NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.12
Volume:	264.122
LogP:	3.53
LogD:	3.238
LogS:	-2.898
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	2.735
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.65
MDCK Permeability:	2.331010182388127e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.146
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	96.09893035888672%
Volume Distribution (VD):	0.633
Pgp-substrate:	5.132444858551025%

ADMET: Metabolism

CYP1A2-inhibitor:	0.915
CYP1A2-substrate:	0.329
CYP2C19-inhibitor:	0.482
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.654
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.817
CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.274
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	15.022
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.536
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.146
Rat Oral Acute Toxicity:	0.582
Maximum Recommended Daily Dose:	0.79
Skin Sensitization:	0.939
Carcinogencity:	0.676
Eye Corrosion:	0.368
Eye Irritation:	0.746
Respiratory Toxicity:	0.684

Download Data

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

Natural Product: NPC233669

Natural Product ID:	NPC233669
*Common Name:**	(S)-1'-Methylbutyl Caffeate
IUPAC Name:	[(2S)-pentan-2-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	(S)-1'-Methylbutyl Caffeate
Standard InCHIKey:	AGXDVPULWUXVDT-PCGIRMHASA-N
Standard InCHI:	InChI=1S/C14H18O4/c1-3-4-10(2)18-14(17)8-6-11-5-7-12(15)13(16)9-11/h5-10,15-16H,3-4H2,1-2H3/b8-6+/t10-/m0/s1
SMILES:	CCC[C@H](C)OC(=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641896
PubChem CID:	50901244
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO20527	Piper sanguineispicum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20954722]
NPO20527	Piper sanguineispicum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20954722]
NPO20527	Piper sanguineispicum	Species	Piperaceae	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
IC50	4

Activity Type	# Activity
Cell Line	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	62000.0	nM	PMID[509028]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	14000.0	nM	PMID[509028]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	2000.0	nM	PMID[509028]
NPT27	Others	Unspecified		IC50	=	72000.0	nM	PMID[509028]

