NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.03
Volume:	242.021
LogP:	1.781
LogD:	1.104
LogS:	-3.291
# Rotatable Bonds:	0
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	2.541
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.206
MDCK Permeability:	7.757450475764927e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.268
20% Bioavailability (F20%):	0.315
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	94.8549575805664%
Volume Distribution (VD):	0.61
Pgp-substrate:	12.333170890808105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.945
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.546
CYP2C9-substrate:	0.515
CYP2D6-inhibitor:	0.312
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	5.957
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.767
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.207
Skin Sensitization:	0.937
Carcinogencity:	0.306
Eye Corrosion:	0.105
Eye Irritation:	0.937
Respiratory Toxicity:	0.172

Download Data

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

Natural Product: NPC251110

Natural Product ID:	NPC251110
*Common Name:**	1,2,3,5-Tetrahydroxyxanthone
IUPAC Name:	1,2,3,5-tetrahydroxyxanthen-9-one
Synonyms:	1,2,3,5-Tetrahydroxyxanthone
Standard InCHIKey:	PGCJOTJPPYIRHQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O6/c14-6-3-1-2-5-10(16)9-8(19-13(5)6)4-7(15)11(17)12(9)18/h1-4,14-15,17-18H
SMILES:	Oc1cc2oc3c(O)cccc3c(=O)c2c(c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2029866
PubChem CID:	60168075
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
NPO32798	polygala karensium	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22552195]

☑ 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	4
Others	1

Activity Type	# Activity
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	13.68	ug.mL-1	PMID[449676]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	19.81	ug.mL-1	PMID[449676]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	26.87	ug.mL-1	PMID[449676]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	10.8	ug.mL-1	PMID[449676]
NPT2	Others	Unspecified		Ratio IC50	=	243.0	n.a.	PMID[449676]

☑ 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 NPC251110 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	588
0.1-0.2	2324
0.2-0.3	6102
0.3-0.4	11571
0.4-0.5	4598
0.5-0.6	4286
0.6-0.7	5206
0.7-0.8	4747
0.8-0.85	1653
0.85-0.9	918
0.9-0.95	455
0.95-1	249

