NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	306.04
Volume:	279.885
LogP:	5.018
LogD:	3.18
LogS:	-4.174
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	2.539
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	2.085263440676499e-05
Pgp-inhibitor:	0.197
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	100.17359161376953%
Volume Distribution (VD):	1.346
Pgp-substrate:	1.0619841814041138%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.818
CYP2C19-inhibitor:	0.52
CYP2C19-substrate:	0.497
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.522
CYP2D6-substrate:	0.294
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	5.145
Half-life (T1/2):	0.253

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.775
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.454
Maximum Recommended Daily Dose:	0.127
Skin Sensitization:	0.875
Carcinogencity:	0.288
Eye Corrosion:	0.003
Eye Irritation:	0.925
Respiratory Toxicity:	0.808

Download Data

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

Natural Product: NPC200207

Natural Product ID:	NPC200207
*Common Name:**	1-(3,5-Dichloro-2,6-Dihydroxy-4-Methoxyphenyl)Hexan-1-One
IUPAC Name:	1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one
Synonyms:
Standard InCHIKey:	VUDQSRFCCHQIIU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H16Cl2O4/c1-3-4-5-6-7(16)8-11(17)9(14)13(19-2)10(15)12(8)18/h17-18H,3-6H2,1-2H3
SMILES:	CCCCCC(=O)c1c(O)c(Cl)c(c(c1O)Cl)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409648
PubChem CID:	123886
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO33123	polysphondylium filamentosum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[23746784]
NPO31072	Dictyostelium	Genus	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9446571]

☑ 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	3

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5128	Organism	Dictyostelium discoideum	Dictyostelium discoideum	Activity	>	80.0	%	PMID[487777]
NPT1414	Organism	Drosophila	Drosophila	CC50	=	22500.0	nM	PMID[487778]
NPT1414	Organism	Drosophila	Drosophila	IC50	=	4600.0	nM	PMID[487778]
NPT1414	Organism	Drosophila	Drosophila	Ratio CC50/IC50	=	4.9	n.a.	PMID[487778]

