NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	278.782
LogP:	3.684
LogD:	3.903
LogS:	-3.563
# Rotatable Bonds:	6
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.503
Synthetic Accessibility Score:	2.281
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.604
MDCK Permeability:	2.3690445232205093e-05
Pgp-inhibitor:	0.183
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.198
30% Bioavailability (F30%):	0.674

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.61
Plasma Protein Binding (PPB):	95.05329132080078%
Volume Distribution (VD):	2.062
Pgp-substrate:	7.241682052612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.707
CYP2C19-inhibitor:	0.916
CYP2C19-substrate:	0.532
CYP2C9-inhibitor:	0.769
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.625
CYP2D6-substrate:	0.844
CYP3A4-inhibitor:	0.416
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	14.167
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.914
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.248
Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.166
Skin Sensitization:	0.908
Carcinogencity:	0.266
Eye Corrosion:	0.013
Eye Irritation:	0.535
Respiratory Toxicity:	0.611

Download Data

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

Natural Product: NPC204466

Natural Product ID:	NPC204466
*Common Name:**	Ferulic Acid 3',3'-Dimethylallyl Ester
IUPAC Name:	3-methylbut-2-enyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	LGFZYQVEWDKGLZ-FNORWQNLSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-11(2)8-9-19-15(17)7-5-12-4-6-13(16)14(10-12)18-3/h4-8,10,16H,9H2,1-3H3/b7-5+
SMILES:	COc1cc(/C=C/C(=O)OCC=C(C)C)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3311503
PubChem CID:	11369032
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
NPO33094	korean propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24928402]

☑ 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
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio IC50	=	23.1	n.a.	PMID[475317]
NPT2	Others	Unspecified		Ratio IC50	=	105.0	n.a.	PMID[475317]

☑ 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 NPC204466 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	260
0.1-0.2	1436
0.2-0.3	4873
0.3-0.4	11522
0.4-0.5	6400
0.5-0.6	5156
0.6-0.7	9502
0.7-0.8	2983
0.8-0.85	400
0.85-0.9	104
0.9-0.95	45
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC202474
0.9912	High Similarity	NPC70752
0.9735	High Similarity	NPC164706
0.9735	High Similarity	NPC137537
0.9735	High Similarity	NPC70744
0.9735	High Similarity	NPC272471
0.9735	High Similarity	NPC107588
0.9658	High Similarity	NPC20443
0.9658	High Similarity	NPC246704
0.9658	High Similarity	NPC146886
0.9658	High Similarity	NPC60517
0.9576	High Similarity	NPC289459
0.9565	High Similarity	NPC2058
0.9496	High Similarity	NPC213552
0.9496	High Similarity	NPC120225
0.9478	High Similarity	NPC37858
0.9381	High Similarity	NPC294941
0.9381	High Similarity	NPC33749
0.9381	High Similarity	NPC261453
0.9381	High Similarity	NPC328593
0.9339	High Similarity	NPC110313
0.9339	High Similarity	NPC109275
0.9304	High Similarity	NPC39793
0.9298	High Similarity	NPC474967
0.9298	High Similarity	NPC233669
0.9292	High Similarity	NPC95381
0.9262	High Similarity	NPC48315
0.9262	High Similarity	NPC83062
0.9224	High Similarity	NPC124916
0.9217	High Similarity	NPC281277
0.9211	High Similarity	NPC217472
0.9153	High Similarity	NPC60962
0.9153	High Similarity	NPC269843
0.9153	High Similarity	NPC224814
0.9153	High Similarity	NPC109083
0.9153	High Similarity	NPC189844
0.9153	High Similarity	NPC14007
0.9138	High Similarity	NPC65791
