NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.08
Volume:	223.661
LogP:	2.51
LogD:	1.762
LogS:	-2.444
# Rotatable Bonds:	5
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	2.083
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.765
MDCK Permeability:	1.9835228158626705e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	94.4681625366211%
Volume Distribution (VD):	0.351
Pgp-substrate:	4.926600456237793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.906
CYP1A2-substrate:	0.424
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.439
CYP2C9-substrate:	0.495
CYP2D6-inhibitor:	0.408
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.217
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	17.089
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.321
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.941
Carcinogencity:	0.041
Eye Corrosion:	0.496
Eye Irritation:	0.955
Respiratory Toxicity:	0.123

Download Data

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

Natural Product: NPC156124

Natural Product ID:	NPC156124
*Common Name:**	Butyl Gallate
IUPAC Name:	butyl 3,4,5-trihydroxybenzoate
Synonyms:	Butyl Gallate
Standard InCHIKey:	XOPOEBVTQYAOSV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O5/c1-2-3-4-16-11(15)7-5-8(12)10(14)9(13)6-7/h5-6,12-14H,2-4H2,1H3
SMILES:	CCCCOC(=O)c1cc(O)c(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494005
PubChem CID:	14128
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0001251] Gallic acid and derivatives [CHEMONTID:0003539] Galloyl esters

*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
NPO21458	Radix paeoniae rubra	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
EC50	3
IC50	1
MIC	12
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	2
Organism	14
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT333	Cell Line	CEM	Homo sapiens	CC50	=	55000.0	nM	PMID[514274]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	=	8970.0	nM	PMID[514275]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	=	50.0	ug.mL-1	PMID[514273]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	50.0	ug.mL-1	PMID[514273]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	=	100.0	ug.mL-1	PMID[514273]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	100.0	ug.mL-1	PMID[514273]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	250.0	ug.mL-1	PMID[514273]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	>	250.0	ug.mL-1	PMID[514273]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	250.0	ug.mL-1	PMID[514273]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	250.0	ug.mL-1	PMID[514273]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	250.0	ug.mL-1	PMID[514273]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	>	250.0	ug.mL-1	PMID[514273]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	250.0	ug.mL-1	PMID[514273]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	10000.0	nM	PMID[514274]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	>	10000.0	nM	PMID[514274]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	13000.0	nM	PMID[514274]
NPT27	Others	Unspecified		CC50	=	29000.0	nM	PMID[514274]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC90	>	29.0	uM	PMID[514274]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2055000.0	nM	PMID[514275]

☑ 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 NPC156124 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	321
0.1-0.2	1465
0.2-0.3	4349
0.3-0.4	9296
0.4-0.5	8916
0.5-0.6	3858
0.6-0.7	6926
0.7-0.8	6817
0.8-0.85	634
0.85-0.9	87
0.9-0.95	22
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304929
1.0	High Similarity	NPC1321
0.9844	High Similarity	NPC18646
0.9841	High Similarity	NPC264145
0.9767	High Similarity	NPC156892
0.9528	High Similarity	NPC226855
0.947	High Similarity	NPC239943
0.9398	High Similarity	NPC105525
