NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.13
Volume:	177.365
LogP:	-0.588
LogD:	-0.445
LogS:	0.624
# Rotatable Bonds:	2
TPSA:	0.0
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	2.006
Fsp3:	0.4
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:	-5.372
MDCK Permeability:	4.6684763219673187e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.688
Human Intestinal Absorption (HIA):	0.945
20% Bioavailability (F20%):	0.758
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.306
Plasma Protein Binding (PPB):	16.949417114257812%
Volume Distribution (VD):	1.597
Pgp-substrate:	72.54371643066406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.116
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	7.905
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.007
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.557
Maximum Recommended Daily Dose:	0.259
Skin Sensitization:	0.088
Carcinogencity:	0.032
Eye Corrosion:	0.645
Eye Irritation:	0.723
Respiratory Toxicity:	0.491

Download Data

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

Natural Product: NPC271642

Natural Product ID:	NPC271642
*Common Name:**	Benzyl(Trimethyl)Azanium;Chloride
IUPAC Name:	benzyl(trimethyl)azanium;chloride
Synonyms:
Standard InCHIKey:	KXHPPCXNWTUNSB-UHFFFAOYSA-M
Standard InCHI:	InChI=1S/C10H16N.ClH/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H/q+1;/p-1
SMILES:	C[N+](Cc1ccccc1)(C)C.[Cl-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1372143
PubChem CID:	5963
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0003976] Alkyldimethylbenzylammonium halides [CHEMONTID:0003977] Alkyldimethylbenzylammonium chlorides

*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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	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
Potency	15

Activity Type	# Activity
Cell Line	1
Individual Protein	5
Organism	2
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PMID[543653]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	7943.3	nM	PMID[543654]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	12589.3	nM	PMID[543654]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	158.5	nM	PMID[543655]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	33.5	nM	PMID[543654]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[543654]
NPT2	Others	Unspecified		Potency	=	125.9	nM	PMID[543654]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1041.8	nM	PMID[543653]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2078.7	nM	PMID[543653]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[543653]
NPT2	Others	Unspecified		Potency	n.a.	43233.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	5464.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48918.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	34341.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	60757.8	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 NPC271642 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	502
0.1-0.2	8090
0.2-0.3	14431
0.3-0.4	14393
0.4-0.5	4139
0.5-0.6	892
0.6-0.7	174
0.7-0.8	61
0.8-0.85	9
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC98976
0.9189	High Similarity	NPC12857
0.8846	High Similarity	NPC104070
0.85	High Similarity	NPC169016
0.8493	Intermediate Similarity	NPC219246
0.8421	Intermediate Similarity	NPC139658
