NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	148.09
Volume:	171.204
LogP:	1.706
LogD:	1.883
LogS:	-1.949
# Rotatable Bonds:	3
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.642
Synthetic Accessibility Score:	1.363
Fsp3:	0.3
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:	-4.33
MDCK Permeability:	2.957653305202257e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.901
Plasma Protein Binding (PPB):	84.77043151855469%
Volume Distribution (VD):	1.084
Pgp-substrate:	11.912028312683105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.877
CYP2C19-inhibitor:	0.774
CYP2C19-substrate:	0.49
CYP2C9-inhibitor:	0.174
CYP2C9-substrate:	0.461
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.65
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.331

ADMET: Excretion

Clearance (CL):	8.074
Half-life (T1/2):	0.812

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.322
Carcinogencity:	0.344
Eye Corrosion:	0.932
Eye Irritation:	0.99
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC74458

Natural Product ID:	NPC74458
*Common Name:**	Benzylacetone
IUPAC Name:	4-phenylbutan-2-one
Synonyms:
Standard InCHIKey:	AKGGYBADQZYZPD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3
SMILES:	CC(=O)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1490851
PubChem CID:	17355
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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO18673	Rhododendron anthopogonoides	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20586436]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO1903	Cyperus haspan	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18673	Rhododendron anthopogonoides	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18673	Rhododendron anthopogonoides	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4711	Goniothalamus thwaitesii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1903	Cyperus haspan	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18673	Rhododendron anthopogonoides	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1903	Cyperus haspan	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO51	Petalonia fascia	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1903	Cyperus haspan	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5646	Phoma violacea	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17388	Schefferomitra subaequalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO979	Salvinia imbricata	Species	Salviniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18673	Rhododendron anthopogonoides	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6605	Neodiprion sertifer	Species	Diprionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4711	Goniothalamus thwaitesii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23628	Imperata cylindrica	Species	Poaceae	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

Activity Type	# Activity
IC50	1
Others	4
Potency	9

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Organism	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	389	nM	PubChem BioAssay data set
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[474964]
NPT80	Cell Line	Raji	Homo sapiens	IC50	=	222.0	molar ratio	PMID[474966]
NPT2	Others	Unspecified		Potency	n.a.	2775.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	489.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	69707.2	nM	PubChem BioAssay data set