0.9398	High Similarity	NPC12218
0.9398	High Similarity	NPC75763
0.9398	High Similarity	NPC225036
0.9394	High Similarity	NPC25305
0.9394	High Similarity	NPC110899
0.9394	High Similarity	NPC125417
0.9394	High Similarity	NPC112068
0.9394	High Similarity	NPC95679
0.937	High Similarity	NPC158654
0.9167	High Similarity	NPC155098
0.9127	High Similarity	NPC225710
0.9124	High Similarity	NPC50221
0.9124	High Similarity	NPC190587
0.9124	High Similarity	NPC226738
0.9124	High Similarity	NPC229036
0.9124	High Similarity	NPC121573
0.9124	High Similarity	NPC114242
0.9124	High Similarity	NPC22176
0.9111	High Similarity	NPC471819
0.9077	High Similarity	NPC94810
0.9058	High Similarity	NPC108455
0.8955	High Similarity	NPC274613
0.8955	High Similarity	NPC208760
0.8947	High Similarity	NPC283823
0.8947	High Similarity	NPC239855
0.8947	High Similarity	NPC159418
0.8947	High Similarity	NPC288743
0.8897	High Similarity	NPC207516
0.8889	High Similarity	NPC475111
0.8881	High Similarity	NPC237330
0.8881	High Similarity	NPC248150
0.8873	High Similarity	NPC306343
0.8872	High Similarity	NPC111888
0.8865	High Similarity	NPC120621
0.8865	High Similarity	NPC43123
0.8865	High Similarity	NPC248257
0.8865	High Similarity	NPC142528
0.8864	High Similarity	NPC299010
0.8849	High Similarity	NPC134975
0.8832	High Similarity	NPC4796
0.8803	High Similarity	NPC92117
0.8803	High Similarity	NPC75945
0.8803	High Similarity	NPC42464
0.8803	High Similarity	NPC107636
0.8794	High Similarity	NPC268366
0.875	High Similarity	NPC156307
0.875	High Similarity	NPC221249
0.875	High Similarity	NPC75695
0.8723	High Similarity	NPC262282
0.8722	High Similarity	NPC285776
0.8692	High Similarity	NPC145134
0.869	High Similarity	NPC310661
0.869	High Similarity	NPC105827
0.8681	High Similarity	NPC252979
0.8681	High Similarity	NPC96501
0.8681	High Similarity	NPC140151
0.8667	High Similarity	NPC153783
0.8661	High Similarity	NPC156654
0.8643	High Similarity	NPC299154
0.8636	High Similarity	NPC214620
0.8633	High Similarity	NPC326065
0.863	High Similarity	NPC281703
0.863	High Similarity	NPC125487
0.8623	High Similarity	NPC112135
0.8611	High Similarity	NPC473091
0.8601	High Similarity	NPC476463
0.8583	High Similarity	NPC27633
0.8583	High Similarity	NPC94298
0.8582	High Similarity	NPC469615
0.8571	High Similarity	NPC156624
0.8571	High Similarity	NPC145425
0.8571	High Similarity	NPC172920
0.8562	High Similarity	NPC61152
0.8562	High Similarity	NPC205037
0.8562	High Similarity	NPC16024
0.8562	High Similarity	NPC161159
0.8562	High Similarity	NPC3746
0.8562	High Similarity	NPC44260
0.8561	High Similarity	NPC474875
0.8561	High Similarity	NPC295492
0.8561	High Similarity	NPC26241
0.8561	High Similarity	NPC274891
0.8561	High Similarity	NPC476819
0.8561	High Similarity	NPC476820
0.8561	High Similarity	NPC205751
0.8561	High Similarity	NPC95309
0.8561	High Similarity	NPC303683
0.8529	High Similarity	NPC157478
0.8529	High Similarity	NPC200422
0.8529	High Similarity	NPC289572
0.8529	High Similarity	NPC295406
0.8521	High Similarity	NPC469683
0.8521	High Similarity	NPC257025
0.8519	High Similarity	NPC219892
0.8519	High Similarity	NPC189823
0.8519	High Similarity	NPC318799
0.8511	High Similarity	NPC312256
0.8503	High Similarity	NPC238672
0.8503	High Similarity	NPC144801
0.8503	High Similarity	NPC281477
0.8503	High Similarity	NPC197188
0.8503	High Similarity	NPC43872
0.8503	High Similarity	NPC291510
0.8503	High Similarity	NPC116850
0.85	High Similarity	NPC187690
0.85	High Similarity	NPC158472
0.85	High Similarity	NPC50823
0.8496	Intermediate Similarity	NPC107672
0.8493	Intermediate Similarity	NPC204350
0.8493	Intermediate Similarity	NPC92747
0.8493	Intermediate Similarity	NPC265862
0.8489	Intermediate Similarity	NPC302857
0.8489	Intermediate Similarity	NPC142703
0.8489	Intermediate Similarity	NPC219428
0.8489	Intermediate Similarity	NPC278068
