Structure

Physi-Chem Properties

Molecular Weight:  166.06
Volume:  171.489
LogP:  2.333
LogD:  2.503
LogS:  -2.806
# Rotatable Bonds:  3
TPSA:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.624
Synthetic Accessibility Score:  1.201
Fsp3:  0.222
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:  -4.437
MDCK Permeability:  3.2058505894383416e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.783
Plasma Protein Binding (PPB):  83.43257904052734%
Volume Distribution (VD):  0.796
Pgp-substrate:  14.246999740600586%

ADMET: Metabolism

CYP1A2-inhibitor:  0.977
CYP1A2-substrate:  0.953
CYP2C19-inhibitor:  0.917
CYP2C19-substrate:  0.647
CYP2C9-inhibitor:  0.286
CYP2C9-substrate:  0.874
CYP2D6-inhibitor:  0.211
CYP2D6-substrate:  0.874
CYP3A4-inhibitor:  0.192
CYP3A4-substrate:  0.281

ADMET: Excretion

Clearance (CL):  10.874
Half-life (T1/2):  0.845

ADMET: Toxicity

hERG Blockers:  0.137
Human Hepatotoxicity (H-HT):  0.075
Drug-inuced Liver Injury (DILI):  0.584
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.024
Maximum Recommended Daily Dose:  0.018
Skin Sensitization:  0.574
Carcinogencity:  0.227
Eye Corrosion:  0.04
Eye Irritation:  0.986
Respiratory Toxicity:  0.11

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  Natural Product: NPC220540

Natural Product ID:  NPC220540
Common Name*:   Methyl 4-Methoxybenzoate
IUPAC Name:   methyl 4-methoxybenzoate
Synonyms:   Methyl 4-Methoxybenzoate
Standard InCHIKey:  DDIZAANNODHTRB-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H10O3/c1-11-8-5-3-7(4-6-8)9(10)12-2/h3-6H,1-2H3
SMILES:  COc1ccc(cc1)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1762668
PubChem CID:   8499
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0002344] Methoxybenzoic acids and derivatives
            • [CHEMONTID:0002346] P-methoxybenzoic acids and 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
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jep.2005.01.054]
NPO19242 Eucalyptus albens Species Myrtaceae Eukaryota flowers n.a. n.a. PMID[10075775]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[10479331]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Seeds n.a. n.a. PMID[15387664]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17996677]
NPO19083 Alstonia angustiloba Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[18524603]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. stem n.a. PMID[21443171]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota leaves and branches San Antonio, Texas 2004-JUN PMID[25685941]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota leaves and branches n.a. n.a. PMID[25685941]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[26238319]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota Roots n.a. n.a. PMID[29924604]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31181920]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31418264]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. Suriname rainforest n.a. PMID[9428162]
NPO13274 Illicium verum Species Schisandraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO13274 Illicium verum Species Schisandraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13274 Illicium verum Species Schisandraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19436 Annona cherimola Species Annonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5740 Phellodendron japonicum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14233 Ormosia dasycarpa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24402.1 Coffea liberica var. dewevrei Varieties Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13358 Piper brachystachyum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5740 Phellodendron japonicum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11967 Delphinium giraldii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10492 Artemisia montana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17499 Bursera kerberi Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18765 Juniperus scopulorum Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15802 Papaver pseudocanescens Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16325 Sideritis dasygnaphala Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16981 Gutierrezia dracunculoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18169 Creosphaeria sassafras Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19436 Annona cherimola Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19769 Boschniakia rossica Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15127 Senecio congestus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14233 Ormosia dasycarpa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19170 Lasianthaea podocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18262 Aspergillus microcysticus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18602 Melampodium leucanthum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19083 Alstonia angustiloba Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11646 Morella pensylvanica Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12223 Stellaria media Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17296 Beesia calthifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18424 Selinum libanotis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19572 Pellacalyx axillaris Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19709 Pseudocyphellaria australiensis Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12914 Sarcophyton flexuosum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11967 Delphinium giraldii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13358 Piper brachystachyum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29531 Lupinus cosentinii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11164 Renealmia alpinia Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18927 Clinacanthus nutans Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18348 Crotalaria stolzii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17354 Micromonospora echinospora Species Micromonosporaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17230 Psidium acutangulum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8172 Emericellopsis minima Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17759 Rhododendron mucronulatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19242 Eucalyptus albens Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18533 Delisea elegans Species Bonnemaisoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19371 Costasiella ocellifera Species Costasiellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18676 Clerodendrum trichotomum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5455 Euploca racemosa Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18048 Phlomis crinita Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24402.1 Coffea liberica var. dewevrei Varieties Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5740 Phellodendron japonicum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4679 Hedysarum gmelini Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17630 Helenium integrifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13737 Tephroseris kirilowii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9906 Zephyranthes flava Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO968 Artemisia pectinata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10492 Artemisia montana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29450 Streptomyces parvisporogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17114 Streptomyces melanogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11081 Baccharis grandicapitulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25370 Botrychium ternatum Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1783 Euonymus fortunei Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12870 Curcuma aeruginosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16135 Pestalotiopsis oenotherae Species Sporocadaceae 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
NPO13274 NPC220540 Other Fruit 15.05 0.1 30 mg/100g Database [DUKE]

