NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.08
Volume:	247.06
LogP:	2.409
LogD:	1.983
LogS:	-2.667
# Rotatable Bonds:	2
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.884
Synthetic Accessibility Score:	2.558
Fsp3:	0.308
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:	-4.745
MDCK Permeability:	1.8319784430786967e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	80.21680450439453%
Volume Distribution (VD):	0.917
Pgp-substrate:	14.711793899536133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.818
CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.216
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.224
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.669
CYP3A4-inhibitor:	0.208
CYP3A4-substrate:	0.516

ADMET: Excretion

Clearance (CL):	4.444
Half-life (T1/2):	0.541

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.288
Rat Oral Acute Toxicity:	0.591
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.575
Carcinogencity:	0.069
Eye Corrosion:	0.005
Eye Irritation:	0.452
Respiratory Toxicity:	0.085

Download Data

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

Natural Product: NPC251188

Natural Product ID:	NPC251188
*Common Name:**	5-Hydroxy-2,8-Dimethyl-6,7-Dimethoxy Chromone
IUPAC Name:	5-hydroxy-6,7-dimethoxy-2,8-dimethylchromen-4-one
Synonyms:
Standard InCHIKey:	LTVYEBXCAHVDNQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H14O5/c1-6-5-8(14)9-10(15)13(17-4)12(16-3)7(2)11(9)18-6/h5,15H,1-4H3
SMILES:	COc1c(C)c2oc(C)cc(=O)c2c(c1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454840
PubChem CID:	336375
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11269	Couepia paraensis	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6854338]
NPO11269	Couepia paraensis	Species	Chrysobalanaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	60.0	ug ml-1	PMID[540261]

