Structure

Physi-Chem Properties

Molecular Weight:  164.06
Volume:  201.12
LogP:  4.516
LogD:  3.681
LogS:  -4.968
# Rotatable Bonds:  0
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.515
Synthetic Accessibility Score:  2.812
Fsp3:  0.077
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -3.94
MDCK Permeability:  6.908748036948964e-05
Pgp-inhibitor:  0.05
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.058
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.38

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  101.10640716552734%
Volume Distribution (VD):  1.783
Pgp-substrate:  2.317840099334717%

ADMET: Metabolism

CYP1A2-inhibitor:  0.981
CYP1A2-substrate:  0.492
CYP2C19-inhibitor:  0.884
CYP2C19-substrate:  0.554
CYP2C9-inhibitor:  0.897
CYP2C9-substrate:  0.888
CYP2D6-inhibitor:  0.083
CYP2D6-substrate:  0.397
CYP3A4-inhibitor:  0.615
CYP3A4-substrate:  0.291

ADMET: Excretion

Clearance (CL):  8.463
Half-life (T1/2):  0.102

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.067
Drug-inuced Liver Injury (DILI):  0.984
AMES Toxicity:  0.575
Rat Oral Acute Toxicity:  0.031
Maximum Recommended Daily Dose:  0.277
Skin Sensitization:  0.961
Carcinogencity:  0.526
Eye Corrosion:  0.985
Eye Irritation:  0.996
Respiratory Toxicity:  0.82

