NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	171.1
Volume:	196.81
LogP:	3.482
LogD:	3.358
LogS:	-3.576
# Rotatable Bonds:	2
TPSA:	12.89
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.676
Synthetic Accessibility Score:	1.666
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.567
MDCK Permeability:	1.928138044604566e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.521

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.957
Plasma Protein Binding (PPB):	94.15547943115234%
Volume Distribution (VD):	1.255
Pgp-substrate:	6.084150314331055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.739
CYP2C19-substrate:	0.154
CYP2C9-inhibitor:	0.509
CYP2C9-substrate:	0.727
CYP2D6-inhibitor:	0.227
CYP2D6-substrate:	0.85
CYP3A4-inhibitor:	0.143
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	4.699
Half-life (T1/2):	0.333

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.136
AMES Toxicity:	0.401
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.188
Skin Sensitization:	0.449
Carcinogencity:	0.579
Eye Corrosion:	0.034
Eye Irritation:	0.959
Respiratory Toxicity:	0.705

Download Data

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

Natural Product: NPC148140

Natural Product ID:	NPC148140
*Common Name:**	2-Propylquinoline
IUPAC Name:	2-propylquinoline
Synonyms:	2-N-Propylquinoleine; 2-Propyl-Quinoline
Standard InCHIKey:	IZXJPGLOYYDHRM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H13N/c1-2-5-11-9-8-10-6-3-4-7-12(10)13-11/h3-4,6-9H,2,5H2,1H3
SMILES:	CCCc1ccc2c(n1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL354607
PubChem CID:	74166
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and 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
NPO17983	Nigrosabulum globosum	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374942]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499324]
NPO19065	Galipea longiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19065	Galipea longiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10698	Galipea bracteata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18972	Astropecten indicus	Species	Astropectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18402	Tecoma peroba	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17868	Eucryphia glutinosa	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO83	Saccharina angustata	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18897	Cephalosporium gregatum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14518	Ateleia herbert-smithii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16708	Pinus abies	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19065	Galipea longiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10698	Galipea bracteata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16452	Iochroma coccineum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19489	Tylosema esculentum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19680	Haminoea orteai	Species	Haminoeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16032	Xanthoparmelia quintaria	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17983	Nigrosabulum globosum	Species	Bionectriaceae	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	8

Activity Type	# Activity
Cell Line	1
Organism	4
Others	3
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	125580.0	nM	PMID[492408]
NPT3954	Organism	Human T-lymphotropic virus 1	Human T-lymphotropic virus 1	Inhibition	=	0.0	%	PMID[492406]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC90	=	50.0	ug.mL-1	PMID[492407]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC90	=	50.0	ug.mL-1	PMID[492407]
NPT27	Others	Unspecified		Drug metabolism	=	100.0	%	PMID[492408]
NPT433	Subcellular	Liver microsomes	Homo sapiens	Drug metabolism	=	98.0	%	PMID[492408]
NPT35	Others	n.a.		Solubility	>	100000.0	ug.mL-1	PMID[492408]
NPT2	Others	Unspecified		Ratio CC50/IC50	<	1.25	n.a.	PMID[492408]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	100000.0	nM	PMID[492408]

