NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	178.06
Volume:	180.228
LogP:	1.593
LogD:	1.667
LogS:	-2.378
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.651
Synthetic Accessibility Score:	3.094
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.552
MDCK Permeability:	2.1436993847601116e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.94
Plasma Protein Binding (PPB):	77.48738861083984%
Volume Distribution (VD):	1.006
Pgp-substrate:	17.010528564453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.848
CYP1A2-substrate:	0.765
CYP2C19-inhibitor:	0.288
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.408
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.673
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.408

ADMET: Excretion

Clearance (CL):	6.043
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.072
Carcinogencity:	0.052
Eye Corrosion:	0.004
Eye Irritation:	0.548
Respiratory Toxicity:	0.125

Download Data

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

Natural Product: NPC324488

Natural Product ID:	NPC324488
*Common Name:**	2-Hydroxy-2,6-Dimethyl-1-Benzofuran-3-One
IUPAC Name:	2-hydroxy-2,6-dimethyl-1-benzofuran-3-one
Synonyms:
Standard InCHIKey:	ZRKDKQNGWJTUNM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H10O3/c1-6-3-4-7-8(5-6)13-10(2,12)9(7)11/h3-5,12H,1-2H3
SMILES:	CC1=CC2=C(C=C1)C(=O)C(O2)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1795988
PubChem CID:	53355238
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21391659]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30653318]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	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
Others	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	0.02	%	PMID[469036]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	17.3	%	PMID[469036]

☑ 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 NPC324488 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	327
0.1-0.2	1662
0.2-0.3	4495
0.3-0.4	11310
0.4-0.5	6983
0.5-0.6	4927
0.6-0.7	8766
0.7-0.8	4159
0.8-0.85	61
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.938	High Similarity	NPC477536
0.9242	High Similarity	NPC477534
0.9037	High Similarity	NPC477537
0.8897	High Similarity	NPC477535
0.872	High Similarity	NPC171023
0.8605	High Similarity	NPC93730
0.8529	High Similarity	NPC217914
0.8478	Intermediate Similarity	NPC98395
0.8473	Intermediate Similarity	NPC224657
0.8473	Intermediate Similarity	NPC287473
0.8438	Intermediate Similarity	NPC470092
0.8433	Intermediate Similarity	NPC278787
0.838	Intermediate Similarity	NPC469385
0.837	Intermediate Similarity	NPC141549
0.837	Intermediate Similarity	NPC205360
0.8356	Intermediate Similarity	NPC175617
0.8333	Intermediate Similarity	NPC252208
0.8321	Intermediate Similarity	NPC265793
0.831	Intermediate Similarity	NPC471520
0.8309	Intermediate Similarity	NPC118253
0.8299	Intermediate Similarity	NPC471347
0.8299	Intermediate Similarity	NPC471349
0.8296	Intermediate Similarity	NPC7569
0.8288	Intermediate Similarity	NPC475717
0.8286	Intermediate Similarity	NPC268691
0.8258	Intermediate Similarity	NPC56332
0.8244	Intermediate Similarity	NPC311219
0.8239	Intermediate Similarity	NPC310128
0.8235	Intermediate Similarity	NPC301717
0.8222	Intermediate Similarity	NPC473019
0.8217	Intermediate Similarity	NPC35744
0.8209	Intermediate Similarity	NPC298884
0.8207	Intermediate Similarity	NPC469425
0.8201	Intermediate Similarity	NPC232996
0.8194	Intermediate Similarity	NPC71210
0.8189	Intermediate Similarity	NPC161304
0.8156	Intermediate Similarity	NPC477408
0.8156	Intermediate Similarity	NPC112757
0.8151	Intermediate Similarity	NPC219560
0.8148	Intermediate Similarity	NPC201419
0.8143	Intermediate Similarity	NPC130976
