Structure

Physi-Chem Properties

Molecular Weight:  228.08
Volume:  241.503
LogP:  3.65
LogD:  3.898
LogS:  -3.497
# Rotatable Bonds:  4
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.821
Synthetic Accessibility Score:  1.444
Fsp3:  0.071
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.601
MDCK Permeability:  3.233164534321986e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.202
30% Bioavailability (F30%):  0.763

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.552
Plasma Protein Binding (PPB):  97.6719970703125%
Volume Distribution (VD):  0.911
Pgp-substrate:  2.9865736961364746%

ADMET: Metabolism

CYP1A2-inhibitor:  0.983
CYP1A2-substrate:  0.162
CYP2C19-inhibitor:  0.959
CYP2C19-substrate:  0.069
CYP2C9-inhibitor:  0.754
CYP2C9-substrate:  0.192
CYP2D6-inhibitor:  0.685
CYP2D6-substrate:  0.242
CYP3A4-inhibitor:  0.102
CYP3A4-substrate:  0.221

ADMET: Excretion

Clearance (CL):  13.765
Half-life (T1/2):  0.803

ADMET: Toxicity

hERG Blockers:  0.039
Human Hepatotoxicity (H-HT):  0.025
Drug-inuced Liver Injury (DILI):  0.8
AMES Toxicity:  0.046
Rat Oral Acute Toxicity:  0.02
Maximum Recommended Daily Dose:  0.007
Skin Sensitization:  0.442
Carcinogencity:  0.479
Eye Corrosion:  0.143
Eye Irritation:  0.984
Respiratory Toxicity:  0.046

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC233282

Natural Product ID:  NPC233282
Common Name*:   Benzyl Salicylate
IUPAC Name:   benzyl 2-hydroxybenzoate
Synonyms:   Benzyl Salicylate
Standard InCHIKey:  ZCTQGTTXIYCGGC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H12O3/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9,15H,10H2
SMILES:  O=C(c1ccccc1O)OCc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL460124
PubChem CID:   8363
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001350] Benzoic acid esters
            • [CHEMONTID:0004700] o-Hydroxybenzoic acid esters

*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
NPO22583 Daedaleopsis confragosa Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[11014261]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. PMID[15387653]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. PMID[17711348]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. PMID[19919067]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. The fungus is isolated from the leaves of L. rhodostegia, collected in June 2007 at Nanning, Guangxi Province, China 2007-JUN PMID[20550196]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. PMID[22325941]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. PMID[24328302]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24471493]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28116906]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. aerial part n.a. PMID[7764590]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24284 Hypoestes serpens Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11614 Dianthus chinensis Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16234 Orgyia australis postica Species Lymantriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24173 Plutella xylostella Species Plutellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22583 Daedaleopsis confragosa Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24284 Hypoestes serpens Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24329 Primula farinosa Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20617 Tilletia laevis Species Tilletiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24216 Lolium perenne Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23916 Anthocleista grandiflora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23957 Helleborus caucasicus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23323 Dianthus superbus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17647 Schkuhria multiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ 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
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 31622.8 nM PMID[455578]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 79432.8 nM PMID[455579]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 50118.7 nM PMID[455579]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 32629.4 nM PMID[455579]
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency n.a. 5011.9 nM PMID[455580]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 56234.1 nM PMID[455579]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 47307.9 nM PMID[455578]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 145.8 nM PMID[455579]
NPT103 Individual Protein Nuclear receptor ROR-gamma Homo sapiens Potency n.a. 13333.2 nM PMID[455578]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 54578.2 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 54578.2 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 54947.7 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 19365.1 nM PubChem BioAssay data set
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 61652.4 nM PubChem BioAssay data set
NPT2557 Organism Dermatophagoides pteronyssinus Dermatophagoides pteronyssinus EC50 = 0.025 g/m2 PMID[455577]
NPT2 Others Unspecified Potency = 31622.8 nM PMID[455578]
NPT2 Others Unspecified Potency n.a. 29092.9 nM PMID[455579]
NPT98 Individual Protein HERG Homo sapiens Potency n.a. 39810.7 nM PMID[455578]
NPT35 Others n.a. LogP = 4.31 n.a. PMID[455581]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = -34.0 % PMID[455581]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = -29.0 % PMID[455581]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 29.0 % PMID[455581]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 46.0 % PMID[455581]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 25.0 % PMID[455581]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 78.0 % PMID[455581]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 74.0 % PMID[455581]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 65.0 % PMID[455581]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 94.0 % PMID[455581]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Repellency = 99.0 % PMID[455581]
NPT29 Organism Rattus norvegicus Rattus norvegicus pLD50 = 7.71 n.a. PMID[455582]
NPT191 Organism Hepatitis C virus Hepatitis C virus Inhibition = 25.0 % PMID[455583]
NPT2 Others Unspecified Potency n.a. 28183.8 nM PMID[455579]
NPT2 Others Unspecified Potency n.a. 15848.9 nM PMID[455579]
NPT2 Others Unspecified Potency n.a. 61237.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24336.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 5494.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27111.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76411.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54578.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 30899.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68101.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19193.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1089 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 9619.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12197.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19496.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 7695.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 7641.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 17106.4 nM PubChem BioAssay data set