0.84	Intermediate Similarity	NPC299134
0.8312	Intermediate Similarity	NPC98269
0.8312	Intermediate Similarity	NPC325662
0.8235	Intermediate Similarity	NPC470926
0.8125	Intermediate Similarity	NPC231986
0.8072	Intermediate Similarity	NPC258046
0.8026	Intermediate Similarity	NPC244738
0.8	Intermediate Similarity	NPC229235
0.7927	Intermediate Similarity	NPC474088
0.7922	Intermediate Similarity	NPC112609
0.7922	Intermediate Similarity	NPC113000
0.7922	Intermediate Similarity	NPC122327
0.7821	Intermediate Similarity	NPC276699
0.7765	Intermediate Similarity	NPC473031
0.7711	Intermediate Similarity	NPC119677
0.7667	Intermediate Similarity	NPC471320
0.7667	Intermediate Similarity	NPC471319
0.764	Intermediate Similarity	NPC469330
0.764	Intermediate Similarity	NPC322040
0.7625	Intermediate Similarity	NPC290638
0.7586	Intermediate Similarity	NPC470877
0.7571	Intermediate Similarity	NPC269586
0.7558	Intermediate Similarity	NPC17497
0.7558	Intermediate Similarity	NPC305602
0.7556	Intermediate Similarity	NPC108339
0.7556	Intermediate Similarity	NPC329430
0.7528	Intermediate Similarity	NPC473661
0.75	Intermediate Similarity	NPC471307
0.75	Intermediate Similarity	NPC74936
0.75	Intermediate Similarity	NPC209764
0.75	Intermediate Similarity	NPC159178
0.75	Intermediate Similarity	NPC78041
0.75	Intermediate Similarity	NPC141139
0.75	Intermediate Similarity	NPC121872
0.7465	Intermediate Similarity	NPC65873
0.7465	Intermediate Similarity	NPC300345
0.7465	Intermediate Similarity	NPC120441
0.7465	Intermediate Similarity	NPC212114
0.7447	Intermediate Similarity	NPC291610
0.7447	Intermediate Similarity	NPC239854
0.7429	Intermediate Similarity	NPC149436
0.7429	Intermediate Similarity	NPC277704
0.7397	Intermediate Similarity	NPC210849
0.7361	Intermediate Similarity	NPC8235
0.7349	Intermediate Similarity	NPC475289
0.7349	Intermediate Similarity	NPC475573
0.7324	Intermediate Similarity	NPC198841
0.726	Intermediate Similarity	NPC147062
0.726	Intermediate Similarity	NPC169110
0.7253	Intermediate Similarity	NPC471309
0.7216	Intermediate Similarity	NPC474695
0.7209	Intermediate Similarity	NPC133162
0.72	Intermediate Similarity	NPC50266
0.7162	Intermediate Similarity	NPC150196
0.7162	Intermediate Similarity	NPC310758
0.7162	Intermediate Similarity	NPC54368
0.7162	Intermediate Similarity	NPC238023
0.7162	Intermediate Similarity	NPC135924
0.7162	Intermediate Similarity	NPC248705
0.7123	Intermediate Similarity	NPC36357
0.7123	Intermediate Similarity	NPC64270
0.7123	Intermediate Similarity	NPC114327
0.7105	Intermediate Similarity	NPC198023
0.7105	Intermediate Similarity	NPC155172
0.7105	Intermediate Similarity	NPC32312
0.7079	Intermediate Similarity	NPC12429
0.7067	Intermediate Similarity	NPC29680
0.7067	Intermediate Similarity	NPC22786
0.7065	Intermediate Similarity	NPC474974
0.7045	Intermediate Similarity	NPC203076
0.7041	Intermediate Similarity	NPC476198
0.7013	Intermediate Similarity	NPC178527
0.6977	Remote Similarity	NPC14326
0.6974	Remote Similarity	NPC45756
0.6974	Remote Similarity	NPC88566
0.6966	Remote Similarity	NPC53492
0.6966	Remote Similarity	NPC471638
0.6962	Remote Similarity	NPC200936
0.6947	Remote Similarity	NPC322598
0.6933	Remote Similarity	NPC246588
0.6923	Remote Similarity	NPC78154
0.6889	Remote Similarity	NPC30445
0.6889	Remote Similarity	NPC111233
