NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	135.03
Volume:	130.547
LogP:	1.208
LogD:	1.245
LogS:	-1.878
# Rotatable Bonds:	0
TPSA:	46.0
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	2.513
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:	-5.077
MDCK Permeability:	1.5089494809217285e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.753
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.163

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.874
Plasma Protein Binding (PPB):	74.99681854248047%
Volume Distribution (VD):	0.627
Pgp-substrate:	20.676979064941406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.257
CYP2C19-substrate:	0.197
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.466
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	5.763
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.772
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.852
Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.671
Carcinogencity:	0.903
Eye Corrosion:	0.495
Eye Irritation:	0.989
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC264400

Natural Product ID:	NPC264400
*Common Name:**	1,2-Benzoxazol-3-One
IUPAC Name:	1,2-benzoxazol-3-one
Synonyms:	Benzo[D]Isoxazol-3-Ol
Standard InCHIKey:	QLDQYRDCPNBPII-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H5NO2/c9-7-5-3-1-2-4-6(5)10-8-7/h1-4H,(H,8,9)
SMILES:	Oc1noc2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444173
PubChem CID:	210830
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002332] Benzisoxazoles [CHEMONTID:0002333] Benzisoxazolones

*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
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13274	Illicium verum	Species	Schisandraceae	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
Kd	2
Others	1

Activity Type	# Activity
Individual Protein	3
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2587	Individual Protein	D-amino-acid oxidase	Sus scrofa	IC50	=	1880.0	nM	PMID[525787]
NPT645	Individual Protein	D-amino-acid oxidase	Homo sapiens	IC50	=	418.0	nM	PMID[525789]
NPT2587	Individual Protein	D-amino-acid oxidase	Sus scrofa	Kd	=	440.0	nM	PMID[525789]
NPT25569	SINGLE PROTEIN	D-3-phosphoglycerate dehydrogenase	Homo sapiens	Delta Tm	=	2.5	degrees C	PMID[525788]
NPT25569	SINGLE PROTEIN	D-3-phosphoglycerate dehydrogenase	Homo sapiens	Kd	=	6500000.0	nM	PMID[525788]

☑ 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 NPC264400 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	463
0.1-0.2	3613
0.2-0.3	12023
0.3-0.4	4682
0.4-0.5	14234
0.5-0.6	7375
0.6-0.7	306
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7107	Intermediate Similarity	NPC301702
0.707	Intermediate Similarity	NPC316574
0.7033	Intermediate Similarity	NPC56170
0.7019	Intermediate Similarity	NPC323798
0.6875	Remote Similarity	NPC181526
0.6842	Remote Similarity	NPC475983
0.6783	Remote Similarity	NPC100551
0.675	Remote Similarity	NPC43218
0.6705	Remote Similarity	NPC204867
0.6667	Remote Similarity	NPC150308
0.6667	Remote Similarity	NPC224584
0.6648	Remote Similarity	NPC9475
0.6622	Remote Similarity	NPC276111
0.6622	Remote Similarity	NPC118288
0.6597	Remote Similarity	NPC303264
0.6577	Remote Similarity	NPC160179
0.6575	Remote Similarity	NPC298320
0.6554	Remote Similarity	NPC223004
0.6536	Remote Similarity	NPC297186
0.6519	Remote Similarity	NPC164340
0.6513	Remote Similarity	NPC195262
0.6513	Remote Similarity	NPC188814
0.6513	Remote Similarity	NPC161617
0.6494	Remote Similarity	NPC73532
0.6494	Remote Similarity	NPC156139
0.6494	Remote Similarity	NPC45438
0.6494	Remote Similarity	NPC267552
0.6494	Remote Similarity	NPC115159
0.6494	Remote Similarity	NPC224273
