NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.24
Volume:	323.635
LogP:	6.881
LogD:	3.321
LogS:	-5.267
# Rotatable Bonds:	13
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	2.704
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.0
MDCK Permeability:	2.93451903417008e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.549
30% Bioavailability (F30%):	0.745

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	98.87126922607422%
Volume Distribution (VD):	0.744
Pgp-substrate:	0.969560980796814%

ADMET: Metabolism

CYP1A2-inhibitor:	0.242
CYP1A2-substrate:	0.213
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.292
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.03

ADMET: Excretion

Clearance (CL):	2.093
Half-life (T1/2):	0.512

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.939
Carcinogencity:	0.103
Eye Corrosion:	0.955
Eye Irritation:	0.974
Respiratory Toxicity:	0.862

Download Data

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

Natural Product: NPC174560

Natural Product ID:	NPC174560
*Common Name:**	13-(Cyclopent-2-Enyl)Tridecanoic Acid
IUPAC Name:	13-cyclopent-2-en-1-yltridecanoic acid
Synonyms:
Standard InCHIKey:	XMVQWNRDPAAMJB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H32O2/c19-18(20)16-10-8-6-4-2-1-3-5-7-9-13-17-14-11-12-15-17/h11,14,17H,1-10,12-13,15-16H2,(H,19,20)
SMILES:	OC(=O)CCCCCCCCCCCCC1C=CCC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1649743
PubChem CID:	72853
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

*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
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22966846]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11144	Centella asiatica	Species	Apiaceae	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	1
Others	5

Activity Type	# Activity
Individual Protein	4
PROTEIN COMPLEX	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4006	Individual Protein	Telomere resolvase resT	Borrelia burgdorferi (strain ATCC 35210 / B31 / CIP 102532 / DSM4680)	IC50	=	2620.0	nM	PMID[572563]
NPT4006	Individual Protein	Telomere resolvase resT	Borrelia burgdorferi (strain ATCC 35210 / B31 / CIP 102532 / DSM4680)	Inhibition	=	75.0	%	PMID[572563]
NPT4006	Individual Protein	Telomere resolvase resT	Borrelia burgdorferi (strain ATCC 35210 / B31 / CIP 102532 / DSM4680)	Inhibition	=	70.0	%	PMID[572563]
NPT4006	Individual Protein	Telomere resolvase resT	Borrelia burgdorferi (strain ATCC 35210 / B31 / CIP 102532 / DSM4680)	Inhibition	=	5.0	%	PMID[572563]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	91.0	%	PMID[572564]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	100.0	%	PMID[572564]

