NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.09
Volume:	276.329
LogP:	4.141
LogD:	3.66
LogS:	-3.685
# Rotatable Bonds:	2
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	2.194
Fsp3:	0.125
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:	-4.838
MDCK Permeability:	1.4175701835483778e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.963
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.177

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	98.94841766357422%
Volume Distribution (VD):	0.539
Pgp-substrate:	1.6989327669143677%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.927
CYP2C19-inhibitor:	0.876
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.639
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.886
CYP2D6-substrate:	0.934
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	10.163
Half-life (T1/2):	0.631

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.586
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.473
Carcinogencity:	0.341
Eye Corrosion:	0.02
Eye Irritation:	0.936
Respiratory Toxicity:	0.312

Download Data

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

Natural Product: NPC230943

Natural Product ID:	NPC230943
*Common Name:**	2-(2',4'-Dihydroxyphenyl)-3-Methyl-6-Methoxybenzofuran
IUPAC Name:	4-(6-methoxy-3-methyl-1-benzofuran-2-yl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	IBGFDOZOOQCQNZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O4/c1-9-12-6-4-11(19-2)8-15(12)20-16(9)13-5-3-10(17)7-14(13)18/h3-8,17-18H,1-2H3
SMILES:	Cc1c2ccc(cc2oc1c1ccc(cc1O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253277
PubChem CID:	44446828
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[17950610]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[18440233]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26938776]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32525315]

☑ 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	6
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	=	50.0	uM	PMID[552745]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	42600.0	nM	PMID[552746]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	36100.0	nM	PMID[552746]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	38700.0	nM	PMID[552746]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	44800.0	nM	PMID[552746]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34400.0	nM	PMID[552746]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	27800.0	nM	PMID[552746]

