NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	261.435
LogP:	1.77
LogD:	-0.331
LogS:	-1.847
# Rotatable Bonds:	4
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	2.144
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.7
MDCK Permeability:	2.7464651793707162e-05
Pgp-inhibitor:	0.804
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.451
Plasma Protein Binding (PPB):	54.021240234375%
Volume Distribution (VD):	0.858
Pgp-substrate:	46.662635803222656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.735
CYP2C19-inhibitor:	0.419
CYP2C19-substrate:	0.154
CYP2C9-inhibitor:	0.246
CYP2C9-substrate:	0.758
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.469
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.478

ADMET: Excretion

Clearance (CL):	7.962
Half-life (T1/2):	0.751

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.483
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.67
Carcinogencity:	0.026
Eye Corrosion:	0.074
Eye Irritation:	0.592
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC477703

Natural Product ID:	NPC477703
*Common Name:**	2-(3-Phenylpropanoyl)cyclohexane-1,3-dione
IUPAC Name:	2-(3-phenylpropanoyl)cyclohexane-1,3-dione
Synonyms:
Standard InCHIKey:	ZUQGGYYTTZREMA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O3/c16-12-7-4-8-13(17)15(12)14(18)10-9-11-5-2-1-3-6-11/h1-3,5-6,15H,4,7-10H2
SMILES:	C1CC(=O)C(C(=O)C1)C(=O)CCC2=CC=CC=C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44566543
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000133] 1,3-dicarbonyl compounds [CHEMONTID:0003926] Beta-diketones

*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
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16309318]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16724842]
NPO27718	Peperomia dindygulensis	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	40.5	ug/ml	PMID[16309318]

☑ 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 NPC477703 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	225
0.1-0.2	1673
0.2-0.3	4671
0.3-0.4	15518
0.4-0.5	16436
0.5-0.6	3489
0.6-0.7	521
0.7-0.8	142
0.8-0.85	17
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9342	High Similarity	NPC272260
0.9079	High Similarity	NPC9796
0.8718	High Similarity	NPC103488
0.8667	High Similarity	NPC74458
0.8642	High Similarity	NPC273758
0.8608	High Similarity	NPC151405
0.8608	High Similarity	NPC139901
0.8553	High Similarity	NPC285679
0.85	High Similarity	NPC17408
0.85	High Similarity	NPC285716
0.85	High Similarity	NPC95868
0.8395	Intermediate Similarity	NPC273033
0.8395	Intermediate Similarity	NPC12936
0.8354	Intermediate Similarity	NPC179726
0.8272	Intermediate Similarity	NPC190567
0.8272	Intermediate Similarity	NPC71664
0.8272	Intermediate Similarity	NPC164086
0.8235	Intermediate Similarity	NPC69057
0.8214	Intermediate Similarity	NPC123476
0.8148	Intermediate Similarity	NPC300205
0.8125	Intermediate Similarity	NPC245966
0.8125	Intermediate Similarity	NPC298023
0.8077	Intermediate Similarity	NPC271437
0.8049	Intermediate Similarity	NPC157055
0.8046	Intermediate Similarity	NPC298115
0.8046	Intermediate Similarity	NPC231591
0.8025	Intermediate Similarity	NPC2785
0.8025	Intermediate Similarity	NPC285470
0.8025	Intermediate Similarity	NPC36342
0.7975	Intermediate Similarity	NPC208075
0.7952	Intermediate Similarity	NPC145053
0.7931	Intermediate Similarity	NPC477693
0.7931	Intermediate Similarity	NPC477704
0.7865	Intermediate Similarity	NPC141607
0.7865	Intermediate Similarity	NPC133461
0.7865	Intermediate Similarity	NPC187725
0.7857	Intermediate Similarity	NPC230068
0.7821	Intermediate Similarity	NPC95289
0.7805	Intermediate Similarity	NPC76455
0.7805	Intermediate Similarity	NPC137847
0.7789	Intermediate Similarity	NPC475939
