NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.15
Volume:	251.998
LogP:	3.366
LogD:	3.16
LogS:	-3.335
# Rotatable Bonds:	0
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	5.137
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.708
MDCK Permeability:	1.875100497272797e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.949
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.686

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	94.0760269165039%
Volume Distribution (VD):	1.969
Pgp-substrate:	5.56087589263916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.224
CYP1A2-substrate:	0.742
CYP2C19-inhibitor:	0.819
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.799
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.666
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.566

ADMET: Excretion

Clearance (CL):	10.686
Half-life (T1/2):	0.259

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.543
Drug-inuced Liver Injury (DILI):	0.306
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.86
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.049
Carcinogencity:	0.139
Eye Corrosion:	0.01
Eye Irritation:	0.161
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC472376

Natural Product ID:	NPC472376
*Common Name:**	AURHAUOFBQPZMC-KGYLQXTDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AURHAUOFBQPZMC-KGYLQXTDSA-N
Standard InCHI:	InChI=1S/C15H20O2/c1-9-6-10-8-15(2,3)12(9)7-13(16)11-4-5-17-14(10)11/h4-6,10,12-13,16H,7-8H2,1-3H3/t10-,12+,13-/m1/s1
SMILES:	CC1=C[C@@H]2CC([C@H]1C[C@H](c1c2occ1)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397811
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004144] Heteroaromatic compounds

*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
NPO33203	euryspongia sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434422]
NPO33203	euryspongia sp.	Species	Dysideidae	Eukaryota	n.a.	Iriomote Island	n.a.	PMID[25600405]

☑ 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	4

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	40000.0	nM	PMID[505621]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[505621]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[505621]
NPT27	Others	Unspecified		IC50	>	40000.0	nM	PMID[505621]

