NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.06
Volume:	261.953
LogP:	1.101
LogD:	0.99
LogS:	-3.697
# Rotatable Bonds:	1
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	3.357
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.206
MDCK Permeability:	9.362475793750491e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.345
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.635
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	73.50199890136719%
Volume Distribution (VD):	0.571
Pgp-substrate:	11.201512336730957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.454
CYP1A2-substrate:	0.536
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.128
CYP2C9-inhibitor:	0.296
CYP2C9-substrate:	0.833
CYP2D6-inhibitor:	0.356
CYP2D6-substrate:	0.27
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.515

ADMET: Excretion

Clearance (CL):	9.416
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.014
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.515
Rat Oral Acute Toxicity:	0.849
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.932
Carcinogencity:	0.27
Eye Corrosion:	0.003
Eye Irritation:	0.891
Respiratory Toxicity:	0.732

Download Data

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

Natural Product: NPC475076

Natural Product ID:	NPC475076
*Common Name:**	1-Methoxy-2,5,7-Trihydroxyxanthone
IUPAC Name:	2,5,7-trihydroxy-1-methoxy-4a,9a-dihydroxanthen-9-one
Synonyms:
Standard InCHIKey:	QFLSYBURRGPQJZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O6/c1-19-14-8(16)2-3-10-11(14)12(18)7-4-6(15)5-9(17)13(7)20-10/h2-5,10-11,15-17H,1H3
SMILES:	COC1=C(C=CC2C1C(=O)C3=C(O2)C(=CC(=C3)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495857
PubChem CID:	44583783
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO20815	Lindera fruticosa	Species	Lauraceae	Eukaryota	roots	n.a.	n.a.	PMID[16724860]
NPO20815	Lindera fruticosa	Species	Lauraceae	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
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	7.0	%	PMID[530165]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	524000.0	nM	PMID[530165]