☑ 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 NPC233282 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
0.9646 High Similarity NPC94637
0.9561 High Similarity NPC328459
0.9561 High Similarity NPC90522
0.9492 High Similarity NPC4164
0.9478 High Similarity NPC72977
0.9469 High Similarity NPC128825
0.8952 High Similarity NPC12694
0.8929 High Similarity NPC100551
0.8889 High Similarity NPC217423
0.8889 High Similarity NPC45104
0.877 High Similarity NPC193805
0.877 High Similarity NPC91475
0.877 High Similarity NPC265910
0.876 High Similarity NPC311219
0.8718 High Similarity NPC188907
0.8707 High Similarity NPC211421
0.8629 High Similarity NPC95309
0.8583 High Similarity NPC214702
0.8583 High Similarity NPC470831
0.8571 High Similarity NPC238309
0.856 High Similarity NPC181715
0.856 High Similarity NPC71525
0.8525 High Similarity NPC198336
0.8512 High Similarity NPC230951
0.8509 High Similarity NPC141523
0.8509 High Similarity NPC303264
0.85 High Similarity NPC184527
0.85 High Similarity NPC94298
0.85 High Similarity NPC27633
0.8487 Intermediate Similarity NPC128249
0.8475 Intermediate Similarity NPC81808
0.8473 Intermediate Similarity NPC261292
0.8473 Intermediate Similarity NPC301915
0.8468 Intermediate Similarity NPC6888
0.8455 Intermediate Similarity NPC217756
0.8455 Intermediate Similarity NPC244351
0.8455 Intermediate Similarity NPC283514
0.845 Intermediate Similarity NPC43627
0.845 Intermediate Similarity NPC200422
0.845 Intermediate Similarity NPC287533
0.845 Intermediate Similarity NPC157478
0.845 Intermediate Similarity NPC289572
0.845 Intermediate Similarity NPC472591
0.845 Intermediate Similarity NPC295406
0.8438 Intermediate Similarity NPC7012
0.8435 Intermediate Similarity NPC224584
0.8435 Intermediate Similarity NPC206341
0.8417 Intermediate Similarity NPC125252
0.8413 Intermediate Similarity NPC264428
0.839 Intermediate Similarity NPC223004
0.8385 Intermediate Similarity NPC474097
0.8359 Intermediate Similarity NPC307732
0.8359 Intermediate Similarity NPC42292
0.8346 Intermediate Similarity NPC19622
0.8346 Intermediate Similarity NPC112789
0.8333 Intermediate Similarity NPC131192
0.8333 Intermediate Similarity NPC312800
0.8321 Intermediate Similarity NPC142027
0.8321 Intermediate Similarity NPC29317
0.8321 Intermediate Similarity NPC27407
0.8321 Intermediate Similarity NPC229638
0.8321 Intermediate Similarity NPC267539
0.8321 Intermediate Similarity NPC176102
0.8321 Intermediate Similarity NPC204257
0.8321 Intermediate Similarity NPC254832
0.8321 Intermediate Similarity NPC71108
0.832 Intermediate Similarity NPC184219
0.832 Intermediate Similarity NPC236189
0.8306 Intermediate Similarity NPC46634
