Structure

Physi-Chem Properties

Molecular Weight:  263.19
Volume:  300.687
LogP:  1.421
LogD:  0.919
LogS:  -2.181
# Rotatable Bonds:  9
TPSA:  49.33
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  0
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.522
Synthetic Accessibility Score:  3.27
Fsp3:  0.438
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.08
MDCK Permeability:  4.3783762521343306e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.854
Plasma Protein Binding (PPB):  68.44783782958984%
Volume Distribution (VD):  1.125
Pgp-substrate:  24.498262405395508%

ADMET: Metabolism

CYP1A2-inhibitor:  0.187
CYP1A2-substrate:  0.239
CYP2C19-inhibitor:  0.358
CYP2C19-substrate:  0.419
CYP2C9-inhibitor:  0.177
CYP2C9-substrate:  0.927
CYP2D6-inhibitor:  0.636
CYP2D6-substrate:  0.625
CYP3A4-inhibitor:  0.58
CYP3A4-substrate:  0.155

ADMET: Excretion

Clearance (CL):  9.037
Half-life (T1/2):  0.742

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.1
Drug-inuced Liver Injury (DILI):  0.029
AMES Toxicity:  0.14
Rat Oral Acute Toxicity:  0.028
Maximum Recommended Daily Dose:  0.428
Skin Sensitization:  0.929
Carcinogencity:  0.498
Eye Corrosion:  0.028
Eye Irritation:  0.355
Respiratory Toxicity:  0.863

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  Natural Product: NPC184014

Natural Product ID:  NPC184014
Common Name*:   Hydroxy-Alpha-Sanshool
IUPAC Name:   (2E,6Z,8E,10E)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide
Synonyms:   Hydroxy-Alpha-Sanshool
Standard InCHIKey:  LHFKHAVGGJJQFF-UEOYEZOQSA-N
Standard InCHI:  InChI=1S/C16H25NO2/c1-4-5-6-7-8-9-10-11-12-13-15(18)17-14-16(2,3)19/h4-9,12-13,19H,10-11,14H2,1-3H3,(H,17,18)/b5-4+,7-6+,9-8-,13-12+
SMILES:  C/C=C/C=C/C=CCC/C=C/C(=NCC(O)(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1084610
PubChem CID:   10084135
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000331] Fatty amides
          • [CHEMONTID:0001096] N-acyl amines

