NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.06
Volume:	241.737
LogP:	2.915
LogD:	2.663
LogS:	-3.485
# Rotatable Bonds:	1
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	2.118
Fsp3:	0.071
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:	-4.816
MDCK Permeability:	2.1538064174819738e-05
Pgp-inhibitor:	0.172
Pgp-substrate:	0.208
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.094

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	92.54865264892578%
Volume Distribution (VD):	0.559
Pgp-substrate:	10.584641456604004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.747
CYP2C19-substrate:	0.199
CYP2C9-inhibitor:	0.615
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.705
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.501
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	2.214
Half-life (T1/2):	0.562

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.764
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.822
Carcinogencity:	0.879
Eye Corrosion:	0.193
Eye Irritation:	0.981
Respiratory Toxicity:	0.259

Download Data

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

Natural Product: NPC200221

Natural Product ID:	NPC200221
*Common Name:**	2-Hydroxy-1-Methoxyxanthone
IUPAC Name:	2-hydroxy-1-methoxyxanthen-9-one
Synonyms:
Standard InCHIKey:	ATPZBKJDXXSOFC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O4/c1-17-14-9(15)6-7-11-12(14)13(16)8-4-2-3-5-10(8)18-11/h2-7,15H,1H3
SMILES:	COc1c(ccc2c1c(=O)c1ccccc1o2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923834
PubChem CID:	10399460
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
NPO40174	Kielmeyera variabilis	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26900954]
NPO18656	Iphigenia indica	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18656	Iphigenia indica	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18656	Iphigenia indica	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27687	Peliosanthes sinica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18656	Iphigenia indica	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19688	Mangifera odorata	Species	Anacardiaceae	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
MIC	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	31.3	ug.mL-1	PMID[541923]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	125.0	ug.mL-1	PMID[541923]
NPT1140	Organism	Escherichia coli ATCC 8739	Escherichia coli ATCC 8739	MIC	=	125.0	ug.mL-1	PMID[541923]
NPT1121	Organism	Moraxella catarrhalis	Moraxella catarrhalis	MIC	=	125.0	ug.mL-1	PMID[541923]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	15.6	ug.mL-1	PMID[541923]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	31.3	ug.mL-1	PMID[541923]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[541924]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[541924]
NPT1101	Organism	Staphylococcus aureus subsp. aureus RN4220	Staphylococcus aureus subsp. aureus RN4220	MIC	=	64.0	ug.mL-1	PMID[541924]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[541924]

☑ 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 NPC200221 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	502
0.1-0.2	2097
0.2-0.3	5489
0.3-0.4	11915
0.4-0.5	5034
0.5-0.6	4154
0.6-0.7	5387
0.7-0.8	4924
0.8-0.85	1710
0.85-0.9	880
0.9-0.95	468
0.95-1	137