☑ 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 NPC230943 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	404
0.1-0.2	1776
0.2-0.3	4240
0.3-0.4	11223
0.4-0.5	6779
0.5-0.6	4050
0.6-0.7	5936
0.7-0.8	4741
0.8-0.85	2017
0.85-0.9	1206
0.9-0.95	312
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC302181
0.9855	High Similarity	NPC53192
0.9787	High Similarity	NPC135325
0.9716	High Similarity	NPC130581
0.9716	High Similarity	NPC12148
0.9645	High Similarity	NPC51641
0.9645	High Similarity	NPC300267
0.9645	High Similarity	NPC210826
0.9643	High Similarity	NPC225884
0.9583	High Similarity	NPC115324
0.9583	High Similarity	NPC156244
0.958	High Similarity	NPC226644
0.958	High Similarity	NPC39929
0.958	High Similarity	NPC296030
0.958	High Similarity	NPC37226
0.9577	High Similarity	NPC17816
0.9517	High Similarity	NPC207624
0.9517	High Similarity	NPC67654
0.9452	High Similarity	NPC1477
0.9452	High Similarity	NPC213608
0.9448	High Similarity	NPC193976
0.9448	High Similarity	NPC106372
0.9448	High Similarity	NPC170169
0.9448	High Similarity	NPC23668
0.9448	High Similarity	NPC58668
0.9444	High Similarity	NPC37208
0.9444	High Similarity	NPC221868
0.9437	High Similarity	NPC98926
0.9437	High Similarity	NPC155144
0.9388	High Similarity	NPC148938
0.9384	High Similarity	NPC142308
0.9384	High Similarity	NPC5871
0.9379	High Similarity	NPC167576
0.9379	High Similarity	NPC78335
0.9379	High Similarity	NPC230713
0.9375	High Similarity	NPC272194
0.9324	High Similarity	NPC247677
0.9324	High Similarity	NPC160015
0.932	High Similarity	NPC122365
0.932	High Similarity	NPC235333
0.931	High Similarity	NPC178202
0.9296	High Similarity	NPC202981
0.9286	High Similarity	NPC124269
0.9262	High Similarity	NPC296957
0.9262	High Similarity	NPC246647
0.9262	High Similarity	NPC260902
0.9262	High Similarity	NPC212967
0.9262	High Similarity	NPC164110
0.9262	High Similarity	NPC65504
0.9262	High Similarity	NPC96342
0.9257	High Similarity	NPC198490
0.9257	High Similarity	NPC297531
0.9257	High Similarity	NPC213936
0.9257	High Similarity	NPC99199
0.9252	High Similarity	NPC263676
0.9214	High Similarity	NPC228661
0.9214	High Similarity	NPC250266
0.9214	High Similarity	NPC266597
0.9214	High Similarity	NPC188879
0.92	High Similarity	NPC40583
0.92	High Similarity	NPC476350
0.92	High Similarity	NPC476349
0.9195	High Similarity	NPC180924
0.9189	High Similarity	NPC183874
0.9189	High Similarity	NPC72370
0.9189	High Similarity	NPC472462
0.9184	High Similarity	NPC116604
0.9167	High Similarity	NPC184649
0.9167	High Similarity	NPC303185
0.9155	High Similarity	NPC28337
0.9149	High Similarity	NPC188947
0.9149	High Similarity	NPC99333
0.9149	High Similarity	NPC280284
0.9143	High Similarity	NPC473887
0.9143	High Similarity	NPC127447
0.9143	High Similarity	NPC213603
0.9143	High Similarity	NPC234133
0.9143	High Similarity	NPC194281
0.9143	High Similarity	NPC231772
0.9143	High Similarity	NPC47815
0.9143	High Similarity	NPC29353
0.9143	High Similarity	NPC240593
0.9143	High Similarity	NPC124784
0.9139	High Similarity	NPC260296
0.9139	High Similarity	NPC115432
0.9137	High Similarity	NPC286336
0.9133	High Similarity	NPC268360
0.913	High Similarity	NPC205468
0.913	High Similarity	NPC212631
0.913	High Similarity	NPC129132
0.913	High Similarity	NPC257756
0.913	High Similarity	NPC87231
0.9122	High Similarity	NPC41326
0.911	High Similarity	NPC168085
0.9103	High Similarity	NPC299011
0.9103	High Similarity	NPC477955
