NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	272.862
LogP:	2.516
LogD:	1.59
LogS:	-3.37
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.855
Synthetic Accessibility Score:	3.33
Fsp3:	0.467
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:	-5.162
MDCK Permeability:	2.3534143110737205e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.865
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	83.95903778076172%
Volume Distribution (VD):	0.195
Pgp-substrate:	23.737884521484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.517
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.145
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.233
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	1.796
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.367
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.469
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.047
Carcinogencity:	0.068
Eye Corrosion:	0.004
Eye Irritation:	0.274
Respiratory Toxicity:	0.193

Download Data

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

Natural Product: NPC472708

Natural Product ID:	NPC472708
*Common Name:**	KJCUFCRMRPHAFY-SWLSCSKDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KJCUFCRMRPHAFY-SWLSCSKDSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-14(2)12(17)11(16)8-15(14,3)10-6-4-9(5-7-10)13(18)19/h4-7,12,17H,8H2,1-3H3,(H,18,19)/t12-,15+/m0/s1
SMILES:	CC1(C(C(=O)CC1(C)C2=CC=C(C=C2)C(=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581625
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32768	basidiomycete deconica sp. 471	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25871540]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[451029]

☑ 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 NPC472708 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	206
0.1-0.2	930
0.2-0.3	2201
0.3-0.4	6339
0.4-0.5	13100
0.5-0.6	14586
0.6-0.7	4708
0.7-0.8	570
0.8-0.85	52
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8919	High Similarity	NPC249811
0.8699	High Similarity	NPC472706
0.8629	High Similarity	NPC472707
0.8468	Intermediate Similarity	NPC25458
0.8455	Intermediate Similarity	NPC472704
0.845	Intermediate Similarity	NPC232888
0.845	Intermediate Similarity	NPC477367
0.8374	Intermediate Similarity	NPC472703
0.8372	Intermediate Similarity	NPC477368
0.8346	Intermediate Similarity	NPC272946
0.8304	Intermediate Similarity	NPC304873
0.8295	Intermediate Similarity	NPC477364
0.8288	Intermediate Similarity	NPC217621
0.8279	Intermediate Similarity	NPC133302
0.8235	Intermediate Similarity	NPC476357
0.8235	Intermediate Similarity	NPC274839
0.8231	Intermediate Similarity	NPC477359
0.8203	Intermediate Similarity	NPC82712
0.8158	Intermediate Similarity	NPC249067
0.8145	Intermediate Similarity	NPC18785
0.811	Intermediate Similarity	NPC477365
0.8108	Intermediate Similarity	NPC253423
0.8103	Intermediate Similarity	NPC112903
0.8087	Intermediate Similarity	NPC105899
0.8077	Intermediate Similarity	NPC233692
0.8065	Intermediate Similarity	NPC472981
0.8062	Intermediate Similarity	NPC42234
0.8049	Intermediate Similarity	NPC204784
0.8047	Intermediate Similarity	NPC477370
0.8031	Intermediate Similarity	NPC477366
0.803	Intermediate Similarity	NPC472247
0.8018	Intermediate Similarity	NPC61944
0.8016	Intermediate Similarity	NPC85511
0.8	Intermediate Similarity	NPC72915
0.8	Intermediate Similarity	NPC167323
0.8	Intermediate Similarity	NPC269923
0.7955	Intermediate Similarity	NPC311492
0.7955	Intermediate Similarity	NPC28836
0.7953	Intermediate Similarity	NPC295664
0.7939	Intermediate Similarity	NPC239358
0.7939	Intermediate Similarity	NPC477360
0.7931	Intermediate Similarity	NPC321670
0.7907	Intermediate Similarity	NPC51448
