NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.09
Volume:	238.27
LogP:	3.304
LogD:	2.863
LogS:	-3.071
# Rotatable Bonds:	3
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.886
Synthetic Accessibility Score:	2.323
Fsp3:	0.308
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:	-4.778
MDCK Permeability:	1.5901949154795147e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.772
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	94.02947235107422%
Volume Distribution (VD):	0.669
Pgp-substrate:	8.37342357635498%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.869
CYP2C19-substrate:	0.468
CYP2C9-inhibitor:	0.772
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.695
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.426
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	4.636
Half-life (T1/2):	0.578

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.546
AMES Toxicity:	0.64
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.513
Skin Sensitization:	0.78
Carcinogencity:	0.075
Eye Corrosion:	0.083
Eye Irritation:	0.962
Respiratory Toxicity:	0.427

Download Data

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

Natural Product: NPC475589

Natural Product ID:	NPC475589
*Common Name:**	5-Hydroxy-7-Methoxy-2-Propylchromone
IUPAC Name:	5-hydroxy-7-methoxy-2-propylchromen-4-one
Synonyms:
Standard InCHIKey:	TYOICPGJEBACJB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H14O4/c1-3-4-8-5-10(14)13-11(15)6-9(16-2)7-12(13)17-8/h5-7,15H,3-4H2,1-2H3
SMILES:	CCCC1=CC(=O)C2=C(C=C(C=C2O1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508780
PubChem CID:	10421528
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
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(98)00534-2]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932146]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	aerial parts	Nanning, Guangxi Province, China	2014-OCT	PMID[28753309]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11277	Baeckea frutescens	Species	Myrtaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	31.5	ug.mL-1	PMID[457136]

☑ 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 NPC475589 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	354
0.1-0.2	1708
0.2-0.3	4776
0.3-0.4	12077
0.4-0.5	5849
0.5-0.6	4466
0.6-0.7	5708
0.7-0.8	4207
0.8-0.85	2053
0.85-0.9	1140
0.9-0.95	327
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC31872
1.0	High Similarity	NPC473584
0.9921	High Similarity	NPC25937
0.992	High Similarity	NPC270369
0.992	High Similarity	NPC5515
0.9843	High Similarity	NPC223457
0.9766	High Similarity	NPC125920
0.9764	High Similarity	NPC10971
0.969	High Similarity	NPC60667
0.9688	High Similarity	NPC108113
0.9688	High Similarity	NPC93756
0.9615	High Similarity	NPC127447
0.9615	High Similarity	NPC473887
0.9615	High Similarity	NPC124784
0.9615	High Similarity	NPC234133
0.9615	High Similarity	NPC231772
0.9615	High Similarity	NPC47815
0.9615	High Similarity	NPC194281
0.9615	High Similarity	NPC174999
0.9615	High Similarity	NPC29353
0.9609	High Similarity	NPC203817
0.96	High Similarity	NPC305518
0.96	High Similarity	NPC475496
0.96	High Similarity	NPC49852
0.96	High Similarity	NPC128428
0.9542	High Similarity	NPC266597
0.9542	High Similarity	NPC250266
0.9535	High Similarity	NPC50898
0.9535	High Similarity	NPC274121
0.9535	High Similarity	NPC78540
0.9535	High Similarity	NPC213216
0.9524	High Similarity	NPC473907
0.947	High Similarity	NPC131130
0.9466	High Similarity	NPC13408
0.9462	High Similarity	NPC172262
0.9462	High Similarity	NPC144027
