NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	199.14
Volume:	231.402
LogP:	4.529
LogD:	3.995
LogS:	-4.959
# Rotatable Bonds:	4
TPSA:	12.89
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	1.69
Fsp3:	0.357
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:	-4.637
MDCK Permeability:	1.443402925360715e-05
Pgp-inhibitor:	0.486
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.932
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.967
Plasma Protein Binding (PPB):	95.91065216064453%
Volume Distribution (VD):	1.324
Pgp-substrate:	2.999704360961914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.744
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.611
CYP2C9-substrate:	0.743
CYP2D6-inhibitor:	0.36
CYP2D6-substrate:	0.65
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	4.285
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.263
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.168
AMES Toxicity:	0.228
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.167
Skin Sensitization:	0.722
Carcinogencity:	0.445
Eye Corrosion:	0.047
Eye Irritation:	0.968
Respiratory Toxicity:	0.653

Download Data

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

Natural Product: NPC81561

Natural Product ID:	NPC81561
*Common Name:**	2-Pentylquinoline
IUPAC Name:	2-pentylquinoline
Synonyms:	2-N-Pentylquinoleine; 2-Pentyl-Quinoline
Standard InCHIKey:	GMTGCIAJHZEUNB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H17N/c1-2-3-4-8-13-11-10-12-7-5-6-9-14(12)15-13/h5-7,9-11H,2-4,8H2,1H3
SMILES:	CCCCCc1ccc2ccccc2n1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL170722
PubChem CID:	185231
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]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
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]
NPO13657	Peperomia pellucida	Species	Piperaceae	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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3954	Organism	Human T-lymphotropic virus 1	Human T-lymphotropic virus 1	Inhibition	=	0.0	%	PMID[485008]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC90	=	100.0	ug.mL-1	PMID[485009]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC90	=	100.0	ug.mL-1	PMID[485009]

☑ 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 NPC81561 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	992
0.1-0.2	11148
0.2-0.3	16639
0.3-0.4	8366
0.4-0.5	2627
0.5-0.6	1790
0.6-0.7	815
0.7-0.8	244
0.8-0.85	58
0.85-0.9	11
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC148140
0.9561	High Similarity	NPC215519
0.9558	High Similarity	NPC162689
0.9558	High Similarity	NPC54102
0.9237	High Similarity	NPC122718
0.8926	High Similarity	NPC476140
0.8833	High Similarity	NPC46358
0.875	High Similarity	NPC41174
0.8618	High Similarity	NPC250361
0.8571	High Similarity	NPC475450
0.856	High Similarity	NPC473587
0.8527	High Similarity	NPC251722
0.8527	High Similarity	NPC314102
0.8516	High Similarity	NPC198988
0.8492	Intermediate Similarity	NPC475428
0.8492	Intermediate Similarity	NPC22079
0.848	Intermediate Similarity	NPC473762
0.845	Intermediate Similarity	NPC325252
0.8425	Intermediate Similarity	NPC179365
0.8397	Intermediate Similarity	NPC104483
0.8364	Intermediate Similarity	NPC213774
0.8333	Intermediate Similarity	NPC2949
0.8333	Intermediate Similarity	NPC59084
0.8271	Intermediate Similarity	NPC63157
0.8271	Intermediate Similarity	NPC473868
0.8264	Intermediate Similarity	NPC91958
0.8258	Intermediate Similarity	NPC88097
0.8217	Intermediate Similarity	NPC473930
0.8209	Intermediate Similarity	NPC20144
0.8195	Intermediate Similarity	NPC115611
0.8182	Intermediate Similarity	NPC169433
0.8106	Intermediate Similarity	NPC150259
0.806	Intermediate Similarity	NPC284635
0.803	Intermediate Similarity	NPC29886
0.803	Intermediate Similarity	NPC261195
0.803	Intermediate Similarity	NPC218268
