NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.08
Volume:	211.273
LogP:	2.997
LogD:	2.863
LogS:	-3.388
# Rotatable Bonds:	1
TPSA:	28.68
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	2.458
Fsp3:	0.0
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:	-4.883
MDCK Permeability:	2.23745264520403e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.829
30% Bioavailability (F30%):	0.513

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.893
Plasma Protein Binding (PPB):	90.51490020751953%
Volume Distribution (VD):	1.335
Pgp-substrate:	6.088517665863037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.993
CYP1A2-substrate:	0.767
CYP2C19-inhibitor:	0.425
CYP2C19-substrate:	0.506
CYP2C9-inhibitor:	0.362
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.747
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.508
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	4.153
Half-life (T1/2):	0.313

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.87
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.6
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.766
Skin Sensitization:	0.872
Carcinogencity:	0.712
Eye Corrosion:	0.201
Eye Irritation:	0.989
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC469811

Natural Product ID:	NPC469811
*Common Name:**	LXQSIICQACNSSW-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LXQSIICQACNSSW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10N2/c1-2-11-13-10(7-8-14-11)9-5-3-4-6-12(9)15-13/h2-8,14H,1H2
SMILES:	C=Cc1[nH]ccc2c1nc1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL11991
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	Alderman Islands off the North Island of New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[19220033]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19220033]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	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
Ki	1
Others	3

Activity Type	# Activity
Cell Line	1
Organism	3
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.1	ug.mL-1	PMID[531321]
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	Ki	=	250000.0	nM	PMID[531320]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MID	=	0.1	ug ml-1	PMID[531321]
NPT20	Organism	Candida albicans	Candida albicans	MID	=	1.9	ug ml-1	PMID[531321]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MID	=	1.9	ug ml-1	PMID[531321]

☑ 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 NPC469811 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	2047
0.1-0.2	14676
0.2-0.3	16870
0.3-0.4	4182
0.4-0.5	1977
0.5-0.6	1523
0.6-0.7	893
0.7-0.8	397
0.8-0.85	84
0.85-0.9	29
0.9-0.95	18
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC63545
0.9928	High Similarity	NPC321911
0.9856	High Similarity	NPC179787
0.9856	High Similarity	NPC201380
0.9718	High Similarity	NPC325903
0.9388	High Similarity	NPC470204
0.9388	High Similarity	NPC122141
0.9384	High Similarity	NPC236711
0.9324	High Similarity	NPC470203
0.9286	High Similarity	NPC115611
0.9275	High Similarity	NPC96102
0.9262	High Similarity	NPC317105
0.9209	High Similarity	NPC105127
0.9209	High Similarity	NPC84911
0.9137	High Similarity	NPC29886
0.9137	High Similarity	NPC261195
0.9097	High Similarity	NPC288838
0.9078	High Similarity	NPC73767
0.9078	High Similarity	NPC110126
0.9073	High Similarity	NPC274229
0.9014	High Similarity	NPC469768
0.9014	High Similarity	NPC469779
0.9014	High Similarity	NPC469761
0.9014	High Similarity	NPC469783
0.9014	High Similarity	NPC469784
0.9014	High Similarity	NPC469780
0.9014	High Similarity	NPC279081
0.9014	High Similarity	NPC469767
0.9	High Similarity	NPC325252
0.8986	High Similarity	NPC82295
0.8951	High Similarity	NPC469766
0.8929	High Similarity	NPC198988
