NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	330.07
Volume:	317.359
LogP:	2.184
LogD:	1.859
LogS:	-3.926
# Rotatable Bonds:	3
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.722
Synthetic Accessibility Score:	3.312
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.453
MDCK Permeability:	9.025396138895303e-06
Pgp-inhibitor:	0.016
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.417
30% Bioavailability (F30%):	0.877

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	92.66874694824219%
Volume Distribution (VD):	0.581
Pgp-substrate:	8.469780921936035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.664
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.426
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.812
CYP2D6-substrate:	0.289
CYP3A4-inhibitor:	0.908
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	2.743
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.263
Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.302
Carcinogencity:	0.446
Eye Corrosion:	0.004
Eye Irritation:	0.807
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC477941

Natural Product ID:	NPC477941
*Common Name:**	(2R,3S)-3-Acetoxy-4',5,7-trihydroxy-2,3-dihydroflavone
IUPAC Name:	[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl] acetate
Synonyms:
Standard InCHIKey:	WJMRMTQQBTZCNV-IAGOWNOFSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-8(18)23-17-15(22)14-12(21)6-11(20)7-13(14)24-16(17)9-2-4-10(19)5-3-9/h2-7,16-17,19-21H,1H3/t16-,17-/m1/s1
SMILES:	CC(=O)O[C@H]1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10426746
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones [CHEMONTID:0001362] Flavanonols

*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
NPO12618	Siparuna andina	Species	Siparunaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19299148]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	24.3	ug/ml	PMID[19299148]

☑ 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 NPC477941 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	339
0.1-0.2	1478
0.2-0.3	3925
0.3-0.4	8829
0.4-0.5	9390
0.5-0.6	3771
0.6-0.7	5422
0.7-0.8	5169
0.8-0.85	2895
0.85-0.9	1216
0.9-0.95	254
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC295650
0.9583	High Similarity	NPC44721
0.9583	High Similarity	NPC122828
0.9583	High Similarity	NPC40086
0.9583	High Similarity	NPC176869
0.9583	High Similarity	NPC211466
0.9583	High Similarity	NPC3779
0.9583	High Similarity	NPC476182
0.951	High Similarity	NPC470216
0.9448	High Similarity	NPC472918
0.9444	High Similarity	NPC142731
0.9444	High Similarity	NPC306607
0.9444	High Similarity	NPC4152
0.9444	High Similarity	NPC49130
0.9444	High Similarity	NPC279417
0.9444	High Similarity	NPC326506
0.9444	High Similarity	NPC208176
0.9444	High Similarity	NPC62290
0.9404	High Similarity	NPC471744
0.9379	High Similarity	NPC1940
0.9379	High Similarity	NPC148011
0.9379	High Similarity	NPC229190
0.9366	High Similarity	NPC20709
0.9366	High Similarity	NPC222342
0.9366	High Similarity	NPC150648
0.9366	High Similarity	NPC225153
0.9366	High Similarity	NPC274784
0.9366	High Similarity	NPC310135
0.9366	High Similarity	NPC329203
0.9366	High Similarity	NPC265871
0.9342	High Similarity	NPC112418
0.9338	High Similarity	NPC104677
0.9329	High Similarity	NPC236756
0.9329	High Similarity	NPC311579
0.9324	High Similarity	NPC262039
0.9324	High Similarity	NPC319910
0.9324	High Similarity	NPC254412
0.9324	High Similarity	NPC262038
0.9324	High Similarity	NPC278476
0.932	High Similarity	NPC277032