0.8293 Intermediate Similarity NPC297186
0.8284 Intermediate Similarity NPC275903
0.8284 Intermediate Similarity NPC155205
0.8281 Intermediate Similarity NPC197425
0.8279 Intermediate Similarity NPC201284
0.8279 Intermediate Similarity NPC184579
0.8279 Intermediate Similarity NPC195262
0.8279 Intermediate Similarity NPC188814
0.8279 Intermediate Similarity NPC233165
0.8268 Intermediate Similarity NPC22783
0.8258 Intermediate Similarity NPC291454
0.8254 Intermediate Similarity NPC287473
0.824 Intermediate Similarity NPC93730
0.8235 Intermediate Similarity NPC53953
0.8235 Intermediate Similarity NPC279916
0.8231 Intermediate Similarity NPC313618
0.8231 Intermediate Similarity NPC64359
0.8231 Intermediate Similarity NPC308037
0.8231 Intermediate Similarity NPC262359
0.8226 Intermediate Similarity NPC224273
0.8226 Intermediate Similarity NPC19174
0.8226 Intermediate Similarity NPC73532
0.8226 Intermediate Similarity NPC115159
0.8226 Intermediate Similarity NPC143427
0.8226 Intermediate Similarity NPC156139
0.8226 Intermediate Similarity NPC45438
0.8226 Intermediate Similarity NPC267552
0.8226 Intermediate Similarity NPC314329
0.822 Intermediate Similarity NPC158282
0.8217 Intermediate Similarity NPC39753
0.8217 Intermediate Similarity NPC115998
0.8214 Intermediate Similarity NPC118343
0.8203 Intermediate Similarity NPC95537
0.8203 Intermediate Similarity NPC2596
0.8203 Intermediate Similarity NPC293453
0.8197 Intermediate Similarity NPC241089
0.8197 Intermediate Similarity NPC32298
0.8195 Intermediate Similarity NPC240593
0.8195 Intermediate Similarity NPC62907
0.819 Intermediate Similarity NPC260952
0.8175 Intermediate Similarity NPC4012
0.8168 Intermediate Similarity NPC212631
0.8168 Intermediate Similarity NPC205468
0.8168 Intermediate Similarity NPC257756
0.8168 Intermediate Similarity NPC87231
0.8168 Intermediate Similarity NPC129132
0.8168 Intermediate Similarity NPC153783
0.8167 Intermediate Similarity NPC276111
0.8167 Intermediate Similarity NPC118288
0.816 Intermediate Similarity NPC67300
0.816 Intermediate Similarity NPC133909
0.816 Intermediate Similarity NPC32032
0.8154 Intermediate Similarity NPC198249
0.8154 Intermediate Similarity NPC137264
0.8145 Intermediate Similarity NPC26433
0.8145 Intermediate Similarity NPC115188
0.8145 Intermediate Similarity NPC159760
0.8145 Intermediate Similarity NPC272454
0.8145 Intermediate Similarity NPC301987
0.8145 Intermediate Similarity NPC244994
0.8145 Intermediate Similarity NPC222876
0.8145 Intermediate Similarity NPC179092
0.8145 Intermediate Similarity NPC292665
0.8145 Intermediate Similarity NPC35856
0.8145 Intermediate Similarity NPC178395
