NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.02
Volume:	177.876
LogP:	0.956
LogD:	1.215
LogS:	-2.676
# Rotatable Bonds:	0
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	2.68
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.832
MDCK Permeability:	6.879393822600832e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.711
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.683
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	88.34893035888672%
Volume Distribution (VD):	0.681
Pgp-substrate:	20.60480499267578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.9
CYP1A2-substrate:	0.209
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.393
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.423
CYP2D6-substrate:	0.323
CYP3A4-inhibitor:	0.255
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	11.216
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.115
Drug-inuced Liver Injury (DILI):	0.708
AMES Toxicity:	0.217
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.147
Skin Sensitization:	0.897
Carcinogencity:	0.18
Eye Corrosion:	0.721
Eye Irritation:	0.968
Respiratory Toxicity:	0.19

Download Data

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

Natural Product: NPC65060

Natural Product ID:	NPC65060
*Common Name:**	3,5,7-Trihydroxychromen-4-One
IUPAC Name:	3,5,7-trihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	OZNMEZAXFKUCPN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H6O5/c10-4-1-5(11)8-7(2-4)14-3-6(12)9(8)13/h1-3,10-12H
SMILES:	Oc1cc(O)c2c(c1)occ(c2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1093494
PubChem CID:	46886154
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
NPO31017	Polygonum orientale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31017	Polygonum orientale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[469263]

☑ 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 NPC65060 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	511
0.1-0.2	2160
0.2-0.3	6245
0.3-0.4	11460
0.4-0.5	5107
0.5-0.6	4464
0.6-0.7	5724
0.7-0.8	4235
0.8-0.85	2015
0.85-0.9	708
0.9-0.95	67
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9683	High Similarity	NPC185497
0.9603	High Similarity	NPC60558
0.9323	High Similarity	NPC25427
0.9291	High Similarity	NPC128428
0.9291	High Similarity	NPC305518
0.9254	High Similarity	NPC49242
0.9248	High Similarity	NPC299379
0.9242	High Similarity	NPC234560
0.9242	High Similarity	NPC39426
0.9237	High Similarity	NPC223457
0.9231	High Similarity	NPC475589
0.9231	High Similarity	NPC31872
0.9231	High Similarity	NPC473584
0.9219	High Similarity	NPC80694
0.9219	High Similarity	NPC186098
0.9185	High Similarity	NPC281207
0.9185	High Similarity	NPC269652
0.9173	High Similarity	NPC240147
0.9173	High Similarity	NPC256042
0.9173	High Similarity	NPC116775
0.9173	High Similarity	NPC281917
0.9173	High Similarity	NPC187432
0.9173	High Similarity	NPC193792
0.9173	High Similarity	NPC121243
0.9173	High Similarity	NPC87545
0.9173	High Similarity	NPC235428
0.9173	High Similarity	NPC216361
0.916	High Similarity	NPC25937
0.916	High Similarity	NPC212631
0.916	High Similarity	NPC129132
0.916	High Similarity	NPC257756
0.916	High Similarity	NPC205468
0.916	High Similarity	NPC87231
0.9154	High Similarity	NPC5515
0.9154	High Similarity	NPC270369
0.9147	High Similarity	NPC212379
0.9147	High Similarity	NPC69235
0.9118	High Similarity	NPC136840
0.9118	High Similarity	NPC150023
0.9111	High Similarity	NPC241838
0.9111	High Similarity	NPC143799
0.9111	High Similarity	NPC152042
0.9111	High Similarity	NPC201541
0.9104	High Similarity	NPC294409
0.9104	High Similarity	NPC162680
0.9104	High Similarity	NPC181124
0.9104	High Similarity	NPC116632
0.9104	High Similarity	NPC303644
0.9104	High Similarity	NPC212767
0.9104	High Similarity	NPC7013
0.9104	High Similarity	NPC209560
0.9098	High Similarity	NPC60667
0.9091	High Similarity	NPC263670
0.9091	High Similarity	NPC312318
0.9091	High Similarity	NPC472365
0.9091	High Similarity	NPC139813
0.9091	High Similarity	NPC175098
0.9091	High Similarity	NPC188646
0.9091	High Similarity	NPC56031
0.9091	High Similarity	NPC192304
0.9091	High Similarity	NPC242294
0.9091	High Similarity	NPC337373
0.9084	High Similarity	NPC64359
0.9084	High Similarity	NPC262359
0.9084	High Similarity	NPC313618
0.9084	High Similarity	NPC308037