☑ 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 NPC233669 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	226
0.1-0.2	1202
0.2-0.3	4321
0.3-0.4	10467
0.4-0.5	8202
0.5-0.6	7089
0.6-0.7	8681
0.7-0.8	2209
0.8-0.85	202
0.85-0.9	57
0.9-0.95	28
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC261453
0.9907	High Similarity	NPC281277
0.9907	High Similarity	NPC33749
0.9907	High Similarity	NPC328593
0.9815	High Similarity	NPC474967
0.9813	High Similarity	NPC95381
0.9727	High Similarity	NPC309434
0.9636	High Similarity	NPC65791
0.9626	High Similarity	NPC226250
0.955	High Similarity	NPC203124
0.9541	High Similarity	NPC217472
0.9469	High Similarity	NPC470849
0.9469	High Similarity	NPC470848
0.9298	High Similarity	NPC204466
0.9292	High Similarity	NPC263386
0.9292	High Similarity	NPC141791
0.9217	High Similarity	NPC70752
0.9211	High Similarity	NPC202474
0.9204	High Similarity	NPC275519
0.9182	High Similarity	NPC131530
0.9159	High Similarity	NPC1075
0.9159	High Similarity	NPC294902
0.9159	High Similarity	NPC1786
0.906	High Similarity	NPC224208
0.906	High Similarity	NPC474275
0.9052	High Similarity	NPC147654
0.9035	High Similarity	NPC137537
0.9035	High Similarity	NPC70744
0.9035	High Similarity	NPC107588
0.9035	High Similarity	NPC272471
0.9035	High Similarity	NPC164706
0.8983	High Similarity	NPC246704
0.8983	High Similarity	NPC20443
0.8983	High Similarity	NPC60517
0.8983	High Similarity	NPC146886
0.8957	High Similarity	NPC241634
0.8947	High Similarity	NPC175799
0.8947	High Similarity	NPC610
0.8947	High Similarity	NPC145023
0.8947	High Similarity	NPC200988
0.8929	High Similarity	NPC264558
0.8908	High Similarity	NPC289459
0.8879	High Similarity	NPC2058
0.8879	High Similarity	NPC304638
0.887	High Similarity	NPC86198
0.8833	High Similarity	NPC147192
0.8833	High Similarity	NPC118584
0.8833	High Similarity	NPC120225
0.8833	High Similarity	NPC475695
0.8833	High Similarity	NPC213552
0.8807	High Similarity	NPC19149
0.8796	High Similarity	NPC79672
0.8796	High Similarity	NPC52087
0.8793	High Similarity	NPC470215
0.8793	High Similarity	NPC470214
0.8793	High Similarity	NPC37858
0.8793	High Similarity	NPC70084
0.8793	High Similarity	NPC109371
0.8785	High Similarity	NPC94343
0.876	High Similarity	NPC476873
0.875	High Similarity	NPC132921
0.875	High Similarity	NPC67951
0.8692	High Similarity	NPC253746
0.8689	High Similarity	NPC110313
0.8689	High Similarity	NPC232880
0.8689	High Similarity	NPC109275
0.8684	High Similarity	NPC294941
0.8678	High Similarity	NPC168653
0.8678	High Similarity	NPC251407
0.8667	High Similarity	NPC469568
0.8621	High Similarity	NPC39793
0.8618	High Similarity	NPC30174
0.8618	High Similarity	NPC48315
0.8618	High Similarity	NPC83062
0.8618	High Similarity	NPC477294
0.8618	High Similarity	NPC229784
0.8618	High Similarity	NPC477293
0.8598	High Similarity	NPC171843
0.8596	High Similarity	NPC148969
0.8595	High Similarity	NPC197832
0.8584	High Similarity	NPC139946
0.8583	High Similarity	NPC285345
0.8583	High Similarity	NPC306100
0.856	High Similarity	NPC473285
0.8559	High Similarity	NPC260952
0.8548	High Similarity	NPC32626
0.8548	High Similarity	NPC237506
0.8548	High Similarity	NPC217052
0.8548	High Similarity	NPC329344
0.8547	High Similarity	NPC124916
0.8545	High Similarity	NPC127676
0.8512	High Similarity	NPC288945
0.8496	Intermediate Similarity	NPC183700
0.8492	Intermediate Similarity	NPC155209
0.8492	Intermediate Similarity	NPC475468
0.8492	Intermediate Similarity	NPC168799
0.8492	Intermediate Similarity	NPC254398
0.8487	Intermediate Similarity	NPC14007
0.8487	Intermediate Similarity	NPC224814
0.8487	Intermediate Similarity	NPC109083
0.8487	Intermediate Similarity	NPC60962
0.8487	Intermediate Similarity	NPC189844
0.8487	Intermediate Similarity	NPC269843
0.848	Intermediate Similarity	NPC198388
0.848	Intermediate Similarity	NPC219677
0.8468	Intermediate Similarity	NPC226855