0.9115	High Similarity	NPC226250
0.9091	High Similarity	NPC58279
0.9091	High Similarity	NPC280767
0.9091	High Similarity	NPC300326
0.906	High Similarity	NPC203124
0.906	High Similarity	NPC309434
0.906	High Similarity	NPC277460
0.9024	High Similarity	NPC478215
0.9	High Similarity	NPC286573
0.8992	High Similarity	NPC158949
0.8968	High Similarity	NPC475468
0.8947	High Similarity	NPC78918
0.8947	High Similarity	NPC139617
0.8938	High Similarity	NPC7097
0.8938	High Similarity	NPC36108
0.8938	High Similarity	NPC233731
0.8938	High Similarity	NPC246358
0.8934	High Similarity	NPC27352
0.8926	High Similarity	NPC160900
0.8926	High Similarity	NPC18984
0.8926	High Similarity	NPC106659
0.8926	High Similarity	NPC229084
0.8917	High Similarity	NPC194416
0.8917	High Similarity	NPC177291
0.8898	High Similarity	NPC275519
0.8898	High Similarity	NPC135127
0.8898	High Similarity	NPC471110
0.8898	High Similarity	NPC212743
0.887	High Similarity	NPC131530
0.8843	High Similarity	NPC114298
0.8833	High Similarity	NPC470848
0.8833	High Similarity	NPC470849
0.8824	High Similarity	NPC57501
0.8824	High Similarity	NPC141791
0.8824	High Similarity	NPC263386
0.8814	High Similarity	NPC280001
0.8783	High Similarity	NPC156840
0.8783	High Similarity	NPC8547
0.8783	High Similarity	NPC257124
0.8783	High Similarity	NPC173746
0.878	High Similarity	NPC87113
0.878	High Similarity	NPC271985
0.877	High Similarity	NPC257976
0.877	High Similarity	NPC4181
0.877	High Similarity	NPC238810
0.877	High Similarity	NPC164778
0.877	High Similarity	NPC242372
0.876	High Similarity	NPC114845
0.876	High Similarity	NPC157554
0.876	High Similarity	NPC310373
0.876	High Similarity	NPC90431
0.876	High Similarity	NPC120852
0.875	High Similarity	NPC111635
0.871	High Similarity	NPC276014
0.8699	High Similarity	NPC312404
0.8699	High Similarity	NPC273686
0.8696	High Similarity	NPC179309
0.8692	High Similarity	NPC126206
0.8689	High Similarity	NPC288238
0.8678	High Similarity	NPC307253
0.8673	High Similarity	NPC294902
0.8673	High Similarity	NPC1786
0.8673	High Similarity	NPC1075
0.8667	High Similarity	NPC24474
0.8667	High Similarity	NPC69670
0.8667	High Similarity	NPC311595
0.8667	High Similarity	NPC241634
0.8655	High Similarity	NPC212643
0.8655	High Similarity	NPC164386
0.8655	High Similarity	NPC293619
0.8655	High Similarity	NPC199209
0.8651	High Similarity	NPC241354
0.864	High Similarity	NPC5018
0.864	High Similarity	NPC123228
0.864	High Similarity	NPC151167
0.864	High Similarity	NPC123722
0.864	High Similarity	NPC276466
0.8626	High Similarity	NPC100389
0.8626	High Similarity	NPC226005
0.8626	High Similarity	NPC284409
0.8626	High Similarity	NPC132723
0.8626	High Similarity	NPC76032
0.8621	High Similarity	NPC55300
0.8621	High Similarity	NPC245552
0.8618	High Similarity	NPC224208
0.8618	High Similarity	NPC474275
0.8615	High Similarity	NPC471665
0.8615	High Similarity	NPC186418
0.8615	High Similarity	NPC471664
0.8607	High Similarity	NPC470804
0.8607	High Similarity	NPC147654
0.8605	High Similarity	NPC92830
0.8596	High Similarity	NPC227894
0.8595	High Similarity	NPC222175
0.8594	High Similarity	NPC245120
0.8594	High Similarity	NPC111888
0.8584	High Similarity	NPC288760
0.8583	High Similarity	NPC255675
0.8583	High Similarity	NPC470626
0.8583	High Similarity	NPC205502
0.8583	High Similarity	NPC159916
0.8571	High Similarity	NPC221049
0.8561	High Similarity	NPC106055
0.8561	High Similarity	NPC288452
0.8561	High Similarity	NPC110699
0.8561	High Similarity	NPC289690
0.856	High Similarity	NPC303680
0.856	High Similarity	NPC179777
0.856	High Similarity	NPC118584
0.856	High Similarity	NPC84076
