Structure

Physi-Chem Properties

Molecular Weight:  214.19
Volume:  248.348
LogP:  5.231
LogD:  3.975
LogS:  -5.22
# Rotatable Bonds:  11
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.404
Synthetic Accessibility Score:  1.639
Fsp3:  0.923
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.591
MDCK Permeability:  2.102549660776276e-05
Pgp-inhibitor:  0.442
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.986
30% Bioavailability (F30%):  0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.943
Plasma Protein Binding (PPB):  95.57097625732422%
Volume Distribution (VD):  0.813
Pgp-substrate:  3.4345309734344482%

ADMET: Metabolism

CYP1A2-inhibitor:  0.95
CYP1A2-substrate:  0.465
CYP2C19-inhibitor:  0.668
CYP2C19-substrate:  0.357
CYP2C9-inhibitor:  0.45
CYP2C9-substrate:  0.919
CYP2D6-inhibitor:  0.047
CYP2D6-substrate:  0.102
CYP3A4-inhibitor:  0.344
CYP3A4-substrate:  0.107

ADMET: Excretion

Clearance (CL):  6.514
Half-life (T1/2):  0.562

ADMET: Toxicity

hERG Blockers:  0.113
Human Hepatotoxicity (H-HT):  0.029
Drug-inuced Liver Injury (DILI):  0.234
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.021
Skin Sensitization:  0.941
Carcinogencity:  0.114
Eye Corrosion:  0.957
Eye Irritation:  0.976
Respiratory Toxicity:  0.84

