nM PMID[549495]
NPT2 Others Unspecified Ratio > 10000.0 n.a. PMID[549495]
NPT422 Protein Family Muscarinic acetylcholine receptor Rattus norvegicus Ki = 4400.0 nM PMID[549495]
NPT422 Protein Family Muscarinic acetylcholine receptor Rattus norvegicus Ki = 8.3 nM PMID[549495]
NPT422 Protein Family Muscarinic acetylcholine receptor Rattus norvegicus Ratio = 530.0 n.a. PMID[549495]
NPT938 Organism Cavia porcellus Cavia porcellus EC50 = 58.88 nM PMID[549496]
NPT938 Organism Cavia porcellus Cavia porcellus EC50 = 31.62 nM PMID[549496]
NPT2 Others Unspecified ER = 331.0 n.a. PMID[549496]
NPT29 Organism Rattus norvegicus Rattus norvegicus EC50 = 154.88 nM PMID[549496]
NPT29 Organism Rattus norvegicus Rattus norvegicus EC50 = 575.44 nM PMID[549496]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus K app = 28.0 uM PMID[549497]
NPT29 Organism Rattus norvegicus Rattus norvegicus EC50 = 169.82 nM PMID[549497]
NPT29 Organism Rattus norvegicus Rattus norvegicus FE = 1.1 n.a. PMID[549497]
NPT1300 Others Muscarinic acetylcholine receptors; M1 & M2 Homo sapiens K app ratio = 0.082 n.a. PMID[549497]
NPT938 Organism Cavia porcellus Cavia porcellus ED50 = 7.94 n.a. PMID[549499]
NPT2 Others Unspecified EPMR = 0.8 n.a. PMID[549499]
NPT2 Others Unspecified ED50 > 5.0 n.a. PMID[549499]
NPT2 Others Unspecified EPMR > 95.0 n.a. PMID[549499]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus ED50 = 0.0025 mg.kg-1 PMID[549500]
NPT938 Organism Cavia porcellus Cavia porcellus Kd = 19952.62 nM PMID[549500]
NPT938 Organism Cavia porcellus Cavia porcellus Kd = 24547.09 nM PMID[549500]
NPT938 Organism Cavia porcellus Cavia porcellus Kd = 1122.02 nM PMID[549500]
NPT938 Organism Cavia porcellus Cavia porcellus Kd = 23988.33 nM PMID[549500]
NPT938 Organism Cavia porcellus Cavia porcellus ED50 = 0.0000000794 n.a. PMID[549501]
NPT2 Others Unspecified Ratio = 0.4 n.a. PMID[549501]
NPT2 Others Unspecified ED50 > 0.0005 n.a. PMID[549501]
NPT2 Others Unspecified Ratio > 124.0 n.a. PMID[549501]
NPT2 Others Unspecified Ratio > 6300.0 n.a. PMID[549501]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Inhibition = 3.0 % PMID[549502]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Ki = 27.0 nM PMID[549502]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Inhibition = 15.0 % PMID[549502]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus EC50 = 219.0 nM PMID[549502]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Inhibition = 3.0 % PMID[549503]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Ki = 27.0 nM PMID[549503]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus pD2 = 6.8 n.a. PMID[549504]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Efficacy = 100.0 % PMID[549504]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus pD2 = 7.4 n.a. PMID[549504]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Ki = 12.0 nM PMID[549504]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Ki = 5680.0 nM PMID[549504]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Potency = 2511.9 nM PMID[549506]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 23778.1 nM PMID[549507]

☑ 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 NPC293551 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
0.7288 Intermediate Similarity NPC275727
0.7164 Intermediate Similarity NPC473419
0.7164 Intermediate Similarity NPC475715
0.7164 Intermediate Similarity NPC475127
0.7121 Intermediate Similarity NPC59221
0.7077 Intermediate Similarity NPC233034
0.7015 Intermediate Similarity NPC266242
0.7015 Intermediate Similarity NPC254617
0.7015 Intermediate Similarity NPC171850
0.7015 Intermediate Similarity NPC306763
0.7015 Intermediate Similarity NPC74555
0.7015 Intermediate Similarity NPC474469
0.7 Intermediate Similarity NPC315806
0.6866 Remote Similarity NPC184150
0.6866 Remote Similarity NPC141156