☑ 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 NPC472376 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	322
0.1-0.2	1383
0.2-0.3	3403
0.3-0.4	8849
0.4-0.5	11082
0.5-0.6	6082
0.6-0.7	9589
0.7-0.8	1907
0.8-0.85	71
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC473885
0.9	High Similarity	NPC471074
0.8824	High Similarity	NPC106247
0.8797	High Similarity	NPC329707
0.8768	High Similarity	NPC473268
0.8676	High Similarity	NPC473982
0.8636	High Similarity	NPC118853
0.8582	High Similarity	NPC290955
0.8531	High Similarity	NPC64568
0.8521	High Similarity	NPC205765
0.8507	High Similarity	NPC23086
0.85	High Similarity	NPC186626
0.8485	Intermediate Similarity	NPC477967
0.8485	Intermediate Similarity	NPC263870
0.8467	Intermediate Similarity	NPC61788
0.8456	Intermediate Similarity	NPC59502
0.8444	Intermediate Similarity	NPC95567
0.8444	Intermediate Similarity	NPC319140
0.8403	Intermediate Similarity	NPC476946
0.8382	Intermediate Similarity	NPC279877
0.8357	Intermediate Similarity	NPC159786
0.8357	Intermediate Similarity	NPC92941
0.8356	Intermediate Similarity	NPC97904
0.8355	Intermediate Similarity	NPC116639
0.8345	Intermediate Similarity	NPC476944
0.8322	Intermediate Similarity	NPC473681
0.8322	Intermediate Similarity	NPC61157
0.8322	Intermediate Similarity	NPC218204
0.831	Intermediate Similarity	NPC220094
0.8309	Intermediate Similarity	NPC246392
0.8299	Intermediate Similarity	NPC250228
0.8276	Intermediate Similarity	NPC267632
0.8271	Intermediate Similarity	NPC97566
0.8271	Intermediate Similarity	NPC79557
0.8261	Intermediate Similarity	NPC21460
0.8252	Intermediate Similarity	NPC202260
0.8252	Intermediate Similarity	NPC90953
0.8248	Intermediate Similarity	NPC207294
0.8248	Intermediate Similarity	NPC112706
0.8248	Intermediate Similarity	NPC26532
0.8239	Intermediate Similarity	NPC310830
0.8239	Intermediate Similarity	NPC470742
0.8235	Intermediate Similarity	NPC474611
0.8231	Intermediate Similarity	NPC346
0.8227	Intermediate Similarity	NPC158525
0.8219	Intermediate Similarity	NPC84479
0.8214	Intermediate Similarity	NPC218838
0.8212	Intermediate Similarity	NPC114880
0.82	Intermediate Similarity	NPC472787
0.8194	Intermediate Similarity	NPC201370
0.8194	Intermediate Similarity	NPC18904
0.8194	Intermediate Similarity	NPC148374
0.8194	Intermediate Similarity	NPC473983
0.8188	Intermediate Similarity	NPC211625
0.8182	Intermediate Similarity	NPC476943
0.8176	Intermediate Similarity	NPC476938
0.8176	Intermediate Similarity	NPC476937
0.8175	Intermediate Similarity	NPC83178
0.8162	Intermediate Similarity	NPC300098
0.8141	Intermediate Similarity	NPC261184
0.8121	Intermediate Similarity	NPC476942
0.8121	Intermediate Similarity	NPC113428
0.8121	Intermediate Similarity	NPC61284
0.8121	Intermediate Similarity	NPC476941
0.8112	Intermediate Similarity	NPC215109
0.8112	Intermediate Similarity	NPC170604
0.8102	Intermediate Similarity	NPC216810
0.8102	Intermediate Similarity	NPC138139
0.8102	Intermediate Similarity	NPC46536
0.8095	Intermediate Similarity	NPC137295
0.8095	Intermediate Similarity	NPC158871
0.8092	Intermediate Similarity	NPC150895
0.8092	Intermediate Similarity	NPC205523
0.8088	Intermediate Similarity	NPC65735
0.8088	Intermediate Similarity	NPC243269
0.8088	Intermediate Similarity	NPC188377
0.8085	Intermediate Similarity	NPC470740
0.8082	Intermediate Similarity	NPC52412
0.8082	Intermediate Similarity	NPC263337
0.8071	Intermediate Similarity	NPC477645
0.8071	Intermediate Similarity	NPC136340
0.8054	Intermediate Similarity	NPC308799
0.8052	Intermediate Similarity	NPC221992
0.8045	Intermediate Similarity	NPC243704
0.8042	Intermediate Similarity	NPC146872
0.8042	Intermediate Similarity	NPC46896
0.8039	Intermediate Similarity	NPC75310
0.8039	Intermediate Similarity	NPC35000
0.8039	Intermediate Similarity	NPC472785
0.8039	Intermediate Similarity	NPC158261
0.8039	Intermediate Similarity	NPC42458
0.8029	Intermediate Similarity	NPC290193
0.8027	Intermediate Similarity	NPC254198
0.8	Intermediate Similarity	NPC474722
0.8	Intermediate Similarity	NPC939
0.7987	Intermediate Similarity	NPC62799
0.7986	Intermediate Similarity	NPC307401
0.7974	Intermediate Similarity	NPC30222