0.814	Intermediate Similarity	NPC41567
0.814	Intermediate Similarity	NPC32298
0.8134	Intermediate Similarity	NPC474264
0.812	Intermediate Similarity	NPC193805
0.812	Intermediate Similarity	NPC4012
0.8116	Intermediate Similarity	NPC470871
0.8095	Intermediate Similarity	NPC228906
0.8095	Intermediate Similarity	NPC471348
0.8095	Intermediate Similarity	NPC226578
0.8095	Intermediate Similarity	NPC469416
0.8088	Intermediate Similarity	NPC939
0.8077	Intermediate Similarity	NPC54243
0.8074	Intermediate Similarity	NPC71525
0.8074	Intermediate Similarity	NPC470841
0.8071	Intermediate Similarity	NPC472881
0.8062	Intermediate Similarity	NPC240664
0.8045	Intermediate Similarity	NPC182646
0.8045	Intermediate Similarity	NPC141252
0.8045	Intermediate Similarity	NPC11799
0.803	Intermediate Similarity	NPC314329
0.8015	Intermediate Similarity	NPC230951
0.8014	Intermediate Similarity	NPC301341
0.8014	Intermediate Similarity	NPC308799
0.8014	Intermediate Similarity	NPC471346
0.8014	Intermediate Similarity	NPC284184
0.8	Intermediate Similarity	NPC470331
0.8	Intermediate Similarity	NPC237868
0.8	Intermediate Similarity	NPC22222
0.8	Intermediate Similarity	NPC281513
0.8	Intermediate Similarity	NPC152159
0.7972	Intermediate Similarity	NPC137009
0.7971	Intermediate Similarity	NPC279596
0.7971	Intermediate Similarity	NPC477412
0.7971	Intermediate Similarity	NPC11173
0.7959	Intermediate Similarity	NPC113428
0.7959	Intermediate Similarity	NPC61284
0.7958	Intermediate Similarity	NPC265181
0.7958	Intermediate Similarity	NPC254841
0.7945	Intermediate Similarity	NPC98926
0.7943	Intermediate Similarity	NPC278832
0.7943	Intermediate Similarity	NPC64157
0.7941	Intermediate Similarity	NPC22783
0.7941	Intermediate Similarity	NPC45537
0.7939	Intermediate Similarity	NPC201284
0.7931	Intermediate Similarity	NPC476310
0.7931	Intermediate Similarity	NPC1534
0.7931	Intermediate Similarity	NPC476164
0.7929	Intermediate Similarity	NPC477210
0.7926	Intermediate Similarity	NPC470858
0.7923	Intermediate Similarity	NPC217423
0.7919	Intermediate Similarity	NPC167576
0.7917	Intermediate Similarity	NPC145673
0.7914	Intermediate Similarity	NPC474340
0.7914	Intermediate Similarity	NPC472882
0.7914	Intermediate Similarity	NPC477406
0.791	Intermediate Similarity	NPC472888
0.7907	Intermediate Similarity	NPC240163
0.7907	Intermediate Similarity	NPC188907
0.7905	Intermediate Similarity	NPC19545
0.7902	Intermediate Similarity	NPC18457
0.7899	Intermediate Similarity	NPC198305
0.7891	Intermediate Similarity	NPC279916
0.7891	Intermediate Similarity	NPC53953
0.7883	Intermediate Similarity	NPC237225
0.7881	Intermediate Similarity	NPC301233
0.7879	Intermediate Similarity	NPC246214
0.7877	Intermediate Similarity	NPC105381
0.7877	Intermediate Similarity	NPC471600
0.7877	Intermediate Similarity	NPC10302
0.7872	Intermediate Similarity	NPC22644
0.7872	Intermediate Similarity	NPC298900
0.7868	Intermediate Similarity	NPC51037
0.7862	Intermediate Similarity	NPC329493
0.7857	Intermediate Similarity	NPC287533
0.7857	Intermediate Similarity	NPC269906
0.7857	Intermediate Similarity	NPC171968
0.7857	Intermediate Similarity	NPC128216
0.7852	Intermediate Similarity	NPC269420
0.7852	Intermediate Similarity	NPC265910
0.7852	Intermediate Similarity	NPC91475
0.7852	Intermediate Similarity	NPC70764
0.7852	Intermediate Similarity	NPC470163
0.7852	Intermediate Similarity	NPC470162
0.7843	Intermediate Similarity	NPC476404
0.7843	Intermediate Similarity	NPC317900
0.7843	Intermediate Similarity	NPC294300
0.7842	Intermediate Similarity	NPC473982
0.7842	Intermediate Similarity	NPC7012
0.7838	Intermediate Similarity	NPC86847
0.7838	Intermediate Similarity	NPC140840
0.7836	Intermediate Similarity	NPC46634
0.7829	Intermediate Similarity	NPC237560
