NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.2
Volume:	268.877
LogP:	4.037
LogD:	3.895
LogS:	-4.537
# Rotatable Bonds:	7
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	3.452
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.546
MDCK Permeability:	2.41845100390492e-05
Pgp-inhibitor:	0.543
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.911
30% Bioavailability (F30%):	0.285

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.662
Plasma Protein Binding (PPB):	97.76927947998047%
Volume Distribution (VD):	1.903
Pgp-substrate:	3.0592386722564697%

ADMET: Metabolism

CYP1A2-inhibitor:	0.351
CYP1A2-substrate:	0.45
CYP2C19-inhibitor:	0.51
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.265
CYP2D6-substrate:	0.308
CYP3A4-inhibitor:	0.659
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	6.748
Half-life (T1/2):	0.688

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.935
Carcinogencity:	0.15
Eye Corrosion:	0.81
Eye Irritation:	0.984
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC209278

Natural Product ID:	NPC209278
*Common Name:**	5-Hydroxy-1-Methoxyxanthen-9-One
IUPAC Name:	5-hydroxy-1-methoxyxanthen-9-one
Synonyms:
Standard InCHIKey:	GCAMSSLNXVYMKS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O4/c1-17-10-6-3-7-11-12(10)13(16)8-4-2-5-9(15)14(8)18-11/h2-7,15H,1H3
SMILES:	COc1cccc2c1c(=O)c1cccc(c1o2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL187159
PubChem CID:	479656
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
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22290	Garcinia linii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22290	Garcinia linii	Species	Clusiaceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	51000.0	nM	PMID[511951]

☑ 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 NPC209278 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	498
0.1-0.2	2086
0.2-0.3	5482
0.3-0.4	11804
0.4-0.5	5120
0.5-0.6	4303
0.6-0.7	5365
0.7-0.8	4799
0.8-0.85	1839
0.85-0.9	899
0.9-0.95	419
0.95-1	83