0.7974	Intermediate Similarity	NPC178932
0.7973	Intermediate Similarity	NPC142113
0.7972	Intermediate Similarity	NPC476947
0.797	Intermediate Similarity	NPC312525
0.797	Intermediate Similarity	NPC217180
0.7962	Intermediate Similarity	NPC88841
0.7962	Intermediate Similarity	NPC288602
0.7958	Intermediate Similarity	NPC214097
0.7956	Intermediate Similarity	NPC477038
0.7956	Intermediate Similarity	NPC178382
0.7956	Intermediate Similarity	NPC477965
0.7947	Intermediate Similarity	NPC195325
0.7947	Intermediate Similarity	NPC329180
0.7947	Intermediate Similarity	NPC470998
0.7943	Intermediate Similarity	NPC89133
0.7943	Intermediate Similarity	NPC298190
0.7941	Intermediate Similarity	NPC270807
0.7941	Intermediate Similarity	NPC174915
0.7941	Intermediate Similarity	NPC317217
0.7935	Intermediate Similarity	NPC304692
0.7931	Intermediate Similarity	NPC177262
0.7931	Intermediate Similarity	NPC236532
0.7922	Intermediate Similarity	NPC281258
0.7922	Intermediate Similarity	NPC469336
0.791	Intermediate Similarity	NPC187547
0.791	Intermediate Similarity	NPC21831
0.791	Intermediate Similarity	NPC87466
0.7908	Intermediate Similarity	NPC475777
0.7908	Intermediate Similarity	NPC476940
0.7908	Intermediate Similarity	NPC469503
0.7908	Intermediate Similarity	NPC75906
0.7908	Intermediate Similarity	NPC44577
0.7908	Intermediate Similarity	NPC476939
0.7905	Intermediate Similarity	NPC205071
0.7905	Intermediate Similarity	NPC223415
0.7905	Intermediate Similarity	NPC243577
0.7905	Intermediate Similarity	NPC470741
0.7898	Intermediate Similarity	NPC188649
0.7898	Intermediate Similarity	NPC18986
0.7895	Intermediate Similarity	NPC212257
0.7895	Intermediate Similarity	NPC45536
0.7891	Intermediate Similarity	NPC477537
0.7887	Intermediate Similarity	NPC471995
0.7885	Intermediate Similarity	NPC140952
0.7883	Intermediate Similarity	NPC16922
0.7881	Intermediate Similarity	NPC93666
0.7881	Intermediate Similarity	NPC19747
0.7877	Intermediate Similarity	NPC107571
0.7875	Intermediate Similarity	NPC296558
0.7871	Intermediate Similarity	NPC41880
0.7871	Intermediate Similarity	NPC104736
0.7868	Intermediate Similarity	NPC1848
0.7862	Intermediate Similarity	NPC64157
0.7862	Intermediate Similarity	NPC278832
0.7862	Intermediate Similarity	NPC121995
0.7857	Intermediate Similarity	NPC477966
0.7857	Intermediate Similarity	NPC477123
0.7857	Intermediate Similarity	NPC57998
0.7857	Intermediate Similarity	NPC477039
0.7857	Intermediate Similarity	NPC44606
0.7847	Intermediate Similarity	NPC265793
0.7838	Intermediate Similarity	NPC473152
0.7838	Intermediate Similarity	NPC20578
0.7838	Intermediate Similarity	NPC475519
0.7838	Intermediate Similarity	NPC62103
0.7834	Intermediate Similarity	NPC476350
0.7834	Intermediate Similarity	NPC287559
0.7834	Intermediate Similarity	NPC476349
0.7834	Intermediate Similarity	NPC477402
0.7832	Intermediate Similarity	NPC474426
0.7832	Intermediate Similarity	NPC474425
0.7832	Intermediate Similarity	NPC474407
0.7832	Intermediate Similarity	NPC471006
0.7832	Intermediate Similarity	NPC293253
0.7829	Intermediate Similarity	NPC472654
0.7823	Intermediate Similarity	NPC90296
0.7823	Intermediate Similarity	NPC67003
0.7821	Intermediate Similarity	NPC472776
0.7821	Intermediate Similarity	NPC472777
0.7821	Intermediate Similarity	NPC194499
0.7821	Intermediate Similarity	NPC81405
0.7821	Intermediate Similarity	NPC472778
0.7815	Intermediate Similarity	NPC224418
0.7812	Intermediate Similarity	NPC472784
0.781	Intermediate Similarity	NPC473379
0.781	Intermediate Similarity	NPC471549
0.781	Intermediate Similarity	NPC323118
0.7806	Intermediate Similarity	NPC179170
0.7806	Intermediate Similarity	NPC264943
0.7801	Intermediate Similarity	NPC208389
0.78	Intermediate Similarity	NPC247221
0.78	Intermediate Similarity	NPC469385
0.78	Intermediate Similarity	NPC185456
0.7792	Intermediate Similarity	NPC121615
0.7792	Intermediate Similarity	NPC33938
0.7792	Intermediate Similarity	NPC145830
0.7792	Intermediate Similarity	NPC294511
0.7785	Intermediate Similarity	NPC329493
0.7778	Intermediate Similarity	NPC470997
0.7778	Intermediate Similarity	NPC471998
0.7771	Intermediate Similarity	NPC262872
0.7771	Intermediate Similarity	NPC477403