☑ 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 NPC475076 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	399
0.1-0.2	1446
0.2-0.3	4129
0.3-0.4	9585
0.4-0.5	8806
0.5-0.6	3458
0.6-0.7	5264
0.7-0.8	6645
0.8-0.85	2177
0.85-0.9	716
0.9-0.95	71
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9589	High Similarity	NPC294502
0.9589	High Similarity	NPC200221
0.9452	High Similarity	NPC46941
0.9404	High Similarity	NPC99597
0.9404	High Similarity	NPC210084
0.9384	High Similarity	NPC209278
0.9338	High Similarity	NPC255106
0.9338	High Similarity	NPC235165
0.9333	High Similarity	NPC271779
0.9333	High Similarity	NPC206238
0.9333	High Similarity	NPC88645
0.9333	High Similarity	NPC167091
0.9333	High Similarity	NPC292214
0.9276	High Similarity	NPC156057
0.9276	High Similarity	NPC222814
0.9276	High Similarity	NPC475267
0.9276	High Similarity	NPC472910
0.9276	High Similarity	NPC474836
0.9276	High Similarity	NPC48208
0.9276	High Similarity	NPC245758
0.9276	High Similarity	NPC162869
0.9276	High Similarity	NPC474208
0.9276	High Similarity	NPC472911
0.9276	High Similarity	NPC472913
0.9276	High Similarity	NPC96167
0.9276	High Similarity	NPC472914
0.9272	High Similarity	NPC2928
0.9267	High Similarity	NPC39007
0.9267	High Similarity	NPC161277
0.9267	High Similarity	NPC75069
0.9267	High Similarity	NPC180234
0.9267	High Similarity	NPC101996
0.9267	High Similarity	NPC120537
0.9267	High Similarity	NPC199100
0.9247	High Similarity	NPC59551
0.9221	High Similarity	NPC308992
0.9211	High Similarity	NPC472916
0.9211	High Similarity	NPC317383
0.92	High Similarity	NPC149614
0.92	High Similarity	NPC251110
0.92	High Similarity	NPC171010
0.92	High Similarity	NPC204515
0.9156	High Similarity	NPC263449
0.915	High Similarity	NPC129684
0.915	High Similarity	NPC181960
0.915	High Similarity	NPC469584
0.915	High Similarity	NPC299520
0.9145	High Similarity	NPC37392
0.9145	High Similarity	NPC472909
0.9139	High Similarity	NPC219582
0.9139	High Similarity	NPC236637
0.9139	High Similarity	NPC302950
0.9133	High Similarity	NPC248102
0.9133	High Similarity	NPC179183
0.9133	High Similarity	NPC61620
0.9133	High Similarity	NPC62042
0.9133	High Similarity	NPC29231
0.9128	High Similarity	NPC191634
0.9097	High Similarity	NPC266314
0.9091	High Similarity	NPC250214
0.9091	High Similarity	NPC95936
0.9085	High Similarity	NPC201837
0.9079	High Similarity	NPC469550
0.9079	High Similarity	NPC18727
0.9079	High Similarity	NPC472915
0.9073	High Similarity	NPC117579
0.9073	High Similarity	NPC31363
0.9067	High Similarity	NPC1612
0.9067	High Similarity	NPC183959
0.906	High Similarity	NPC30647
0.906	High Similarity	NPC61871
0.906	High Similarity	NPC55557
0.9054	High Similarity	NPC472917
0.9041	High Similarity	NPC145673
0.9026	High Similarity	NPC36852
0.9026	High Similarity	NPC470402
0.9026	High Similarity	NPC291508
0.9026	High Similarity	NPC223787
0.9026	High Similarity	NPC262286
0.9026	High Similarity	NPC78225
0.9026	High Similarity	NPC52530
0.902	High Similarity	NPC31018
0.902	High Similarity	NPC255807
0.902	High Similarity	NPC20830
0.902	High Similarity	NPC256612
0.902	High Similarity	NPC213622
0.9013	High Similarity	NPC269451
0.9013	High Similarity	NPC100263
0.9013	High Similarity	NPC188203
0.9013	High Similarity	NPC472912
0.9013	High Similarity	NPC156222
0.9013	High Similarity	NPC239128
0.9013	High Similarity	NPC241498
0.9013	High Similarity	NPC257648
0.9013	High Similarity	NPC209487
