Structure

Physi-Chem Properties

Molecular Weight:  154.03
Volume:  145.687
LogP:  1.63
LogD:  1.422
LogS:  -1.715
# Rotatable Bonds:  1
TPSA:  77.76
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.559
Synthetic Accessibility Score:  1.771
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.459
MDCK Permeability:  5.312598204909591e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.267
30% Bioavailability (F30%):  0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.138
Plasma Protein Binding (PPB):  51.21785354614258%
Volume Distribution (VD):  0.355
Pgp-substrate:  41.70699691772461%

ADMET: Metabolism

CYP1A2-inhibitor:  0.052
CYP1A2-substrate:  0.082
CYP2C19-inhibitor:  0.039
CYP2C19-substrate:  0.046
CYP2C9-inhibitor:  0.172
CYP2C9-substrate:  0.194
CYP2D6-inhibitor:  0.027
CYP2D6-substrate:  0.141
CYP3A4-inhibitor:  0.076
CYP3A4-substrate:  0.039

ADMET: Excretion

Clearance (CL):  11.11
Half-life (T1/2):  0.941

ADMET: Toxicity

hERG Blockers:  0.041
Human Hepatotoxicity (H-HT):  0.548
Drug-inuced Liver Injury (DILI):  0.864
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.214
Maximum Recommended Daily Dose:  0.007
Skin Sensitization:  0.252
Carcinogencity:  0.044
Eye Corrosion:  0.035
Eye Irritation:  0.959
Respiratory Toxicity:  0.505