0.6812 Remote Similarity NPC163538
0.6812 Remote Similarity NPC115800
0.6769 Remote Similarity NPC17455
0.6765 Remote Similarity NPC126664
0.6765 Remote Similarity NPC34291
0.6716 Remote Similarity NPC294883
0.6716 Remote Similarity NPC12514
0.6667 Remote Similarity NPC471419
0.6667 Remote Similarity NPC163134
0.6615 Remote Similarity NPC474014
0.6615 Remote Similarity NPC57846
0.6615 Remote Similarity NPC30126
0.6562 Remote Similarity NPC471421
0.6562 Remote Similarity NPC170172
0.6562 Remote Similarity NPC233364
0.6508 Remote Similarity NPC10262
0.6508 Remote Similarity NPC311668
0.6508 Remote Similarity NPC65832
0.6486 Remote Similarity NPC329077
0.6462 Remote Similarity NPC201338
0.6462 Remote Similarity NPC328786
0.6462 Remote Similarity NPC474627
0.6406 Remote Similarity NPC204709
0.64 Remote Similarity NPC325902
0.6364 Remote Similarity NPC62507
0.6364 Remote Similarity NPC8087
0.6338 Remote Similarity NPC475694
0.6338 Remote Similarity NPC473710
0.6324 Remote Similarity NPC474928
0.6316 Remote Similarity NPC150557
0.629 Remote Similarity NPC272396
0.6234 Remote Similarity NPC100204
0.6234 Remote Similarity NPC83248
0.622 Remote Similarity NPC52533
0.619 Remote Similarity NPC471442
0.619 Remote Similarity NPC471423
0.6154 Remote Similarity NPC471420
0.6111 Remote Similarity NPC327753
0.6111 Remote Similarity NPC327486
0.6111 Remote Similarity NPC223174
0.6102 Remote Similarity NPC81384
0.6061 Remote Similarity NPC76726
0.6061 Remote Similarity NPC193593
0.6061 Remote Similarity NPC143809
0.6061 Remote Similarity NPC290106
0.6032 Remote Similarity NPC178263
0.6032 Remote Similarity NPC277072
0.6 Remote Similarity NPC238646
0.6 Remote Similarity NPC471605
0.6 Remote Similarity NPC101746
0.6 Remote Similarity NPC165119
0.6 Remote Similarity NPC69798
0.6 Remote Similarity NPC77191
0.6 Remote Similarity NPC116377
0.6 Remote Similarity NPC471443
0.6 Remote Similarity NPC473952
0.5974 Remote Similarity NPC233108
0.5972 Remote Similarity NPC268922
0.5946 Remote Similarity NPC474468
0.5904 Remote Similarity NPC210456
0.5904 Remote Similarity NPC163352
0.5873 Remote Similarity NPC470664
0.5873 Remote Similarity NPC325180
0.5873 Remote Similarity NPC35816
0.5857 Remote Similarity NPC160661
0.5854 Remote Similarity NPC325723
0.5843 Remote Similarity NPC313821
0.5833 Remote Similarity NPC471418
0.5833 Remote Similarity NPC328806
0.5823 Remote Similarity NPC70574
0.5811 Remote Similarity NPC137554
0.5811 Remote Similarity NPC299603
0.5811 Remote Similarity NPC255535
0.5811 Remote Similarity NPC476694
0.5811 Remote Similarity NPC476695
0.5811 Remote Similarity NPC476696
0.5811 Remote Similarity NPC285014
0.5811 Remote Similarity NPC28959
0.5806 Remote Similarity NPC27359
0.5806 Remote Similarity NPC295832
0.5806 Remote Similarity NPC198398
0.5806 Remote Similarity NPC224624
0.5802 Remote Similarity NPC93630
0.5797 Remote Similarity NPC306462
0.5797 Remote Similarity NPC69669
0.5797 Remote Similarity NPC2432
0.5797 Remote Similarity NPC150680
0.5797 Remote Similarity NPC22774
0.5797 Remote Similarity NPC218150
0.5783 Remote Similarity NPC43246
0.5783 Remote Similarity NPC89051
0.5781 Remote Similarity NPC270041
0.5775 Remote Similarity NPC303798
0.5775 Remote Similarity NPC286851
0.5775 Remote Similarity NPC315980
0.5769 Remote Similarity NPC314968
0.5769 Remote Similarity NPC314772
0.5758 Remote Similarity NPC8979
0.5732 Remote Similarity NPC112842
0.5732 Remote Similarity NPC71339
0.5714 Remote Similarity NPC190334
0.5714 Remote Similarity NPC306838
0.5714 Remote Similarity NPC62927
0.5714 Remote Similarity NPC3094
0.5696 Remote Similarity NPC316807
0.5696 Remote Similarity NPC98750
0.5694 Remote Similarity NPC322801
0.5694 Remote Similarity NPC129100
0.5694 Remote Similarity NPC291650
0.5692 Remote Similarity NPC471917
0.5679 Remote Similarity NPC271772
0.5679 Remote Similarity NPC81006