*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
NPO5852 Litsea glutinosa Species Lauraceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(00)88469-1]
NPO5852 Litsea glutinosa Species Lauraceae Eukaryota n.a. stem n.a. DOI[10.1016/S0031-9422(00)88469-1]
NPO9553 Phyllodium pulchellum Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[15921433]
NPO33007 nepalese zanthoxylum armatum Species n.a. n.a. pericarp n.a. n.a. PMID[23268719]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[24175626]
NPO12970 Aspergillus fischeri Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31920082]
NPO10128 Aplysia punctata Species Aplysiidae Eukaryota n.a. n.a. n.a. PMID[9213585]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5131 Scorzonera hispanica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8642 Lithospermum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4340 Peucedanum praeruptorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6320 Echinosophora koreensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4120 Ulmus americana Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5852 Litsea glutinosa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9087 Sarcococca vagans Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8471 Angelica taiwaniana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1070 Matricaria suffruticosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2892 Wikstroemia chamaedaphne Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9783 Mikania scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8642 Lithospermum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5852 Litsea glutinosa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2892 Wikstroemia chamaedaphne Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5131 Scorzonera hispanica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8471 Angelica taiwaniana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4340 Peucedanum praeruptorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4120 Ulmus americana Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9087 Sarcococca vagans Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6320 Echinosophora koreensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1070 Matricaria suffruticosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9783 Mikania scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26898 Jacobaea vulgaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9783 Mikania scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8642 Lithospermum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9087 Sarcococca vagans Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4340 Peucedanum praeruptorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4340 Peucedanum praeruptorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4120 Ulmus americana Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14793 Erica glauca Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16266 Didymium bahiense Species Didymiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9733 Spongia bilamellata Species Spongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6378 Wilcoxia viperina n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4340 Peucedanum praeruptorum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8253 Alexandrium hiranoi Species Gonyaulacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9221 Trachelospermum lucidum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12591 Archaster typicus Species Archasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20059.1 Lactobacillus delbrueckii subsp. bulgaricus Subspecies Lactobacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12367 Diospyros elliptifolia Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1070 Matricaria suffruticosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6386 Gutenbergia cordifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9361 Aplophyllum villosum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13555 Beaucarnea recurvata Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9476 Metapenaeus bennettae Species Penaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7870 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9590 Xanthoria aureola Species Teloschistaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO777 Kielmeyera coriacea Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8601 Petrosia volcano Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6894 Elegia deusta Species Restionaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12233 Diospyros peregrina Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2199 Tecoma pentaphylla Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10264 Platonia insignis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12819 Clitocybe subilludens Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3341 Leishmania major Species Trypanosomatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22899 Phaeotremella fagi Species Phaeotremellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7028 Sida veronicaefolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1682 Rhytidoponera metallica Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7847 Senecio densiflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2892 Wikstroemia chamaedaphne Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7841 Solanum transcaucasicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10128 Aplysia punctata Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7650 Salvia munzii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8471 Angelica taiwaniana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13438 Centaurea calcitrapa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9995 Cynara humilis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5604 Chelonia japonica Species Cheloniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8642 Lithospermum officinale Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4746 Centaurea arenaria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4523 Reaumuria hirtella Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9553 Phyllodium pulchellum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11333 Trapa japonica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6320 Echinosophora koreensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6801 Bellium bellidioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1326 Cratystylis conocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6556 Garcinia intermedia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2015 Udotea petiolata Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12970 Aspergillus fischeri Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8022 Consolida hohenackeri Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9989 Cotylelobium scabriusculum Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1467 Wedelia prostrata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15558 Leucas neufliseana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13042 Diospyros abyssinica Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26898 Jacobaea vulgaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9087 Sarcococca vagans Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9783 Mikania scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2999 Coprinellus flocculosus Species Psathyrellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5852 Litsea glutinosa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4895 Coleus esquirolii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5131 Scorzonera hispanica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24083.1 Melanelixia fuliginosa subsp. glabratula Subspecies Parmeliaceae 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
NPT346 Individual Protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens EC50 = 6600.0 nM PMID[478695]
NPT472 Individual Protein Vanilloid receptor Homo sapiens EC50 = 1100.0 nM PMID[478695]
NPT1287 Individual Protein Cannabinoid CB2 receptor Homo sapiens Inhibition = 29.0 % PMID[478697]
NPT1287 Individual Protein Cannabinoid CB2 receptor Homo sapiens IC50 = 59.0 nM PMID[478697]
NPT232 Individual Protein Cannabinoid CB1 receptor Homo sapiens Inhibition = 29.0 % PMID[478697]
NPT232 Individual Protein Cannabinoid CB1 receptor Homo sapiens IC50 = 7400.0 nM PMID[478697]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI = 53.0 % PMID[478696]
NPT27 Others Unspecified Activity = 106.0 % PMID[478696]
NPT2 Others Unspecified Ratio IC50 = 1254.0 n.a. PMID[478697]

