NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	157.09
Volume:	179.514
LogP:	2.818
LogD:	2.946
LogS:	-2.266
# Rotatable Bonds:	0
TPSA:	12.89
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.573
Synthetic Accessibility Score:	1.625
Fsp3:	0.182
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:	-4.594
MDCK Permeability:	2.225041862402577e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.18
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.969
Plasma Protein Binding (PPB):	92.49066925048828%
Volume Distribution (VD):	0.7
Pgp-substrate:	6.766606330871582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.524
CYP2C19-substrate:	0.649
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.543
CYP2D6-inhibitor:	0.718
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.448

ADMET: Excretion

Clearance (CL):	5.079
Half-life (T1/2):	0.396

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.297
Drug-inuced Liver Injury (DILI):	0.281
AMES Toxicity:	0.844
Rat Oral Acute Toxicity:	0.197
Maximum Recommended Daily Dose:	0.128
Skin Sensitization:	0.329
Carcinogencity:	0.797
Eye Corrosion:	0.404
Eye Irritation:	0.984
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC215519

Natural Product ID:	NPC215519
*Common Name:**	2,6-Dimethylquinoline
IUPAC Name:	2,6-dimethylquinoline
Synonyms:	2,6-Dimethyl-Quinoline; 2,6-Dimethylquinoline
Standard InCHIKey:	JJPSZKIOGBRMHK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H11N/c1-8-3-6-11-10(7-8)5-4-9(2)12-11/h3-7H,1-2H3
SMILES:	Cc1ccc2c(c1)ccc(n2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL194502
PubChem CID:	13414
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
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[22784551]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[25068578]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	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	5
Others	1

Activity Type	# Activity
Individual Protein	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	3300.0	nM	PMID[507884]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	280000.0	nM	PMID[507885]
NPT1420	Individual Protein	Cytochrome P450 2A5	Mus musculus	IC50	=	40000.0	nM	PMID[507885]
NPT1420	Individual Protein	Cytochrome P450 2A5	Mus musculus	IC50	=	39994.47	nM	PMID[507886]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	279898.13	nM	PMID[507886]
NPT27	Others	Unspecified		Ratio	=	7.0	n.a.	PMID[507885]

☑ 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 NPC215519 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	1236
0.1-0.2	12104
0.2-0.3	16599
0.3-0.4	7530
0.4-0.5	2485
0.5-0.6	1753
0.6-0.7	723
0.7-0.8	221
0.8-0.85	31
0.85-0.9	9
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9658	High Similarity	NPC122718
0.9646	High Similarity	NPC148140
0.9561	High Similarity	NPC81561
0.931	High Similarity	NPC162689
0.931	High Similarity	NPC54102
0.881	High Similarity	NPC179365
0.871	High Similarity	NPC476140
0.8651	High Similarity	NPC473587
0.8618	High Similarity	NPC46358
0.8583	High Similarity	NPC475428
0.8571	High Similarity	NPC473762
0.855	High Similarity	NPC169433
0.8537	High Similarity	NPC41174
0.8516	High Similarity	NPC475450
0.8473	Intermediate Similarity	NPC314102
0.8473	Intermediate Similarity	NPC251722
0.8413	Intermediate Similarity	NPC250361
0.8321	Intermediate Similarity	NPC198988
0.8308	Intermediate Similarity	NPC473930
0.8295	Intermediate Similarity	NPC22079
0.8258	Intermediate Similarity	NPC325252
0.8142	Intermediate Similarity	NPC213774
0.8074	Intermediate Similarity	NPC104483
0.8065	Intermediate Similarity	NPC91958
0.8015	Intermediate Similarity	NPC2949
0.8015	Intermediate Similarity	NPC59084
0.8015	Intermediate Similarity	NPC115611
0.7956	Intermediate Similarity	NPC473868
0.7956	Intermediate Similarity	NPC63157
0.7941	Intermediate Similarity	NPC312092
0.7941	Intermediate Similarity	NPC88097