0.7907	Intermediate Similarity	NPC115797
0.7891	Intermediate Similarity	NPC477363
0.7881	Intermediate Similarity	NPC469636
0.7879	Intermediate Similarity	NPC472248
0.7876	Intermediate Similarity	NPC229242
0.7876	Intermediate Similarity	NPC160548
0.7876	Intermediate Similarity	NPC210529
0.7876	Intermediate Similarity	NPC175852
0.7874	Intermediate Similarity	NPC477362
0.7868	Intermediate Similarity	NPC475413
0.7868	Intermediate Similarity	NPC242355
0.7868	Intermediate Similarity	NPC473497
0.7868	Intermediate Similarity	NPC474303
0.7863	Intermediate Similarity	NPC37914
0.7863	Intermediate Similarity	NPC185763
0.7863	Intermediate Similarity	NPC83409
0.7851	Intermediate Similarity	NPC196673
0.7846	Intermediate Similarity	NPC37968
0.784	Intermediate Similarity	NPC473243
0.784	Intermediate Similarity	NPC470585
0.7836	Intermediate Similarity	NPC202729
0.7833	Intermediate Similarity	NPC66208
0.7829	Intermediate Similarity	NPC477357
0.7826	Intermediate Similarity	NPC320891
0.7826	Intermediate Similarity	NPC284477
0.782	Intermediate Similarity	NPC472250
0.782	Intermediate Similarity	NPC203486
0.782	Intermediate Similarity	NPC126516
0.7805	Intermediate Similarity	NPC158157
0.7803	Intermediate Similarity	NPC233860
0.7797	Intermediate Similarity	NPC211439
0.7787	Intermediate Similarity	NPC186933
0.7778	Intermediate Similarity	NPC27721
0.7761	Intermediate Similarity	NPC475262
0.7761	Intermediate Similarity	NPC265459
0.7761	Intermediate Similarity	NPC270364
0.7761	Intermediate Similarity	NPC290833
0.7761	Intermediate Similarity	NPC200154
0.7759	Intermediate Similarity	NPC160382
0.7759	Intermediate Similarity	NPC255676
0.7754	Intermediate Similarity	NPC153214
0.7754	Intermediate Similarity	NPC45307
0.7752	Intermediate Similarity	NPC275576
0.7752	Intermediate Similarity	NPC472592
0.775	Intermediate Similarity	NPC476003
0.775	Intermediate Similarity	NPC474057
0.7742	Intermediate Similarity	NPC80605
0.7742	Intermediate Similarity	NPC222968
0.7742	Intermediate Similarity	NPC323440
0.7734	Intermediate Similarity	NPC228739
0.7734	Intermediate Similarity	NPC328107
0.7731	Intermediate Similarity	NPC318327
0.7724	Intermediate Similarity	NPC9274
0.7721	Intermediate Similarity	NPC473301
0.7705	Intermediate Similarity	NPC307651
0.7705	Intermediate Similarity	NPC474363
0.7704	Intermediate Similarity	NPC285221
0.7704	Intermediate Similarity	NPC217673
0.7704	Intermediate Similarity	NPC477358
0.7704	Intermediate Similarity	NPC194769
0.7704	Intermediate Similarity	NPC52523
0.7692	Intermediate Similarity	NPC169913
0.7687	Intermediate Similarity	NPC329913
0.7686	Intermediate Similarity	NPC471188
0.7686	Intermediate Similarity	NPC321852
0.7676	Intermediate Similarity	NPC477101
0.7676	Intermediate Similarity	NPC477099
0.7676	Intermediate Similarity	NPC477097
0.7674	Intermediate Similarity	NPC117794
0.7661	Intermediate Similarity	NPC212891
0.766	Intermediate Similarity	NPC205389
0.7658	Intermediate Similarity	NPC110704
0.7656	Intermediate Similarity	NPC223351
0.7652	Intermediate Similarity	NPC228435
0.7652	Intermediate Similarity	NPC203925
0.7647	Intermediate Similarity	NPC86772
0.7642	Intermediate Similarity	NPC93181
0.763	Intermediate Similarity	NPC79699
0.763	Intermediate Similarity	NPC23894
0.7623	Intermediate Similarity	NPC306977
0.7623	Intermediate Similarity	NPC287055
0.7623	Intermediate Similarity	NPC272524
0.7623	Intermediate Similarity	NPC242957
0.7623	Intermediate Similarity	NPC128368
0.7623	Intermediate Similarity	NPC206414
0.7619	Intermediate Similarity	NPC476645
0.7615	Intermediate Similarity	NPC476599
0.7615	Intermediate Similarity	NPC287473
0.7607	Intermediate Similarity	NPC301943
0.7607	Intermediate Similarity	NPC474365
0.7603	Intermediate Similarity	NPC260818