0.7826	Intermediate Similarity	NPC170546
0.7826	Intermediate Similarity	NPC66246
0.7826	Intermediate Similarity	NPC57552
0.7826	Intermediate Similarity	NPC187907
0.7823	Intermediate Similarity	NPC469764
0.7823	Intermediate Similarity	NPC47152
0.7823	Intermediate Similarity	NPC473951
0.7823	Intermediate Similarity	NPC155144
0.7817	Intermediate Similarity	NPC141934
0.7815	Intermediate Similarity	NPC473967
0.7815	Intermediate Similarity	NPC275878
0.7808	Intermediate Similarity	NPC316691
0.7803	Intermediate Similarity	NPC98748
0.7801	Intermediate Similarity	NPC211164
0.7801	Intermediate Similarity	NPC209858
0.7794	Intermediate Similarity	NPC2771
0.7794	Intermediate Similarity	NPC4164
0.7793	Intermediate Similarity	NPC124365
0.7786	Intermediate Similarity	NPC160199
0.7786	Intermediate Similarity	NPC470160
0.7786	Intermediate Similarity	NPC269414
0.7785	Intermediate Similarity	NPC228012
0.7785	Intermediate Similarity	NPC280025
0.7778	Intermediate Similarity	NPC224584
0.7778	Intermediate Similarity	NPC473988
0.7778	Intermediate Similarity	NPC154341
0.7778	Intermediate Similarity	NPC1268
0.777	Intermediate Similarity	NPC183348
0.777	Intermediate Similarity	NPC469758
0.777	Intermediate Similarity	NPC109778
0.777	Intermediate Similarity	NPC130176
0.777	Intermediate Similarity	NPC282230
0.777	Intermediate Similarity	NPC196114
0.777	Intermediate Similarity	NPC99454
0.7763	Intermediate Similarity	NPC279930
0.7763	Intermediate Similarity	NPC72370
0.7763	Intermediate Similarity	NPC290927
0.7763	Intermediate Similarity	NPC189130
0.7762	Intermediate Similarity	NPC471542
0.7755	Intermediate Similarity	NPC274085
0.7755	Intermediate Similarity	NPC306816
0.7755	Intermediate Similarity	NPC89664
0.7755	Intermediate Similarity	NPC469642
0.7755	Intermediate Similarity	NPC477409
0.7754	Intermediate Similarity	NPC125887
0.7748	Intermediate Similarity	NPC318424
0.7748	Intermediate Similarity	NPC39819
0.7746	Intermediate Similarity	NPC248872
0.7746	Intermediate Similarity	NPC204592
0.7744	Intermediate Similarity	NPC14177
0.7742	Intermediate Similarity	NPC313368
0.774	Intermediate Similarity	NPC136840
0.774	Intermediate Similarity	NPC24075
0.7727	Intermediate Similarity	NPC473282
0.7727	Intermediate Similarity	NPC161650
0.7727	Intermediate Similarity	NPC94637
0.7727	Intermediate Similarity	NPC206007
0.7727	Intermediate Similarity	NPC217602
0.7727	Intermediate Similarity	NPC104380
0.7727	Intermediate Similarity	NPC210048
0.7724	Intermediate Similarity	NPC109232
0.7724	Intermediate Similarity	NPC37206
0.7721	Intermediate Similarity	NPC310540
0.7718	Intermediate Similarity	NPC17816
0.7718	Intermediate Similarity	NPC117463
0.7718	Intermediate Similarity	NPC71055
0.7718	Intermediate Similarity	NPC150215

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 NPC324488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	1004
0.2-0.3	1495
0.3-0.4	2670
0.4-0.5	1938
0.5-0.6	1151
0.6-0.7	462
0.7-0.8	107
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8345	Intermediate Similarity	NPD2346	Discontinued
0.8296	Intermediate Similarity	NPD411	Approved
0.8271	Intermediate Similarity	NPD2798	Approved
0.8244	Intermediate Similarity	NPD9717	Approved
0.8162	Intermediate Similarity	NPD2313	Discontinued
0.8116	Intermediate Similarity	NPD447	Suspended
0.803	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1471	Phase 3
0.7958	Intermediate Similarity	NPD2344	Approved
0.7943	Intermediate Similarity	NPD2799	Discontinued
0.7926	Intermediate Similarity	NPD1203	Approved
0.7852	Intermediate Similarity	NPD3226	Approved
0.7762	Intermediate Similarity	NPD2935	Discontinued
0.774	Intermediate Similarity	NPD2309	Approved
0.7737	Intermediate Similarity	NPD1019	Discontinued
0.773	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD9493	Approved