Download Data

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

  Natural Product: NPC201622

Natural Product ID:  NPC201622
Common Name*:   Methyl Dodecanoate
IUPAC Name:   methyl dodecanoate
Synonyms:  
Standard InCHIKey:  UQDUPQYQJKYHQI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H26O2/c1-3-4-5-6-7-8-9-10-11-12-13(14)15-2/h3-12H2,1-2H3
SMILES:  CCCCCCCCCCCC(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1894365
PubChem CID:   8139
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000324] Fatty acid esters
          • [CHEMONTID:0003417] Fatty acid methyl 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
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Nigeria(latitude 80°N and longitude 4°E) 2005; 2006 DOI[10.1002/ejlt.201000080]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-010-0259-y]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-014-0638-x]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytol.2008.07.007]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Plovdiv, Plovdiv region in South Bulgaria DOI[10.1051/CTV/20163101031]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. DOI[10.5012/bkcs.2003.24.11.1699]
NPO1394 Penicillium sclerotigenum Species Aspergillaceae Eukaryota sclerotia n.a. n.a. PMID[10217735]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[10336650]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11170689]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. leaf n.a. PMID[11312782]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[11312782]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11408943]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. PMID[11473446]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[12105962]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[15679315]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[16252923]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[17624889]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18611049]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18768384]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete 2007 PMID[19256538]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[19476340]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[20826702]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[21912858]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[22111577]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. flower n.a. PMID[22166201]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[23759170]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[23790907]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stalks n.a. n.a. PMID[24521157]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[24948953]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[25564559]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27444348]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[29099182]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[29154541]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Benedictine Pannonhalma Archabbey, Hungary PMID[29803478]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[31433178]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota Roots n.a. n.a. PMID[31464439]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruits n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Fruits n.a. Database[FooDB]
NPO22234 Ficus carica Species Moraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO201 Gmelina arborea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29399 Microdochium nivale Species Microdochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11327 Lactarius necator Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO201 Gmelina arborea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23213 Bistorta officinalis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO201 Gmelina arborea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31286 Dolichos lablab Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23213 Bistorta officinalis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25547 Spirodela polyrhiza Species Araceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26378 Bistorta manshuriensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1394 Penicillium sclerotigenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8243 Euphorbia supina Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3471 Suillellus luridus Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11327 Lactarius necator Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22234 Ficus carica Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26378 Bistorta manshuriensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9266 Stephania delavayi Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7167 Hosta undulata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29399 Microdochium nivale Species Microdochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO201 Gmelina arborea Species Lamiaceae 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
NPT546 Individual Protein Retinoid X receptor alpha Homo sapiens Potency n.a. 22387.2 nM PMID[505564]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Potency n.a. 35481.3 nM PMID[505564]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 7079.5 nM PMID[505564]
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency n.a. 31622.8 nM PMID[505564]
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens Potency n.a. 19952.6 nM PMID[505564]
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency n.a. 39810.7 nM PMID[505564]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 25118.9 nM PMID[505564]
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 3162.3 nM PMID[505564]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Potency n.a. 22387.2 nM PMID[505564]
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 15848.9 nM PMID[505564]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 25118.9 nM PMID[505564]
NPT249 Individual Protein Glucocorticoid receptor Homo sapiens Potency n.a. 50118.7 nM PMID[505564]
NPT546 Individual Protein Retinoid X receptor alpha Homo sapiens Potency n.a. 35481.3 nM PMID[505564]
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 39810.7 nM PMID[505564]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency n.a. 35481.3 nM PMID[505564]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 24336.5 nM PMID[505564]
NPT158 Individual Protein Nuclear receptor subfamily 1 group I member 2 Rattus norvegicus Potency n.a. 22387.2 nM PMID[505564]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 9688.5 nM PMID[505564]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens Potency n.a. 31622.8 nM PMID[505564]
NPT610 Others Molecular identity unknown Potency n.a. 50118.7 nM PMID[505564]
NPT610 Others Molecular identity unknown Potency n.a. 35481.3 nM PMID[505564]
NPT2 Others Unspecified Potency n.a. 24541.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 30637.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 28183.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 25118.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24535.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19489 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 NPC201622 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