☑ 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 NPC174560 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	174
0.1-0.2	1648
0.2-0.3	11972
0.3-0.4	14982
0.4-0.5	7878
0.5-0.6	4798
0.6-0.7	1061
0.7-0.8	152
0.8-0.85	27
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC125312
0.875	High Similarity	NPC476614
0.8448	Intermediate Similarity	NPC154245
0.8448	Intermediate Similarity	NPC88966
0.8448	Intermediate Similarity	NPC32467
0.8448	Intermediate Similarity	NPC261831
0.8448	Intermediate Similarity	NPC85813
0.8448	Intermediate Similarity	NPC87564
0.8448	Intermediate Similarity	NPC424
0.8448	Intermediate Similarity	NPC281972
0.8448	Intermediate Similarity	NPC6095
0.8448	Intermediate Similarity	NPC25417
0.8448	Intermediate Similarity	NPC290563
0.8276	Intermediate Similarity	NPC294548
0.8276	Intermediate Similarity	NPC70387
0.8276	Intermediate Similarity	NPC139029
0.8276	Intermediate Similarity	NPC321062
0.8276	Intermediate Similarity	NPC1813
0.8276	Intermediate Similarity	NPC36061
0.8197	Intermediate Similarity	NPC329819
0.8167	Intermediate Similarity	NPC477201
0.8167	Intermediate Similarity	NPC18951
0.8125	Intermediate Similarity	NPC234767
0.8103	Intermediate Similarity	NPC92114
0.8103	Intermediate Similarity	NPC281245
0.803	Intermediate Similarity	NPC60120
0.8	Intermediate Similarity	NPC54766
0.7931	Intermediate Similarity	NPC262968
0.7931	Intermediate Similarity	NPC48162
0.7917	Intermediate Similarity	NPC192006
0.7887	Intermediate Similarity	NPC279537
0.7869	Intermediate Similarity	NPC187777
0.7869	Intermediate Similarity	NPC179764
0.7857	Intermediate Similarity	NPC55527
0.7826	Intermediate Similarity	NPC160817
0.7794	Intermediate Similarity	NPC67608
0.7778	Intermediate Similarity	NPC274927
0.7778	Intermediate Similarity	NPC106851
0.7759	Intermediate Similarity	NPC224227
0.7759	Intermediate Similarity	NPC59051
0.7746	Intermediate Similarity	NPC476844
0.7746	Intermediate Similarity	NPC201027
0.7742	Intermediate Similarity	NPC225929
0.7719	Intermediate Similarity	NPC207292
0.7719	Intermediate Similarity	NPC180534
0.7705	Intermediate Similarity	NPC274290
0.7705	Intermediate Similarity	NPC477984
0.7705	Intermediate Similarity	NPC473863
0.7671	Intermediate Similarity	NPC11796
0.7671	Intermediate Similarity	NPC218817
0.7667	Intermediate Similarity	NPC39633
0.7667	Intermediate Similarity	NPC139545
0.7667	Intermediate Similarity	NPC309606
0.7656	Intermediate Similarity	NPC243532
0.7647	Intermediate Similarity	NPC53302
0.7639	Intermediate Similarity	NPC469514
0.7612	Intermediate Similarity	NPC308294
0.7612	Intermediate Similarity	NPC142423
0.7606	Intermediate Similarity	NPC161923
0.7606	Intermediate Similarity	NPC476046
0.7606	Intermediate Similarity	NPC3753
0.7606	Intermediate Similarity	NPC103958
0.7606	Intermediate Similarity	NPC251970
0.7606	Intermediate Similarity	NPC183503
0.7606	Intermediate Similarity	NPC283908
0.7606	Intermediate Similarity	NPC237591
0.7606	Intermediate Similarity	NPC241854
0.7586	Intermediate Similarity	NPC5413
0.7586	Intermediate Similarity	NPC149821
0.7571	Intermediate Similarity	NPC29328
0.7571	Intermediate Similarity	NPC288667
0.7568	Intermediate Similarity	NPC209995
0.7541	Intermediate Similarity	NPC87394
0.7538	Intermediate Similarity	NPC201939
0.7534	Intermediate Similarity	NPC120776
0.7534	Intermediate Similarity	NPC240170
0.7534	Intermediate Similarity	NPC281296
0.75	Intermediate Similarity	NPC278895
0.75	Intermediate Similarity	NPC18357
0.75	Intermediate Similarity	NPC279666
0.75	Intermediate Similarity	NPC192540
0.75	Intermediate Similarity	NPC472875
0.75	Intermediate Similarity	NPC476626
0.7467	Intermediate Similarity	NPC200446
0.7465	Intermediate Similarity	NPC321017
0.7463	Intermediate Similarity	NPC474329
0.7463	Intermediate Similarity	NPC474304
0.7432	Intermediate Similarity	NPC121200
0.7432	Intermediate Similarity	NPC179028
0.7432	Intermediate Similarity	NPC169095
0.7432	Intermediate Similarity	NPC469495
0.7429	Intermediate Similarity	NPC318766
0.7429	Intermediate Similarity	NPC67183
0.7424	Intermediate Similarity	NPC322457
0.7419	Intermediate Similarity	NPC128061
0.7419	Intermediate Similarity	NPC223677
0.7419	Intermediate Similarity	NPC228473