☑ 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 NPC148140 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	1167
0.1-0.2	12147
0.2-0.3	16451
0.3-0.4	7524
0.4-0.5	2546
0.5-0.6	1770
0.6-0.7	771
0.7-0.8	247
0.8-0.85	58
0.85-0.9	9
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC81561
0.9646	High Similarity	NPC215519
0.9643	High Similarity	NPC162689
0.9643	High Similarity	NPC54102
0.9316	High Similarity	NPC122718
0.9	High Similarity	NPC476140
0.8908	High Similarity	NPC46358
0.8824	High Similarity	NPC41174
0.8689	High Similarity	NPC250361
0.8629	High Similarity	NPC473587
0.8583	High Similarity	NPC198988
0.856	High Similarity	NPC475428
0.856	High Similarity	NPC22079
0.8548	High Similarity	NPC473762
0.8516	High Similarity	NPC325252
0.8492	Intermediate Similarity	NPC179365
0.8492	Intermediate Similarity	NPC475450
0.845	Intermediate Similarity	NPC314102
0.845	Intermediate Similarity	NPC251722
0.844	Intermediate Similarity	NPC213774
0.8333	Intermediate Similarity	NPC91958
0.8321	Intermediate Similarity	NPC104483
0.8281	Intermediate Similarity	NPC473930
0.8258	Intermediate Similarity	NPC59084
0.8258	Intermediate Similarity	NPC115611
0.8258	Intermediate Similarity	NPC2949
0.8244	Intermediate Similarity	NPC169433
0.8195	Intermediate Similarity	NPC473868
0.8195	Intermediate Similarity	NPC63157
0.8182	Intermediate Similarity	NPC88097
0.8134	Intermediate Similarity	NPC20144
0.812	Intermediate Similarity	NPC284635
0.8092	Intermediate Similarity	NPC29886
0.8092	Intermediate Similarity	NPC261195
0.8033	Intermediate Similarity	NPC143603
0.803	Intermediate Similarity	NPC84911
0.803	Intermediate Similarity	NPC150259
0.8017	Intermediate Similarity	NPC302790
0.8015	Intermediate Similarity	NPC470440
0.8	Intermediate Similarity	NPC143156
0.7956	Intermediate Similarity	NPC478186
0.7955	Intermediate Similarity	NPC96102
0.7955	Intermediate Similarity	NPC218268
0.7923	Intermediate Similarity	NPC256893
0.7923	Intermediate Similarity	NPC82295
0.791	Intermediate Similarity	NPC312092
0.791	Intermediate Similarity	NPC110126
0.791	Intermediate Similarity	NPC73767
0.7899	Intermediate Similarity	NPC179787
0.7899	Intermediate Similarity	NPC21605
0.7899	Intermediate Similarity	NPC201380
0.7899	Intermediate Similarity	NPC470111
0.7895	Intermediate Similarity	NPC125746
0.7895	Intermediate Similarity	NPC105127
0.7891	Intermediate Similarity	NPC278451
0.7883	Intermediate Similarity	NPC204141
0.7869	Intermediate Similarity	NPC476566
0.7852	Intermediate Similarity	NPC469784
0.7852	Intermediate Similarity	NPC469780
0.7852	Intermediate Similarity	NPC469783
0.7852	Intermediate Similarity	NPC469761
0.7852	Intermediate Similarity	NPC469768
0.7852	Intermediate Similarity	NPC469779
0.7852	Intermediate Similarity	NPC238499
0.7852	Intermediate Similarity	NPC469767
0.7846	Intermediate Similarity	NPC282398
0.7842	Intermediate Similarity	NPC321911
0.7826	Intermediate Similarity	NPC63545
0.7815	Intermediate Similarity	NPC27802
0.781	Intermediate Similarity	NPC242556
0.7805	Intermediate Similarity	NPC471402
0.7805	Intermediate Similarity	NPC297486
0.7805	Intermediate Similarity	NPC240136
0.7794	Intermediate Similarity	NPC469766
0.7794	Intermediate Similarity	NPC60553
0.7794	Intermediate Similarity	NPC277157
0.7786	Intermediate Similarity	NPC33421
0.7786	Intermediate Similarity	NPC40070
0.777	Intermediate Similarity	NPC469811
0.7737	Intermediate Similarity	NPC190296
0.7721	Intermediate Similarity	NPC279081
0.7698	Intermediate Similarity	NPC182570
0.7698	Intermediate Similarity	NPC265605
0.7698	Intermediate Similarity	NPC48564
0.7676	Intermediate Similarity	NPC26872
0.7647	Intermediate Similarity	NPC315348
0.7647	Intermediate Similarity	NPC316811
0.7647	Intermediate Similarity	NPC32002
0.7643	Intermediate Similarity	NPC477134
0.7626	Intermediate Similarity	NPC314372
0.7626	Intermediate Similarity	NPC285731
0.7626	Intermediate Similarity	NPC86288
0.7622	Intermediate Similarity	NPC476219
0.7622	Intermediate Similarity	NPC476297
0.7597	Intermediate Similarity	NPC166424
0.7597	Intermediate Similarity	NPC146373
0.7597	Intermediate Similarity	NPC245244
0.7591	Intermediate Similarity	NPC230002
