NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.08
Volume:	238.321
LogP:	2.801
LogD:	2.399
LogS:	-2.615
# Rotatable Bonds:	6
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	2.166
Fsp3:	0.333
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:	-4.634
MDCK Permeability:	2.5165052647935227e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357
Plasma Protein Binding (PPB):	94.36685180664062%
Volume Distribution (VD):	0.285
Pgp-substrate:	4.311212539672852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.258
CYP2C19-inhibitor:	0.787
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.864
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.446
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	13.757
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.036
Drug-inuced Liver Injury (DILI):	0.615
AMES Toxicity:	0.604
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.77
Carcinogencity:	0.134
Eye Corrosion:	0.115
Eye Irritation:	0.978
Respiratory Toxicity:	0.056

Download Data

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

Natural Product: NPC198249

Natural Product ID:	NPC198249
*Common Name:**	Fukaneketoester A
IUPAC Name:	butyl 2-(2,4-dihydroxyphenyl)-2-oxoacetate
Synonyms:
Standard InCHIKey:	OZPJJHQMIOVIKX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14O5/c1-2-3-6-17-12(16)11(15)9-5-4-8(13)7-10(9)14/h4-5,7,13-14H,2-3,6H2,1H3
SMILES:	CCCCOC(=O)C(=O)c1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469921
PubChem CID:	11322356
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15043424]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043424]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15467238]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787437]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378364]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	112600.0	nM	PMID[507659]

☑ 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 NPC198249 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	303
0.1-0.2	1380
0.2-0.3	4067
0.3-0.4	9352
0.4-0.5	9761
0.5-0.6	4782
0.6-0.7	6587
0.7-0.8	5737
0.8-0.85	628
0.85-0.9	97
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9104	High Similarity	NPC52358
0.8984	High Similarity	NPC95309
0.8952	High Similarity	NPC161617
0.8923	High Similarity	NPC102829
0.8923	High Similarity	NPC120488
0.8871	High Similarity	NPC40649
0.8871	High Similarity	NPC241089
0.8871	High Similarity	NPC209486
0.8832	High Similarity	NPC244923
0.875	High Similarity	NPC177307
0.875	High Similarity	NPC9121
0.8741	High Similarity	NPC475955
0.8741	High Similarity	NPC474726
0.874	High Similarity	NPC115159
0.874	High Similarity	NPC45438
0.874	High Similarity	NPC224273
0.874	High Similarity	NPC267552
0.874	High Similarity	NPC73532
0.874	High Similarity	NPC143427
0.874	High Similarity	NPC19174
0.873	High Similarity	NPC294037
0.8712	High Similarity	NPC42292
0.8712	High Similarity	NPC307732
0.8705	High Similarity	NPC354984
0.8686	High Similarity	NPC19622
0.8686	High Similarity	NPC112789
0.8672	High Similarity	NPC133909
0.8672	High Similarity	NPC32032
0.8672	High Similarity	NPC309765
0.8667	High Similarity	NPC70859
0.8667	High Similarity	NPC61153
0.8667	High Similarity	NPC283590
0.8667	High Similarity	NPC130899
0.8661	High Similarity	NPC146642
0.8661	High Similarity	NPC149246
0.8661	High Similarity	NPC297186
0.8657	High Similarity	NPC153783
0.8643	High Similarity	NPC470216
0.8623	High Similarity	NPC275903
0.8615	High Similarity	NPC262671
0.8615	High Similarity	NPC287473