0.7985	Intermediate Similarity	NPC73767
0.7971	Intermediate Similarity	NPC470111
0.7971	Intermediate Similarity	NPC21605
0.797	Intermediate Similarity	NPC84911
0.7969	Intermediate Similarity	NPC278451
0.7967	Intermediate Similarity	NPC143603
0.7956	Intermediate Similarity	NPC470440
0.7956	Intermediate Similarity	NPC204141
0.7951	Intermediate Similarity	NPC476566
0.7949	Intermediate Similarity	NPC302790
0.7934	Intermediate Similarity	NPC143156
0.7926	Intermediate Similarity	NPC469779
0.7926	Intermediate Similarity	NPC469783
0.7926	Intermediate Similarity	NPC469761
0.7926	Intermediate Similarity	NPC469768
0.7926	Intermediate Similarity	NPC469784
0.7926	Intermediate Similarity	NPC469767
0.7926	Intermediate Similarity	NPC469780
0.7899	Intermediate Similarity	NPC478186
0.7895	Intermediate Similarity	NPC96102
0.7886	Intermediate Similarity	NPC297486
0.7886	Intermediate Similarity	NPC240136
0.7886	Intermediate Similarity	NPC471402
0.7883	Intermediate Similarity	NPC242556
0.7868	Intermediate Similarity	NPC469766
0.7863	Intermediate Similarity	NPC82295
0.7863	Intermediate Similarity	NPC256893
0.7857	Intermediate Similarity	NPC40070
0.7857	Intermediate Similarity	NPC33421
0.7852	Intermediate Similarity	NPC312092
0.7852	Intermediate Similarity	NPC110126
0.7842	Intermediate Similarity	NPC201380
0.7842	Intermediate Similarity	NPC179787
0.7836	Intermediate Similarity	NPC105127
0.7836	Intermediate Similarity	NPC125746
0.7794	Intermediate Similarity	NPC238499
0.7786	Intermediate Similarity	NPC321911
0.7786	Intermediate Similarity	NPC282398
0.777	Intermediate Similarity	NPC63545
0.775	Intermediate Similarity	NPC27802
0.7746	Intermediate Similarity	NPC26872
0.7737	Intermediate Similarity	NPC60553
0.7737	Intermediate Similarity	NPC277157
0.7721	Intermediate Similarity	NPC32002
0.7721	Intermediate Similarity	NPC315348
0.7721	Intermediate Similarity	NPC316811
0.7714	Intermediate Similarity	NPC469811
0.7714	Intermediate Similarity	NPC477134
0.7698	Intermediate Similarity	NPC314372
0.7692	Intermediate Similarity	NPC476219
0.7692	Intermediate Similarity	NPC476297
0.7681	Intermediate Similarity	NPC190296
0.7664	Intermediate Similarity	NPC279081
0.766	Intermediate Similarity	NPC124005
0.766	Intermediate Similarity	NPC37548
0.7656	Intermediate Similarity	NPC290094
0.7638	Intermediate Similarity	NPC182570
0.7638	Intermediate Similarity	NPC48564
0.7638	Intermediate Similarity	NPC265605
0.7606	Intermediate Similarity	NPC53947
0.7597	Intermediate Similarity	NPC476322
0.7571	Intermediate Similarity	NPC469525
0.7571	Intermediate Similarity	NPC86288
0.7571	Intermediate Similarity	NPC285731
0.7552	Intermediate Similarity	NPC470233
0.7538	Intermediate Similarity	NPC245244
0.7538	Intermediate Similarity	NPC166424
0.7538	Intermediate Similarity	NPC146373
0.7536	Intermediate Similarity	NPC230002
0.7535	Intermediate Similarity	NPC187951
0.7535	Intermediate Similarity	NPC2272
0.7534	Intermediate Similarity	NPC6436
0.7534	Intermediate Similarity	NPC221786
0.7534	Intermediate Similarity	NPC475990
0.7534	Intermediate Similarity	NPC474880
0.7534	Intermediate Similarity	NPC56765
0.752	Intermediate Similarity	NPC192209
0.7518	Intermediate Similarity	NPC129042
0.7518	Intermediate Similarity	NPC143872
0.7518	Intermediate Similarity	NPC288838
0.7517	Intermediate Similarity	NPC476464
0.75	Intermediate Similarity	NPC325903
0.75	Intermediate Similarity	NPC76540
0.75	Intermediate Similarity	NPC231655
0.75	Intermediate Similarity	NPC200743
0.7483	Intermediate Similarity	NPC81229
0.7483	Intermediate Similarity	NPC229173
0.7483	Intermediate Similarity	NPC148592
0.7483	Intermediate Similarity	NPC255229
0.7483	Intermediate Similarity	NPC105818
0.7483	Intermediate Similarity	NPC24678
0.7481	Intermediate Similarity	NPC169625
0.7481	Intermediate Similarity	NPC202957
0.7466	Intermediate Similarity	NPC26850
0.7466	Intermediate Similarity	NPC129721