0.8489	Intermediate Similarity	NPC37250
0.8489	Intermediate Similarity	NPC152942
0.8478	Intermediate Similarity	NPC326847
0.8478	Intermediate Similarity	NPC235115
0.8472	Intermediate Similarity	NPC472969
0.8467	Intermediate Similarity	NPC106406
0.8462	Intermediate Similarity	NPC83272
0.8462	Intermediate Similarity	NPC473867
0.8456	Intermediate Similarity	NPC1913
0.8456	Intermediate Similarity	NPC104275
0.8456	Intermediate Similarity	NPC472860
0.8456	Intermediate Similarity	NPC4747
0.8451	Intermediate Similarity	NPC287722
0.8446	Intermediate Similarity	NPC203757
0.8446	Intermediate Similarity	NPC199926
0.8446	Intermediate Similarity	NPC79998
0.8446	Intermediate Similarity	NPC82592
0.8446	Intermediate Similarity	NPC16082
0.844	Intermediate Similarity	NPC90411
0.844	Intermediate Similarity	NPC110419
0.8433	Intermediate Similarity	NPC79332
0.8433	Intermediate Similarity	NPC304747
0.8433	Intermediate Similarity	NPC109275
0.8429	Intermediate Similarity	NPC52358
0.8429	Intermediate Similarity	NPC203351
0.8429	Intermediate Similarity	NPC247409
0.8429	Intermediate Similarity	NPC275356
0.8425	Intermediate Similarity	NPC131192
0.8421	Intermediate Similarity	NPC154275
0.8417	Intermediate Similarity	NPC70380
0.8417	Intermediate Similarity	NPC135837
0.8414	Intermediate Similarity	NPC476394
0.8414	Intermediate Similarity	NPC98809
0.8406	Intermediate Similarity	NPC176102
0.8406	Intermediate Similarity	NPC29317
0.8406	Intermediate Similarity	NPC267539
0.8406	Intermediate Similarity	NPC204257
0.8406	Intermediate Similarity	NPC139519
0.8406	Intermediate Similarity	NPC254832
0.8406	Intermediate Similarity	NPC229638
0.8406	Intermediate Similarity	NPC71108
0.8403	Intermediate Similarity	NPC138978
0.8403	Intermediate Similarity	NPC143903
0.8403	Intermediate Similarity	NPC165389
0.8403	Intermediate Similarity	NPC229264
0.8403	Intermediate Similarity	NPC226987
0.84	Intermediate Similarity	NPC289811
0.84	Intermediate Similarity	NPC160780
0.84	Intermediate Similarity	NPC87317
0.8392	Intermediate Similarity	NPC207732
0.8392	Intermediate Similarity	NPC105213
0.8392	Intermediate Similarity	NPC113397
0.8389	Intermediate Similarity	NPC239019
0.8389	Intermediate Similarity	NPC250436
0.8389	Intermediate Similarity	NPC150227
0.8389	Intermediate Similarity	NPC300845
0.8389	Intermediate Similarity	NPC134925
0.8389	Intermediate Similarity	NPC318432
0.8389	Intermediate Similarity	NPC104983
0.8389	Intermediate Similarity	NPC88803
0.8389	Intermediate Similarity	NPC247629
0.8389	Intermediate Similarity	NPC291948
0.838	Intermediate Similarity	NPC43158
0.838	Intermediate Similarity	NPC472016
0.838	Intermediate Similarity	NPC258469
0.838	Intermediate Similarity	NPC277315
0.838	Intermediate Similarity	NPC192831
0.838	Intermediate Similarity	NPC284556
0.838	Intermediate Similarity	NPC301178
0.837	Intermediate Similarity	NPC48315
0.8369	Intermediate Similarity	NPC290664
0.8369	Intermediate Similarity	NPC327187
0.8367	Intermediate Similarity	NPC93498
0.8367	Intermediate Similarity	NPC163883
0.8358	Intermediate Similarity	NPC281020
0.8357	Intermediate Similarity	NPC94248
0.8357	Intermediate Similarity	NPC478200

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 NPC156124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	891
0.2-0.3	1973
0.3-0.4	2702
0.4-0.5	1759
0.5-0.6	1052
0.6-0.7	386
0.7-0.8	98
0.8-0.85	7
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD230	Phase 1
0.9127	High Similarity	NPD9269	Phase 2
0.881	High Similarity	NPD9268	Approved
0.8583	High Similarity	NPD9545	Approved
0.8389	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD6190	Approved
0.8222	Intermediate Similarity	NPD9494	Approved
0.8188	Intermediate Similarity	NPD943	Approved
0.8169	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1511	Approved
0.8085	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1934	Approved
