NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.07
Volume:	267.823
LogP:	2.21
LogD:	2.14
LogS:	-2.833
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	3.058
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.667
MDCK Permeability:	1.320468436460942e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.23
30% Bioavailability (F30%):	0.296

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	92.01145935058594%
Volume Distribution (VD):	0.622
Pgp-substrate:	6.558170795440674%

ADMET: Metabolism

CYP1A2-inhibitor:	0.801
CYP1A2-substrate:	0.425
CYP2C19-inhibitor:	0.634
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.529
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.477
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.705
CYP3A4-substrate:	0.36

ADMET: Excretion

Clearance (CL):	14.225
Half-life (T1/2):	0.864

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.048
Drug-inuced Liver Injury (DILI):	0.774
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.684
Carcinogencity:	0.611
Eye Corrosion:	0.003
Eye Irritation:	0.09
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC471520

Natural Product ID:	NPC471520
*Common Name:**	2,6-Dihydroxy-2-[(4-Hydroxyphenyl)Methyl]-3-Benzofuranone
IUPAC Name:	2,6-dihydroxy-2-[(4-hydroxyphenyl)methyl]-1-benzofuran-3-one
Synonyms:
Standard InCHIKey:	UKGVAZCDAQXEKX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O5/c16-10-3-1-9(2-4-10)8-15(19)14(18)12-6-5-11(17)7-13(12)20-15/h1-7,16-17,19H,8H2
SMILES:	C1=CC(=CC=C1CC2(C(=O)C3=C(O2)C=C(C=C3)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254528
PubChem CID:	44446830
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001631] Aurone flavonoids [CHEMONTID:0003471] Auronols

*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	>	100.0	uM	PMID[525724]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[525725]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[525725]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[525725]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25900.0	nM	PMID[525725]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[525725]