0.7466	Intermediate Similarity	NPC236711
0.7465	Intermediate Similarity	NPC471957
0.7448	Intermediate Similarity	NPC471458
0.7448	Intermediate Similarity	NPC470507
0.7448	Intermediate Similarity	NPC38736
0.7447	Intermediate Similarity	NPC159856
0.7432	Intermediate Similarity	NPC194881
0.7415	Intermediate Similarity	NPC477591
0.7397	Intermediate Similarity	NPC51054
0.7397	Intermediate Similarity	NPC184476
0.7397	Intermediate Similarity	NPC285469
0.7388	Intermediate Similarity	NPC69914
0.7383	Intermediate Similarity	NPC21174
0.7383	Intermediate Similarity	NPC90723
0.7383	Intermediate Similarity	NPC478182
0.7383	Intermediate Similarity	NPC271797
0.7379	Intermediate Similarity	NPC259644
0.7379	Intermediate Similarity	NPC73952
0.7379	Intermediate Similarity	NPC469765
0.7379	Intermediate Similarity	NPC281094
0.7379	Intermediate Similarity	NPC200214
0.7379	Intermediate Similarity	NPC25008
0.7379	Intermediate Similarity	NPC469760
0.7379	Intermediate Similarity	NPC469763
0.7379	Intermediate Similarity	NPC469786
0.7368	Intermediate Similarity	NPC89490
0.7365	Intermediate Similarity	NPC215584
0.7365	Intermediate Similarity	NPC44773
0.7365	Intermediate Similarity	NPC470204
0.7357	Intermediate Similarity	NPC88121
0.7347	Intermediate Similarity	NPC286427
0.7347	Intermediate Similarity	NPC299594
0.7339	Intermediate Similarity	NPC296163
0.7339	Intermediate Similarity	NPC187036
0.7333	Intermediate Similarity	NPC101165
0.7333	Intermediate Similarity	NPC195507
0.7333	Intermediate Similarity	NPC2165
0.7329	Intermediate Similarity	NPC70922
0.7329	Intermediate Similarity	NPC75540
0.7329	Intermediate Similarity	NPC211572
0.7329	Intermediate Similarity	NPC212376
0.7329	Intermediate Similarity	NPC80597
0.7328	Intermediate Similarity	NPC27740
0.7315	Intermediate Similarity	NPC470203
0.7313	Intermediate Similarity	NPC475105
0.7313	Intermediate Similarity	NPC329896
0.7313	Intermediate Similarity	NPC475090
0.7313	Intermediate Similarity	NPC476131
0.731	Intermediate Similarity	NPC470823
0.7308	Intermediate Similarity	NPC329825
0.7297	Intermediate Similarity	NPC318065
0.7297	Intermediate Similarity	NPC293487
0.7297	Intermediate Similarity	NPC206819
0.7297	Intermediate Similarity	NPC41257
0.7292	Intermediate Similarity	NPC288445
0.7267	Intermediate Similarity	NPC247987
0.726	Intermediate Similarity	NPC141926
0.726	Intermediate Similarity	NPC138842
0.726	Intermediate Similarity	NPC161108
0.7248	Intermediate Similarity	NPC473320
0.7248	Intermediate Similarity	NPC122141
0.7244	Intermediate Similarity	NPC313449
0.7237	Intermediate Similarity	NPC44161
0.723	Intermediate Similarity	NPC216643
0.7211	Intermediate Similarity	NPC207726
0.7211	Intermediate Similarity	NPC34844
0.72	Intermediate Similarity	NPC16667
0.72	Intermediate Similarity	NPC225018
0.72	Intermediate Similarity	NPC314141

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 NPC81561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	513
0.1-0.2	870
0.2-0.3	947
0.3-0.4	2032
0.4-0.5	2470
0.5-0.6	1608
0.6-0.7	587
0.7-0.8	100
0.8-0.85	18
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.873	High Similarity	NPD3385	Approved
0.871	High Similarity	NPD947	Approved
0.8571	High Similarity	NPD1251	Discontinued
0.856	High Similarity	NPD3654	Approved
0.845	Intermediate Similarity	NPD1254	Approved
0.845	Intermediate Similarity	NPD1255	Approved
0.845	Intermediate Similarity	NPD1253	Approved
0.845	Intermediate Similarity	NPD1256	Approved
0.84	Intermediate Similarity	NPD2118	Approved
0.84	Intermediate Similarity	NPD2119	Approved
0.8385	Intermediate Similarity	NPD45	Approved
0.8385	Intermediate Similarity	NPD6554	Approved
0.8293	Intermediate Similarity	NPD1561	Phase 2
0.8209	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8203	Intermediate Similarity	NPD3475	Approved
0.8203	Intermediate Similarity	NPD3476	Approved
0.8148	Intermediate Similarity	NPD4509	Discontinued