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC59551
0.9789	High Similarity	NPC294502
0.9789	High Similarity	NPC200221
0.972	High Similarity	NPC29231
0.9648	High Similarity	NPC46941
0.958	High Similarity	NPC196277
0.958	High Similarity	NPC272721
0.958	High Similarity	NPC43669
0.9521	High Similarity	NPC88645
0.9521	High Similarity	NPC271779
0.9521	High Similarity	NPC167091
0.9521	High Similarity	NPC206238
0.9521	High Similarity	NPC292214
0.9517	High Similarity	NPC31363
0.951	High Similarity	NPC77378
0.9456	High Similarity	NPC117992
0.9456	High Similarity	NPC230149
0.9456	High Similarity	NPC57674
0.9456	High Similarity	NPC152951
0.9456	High Similarity	NPC168247
0.9452	High Similarity	NPC180234
0.9452	High Similarity	NPC101996
0.9452	High Similarity	NPC477231
0.9452	High Similarity	NPC39007
0.9452	High Similarity	NPC120537
0.9452	High Similarity	NPC75069
0.9452	High Similarity	NPC161277
0.9452	High Similarity	NPC199100
0.9452	High Similarity	NPC257648
0.9388	High Similarity	NPC273462
0.9388	High Similarity	NPC33051
0.9388	High Similarity	NPC469550
0.9388	High Similarity	NPC49402
0.9388	High Similarity	NPC70433
0.9388	High Similarity	NPC227337
0.9384	High Similarity	NPC149614
0.9384	High Similarity	NPC171010
0.9384	High Similarity	NPC251110
0.9384	High Similarity	NPC475076
0.9375	High Similarity	NPC168803
0.9329	High Similarity	NPC129684
0.9329	High Similarity	NPC99597
0.9329	High Similarity	NPC210084
0.9329	High Similarity	NPC299520
0.9324	High Similarity	NPC256925
0.9324	High Similarity	NPC2928
0.932	High Similarity	NPC39732
0.932	High Similarity	NPC60972
0.932	High Similarity	NPC260979
0.932	High Similarity	NPC219582
0.932	High Similarity	NPC236637
0.932	High Similarity	NPC472912
0.932	High Similarity	NPC302950
0.9315	High Similarity	NPC62042
0.9315	High Similarity	NPC248102
0.9315	High Similarity	NPC179183
0.9315	High Similarity	NPC151473
0.9315	High Similarity	NPC61620
0.9267	High Similarity	NPC204879
0.9267	High Similarity	NPC55738
0.9262	High Similarity	NPC255106
0.9262	High Similarity	NPC6633
0.9262	High Similarity	NPC133970
0.9262	High Similarity	NPC5322
0.9262	High Similarity	NPC474638
0.9262	High Similarity	NPC472455
0.9262	High Similarity	NPC472916
0.9262	High Similarity	NPC235165
0.9257	High Similarity	NPC18727
0.9252	High Similarity	NPC117579
0.9247	High Similarity	NPC264289
0.9247	High Similarity	NPC223579
0.9247	High Similarity	NPC200060
0.9247	High Similarity	NPC183959
0.9247	High Similarity	NPC333691
0.9247	High Similarity	NPC287101
0.9247	High Similarity	NPC1612
0.9247	High Similarity	NPC142876
0.9247	High Similarity	NPC183950
0.9247	High Similarity	NPC40290
0.9247	High Similarity	NPC139293
0.9247	High Similarity	NPC264550
0.9247	High Similarity	NPC69430
0.9247	High Similarity	NPC137062
0.9247	High Similarity	NPC195763
0.9247	High Similarity	NPC52005
0.9247	High Similarity	NPC105512
0.9241	High Similarity	NPC125449
0.9241	High Similarity	NPC95864
0.9241	High Similarity	NPC188074
0.9231	High Similarity	NPC287722
0.9225	High Similarity	NPC145673
0.92	High Similarity	NPC472911
0.92	High Similarity	NPC218313
0.92	High Similarity	NPC48208
0.92	High Similarity	NPC245758
0.92	High Similarity	NPC291508
0.92	High Similarity	NPC262286
0.92	High Similarity	NPC156057
0.92	High Similarity	NPC36852
0.92	High Similarity	NPC161960
0.92	High Similarity	NPC180011
0.92	High Similarity	NPC78225
0.92	High Similarity	NPC472914
0.92	High Similarity	NPC187745
0.92	High Similarity	NPC219867
0.92	High Similarity	NPC475267
0.92	High Similarity	NPC472910
0.92	High Similarity	NPC52530
0.92	High Similarity	NPC162869
0.92	High Similarity	NPC472913
0.92	High Similarity	NPC67876
0.92	High Similarity	NPC472963
0.92	High Similarity	NPC474681
0.92	High Similarity	NPC304008
0.92	High Similarity	NPC474208
0.92	High Similarity	NPC474836
0.92	High Similarity	NPC222814
0.92	High Similarity	NPC96167
0.9195	High Similarity	NPC200246
0.9195	High Similarity	NPC20830
0.9195	High Similarity	NPC255807
0.9195	High Similarity	NPC31018
0.9195	High Similarity	NPC472280
0.9195	High Similarity	NPC234255
0.9195	High Similarity	NPC256612
0.9189	High Similarity	NPC301323
0.9189	High Similarity	NPC100887
0.9189	High Similarity	NPC222830
0.9189	High Similarity	NPC275836
0.9189	High Similarity	NPC198826
0.9189	High Similarity	NPC57030
0.9189	High Similarity	NPC120163
0.9189	High Similarity	NPC256283
0.9189	High Similarity	NPC212678
0.9189	High Similarity	NPC55205
0.9189	High Similarity	NPC71334
0.9189	High Similarity	NPC162313
0.9189	High Similarity	NPC131624
0.9189	High Similarity	NPC293183
0.9189	High Similarity	NPC187498
0.9189	High Similarity	NPC25270
0.9189	High Similarity	NPC239128
0.9189	High Similarity	NPC156222
0.9189	High Similarity	NPC275722
0.9189	High Similarity	NPC188203
0.9189	High Similarity	NPC83508
0.9189	High Similarity	NPC241498
0.9184	High Similarity	NPC45873
0.9178	High Similarity	NPC194653
0.9178	High Similarity	NPC3036
0.9178	High Similarity	NPC139364
0.9178	High Similarity	NPC194856
0.9178	High Similarity	NPC80710
0.9178	High Similarity	NPC203747
0.9178	High Similarity	NPC254702
0.9178	High Similarity	NPC321011
0.9178	High Similarity	NPC294852
0.9178	High Similarity	NPC287395
0.9178	High Similarity	NPC183655
0.9178	High Similarity	NPC276930
0.9178	High Similarity	NPC120464
0.9178	High Similarity	NPC188679
0.9167	High Similarity	NPC142165
0.9145	High Similarity	NPC308992
0.9133	High Similarity	NPC115853
0.9133	High Similarity	NPC195796
0.9133	High Similarity	NPC191146
0.9133	High Similarity	NPC138243
0.9133	High Similarity	NPC470600
0.9133	High Similarity	NPC35038
0.9133	High Similarity	NPC472907
0.9133	High Similarity	NPC278778
0.9133	High Similarity	NPC13858
0.9133	High Similarity	NPC265511
0.9133	High Similarity	NPC326037
0.9133	High Similarity	NPC320825
0.9133	High Similarity	NPC68093
0.9133	High Similarity	NPC291878
0.9128	High Similarity	NPC27532
0.9128	High Similarity	NPC141212
0.9128	High Similarity	NPC472905
0.9128	High Similarity	NPC256346
0.9128	High Similarity	NPC69394
0.9128	High Similarity	NPC255350
0.9128	High Similarity	NPC160951
0.9128	High Similarity	NPC274327
0.9128	High Similarity	NPC472915
0.9128	High Similarity	NPC231018
0.9128	High Similarity	NPC176775
0.9128	High Similarity	NPC246328
0.9128	High Similarity	NPC325028
0.9128	High Similarity	NPC183878
0.9128	High Similarity	NPC145379
0.9128	High Similarity	NPC22519
0.9128	High Similarity	NPC47781
0.9122	High Similarity	NPC200740
0.9122	High Similarity	NPC54394
0.9122	High Similarity	NPC204515
0.9122	High Similarity	NPC125062