0.9301	High Similarity	NPC110228
0.9301	High Similarity	NPC184536
0.9301	High Similarity	NPC103342
0.9301	High Similarity	NPC103904
0.9301	High Similarity	NPC6407
0.9301	High Similarity	NPC146679
0.9301	High Similarity	NPC59951
0.9301	High Similarity	NPC188243
0.9301	High Similarity	NPC230285
0.9281	High Similarity	NPC471745
0.9267	High Similarity	NPC473241
0.9262	High Similarity	NPC138288
0.9262	High Similarity	NPC35567
0.9262	High Similarity	NPC216035
0.9262	High Similarity	NPC217149
0.9262	High Similarity	NPC171651
0.9262	High Similarity	NPC243171
0.9257	High Similarity	NPC105136
0.9257	High Similarity	NPC267117
0.9252	High Similarity	NPC218569
0.9247	High Similarity	NPC153758
0.9236	High Similarity	NPC136840
0.9236	High Similarity	NPC213322
0.9236	High Similarity	NPC312391
0.9236	High Similarity	NPC90582
0.9236	High Similarity	NPC262094
0.9236	High Similarity	NPC324386
0.9236	High Similarity	NPC4743
0.9231	High Similarity	NPC143799
0.9231	High Similarity	NPC152042
0.9231	High Similarity	NPC241838
0.9231	High Similarity	NPC140890
0.9225	High Similarity	NPC295261
0.9225	High Similarity	NPC13768
0.9225	High Similarity	NPC287246
0.9225	High Similarity	NPC107586
0.9225	High Similarity	NPC296490
0.9225	High Similarity	NPC32441
0.9225	High Similarity	NPC12296
0.9225	High Similarity	NPC79943
0.9225	High Similarity	NPC243083
0.9216	High Similarity	NPC129217
0.9216	High Similarity	NPC159579
0.9216	High Similarity	NPC224530
0.9216	High Similarity	NPC259957
0.9216	High Similarity	NPC216496
0.9216	High Similarity	NPC85707
0.9216	High Similarity	NPC48093
0.9205	High Similarity	NPC471500
0.9205	High Similarity	NPC127406
0.92	High Similarity	NPC293286
0.92	High Similarity	NPC203080
0.9195	High Similarity	NPC471229
0.9184	High Similarity	NPC21835
0.9178	High Similarity	NPC71210
0.9172	High Similarity	NPC37496
0.9172	High Similarity	NPC107572
0.9172	High Similarity	NPC78
0.9172	High Similarity	NPC166482
0.9172	High Similarity	NPC40833
0.9172	High Similarity	NPC306829
0.9172	High Similarity	NPC76372
0.9172	High Similarity	NPC177354
0.9172	High Similarity	NPC64915
0.9172	High Similarity	NPC76338
0.9172	High Similarity	NPC148757
0.9172	High Similarity	NPC125855
0.9172	High Similarity	NPC167624
0.9172	High Similarity	NPC1089
0.9172	High Similarity	NPC194432
0.9172	High Similarity	NPC220998
0.9172	High Similarity	NPC73028
0.9172	High Similarity	NPC32739
0.9172	High Similarity	NPC10937
0.9172	High Similarity	NPC227579
0.9172	High Similarity	NPC228504
0.9172	High Similarity	NPC324436
0.9172	High Similarity	NPC223500
0.9172	High Similarity	NPC328164
0.9172	High Similarity	NPC265040
0.9172	High Similarity	NPC296917
0.9172	High Similarity	NPC166934
0.9172	High Similarity	NPC66515
0.9172	High Similarity	NPC324134
0.9172	High Similarity	NPC182852
0.9172	High Similarity	NPC161506
0.9167	High Similarity	NPC129853
0.9167	High Similarity	NPC76445
0.9167	High Similarity	NPC281207
0.9167	High Similarity	NPC269652
0.9167	High Similarity	NPC284550
0.9161	High Similarity	NPC472460
0.9161	High Similarity	NPC188947
0.9161	High Similarity	NPC147686
0.9161	High Similarity	NPC99333
0.9161	High Similarity	NPC280284
0.9161	High Similarity	NPC118813
0.9161	High Similarity	NPC329225
0.9156	High Similarity	NPC27942
0.915	High Similarity	NPC153342
0.9145	High Similarity	NPC471479
0.9145	High Similarity	NPC471515
0.9145	High Similarity	NPC6985
0.9145	High Similarity	NPC43638
0.9145	High Similarity	NPC108456
0.9139	High Similarity	NPC48579
0.9139	High Similarity	NPC259710
0.9139	High Similarity	NPC217706