0.856	High Similarity	NPC90128
0.8547	High Similarity	NPC165646
0.8538	High Similarity	NPC477301
0.8534	High Similarity	NPC137685
0.8527	High Similarity	NPC159418
0.8527	High Similarity	NPC283823
0.8525	High Similarity	NPC207613
0.8525	High Similarity	NPC471877
0.8512	High Similarity	NPC320987
0.8512	High Similarity	NPC299406
0.8512	High Similarity	NPC181969
0.8504	High Similarity	NPC304622
0.8496	Intermediate Similarity	NPC2518
0.8492	Intermediate Similarity	NPC281020
0.8492	Intermediate Similarity	NPC117237
0.8492	Intermediate Similarity	NPC203719
0.8485	Intermediate Similarity	NPC13067
0.848	Intermediate Similarity	NPC67951
0.8475	Intermediate Similarity	NPC303522
0.8475	Intermediate Similarity	NPC264558
0.8473	Intermediate Similarity	NPC37468
0.8468	Intermediate Similarity	NPC21238
0.8468	Intermediate Similarity	NPC163083
0.8468	Intermediate Similarity	NPC317769
0.8468	Intermediate Similarity	NPC31344
0.8462	Intermediate Similarity	NPC68779
0.8462	Intermediate Similarity	NPC249791
0.8462	Intermediate Similarity	NPC237594
0.8462	Intermediate Similarity	NPC476387
0.8462	Intermediate Similarity	NPC300776
0.8462	Intermediate Similarity	NPC119060
0.8462	Intermediate Similarity	NPC195873
0.8462	Intermediate Similarity	NPC5310
0.8462	Intermediate Similarity	NPC4982
0.8462	Intermediate Similarity	NPC67247
0.8462	Intermediate Similarity	NPC176814
0.8455	Intermediate Similarity	NPC113865
0.8455	Intermediate Similarity	NPC201777
0.8455	Intermediate Similarity	NPC343720
0.8455	Intermediate Similarity	NPC470212
0.8455	Intermediate Similarity	NPC324571
0.8455	Intermediate Similarity	NPC54872
0.8455	Intermediate Similarity	NPC312675
0.8455	Intermediate Similarity	NPC476343
0.8455	Intermediate Similarity	NPC473853
0.8455	Intermediate Similarity	NPC262156
0.8455	Intermediate Similarity	NPC184651
0.8455	Intermediate Similarity	NPC193484
0.845	Intermediate Similarity	NPC5423
0.8443	Intermediate Similarity	NPC242885
0.8443	Intermediate Similarity	NPC35071
0.8443	Intermediate Similarity	NPC232316

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 NPC204466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	879
0.2-0.3	1802
0.3-0.4	2737
0.4-0.5	1736
0.5-0.6	1025
0.6-0.7	655
0.7-0.8	92
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8926	High Similarity	NPD4379	Clinical (unspecified phase)
0.8783	High Similarity	NPD228	Approved
0.8761	High Similarity	NPD1358	Approved
0.8492	Intermediate Similarity	NPD9494	Approved
0.8348	Intermediate Similarity	NPD3134	Approved
0.8347	Intermediate Similarity	NPD5536	Phase 2
0.8211	Intermediate Similarity	NPD1357	Approved
0.7939	Intermediate Similarity	NPD3027	Phase 3
0.7937	Intermediate Similarity	NPD3496	Discontinued
0.7895	Intermediate Similarity	NPD4060	Phase 1
0.7887	Intermediate Similarity	NPD1653	Approved
0.7869	Intermediate Similarity	NPD5283	Phase 1
0.7857	Intermediate Similarity	NPD4626	Approved
0.7836	Intermediate Similarity	NPD447	Suspended
0.7836	Intermediate Similarity	NPD230	Phase 1
0.781	Intermediate Similarity	NPD7266	Discontinued
0.7788	Intermediate Similarity	NPD9296	Approved
0.7778	Intermediate Similarity	NPD5691	Approved
0.775	Intermediate Similarity	NPD2684	Approved
0.7642	Intermediate Similarity	NPD7843	Approved
0.7612	Intermediate Similarity	NPD3145	Approved
0.7612	Intermediate Similarity	NPD3144	Approved
0.7606	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7157	Approved
0.7597	Intermediate Similarity	NPD3705	Approved
0.7578	Intermediate Similarity	NPD1778	Approved
0.7559	Intermediate Similarity	NPD9545	Approved
0.7556	Intermediate Similarity	NPD2674	Phase 3
