NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.1
Volume:	255.566
LogP:	3.207
LogD:	2.994
LogS:	-3.885
# Rotatable Bonds:	4
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.834
Synthetic Accessibility Score:	2.232
Fsp3:	0.357
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:	-4.723
MDCK Permeability:	2.2158581487019546e-05
Pgp-inhibitor:	0.886
Pgp-substrate:	0.368
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.618

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.317
Plasma Protein Binding (PPB):	87.0976791381836%
Volume Distribution (VD):	0.848
Pgp-substrate:	10.436985969543457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.915
CYP2C19-substrate:	0.869
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.415
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.484
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	5.409
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.223
Drug-inuced Liver Injury (DILI):	0.716
AMES Toxicity:	0.642
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.383
Skin Sensitization:	0.562
Carcinogencity:	0.054
Eye Corrosion:	0.075
Eye Irritation:	0.928
Respiratory Toxicity:	0.456

Download Data

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

Natural Product: NPC473907

Natural Product ID:	NPC473907
*Common Name:**	5,7-Dimethoxy-2-Propylchromen-4-One
IUPAC Name:	5,7-dimethoxy-2-propylchromen-4-one
Synonyms:
Standard InCHIKey:	OWKICUYZFSTQDO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H16O4/c1-4-5-9-6-11(15)14-12(17-3)7-10(16-2)8-13(14)18-9/h6-8H,4-5H2,1-3H3
SMILES:	CCCc1cc(=O)c2c(o1)cc(cc2OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454845
PubChem CID:	44559643
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	=	106.0	ug.mL-1	PMID[505312]