0.8615	High Similarity	NPC201728
0.8613	High Similarity	NPC33144
0.8613	High Similarity	NPC478200
0.8613	High Similarity	NPC472403
0.8594	High Similarity	NPC303737
0.8594	High Similarity	NPC215392
0.8594	High Similarity	NPC156139
0.8594	High Similarity	NPC242895
0.8582	High Similarity	NPC478190
0.8582	High Similarity	NPC65060
0.8571	High Similarity	NPC283844
0.8561	High Similarity	NPC41263
0.8561	High Similarity	NPC80694
0.8561	High Similarity	NPC478201
0.8561	High Similarity	NPC472035
0.8561	High Similarity	NPC293453
0.8561	High Similarity	NPC186098
0.855	High Similarity	NPC8745
0.8548	High Similarity	NPC118288
0.8548	High Similarity	NPC276111
0.8542	High Similarity	NPC56204
0.854	High Similarity	NPC65837
0.854	High Similarity	NPC121243
0.854	High Similarity	NPC149372
0.854	High Similarity	NPC71256
0.854	High Similarity	NPC474771
0.854	High Similarity	NPC240147
0.854	High Similarity	NPC474849
0.854	High Similarity	NPC178467
0.8538	High Similarity	NPC13238
0.8529	High Similarity	NPC470210
0.8527	High Similarity	NPC91105
0.8521	High Similarity	NPC202112
0.8521	High Similarity	NPC51513
0.8519	High Similarity	NPC213485
0.8519	High Similarity	NPC40524
0.8519	High Similarity	NPC139074
0.8511	High Similarity	NPC126882
0.8511	High Similarity	NPC210966
0.8511	High Similarity	NPC478203
0.8507	High Similarity	NPC475042
0.8507	High Similarity	NPC219892
0.8507	High Similarity	NPC189823
0.8504	High Similarity	NPC158222
0.85	High Similarity	NPC136840
0.8496	Intermediate Similarity	NPC476119
0.8492	Intermediate Similarity	NPC230349
0.8489	Intermediate Similarity	NPC49242
0.8489	Intermediate Similarity	NPC230902
0.8485	Intermediate Similarity	NPC105157
0.8485	Intermediate Similarity	NPC23126
0.8485	Intermediate Similarity	NPC103356
0.8485	Intermediate Similarity	NPC100067
0.8485	Intermediate Similarity	NPC30501
0.8485	Intermediate Similarity	NPC98254
0.8485	Intermediate Similarity	NPC190043
0.8485	Intermediate Similarity	NPC266689
0.8485	Intermediate Similarity	NPC72158
0.8485	Intermediate Similarity	NPC169250
0.8485	Intermediate Similarity	NPC162612
0.8485	Intermediate Similarity	NPC128428
0.8485	Intermediate Similarity	NPC305518
0.8478	Intermediate Similarity	NPC475974
0.8478	Intermediate Similarity	NPC191835
0.8473	Intermediate Similarity	NPC10926
0.8472	Intermediate Similarity	NPC84142
0.8472	Intermediate Similarity	NPC477941
0.8468	Intermediate Similarity	NPC11824
0.8468	Intermediate Similarity	NPC223004
0.8467	Intermediate Similarity	NPC235115
0.8462	Intermediate Similarity	NPC472029
0.8462	Intermediate Similarity	NPC65761
0.8451	Intermediate Similarity	NPC257558
0.845	Intermediate Similarity	NPC226275
0.8444	Intermediate Similarity	NPC262359
0.844	Intermediate Similarity	NPC476310
0.844	Intermediate Similarity	NPC476164
0.8438	Intermediate Similarity	NPC159525
0.8433	Intermediate Similarity	NPC247477
0.8433	Intermediate Similarity	NPC147757
0.8433	Intermediate Similarity	NPC17840
0.8433	Intermediate Similarity	NPC185497
0.8429	Intermediate Similarity	NPC90411
0.8429	Intermediate Similarity	NPC59951
0.8429	Intermediate Similarity	NPC230285
0.8429	Intermediate Similarity	NPC103342
0.8429	Intermediate Similarity	NPC478217
0.8429	Intermediate Similarity	NPC103904
0.8429	Intermediate Similarity	NPC269652
0.8429	Intermediate Similarity	NPC281207
0.8429	Intermediate Similarity	NPC313123
0.8429	Intermediate Similarity	NPC184536
0.8429	Intermediate Similarity	NPC146679
0.8425	Intermediate Similarity	NPC94637
0.8421	Intermediate Similarity	NPC221777
0.8421	Intermediate Similarity	NPC473017