0.6882	Remote Similarity	NPC71140
0.6848	Remote Similarity	NPC245259
0.6842	Remote Similarity	NPC66517
0.6842	Remote Similarity	NPC200745
0.6842	Remote Similarity	NPC71009
0.6809	Remote Similarity	NPC256452
0.6804	Remote Similarity	NPC214200
0.6804	Remote Similarity	NPC228400
0.679	Remote Similarity	NPC121708
0.679	Remote Similarity	NPC125144
0.6778	Remote Similarity	NPC262295
0.6778	Remote Similarity	NPC60408
0.6768	Remote Similarity	NPC469974
0.6753	Remote Similarity	NPC21211
0.6753	Remote Similarity	NPC113670
0.6742	Remote Similarity	NPC3210
0.6711	Remote Similarity	NPC45255
0.6709	Remote Similarity	NPC6107
0.6709	Remote Similarity	NPC52330
0.6709	Remote Similarity	NPC267443
0.6705	Remote Similarity	NPC134825
0.6702	Remote Similarity	NPC7067
0.6667	Remote Similarity	NPC202613
0.6667	Remote Similarity	NPC110264
0.6667	Remote Similarity	NPC471310
0.6667	Remote Similarity	NPC291066
0.6667	Remote Similarity	NPC164802
0.6667	Remote Similarity	NPC472258
0.6667	Remote Similarity	NPC471317
0.6633	Remote Similarity	NPC289381
0.6633	Remote Similarity	NPC155847
0.6633	Remote Similarity	NPC474582
0.6632	Remote Similarity	NPC161972
0.6632	Remote Similarity	NPC303045
0.6632	Remote Similarity	NPC58674
0.663	Remote Similarity	NPC173991
0.663	Remote Similarity	NPC176858
0.6625	Remote Similarity	NPC311343
0.6582	Remote Similarity	NPC36440
0.6582	Remote Similarity	NPC113837
0.6582	Remote Similarity	NPC289915
0.6579	Remote Similarity	NPC147578
0.6569	Remote Similarity	NPC55529
0.6562	Remote Similarity	NPC25565
0.6559	Remote Similarity	NPC191444
0.6559	Remote Similarity	NPC316108
0.6543	Remote Similarity	NPC139416
0.6543	Remote Similarity	NPC98880
0.6543	Remote Similarity	NPC246822
0.6543	Remote Similarity	NPC213570
0.6535	Remote Similarity	NPC473418
0.6509	Remote Similarity	NPC187036
0.6506	Remote Similarity	NPC54269
0.6495	Remote Similarity	NPC475439
0.6495	Remote Similarity	NPC473501
0.6494	Remote Similarity	NPC200624
0.6489	Remote Similarity	NPC226438
0.6463	Remote Similarity	NPC95289
0.6422	Remote Similarity	NPC313449
0.6421	Remote Similarity	NPC108800
0.642	Remote Similarity	NPC239931
0.642	Remote Similarity	NPC22760
0.642	Remote Similarity	NPC78954
0.642	Remote Similarity	NPC82770
0.64	Remote Similarity	NPC329375
0.64	Remote Similarity	NPC327226
0.6386	Remote Similarity	NPC326200
0.6386	Remote Similarity	NPC87099
0.6386	Remote Similarity	NPC280135
0.6386	Remote Similarity	NPC226999
0.6386	Remote Similarity	NPC1008
0.6386	Remote Similarity	NPC193578
0.6386	Remote Similarity	NPC39799
0.6386	Remote Similarity	NPC74458
0.6386	Remote Similarity	NPC135433
0.6386	Remote Similarity	NPC158028
0.6383	Remote Similarity	NPC172128
0.6373	Remote Similarity	NPC167336
0.6373	Remote Similarity	NPC143516
0.6355	Remote Similarity	NPC57051
0.6355	Remote Similarity	NPC296163
0.6354	Remote Similarity	NPC246757
0.6354	Remote Similarity	NPC291070
0.6346	Remote Similarity	NPC77294
0.6341	Remote Similarity	NPC5324
0.6341	Remote Similarity	NPC16190
0.6341	Remote Similarity	NPC235059
0.6341	Remote Similarity	NPC297358
0.6341	Remote Similarity	NPC169222
0.6341	Remote Similarity	NPC473206
0.633	Remote Similarity	NPC313673
0.6327	Remote Similarity	NPC311242
0.6311	Remote Similarity	NPC471447
0.6311	Remote Similarity	NPC130898
0.6311	Remote Similarity	NPC474973
0.6311	Remote Similarity	NPC474804
0.6311	Remote Similarity	NPC45033