☑ 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 NPC471520 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	1961
0.2-0.3	5037
0.3-0.4	11096
0.4-0.5	6302
0.5-0.6	4141
0.6-0.7	6062
0.7-0.8	4966
0.8-0.85	1989
0.85-0.9	684
0.9-0.95	33
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC310128
0.9712	High Similarity	NPC71210
0.9632	High Similarity	NPC254841
0.9348	High Similarity	NPC299379
0.9275	High Similarity	NPC256042
0.9275	High Similarity	NPC216361
0.9275	High Similarity	NPC281917
0.9275	High Similarity	NPC116775
0.9275	High Similarity	NPC187432
0.922	High Similarity	NPC136840
0.9203	High Similarity	NPC9985
0.9203	High Similarity	NPC239495
0.9149	High Similarity	NPC230285
0.9149	High Similarity	NPC146679
0.9149	High Similarity	NPC281207
0.9149	High Similarity	NPC59951
0.9149	High Similarity	NPC269652
0.9149	High Similarity	NPC184536
0.9149	High Similarity	NPC103342
0.9149	High Similarity	NPC103904
0.913	High Similarity	NPC172262
0.913	High Similarity	NPC248872
0.9103	High Similarity	NPC19545
0.9091	High Similarity	NPC470216
0.9085	High Similarity	NPC262094
0.9085	High Similarity	NPC90582
0.9078	High Similarity	NPC143799
0.9078	High Similarity	NPC152042
0.9078	High Similarity	NPC241838
0.9058	High Similarity	NPC57601
0.9058	High Similarity	NPC78540
0.9058	High Similarity	NPC213216
0.9058	High Similarity	NPC50898
0.9058	High Similarity	NPC274121
0.9048	High Similarity	NPC318424
0.9034	High Similarity	NPC86847
0.9034	High Similarity	NPC140840
0.9028	High Similarity	NPC155144
0.9021	High Similarity	NPC473042
0.9021	High Similarity	NPC200694
0.9021	High Similarity	NPC53192
0.9007	High Similarity	NPC147686
0.9007	High Similarity	NPC472460
0.9007	High Similarity	NPC124269
0.9007	High Similarity	NPC329225
0.9007	High Similarity	NPC306978
0.9	High Similarity	NPC161650
0.9	High Similarity	NPC210048
0.8986	High Similarity	NPC128216
0.8966	High Similarity	NPC306488
0.8966	High Similarity	NPC178343
0.8966	High Similarity	NPC5820
0.8966	High Similarity	NPC153758
0.8966	High Similarity	NPC229190
0.8966	High Similarity	NPC1940
0.8966	High Similarity	NPC148011
0.8958	High Similarity	NPC302181
0.8958	High Similarity	NPC212932
0.8958	High Similarity	NPC9117
0.8958	High Similarity	NPC158874
0.8958	High Similarity	NPC190637
0.8958	High Similarity	NPC24821
0.8958	High Similarity	NPC293053
0.8944	High Similarity	NPC261234
0.894	High Similarity	NPC311574
0.894	High Similarity	NPC264932
0.8936	High Similarity	NPC275055
0.8936	High Similarity	NPC32441
0.8936	High Similarity	NPC79943
0.8936	High Similarity	NPC228661
0.8936	High Similarity	NPC13768
0.8936	High Similarity	NPC12296
0.8936	High Similarity	NPC250266
0.8936	High Similarity	NPC84585
0.8936	High Similarity	NPC476480
0.8936	High Similarity	NPC295261
0.8936	High Similarity	NPC287246
0.8936	High Similarity	NPC243083
0.8936	High Similarity	NPC266597
0.8936	High Similarity	NPC107586
0.8936	High Similarity	NPC290291
0.8936	High Similarity	NPC296490
0.8936	High Similarity	NPC188879
0.8913	High Similarity	NPC113006
0.8913	High Similarity	NPC313618
0.8912	High Similarity	NPC477941
0.8897	High Similarity	NPC230943
0.8897	High Similarity	NPC326500
0.8897	High Similarity	NPC49130
0.8897	High Similarity	NPC4152
0.8897	High Similarity	NPC216538
0.8897	High Similarity	NPC326506
0.8897	High Similarity	NPC142731
0.8897	High Similarity	NPC279417
0.8897	High Similarity	NPC273538
0.8897	High Similarity	NPC208176