0.7603	Intermediate Similarity	NPC265513
0.7597	Intermediate Similarity	NPC8990
0.7591	Intermediate Similarity	NPC272523
0.7591	Intermediate Similarity	NPC477592
0.7591	Intermediate Similarity	NPC170718
0.7591	Intermediate Similarity	NPC325805
0.7591	Intermediate Similarity	NPC276652
0.7589	Intermediate Similarity	NPC170668
0.7586	Intermediate Similarity	NPC70624
0.7586	Intermediate Similarity	NPC282895
0.7586	Intermediate Similarity	NPC469481
0.7583	Intermediate Similarity	NPC85493
0.7583	Intermediate Similarity	NPC83628
0.7583	Intermediate Similarity	NPC265407
0.7578	Intermediate Similarity	NPC369
0.7578	Intermediate Similarity	NPC293831
0.7568	Intermediate Similarity	NPC62765
0.7565	Intermediate Similarity	NPC317280
0.7565	Intermediate Similarity	NPC329387
0.7561	Intermediate Similarity	NPC471721
0.7561	Intermediate Similarity	NPC153053
0.7559	Intermediate Similarity	NPC234337
0.7559	Intermediate Similarity	NPC183339
0.7559	Intermediate Similarity	NPC133389
0.7557	Intermediate Similarity	NPC110211
0.7556	Intermediate Similarity	NPC48929
0.7552	Intermediate Similarity	NPC125033
0.7552	Intermediate Similarity	NPC232583
0.7552	Intermediate Similarity	NPC25484
0.7541	Intermediate Similarity	NPC212718
0.7541	Intermediate Similarity	NPC474314
0.7541	Intermediate Similarity	NPC158282
0.7541	Intermediate Similarity	NPC292834
0.754	Intermediate Similarity	NPC318173
0.7538	Intermediate Similarity	NPC477369
0.7537	Intermediate Similarity	NPC125153
0.7536	Intermediate Similarity	NPC475660
0.7536	Intermediate Similarity	NPC251294
0.7521	Intermediate Similarity	NPC188895
0.7519	Intermediate Similarity	NPC475508
0.7519	Intermediate Similarity	NPC65627
0.7519	Intermediate Similarity	NPC471832
0.7519	Intermediate Similarity	NPC475192
0.7517	Intermediate Similarity	NPC477100
0.7517	Intermediate Similarity	NPC477098
0.75	Intermediate Similarity	NPC306740
0.75	Intermediate Similarity	NPC474659
0.75	Intermediate Similarity	NPC262936
0.75	Intermediate Similarity	NPC50872
0.75	Intermediate Similarity	NPC30491
0.75	Intermediate Similarity	NPC165197
0.75	Intermediate Similarity	NPC79917
0.7482	Intermediate Similarity	NPC473654
0.7481	Intermediate Similarity	NPC236405
0.748	Intermediate Similarity	NPC143768
0.748	Intermediate Similarity	NPC473767
0.748	Intermediate Similarity	NPC202015
0.748	Intermediate Similarity	NPC93287
0.7479	Intermediate Similarity	NPC172483
0.7478	Intermediate Similarity	NPC289201
0.7464	Intermediate Similarity	NPC9905
0.7462	Intermediate Similarity	NPC318067
0.7462	Intermediate Similarity	NPC471466
0.746	Intermediate Similarity	NPC160199
0.7459	Intermediate Similarity	NPC475002
0.7459	Intermediate Similarity	NPC95126

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 NPC472708 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	742
0.2-0.3	1438
0.3-0.4	2699
0.4-0.5	2427
0.5-0.6	1319
0.6-0.7	289
0.7-0.8	50
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
0.8158	Intermediate Similarity	NPD1237	Approved
0.7934	Intermediate Similarity	NPD5951	Approved
0.7899	Intermediate Similarity	NPD7236	Approved
0.7881	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD9495	Approved
0.7829	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD2629	Approved
0.7768	Intermediate Similarity	NPD1693	Approved
0.7746	Intermediate Similarity	NPD7239	Suspended
0.7652	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD2066	Phase 3
0.7607	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6647	Phase 2
0.7603	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1088	Approved
0.7568	Intermediate Similarity	NPD9256	Approved
0.7568	Intermediate Similarity	NPD9258	Approved
0.7559	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7008	Discontinued