☑ 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 NPC473907 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	426
0.1-0.2	1904
0.2-0.3	5403
0.3-0.4	12581
0.4-0.5	4901
0.5-0.6	4972
0.6-0.7	5924
0.7-0.8	4102
0.8-0.85	1682
0.85-0.9	683
0.9-0.95	105
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC473894
0.9917	High Similarity	NPC49852
0.9917	High Similarity	NPC475496
0.9603	High Similarity	NPC101294
0.9603	High Similarity	NPC473655
0.9524	High Similarity	NPC278556
0.9524	High Similarity	NPC473584
0.9524	High Similarity	NPC475589
0.9524	High Similarity	NPC31872
0.9449	High Similarity	NPC229646
0.9449	High Similarity	NPC25937
0.9449	High Similarity	NPC10971
0.9444	High Similarity	NPC270369
0.9444	High Similarity	NPC5515
0.9431	High Similarity	NPC65041
0.938	High Similarity	NPC46869
0.9375	High Similarity	NPC223457
0.937	High Similarity	NPC284424
0.9308	High Similarity	NPC72452
0.9308	High Similarity	NPC268081
0.9308	High Similarity	NPC254741
0.9308	High Similarity	NPC174999
0.9308	High Similarity	NPC161196
0.9308	High Similarity	NPC61546
0.9302	High Similarity	NPC125269
0.9302	High Similarity	NPC125920
0.9297	High Similarity	NPC203817
0.9286	High Similarity	NPC211120
0.9237	High Similarity	NPC253616
0.9231	High Similarity	NPC60667
0.9231	High Similarity	NPC99854
0.9225	High Similarity	NPC93756
0.9225	High Similarity	NPC108113
0.9225	High Similarity	NPC292998
0.9167	High Similarity	NPC131130
0.9167	High Similarity	NPC36414
0.9167	High Similarity	NPC276905
0.9167	High Similarity	NPC17848
0.916	High Similarity	NPC47815
0.916	High Similarity	NPC234133
0.916	High Similarity	NPC231772
0.916	High Similarity	NPC472883
0.916	High Similarity	NPC29353
0.916	High Similarity	NPC473887
0.916	High Similarity	NPC127447
0.916	High Similarity	NPC194281
0.916	High Similarity	NPC13408
0.916	High Similarity	NPC124784
0.9154	High Similarity	NPC144027
0.9154	High Similarity	NPC236974
0.9127	High Similarity	NPC305518
0.9127	High Similarity	NPC41721
0.9127	High Similarity	NPC128428
0.9098	High Similarity	NPC139554
0.9098	High Similarity	NPC23257
0.9091	High Similarity	NPC250266
0.9091	High Similarity	NPC266597
0.9091	High Similarity	NPC188879
0.9091	High Similarity	NPC259685
0.9077	High Similarity	NPC50898
0.9077	High Similarity	NPC78540
0.9077	High Similarity	NPC213216
0.9077	High Similarity	NPC223354
0.9077	High Similarity	NPC247743
0.9077	High Similarity	NPC274121
0.9055	High Similarity	NPC475017
0.903	High Similarity	NPC150522
0.903	High Similarity	NPC471587
0.903	High Similarity	NPC159275
0.903	High Similarity	NPC241100
0.9023	High Similarity	NPC470669
0.9023	High Similarity	NPC470668
0.9023	High Similarity	NPC124269
0.9015	High Similarity	NPC121243
0.9015	High Similarity	NPC470398
0.9015	High Similarity	NPC187826
0.9015	High Similarity	NPC470397
0.9015	High Similarity	NPC240593
0.9015	High Similarity	NPC156910
0.9015	High Similarity	NPC240147
0.9008	High Similarity	NPC172262
0.9	High Similarity	NPC182428
0.8984	High Similarity	NPC187907
0.8984	High Similarity	NPC212379
0.8984	High Similarity	NPC69235
0.8963	High Similarity	NPC471640
0.8963	High Similarity	NPC110969
0.8963	High Similarity	NPC282300
0.8963	High Similarity	NPC103362
0.8963	High Similarity	NPC29536
0.8963	High Similarity	NPC262094
0.8963	High Similarity	NPC471644
0.8963	High Similarity	NPC90582
0.8955	High Similarity	NPC136095
0.8955	High Similarity	NPC152042
0.8955	High Similarity	NPC303633