Download Data

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

  Natural Product: NPC169110

Natural Product ID:  NPC169110
Common Name*:   Phenylheptatriyne
IUPAC Name:   hepta-1,3,5-triynylbenzene
Synonyms:   Phenylheptatriyne
Standard InCHIKey:  ACKWHAMNCLDPRO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H8/c1-2-3-4-5-7-10-13-11-8-6-9-12-13/h6,8-9,11-12H,1H3
SMILES:  CC#CC#CC#Cc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL444776
PubChem CID:   77981
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted 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
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)88710-5]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np50070a031]
NPO24753 Ballota limbata Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[15056960]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[15165144]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[15844878]
NPO25104 Grindelia scorzonerifolia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15844947]
NPO20454 Bidens pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[16041399]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[16209522]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[17279797]
NPO28581 Aspergillus fumisynnematus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17523650]
NPO9392 Elaeodendron alluaudianum Species Celastraceae Eukaryota n.a. Madagascar Rainforest n.a. PMID[19058971]
NPO9392 Elaeodendron alluaudianum Species Celastraceae Eukaryota n.a. stem n.a. PMID[19058971]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota rhizomes n.a. n.a. PMID[19739599]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. PMID[20488581]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. PMID[20583752]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23186307]
NPO24718 Streptomyces parvulus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23423168]
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[23876370]
NPO1707 Coreopsis lanceolata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24236492]
NPO20454 Bidens pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[469551]
NPO23108 Pinus flexilis Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[9834165]
NPO24190 Uncaria sterrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22685 Astragalus bisulcatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24771 Boenninghausenia albiflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23286 Galium mollugo Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3871 Maclura pomifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22165 Polyscias murrayi Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24771 Boenninghausenia albiflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25266 Baccharoides lasiopus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24753 Ballota limbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22685 Astragalus bisulcatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3871 Maclura pomifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24190 Uncaria sterrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23286 Galium mollugo Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1707 Coreopsis lanceolata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23853 Senegalia mellifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22685 Astragalus bisulcatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24771 Boenninghausenia albiflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24321 Vicia amoena Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4026 Eucalyptus spathulata Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24020 Raputia praetermissa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4837 Cananga latifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9392 Elaeodendron alluaudianum Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24771 Boenninghausenia albiflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23365 Drummondita hassellii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23440 Aconitum napellus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25225 Radianthus kuekenthali n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24687 Sabadilla officinalis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13694 Rhodococcus erythropolis Species 0cardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24405 Farlowia mollis Species Dumontiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22165 Polyscias murrayi Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24718 Streptomyces parvulus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24657 Bothriocline ripensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19691 Mycena fagetorum Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24935 Coronilla cretica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20454 Bidens pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3871 Maclura pomifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24491 Flindersia xanthoxyla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17874 Mus striatus Species Muridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24558 Calea lantanoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24522 Sepia officinalis Species Sepiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3276 Vanillosmopsis pohlii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25190 Lonchocarpus atropurpureus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23286 Galium mollugo Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24190 Uncaria sterrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22685 Astragalus bisulcatus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23144 Brachyglottis bidwillii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24588 Phellinus igniarius Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23749 Achillea nana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO249 Dysosma pleianthum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24811 Cibotium barometz Species Cibotiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22911 Enterococcus faecalis Species Enterococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO1707 Coreopsis lanceolata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23853 Senegalia mellifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25150 Haliclona cribricutis Species Chalinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23656 Typha latifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21796 Lepidium graminifolium Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25104 Grindelia scorzonerifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24753 Ballota limbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12382 Xylaria grammica Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25266 Baccharoides lasiopus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24968 Delphinus globiceps Species Delphinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7066 Gomesa radicans Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24321 Vicia amoena Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24899 Chroogomphus helveticus Species Gomphidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23108 Pinus flexilis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24112 Pisaster giganteus Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25129 Tricholoma acerbum Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19904 Paris delavayi Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28581 Aspergillus fumisynnematus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19819 Trichoderma viride Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22025 Drosera indica Species Droseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15117 Chromolaena odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25065 Gardenia imperialis Species Rubiaceae 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
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 2.57 n.a. PMID[559574]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 0.02 n.a. PMID[559574]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 0.0 n.a. PMID[559574]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 24.2 n.a. PMID[559574]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 35.8 n.a. PMID[559574]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 48.3 n.a. PMID[559574]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 53.5 n.a. PMID[559574]
NPT27 Others Unspecified Activity = 95.0 % PMID[559574]
NPT27 Others Unspecified Activity = 50.0 % PMID[559574]
NPT27 Others Unspecified Activity = 0.0 % PMID[559574]
NPT27 Others Unspecified Activity = 100.0 % PMID[559574]
NPT20 Organism Candida albicans Candida albicans IZ = 11.0 mm PMID[559574]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IZ = 10.0 mm PMID[559574]
NPT1514 Uncleic Acid DNA Bos taurus Activity = 0.18 n.a. PMID[559574]
NPT1514 Uncleic Acid DNA Bos taurus Activity = 0.03 n.a. PMID[559574]
NPT1514 Uncleic Acid DNA Bos taurus Activity = 0.02 n.a. PMID[559574]
NPT1514 Uncleic Acid DNA Bos taurus Activity = 0.01 n.a. PMID[559574]
NPT1514 Uncleic Acid DNA Bos taurus Activity = 0.0 n.a. PMID[559574]
NPT1514 Uncleic Acid DNA Bos taurus Activity = 0.17 n.a. PMID[559574]
NPT1514 Uncleic Acid DNA Bos taurus Activity = 0.19 n.a. PMID[559574]

