NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.04
Volume:	228.056
LogP:	1.437
LogD:	0.848
LogS:	-2.879
# Rotatable Bonds:	2
TPSA:	53.27
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	3.693
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.65
MDCK Permeability:	4.108751818421297e-05
Pgp-inhibitor:	0.197
Pgp-substrate:	0.402
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	85.6429672241211%
Volume Distribution (VD):	0.873
Pgp-substrate:	21.050146102905273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.606
CYP2C9-inhibitor:	0.089
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.762
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	2.53
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.457
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.948
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.628
Skin Sensitization:	0.551
Carcinogencity:	0.946
Eye Corrosion:	0.012
Eye Irritation:	0.937
Respiratory Toxicity:	0.656

Download Data

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

Natural Product: NPC472888

Natural Product ID:	NPC472888
*Common Name:**	BKKJJPYCWUZIFF-VOTSOKGWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BKKJJPYCWUZIFF-VOTSOKGWSA-N
Standard InCHI:	InChI=1S/C12H10O3S/c1-16(14)7-6-9-8-11(13)10-4-2-3-5-12(10)15-9/h2-8H,1H3/b7-6+
SMILES:	CS(=O)/C=C/c1cc(=O)c2c(o1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593563
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579873]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26225905]
NPO23424	Dirca palustris	Species	Thymelaeaceae	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	3
Others	3

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	10000.0	nM	PMID[527365]
NPT81	Cell Line	A549	Homo sapiens	Ratio IC50	=	5.0	n.a.	PMID[527365]
NPT579	Cell Line	DLD-1	Homo sapiens	Ratio IC50	=	5.0	n.a.	PMID[527365]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1000.0	nM	PMID[527365]
NPT27	Others	Unspecified		IC50	=	9000.0	nM	PMID[527365]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC90	=	3.7	ug.mL-1	PMID[527365]

☑ 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 NPC472888 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	452
0.1-0.2	2762
0.2-0.3	7318
0.3-0.4	11447
0.4-0.5	4693
0.5-0.6	7973
0.6-0.7	6440
0.7-0.8	1562
0.8-0.85	42
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.928	High Similarity	NPC472882
0.8992	High Similarity	NPC472881
0.8992	High Similarity	NPC32298
0.8923	High Similarity	NPC472883
0.8917	High Similarity	NPC54243
0.876	High Similarity	NPC35744
0.8729	High Similarity	NPC279916
0.8571	High Similarity	NPC2771
0.856	High Similarity	NPC93730
0.8548	High Similarity	NPC314329
0.8537	High Similarity	NPC470092
0.8492	Intermediate Similarity	NPC193805
0.8455	Intermediate Similarity	NPC201284
0.8438	Intermediate Similarity	NPC298884
0.8425	Intermediate Similarity	NPC224657
0.8417	Intermediate Similarity	NPC53953
0.8387	Intermediate Similarity	NPC230951
0.8374	Intermediate Similarity	NPC171023
0.8372	Intermediate Similarity	NPC125887
0.8359	Intermediate Similarity	NPC237868
0.8295	Intermediate Similarity	NPC41721
0.8295	Intermediate Similarity	NPC22783
0.8293	Intermediate Similarity	NPC217423
0.8286	Intermediate Similarity	NPC472885
0.8279	Intermediate Similarity	NPC188907
0.8231	Intermediate Similarity	NPC196034
0.8189	Intermediate Similarity	NPC311219
0.8182	Intermediate Similarity	NPC301717
0.8168	Intermediate Similarity	NPC187907
0.8168	Intermediate Similarity	NPC473019
0.8154	Intermediate Similarity	NPC49852
0.8154	Intermediate Similarity	NPC475496
0.8125	Intermediate Similarity	NPC182646
0.812	Intermediate Similarity	NPC284424
0.8112	Intermediate Similarity	NPC472884