0.5679 Remote Similarity NPC288415
0.5679 Remote Similarity NPC31313
0.5679 Remote Similarity NPC45906
0.5679 Remote Similarity NPC36927
0.5679 Remote Similarity NPC319753
0.5679 Remote Similarity NPC149908
0.566 Remote Similarity NPC227267
0.5645 Remote Similarity NPC82512
0.5634 Remote Similarity NPC75435
0.5634 Remote Similarity NPC142290
0.5634 Remote Similarity NPC198341
0.5634 Remote Similarity NPC471780
0.5634 Remote Similarity NPC471892
0.5634 Remote Similarity NPC223386
0.5632 Remote Similarity NPC476019
0.5625 Remote Similarity NPC123814
0.5616 Remote Similarity NPC316445
0.561 Remote Similarity NPC106780
0.56 Remote Similarity NPC114640
0.56 Remote Similarity NPC170963
0.56 Remote Similarity NPC169976
0.56 Remote Similarity NPC33267
0.56 Remote Similarity NPC126366
0.56 Remote Similarity NPC324165

  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 NPC293551 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
0.7077 Intermediate Similarity NPD9440 Discontinued
0.7 Intermediate Similarity NPD9653 Clinical (unspecified phase)
0.6984 Remote Similarity NPD9240 Approved
0.6984 Remote Similarity NPD9239 Approved
0.6875 Remote Similarity NPD393 Approved
0.6842 Remote Similarity NPD883 Phase 2
0.6842 Remote Similarity NPD882 Phase 2
0.6765 Remote Similarity NPD9443 Clinical (unspecified phase)
0.6719 Remote Similarity NPD9455 Approved
0.6712 Remote Similarity NPD372 Clinical (unspecified phase)
0.6575 Remote Similarity NPD9407 Approved
0.6567 Remote Similarity NPD1457 Discontinued
0.6522 Remote Similarity NPD9444 Discontinued
0.6389 Remote Similarity NPD9405 Approved
0.6349 Remote Similarity NPD9659 Approved
0.6282 Remote Similarity NPD2691 Clinical (unspecified phase)
0.6234 Remote Similarity NPD9429 Discontinued
0.6176 Remote Similarity NPD9211 Clinical (unspecified phase)
0.6119 Remote Similarity NPD9022 Phase 2
0.6119 Remote Similarity NPD9024 Phase 2
0.6111 Remote Similarity NPD9445 Approved
0.6102 Remote Similarity NPD9463 Phase 3
0.6102 Remote Similarity NPD9462 Approved
0.6 Remote Similarity NPD6943 Clinical (unspecified phase)
0.5949 Remote Similarity NPD9558 Phase 3
0.5873 Remote Similarity NPD9660 Approved
0.5846 Remote Similarity NPD6950 Discontinued
0.5843 Remote Similarity NPD3189 Approved
0.5843 Remote Similarity NPD3190 Approved
0.5843 Remote Similarity NPD3191 Approved
0.5806 Remote Similarity NPD9226 Approved
0.5806 Remote Similarity NPD9225 Phase 3
0.5797 Remote Similarity NPD9028 Phase 2
0.5797 Remote Similarity NPD9026 Phase 2
0.5797 Remote Similarity NPD9029 Phase 3
0.5797 Remote Similarity NPD9027 Phase 3
0.5789 Remote Similarity NPD9457 Approved
0.5789 Remote Similarity NPD9456 Approved
0.5783 Remote Similarity NPD9581 Clinical (unspecified phase)
0.5783 Remote Similarity NPD9580 Clinical (unspecified phase)
0.5769 Remote Similarity NPD9435 Approved
0.5769 Remote Similarity NPD9434 Approved
0.5765 Remote Similarity NPD755 Phase 3
0.575 Remote Similarity NPD9556 Approved
0.5733 Remote Similarity NPD6704 Discontinued
0.5732 Remote Similarity NPD280 Approved
0.5714 Remote Similarity NPD11 Approved
0.5714 Remote Similarity NPD1760 Approved
0.5714 Remote Similarity NPD9604 Approved
0.5714 Remote Similarity NPD376 Approved
0.5714 Remote Similarity NPD9603 Phase 3
0.5714 Remote Similarity NPD9602 Phase 3
0.5694 Remote Similarity NPD9031 Approved
0.5694 Remote Similarity NPD9032 Approved
0.5694 Remote Similarity NPD9030 Approved
0.5694 Remote Similarity NPD9033 Approved
0.5679 Remote Similarity NPD9561 Approved
0.5679 Remote Similarity NPD9560 Approved
0.5679 Remote Similarity NPD9573 Phase 2
0.5672 Remote Similarity NPD9657 Discontinued
0.5634 Remote Similarity NPD4272 Discontinued
0.5625 Remote Similarity NPD3215 Phase 1
0.561 Remote Similarity NPD9546 Phase 2
0.561 Remote Similarity NPD9559 Phase 1

  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