0.7708	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4308	Phase 3
0.7676	Intermediate Similarity	NPD1607	Approved
0.7639	Intermediate Similarity	NPD1551	Phase 2
0.7626	Intermediate Similarity	NPD6832	Phase 2
0.7615	Intermediate Similarity	NPD1241	Discontinued
0.7612	Intermediate Similarity	NPD1778	Approved
0.7584	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1608	Approved
0.7566	Intermediate Similarity	NPD6599	Discontinued
0.7548	Intermediate Similarity	NPD3882	Suspended
0.7535	Intermediate Similarity	NPD1240	Approved
0.7535	Intermediate Similarity	NPD4307	Phase 2
0.7533	Intermediate Similarity	NPD1512	Approved
0.7517	Intermediate Similarity	NPD6799	Approved
0.7483	Intermediate Similarity	NPD1243	Approved
0.7483	Intermediate Similarity	NPD1933	Approved
0.7444	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1549	Phase 2
0.741	Intermediate Similarity	NPD2797	Approved
0.74	Intermediate Similarity	NPD1511	Approved
0.7397	Intermediate Similarity	NPD2796	Approved
0.7378	Intermediate Similarity	NPD6559	Discontinued
0.7372	Intermediate Similarity	NPD1201	Approved
0.7372	Intermediate Similarity	NPD5402	Approved
0.7372	Intermediate Similarity	NPD3817	Phase 2
0.7361	Intermediate Similarity	NPD6355	Discontinued
0.7353	Intermediate Similarity	NPD17	Approved
0.7351	Intermediate Similarity	NPD2533	Approved
0.7351	Intermediate Similarity	NPD5401	Approved
0.7351	Intermediate Similarity	NPD2534	Approved
0.7351	Intermediate Similarity	NPD2532	Approved
0.7347	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD919	Approved
0.7338	Intermediate Similarity	NPD1283	Approved
0.7329	Intermediate Similarity	NPD1510	Phase 2
0.7319	Intermediate Similarity	NPD3972	Approved
0.7308	Intermediate Similarity	NPD7819	Suspended
0.7299	Intermediate Similarity	NPD3496	Discontinued
0.7297	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD9264	Approved
0.7287	Intermediate Similarity	NPD9263	Approved
0.7287	Intermediate Similarity	NPD9267	Approved
0.7286	Intermediate Similarity	NPD1470	Approved
0.7278	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7267	Intermediate Similarity	NPD2354	Approved
0.7255	Intermediate Similarity	NPD920	Approved
0.7255	Intermediate Similarity	NPD5403	Approved
0.725	Intermediate Similarity	NPD1247	Approved
0.7248	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2800	Approved
0.7244	Intermediate Similarity	NPD1934	Approved
0.7244	Intermediate Similarity	NPD6844	Discontinued
0.7239	Intermediate Similarity	NPD3818	Discontinued
0.7239	Intermediate Similarity	NPD6671	Approved
0.7237	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD74	Approved
0.7231	Intermediate Similarity	NPD9266	Approved
0.7226	Intermediate Similarity	NPD4626	Approved
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1876	Approved
0.72	Intermediate Similarity	NPD3750	Approved
0.72	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4628	Phase 3
0.7197	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5049	Phase 3
0.719	Intermediate Similarity	NPD6273	Approved
0.717	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3266	Approved
0.7163	Intermediate Similarity	NPD3267	Approved
0.7161	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1651	Approved
0.7153	Intermediate Similarity	NPD5691	Approved
0.7152	Intermediate Similarity	NPD2296	Approved
0.7134	Intermediate Similarity	NPD6801	Discontinued
0.7132	Intermediate Similarity	NPD9697	Approved
0.7124	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4662	Approved
0.7124	Intermediate Similarity	NPD4661	Approved
0.7122	Intermediate Similarity	NPD1611	Approved
0.7122	Intermediate Similarity	NPD1281	Approved
0.7114	Intermediate Similarity	NPD2353	Approved
0.7114	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD9261	Approved