☑ 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
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ki = 3530.0 nM PMID[454378]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ki = 3840.0 nM PMID[454378]
NPT2 Others Unspecified Ki = 67.0 nM PMID[454378]
NPT2 Others Unspecified Ki = 610.0 nM PMID[454378]
NPT2 Others Unspecified Ratio Ki = 52.7 n.a. PMID[454378]
NPT2 Others Unspecified Ratio Ki = 5.78 n.a. PMID[454378]
NPT21912 ORGANISM Hylobius abietis Hylobius abietis AFI = 54.0 % PMID[454379]
NPT29 Organism Rattus norvegicus Rattus norvegicus pLD50 = 8.52 n.a. PMID[454380]
NPT2 Others Unspecified Potency n.a. 34376.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27306 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3890 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54947.7 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 NPC220540 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
0.964 High Similarity NPC61779
0.9304 High Similarity NPC69403
0.9304 High Similarity NPC291189
0.9266 High Similarity NPC23332
0.9196 High Similarity NPC131192
0.9174 High Similarity NPC183648
0.9145 High Similarity NPC221798
0.9091 High Similarity NPC57879
0.9068 High Similarity NPC165556
0.9035 High Similarity NPC94298
0.9035 High Similarity NPC27633
0.9027 High Similarity NPC470860
0.8992 High Similarity NPC475236
0.8992 High Similarity NPC154275
0.8981 High Similarity NPC1065
0.885 High Similarity NPC252004
0.8843 High Similarity NPC2596
0.8783 High Similarity NPC469954
0.8772 High Similarity NPC322358
0.8772 High Similarity NPC188907
0.876 High Similarity NPC37512
0.876 High Similarity NPC121104
0.8739 High Similarity NPC234639
0.8716 High Similarity NPC238115
0.8699 High Similarity NPC42292
0.8699 High Similarity NPC307732
0.8699 High Similarity NPC285776
0.8689 High Similarity NPC2401
0.8667 High Similarity NPC255073
0.8655 High Similarity NPC67300
0.8624 High Similarity NPC38209
0.8621 High Similarity NPC45104
0.8621 High Similarity NPC240664
0.8621 High Similarity NPC217423
0.8595 High Similarity NPC65041
0.8548 High Similarity NPC299010
0.8548 High Similarity NPC109778
0.8537 High Similarity NPC293453
0.8532 High Similarity NPC179686
0.8532 High Similarity NPC298224
0.8512 High Similarity NPC184219
0.8492 Intermediate Similarity NPC283823
0.8492 Intermediate Similarity NPC159418
0.8487 Intermediate Similarity NPC225245
0.848 Intermediate Similarity NPC104854
0.8468 Intermediate Similarity NPC184658
0.8455 Intermediate Similarity NPC2518
0.8455 Intermediate Similarity NPC293387
0.8443 Intermediate Similarity NPC49938
0.8435 Intermediate Similarity NPC109241
0.8435 Intermediate Similarity NPC53953
0.8425 Intermediate Similarity NPC311339
0.8421 Intermediate Similarity NPC54626
0.8413 Intermediate Similarity NPC111888
0.8407 Intermediate Similarity NPC259554
0.8403 Intermediate Similarity NPC230951