0.8912	High Similarity	NPC53947
0.8904	High Similarity	NPC470111
0.8896	High Similarity	NPC97343
0.8889	High Similarity	NPC190296
0.8881	High Similarity	NPC230002
0.8839	High Similarity	NPC82331
0.8836	High Similarity	NPC143872
0.8816	High Similarity	NPC225018
0.879	High Similarity	NPC474958
0.8767	High Similarity	NPC159856
0.8767	High Similarity	NPC314372
0.875	High Similarity	NPC284635
0.8725	High Similarity	NPC470233
0.8681	High Similarity	NPC88097
0.8671	High Similarity	NPC280852
0.8649	High Similarity	NPC471957
0.8627	High Similarity	NPC215584
0.8627	High Similarity	NPC44773
0.8618	High Similarity	NPC216643
0.8601	High Similarity	NPC218268
0.8571	High Similarity	NPC307191
0.8562	High Similarity	NPC56765
0.8562	High Similarity	NPC92796
0.8562	High Similarity	NPC135141
0.8533	High Similarity	NPC105818
0.8533	High Similarity	NPC24678
0.8516	High Similarity	NPC478184
0.8514	High Similarity	NPC204141
0.8511	High Similarity	NPC22079
0.8491	Intermediate Similarity	NPC471579
0.8489	Intermediate Similarity	NPC250361
0.8487	Intermediate Similarity	NPC476219
0.8487	Intermediate Similarity	NPC476297
0.8477	Intermediate Similarity	NPC470823
0.8477	Intermediate Similarity	NPC216713
0.8457	Intermediate Similarity	NPC191415
0.8442	Intermediate Similarity	NPC293487
0.8442	Intermediate Similarity	NPC477591
0.8421	Intermediate Similarity	NPC469786
0.8421	Intermediate Similarity	NPC469763
0.8421	Intermediate Similarity	NPC469760
0.8421	Intermediate Similarity	NPC469765
0.8421	Intermediate Similarity	NPC259644
0.8421	Intermediate Similarity	NPC73952
0.8421	Intermediate Similarity	NPC141926
0.8421	Intermediate Similarity	NPC25008
0.8421	Intermediate Similarity	NPC200214
0.8411	Intermediate Similarity	NPC40070
0.8406	Intermediate Similarity	NPC46358
0.8405	Intermediate Similarity	NPC102755
0.8405	Intermediate Similarity	NPC48938
0.8397	Intermediate Similarity	NPC90723
0.8389	Intermediate Similarity	NPC470440
0.8377	Intermediate Similarity	NPC286427
0.8369	Intermediate Similarity	NPC473762
0.8367	Intermediate Similarity	NPC2949
0.8367	Intermediate Similarity	NPC59084
0.8366	Intermediate Similarity	NPC34844
0.8366	Intermediate Similarity	NPC70922
0.8366	Intermediate Similarity	NPC211572
0.8366	Intermediate Similarity	NPC212376
0.8366	Intermediate Similarity	NPC75540
0.8366	Intermediate Similarity	NPC80597
0.8354	Intermediate Similarity	NPC284678
0.8323	Intermediate Similarity	NPC206819
0.8323	Intermediate Similarity	NPC41257
0.8323	Intermediate Similarity	NPC318065
0.8312	Intermediate Similarity	NPC469785
0.8311	Intermediate Similarity	NPC473868
0.8311	Intermediate Similarity	NPC63157
0.831	Intermediate Similarity	NPC473587
0.8288	Intermediate Similarity	NPC251722
0.8288	Intermediate Similarity	NPC125746
0.8288	Intermediate Similarity	NPC314102
0.828	Intermediate Similarity	NPC478182
0.8269	Intermediate Similarity	NPC279918
0.8258	Intermediate Similarity	NPC469762
0.8253	Intermediate Similarity	NPC62749
0.8252	Intermediate Similarity	NPC475428
0.8217	Intermediate Similarity	NPC478185
0.8217	Intermediate Similarity	NPC282231
0.8214	Intermediate Similarity	NPC27740
0.8212	Intermediate Similarity	NPC316069
0.8201	Intermediate Similarity	NPC41174
0.8194	Intermediate Similarity	NPC475450
0.8194	Intermediate Similarity	NPC179365
0.8176	Intermediate Similarity	NPC478183
0.8176	Intermediate Similarity	NPC56233
0.8163	Intermediate Similarity	NPC150259
0.8153	Intermediate Similarity	NPC131718
0.8138	Intermediate Similarity	NPC473930
0.8133	Intermediate Similarity	NPC108011
0.8125	Intermediate Similarity	NPC282398
0.8125	Intermediate Similarity	NPC63751
0.8118	Intermediate Similarity	NPC324149
0.8113	Intermediate Similarity	NPC17751
0.8113	Intermediate Similarity	NPC280864
0.8108	Intermediate Similarity	NPC169433