0.9139	High Similarity	NPC207809
0.9139	High Similarity	NPC304745
0.9139	High Similarity	NPC304207
0.9139	High Similarity	NPC111341
0.9133	High Similarity	NPC210597
0.9128	High Similarity	NPC180351
0.9122	High Similarity	NPC211811
0.9116	High Similarity	NPC5820
0.9116	High Similarity	NPC472629
0.9116	High Similarity	NPC470458
0.9116	High Similarity	NPC178343
0.9116	High Similarity	NPC306488
0.911	High Similarity	NPC214166
0.911	High Similarity	NPC125894
0.911	High Similarity	NPC39329
0.911	High Similarity	NPC257097
0.911	High Similarity	NPC478086
0.911	High Similarity	NPC68104
0.911	High Similarity	NPC221432
0.911	High Similarity	NPC169591
0.911	High Similarity	NPC158874
0.911	High Similarity	NPC185276
0.911	High Similarity	NPC77794
0.911	High Similarity	NPC150408
0.911	High Similarity	NPC149026
0.911	High Similarity	NPC164980
0.911	High Similarity	NPC81697
0.911	High Similarity	NPC107177
0.911	High Similarity	NPC143896
0.911	High Similarity	NPC175504
0.911	High Similarity	NPC113770
0.911	High Similarity	NPC75049
0.911	High Similarity	NPC85162
0.911	High Similarity	NPC310130
0.911	High Similarity	NPC91560
0.911	High Similarity	NPC316816
0.911	High Similarity	NPC223812
0.911	High Similarity	NPC278249
0.9103	High Similarity	NPC3188
0.9103	High Similarity	NPC258630
0.9103	High Similarity	NPC150023
0.9103	High Similarity	NPC279650
0.9103	High Similarity	NPC156190
0.9103	High Similarity	NPC248372
0.9103	High Similarity	NPC17170
0.9103	High Similarity	NPC166689
0.9103	High Similarity	NPC96408
0.9103	High Similarity	NPC110038
0.9097	High Similarity	NPC121703
0.9097	High Similarity	NPC261234
0.9091	High Similarity	NPC476480
0.9091	High Similarity	NPC290291

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 NPC477941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	879
0.2-0.3	1685
0.3-0.4	2555
0.4-0.5	1876
0.5-0.6	1162
0.6-0.7	474
0.7-0.8	147
0.8-0.85	44
0.85-0.9	15
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.94	High Similarity	NPD7075	Discontinued
0.9329	High Similarity	NPD7096	Clinical (unspecified phase)
0.9241	High Similarity	NPD6799	Approved
0.9225	High Similarity	NPD1550	Clinical (unspecified phase)
0.9225	High Similarity	NPD1552	Clinical (unspecified phase)
0.9161	High Similarity	NPD1549	Phase 2
0.9133	High Similarity	NPD6801	Discontinued
0.9048	High Similarity	NPD4378	Clinical (unspecified phase)
0.9007	High Similarity	NPD1934	Approved
0.9	High Similarity	NPD6599	Discontinued
0.8889	High Similarity	NPD3817	Phase 2
0.8824	High Similarity	NPD2393	Clinical (unspecified phase)
0.8816	High Similarity	NPD7411	Suspended
0.88	High Similarity	NPD5403	Approved
0.8792	High Similarity	NPD5401	Approved
0.8774	High Similarity	NPD4381	Clinical (unspecified phase)
0.875	High Similarity	NPD7804	Clinical (unspecified phase)
0.875	High Similarity	NPD4380	Phase 2
0.869	High Similarity	NPD1510	Phase 2
0.8679	High Similarity	NPD6167	Clinical (unspecified phase)
0.8679	High Similarity	NPD6168	Clinical (unspecified phase)
0.8679	High Similarity	NPD6166	Phase 2
0.8671	High Similarity	NPD1240	Approved
0.863	High Similarity	NPD2796	Approved
0.8609	High Similarity	NPD1512	Approved
0.859	High Similarity	NPD3882	Suspended
0.8581	High Similarity	NPD7819	Suspended
0.8552	High Similarity	NPD1607	Approved
0.8537	High Similarity	NPD4338	Clinical (unspecified phase)
0.8528	High Similarity	NPD6797	Phase 2
0.8526	High Similarity	NPD8443	Clinical (unspecified phase)
0.8526	High Similarity	NPD5402	Approved
0.8477	Intermediate Similarity	NPD1511	Approved
0.8476	Intermediate Similarity	NPD7251	Discontinued