0.8106	Intermediate Similarity	NPC7569
0.8099	Intermediate Similarity	NPC23332
0.8095	Intermediate Similarity	NPC246214
0.8092	Intermediate Similarity	NPC473907
0.808	Intermediate Similarity	NPC152159
0.8077	Intermediate Similarity	NPC474264
0.8065	Intermediate Similarity	NPC470860
0.8062	Intermediate Similarity	NPC56332
0.806	Intermediate Similarity	NPC229646
0.803	Intermediate Similarity	NPC197425
0.803	Intermediate Similarity	NPC473894
0.8017	Intermediate Similarity	NPC183648
0.8	Intermediate Similarity	NPC292998
0.8	Intermediate Similarity	NPC45104
0.7985	Intermediate Similarity	NPC278556
0.7984	Intermediate Similarity	NPC141252
0.7984	Intermediate Similarity	NPC11799
0.797	Intermediate Similarity	NPC228184
0.797	Intermediate Similarity	NPC39753
0.797	Intermediate Similarity	NPC115998
0.797	Intermediate Similarity	NPC278787
0.7937	Intermediate Similarity	NPC206007
0.7926	Intermediate Similarity	NPC101294
0.7926	Intermediate Similarity	NPC473655
0.791	Intermediate Similarity	NPC11173
0.791	Intermediate Similarity	NPC141549
0.791	Intermediate Similarity	NPC270369
0.791	Intermediate Similarity	NPC324488
0.791	Intermediate Similarity	NPC5515
0.791	Intermediate Similarity	NPC137264
0.7903	Intermediate Similarity	NPC252004
0.7891	Intermediate Similarity	NPC472887
0.7883	Intermediate Similarity	NPC77955
0.7883	Intermediate Similarity	NPC151113
0.7879	Intermediate Similarity	NPC45537
0.7874	Intermediate Similarity	NPC43435
0.7868	Intermediate Similarity	NPC57601
0.7863	Intermediate Similarity	NPC165556
0.7863	Intermediate Similarity	NPC470858
0.7863	Intermediate Similarity	NPC65041
0.7863	Intermediate Similarity	NPC4164
0.7857	Intermediate Similarity	NPC469954
0.7852	Intermediate Similarity	NPC475589
0.7852	Intermediate Similarity	NPC113006
0.7852	Intermediate Similarity	NPC31872
0.7852	Intermediate Similarity	NPC473584
0.7852	Intermediate Similarity	NPC118253
0.7851	Intermediate Similarity	NPC224584
0.7826	Intermediate Similarity	NPC254741
0.7826	Intermediate Similarity	NPC472516
0.7815	Intermediate Similarity	NPC38209
0.7812	Intermediate Similarity	NPC474874
0.7812	Intermediate Similarity	NPC168050
0.781	Intermediate Similarity	NPC125269
0.781	Intermediate Similarity	NPC172262
0.781	Intermediate Similarity	NPC298900
0.781	Intermediate Similarity	NPC66705
0.781	Intermediate Similarity	NPC217914
0.7805	Intermediate Similarity	NPC233238
0.7794	Intermediate Similarity	NPC287533
0.7794	Intermediate Similarity	NPC25937
0.7794	Intermediate Similarity	NPC128216
0.7794	Intermediate Similarity	NPC10971
0.7787	Intermediate Similarity	NPC259554
0.7786	Intermediate Similarity	NPC107846
0.7778	Intermediate Similarity	NPC316062
0.777	Intermediate Similarity	NPC157855
0.777	Intermediate Similarity	NPC250266
0.777	Intermediate Similarity	NPC253616
0.777	Intermediate Similarity	NPC228661
0.777	Intermediate Similarity	NPC332594
0.777	Intermediate Similarity	NPC103001
0.777	Intermediate Similarity	NPC266597
0.7761	Intermediate Similarity	NPC211120
0.7754	Intermediate Similarity	NPC46869
0.775	Intermediate Similarity	NPC139891
0.7744	Intermediate Similarity	NPC293387
0.7744	Intermediate Similarity	NPC470841
0.7744	Intermediate Similarity	NPC37512
0.7737	Intermediate Similarity	NPC223457
0.7737	Intermediate Similarity	NPC50898
0.7737	Intermediate Similarity	NPC108113
0.7737	Intermediate Similarity	NPC213216
0.7737	Intermediate Similarity	NPC93756
0.7737	Intermediate Similarity	NPC274121
0.7737	Intermediate Similarity	NPC78540
0.7733	Intermediate Similarity	NPC472886
0.7731	Intermediate Similarity	NPC298224
0.7721	Intermediate Similarity	NPC474340
0.7714	Intermediate Similarity	NPC36414
0.7698	Intermediate Similarity	NPC72452