0.7929	Intermediate Similarity	NPC21605
0.7899	Intermediate Similarity	NPC20144
0.7883	Intermediate Similarity	NPC284635
0.7879	Intermediate Similarity	NPC282398
0.7872	Intermediate Similarity	NPC124005
0.7852	Intermediate Similarity	NPC29886
0.7852	Intermediate Similarity	NPC261195
0.7817	Intermediate Similarity	NPC33421
0.7794	Intermediate Similarity	NPC84911
0.7794	Intermediate Similarity	NPC150259
0.7786	Intermediate Similarity	NPC470440
0.7778	Intermediate Similarity	NPC143603
0.775	Intermediate Similarity	NPC302790
0.7742	Intermediate Similarity	NPC143156
0.773	Intermediate Similarity	NPC129042
0.773	Intermediate Similarity	NPC478186
0.7721	Intermediate Similarity	NPC96102
0.7721	Intermediate Similarity	NPC218268
0.7687	Intermediate Similarity	NPC215584
0.7687	Intermediate Similarity	NPC82295
0.7687	Intermediate Similarity	NPC256893
0.7687	Intermediate Similarity	NPC44773
0.7681	Intermediate Similarity	NPC110126
0.7681	Intermediate Similarity	NPC73767
0.7676	Intermediate Similarity	NPC179787
0.7676	Intermediate Similarity	NPC201380
0.7676	Intermediate Similarity	NPC470111
0.7664	Intermediate Similarity	NPC125746
0.7664	Intermediate Similarity	NPC105127
0.766	Intermediate Similarity	NPC204141
0.7655	Intermediate Similarity	NPC38736
0.7652	Intermediate Similarity	NPC278451
0.7626	Intermediate Similarity	NPC238499
0.7626	Intermediate Similarity	NPC469767
0.7626	Intermediate Similarity	NPC469779
0.7626	Intermediate Similarity	NPC469780
0.7626	Intermediate Similarity	NPC469761
0.7626	Intermediate Similarity	NPC469783
0.7626	Intermediate Similarity	NPC469784
0.7626	Intermediate Similarity	NPC469768
0.7622	Intermediate Similarity	NPC321911
0.7619	Intermediate Similarity	NPC476566
0.7606	Intermediate Similarity	NPC63545
0.7603	Intermediate Similarity	NPC184476
0.7589	Intermediate Similarity	NPC242556
0.7586	Intermediate Similarity	NPC161108
0.7584	Intermediate Similarity	NPC90723
0.7571	Intermediate Similarity	NPC60553
0.7571	Intermediate Similarity	NPC469766
0.7571	Intermediate Similarity	NPC277157
0.7569	Intermediate Similarity	NPC40070
0.7561	Intermediate Similarity	NPC27802
0.7559	Intermediate Similarity	NPC297486
0.7559	Intermediate Similarity	NPC471402
0.7559	Intermediate Similarity	NPC240136
0.7552	Intermediate Similarity	NPC469811
0.7552	Intermediate Similarity	NPC477134
0.7518	Intermediate Similarity	NPC190296
0.75	Intermediate Similarity	NPC6436
0.75	Intermediate Similarity	NPC279081
0.75	Intermediate Similarity	NPC56765
0.75	Intermediate Similarity	NPC187951
0.7466	Intermediate Similarity	NPC200743
0.7466	Intermediate Similarity	NPC26872
0.7462	Intermediate Similarity	NPC48564
0.7462	Intermediate Similarity	NPC265605
0.7462	Intermediate Similarity	NPC182570
0.745	Intermediate Similarity	NPC473320
0.7447	Intermediate Similarity	NPC88121
0.7432	Intermediate Similarity	NPC76982
0.7429	Intermediate Similarity	NPC32002
0.7429	Intermediate Similarity	NPC315348
0.7429	Intermediate Similarity	NPC316811
0.7415	Intermediate Similarity	NPC476219
0.7415	Intermediate Similarity	NPC476297
0.7413	Intermediate Similarity	NPC314372
0.7413	Intermediate Similarity	NPC86288
0.7413	Intermediate Similarity	NPC285731
0.74	Intermediate Similarity	NPC16667
0.7379	Intermediate Similarity	NPC37548
0.7376	Intermediate Similarity	NPC230002
0.7368	Intermediate Similarity	NPC245244
0.7368	Intermediate Similarity	NPC166424
0.7368	Intermediate Similarity	NPC146373
0.7365	Intermediate Similarity	NPC51054
0.7361	Intermediate Similarity	NPC288838
0.7361	Intermediate Similarity	NPC143872
0.7351	Intermediate Similarity	NPC271734
0.7348	Intermediate Similarity	NPC290094
0.7347	Intermediate Similarity	NPC325903
0.7329	Intermediate Similarity	NPC148592
0.7329	Intermediate Similarity	NPC53947
0.7317	Intermediate Similarity	NPC76540
0.7317	Intermediate Similarity	NPC231655
0.7315	Intermediate Similarity	NPC26850