0.84 Intermediate Similarity NPC86774
0.84 Intermediate Similarity NPC327457
0.8393 Intermediate Similarity NPC29883
0.839 Intermediate Similarity NPC293424
0.839 Intermediate Similarity NPC166591
0.8387 Intermediate Similarity NPC80694
0.8387 Intermediate Similarity NPC186098
0.8378 Intermediate Similarity NPC128730
0.8374 Intermediate Similarity NPC95309
0.8374 Intermediate Similarity NPC204579
0.8374 Intermediate Similarity NPC110211
0.8361 Intermediate Similarity NPC145134
0.8361 Intermediate Similarity NPC6888
0.8346 Intermediate Similarity NPC288743
0.8346 Intermediate Similarity NPC66158
0.8333 Intermediate Similarity NPC175298
0.8333 Intermediate Similarity NPC295317
0.832 Intermediate Similarity NPC78662
0.832 Intermediate Similarity NPC66246
0.832 Intermediate Similarity NPC8005
0.832 Intermediate Similarity NPC211120
0.832 Intermediate Similarity NPC170546
0.8319 Intermediate Similarity NPC291837
0.8306 Intermediate Similarity NPC158654
0.8304 Intermediate Similarity NPC326447
0.8304 Intermediate Similarity NPC176971
0.8293 Intermediate Similarity NPC2771
0.8293 Intermediate Similarity NPC52035
0.8288 Intermediate Similarity NPC109637
0.8281 Intermediate Similarity NPC155098
0.8279 Intermediate Similarity NPC141252
0.8279 Intermediate Similarity NPC11799
0.8279 Intermediate Similarity NPC474691
0.8254 Intermediate Similarity NPC473271
0.8254 Intermediate Similarity NPC282230
0.8254 Intermediate Similarity NPC183348
0.8254 Intermediate Similarity NPC247779
0.824 Intermediate Similarity NPC473744
0.823 Intermediate Similarity NPC151530
0.823 Intermediate Similarity NPC157473
0.8224 Intermediate Similarity NPC130398
0.8217 Intermediate Similarity NPC470844
0.8214 Intermediate Similarity NPC227255
0.8205 Intermediate Similarity NPC81808
0.8189 Intermediate Similarity NPC470976
0.8189 Intermediate Similarity NPC196979
0.8189 Intermediate Similarity NPC470977
0.8189 Intermediate Similarity NPC125153
0.8189 Intermediate Similarity NPC15083
0.8182 Intermediate Similarity NPC13755
0.8175 Intermediate Similarity NPC226855
0.8175 Intermediate Similarity NPC194979
0.8174 Intermediate Similarity NPC88868
0.8174 Intermediate Similarity NPC25067
0.8174 Intermediate Similarity NPC231251
0.8174 Intermediate Similarity NPC473809
0.8168 Intermediate Similarity NPC253616
0.816 Intermediate Similarity NPC475496
0.816 Intermediate Similarity NPC305518
0.816 Intermediate Similarity NPC286683
0.816 Intermediate Similarity NPC128428
0.816 Intermediate Similarity NPC49852
0.816 Intermediate Similarity NPC281020
0.816 Intermediate Similarity NPC264428
0.8145 Intermediate Similarity NPC470858
0.814 Intermediate Similarity NPC45404
0.8125 Intermediate Similarity NPC309717
0.8125 Intermediate Similarity NPC164236
0.8125 Intermediate Similarity NPC470859
0.8125 Intermediate Similarity NPC128348
0.8125 Intermediate Similarity NPC308037
0.8125 Intermediate Similarity NPC112192