0.7589	Intermediate Similarity	NPC37548
0.7589	Intermediate Similarity	NPC124005
0.7578	Intermediate Similarity	NPC290094
0.7571	Intermediate Similarity	NPC288838
0.7571	Intermediate Similarity	NPC143872
0.7563	Intermediate Similarity	NPC231655
0.7563	Intermediate Similarity	NPC76540
0.7552	Intermediate Similarity	NPC325903
0.7535	Intermediate Similarity	NPC148592
0.7535	Intermediate Similarity	NPC53947
0.7519	Intermediate Similarity	NPC476322
0.7518	Intermediate Similarity	NPC471957
0.7517	Intermediate Similarity	NPC26850
0.7517	Intermediate Similarity	NPC236711
0.75	Intermediate Similarity	NPC469525
0.75	Intermediate Similarity	NPC159856
0.7483	Intermediate Similarity	NPC470233
0.7466	Intermediate Similarity	NPC477591
0.7466	Intermediate Similarity	NPC475990
0.7466	Intermediate Similarity	NPC6436
0.7466	Intermediate Similarity	NPC474880
0.7466	Intermediate Similarity	NPC56765
0.7466	Intermediate Similarity	NPC221786
0.7465	Intermediate Similarity	NPC2272
0.7465	Intermediate Similarity	NPC187951
0.7448	Intermediate Similarity	NPC476464
0.7447	Intermediate Similarity	NPC129042
0.744	Intermediate Similarity	NPC192209
0.7431	Intermediate Similarity	NPC281094
0.7431	Intermediate Similarity	NPC200743
0.7415	Intermediate Similarity	NPC229173
0.7415	Intermediate Similarity	NPC215584
0.7415	Intermediate Similarity	NPC44773
0.7415	Intermediate Similarity	NPC81229
0.7415	Intermediate Similarity	NPC255229
0.7413	Intermediate Similarity	NPC24678
0.7413	Intermediate Similarity	NPC105818
0.741	Intermediate Similarity	NPC88121
0.7405	Intermediate Similarity	NPC169625
0.7405	Intermediate Similarity	NPC202957
0.7398	Intermediate Similarity	NPC187036
0.7398	Intermediate Similarity	NPC296163
0.7397	Intermediate Similarity	NPC129721
0.7388	Intermediate Similarity	NPC101165
0.7385	Intermediate Similarity	NPC27740
0.7379	Intermediate Similarity	NPC470507
0.7379	Intermediate Similarity	NPC471458
0.7379	Intermediate Similarity	NPC38736
0.7365	Intermediate Similarity	NPC194881
0.7361	Intermediate Similarity	NPC470823
0.7347	Intermediate Similarity	NPC293487
0.7343	Intermediate Similarity	NPC288445
0.7329	Intermediate Similarity	NPC51054
0.7329	Intermediate Similarity	NPC285469
0.7329	Intermediate Similarity	NPC184476
0.7315	Intermediate Similarity	NPC478182
0.7315	Intermediate Similarity	NPC271797
0.7315	Intermediate Similarity	NPC90723
0.7315	Intermediate Similarity	NPC21174
0.7313	Intermediate Similarity	NPC69914
0.731	Intermediate Similarity	NPC25008
0.731	Intermediate Similarity	NPC469760
0.731	Intermediate Similarity	NPC141926
0.731	Intermediate Similarity	NPC469763
0.731	Intermediate Similarity	NPC73952
0.731	Intermediate Similarity	NPC469786
0.731	Intermediate Similarity	NPC161108
0.731	Intermediate Similarity	NPC469765
0.731	Intermediate Similarity	NPC138842
0.731	Intermediate Similarity	NPC200214
0.731	Intermediate Similarity	NPC259644
0.7297	Intermediate Similarity	NPC122141
0.7297	Intermediate Similarity	NPC470204
0.7293	Intermediate Similarity	NPC89490
0.7279	Intermediate Similarity	NPC286427
0.7279	Intermediate Similarity	NPC299594
0.7267	Intermediate Similarity	NPC195507
0.7267	Intermediate Similarity	NPC2165
0.726	Intermediate Similarity	NPC80597
0.726	Intermediate Similarity	NPC75540
0.726	Intermediate Similarity	NPC70922
0.726	Intermediate Similarity	NPC211572
0.726	Intermediate Similarity	NPC34844
0.726	Intermediate Similarity	NPC212376
0.7258	Intermediate Similarity	NPC314141
0.7248	Intermediate Similarity	NPC470203
0.7248	Intermediate Similarity	NPC225018
0.7241	Intermediate Similarity	NPC216713
0.7239	Intermediate Similarity	NPC475090
0.7239	Intermediate Similarity	NPC476131
0.7239	Intermediate Similarity	NPC329896
0.7239	Intermediate Similarity	NPC475105
0.7231	Intermediate Similarity	NPC329825
0.723	Intermediate Similarity	NPC41257
0.723	Intermediate Similarity	NPC474791
0.723	Intermediate Similarity	NPC318065
0.723	Intermediate Similarity	NPC206819
0.7211	Intermediate Similarity	NPC141353
0.7203	Intermediate Similarity	NPC316069
0.72	Intermediate Similarity	NPC478184
0.72	Intermediate Similarity	NPC317105
0.72	Intermediate Similarity	NPC247987