0.8443	Intermediate Similarity	NPC300326
0.8443	Intermediate Similarity	NPC58279
0.8443	Intermediate Similarity	NPC280767
0.843	Intermediate Similarity	NPC212541
0.8426	Intermediate Similarity	NPC131587
0.8425	Intermediate Similarity	NPC471883
0.8425	Intermediate Similarity	NPC471110
0.8425	Intermediate Similarity	NPC135127
0.8425	Intermediate Similarity	NPC106406
0.8421	Intermediate Similarity	NPC297657
0.8413	Intermediate Similarity	NPC25581
0.8413	Intermediate Similarity	NPC473924
0.8413	Intermediate Similarity	NPC18074
0.8413	Intermediate Similarity	NPC5419
0.8413	Intermediate Similarity	NPC61
0.839	Intermediate Similarity	NPC277460
0.8387	Intermediate Similarity	NPC478215
0.8362	Intermediate Similarity	NPC41851
0.8348	Intermediate Similarity	NPC51698
0.8347	Intermediate Similarity	NPC286573
0.8333	Intermediate Similarity	NPC158949
0.8333	Intermediate Similarity	NPC318799
0.8333	Intermediate Similarity	NPC222084
0.832	Intermediate Similarity	NPC477300
0.8319	Intermediate Similarity	NPC477803
0.8319	Intermediate Similarity	NPC206341
0.8318	Intermediate Similarity	NPC257182
0.8318	Intermediate Similarity	NPC107522
0.8306	Intermediate Similarity	NPC158654
0.8305	Intermediate Similarity	NPC278652
0.8305	Intermediate Similarity	NPC122117
0.8295	Intermediate Similarity	NPC476699
0.8295	Intermediate Similarity	NPC157554
0.8295	Intermediate Similarity	NPC154485
0.8295	Intermediate Similarity	NPC471872
0.8293	Intermediate Similarity	NPC27352
0.8281	Intermediate Similarity	NPC34293
0.8281	Intermediate Similarity	NPC287597
0.8281	Intermediate Similarity	NPC886
0.8281	Intermediate Similarity	NPC474895
0.8279	Intermediate Similarity	NPC160900
0.8279	Intermediate Similarity	NPC18984
0.8279	Intermediate Similarity	NPC229084
0.8279	Intermediate Similarity	NPC106659
0.8273	Intermediate Similarity	NPC110764
0.8264	Intermediate Similarity	NPC472271
0.8264	Intermediate Similarity	NPC194416
0.8264	Intermediate Similarity	NPC322332
0.8264	Intermediate Similarity	NPC177291
0.8261	Intermediate Similarity	NPC139617
0.8261	Intermediate Similarity	NPC78918
0.8254	Intermediate Similarity	NPC285361
0.8246	Intermediate Similarity	NPC36108
0.8246	Intermediate Similarity	NPC7097
0.8246	Intermediate Similarity	NPC75272
0.8246	Intermediate Similarity	NPC246358
0.8246	Intermediate Similarity	NPC471954
0.8246	Intermediate Similarity	NPC233731
0.824	Intermediate Similarity	NPC46192
0.8235	Intermediate Similarity	NPC212743
0.8235	Intermediate Similarity	NPC63126
0.8231	Intermediate Similarity	NPC476376
0.8231	Intermediate Similarity	NPC126206
0.8224	Intermediate Similarity	NPC81010
0.8224	Intermediate Similarity	NPC32977
0.8217	Intermediate Similarity	NPC476870
0.8214	Intermediate Similarity	NPC288760
0.8198	Intermediate Similarity	NPC196479
0.8198	Intermediate Similarity	NPC477801
0.8198	Intermediate Similarity	NPC477802
0.8197	Intermediate Similarity	NPC327070
0.8197	Intermediate Similarity	NPC114298
0.8182	Intermediate Similarity	NPC476872
0.8182	Intermediate Similarity	NPC223393
0.8175	Intermediate Similarity	NPC64111
0.8175	Intermediate Similarity	NPC208536
0.8174	Intermediate Similarity	NPC147634
0.8174	Intermediate Similarity	NPC226401
0.8174	Intermediate Similarity	NPC120982
0.8174	Intermediate Similarity	NPC79793
0.8174	Intermediate Similarity	NPC174096
0.8168	Intermediate Similarity	NPC220942
0.8168	Intermediate Similarity	NPC100389
0.8168	Intermediate Similarity	NPC182249
0.8168	Intermediate Similarity	NPC68092
0.8168	Intermediate Similarity	NPC226005
0.8168	Intermediate Similarity	NPC197316
0.8168	Intermediate Similarity	NPC64141
0.8168	Intermediate Similarity	NPC89105
0.8168	Intermediate Similarity	NPC472350
0.8168	Intermediate Similarity	NPC476383
0.8168	Intermediate Similarity	NPC81515
0.8167	Intermediate Similarity	NPC24474
0.8167	Intermediate Similarity	NPC311595