☑ 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 NPC251188 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	422
0.1-0.2	1914
0.2-0.3	5055
0.3-0.4	11570
0.4-0.5	5903
0.5-0.6	3878
0.6-0.7	4892
0.7-0.8	4902
0.8-0.85	2387
0.85-0.9	1091
0.9-0.95	665
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.958	High Similarity	NPC61871
0.958	High Similarity	NPC55557
0.958	High Similarity	NPC30647
0.9272	High Similarity	NPC246478
0.9272	High Similarity	NPC476980
0.9267	High Similarity	NPC78225
0.9267	High Similarity	NPC262286
0.9267	High Similarity	NPC36852
0.9257	High Similarity	NPC212678
0.9257	High Similarity	NPC83508
0.9257	High Similarity	NPC71334
0.9257	High Similarity	NPC100887
0.9257	High Similarity	NPC275836
0.9257	High Similarity	NPC301323
0.9257	High Similarity	NPC239128
0.9257	High Similarity	NPC25270
0.9257	High Similarity	NPC222830
0.9257	High Similarity	NPC156222
0.9257	High Similarity	NPC180234
0.9257	High Similarity	NPC57030
0.9257	High Similarity	NPC293183
0.9257	High Similarity	NPC120537
0.9257	High Similarity	NPC256283
0.9257	High Similarity	NPC187498
0.9257	High Similarity	NPC162313
0.9257	High Similarity	NPC471982
0.9257	High Similarity	NPC188203
0.9257	High Similarity	NPC131624
0.9257	High Similarity	NPC275722
0.9257	High Similarity	NPC120163
0.9257	High Similarity	NPC241498
0.9257	High Similarity	NPC198826
0.9257	High Similarity	NPC101996
0.9257	High Similarity	NPC199100
0.9211	High Similarity	NPC258331
0.9205	High Similarity	NPC250214
0.9205	High Similarity	NPC95936
0.92	High Similarity	NPC68093
0.92	High Similarity	NPC191146
0.92	High Similarity	NPC317383
0.92	High Similarity	NPC138243
0.9195	High Similarity	NPC292214
0.9195	High Similarity	NPC22519
0.9195	High Similarity	NPC176775
0.9195	High Similarity	NPC276409
0.9195	High Similarity	NPC274327
0.9195	High Similarity	NPC183878
0.9195	High Similarity	NPC271779
0.9195	High Similarity	NPC255350
0.9195	High Similarity	NPC145379
0.9195	High Similarity	NPC206238
0.9195	High Similarity	NPC69394
0.9195	High Similarity	NPC88645
0.9195	High Similarity	NPC75279
0.9195	High Similarity	NPC160951
0.9195	High Similarity	NPC231018
0.9195	High Similarity	NPC47781
0.9195	High Similarity	NPC250822
0.9195	High Similarity	NPC167091
0.9189	High Similarity	NPC171010
0.9184	High Similarity	NPC296197
0.9184	High Similarity	NPC259713
0.9184	High Similarity	NPC216318
0.9184	High Similarity	NPC17286
0.9172	High Similarity	NPC472917
0.915	High Similarity	NPC81679
0.915	High Similarity	NPC472448
0.915	High Similarity	NPC294965
0.915	High Similarity	NPC83922
0.9145	High Similarity	NPC56085
0.9145	High Similarity	NPC228785
0.9145	High Similarity	NPC204290
0.9145	High Similarity	NPC14353
0.9139	High Similarity	NPC476981
0.9139	High Similarity	NPC223787
0.9133	High Similarity	NPC201136
0.9133	High Similarity	NPC146165
0.9133	High Similarity	NPC2476
0.9133	High Similarity	NPC167815
0.9133	High Similarity	NPC4455
0.9133	High Similarity	NPC201451
0.9133	High Similarity	NPC213622
0.9133	High Similarity	NPC138360
0.9133	High Similarity	NPC208197
0.9133	High Similarity	NPC18954
0.9133	High Similarity	NPC280339
0.9133	High Similarity	NPC39184
0.9133	High Similarity	NPC20830
0.9133	High Similarity	NPC183597
0.9133	High Similarity	NPC26227
0.9133	High Similarity	NPC196439
0.9133	High Similarity	NPC44079
0.9133	High Similarity	NPC163780
0.9133	High Similarity	NPC256612
0.9133	High Similarity	NPC227325