Download Data

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

  Natural Product: NPC241089

Natural Product ID:  NPC241089
Common Name*:   2,4-Dihydroxybenzoic Acid
IUPAC Name:   2,4-dihydroxybenzoic acid
Synonyms:   2,4-Dihydroxy-Benzoic Acid; 2,4-Dihydroxybenzoic Acid; Beta-Resorcylic Acid
Standard InCHIKey:  UIAFKZKHHVMJGS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H6O4/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,8-9H,(H,10,11)
SMILES:  Oc1ccc(c(c1)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL328910
PubChem CID:   1491
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*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
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. whole plant n.a. DOI[10.1007/BF02329610]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. root n.a. DOI[10.1016/0031-9422(95)00135-T]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota Fruit n.a. n.a. DOI[10.1016/S0963-9969(99)00095-2]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota Ripe fruits n.a. n.a. PMID[11000024]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. fruit n.a. PMID[12802735]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[15270561]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. root n.a. PMID[16564530]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. fruit n.a. PMID[18384095]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota n.a. fruit n.a. PMID[21648406]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. fruit n.a. PMID[22014120]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. leaf n.a. PMID[22014120]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. leaf n.a. PMID[22014168]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Wood n.a. n.a. PMID[23113717]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[23540838]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[24295708]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. leaf n.a. PMID[25102361]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. fruit n.a. PMID[25306330]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[29359942]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[31944695]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota Roots; Tubers n.a. n.a. PMID[7714535]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. formosan n.a. PMID[8864236]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO28608 Olea europaea Species Oleaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO28608 Olea europaea Species Oleaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota Fruits n.a. Database[FooDB]
NPO30242 Sterculia lychnophora Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28231 Abelmoschus manihot Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4916 Toxicodendron vernicifluum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28231 Abelmoschus manihot Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21818 Vaccinium macrocarpon Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30242 Sterculia lychnophora Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4916 Toxicodendron vernicifluum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29417 Fallopia multiflora Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28231 Abelmoschus manihot Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4916 Toxicodendron vernicifluum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28608 Olea europaea Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28231 Abelmoschus manihot Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21818 Vaccinium macrocarpon Species Ericaceae 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
NPO28608 NPC241089 Oil n.a. 0.00481575 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO21818 NPC241089 Raw n.a. 0.806999981 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO28608 NPC241089 Raw n.a. 0.213999997 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO21818 NPC241089 Raw n.a. 4.25 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO21818 NPC241089 n.a. Fruits 0.8 n.a. n.a. mg/100g of FW Database [Phenol-Explorer]