0.8125 Intermediate Similarity NPC66384
0.8125 Intermediate Similarity NPC313618
0.8125 Intermediate Similarity NPC64359
0.8125 Intermediate Similarity NPC189106
0.8125 Intermediate Similarity NPC284424
0.812 Intermediate Similarity NPC279916
0.8106 Intermediate Similarity NPC36414
0.8103 Intermediate Similarity NPC233238
0.8095 Intermediate Similarity NPC304747
0.8095 Intermediate Similarity NPC125887
0.8095 Intermediate Similarity NPC473907
0.8092 Intermediate Similarity NPC112068
0.8092 Intermediate Similarity NPC110899
0.8092 Intermediate Similarity NPC268081
0.8092 Intermediate Similarity NPC25305
0.8092 Intermediate Similarity NPC125417
0.8092 Intermediate Similarity NPC95679
0.8083 Intermediate Similarity NPC474890
0.8083 Intermediate Similarity NPC161943
0.8083 Intermediate Similarity NPC273282
0.8083 Intermediate Similarity NPC265547
0.8083 Intermediate Similarity NPC171023
0.808 Intermediate Similarity NPC177925
0.8077 Intermediate Similarity NPC180905
0.8077 Intermediate Similarity NPC66705
0.8077 Intermediate Similarity NPC182496
0.8073 Intermediate Similarity NPC276775
0.8073 Intermediate Similarity NPC92754
0.8073 Intermediate Similarity NPC249912
0.807 Intermediate Similarity NPC226699
0.8067 Intermediate Similarity NPC19290
0.8067 Intermediate Similarity NPC128825
0.8065 Intermediate Similarity NPC30216
0.8065 Intermediate Similarity NPC107846
0.8062 Intermediate Similarity NPC229646
0.8062 Intermediate Similarity NPC87231
0.8062 Intermediate Similarity NPC257756
0.8062 Intermediate Similarity NPC182428
0.8062 Intermediate Similarity NPC129132
0.8062 Intermediate Similarity NPC212631
0.8062 Intermediate Similarity NPC205468
0.8053 Intermediate Similarity NPC288760
0.8053 Intermediate Similarity NPC473855
0.8049 Intermediate Similarity NPC311219
0.8047 Intermediate Similarity NPC473777
0.8045 Intermediate Similarity NPC326065
0.8045 Intermediate Similarity NPC51181
0.8045 Intermediate Similarity NPC136095
0.8034 Intermediate Similarity NPC199462
0.8031 Intermediate Similarity NPC212379
0.8031 Intermediate Similarity NPC69235
0.8031 Intermediate Similarity NPC473894
0.8031 Intermediate Similarity NPC60558
0.803 Intermediate Similarity NPC103001
0.8018 Intermediate Similarity NPC107101
0.8017 Intermediate Similarity NPC264976
0.8017 Intermediate Similarity NPC281356
0.8017 Intermediate Similarity NPC298796
0.8016 Intermediate Similarity NPC16651
0.8016 Intermediate Similarity NPC32163
0.8 Intermediate Similarity NPC312318
0.8 Intermediate Similarity NPC223354
0.8 Intermediate Similarity NPC78701
0.8 Intermediate Similarity NPC139813
0.8 Intermediate Similarity NPC263670
0.8 Intermediate Similarity NPC35448
0.8 Intermediate Similarity NPC225060
0.8 Intermediate Similarity NPC337373
0.8 Intermediate Similarity NPC192304
0.8 Intermediate Similarity NPC473626
0.8 Intermediate Similarity NPC4164
0.8 Intermediate Similarity NPC242294