0.631	Remote Similarity	NPC285679
0.631	Remote Similarity	NPC212463
0.6292	Remote Similarity	NPC307456
0.6275	Remote Similarity	NPC304761
0.6275	Remote Similarity	NPC150254
0.6275	Remote Similarity	NPC226778
0.6275	Remote Similarity	NPC147000
0.6275	Remote Similarity	NPC275467
0.6273	Remote Similarity	NPC192209
0.6265	Remote Similarity	NPC251490
0.6265	Remote Similarity	NPC72670
0.6265	Remote Similarity	NPC271732
0.6265	Remote Similarity	NPC263385
0.625	Remote Similarity	NPC316582

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 NPC271642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	1101
0.2-0.3	1234
0.3-0.4	3076
0.4-0.5	2299
0.5-0.6	824
0.6-0.7	241
0.7-0.8	90
0.8-0.85	15
0.85-0.9	2
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9859	High Similarity	NPD603	Approved
0.9459	High Similarity	NPD5371	Approved
0.9459	High Similarity	NPD5372	Approved
0.9324	High Similarity	NPD508	Approved
0.9324	High Similarity	NPD507	Approved
0.8974	High Similarity	NPD2539	Approved
0.8974	High Similarity	NPD2538	Approved
0.8571	High Similarity	NPD1052	Approved
0.8571	High Similarity	NPD1053	Approved
0.8571	High Similarity	NPD1051	Approved
0.8553	High Similarity	NPD4147	Approved
0.8553	High Similarity	NPD4144	Approved
0.8537	High Similarity	NPD588	Approved
0.8537	High Similarity	NPD587	Approved
0.8434	Intermediate Similarity	NPD5656	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3000	Approved
0.8235	Intermediate Similarity	NPD2998	Approved
0.8235	Intermediate Similarity	NPD2997	Approved
0.8205	Intermediate Similarity	NPD293	Approved
0.8205	Intermediate Similarity	NPD295	Approved
0.8205	Intermediate Similarity	NPD296	Approved
0.8171	Intermediate Similarity	NPD9505	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD4407	Approved
0.814	Intermediate Similarity	NPD4408	Approved
0.814	Intermediate Similarity	NPD4405	Approved
0.8125	Intermediate Similarity	NPD4027	Approved
0.8125	Intermediate Similarity	NPD4026	Approved
0.8125	Intermediate Similarity	NPD3035	Approved
0.8101	Intermediate Similarity	NPD590	Approved
0.8101	Intermediate Similarity	NPD589	Approved
0.8049	Intermediate Similarity	NPD5178	Approved
0.8046	Intermediate Similarity	NPD4542	Approved
0.8046	Intermediate Similarity	NPD4545	Approved
0.8026	Intermediate Similarity	NPD9728	Phase 1
0.8025	Intermediate Similarity	NPD4701	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4169	Approved
0.8025	Intermediate Similarity	NPD4170	Approved
0.8023	Intermediate Similarity	NPD7160	Approved
0.8	Intermediate Similarity	NPD297	Approved
0.8	Intermediate Similarity	NPD9	Approved
0.7927	Intermediate Similarity	NPD831	Approved
0.7927	Intermediate Similarity	NPD1800	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4635	Approved
0.7927	Intermediate Similarity	NPD830	Approved
0.7922	Intermediate Similarity	NPD80	Approved
0.7922	Intermediate Similarity	NPD9593	Approved
0.7922	Intermediate Similarity	NPD9594	Approved
0.7922	Intermediate Similarity	NPD9592	Approved
0.7922	Intermediate Similarity	NPD9590	Approved
0.7922	Intermediate Similarity	NPD9589	Approved
0.7922	Intermediate Similarity	NPD9591	Approved
0.7922	Intermediate Similarity	NPD9588	Approved
0.7882	Intermediate Similarity	NPD3345	Approved
0.7857	Intermediate Similarity	NPD5252	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6548	Approved