NPO21818 NPC241089 n.a. Fruits 4.25 n.a. n.a. mg/100g of FW 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
NPT347 Cell Line Lymphoblastoid cells Homo sapiens Potency = 31.6 nM PMID[571552]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 3162.3 nM PMID[571552]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 7943.3 nM PMID[571553]
NPT347 Cell Line Lymphoblastoid cells Homo sapiens Potency = 31622.8 nM PMID[571553]
NPT280 Individual Protein Matrix metalloproteinase 9 Homo sapiens Inhibition = -8.0 % PMID[571555]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Inhibition = -62.0 % PMID[571555]
NPT270 Individual Protein Nitric oxide synthase, inducible Mus musculus Inhibition = 16.0 % PMID[571555]
NPT569 Individual Protein Matrix metalloproteinase 8 Homo sapiens Inhibition = -1.0 % PMID[571555]
NPT567 Individual Protein Matrix metalloproteinase 3 Homo sapiens Inhibition = 3.0 % PMID[571555]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens Inhibition = -7.0 % PMID[571555]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Inhibition = 7.0 % PMID[571555]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 91.0 % PMID[571555]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 580.2 nM PMID[571554]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 63095.7 nM PMID[571554]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 39.8 nM PMID[571553]
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 125.9 nM PMID[571552]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 18356.4 nM PMID[571554]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 66824.2 nM PMID[571552]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 28183.8 nM PMID[571554]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ki = 4900.0 nM PMID[571558]
NPT446 Individual Protein Rap guanine nucleotide exchange factor 3 Homo sapiens Potency n.a. 79432.8 nM PMID[571554]
NPT441 Individual Protein Cytochrome P450 19A1 Homo sapiens Activity = 93.9 % PMID[571560]
NPT1598 Individual Protein Casein kinase II alpha Homo sapiens Delta Tm = 3.2 degrees C PMID[571563]
NPT27 Others Unspecified IC50 = 22000000.0 nM PMID[571547]
NPT2 Others Unspecified Activity = 91.0 % PMID[571548]
NPT2 Others Unspecified IC50 = 30500000.0 nM PMID[571549]
NPT2 Others Unspecified IC50 = 33113112148.26 nM PMID[571549]
NPT2 Others Unspecified Inhibition = 47.7 % PMID[571551]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 25118.9 nM PMID[571553]
NPT2 Others Unspecified Potency = 1158.2 nM PMID[571554]
NPT69 Individual Protein Matrix metalloproteinase-1 Homo sapiens Inhibition = 14.0 % PMID[571555]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 2936.2 nM PMID[571554]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens Potency n.a. 50118.7 nM PMID[571553]
NPT2 Others Unspecified Potency n.a. 7079.5 nM PMID[571554]
NPT2 Others Unspecified Potency n.a. 2511.9 nM PMID[571554]
NPT2 Others Unspecified IC50 > 100000.0 nM PMID[571556]
NPT954 Individual Protein Carbonic anhydrase XIV Homo sapiens Ki = 70000.0 nM PMID[571558]
NPT949 Individual Protein Carbonic anhydrase XII Homo sapiens Ki = 7500.0 nM PMID[571558]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens Ki = 68000.0 nM PMID[571558]
NPT955 Individual Protein Carbonic anhydrase VII Homo sapiens Ki = 72000.0 nM PMID[571558]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ki = 5200.0 nM PMID[571558]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 1158.2 nM PMID[571554]
NPT2 Others Unspecified Activity = 76.0 % PMID[571559]
NPT35 Others n.a. LogD = -1.5 n.a. PMID[571561]
NPT35 Others n.a. LogP = 1.6 n.a. PMID[571561]
NPT35 Others n.a. pKa = 4.7 n.a. PMID[571561]
NPT35 Others n.a. pKa = 3.1 n.a. PMID[571561]
NPT2 Others Unspecified FC = -1.0 n.a. PMID[571561]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei EC50 = 17100.0 nM PMID[571562]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei EC50 = 19000.0 nM PMID[571562]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei Ratio EC50 = 1.11 n.a. PMID[571562]