☑ 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 NPC169110 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
0.9464 High Similarity NPC269586
0.9322 High Similarity NPC200745
0.9298 High Similarity NPC65873
0.9298 High Similarity NPC212114
0.9298 High Similarity NPC300345
0.9298 High Similarity NPC120441
0.9286 High Similarity NPC277704
0.9286 High Similarity NPC149436
0.9138 High Similarity NPC8235
0.9123 High Similarity NPC198841
0.8983 High Similarity NPC147062
0.8833 High Similarity NPC238023
0.8833 High Similarity NPC248705
0.8833 High Similarity NPC135924
0.8833 High Similarity NPC210849
0.8833 High Similarity NPC54368
0.8833 High Similarity NPC310758
0.8833 High Similarity NPC150196
0.8814 High Similarity NPC64270
0.8814 High Similarity NPC114327
0.8814 High Similarity NPC36357
0.8689 High Similarity NPC29680
0.8548 High Similarity NPC88566
0.8525 High Similarity NPC246588
0.8413 Intermediate Similarity NPC198023
0.8413 Intermediate Similarity NPC32312
0.8413 Intermediate Similarity NPC155172
0.8387 Intermediate Similarity NPC22786
0.8387 Intermediate Similarity NPC66517
0.8387 Intermediate Similarity NPC71009
0.8281 Intermediate Similarity NPC178527
0.8254 Intermediate Similarity NPC45756
0.8254 Intermediate Similarity NPC21211
0.8254 Intermediate Similarity NPC113670
0.8226 Intermediate Similarity NPC45255
0.8154 Intermediate Similarity NPC267443
0.8154 Intermediate Similarity NPC6107
0.8125 Intermediate Similarity NPC291066
0.8065 Intermediate Similarity NPC147578
0.803 Intermediate Similarity NPC311343
0.8 Intermediate Similarity NPC36440
0.8 Intermediate Similarity NPC113837
0.8 Intermediate Similarity NPC289915
0.7969 Intermediate Similarity NPC50266
0.7937 Intermediate Similarity NPC200624
0.791 Intermediate Similarity NPC139416
0.791 Intermediate Similarity NPC98880
0.791 Intermediate Similarity NPC213570
0.791 Intermediate Similarity NPC246822
0.7794 Intermediate Similarity NPC95289
0.7761 Intermediate Similarity NPC82770
0.7761 Intermediate Similarity NPC239931
0.7761 Intermediate Similarity NPC78954
0.7681 Intermediate Similarity NPC74458
0.7681 Intermediate Similarity NPC135433
0.7681 Intermediate Similarity NPC326200
0.7681 Intermediate Similarity NPC226999
0.7681 Intermediate Similarity NPC1008
0.7681 Intermediate Similarity NPC280135
0.7681 Intermediate Similarity NPC87099
0.7681 Intermediate Similarity NPC39799
0.7681 Intermediate Similarity NPC193578
0.7681 Intermediate Similarity NPC158028
0.7679 Intermediate Similarity NPC11150
0.7647 Intermediate Similarity NPC235059
0.7647 Intermediate Similarity NPC200936
0.7647 Intermediate Similarity NPC169222
0.7647 Intermediate Similarity NPC5324
0.7647 Intermediate Similarity NPC473206
0.7647 Intermediate Similarity NPC16190
0.7612 Intermediate Similarity NPC52330
0.7576 Intermediate Similarity NPC264470
0.7571 Intermediate Similarity NPC285679
0.7571 Intermediate Similarity NPC54269
0.7571 Intermediate Similarity NPC212463
0.7536 Intermediate Similarity NPC251490
0.7536 Intermediate Similarity NPC263385
0.7536 Intermediate Similarity NPC72670
0.7536 Intermediate Similarity NPC229235
0.75 Intermediate Similarity NPC22760
0.7465 Intermediate Similarity NPC122327
0.7465 Intermediate Similarity NPC113000
0.7465 Intermediate Similarity NPC112609
0.7429 Intermediate Similarity NPC208302
0.7429 Intermediate Similarity NPC155429
0.7391 Intermediate Similarity NPC297358
0.7361 Intermediate Similarity NPC189371
0.7361 Intermediate Similarity NPC276699
0.7361 Intermediate Similarity NPC98976
0.7361 Intermediate Similarity NPC307195
0.7324 Intermediate Similarity NPC1901
0.7324 Intermediate Similarity NPC271437
0.7324 Intermediate Similarity NPC244738
0.7286 Intermediate Similarity NPC219246
0.726 Intermediate Similarity NPC139658
0.726 Intermediate Similarity NPC175393