0.9097	High Similarity	NPC106985
0.9097	High Similarity	NPC18585
0.9097	High Similarity	NPC113770
0.9097	High Similarity	NPC17262
0.9097	High Similarity	NPC166138
0.9091	High Similarity	NPC3188
0.9091	High Similarity	NPC110969
0.9085	High Similarity	NPC274784
0.9085	High Similarity	NPC316480
0.9085	High Similarity	NPC20709
0.9085	High Similarity	NPC225153
0.9085	High Similarity	NPC261234
0.9085	High Similarity	NPC310135
0.9085	High Similarity	NPC265871
0.9085	High Similarity	NPC222342
0.9085	High Similarity	NPC78913
0.9085	High Similarity	NPC150648
0.9085	High Similarity	NPC329203
0.9085	High Similarity	NPC18260
0.9079	High Similarity	NPC188486
0.9078	High Similarity	NPC290291
0.9078	High Similarity	NPC7013
0.9078	High Similarity	NPC116632
0.9078	High Similarity	NPC62735
0.9078	High Similarity	NPC181124
0.9078	High Similarity	NPC275055
0.9078	High Similarity	NPC209560
0.9078	High Similarity	NPC294409
0.9078	High Similarity	NPC254841
0.9078	High Similarity	NPC162680
0.9078	High Similarity	NPC303644
0.9073	High Similarity	NPC472877
0.9073	High Similarity	NPC244750
0.9071	High Similarity	NPC9985
0.9071	High Similarity	NPC239495
0.9071	High Similarity	NPC163029
0.9067	High Similarity	NPC45131
0.9067	High Similarity	NPC137100
0.9065	High Similarity	NPC242294
0.9065	High Similarity	NPC192304
0.9065	High Similarity	NPC28753
0.9065	High Similarity	NPC56031
0.9065	High Similarity	NPC20560
0.9065	High Similarity	NPC337373
0.9065	High Similarity	NPC18877
0.9065	High Similarity	NPC82225
0.9065	High Similarity	NPC263670
0.9065	High Similarity	NPC144051
0.9065	High Similarity	NPC294593
0.9065	High Similarity	NPC159623
0.9065	High Similarity	NPC204960
0.9065	High Similarity	NPC472365
0.9065	High Similarity	NPC188646
0.9065	High Similarity	NPC175098
0.9065	High Similarity	NPC312318
0.9065	High Similarity	NPC139813
0.9058	High Similarity	NPC313618
0.9058	High Similarity	NPC308037
0.9058	High Similarity	NPC262359
0.9058	High Similarity	NPC64359
0.9048	High Similarity	NPC317492
0.9034	High Similarity	NPC311741
0.9034	High Similarity	NPC311144
0.9034	High Similarity	NPC271288
0.9034	High Similarity	NPC71210
0.9034	High Similarity	NPC234629
0.9028	High Similarity	NPC144499
0.9028	High Similarity	NPC226636
0.9028	High Similarity	NPC310340
0.9028	High Similarity	NPC11561
0.9021	High Similarity	NPC110228
0.9021	High Similarity	NPC159275
0.9021	High Similarity	NPC129853
0.9021	High Similarity	NPC188243
0.9021	High Similarity	NPC6407
0.9021	High Similarity	NPC269652
0.9021	High Similarity	NPC270883
0.9021	High Similarity	NPC76445
0.9021	High Similarity	NPC284550
0.9021	High Similarity	NPC281207
0.9021	High Similarity	NPC261227
0.9021	High Similarity	NPC241100
0.9021	High Similarity	NPC172986
0.9021	High Similarity	NPC69769
0.9021	High Similarity	NPC11056
0.902	High Similarity	NPC312056
0.902	High Similarity	NPC84515
0.9014	High Similarity	NPC472460
0.9014	High Similarity	NPC118813
0.9014	High Similarity	NPC309154
0.9014	High Similarity	NPC201395
0.9014	High Similarity	NPC329225
0.9014	High Similarity	NPC12175
0.9014	High Similarity	NPC472368
0.9014	High Similarity	NPC55162
0.9014	High Similarity	NPC279668
0.9014	High Similarity	NPC278323
0.9014	High Similarity	NPC90665
0.9014	High Similarity	NPC21350
0.9014	High Similarity	NPC147686
0.9007	High Similarity	NPC476333
0.9007	High Similarity	NPC249606
0.9007	High Similarity	NPC13408
0.9007	High Similarity	NPC12165