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC248102
0.9931	High Similarity	NPC61620
0.9863	High Similarity	NPC271779
0.9863	High Similarity	NPC88645
0.9863	High Similarity	NPC167091
0.9863	High Similarity	NPC292214
0.9863	High Similarity	NPC206238
0.9795	High Similarity	NPC161277
0.9795	High Similarity	NPC101996
0.9795	High Similarity	NPC180234
0.9795	High Similarity	NPC120537
0.9795	High Similarity	NPC199100
0.9795	High Similarity	NPC39007
0.9793	High Similarity	NPC45873
0.9792	High Similarity	NPC276930
0.9792	High Similarity	NPC272721
0.9792	High Similarity	NPC43669
0.9792	High Similarity	NPC194856
0.9792	High Similarity	NPC196277
0.9726	High Similarity	NPC149614
0.9726	High Similarity	NPC171010
0.9724	High Similarity	NPC216318
0.9724	High Similarity	NPC17286
0.9724	High Similarity	NPC259713
0.9724	High Similarity	NPC296197
0.9722	High Similarity	NPC77378
0.9722	High Similarity	NPC207729
0.9664	High Similarity	NPC99597
0.9664	High Similarity	NPC210084
0.9662	High Similarity	NPC2928
0.9658	High Similarity	NPC62042
0.9658	High Similarity	NPC29231
0.9658	High Similarity	NPC179183
0.9655	High Similarity	NPC118726
0.9655	High Similarity	NPC12367
0.9597	High Similarity	NPC68093
0.9597	High Similarity	NPC255106
0.9597	High Similarity	NPC138243
0.9597	High Similarity	NPC472916
0.9597	High Similarity	NPC235165
0.9597	High Similarity	NPC191146
0.9592	High Similarity	NPC204515
0.9592	High Similarity	NPC117579
0.9592	High Similarity	NPC225731
0.9589	High Similarity	NPC294502
0.9589	High Similarity	NPC200221
0.9586	High Similarity	NPC130230
0.9586	High Similarity	NPC168803
0.9586	High Similarity	NPC275772
0.9586	High Similarity	NPC239312
0.9533	High Similarity	NPC222814
0.9533	High Similarity	NPC472914
0.9533	High Similarity	NPC96167
0.9533	High Similarity	NPC474836
0.9533	High Similarity	NPC36852
0.9533	High Similarity	NPC162869
0.9533	High Similarity	NPC262286
0.9533	High Similarity	NPC48208
0.9533	High Similarity	NPC472913
0.9533	High Similarity	NPC245758
0.9533	High Similarity	NPC475267
0.9533	High Similarity	NPC474208
0.9533	High Similarity	NPC156057
0.9533	High Similarity	NPC472910
0.9533	High Similarity	NPC472911
0.9533	High Similarity	NPC78225
0.953	High Similarity	NPC20830
0.953	High Similarity	NPC256612
0.9527	High Similarity	NPC131624
0.9527	High Similarity	NPC27208
0.9527	High Similarity	NPC256283
0.9527	High Similarity	NPC71334
0.9527	High Similarity	NPC120163
0.9527	High Similarity	NPC188203
0.9527	High Similarity	NPC275836
0.9527	High Similarity	NPC275722
0.9527	High Similarity	NPC100887
0.9527	High Similarity	NPC222830
0.9527	High Similarity	NPC25270
0.9527	High Similarity	NPC212678
0.9527	High Similarity	NPC239128
0.9527	High Similarity	NPC198826
0.9527	High Similarity	NPC293183
0.9527	High Similarity	NPC187498
0.9527	High Similarity	NPC83508
0.9527	High Similarity	NPC57030
0.9527	High Similarity	NPC241498
0.9527	High Similarity	NPC301323
0.9527	High Similarity	NPC162313
0.9527	High Similarity	NPC156222
0.9521	High Similarity	NPC183655
0.9521	High Similarity	NPC287395
0.9514	High Similarity	NPC59551
0.9474	High Similarity	NPC308992
0.9474	High Similarity	NPC162668
0.9474	High Similarity	NPC167678
0.9474	High Similarity	NPC29876
0.9467	High Similarity	NPC474638
0.9467	High Similarity	NPC274730