0.8027	Intermediate Similarity	NPD1512	Approved
0.8026	Intermediate Similarity	NPD3882	Suspended
0.8013	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1465	Phase 2
0.8013	Intermediate Similarity	NPD2801	Approved
0.7872	Intermediate Similarity	NPD447	Suspended
0.7843	Intermediate Similarity	NPD3817	Phase 2
0.7838	Intermediate Similarity	NPD2532	Approved
0.7838	Intermediate Similarity	NPD2534	Approved
0.7838	Intermediate Similarity	NPD2533	Approved
0.7764	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD9493	Approved
0.7727	Intermediate Similarity	NPD5353	Approved
0.7717	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1510	Phase 2
0.7688	Intermediate Similarity	NPD3818	Discontinued
0.7676	Intermediate Similarity	NPD1240	Approved
0.7658	Intermediate Similarity	NPD6232	Discontinued
0.7655	Intermediate Similarity	NPD1551	Phase 2
0.7651	Intermediate Similarity	NPD6799	Approved
0.7616	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1607	Approved
0.7568	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4628	Phase 3
0.7562	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6166	Phase 2
0.7561	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1549	Phase 2
0.7535	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3764	Approved
0.7531	Intermediate Similarity	NPD5844	Phase 1
0.7531	Intermediate Similarity	NPD7054	Approved
0.7516	Intermediate Similarity	NPD7473	Discontinued
0.7516	Intermediate Similarity	NPD7075	Discontinued
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD7472	Approved
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7266	Discontinued
0.7468	Intermediate Similarity	NPD6234	Discontinued
0.7468	Intermediate Similarity	NPD4380	Phase 2
0.7465	Intermediate Similarity	NPD3027	Phase 3
0.7451	Intermediate Similarity	NPD1653	Approved
0.745	Intermediate Similarity	NPD3750	Approved
0.7439	Intermediate Similarity	NPD6797	Phase 2
0.7436	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7819	Suspended
0.7417	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2935	Discontinued
0.7403	Intermediate Similarity	NPD3455	Phase 2
0.7394	Intermediate Similarity	NPD7685	Pre-registration
0.7394	Intermediate Similarity	NPD7251	Discontinued
0.7391	Intermediate Similarity	NPD5242	Approved
0.7368	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD919	Approved
0.7355	Intermediate Similarity	NPD6599	Discontinued
0.7347	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD9717	Approved
0.7333	Intermediate Similarity	NPD8166	Discontinued
0.7324	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1613	Approved
0.7308	Intermediate Similarity	NPD7411	Suspended
0.7308	Intermediate Similarity	NPD6385	Approved
0.7308	Intermediate Similarity	NPD6386	Approved
0.7296	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5402	Approved
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD920	Approved
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD422	Phase 1
0.7261	Intermediate Similarity	NPD6801	Discontinued
0.7261	Intermediate Similarity	NPD37	Approved
0.7246	Intermediate Similarity	NPD7808	Phase 3
0.7233	Intermediate Similarity	NPD4967	Phase 2
0.7233	Intermediate Similarity	NPD4966	Approved
0.7233	Intermediate Similarity	NPD4965	Approved
0.7219	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1608	Approved
0.7205	Intermediate Similarity	NPD5494	Approved
0.7192	Intermediate Similarity	NPD826	Approved
0.7192	Intermediate Similarity	NPD825	Approved
0.7183	Intermediate Similarity	NPD1203	Approved
0.7181	Intermediate Similarity	NPD2796	Approved
0.7172	Intermediate Similarity	NPD411	Approved
0.716	Intermediate Similarity	NPD1247	Approved
0.7152	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD2800	Approved
0.7152	Intermediate Similarity	NPD1243	Approved
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD555	Phase 2
0.7125	Intermediate Similarity	NPD7768	Phase 2