0.7698	Intermediate Similarity	NPC47815
0.7698	Intermediate Similarity	NPC13408
0.7698	Intermediate Similarity	NPC161196
0.7698	Intermediate Similarity	NPC61546
0.7698	Intermediate Similarity	NPC194281
0.7698	Intermediate Similarity	NPC268081
0.7698	Intermediate Similarity	NPC29353
0.7698	Intermediate Similarity	NPC240593
0.7698	Intermediate Similarity	NPC231772
0.7698	Intermediate Similarity	NPC127447
0.7698	Intermediate Similarity	NPC234133
0.7698	Intermediate Similarity	NPC124784
0.7698	Intermediate Similarity	NPC473887
0.7687	Intermediate Similarity	NPC186098
0.7687	Intermediate Similarity	NPC80694
0.7687	Intermediate Similarity	NPC2401
0.7687	Intermediate Similarity	NPC475017
0.7681	Intermediate Similarity	NPC125920
0.7681	Intermediate Similarity	NPC248872
0.7664	Intermediate Similarity	NPC477536
0.7664	Intermediate Similarity	NPC182428
0.7661	Intermediate Similarity	NPC54626
0.7661	Intermediate Similarity	NPC57879
0.766	Intermediate Similarity	NPC136095
0.7656	Intermediate Similarity	NPC94637
0.7652	Intermediate Similarity	NPC4012
0.7652	Intermediate Similarity	NPC255073
0.7652	Intermediate Similarity	NPC265910
0.7652	Intermediate Similarity	NPC470008
0.7652	Intermediate Similarity	NPC470162
0.7652	Intermediate Similarity	NPC91475
0.7652	Intermediate Similarity	NPC470163
0.7647	Intermediate Similarity	NPC205360
0.7647	Intermediate Similarity	NPC477412
0.7643	Intermediate Similarity	NPC188879
0.7643	Intermediate Similarity	NPC160972
0.7643	Intermediate Similarity	NPC299379
0.7638	Intermediate Similarity	NPC128825
0.763	Intermediate Similarity	NPC939
0.763	Intermediate Similarity	NPC60558
0.763	Intermediate Similarity	NPC238309
0.763	Intermediate Similarity	NPC66246
0.763	Intermediate Similarity	NPC57552
0.763	Intermediate Similarity	NPC170546
0.7626	Intermediate Similarity	NPC242712
0.7626	Intermediate Similarity	NPC60667
0.7626	Intermediate Similarity	NPC9985
0.7626	Intermediate Similarity	NPC99854
0.7626	Intermediate Similarity	NPC239495
0.7619	Intermediate Similarity	NPC114144
0.7612	Intermediate Similarity	NPC264428
0.7609	Intermediate Similarity	NPC223354
0.7609	Intermediate Similarity	NPC247743
0.7606	Intermediate Similarity	NPC281207
0.7606	Intermediate Similarity	NPC269652
0.7606	Intermediate Similarity	NPC475680
0.7606	Intermediate Similarity	NPC270883
0.7606	Intermediate Similarity	NPC261227
0.7606	Intermediate Similarity	NPC305355
0.7606	Intermediate Similarity	NPC472409
0.7606	Intermediate Similarity	NPC172986
0.7606	Intermediate Similarity	NPC235239
0.7597	Intermediate Similarity	NPC90522
0.7597	Intermediate Similarity	NPC328459
0.7591	Intermediate Similarity	NPC64359
0.7591	Intermediate Similarity	NPC308037
0.7591	Intermediate Similarity	NPC313618
0.7591	Intermediate Similarity	NPC262359
0.7589	Intermediate Similarity	NPC470669
0.7589	Intermediate Similarity	NPC201395
0.7589	Intermediate Similarity	NPC280284
0.7589	Intermediate Similarity	NPC470668
0.7589	Intermediate Similarity	NPC99333
0.7589	Intermediate Similarity	NPC17848

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 NPC472888 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	1073
0.2-0.3	1393
0.3-0.4	2803
0.4-0.5	2078
0.5-0.6	1057
0.6-0.7	278
0.7-0.8	71
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8548	High Similarity	NPD1547	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD1241	Discontinued
0.8189	Intermediate Similarity	NPD9717	Approved
0.8092	Intermediate Similarity	NPD6832	Phase 2
0.8077	Intermediate Similarity	NPD2798	Approved
0.8	Intermediate Similarity	NPD1203	Approved
0.797	Intermediate Similarity	NPD2313	Discontinued
0.7939	Intermediate Similarity	NPD1019	Discontinued