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC294502
0.9859	High Similarity	NPC46941
0.9789	High Similarity	NPC209278
0.9726	High Similarity	NPC292214
0.9726	High Similarity	NPC167091
0.9726	High Similarity	NPC88645
0.9726	High Similarity	NPC271779
0.9726	High Similarity	NPC206238
0.9658	High Similarity	NPC75069
0.9658	High Similarity	NPC101996
0.9658	High Similarity	NPC39007
0.9658	High Similarity	NPC120537
0.9658	High Similarity	NPC199100
0.9658	High Similarity	NPC161277
0.9658	High Similarity	NPC180234
0.9648	High Similarity	NPC59551
0.9589	High Similarity	NPC171010
0.9589	High Similarity	NPC149614
0.9589	High Similarity	NPC251110
0.9589	High Similarity	NPC475076
0.953	High Similarity	NPC99597
0.953	High Similarity	NPC210084
0.9527	High Similarity	NPC2928
0.9521	High Similarity	NPC179183
0.9521	High Similarity	NPC29231
0.9521	High Similarity	NPC62042
0.9521	High Similarity	NPC61620
0.9521	High Similarity	NPC248102
0.9463	High Similarity	NPC472916
0.9463	High Similarity	NPC255106
0.9463	High Similarity	NPC235165
0.9456	High Similarity	NPC117579
0.9437	High Similarity	NPC145673
0.94	High Similarity	NPC472911
0.94	High Similarity	NPC245758
0.94	High Similarity	NPC156057
0.94	High Similarity	NPC262286
0.94	High Similarity	NPC36852
0.94	High Similarity	NPC48208
0.94	High Similarity	NPC78225
0.94	High Similarity	NPC472914
0.94	High Similarity	NPC475267
0.94	High Similarity	NPC472910
0.94	High Similarity	NPC162869
0.94	High Similarity	NPC472913
0.94	High Similarity	NPC474208
0.94	High Similarity	NPC474836
0.94	High Similarity	NPC222814
0.94	High Similarity	NPC96167
0.9396	High Similarity	NPC256612
0.9396	High Similarity	NPC20830
0.9392	High Similarity	NPC239128
0.9392	High Similarity	NPC25270
0.9392	High Similarity	NPC71334
0.9392	High Similarity	NPC256283
0.9392	High Similarity	NPC187498
0.9392	High Similarity	NPC156222
0.9392	High Similarity	NPC222830
0.9392	High Similarity	NPC188203
0.9392	High Similarity	NPC241498
0.9392	High Similarity	NPC162313
0.9392	High Similarity	NPC120163
0.9392	High Similarity	NPC293183
0.9392	High Similarity	NPC275836
0.9392	High Similarity	NPC275722
0.9392	High Similarity	NPC131624
0.9392	High Similarity	NPC301323
0.9392	High Similarity	NPC198826
0.9392	High Similarity	NPC100887
0.9392	High Similarity	NPC57030
0.9392	High Similarity	NPC83508
0.9392	High Similarity	NPC212678
0.9388	High Similarity	NPC45873
0.9384	High Similarity	NPC272721
0.9384	High Similarity	NPC183655
0.9384	High Similarity	NPC287395
0.9384	High Similarity	NPC194856
0.9384	High Similarity	NPC196277
0.9384	High Similarity	NPC276930
0.9384	High Similarity	NPC43669
0.9342	High Similarity	NPC308992
0.9333	High Similarity	NPC191146
0.9333	High Similarity	NPC68093
0.9333	High Similarity	NPC138243
0.9329	High Similarity	NPC176775
0.9329	High Similarity	NPC274327
0.9329	High Similarity	NPC255350
0.9329	High Similarity	NPC69394
0.9329	High Similarity	NPC22519
0.9329	High Similarity	NPC47781
0.9329	High Similarity	NPC145379
0.9329	High Similarity	NPC231018
0.9329	High Similarity	NPC160951
0.9329	High Similarity	NPC472915
0.9329	High Similarity	NPC183878
0.9324	High Similarity	NPC204515
0.9324	High Similarity	NPC31363
0.932	High Similarity	NPC17286
0.932	High Similarity	NPC259713
0.932	High Similarity	NPC296197