NPT2 Others Unspecified IC50 = 116000.0 nM PMID[571562]
NPT2 Others Unspecified IC50 = 116000.0 nM PMID[571564]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei EC50 = 17100.0 nM PMID[571564]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei EC50 = 16600.0 nM PMID[571564]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei Ratio EC50 = 0.96 n.a. PMID[571564]
NPT2 Others Unspecified Potency n.a. 613.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 9817.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 779.9 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 NPC241089 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
0.9545 High Similarity NPC223004
0.9298 High Similarity NPC283844
0.9244 High Similarity NPC95309
0.9217 High Similarity NPC161617
0.9211 High Similarity NPC230349
0.9145 High Similarity NPC143427
0.9145 High Similarity NPC115159
0.9145 High Similarity NPC45438
0.9145 High Similarity NPC267552
0.9145 High Similarity NPC73532
0.9145 High Similarity NPC19174
0.9145 High Similarity NPC224273
0.913 High Similarity NPC40649
0.913 High Similarity NPC209486
0.9091 High Similarity NPC100551
0.9068 High Similarity NPC133909
0.9068 High Similarity NPC32032
0.906 High Similarity NPC297186
0.9008 High Similarity NPC214620
0.9 High Similarity NPC29883
0.9 High Similarity NPC201728
0.9 High Similarity NPC262671
0.8983 High Similarity NPC242895
0.8983 High Similarity NPC156139
0.8974 High Similarity NPC294037
0.8943 High Similarity NPC307732
0.8943 High Similarity NPC42292
0.8917 High Similarity NPC13238
0.8909 High Similarity NPC184658
0.8908 High Similarity NPC309765
0.8898 High Similarity NPC149246
0.8898 High Similarity NPC146642
0.8889 High Similarity NPC158222
0.8871 High Similarity NPC198249
0.8824 High Similarity NPC215392
0.8824 High Similarity NPC303737
0.8814 High Similarity NPC159525
0.879 High Similarity NPC247477
0.879 High Similarity NPC17840
0.8783 High Similarity NPC276111
0.8783 High Similarity NPC118288
0.878 High Similarity NPC293453
0.878 High Similarity NPC41263
0.877 High Similarity NPC8745
0.875 High Similarity NPC91105
0.8699 High Similarity NPC98254
0.8699 High Similarity NPC23126
0.8699 High Similarity NPC72158
0.8699 High Similarity NPC30501
0.8699 High Similarity NPC190043
0.8699 High Similarity NPC162612
0.8699 High Similarity NPC105157
0.8699 High Similarity NPC103356
0.8699 High Similarity NPC100067
0.8699 High Similarity NPC266689
0.8699 High Similarity NPC169250
0.8696 High Similarity NPC98543
0.8689 High Similarity NPC10926
0.8678 High Similarity NPC65761
0.8678 High Similarity NPC472029
0.8667 High Similarity NPC226275
0.8667 High Similarity NPC196976
0.8632 High Similarity NPC312800
0.8629 High Similarity NPC473017
0.8629 High Similarity NPC21305
0.8629 High Similarity NPC221777
0.8618 High Similarity NPC62952
0.8618 High Similarity NPC267846
0.8595 High Similarity NPC225710
0.8571 High Similarity NPC219892
0.8571 High Similarity NPC189823
0.856 High Similarity NPC474998
0.856 High Similarity NPC102829
0.856 High Similarity NPC120488
0.8559 High Similarity NPC121259
0.8548 High Similarity NPC116513
0.8537 High Similarity NPC475733
0.8534 High Similarity NPC211421
0.8527 High Similarity NPC474726
0.8527 High Similarity NPC475955
0.8492 Intermediate Similarity NPC185497
0.8492 Intermediate Similarity NPC26697
0.8487 Intermediate Similarity NPC474890
0.8487 Intermediate Similarity NPC161943
0.8487 Intermediate Similarity NPC273282
0.848 Intermediate Similarity NPC80694
0.848 Intermediate Similarity NPC179898
0.848 Intermediate Similarity NPC186098
0.8475 Intermediate Similarity NPC128825
0.8468 Intermediate Similarity NPC473751
0.8455 Intermediate Similarity NPC6888
0.8438 Intermediate Similarity NPC48036
0.8438 Intermediate Similarity NPC180261
0.8438 Intermediate Similarity NPC37299
0.8438 Intermediate Similarity NPC153783
0.843 Intermediate Similarity NPC248363
0.8425 Intermediate Similarity NPC475042
0.8425 Intermediate Similarity NPC469526
0.8425 Intermediate Similarity NPC34070
0.8417 Intermediate Similarity NPC188814