0.7108	Intermediate Similarity	NPD6797	Phase 2
0.7095	Intermediate Similarity	NPD3748	Approved
0.7091	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2801	Approved
0.7086	Intermediate Similarity	NPD7003	Approved
0.7083	Intermediate Similarity	NPD7095	Approved
0.708	Intermediate Similarity	NPD9545	Approved
0.7071	Intermediate Similarity	NPD1481	Phase 2
0.707	Intermediate Similarity	NPD7411	Suspended
0.7066	Intermediate Similarity	NPD7251	Discontinued
0.7063	Intermediate Similarity	NPD9494	Approved
0.7063	Intermediate Similarity	NPD3749	Approved
0.7051	Intermediate Similarity	NPD7458	Discontinued
0.7047	Intermediate Similarity	NPD6100	Approved
0.7047	Intermediate Similarity	NPD6099	Approved
0.7024	Intermediate Similarity	NPD7808	Phase 3
0.7012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6166	Phase 2
0.7012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1535	Discovery
0.6986	Remote Similarity	NPD8032	Phase 2
0.6986	Remote Similarity	NPD6233	Phase 2
0.6982	Remote Similarity	NPD8312	Approved
0.6982	Remote Similarity	NPD8313	Approved
0.6975	Remote Similarity	NPD5494	Approved
0.6972	Remote Similarity	NPD6696	Suspended
0.6957	Remote Similarity	NPD1894	Discontinued
0.6951	Remote Similarity	NPD3926	Phase 2
0.6948	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7074	Phase 3
0.6939	Remote Similarity	NPD4060	Phase 1
0.6937	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6959	Discontinued
0.6933	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3887	Approved
0.6923	Remote Similarity	NPD1164	Approved
0.6923	Remote Similarity	NPD987	Approved
0.6923	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3764	Approved
0.6918	Remote Similarity	NPD6279	Approved
0.6918	Remote Similarity	NPD6280	Approved
0.6912	Remote Similarity	NPD9281	Approved
0.6906	Remote Similarity	NPD5585	Approved
0.6903	Remote Similarity	NPD1578	Phase 2
0.6903	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4380	Phase 2
0.6897	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7768	Phase 2
0.6894	Remote Similarity	NPD290	Approved
0.6887	Remote Similarity	NPD6002	Phase 3
0.6887	Remote Similarity	NPD5762	Approved
0.6887	Remote Similarity	NPD6004	Phase 3
0.6887	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6005	Phase 3
0.6887	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5763	Approved
0.6886	Remote Similarity	NPD7054	Approved
0.6879	Remote Similarity	NPD422	Phase 1
0.6875	Remote Similarity	NPD5647	Approved
0.6871	Remote Similarity	NPD4062	Phase 3
0.6867	Remote Similarity	NPD7033	Discontinued
0.6867	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD709	Approved
0.6853	Remote Similarity	NPD3225	Approved
0.6845	Remote Similarity	NPD7472	Approved
0.6835	Remote Similarity	NPD2651	Approved
0.6835	Remote Similarity	NPD2649	Approved
0.6832	Remote Similarity	NPD7318	Phase 3
0.6832	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3751	Discontinued
0.6824	Remote Similarity	NPD2979	Phase 3
0.6824	Remote Similarity	NPD3140	Approved
0.6824	Remote Similarity	NPD3142	Approved
0.6824	Remote Similarity	NPD943	Approved
0.6821	Remote Similarity	NPD4476	Approved
0.6821	Remote Similarity	NPD4477	Approved
0.6815	Remote Similarity	NPD3869	Phase 3
0.6815	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3873	Phase 3
0.6815	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6232	Discontinued
0.6783	Remote Similarity	NPD4749	Approved
0.6781	Remote Similarity	NPD2614	Approved
0.6779	Remote Similarity	NPD1184	Approved
0.6772	Remote Similarity	NPD844	Approved
0.6766	Remote Similarity	NPD7473	Discontinued
0.6753	Remote Similarity	NPD4110	Phase 3
0.6753	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5952	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