0.932	High Similarity	NPC216318
0.9315	High Similarity	NPC207729
0.9315	High Similarity	NPC77378
0.9296	High Similarity	NPC18457
0.9281	High Similarity	NPC83922
0.9281	High Similarity	NPC472448
0.9276	High Similarity	NPC263449
0.9276	High Similarity	NPC476980
0.9272	High Similarity	NPC300727
0.9272	High Similarity	NPC241904
0.9272	High Similarity	NPC181960
0.9272	High Similarity	NPC469584
0.9272	High Similarity	NPC299520
0.9272	High Similarity	NPC129684
0.9267	High Similarity	NPC196439
0.9267	High Similarity	NPC4455
0.9267	High Similarity	NPC138360
0.9267	High Similarity	NPC280339
0.9267	High Similarity	NPC213622
0.9267	High Similarity	NPC183597
0.9267	High Similarity	NPC113906
0.9267	High Similarity	NPC201136
0.9267	High Similarity	NPC208197
0.9267	High Similarity	NPC152951
0.9267	High Similarity	NPC128863
0.9267	High Similarity	NPC201451
0.9267	High Similarity	NPC37392
0.9267	High Similarity	NPC230149
0.9267	High Similarity	NPC44079
0.9267	High Similarity	NPC227325
0.9267	High Similarity	NPC2476
0.9267	High Similarity	NPC168247
0.9267	High Similarity	NPC50715
0.9267	High Similarity	NPC92659
0.9267	High Similarity	NPC167815
0.9267	High Similarity	NPC26227
0.9267	High Similarity	NPC472909
0.9267	High Similarity	NPC146165
0.9267	High Similarity	NPC117992
0.9267	High Similarity	NPC163780
0.9267	High Similarity	NPC57674
0.9262	High Similarity	NPC181209
0.9262	High Similarity	NPC245382
0.9262	High Similarity	NPC302950
0.9262	High Similarity	NPC209487
0.9262	High Similarity	NPC35763
0.9262	High Similarity	NPC39732
0.9262	High Similarity	NPC269451
0.9262	High Similarity	NPC142540
0.9262	High Similarity	NPC60972
0.9262	High Similarity	NPC219582
0.9262	High Similarity	NPC121522
0.9262	High Similarity	NPC257648
0.9262	High Similarity	NPC236637
0.9262	High Similarity	NPC100263
0.9262	High Similarity	NPC131266
0.9262	High Similarity	NPC216769
0.9262	High Similarity	NPC291802
0.9262	High Similarity	NPC477231
0.9262	High Similarity	NPC100971
0.9257	High Similarity	NPC184136
0.9257	High Similarity	NPC306821
0.9252	High Similarity	NPC118726
0.9252	High Similarity	NPC12367
0.9247	High Similarity	NPC231013
0.9216	High Similarity	NPC266314
0.9216	High Similarity	NPC258331
0.9216	High Similarity	NPC167678
0.9216	High Similarity	NPC29876
0.9216	High Similarity	NPC162668
0.9211	High Similarity	NPC152904
0.9211	High Similarity	NPC55738
0.9211	High Similarity	NPC16935
0.9211	High Similarity	NPC250214
0.9211	High Similarity	NPC95936
0.9211	High Similarity	NPC476242
0.9211	High Similarity	NPC474290
0.9205	High Similarity	NPC247017
0.9205	High Similarity	NPC49824
0.9205	High Similarity	NPC43243
0.9205	High Similarity	NPC274730
0.9205	High Similarity	NPC201837
0.9205	High Similarity	NPC474638
0.9205	High Similarity	NPC98661
0.9205	High Similarity	NPC245546
0.9205	High Similarity	NPC266960
0.92	High Similarity	NPC33051
0.92	High Similarity	NPC276409
0.92	High Similarity	NPC124714
0.92	High Similarity	NPC280937
0.92	High Similarity	NPC75279
0.92	High Similarity	NPC469550
0.92	High Similarity	NPC227337
0.92	High Similarity	NPC18727
0.92	High Similarity	NPC273462
0.92	High Similarity	NPC49402
0.92	High Similarity	NPC250822
0.92	High Similarity	NPC70433
0.9195	High Similarity	NPC45291
0.9195	High Similarity	NPC19980