0.75	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD1930	Approved
0.7458	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD1929	Approved
0.7424	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD6085	Phase 2
0.7411	Intermediate Similarity	NPD1090	Approved
0.7411	Intermediate Similarity	NPD1089	Approved
0.7411	Intermediate Similarity	NPD1086	Approved
0.7373	Intermediate Similarity	NPD1932	Approved
0.7339	Intermediate Similarity	NPD6858	Approved
0.7339	Intermediate Similarity	NPD7094	Approved
0.7321	Intermediate Similarity	NPD800	Approved
0.7311	Intermediate Similarity	NPD5765	Approved
0.7308	Intermediate Similarity	NPD6287	Discontinued
0.7295	Intermediate Similarity	NPD2182	Approved
0.7279	Intermediate Similarity	NPD7961	Discontinued
0.7273	Intermediate Similarity	NPD6685	Approved
0.7267	Intermediate Similarity	NPD7058	Phase 2
0.7267	Intermediate Similarity	NPD7057	Phase 3
0.7266	Intermediate Similarity	NPD7009	Phase 2
0.7254	Intermediate Similarity	NPD4628	Phase 3
0.725	Intermediate Similarity	NPD164	Approved
0.7236	Intermediate Similarity	NPD1317	Discontinued
0.7231	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD1202	Approved
0.7217	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD9257	Approved
0.7207	Intermediate Similarity	NPD9259	Approved
0.7165	Intermediate Similarity	NPD4198	Discontinued
0.7154	Intermediate Similarity	NPD2329	Discontinued
0.7154	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD7305	Phase 1
0.7143	Intermediate Similarity	NPD1087	Approved
0.7123	Intermediate Similarity	NPD6273	Approved
0.712	Intermediate Similarity	NPD9508	Approved
0.7111	Intermediate Similarity	NPD5736	Approved
0.7097	Intermediate Similarity	NPD2067	Discontinued
0.7077	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1238	Approved
0.7054	Intermediate Similarity	NPD7610	Discontinued
0.7043	Intermediate Similarity	NPD1239	Approved
0.7042	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7715	Approved
0.7029	Intermediate Similarity	NPD7714	Approved
0.7	Intermediate Similarity	NPD9545	Approved
0.7	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7799	Discontinued
0.6949	Remote Similarity	NPD1989	Approved
0.694	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5159	Phase 2
0.694	Remote Similarity	NPD5157	Phase 1
0.6937	Remote Similarity	NPD9491	Approved
0.6935	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5277	Phase 2
0.6911	Remote Similarity	NPD5048	Discontinued
0.6894	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5305	Approved
0.6894	Remote Similarity	NPD3019	Approved
0.6894	Remote Similarity	NPD2932	Approved
0.6894	Remote Similarity	NPD5306	Approved
0.6891	Remote Similarity	NPD1564	Approved
0.6891	Remote Similarity	NPD1566	Phase 3
0.6891	Remote Similarity	NPD1565	Approved
0.6866	Remote Similarity	NPD3972	Approved
0.6861	Remote Similarity	NPD3662	Phase 3
0.6861	Remote Similarity	NPD3663	Approved
0.6861	Remote Similarity	NPD3664	Approved
0.6861	Remote Similarity	NPD3661	Approved
0.685	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6912	Phase 3
0.6846	Remote Similarity	NPD9493	Approved
0.6842	Remote Similarity	NPD4106	Approved
0.6842	Remote Similarity	NPD4136	Approved
0.6842	Remote Similarity	NPD4135	Approved
0.6818	Remote Similarity	NPD1245	Approved
0.68	Remote Similarity	NPD9267	Approved
0.68	Remote Similarity	NPD9264	Approved
0.68	Remote Similarity	NPD9263	Approved
0.6791	Remote Similarity	NPD4807	Approved
0.6791	Remote Similarity	NPD4806	Approved
0.6788	Remote Similarity	NPD5647	Approved
0.6757	Remote Similarity	NPD226	Approved
0.6755	Remote Similarity	NPD7458	Discontinued
0.6746	Remote Similarity	NPD74	Approved
0.6746	Remote Similarity	NPD9266	Approved
0.6742	Remote Similarity	NPD3091	Approved