0.726 Intermediate Similarity NPC271642
0.726 Intermediate Similarity NPC110264
0.7246 Intermediate Similarity NPC181786
0.7222 Intermediate Similarity NPC96835
0.7222 Intermediate Similarity NPC208075
0.7222 Intermediate Similarity NPC258492
0.7222 Intermediate Similarity NPC108218
0.7162 Intermediate Similarity NPC325662
0.7162 Intermediate Similarity NPC298023
0.7162 Intermediate Similarity NPC3190
0.7162 Intermediate Similarity NPC329318
0.7162 Intermediate Similarity NPC3672
0.7162 Intermediate Similarity NPC287790
0.7162 Intermediate Similarity NPC249018
0.7162 Intermediate Similarity NPC98269
0.7162 Intermediate Similarity NPC290638
0.7123 Intermediate Similarity NPC32203
0.7123 Intermediate Similarity NPC206800
0.7067 Intermediate Similarity NPC103488
0.7067 Intermediate Similarity NPC2785
0.7067 Intermediate Similarity NPC285470
0.7067 Intermediate Similarity NPC76455
0.7067 Intermediate Similarity NPC224544
0.7067 Intermediate Similarity NPC137847
0.7067 Intermediate Similarity NPC50192
0.7067 Intermediate Similarity NPC36342
0.7067 Intermediate Similarity NPC12857
0.7027 Intermediate Similarity NPC302129
0.6986 Remote Similarity NPC299134
0.6974 Remote Similarity NPC78517
0.6974 Remote Similarity NPC167577
0.6974 Remote Similarity NPC170484
0.6974 Remote Similarity NPC469894
0.6974 Remote Similarity NPC300205
0.6974 Remote Similarity NPC159661
0.6944 Remote Similarity NPC121708
0.6944 Remote Similarity NPC125144
0.6933 Remote Similarity NPC245966
0.6933 Remote Similarity NPC179726
0.6933 Remote Similarity NPC9796
0.6923 Remote Similarity NPC469807
0.6883 Remote Similarity NPC157055
0.6883 Remote Similarity NPC328178
0.6883 Remote Similarity NPC475289
0.6883 Remote Similarity NPC190567
0.6883 Remote Similarity NPC475573
0.6883 Remote Similarity NPC121800
0.6883 Remote Similarity NPC315216
0.6883 Remote Similarity NPC285716
0.6883 Remote Similarity NPC17408
0.6883 Remote Similarity NPC164086
0.6842 Remote Similarity NPC176228
0.6842 Remote Similarity NPC245896
0.6842 Remote Similarity NPC255345
0.6842 Remote Similarity NPC66270
0.6795 Remote Similarity NPC145053
0.6795 Remote Similarity NPC133050
0.6795 Remote Similarity NPC303245
0.6795 Remote Similarity NPC242628
0.6795 Remote Similarity NPC100039
0.6795 Remote Similarity NPC89950
0.6795 Remote Similarity NPC231986
0.6753 Remote Similarity NPC139901
0.6753 Remote Similarity NPC272260
0.6753 Remote Similarity NPC151405
0.6711 Remote Similarity NPC66655
0.6709 Remote Similarity NPC230068
0.6709 Remote Similarity NPC106313
0.6709 Remote Similarity NPC87299
0.6709 Remote Similarity NPC103387
0.6709 Remote Similarity NPC329319
0.6709 Remote Similarity NPC323103
0.6709 Remote Similarity NPC103326
0.6709 Remote Similarity NPC14326
0.6709 Remote Similarity NPC99394
0.6709 Remote Similarity NPC99240
0.6667 Remote Similarity NPC309279
0.6667 Remote Similarity NPC184030
0.6667 Remote Similarity NPC127343
0.6667 Remote Similarity NPC477703
0.6667 Remote Similarity NPC50063
0.6667 Remote Similarity NPC164449
0.6667 Remote Similarity NPC71664
0.6667 Remote Similarity NPC95868
0.6667 Remote Similarity NPC192623
0.6625 Remote Similarity NPC477770
0.6625 Remote Similarity NPC197581
0.6625 Remote Similarity NPC172984
0.6625 Remote Similarity NPC288903
0.6625 Remote Similarity NPC104070
0.6625 Remote Similarity NPC39600
0.6625 Remote Similarity NPC474088
0.6625 Remote Similarity NPC270507
0.6615 Remote Similarity NPC56072
0.6582 Remote Similarity NPC12936
0.6582 Remote Similarity NPC165212
0.6582 Remote Similarity NPC71795
0.6582 Remote Similarity NPC273033
0.6582 Remote Similarity NPC117180
0.6579 Remote Similarity NPC78500
0.6543 Remote Similarity NPC267704
0.6543 Remote Similarity NPC304538
0.6543 Remote Similarity NPC133162
0.6543 Remote Similarity NPC95429

