NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	127.05
Volume:	133.929
LogP:	3.025
LogD:	1.705
LogS:	-2.63
# Rotatable Bonds:	4
TPSA:	12.36
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.244
Synthetic Accessibility Score:	3.545
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.41
MDCK Permeability:	2.948726796603296e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.318
Plasma Protein Binding (PPB):	33.69535827636719%
Volume Distribution (VD):	1.694
Pgp-substrate:	64.21240997314453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.252
CYP1A2-substrate:	0.389
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.482
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.763
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	7.175
Half-life (T1/2):	0.587

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.065
AMES Toxicity:	0.241
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.176
Skin Sensitization:	0.943
Carcinogencity:	0.676
Eye Corrosion:	0.992
Eye Irritation:	0.988
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC138842

Natural Product ID:	NPC138842
*Common Name:**	OEFOMVQWNBXRQW-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	Eupolauridine N-Oxide
Standard InCHIKey:	OEFOMVQWNBXRQW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H8N2O/c17-16-8-6-9-5-7-15-13-10-3-1-2-4-11(10)14(16)12(9)13/h1-8H
SMILES:	O=n1ccc2c3c1c1ccccc1c3ncc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801766
PubChem CID:	460765
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0001857] Naphthyridines

*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
NPO13611	Ambavia gerrardii	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[21504145]
NPO13611	Ambavia gerrardii	Species	Annonaceae	Eukaryota	n.a.	Madagascar Dry Forest	n.a.	PMID[21504145]
NPO13611	Ambavia gerrardii	Species	Annonaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	1770.0	nM	PMID[527327]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	3500.0	nM	PMID[527327]

☑ 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 NPC138842 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	1278
0.1-0.2	12302
0.2-0.3	19219
0.3-0.4	5203
0.4-0.5	2097
0.5-0.6	1793
0.6-0.7	629
0.7-0.8	168
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC86288
0.8013	Intermediate Similarity	NPC169433
0.7962	Intermediate Similarity	NPC40070
0.7949	Intermediate Similarity	NPC470111
0.7947	Intermediate Similarity	NPC314102
0.7947	Intermediate Similarity	NPC251722
0.7937	Intermediate Similarity	NPC236711
0.7917	Intermediate Similarity	NPC46358
0.7817	Intermediate Similarity	NPC143603
0.7817	Intermediate Similarity	NPC91958
0.7802	Intermediate Similarity	NPC323345
0.7802	Intermediate Similarity	NPC470164
0.7799	Intermediate Similarity	NPC470233
0.7785	Intermediate Similarity	NPC282398
0.7784	Intermediate Similarity	NPC329541
0.7665	Intermediate Similarity	NPC32534
0.7658	Intermediate Similarity	NPC63545
0.764	Intermediate Similarity	NPC325903
0.7636	Intermediate Similarity	NPC265100
0.7636	Intermediate Similarity	NPC317105
0.7622	Intermediate Similarity	NPC44773
0.7622	Intermediate Similarity	NPC215584
0.761	Intermediate Similarity	NPC201380
0.761	Intermediate Similarity	NPC179787
0.761	Intermediate Similarity	NPC469811
0.7597	Intermediate Similarity	NPC105127
0.7595	Intermediate Similarity	NPC285731
0.7576	Intermediate Similarity	NPC225018
0.7569	Intermediate Similarity	NPC287437
0.7568	Intermediate Similarity	NPC166424
0.7568	Intermediate Similarity	NPC245244
0.7568	Intermediate Similarity	NPC146373
0.7562	Intermediate Similarity	NPC321911
0.7561	Intermediate Similarity	NPC80681
0.755	Intermediate Similarity	NPC69914