0.7419	Intermediate Similarity	NPC200845
0.7419	Intermediate Similarity	NPC28779
0.7419	Intermediate Similarity	NPC10316
0.7414	Intermediate Similarity	NPC91495
0.7414	Intermediate Similarity	NPC324793
0.7414	Intermediate Similarity	NPC477878
0.7403	Intermediate Similarity	NPC167103
0.7397	Intermediate Similarity	NPC69143
0.7385	Intermediate Similarity	NPC251042
0.7385	Intermediate Similarity	NPC122521
0.7385	Intermediate Similarity	NPC235242
0.7385	Intermediate Similarity	NPC174447
0.7377	Intermediate Similarity	NPC71761
0.7368	Intermediate Similarity	NPC47031
0.7368	Intermediate Similarity	NPC88735
0.7361	Intermediate Similarity	NPC472966
0.7361	Intermediate Similarity	NPC301065
0.7353	Intermediate Similarity	NPC197089
0.7353	Intermediate Similarity	NPC126899
0.7353	Intermediate Similarity	NPC304665
0.7353	Intermediate Similarity	NPC154728
0.7344	Intermediate Similarity	NPC267817
0.7344	Intermediate Similarity	NPC34416
0.7333	Intermediate Similarity	NPC477371
0.7333	Intermediate Similarity	NPC196827
0.7333	Intermediate Similarity	NPC158846
0.7333	Intermediate Similarity	NPC274996
0.7313	Intermediate Similarity	NPC68343
0.7313	Intermediate Similarity	NPC328089
0.7297	Intermediate Similarity	NPC107039
0.7297	Intermediate Similarity	NPC471899
0.7297	Intermediate Similarity	NPC471897
0.7286	Intermediate Similarity	NPC199557
0.7286	Intermediate Similarity	NPC469914
0.7273	Intermediate Similarity	NPC7414
0.7273	Intermediate Similarity	NPC40082
0.726	Intermediate Similarity	NPC199445
0.7241	Intermediate Similarity	NPC21844
0.7222	Intermediate Similarity	NPC35656
0.7222	Intermediate Similarity	NPC167145
0.7222	Intermediate Similarity	NPC470237
0.7213	Intermediate Similarity	NPC216407
0.7206	Intermediate Similarity	NPC136164
0.7206	Intermediate Similarity	NPC255863
0.7206	Intermediate Similarity	NPC245947
0.7206	Intermediate Similarity	NPC326268
0.7206	Intermediate Similarity	NPC318420
0.72	Intermediate Similarity	NPC239098
0.72	Intermediate Similarity	NPC110094
0.72	Intermediate Similarity	NPC280654
0.72	Intermediate Similarity	NPC260385
0.72	Intermediate Similarity	NPC321514
0.7183	Intermediate Similarity	NPC475310
0.7162	Intermediate Similarity	NPC180886
0.7162	Intermediate Similarity	NPC309399
0.7162	Intermediate Similarity	NPC110461
0.7162	Intermediate Similarity	NPC12740
0.7162	Intermediate Similarity	NPC89294
0.7162	Intermediate Similarity	NPC61863
0.7143	Intermediate Similarity	NPC38350
0.7143	Intermediate Similarity	NPC477372
0.7143	Intermediate Similarity	NPC273508
0.7143	Intermediate Similarity	NPC290445
0.7143	Intermediate Similarity	NPC36616
0.7143	Intermediate Similarity	NPC201912
0.7143	Intermediate Similarity	NPC147066
0.7143	Intermediate Similarity	NPC209327
0.7123	Intermediate Similarity	NPC330016
0.7123	Intermediate Similarity	NPC166797
0.7123	Intermediate Similarity	NPC255168
0.7123	Intermediate Similarity	NPC46610
0.7123	Intermediate Similarity	NPC213223
0.7123	Intermediate Similarity	NPC18819
0.7123	Intermediate Similarity	NPC227396
0.7105	Intermediate Similarity	NPC231431
0.7105	Intermediate Similarity	NPC308545
0.7105	Intermediate Similarity	NPC82488
0.7105	Intermediate Similarity	NPC16394
0.7105	Intermediate Similarity	NPC201225
0.7105	Intermediate Similarity	NPC199595
0.7105	Intermediate Similarity	NPC327674
0.7101	Intermediate Similarity	NPC100719
0.7101	Intermediate Similarity	NPC166791
0.7101	Intermediate Similarity	NPC18252
0.7101	Intermediate Similarity	NPC322035
0.7089	Intermediate Similarity	NPC19849
0.7089	Intermediate Similarity	NPC472865
0.7089	Intermediate Similarity	NPC472864
0.7083	Intermediate Similarity	NPC67076
0.7083	Intermediate Similarity	NPC477983
0.7083	Intermediate Similarity	NPC319163
0.7083	Intermediate Similarity	NPC477981
0.7069	Intermediate Similarity	NPC314679
0.7069	Intermediate Similarity	NPC117572
0.7067	Intermediate Similarity	NPC472014
0.7067	Intermediate Similarity	NPC61952
0.7067	Intermediate Similarity	NPC107668
0.7067	Intermediate Similarity	NPC165711
0.7059	Intermediate Similarity	NPC470325
0.7059	Intermediate Similarity	NPC470320
0.7059	Intermediate Similarity	NPC34883
0.7059	Intermediate Similarity	NPC53642
0.7059	Intermediate Similarity	NPC469723