  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 NPC169110 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
0.8254 Intermediate Similarity NPD675 Discontinued
0.8125 Intermediate Similarity NPD173 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD294 Approved
0.7681 Intermediate Similarity NPD292 Approved
0.7647 Intermediate Similarity NPD9497 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD80 Approved
0.7465 Intermediate Similarity NPD9593 Approved
0.7465 Intermediate Similarity NPD9588 Approved
0.7465 Intermediate Similarity NPD9591 Approved
0.7465 Intermediate Similarity NPD9589 Approved
0.7465 Intermediate Similarity NPD9592 Approved
0.7465 Intermediate Similarity NPD9594 Approved
0.7465 Intermediate Similarity NPD9590 Approved
0.7432 Intermediate Similarity NPD1053 Approved
0.7432 Intermediate Similarity NPD507 Approved
0.7432 Intermediate Similarity NPD1052 Approved
0.7432 Intermediate Similarity NPD508 Approved
0.7432 Intermediate Similarity NPD1051 Approved
0.7391 Intermediate Similarity NPD1673 Approved
0.7324 Intermediate Similarity NPD9728 Phase 1
0.7222 Intermediate Similarity NPD505 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD4144 Approved
0.7162 Intermediate Similarity NPD4147 Approved
0.7162 Intermediate Similarity NPD603 Approved
0.7123 Intermediate Similarity NPD9716 Approved
0.7067 Intermediate Similarity NPD293 Approved
0.7067 Intermediate Similarity NPD296 Approved
0.7067 Intermediate Similarity NPD295 Approved
0.6974 Remote Similarity NPD589 Approved
0.6974 Remote Similarity NPD590 Approved
0.6883 Remote Similarity NPD3979 Approved
0.6883 Remote Similarity NPD5372 Approved
0.6883 Remote Similarity NPD3903 Approved
0.6883 Remote Similarity NPD260 Discontinued
0.6883 Remote Similarity NPD3904 Approved
0.6883 Remote Similarity NPD5371 Approved
0.6883 Remote Similarity NPD3981 Approved
0.6842 Remote Similarity NPD9563 Approved
0.6842 Remote Similarity NPD9564 Approved
0.6842 Remote Similarity NPD227 Approved
0.6842 Remote Similarity NPD9393 Approved
0.6842 Remote Similarity NPD9397 Approved
0.6842 Remote Similarity NPD79 Approved
0.6842 Remote Similarity NPD225 Approved
0.6795 Remote Similarity NPD4027 Approved
0.6795 Remote Similarity NPD472 Approved
0.6795 Remote Similarity NPD3035 Approved
0.6795 Remote Similarity NPD4026 Approved
0.6753 Remote Similarity NPD1475 Approved
0.6711 Remote Similarity NPD9294 Approved
0.6709 Remote Similarity NPD4170 Approved
0.6709 Remote Similarity NPD4169 Approved
0.6709 Remote Similarity NPD4701 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1617 Discontinued
0.6625 Remote Similarity NPD4635 Approved
0.6625 Remote Similarity NPD2001 Discontinued
0.6625 Remote Similarity NPD831 Approved
0.6625 Remote Similarity NPD830 Approved
0.6625 Remote Similarity NPD263 Approved
0.6625 Remote Similarity NPD1800 Clinical (unspecified phase)
0.6625 Remote Similarity NPD262 Approved
0.6625 Remote Similarity NPD3971 Phase 1
0.6613 Remote Similarity NPD9072 Clinical (unspecified phase)