0.9462	High Similarity	NPC236974
0.9449	High Similarity	NPC69235
0.9449	High Similarity	NPC212379
0.9449	High Similarity	NPC473894
0.9398	High Similarity	NPC139554
0.9398	High Similarity	NPC78913
0.9398	High Similarity	NPC471697
0.9398	High Similarity	NPC23257
0.9398	High Similarity	NPC18260
0.9398	High Similarity	NPC241838
0.9398	High Similarity	NPC152042
0.9398	High Similarity	NPC143799
0.9394	High Similarity	NPC188879
0.9389	High Similarity	NPC242712
0.9389	High Similarity	NPC151113
0.9385	High Similarity	NPC57601
0.938	High Similarity	NPC113006
0.9375	High Similarity	NPC185497
0.937	High Similarity	NPC186098
0.937	High Similarity	NPC80694
0.9328	High Similarity	NPC471587
0.9328	High Similarity	NPC269652
0.9328	High Similarity	NPC241100
0.9328	High Similarity	NPC230285
0.9328	High Similarity	NPC184536
0.9328	High Similarity	NPC281207
0.9328	High Similarity	NPC103342
0.9328	High Similarity	NPC159275
0.9328	High Similarity	NPC103904
0.9328	High Similarity	NPC146679
0.9328	High Similarity	NPC59951
0.9323	High Similarity	NPC124269
0.9323	High Similarity	NPC280284
0.9323	High Similarity	NPC99333
0.9323	High Similarity	NPC470668
0.9323	High Similarity	NPC57380
0.9323	High Similarity	NPC470669
0.9323	High Similarity	NPC188947
0.9323	High Similarity	NPC201395
0.9318	High Similarity	NPC121243
0.9318	High Similarity	NPC470398
0.9318	High Similarity	NPC187826
0.9318	High Similarity	NPC240147
0.9318	High Similarity	NPC281917
0.9318	High Similarity	NPC470397
0.9318	High Similarity	NPC116775
0.9318	High Similarity	NPC187432
0.9318	High Similarity	NPC156910
0.9318	High Similarity	NPC256042
0.9318	High Similarity	NPC216361
0.9318	High Similarity	NPC240593
0.9308	High Similarity	NPC212631
0.9308	High Similarity	NPC257756
0.9308	High Similarity	NPC205468
0.9308	High Similarity	NPC87231
0.9308	High Similarity	NPC129132
0.9297	High Similarity	NPC187907
0.9297	High Similarity	NPC230818
0.9297	High Similarity	NPC60558
0.9259	High Similarity	NPC110969
0.9259	High Similarity	NPC282300
0.9259	High Similarity	NPC136840
0.9259	High Similarity	NPC90582
0.9259	High Similarity	NPC262094
0.9254	High Similarity	NPC303633
0.9254	High Similarity	NPC53181
0.9254	High Similarity	NPC473076
0.9254	High Similarity	NPC217186
0.9254	High Similarity	NPC96565
0.9254	High Similarity	NPC140890
0.9254	High Similarity	NPC216978
0.9254	High Similarity	NPC310135
0.9254	High Similarity	NPC20709
0.9254	High Similarity	NPC329203
0.9254	High Similarity	NPC55018
0.9254	High Similarity	NPC150648
0.9254	High Similarity	NPC220062
0.9254	High Similarity	NPC225153
0.9254	High Similarity	NPC274784
0.9254	High Similarity	NPC301217
0.9254	High Similarity	NPC265871
0.9254	High Similarity	NPC222342
0.9248	High Similarity	NPC79943
0.9248	High Similarity	NPC107586
0.9248	High Similarity	NPC287246
0.9248	High Similarity	NPC299379
0.9248	High Similarity	NPC296490
0.9248	High Similarity	NPC243083
0.9248	High Similarity	NPC275055
0.9248	High Similarity	NPC290291
0.9248	High Similarity	NPC12296
0.9248	High Similarity	NPC228661
0.9248	High Similarity	NPC160972
0.9248	High Similarity	NPC295261
0.9248	High Similarity	NPC13768
0.9248	High Similarity	NPC32441
0.9242	High Similarity	NPC101752
0.9242	High Similarity	NPC239495
0.9242	High Similarity	NPC9985
0.9237	High Similarity	NPC242294
0.9237	High Similarity	NPC18877
0.9237	High Similarity	NPC337373
0.9237	High Similarity	NPC82225
0.9237	High Similarity	NPC144051
0.9237	High Similarity	NPC28753
0.9237	High Similarity	NPC56031
0.9237	High Similarity	NPC175098
0.9237	High Similarity	NPC192304