  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 NPC220540 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
0.9035 High Similarity NPD9545 Approved
0.8435 Intermediate Similarity NPD1241 Discontinued
0.8393 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.8347 Intermediate Similarity NPD3972 Approved
0.8304 Intermediate Similarity NPD3134 Approved
0.825 Intermediate Similarity NPD17 Approved
0.823 Intermediate Similarity NPD1358 Approved
0.8125 Intermediate Similarity NPD1240 Approved
0.8067 Intermediate Similarity NPD9493 Approved
0.8049 Intermediate Similarity NPD1608 Approved
0.8049 Intermediate Similarity NPD9717 Approved
0.8045 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD1607 Approved
0.7985 Intermediate Similarity NPD4628 Phase 3
0.7937 Intermediate Similarity NPD1019 Discontinued
0.792 Intermediate Similarity NPD1876 Approved
0.7874 Intermediate Similarity NPD9494 Approved
0.7836 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD1281 Approved
0.782 Intermediate Similarity NPD2796 Approved
0.7812 Intermediate Similarity NPD6832 Phase 2
0.781 Intermediate Similarity NPD6799 Approved
0.7786 Intermediate Similarity NPD230 Phase 1
0.7778 Intermediate Similarity NPD1243 Approved
0.7768 Intermediate Similarity NPD1238 Approved
0.7744 Intermediate Similarity NPD3748 Approved
0.7744 Intermediate Similarity NPD1510 Phase 2
0.7739 Intermediate Similarity NPD9697 Approved
0.7719 Intermediate Similarity NPD9261 Approved
0.7717 Intermediate Similarity NPD1203 Approved
0.771 Intermediate Similarity NPD3142 Approved
0.771 Intermediate Similarity NPD3140 Approved
0.7698 Intermediate Similarity NPD2186 Approved
0.768 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD1778 Approved
0.7652 Intermediate Similarity NPD164 Approved
0.7643 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7642 Intermediate Similarity NPD1894 Discontinued
0.7638 Intermediate Similarity NPD1283 Approved
0.763 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD2353 Approved
0.7609 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD1549 Phase 2
0.7557 Intermediate Similarity NPD1296 Phase 2
0.7557 Intermediate Similarity NPD3764 Approved
0.7556 Intermediate Similarity NPD1551 Phase 2
0.7556 Intermediate Similarity NPD2935 Discontinued
0.754 Intermediate Similarity NPD422 Phase 1
0.7536 Intermediate Similarity NPD3887 Approved
0.7519 Intermediate Similarity NPD1933 Approved
0.7519 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD2798 Approved
0.7518 Intermediate Similarity NPD920 Approved
0.75 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6599 Discontinued
0.7481 Intermediate Similarity NPD2799 Discontinued
0.748 Intermediate Similarity NPD1481 Phase 2
0.7477 Intermediate Similarity NPD9257 Approved
0.7477 Intermediate Similarity NPD9259 Approved
0.7464 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD3750 Approved
0.746 Intermediate Similarity NPD3847 Discontinued
0.7458 Intermediate Similarity NPD9263 Approved
0.7458 Intermediate Similarity NPD9267 Approved
0.7458 Intermediate Similarity NPD9264 Approved
0.7444 Intermediate Similarity NPD4307 Phase 2
0.7442 Intermediate Similarity NPD3266 Approved
0.7442 Intermediate Similarity NPD3267 Approved
0.744 Intermediate Similarity NPD5691 Approved
0.744 Intermediate Similarity NPD1651 Approved
0.7438 Intermediate Similarity NPD5535 Approved
0.7431 Intermediate Similarity NPD6385 Approved
0.7431 Intermediate Similarity NPD6386 Approved
0.7431 Intermediate Similarity NPD7411 Suspended
0.7429 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD411 Approved
0.7419 Intermediate Similarity NPD5536 Phase 2
0.7417 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD2354 Approved
0.7407 Intermediate Similarity NPD743 Approved
0.7402 Intermediate Similarity NPD1535 Discovery
0.7395 Intermediate Similarity NPD9266 Approved
0.7395 Intermediate Similarity NPD2182 Approved
0.7395 Intermediate Similarity NPD74 Approved
0.7391 Intermediate Similarity NPD2654 Approved
0.7388 Intermediate Similarity NPD447 Suspended
0.7381 Intermediate Similarity NPD4626 Approved
0.7364 Intermediate Similarity NPD196 Phase 1
0.7364 Intermediate Similarity NPD3225 Approved
0.7355 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD7003 Approved
0.7329 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD7819 Suspended
0.7328 Intermediate Similarity NPD454 Approved
0.7321 Intermediate Similarity NPD1202 Approved
0.7308 Intermediate Similarity NPD2797 Approved
0.7302 Intermediate Similarity NPD9268 Approved