0.8421	Intermediate Similarity	NPC179898
0.8421	Intermediate Similarity	NPC21305
0.8417	Intermediate Similarity	NPC92655
0.8417	Intermediate Similarity	NPC474655
0.8417	Intermediate Similarity	NPC268052
0.8417	Intermediate Similarity	NPC275356
0.8417	Intermediate Similarity	NPC25427
0.8414	Intermediate Similarity	NPC164762
0.8414	Intermediate Similarity	NPC116822
0.8409	Intermediate Similarity	NPC267846
0.8409	Intermediate Similarity	NPC62952
0.8406	Intermediate Similarity	NPC135837
0.8406	Intermediate Similarity	NPC70380
0.8403	Intermediate Similarity	NPC215711
0.8403	Intermediate Similarity	NPC73411
0.8394	Intermediate Similarity	NPC164136
0.8392	Intermediate Similarity	NPC153758
0.8392	Intermediate Similarity	NPC472033
0.8382	Intermediate Similarity	NPC129132
0.8382	Intermediate Similarity	NPC212631
0.8382	Intermediate Similarity	NPC257756
0.8382	Intermediate Similarity	NPC205468
0.8382	Intermediate Similarity	NPC87231
0.8382	Intermediate Similarity	NPC203817
0.8369	Intermediate Similarity	NPC150023
0.8369	Intermediate Similarity	NPC90582
0.8369	Intermediate Similarity	NPC262094
0.8359	Intermediate Similarity	NPC90522
0.8359	Intermediate Similarity	NPC328459
0.8358	Intermediate Similarity	NPC474998
0.8358	Intermediate Similarity	NPC78662
0.8358	Intermediate Similarity	NPC8005
0.8358	Intermediate Similarity	NPC60558
0.8358	Intermediate Similarity	NPC69235
0.8358	Intermediate Similarity	NPC212379
0.8357	Intermediate Similarity	NPC158472
0.8357	Intermediate Similarity	NPC152042
0.8357	Intermediate Similarity	NPC143799
0.8357	Intermediate Similarity	NPC241838
0.8356	Intermediate Similarity	NPC91809
0.8356	Intermediate Similarity	NPC295650
0.8346	Intermediate Similarity	NPC121259
0.8346	Intermediate Similarity	NPC214620
0.8346	Intermediate Similarity	NPC116513
0.8345	Intermediate Similarity	NPC212693
0.8345	Intermediate Similarity	NPC254841
0.8345	Intermediate Similarity	NPC299379
0.8345	Intermediate Similarity	NPC175552
0.8345	Intermediate Similarity	NPC94248
0.8345	Intermediate Similarity	NPC188879
0.8333	Intermediate Similarity	NPC475733
0.8333	Intermediate Similarity	NPC210320
0.8333	Intermediate Similarity	NPC472036
0.8322	Intermediate Similarity	NPC472034
0.8322	Intermediate Similarity	NPC71210
0.8322	Intermediate Similarity	NPC83272
0.8321	Intermediate Similarity	NPC175098
0.8321	Intermediate Similarity	NPC223457
0.8321	Intermediate Similarity	NPC312318
0.8321	Intermediate Similarity	NPC139813
0.8321	Intermediate Similarity	NPC188646
0.8321	Intermediate Similarity	NPC337373
0.8321	Intermediate Similarity	NPC192304

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 NPC198249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	891
0.2-0.3	1752
0.3-0.4	2759
0.4-0.5	2010
0.5-0.6	998
0.6-0.7	351
0.7-0.8	114
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.838	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1240	Approved
0.8281	Intermediate Similarity	NPD9545	Approved
0.8268	Intermediate Similarity	NPD9493	Approved
0.8248	Intermediate Similarity	NPD230	Phase 1
0.8201	Intermediate Similarity	NPD1510	Phase 2
0.8188	Intermediate Similarity	NPD1607	Approved
0.8175	Intermediate Similarity	NPD943	Approved
0.8156	Intermediate Similarity	NPD1549	Phase 2
0.8156	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7075	Discontinued
0.8069	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD74	Approved
0.8065	Intermediate Similarity	NPD9266	Approved
0.8042	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD9263	Approved