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 NPC200221 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	479
0.1-0.2	1016
0.2-0.3	1843
0.3-0.4	2703
0.4-0.5	1719
0.5-0.6	955
0.6-0.7	294
0.7-0.8	93
0.8-0.85	34
0.85-0.9	8
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9329	High Similarity	NPD2801	Approved
0.9262	High Similarity	NPD1934	Approved
0.898	High Similarity	NPD1511	Approved
0.8947	High Similarity	NPD2393	Clinical (unspecified phase)
0.8859	High Similarity	NPD1512	Approved
0.8831	High Similarity	NPD3882	Suspended
0.8679	High Similarity	NPD6168	Clinical (unspecified phase)
0.8679	High Similarity	NPD6167	Clinical (unspecified phase)
0.8679	High Similarity	NPD6166	Phase 2
0.8571	High Similarity	NPD3818	Discontinued
0.8544	High Similarity	NPD5494	Approved
0.8514	High Similarity	NPD1549	Phase 2
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7074	Phase 3
0.8446	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD3817	Phase 2
0.8408	Intermediate Similarity	NPD5402	Approved
0.8405	Intermediate Similarity	NPD7054	Approved
0.8356	Intermediate Similarity	NPD447	Suspended
0.8354	Intermediate Similarity	NPD7472	Approved
0.8344	Intermediate Similarity	NPD1465	Phase 2
0.8311	Intermediate Similarity	NPD1510	Phase 2
0.8301	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1240	Approved
0.8288	Intermediate Similarity	NPD943	Approved
0.8269	Intermediate Similarity	NPD4380	Phase 2
0.8264	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6797	Phase 2
0.8187	Intermediate Similarity	NPD7075	Discontinued
0.8187	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1607	Approved
0.8163	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1613	Approved
0.8148	Intermediate Similarity	NPD1247	Approved
0.8144	Intermediate Similarity	NPD7251	Discontinued
0.8133	Intermediate Similarity	NPD1551	Phase 2
0.8113	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6232	Discontinued
0.8095	Intermediate Similarity	NPD7808	Phase 3
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8013	Intermediate Similarity	NPD2935	Discontinued
0.8013	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD6799	Approved
0.7987	Intermediate Similarity	NPD1933	Approved
0.7976	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD5403	Approved
0.7949	Intermediate Similarity	NPD5401	Approved
0.7949	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6559	Discontinued
0.7922	Intermediate Similarity	NPD3750	Approved
0.7875	Intermediate Similarity	NPD7411	Suspended
0.7867	Intermediate Similarity	NPD230	Phase 1
0.7843	Intermediate Similarity	NPD2346	Discontinued
0.784	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD3926	Phase 2
0.7826	Intermediate Similarity	NPD6801	Discontinued
0.7812	Intermediate Similarity	NPD6599	Discontinued
0.7808	Intermediate Similarity	NPD1203	Approved
0.7806	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD919	Approved
0.7799	Intermediate Similarity	NPD1653	Approved
0.7792	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2313	Discontinued
0.7778	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3226	Approved
0.7744	Intermediate Similarity	NPD3749	Approved
0.7718	Intermediate Similarity	NPD3027	Phase 3
0.7712	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6959	Discontinued
0.7683	Intermediate Similarity	NPD7768	Phase 2
0.7628	Intermediate Similarity	NPD2800	Approved
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD9717	Approved
0.7597	Intermediate Similarity	NPD3748	Approved
0.7588	Intermediate Similarity	NPD3751	Discontinued
0.7584	Intermediate Similarity	NPD9494	Approved
0.758	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6100	Approved
0.7548	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD6844	Discontinued
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1470	Approved
0.7434	Intermediate Similarity	NPD411	Approved
0.7432	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD8313	Approved
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7415	Intermediate Similarity	NPD1610	Phase 2
0.7405	Intermediate Similarity	NPD1243	Approved
0.7405	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2798	Approved
0.7391	Intermediate Similarity	NPD2532	Approved
0.7391	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2533	Approved
0.7391	Intermediate Similarity	NPD2534	Approved
0.7372	Intermediate Similarity	NPD4308	Phase 3
0.7358	Intermediate Similarity	NPD4628	Phase 3
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2309	Approved
0.7312	Intermediate Similarity	NPD6190	Approved
0.7303	Intermediate Similarity	NPD4908	Phase 1
0.7297	Intermediate Similarity	NPD1201	Approved
0.7294	Intermediate Similarity	NPD7199	Phase 2
0.7289	Intermediate Similarity	NPD37	Approved
0.7283	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD4966	Approved
0.7262	Intermediate Similarity	NPD4967	Phase 2
0.726	Intermediate Similarity	NPD1548	Phase 1
0.7257	Intermediate Similarity	NPD5953	Discontinued
0.7255	Intermediate Similarity	NPD4625	Phase 3
0.7248	Intermediate Similarity	NPD1608	Approved
0.7248	Intermediate Similarity	NPD9269	Phase 2
0.7241	Intermediate Similarity	NPD7286	Phase 2
0.7241	Intermediate Similarity	NPD9493	Approved
0.7219	Intermediate Similarity	NPD2797	Approved
0.7209	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3268	Approved
0.7208	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4749	Approved
0.7181	Intermediate Similarity	NPD422	Phase 1
0.7171	Intermediate Similarity	NPD1019	Discontinued
0.716	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6778	Approved
0.7151	Intermediate Similarity	NPD6781	Approved
0.7151	Intermediate Similarity	NPD6782	Approved
0.7151	Intermediate Similarity	NPD6780	Approved
0.7151	Intermediate Similarity	NPD6779	Approved
0.7151	Intermediate Similarity	NPD6777	Approved
0.7151	Intermediate Similarity	NPD6776	Approved
0.7134	Intermediate Similarity	NPD6651	Approved
0.7124	Intermediate Similarity	NPD2861	Phase 2
0.7119	Intermediate Similarity	NPD7685	Pre-registration
0.7117	Intermediate Similarity	NPD4357	Discontinued
0.7115	Intermediate Similarity	NPD4307	Phase 2
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.7111	Intermediate Similarity	NPD8150	Discontinued
0.711	Intermediate Similarity	NPD5242	Approved
0.7108	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7549	Discontinued
0.7075	Intermediate Similarity	NPD5536	Phase 2
0.7074	Intermediate Similarity	NPD6823	Phase 2
0.7073	Intermediate Similarity	NPD4662	Approved
0.7073	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4661	Approved
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6671	Approved
0.7051	Intermediate Similarity	NPD6233	Phase 2
0.7047	Intermediate Similarity	NPD17	Approved
0.7044	Intermediate Similarity	NPD7033	Discontinued
0.7039	Intermediate Similarity	NPD3225	Approved
0.7037	Intermediate Similarity	NPD7435	Discontinued
0.7024	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1481	Phase 2
0.7014	Intermediate Similarity	NPD228	Approved
0.7013	Intermediate Similarity	NPD3018	Phase 2
0.7012	Intermediate Similarity	NPD7390	Discontinued
0.7007	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD5353	Approved
0.6993	Remote Similarity	NPD3267	Approved
0.6993	Remote Similarity	NPD3266	Approved
0.6987	Remote Similarity	NPD6798	Discontinued
0.6987	Remote Similarity	NPD3764	Approved
0.6987	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.698	Remote Similarity	NPD9268	Approved
0.6975	Remote Similarity	NPD1652	Phase 2
0.6971	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2899	Discontinued
0.6957	Remote Similarity	NPD7266	Discontinued
0.6957	Remote Similarity	NPD1471	Phase 3
0.6954	Remote Similarity	NPD5710	Approved
0.6954	Remote Similarity	NPD5711	Approved
0.6954	Remote Similarity	NPD1535	Discovery
0.6947	Remote Similarity	NPD7696	Phase 3
0.6947	Remote Similarity	NPD7698	Approved
0.6947	Remote Similarity	NPD7697	Approved
0.6928	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6386	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