0.7789	Intermediate Similarity	NPC472691
0.7789	Intermediate Similarity	NPC471829
0.7789	Intermediate Similarity	NPC474866
0.7778	Intermediate Similarity	NPC188844
0.7778	Intermediate Similarity	NPC59677
0.7778	Intermediate Similarity	NPC153885
0.7778	Intermediate Similarity	NPC1682
0.7766	Intermediate Similarity	NPC109514
0.7765	Intermediate Similarity	NPC215008
0.7765	Intermediate Similarity	NPC44830
0.7753	Intermediate Similarity	NPC67585
0.7753	Intermediate Similarity	NPC19256
0.7753	Intermediate Similarity	NPC110420
0.7753	Intermediate Similarity	NPC303967
0.7738	Intermediate Similarity	NPC73978
0.7727	Intermediate Similarity	NPC157778
0.7727	Intermediate Similarity	NPC267262
0.7692	Intermediate Similarity	NPC238219
0.7692	Intermediate Similarity	NPC98880
0.7683	Intermediate Similarity	NPC329318
0.7667	Intermediate Similarity	NPC284475
0.766	Intermediate Similarity	NPC54647
0.764	Intermediate Similarity	NPC113307
0.764	Intermediate Similarity	NPC418308
0.7634	Intermediate Similarity	NPC239185
0.7619	Intermediate Similarity	NPC127343
0.7614	Intermediate Similarity	NPC43945
0.7609	Intermediate Similarity	NPC206764
0.7609	Intermediate Similarity	NPC260233
0.7586	Intermediate Similarity	NPC95965
0.7582	Intermediate Similarity	NPC155232
0.7582	Intermediate Similarity	NPC323420
0.7564	Intermediate Similarity	NPC311343
0.7556	Intermediate Similarity	NPC173413
0.7556	Intermediate Similarity	NPC84288
0.7556	Intermediate Similarity	NPC277277
0.7553	Intermediate Similarity	NPC134882
0.7553	Intermediate Similarity	NPC49994
0.7551	Intermediate Similarity	NPC472699
0.7551	Intermediate Similarity	NPC472700
0.7527	Intermediate Similarity	NPC219573
0.7527	Intermediate Similarity	NPC185208
0.75	Intermediate Similarity	NPC160339
0.75	Intermediate Similarity	NPC289883
0.75	Intermediate Similarity	NPC307
0.7475	Intermediate Similarity	NPC472696
0.7475	Intermediate Similarity	NPC472683
0.7475	Intermediate Similarity	NPC472701
0.7475	Intermediate Similarity	NPC472695
0.7474	Intermediate Similarity	NPC476042
0.7473	Intermediate Similarity	NPC125226
0.7467	Intermediate Similarity	NPC246588
0.7447	Intermediate Similarity	NPC265220
0.7444	Intermediate Similarity	NPC9822
0.7416	Intermediate Similarity	NPC194326
0.7416	Intermediate Similarity	NPC322387
0.7396	Intermediate Similarity	NPC476993
0.7391	Intermediate Similarity	NPC77273
0.7386	Intermediate Similarity	NPC252067
0.7368	Intermediate Similarity	NPC329387
0.7368	Intermediate Similarity	NPC317280
0.7368	Intermediate Similarity	NPC145052
0.7368	Intermediate Similarity	NPC22786
0.7368	Intermediate Similarity	NPC75724
0.7363	Intermediate Similarity	NPC70940
0.7363	Intermediate Similarity	NPC274455
0.7363	Intermediate Similarity	NPC86670
0.7356	Intermediate Similarity	NPC197581
0.7356	Intermediate Similarity	NPC324624
0.7356	Intermediate Similarity	NPC285773
0.7356	Intermediate Similarity	NPC288903
0.7312	Intermediate Similarity	NPC34243
0.7284	Intermediate Similarity	NPC155429
0.7283	Intermediate Similarity	NPC476484
0.7273	Intermediate Similarity	NPC113670
0.7263	Intermediate Similarity	NPC477767
0.7263	Intermediate Similarity	NPC289201
0.7263	Intermediate Similarity	NPC103048
0.7263	Intermediate Similarity	NPC240042
0.7263	Intermediate Similarity	NPC226041
0.7253	Intermediate Similarity	NPC325709
0.7237	Intermediate Similarity	NPC135924
0.7237	Intermediate Similarity	NPC210849
0.7234	Intermediate Similarity	NPC472880
0.7228	Intermediate Similarity	NPC470252
0.7216	Intermediate Similarity	NPC225079
0.7216	Intermediate Similarity	NPC472879
0.72	Intermediate Similarity	NPC244933
0.72	Intermediate Similarity	NPC114327
0.72	Intermediate Similarity	NPC36357
0.72	Intermediate Similarity	NPC85560
0.7191	Intermediate Similarity	NPC475710
0.7191	Intermediate Similarity	NPC294134