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	5011.9	nM	PMID[474963]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	25118.9	nM	PMID[474963]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[474964]
NPT724	Organism	Corticium	Corticium	GI	=	100.0	%	PMID[474965]
NPT724	Organism	Corticium	Corticium	GI	=	30.5	%	PMID[474965]
NPT723	Organism	Pythium	Pythium	GI	=	100.0	%	PMID[474965]
NPT723	Organism	Pythium	Pythium	GI	=	24.5	%	PMID[474965]

☑ 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 NPC74458 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	2300
0.2-0.3	7329
0.3-0.4	16696
0.4-0.5	12566
0.5-0.6	2738
0.6-0.7	584
0.7-0.8	177
0.8-0.85	24
0.85-0.9	23
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC285679
0.9167	High Similarity	NPC2785
0.9167	High Similarity	NPC285470
0.9167	High Similarity	NPC103488
0.9167	High Similarity	NPC36342
0.9041	High Similarity	NPC300205
0.9028	High Similarity	NPC245966
0.9028	High Similarity	NPC9796
0.9	High Similarity	NPC271437
0.8919	High Similarity	NPC285716
0.8919	High Similarity	NPC164086
0.8919	High Similarity	NPC190567
0.8919	High Similarity	NPC17408
0.8873	High Similarity	NPC208075
0.8841	High Similarity	NPC98880
0.88	High Similarity	NPC145053
0.8784	High Similarity	NPC139901
0.8784	High Similarity	NPC272260
0.8784	High Similarity	NPC151405
0.8767	High Similarity	NPC298023
0.8714	High Similarity	NPC95289
0.8696	High Similarity	NPC311343
0.8667	High Similarity	NPC95868
0.8667	High Similarity	NPC477703
0.8667	High Similarity	NPC71664
0.8649	High Similarity	NPC137847
0.8649	High Similarity	NPC76455
0.8553	High Similarity	NPC12936
0.8553	High Similarity	NPC273033
0.8514	High Similarity	NPC329318
0.8421	Intermediate Similarity	NPC157055
0.8333	Intermediate Similarity	NPC273758
0.8312	Intermediate Similarity	NPC73978
0.825	Intermediate Similarity	NPC160339
0.825	Intermediate Similarity	NPC307
0.8205	Intermediate Similarity	NPC230068
0.8182	Intermediate Similarity	NPC212114
0.8182	Intermediate Similarity	NPC300345
0.8182	Intermediate Similarity	NPC127343
0.8182	Intermediate Similarity	NPC120441
0.8182	Intermediate Similarity	NPC65873
0.8148	Intermediate Similarity	NPC43945
0.8148	Intermediate Similarity	NPC69057
0.8125	Intermediate Similarity	NPC123476
0.8125	Intermediate Similarity	NPC95965
0.8101	Intermediate Similarity	NPC39600
0.8101	Intermediate Similarity	NPC215008
0.8101	Intermediate Similarity	NPC324624
0.8101	Intermediate Similarity	NPC288903
0.8101	Intermediate Similarity	NPC197581
0.8082	Intermediate Similarity	NPC326200
0.8077	Intermediate Similarity	NPC100039
0.8049	Intermediate Similarity	NPC157778
0.803	Intermediate Similarity	NPC198841
0.803	Intermediate Similarity	NPC269586
0.8026	Intermediate Similarity	NPC179726
0.7952	Intermediate Similarity	NPC231591
0.7952	Intermediate Similarity	NPC298115
0.7901	Intermediate Similarity	NPC252067
0.7901	Intermediate Similarity	NPC294134
0.7895	Intermediate Similarity	NPC78500
0.7879	Intermediate Similarity	NPC149436
0.7879	Intermediate Similarity	NPC277704
0.7875	Intermediate Similarity	NPC44830
0.7875	Intermediate Similarity	NPC285773
0.7857	Intermediate Similarity	NPC110420
0.7857	Intermediate Similarity	NPC173413
0.7857	Intermediate Similarity	NPC67585
0.7857	Intermediate Similarity	NPC277277
0.7857	Intermediate Similarity	NPC303967
0.7838	Intermediate Similarity	NPC155429
0.7831	Intermediate Similarity	NPC267262
0.7831	Intermediate Similarity	NPC477693
0.7831	Intermediate Similarity	NPC473345