☑ 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 NPC200207 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	407
0.1-0.2	2475
0.2-0.3	8303
0.3-0.4	12287
0.4-0.5	5220
0.5-0.6	7130
0.6-0.7	5535
0.7-0.8	1311
0.8-0.85	24
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9118	High Similarity	NPC320819
0.8608	High Similarity	NPC148480
0.8418	Intermediate Similarity	NPC68850
0.8221	Intermediate Similarity	NPC470422
0.8121	Intermediate Similarity	NPC45072
0.8112	Intermediate Similarity	NPC84772
0.8112	Intermediate Similarity	NPC186628
0.8098	Intermediate Similarity	NPC107283
0.8086	Intermediate Similarity	NPC472032
0.8056	Intermediate Similarity	NPC279566
0.8056	Intermediate Similarity	NPC324482
0.8042	Intermediate Similarity	NPC212379
0.8042	Intermediate Similarity	NPC230818
0.8042	Intermediate Similarity	NPC69235
0.8028	Intermediate Similarity	NPC305518
0.8028	Intermediate Similarity	NPC128428
0.8	Intermediate Similarity	NPC27490
0.7988	Intermediate Similarity	NPC470562
0.7988	Intermediate Similarity	NPC470565
0.7988	Intermediate Similarity	NPC277865
0.7952	Intermediate Similarity	NPC477568
0.795	Intermediate Similarity	NPC474096
0.7945	Intermediate Similarity	NPC215875
0.7945	Intermediate Similarity	NPC15834
0.7945	Intermediate Similarity	NPC285054
0.7945	Intermediate Similarity	NPC103105
0.7939	Intermediate Similarity	NPC470560
0.7939	Intermediate Similarity	NPC474857
0.7931	Intermediate Similarity	NPC250057
0.7901	Intermediate Similarity	NPC470081
0.7895	Intermediate Similarity	NPC474499
0.7891	Intermediate Similarity	NPC20560
0.7891	Intermediate Similarity	NPC16197
0.7891	Intermediate Similarity	NPC18877
0.7891	Intermediate Similarity	NPC204960
0.7891	Intermediate Similarity	NPC82225
0.7891	Intermediate Similarity	NPC159623
0.7891	Intermediate Similarity	NPC144051
0.7891	Intermediate Similarity	NPC294593
0.7891	Intermediate Similarity	NPC28753
0.7888	Intermediate Similarity	NPC298401
0.787	Intermediate Similarity	NPC151292
0.7853	Intermediate Similarity	NPC234053
0.7847	Intermediate Similarity	NPC80694
0.7847	Intermediate Similarity	NPC186098
0.7844	Intermediate Similarity	NPC264922
0.784	Intermediate Similarity	NPC473696
0.7838	Intermediate Similarity	NPC164136
0.7838	Intermediate Similarity	NPC103842
0.7838	Intermediate Similarity	NPC236974
0.7838	Intermediate Similarity	NPC286336
0.7838	Intermediate Similarity	NPC144027
0.7836	Intermediate Similarity	NPC471809
0.7836	Intermediate Similarity	NPC471811
0.7823	Intermediate Similarity	NPC203817
0.7806	Intermediate Similarity	NPC477569
0.7805	Intermediate Similarity	NPC474061
0.7785	Intermediate Similarity	NPC156092
0.7785	Intermediate Similarity	NPC84699
0.7785	Intermediate Similarity	NPC13575
0.7785	Intermediate Similarity	NPC101752
0.7778	Intermediate Similarity	NPC195675
0.7778	Intermediate Similarity	NPC471808
0.7778	Intermediate Similarity	NPC471814
0.777	Intermediate Similarity	NPC337373
0.777	Intermediate Similarity	NPC312318
0.777	Intermediate Similarity	NPC175098
0.777	Intermediate Similarity	NPC242294
0.777	Intermediate Similarity	NPC139813
0.777	Intermediate Similarity	NPC192304
0.777	Intermediate Similarity	NPC263670
0.777	Intermediate Similarity	NPC472365
0.777	Intermediate Similarity	NPC188646
0.777	Intermediate Similarity	NPC56031
0.7755	Intermediate Similarity	NPC475008
0.7755	Intermediate Similarity	NPC473584
0.7755	Intermediate Similarity	NPC186097
0.7755	Intermediate Similarity	NPC475009
0.7755	Intermediate Similarity	NPC31872
0.7755	Intermediate Similarity	NPC313618
0.7755	Intermediate Similarity	NPC475589
0.7744	Intermediate Similarity	NPC58653
0.7744	Intermediate Similarity	NPC173352
0.7733	Intermediate Similarity	NPC41461
0.7733	Intermediate Similarity	NPC477244
0.7733	Intermediate Similarity	NPC25287
0.7733	Intermediate Similarity	NPC150399
0.7733	Intermediate Similarity	NPC249606
0.7733	Intermediate Similarity	NPC186838
0.7733	Intermediate Similarity	NPC168105
0.7733	Intermediate Similarity	NPC470397
0.7733	Intermediate Similarity	NPC274109
0.7733	Intermediate Similarity	NPC187826
0.7733	Intermediate Similarity	NPC156910
0.7733	Intermediate Similarity	NPC1486
0.7733	Intermediate Similarity	NPC191606
0.7733	Intermediate Similarity	NPC174999