0.8417 Intermediate Similarity NPC195262
0.8413 Intermediate Similarity NPC60558
0.8413 Intermediate Similarity NPC8005
0.8413 Intermediate Similarity NPC476119
0.8413 Intermediate Similarity NPC78662
0.84 Intermediate Similarity NPC128428
0.84 Intermediate Similarity NPC305518
0.8397 Intermediate Similarity NPC9121
0.8397 Intermediate Similarity NPC177307
0.8387 Intermediate Similarity NPC477454
0.8385 Intermediate Similarity NPC118919
0.8372 Intermediate Similarity NPC175943
0.8361 Intermediate Similarity NPC198336
0.8359 Intermediate Similarity NPC262359
0.8359 Intermediate Similarity NPC135801
0.8347 Intermediate Similarity NPC260837
0.8346 Intermediate Similarity NPC233056
0.8333 Intermediate Similarity NPC19622
0.8333 Intermediate Similarity NPC52358
0.8333 Intermediate Similarity NPC112789
0.8333 Intermediate Similarity NPC94637
0.8333 Intermediate Similarity NPC95537
0.8333 Intermediate Similarity NPC303264
0.8321 Intermediate Similarity NPC71256
0.832 Intermediate Similarity NPC473691
0.8319 Intermediate Similarity NPC131192
0.8319 Intermediate Similarity NPC83718
0.8308 Intermediate Similarity NPC182496
0.8308 Intermediate Similarity NPC180905
0.8308 Intermediate Similarity NPC470210
0.8308 Intermediate Similarity NPC290803
0.8308 Intermediate Similarity NPC278375
0.8295 Intermediate Similarity NPC139074
0.8295 Intermediate Similarity NPC87231
0.8295 Intermediate Similarity NPC205468
0.8295 Intermediate Similarity NPC212631
0.8295 Intermediate Similarity NPC213485
0.8295 Intermediate Similarity NPC129132
0.8295 Intermediate Similarity NPC40524
0.8295 Intermediate Similarity NPC257756
0.8293 Intermediate Similarity NPC283514
0.8271 Intermediate Similarity NPC275903
0.8268 Intermediate Similarity NPC109123
0.8268 Intermediate Similarity NPC69235
0.8268 Intermediate Similarity NPC92624
0.8268 Intermediate Similarity NPC212379
0.8264 Intermediate Similarity NPC90522
0.8264 Intermediate Similarity NPC156654
0.8264 Intermediate Similarity NPC328459
0.8261 Intermediate Similarity NPC224584
0.8258 Intermediate Similarity NPC478200
0.8258 Intermediate Similarity NPC33144
0.8258 Intermediate Similarity NPC472403
0.8254 Intermediate Similarity NPC209959
0.825 Intermediate Similarity NPC125252
0.8244 Intermediate Similarity NPC223836
0.8244 Intermediate Similarity NPC158481
0.8244 Intermediate Similarity NPC235115
0.8231 Intermediate Similarity NPC312318
0.8231 Intermediate Similarity NPC472365
0.8231 Intermediate Similarity NPC56031
0.8231 Intermediate Similarity NPC242294
0.8231 Intermediate Similarity NPC192304
0.8231 Intermediate Similarity NPC139813
0.8231 Intermediate Similarity NPC337373
0.8231 Intermediate Similarity NPC175098
0.8231 Intermediate Similarity NPC263670
0.8231 Intermediate Similarity NPC166480
0.8231 Intermediate Similarity NPC188646
0.8231 Intermediate Similarity NPC44437
0.8231 Intermediate Similarity NPC282780
0.8217 Intermediate Similarity NPC313618
0.8217 Intermediate Similarity NPC175738
0.8217 Intermediate Similarity NPC64359
0.8217 Intermediate Similarity NPC308037
0.8217 Intermediate Similarity NPC65060
0.8209 Intermediate Similarity NPC472035
0.8209 Intermediate Similarity NPC478201
0.8205 Intermediate Similarity NPC114682
0.8203 Intermediate Similarity NPC147757
0.8203 Intermediate Similarity NPC470987
0.8203 Intermediate Similarity NPC259942
0.8203 Intermediate Similarity NPC21378
0.8203 Intermediate Similarity NPC12694
0.8197 Intermediate Similarity NPC72977
0.8197 Intermediate Similarity NPC294964
0.8197 Intermediate Similarity NPC233282
0.8195 Intermediate Similarity NPC92655
0.8182 Intermediate Similarity NPC474771
0.8182 Intermediate Similarity NPC135837
0.8182 Intermediate Similarity NPC474849
0.8182 Intermediate Similarity NPC65837
0.8182 Intermediate Similarity NPC70380
0.8182 Intermediate Similarity NPC149372
0.8182 Intermediate Similarity NPC27633
0.8182 Intermediate Similarity NPC94298
0.8182 Intermediate Similarity NPC194579
0.8182 Intermediate Similarity NPC178467
0.8174 Intermediate Similarity NPC226699
0.8168 Intermediate Similarity NPC70859