0.6494	Remote Similarity	NPC19174
0.6494	Remote Similarity	NPC143427
0.649	Remote Similarity	NPC121259
0.6488	Remote Similarity	NPC314633
0.6483	Remote Similarity	NPC141523
0.6471	Remote Similarity	NPC130931
0.6457	Remote Similarity	NPC199737
0.6452	Remote Similarity	NPC32032
0.6452	Remote Similarity	NPC133909
0.6447	Remote Similarity	NPC241089
0.6447	Remote Similarity	NPC283844
0.6443	Remote Similarity	NPC211421
0.6442	Remote Similarity	NPC159722
0.6433	Remote Similarity	NPC314278
0.6424	Remote Similarity	NPC128825
0.6424	Remote Similarity	NPC312800
0.641	Remote Similarity	NPC317572
0.6392	Remote Similarity	NPC155792
0.6387	Remote Similarity	NPC242895
0.6387	Remote Similarity	NPC196976
0.6386	Remote Similarity	NPC13696
0.6369	Remote Similarity	NPC473196
0.6369	Remote Similarity	NPC13238
0.6364	Remote Similarity	NPC86834
0.6364	Remote Similarity	NPC210828
0.6364	Remote Similarity	NPC233282
0.6358	Remote Similarity	NPC161304
0.6358	Remote Similarity	NPC240163
0.6354	Remote Similarity	NPC303225
0.6346	Remote Similarity	NPC309765
0.6343	Remote Similarity	NPC473194
0.634	Remote Similarity	NPC40649
0.634	Remote Similarity	NPC94637
0.634	Remote Similarity	NPC209486
0.6327	Remote Similarity	NPC134848
0.6316	Remote Similarity	NPC108288
0.6316	Remote Similarity	NPC144691
0.6316	Remote Similarity	NPC241392
0.631	Remote Similarity	NPC297322
0.6305	Remote Similarity	NPC3207
0.6299	Remote Similarity	NPC90522
0.6299	Remote Similarity	NPC158222
0.6299	Remote Similarity	NPC328459
0.6294	Remote Similarity	NPC476444
0.6291	Remote Similarity	NPC163154
0.6289	Remote Similarity	NPC160499
0.6289	Remote Similarity	NPC62952
0.6289	Remote Similarity	NPC8745
0.6282	Remote Similarity	NPC303737
0.6278	Remote Similarity	NPC471778
0.6277	Remote Similarity	NPC206186
0.6277	Remote Similarity	NPC238242
0.6275	Remote Similarity	NPC125252
0.6275	Remote Similarity	NPC230349
0.6275	Remote Similarity	NPC269414
0.6269	Remote Similarity	NPC23294
0.6268	Remote Similarity	NPC315921
0.6266	Remote Similarity	NPC193805
0.6265	Remote Similarity	NPC314252
0.6265	Remote Similarity	NPC238108
0.6258	Remote Similarity	NPC72977
0.6258	Remote Similarity	NPC260837
0.6258	Remote Similarity	NPC159525
0.6258	Remote Similarity	NPC294037
0.6257	Remote Similarity	NPC295158
0.625	Remote Similarity	NPC30501
0.625	Remote Similarity	NPC162612
0.625	Remote Similarity	NPC98254
0.625	Remote Similarity	NPC169250
0.625	Remote Similarity	NPC190043
0.625	Remote Similarity	NPC72158
0.625	Remote Similarity	NPC23126
0.625	Remote Similarity	NPC105157
0.625	Remote Similarity	NPC266689
0.625	Remote Similarity	NPC100067
0.625	Remote Similarity	NPC103356
0.6243	Remote Similarity	NPC44354
0.6243	Remote Similarity	NPC112336
0.6243	Remote Similarity	NPC474814
0.6234	Remote Similarity	NPC184527
0.6234	Remote Similarity	NPC41567
0.623	Remote Similarity	NPC114039
0.623	Remote Similarity	NPC206109
0.6226	Remote Similarity	NPC10926
0.6219	Remote Similarity	NPC303951
0.6218	Remote Similarity	NPC149246
0.6218	Remote Similarity	NPC146642
0.6215	Remote Similarity	NPC473193
0.6211	Remote Similarity	NPC473017
0.6211	Remote Similarity	NPC144381
0.6211	Remote Similarity	NPC21305
0.6211	Remote Similarity	NPC221777
0.6209	Remote Similarity	NPC477453
0.62	Remote Similarity	NPC114682
0.6199	Remote Similarity	NPC315829
0.6194	Remote Similarity	NPC233165
0.6194	Remote Similarity	NPC184579
0.6188	Remote Similarity	NPC267846
0.6186	Remote Similarity	NPC90229
0.6178	Remote Similarity	NPC215392
0.6178	Remote Similarity	NPC268348
0.6178	Remote Similarity	NPC198336
0.6173	Remote Similarity	NPC102829
0.6173	Remote Similarity	NPC474998
0.6173	Remote Similarity	NPC109123
0.6173	Remote Similarity	NPC120488