0.7188	Intermediate Similarity	NPC179411
0.7179	Intermediate Similarity	NPC198023
0.7179	Intermediate Similarity	NPC155172
0.7179	Intermediate Similarity	NPC32312
0.7162	Intermediate Similarity	NPC198841
0.7159	Intermediate Similarity	NPC39600
0.7159	Intermediate Similarity	NPC270507
0.7158	Intermediate Similarity	NPC12695
0.7143	Intermediate Similarity	NPC71009
0.7143	Intermediate Similarity	NPC78500
0.7143	Intermediate Similarity	NPC329064
0.7129	Intermediate Similarity	NPC470007
0.7126	Intermediate Similarity	NPC100039
0.7115	Intermediate Similarity	NPC471481
0.7113	Intermediate Similarity	NPC221825
0.71	Intermediate Similarity	NPC474307
0.71	Intermediate Similarity	NPC471186
0.7097	Intermediate Similarity	NPC103346
0.7073	Intermediate Similarity	NPC326200
0.7071	Intermediate Similarity	NPC329556
0.7071	Intermediate Similarity	NPC247976
0.7067	Intermediate Similarity	NPC120441
0.7067	Intermediate Similarity	NPC212114
0.7067	Intermediate Similarity	NPC65873
0.7067	Intermediate Similarity	NPC300345
0.7053	Intermediate Similarity	NPC172925
0.7051	Intermediate Similarity	NPC88566
0.7051	Intermediate Similarity	NPC45756
0.7048	Intermediate Similarity	NPC234637
0.7048	Intermediate Similarity	NPC130591
0.7048	Intermediate Similarity	NPC294458
0.7045	Intermediate Similarity	NPC121478
0.7045	Intermediate Similarity	NPC323103
0.7045	Intermediate Similarity	NPC103387
0.7045	Intermediate Similarity	NPC73637
0.7041	Intermediate Similarity	NPC133809
0.7041	Intermediate Similarity	NPC136810
0.7041	Intermediate Similarity	NPC128248
0.7037	Intermediate Similarity	NPC16190
0.7037	Intermediate Similarity	NPC169222
0.7037	Intermediate Similarity	NPC235059
0.703	Intermediate Similarity	NPC475905
0.703	Intermediate Similarity	NPC188677
0.703	Intermediate Similarity	NPC25385
0.703	Intermediate Similarity	NPC193640
0.7027	Intermediate Similarity	NPC149436
0.7019	Intermediate Similarity	NPC280789
0.7019	Intermediate Similarity	NPC474689
0.7013	Intermediate Similarity	NPC150196
0.7013	Intermediate Similarity	NPC248705
0.7013	Intermediate Similarity	NPC54368
0.7011	Intermediate Similarity	NPC184030
0.7011	Intermediate Similarity	NPC164449
0.701	Intermediate Similarity	NPC271475
0.7	Intermediate Similarity	NPC120693
0.7	Intermediate Similarity	NPC267443
0.7	Intermediate Similarity	NPC329282
0.7	Intermediate Similarity	NPC8931
0.7	Intermediate Similarity	NPC261573
0.6989	Remote Similarity	NPC58872
0.6988	Remote Similarity	NPC54269
0.6966	Remote Similarity	NPC477770
0.6962	Remote Similarity	NPC291066
0.6957	Remote Similarity	NPC473345
0.6957	Remote Similarity	NPC153308
0.6952	Remote Similarity	NPC93287

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 NPC477703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	1038
0.2-0.3	1419
0.3-0.4	3552
0.4-0.5	2037
0.5-0.6	724
0.6-0.7	128
0.7-0.8	34
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
0.85	High Similarity	NPD1507	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD942	Approved
0.7978	Intermediate Similarity	NPD1508	Approved
0.7805	Intermediate Similarity	NPD227	Approved
0.7805	Intermediate Similarity	NPD225	Approved
0.7778	Intermediate Similarity	NPD7631	Approved
0.7717	Intermediate Similarity	NPD1843	Approved
0.7692	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7609	Phase 3
0.7634	Intermediate Similarity	NPD3495	Discontinued
0.7614	Intermediate Similarity	NPD1087	Approved
0.7614	Intermediate Similarity	NPD650	Approved
0.7529	Intermediate Similarity	NPD226	Approved
0.75	Intermediate Similarity	NPD9490	Approved
0.7474	Intermediate Similarity	NPD2066	Phase 3
0.7444	Intermediate Similarity	NPD800	Approved
0.7444	Intermediate Similarity	NPD5347	Phase 2
0.7444	Intermediate Similarity	NPD5346	Phase 2
0.7419	Intermediate Similarity	NPD4094	Approved