0.7542	Intermediate Similarity	NPD291	Approved
0.7541	Intermediate Similarity	NPD3022	Approved
0.7541	Intermediate Similarity	NPD3021	Approved
0.7537	Intermediate Similarity	NPD7095	Approved
0.7521	Intermediate Similarity	NPD290	Approved
0.7518	Intermediate Similarity	NPD4110	Phase 3
0.7518	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD8166	Discontinued
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3620	Phase 2
0.75	Intermediate Similarity	NPD1613	Approved
0.7465	Intermediate Similarity	NPD6190	Approved
0.7463	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD422	Phase 1
0.7426	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7391	Intermediate Similarity	NPD6653	Approved
0.7388	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD825	Approved
0.7372	Intermediate Similarity	NPD1558	Phase 1
0.7372	Intermediate Similarity	NPD826	Approved
0.736	Intermediate Similarity	NPD5535	Approved
0.7357	Intermediate Similarity	NPD2935	Discontinued
0.7355	Intermediate Similarity	NPD9697	Approved
0.7353	Intermediate Similarity	NPD6798	Discontinued
0.7348	Intermediate Similarity	NPD2983	Phase 2
0.7348	Intermediate Similarity	NPD2982	Phase 2
0.7347	Intermediate Similarity	NPD3455	Phase 2
0.7347	Intermediate Similarity	NPD3111	Phase 1
0.7319	Intermediate Similarity	NPD4340	Discontinued
0.7319	Intermediate Similarity	NPD6355	Discontinued
0.7302	Intermediate Similarity	NPD1241	Discontinued
0.7299	Intermediate Similarity	NPD4062	Phase 3
0.7299	Intermediate Similarity	NPD6233	Phase 2
0.7295	Intermediate Similarity	NPD968	Approved
0.7285	Intermediate Similarity	NPD3882	Suspended
0.7285	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3687	Approved
0.7279	Intermediate Similarity	NPD3686	Approved
0.7273	Intermediate Similarity	NPD9717	Approved
0.7273	Intermediate Similarity	NPD2981	Phase 2
0.7266	Intermediate Similarity	NPD2653	Approved
0.7252	Intermediate Similarity	NPD3847	Discontinued
0.7241	Intermediate Similarity	NPD4357	Discontinued
0.7239	Intermediate Similarity	NPD987	Approved
0.7231	Intermediate Similarity	NPD5585	Approved
0.723	Intermediate Similarity	NPD824	Approved
0.7222	Intermediate Similarity	NPD821	Approved
0.72	Intermediate Similarity	NPD1934	Approved
0.7197	Intermediate Similarity	NPD1535	Discovery
0.7194	Intermediate Similarity	NPD555	Phase 2
0.7188	Intermediate Similarity	NPD6671	Approved
0.7185	Intermediate Similarity	NPD5647	Approved
0.7164	Intermediate Similarity	NPD1283	Approved
0.7154	Intermediate Similarity	NPD1894	Discontinued
0.7152	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2492	Phase 1
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7132	Intermediate Similarity	NPD3018	Phase 2
0.7132	Intermediate Similarity	NPD9493	Approved
0.7122	Intermediate Similarity	NPD4140	Approved
0.712	Intermediate Similarity	NPD556	Approved
0.7114	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1203	Approved
0.7105	Intermediate Similarity	NPD3817	Phase 2
0.7101	Intermediate Similarity	NPD411	Approved
0.7101	Intermediate Similarity	NPD1048	Approved
0.709	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3060	Approved
0.7083	Intermediate Similarity	NPD1652	Phase 2
0.708	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6234	Discontinued
0.7071	Intermediate Similarity	NPD1933	Approved
0.7069	Intermediate Similarity	NPD9365	Approved
0.7068	Intermediate Similarity	NPD1091	Approved
0.7063	Intermediate Similarity	NPD5763	Approved
0.7063	Intermediate Similarity	NPD5762	Approved
0.7063	Intermediate Similarity	NPD1375	Discontinued
0.7059	Intermediate Similarity	NPD257	Approved
0.7059	Intermediate Similarity	NPD258	Approved