0.8897	High Similarity	NPC62290
0.8897	High Similarity	NPC306607
0.8889	High Similarity	NPC169479
0.8889	High Similarity	NPC159855
0.8889	High Similarity	NPC266725
0.8882	High Similarity	NPC172687
0.8882	High Similarity	NPC269906
0.8881	High Similarity	NPC172986
0.8881	High Similarity	NPC270883
0.8881	High Similarity	NPC261227
0.8881	High Similarity	NPC69769
0.8874	High Similarity	NPC288084
0.8873	High Similarity	NPC188947
0.8873	High Similarity	NPC280284
0.8873	High Similarity	NPC99333
0.8873	High Similarity	NPC276905
0.8873	High Similarity	NPC118813
0.8873	High Similarity	NPC201395
0.8865	High Similarity	NPC231772
0.8865	High Similarity	NPC240593
0.8865	High Similarity	NPC47815
0.8865	High Similarity	NPC194281
0.8865	High Similarity	NPC234133
0.8865	High Similarity	NPC473887
0.8865	High Similarity	NPC127447
0.8865	High Similarity	NPC29353
0.8865	High Similarity	NPC13408
0.8865	High Similarity	NPC124784
0.8857	High Similarity	NPC286336
0.8851	High Similarity	NPC260582
0.8849	High Similarity	NPC87231
0.8849	High Similarity	NPC129132
0.8849	High Similarity	NPC205468
0.8849	High Similarity	NPC212631
0.8849	High Similarity	NPC257756
0.8844	High Similarity	NPC168085
0.8841	High Similarity	NPC5515
0.8841	High Similarity	NPC270369
0.8836	High Similarity	NPC470458
0.8836	High Similarity	NPC210826
0.8836	High Similarity	NPC124729
0.8828	High Similarity	NPC225884
0.8819	High Similarity	NPC150023
0.8819	High Similarity	NPC147688
0.8819	High Similarity	NPC205006
0.8819	High Similarity	NPC156590
0.8819	High Similarity	NPC118840
0.8819	High Similarity	NPC110969
0.8819	High Similarity	NPC3188
0.8819	High Similarity	NPC64908
0.8811	High Similarity	NPC225153
0.8811	High Similarity	NPC96565
0.8811	High Similarity	NPC216978
0.8811	High Similarity	NPC222342
0.8811	High Similarity	NPC265871
0.8811	High Similarity	NPC137009
0.8811	High Similarity	NPC20709
0.8811	High Similarity	NPC303633
0.8811	High Similarity	NPC274784
0.8811	High Similarity	NPC316480
0.8811	High Similarity	NPC18260
0.8811	High Similarity	NPC220062
0.8811	High Similarity	NPC78913
0.8811	High Similarity	NPC150648
0.8811	High Similarity	NPC310135
0.8811	High Similarity	NPC301217
0.8811	High Similarity	NPC329203
0.8811	High Similarity	NPC55018
0.8808	High Similarity	NPC13879
0.88	High Similarity	NPC189130
0.8794	High Similarity	NPC151113
0.8794	High Similarity	NPC39426
0.8794	High Similarity	NPC234560
0.8792	High Similarity	NPC295650
0.8786	High Similarity	NPC188646
0.8786	High Similarity	NPC242294
0.8786	High Similarity	NPC56031
0.8786	High Similarity	NPC139813
0.8786	High Similarity	NPC144051
0.8786	High Similarity	NPC472365
0.8786	High Similarity	NPC108113
0.8786	High Similarity	NPC28753
0.8786	High Similarity	NPC337373
0.8786	High Similarity	NPC192304
0.8786	High Similarity	NPC175098
0.8786	High Similarity	NPC204960
0.8786	High Similarity	NPC159623
0.8786	High Similarity	NPC20560
0.8786	High Similarity	NPC312318
0.8786	High Similarity	NPC294593
0.8786	High Similarity	NPC263670
0.8786	High Similarity	NPC18877
0.8786	High Similarity	NPC82225
0.8786	High Similarity	NPC93756
0.8784	High Similarity	NPC37226
0.8784	High Similarity	NPC317492
0.8784	High Similarity	NPC470461
0.8784	High Similarity	NPC226644
0.8777	High Similarity	NPC31872
0.8777	High Similarity	NPC65060
0.8777	High Similarity	NPC262359
0.8777	High Similarity	NPC308037
0.8777	High Similarity	NPC475589
0.8777	High Similarity	NPC64359