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 NPC148140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	571
0.1-0.2	871
0.2-0.3	959
0.3-0.4	2059
0.4-0.5	2458
0.5-0.6	1581
0.6-0.7	537
0.7-0.8	92
0.8-0.85	19
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD947	Approved
0.8651	High Similarity	NPD3385	Approved
0.864	High Similarity	NPD1251	Discontinued
0.8516	High Similarity	NPD1255	Approved
0.8516	High Similarity	NPD1256	Approved
0.8516	High Similarity	NPD1254	Approved
0.8516	High Similarity	NPD1253	Approved
0.848	Intermediate Similarity	NPD3654	Approved
0.8361	Intermediate Similarity	NPD1561	Phase 2
0.832	Intermediate Similarity	NPD2119	Approved
0.832	Intermediate Similarity	NPD2118	Approved
0.8308	Intermediate Similarity	NPD45	Approved
0.8308	Intermediate Similarity	NPD6554	Approved
0.8175	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD991	Phase 2
0.8134	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3476	Approved
0.8125	Intermediate Similarity	NPD3475	Approved
0.8125	Intermediate Similarity	NPD715	Phase 3
0.8074	Intermediate Similarity	NPD4509	Discontinued
0.8074	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD1722	Approved
0.803	Intermediate Similarity	NPD1262	Discovery
0.8	Intermediate Similarity	NPD2006	Phase 2
0.7985	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1683	Approved
0.7955	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD9583	Approved
0.7939	Intermediate Similarity	NPD4028	Approved
0.7939	Intermediate Similarity	NPD3942	Approved
0.7939	Intermediate Similarity	NPD3944	Approved
0.7939	Intermediate Similarity	NPD4029	Approved
0.7939	Intermediate Similarity	NPD4030	Approved
0.791	Intermediate Similarity	NPD786	Approved
0.7899	Intermediate Similarity	NPD4547	Phase 3
0.7842	Intermediate Similarity	NPD2430	Phase 2
0.781	Intermediate Similarity	NPD5254	Discontinued
0.7795	Intermediate Similarity	NPD9357	Approved
0.7737	Intermediate Similarity	NPD4047	Discontinued
0.773	Intermediate Similarity	NPD2882	Phase 1
0.773	Intermediate Similarity	NPD6158	Phase 2
0.773	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD271	Approved
0.7698	Intermediate Similarity	NPD268	Approved
0.7681	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2075	Approved
0.7647	Intermediate Similarity	NPD2073	Approved
0.7647	Intermediate Similarity	NPD2074	Approved
0.7647	Intermediate Similarity	NPD2070	Approved
0.7647	Intermediate Similarity	NPD2072	Approved
0.7647	Intermediate Similarity	NPD2071	Approved
0.7647	Intermediate Similarity	NPD2069	Approved
0.7647	Intermediate Similarity	NPD2068	Approved
0.7643	Intermediate Similarity	NPD1661	Suspended
0.7589	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD3100	Discontinued
0.7574	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD9098	Phase 3
0.7552	Intermediate Similarity	NPD2837	Discontinued
0.7542	Intermediate Similarity	NPD993	Approved
0.7542	Intermediate Similarity	NPD990	Approved
0.7536	Intermediate Similarity	NPD5020	Approved
0.7535	Intermediate Similarity	NPD4463	Approved
0.7535	Intermediate Similarity	NPD4462	Approved
0.7517	Intermediate Similarity	NPD4326	Phase 2
0.75	Intermediate Similarity	NPD2165	Phase 1
0.75	Intermediate Similarity	NPD5787	Discontinued
0.75	Intermediate Similarity	NPD6285	Phase 2
0.7481	Intermediate Similarity	NPD1598	Discontinued
0.7481	Intermediate Similarity	NPD4880	Discontinued
0.7465	Intermediate Similarity	NPD1183	Approved
0.7465	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1993	Approved
0.7463	Intermediate Similarity	NPD1994	Approved
0.7463	Intermediate Similarity	NPD1995	Approved
0.7448	Intermediate Similarity	NPD2150	Discontinued
0.7448	Intermediate Similarity	NPD3115	Approved
0.7448	Intermediate Similarity	NPD3113	Approved
0.7448	Intermediate Similarity	NPD3114	Approved
0.7448	Intermediate Similarity	NPD3112	Approved
0.7431	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5671	Approved
0.7413	Intermediate Similarity	NPD2172	Phase 1
0.741	Intermediate Similarity	NPD1592	Phase 3
0.7397	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD9392	Approved
0.7381	Intermediate Similarity	NPD9396	Approved
0.7365	Intermediate Similarity	NPD5315	Discontinued
0.736	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4811	Discontinued
0.7333	Intermediate Similarity	NPD6299	Approved