0.8142 Intermediate Similarity NPC42211
0.814 Intermediate Similarity NPC78662
0.814 Intermediate Similarity NPC8005
0.814 Intermediate Similarity NPC60558
0.814 Intermediate Similarity NPC214246
0.8136 Intermediate Similarity NPC183700
0.8134 Intermediate Similarity NPC197666
0.8134 Intermediate Similarity NPC126739
0.8134 Intermediate Similarity NPC84585
0.8134 Intermediate Similarity NPC290291
0.8134 Intermediate Similarity NPC188879
0.8134 Intermediate Similarity NPC476480
0.8134 Intermediate Similarity NPC275055
0.8134 Intermediate Similarity NPC221104
0.813 Intermediate Similarity NPC54243
0.813 Intermediate Similarity NPC35744
0.812 Intermediate Similarity NPC235115
0.812 Intermediate Similarity NPC234560
0.812 Intermediate Similarity NPC39426
0.8115 Intermediate Similarity NPC240664
0.811 Intermediate Similarity NPC240744
0.811 Intermediate Similarity NPC167055
0.8106 Intermediate Similarity NPC56031
0.8106 Intermediate Similarity NPC472365
0.8106 Intermediate Similarity NPC242294
0.8106 Intermediate Similarity NPC57601
0.8106 Intermediate Similarity NPC263670
0.8106 Intermediate Similarity NPC337373
0.8106 Intermediate Similarity NPC192304
0.8106 Intermediate Similarity NPC312318
0.8106 Intermediate Similarity NPC139813
0.8106 Intermediate Similarity NPC188646
0.8106 Intermediate Similarity NPC175098
0.8092 Intermediate Similarity NPC186097
0.8092 Intermediate Similarity NPC475009
0.8092 Intermediate Similarity NPC475008
0.8092 Intermediate Similarity NPC470160
0.8092 Intermediate Similarity NPC113006
0.8088 Intermediate Similarity NPC470842
0.8088 Intermediate Similarity NPC130485
0.808 Intermediate Similarity NPC242895
0.808 Intermediate Similarity NPC196976
0.8077 Intermediate Similarity NPC278787
0.8077 Intermediate Similarity NPC185497
0.8077 Intermediate Similarity NPC7569
0.8077 Intermediate Similarity NPC31539
0.8074 Intermediate Similarity NPC472460
0.8074 Intermediate Similarity NPC280284
0.8074 Intermediate Similarity NPC99333
0.8074 Intermediate Similarity NPC124269
0.8074 Intermediate Similarity NPC188947
0.8074 Intermediate Similarity NPC329225
0.8074 Intermediate Similarity NPC134969
0.8074 Intermediate Similarity NPC52358
0.8074 Intermediate Similarity NPC147686
0.8067 Intermediate Similarity NPC114682
0.8065 Intermediate Similarity NPC470092
0.8065 Intermediate Similarity NPC473662
0.8065 Intermediate Similarity NPC474874
0.8065 Intermediate Similarity NPC260837
0.8065 Intermediate Similarity NPC216297
0.8065 Intermediate Similarity NPC7151
0.8062 Intermediate Similarity NPC80694
0.8062 Intermediate Similarity NPC186098
0.806 Intermediate Similarity NPC87545
0.806 Intermediate Similarity NPC235428