0.7419	Intermediate Similarity	NPD1693	Approved
0.7416	Intermediate Similarity	NPD4793	Discontinued
0.7363	Intermediate Similarity	NPD3672	Approved
0.7363	Intermediate Similarity	NPD1086	Approved
0.7363	Intermediate Similarity	NPD1089	Approved
0.7363	Intermediate Similarity	NPD1090	Approved
0.7363	Intermediate Similarity	NPD3673	Approved
0.7356	Intermediate Similarity	NPD9491	Approved
0.7312	Intermediate Similarity	NPD1563	Approved
0.7283	Intermediate Similarity	NPD1239	Approved
0.7273	Intermediate Similarity	NPD675	Discontinued
0.7263	Intermediate Similarity	NPD4657	Approved
0.7263	Intermediate Similarity	NPD4655	Approved
0.7222	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD1088	Approved
0.7158	Intermediate Similarity	NPD1989	Approved
0.7083	Intermediate Similarity	NPD1564	Approved
0.7083	Intermediate Similarity	NPD1565	Approved
0.7083	Intermediate Similarity	NPD1566	Phase 3
0.7071	Intermediate Similarity	NPD1929	Approved
0.7071	Intermediate Similarity	NPD1930	Approved
0.7071	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3135	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5909	Discontinued
0.6979	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2648	Phase 3
0.697	Remote Similarity	NPD2193	Phase 2
0.697	Remote Similarity	NPD6024	Approved
0.697	Remote Similarity	NPD1932	Approved
0.697	Remote Similarity	NPD6027	Approved
0.6966	Remote Similarity	NPD3971	Phase 1
0.6939	Remote Similarity	NPD7798	Approved
0.6832	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1237	Approved
0.6824	Remote Similarity	NPD9716	Approved
0.68	Remote Similarity	NPD2171	Approved
0.68	Remote Similarity	NPD2196	Discontinued
0.6771	Remote Similarity	NPD1202	Approved
0.6735	Remote Similarity	NPD1099	Approved
0.6735	Remote Similarity	NPD1100	Approved
0.6731	Remote Similarity	NPD2329	Discontinued
0.6667	Remote Similarity	NPD466	Approved
0.6667	Remote Similarity	NPD253	Approved
0.6636	Remote Similarity	NPD6858	Approved
0.6636	Remote Similarity	NPD7094	Approved
0.663	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5048	Discontinued
0.6602	Remote Similarity	NPD1677	Discontinued
0.66	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3357	Discontinued
0.6562	Remote Similarity	NPD1007	Discontinued
0.6559	Remote Similarity	NPD9259	Approved
0.6559	Remote Similarity	NPD9257	Approved
0.6543	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6049	Phase 2
0.6514	Remote Similarity	NPD1711	Phase 2
0.6509	Remote Similarity	NPD1317	Discontinued
0.65	Remote Similarity	NPD9495	Approved
0.65	Remote Similarity	NPD5926	Approved
0.6471	Remote Similarity	NPD4803	Discontinued
0.6455	Remote Similarity	NPD3317	Approved
0.6449	Remote Similarity	NPD3644	Approved
0.6449	Remote Similarity	NPD3642	Approved
0.6449	Remote Similarity	NPD3643	Approved
0.6442	Remote Similarity	NPD2197	Approved
0.6442	Remote Similarity	NPD2192	Approved
0.6436	Remote Similarity	NPD1238	Approved
0.6436	Remote Similarity	NPD742	Approved
0.6429	Remote Similarity	NPD1673	Approved
0.6408	Remote Similarity	NPD5765	Approved
0.6408	Remote Similarity	NPD6647	Phase 2
0.64	Remote Similarity	NPD9566	Approved
0.6374	Remote Similarity	NPD3035	Approved
0.6364	Remote Similarity	NPD2629	Approved
0.6355	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7610	Discontinued
0.6333	Remote Similarity	NPD1475	Approved
0.6316	Remote Similarity	NPD1282	Approved
0.6304	Remote Similarity	NPD4169	Approved
0.6304	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4170	Approved
0.6292	Remote Similarity	NPD4144	Approved
0.6292	Remote Similarity	NPD4147	Approved
0.6289	Remote Similarity	NPD9256	Approved
0.6289	Remote Similarity	NPD9258	Approved
0.6286	Remote Similarity	NPD1767	Approved
0.6286	Remote Similarity	NPD1763	Approved
0.6286	Remote Similarity	NPD1761	Approved