0.9237	High Similarity	NPC139813
0.9237	High Similarity	NPC263670
0.9237	High Similarity	NPC294593
0.9237	High Similarity	NPC188646
0.9237	High Similarity	NPC312318
0.9237	High Similarity	NPC159623
0.9237	High Similarity	NPC204960
0.9237	High Similarity	NPC472365
0.9237	High Similarity	NPC20560
0.9231	High Similarity	NPC278556
0.9231	High Similarity	NPC308037
0.9231	High Similarity	NPC64359
0.9231	High Similarity	NPC65060
0.9231	High Similarity	NPC313618
0.9231	High Similarity	NPC262359
0.9225	High Similarity	NPC84772
0.9219	High Similarity	NPC293453
0.9191	High Similarity	NPC226636
0.9191	High Similarity	NPC11561
0.9185	High Similarity	NPC110228
0.9185	High Similarity	NPC6407
0.9185	High Similarity	NPC129853
0.9185	High Similarity	NPC76445
0.9185	High Similarity	NPC150522
0.9185	High Similarity	NPC188243
0.9185	High Similarity	NPC284550
0.9185	High Similarity	NPC172986
0.9185	High Similarity	NPC261227
0.9185	High Similarity	NPC270883
0.9179	High Similarity	NPC147686
0.9179	High Similarity	NPC470399
0.9179	High Similarity	NPC470672
0.9179	High Similarity	NPC276905
0.9179	High Similarity	NPC470671
0.9179	High Similarity	NPC118813
0.9179	High Similarity	NPC474504
0.9179	High Similarity	NPC472460
0.9179	High Similarity	NPC474487
0.9179	High Similarity	NPC329225
0.9167	High Similarity	NPC248872
0.9167	High Similarity	NPC286336
0.916	High Similarity	NPC473655
0.916	High Similarity	NPC101294
0.9154	High Similarity	NPC137264
0.9154	High Similarity	NPC324482
0.9147	High Similarity	NPC197425
0.9124	High Similarity	NPC242100
0.9124	High Similarity	NPC255133
0.9124	High Similarity	NPC470216
0.9124	High Similarity	NPC158874
0.9118	High Similarity	NPC147688
0.9118	High Similarity	NPC166689
0.9118	High Similarity	NPC156590
0.9118	High Similarity	NPC4743
0.9118	High Similarity	NPC64908
0.9118	High Similarity	NPC118840

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 NPC475589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	985
0.2-0.3	1624
0.3-0.4	2721
0.4-0.5	1785
0.5-0.6	1167
0.6-0.7	354
0.7-0.8	113
0.8-0.85	43
0.85-0.9	10
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9248	High Similarity	NPD1552	Clinical (unspecified phase)
0.9248	High Similarity	NPD1550	Clinical (unspecified phase)
0.9231	High Similarity	NPD1240	Approved
0.9179	High Similarity	NPD1549	Phase 2
0.9098	High Similarity	NPD1510	Phase 2
0.9091	High Similarity	NPD1607	Approved
0.9058	High Similarity	NPD4378	Clinical (unspecified phase)
0.9037	High Similarity	NPD970	Clinical (unspecified phase)
0.8849	High Similarity	NPD1511	Approved
0.8786	High Similarity	NPD7410	Clinical (unspecified phase)
0.875	High Similarity	NPD2796	Approved
0.8723	High Similarity	NPD1512	Approved
0.8582	High Similarity	NPD6799	Approved
0.8562	High Similarity	NPD2801	Approved
0.8561	High Similarity	NPD2800	Approved
0.8493	Intermediate Similarity	NPD1934	Approved
0.8478	Intermediate Similarity	NPD1551	Phase 2
0.8435	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD1243	Approved
0.8425	Intermediate Similarity	NPD7411	Suspended
0.8394	Intermediate Similarity	NPD6651	Approved
0.8385	Intermediate Similarity	NPD422	Phase 1
0.8378	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD3750	Approved
0.8356	Intermediate Similarity	NPD4380	Phase 2
0.8322	Intermediate Similarity	NPD3882	Suspended
0.8321	Intermediate Similarity	NPD9717	Approved
0.8271	Intermediate Similarity	NPD1203	Approved
0.8267	Intermediate Similarity	NPD7075	Discontinued
0.8267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD6801	Discontinued