0.9467	High Similarity	NPC201837
0.9463	High Similarity	NPC70433
0.9463	High Similarity	NPC47781
0.9463	High Similarity	NPC49402
0.9463	High Similarity	NPC22519
0.9463	High Similarity	NPC176775
0.9463	High Similarity	NPC33051
0.9463	High Similarity	NPC160951
0.9463	High Similarity	NPC274327
0.9463	High Similarity	NPC227337
0.9463	High Similarity	NPC231018
0.9463	High Similarity	NPC255350
0.9463	High Similarity	NPC472915
0.9463	High Similarity	NPC145379
0.9463	High Similarity	NPC69394
0.9463	High Similarity	NPC183878
0.9463	High Similarity	NPC273462
0.9459	High Similarity	NPC31363
0.9459	High Similarity	NPC202157
0.9456	High Similarity	NPC195351
0.9456	High Similarity	NPC1612
0.9456	High Similarity	NPC183959
0.9452	High Similarity	NPC46941
0.9448	High Similarity	NPC70136
0.9444	High Similarity	NPC169479
0.9444	High Similarity	NPC159855
0.9412	High Similarity	NPC83922
0.9412	High Similarity	NPC472448
0.9408	High Similarity	NPC139036
0.9408	High Similarity	NPC476980
0.9408	High Similarity	NPC204290
0.9408	High Similarity	NPC263449
0.9404	High Similarity	NPC299520
0.9404	High Similarity	NPC300727
0.9404	High Similarity	NPC181960
0.9404	High Similarity	NPC469584
0.9404	High Similarity	NPC129684
0.9404	High Similarity	NPC241904
0.94	High Similarity	NPC196439
0.94	High Similarity	NPC117992
0.94	High Similarity	NPC138360
0.94	High Similarity	NPC37392
0.94	High Similarity	NPC92659
0.94	High Similarity	NPC50715
0.94	High Similarity	NPC113906
0.94	High Similarity	NPC4455
0.94	High Similarity	NPC57674
0.94	High Similarity	NPC213622
0.94	High Similarity	NPC2476
0.94	High Similarity	NPC44079
0.94	High Similarity	NPC230149
0.94	High Similarity	NPC280339
0.94	High Similarity	NPC167815
0.94	High Similarity	NPC201136
0.94	High Similarity	NPC163780
0.94	High Similarity	NPC26227
0.94	High Similarity	NPC128863
0.94	High Similarity	NPC208197
0.94	High Similarity	NPC201451
0.94	High Similarity	NPC183597
0.94	High Similarity	NPC472909
0.94	High Similarity	NPC168247
0.94	High Similarity	NPC146165
0.94	High Similarity	NPC227325
0.94	High Similarity	NPC152951
0.9396	High Similarity	NPC477231
0.9396	High Similarity	NPC121522
0.9396	High Similarity	NPC216769
0.9396	High Similarity	NPC257648
0.9396	High Similarity	NPC181209
0.9396	High Similarity	NPC100971
0.9396	High Similarity	NPC291802
0.9396	High Similarity	NPC75069
0.9396	High Similarity	NPC39732
0.9396	High Similarity	NPC209487
0.9396	High Similarity	NPC302950
0.9396	High Similarity	NPC236637
0.9396	High Similarity	NPC131266
0.9396	High Similarity	NPC269451
0.9396	High Similarity	NPC219582
0.9396	High Similarity	NPC245382
0.9396	High Similarity	NPC142540
0.9396	High Similarity	NPC60972
0.9396	High Similarity	NPC100263
0.9396	High Similarity	NPC35763
0.9392	High Similarity	NPC77858
0.9392	High Similarity	NPC184136
0.9392	High Similarity	NPC306821
0.9392	High Similarity	NPC151473
0.9388	High Similarity	NPC294852
0.9388	High Similarity	NPC218490
0.9388	High Similarity	NPC321011
0.9388	High Similarity	NPC188679
0.9384	High Similarity	NPC209278
0.9384	High Similarity	NPC231013
0.9379	High Similarity	NPC279121
0.9346	High Similarity	NPC258331
0.9346	High Similarity	NPC266314
0.9346	High Similarity	NPC259456
0.9342	High Similarity	NPC172770
0.9342	High Similarity	NPC476242