0.9013	High Similarity	NPC100971
0.9013	High Similarity	NPC121522
0.9013	High Similarity	NPC131266
0.9013	High Similarity	NPC198826
0.9013	High Similarity	NPC83508
0.9013	High Similarity	NPC100887
0.9013	High Similarity	NPC301323
0.9013	High Similarity	NPC35763
0.9013	High Similarity	NPC212678
0.9013	High Similarity	NPC260979
0.9013	High Similarity	NPC181209
0.9013	High Similarity	NPC256283
0.9013	High Similarity	NPC25270
0.9013	High Similarity	NPC71334
0.9013	High Similarity	NPC222830
0.9013	High Similarity	NPC275836
0.9013	High Similarity	NPC291802
0.9013	High Similarity	NPC216769
0.9013	High Similarity	NPC275722
0.9013	High Similarity	NPC477231
0.9013	High Similarity	NPC57030
0.9013	High Similarity	NPC293183
0.9013	High Similarity	NPC162313
0.9013	High Similarity	NPC120163
0.9013	High Similarity	NPC187498
0.9013	High Similarity	NPC245382
0.9013	High Similarity	NPC131624
0.9007	High Similarity	NPC45873
0.9	High Similarity	NPC188679
0.9	High Similarity	NPC43669
0.9	High Similarity	NPC196277
0.9	High Similarity	NPC183655
0.9	High Similarity	NPC276930
0.9	High Similarity	NPC321011
0.9	High Similarity	NPC294852
0.9	High Similarity	NPC194856
0.9	High Similarity	NPC272721
0.9	High Similarity	NPC287395
0.8993	High Similarity	NPC226987
0.8993	High Similarity	NPC143903
0.8968	High Similarity	NPC152904
0.8968	High Similarity	NPC55738
0.8961	High Similarity	NPC191146
0.8961	High Similarity	NPC138243
0.8961	High Similarity	NPC291878
0.8961	High Similarity	NPC195796
0.8961	High Similarity	NPC474638
0.8961	High Similarity	NPC35038
0.8961	High Similarity	NPC13858
0.8961	High Similarity	NPC68093
0.8961	High Similarity	NPC278778
0.8961	High Similarity	NPC320825
0.8961	High Similarity	NPC326037
0.8954	High Similarity	NPC274327
0.8954	High Similarity	NPC124714
0.8954	High Similarity	NPC255350
0.8954	High Similarity	NPC47781
0.8954	High Similarity	NPC145379
0.8954	High Similarity	NPC160951
0.8954	High Similarity	NPC280937
0.8954	High Similarity	NPC176775
0.8954	High Similarity	NPC231018
0.8954	High Similarity	NPC246328
0.8954	High Similarity	NPC256346
0.8954	High Similarity	NPC183878
0.8954	High Similarity	NPC22519
0.8954	High Similarity	NPC69394
0.8954	High Similarity	NPC325028
0.8954	High Similarity	NPC27532
0.8947	High Similarity	NPC19980
0.8947	High Similarity	NPC45291
0.8947	High Similarity	NPC207346
0.8947	High Similarity	NPC46564
0.894	High Similarity	NPC105512
0.894	High Similarity	NPC17286
0.894	High Similarity	NPC259713
0.894	High Similarity	NPC216318
0.894	High Similarity	NPC296197
0.8933	High Similarity	NPC207729
0.8933	High Similarity	NPC77378
0.8931	High Similarity	NPC243877
0.8931	High Similarity	NPC14662
0.8924	High Similarity	NPC224280
0.8924	High Similarity	NPC234052
0.8917	High Similarity	NPC83922
0.8917	High Similarity	NPC81679
0.8917	High Similarity	NPC472448
0.891	High Similarity	NPC476980
0.8904	High Similarity	NPC18457
0.8903	High Similarity	NPC471479
0.8903	High Similarity	NPC474055
0.8903	High Similarity	NPC300727
0.8903	High Similarity	NPC472598
0.8903	High Similarity	NPC67876
0.8903	High Similarity	NPC471515
0.8903	High Similarity	NPC241904
0.8903	High Similarity	NPC27337
0.8896	High Similarity	NPC152951
0.8896	High Similarity	NPC50715
0.8896	High Similarity	NPC117992
0.8896	High Similarity	NPC201136
0.8896	High Similarity	NPC39184
0.8896	High Similarity	NPC230149
0.8896	High Similarity	NPC128863
0.8896	High Similarity	NPC201451