0.617	Remote Similarity	NPC132751
0.617	Remote Similarity	NPC241025
0.6169	Remote Similarity	NPC28169
0.6164	Remote Similarity	NPC236189
0.6163	Remote Similarity	NPC237649
0.6163	Remote Similarity	NPC300596
0.6158	Remote Similarity	NPC113812
0.6154	Remote Similarity	NPC472284
0.6154	Remote Similarity	NPC294964
0.6154	Remote Similarity	NPC206778
0.6154	Remote Similarity	NPC285829
0.615	Remote Similarity	NPC183777
0.6149	Remote Similarity	NPC226699
0.6149	Remote Similarity	NPC116513
0.6149	Remote Similarity	NPC34715
0.6145	Remote Similarity	NPC236795
0.6139	Remote Similarity	NPC300274
0.6139	Remote Similarity	NPC91105
0.6139	Remote Similarity	NPC283514
0.6139	Remote Similarity	NPC244351
0.6135	Remote Similarity	NPC26697
0.6134	Remote Similarity	NPC170333
0.6131	Remote Similarity	NPC33011
0.6129	Remote Similarity	NPC229353
0.6125	Remote Similarity	NPC4164
0.6118	Remote Similarity	NPC242136
0.6115	Remote Similarity	NPC272454
0.6115	Remote Similarity	NPC301987
0.6115	Remote Similarity	NPC244994
0.6115	Remote Similarity	NPC35856
0.6115	Remote Similarity	NPC292665
0.6115	Remote Similarity	NPC159760
0.6115	Remote Similarity	NPC26433
0.6115	Remote Similarity	NPC179092
0.6115	Remote Similarity	NPC222876
0.6115	Remote Similarity	NPC178395
0.6115	Remote Similarity	NPC115188
0.6111	Remote Similarity	NPC186098
0.6111	Remote Similarity	NPC95537
0.6111	Remote Similarity	NPC80694
0.6108	Remote Similarity	NPC471316
0.6108	Remote Similarity	NPC220337
0.6107	Remote Similarity	NPC17525
0.6106	Remote Similarity	NPC174760
0.6101	Remote Similarity	NPC65761
0.6101	Remote Similarity	NPC375356
0.6101	Remote Similarity	NPC472029
0.6098	Remote Similarity	NPC34070
0.6098	Remote Similarity	NPC475042
0.6098	Remote Similarity	NPC469526
0.6098	Remote Similarity	NPC328070
0.609	Remote Similarity	NPC232178
0.6087	Remote Similarity	NPC95309
0.6087	Remote Similarity	NPC247803
0.6083	Remote Similarity	NPC477589
0.6083	Remote Similarity	NPC477587
0.6081	Remote Similarity	NPC187913
0.6081	Remote Similarity	NPC6984
0.6078	Remote Similarity	NPC12344
0.6076	Remote Similarity	NPC226275
0.6074	Remote Similarity	NPC476119
0.6074	Remote Similarity	NPC60558
0.6074	Remote Similarity	NPC92624
0.6074	Remote Similarity	NPC197425
0.6067	Remote Similarity	NPC95172

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 NPC264400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	866
0.2-0.3	956
0.3-0.4	2276
0.4-0.5	3774
0.5-0.6	834
0.6-0.7	77
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD9487	Approved
0.7543	Intermediate Similarity	NPD2792	Approved
0.7283	Intermediate Similarity	NPD3239	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3004	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3327	Approved
0.7158	Intermediate Similarity	NPD5726	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1925	Approved
0.7107	Intermediate Similarity	NPD75	Approved
0.7107	Intermediate Similarity	NPD9277	Approved
0.7077	Intermediate Similarity	NPD6198	Phase 1
0.707	Intermediate Similarity	NPD9279	Approved
0.7069	Intermediate Similarity	NPD3325	Approved
0.7044	Intermediate Similarity	NPD9274	Approved
0.7044	Intermediate Similarity	NPD9276	Approved
0.7044	Intermediate Similarity	NPD9278	Suspended
0.7044	Intermediate Similarity	NPD9275	Approved
0.6914	Remote Similarity	NPD1196	Approved
0.6882	Remote Similarity	NPD5591	Approved
0.6852	Remote Similarity	NPD1195	Approved
0.6828	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3351	Approved
0.6788	Remote Similarity	NPD1543	Discontinued
0.6783	Remote Similarity	NPD74	Approved
0.6783	Remote Similarity	NPD9266	Approved
0.6753	Remote Similarity	NPD5594	Approved
0.6753	Remote Similarity	NPD5593	Approved