0.7547	Intermediate Similarity	NPC288838
0.7546	Intermediate Similarity	NPC51054
0.7544	Intermediate Similarity	NPC237188
0.7532	Intermediate Similarity	NPC96102
0.7529	Intermediate Similarity	NPC471579
0.75	Intermediate Similarity	NPC256893
0.75	Intermediate Similarity	NPC476322
0.75	Intermediate Similarity	NPC110126
0.7484	Intermediate Similarity	NPC150259
0.7484	Intermediate Similarity	NPC84911
0.7483	Intermediate Similarity	NPC476131
0.7455	Intermediate Similarity	NPC293487
0.7448	Intermediate Similarity	NPC162689
0.7448	Intermediate Similarity	NPC54102
0.744	Intermediate Similarity	NPC56233
0.7432	Intermediate Similarity	NPC290094
0.7427	Intermediate Similarity	NPC297034
0.7425	Intermediate Similarity	NPC478184
0.7419	Intermediate Similarity	NPC261195
0.7419	Intermediate Similarity	NPC29886
0.7415	Intermediate Similarity	NPC182570
0.7415	Intermediate Similarity	NPC48564
0.7415	Intermediate Similarity	NPC265605
0.7412	Intermediate Similarity	NPC201634
0.7407	Intermediate Similarity	NPC53947
0.7389	Intermediate Similarity	NPC73767
0.7386	Intermediate Similarity	NPC101165
0.7358	Intermediate Similarity	NPC20144
0.7358	Intermediate Similarity	NPC190296
0.7349	Intermediate Similarity	NPC56765
0.7342	Intermediate Similarity	NPC469761
0.7342	Intermediate Similarity	NPC469779
0.7342	Intermediate Similarity	NPC469767
0.7342	Intermediate Similarity	NPC469780
0.7342	Intermediate Similarity	NPC279081
0.7342	Intermediate Similarity	NPC469784
0.7342	Intermediate Similarity	NPC469783
0.7342	Intermediate Similarity	NPC469768
0.7341	Intermediate Similarity	NPC157583
0.7321	Intermediate Similarity	NPC478182
0.731	Intermediate Similarity	NPC148140
0.7305	Intermediate Similarity	NPC122141
0.7296	Intermediate Similarity	NPC469766
0.7289	Intermediate Similarity	NPC216643
0.7285	Intermediate Similarity	NPC169625
0.7285	Intermediate Similarity	NPC202957
0.7278	Intermediate Similarity	NPC316811
0.7278	Intermediate Similarity	NPC88097
0.7278	Intermediate Similarity	NPC32002
0.7278	Intermediate Similarity	NPC315348
0.7273	Intermediate Similarity	NPC82295
0.7267	Intermediate Similarity	NPC27740
0.7267	Intermediate Similarity	NPC159856
0.7267	Intermediate Similarity	NPC314372
0.7262	Intermediate Similarity	NPC478185
0.726	Intermediate Similarity	NPC240136
0.726	Intermediate Similarity	NPC297486
0.726	Intermediate Similarity	NPC81561
0.726	Intermediate Similarity	NPC471402
0.7248	Intermediate Similarity	NPC329825
0.7246	Intermediate Similarity	NPC92796
0.7246	Intermediate Similarity	NPC477591
0.7246	Intermediate Similarity	NPC135141
0.7235	Intermediate Similarity	NPC478183
0.7233	Intermediate Similarity	NPC284635
0.7233	Intermediate Similarity	NPC230002
0.7222	Intermediate Similarity	NPC143872
0.7202	Intermediate Similarity	NPC470204
0.719	Intermediate Similarity	NPC89490
0.7186	Intermediate Similarity	NPC286427
0.7184	Intermediate Similarity	NPC280852
0.7178	Intermediate Similarity	NPC471957
0.717	Intermediate Similarity	NPC104483
0.7169	Intermediate Similarity	NPC476219
0.716	Intermediate Similarity	NPC470203
0.716	Intermediate Similarity	NPC469525
0.7152	Intermediate Similarity	NPC122718
0.7151	Intermediate Similarity	NPC91895
0.7143	Intermediate Similarity	NPC475090
0.7143	Intermediate Similarity	NPC318065
0.7143	Intermediate Similarity	NPC329896
0.7143	Intermediate Similarity	NPC475105
0.7143	Intermediate Similarity	NPC41257
0.7143	Intermediate Similarity	NPC206819
0.7135	Intermediate Similarity	NPC467063
0.7134	Intermediate Similarity	NPC198988
0.7133	Intermediate Similarity	NPC27802
0.7126	Intermediate Similarity	NPC476464
0.7126	Intermediate Similarity	NPC317054
0.7125	Intermediate Similarity	NPC115611
0.7118	Intermediate Similarity	NPC90723