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 NPC251110 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	507
0.1-0.2	1069
0.2-0.3	2006
0.3-0.4	2680
0.4-0.5	1551
0.5-0.6	920
0.6-0.7	280
0.7-0.8	91
0.8-0.85	27
0.85-0.9	12
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9463	High Similarity	NPD2801	Approved
0.9396	High Similarity	NPD1934	Approved
0.9379	High Similarity	NPD1511	Approved
0.9252	High Similarity	NPD1512	Approved
0.9079	High Similarity	NPD2393	Clinical (unspecified phase)
0.8961	High Similarity	NPD3882	Suspended
0.8812	High Similarity	NPD3818	Discontinued
0.8805	High Similarity	NPD6167	Clinical (unspecified phase)
0.8805	High Similarity	NPD6166	Phase 2
0.8805	High Similarity	NPD6168	Clinical (unspecified phase)
0.8776	High Similarity	NPD1549	Phase 2
0.8718	High Similarity	NPD4868	Clinical (unspecified phase)
0.871	High Similarity	NPD1465	Phase 2
0.8707	High Similarity	NPD1552	Clinical (unspecified phase)
0.8707	High Similarity	NPD1550	Clinical (unspecified phase)
0.8681	High Similarity	NPD943	Approved
0.8671	High Similarity	NPD5494	Approved
0.8659	High Similarity	NPD4338	Clinical (unspecified phase)
0.8589	High Similarity	NPD7074	Phase 3
0.8571	High Similarity	NPD1510	Phase 2
0.8535	High Similarity	NPD3817	Phase 2
0.8528	High Similarity	NPD7054	Approved
0.8516	High Similarity	NPD4380	Phase 2
0.8476	Intermediate Similarity	NPD7472	Approved
0.8431	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1240	Approved
0.8403	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6797	Phase 2
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8311	Intermediate Similarity	NPD1607	Approved
0.8272	Intermediate Similarity	NPD1247	Approved
0.8263	Intermediate Similarity	NPD7251	Discontinued
0.8239	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6232	Discontinued
0.8214	Intermediate Similarity	NPD7808	Phase 3
0.8204	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD5844	Phase 1
0.8187	Intermediate Similarity	NPD5402	Approved
0.8182	Intermediate Similarity	NPD7473	Discontinued
0.8176	Intermediate Similarity	NPD1613	Approved
0.8176	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD2796	Approved
0.8129	Intermediate Similarity	NPD6799	Approved
0.8125	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD447	Suspended
0.8086	Intermediate Similarity	NPD3749	Approved
0.8079	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD230	Phase 1
0.8	Intermediate Similarity	NPD7411	Suspended
0.7963	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3926	Phase 2
0.795	Intermediate Similarity	NPD6801	Discontinued
0.7937	Intermediate Similarity	NPD6599	Discontinued
0.7927	Intermediate Similarity	NPD919	Approved
0.7922	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD1551	Phase 2
0.7871	Intermediate Similarity	NPD2800	Approved
0.787	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6559	Discontinued
0.7831	Intermediate Similarity	NPD6959	Discontinued
0.7812	Intermediate Similarity	NPD1653	Approved
0.775	Intermediate Similarity	NPD5403	Approved
0.775	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2344	Approved
0.7736	Intermediate Similarity	NPD5401	Approved
0.7727	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3748	Approved
0.7718	Intermediate Similarity	NPD9494	Approved
0.7706	Intermediate Similarity	NPD3751	Discontinued
0.7703	Intermediate Similarity	NPD1203	Approved
0.7692	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2313	Discontinued
0.7654	Intermediate Similarity	NPD3226	Approved
0.7647	Intermediate Similarity	NPD1933	Approved
0.7643	Intermediate Similarity	NPD1243	Approved
0.764	Intermediate Similarity	NPD920	Approved
0.7628	Intermediate Similarity	NPD2346	Discontinued
0.7627	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD9269	Phase 2
0.7616	Intermediate Similarity	NPD3027	Phase 3
0.759	Intermediate Similarity	NPD7768	Phase 2
0.7564	Intermediate Similarity	NPD6099	Approved
0.7564	Intermediate Similarity	NPD6100	Approved
0.7551	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2309	Approved
0.7547	Intermediate Similarity	NPD6190	Approved
0.7541	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2532	Approved
0.7516	Intermediate Similarity	NPD2534	Approved