0.7733	Intermediate Similarity	NPC12165
0.7733	Intermediate Similarity	NPC477243
0.7733	Intermediate Similarity	NPC470398
0.7733	Intermediate Similarity	NPC98115
0.7733	Intermediate Similarity	NPC66349
0.7733	Intermediate Similarity	NPC477242
0.773	Intermediate Similarity	NPC245122
0.7724	Intermediate Similarity	NPC293453
0.7718	Intermediate Similarity	NPC125920
0.7707	Intermediate Similarity	NPC477567
0.7707	Intermediate Similarity	NPC477566
0.7703	Intermediate Similarity	NPC87231
0.7703	Intermediate Similarity	NPC205468
0.7703	Intermediate Similarity	NPC129132
0.7703	Intermediate Similarity	NPC257756
0.7703	Intermediate Similarity	NPC10971
0.7703	Intermediate Similarity	NPC25937
0.7703	Intermediate Similarity	NPC212631
0.7702	Intermediate Similarity	NPC472404
0.7701	Intermediate Similarity	NPC39409
0.7697	Intermediate Similarity	NPC28669
0.7687	Intermediate Similarity	NPC270369
0.7687	Intermediate Similarity	NPC5515
0.7682	Intermediate Similarity	NPC317119
0.7682	Intermediate Similarity	NPC472419
0.7682	Intermediate Similarity	NPC322301
0.7682	Intermediate Similarity	NPC153979
0.7682	Intermediate Similarity	NPC255801
0.7674	Intermediate Similarity	NPC99937
0.7667	Intermediate Similarity	NPC60667
0.7667	Intermediate Similarity	NPC131039
0.7657	Intermediate Similarity	NPC471810
0.7657	Intermediate Similarity	NPC471806
0.7651	Intermediate Similarity	NPC108113
0.7651	Intermediate Similarity	NPC93756
0.7651	Intermediate Similarity	NPC223457
0.7644	Intermediate Similarity	NPC471804
0.7644	Intermediate Similarity	NPC471812
0.764	Intermediate Similarity	NPC280497
0.7639	Intermediate Similarity	NPC65041
0.7635	Intermediate Similarity	NPC189106
0.7635	Intermediate Similarity	NPC164236
0.7635	Intermediate Similarity	NPC262359
0.7635	Intermediate Similarity	NPC128348
0.7635	Intermediate Similarity	NPC309717
0.7635	Intermediate Similarity	NPC112192
0.7635	Intermediate Similarity	NPC66384
0.7635	Intermediate Similarity	NPC64359
0.7635	Intermediate Similarity	NPC308037
0.7632	Intermediate Similarity	NPC131130
0.7632	Intermediate Similarity	NPC21350
0.7632	Intermediate Similarity	NPC272844
0.7632	Intermediate Similarity	NPC251681
0.7632	Intermediate Similarity	NPC471620
0.7632	Intermediate Similarity	NPC124269
0.7632	Intermediate Similarity	NPC477056
0.7632	Intermediate Similarity	NPC248995
0.7632	Intermediate Similarity	NPC470399
0.7632	Intermediate Similarity	NPC472368
0.7632	Intermediate Similarity	NPC254168
0.7632	Intermediate Similarity	NPC243528
0.7632	Intermediate Similarity	NPC477055
0.7622	Intermediate Similarity	NPC470561
0.7619	Intermediate Similarity	NPC42292
0.7619	Intermediate Similarity	NPC185497
0.7619	Intermediate Similarity	NPC307732
0.7616	Intermediate Similarity	NPC470983
0.7616	Intermediate Similarity	NPC470982
0.7616	Intermediate Similarity	NPC472364
0.7616	Intermediate Similarity	NPC222633
0.7616	Intermediate Similarity	NPC476333
0.7616	Intermediate Similarity	NPC472367
0.7616	Intermediate Similarity	NPC213603
0.7616	Intermediate Similarity	NPC473391
0.7616	Intermediate Similarity	NPC121243
0.7616	Intermediate Similarity	NPC240147
0.76	Intermediate Similarity	NPC471813
0.76	Intermediate Similarity	NPC121100
0.76	Intermediate Similarity	NPC471805
0.7582	Intermediate Similarity	NPC470211
0.7582	Intermediate Similarity	NPC472366
0.7582	Intermediate Similarity	NPC217186
0.7582	Intermediate Similarity	NPC53181
0.7582	Intermediate Similarity	NPC139554
0.7582	Intermediate Similarity	NPC23257
0.7582	Intermediate Similarity	NPC240305
0.7582	Intermediate Similarity	NPC140890
0.7582	Intermediate Similarity	NPC477956
0.7582	Intermediate Similarity	NPC283429
0.7576	Intermediate Similarity	NPC470563
0.7566	Intermediate Similarity	NPC131782
0.7566	Intermediate Similarity	NPC294409
0.7566	Intermediate Similarity	NPC188879
0.7566	Intermediate Similarity	NPC138047
0.7566	Intermediate Similarity	NPC162680
0.7566	Intermediate Similarity	NPC474624
0.7566	Intermediate Similarity	NPC7013
0.7566	Intermediate Similarity	NPC209560
0.7566	Intermediate Similarity	NPC303644
0.7566	Intermediate Similarity	NPC181124
0.7566	Intermediate Similarity	NPC116632
0.7561	Intermediate Similarity	NPC472405
0.7557	Intermediate Similarity	NPC471807