0.7831	Intermediate Similarity	NPC477704
0.7826	Intermediate Similarity	NPC238023
0.7826	Intermediate Similarity	NPC54368
0.7826	Intermediate Similarity	NPC310758
0.7826	Intermediate Similarity	NPC135924
0.7826	Intermediate Similarity	NPC210849
0.7826	Intermediate Similarity	NPC150196
0.7826	Intermediate Similarity	NPC248705
0.7808	Intermediate Similarity	NPC235059
0.7808	Intermediate Similarity	NPC169222
0.7808	Intermediate Similarity	NPC16190
0.7794	Intermediate Similarity	NPC8235
0.7765	Intermediate Similarity	NPC133461
0.7765	Intermediate Similarity	NPC284475
0.7765	Intermediate Similarity	NPC476484
0.7738	Intermediate Similarity	NPC418308
0.7738	Intermediate Similarity	NPC113307
0.7714	Intermediate Similarity	NPC29680
0.7711	Intermediate Similarity	NPC322387
0.7681	Intermediate Similarity	NPC147062
0.7681	Intermediate Similarity	NPC169110
0.7674	Intermediate Similarity	NPC59677
0.7674	Intermediate Similarity	NPC155232
0.7674	Intermediate Similarity	NPC153885
0.7674	Intermediate Similarity	NPC1682
0.7674	Intermediate Similarity	NPC188844
0.7654	Intermediate Similarity	NPC149263
0.7647	Intermediate Similarity	NPC84288
0.7647	Intermediate Similarity	NPC19256
0.7619	Intermediate Similarity	NPC329064
0.7619	Intermediate Similarity	NPC153308
0.7606	Intermediate Similarity	NPC88566
0.759	Intermediate Similarity	NPC164526
0.7586	Intermediate Similarity	NPC289883
0.7586	Intermediate Similarity	NPC238219
0.7586	Intermediate Similarity	NPC291070
0.7586	Intermediate Similarity	NPC246757
0.7571	Intermediate Similarity	NPC246588
0.7558	Intermediate Similarity	NPC141607
0.7558	Intermediate Similarity	NPC187725
0.7536	Intermediate Similarity	NPC36357
0.7536	Intermediate Similarity	NPC114327
0.7536	Intermediate Similarity	NPC64270
0.7532	Intermediate Similarity	NPC189371
0.7531	Intermediate Similarity	NPC323103
0.75	Intermediate Similarity	NPC121800
0.75	Intermediate Similarity	NPC198023
0.75	Intermediate Similarity	NPC194326
0.75	Intermediate Similarity	NPC155172
0.75	Intermediate Similarity	NPC260233
0.75	Intermediate Similarity	NPC32312
0.7471	Intermediate Similarity	NPC323420
0.7471	Intermediate Similarity	NPC77273
0.7465	Intermediate Similarity	NPC71009
0.7465	Intermediate Similarity	NPC22786
0.7465	Intermediate Similarity	NPC66517
0.7442	Intermediate Similarity	NPC274455
0.7442	Intermediate Similarity	NPC58872
0.7442	Intermediate Similarity	NPC86670
0.7442	Intermediate Similarity	NPC70940
0.7439	Intermediate Similarity	NPC270507
0.7436	Intermediate Similarity	NPC175393
0.7432	Intermediate Similarity	NPC239931
0.7432	Intermediate Similarity	NPC82770
0.7432	Intermediate Similarity	NPC78954
0.7416	Intermediate Similarity	NPC185208
0.7416	Intermediate Similarity	NPC219573
0.7416	Intermediate Similarity	NPC12695
0.7397	Intermediate Similarity	NPC178527
0.7386	Intermediate Similarity	NPC34243
0.7375	Intermediate Similarity	NPC170484
0.7368	Intermediate Similarity	NPC208302
0.7361	Intermediate Similarity	NPC21211
0.7361	Intermediate Similarity	NPC45756
0.7361	Intermediate Similarity	NPC113670
0.7356	Intermediate Similarity	NPC317645
0.7356	Intermediate Similarity	NPC110704
0.7356	Intermediate Similarity	NPC125226
0.7342	Intermediate Similarity	NPC3672
0.7342	Intermediate Similarity	NPC287790
0.7333	Intermediate Similarity	NPC103048
0.7333	Intermediate Similarity	NPC239185
0.7333	Intermediate Similarity	NPC240042
0.7326	Intermediate Similarity	NPC325709
0.7326	Intermediate Similarity	NPC9822
0.7317	Intermediate Similarity	NPC103387