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 NPC471520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	980
0.2-0.3	1667
0.3-0.4	2712
0.4-0.5	1808
0.5-0.6	1068
0.6-0.7	337
0.7-0.8	126
0.8-0.85	32
0.85-0.9	10
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9007	High Similarity	NPD1549	Phase 2
0.8936	High Similarity	NPD1552	Clinical (unspecified phase)
0.8936	High Similarity	NPD1550	Clinical (unspecified phase)
0.8913	High Similarity	NPD1240	Approved
0.8897	High Similarity	NPD4378	Clinical (unspecified phase)
0.8794	High Similarity	NPD1510	Phase 2
0.8786	High Similarity	NPD1607	Approved
0.8707	High Similarity	NPD1512	Approved
0.8699	High Similarity	NPD6799	Approved
0.8571	High Similarity	NPD1511	Approved
0.8562	High Similarity	NPD3882	Suspended
0.8514	High Similarity	NPD7410	Clinical (unspecified phase)
0.8506	High Similarity	NPD7075	Discontinued
0.8506	High Similarity	NPD4381	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD6599	Discontinued
0.8431	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD3749	Approved
0.8367	Intermediate Similarity	NPD3750	Approved
0.8366	Intermediate Similarity	NPD6801	Discontinued
0.8345	Intermediate Similarity	NPD2796	Approved
0.8345	Intermediate Similarity	NPD1551	Phase 2
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8301	Intermediate Similarity	NPD7411	Suspended
0.8299	Intermediate Similarity	NPD2800	Approved
0.8299	Intermediate Similarity	NPD1243	Approved
0.8273	Intermediate Similarity	NPD1203	Approved
0.8261	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD1934	Approved
0.8235	Intermediate Similarity	NPD4380	Phase 2
0.8194	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD2344	Approved
0.8158	Intermediate Similarity	NPD5403	Approved
0.8158	Intermediate Similarity	NPD920	Approved
0.8146	Intermediate Similarity	NPD5401	Approved
0.8146	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD3817	Phase 2
0.8133	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7819	Suspended
0.8077	Intermediate Similarity	NPD2801	Approved
0.8049	Intermediate Similarity	NPD6797	Phase 2
0.8027	Intermediate Similarity	NPD3748	Approved
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7987	Intermediate Similarity	NPD919	Approved
0.7986	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6166	Phase 2
0.7963	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7808	Phase 3
0.7947	Intermediate Similarity	NPD2309	Approved
0.7933	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD9717	Approved
0.7911	Intermediate Similarity	NPD5402	Approved
0.7892	Intermediate Similarity	NPD6559	Discontinued
0.7888	Intermediate Similarity	NPD1247	Approved
0.7879	Intermediate Similarity	NPD7074	Phase 3
0.7877	Intermediate Similarity	NPD943	Approved
0.7862	Intermediate Similarity	NPD2313	Discontinued
0.7862	Intermediate Similarity	NPD7768	Phase 2
0.7853	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD2935	Discontinued
0.7818	Intermediate Similarity	NPD7054	Approved
0.7792	Intermediate Similarity	NPD2533	Approved
0.7792	Intermediate Similarity	NPD2534	Approved
0.7792	Intermediate Similarity	NPD2532	Approved
0.7785	Intermediate Similarity	NPD2799	Discontinued
0.7771	Intermediate Similarity	NPD7472	Approved
0.775	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD422	Phase 1
0.7716	Intermediate Similarity	NPD5494	Approved
0.7711	Intermediate Similarity	NPD7286	Phase 2
0.7708	Intermediate Similarity	NPD2798	Approved
0.7683	Intermediate Similarity	NPD3926	Phase 2
0.7682	Intermediate Similarity	NPD1471	Phase 3
0.7669	Intermediate Similarity	NPD6959	Discontinued
0.7651	Intermediate Similarity	NPD6651	Approved
0.7625	Intermediate Similarity	NPD1465	Phase 2
0.7619	Intermediate Similarity	NPD5953	Discontinued
0.7603	Intermediate Similarity	NPD6832	Phase 2
0.7595	Intermediate Similarity	NPD3226	Approved
0.758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1548	Phase 1
0.755	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3751	Discontinued
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6232	Discontinued
0.7515	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD3268	Approved
0.75	Intermediate Similarity	NPD3764	Approved
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7484	Intermediate Similarity	NPD2354	Approved
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7468	Intermediate Similarity	NPD2654	Approved
0.7467	Intermediate Similarity	NPD447	Suspended
0.7467	Intermediate Similarity	NPD1933	Approved
0.7451	Intermediate Similarity	NPD2346	Discontinued
0.7448	Intermediate Similarity	NPD3225	Approved
0.7447	Intermediate Similarity	NPD9545	Approved
0.7434	Intermediate Similarity	NPD4308	Phase 3
0.7434	Intermediate Similarity	NPD7033	Discontinued
0.7431	Intermediate Similarity	NPD1608	Approved
0.7431	Intermediate Similarity	NPD1481	Phase 2
0.7429	Intermediate Similarity	NPD9493	Approved
0.7397	Intermediate Similarity	NPD2797	Approved
0.7386	Intermediate Similarity	NPD6100	Approved
0.7386	Intermediate Similarity	NPD6099	Approved
0.7383	Intermediate Similarity	NPD411	Approved
0.7371	Intermediate Similarity	NPD4287	Approved
0.7365	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4288	Approved
0.7362	Intermediate Similarity	NPD2296	Approved
0.7361	Intermediate Similarity	NPD1535	Discovery
0.7353	Intermediate Similarity	NPD1729	Discontinued
0.7351	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD230	Phase 1
0.7347	Intermediate Similarity	NPD1019	Discontinued
0.7338	Intermediate Similarity	NPD2353	Approved
0.7338	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2403	Approved
0.7318	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3787	Discontinued
0.7297	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5844	Phase 1
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3267	Approved
0.7279	Intermediate Similarity	NPD1164	Approved
0.7279	Intermediate Similarity	NPD3266	Approved
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7248	Intermediate Similarity	NPD4908	Phase 1
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD17	Approved
0.7214	Intermediate Similarity	NPD1241	Discontinued
0.7202	Intermediate Similarity	NPD5710	Approved
0.7202	Intermediate Similarity	NPD5711	Approved
0.7192	Intermediate Similarity	NPD3972	Approved
0.7188	Intermediate Similarity	NPD5049	Phase 3
0.7171	Intermediate Similarity	NPD4307	Phase 2
0.7171	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1613	Approved
0.717	Intermediate Similarity	NPD7390	Discontinued
0.7162	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD3887	Approved
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1201	Approved
0.7118	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7101	Intermediate Similarity	NPD74	Approved
0.7101	Intermediate Similarity	NPD9266	Approved
0.7073	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4361	Phase 2
0.7062	Intermediate Similarity	NPD8434	Phase 2
0.7055	Intermediate Similarity	NPD7458	Discontinued
0.7029	Intermediate Similarity	NPD9263	Approved
0.7029	Intermediate Similarity	NPD9264	Approved
0.7029	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD9267	Approved
0.702	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4363	Phase 3
0.7017	Intermediate Similarity	NPD4360	Phase 2
0.7006	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7229	Phase 3
0.6989	Remote Similarity	NPD8312	Approved
0.6989	Remote Similarity	NPD8313	Approved
0.698	Remote Similarity	NPD1876	Approved
0.6971	Remote Similarity	NPD6104	Discontinued
0.6968	Remote Similarity	NPD7584	Approved
0.6966	Remote Similarity	NPD1894	Discontinued
0.6959	Remote Similarity	NPD9269	Phase 2
0.6943	Remote Similarity	NPD5404	Approved
0.6943	Remote Similarity	NPD5405	Approved
0.6943	Remote Similarity	NPD5406	Approved
0.6943	Remote Similarity	NPD5408	Approved
0.6937	Remote Similarity	NPD6190	Approved
0.6936	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6279	Approved
0.6928	Remote Similarity	NPD6280	Approved
0.6928	Remote Similarity	NPD37	Approved
0.6923	Remote Similarity	NPD6234	Discontinued
0.6919	Remote Similarity	NPD6776	Approved
0.6919	Remote Similarity	NPD6782	Approved
0.6919	Remote Similarity	NPD6780	Approved
0.6919	Remote Similarity	NPD6777	Approved
0.6919	Remote Similarity	NPD6781	Approved
0.6919	Remote Similarity	NPD6779	Approved
0.6919	Remote Similarity	NPD6778	Approved
0.6918	Remote Similarity	NPD9268	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data