0.7826	Intermediate Similarity	NPD2796	Approved
0.7754	Intermediate Similarity	NPD2799	Discontinued
0.775	Intermediate Similarity	NPD9697	Approved
0.7687	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1933	Approved
0.7643	Intermediate Similarity	NPD2344	Approved
0.7638	Intermediate Similarity	NPD9493	Approved
0.7594	Intermediate Similarity	NPD3267	Approved
0.7594	Intermediate Similarity	NPD3266	Approved
0.7591	Intermediate Similarity	NPD1240	Approved
0.7591	Intermediate Similarity	NPD4307	Phase 2
0.7574	Intermediate Similarity	NPD411	Approved
0.7536	Intermediate Similarity	NPD447	Suspended
0.7535	Intermediate Similarity	NPD1243	Approved
0.7518	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD3972	Approved
0.7482	Intermediate Similarity	NPD1607	Approved
0.7465	Intermediate Similarity	NPD1549	Phase 2
0.7463	Intermediate Similarity	NPD2797	Approved
0.7438	Intermediate Similarity	NPD9261	Approved
0.7431	Intermediate Similarity	NPD2309	Approved
0.7394	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1471	Phase 3
0.7394	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1876	Approved
0.7376	Intermediate Similarity	NPD4308	Phase 3
0.7376	Intermediate Similarity	NPD3748	Approved
0.7376	Intermediate Similarity	NPD1510	Phase 2
0.7347	Intermediate Similarity	NPD5049	Phase 3
0.7338	Intermediate Similarity	NPD3140	Approved
0.7338	Intermediate Similarity	NPD3142	Approved
0.7329	Intermediate Similarity	NPD6799	Approved
0.7324	Intermediate Similarity	NPD1551	Phase 2
0.7319	Intermediate Similarity	NPD3268	Approved
0.7279	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4662	Approved
0.7279	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4661	Approved
0.7279	Intermediate Similarity	NPD5401	Approved
0.7273	Intermediate Similarity	NPD17	Approved
0.726	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7440	Discontinued
0.7244	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1511	Approved
0.7203	Intermediate Similarity	NPD2935	Discontinued
0.72	Intermediate Similarity	NPD9263	Approved
0.72	Intermediate Similarity	NPD9264	Approved
0.72	Intermediate Similarity	NPD9267	Approved
0.7194	Intermediate Similarity	NPD1296	Phase 2
0.7181	Intermediate Similarity	NPD5403	Approved
0.7181	Intermediate Similarity	NPD920	Approved
0.7172	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD4062	Phase 3
0.7143	Intermediate Similarity	NPD9266	Approved
0.7123	Intermediate Similarity	NPD3750	Approved
0.7114	Intermediate Similarity	NPD1512	Approved
0.7111	Intermediate Similarity	NPD1608	Approved
0.7103	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3226	Approved
0.7083	Intermediate Similarity	NPD2531	Phase 2
0.7075	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7039	Intermediate Similarity	NPD6585	Discontinued
0.7039	Intermediate Similarity	NPD6599	Discontinued
0.7037	Intermediate Similarity	NPD422	Phase 1
0.7034	Intermediate Similarity	NPD2353	Approved
0.7034	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3225	Approved
0.6993	Remote Similarity	NPD5890	Approved
0.6993	Remote Similarity	NPD5889	Approved
0.6993	Remote Similarity	NPD7411	Suspended
0.6992	Remote Similarity	NPD9545	Approved
0.6992	Remote Similarity	NPD1894	Discontinued
0.6985	Remote Similarity	NPD1481	Phase 2
0.6984	Remote Similarity	NPD3134	Approved
0.6948	Remote Similarity	NPD6801	Discontinued
0.6948	Remote Similarity	NPD6279	Approved
0.6948	Remote Similarity	NPD6280	Approved
0.694	Remote Similarity	NPD1651	Approved
0.6929	Remote Similarity	NPD290	Approved
0.6929	Remote Similarity	NPD1358	Approved
0.6923	Remote Similarity	NPD5535	Approved
0.6918	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7286	Phase 2
0.6912	Remote Similarity	NPD1201	Approved