0.7516	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7458	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1610	Phase 2
0.7412	Intermediate Similarity	NPD7199	Phase 2
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7383	Intermediate Similarity	NPD9717	Approved
0.7375	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5953	Discontinued
0.7356	Intermediate Similarity	NPD7286	Phase 2
0.7351	Intermediate Similarity	NPD1470	Approved
0.7347	Intermediate Similarity	NPD9268	Approved
0.7326	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1548	Phase 1
0.7267	Intermediate Similarity	NPD1608	Approved
0.7261	Intermediate Similarity	NPD6651	Approved
0.7247	Intermediate Similarity	NPD8312	Approved
0.7247	Intermediate Similarity	NPD8313	Approved
0.7239	Intermediate Similarity	NPD7390	Discontinued
0.7232	Intermediate Similarity	NPD7685	Pre-registration
0.7226	Intermediate Similarity	NPD411	Approved
0.7225	Intermediate Similarity	NPD5242	Approved
0.7208	Intermediate Similarity	NPD4908	Phase 1
0.7202	Intermediate Similarity	NPD6844	Discontinued
0.7202	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD1201	Approved
0.72	Intermediate Similarity	NPD7228	Approved
0.72	Intermediate Similarity	NPD422	Phase 1
0.7197	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2798	Approved
0.7176	Intermediate Similarity	NPD4967	Phase 2
0.7176	Intermediate Similarity	NPD4966	Approved
0.7176	Intermediate Similarity	NPD4965	Approved
0.717	Intermediate Similarity	NPD4308	Phase 3
0.7166	Intermediate Similarity	NPD6777	Approved
0.7166	Intermediate Similarity	NPD6779	Approved
0.7166	Intermediate Similarity	NPD6780	Approved
0.7166	Intermediate Similarity	NPD6782	Approved
0.7166	Intermediate Similarity	NPD6776	Approved
0.7166	Intermediate Similarity	NPD6778	Approved
0.7166	Intermediate Similarity	NPD6781	Approved
0.7152	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7127	Intermediate Similarity	NPD8434	Phase 2
0.7118	Intermediate Similarity	NPD5353	Approved
0.7118	Intermediate Similarity	NPD4288	Approved
0.7115	Intermediate Similarity	NPD3268	Approved
0.7115	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3764	Approved
0.7097	Intermediate Similarity	NPD6832	Phase 2
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1535	Discovery
0.7081	Intermediate Similarity	NPD1471	Phase 3
0.7071	Intermediate Similarity	NPD2899	Discontinued
0.7069	Intermediate Similarity	NPD5710	Approved
0.7069	Intermediate Similarity	NPD5711	Approved
0.7067	Intermediate Similarity	NPD17	Approved
0.7059	Intermediate Similarity	NPD3225	Approved
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7051	Intermediate Similarity	NPD4625	Phase 3
0.7041	Intermediate Similarity	NPD6386	Approved
0.7041	Intermediate Similarity	NPD6385	Approved
0.7033	Intermediate Similarity	NPD8150	Discontinued
0.703	Intermediate Similarity	NPD4357	Discontinued
0.7018	Intermediate Similarity	NPD2296	Approved
0.7013	Intermediate Similarity	NPD2797	Approved
0.7012	Intermediate Similarity	NPD2354	Approved
0.7006	Intermediate Similarity	NPD1296	Phase 2
0.7005	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7549	Discontinued
0.6993	Remote Similarity	NPD4749	Approved
0.6989	Remote Similarity	NPD2403	Approved
0.6989	Remote Similarity	NPD4363	Phase 3
0.6989	Remote Similarity	NPD4360	Phase 2
0.6988	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5536	Phase 2
0.6977	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7697	Approved
0.6963	Remote Similarity	NPD7696	Phase 3
0.6963	Remote Similarity	NPD7698	Approved
0.6962	Remote Similarity	NPD6233	Phase 2
0.6959	Remote Similarity	NPD8151	Discontinued
0.6957	Remote Similarity	NPD7033	Discontinued
0.6943	Remote Similarity	NPD7584	Approved
0.6941	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD9545	Approved
0.6927	Remote Similarity	NPD7870	Phase 2
0.6927	Remote Similarity	NPD7871	Phase 2
0.6923	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3018	Phase 2
0.6918	Remote Similarity	NPD228	Approved
0.6918	Remote Similarity	NPD4307	Phase 2
0.6918	Remote Similarity	NPD1558	Phase 1
0.6914	Remote Similarity	NPD5406	Approved

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