0.6744	Remote Similarity	NPD738	Approved
0.6737	Remote Similarity	NPD5552	Discontinued
0.6736	Remote Similarity	NPD3350	Approved
0.6713	Remote Similarity	NPD9267	Approved
0.6713	Remote Similarity	NPD9264	Approved
0.6713	Remote Similarity	NPD9263	Approved
0.6514	Remote Similarity	NPD955	Approved
0.6477	Remote Similarity	NPD3252	Approved
0.6465	Remote Similarity	NPD5914	Approved
0.6462	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD5637	Discontinued
0.6447	Remote Similarity	NPD1759	Phase 1
0.6434	Remote Similarity	NPD9261	Approved
0.6432	Remote Similarity	NPD927	Approved
0.6425	Remote Similarity	NPD6870	Phase 1
0.6424	Remote Similarity	NPD9493	Approved
0.6422	Remote Similarity	NPD3308	Approved
0.6416	Remote Similarity	NPD2366	Approved
0.64	Remote Similarity	NPD9281	Approved
0.6398	Remote Similarity	NPD520	Approved
0.6382	Remote Similarity	NPD1758	Phase 1
0.6373	Remote Similarity	NPD3307	Approved
0.6373	Remote Similarity	NPD2884	Phase 1
0.6373	Remote Similarity	NPD5519	Discontinued
0.6352	Remote Similarity	NPD9107	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD710	Clinical (unspecified phase)
0.634	Remote Similarity	NPD5879	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD405	Clinical (unspecified phase)
0.63	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD1220	Phase 1
0.6296	Remote Similarity	NPD1852	Discontinued
0.628	Remote Similarity	NPD3271	Approved
0.628	Remote Similarity	NPD3275	Approved
0.6271	Remote Similarity	NPD5161	Approved
0.6269	Remote Similarity	NPD1842	Approved
0.6268	Remote Similarity	NPD9273	Approved
0.6236	Remote Similarity	NPD923	Approved
0.6232	Remote Similarity	NPD3270	Approved
0.6231	Remote Similarity	NPD3910	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5937	Approved
0.623	Remote Similarity	NPD2361	Approved
0.6226	Remote Similarity	NPD1164	Approved
0.6226	Remote Similarity	NPD1593	Approved
0.6201	Remote Similarity	NPD1168	Approved
0.6196	Remote Similarity	NPD1221	Approved
0.6188	Remote Similarity	NPD1839	Phase 1
0.6185	Remote Similarity	NPD3869	Phase 3
0.6185	Remote Similarity	NPD3873	Phase 3
0.6175	Remote Similarity	NPD2359	Approved
0.6175	Remote Similarity	NPD4613	Phase 2
0.6167	Remote Similarity	NPD3251	Approved
0.6154	Remote Similarity	NPD1913	Phase 1
0.6154	Remote Similarity	NPD4053	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2672	Discontinued
0.6133	Remote Similarity	NPD2821	Approved
0.6125	Remote Similarity	NPD1203	Approved
0.6114	Remote Similarity	NPD511	Approved
0.6114	Remote Similarity	NPD1162	Approved
0.6114	Remote Similarity	NPD512	Approved
0.6078	Remote Similarity	NPD7605	Discovery
0.6076	Remote Similarity	NPD1201	Approved
0.6066	Remote Similarity	NPD3925	Approved
0.6061	Remote Similarity	NPD943	Approved
0.6061	Remote Similarity	NPD1240	Approved
0.6051	Remote Similarity	NPD9272	Approved
0.6049	Remote Similarity	NPD9106	Phase 3
0.604	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD9717	Approved
0.6025	Remote Similarity	NPD1470	Approved
0.6022	Remote Similarity	NPD6020	Phase 2
0.6011	Remote Similarity	NPD1161	Approved
0.6011	Remote Similarity	NPD6104	Discontinued
0.6	Remote Similarity	NPD788	Discontinued
0.6	Remote Similarity	NPD7556	Discontinued
0.6	Remote Similarity	NPD3242	Phase 1
0.6	Remote Similarity	NPD711	Discontinued
0.5988	Remote Similarity	NPD1607	Approved
0.5987	Remote Similarity	NPD8582	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4941	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD1631	Approved
0.5963	Remote Similarity	NPD1574	Approved
0.5962	Remote Similarity	NPD9247	Phase 3
0.5956	Remote Similarity	NPD1921	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD2344	Approved
0.5938	Remote Similarity	NPD4948	Discontinued