0.7118	Intermediate Similarity	NPC97367
0.7114	Intermediate Similarity	NPC215519
0.7091	Intermediate Similarity	NPC105818
0.7091	Intermediate Similarity	NPC24678
0.7089	Intermediate Similarity	NPC325252
0.7083	Intermediate Similarity	NPC129721
0.7076	Intermediate Similarity	NPC274229
0.7073	Intermediate Similarity	NPC21605
0.7059	Intermediate Similarity	NPC135488
0.7051	Intermediate Similarity	NPC324611
0.7048	Intermediate Similarity	NPC216713
0.7019	Intermediate Similarity	NPC59084
0.7011	Intermediate Similarity	NPC82331
0.7006	Intermediate Similarity	NPC469786
0.7006	Intermediate Similarity	NPC469760
0.7006	Intermediate Similarity	NPC469763
0.7006	Intermediate Similarity	NPC259644
0.7006	Intermediate Similarity	NPC73952
0.7006	Intermediate Similarity	NPC469765
0.7006	Intermediate Similarity	NPC25008
0.7006	Intermediate Similarity	NPC200214
0.6987	Remote Similarity	NPC22079
0.6982	Remote Similarity	NPC469897
0.6978	Remote Similarity	NPC255909
0.6978	Remote Similarity	NPC103119
0.6975	Remote Similarity	NPC473868
0.6975	Remote Similarity	NPC63157
0.6964	Remote Similarity	NPC211572
0.6964	Remote Similarity	NPC70922
0.6964	Remote Similarity	NPC80597
0.6964	Remote Similarity	NPC212376
0.6964	Remote Similarity	NPC75540
0.6954	Remote Similarity	NPC116961
0.6954	Remote Similarity	NPC194411
0.6954	Remote Similarity	NPC97343
0.6948	Remote Similarity	NPC250361
0.6946	Remote Similarity	NPC470823
0.6941	Remote Similarity	NPC6436
0.6923	Remote Similarity	NPC76540
0.6923	Remote Similarity	NPC231655
0.6923	Remote Similarity	NPC469785
0.6914	Remote Similarity	NPC2949
0.691	Remote Similarity	NPC12649
0.6905	Remote Similarity	NPC141926
0.6903	Remote Similarity	NPC471313
0.6903	Remote Similarity	NPC471311
0.6901	Remote Similarity	NPC229173
0.6901	Remote Similarity	NPC279918
0.6899	Remote Similarity	NPC473930
0.6897	Remote Similarity	NPC63751
0.6893	Remote Similarity	NPC474958
0.6893	Remote Similarity	NPC203754
0.6893	Remote Similarity	NPC150048
0.6886	Remote Similarity	NPC33421
0.6882	Remote Similarity	NPC469762
0.6875	Remote Similarity	NPC475288
0.6875	Remote Similarity	NPC477611
0.6872	Remote Similarity	NPC24864
0.6865	Remote Similarity	NPC216550
0.6864	Remote Similarity	NPC34844
0.6864	Remote Similarity	NPC476297
0.686	Remote Similarity	NPC282231
0.686	Remote Similarity	NPC242116
0.6859	Remote Similarity	NPC473762
0.6857	Remote Similarity	NPC474897
0.6854	Remote Similarity	NPC59269
0.6852	Remote Similarity	NPC312092
0.6851	Remote Similarity	NPC108011
0.6848	Remote Similarity	NPC470440
0.6848	Remote Similarity	NPC231536
0.6845	Remote Similarity	NPC128244
0.6836	Remote Similarity	NPC37423
0.6836	Remote Similarity	NPC275305
0.6832	Remote Similarity	NPC65408

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 NPC138842 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	572
0.1-0.2	765
0.2-0.3	1159
0.3-0.4	2451
0.4-0.5	2158
0.5-0.6	1501
0.6-0.7	454
0.7-0.8	85
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8108	Intermediate Similarity	NPD4030	Approved
0.8108	Intermediate Similarity	NPD3944	Approved
0.8108	Intermediate Similarity	NPD4029	Approved
0.8108	Intermediate Similarity	NPD3942	Approved
0.8108	Intermediate Similarity	NPD4028	Approved
0.8065	Intermediate Similarity	NPD4547	Phase 3
0.8	Intermediate Similarity	NPD5418	Discontinued
0.7925	Intermediate Similarity	NPD975	Approved
0.7925	Intermediate Similarity	NPD977	Approved
0.7925	Intermediate Similarity	NPD976	Approved
0.7922	Intermediate Similarity	NPD2006	Phase 2
0.7905	Intermediate Similarity	NPD715	Phase 3
0.7901	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD2430	Phase 2
0.7862	Intermediate Similarity	NPD2837	Discontinued