0.9051	High Similarity	NPC162476
0.9044	High Similarity	NPC184536
0.9044	High Similarity	NPC146679
0.9044	High Similarity	NPC103342
0.9044	High Similarity	NPC59951
0.9044	High Similarity	NPC103904
0.9044	High Similarity	NPC230285
0.9037	High Similarity	NPC12175
0.9037	High Similarity	NPC55162
0.9037	High Similarity	NPC309154
0.9037	High Similarity	NPC90665
0.9037	High Similarity	NPC279668
0.9037	High Similarity	NPC278323
0.9023	High Similarity	NPC125920
0.9023	High Similarity	NPC286336
0.9023	High Similarity	NPC164136
0.9023	High Similarity	NPC172262
0.9023	High Similarity	NPC248872
0.9015	High Similarity	NPC10971
0.9015	High Similarity	NPC203817
0.9008	High Similarity	NPC250057
0.9	High Similarity	NPC78662
0.9	High Similarity	NPC230818
0.9	High Similarity	NPC8005
0.8986	High Similarity	NPC245482
0.8986	High Similarity	NPC301751
0.8978	High Similarity	NPC469404
0.8978	High Similarity	NPC262094
0.8978	High Similarity	NPC90582
0.8971	High Similarity	NPC469523
0.8971	High Similarity	NPC295384
0.8963	High Similarity	NPC266597
0.8963	High Similarity	NPC290291
0.8963	High Similarity	NPC188879
0.8963	High Similarity	NPC275055
0.8963	High Similarity	NPC250266
0.8963	High Similarity	NPC254841
0.8955	High Similarity	NPC84699
0.8947	High Similarity	NPC57601
0.8947	High Similarity	NPC144051
0.8947	High Similarity	NPC28753
0.8947	High Similarity	NPC82225
0.8947	High Similarity	NPC159623
0.8947	High Similarity	NPC108113
0.8947	High Similarity	NPC20560
0.8947	High Similarity	NPC213216
0.8947	High Similarity	NPC274121
0.8947	High Similarity	NPC50898
0.8947	High Similarity	NPC204960
0.8947	High Similarity	NPC18877
0.8947	High Similarity	NPC294593
0.8947	High Similarity	NPC78540
0.8947	High Similarity	NPC93756
0.8931	High Similarity	NPC42292
0.8931	High Similarity	NPC247779
0.8931	High Similarity	NPC84772
0.8931	High Similarity	NPC307732
0.8923	High Similarity	NPC293453
0.8913	High Similarity	NPC148545
0.8905	High Similarity	NPC144118
0.8905	High Similarity	NPC80962
0.8905	High Similarity	NPC101366
0.8905	High Similarity	NPC326109
0.8905	High Similarity	NPC219917
0.8905	High Similarity	NPC253822
0.8905	High Similarity	NPC204985
0.8905	High Similarity	NPC215311
0.8905	High Similarity	NPC172250
0.8905	High Similarity	NPC213659
0.8905	High Similarity	NPC48624
0.8905	High Similarity	NPC259166
0.8897	High Similarity	NPC472460
0.8897	High Similarity	NPC124269
0.8897	High Similarity	NPC188947
0.8897	High Similarity	NPC99333
0.8897	High Similarity	NPC276905
0.8897	High Similarity	NPC329225
0.8897	High Similarity	NPC280284
0.8897	High Similarity	NPC147686
0.8889	High Similarity	NPC66349
0.8889	High Similarity	NPC234133
0.8889	High Similarity	NPC127447
0.8889	High Similarity	NPC194281
0.8889	High Similarity	NPC477244
0.8889	High Similarity	NPC249606
0.8889	High Similarity	NPC186838
0.8889	High Similarity	NPC41461
0.8889	High Similarity	NPC168105
0.8889	High Similarity	NPC12165
0.8889	High Similarity	NPC231772
0.8889	High Similarity	NPC174999
0.8889	High Similarity	NPC124784
0.8889	High Similarity	NPC473887
0.8889	High Similarity	NPC1486
0.8889	High Similarity	NPC25287
0.8889	High Similarity	NPC98115
0.8889	High Similarity	NPC473391
0.8889	High Similarity	NPC29353
0.8889	High Similarity	NPC47815
0.8889	High Similarity	NPC222633
0.8889	High Similarity	NPC477243
0.8889	High Similarity	NPC472367
0.8889	High Similarity	NPC150399
0.8889	High Similarity	NPC476333
0.8889	High Similarity	NPC274109
0.8889	High Similarity	NPC477242
0.8889	High Similarity	NPC240593
0.8889	High Similarity	NPC472364
0.8881	High Similarity	NPC144027
0.8881	High Similarity	NPC236974
0.8872	High Similarity	NPC128216
0.8864	High Similarity	NPC324482
0.8857	High Similarity	NPC148011
0.8857	High Similarity	NPC229190
0.8857	High Similarity	NPC1940
0.8857	High Similarity	NPC470458
0.8849	High Similarity	NPC475705
0.8849	High Similarity	NPC95751
0.8849	High Similarity	NPC470216
0.8849	High Similarity	NPC476178
0.8849	High Similarity	NPC51887
0.8849	High Similarity	NPC158874
0.8849	High Similarity	NPC117836
0.8846	High Similarity	NPC49852
0.8846	High Similarity	NPC475496
0.8841	High Similarity	NPC52789
0.8841	High Similarity	NPC268204
0.8841	High Similarity	NPC321980
0.8841	High Similarity	NPC55832
0.8841	High Similarity	NPC470089
0.8841	High Similarity	NPC470087