0.8955	High Similarity	NPC96565
0.8955	High Similarity	NPC216978
0.8955	High Similarity	NPC220062
0.8955	High Similarity	NPC241838
0.8955	High Similarity	NPC55018
0.8955	High Similarity	NPC472515
0.8955	High Similarity	NPC78913
0.8955	High Similarity	NPC301217
0.8955	High Similarity	NPC11566
0.8955	High Similarity	NPC140890
0.8955	High Similarity	NPC18260
0.8955	High Similarity	NPC217186
0.8955	High Similarity	NPC471697
0.8955	High Similarity	NPC53181
0.8955	High Similarity	NPC143799
0.8947	High Similarity	NPC103001
0.8947	High Similarity	NPC157855
0.8939	High Similarity	NPC151113
0.8939	High Similarity	NPC101752
0.8939	High Similarity	NPC242712
0.8931	High Similarity	NPC188646
0.8931	High Similarity	NPC18877
0.8931	High Similarity	NPC56031
0.8931	High Similarity	NPC294593
0.8931	High Similarity	NPC204960
0.8931	High Similarity	NPC242294
0.8931	High Similarity	NPC312318
0.8931	High Similarity	NPC57601
0.8931	High Similarity	NPC263670
0.8931	High Similarity	NPC472365
0.8931	High Similarity	NPC192304
0.8931	High Similarity	NPC144051
0.8931	High Similarity	NPC139813
0.8931	High Similarity	NPC82225
0.8931	High Similarity	NPC159623
0.8931	High Similarity	NPC337373
0.8931	High Similarity	NPC28753
0.8931	High Similarity	NPC175098
0.8931	High Similarity	NPC20560
0.8923	High Similarity	NPC113006
0.8915	High Similarity	NPC84772
0.8915	High Similarity	NPC185497
0.8906	High Similarity	NPC80694
0.8906	High Similarity	NPC186098
0.8897	High Similarity	NPC11561
0.8897	High Similarity	NPC226636
0.8897	High Similarity	NPC9966
0.8897	High Similarity	NPC70853
0.8889	High Similarity	NPC103904
0.8889	High Similarity	NPC171094
0.8889	High Similarity	NPC281207
0.8889	High Similarity	NPC184536
0.8889	High Similarity	NPC188243
0.8889	High Similarity	NPC76445
0.8889	High Similarity	NPC146679
0.8889	High Similarity	NPC255073
0.8889	High Similarity	NPC284550
0.8889	High Similarity	NPC172986
0.8889	High Similarity	NPC270883
0.8889	High Similarity	NPC6407
0.8889	High Similarity	NPC269652
0.8889	High Similarity	NPC474037
0.8889	High Similarity	NPC103342
0.8889	High Similarity	NPC261227
0.8889	High Similarity	NPC230285
0.8889	High Similarity	NPC129853
0.8889	High Similarity	NPC110228
0.8889	High Similarity	NPC59951
0.8889	High Similarity	NPC472409
0.8881	High Similarity	NPC470671
0.8881	High Similarity	NPC470399
0.8881	High Similarity	NPC470672
0.8881	High Similarity	NPC474487
0.8881	High Similarity	NPC474504
0.8881	High Similarity	NPC188947
0.8881	High Similarity	NPC201395
0.8881	High Similarity	NPC57380
0.8881	High Similarity	NPC280284
0.8881	High Similarity	NPC99333
0.8872	High Similarity	NPC281917
0.8872	High Similarity	NPC256042
0.8872	High Similarity	NPC216361
0.8872	High Similarity	NPC187432
0.8872	High Similarity	NPC116775
0.8872	High Similarity	NPC472516
0.8864	High Similarity	NPC286336
0.8864	High Similarity	NPC66705
0.8855	High Similarity	NPC212631
0.8855	High Similarity	NPC257756
0.8855	High Similarity	NPC205468
0.8855	High Similarity	NPC87231
0.8855	High Similarity	NPC129132
0.8846	High Similarity	NPC324482
0.8837	High Similarity	NPC230818
0.8837	High Similarity	NPC60558
0.8832	High Similarity	NPC113089
0.8832	High Similarity	NPC158874
0.8832	High Similarity	NPC59522
0.8832	High Similarity	NPC189650
0.8824	High Similarity	NPC205006
0.8824	High Similarity	NPC156590
0.8824	High Similarity	NPC118840
0.8824	High Similarity	NPC147688
0.8824	High Similarity	NPC17170