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 NPC209278 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	471
0.1-0.2	1024
0.2-0.3	1806
0.3-0.4	2703
0.4-0.5	1705
0.5-0.6	991
0.6-0.7	302
0.7-0.8	93
0.8-0.85	39
0.85-0.9	9
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.932	High Similarity	NPD1934	Approved
0.9128	High Similarity	NPD2801	Approved
0.9034	High Similarity	NPD1511	Approved
0.9007	High Similarity	NPD3882	Suspended
0.9	High Similarity	NPD2393	Clinical (unspecified phase)
0.8912	High Similarity	NPD1512	Approved
0.8726	High Similarity	NPD6168	Clinical (unspecified phase)
0.8726	High Similarity	NPD6167	Clinical (unspecified phase)
0.8726	High Similarity	NPD6166	Phase 2
0.869	High Similarity	NPD1549	Phase 2
0.8621	High Similarity	NPD1552	Clinical (unspecified phase)
0.8621	High Similarity	NPD1550	Clinical (unspecified phase)
0.8616	High Similarity	NPD3818	Discontinued
0.8516	High Similarity	NPD4868	Clinical (unspecified phase)
0.8509	High Similarity	NPD7074	Phase 3
0.8483	Intermediate Similarity	NPD1510	Phase 2
0.8462	Intermediate Similarity	NPD1240	Approved
0.8462	Intermediate Similarity	NPD943	Approved
0.8452	Intermediate Similarity	NPD3817	Phase 2
0.8447	Intermediate Similarity	NPD7054	Approved
0.8403	Intermediate Similarity	NPD447	Suspended
0.8395	Intermediate Similarity	NPD7472	Approved
0.8387	Intermediate Similarity	NPD1465	Phase 2
0.8354	Intermediate Similarity	NPD5494	Approved
0.8345	Intermediate Similarity	NPD1607	Approved
0.8344	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7075	Discontinued
0.8312	Intermediate Similarity	NPD4380	Phase 2
0.831	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1551	Phase 2
0.8269	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6797	Phase 2
0.8228	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5402	Approved
0.8207	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1613	Approved
0.8182	Intermediate Similarity	NPD7251	Discontinued
0.8176	Intermediate Similarity	NPD2796	Approved
0.8158	Intermediate Similarity	NPD6799	Approved
0.8153	Intermediate Similarity	NPD7819	Suspended
0.8151	Intermediate Similarity	NPD1933	Approved
0.8137	Intermediate Similarity	NPD6232	Discontinued
0.8133	Intermediate Similarity	NPD7808	Phase 3
0.8117	Intermediate Similarity	NPD5403	Approved
0.8105	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD5401	Approved
0.8098	Intermediate Similarity	NPD7473	Discontinued
0.8079	Intermediate Similarity	NPD3750	Approved
0.8025	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3926	Phase 2
0.7975	Intermediate Similarity	NPD6801	Discontinued
0.7972	Intermediate Similarity	NPD1203	Approved
0.7964	Intermediate Similarity	NPD6559	Discontinued
0.7963	Intermediate Similarity	NPD1247	Approved
0.7962	Intermediate Similarity	NPD6599	Discontinued
0.7961	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD919	Approved
0.7947	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD230	Phase 1
0.7892	Intermediate Similarity	NPD5844	Phase 1
0.7888	Intermediate Similarity	NPD3749	Approved
0.7881	Intermediate Similarity	NPD2346	Discontinued
0.7826	Intermediate Similarity	NPD7768	Phase 2
0.7823	Intermediate Similarity	NPD2313	Discontinued
0.7815	Intermediate Similarity	NPD2935	Discontinued
0.7785	Intermediate Similarity	NPD3226	Approved
0.7784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD9717	Approved
0.7755	Intermediate Similarity	NPD3027	Phase 3
0.7748	Intermediate Similarity	NPD3748	Approved
0.7748	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6959	Discontinued
0.774	Intermediate Similarity	NPD9494	Approved
0.7727	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6099	Approved
0.7697	Intermediate Similarity	NPD6100	Approved
0.7662	Intermediate Similarity	NPD2800	Approved
0.7647	Intermediate Similarity	NPD2344	Approved
0.7632	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2799	Discontinued
0.761	Intermediate Similarity	NPD1653	Approved
0.7603	Intermediate Similarity	NPD1470	Approved
0.7584	Intermediate Similarity	NPD411	Approved
0.7569	Intermediate Similarity	NPD1610	Phase 2
0.7568	Intermediate Similarity	NPD6832	Phase 2
0.7556	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2798	Approved
0.755	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1243	Approved