0.7315	Intermediate Similarity	NPC236711
0.731	Intermediate Similarity	NPC471957
0.7293	Intermediate Similarity	NPC476322
0.7292	Intermediate Similarity	NPC159856
0.7292	Intermediate Similarity	NPC469525
0.7279	Intermediate Similarity	NPC470233
0.7267	Intermediate Similarity	NPC477591
0.7267	Intermediate Similarity	NPC221786
0.7267	Intermediate Similarity	NPC206819
0.7267	Intermediate Similarity	NPC318065
0.7267	Intermediate Similarity	NPC474880
0.7267	Intermediate Similarity	NPC475990
0.7267	Intermediate Similarity	NPC67056
0.7267	Intermediate Similarity	NPC474791
0.726	Intermediate Similarity	NPC2272
0.7248	Intermediate Similarity	NPC476464
0.7237	Intermediate Similarity	NPC472587
0.723	Intermediate Similarity	NPC281094
0.7219	Intermediate Similarity	NPC81229
0.7219	Intermediate Similarity	NPC255229
0.7219	Intermediate Similarity	NPC229173
0.7211	Intermediate Similarity	NPC105818
0.7211	Intermediate Similarity	NPC24678
0.7209	Intermediate Similarity	NPC192209
0.72	Intermediate Similarity	NPC129721
0.72	Intermediate Similarity	NPC286427
0.7185	Intermediate Similarity	NPC169625
0.7185	Intermediate Similarity	NPC202957
0.7181	Intermediate Similarity	NPC207726
0.7181	Intermediate Similarity	NPC471458
0.7181	Intermediate Similarity	NPC470507
0.7174	Intermediate Similarity	NPC101165
0.7171	Intermediate Similarity	NPC194881
0.7165	Intermediate Similarity	NPC187036
0.7165	Intermediate Similarity	NPC296163
0.7164	Intermediate Similarity	NPC27740
0.7162	Intermediate Similarity	NPC470823
0.7161	Intermediate Similarity	NPC280548
0.7152	Intermediate Similarity	NPC293487
0.7152	Intermediate Similarity	NPC41257
0.7143	Intermediate Similarity	NPC288445
0.7133	Intermediate Similarity	NPC285469
0.7124	Intermediate Similarity	NPC21174
0.7124	Intermediate Similarity	NPC271797
0.7124	Intermediate Similarity	NPC478182
0.7115	Intermediate Similarity	NPC6982
0.7114	Intermediate Similarity	NPC469763
0.7114	Intermediate Similarity	NPC138842
0.7114	Intermediate Similarity	NPC25008
0.7114	Intermediate Similarity	NPC200214
0.7114	Intermediate Similarity	NPC469765
0.7114	Intermediate Similarity	NPC73952
0.7114	Intermediate Similarity	NPC141926
0.7114	Intermediate Similarity	NPC469786
0.7114	Intermediate Similarity	NPC469760
0.7114	Intermediate Similarity	NPC259644
0.7105	Intermediate Similarity	NPC122141
0.7105	Intermediate Similarity	NPC470204
0.7101	Intermediate Similarity	NPC69914
0.7086	Intermediate Similarity	NPC299594
0.708	Intermediate Similarity	NPC89490
0.7078	Intermediate Similarity	NPC470508
0.7078	Intermediate Similarity	NPC115232
0.7078	Intermediate Similarity	NPC195507
0.7078	Intermediate Similarity	NPC2165
0.707	Intermediate Similarity	NPC34508
0.7067	Intermediate Similarity	NPC34844
0.7067	Intermediate Similarity	NPC75540
0.7067	Intermediate Similarity	NPC70922
0.7067	Intermediate Similarity	NPC212376
0.7067	Intermediate Similarity	NPC80597
0.7067	Intermediate Similarity	NPC211572
0.7059	Intermediate Similarity	NPC470203
0.7059	Intermediate Similarity	NPC225018

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 NPC215519 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	592
0.1-0.2	851
0.2-0.3	993
0.3-0.4	2166
0.4-0.5	2429
0.5-0.6	1560
0.6-0.7	462
0.7-0.8	85
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD947	Approved
0.8661	High Similarity	NPD1251	Discontinued
0.8538	High Similarity	NPD1254	Approved
0.8538	High Similarity	NPD1253	Approved
0.8538	High Similarity	NPD1255	Approved
0.8538	High Similarity	NPD1256	Approved
0.8385	Intermediate Similarity	NPD3385	Approved
0.8248	Intermediate Similarity	NPD1683	Approved
0.8217	Intermediate Similarity	NPD3654	Approved
0.8188	Intermediate Similarity	NPD4547	Phase 3
0.8095	Intermediate Similarity	NPD1561	Phase 2
0.8062	Intermediate Similarity	NPD2119	Approved
0.8062	Intermediate Similarity	NPD2118	Approved
0.806	Intermediate Similarity	NPD45	Approved