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 NPC472376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	946
0.2-0.3	1654
0.3-0.4	2632
0.4-0.5	2107
0.5-0.6	1156
0.6-0.7	313
0.7-0.8	37
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
0.7877	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD5760	Phase 2
0.7806	Intermediate Similarity	NPD5761	Phase 2
0.7619	Intermediate Similarity	NPD8434	Phase 2
0.7517	Intermediate Similarity	NPD2344	Approved
0.7383	Intermediate Similarity	NPD2799	Discontinued
0.7376	Intermediate Similarity	NPD9717	Approved
0.7355	Intermediate Similarity	NPD6273	Approved
0.732	Intermediate Similarity	NPD2309	Approved
0.7308	Intermediate Similarity	NPD920	Approved
0.7305	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2800	Approved
0.729	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1471	Phase 3
0.7284	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1241	Discontinued
0.7255	Intermediate Similarity	NPD4628	Phase 3
0.7211	Intermediate Similarity	NPD2313	Discontinued
0.7181	Intermediate Similarity	NPD447	Suspended
0.7172	Intermediate Similarity	NPD5647	Approved
0.7172	Intermediate Similarity	NPD2798	Approved
0.7171	Intermediate Similarity	NPD2346	Discontinued
0.7161	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1549	Phase 2
0.7118	Intermediate Similarity	NPD6764	Approved
0.7118	Intermediate Similarity	NPD6559	Discontinued
0.7118	Intermediate Similarity	NPD6765	Approved
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1551	Phase 2
0.7105	Intermediate Similarity	NPD2796	Approved
0.7105	Intermediate Similarity	NPD2935	Discontinued
0.7103	Intermediate Similarity	NPD2797	Approved
0.7103	Intermediate Similarity	NPD1203	Approved
0.7075	Intermediate Similarity	NPD6832	Phase 2
0.707	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6004	Phase 3
0.7059	Intermediate Similarity	NPD6002	Phase 3
0.7059	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6005	Phase 3
0.7059	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1019	Discontinued
0.7042	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1876	Approved
0.7014	Intermediate Similarity	NPD3972	Approved
0.7	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD1240	Approved
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3268	Approved
0.698	Remote Similarity	NPD411	Approved
0.6968	Remote Similarity	NPD1243	Approved
0.6962	Remote Similarity	NPD2534	Approved
0.6962	Remote Similarity	NPD2532	Approved
0.6962	Remote Similarity	NPD2533	Approved
0.6957	Remote Similarity	NPD4380	Phase 2
0.6954	Remote Similarity	NPD6784	Approved
0.6954	Remote Similarity	NPD6785	Approved
0.6934	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7819	Suspended
0.6933	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5494	Approved
0.6928	Remote Similarity	NPD1510	Phase 2
0.6923	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7003	Approved
0.6923	Remote Similarity	NPD3750	Approved
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3749	Approved
0.6908	Remote Similarity	NPD1607	Approved
0.6903	Remote Similarity	NPD2424	Discontinued
0.6894	Remote Similarity	NPD3226	Approved
0.6892	Remote Similarity	NPD9494	Approved
0.689	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1247	Approved
0.6859	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6599	Discontinued
0.6848	Remote Similarity	NPD3882	Suspended
0.6842	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD9092	Discovery
0.6829	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4308	Phase 3
0.681	Remote Similarity	NPD7411	Suspended
0.6807	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7075	Discontinued
0.6797	Remote Similarity	NPD6653	Approved
0.6795	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5402	Approved
0.6788	Remote Similarity	NPD2296	Approved
0.6784	Remote Similarity	NPD3818	Discontinued
0.6781	Remote Similarity	NPD1608	Approved
0.6776	Remote Similarity	NPD4140	Approved
0.6774	Remote Similarity	NPD6100	Approved
0.6774	Remote Similarity	NPD6099	Approved
0.677	Remote Similarity	NPD5403	Approved
0.6768	Remote Similarity	NPD6844	Discontinued
0.6768	Remote Similarity	NPD6280	Approved