1.0 High Similarity NPC305660
1.0 High Similarity NPC22903
1.0 High Similarity NPC54980
0.9722 High Similarity NPC219536
0.9722 High Similarity NPC31551
0.9459 High Similarity NPC149299
0.9459 High Similarity NPC28598
0.9459 High Similarity NPC40597
0.9459 High Similarity NPC256163
0.9459 High Similarity NPC250028
0.9459 High Similarity NPC161097
0.9211 High Similarity NPC53541
0.9189 High Similarity NPC80234
0.9189 High Similarity NPC223249
0.9143 High Similarity NPC156630
0.8974 High Similarity NPC236579
0.8974 High Similarity NPC203531
0.8947 High Similarity NPC12156
0.8947 High Similarity NPC165533
0.8684 High Similarity NPC301696
0.8684 High Similarity NPC201844
0.8684 High Similarity NPC113928
0.8684 High Similarity NPC14227
0.8684 High Similarity NPC261080
0.8684 High Similarity NPC301585
0.8684 High Similarity NPC154186
0.8684 High Similarity NPC279026
0.8537 High Similarity NPC287231
0.8537 High Similarity NPC47363
0.8378 Intermediate Similarity NPC80396
0.8378 Intermediate Similarity NPC80641
0.8378 Intermediate Similarity NPC154642
0.8333 Intermediate Similarity NPC63182
0.8333 Intermediate Similarity NPC145045
0.8333 Intermediate Similarity NPC57499
0.8333 Intermediate Similarity NPC105329
0.8333 Intermediate Similarity NPC30195
0.8333 Intermediate Similarity NPC52700
0.8333 Intermediate Similarity NPC12438
0.8293 Intermediate Similarity NPC317128
0.825 Intermediate Similarity NPC216630
0.825 Intermediate Similarity NPC209970
0.825 Intermediate Similarity NPC307783
0.825 Intermediate Similarity NPC171736
0.825 Intermediate Similarity NPC149184
0.825 Intermediate Similarity NPC196924
0.8205 Intermediate Similarity NPC118968
0.8205 Intermediate Similarity NPC183424
0.8205 Intermediate Similarity NPC214610
0.8205 Intermediate Similarity NPC294085
0.814 Intermediate Similarity NPC326957
0.8108 Intermediate Similarity NPC301398
0.8108 Intermediate Similarity NPC196442
0.8108 Intermediate Similarity NPC86545
0.8108 Intermediate Similarity NPC223374
0.8095 Intermediate Similarity NPC273545
0.8049 Intermediate Similarity NPC67462
0.7955 Intermediate Similarity NPC216130
0.7955 Intermediate Similarity NPC106872
0.7949 Intermediate Similarity NPC268826
0.7895 Intermediate Similarity NPC155263
0.7857 Intermediate Similarity NPC255837
0.7857 Intermediate Similarity NPC19305
0.7857 Intermediate Similarity NPC74845
0.7838 Intermediate Similarity NPC286498
0.7838 Intermediate Similarity NPC154396
0.7778 Intermediate Similarity NPC26253
0.775 Intermediate Similarity NPC81263
0.7727 Intermediate Similarity NPC324004
0.7727 Intermediate Similarity NPC328497
0.7692 Intermediate Similarity NPC128996
0.7674 Intermediate Similarity NPC8219
0.7674 Intermediate Similarity NPC55023
0.7619 Intermediate Similarity NPC176500
0.7609 Intermediate Similarity NPC305182
0.7609 Intermediate Similarity NPC55678
0.7568 Intermediate Similarity NPC286695
0.7568 Intermediate Similarity NPC322892
0.7556 Intermediate Similarity NPC200618
0.7556 Intermediate Similarity NPC131770
0.75 Intermediate Similarity NPC314679
0.7447 Intermediate Similarity NPC287811
0.7447 Intermediate Similarity NPC314084
0.7436 Intermediate Similarity NPC134782
0.7391 Intermediate Similarity NPC304162
0.7391 Intermediate Similarity NPC250919
0.7381 Intermediate Similarity NPC103286
0.7381 Intermediate Similarity NPC163746
0.7333 Intermediate Similarity NPC21844
0.7333 Intermediate Similarity NPC249754
0.7297 Intermediate Similarity NPC40965
0.7297 Intermediate Similarity NPC12904
0.7292 Intermediate Similarity NPC161366
0.7292 Intermediate Similarity NPC310746
0.725 Intermediate Similarity NPC14608
0.7234 Intermediate Similarity NPC90904
0.7209 Intermediate Similarity NPC129972
0.7209 Intermediate Similarity NPC71317
0.7209 Intermediate Similarity NPC301528
0.7179 Intermediate Similarity NPC289344
0.7179 Intermediate Similarity NPC155872
0.7174 Intermediate Similarity NPC477878
0.7174 Intermediate Similarity NPC324793
0.7143 Intermediate Similarity NPC39633
0.7143 Intermediate Similarity NPC139545
0.7143 Intermediate Similarity NPC309606
0.7111 Intermediate Similarity NPC282440
0.7111 Intermediate Similarity NPC308301
0.7105 Intermediate Similarity NPC175342
0.7105 Intermediate Similarity NPC147054
0.7073 Intermediate Similarity NPC73245
0.7045 Intermediate Similarity NPC76051
0.7027 Intermediate Similarity NPC168982
0.7 Intermediate Similarity NPC319589
0.7 Intermediate Similarity NPC320588
0.7 Intermediate Similarity NPC53463
0.7 Intermediate Similarity NPC23155
0.7 Intermediate Similarity NPC469937
0.6977 Remote Similarity NPC248763
0.6977 Remote Similarity NPC325452
0.6905 Remote Similarity NPC94368
0.6889 Remote Similarity NPC469781
0.6875 Remote Similarity NPC224227
0.6863 Remote Similarity NPC223677
0.6863 Remote Similarity NPC10316
0.6863 Remote Similarity NPC28779
0.6863 Remote Similarity NPC200845
0.6863 Remote Similarity NPC128061
0.6863 Remote Similarity NPC228473
0.6842 Remote Similarity NPC179831
0.6842 Remote Similarity NPC49151
0.6842 Remote Similarity NPC261991
0.6842 Remote Similarity NPC262505
0.6842 Remote Similarity NPC254713
0.6818 Remote Similarity NPC289686
0.6809 Remote Similarity NPC13105
0.6809 Remote Similarity NPC180534
0.68 Remote Similarity NPC71761
0.6757 Remote Similarity NPC221192
0.6757 Remote Similarity NPC29561
0.6757 Remote Similarity NPC153439
0.6757 Remote Similarity NPC222997
0.6757 Remote Similarity NPC79887
0.6757 Remote Similarity NPC196434
0.6757 Remote Similarity NPC4962
0.6757 Remote Similarity NPC42403
0.675 Remote Similarity NPC317203
0.6739 Remote Similarity NPC166287
0.6739 Remote Similarity NPC172042
0.6735 Remote Similarity NPC470412
0.6735 Remote Similarity NPC262968
0.6735 Remote Similarity NPC100096
0.6735 Remote Similarity NPC470410
0.6667 Remote Similarity NPC18224
0.6667 Remote Similarity NPC328710
0.6667 Remote Similarity NPC316546
0.66 Remote Similarity NPC281245
0.6585 Remote Similarity NPC301919
0.6571 Remote Similarity NPC28246
0.6531 Remote Similarity NPC50457
0.6512 Remote Similarity NPC3531
0.65 Remote Similarity NPC49615
0.6486 Remote Similarity NPC198118
0.6486 Remote Similarity NPC295442
0.6486 Remote Similarity NPC38859
0.6471 Remote Similarity NPC72722
0.6471 Remote Similarity NPC139029
0.6471 Remote Similarity NPC1813
0.6471 Remote Similarity NPC36061
0.6471 Remote Similarity NPC294548
0.6458 Remote Similarity NPC68577
0.6429 Remote Similarity NPC252843
0.6429 Remote Similarity NPC158179
0.6429 Remote Similarity NPC109026
0.641 Remote Similarity NPC268596
0.641 Remote Similarity NPC16578
0.641 Remote Similarity NPC225318
0.641 Remote Similarity NPC76608
0.641 Remote Similarity NPC149101
0.6364 Remote Similarity NPC17935
0.6364 Remote Similarity NPC472020
0.6364 Remote Similarity NPC472019
0.6364 Remote Similarity NPC226602
0.6364 Remote Similarity NPC470363
0.6346 Remote Similarity NPC32467
0.6346 Remote Similarity NPC281972
0.6346 Remote Similarity NPC88966
0.6346 Remote Similarity NPC87394
0.6346 Remote Similarity NPC25417
0.6346 Remote Similarity NPC87564
0.6346 Remote Similarity NPC6095
0.6346 Remote Similarity NPC424
0.6346 Remote Similarity NPC290563
0.6346 Remote Similarity NPC261831
0.6346 Remote Similarity NPC154245
0.6346 Remote Similarity NPC85813
0.6327 Remote Similarity NPC163345
0.6327 Remote Similarity NPC223675
0.6316 Remote Similarity NPC174368
0.6279 Remote Similarity NPC326532