0.8107	Intermediate Similarity	NPC231536
0.8089	Intermediate Similarity	NPC475990
0.8089	Intermediate Similarity	NPC230869
0.8089	Intermediate Similarity	NPC221786
0.8089	Intermediate Similarity	NPC474880
0.8086	Intermediate Similarity	NPC477611
0.8075	Intermediate Similarity	NPC91895
0.8075	Intermediate Similarity	NPC32534
0.807	Intermediate Similarity	NPC326422
0.8063	Intermediate Similarity	NPC474561
0.8063	Intermediate Similarity	NPC49954
0.8063	Intermediate Similarity	NPC54988
0.805	Intermediate Similarity	NPC311276
0.8043	Intermediate Similarity	NPC91958
0.8039	Intermediate Similarity	NPC21605
0.8038	Intermediate Similarity	NPC229173
0.8028	Intermediate Similarity	NPC166424
0.8028	Intermediate Similarity	NPC245244
0.8028	Intermediate Similarity	NPC146373
0.7963	Intermediate Similarity	NPC194411
0.795	Intermediate Similarity	NPC160105
0.795	Intermediate Similarity	NPC49217
0.7939	Intermediate Similarity	NPC59269
0.7937	Intermediate Similarity	NPC102423
0.7937	Intermediate Similarity	NPC40779
0.7937	Intermediate Similarity	NPC149265
0.7935	Intermediate Similarity	NPC33421
0.7927	Intermediate Similarity	NPC317054
0.7914	Intermediate Similarity	NPC470498
0.7908	Intermediate Similarity	NPC86288
0.7901	Intermediate Similarity	NPC201700
0.7895	Intermediate Similarity	NPC20144
0.7892	Intermediate Similarity	NPC11126
0.7886	Intermediate Similarity	NPC265576
0.787	Intermediate Similarity	NPC99939
0.787	Intermediate Similarity	NPC308931
0.787	Intermediate Similarity	NPC15102
0.7844	Intermediate Similarity	NPC314919
0.7831	Intermediate Similarity	NPC240088
0.7831	Intermediate Similarity	NPC284775
0.7831	Intermediate Similarity	NPC473380
0.7826	Intermediate Similarity	NPC247987
0.7826	Intermediate Similarity	NPC194640
0.7823	Intermediate Similarity	NPC101165
0.7818	Intermediate Similarity	NPC275305
0.7818	Intermediate Similarity	NPC37423
0.7815	Intermediate Similarity	NPC312092
0.7792	Intermediate Similarity	NPC285731
0.7791	Intermediate Similarity	NPC78020
0.7786	Intermediate Similarity	NPC54102
0.7786	Intermediate Similarity	NPC162689
0.7786	Intermediate Similarity	NPC143603
0.7784	Intermediate Similarity	NPC265710
0.7784	Intermediate Similarity	NPC12649
0.7778	Intermediate Similarity	NPC42372
0.777	Intermediate Similarity	NPC148140
0.7758	Intermediate Similarity	NPC314603
0.7756	Intermediate Similarity	NPC2272
0.7746	Intermediate Similarity	NPC48564
0.7746	Intermediate Similarity	NPC265605
0.7746	Intermediate Similarity	NPC182570
0.7744	Intermediate Similarity	NPC474897
0.7742	Intermediate Similarity	NPC478186
0.774	Intermediate Similarity	NPC237414
0.7738	Intermediate Similarity	NPC24864
0.7738	Intermediate Similarity	NPC16659
0.7738	Intermediate Similarity	NPC164228
0.7736	Intermediate Similarity	NPC476464
0.7725	Intermediate Similarity	NPC248454
0.7725	Intermediate Similarity	NPC68354

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 NPC469811 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	518
0.1-0.2	1010
0.2-0.3	954
0.3-0.4	2226
0.4-0.5	2164
0.5-0.6	1510
0.6-0.7	597
0.7-0.8	153
0.8-0.85	14
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9357	High Similarity	NPD1722	Approved
0.9275	High Similarity	NPD198	Clinical (unspecified phase)
0.9078	High Similarity	NPD786	Approved
0.8919	High Similarity	NPD2837	Discontinued
0.8844	High Similarity	NPD4374	Clinical (unspecified phase)
0.8716	High Similarity	NPD3100	Discontinued
0.8571	High Similarity	NPD1853	Clinical (unspecified phase)
0.8533	High Similarity	NPD2172	Phase 1
0.8516	High Similarity	NPD3323	Discontinued
0.8511	High Similarity	NPD715	Phase 3
0.8503	High Similarity	NPD4637	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD991	Phase 2
0.8429	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD977	Approved