0.8841	High Similarity	NPC26051
0.8837	High Similarity	NPC65041
0.8832	High Similarity	NPC471697

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 NPC65060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	472
0.1-0.2	1039
0.2-0.3	2139
0.3-0.4	2661
0.4-0.5	1552
0.5-0.6	913
0.6-0.7	251
0.7-0.8	81
0.8-0.85	32
0.85-0.9	7
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9242	High Similarity	NPD1510	Phase 2
0.9084	High Similarity	NPD1240	Approved
0.8947	High Similarity	NPD1607	Approved
0.8897	High Similarity	NPD1549	Phase 2
0.8824	High Similarity	NPD1552	Clinical (unspecified phase)
0.8824	High Similarity	NPD1550	Clinical (unspecified phase)
0.8786	High Similarity	NPD4378	Clinical (unspecified phase)
0.8623	High Similarity	NPD970	Clinical (unspecified phase)
0.8592	High Similarity	NPD1512	Approved
0.8483	Intermediate Similarity	NPD4380	Phase 2
0.8451	Intermediate Similarity	NPD6799	Approved
0.8451	Intermediate Similarity	NPD1511	Approved
0.8369	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD2796	Approved
0.8264	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1551	Phase 2
0.82	Intermediate Similarity	NPD3882	Suspended
0.8146	Intermediate Similarity	NPD7075	Discontinued
0.8146	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6651	Approved
0.8121	Intermediate Similarity	NPD6801	Discontinued
0.8121	Intermediate Similarity	NPD1934	Approved
0.8108	Intermediate Similarity	NPD6599	Discontinued
0.8067	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD2801	Approved
0.8067	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD7411	Suspended
0.8042	Intermediate Similarity	NPD2800	Approved
0.8027	Intermediate Similarity	NPD5403	Approved
0.8014	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD5401	Approved
0.8013	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3750	Approved
0.7917	Intermediate Similarity	NPD1243	Approved
0.7905	Intermediate Similarity	NPD920	Approved
0.7895	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2532	Approved
0.7891	Intermediate Similarity	NPD2533	Approved
0.7891	Intermediate Similarity	NPD2534	Approved
0.7887	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1203	Approved
0.7857	Intermediate Similarity	NPD943	Approved
0.7842	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6166	Phase 2
0.7834	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD2935	Discontinued
0.7829	Intermediate Similarity	NPD7819	Suspended
0.7803	Intermediate Similarity	NPD9545	Approved
0.7801	Intermediate Similarity	NPD230	Phase 1
0.7799	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD2654	Approved
0.7786	Intermediate Similarity	NPD9493	Approved
0.7778	Intermediate Similarity	NPD9717	Approved
0.7778	Intermediate Similarity	NPD5402	Approved
0.7736	Intermediate Similarity	NPD3818	Discontinued
0.7704	Intermediate Similarity	NPD422	Phase 1
0.7702	Intermediate Similarity	NPD6797	Phase 2
0.7677	Intermediate Similarity	NPD3749	Approved
0.7671	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1548	Phase 1
0.7654	Intermediate Similarity	NPD7251	Discontinued
0.7643	Intermediate Similarity	NPD1247	Approved
0.7643	Intermediate Similarity	NPD6959	Discontinued
0.7639	Intermediate Similarity	NPD3748	Approved
0.7639	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD919	Approved
0.7613	Intermediate Similarity	NPD7768	Phase 2
0.7613	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7808	Phase 3
0.7578	Intermediate Similarity	NPD7054	Approved
0.7574	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2344	Approved
0.7531	Intermediate Similarity	NPD7472	Approved
0.7484	Intermediate Similarity	NPD6232	Discontinued
0.7469	Intermediate Similarity	NPD7286	Phase 2
0.7465	Intermediate Similarity	NPD2313	Discontinued
0.7453	Intermediate Similarity	NPD7473	Discontinued
0.7447	Intermediate Similarity	NPD6832	Phase 2
0.7442	Intermediate Similarity	NPD74	Approved
0.7442	Intermediate Similarity	NPD9266	Approved
0.7429	Intermediate Similarity	NPD2798	Approved
0.7429	Intermediate Similarity	NPD1019	Discontinued
0.7424	Intermediate Similarity	NPD1241	Discontinued
0.7423	Intermediate Similarity	NPD7074	Phase 3
0.7391	Intermediate Similarity	NPD9269	Phase 2
0.7378	Intermediate Similarity	NPD5953	Discontinued
0.7378	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1465	Phase 2