0.7984	Intermediate Similarity	NPD9267	Approved
0.7984	Intermediate Similarity	NPD9264	Approved
0.797	Intermediate Similarity	NPD9269	Phase 2
0.7943	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD9268	Approved
0.7933	Intermediate Similarity	NPD6801	Discontinued
0.7895	Intermediate Similarity	NPD3882	Suspended
0.7887	Intermediate Similarity	NPD1551	Phase 2
0.7867	Intermediate Similarity	NPD7411	Suspended
0.7836	Intermediate Similarity	NPD9717	Approved
0.7829	Intermediate Similarity	NPD3817	Phase 2
0.7823	Intermediate Similarity	NPD2533	Approved
0.7823	Intermediate Similarity	NPD2532	Approved
0.7823	Intermediate Similarity	NPD2534	Approved
0.777	Intermediate Similarity	NPD1512	Approved
0.7718	Intermediate Similarity	NPD5403	Approved
0.7718	Intermediate Similarity	NPD920	Approved
0.7703	Intermediate Similarity	NPD5401	Approved
0.7692	Intermediate Similarity	NPD9281	Approved
0.7682	Intermediate Similarity	NPD4380	Phase 2
0.7664	Intermediate Similarity	NPD1164	Approved
0.7664	Intermediate Similarity	NPD1203	Approved
0.7661	Intermediate Similarity	NPD9261	Approved
0.7647	Intermediate Similarity	NPD7819	Suspended
0.7643	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD2796	Approved
0.7639	Intermediate Similarity	NPD2935	Discontinued
0.7635	Intermediate Similarity	NPD1511	Approved
0.7597	Intermediate Similarity	NPD5402	Approved
0.7589	Intermediate Similarity	NPD520	Approved
0.7584	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1934	Approved
0.7551	Intermediate Similarity	NPD3750	Approved
0.7532	Intermediate Similarity	NPD2801	Approved
0.7532	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD1243	Approved
0.7483	Intermediate Similarity	NPD2800	Approved
0.7483	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1019	Discontinued
0.7452	Intermediate Similarity	NPD919	Approved
0.745	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7768	Phase 2
0.741	Intermediate Similarity	NPD1470	Approved
0.7407	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7286	Phase 2
0.74	Intermediate Similarity	NPD7390	Discontinued
0.7383	Intermediate Similarity	NPD6190	Approved
0.7376	Intermediate Similarity	NPD6832	Phase 2
0.7372	Intermediate Similarity	NPD422	Phase 1
0.7372	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD6166	Phase 2
0.7329	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6797	Phase 2
0.7317	Intermediate Similarity	NPD5953	Discontinued
0.7312	Intermediate Similarity	NPD6232	Discontinued
0.731	Intermediate Similarity	NPD6651	Approved
0.7302	Intermediate Similarity	NPD940	Approved
0.7302	Intermediate Similarity	NPD846	Approved
0.7284	Intermediate Similarity	NPD7473	Discontinued
0.7279	Intermediate Similarity	NPD5406	Approved
0.7279	Intermediate Similarity	NPD5404	Approved
0.7279	Intermediate Similarity	NPD5405	Approved
0.7279	Intermediate Similarity	NPD5408	Approved
0.7279	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7251	Discontinued
0.7273	Intermediate Similarity	NPD2313	Discontinued
0.7273	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD3764	Approved
0.725	Intermediate Similarity	NPD1247	Approved
0.7246	Intermediate Similarity	NPD1201	Approved
0.7239	Intermediate Similarity	NPD3818	Discontinued
0.723	Intermediate Similarity	NPD2344	Approved
0.7229	Intermediate Similarity	NPD7808	Phase 3
0.7211	Intermediate Similarity	NPD3748	Approved
0.7133	Intermediate Similarity	NPD2654	Approved
0.7123	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5711	Approved
0.7099	Intermediate Similarity	NPD5710	Approved
0.7091	Intermediate Similarity	NPD7054	Approved