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 NPC230943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	990
0.2-0.3	1451
0.3-0.4	2664
0.4-0.5	1884
0.5-0.6	1206
0.6-0.7	379
0.7-0.8	122
0.8-0.85	45
0.85-0.9	14
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9078	High Similarity	NPD2344	Approved
0.9058	High Similarity	NPD1240	Approved
0.9014	High Similarity	NPD1549	Phase 2
0.9007	High Similarity	NPD3749	Approved
0.8944	High Similarity	NPD1550	Clinical (unspecified phase)
0.8944	High Similarity	NPD1552	Clinical (unspecified phase)
0.8936	High Similarity	NPD1510	Phase 2
0.8929	High Similarity	NPD1607	Approved
0.8904	High Similarity	NPD4378	Clinical (unspecified phase)
0.8828	High Similarity	NPD2309	Approved
0.8776	High Similarity	NPD7410	Clinical (unspecified phase)
0.8741	High Similarity	NPD2796	Approved
0.869	High Similarity	NPD1243	Approved
0.8627	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD3882	Suspended
0.8562	High Similarity	NPD2800	Approved
0.8553	High Similarity	NPD7411	Suspended
0.8533	High Similarity	NPD920	Approved
0.8514	High Similarity	NPD643	Clinical (unspecified phase)
0.8503	High Similarity	NPD3750	Approved
0.8497	Intermediate Similarity	NPD1934	Approved
0.8456	Intermediate Similarity	NPD6799	Approved
0.8456	Intermediate Similarity	NPD1511	Approved
0.8452	Intermediate Similarity	NPD7768	Phase 2
0.8442	Intermediate Similarity	NPD7819	Suspended
0.8442	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7075	Discontinued
0.8367	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD4380	Phase 2
0.8366	Intermediate Similarity	NPD6599	Discontinued
0.8365	Intermediate Similarity	NPD3926	Phase 2
0.8356	Intermediate Similarity	NPD1551	Phase 2
0.8344	Intermediate Similarity	NPD1512	Approved
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD2801	Approved
0.828	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6959	Discontinued
0.8232	Intermediate Similarity	NPD6559	Discontinued
0.8188	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD3748	Approved
0.8153	Intermediate Similarity	NPD2296	Approved
0.8141	Intermediate Similarity	NPD6801	Discontinued
0.8125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD919	Approved
0.8098	Intermediate Similarity	NPD3818	Discontinued
0.8086	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6166	Phase 2
0.8086	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5494	Approved
0.8041	Intermediate Similarity	NPD2799	Discontinued
0.8039	Intermediate Similarity	NPD2533	Approved
0.8039	Intermediate Similarity	NPD2534	Approved
0.8039	Intermediate Similarity	NPD2532	Approved
0.8028	Intermediate Similarity	NPD1203	Approved
0.8013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1247	Approved
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7964	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6232	Discontinued
0.7933	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7473	Discontinued
0.7925	Intermediate Similarity	NPD3817	Phase 2
0.7905	Intermediate Similarity	NPD6651	Approved
0.7895	Intermediate Similarity	NPD4628	Phase 3
0.7895	Intermediate Similarity	NPD4287	Approved
0.7891	Intermediate Similarity	NPD943	Approved
0.7875	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4908	Phase 1
0.7844	Intermediate Similarity	NPD5953	Discontinued
0.7831	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5403	Approved
0.7817	Intermediate Similarity	NPD9717	Approved
0.7815	Intermediate Similarity	NPD1471	Phase 3
0.7806	Intermediate Similarity	NPD5401	Approved
0.78	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6280	Approved
0.7799	Intermediate Similarity	NPD6279	Approved
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7755	Intermediate Similarity	NPD3764	Approved
0.7755	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2313	Discontinued
0.7748	Intermediate Similarity	NPD6100	Approved
0.7748	Intermediate Similarity	NPD6099	Approved
0.7746	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1610	Phase 2
0.774	Intermediate Similarity	NPD6832	Phase 2
0.7725	Intermediate Similarity	NPD7286	Phase 2
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7725	Intermediate Similarity	NPD7054	Approved
0.7724	Intermediate Similarity	NPD2798	Approved
0.7722	Intermediate Similarity	NPD3226	Approved
0.7712	Intermediate Similarity	NPD2654	Approved
0.7707	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7472	Approved
0.7665	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1465	Phase 2
0.7636	Intermediate Similarity	NPD6808	Phase 2
0.7635	Intermediate Similarity	NPD3268	Approved
0.7633	Intermediate Similarity	NPD6797	Phase 2
0.7628	Intermediate Similarity	NPD7390	Discontinued
0.7622	Intermediate Similarity	NPD422	Phase 1
0.7593	Intermediate Similarity	NPD5402	Approved
0.7589	Intermediate Similarity	NPD1548	Phase 1
0.7588	Intermediate Similarity	NPD7251	Discontinued
0.7582	Intermediate Similarity	NPD2346	Discontinued
0.758	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1729	Discontinued
0.7569	Intermediate Similarity	NPD3972	Approved
0.7569	Intermediate Similarity	NPD1608	Approved
0.7566	Intermediate Similarity	NPD7033	Discontinued
0.7566	Intermediate Similarity	NPD4308	Phase 3
0.7548	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7808	Phase 3
0.7534	Intermediate Similarity	NPD2797	Approved
0.7485	Intermediate Similarity	NPD4288	Approved
0.7483	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD4361	Phase 2
0.7466	Intermediate Similarity	NPD1876	Approved
0.7465	Intermediate Similarity	NPD9545	Approved
0.7447	Intermediate Similarity	NPD9493	Approved
0.7442	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5711	Approved
0.7425	Intermediate Similarity	NPD5710	Approved
0.7425	Intermediate Similarity	NPD7229	Phase 3
0.7415	Intermediate Similarity	NPD3266	Approved
0.7415	Intermediate Similarity	NPD3267	Approved
0.7415	Intermediate Similarity	NPD1164	Approved
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD411	Approved
0.7368	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7368	Intermediate Similarity	NPD1933	Approved
0.7365	Intermediate Similarity	NPD7199	Phase 2
0.7361	Intermediate Similarity	NPD17	Approved
0.7357	Intermediate Similarity	NPD1241	Discontinued
0.7347	Intermediate Similarity	NPD3225	Approved
0.7338	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2403	Approved
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7325	Intermediate Similarity	NPD7003	Approved
0.7318	Intermediate Similarity	NPD4360	Phase 2
0.7318	Intermediate Similarity	NPD4363	Phase 3
0.7317	Intermediate Similarity	NPD5761	Phase 2
0.7317	Intermediate Similarity	NPD5760	Phase 2
0.7303	Intermediate Similarity	NPD4307	Phase 2
0.7297	Intermediate Similarity	NPD1470	Approved
0.729	Intermediate Similarity	NPD5406	Approved
0.729	Intermediate Similarity	NPD5408	Approved
0.729	Intermediate Similarity	NPD5405	Approved
0.729	Intermediate Similarity	NPD5404	Approved
0.7285	Intermediate Similarity	NPD1296	Phase 2
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1201	Approved
0.7255	Intermediate Similarity	NPD6355	Discontinued
0.7251	Intermediate Similarity	NPD3751	Discontinued
0.7248	Intermediate Similarity	NPD1019	Discontinued
0.7238	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1613	Approved
0.7186	Intermediate Similarity	NPD6971	Discontinued
0.7184	Intermediate Similarity	NPD6104	Discontinued
0.7178	Intermediate Similarity	NPD7458	Discontinued
0.7171	Intermediate Similarity	NPD6798	Discontinued
0.717	Intermediate Similarity	NPD2354	Approved
0.7162	Intermediate Similarity	NPD4749	Approved
0.712	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1481	Phase 2
0.7091	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2861	Phase 2
0.7052	Intermediate Similarity	NPD7177	Discontinued
0.7048	Intermediate Similarity	NPD7577	Discontinued
0.7037	Intermediate Similarity	NPD4662	Approved
0.7037	Intermediate Similarity	NPD4661	Approved
0.7032	Intermediate Similarity	NPD5124	Phase 1
0.7032	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1535	Discovery
0.7025	Intermediate Similarity	NPD6005	Phase 3
0.7025	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6004	Phase 3
0.7025	Intermediate Similarity	NPD2353	Approved
0.7025	Intermediate Similarity	NPD6002	Phase 3
0.7025	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3787	Discontinued
0.7017	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8312	Approved
0.7006	Intermediate Similarity	NPD8313	Approved
0.7	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)

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