  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 NPC241089 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
0.9091 High Similarity NPD74 Approved
0.9091 High Similarity NPD9266 Approved
0.9 High Similarity NPD9267 Approved
0.9 High Similarity NPD9265 Clinical (unspecified phase)
0.9 High Similarity NPD9263 Approved
0.9 High Similarity NPD9264 Approved
0.8636 High Similarity NPD9261 Approved
0.8621 High Similarity NPD9281 Approved
0.8595 High Similarity NPD9269 Phase 2
0.8571 High Similarity NPD9268 Approved
0.8475 Intermediate Similarity NPD9493 Approved
0.8359 Intermediate Similarity NPD943 Approved
0.8217 Intermediate Similarity NPD1240 Approved
0.8182 Intermediate Similarity NPD9545 Approved
0.8106 Intermediate Similarity NPD1510 Phase 2
0.8106 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD1164 Approved
0.8092 Intermediate Similarity NPD1607 Approved
0.806 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD9717 Approved
0.797 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7953 Intermediate Similarity NPD1203 Approved
0.7926 Intermediate Similarity NPD1549 Phase 2
0.791 Intermediate Similarity NPD1551 Phase 2
0.7879 Intermediate Similarity NPD230 Phase 1
0.7852 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD5405 Approved
0.7647 Intermediate Similarity NPD5404 Approved
0.7647 Intermediate Similarity NPD5406 Approved
0.7647 Intermediate Similarity NPD5408 Approved
0.7643 Intermediate Similarity NPD6799 Approved
0.7636 Intermediate Similarity NPD9258 Approved
0.7636 Intermediate Similarity NPD9256 Approved
0.7594 Intermediate Similarity NPD520 Approved
0.7586 Intermediate Similarity NPD846 Approved
0.7586 Intermediate Similarity NPD940 Approved
0.7554 Intermediate Similarity NPD3750 Approved
0.7538 Intermediate Similarity NPD1470 Approved
0.7519 Intermediate Similarity NPD411 Approved
0.7518 Intermediate Similarity NPD1511 Approved
0.7518 Intermediate Similarity NPD2935 Discontinued
0.7517 Intermediate Similarity NPD7411 Suspended
0.75 Intermediate Similarity NPD1201 Approved
0.7465 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD1512 Approved
0.7402 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7390 Discontinued
0.7388 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD7075 Discontinued
0.7383 Intermediate Similarity NPD3749 Approved
0.7364 Intermediate Similarity NPD422 Phase 1
0.7357 Intermediate Similarity NPD1243 Approved
0.7353 Intermediate Similarity NPD447 Suspended
0.7343 Intermediate Similarity NPD2534 Approved
0.7343 Intermediate Similarity NPD2532 Approved
0.7343 Intermediate Similarity NPD2533 Approved
0.7329 Intermediate Similarity NPD6599 Discontinued
0.7329 Intermediate Similarity NPD4380 Phase 2
0.7324 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7819 Suspended
0.7273 Intermediate Similarity NPD9259 Approved
0.7273 Intermediate Similarity NPD9257 Approved
0.7266 Intermediate Similarity NPD2796 Approved
0.7259 Intermediate Similarity NPD3764 Approved
0.7246 Intermediate Similarity NPD9279 Approved
0.723 Intermediate Similarity NPD6801 Discontinued
0.7222 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD1019 Discontinued
0.7203 Intermediate Similarity NPD1242 Phase 1
0.72 Intermediate Similarity NPD7768 Phase 2
0.7194 Intermediate Similarity NPD3748 Approved
0.7188 Intermediate Similarity NPD1759 Phase 1
0.7174 Intermediate Similarity NPD6651 Approved
0.7152 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD920 Approved
0.7123 Intermediate Similarity NPD5403 Approved
0.7114 Intermediate Similarity NPD1934 Approved
0.7113 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD2800 Approved
0.7111 Intermediate Similarity NPD6832 Phase 2
0.7109 Intermediate Similarity NPD1758 Phase 1
0.7103 Intermediate Similarity NPD5401 Approved
0.7097 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD3882 Suspended
0.7078 Intermediate Similarity NPD6232 Discontinued
0.7071 Intermediate Similarity NPD2799 Discontinued
0.7067 Intermediate Similarity NPD2801 Approved
0.7067 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1196 Approved
0.7042 Intermediate Similarity NPD75 Approved
0.7042 Intermediate Similarity NPD9277 Approved
0.702 Intermediate Similarity NPD3817 Phase 2
0.702 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD2313 Discontinued
0.7007 Intermediate Similarity NPD1296 Phase 2