0.8366	Intermediate Similarity	NPD976	Approved
0.8366	Intermediate Similarity	NPD975	Approved
0.8344	Intermediate Similarity	NPD1895	Discontinued
0.8282	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD4547	Phase 3
0.8258	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD2006	Phase 2
0.8243	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD2641	Approved
0.8239	Intermediate Similarity	NPD2640	Approved
0.8224	Intermediate Similarity	NPD2430	Phase 2
0.8212	Intermediate Similarity	NPD1683	Approved
0.82	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD4181	Approved
0.8153	Intermediate Similarity	NPD1403	Approved
0.8153	Intermediate Similarity	NPD1404	Approved
0.8148	Intermediate Similarity	NPD5065	Approved
0.8137	Intermediate Similarity	NPD3609	Approved
0.8137	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3610	Approved
0.8125	Intermediate Similarity	NPD3476	Approved
0.8125	Intermediate Similarity	NPD3475	Approved
0.8125	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD3385	Approved
0.8079	Intermediate Similarity	NPD5254	Discontinued
0.8069	Intermediate Similarity	NPD803	Phase 1
0.8042	Intermediate Similarity	NPD2118	Approved
0.8042	Intermediate Similarity	NPD2119	Approved
0.8041	Intermediate Similarity	NPD1262	Discovery
0.8037	Intermediate Similarity	NPD4128	Approved
0.8012	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD2639	Approved
0.795	Intermediate Similarity	NPD2642	Approved
0.7935	Intermediate Similarity	NPD4463	Approved
0.7935	Intermediate Similarity	NPD4462	Approved
0.7922	Intermediate Similarity	NPD1661	Suspended
0.7901	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD9598	Discontinued
0.787	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2580	Discontinued
0.7847	Intermediate Similarity	NPD9583	Approved
0.7844	Intermediate Similarity	NPD6595	Phase 3
0.784	Intermediate Similarity	NPD1248	Discontinued
0.7838	Intermediate Similarity	NPD4028	Approved
0.7838	Intermediate Similarity	NPD4029	Approved
0.7838	Intermediate Similarity	NPD4030	Approved
0.7831	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3654	Approved
0.7799	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2333	Discontinued
0.7785	Intermediate Similarity	NPD2165	Phase 1
0.7784	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4075	Phase 2
0.7751	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5418	Discontinued
0.7746	Intermediate Similarity	NPD268	Approved
0.7746	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD271	Approved
0.7744	Intermediate Similarity	NPD5436	Phase 1
0.7736	Intermediate Similarity	NPD3115	Approved
0.7736	Intermediate Similarity	NPD3112	Approved
0.7736	Intermediate Similarity	NPD3114	Approved
0.7736	Intermediate Similarity	NPD3113	Approved
0.7733	Intermediate Similarity	NPD1255	Approved
0.7733	Intermediate Similarity	NPD1253	Approved
0.7733	Intermediate Similarity	NPD1256	Approved
0.7733	Intermediate Similarity	NPD1254	Approved
0.7725	Intermediate Similarity	NPD3506	Approved
0.7725	Intermediate Similarity	NPD3505	Approved
0.7719	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD3944	Approved
0.7718	Intermediate Similarity	NPD3942	Approved
0.7714	Intermediate Similarity	NPD9392	Approved
0.7714	Intermediate Similarity	NPD9396	Approved
0.7711	Intermediate Similarity	NPD482	Approved
0.7708	Intermediate Similarity	NPD9357	Approved
0.7698	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1707	Approved
0.7692	Intermediate Similarity	NPD1708	Approved
0.7687	Intermediate Similarity	NPD947	Approved
0.7682	Intermediate Similarity	NPD45	Approved
0.7682	Intermediate Similarity	NPD6554	Approved
0.7679	Intermediate Similarity	NPD4079	Approved
0.7679	Intermediate Similarity	NPD4076	Approved