0.6582 Remote Similarity NPD942 Approved
0.6582 Remote Similarity NPD226 Approved
0.6543 Remote Similarity NPD3427 Approved
0.6543 Remote Similarity NPD5178 Approved
0.6543 Remote Similarity NPD4544 Approved
0.6543 Remote Similarity NPD9395 Approved
0.6543 Remote Similarity NPD785 Approved
0.6543 Remote Similarity NPD2538 Approved
0.6543 Remote Similarity NPD2539 Approved
0.6543 Remote Similarity NPD3429 Approved
0.6538 Remote Similarity NPD9490 Approved
0.6463 Remote Similarity NPD2208 Approved
0.6463 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6463 Remote Similarity NPD2205 Approved
0.6456 Remote Similarity NPD914 Suspended
0.6437 Remote Similarity NPD4545 Approved
0.6437 Remote Similarity NPD4542 Approved
0.642 Remote Similarity NPD5288 Clinical (unspecified phase)
0.642 Remote Similarity NPD9491 Approved
0.642 Remote Similarity NPD1185 Approved
0.6386 Remote Similarity NPD4636 Approved
0.6386 Remote Similarity NPD4406 Approved
0.6386 Remote Similarity NPD5252 Clinical (unspecified phase)
0.6386 Remote Similarity NPD4409 Approved
0.631 Remote Similarity NPD1282 Approved
0.631 Remote Similarity NPD650 Approved
0.631 Remote Similarity NPD781 Approved
0.631 Remote Similarity NPD2002 Discontinued
0.631 Remote Similarity NPD3426 Approved
0.631 Remote Similarity NPD1087 Approved
0.631 Remote Similarity NPD780 Approved
0.631 Remote Similarity NPD782 Approved
0.631 Remote Similarity NPD506 Clinical (unspecified phase)
0.631 Remote Similarity NPD4145 Approved
0.631 Remote Similarity NPD783 Approved
0.631 Remote Similarity NPD4146 Approved
0.631 Remote Similarity NPD3428 Approved
0.6265 Remote Similarity NPD111 Approved
0.6265 Remote Similarity NPD5916 Discontinued
0.6265 Remote Similarity NPD9505 Clinical (unspecified phase)
0.6235 Remote Similarity NPD588 Approved
0.6235 Remote Similarity NPD3345 Approved
0.6235 Remote Similarity NPD1101 Approved
0.6235 Remote Similarity NPD5675 Discontinued
0.6235 Remote Similarity NPD587 Approved
0.622 Remote Similarity NPD423 Phase 3
0.622 Remote Similarity NPD4000 Phase 3
0.619 Remote Similarity NPD3099 Discontinued
0.619 Remote Similarity NPD304 Approved
0.619 Remote Similarity NPD305 Approved
0.6173 Remote Similarity NPD9250 Approved
0.6163 Remote Similarity NPD9 Approved
0.6163 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6163 Remote Similarity NPD800 Approved
0.6163 Remote Similarity NPD5346 Phase 2
0.6163 Remote Similarity NPD771 Phase 3
0.6163 Remote Similarity NPD5347 Phase 2
0.6163 Remote Similarity NPD297 Approved
0.6118 Remote Similarity NPD187 Approved
0.6118 Remote Similarity NPD9538 Approved
0.6118 Remote Similarity NPD4793 Discontinued
0.6092 Remote Similarity NPD5915 Approved
0.6092 Remote Similarity NPD3344 Approved
0.6092 Remote Similarity NPD1090 Approved
0.6092 Remote Similarity NPD3673 Approved
0.6092 Remote Similarity NPD3346 Approved
0.6092 Remote Similarity NPD4728 Approved
0.6092 Remote Similarity NPD3672 Approved
0.6092 Remote Similarity NPD1086 Approved