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 NPC174560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	2399
0.2-0.3	4074
0.3-0.4	1698
0.4-0.5	562
0.5-0.6	222
0.6-0.7	40
0.7-0.8	15
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8448	Intermediate Similarity	NPD3196	Approved
0.8448	Intermediate Similarity	NPD3194	Approved
0.8448	Intermediate Similarity	NPD4266	Approved
0.8448	Intermediate Similarity	NPD3195	Phase 2
0.8276	Intermediate Similarity	NPD3172	Approved
0.7931	Intermediate Similarity	NPD28	Approved
0.7931	Intermediate Similarity	NPD29	Approved
0.7719	Intermediate Similarity	NPD622	Approved
0.7586	Intermediate Similarity	NPD3173	Approved
0.7467	Intermediate Similarity	NPD5368	Approved
0.7432	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7154	Phase 3
0.7403	Intermediate Similarity	NPD5362	Discontinued
0.7368	Intermediate Similarity	NPD5369	Approved
0.7353	Intermediate Similarity	NPD7331	Phase 2
0.7313	Intermediate Similarity	NPD3197	Phase 1
0.7273	Intermediate Similarity	NPD6435	Approved
0.7273	Intermediate Similarity	NPD4270	Approved
0.7273	Intermediate Similarity	NPD4269	Approved
0.7069	Intermediate Similarity	NPD39	Approved
0.7069	Intermediate Similarity	NPD3174	Discontinued
0.7069	Intermediate Similarity	NPD634	Phase 3
0.7069	Intermediate Similarity	NPD4222	Approved
0.7013	Intermediate Similarity	NPD4821	Approved
0.7013	Intermediate Similarity	NPD4820	Approved
0.7013	Intermediate Similarity	NPD4822	Approved
0.7013	Intermediate Similarity	NPD4252	Approved
0.7013	Intermediate Similarity	NPD4819	Approved
0.7	Intermediate Similarity	NPD5363	Approved
0.6974	Remote Similarity	NPD3732	Approved
0.6974	Remote Similarity	NPD4268	Approved
0.6974	Remote Similarity	NPD4271	Approved
0.6957	Remote Similarity	NPD7341	Phase 2
0.6935	Remote Similarity	NPD3186	Phase 1
0.6923	Remote Similarity	NPD4790	Discontinued
0.6923	Remote Similarity	NPD857	Phase 3
0.6914	Remote Similarity	NPD5786	Approved
0.68	Remote Similarity	NPD8039	Approved
0.6795	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5332	Approved
0.675	Remote Similarity	NPD5331	Approved
0.6724	Remote Similarity	NPD5326	Phase 3
0.6618	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5785	Approved
0.6471	Remote Similarity	NPD5347	Phase 2
0.6471	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6101	Approved
0.6471	Remote Similarity	NPD3198	Approved
0.6471	Remote Similarity	NPD5346	Phase 2
0.6429	Remote Similarity	NPD4793	Discontinued
0.6379	Remote Similarity	NPD2270	Approved
0.6322	Remote Similarity	NPD7983	Approved
0.6322	Remote Similarity	NPD5284	Approved
0.6322	Remote Similarity	NPD6411	Approved
0.6322	Remote Similarity	NPD5281	Approved
0.631	Remote Similarity	NPD4519	Discontinued
0.631	Remote Similarity	NPD4623	Approved
0.629	Remote Similarity	NPD5343	Approved
0.6279	Remote Similarity	NPD5370	Suspended
0.6265	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6235	Remote Similarity	NPD4250	Approved
0.6235	Remote Similarity	NPD4251	Approved
0.622	Remote Similarity	NPD4221	Approved
0.622	Remote Similarity	NPD4223	Phase 3
0.622	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3667	Approved
0.6212	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6698	Approved
0.6207	Remote Similarity	NPD46	Approved
0.6197	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5329	Approved
0.6173	Remote Similarity	NPD4695	Discontinued
0.6136	Remote Similarity	NPD7515	Phase 2
0.6136	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6409	Approved
0.6118	Remote Similarity	NPD7146	Approved
0.6118	Remote Similarity	NPD5690	Phase 2
0.6118	Remote Similarity	NPD6422	Discontinued
0.6118	Remote Similarity	NPD7334	Approved
0.6118	Remote Similarity	NPD6684	Approved
0.6118	Remote Similarity	NPD4249	Approved
0.6118	Remote Similarity	NPD5330	Approved
0.6118	Remote Similarity	NPD6098	Approved
0.6118	Remote Similarity	NPD7521	Approved
0.6111	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD226	Approved
0.6092	Remote Similarity	NPD800	Approved
0.6092	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3133	Approved
0.6071	Remote Similarity	NPD4197	Approved