0.7674	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1598	Discontinued
0.767	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1313	Approved
0.7669	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1227	Phase 2
0.7647	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5105	Approved
0.7647	Intermediate Similarity	NPD5106	Approved
0.7628	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2144	Approved
0.7616	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7619	Phase 3
0.7614	Intermediate Similarity	NPD7618	Phase 3
0.7586	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3961	Discontinued
0.756	Intermediate Similarity	NPD3348	Phase 2
0.7546	Intermediate Similarity	NPD5315	Discontinued
0.753	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD2880	Discontinued
0.7516	Intermediate Similarity	NPD2927	Phase 3
0.7516	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7111	Discontinued
0.7514	Intermediate Similarity	NPD2793	Discontinued
0.7514	Intermediate Similarity	NPD6217	Discontinued
0.75	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3339	Approved
0.7485	Intermediate Similarity	NPD6828	Phase 2
0.7485	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3038	Discontinued
0.7472	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8431	Approved
0.7468	Intermediate Similarity	NPD2074	Approved
0.7468	Intermediate Similarity	NPD2075	Approved
0.7468	Intermediate Similarity	NPD2068	Approved
0.7468	Intermediate Similarity	NPD2073	Approved
0.7468	Intermediate Similarity	NPD2069	Approved
0.7468	Intermediate Similarity	NPD2070	Approved
0.7468	Intermediate Similarity	NPD2071	Approved
0.7468	Intermediate Similarity	NPD2072	Approved
0.7458	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2720	Phase 1
0.7455	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD509	Phase 3
0.7448	Intermediate Similarity	NPD1561	Phase 2
0.7442	Intermediate Similarity	NPD2092	Phase 2
0.7442	Intermediate Similarity	NPD2094	Phase 2
0.7442	Intermediate Similarity	NPD2095	Phase 2
0.744	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1016	Phase 2
0.7439	Intermediate Similarity	NPD1015	Phase 2
0.7427	Intermediate Similarity	NPD5962	Phase 2
0.7427	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3015	Discontinued
0.7414	Intermediate Similarity	NPD706	Phase 1
0.7407	Intermediate Similarity	NPD2150	Discontinued
0.7405	Intermediate Similarity	NPD7469	Discontinued
0.7399	Intermediate Similarity	NPD6178	Phase 3
0.7399	Intermediate Similarity	NPD2096	Phase 2
0.7399	Intermediate Similarity	NPD2091	Phase 2
0.7378	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1030	Approved
0.7375	Intermediate Similarity	NPD1027	Approved
0.7371	Intermediate Similarity	NPD7394	Phase 2
0.7368	Intermediate Similarity	NPD1327	Discontinued
0.7358	Intermediate Similarity	NPD4703	Approved
0.7358	Intermediate Similarity	NPD4702	Approved
0.7351	Intermediate Similarity	NPD1251	Discontinued
0.7349	Intermediate Similarity	NPD1333	Phase 3
0.7345	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD750	Phase 2
0.7333	Intermediate Similarity	NPD6771	Discontinued
0.7329	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4047	Discontinued
0.732	Intermediate Similarity	NPD4880	Discontinued
0.7314	Intermediate Similarity	NPD4902	Discontinued
0.7312	Intermediate Similarity	NPD1183	Approved
0.7303	Intermediate Similarity	NPD4922	Phase 2
0.7303	Intermediate Similarity	NPD4615	Phase 2
0.7299	Intermediate Similarity	NPD4957	Phase 2
0.7297	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2008	Discontinued
0.7289	Intermediate Similarity	NPD3583	Phase 2
0.7288	Intermediate Similarity	NPD6133	Discontinued
0.7278	Intermediate Similarity	NPD5934	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