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 NPC200207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	1350
0.2-0.3	2438
0.3-0.4	2745
0.4-0.5	1605
0.5-0.6	502
0.6-0.7	128
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7891	Intermediate Similarity	NPD6651	Approved
0.7853	Intermediate Similarity	NPD2403	Approved
0.7755	Intermediate Similarity	NPD1240	Approved
0.7651	Intermediate Similarity	NPD1607	Approved
0.755	Intermediate Similarity	NPD1510	Phase 2
0.7451	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1549	Phase 2
0.7355	Intermediate Similarity	NPD2800	Approved
0.7342	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2533	Approved
0.7233	Intermediate Similarity	NPD2534	Approved
0.7233	Intermediate Similarity	NPD2532	Approved
0.7233	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2796	Approved
0.7012	Intermediate Similarity	NPD4380	Phase 2
0.6988	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7411	Suspended
0.6957	Remote Similarity	NPD1511	Approved
0.6957	Remote Similarity	NPD6799	Approved
0.6954	Remote Similarity	NPD454	Approved
0.6946	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1934	Approved
0.6918	Remote Similarity	NPD2654	Approved
0.6903	Remote Similarity	NPD1184	Approved
0.6886	Remote Similarity	NPD2801	Approved
0.6875	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1512	Approved
0.6867	Remote Similarity	NPD958	Approved
0.6864	Remote Similarity	NPD7075	Discontinued
0.6826	Remote Similarity	NPD6801	Discontinued
0.6807	Remote Similarity	NPD6599	Discontinued
0.6807	Remote Similarity	NPD1715	Phase 1
0.6807	Remote Similarity	NPD1714	Approved
0.6805	Remote Similarity	NPD3882	Suspended
0.6788	Remote Similarity	NPD957	Approved
0.6786	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7819	Suspended
0.6765	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6959	Discontinued
0.6739	Remote Similarity	NPD4360	Phase 2
0.6739	Remote Similarity	NPD6312	Discontinued
0.6739	Remote Similarity	NPD4363	Phase 3
0.673	Remote Similarity	NPD2935	Discontinued
0.673	Remote Similarity	NPD1551	Phase 2
0.671	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1243	Approved
0.6703	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4361	Phase 2
0.6667	Remote Similarity	NPD3750	Approved
0.6647	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6166	Phase 2
0.6629	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD920	Approved
0.6624	Remote Similarity	NPD943	Approved
0.6623	Remote Similarity	NPD9717	Approved
0.6609	Remote Similarity	NPD5710	Approved
0.6609	Remote Similarity	NPD5711	Approved
0.6609	Remote Similarity	NPD6232	Discontinued
0.6608	Remote Similarity	NPD7768	Phase 2
0.6605	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD9493	Approved
0.6591	Remote Similarity	NPD7473	Discontinued
0.657	Remote Similarity	NPD3749	Approved
0.6562	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.655	Remote Similarity	NPD3817	Phase 2
0.6524	Remote Similarity	NPD2354	Approved
0.6517	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7286	Phase 2
0.651	Remote Similarity	NPD9545	Approved
0.6494	Remote Similarity	NPD1203	Approved
0.6485	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD2344	Approved
0.648	Remote Similarity	NPD7074	Phase 3
0.6478	Remote Similarity	NPD230	Phase 1
0.6461	Remote Similarity	NPD3818	Discontinued
0.6447	Remote Similarity	NPD422	Phase 1
0.6444	Remote Similarity	NPD5953	Discontinued
0.6429	Remote Similarity	NPD5403	Approved
0.6425	Remote Similarity	NPD7054	Approved
0.6424	Remote Similarity	NPD3887	Approved
0.642	Remote Similarity	NPD6100	Approved
0.642	Remote Similarity	NPD6099	Approved
0.6416	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1729	Discontinued
0.6389	Remote Similarity	NPD7472	Approved
0.638	Remote Similarity	NPD2353	Approved
0.638	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2799	Discontinued
0.6358	Remote Similarity	NPD3748	Approved
0.6358	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6797	Phase 2