0.6993 Remote Similarity NPD1195 Approved
0.6993 Remote Similarity NPD2654 Approved
0.6983 Remote Similarity NPD1202 Approved
0.6974 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6972 Remote Similarity NPD9278 Suspended
0.6972 Remote Similarity NPD2344 Approved
0.6972 Remote Similarity NPD9276 Approved
0.6972 Remote Similarity NPD9274 Approved
0.6972 Remote Similarity NPD9275 Approved
0.6954 Remote Similarity NPD1465 Phase 2
0.6953 Remote Similarity NPD255 Approved
0.6953 Remote Similarity NPD256 Approved
0.6943 Remote Similarity NPD7473 Discontinued
0.694 Remote Similarity NPD3225 Approved
0.6918 Remote Similarity NPD1543 Discontinued
0.6909 Remote Similarity NPD9089 Approved
0.6899 Remote Similarity NPD9568 Approved
0.6875 Remote Similarity NPD111 Approved
0.6875 Remote Similarity NPD5953 Discontinued
0.6857 Remote Similarity NPD1933 Approved
0.6857 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6855 Remote Similarity NPD7286 Phase 2
0.6838 Remote Similarity NPD2798 Approved
0.6831 Remote Similarity NPD4308 Phase 3
0.6828 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6828 Remote Similarity NPD4628 Phase 3
0.6818 Remote Similarity NPD9093 Approved
0.68 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6797 Remote Similarity NPD5402 Approved
0.6792 Remote Similarity NPD3818 Discontinued
0.6791 Remote Similarity NPD1481 Phase 2
0.6788 Remote Similarity NPD9494 Approved
0.6786 Remote Similarity NPD468 Phase 1
0.6781 Remote Similarity NPD2309 Approved
0.6781 Remote Similarity NPD6190 Approved
0.678 Remote Similarity NPD9260 Approved
0.6774 Remote Similarity NPD919 Approved
0.6765 Remote Similarity NPD2797 Approved
0.6763 Remote Similarity NPD3268 Approved
0.675 Remote Similarity NPD9273 Approved
0.6746 Remote Similarity NPD4750 Phase 3
0.6716 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6716 Remote Similarity NPD1535 Discovery
0.6689 Remote Similarity NPD3226 Approved
0.6688 Remote Similarity NPD4288 Approved
0.6687 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1608 Approved
0.6667 Remote Similarity NPD1548 Phase 1
0.6667 Remote Similarity NPD6166 Phase 2
0.6667 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6646 Remote Similarity NPD5711 Approved
0.6646 Remote Similarity NPD5710 Approved
0.6646 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6646 Remote Similarity NPD7054 Approved
0.6639 Remote Similarity NPD2934 Approved
0.6639 Remote Similarity NPD2933 Approved
0.6621 Remote Similarity NPD2346 Discontinued
0.6619 Remote Similarity NPD1008 Clinical (unspecified phase)
0.6613 Remote Similarity NPD1237 Approved
0.6612 Remote Similarity NPD9495 Approved
0.6605 Remote Similarity NPD7074 Phase 3
0.6605 Remote Similarity NPD7472 Approved
0.66 Remote Similarity NPD9509 Clinical (unspecified phase)
0.6599 Remote Similarity NPD3400 Discontinued
0.6597 Remote Similarity NPD7033 Discontinued
0.6583 Remote Similarity NPD2859 Approved
0.6583 Remote Similarity NPD2860 Approved
0.6582 Remote Similarity NPD6959 Discontinued
0.6564 Remote Similarity NPD6797 Phase 2
0.656 Remote Similarity NPD9697 Approved
0.6557 Remote Similarity NPD1238 Approved
0.6552 Remote Similarity NPD9570 Approved
0.6552 Remote Similarity NPD9094 Approved
0.6549 Remote Similarity NPD4307 Phase 2
0.6549 Remote Similarity NPD9491 Approved
0.6544 Remote Similarity NPD3972 Approved
0.6543 Remote Similarity NPD6020 Phase 2
0.6543 Remote Similarity NPD5844 Phase 1
0.6538 Remote Similarity NPD1241 Discontinued
0.6524 Remote Similarity NPD7251 Discontinued
0.6524 Remote Similarity NPD6559 Discontinued
0.6522 Remote Similarity NPD3266 Approved
0.6522 Remote Similarity NPD3267 Approved
0.6512 Remote Similarity NPD9508 Approved
0.651 Remote Similarity NPD3300 Phase 2
0.65 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6486 Remote Similarity NPD7003 Approved
0.6485 Remote Similarity NPD7808 Phase 3
0.648 Remote Similarity NPD164 Approved
0.6475 Remote Similarity NPD257 Approved
0.6475 Remote Similarity NPD258 Approved
0.6475 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6474 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7458 Discontinued
0.6471 Remote Similarity NPD1610 Phase 2
0.6463 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6462 Remote Similarity NPD5277 Phase 2
0.6457 Remote Similarity NPD1358 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