0.7308	Intermediate Similarity	NPC32203
0.7308	Intermediate Similarity	NPC206800
0.7303	Intermediate Similarity	NPC472880
0.7303	Intermediate Similarity	NPC206764
0.7297	Intermediate Similarity	NPC6107
0.7297	Intermediate Similarity	NPC267443
0.726	Intermediate Similarity	NPC291066
0.7253	Intermediate Similarity	NPC134882
0.7253	Intermediate Similarity	NPC145052
0.7253	Intermediate Similarity	NPC49994
0.7253	Intermediate Similarity	NPC75724
0.7253	Intermediate Similarity	NPC260000
0.725	Intermediate Similarity	NPC50192
0.7222	Intermediate Similarity	NPC200745
0.7195	Intermediate Similarity	NPC89950
0.7191	Intermediate Similarity	NPC71140
0.7179	Intermediate Similarity	NPC108218
0.7174	Intermediate Similarity	NPC476042
0.7174	Intermediate Similarity	NPC280869
0.7174	Intermediate Similarity	NPC54647
0.7162	Intermediate Similarity	NPC113837
0.7162	Intermediate Similarity	NPC289915
0.716	Intermediate Similarity	NPC167577
0.716	Intermediate Similarity	NPC78517
0.7159	Intermediate Similarity	NPC103346
0.7159	Intermediate Similarity	NPC86987
0.7143	Intermediate Similarity	NPC477767
0.7143	Intermediate Similarity	NPC265220
0.7143	Intermediate Similarity	NPC267704
0.7143	Intermediate Similarity	NPC289201
0.7123	Intermediate Similarity	NPC50266
0.7108	Intermediate Similarity	NPC99240
0.7105	Intermediate Similarity	NPC246822
0.7105	Intermediate Similarity	NPC139416
0.7105	Intermediate Similarity	NPC213570
0.7097	Intermediate Similarity	NPC109514
0.7097	Intermediate Similarity	NPC476993
0.7097	Intermediate Similarity	NPC112552
0.7083	Intermediate Similarity	NPC45255
0.7079	Intermediate Similarity	NPC323164

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 NPC74458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	1100
0.2-0.3	1808
0.3-0.4	3417
0.4-0.5	1758
0.5-0.6	658
0.6-0.7	135
0.7-0.8	31
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD1507	Clinical (unspecified phase)
0.8553	High Similarity	NPD942	Approved
0.84	Intermediate Similarity	NPD225	Approved
0.84	Intermediate Similarity	NPD227	Approved
0.8148	Intermediate Similarity	NPD650	Approved
0.8148	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD226	Approved
0.8052	Intermediate Similarity	NPD9490	Approved
0.7875	Intermediate Similarity	NPD9491	Approved
0.7765	Intermediate Similarity	NPD7609	Phase 3
0.7711	Intermediate Similarity	NPD1087	Approved
0.7674	Intermediate Similarity	NPD7631	Approved
0.7586	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5346	Phase 2
0.7529	Intermediate Similarity	NPD5347	Phase 2
0.7529	Intermediate Similarity	NPD800	Approved
0.75	Intermediate Similarity	NPD4094	Approved
0.75	Intermediate Similarity	NPD1693	Approved
0.75	Intermediate Similarity	NPD4793	Discontinued
0.7471	Intermediate Similarity	NPD1508	Approved
0.7442	Intermediate Similarity	NPD3672	Approved
0.7442	Intermediate Similarity	NPD1086	Approved
0.7442	Intermediate Similarity	NPD1090	Approved
0.7442	Intermediate Similarity	NPD3673	Approved
0.7442	Intermediate Similarity	NPD1089	Approved
0.7361	Intermediate Similarity	NPD675	Discontinued
0.7333	Intermediate Similarity	NPD1100	Approved
0.7333	Intermediate Similarity	NPD1099	Approved
0.7333	Intermediate Similarity	NPD4655	Approved
0.7333	Intermediate Similarity	NPD4657	Approved
0.7333	Intermediate Similarity	NPD3495	Discontinued
0.7308	Intermediate Similarity	NPD9716	Approved
0.7273	Intermediate Similarity	NPD1088	Approved
0.726	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1843	Approved