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 NPC233669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	805
0.2-0.3	1740
0.3-0.4	2816
0.4-0.5	1836
0.5-0.6	1186
0.6-0.7	511
0.7-0.8	57
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
0.8279	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.823	Intermediate Similarity	NPD1358	Approved
0.8168	Intermediate Similarity	NPD7266	Discontinued
0.8103	Intermediate Similarity	NPD228	Approved
0.8062	Intermediate Similarity	NPD230	Phase 1
0.7982	Intermediate Similarity	NPD3134	Approved
0.7931	Intermediate Similarity	NPD3022	Approved
0.7931	Intermediate Similarity	NPD3021	Approved
0.7874	Intermediate Similarity	NPD9494	Approved
0.7852	Intermediate Similarity	NPD8166	Discontinued
0.7794	Intermediate Similarity	NPD6190	Approved
0.7787	Intermediate Similarity	NPD9545	Approved
0.7724	Intermediate Similarity	NPD1357	Approved
0.771	Intermediate Similarity	NPD826	Approved
0.771	Intermediate Similarity	NPD825	Approved
0.7705	Intermediate Similarity	NPD5536	Phase 2
0.76	Intermediate Similarity	NPD3496	Discontinued
0.7535	Intermediate Similarity	NPD3455	Phase 2
0.752	Intermediate Similarity	NPD4626	Approved
0.7519	Intermediate Similarity	NPD555	Phase 2
0.7481	Intermediate Similarity	NPD3027	Phase 3
0.748	Intermediate Similarity	NPD9269	Phase 2
0.7465	Intermediate Similarity	NPD1653	Approved
0.7444	Intermediate Similarity	NPD4060	Phase 1
0.744	Intermediate Similarity	NPD5691	Approved
0.7385	Intermediate Similarity	NPD257	Approved
0.7385	Intermediate Similarity	NPD258	Approved
0.7383	Intermediate Similarity	NPD111	Approved
0.7368	Intermediate Similarity	NPD259	Phase 1
0.7339	Intermediate Similarity	NPD9493	Approved
0.7295	Intermediate Similarity	NPD9379	Approved
0.7295	Intermediate Similarity	NPD9377	Approved
0.7273	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD447	Suspended
0.7257	Intermediate Similarity	NPD2933	Approved
0.7257	Intermediate Similarity	NPD2934	Approved
0.7257	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2684	Approved
0.7244	Intermediate Similarity	NPD1778	Approved
0.7244	Intermediate Similarity	NPD9381	Approved
0.7244	Intermediate Similarity	NPD9384	Approved
0.7236	Intermediate Similarity	NPD5283	Phase 1
0.7197	Intermediate Similarity	NPD9569	Approved
0.7197	Intermediate Similarity	NPD5736	Approved
0.7193	Intermediate Similarity	NPD2859	Approved
0.7193	Intermediate Similarity	NPD2860	Approved
0.7193	Intermediate Similarity	NPD844	Approved
0.7185	Intermediate Similarity	NPD1613	Approved
0.7185	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD290	Approved
0.7165	Intermediate Similarity	NPD9268	Approved
0.7155	Intermediate Similarity	NPD3020	Approved
0.7154	Intermediate Similarity	NPD7843	Approved
0.7154	Intermediate Similarity	NPD9622	Approved
0.7132	Intermediate Similarity	NPD422	Phase 1
0.712	Intermediate Similarity	NPD7157	Approved
0.7105	Intermediate Similarity	NPD9296	Approved
0.7094	Intermediate Similarity	NPD1242	Phase 1
0.7092	Intermediate Similarity	NPD4110	Phase 3
0.7092	Intermediate Similarity	NPD4628	Phase 3
0.7092	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7095	Approved
0.708	Intermediate Similarity	NPD6653	Approved
0.7073	Intermediate Similarity	NPD969	Suspended
0.7063	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3620	Phase 2
0.7059	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD9570	Approved
0.705	Intermediate Similarity	NPD2935	Discontinued
0.7037	Intermediate Similarity	NPD6798	Discontinued
0.7037	Intermediate Similarity	NPD3144	Approved
0.7037	Intermediate Similarity	NPD3145	Approved
0.7034	Intermediate Similarity	NPD291	Approved
0.7016	Intermediate Similarity	NPD5535	Approved
0.7015	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD274	Approved
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD275	Approved
0.7	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9697	Approved
0.7	Intermediate Similarity	NPD3705	Approved
0.6992	Remote Similarity	NPD9619	Approved
0.6992	Remote Similarity	NPD9621	Approved
0.6992	Remote Similarity	NPD9620	Approved
0.6985	Remote Similarity	NPD2674	Phase 3
0.6985	Remote Similarity	NPD4062	Phase 3
0.6985	Remote Similarity	NPD6663	Approved
0.6985	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6233	Phase 2
0.6983	Remote Similarity	NPD288	Approved
0.6963	Remote Similarity	NPD9537	Phase 1