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 NPC475076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	895
0.2-0.3	1869
0.3-0.4	2637
0.4-0.5	1761
0.5-0.6	1021
0.6-0.7	467
0.7-0.8	130
0.8-0.85	18
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9139	High Similarity	NPD1934	Approved
0.8954	High Similarity	NPD2801	Approved
0.8831	High Similarity	NPD2393	Clinical (unspecified phase)
0.8609	High Similarity	NPD1511	Approved
0.8599	High Similarity	NPD3882	Suspended
0.8571	High Similarity	NPD6167	Clinical (unspecified phase)
0.8571	High Similarity	NPD6166	Phase 2
0.8571	High Similarity	NPD6168	Clinical (unspecified phase)
0.8553	High Similarity	NPD5494	Approved
0.8497	Intermediate Similarity	NPD1512	Approved
0.8466	Intermediate Similarity	NPD3818	Discontinued
0.84	Intermediate Similarity	NPD1549	Phase 2
0.8365	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7074	Phase 3
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7054	Approved
0.8302	Intermediate Similarity	NPD5402	Approved
0.8253	Intermediate Similarity	NPD7472	Approved
0.8243	Intermediate Similarity	NPD447	Suspended
0.8187	Intermediate Similarity	NPD3817	Phase 2
0.8165	Intermediate Similarity	NPD4380	Phase 2
0.8095	Intermediate Similarity	NPD6797	Phase 2
0.8086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7075	Discontinued
0.8079	Intermediate Similarity	NPD1510	Phase 2
0.8054	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1613	Approved
0.8049	Intermediate Similarity	NPD1247	Approved
0.8047	Intermediate Similarity	NPD7251	Discontinued
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7808	Phase 3
0.7976	Intermediate Similarity	NPD5844	Phase 1
0.7962	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD943	Approved
0.7933	Intermediate Similarity	NPD1240	Approved
0.7925	Intermediate Similarity	NPD1653	Approved
0.7908	Intermediate Similarity	NPD2796	Approved
0.7908	Intermediate Similarity	NPD1551	Phase 2
0.7905	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD230	Phase 1
0.7862	Intermediate Similarity	NPD5403	Approved
0.7857	Intermediate Similarity	NPD7473	Discontinued
0.7853	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5401	Approved
0.7838	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6559	Discontinued
0.7829	Intermediate Similarity	NPD1607	Approved
0.7821	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7785	Intermediate Similarity	NPD6799	Approved
0.7784	Intermediate Similarity	NPD6232	Discontinued
0.773	Intermediate Similarity	NPD6801	Discontinued
0.7711	Intermediate Similarity	NPD919	Approved
0.7707	Intermediate Similarity	NPD3750	Approved
0.7707	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2935	Discontinued
0.7671	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7411	Suspended
0.7661	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1933	Approved
0.7643	Intermediate Similarity	NPD2800	Approved
0.7627	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6959	Discontinued
0.7616	Intermediate Similarity	NPD3027	Phase 3
0.7613	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6599	Discontinued
0.7602	Intermediate Similarity	NPD3751	Discontinued
0.76	Intermediate Similarity	NPD9494	Approved
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD9717	Approved
0.7485	Intermediate Similarity	NPD7768	Phase 2
0.7467	Intermediate Similarity	NPD1203	Approved
0.7452	Intermediate Similarity	NPD6099	Approved
0.7452	Intermediate Similarity	NPD6100	Approved
0.7451	Intermediate Similarity	NPD2313	Discontinued
0.7443	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD8312	Approved
0.744	Intermediate Similarity	NPD3749	Approved
0.7439	Intermediate Similarity	NPD3226	Approved
0.7423	Intermediate Similarity	NPD920	Approved
0.741	Intermediate Similarity	NPD6844	Discontinued
0.7407	Intermediate Similarity	NPD2533	Approved
0.7407	Intermediate Similarity	NPD2534	Approved
0.7407	Intermediate Similarity	NPD2532	Approved
0.7389	Intermediate Similarity	NPD3748	Approved
0.7384	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD411	Approved
0.7333	Intermediate Similarity	NPD4749	Approved
0.7317	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1610	Phase 2
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD37	Approved
0.7301	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7261	Intermediate Similarity	NPD6651	Approved
0.7258	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD8150	Discontinued
0.7222	Intermediate Similarity	NPD6190	Approved
0.7219	Intermediate Similarity	NPD5353	Approved
0.7219	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7199	Phase 2
0.7208	Intermediate Similarity	NPD6832	Phase 2
0.7208	Intermediate Similarity	NPD4908	Phase 1
0.7205	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1243	Approved
0.719	Intermediate Similarity	NPD2798	Approved
0.719	Intermediate Similarity	NPD1019	Discontinued
0.7188	Intermediate Similarity	NPD2344	Approved
0.7178	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD9269	Phase 2
0.7143	Intermediate Similarity	NPD9493	Approved
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1470	Approved
0.7115	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1652	Phase 2
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD422	Phase 1
0.7079	Intermediate Similarity	NPD5953	Discontinued
0.7076	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6782	Approved
0.7074	Intermediate Similarity	NPD6777	Approved
0.7074	Intermediate Similarity	NPD6779	Approved
0.7074	Intermediate Similarity	NPD6778	Approved
0.7074	Intermediate Similarity	NPD6781	Approved
0.7074	Intermediate Similarity	NPD6780	Approved
0.7074	Intermediate Similarity	NPD6776	Approved
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7062	Intermediate Similarity	NPD7286	Phase 2
0.7055	Intermediate Similarity	NPD1241	Discontinued
0.7047	Intermediate Similarity	NPD1548	Phase 1
0.7041	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1608	Approved
0.7037	Intermediate Similarity	NPD2424	Discontinued
0.703	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2797	Approved
0.7012	Intermediate Similarity	NPD2309	Approved
0.7006	Intermediate Similarity	NPD3268	Approved
0.7	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD6823	Phase 2
0.6989	Remote Similarity	NPD2403	Approved
0.6988	Remote Similarity	NPD4662	Approved
0.6988	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4661	Approved
0.6981	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5124	Phase 1
0.6975	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1201	Approved
0.6974	Remote Similarity	NPD1091	Approved
0.6971	Remote Similarity	NPD5710	Approved
0.6971	Remote Similarity	NPD5711	Approved
0.6963	Remote Similarity	NPD7435	Discontinued
0.6962	Remote Similarity	NPD6233	Phase 2
0.6959	Remote Similarity	NPD6671	Approved
0.6957	Remote Similarity	NPD7033	Discontinued
0.6943	Remote Similarity	NPD4625	Phase 3
0.6932	Remote Similarity	NPD5242	Approved
0.6918	Remote Similarity	NPD228	Approved
0.6914	Remote Similarity	NPD8127	Discontinued
0.6908	Remote Similarity	NPD3496	Discontinued
0.69	Remote Similarity	NPD4665	Approved
0.69	Remote Similarity	NPD4111	Phase 1
0.6899	Remote Similarity	NPD6798	Discontinued
0.6899	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD4363	Phase 3
0.6898	Remote Similarity	NPD4360	Phase 2
0.6893	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD9268	Approved
0.6875	Remote Similarity	NPD7696	Phase 3
0.6875	Remote Similarity	NPD7697	Approved
0.6875	Remote Similarity	NPD7698	Approved
0.6875	Remote Similarity	NPD6355	Discontinued
0.6871	Remote Similarity	NPD7266	Discontinued
0.6859	Remote Similarity	NPD5647	Approved
0.6851	Remote Similarity	NPD7240	Approved
0.6848	Remote Similarity	NPD8166	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