0.7191	Intermediate Similarity	NPD1563	Approved
0.7174	Intermediate Similarity	NPD2066	Phase 3
0.7159	Intermediate Similarity	NPD1239	Approved
0.7105	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD1989	Approved
0.7024	Intermediate Similarity	NPD3971	Phase 1
0.7021	Intermediate Similarity	NPD2196	Discontinued
0.7021	Intermediate Similarity	NPD2171	Approved
0.7021	Intermediate Similarity	NPD6027	Approved
0.7021	Intermediate Similarity	NPD2193	Phase 2
0.7021	Intermediate Similarity	NPD6024	Approved
0.7021	Intermediate Similarity	NPD2648	Phase 3
0.6977	Remote Similarity	NPD9259	Approved
0.6977	Remote Similarity	NPD9257	Approved
0.6966	Remote Similarity	NPD1007	Discontinued
0.6957	Remote Similarity	NPD1566	Phase 3
0.6957	Remote Similarity	NPD1565	Approved
0.6957	Remote Similarity	NPD1564	Approved
0.6947	Remote Similarity	NPD1929	Approved
0.6947	Remote Similarity	NPD3357	Discontinued
0.6947	Remote Similarity	NPD1930	Approved
0.6947	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD292	Approved
0.6923	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD294	Approved
0.6882	Remote Similarity	NPD466	Approved
0.6882	Remote Similarity	NPD9495	Approved
0.686	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1932	Approved
0.6813	Remote Similarity	NPD1202	Approved
0.6809	Remote Similarity	NPD7798	Approved
0.6809	Remote Similarity	NPD742	Approved
0.6804	Remote Similarity	NPD1677	Discontinued
0.6804	Remote Similarity	NPD2192	Approved
0.6804	Remote Similarity	NPD2197	Approved
0.6774	Remote Similarity	NPD9566	Approved
0.675	Remote Similarity	NPD9590	Approved
0.675	Remote Similarity	NPD9593	Approved
0.675	Remote Similarity	NPD80	Approved
0.675	Remote Similarity	NPD9594	Approved
0.675	Remote Similarity	NPD9588	Approved
0.675	Remote Similarity	NPD9592	Approved
0.675	Remote Similarity	NPD9591	Approved
0.675	Remote Similarity	NPD9589	Approved
0.6737	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1282	Approved
0.6702	Remote Similarity	NPD253	Approved
0.6701	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5909	Discontinued
0.6701	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD1673	Approved
0.6667	Remote Similarity	NPD9258	Approved
0.6667	Remote Similarity	NPD9256	Approved
0.6667	Remote Similarity	NPD4803	Discontinued
0.6632	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1066	Discontinued
0.6625	Remote Similarity	NPD9728	Phase 1
0.66	Remote Similarity	NPD2329	Discontinued
0.6598	Remote Similarity	NPD6647	Phase 2
0.6543	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1317	Discontinued
0.6531	Remote Similarity	NPD164	Approved
0.6506	Remote Similarity	NPD9294	Approved
0.6506	Remote Similarity	NPD4147	Approved
0.6506	Remote Similarity	NPD4144	Approved
0.6495	Remote Similarity	NPD813	Approved
0.6471	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD1763	Approved
0.6465	Remote Similarity	NPD5048	Discontinued
0.6465	Remote Similarity	NPD1767	Approved
0.6465	Remote Similarity	NPD1765	Approved
0.6465	Remote Similarity	NPD1018	Approved
0.6465	Remote Similarity	NPD1761	Approved
0.6465	Remote Similarity	NPD1766	Approved
0.6458	Remote Similarity	NPD1238	Approved
0.6429	Remote Similarity	NPD296	Approved
0.6429	Remote Similarity	NPD295	Approved
0.6429	Remote Similarity	NPD293	Approved
0.6408	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.64	Remote Similarity	NPD467	Phase 1
0.6383	Remote Similarity	NPD9260	Approved
0.6373	Remote Similarity	NPD664	Approved