0.9133	High Similarity	NPC128863
0.9133	High Similarity	NPC134287
0.9133	High Similarity	NPC92659
0.9133	High Similarity	NPC113906
0.9133	High Similarity	NPC130589
0.9133	High Similarity	NPC50715
0.9128	High Similarity	NPC249570
0.9128	High Similarity	NPC161277
0.9128	High Similarity	NPC39007
0.9128	High Similarity	NPC142540
0.9122	High Similarity	NPC184136
0.9122	High Similarity	NPC45873
0.9122	High Similarity	NPC306821
0.9122	High Similarity	NPC62042
0.9122	High Similarity	NPC179183
0.9122	High Similarity	NPC61620
0.9116	High Similarity	NPC287395
0.9116	High Similarity	NPC183655
0.9116	High Similarity	NPC120464
0.911	High Similarity	NPC143903
0.911	High Similarity	NPC226987
0.9091	High Similarity	NPC470459
0.9091	High Similarity	NPC270837
0.9085	High Similarity	NPC266314
0.9085	High Similarity	NPC278052
0.9085	High Similarity	NPC40491
0.9085	High Similarity	NPC29876
0.9085	High Similarity	NPC61010
0.9085	High Similarity	NPC259456
0.9085	High Similarity	NPC167678
0.9079	High Similarity	NPC100123
0.9073	High Similarity	NPC245546
0.9073	High Similarity	NPC49824
0.9073	High Similarity	NPC292107
0.9073	High Similarity	NPC98661
0.9073	High Similarity	NPC247017
0.9073	High Similarity	NPC266960
0.9073	High Similarity	NPC474520
0.9073	High Similarity	NPC472455
0.9073	High Similarity	NPC235165
0.9073	High Similarity	NPC43243
0.9073	High Similarity	NPC255106
0.9067	High Similarity	NPC476631
0.9067	High Similarity	NPC280937
0.906	High Similarity	NPC225731
0.906	High Similarity	NPC117579
0.906	High Similarity	NPC226973
0.906	High Similarity	NPC208043
0.906	High Similarity	NPC251110
0.906	High Similarity	NPC149614
0.906	High Similarity	NPC45291
0.906	High Similarity	NPC19980
0.9054	High Similarity	NPC328119
0.9054	High Similarity	NPC137062
0.9054	High Similarity	NPC287101
0.9054	High Similarity	NPC52005
0.9054	High Similarity	NPC48479
0.9054	High Similarity	NPC183950
0.9054	High Similarity	NPC177298
0.9054	High Similarity	NPC223579
0.9048	High Similarity	NPC239312
0.9048	High Similarity	NPC275772
0.9048	High Similarity	NPC130230
0.9032	High Similarity	NPC470457
0.9032	High Similarity	NPC275780
0.9032	High Similarity	NPC239752
0.9032	High Similarity	NPC472450
0.9026	High Similarity	NPC261470
0.902	High Similarity	NPC320359
0.9013	High Similarity	NPC241904
0.9013	High Similarity	NPC48208
0.9013	High Similarity	NPC305663
0.9013	High Similarity	NPC210084
0.9013	High Similarity	NPC162869
0.9013	High Similarity	NPC472911
0.9013	High Similarity	NPC75215
0.9013	High Similarity	NPC93376
0.9013	High Similarity	NPC165977
0.9013	High Similarity	NPC472914
0.9013	High Similarity	NPC78302
0.9013	High Similarity	NPC227192
0.9013	High Similarity	NPC203891
0.9013	High Similarity	NPC217677
0.9013	High Similarity	NPC245758
0.9013	High Similarity	NPC287979
0.9013	High Similarity	NPC29841
0.9013	High Similarity	NPC101830
0.9013	High Similarity	NPC472438
0.9013	High Similarity	NPC96167
0.9013	High Similarity	NPC475267
0.9013	High Similarity	NPC99597
0.9013	High Similarity	NPC222814
0.9013	High Similarity	NPC300727
0.9013	High Similarity	NPC474836
0.9013	High Similarity	NPC110070
0.9013	High Similarity	NPC472913
0.9013	High Similarity	NPC472910
0.9013	High Similarity	NPC224137
0.9013	High Similarity	NPC163524
0.9013	High Similarity	NPC235215
0.9013	High Similarity	NPC189179
0.9013	High Similarity	NPC469584
0.9013	High Similarity	NPC78103
0.9013	High Similarity	NPC470402
0.9013	High Similarity	NPC7973