0.5936	Remote Similarity	NPD1170	Approved
0.5933	Remote Similarity	NPD1926	Approved
0.593	Remote Similarity	NPD1199	Approved
0.593	Remote Similarity	NPD1200	Approved
0.5922	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD1510	Phase 2
0.5917	Remote Similarity	NPD1169	Approved
0.5912	Remote Similarity	NPD9693	Approved
0.5912	Remote Similarity	NPD9692	Approved
0.5907	Remote Similarity	NPD1898	Discontinued
0.5905	Remote Similarity	NPD6974	Phase 3
0.5904	Remote Similarity	NPD1729	Discontinued
0.5902	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD1514	Discontinued
0.5882	Remote Similarity	NPD9508	Approved
0.5874	Remote Similarity	NPD1172	Discovery
0.5867	Remote Similarity	NPD4539	Phase 1
0.5867	Remote Similarity	NPD4466	Phase 1
0.5864	Remote Similarity	NPD7546	Discontinued
0.5862	Remote Similarity	NPD3300	Phase 2
0.5862	Remote Similarity	NPD160	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD9477	Approved
0.5846	Remote Similarity	NPD5849	Approved
0.5843	Remote Similarity	NPD3229	Phase 2
0.5842	Remote Similarity	NPD4133	Approved
0.5838	Remote Similarity	NPD1573	Approved
0.5838	Remote Similarity	NPD1575	Approved
0.5829	Remote Similarity	NPD1198	Approved
0.5829	Remote Similarity	NPD4704	Discontinued
0.5829	Remote Similarity	NPD4312	Approved
0.5826	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD651	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD1014	Approved
0.5814	Remote Similarity	NPD1549	Phase 2
0.5814	Remote Similarity	NPD1189	Approved
0.5813	Remote Similarity	NPD1983	Approved
0.5813	Remote Similarity	NPD1980	Approved
0.5813	Remote Similarity	NPD4156	Approved
0.5813	Remote Similarity	NPD1981	Approved
0.5812	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.581	Remote Similarity	NPD3684	Discontinued
0.5805	Remote Similarity	NPD2309	Approved
0.5805	Remote Similarity	NPD1835	Phase 1
0.5804	Remote Similarity	NPD4946	Phase 2
0.5803	Remote Similarity	NPD3153	Approved
0.5803	Remote Similarity	NPD3154	Approved
0.5801	Remote Similarity	NPD1630	Approved
0.5797	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD6282	Discontinued
0.5793	Remote Similarity	NPD1019	Discontinued
0.5792	Remote Similarity	NPD2779	Approved
0.5789	Remote Similarity	NPD1551	Phase 2
0.5789	Remote Similarity	NPD5445	Approved
0.578	Remote Similarity	NPD1625	Approved
0.578	Remote Similarity	NPD2654	Approved
0.5779	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD2248	Approved
0.5775	Remote Similarity	NPD2246	Approved
0.5771	Remote Similarity	NPD9075	Approved
0.5771	Remote Similarity	NPD9074	Approved
0.5769	Remote Similarity	NPD7318	Phase 3
0.5769	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD4400	Approved
0.5756	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.5756	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.5751	Remote Similarity	NPD6045	Phase 3
0.5749	Remote Similarity	NPD411	Approved
0.5749	Remote Similarity	NPD9471	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD3446	Phase 1
0.574	Remote Similarity	NPD4561	Discontinued
0.5735	Remote Similarity	NPD4465	Phase 2
0.5735	Remote Similarity	NPD4467	Phase 2
0.5732	Remote Similarity	NPD255	Approved
0.5732	Remote Similarity	NPD256	Approved
0.5723	Remote Similarity	NPD4207	Discontinued
0.5722	Remote Similarity	NPD948	Phase 3
0.5721	Remote Similarity	NPD5416	Discontinued
0.5714	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5195	Discontinued
0.5699	Remote Similarity	NPD3286	Discontinued
0.5698	Remote Similarity	NPD5406	Approved
0.5698	Remote Similarity	NPD5404	Approved
0.5698	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD2935	Discontinued

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