0.7086	Intermediate Similarity	NPD4628	Phase 3
0.7051	Intermediate Similarity	NPD3226	Approved
0.7048	Intermediate Similarity	NPD7472	Approved
0.7048	Intermediate Similarity	NPD7074	Phase 3
0.7039	Intermediate Similarity	NPD2309	Approved
0.7037	Intermediate Similarity	NPD6959	Discontinued
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2346	Discontinued
0.6994	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1465	Phase 2
0.6975	Remote Similarity	NPD5494	Approved
0.6964	Remote Similarity	NPD6559	Discontinued
0.6963	Remote Similarity	NPD1241	Discontinued
0.6944	Remote Similarity	NPD9494	Approved
0.6932	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2354	Approved
0.6923	Remote Similarity	NPD1237	Approved
0.6918	Remote Similarity	NPD6798	Discontinued
0.6918	Remote Similarity	NPD1296	Phase 2
0.6918	Remote Similarity	NPD3268	Approved
0.6912	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1933	Approved
0.6886	Remote Similarity	NPD5844	Phase 1
0.6875	Remote Similarity	NPD2798	Approved
0.6871	Remote Similarity	NPD6233	Phase 2
0.6867	Remote Similarity	NPD7033	Discontinued
0.6867	Remote Similarity	NPD4308	Phase 3
0.6863	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8150	Discontinued
0.6848	Remote Similarity	NPD3926	Phase 2
0.6842	Remote Similarity	NPD2182	Approved
0.6835	Remote Similarity	NPD1759	Phase 1
0.6835	Remote Similarity	NPD1548	Phase 1
0.6831	Remote Similarity	NPD1481	Phase 2
0.6826	Remote Similarity	NPD3751	Discontinued
0.6818	Remote Similarity	NPD3887	Approved
0.6815	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2797	Approved
0.6797	Remote Similarity	NPD9495	Approved
0.6794	Remote Similarity	NPD164	Approved
0.6779	Remote Similarity	NPD6355	Discontinued
0.6776	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2353	Approved
0.6776	Remote Similarity	NPD1471	Phase 3
0.6774	Remote Similarity	NPD9258	Approved
0.6774	Remote Similarity	NPD9256	Approved
0.6763	Remote Similarity	NPD1758	Phase 1
0.6761	Remote Similarity	NPD1535	Discovery
0.6759	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1729	Discontinued
0.6739	Remote Similarity	NPD256	Approved
0.6739	Remote Similarity	NPD255	Approved
0.6736	Remote Similarity	NPD3225	Approved
0.673	Remote Similarity	NPD7458	Discontinued
0.6725	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3972	Approved
0.6713	Remote Similarity	NPD1608	Approved
0.6707	Remote Similarity	NPD2403	Approved
0.6692	Remote Similarity	NPD1242	Phase 1
0.669	Remote Similarity	NPD3267	Approved
0.669	Remote Similarity	NPD3266	Approved
0.6688	Remote Similarity	NPD1652	Phase 2
0.6688	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2067	Discontinued
0.6667	Remote Similarity	NPD3300	Phase 2
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5124	Phase 1
0.6646	Remote Similarity	NPD958	Approved
0.6646	Remote Similarity	NPD5049	Phase 3
0.6645	Remote Similarity	NPD1196	Approved
0.6645	Remote Similarity	NPD3400	Discontinued
0.6644	Remote Similarity	NPD4062	Phase 3
0.6643	Remote Similarity	NPD1610	Phase 2
0.6642	Remote Similarity	NPD1358	Approved
0.6626	Remote Similarity	NPD4288	Approved
0.6626	Remote Similarity	NPD5353	Approved
0.6624	Remote Similarity	NPD1543	Discontinued
0.662	Remote Similarity	NPD1778	Approved
0.6618	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5048	Discontinued
0.6615	Remote Similarity	NPD1238	Approved
0.6612	Remote Similarity	NPD7435	Discontinued
0.6601	Remote Similarity	NPD9570	Approved
0.6601	Remote Similarity	NPD6100	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