0.8231	Intermediate Similarity	NPD6599	Discontinued
0.8188	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD7819	Suspended
0.8151	Intermediate Similarity	NPD920	Approved
0.8133	Intermediate Similarity	NPD3817	Phase 2
0.8125	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1548	Phase 1
0.8042	Intermediate Similarity	NPD2654	Approved
0.8042	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD2344	Approved
0.8027	Intermediate Similarity	NPD5403	Approved
0.8026	Intermediate Similarity	NPD3749	Approved
0.8014	Intermediate Similarity	NPD3748	Approved
0.8014	Intermediate Similarity	NPD2532	Approved
0.8014	Intermediate Similarity	NPD2533	Approved
0.8014	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2534	Approved
0.8014	Intermediate Similarity	NPD5401	Approved
0.7987	Intermediate Similarity	NPD6959	Discontinued
0.7961	Intermediate Similarity	NPD7768	Phase 2
0.7949	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6166	Phase 2
0.7939	Intermediate Similarity	NPD9545	Approved
0.7923	Intermediate Similarity	NPD9493	Approved
0.7911	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7054	Approved
0.7862	Intermediate Similarity	NPD7472	Approved
0.7857	Intermediate Similarity	NPD943	Approved
0.7848	Intermediate Similarity	NPD3818	Discontinued
0.7842	Intermediate Similarity	NPD1296	Phase 2
0.7836	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD2935	Discontinued
0.7832	Intermediate Similarity	NPD6100	Approved
0.7832	Intermediate Similarity	NPD6099	Approved
0.7829	Intermediate Similarity	NPD1241	Discontinued
0.7826	Intermediate Similarity	NPD6832	Phase 2
0.7812	Intermediate Similarity	NPD6797	Phase 2
0.7808	Intermediate Similarity	NPD2309	Approved
0.7801	Intermediate Similarity	NPD230	Phase 1
0.7764	Intermediate Similarity	NPD7251	Discontinued
0.7762	Intermediate Similarity	NPD2799	Discontinued
0.7762	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7074	Phase 3
0.7742	Intermediate Similarity	NPD919	Approved
0.7727	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7808	Phase 3
0.7714	Intermediate Similarity	NPD3268	Approved
0.7714	Intermediate Similarity	NPD2313	Discontinued
0.7714	Intermediate Similarity	NPD411	Approved
0.7704	Intermediate Similarity	NPD1610	Phase 2
0.7702	Intermediate Similarity	NPD5953	Discontinued
0.7688	Intermediate Similarity	NPD7286	Phase 2
0.7681	Intermediate Similarity	NPD1019	Discontinued
0.7676	Intermediate Similarity	NPD447	Suspended
0.7664	Intermediate Similarity	NPD3225	Approved
0.7662	Intermediate Similarity	NPD5402	Approved
0.7643	Intermediate Similarity	NPD1247	Approved
0.7639	Intermediate Similarity	NPD7033	Discontinued
0.7619	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4628	Phase 3
0.7609	Intermediate Similarity	NPD2797	Approved
0.7607	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6232	Discontinued
0.758	Intermediate Similarity	NPD5494	Approved
0.7571	Intermediate Similarity	NPD4908	Phase 1
0.7571	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7473	Discontinued
0.7554	Intermediate Similarity	NPD2798	Approved
0.7518	Intermediate Similarity	NPD1608	Approved
0.7517	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4308	Phase 3
0.7484	Intermediate Similarity	NPD1465	Phase 2
0.7482	Intermediate Similarity	NPD3266	Approved
0.7482	Intermediate Similarity	NPD3267	Approved
0.7465	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3226	Approved
0.7439	Intermediate Similarity	NPD6559	Discontinued
0.7438	Intermediate Similarity	NPD3926	Phase 2
0.7431	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5124	Phase 1