0.8148	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD1722	Approved
0.811	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD991	Phase 2
0.8074	Intermediate Similarity	NPD2006	Phase 2
0.8062	Intermediate Similarity	NPD715	Phase 3
0.806	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD1683	Approved
0.8015	Intermediate Similarity	NPD3944	Approved
0.8015	Intermediate Similarity	NPD4029	Approved
0.8015	Intermediate Similarity	NPD3942	Approved
0.8015	Intermediate Similarity	NPD4030	Approved
0.8015	Intermediate Similarity	NPD4028	Approved
0.7985	Intermediate Similarity	NPD786	Approved
0.7971	Intermediate Similarity	NPD4547	Phase 3
0.797	Intermediate Similarity	NPD1262	Discovery
0.7914	Intermediate Similarity	NPD2430	Phase 2
0.7895	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD9583	Approved
0.7883	Intermediate Similarity	NPD5254	Discontinued
0.781	Intermediate Similarity	NPD4047	Discontinued
0.7801	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD6158	Phase 2
0.7801	Intermediate Similarity	NPD2882	Phase 1
0.7734	Intermediate Similarity	NPD9357	Approved
0.7721	Intermediate Similarity	NPD2072	Approved
0.7721	Intermediate Similarity	NPD2068	Approved
0.7721	Intermediate Similarity	NPD2069	Approved
0.7721	Intermediate Similarity	NPD2075	Approved
0.7721	Intermediate Similarity	NPD2071	Approved
0.7721	Intermediate Similarity	NPD2070	Approved
0.7721	Intermediate Similarity	NPD2074	Approved
0.7721	Intermediate Similarity	NPD2073	Approved
0.7714	Intermediate Similarity	NPD1661	Suspended
0.766	Intermediate Similarity	NPD3100	Discontinued
0.766	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD268	Approved
0.7638	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD271	Approved
0.7626	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2837	Discontinued
0.7609	Intermediate Similarity	NPD5020	Approved
0.7606	Intermediate Similarity	NPD4462	Approved
0.7606	Intermediate Similarity	NPD4463	Approved
0.7586	Intermediate Similarity	NPD4326	Phase 2
0.7578	Intermediate Similarity	NPD5787	Discontinued
0.7569	Intermediate Similarity	NPD2165	Phase 1
0.7569	Intermediate Similarity	NPD6285	Phase 2
0.7556	Intermediate Similarity	NPD4880	Discontinued
0.7537	Intermediate Similarity	NPD1995	Approved
0.7537	Intermediate Similarity	NPD1994	Approved
0.7537	Intermediate Similarity	NPD1993	Approved
0.7535	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3112	Approved
0.7517	Intermediate Similarity	NPD3115	Approved
0.7517	Intermediate Similarity	NPD2150	Discontinued
0.7517	Intermediate Similarity	NPD3114	Approved
0.7517	Intermediate Similarity	NPD3113	Approved
0.75	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9098	Phase 3
0.75	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5671	Approved
0.7483	Intermediate Similarity	NPD2172	Phase 1
0.7479	Intermediate Similarity	NPD990	Approved
0.7479	Intermediate Similarity	NPD993	Approved
0.7466	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5315	Discontinued
0.7429	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1598	Discontinued
0.7422	Intermediate Similarity	NPD4811	Discontinued
0.7417	Intermediate Similarity	NPD6300	Approved
0.7417	Intermediate Similarity	NPD6299	Approved
0.7413	Intermediate Similarity	NPD1183	Approved
0.7394	Intermediate Similarity	NPD7469	Discontinued
0.7383	Intermediate Similarity	NPD3323	Discontinued
0.7361	Intermediate Similarity	NPD3835	Phase 3
0.7361	Intermediate Similarity	NPD3833	Phase 3
0.7357	Intermediate Similarity	NPD1592	Phase 3
0.7347	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4703	Approved
0.7343	Intermediate Similarity	NPD4702	Approved
0.7339	Intermediate Similarity	NPD4824	Approved
0.7339	Intermediate Similarity	NPD4823	Approved
0.7333	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2915	Discontinued
0.7323	Intermediate Similarity	NPD9396	Approved
0.7323	Intermediate Similarity	NPD9392	Approved