0.6373	Remote Similarity	NPD2067	Discontinued
0.6353	Remote Similarity	NPD1052	Approved
0.6353	Remote Similarity	NPD1051	Approved
0.6353	Remote Similarity	NPD589	Approved
0.6353	Remote Similarity	NPD1053	Approved
0.6353	Remote Similarity	NPD590	Approved
0.6346	Remote Similarity	NPD6858	Approved
0.6346	Remote Similarity	NPD7094	Approved
0.6311	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.631	Remote Similarity	NPD603	Approved
0.6292	Remote Similarity	NPD111	Approved
0.6286	Remote Similarity	NPD7076	Approved
0.6286	Remote Similarity	NPD1241	Discontinued
0.6286	Remote Similarity	NPD7077	Approved
0.6279	Remote Similarity	NPD260	Discontinued
0.6279	Remote Similarity	NPD5371	Approved
0.6279	Remote Similarity	NPD3979	Approved
0.6279	Remote Similarity	NPD3904	Approved
0.6279	Remote Similarity	NPD3903	Approved
0.6279	Remote Similarity	NPD3981	Approved
0.6279	Remote Similarity	NPD5372	Approved
0.6275	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD2182	Approved
0.6264	Remote Similarity	NPD1101	Approved
0.6263	Remote Similarity	NPD5765	Approved
0.6263	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6685	Approved
0.6235	Remote Similarity	NPD9563	Approved
0.6235	Remote Similarity	NPD9393	Approved
0.6235	Remote Similarity	NPD9564	Approved
0.6235	Remote Similarity	NPD9397	Approved
0.6235	Remote Similarity	NPD79	Approved
0.6226	Remote Similarity	NPD1022	Approved
0.6226	Remote Similarity	NPD1023	Approved
0.6226	Remote Similarity	NPD1074	Approved
0.6226	Remote Similarity	NPD1711	Phase 2
0.6226	Remote Similarity	NPD1073	Approved
0.6226	Remote Similarity	NPD1246	Approved
0.6226	Remote Similarity	NPD1075	Approved
0.6226	Remote Similarity	NPD1020	Approved
0.6226	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1021	Approved
0.6224	Remote Similarity	NPD5630	Phase 1
0.6214	Remote Similarity	NPD4234	Approved
0.6214	Remote Similarity	NPD4233	Approved
0.6214	Remote Similarity	NPD1756	Approved
0.6214	Remote Similarity	NPD5278	Discontinued
0.6214	Remote Similarity	NPD1752	Approved
0.6211	Remote Similarity	NPD6049	Phase 2
0.6211	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3035	Approved
0.6207	Remote Similarity	NPD4027	Approved
0.6207	Remote Similarity	NPD4026	Approved
0.6207	Remote Similarity	NPD472	Approved
0.6196	Remote Similarity	NPD689	Discontinued
0.6186	Remote Similarity	NPD5926	Approved
0.6168	Remote Similarity	NPD3317	Approved
0.6163	Remote Similarity	NPD508	Approved
0.6163	Remote Similarity	NPD1475	Approved
0.6163	Remote Similarity	NPD507	Approved
0.6154	Remote Similarity	NPD9538	Approved
0.6154	Remote Similarity	NPD3644	Approved
0.6154	Remote Similarity	NPD3643	Approved
0.6154	Remote Similarity	NPD3642	Approved
0.6136	Remote Similarity	NPD4169	Approved
0.6136	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4170	Approved
0.6132	Remote Similarity	NPD2652	Approved
0.6132	Remote Similarity	NPD2650	Approved
0.6105	Remote Similarity	NPD845	Approved
0.6105	Remote Similarity	NPD719	Approved
0.6105	Remote Similarity	NPD720	Approved
0.61	Remote Similarity	NPD9261	Approved
0.6095	Remote Similarity	NPD2124	Approved
0.6095	Remote Similarity	NPD753	Approved
0.6092	Remote Similarity	NPD1617	Discontinued
0.6087	Remote Similarity	NPD531	Approved
0.6075	Remote Similarity	NPD2629	Approved
0.6075	Remote Similarity	NPD2319	Discontinued
0.6067	Remote Similarity	NPD262	Approved
0.6067	Remote Similarity	NPD263	Approved
0.6067	Remote Similarity	NPD831	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