0.7841	Intermediate Similarity	NPD6549	Approved
0.7831	Intermediate Similarity	NPD785	Approved
0.7791	Intermediate Similarity	NPD9349	Approved
0.7791	Intermediate Similarity	NPD9350	Approved
0.7791	Intermediate Similarity	NPD9348	Approved
0.7791	Intermediate Similarity	NPD9351	Phase 3
0.7778	Intermediate Similarity	NPD5597	Approved
0.7778	Intermediate Similarity	NPD3904	Approved
0.7778	Intermediate Similarity	NPD3903	Approved
0.7778	Intermediate Similarity	NPD3981	Approved
0.7778	Intermediate Similarity	NPD5598	Approved
0.7778	Intermediate Similarity	NPD3979	Approved
0.7753	Intermediate Similarity	NPD5554	Approved
0.7738	Intermediate Similarity	NPD2205	Approved
0.7738	Intermediate Similarity	NPD2208	Approved
0.7738	Intermediate Similarity	NPD5916	Discontinued
0.7692	Intermediate Similarity	NPD505	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5675	Discontinued
0.7667	Intermediate Similarity	NPD2005	Discontinued
0.7667	Intermediate Similarity	NPD157	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD292	Approved
0.7662	Intermediate Similarity	NPD294	Approved
0.7647	Intermediate Similarity	NPD4636	Approved
0.7647	Intermediate Similarity	NPD4409	Approved
0.7647	Intermediate Similarity	NPD4406	Approved
0.764	Intermediate Similarity	NPD8	Approved
0.764	Intermediate Similarity	NPD243	Approved
0.7619	Intermediate Similarity	NPD9395	Approved
0.7558	Intermediate Similarity	NPD782	Approved
0.7558	Intermediate Similarity	NPD783	Approved
0.7558	Intermediate Similarity	NPD781	Approved
0.7558	Intermediate Similarity	NPD780	Approved
0.75	Intermediate Similarity	NPD3346	Approved
0.75	Intermediate Similarity	NPD6499	Approved
0.75	Intermediate Similarity	NPD6498	Approved
0.75	Intermediate Similarity	NPD3344	Approved
0.747	Intermediate Similarity	NPD472	Approved
0.7447	Intermediate Similarity	NPD813	Approved
0.7444	Intermediate Similarity	NPD735	Approved
0.7444	Intermediate Similarity	NPD736	Approved
0.7442	Intermediate Similarity	NPD3099	Discontinued
0.7419	Intermediate Similarity	NPD787	Suspended
0.7412	Intermediate Similarity	NPD4544	Approved
0.7368	Intermediate Similarity	NPD1396	Approved
0.7356	Intermediate Similarity	NPD2002	Discontinued
0.7356	Intermediate Similarity	NPD3428	Approved
0.7356	Intermediate Similarity	NPD187	Approved
0.7356	Intermediate Similarity	NPD4145	Approved
0.7356	Intermediate Similarity	NPD3426	Approved
0.7356	Intermediate Similarity	NPD4146	Approved
0.7349	Intermediate Similarity	NPD260	Discontinued
0.7333	Intermediate Similarity	NPD6690	Approved
0.7333	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD9397	Approved
0.7317	Intermediate Similarity	NPD79	Approved
0.7317	Intermediate Similarity	NPD9393	Approved
0.7317	Intermediate Similarity	NPD9564	Approved
0.7317	Intermediate Similarity	NPD9563	Approved
0.7303	Intermediate Similarity	NPD5915	Approved
0.7292	Intermediate Similarity	NPD2937	Phase 1
0.7292	Intermediate Similarity	NPD2939	Approved
0.7263	Intermediate Similarity	NPD4734	Approved
0.7263	Intermediate Similarity	NPD4735	Approved
0.7253	Intermediate Similarity	NPD1080	Approved
0.7241	Intermediate Similarity	NPD305	Approved
0.7241	Intermediate Similarity	NPD304	Approved
0.7234	Intermediate Similarity	NPD1946	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4543	Discontinued
0.7209	Intermediate Similarity	NPD3429	Approved