0.6963	Remote Similarity	NPD9536	Phase 1
0.696	Remote Similarity	NPD1241	Discontinued
0.6949	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD9717	Approved
0.6942	Remote Similarity	NPD968	Approved
0.694	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1282	Approved
0.6934	Remote Similarity	NPD943	Approved
0.6934	Remote Similarity	NPD4140	Approved
0.6923	Remote Similarity	NPD3847	Discontinued
0.6912	Remote Similarity	NPD597	Approved
0.6912	Remote Similarity	NPD598	Approved
0.6912	Remote Similarity	NPD601	Approved
0.6912	Remote Similarity	NPD3764	Approved
0.6899	Remote Similarity	NPD5585	Approved
0.6891	Remote Similarity	NPD940	Approved
0.6891	Remote Similarity	NPD846	Approved
0.6884	Remote Similarity	NPD4340	Discontinued
0.688	Remote Similarity	NPD821	Approved
0.6879	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3686	Approved
0.6871	Remote Similarity	NPD3687	Approved
0.687	Remote Similarity	NPD1535	Discovery
0.687	Remote Similarity	NPD3092	Approved
0.6867	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5647	Approved
0.6861	Remote Similarity	NPD1132	Approved
0.6861	Remote Similarity	NPD1130	Approved
0.6861	Remote Similarity	NPD1136	Approved
0.685	Remote Similarity	NPD6671	Approved
0.685	Remote Similarity	NPD4198	Discontinued
0.6842	Remote Similarity	NPD1283	Approved
0.6842	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6647	Phase 2
0.6829	Remote Similarity	NPD74	Approved
0.6829	Remote Similarity	NPD9266	Approved
0.6824	Remote Similarity	NPD3111	Phase 1
0.6822	Remote Similarity	NPD1894	Discontinued
0.6822	Remote Similarity	NPD3091	Approved
0.6818	Remote Similarity	NPD1481	Phase 2
0.6812	Remote Similarity	NPD1558	Phase 1
0.6812	Remote Similarity	NPD3061	Approved
0.6812	Remote Similarity	NPD3062	Approved
0.6812	Remote Similarity	NPD3059	Approved
0.68	Remote Similarity	NPD1934	Approved
0.6791	Remote Similarity	NPD3094	Phase 2
0.6791	Remote Similarity	NPD987	Approved
0.6791	Remote Similarity	NPD1203	Approved
0.6791	Remote Similarity	NPD3053	Approved
0.6791	Remote Similarity	NPD3055	Approved
0.6788	Remote Similarity	NPD411	Approved
0.6788	Remote Similarity	NPD1048	Approved
0.6783	Remote Similarity	NPD1652	Phase 2
0.678	Remote Similarity	NPD9495	Approved
0.6776	Remote Similarity	NPD3882	Suspended
0.6772	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2629	Approved
0.6767	Remote Similarity	NPD2983	Phase 2
0.6767	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD2982	Phase 2
0.6761	Remote Similarity	NPD5762	Approved
0.6761	Remote Similarity	NPD5763	Approved
0.6752	Remote Similarity	NPD1809	Phase 2
0.6748	Remote Similarity	NPD9263	Approved
0.6748	Remote Similarity	NPD9264	Approved
0.6748	Remote Similarity	NPD9267	Approved
0.6742	Remote Similarity	NPD1091	Approved
0.6741	Remote Similarity	NPD6584	Phase 3
0.6738	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD845	Approved
0.6719	Remote Similarity	NPD256	Approved
0.6719	Remote Similarity	NPD255	Approved
0.6716	Remote Similarity	NPD5310	Approved
0.6716	Remote Similarity	NPD5311	Approved
0.6714	Remote Similarity	NPD5314	Approved
0.6714	Remote Similarity	NPD2653	Approved
0.6713	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1511	Approved
0.6712	Remote Similarity	NPD4357	Discontinued
0.6711	Remote Similarity	NPD824	Approved
0.6692	Remote Similarity	NPD2981	Phase 2
0.6692	Remote Similarity	NPD1608	Approved
0.6692	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2861	Phase 2
0.669	Remote Similarity	NPD6032	Approved
0.6688	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD3060	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD1445	Approved
0.6667	Remote Similarity	NPD1444	Approved
0.6667	Remote Similarity	NPD689	Discontinued
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7685	Pre-registration
0.6645	Remote Similarity	NPD2801	Approved
0.6645	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5124	Phase 1
0.6643	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4359	Approved
0.6642	Remote Similarity	NPD3685	Discontinued
0.6641	Remote Similarity	NPD9614	Approved
0.6641	Remote Similarity	NPD9618	Approved
0.664	Remote Similarity	NPD556	Approved
0.664	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.664	Remote Similarity	NPD2067	Discontinued
0.6622	Remote Similarity	NPD1512	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