0.7823	Intermediate Similarity	NPD2119	Approved
0.7823	Intermediate Similarity	NPD2118	Approved
0.7823	Intermediate Similarity	NPD991	Phase 2
0.7823	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3476	Approved
0.7667	Intermediate Similarity	NPD3475	Approved
0.764	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3385	Approved
0.7628	Intermediate Similarity	NPD1722	Approved
0.7607	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2580	Discontinued
0.7532	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6497	Approved
0.7485	Intermediate Similarity	NPD2720	Phase 1
0.7485	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7469	Discontinued
0.7419	Intermediate Similarity	NPD1254	Approved
0.7419	Intermediate Similarity	NPD1255	Approved
0.7419	Intermediate Similarity	NPD1256	Approved
0.7419	Intermediate Similarity	NPD1253	Approved
0.7415	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD268	Approved
0.7415	Intermediate Similarity	NPD271	Approved
0.74	Intermediate Similarity	NPD9583	Approved
0.7396	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD786	Approved
0.7384	Intermediate Similarity	NPD2771	Approved
0.7368	Intermediate Similarity	NPD947	Approved
0.7346	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3323	Discontinued
0.7317	Intermediate Similarity	NPD3339	Approved
0.7314	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2068	Approved
0.7278	Intermediate Similarity	NPD2070	Approved
0.7278	Intermediate Similarity	NPD2074	Approved
0.7278	Intermediate Similarity	NPD2073	Approved
0.7278	Intermediate Similarity	NPD2075	Approved
0.7278	Intermediate Similarity	NPD2072	Approved
0.7278	Intermediate Similarity	NPD2071	Approved
0.7278	Intermediate Similarity	NPD2069	Approved
0.7267	Intermediate Similarity	NPD9357	Approved
0.7267	Intermediate Similarity	NPD7217	Approved
0.7267	Intermediate Similarity	NPD7216	Approved
0.7262	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5315	Discontinued
0.7261	Intermediate Similarity	NPD6554	Approved
0.7261	Intermediate Similarity	NPD45	Approved
0.7255	Intermediate Similarity	NPD3654	Approved
0.725	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1598	Discontinued
0.7207	Intermediate Similarity	NPD7394	Phase 2
0.7193	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2751	Phase 1
0.7178	Intermediate Similarity	NPD1661	Suspended
0.7169	Intermediate Similarity	NPD2165	Phase 1
0.7161	Intermediate Similarity	NPD1251	Discontinued
0.716	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4615	Phase 2
0.7135	Intermediate Similarity	NPD4957	Phase 2
0.7134	Intermediate Similarity	NPD3100	Discontinued
0.7127	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3113	Approved
0.7126	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3115	Approved
0.7126	Intermediate Similarity	NPD3112	Approved
0.7126	Intermediate Similarity	NPD3114	Approved
0.7095	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5555	Phase 1
0.7093	Intermediate Similarity	NPD5862	Discovery
0.7091	Intermediate Similarity	NPD2462	Phase 3
0.7091	Intermediate Similarity	NPD2466	Phase 3
0.7091	Intermediate Similarity	NPD2465	Approved
0.7073	Intermediate Similarity	NPD4703	Approved
0.7073	Intermediate Similarity	NPD4702	Approved
0.7066	Intermediate Similarity	NPD6285	Phase 2
0.7063	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5400	Approved
0.7059	Intermediate Similarity	NPD6771	Discontinued
0.7045	Intermediate Similarity	NPD2753	Discontinued
0.7045	Intermediate Similarity	NPD7111	Discontinued
0.7045	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5255	Approved
0.7035	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1183	Approved
0.7029	Intermediate Similarity	NPD5065	Approved