0.7209	Intermediate Similarity	NPD3427	Approved
0.7191	Intermediate Similarity	NPD771	Phase 3
0.7188	Intermediate Similarity	NPD5103	Approved
0.7174	Intermediate Similarity	NPD2655	Approved
0.7174	Intermediate Similarity	NPD2656	Approved
0.7143	Intermediate Similarity	NPD1064	Approved
0.7143	Intermediate Similarity	NPD1065	Approved
0.7143	Intermediate Similarity	NPD3546	Approved
0.7143	Intermediate Similarity	NPD3545	Approved
0.7113	Intermediate Similarity	NPD4937	Approved
0.7113	Intermediate Similarity	NPD4936	Approved
0.7097	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6472	Discontinued
0.7093	Intermediate Similarity	NPD4000	Phase 3
0.7093	Intermediate Similarity	NPD2001	Discontinued
0.7083	Intermediate Similarity	NPD1419	Approved
0.7083	Intermediate Similarity	NPD1417	Approved
0.7071	Intermediate Similarity	NPD4115	Approved
0.7071	Intermediate Similarity	NPD5253	Approved
0.7071	Intermediate Similarity	NPD4114	Approved
0.7065	Intermediate Similarity	NPD2878	Approved
0.7041	Intermediate Similarity	NPD959	Discontinued
0.7021	Intermediate Similarity	NPD1099	Approved
0.7021	Intermediate Similarity	NPD1100	Approved
0.701	Intermediate Similarity	NPD2244	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD154	Discontinued
0.7	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8010	Approved
0.7	Intermediate Similarity	NPD8009	Approved
0.6989	Remote Similarity	NPD4094	Approved
0.6979	Remote Similarity	NPD1916	Discontinued
0.697	Remote Similarity	NPD7170	Discontinued
0.6947	Remote Similarity	NPD5832	Phase 3
0.6941	Remote Similarity	NPD1617	Discontinued
0.6939	Remote Similarity	NPD3407	Phase 3
0.6931	Remote Similarity	NPD6236	Approved
0.6931	Remote Similarity	NPD7120	Approved
0.6931	Remote Similarity	NPD6235	Approved
0.6931	Remote Similarity	NPD7633	Discontinued
0.6931	Remote Similarity	NPD4116	Approved
0.6915	Remote Similarity	NPD1738	Approved
0.6915	Remote Similarity	NPD5964	Phase 2
0.6915	Remote Similarity	NPD5963	Phase 2
0.69	Remote Similarity	NPD6299	Approved
0.69	Remote Similarity	NPD6300	Approved
0.6889	Remote Similarity	NPD9186	Approved
0.6889	Remote Similarity	NPD9184	Approved
0.6882	Remote Similarity	NPD3980	Approved
0.6882	Remote Similarity	NPD3982	Approved
0.6842	Remote Similarity	NPD4655	Approved
0.6842	Remote Similarity	NPD4657	Approved
0.6832	Remote Similarity	NPD2679	Approved
0.6832	Remote Similarity	NPD2678	Approved
0.6804	Remote Similarity	NPD1795	Discontinued
0.6796	Remote Similarity	NPD2038	Approved
0.6796	Remote Similarity	NPD2999	Approved
0.6796	Remote Similarity	NPD2039	Approved
0.6796	Remote Similarity	NPD3001	Approved
0.6774	Remote Similarity	NPD1812	Approved
0.6774	Remote Similarity	NPD1814	Approved
0.6771	Remote Similarity	NPD1724	Approved
0.6771	Remote Similarity	NPD4263	Approved
0.6771	Remote Similarity	NPD4117	Approved
0.6771	Remote Similarity	NPD4813	Approved
0.6768	Remote Similarity	NPD489	Approved
0.6768	Remote Similarity	NPD488	Approved
0.6753	Remote Similarity	NPD675	Discontinued
0.6739	Remote Similarity	NPD4728	Approved
0.6735	Remote Similarity	NPD854	Approved
0.6735	Remote Similarity	NPD855	Approved
0.6735	Remote Similarity	NPD4803	Discontinued
0.6735	Remote Similarity	NPD5753	Discontinued
0.6733	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7121	Approved
0.6731	Remote Similarity	NPD3066	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