0.7302 Intermediate Similarity NPD5585 Approved
0.7293 Intermediate Similarity NPD2313 Discontinued
0.7273 Intermediate Similarity NPD1670 Discontinued
0.7273 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD6801 Discontinued
0.7254 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD2344 Approved
0.7226 Intermediate Similarity NPD4308 Phase 3
0.7222 Intermediate Similarity NPD957 Approved
0.7209 Intermediate Similarity NPD9269 Phase 2
0.7207 Intermediate Similarity NPD9258 Approved
0.7207 Intermediate Similarity NPD9256 Approved
0.7203 Intermediate Similarity NPD9509 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD2979 Phase 3
0.7181 Intermediate Similarity NPD7075 Discontinued
0.7172 Intermediate Similarity NPD7458 Discontinued
0.7164 Intermediate Similarity NPD3268 Approved
0.7164 Intermediate Similarity NPD6798 Discontinued
0.7162 Intermediate Similarity NPD3817 Phase 2
0.7162 Intermediate Similarity NPD5353 Approved
0.7133 Intermediate Similarity NPD2533 Approved
0.7133 Intermediate Similarity NPD919 Approved
0.7133 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD2534 Approved
0.7133 Intermediate Similarity NPD5401 Approved
0.7133 Intermediate Similarity NPD3146 Approved
0.7133 Intermediate Similarity NPD2532 Approved
0.7133 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD7440 Discontinued
0.7113 Intermediate Similarity NPD6652 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD4062 Phase 3
0.7111 Intermediate Similarity NPD6233 Phase 2
0.7107 Intermediate Similarity NPD2684 Approved
0.7101 Intermediate Similarity NPD7033 Discontinued
0.7083 Intermediate Similarity NPD6273 Approved
0.7075 Intermediate Similarity NPD958 Approved
0.7063 Intermediate Similarity NPD1511 Approved
0.7055 Intermediate Similarity NPD3226 Approved
0.7054 Intermediate Similarity NPD3496 Discontinued
0.7049 Intermediate Similarity NPD5451 Approved
0.7042 Intermediate Similarity NPD2309 Approved
0.704 Intermediate Similarity NPD9281 Approved
0.704 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD2249 Approved
0.7039 Intermediate Similarity NPD2247 Approved
0.7034 Intermediate Similarity NPD5403 Approved
0.7031 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD4359 Approved
0.7015 Intermediate Similarity NPD2614 Approved
0.7007 Intermediate Similarity NPD6355 Discontinued
0.7007 Intermediate Similarity NPD4380 Phase 2
0.7 Intermediate Similarity NPD7768 Phase 2
0.7 Intermediate Similarity NPD1471 Phase 3
0.7 Intermediate Similarity NPD2346 Discontinued
0.7 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.6985 Remote Similarity NPD8032 Phase 2
0.6966 Remote Similarity NPD1512 Approved
0.6957 Remote Similarity NPD6651 Approved
0.6957 Remote Similarity NPD9260 Approved
0.6954 Remote Similarity NPD3749 Approved
0.6948 Remote Similarity NPD5242 Approved
0.6935 Remote Similarity NPD228 Approved
0.6929 Remote Similarity NPD2531 Phase 2
0.6929 Remote Similarity NPD4476 Approved
0.6929 Remote Similarity NPD4477 Approved
0.6929 Remote Similarity NPD2438 Suspended
0.6918 Remote Similarity NPD5586 Clinical (unspecified phase)
0.6917 Remote Similarity NPD1164 Approved
0.6913 Remote Similarity NPD1934 Approved
0.6903 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6887 Remote Similarity NPD3882 Suspended
0.6885 Remote Similarity NPD290 Approved
0.6884 Remote Similarity NPD4622 Approved
0.6884 Remote Similarity NPD4340 Discontinued
0.6884 Remote Similarity NPD4618 Approved
0.6883 Remote Similarity NPD6232 Discontinued
0.688 Remote Similarity NPD821 Approved
0.688 Remote Similarity NPD7843 Approved
0.6867 Remote Similarity NPD2801 Approved
0.6867 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6853 Remote Similarity NPD6398 Clinical (unspecified phase)
0.685 Remote Similarity NPD255 Approved
0.685 Remote Similarity NPD256 Approved
0.6849 Remote Similarity NPD5049 Phase 3
0.6846 Remote Similarity NPD6873 Phase 2
0.6842 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6825 Remote Similarity NPD5283 Phase 1
0.6822 Remote Similarity NPD1548 Phase 1
0.6821 Remote Similarity NPD4288 Approved
0.6821 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6815 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6809 Remote Similarity NPD2239 Approved
0.6809 Remote Similarity NPD2240 Approved
0.6806 Remote Similarity NPD6190 Approved
0.6803 Remote Similarity NPD968 Approved
0.6791 Remote Similarity NPD987 Approved
0.6786 Remote Similarity NPD5689 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