0.7027	Intermediate Similarity	NPD9392	Approved
0.7027	Intermediate Similarity	NPD9396	Approved
0.702	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3610	Approved
0.7011	Intermediate Similarity	NPD3609	Approved
0.7011	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3409	Phase 1
0.7006	Intermediate Similarity	NPD1994	Approved
0.7006	Intermediate Similarity	NPD1995	Approved
0.7006	Intermediate Similarity	NPD1993	Approved
0.6994	Remote Similarity	NPD4639	Approved
0.6994	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4638	Approved
0.6994	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3813	Approved
0.6994	Remote Similarity	NPD4640	Approved
0.6989	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3238	Discontinued
0.6988	Remote Similarity	NPD2172	Phase 1
0.6982	Remote Similarity	NPD4326	Phase 2
0.6981	Remote Similarity	NPD792	Discontinued
0.6966	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4902	Discontinued
0.6961	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4973	Approved
0.6952	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5995	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4181	Approved
0.6944	Remote Similarity	NPD7564	Discontinued
0.6936	Remote Similarity	NPD6446	Discontinued
0.6932	Remote Similarity	NPD3799	Suspended
0.6923	Remote Similarity	NPD9098	Phase 3
0.6923	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1683	Approved
0.6906	Remote Similarity	NPD3771	Phase 3
0.6906	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2333	Discontinued
0.6897	Remote Similarity	NPD1343	Approved
0.6897	Remote Similarity	NPD2641	Approved
0.6897	Remote Similarity	NPD2640	Approved
0.6893	Remote Similarity	NPD4075	Phase 2
0.6892	Remote Similarity	NPD269	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5254	Discontinued
0.689	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD5642	Approved
0.6867	Remote Similarity	NPD1270	Approved
0.6865	Remote Similarity	NPD5505	Discontinued
0.6857	Remote Similarity	NPD5436	Phase 1
0.6851	Remote Similarity	NPD6178	Phase 3
0.6845	Remote Similarity	NPD3262	Approved
0.6845	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4128	Approved
0.6832	Remote Similarity	NPD201	Phase 2
0.6832	Remote Similarity	NPD200	Phase 2
0.6831	Remote Similarity	NPD8021	Approved
0.6831	Remote Similarity	NPD8020	Approved
0.6829	Remote Similarity	NPD4510	Discontinued
0.6826	Remote Similarity	NPD5538	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3583	Phase 2
0.6818	Remote Similarity	NPD3117	Approved
0.6818	Remote Similarity	NPD3116	Approved
0.6816	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6241	Phase 1
0.681	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3830	Phase 1
0.6806	Remote Similarity	NPD6129	Phase 2
0.6802	Remote Similarity	NPD1404	Approved
0.6802	Remote Similarity	NPD1403	Approved
0.6798	Remote Similarity	NPD5100	Phase 3
0.6796	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2896	Discontinued
0.6788	Remote Similarity	NPD1988	Phase 1
0.6788	Remote Similarity	NPD4509	Discontinued
0.6786	Remote Similarity	NPD4462	Approved
0.6786	Remote Similarity	NPD4463	Approved
0.6784	Remote Similarity	NPD2581	Approved
0.6784	Remote Similarity	NPD2582	Approved
0.6782	Remote Similarity	NPD1002	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD926	Approved
0.6782	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD925	Approved
0.6768	Remote Similarity	NPD1382	Phase 2
0.6768	Remote Similarity	NPD1383	Phase 3
0.6765	Remote Similarity	NPD1328	Approved
0.6765	Remote Similarity	NPD2809	Approved
0.6761	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.676	Remote Similarity	NPD3506	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