0.6768	Remote Similarity	NPD1934	Approved
0.6768	Remote Similarity	NPD6801	Discontinued
0.6768	Remote Similarity	NPD6279	Approved
0.6766	Remote Similarity	NPD919	Approved
0.6761	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6362	Approved
0.6755	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4661	Approved
0.675	Remote Similarity	NPD4662	Approved
0.675	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7768	Phase 2
0.6736	Remote Similarity	NPD5585	Approved
0.6732	Remote Similarity	NPD6355	Discontinued
0.6725	Remote Similarity	NPD3446	Phase 1
0.6711	Remote Similarity	NPD8032	Phase 2
0.6711	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.671	Remote Similarity	NPD3748	Approved
0.671	Remote Similarity	NPD7033	Discontinued
0.669	Remote Similarity	NPD7157	Approved
0.669	Remote Similarity	NPD1778	Approved
0.6689	Remote Similarity	NPD1283	Approved
0.6689	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6651	Approved
0.6687	Remote Similarity	NPD6799	Approved
0.6687	Remote Similarity	NPD2651	Approved
0.6687	Remote Similarity	NPD2649	Approved
0.6687	Remote Similarity	NPD7458	Discontinued
0.6686	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD5712	Approved
0.6667	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9545	Approved
0.6648	Remote Similarity	NPD8313	Approved
0.6648	Remote Similarity	NPD8312	Approved
0.6647	Remote Similarity	NPD6808	Phase 2
0.6646	Remote Similarity	NPD5401	Approved
0.6645	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3764	Approved
0.6644	Remote Similarity	NPD3267	Approved
0.6644	Remote Similarity	NPD3266	Approved
0.6644	Remote Similarity	NPD3496	Discontinued
0.6643	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2801	Approved
0.6625	Remote Similarity	NPD7236	Approved
0.6621	Remote Similarity	NPD1651	Approved
0.6604	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4110	Phase 3
0.66	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8404	Phase 2
0.6594	Remote Similarity	NPD290	Approved
0.6591	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8127	Discontinued
0.6584	Remote Similarity	NPD1511	Approved
0.6575	Remote Similarity	NPD2932	Approved
0.6575	Remote Similarity	NPD17	Approved
0.657	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6166	Phase 2
0.657	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4476	Approved
0.6561	Remote Similarity	NPD4477	Approved
0.6558	Remote Similarity	NPD4307	Phase 2
0.6558	Remote Similarity	NPD3142	Approved
0.6558	Remote Similarity	NPD3140	Approved
0.6552	Remote Similarity	NPD5844	Phase 1
0.6552	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD2684	Approved
0.6547	Remote Similarity	NPD2182	Approved
0.6533	Remote Similarity	NPD1470	Approved
0.6516	Remote Similarity	NPD5735	Approved
0.6516	Remote Similarity	NPD1933	Approved
0.6512	Remote Similarity	NPD3926	Phase 2
0.651	Remote Similarity	NPD5327	Phase 3
0.651	Remote Similarity	NPD4359	Approved
0.6507	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1512	Approved
0.65	Remote Similarity	NPD8166	Discontinued
0.6496	Remote Similarity	NPD1237	Approved
0.6494	Remote Similarity	NPD6233	Phase 2
0.6494	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1201	Approved
0.6486	Remote Similarity	NPD1281	Approved
0.6478	Remote Similarity	NPD4534	Discontinued
0.6475	Remote Similarity	NPD9264	Approved
0.6475	Remote Similarity	NPD9267	Approved
0.6475	Remote Similarity	NPD9263	Approved
0.6471	Remote Similarity	NPD7008	Discontinued
0.6467	Remote Similarity	NPD6696	Suspended
0.6467	Remote Similarity	NPD7577	Discontinued
0.6467	Remote Similarity	NPD37	Approved
0.6463	Remote Similarity	NPD3873	Phase 3
0.6463	Remote Similarity	NPD3019	Approved
0.6463	Remote Similarity	NPD3869	Phase 3
0.6463	Remote Similarity	NPD4626	Approved
0.6452	Remote Similarity	NPD2979	Phase 3
0.645	Remote Similarity	NPD4967	Phase 2
0.645	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.645	Remote Similarity	NPD4965	Approved
0.645	Remote Similarity	NPD4966	Approved
0.6446	Remote Similarity	NPD7028	Phase 2
0.6443	Remote Similarity	NPD1481	Phase 2
0.6442	Remote Similarity	NPD1578	Phase 2

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