0.7313	Intermediate Similarity	NPD6451	Discontinued
0.7305	Intermediate Similarity	NPD3525	Discontinued
0.7302	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD4116	Approved
0.7244	Intermediate Similarity	NPD7480	Approved
0.7244	Intermediate Similarity	NPD7481	Approved
0.7237	Intermediate Similarity	NPD2641	Approved
0.7237	Intermediate Similarity	NPD2640	Approved
0.7237	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1647	Phase 1
0.723	Intermediate Similarity	NPD1648	Phase 1
0.7214	Intermediate Similarity	NPD680	Discontinued
0.72	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3546	Approved
0.719	Intermediate Similarity	NPD5412	Discontinued
0.719	Intermediate Similarity	NPD3545	Approved
0.7176	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2142	Approved
0.7174	Intermediate Similarity	NPD2141	Approved
0.7174	Intermediate Similarity	NPD2140	Approved
0.7153	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2896	Discontinued
0.7143	Intermediate Similarity	NPD3609	Approved
0.7143	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3610	Approved
0.7133	Intermediate Similarity	NPD1403	Approved
0.7133	Intermediate Similarity	NPD1404	Approved
0.7131	Intermediate Similarity	NPD4114	Approved
0.7131	Intermediate Similarity	NPD4115	Approved
0.7122	Intermediate Similarity	NPD792	Discontinued
0.7114	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2720	Phase 1
0.7105	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD976	Approved
0.7095	Intermediate Similarity	NPD977	Approved
0.7095	Intermediate Similarity	NPD975	Approved
0.7063	Intermediate Similarity	NPD4510	Discontinued
0.7051	Intermediate Similarity	NPD6492	Phase 2
0.7047	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2580	Discontinued
0.7039	Intermediate Similarity	NPD404	Discontinued
0.7032	Intermediate Similarity	NPD3117	Approved
0.7032	Intermediate Similarity	NPD3116	Approved
0.7027	Intermediate Similarity	NPD3339	Approved
0.702	Intermediate Similarity	NPD6074	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD112	Approved
0.702	Intermediate Similarity	NPD9705	Discontinued
0.7014	Intermediate Similarity	NPD3813	Approved
0.7013	Intermediate Similarity	NPD4640	Approved
0.7013	Intermediate Similarity	NPD4638	Approved
0.7013	Intermediate Similarity	NPD4639	Approved
0.7013	Intermediate Similarity	NPD5021	Discontinued
0.7008	Intermediate Similarity	NPD5631	Phase 3
0.7006	Intermediate Similarity	NPD5104	Approved
0.7006	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2330	Approved
0.7	Intermediate Similarity	NPD2373	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2581	Approved
0.7	Intermediate Similarity	NPD2582	Approved
0.7	Intermediate Similarity	NPD6497	Approved
0.6993	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1002	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1313	Approved
0.6987	Remote Similarity	NPD43	Approved
0.6987	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6182	Approved
0.6985	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5436	Phase 1
0.6968	Remote Similarity	NPD1325	Approved
0.6968	Remote Similarity	NPD1326	Approved
0.6962	Remote Similarity	NPD4181	Approved
0.6962	Remote Similarity	NPD6159	Phase 2
0.6962	Remote Similarity	NPD7111	Discontinued
0.6954	Remote Similarity	NPD5418	Discontinued
0.6954	Remote Similarity	NPD5255	Approved
0.6948	Remote Similarity	NPD2642	Approved
0.6948	Remote Similarity	NPD2639	Approved
0.6944	Remote Similarity	NPD3717	Discontinued
0.6943	Remote Similarity	NPD3799	Suspended
0.6943	Remote Similarity	NPD5065	Approved
0.6933	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2914	Approved
0.6929	Remote Similarity	NPD2913	Approved
0.6923	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6828	Phase 2
0.6908	Remote Similarity	NPD6454	Clinical (unspecified phase)

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