0.806	Intermediate Similarity	NPD6554	Approved
0.7923	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD991	Phase 2
0.7899	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD3475	Approved
0.7879	Intermediate Similarity	NPD715	Phase 3
0.7879	Intermediate Similarity	NPD3476	Approved
0.7872	Intermediate Similarity	NPD3100	Discontinued
0.7842	Intermediate Similarity	NPD4509	Discontinued
0.7842	Intermediate Similarity	NPD5254	Discontinued
0.7842	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1722	Approved
0.7794	Intermediate Similarity	NPD1262	Discovery
0.777	Intermediate Similarity	NPD2006	Phase 2
0.7762	Intermediate Similarity	NPD2882	Phase 1
0.7754	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD9583	Approved
0.7704	Intermediate Similarity	NPD3944	Approved
0.7704	Intermediate Similarity	NPD4028	Approved
0.7704	Intermediate Similarity	NPD4030	Approved
0.7704	Intermediate Similarity	NPD4029	Approved
0.7704	Intermediate Similarity	NPD3942	Approved
0.7692	Intermediate Similarity	NPD2172	Phase 1
0.7681	Intermediate Similarity	NPD786	Approved
0.7622	Intermediate Similarity	NPD2430	Phase 2
0.7557	Intermediate Similarity	NPD9357	Approved
0.7518	Intermediate Similarity	NPD4047	Discontinued
0.7517	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6158	Phase 2
0.7483	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD271	Approved
0.7462	Intermediate Similarity	NPD268	Approved
0.7462	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2641	Approved
0.7434	Intermediate Similarity	NPD2640	Approved
0.7431	Intermediate Similarity	NPD1661	Suspended
0.7429	Intermediate Similarity	NPD2071	Approved
0.7429	Intermediate Similarity	NPD2075	Approved
0.7429	Intermediate Similarity	NPD2072	Approved
0.7429	Intermediate Similarity	NPD2068	Approved
0.7429	Intermediate Similarity	NPD2070	Approved
0.7429	Intermediate Similarity	NPD2074	Approved
0.7429	Intermediate Similarity	NPD2073	Approved
0.7429	Intermediate Similarity	NPD2069	Approved
0.7417	Intermediate Similarity	NPD2720	Phase 1
0.7417	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5315	Discontinued
0.7391	Intermediate Similarity	NPD4880	Discontinued
0.7379	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6299	Approved
0.7377	Intermediate Similarity	NPD6300	Approved
0.7357	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3323	Discontinued
0.7347	Intermediate Similarity	NPD2837	Discontinued
0.7333	Intermediate Similarity	NPD1403	Approved
0.7333	Intermediate Similarity	NPD1404	Approved
0.7329	Intermediate Similarity	NPD4463	Approved
0.7329	Intermediate Similarity	NPD4462	Approved
0.7324	Intermediate Similarity	NPD5020	Approved
0.7317	Intermediate Similarity	NPD9098	Phase 3
0.7317	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4326	Phase 2
0.7303	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6285	Phase 2
0.7297	Intermediate Similarity	NPD2165	Phase 1
0.7295	Intermediate Similarity	NPD993	Approved
0.7295	Intermediate Similarity	NPD990	Approved
0.7273	Intermediate Similarity	NPD5787	Discontinued
0.726	Intermediate Similarity	NPD1183	Approved
0.726	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1598	Discontinued
0.7248	Intermediate Similarity	NPD3115	Approved
0.7248	Intermediate Similarity	NPD3114	Approved
0.7248	Intermediate Similarity	NPD2150	Discontinued
0.7248	Intermediate Similarity	NPD3113	Approved
0.7248	Intermediate Similarity	NPD3112	Approved
0.7246	Intermediate Similarity	NPD1994	Approved
0.7246	Intermediate Similarity	NPD1993	Approved
0.7246	Intermediate Similarity	NPD1995	Approved
0.7222	Intermediate Similarity	NPD5671	Approved
0.7219	Intermediate Similarity	NPD6074	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5021	Discontinued
0.7203	Intermediate Similarity	NPD1592	Phase 3
0.72	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD975	Approved
0.7181	Intermediate Similarity	NPD977	Approved