0.6912	Remote Similarity	NPD1535	Discovery
0.6911	Remote Similarity	NPD1238	Approved
0.6903	Remote Similarity	NPD7819	Suspended
0.6903	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2801	Approved
0.6889	Remote Similarity	NPD1778	Approved
0.6861	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2296	Approved
0.6859	Remote Similarity	NPD5402	Approved
0.6859	Remote Similarity	NPD3817	Phase 2
0.6846	Remote Similarity	NPD3887	Approved
0.6846	Remote Similarity	NPD2354	Approved
0.6842	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7317	Phase 3
0.6839	Remote Similarity	NPD1934	Approved
0.6838	Remote Similarity	NPD3496	Discontinued
0.6835	Remote Similarity	NPD919	Approved
0.6835	Remote Similarity	NPD1470	Approved
0.6831	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6798	Discontinued
0.6824	Remote Similarity	NPD2654	Approved
0.6824	Remote Similarity	NPD1652	Phase 2
0.6824	Remote Similarity	NPD2800	Approved
0.6818	Remote Similarity	NPD9281	Approved
0.6818	Remote Similarity	NPD4380	Phase 2
0.6815	Remote Similarity	NPD3882	Suspended
0.6815	Remote Similarity	NPD5585	Approved
0.6806	Remote Similarity	NPD4618	Approved
0.6806	Remote Similarity	NPD4340	Discontinued
0.6806	Remote Similarity	NPD4622	Approved
0.6795	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5536	Phase 2
0.6788	Remote Similarity	NPD1281	Approved
0.6781	Remote Similarity	NPD7033	Discontinued
0.6779	Remote Similarity	NPD4628	Phase 3
0.6774	Remote Similarity	NPD2366	Approved
0.6772	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7075	Discontinued
0.6767	Remote Similarity	NPD6671	Approved
0.6753	Remote Similarity	NPD2651	Approved
0.6753	Remote Similarity	NPD2649	Approved
0.6752	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7318	Phase 3
0.675	Remote Similarity	NPD1247	Approved
0.6744	Remote Similarity	NPD2684	Approved
0.6738	Remote Similarity	NPD9494	Approved
0.6735	Remote Similarity	NPD5712	Approved
0.6719	Remote Similarity	NPD968	Approved
0.6714	Remote Similarity	NPD1164	Approved
0.6712	Remote Similarity	NPD5688	Approved
0.6712	Remote Similarity	NPD5689	Approved
0.6709	Remote Similarity	NPD7768	Phase 2
0.6693	Remote Similarity	NPD164	Approved
0.6691	Remote Similarity	NPD5691	Approved
0.669	Remote Similarity	NPD6355	Discontinued
0.669	Remote Similarity	NPD1184	Approved
0.6689	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1559	Discontinued
0.6687	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD1611	Approved
0.6643	Remote Similarity	NPD1283	Approved
0.6642	Remote Similarity	NPD2557	Approved
0.6641	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3873	Phase 3
0.6623	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3869	Phase 3
0.6622	Remote Similarity	NPD4476	Approved
0.6622	Remote Similarity	NPD4477	Approved
0.662	Remote Similarity	NPD454	Approved
0.6618	Remote Similarity	NPD1548	Phase 1
0.6615	Remote Similarity	NPD2182	Approved
0.6605	Remote Similarity	NPD6808	Phase 2
0.6573	Remote Similarity	NPD2614	Approved
0.6571	Remote Similarity	NPD4359	Approved
0.6569	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD3926	Phase 2
0.6562	Remote Similarity	NPD6971	Discontinued
0.6558	Remote Similarity	NPD6273	Approved
0.6556	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6233	Phase 2
0.6552	Remote Similarity	NPD520	Approved
0.6552	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2788	Approved
0.6541	Remote Similarity	NPD821	Approved
0.6541	Remote Similarity	NPD7843	Approved
0.6541	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2897	Discontinued
0.6531	Remote Similarity	NPD6651	Approved
0.6524	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3252	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