0.7059	Intermediate Similarity	NPD6584	Phase 3
0.705	Intermediate Similarity	NPD259	Phase 1
0.7039	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6385	Approved
0.702	Intermediate Similarity	NPD6386	Approved
0.7019	Intermediate Similarity	NPD7685	Pre-registration
0.7015	Intermediate Similarity	NPD1608	Approved
0.7014	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1511	Approved
0.6993	Remote Similarity	NPD6032	Approved
0.6993	Remote Similarity	NPD2161	Phase 2
0.6991	Remote Similarity	NPD111	Approved
0.6987	Remote Similarity	NPD8127	Discontinued
0.6985	Remote Similarity	NPD2797	Approved
0.698	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7097	Phase 1
0.6966	Remote Similarity	NPD4162	Approved
0.6966	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4236	Phase 3
0.6966	Remote Similarity	NPD4237	Approved
0.6963	Remote Similarity	NPD4359	Approved
0.6959	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4739	Approved
0.6959	Remote Similarity	NPD3146	Approved
0.6953	Remote Similarity	NPD9379	Approved
0.6953	Remote Similarity	NPD9377	Approved
0.6944	Remote Similarity	NPD3656	Approved
0.694	Remote Similarity	NPD1281	Approved
0.6929	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1465	Phase 2
0.6923	Remote Similarity	NPD2799	Discontinued
0.6917	Remote Similarity	NPD6516	Phase 2
0.6917	Remote Similarity	NPD5846	Approved
0.6913	Remote Similarity	NPD1512	Approved
0.6912	Remote Similarity	NPD3225	Approved
0.6912	Remote Similarity	NPD2922	Phase 1
0.6906	Remote Similarity	NPD5163	Phase 2
0.6897	Remote Similarity	NPD2424	Discontinued
0.6897	Remote Similarity	NPD4534	Discontinued
0.6897	Remote Similarity	NPD9295	Approved
0.6897	Remote Similarity	NPD7153	Discontinued
0.6894	Remote Similarity	NPD1548	Phase 1
0.6892	Remote Similarity	NPD6799	Approved
0.6891	Remote Similarity	NPD2933	Approved
0.6891	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2934	Approved
0.6884	Remote Similarity	NPD2861	Phase 2
0.6884	Remote Similarity	NPD9569	Approved
0.6879	Remote Similarity	NPD2821	Approved
0.6879	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD2240	Approved
0.6875	Remote Similarity	NPD2438	Suspended
0.6875	Remote Similarity	NPD969	Suspended
0.6875	Remote Similarity	NPD1551	Phase 2
0.6875	Remote Similarity	NPD3818	Discontinued
0.6875	Remote Similarity	NPD2239	Approved
0.6871	Remote Similarity	NPD2219	Phase 1
0.687	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD37	Approved
0.6857	Remote Similarity	NPD3268	Approved
0.6857	Remote Similarity	NPD5109	Approved
0.6857	Remote Similarity	NPD5111	Phase 2
0.6857	Remote Similarity	NPD5110	Phase 2
0.6855	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6166	Phase 2
0.6855	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4123	Phase 3
0.6846	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3536	Discontinued
0.6846	Remote Similarity	NPD9299	Approved
0.6846	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9268	Approved
0.6842	Remote Similarity	NPD1651	Approved
0.6842	Remote Similarity	NPD7028	Phase 2
0.6839	Remote Similarity	NPD4965	Approved
0.6839	Remote Similarity	NPD4967	Phase 2
0.6839	Remote Similarity	NPD4966	Approved
0.6838	Remote Similarity	NPD6582	Phase 2
0.6838	Remote Similarity	NPD3685	Discontinued
0.6838	Remote Similarity	NPD6583	Phase 3
0.6835	Remote Similarity	NPD2614	Approved
0.6835	Remote Similarity	NPD6832	Phase 2
0.6835	Remote Similarity	NPD6232	Discontinued
0.6835	Remote Similarity	NPD4908	Phase 1
0.6833	Remote Similarity	NPD2859	Approved
0.6833	Remote Similarity	NPD2860	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