  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 NPC233282 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
0.9469 High Similarity NPD9493 Approved
0.9167 High Similarity NPD1203 Approved
0.8929 High Similarity NPD9266 Approved
0.8929 High Similarity NPD74 Approved
0.8839 High Similarity NPD9263 Approved
0.8839 High Similarity NPD9267 Approved
0.8839 High Similarity NPD9264 Approved
0.876 High Similarity NPD9717 Approved
0.8615 High Similarity NPD1551 Phase 2
0.85 High Similarity NPD9545 Approved
0.8492 Intermediate Similarity NPD6832 Phase 2
0.8482 Intermediate Similarity NPD9261 Approved
0.84 Intermediate Similarity NPD1164 Approved
0.8333 Intermediate Similarity NPD2935 Discontinued
0.8319 Intermediate Similarity NPD9281 Approved
0.8295 Intermediate Similarity NPD520 Approved
0.8231 Intermediate Similarity NPD1240 Approved
0.8226 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD1238 Approved
0.8189 Intermediate Similarity NPD1019 Discontinued
0.8168 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD1510 Phase 2
0.8106 Intermediate Similarity NPD1607 Approved
0.8077 Intermediate Similarity NPD411 Approved
0.8077 Intermediate Similarity NPD2313 Discontinued
0.8074 Intermediate Similarity NPD1549 Phase 2
0.803 Intermediate Similarity NPD1933 Approved
0.803 Intermediate Similarity NPD447 Suspended
0.8 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7969 Intermediate Similarity NPD2797 Approved
0.7956 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD2798 Approved
0.7886 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD4308 Phase 3
0.7852 Intermediate Similarity NPD2799 Discontinued
0.781 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD3764 Approved
0.7795 Intermediate Similarity NPD1201 Approved
0.7786 Intermediate Similarity NPD6799 Approved
0.7752 Intermediate Similarity NPD3225 Approved
0.7746 Intermediate Similarity NPD5403 Approved
0.773 Intermediate Similarity NPD5401 Approved
0.7698 Intermediate Similarity NPD3750 Approved
0.7692 Intermediate Similarity NPD1470 Approved
0.7669 Intermediate Similarity NPD3268 Approved
0.7655 Intermediate Similarity NPD7411 Suspended
0.763 Intermediate Similarity NPD230 Phase 1
0.7626 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD1894 Discontinued
0.7609 Intermediate Similarity NPD2344 Approved
0.7609 Intermediate Similarity NPD2346 Discontinued
0.7597 Intermediate Similarity NPD1481 Phase 2
0.7568 Intermediate Similarity NPD7768 Phase 2
0.7556 Intermediate Similarity NPD943 Approved
0.7556 Intermediate Similarity NPD4307 Phase 2
0.7537 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD2796 Approved
0.7536 Intermediate Similarity NPD5408 Approved
0.7536 Intermediate Similarity NPD5404 Approved
0.7536 Intermediate Similarity NPD5405 Approved
0.7536 Intermediate Similarity NPD5406 Approved
0.7519 Intermediate Similarity NPD1535 Discovery
0.7517 Intermediate Similarity NPD7075 Discontinued
0.75 Intermediate Similarity NPD9258 Approved
0.75 Intermediate Similarity NPD1241 Discontinued
0.75 Intermediate Similarity NPD9256 Approved
0.7483 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD1237 Approved
0.7466 Intermediate Similarity NPD6599 Discontinued
0.7466 Intermediate Similarity NPD4380 Phase 2
0.7456 Intermediate Similarity NPD1202 Approved
0.7447 Intermediate Similarity NPD1196 Approved
0.7432 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD7819 Suspended
0.7424 Intermediate Similarity NPD3266 Approved
0.7424 Intermediate Similarity NPD3267 Approved
0.7417 Intermediate Similarity NPD9697 Approved
0.7413 Intermediate Similarity NPD1511 Approved
0.7397 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD2309 Approved
0.7385 Intermediate Similarity NPD422 Phase 1
0.7383 Intermediate Similarity NPD5402 Approved
0.7376 Intermediate Similarity NPD1195 Approved
0.7365 Intermediate Similarity NPD6801 Discontinued
0.7361 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD968 Approved
0.7343 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD7033 Discontinued
0.7338 Intermediate Similarity NPD3748 Approved
0.7328 Intermediate Similarity NPD1608 Approved
0.7324 Intermediate Similarity NPD7003 Approved
0.7324 Intermediate Similarity NPD4628 Phase 3
0.731 Intermediate Similarity NPD1512 Approved
0.7292 Intermediate Similarity NPD1543 Discontinued
0.7285 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD3749 Approved
0.7285 Intermediate Similarity NPD955 Approved