0.7431	Intermediate Similarity	NPD1933	Approved
0.7431	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1729	Discontinued
0.7391	Intermediate Similarity	NPD1481	Phase 2
0.7391	Intermediate Similarity	NPD3972	Approved
0.7376	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5710	Approved
0.7375	Intermediate Similarity	NPD5711	Approved
0.7351	Intermediate Similarity	NPD7390	Discontinued
0.7338	Intermediate Similarity	NPD4749	Approved
0.7333	Intermediate Similarity	NPD6104	Discontinued
0.7325	Intermediate Similarity	NPD4288	Approved
0.7324	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1535	Discovery
0.7315	Intermediate Similarity	NPD1652	Phase 2
0.7308	Intermediate Similarity	NPD74	Approved
0.7308	Intermediate Similarity	NPD9266	Approved
0.7299	Intermediate Similarity	NPD17	Approved
0.7297	Intermediate Similarity	NPD2346	Discontinued
0.7284	Intermediate Similarity	NPD2403	Approved
0.7273	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4360	Phase 2
0.7267	Intermediate Similarity	NPD4363	Phase 3
0.7256	Intermediate Similarity	NPD5844	Phase 1
0.7254	Intermediate Similarity	NPD9494	Approved
0.7241	Intermediate Similarity	NPD3140	Approved
0.7241	Intermediate Similarity	NPD4307	Phase 2
0.7241	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1613	Approved
0.7241	Intermediate Similarity	NPD3142	Approved
0.7231	Intermediate Similarity	NPD9267	Approved
0.7231	Intermediate Similarity	NPD9263	Approved
0.7231	Intermediate Similarity	NPD9264	Approved
0.7231	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4361	Phase 2
0.7215	Intermediate Similarity	NPD2296	Approved
0.7208	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1201	Approved
0.7184	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1471	Phase 3
0.7174	Intermediate Similarity	NPD1778	Approved
0.7153	Intermediate Similarity	NPD1894	Discontinued
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7134	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1470	Approved
0.7113	Intermediate Similarity	NPD1164	Approved
0.7109	Intermediate Similarity	NPD940	Approved
0.7109	Intermediate Similarity	NPD846	Approved
0.7105	Intermediate Similarity	NPD2354	Approved
0.7103	Intermediate Similarity	NPD6798	Discontinued
0.7103	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3764	Approved
0.7101	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD9268	Approved
0.7078	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1876	Approved
0.7035	Intermediate Similarity	NPD4287	Approved
0.7034	Intermediate Similarity	NPD4625	Phase 3
0.7013	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3751	Discontinued
0.6985	Remote Similarity	NPD9281	Approved
0.6981	Remote Similarity	NPD6844	Discontinued
0.697	Remote Similarity	NPD290	Approved
0.6968	Remote Similarity	NPD4661	Approved
0.6968	Remote Similarity	NPD4662	Approved
0.6959	Remote Similarity	NPD6355	Discontinued
0.6954	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2353	Approved
0.6954	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1091	Approved
0.6947	Remote Similarity	NPD9697	Approved
0.6943	Remote Similarity	NPD1653	Approved
0.6939	Remote Similarity	NPD520	Approved
0.6939	Remote Similarity	NPD6233	Phase 2
0.6923	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9261	Approved
0.6918	Remote Similarity	NPD3027	Phase 3
0.6918	Remote Similarity	NPD5889	Approved
0.6918	Remote Similarity	NPD5890	Approved
0.6914	Remote Similarity	NPD6971	Discontinued
0.6908	Remote Similarity	NPD2424	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