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 NPC473907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	1027
0.2-0.3	1637
0.3-0.4	2793
0.4-0.5	1762
0.5-0.6	1048
0.6-0.7	332
0.7-0.8	109
0.8-0.85	33
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.916	High Similarity	NPD2796	Approved
0.8806	High Similarity	NPD1552	Clinical (unspecified phase)
0.8806	High Similarity	NPD1550	Clinical (unspecified phase)
0.8779	High Similarity	NPD1240	Approved
0.8768	High Similarity	NPD4378	Clinical (unspecified phase)
0.8741	High Similarity	NPD1549	Phase 2
0.8696	High Similarity	NPD6799	Approved
0.8676	High Similarity	NPD1243	Approved
0.8657	High Similarity	NPD1510	Phase 2
0.8647	High Similarity	NPD1607	Approved
0.8603	High Similarity	NPD970	Clinical (unspecified phase)
0.85	High Similarity	NPD7410	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD1511	Approved
0.8406	Intermediate Similarity	NPD2654	Approved
0.838	Intermediate Similarity	NPD920	Approved
0.8357	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.831	Intermediate Similarity	NPD1512	Approved
0.8288	Intermediate Similarity	NPD2801	Approved
0.8276	Intermediate Similarity	NPD7411	Suspended
0.8248	Intermediate Similarity	NPD3748	Approved
0.8239	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD3817	Phase 2
0.8219	Intermediate Similarity	NPD6801	Discontinued
0.8195	Intermediate Similarity	NPD6832	Phase 2
0.8163	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD7819	Suspended
0.8143	Intermediate Similarity	NPD2800	Approved
0.8108	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD6651	Approved
0.8095	Intermediate Similarity	NPD1934	Approved
0.8082	Intermediate Similarity	NPD4380	Phase 2
0.808	Intermediate Similarity	NPD1241	Discontinued
0.8077	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD1296	Phase 2
0.8058	Intermediate Similarity	NPD1551	Phase 2
0.8054	Intermediate Similarity	NPD3882	Suspended
0.8015	Intermediate Similarity	NPD9717	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD5401	Approved
0.7958	Intermediate Similarity	NPD3750	Approved
0.7958	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD919	Approved
0.7939	Intermediate Similarity	NPD422	Phase 1
0.791	Intermediate Similarity	NPD1019	Discontinued
0.7895	Intermediate Similarity	NPD5494	Approved
0.7887	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1247	Approved
0.7836	Intermediate Similarity	NPD1203	Approved
0.7794	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3972	Approved
0.7742	Intermediate Similarity	NPD3926	Phase 2
0.774	Intermediate Similarity	NPD2534	Approved
0.774	Intermediate Similarity	NPD2532	Approved
0.774	Intermediate Similarity	NPD2533	Approved
0.773	Intermediate Similarity	NPD2799	Discontinued
0.7727	Intermediate Similarity	NPD6959	Discontinued
0.7704	Intermediate Similarity	NPD3267	Approved
0.7704	Intermediate Similarity	NPD3266	Approved
0.7697	Intermediate Similarity	NPD7768	Phase 2
0.7692	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6166	Phase 2
0.7692	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7054	Approved
0.7647	Intermediate Similarity	NPD2798	Approved
0.7647	Intermediate Similarity	NPD3749	Approved
0.7643	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1933	Approved
0.7634	Intermediate Similarity	NPD1548	Phase 1
0.7632	Intermediate Similarity	NPD5402	Approved
0.7622	Intermediate Similarity	NPD2344	Approved
0.761	Intermediate Similarity	NPD7472	Approved
0.7595	Intermediate Similarity	NPD3818	Discontinued
0.758	Intermediate Similarity	NPD2403	Approved
0.7571	Intermediate Similarity	NPD3140	Approved
0.7571	Intermediate Similarity	NPD3142	Approved
0.7562	Intermediate Similarity	NPD6797	Phase 2
0.7554	Intermediate Similarity	NPD2313	Discontinued
0.7554	Intermediate Similarity	NPD3268	Approved
0.7552	Intermediate Similarity	NPD6100	Approved
0.7552	Intermediate Similarity	NPD2935	Discontinued
0.7552	Intermediate Similarity	NPD6099	Approved
0.7519	Intermediate Similarity	NPD17	Approved
0.7517	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD9545	Approved
0.7483	Intermediate Similarity	NPD7033	Discontinued
0.7481	Intermediate Similarity	NPD9493	Approved
0.7469	Intermediate Similarity	NPD7808	Phase 3
0.7469	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4628	Phase 3
0.7453	Intermediate Similarity	NPD5953	Discontinued
0.7447	Intermediate Similarity	NPD943	Approved
0.7447	Intermediate Similarity	NPD4307	Phase 2
0.7445	Intermediate Similarity	NPD2797	Approved
0.7438	Intermediate Similarity	NPD7286	Phase 2
0.7429	Intermediate Similarity	NPD411	Approved
0.7415	Intermediate Similarity	NPD2309	Approved
0.7394	Intermediate Similarity	NPD230	Phase 1
0.7394	Intermediate Similarity	NPD447	Suspended
0.7379	Intermediate Similarity	NPD1471	Phase 3
0.7372	Intermediate Similarity	NPD3225	Approved
0.7362	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1608	Approved
0.7347	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6232	Discontinued
0.7312	Intermediate Similarity	NPD7473	Discontinued
0.7301	Intermediate Similarity	NPD6104	Discontinued
0.7286	Intermediate Similarity	NPD4908	Phase 1
0.7279	Intermediate Similarity	NPD1652	Phase 2
0.7279	Intermediate Similarity	NPD1610	Phase 2
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1876	Approved
0.7241	Intermediate Similarity	NPD4308	Phase 3
0.7208	Intermediate Similarity	NPD5889	Approved
0.7208	Intermediate Similarity	NPD5890	Approved
0.7195	Intermediate Similarity	NPD6559	Discontinued
0.719	Intermediate Similarity	NPD3226	Approved
0.7183	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3887	Approved
0.7179	Intermediate Similarity	NPD4288	Approved
0.7178	Intermediate Similarity	NPD1729	Discontinued
0.7165	Intermediate Similarity	NPD9697	Approved
0.7161	Intermediate Similarity	NPD6280	Approved
0.7161	Intermediate Similarity	NPD6279	Approved
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD9261	Approved
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD6585	Discontinued
0.7132	Intermediate Similarity	NPD1778	Approved
0.7125	Intermediate Similarity	NPD5710	Approved
0.7125	Intermediate Similarity	NPD5711	Approved
0.7123	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5844	Phase 1
0.7115	Intermediate Similarity	NPD1465	Phase 2
0.7086	Intermediate Similarity	NPD7390	Discontinued
0.707	Intermediate Similarity	NPD5353	Approved
0.7063	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD1651	Approved
0.7055	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1358	Approved
0.705	Intermediate Similarity	NPD4749	Approved
0.7045	Intermediate Similarity	NPD5535	Approved
0.7039	Intermediate Similarity	NPD4662	Approved
0.7039	Intermediate Similarity	NPD4661	Approved
0.7035	Intermediate Similarity	NPD4360	Phase 2
0.7035	Intermediate Similarity	NPD4363	Phase 3
0.703	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6808	Phase 2
0.6994	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4361	Phase 2
0.6993	Remote Similarity	NPD2186	Approved
0.6987	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1894	Discontinued
0.6978	Remote Similarity	NPD1481	Phase 2
0.6977	Remote Similarity	NPD3134	Approved
0.6972	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2354	Approved
0.6943	Remote Similarity	NPD6844	Discontinued
0.6928	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9263	Approved
0.6923	Remote Similarity	NPD9264	Approved
0.6923	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9267	Approved
0.6918	Remote Similarity	NPD6355	Discontinued
0.6912	Remote Similarity	NPD5536	Phase 2
0.6908	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1535	Discovery
0.6897	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD6971	Discontinued
0.6871	Remote Similarity	NPD5242	Approved
0.687	Remote Similarity	NPD74	Approved
0.687	Remote Similarity	NPD2684	Approved
0.687	Remote Similarity	NPD9266	Approved
0.6867	Remote Similarity	NPD2424	Discontinued
0.6863	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2296	Approved
0.6853	Remote Similarity	NPD9494	Approved
0.6853	Remote Similarity	NPD3018	Phase 2
0.6852	Remote Similarity	NPD7199	Phase 2
0.6849	Remote Similarity	NPD1613	Approved
0.6849	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3496	Discontinued
0.6828	Remote Similarity	NPD6410	Clinical (unspecified phase)

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