0.7279 Intermediate Similarity NPD3226 Approved
0.7279 Intermediate Similarity NPD6798 Discontinued
0.7258 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD1243 Approved
0.7248 Intermediate Similarity NPD1934 Approved
0.7241 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD2182 Approved
0.7231 Intermediate Similarity NPD1778 Approved
0.7226 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7440 Discontinued
0.7219 Intermediate Similarity NPD3882 Suspended
0.7218 Intermediate Similarity NPD1283 Approved
0.7214 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD3134 Approved
0.7209 Intermediate Similarity NPD1759 Phase 1
0.7209 Intermediate Similarity NPD1548 Phase 1
0.72 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD3972 Approved
0.719 Intermediate Similarity NPD164 Approved
0.7185 Intermediate Similarity NPD9494 Approved
0.7181 Intermediate Similarity NPD2366 Approved
0.7154 Intermediate Similarity NPD1358 Approved
0.7152 Intermediate Similarity NPD3817 Phase 2
0.7152 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD920 Approved
0.7143 Intermediate Similarity NPD9257 Approved
0.7143 Intermediate Similarity NPD9279 Approved
0.7143 Intermediate Similarity NPD9259 Approved
0.7132 Intermediate Similarity NPD1758 Phase 1
0.7123 Intermediate Similarity NPD4662 Approved
0.7123 Intermediate Similarity NPD2532 Approved
0.7123 Intermediate Similarity NPD2534 Approved
0.7123 Intermediate Similarity NPD2533 Approved
0.7123 Intermediate Similarity NPD4661 Approved
0.7122 Intermediate Similarity NPD6355 Discontinued
0.7105 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6233 Phase 2
0.7099 Intermediate Similarity NPD17 Approved
0.709 Intermediate Similarity NPD1876 Approved
0.7086 Intermediate Similarity NPD2801 Approved
0.708 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD9269 Phase 2
0.7067 Intermediate Similarity NPD5889 Approved
0.7067 Intermediate Similarity NPD5890 Approved
0.7059 Intermediate Similarity NPD9495 Approved
0.7049 Intermediate Similarity NPD5909 Discontinued
0.7047 Intermediate Similarity NPD7458 Discontinued
0.7047 Intermediate Similarity NPD3455 Phase 2
0.7045 Intermediate Similarity NPD3496 Discontinued
0.7045 Intermediate Similarity NPD3847 Discontinued
0.7042 Intermediate Similarity NPD4477 Approved
0.7042 Intermediate Similarity NPD4476 Approved
0.7034 Intermediate Similarity NPD6190 Approved
0.7031 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD9268 Approved
0.7023 Intermediate Similarity NPD5585 Approved
0.7023 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD290 Approved
0.7007 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5953 Discontinued
0.7 Intermediate Similarity NPD1184 Approved
0.6992 Remote Similarity NPD1281 Approved
0.6992 Remote Similarity NPD1610 Phase 2
0.6987 Remote Similarity NPD6232 Discontinued
0.6985 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7286 Phase 2
0.6978 Remote Similarity NPD4062 Phase 3
0.6972 Remote Similarity NPD651 Clinical (unspecified phase)
0.6967 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6967 Remote Similarity NPD1930 Approved
0.6967 Remote Similarity NPD1929 Approved
0.6966 Remote Similarity NPD6398 Clinical (unspecified phase)
0.696 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6273 Approved
0.6957 Remote Similarity NPD7008 Discontinued
0.6949 Remote Similarity NPD2934 Approved
0.6949 Remote Similarity NPD2933 Approved
0.6944 Remote Similarity NPD75 Approved
0.6944 Remote Similarity NPD9277 Approved
0.6934 Remote Similarity NPD454 Approved
0.6928 Remote Similarity NPD2379 Clinical (unspecified phase)
0.6918 Remote Similarity NPD3818 Discontinued
0.6918 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6918 Remote Similarity NPD2354 Approved
0.6908 Remote Similarity NPD6844 Discontinued
0.6906 Remote Similarity NPD1296 Phase 2
0.6899 Remote Similarity NPD5951 Approved
0.6891 Remote Similarity NPD2859 Approved
0.6891 Remote Similarity NPD2860 Approved
0.6889 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6887 Remote Similarity NPD6585 Discontinued
0.6879 Remote Similarity NPD4618 Approved
0.6879 Remote Similarity NPD4622 Approved
0.6875 Remote Similarity NPD9278 Suspended
0.6875 Remote Similarity NPD9274 Approved
0.6875 Remote Similarity NPD9275 Approved
0.6875 Remote Similarity NPD9276 Approved
0.6866 Remote Similarity NPD6287 Discontinued
0.6861 Remote Similarity NPD5647 Approved

  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