0.6286	Remote Similarity	NPD1765	Approved
0.6286	Remote Similarity	NPD1766	Approved
0.6286	Remote Similarity	NPD1018	Approved
0.6283	Remote Similarity	NPD7009	Phase 2
0.6279	Remote Similarity	NPD294	Approved
0.6279	Remote Similarity	NPD292	Approved
0.6273	Remote Similarity	NPD3598	Phase 3
0.6273	Remote Similarity	NPD7076	Approved
0.6273	Remote Similarity	NPD7077	Approved
0.6264	Remote Similarity	NPD3903	Approved
0.6264	Remote Similarity	NPD3981	Approved
0.6264	Remote Similarity	NPD1617	Discontinued
0.6264	Remote Similarity	NPD3979	Approved
0.6264	Remote Similarity	NPD3904	Approved
0.6263	Remote Similarity	NPD1066	Discontinued
0.6262	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1101	Approved
0.625	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4576	Approved
0.625	Remote Similarity	NPD4574	Approved
0.6239	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD2124	Approved
0.6237	Remote Similarity	NPD4635	Approved
0.6237	Remote Similarity	NPD2001	Discontinued
0.6237	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD3024	Approved
0.6228	Remote Similarity	NPD3025	Approved
0.6226	Remote Similarity	NPD467	Phase 1
0.6226	Remote Similarity	NPD6685	Approved
0.6216	Remote Similarity	NPD3867	Phase 2
0.6216	Remote Similarity	NPD1023	Approved
0.6216	Remote Similarity	NPD1021	Approved
0.6216	Remote Similarity	NPD1020	Approved
0.6216	Remote Similarity	NPD1022	Approved
0.6214	Remote Similarity	NPD5630	Phase 1
0.6204	Remote Similarity	NPD2067	Discontinued
0.6204	Remote Similarity	NPD664	Approved
0.6204	Remote Similarity	NPD1752	Approved
0.6204	Remote Similarity	NPD1756	Approved
0.6196	Remote Similarity	NPD4026	Approved
0.6196	Remote Similarity	NPD4027	Approved
0.6195	Remote Similarity	NPD6065	Approved
0.6186	Remote Similarity	NPD1628	Approved
0.6186	Remote Similarity	NPD1629	Approved
0.6174	Remote Similarity	NPD2932	Approved
0.6174	Remote Similarity	NPD5836	Discontinued
0.6174	Remote Similarity	NPD3019	Approved
0.6154	Remote Similarity	NPD813	Approved
0.6154	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5927	Discontinued
0.6147	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD2859	Approved
0.6139	Remote Similarity	NPD2860	Approved
0.6126	Remote Similarity	NPD1370	Approved
0.6126	Remote Similarity	NPD1371	Approved
0.6126	Remote Similarity	NPD1374	Approved
0.6126	Remote Similarity	NPD2652	Approved
0.6126	Remote Similarity	NPD1373	Approved
0.6126	Remote Similarity	NPD2650	Approved
0.6121	Remote Similarity	NPD3023	Approved
0.6121	Remote Similarity	NPD3026	Approved
0.6121	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD4879	Approved
0.6117	Remote Similarity	NPD3020	Approved
0.6117	Remote Similarity	NPD1067	Discontinued
0.6105	Remote Similarity	NPD5916	Discontinued
0.6087	Remote Similarity	NPD1651	Approved
0.6082	Remote Similarity	NPD531	Approved
0.6071	Remote Similarity	NPD2319	Discontinued
0.6071	Remote Similarity	NPD1246	Approved
0.6071	Remote Similarity	NPD5951	Approved
0.6071	Remote Similarity	NPD3551	Approved
0.6064	Remote Similarity	NPD1185	Approved
0.6055	Remote Similarity	NPD4233	Approved
0.6055	Remote Similarity	NPD3581	Discontinued
0.6055	Remote Similarity	NPD5278	Discontinued
0.6055	Remote Similarity	NPD4234	Approved
0.6055	Remote Similarity	NPD5236	Approved
0.6055	Remote Similarity	NPD5239	Approved
0.6055	Remote Similarity	NPD5235	Approved
0.6055	Remote Similarity	NPD5237	Approved
0.6055	Remote Similarity	NPD5240	Approved
0.6053	Remote Similarity	NPD5991	Approved
0.6053	Remote Similarity	NPD5990	Approved
0.6044	Remote Similarity	NPD79	Approved
0.6044	Remote Similarity	NPD9564	Approved
0.6044	Remote Similarity	NPD9563	Approved
0.604	Remote Similarity	NPD2933	Approved
0.604	Remote Similarity	NPD9260	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