0.6092 Remote Similarity NPD1089 Approved
0.6092 Remote Similarity NPD2811 Clinical (unspecified phase)
0.6067 Remote Similarity NPD735 Approved
0.6067 Remote Similarity NPD736 Approved
0.6047 Remote Similarity NPD531 Approved
0.6023 Remote Similarity NPD3000 Approved
0.6023 Remote Similarity NPD4543 Discontinued
0.6023 Remote Similarity NPD7609 Phase 3
0.6023 Remote Similarity NPD1007 Discontinued
0.6023 Remote Similarity NPD517 Discontinued
0.6023 Remote Similarity NPD2997 Approved
0.6023 Remote Similarity NPD530 Approved
0.6023 Remote Similarity NPD2998 Approved
0.6 Remote Similarity NPD1697 Approved
0.5977 Remote Similarity NPD9349 Approved
0.5977 Remote Similarity NPD1628 Approved
0.5977 Remote Similarity NPD9351 Phase 3
0.5977 Remote Similarity NPD689 Discontinued
0.5977 Remote Similarity NPD1629 Approved
0.5977 Remote Similarity NPD9350 Approved
0.5977 Remote Similarity NPD9348 Approved
0.5955 Remote Similarity NPD1814 Approved
0.5955 Remote Similarity NPD1812 Approved
0.5955 Remote Similarity NPD1088 Approved
0.5955 Remote Similarity NPD4407 Approved
0.5955 Remote Similarity NPD6690 Approved
0.5955 Remote Similarity NPD7631 Approved
0.5955 Remote Similarity NPD4408 Approved
0.5955 Remote Similarity NPD752 Approved
0.5955 Remote Similarity NPD4405 Approved
0.5889 Remote Similarity NPD3719 Approved
0.5889 Remote Similarity NPD5122 Clinical (unspecified phase)
0.5889 Remote Similarity NPD1563 Approved
0.5889 Remote Similarity NPD1066 Discontinued
0.5889 Remote Similarity NPD837 Approved
0.5889 Remote Similarity NPD719 Approved
0.5889 Remote Similarity NPD845 Approved
0.5889 Remote Similarity NPD1409 Phase 3
0.5889 Remote Similarity NPD3980 Approved
0.5889 Remote Similarity NPD2878 Approved
0.5889 Remote Similarity NPD3718 Approved
0.5889 Remote Similarity NPD720 Approved
0.5889 Remote Similarity NPD1080 Approved
0.5889 Remote Similarity NPD3982 Approved
0.5862 Remote Similarity NPD9184 Approved
0.5862 Remote Similarity NPD9186 Approved
0.5843 Remote Similarity NPD7160 Approved
0.5843 Remote Similarity NPD1239 Approved
0.5824 Remote Similarity NPD2933 Approved
0.5824 Remote Similarity NPD4814 Discontinued
0.5824 Remote Similarity NPD2655 Approved
0.5824 Remote Similarity NPD1081 Clinical (unspecified phase)
0.5824 Remote Similarity NPD4094 Approved
0.5824 Remote Similarity NPD2934 Approved
0.5824 Remote Similarity NPD1693 Approved
0.5824 Remote Similarity NPD5554 Approved
0.5824 Remote Similarity NPD2656 Approved
0.5824 Remote Similarity NPD6048 Clinical (unspecified phase)
0.5824 Remote Similarity NPD7343 Discovery
0.5824 Remote Similarity NPD6049 Phase 2
0.5824 Remote Similarity NPD1432 Clinical (unspecified phase)
0.5824 Remote Similarity NPD7344 Phase 1
0.5814 Remote Similarity NPD9259 Approved
0.5814 Remote Similarity NPD9257 Approved
0.5778 Remote Similarity NPD9361 Approved
0.5778 Remote Similarity NPD159 Clinical (unspecified phase)
0.5778 Remote Similarity NPD1508 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