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD2801	Approved
0.8424	Intermediate Similarity	NPD7808	Phase 3
0.8421	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD3750	Approved
0.8378	Intermediate Similarity	NPD1551	Phase 2
0.8354	Intermediate Similarity	NPD7074	Phase 3
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD3749	Approved
0.8293	Intermediate Similarity	NPD7054	Approved
0.8267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7472	Approved
0.8239	Intermediate Similarity	NPD7768	Phase 2
0.8232	Intermediate Similarity	NPD3818	Discontinued
0.8193	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD4628	Phase 3
0.8151	Intermediate Similarity	NPD6798	Discontinued
0.8148	Intermediate Similarity	NPD6959	Discontinued
0.8144	Intermediate Similarity	NPD6559	Discontinued
0.8137	Intermediate Similarity	NPD919	Approved
0.8098	Intermediate Similarity	NPD6232	Discontinued
0.8086	Intermediate Similarity	NPD5494	Approved
0.8077	Intermediate Similarity	NPD920	Approved
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8067	Intermediate Similarity	NPD3748	Approved
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8056	Intermediate Similarity	NPD1203	Approved
0.8039	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2935	Discontinued
0.7974	Intermediate Similarity	NPD2800	Approved
0.7974	Intermediate Similarity	NPD1243	Approved
0.7973	Intermediate Similarity	NPD6233	Phase 2
0.7964	Intermediate Similarity	NPD7286	Phase 2
0.7955	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2532	Approved
0.7949	Intermediate Similarity	NPD2534	Approved
0.7949	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2533	Approved
0.7947	Intermediate Similarity	NPD7033	Discontinued
0.7935	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2313	Discontinued
0.7902	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6832	Phase 2
0.7888	Intermediate Similarity	NPD1465	Phase 2
0.787	Intermediate Similarity	NPD5953	Discontinued
0.7867	Intermediate Similarity	NPD1933	Approved
0.7867	Intermediate Similarity	NPD6355	Discontinued
0.7847	Intermediate Similarity	NPD9717	Approved
0.7829	Intermediate Similarity	NPD2799	Discontinued
0.7829	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD1247	Approved
0.7798	Intermediate Similarity	NPD3751	Discontinued
0.7785	Intermediate Similarity	NPD3268	Approved
0.7784	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD422	Phase 1
0.7764	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2354	Approved
0.7756	Intermediate Similarity	NPD3887	Approved
0.775	Intermediate Similarity	NPD3226	Approved
0.7727	Intermediate Similarity	NPD2344	Approved
0.7727	Intermediate Similarity	NPD2346	Discontinued
0.7697	Intermediate Similarity	NPD6651	Approved
0.7687	Intermediate Similarity	NPD2797	Approved
0.7682	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1613	Approved
0.7665	Intermediate Similarity	NPD3787	Discontinued
0.7655	Intermediate Similarity	NPD1610	Phase 2
0.7651	Intermediate Similarity	NPD4908	Phase 1
0.7632	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5124	Phase 1
0.7632	Intermediate Similarity	NPD230	Phase 1
0.7632	Intermediate Similarity	NPD447	Suspended
0.7628	Intermediate Similarity	NPD1652	Phase 2
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD9545	Approved
0.7622	Intermediate Similarity	NPD1548	Phase 1
0.7619	Intermediate Similarity	NPD3225	Approved
0.7619	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3926	Phase 2
0.7616	Intermediate Similarity	NPD4062	Phase 3