0.7364	Intermediate Similarity	NPD9264	Approved
0.7364	Intermediate Similarity	NPD9267	Approved
0.7364	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9263	Approved
0.7358	Intermediate Similarity	NPD5494	Approved
0.7353	Intermediate Similarity	NPD9268	Approved
0.7343	Intermediate Similarity	NPD1296	Phase 2
0.7343	Intermediate Similarity	NPD411	Approved
0.7333	Intermediate Similarity	NPD2309	Approved
0.7319	Intermediate Similarity	NPD1610	Phase 2
0.731	Intermediate Similarity	NPD447	Suspended
0.7289	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2799	Discontinued
0.7267	Intermediate Similarity	NPD5711	Approved
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7267	Intermediate Similarity	NPD5710	Approved
0.7266	Intermediate Similarity	NPD3972	Approved
0.7259	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD9494	Approved
0.7237	Intermediate Similarity	NPD7390	Discontinued
0.723	Intermediate Similarity	NPD6100	Approved
0.723	Intermediate Similarity	NPD6099	Approved
0.7229	Intermediate Similarity	NPD6559	Discontinued
0.7222	Intermediate Similarity	NPD3926	Phase 2
0.7192	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3225	Approved
0.7162	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3226	Approved
0.7113	Intermediate Similarity	NPD1470	Approved
0.7113	Intermediate Similarity	NPD1164	Approved
0.7111	Intermediate Similarity	NPD9281	Approved
0.7108	Intermediate Similarity	NPD1729	Discontinued
0.7103	Intermediate Similarity	NPD3268	Approved
0.7097	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3751	Discontinued
0.7086	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4908	Phase 1
0.7073	Intermediate Similarity	NPD2403	Approved
0.7071	Intermediate Similarity	NPD1201	Approved
0.7054	Intermediate Similarity	NPD9261	Approved
0.7048	Intermediate Similarity	NPD5844	Phase 1
0.7047	Intermediate Similarity	NPD4308	Phase 3
0.7024	Intermediate Similarity	NPD6104	Discontinued
0.7021	Intermediate Similarity	NPD1481	Phase 2
0.7014	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD4288	Approved
0.6993	Remote Similarity	NPD2797	Approved
0.6986	Remote Similarity	NPD3764	Approved
0.6986	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1652	Phase 2
0.6971	Remote Similarity	NPD4363	Phase 3
0.6971	Remote Similarity	NPD4360	Phase 2
0.697	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5124	Phase 1
0.6959	Remote Similarity	NPD1933	Approved
0.6959	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2346	Discontinued
0.6954	Remote Similarity	NPD1471	Phase 3
0.695	Remote Similarity	NPD1535	Discovery
0.6939	Remote Similarity	NPD520	Approved
0.6923	Remote Similarity	NPD1876	Approved
0.6918	Remote Similarity	NPD3027	Phase 3
0.6901	Remote Similarity	NPD1608	Approved
0.6899	Remote Similarity	NPD7458	Discontinued
0.6892	Remote Similarity	NPD3142	Approved
0.6892	Remote Similarity	NPD3140	Approved
0.6883	Remote Similarity	NPD2354	Approved
0.6883	Remote Similarity	NPD6190	Approved
0.6875	Remote Similarity	NPD3266	Approved
0.6875	Remote Similarity	NPD3267	Approved
0.6871	Remote Similarity	NPD6798	Discontinued
0.6848	Remote Similarity	NPD3787	Discontinued
0.6846	Remote Similarity	NPD846	Approved
0.6846	Remote Similarity	NPD940	Approved
0.6836	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4361	Phase 2
0.6835	Remote Similarity	NPD1653	Approved
0.6824	Remote Similarity	NPD6233	Phase 2
0.6813	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5353	Approved
0.679	Remote Similarity	NPD2296	Approved
0.6786	Remote Similarity	NPD1894	Discontinued
0.6779	Remote Similarity	NPD4307	Phase 2
0.6776	Remote Similarity	NPD5408	Approved
0.6776	Remote Similarity	NPD5406	Approved
0.6776	Remote Similarity	NPD5404	Approved
0.6776	Remote Similarity	NPD5405	Approved
0.6774	Remote Similarity	NPD3887	Approved
0.677	Remote Similarity	NPD6844	Discontinued
0.6752	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4287	Approved
0.6742	Remote Similarity	NPD1237	Approved
0.6736	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4749	Approved
0.6733	Remote Similarity	NPD6355	Discontinued
0.6732	Remote Similarity	NPD2353	Approved
0.6732	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7440	Discontinued
0.6713	Remote Similarity	NPD1091	Approved
0.6712	Remote Similarity	NPD6917	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