0.6741	Remote Similarity	NPD4878	Approved
0.6739	Remote Similarity	NPD5204	Approved
0.6736	Remote Similarity	NPD7137	Phase 2
0.6723	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD9260	Approved
0.6715	Remote Similarity	NPD2626	Approved
0.6715	Remote Similarity	NPD2625	Approved
0.6715	Remote Similarity	NPD2628	Approved
0.6715	Remote Similarity	NPD2160	Approved
0.6715	Remote Similarity	NPD2627	Approved
0.6715	Remote Similarity	NPD2159	Approved
0.6694	Remote Similarity	NPD5909	Discontinued
0.6692	Remote Similarity	NPD4102	Approved
0.6692	Remote Similarity	NPD1246	Approved
0.6692	Remote Similarity	NPD4105	Approved
0.669	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6002	Phase 3
0.669	Remote Similarity	NPD6005	Phase 3
0.669	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD7003	Approved
0.6645	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6966	Discovery
0.6642	Remote Similarity	NPD1104	Approved
0.6642	Remote Similarity	NPD3095	Discontinued
0.6639	Remote Similarity	NPD1563	Approved
0.662	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2650	Approved
0.6615	Remote Similarity	NPD6010	Discontinued
0.6615	Remote Similarity	NPD2652	Approved
0.6613	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3495	Discontinued
0.6601	Remote Similarity	NPD6599	Discontinued
0.66	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3764	Approved
0.6594	Remote Similarity	NPD1164	Approved
0.6594	Remote Similarity	NPD1470	Approved
0.6593	Remote Similarity	NPD3026	Approved
0.6593	Remote Similarity	NPD3023	Approved
0.6591	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5346	Phase 2
0.6581	Remote Similarity	NPD5347	Phase 2
0.6577	Remote Similarity	NPD9490	Approved
0.6573	Remote Similarity	NPD6355	Discontinued
0.6571	Remote Similarity	NPD5203	Approved
0.6571	Remote Similarity	NPD4617	Approved
0.6571	Remote Similarity	NPD4620	Approved
0.6571	Remote Similarity	NPD5201	Approved
0.6567	Remote Similarity	NPD3024	Approved
0.6567	Remote Similarity	NPD3025	Approved
0.6565	Remote Similarity	NPD4766	Approved
0.6565	Remote Similarity	NPD9281	Approved
0.6562	Remote Similarity	NPD4233	Approved
0.6562	Remote Similarity	NPD4234	Approved
0.6554	Remote Similarity	NPD8166	Discontinued
0.6552	Remote Similarity	NPD4793	Discontinued
0.6549	Remote Similarity	NPD7713	Phase 3
0.6544	Remote Similarity	NPD3092	Approved
0.6544	Remote Similarity	NPD1201	Approved
0.6528	Remote Similarity	NPD6653	Approved
0.6528	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD3673	Approved
0.6525	Remote Similarity	NPD3672	Approved
0.6522	Remote Similarity	NPD1876	Approved
0.6522	Remote Similarity	NPD1888	Phase 1
0.6522	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2345	Approved
0.6519	Remote Similarity	NPD1778	Approved
0.6507	Remote Similarity	NPD5408	Approved
0.6507	Remote Similarity	NPD5405	Approved
0.6507	Remote Similarity	NPD5406	Approved
0.6507	Remote Similarity	NPD5404	Approved
0.6503	Remote Similarity	NPD4140	Approved
0.6496	Remote Similarity	NPD9717	Approved
0.6493	Remote Similarity	NPD7741	Discontinued
0.6486	Remote Similarity	NPD227	Approved
0.6486	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD225	Approved
0.6485	Remote Similarity	NPD6764	Approved
0.6485	Remote Similarity	NPD6765	Approved
0.648	Remote Similarity	NPD9261	Approved
0.6479	Remote Similarity	NPD4621	Approved
0.6479	Remote Similarity	NPD4619	Approved
0.6475	Remote Similarity	NPD3094	Phase 2
0.6475	Remote Similarity	NPD6362	Approved
0.6471	Remote Similarity	NPD4879	Approved
0.6471	Remote Similarity	NPD7609	Phase 3
0.6466	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD2346	Discontinued
0.6463	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD969	Suspended

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