0.6071	Remote Similarity	NPD3665	Phase 1
0.6071	Remote Similarity	NPD3666	Approved
0.6066	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD4191	Approved
0.6056	Remote Similarity	NPD4194	Approved
0.6056	Remote Similarity	NPD4193	Approved
0.6056	Remote Similarity	NPD4192	Approved
0.6044	Remote Similarity	NPD7839	Suspended
0.6034	Remote Similarity	NPD9655	Approved
0.6034	Remote Similarity	NPD633	Phase 3
0.6034	Remote Similarity	NPD9450	Approved
0.6034	Remote Similarity	NPD77	Approved
0.6034	Remote Similarity	NPD9448	Phase 2
0.6024	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD1089	Approved
0.6023	Remote Similarity	NPD1086	Approved
0.6023	Remote Similarity	NPD1090	Approved
0.6	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4756	Discovery
0.6	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6083	Phase 2
0.5978	Remote Similarity	NPD6084	Phase 2
0.5977	Remote Similarity	NPD6903	Approved
0.5977	Remote Similarity	NPD6672	Approved
0.5977	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4518	Approved
0.5977	Remote Similarity	NPD5737	Approved
0.5955	Remote Similarity	NPD6079	Approved
0.5952	Remote Similarity	NPD9491	Approved
0.5946	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5695	Phase 3
0.5934	Remote Similarity	NPD1693	Approved
0.593	Remote Similarity	NPD4688	Approved
0.593	Remote Similarity	NPD5280	Approved
0.593	Remote Similarity	NPD4690	Approved
0.593	Remote Similarity	NPD4694	Approved
0.593	Remote Similarity	NPD5279	Phase 3
0.593	Remote Similarity	NPD4689	Approved
0.593	Remote Similarity	NPD4693	Phase 3
0.593	Remote Similarity	NPD4138	Approved
0.593	Remote Similarity	NPD5205	Approved
0.593	Remote Similarity	NPD3618	Phase 1
0.5926	Remote Similarity	NPD3617	Approved
0.5909	Remote Similarity	NPD5328	Approved
0.5909	Remote Similarity	NPD6080	Approved
0.5909	Remote Similarity	NPD6904	Approved
0.5909	Remote Similarity	NPD6673	Approved
0.589	Remote Similarity	NPD7909	Approved
0.5889	Remote Similarity	NPD1088	Approved
0.5889	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD3206	Approved
0.5862	Remote Similarity	NPD3573	Approved
0.5857	Remote Similarity	NPD6109	Phase 1
0.5851	Remote Similarity	NPD6404	Discontinued
0.5843	Remote Similarity	NPD5207	Approved
0.5833	Remote Similarity	NPD5209	Approved
0.5824	Remote Similarity	NPD5282	Discontinued
0.5814	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD1694	Approved
0.5811	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7902	Approved
0.5806	Remote Similarity	NPD6097	Approved
0.5806	Remote Similarity	NPD6096	Approved
0.5795	Remote Similarity	NPD5208	Approved
0.5783	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5694	Approved
0.5778	Remote Similarity	NPD6050	Approved
0.5778	Remote Similarity	NPD7637	Suspended
0.5747	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5696	Approved
0.5733	Remote Similarity	NPD4224	Phase 2
0.5732	Remote Similarity	NPD225	Approved
0.5732	Remote Similarity	NPD227	Approved
0.573	Remote Similarity	NPD4753	Phase 2
0.573	Remote Similarity	NPD1695	Approved
0.5714	Remote Similarity	NPD4139	Approved
0.5714	Remote Similarity	NPD4692	Approved
0.5714	Remote Similarity	NPD4137	Phase 3
0.5699	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD7614	Phase 1
0.5698	Remote Similarity	NPD3668	Phase 3
0.569	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD2066	Phase 3
0.5682	Remote Similarity	NPD1087	Approved
0.5676	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5692	Phase 3
0.5667	Remote Similarity	NPD3673	Approved
0.5667	Remote Similarity	NPD4096	Approved
0.5667	Remote Similarity	NPD7838	Discovery
0.5667	Remote Similarity	NPD3672	Approved
0.5663	Remote Similarity	NPD4195	Approved
0.5657	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD342	Phase 1
0.5641	Remote Similarity	NPD4747	Approved
0.5641	Remote Similarity	NPD7143	Approved
0.5641	Remote Similarity	NPD7144	Approved
0.5641	Remote Similarity	NPD4691	Approved
0.5625	Remote Similarity	NPD4784	Approved
0.5625	Remote Similarity	NPD4687	Approved
0.5625	Remote Similarity	NPD5733	Approved
0.5625	Remote Similarity	NPD4785	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