0.7333	Intermediate Similarity	NPD6300	Approved
0.7324	Intermediate Similarity	NPD7469	Discontinued
0.7315	Intermediate Similarity	NPD3323	Discontinued
0.7292	Intermediate Similarity	NPD3835	Phase 3
0.7292	Intermediate Similarity	NPD3833	Phase 3
0.7279	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4702	Approved
0.7273	Intermediate Similarity	NPD4703	Approved
0.7267	Intermediate Similarity	NPD2915	Discontinued
0.7267	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD680	Discontinued
0.7258	Intermediate Similarity	NPD4824	Approved
0.7258	Intermediate Similarity	NPD4823	Approved
0.7248	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6451	Discontinued
0.7234	Intermediate Similarity	NPD3525	Discontinued
0.7231	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4116	Approved
0.7206	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2640	Approved
0.7171	Intermediate Similarity	NPD2641	Approved
0.7171	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7480	Approved
0.7165	Intermediate Similarity	NPD7481	Approved
0.7162	Intermediate Similarity	NPD1647	Phase 1
0.7162	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1648	Phase 1
0.7152	Intermediate Similarity	NPD2720	Phase 1
0.7152	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD975	Approved
0.7143	Intermediate Similarity	NPD976	Approved
0.7143	Intermediate Similarity	NPD977	Approved
0.7133	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5412	Discontinued
0.7107	Intermediate Similarity	NPD3545	Approved
0.7107	Intermediate Similarity	NPD3546	Approved
0.7101	Intermediate Similarity	NPD2142	Approved
0.7101	Intermediate Similarity	NPD2141	Approved
0.7101	Intermediate Similarity	NPD2140	Approved
0.7095	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD404	Discontinued
0.7078	Intermediate Similarity	NPD3610	Approved
0.7078	Intermediate Similarity	NPD3609	Approved
0.7078	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2896	Discontinued
0.7067	Intermediate Similarity	NPD1404	Approved
0.7067	Intermediate Similarity	NPD1403	Approved
0.7067	Intermediate Similarity	NPD112	Approved
0.7067	Intermediate Similarity	NPD9705	Discontinued
0.705	Intermediate Similarity	NPD792	Discontinued
0.7049	Intermediate Similarity	NPD4114	Approved
0.7049	Intermediate Similarity	NPD4115	Approved
0.7047	Intermediate Similarity	NPD2330	Approved
0.7039	Intermediate Similarity	NPD1002	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4510	Discontinued
0.6987	Remote Similarity	NPD6492	Phase 2
0.698	Remote Similarity	NPD2580	Discontinued
0.698	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3117	Approved
0.6968	Remote Similarity	NPD3116	Approved
0.6959	Remote Similarity	NPD3339	Approved
0.6954	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4640	Approved
0.6948	Remote Similarity	NPD4639	Approved
0.6948	Remote Similarity	NPD4638	Approved
0.6948	Remote Similarity	NPD5021	Discontinued
0.6944	Remote Similarity	NPD3813	Approved
0.6943	Remote Similarity	NPD5104	Approved
0.6943	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2373	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2581	Approved
0.6933	Remote Similarity	NPD2582	Approved
0.6933	Remote Similarity	NPD6497	Approved
0.6929	Remote Similarity	NPD5631	Phase 3
0.6928	Remote Similarity	NPD509	Phase 3
0.6928	Remote Similarity	NPD1313	Approved
0.6923	Remote Similarity	NPD6182	Approved
0.6923	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD43	Approved
0.6923	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1597	Phase 1
0.6912	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5436	Phase 1
0.6903	Remote Similarity	NPD1325	Approved
0.6903	Remote Similarity	NPD1326	Approved
0.6901	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD945	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6159	Phase 2
0.6899	Remote Similarity	NPD4181	Approved
0.6899	Remote Similarity	NPD7111	Discontinued
0.6887	Remote Similarity	NPD5255	Approved
0.6887	Remote Similarity	NPD2308	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5418	Discontinued
0.6883	Remote Similarity	NPD2642	Approved
0.6883	Remote Similarity	NPD2639	Approved
0.6879	Remote Similarity	NPD201	Phase 2
0.6879	Remote Similarity	NPD3799	Suspended
0.6879	Remote Similarity	NPD5065	Approved
0.6879	Remote Similarity	NPD200	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