0.7613	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2353	Approved
0.761	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4308	Phase 3
0.758	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3266	Approved
0.7568	Intermediate Similarity	NPD3267	Approved
0.7566	Intermediate Similarity	NPD943	Approved
0.755	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6099	Approved
0.7548	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2309	Approved
0.7532	Intermediate Similarity	NPD6190	Approved
0.7517	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD8434	Phase 2
0.7483	Intermediate Similarity	NPD1608	Approved
0.7483	Intermediate Similarity	NPD9493	Approved
0.7467	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5711	Approved
0.7456	Intermediate Similarity	NPD5710	Approved
0.7453	Intermediate Similarity	NPD5049	Phase 3
0.7451	Intermediate Similarity	NPD4060	Phase 1
0.7444	Intermediate Similarity	NPD4360	Phase 2
0.7444	Intermediate Similarity	NPD4363	Phase 3
0.7438	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1296	Phase 2
0.7429	Intermediate Similarity	NPD8312	Approved
0.7429	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD7458	Discontinued
0.741	Intermediate Similarity	NPD4288	Approved
0.7405	Intermediate Similarity	NPD7435	Discontinued
0.7403	Intermediate Similarity	NPD4340	Discontinued
0.74	Intermediate Similarity	NPD2798	Approved
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7372	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2403	Approved
0.7365	Intermediate Similarity	NPD1481	Phase 2
0.7349	Intermediate Similarity	NPD8455	Phase 2
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4307	Phase 2
0.732	Intermediate Similarity	NPD411	Approved
0.732	Intermediate Similarity	NPD3764	Approved
0.7318	Intermediate Similarity	NPD4287	Approved
0.7317	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8150	Discontinued
0.7297	Intermediate Similarity	NPD1535	Discovery
0.7296	Intermediate Similarity	NPD2654	Approved
0.7289	Intermediate Similarity	NPD37	Approved
0.7287	Intermediate Similarity	NPD7584	Approved
0.7279	Intermediate Similarity	NPD17	Approved
0.7278	Intermediate Similarity	NPD6234	Discontinued
0.7278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD4967	Phase 2
0.7262	Intermediate Similarity	NPD4966	Approved
0.7261	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1894	Discontinued
0.7256	Intermediate Similarity	NPD1653	Approved
0.7255	Intermediate Similarity	NPD7095	Approved
0.7255	Intermediate Similarity	NPD3027	Phase 3
0.7251	Intermediate Similarity	NPD7229	Phase 3
0.7243	Intermediate Similarity	NPD6782	Approved
0.7243	Intermediate Similarity	NPD6780	Approved
0.7243	Intermediate Similarity	NPD6778	Approved
0.7243	Intermediate Similarity	NPD6777	Approved
0.7243	Intermediate Similarity	NPD6781	Approved
0.7243	Intermediate Similarity	NPD6776	Approved
0.7243	Intermediate Similarity	NPD6779	Approved
0.7233	Intermediate Similarity	NPD4534	Discontinued
0.7233	Intermediate Similarity	NPD2897	Discontinued
0.7229	Intermediate Similarity	NPD5890	Approved
0.7229	Intermediate Similarity	NPD5889	Approved
0.7222	Intermediate Similarity	NPD7390	Discontinued
0.7222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7097	Phase 1
0.7178	Intermediate Similarity	NPD4662	Approved
0.7178	Intermediate Similarity	NPD4661	Approved
0.7176	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7874	Approved
0.7173	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1471	Phase 3

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