0.6348	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD7390	Discontinued
0.6346	Remote Similarity	NPD2798	Approved
0.6325	Remote Similarity	NPD2309	Approved
0.6319	Remote Similarity	NPD7251	Discontinued
0.631	Remote Similarity	NPD5401	Approved
0.631	Remote Similarity	NPD1578	Phase 2
0.6307	Remote Similarity	NPD5494	Approved
0.6299	Remote Similarity	NPD3972	Approved
0.6284	Remote Similarity	NPD7808	Phase 3
0.6273	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5124	Phase 1
0.6266	Remote Similarity	NPD6832	Phase 2
0.6265	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4628	Phase 3
0.625	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.625	Remote Similarity	NPD919	Approved
0.6235	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6104	Discontinued
0.623	Remote Similarity	NPD6559	Discontinued
0.6207	Remote Similarity	NPD1465	Phase 2
0.6201	Remote Similarity	NPD3926	Phase 2
0.6196	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD1157	Approved
0.6188	Remote Similarity	NPD3268	Approved
0.6188	Remote Similarity	NPD1296	Phase 2
0.6188	Remote Similarity	NPD2313	Discontinued
0.6188	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD411	Approved
0.6184	Remote Similarity	NPD1548	Phase 1
0.618	Remote Similarity	NPD1247	Approved
0.6173	Remote Similarity	NPD447	Suspended
0.6171	Remote Similarity	NPD5402	Approved
0.6164	Remote Similarity	NPD4908	Phase 1
0.6159	Remote Similarity	NPD7033	Discontinued
0.6139	Remote Similarity	NPD1019	Discontinued
0.6129	Remote Similarity	NPD1610	Phase 2
0.6125	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD9494	Approved
0.6098	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD1163	Approved
0.6087	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD940	Approved
0.6084	Remote Similarity	NPD846	Approved
0.6076	Remote Similarity	NPD2797	Approved
0.6069	Remote Similarity	NPD3226	Approved
0.6067	Remote Similarity	NPD1241	Discontinued
0.6066	Remote Similarity	NPD5844	Phase 1
0.6054	Remote Similarity	NPD9266	Approved
0.6054	Remote Similarity	NPD74	Approved
0.6034	Remote Similarity	NPD4972	Discontinued
0.6026	Remote Similarity	NPD1201	Approved
0.6026	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD1555	Discontinued
0.5988	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD2346	Discontinued
0.5987	Remote Similarity	NPD9269	Phase 2
0.5987	Remote Similarity	NPD1608	Approved
0.5986	Remote Similarity	NPD9264	Approved
0.5986	Remote Similarity	NPD9263	Approved
0.5986	Remote Similarity	NPD9267	Approved
0.5986	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7458	Discontinued
0.5975	Remote Similarity	NPD1164	Approved
0.5975	Remote Similarity	NPD1470	Approved
0.5965	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD4308	Phase 3
0.5952	Remote Similarity	NPD4534	Discontinued
0.5949	Remote Similarity	NPD4749	Approved
0.5938	Remote Similarity	NPD3819	Phase 2
0.5935	Remote Similarity	NPD9268	Approved
0.5928	Remote Similarity	NPD5404	Approved
0.5928	Remote Similarity	NPD5405	Approved
0.5928	Remote Similarity	NPD5408	Approved
0.5928	Remote Similarity	NPD5406	Approved
0.5926	Remote Similarity	NPD3027	Phase 3
0.5916	Remote Similarity	NPD4287	Approved
0.5912	Remote Similarity	NPD1876	Approved
0.5912	Remote Similarity	NPD3225	Approved
0.5909	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD2296	Approved
0.5899	Remote Similarity	NPD4288	Approved
0.589	Remote Similarity	NPD1852	Discontinued
0.589	Remote Similarity	NPD3764	Approved
0.5882	Remote Similarity	NPD7003	Approved
0.5882	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD1933	Approved
0.5879	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD3266	Approved
0.5875	Remote Similarity	NPD3267	Approved
0.5872	Remote Similarity	NPD7041	Phase 2
0.5872	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.5858	Remote Similarity	NPD5958	Discontinued
0.5855	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD405	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