☑ 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 NPC184014 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 NPC14234
1.0 High Similarity NPC132669
1.0 High Similarity NPC269800
1.0 High Similarity NPC246519
1.0 High Similarity NPC44193
0.9091 High Similarity NPC312826
0.902 High Similarity NPC304223
0.902 High Similarity NPC267340
0.902 High Similarity NPC145032
0.902 High Similarity NPC54542
0.902 High Similarity NPC243539
0.8824 High Similarity NPC307435
0.8824 High Similarity NPC267692
0.8679 High Similarity NPC119655
0.8679 High Similarity NPC303672
0.8621 High Similarity NPC471023
0.8519 High Similarity NPC305288
0.8519 High Similarity NPC163912
0.8519 High Similarity NPC167759
0.8519 High Similarity NPC56028
0.8491 Intermediate Similarity NPC195986
0.8475 Intermediate Similarity NPC253468
0.8475 Intermediate Similarity NPC235311
0.8421 Intermediate Similarity NPC74617
0.8421 Intermediate Similarity NPC150505
0.8364 Intermediate Similarity NPC471992
0.8364 Intermediate Similarity NPC297020
0.8364 Intermediate Similarity NPC273023
0.8364 Intermediate Similarity NPC471991
0.8305 Intermediate Similarity NPC77891
0.8276 Intermediate Similarity NPC6795
0.8214 Intermediate Similarity NPC261158
0.8214 Intermediate Similarity NPC24216
0.8214 Intermediate Similarity NPC306420
0.8214 Intermediate Similarity NPC104138
0.8214 Intermediate Similarity NPC477049
0.8182 Intermediate Similarity NPC123669
0.807 Intermediate Similarity NPC245650
0.7833 Intermediate Similarity NPC273614
0.7812 Intermediate Similarity NPC471022
0.7742 Intermediate Similarity NPC477525
0.7619 Intermediate Similarity NPC315141
0.7619 Intermediate Similarity NPC129995
0.7619 Intermediate Similarity NPC187315
0.7544 Intermediate Similarity NPC124382
0.7544 Intermediate Similarity NPC13011
0.7407 Intermediate Similarity NPC91044
0.7377 Intermediate Similarity NPC130807
0.7258 Intermediate Similarity NPC324077
0.6984 Remote Similarity NPC29468
0.6981 Remote Similarity NPC86121
0.6957 Remote Similarity NPC314678
0.6875 Remote Similarity NPC182758
0.6833 Remote Similarity NPC242930
0.6825 Remote Similarity NPC309877
0.6721 Remote Similarity NPC4881
0.6667 Remote Similarity NPC470439
0.6618 Remote Similarity NPC249713
0.6522 Remote Similarity NPC103712
0.6522 Remote Similarity NPC291196
0.6508 Remote Similarity NPC325734
0.6508 Remote Similarity NPC321030
0.6429 Remote Similarity NPC299114
0.6406 Remote Similarity NPC326524
0.6406 Remote Similarity NPC325550
0.6406 Remote Similarity NPC329003
0.6364 Remote Similarity NPC477106
0.6329 Remote Similarity NPC3210
0.6286 Remote Similarity NPC45060
0.6286 Remote Similarity NPC280065
0.625 Remote Similarity NPC210999
0.625 Remote Similarity NPC138935
0.6184 Remote Similarity NPC313911
0.6184 Remote Similarity NPC314854
0.6164 Remote Similarity NPC288086
0.6119 Remote Similarity NPC316674
0.6111 Remote Similarity NPC56917
0.6066 Remote Similarity NPC208638
0.6 Remote Similarity NPC474460
0.6 Remote Similarity NPC328784
0.6 Remote Similarity NPC291437
0.5902 Remote Similarity NPC71053
0.5902 Remote Similarity NPC59408
0.5893 Remote Similarity NPC180871
0.5893 Remote Similarity NPC67761
0.5893 Remote Similarity NPC68889
0.5893 Remote Similarity NPC194586
0.5893 Remote Similarity NPC206906
0.5893 Remote Similarity NPC88079
0.5893 Remote Similarity NPC108494
0.5893 Remote Similarity NPC209279
0.5893 Remote Similarity NPC51758
0.5882 Remote Similarity NPC55068
0.5867 Remote Similarity NPC476923
0.5789 Remote Similarity NPC263266
0.5789 Remote Similarity NPC116934
0.5763 Remote Similarity NPC282097
0.5763 Remote Similarity NPC180575
0.575 Remote Similarity NPC14326
0.5738 Remote Similarity NPC221467
0.5714 Remote Similarity NPC269823
0.5714 Remote Similarity NPC61177
0.5679 Remote Similarity NPC228638
0.5658 Remote Similarity NPC476924
0.5645 Remote Similarity NPC43053
0.5645 Remote Similarity NPC261571
0.5636 Remote Similarity NPC103213
0.5636 Remote Similarity NPC255042
0.5636 Remote Similarity NPC29091
0.5636 Remote Similarity NPC15934
0.5636 Remote Similarity NPC182840
0.5625 Remote Similarity NPC110732
0.5625 Remote Similarity NPC82799
0.5614 Remote Similarity NPC213538
0.5614 Remote Similarity NPC256766

  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 NPC184014 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
0.6727 Remote Similarity NPD860 Phase 2
0.6102 Remote Similarity NPD4220 Pre-registration
0.5882 Remote Similarity NPD3210 Clinical (unspecified phase)
0.5758 Remote Similarity NPD9368 Phase 2

  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