0.7181	Intermediate Similarity	NPD976	Approved
0.7161	Intermediate Similarity	NPD1326	Approved
0.7161	Intermediate Similarity	NPD5436	Phase 1
0.7161	Intermediate Similarity	NPD1325	Approved
0.7154	Intermediate Similarity	NPD9396	Approved
0.7154	Intermediate Similarity	NPD9392	Approved
0.7153	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7111	Discontinued
0.7143	Intermediate Similarity	NPD2639	Approved
0.7143	Intermediate Similarity	NPD2642	Approved
0.7132	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7469	Discontinued
0.7121	Intermediate Similarity	NPD4811	Discontinued
0.7115	Intermediate Similarity	NPD3609	Approved
0.7115	Intermediate Similarity	NPD3610	Approved
0.7097	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3833	Phase 3
0.7095	Intermediate Similarity	NPD3835	Phase 3
0.7086	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2915	Discontinued
0.7078	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4703	Approved
0.7075	Intermediate Similarity	NPD4702	Approved
0.707	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD680	Discontinued
0.7063	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3525	Discontinued
0.7031	Intermediate Similarity	NPD4824	Approved
0.7031	Intermediate Similarity	NPD4823	Approved
0.7029	Intermediate Similarity	NPD6451	Discontinued
0.702	Intermediate Similarity	NPD2580	Discontinued
0.7015	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4639	Approved
0.6987	Remote Similarity	NPD4638	Approved
0.6987	Remote Similarity	NPD4640	Approved
0.6987	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4116	Approved
0.6981	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1648	Phase 1
0.6974	Remote Similarity	NPD1647	Phase 1
0.6974	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1597	Phase 1
0.6948	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7480	Approved
0.6947	Remote Similarity	NPD7481	Approved
0.6943	Remote Similarity	NPD5412	Discontinued
0.6937	Remote Similarity	NPD4181	Approved
0.6933	Remote Similarity	NPD4957	Phase 2
0.6918	Remote Similarity	NPD3799	Suspended
0.6908	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD404	Discontinued
0.6901	Remote Similarity	NPD2140	Approved
0.6901	Remote Similarity	NPD2141	Approved
0.6901	Remote Similarity	NPD2142	Approved
0.6899	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD9705	Discontinued
0.6883	Remote Similarity	NPD112	Approved
0.688	Remote Similarity	NPD3546	Approved
0.688	Remote Similarity	NPD3545	Approved
0.6875	Remote Similarity	NPD2381	Approved
0.6875	Remote Similarity	NPD2380	Approved
0.6875	Remote Similarity	NPD2896	Discontinued
0.6875	Remote Similarity	NPD2382	Approved
0.6863	Remote Similarity	NPD2330	Approved
0.6859	Remote Similarity	NPD1002	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD792	Discontinued
0.6852	Remote Similarity	NPD6515	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6514	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7633	Discontinued
0.6832	Remote Similarity	NPD2144	Approved
0.6829	Remote Similarity	NPD4735	Approved
0.6829	Remote Similarity	NPD4734	Approved
0.6828	Remote Similarity	NPD1953	Discontinued
0.6825	Remote Similarity	NPD4115	Approved
0.6825	Remote Similarity	NPD4114	Approved
0.6815	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4128	Approved
0.6813	Remote Similarity	NPD6492	Phase 2
0.6807	Remote Similarity	NPD7394	Phase 2
0.6803	Remote Similarity	NPD4510	Discontinued
0.6797	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3116	Approved
0.6792	Remote Similarity	NPD3117	Approved
0.6776	Remote Similarity	NPD3339	Approved
0.6772	Remote Similarity	NPD5862	Discovery
0.6772	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4075	Phase 2
0.677	Remote Similarity	NPD5104	Approved
0.677	Remote Similarity	NPD5100	Phase 3
0.6768	Remote Similarity	NPD5105	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