  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 NPC201622 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
0.8919 High Similarity NPD3206 Approved
0.8684 High Similarity NPD633 Phase 3
0.8684 High Similarity NPD9448 Phase 2
0.8537 High Similarity NPD2699 Approved
0.825 Intermediate Similarity NPD2270 Approved
0.8205 Intermediate Similarity NPD9655 Approved
0.8049 Intermediate Similarity NPD387 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD3199 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD6125 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD634 Phase 3
0.725 Intermediate Similarity NPD9449 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3728 Approved
0.7 Intermediate Similarity NPD3730 Approved
0.6809 Remote Similarity NPD622 Approved
0.675 Remote Similarity NPD9447 Approved
0.6739 Remote Similarity NPD9431 Approved
0.6739 Remote Similarity NPD9430 Approved
0.6735 Remote Similarity NPD29 Approved
0.6735 Remote Similarity NPD28 Approved
0.6667 Remote Similarity NPD3729 Clinical (unspecified phase)
0.66 Remote Similarity NPD3186 Phase 1
0.6512 Remote Similarity NPD9450 Approved
0.6512 Remote Similarity NPD77 Approved
0.6471 Remote Similarity NPD3172 Approved
0.6458 Remote Similarity NPD2266 Phase 2
0.6346 Remote Similarity NPD4266 Approved
0.6346 Remote Similarity NPD3196 Approved
0.6346 Remote Similarity NPD615 Clinical (unspecified phase)
0.6346 Remote Similarity NPD3194 Approved
0.6346 Remote Similarity NPD3195 Phase 2
0.6279 Remote Similarity NPD9513 Phase 1
0.6098 Remote Similarity NPD900 Approved
0.6078 Remote Similarity NPD9638 Phase 2
0.6071 Remote Similarity NPD3198 Approved
0.6042 Remote Similarity NPD3174 Discontinued
0.6 Remote Similarity NPD1461 Approved
0.6 Remote Similarity NPD907 Approved
0.6 Remote Similarity NPD908 Approved
0.5897 Remote Similarity NPD62 Approved
0.5814 Remote Similarity NPD370 Phase 3
0.5714 Remote Similarity NPD8616 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8615 Phase 2
0.5714 Remote Similarity NPD8857 Approved
0.5686 Remote Similarity NPD3173 Approved
0.5667 Remote Similarity NPD3197 Phase 1
0.5667 Remote Similarity NPD7909 Approved
0.5652 Remote Similarity NPD9635 Discontinued

  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