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 NPC251188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	1013
0.2-0.3	1977
0.3-0.4	2715
0.4-0.5	1609
0.5-0.6	944
0.6-0.7	347
0.7-0.8	104
0.8-0.85	33
0.85-0.9	9
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9195	High Similarity	NPD2801	Approved
0.8874	High Similarity	NPD1934	Approved
0.8844	High Similarity	NPD1511	Approved
0.8816	High Similarity	NPD2393	Clinical (unspecified phase)
0.8725	High Similarity	NPD1512	Approved
0.8581	High Similarity	NPD3882	Suspended
0.8446	Intermediate Similarity	NPD2800	Approved
0.8411	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD1247	Approved
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD5494	Approved
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8193	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7054	Approved
0.817	Intermediate Similarity	NPD2534	Approved
0.817	Intermediate Similarity	NPD2532	Approved
0.817	Intermediate Similarity	NPD2533	Approved
0.8141	Intermediate Similarity	NPD4380	Phase 2
0.8133	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7074	Phase 3
0.8121	Intermediate Similarity	NPD7472	Approved
0.8113	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6232	Discontinued
0.8067	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1510	Phase 2
0.8052	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7473	Discontinued
0.8027	Intermediate Similarity	NPD943	Approved
0.8027	Intermediate Similarity	NPD1240	Approved
0.8013	Intermediate Similarity	NPD1549	Phase 2
0.8012	Intermediate Similarity	NPD919	Approved
0.7987	Intermediate Similarity	NPD1465	Phase 2
0.7973	Intermediate Similarity	NPD230	Phase 1
0.7964	Intermediate Similarity	NPD6797	Phase 2
0.795	Intermediate Similarity	NPD7075	Discontinued
0.7919	Intermediate Similarity	NPD6651	Approved
0.7919	Intermediate Similarity	NPD1607	Approved
0.7917	Intermediate Similarity	NPD7251	Discontinued
0.7875	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7808	Phase 3
0.7852	Intermediate Similarity	NPD447	Suspended
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.784	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6801	Discontinued
0.7764	Intermediate Similarity	NPD7819	Suspended
0.7763	Intermediate Similarity	NPD2935	Discontinued
0.7763	Intermediate Similarity	NPD2796	Approved
0.7756	Intermediate Similarity	NPD6799	Approved
0.7738	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1243	Approved
0.7722	Intermediate Similarity	NPD920	Approved
0.7716	Intermediate Similarity	NPD5402	Approved
0.7716	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6959	Discontinued
0.7697	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7411	Suspended
0.7635	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD3926	Phase 2
0.7595	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6599	Discontinued
0.7568	Intermediate Similarity	NPD9494	Approved
0.755	Intermediate Similarity	NPD1613	Approved
0.755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5710	Approved
0.7545	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD6559	Discontinued
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1653	Approved
0.7452	Intermediate Similarity	NPD3750	Approved
0.7452	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1551	Phase 2
0.7417	Intermediate Similarity	NPD2313	Discontinued
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3027	Phase 3
0.7349	Intermediate Similarity	NPD7768	Phase 2
0.7347	Intermediate Similarity	NPD9269	Phase 2
0.7305	Intermediate Similarity	NPD3749	Approved
0.7301	Intermediate Similarity	NPD3226	Approved
0.7284	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5403	Approved
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5401	Approved
0.7262	Intermediate Similarity	NPD6234	Discontinued
0.7261	Intermediate Similarity	NPD2344	Approved
0.7261	Intermediate Similarity	NPD2346	Discontinued
0.7244	Intermediate Similarity	NPD2799	Discontinued
0.7241	Intermediate Similarity	NPD5953	Discontinued
0.7228	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7286	Phase 2
0.7197	Intermediate Similarity	NPD6100	Approved
0.7197	Intermediate Similarity	NPD6099	Approved
0.719	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD422	Phase 1
0.7159	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3748	Approved
0.7127	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4628	Phase 3
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9717	Approved
0.7099	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7390	Discontinued
0.7086	Intermediate Similarity	NPD1203	Approved
0.7081	Intermediate Similarity	NPD2309	Approved
0.7078	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7199	Phase 2
0.7075	Intermediate Similarity	NPD9268	Approved
0.7069	Intermediate Similarity	NPD3751	Discontinued
0.7067	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD37	Approved
0.7055	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2403	Approved
0.7051	Intermediate Similarity	NPD5124	Phase 1
0.7051	Intermediate Similarity	NPD1933	Approved
0.7051	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4966	Approved
0.7041	Intermediate Similarity	NPD4967	Phase 2
0.7041	Intermediate Similarity	NPD4965	Approved
0.7039	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5353	Approved
0.6975	Remote Similarity	NPD6190	Approved
0.6971	Remote Similarity	NPD7228	Approved
0.6968	Remote Similarity	NPD411	Approved
0.6957	Remote Similarity	NPD2654	Approved
0.6936	Remote Similarity	NPD3787	Discontinued
0.6897	Remote Similarity	NPD5242	Approved
0.6894	Remote Similarity	NPD2424	Discontinued
0.6892	Remote Similarity	NPD1548	Phase 1
0.6887	Remote Similarity	NPD1608	Approved
0.6882	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD228	Approved
0.6865	Remote Similarity	NPD4360	Phase 2
0.6865	Remote Similarity	NPD4363	Phase 3
0.6862	Remote Similarity	NPD6782	Approved
0.6862	Remote Similarity	NPD6780	Approved
0.6862	Remote Similarity	NPD6778	Approved
0.6862	Remote Similarity	NPD6777	Approved
0.6862	Remote Similarity	NPD6781	Approved
0.6862	Remote Similarity	NPD6779	Approved
0.6862	Remote Similarity	NPD6776	Approved
0.6859	Remote Similarity	NPD1296	Phase 2
0.6859	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8312	Approved
0.6833	Remote Similarity	NPD8313	Approved
0.6821	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1610	Phase 2
0.6816	Remote Similarity	NPD7685	Pre-registration
0.6813	Remote Similarity	NPD8434	Phase 2
0.6798	Remote Similarity	NPD1729	Discontinued
0.6779	Remote Similarity	NPD9545	Approved
0.6765	Remote Similarity	NPD6844	Discontinued
0.6757	Remote Similarity	NPD9493	Approved
0.6754	Remote Similarity	NPD7435	Discontinued
0.6753	Remote Similarity	NPD1470	Approved
0.6753	Remote Similarity	NPD8151	Discontinued
0.6752	Remote Similarity	NPD3268	Approved
0.6748	Remote Similarity	NPD6674	Discontinued
0.6748	Remote Similarity	NPD1652	Phase 2
0.6743	Remote Similarity	NPD7229	Phase 3
0.6738	Remote Similarity	NPD4361	Phase 2
0.6738	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7584	Approved
0.6732	Remote Similarity	NPD4749	Approved
0.6731	Remote Similarity	NPD6832	Phase 2
0.6731	Remote Similarity	NPD4908	Phase 1
0.6728	Remote Similarity	NPD1471	Phase 3
0.6728	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8150	Discontinued
0.6711	Remote Similarity	NPD1201	Approved
0.671	Remote Similarity	NPD1019	Discontinued
0.671	Remote Similarity	NPD2798	Approved
0.6708	Remote Similarity	NPD7033	Discontinued
0.6708	Remote Similarity	NPD4308	Phase 3
0.6707	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6385	Approved
0.6706	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6386	Approved
0.6689	Remote Similarity	NPD17	Approved
0.6688	Remote Similarity	NPD4625	Phase 3
0.6687	Remote Similarity	NPD4357	Discontinued
0.6684	Remote Similarity	NPD7783	Phase 2
0.6684	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6535	Approved
0.6684	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD1481	Phase 2
0.6667	Remote Similarity	NPD3018	Phase 2
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD1241	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