0.7121	Intermediate Similarity	NPD9266	Approved
0.7121	Intermediate Similarity	NPD74	Approved
0.7118	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5710	Approved
0.7117	Intermediate Similarity	NPD5711	Approved
0.7114	Intermediate Similarity	NPD3748	Approved
0.709	Intermediate Similarity	NPD228	Approved
0.7081	Intermediate Similarity	NPD3749	Approved
0.7067	Intermediate Similarity	NPD9570	Approved
0.7055	Intermediate Similarity	NPD7199	Phase 2
0.7051	Intermediate Similarity	NPD5403	Approved
0.7045	Intermediate Similarity	NPD9263	Approved
0.7045	Intermediate Similarity	NPD9267	Approved
0.7045	Intermediate Similarity	NPD9264	Approved
0.7032	Intermediate Similarity	NPD5401	Approved
0.7032	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD258	Approved
0.7014	Intermediate Similarity	NPD257	Approved
0.7014	Intermediate Similarity	NPD1019	Discontinued
0.7013	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD259	Phase 1
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD1778	Approved
0.6982	Remote Similarity	NPD6559	Discontinued
0.697	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4357	Discontinued
0.6962	Remote Similarity	NPD824	Approved
0.6957	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6959	Discontinued
0.6923	Remote Similarity	NPD5953	Discontinued
0.6923	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1358	Approved
0.6913	Remote Similarity	NPD1933	Approved
0.6905	Remote Similarity	NPD7286	Phase 2
0.6905	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6651	Approved
0.6867	Remote Similarity	NPD3926	Phase 2
0.6866	Remote Similarity	NPD2182	Approved
0.6861	Remote Similarity	NPD1241	Discontinued
0.6859	Remote Similarity	NPD7390	Discontinued
0.6855	Remote Similarity	NPD3226	Approved
0.6853	Remote Similarity	NPD1481	Phase 2
0.6849	Remote Similarity	NPD9569	Approved
0.6846	Remote Similarity	NPD1242	Phase 1
0.6842	Remote Similarity	NPD6100	Approved
0.6842	Remote Similarity	NPD6099	Approved
0.6828	Remote Similarity	NPD1164	Approved
0.6824	Remote Similarity	NPD1296	Phase 2
0.6818	Remote Similarity	NPD164	Approved
0.6818	Remote Similarity	NPD1652	Phase 2
0.6815	Remote Similarity	NPD3146	Approved
0.6815	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD9281	Approved
0.6803	Remote Similarity	NPD6832	Phase 2
0.6786	Remote Similarity	NPD5536	Phase 2
0.6783	Remote Similarity	NPD1535	Discovery
0.6782	Remote Similarity	NPD8150	Discontinued
0.6779	Remote Similarity	NPD6233	Phase 2
0.6779	Remote Similarity	NPD520	Approved
0.6776	Remote Similarity	NPD2799	Discontinued
0.6776	Remote Similarity	NPD4308	Phase 3
0.6772	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1238	Approved
0.6768	Remote Similarity	NPD6971	Discontinued
0.6763	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3225	Approved
0.6759	Remote Similarity	NPD1283	Approved
0.6757	Remote Similarity	NPD9537	Phase 1
0.6757	Remote Similarity	NPD9536	Phase 1
0.6746	Remote Similarity	NPD3751	Discontinued
0.6742	Remote Similarity	NPD9261	Approved
0.6738	Remote Similarity	NPD1548	Phase 1
0.6732	Remote Similarity	NPD5405	Approved
0.6732	Remote Similarity	NPD5406	Approved
0.6732	Remote Similarity	NPD5408	Approved
0.6732	Remote Similarity	NPD5404	Approved
0.6731	Remote Similarity	NPD2354	Approved
0.6723	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3134	Approved
0.6714	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3496	Discontinued
0.6712	Remote Similarity	NPD1470	Approved
0.6711	Remote Similarity	NPD2313	Discontinued
0.671	Remote Similarity	NPD2654	Approved
0.6709	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7229	Phase 3
0.6691	Remote Similarity	NPD3022	Approved
0.6691	Remote Similarity	NPD3021	Approved
0.6691	Remote Similarity	NPD690	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4196	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