0.7547	Intermediate Similarity	NPD920	Approved
0.7516	Intermediate Similarity	NPD4308	Phase 3
0.7515	Intermediate Similarity	NPD3751	Discontinued
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8312	Approved
0.7457	Intermediate Similarity	NPD8313	Approved
0.7452	Intermediate Similarity	NPD2309	Approved
0.745	Intermediate Similarity	NPD4908	Phase 1
0.7448	Intermediate Similarity	NPD1201	Approved
0.7443	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7199	Phase 2
0.7421	Intermediate Similarity	NPD2532	Approved
0.7421	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2534	Approved
0.7421	Intermediate Similarity	NPD2533	Approved
0.7413	Intermediate Similarity	NPD1548	Phase 1
0.7405	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4625	Phase 3
0.7397	Intermediate Similarity	NPD1608	Approved
0.7394	Intermediate Similarity	NPD9493	Approved
0.7384	Intermediate Similarity	NPD5953	Discontinued
0.7365	Intermediate Similarity	NPD2797	Approved
0.7351	Intermediate Similarity	NPD3268	Approved
0.7351	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4749	Approved
0.7337	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD422	Phase 1
0.7317	Intermediate Similarity	NPD6844	Discontinued
0.7317	Intermediate Similarity	NPD37	Approved
0.731	Intermediate Similarity	NPD7228	Approved
0.7289	Intermediate Similarity	NPD4965	Approved
0.7289	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4967	Phase 2
0.7289	Intermediate Similarity	NPD4966	Approved
0.7279	Intermediate Similarity	NPD9269	Phase 2
0.7278	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD6651	Approved
0.7273	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7286	Phase 2
0.7263	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4307	Phase 2
0.725	Intermediate Similarity	NPD4357	Discontinued
0.7239	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6190	Approved
0.7222	Intermediate Similarity	NPD5536	Phase 2
0.7205	Intermediate Similarity	NPD4661	Approved
0.7205	Intermediate Similarity	NPD4662	Approved
0.7205	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1019	Discontinued
0.72	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD17	Approved
0.7181	Intermediate Similarity	NPD3225	Approved
0.7179	Intermediate Similarity	NPD7033	Discontinued
0.7163	Intermediate Similarity	NPD228	Approved
0.7153	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3018	Phase 2
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7135	Intermediate Similarity	NPD5242	Approved
0.7133	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD3267	Approved
0.7126	Intermediate Similarity	NPD4288	Approved
0.7124	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3764	Approved
0.7124	Intermediate Similarity	NPD6798	Discontinued
0.7099	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1471	Phase 3
0.7063	Intermediate Similarity	NPD1241	Discontinued
0.7048	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8150	Discontinued
0.7039	Intermediate Similarity	NPD8434	Phase 2
0.7037	Intermediate Similarity	NPD7390	Discontinued
0.7032	Intermediate Similarity	NPD1558	Phase 1
0.7024	Intermediate Similarity	NPD5353	Approved
0.7013	Intermediate Similarity	NPD1296	Phase 2
0.7011	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD9268	Approved
0.7	Intermediate Similarity	NPD1652	Phase 2
0.7	Intermediate Similarity	NPD2982	Phase 2
0.7	Intermediate Similarity	NPD2983	Phase 2
0.6989	Remote Similarity	NPD6779	Approved
0.6989	Remote Similarity	NPD6780	Approved
0.6989	Remote Similarity	NPD6781	Approved
0.6989	Remote Similarity	NPD6776	Approved
0.6989	Remote Similarity	NPD6782	Approved
0.6989	Remote Similarity	NPD6777	Approved
0.6989	Remote Similarity	NPD6778	Approved
0.6987	Remote Similarity	NPD6355	Discontinued
0.6981	Remote Similarity	NPD7266	Discontinued
0.6977	Remote Similarity	NPD5710	Approved
0.6977	Remote Similarity	NPD5711	Approved
0.6961	Remote Similarity	NPD4287	Approved
0.6946	Remote Similarity	NPD6385	Approved
0.6946	Remote Similarity	NPD6386	Approved
0.6941	Remote Similarity	NPD6971	Discontinued
0.6939	Remote Similarity	NPD9545	Approved
0.6937	Remote Similarity	NPD2424	Discontinued
0.6933	Remote Similarity	NPD2981	Phase 2

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