NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	148.05
Volume:	160.062
LogP:	1.305
LogD:	1.148
LogS:	-1.617
# Rotatable Bonds:	2
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	1.617
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.318
MDCK Permeability:	2.4966626369860023e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.372
Plasma Protein Binding (PPB):	86.6928482055664%
Volume Distribution (VD):	0.333
Pgp-substrate:	7.952584266662598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.59
CYP2C19-inhibitor:	0.517
CYP2C19-substrate:	0.141
CYP2C9-inhibitor:	0.19
CYP2C9-substrate:	0.36
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	3.644
Half-life (T1/2):	0.642

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.028
Drug-inuced Liver Injury (DILI):	0.728
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.844
Carcinogencity:	0.364
Eye Corrosion:	0.774
Eye Irritation:	0.994
Respiratory Toxicity:	0.661

Download Data

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

Natural Product: NPC300205

Natural Product ID:	NPC300205
*Common Name:**	Phenyl-1,2-Propanedione
IUPAC Name:	1-phenylpropane-1,2-dione
Synonyms:	Phenyl-1,2-Propanedione
Standard InCHIKey:	BVQVLAIMHVDZEL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6H,1H3
SMILES:	CC(=O)C(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL192258
PubChem CID:	11363
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21465337]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21875098]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24868863]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25089845]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28682072]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29883114]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO310	Flos mume	Species	Lycaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO310	Flos mume	Species	Lycaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9546	Cinamomum cassia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28125	Ephedra equisetina	Species	Ephedraceae	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
Ki	10

Activity Type	# Activity
Individual Protein	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	Ki	=	1840.0	nM	PMID[463408]
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	Ki	=	5270.0	nM	PMID[463408]
NPT2610	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Oryctolagus cuniculus	Ki	=	4930.0	nM	PMID[463408]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ki	>	100000.0	nM	PMID[463408]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	Ki	>	100000.0	nM	PMID[463408]
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	Ki	=	5270.0	nM	PMID[463409]
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	Ki	=	1840.0	nM	PMID[463409]
NPT2610	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Oryctolagus cuniculus	Ki	=	4930.0	nM	PMID[463409]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ki	>	100000.0	nM	PMID[463409]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	Ki	>	100000.0	nM	PMID[463409]

☑ 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 NPC300205 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	300
0.1-0.2	2574
0.2-0.3	7457
0.3-0.4	14649
0.4-0.5	12474
0.5-0.6	4285
0.6-0.7	720
0.7-0.8	149
0.8-0.85	41
0.85-0.9	26
0.9-0.95	14
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC164086
0.9863	High Similarity	NPC285470
0.9863	High Similarity	NPC2785
0.9863	High Similarity	NPC36342
0.9726	High Similarity	NPC245966
0.96	High Similarity	NPC190567
0.9474	High Similarity	NPC145053
0.9342	High Similarity	NPC71664
0.9231	High Similarity	NPC273758
0.9221	High Similarity	NPC12936
0.9221	High Similarity	NPC73978
0.9221	High Similarity	NPC273033
0.9178	High Similarity	NPC285679
0.9041	High Similarity	NPC74458
0.9012	High Similarity	NPC43945
0.9012	High Similarity	NPC69057
0.8987	High Similarity	NPC215008
0.8902	High Similarity	NPC157778
0.8889	High Similarity	NPC160339
0.8889	High Similarity	NPC307
0.8767	High Similarity	NPC98880
0.875	High Similarity	NPC39600
0.875	High Similarity	NPC324624
0.875	High Similarity	NPC197581
0.8734	High Similarity	NPC100039
0.8718	High Similarity	NPC151405
0.8718	High Similarity	NPC139901
0.869	High Similarity	NPC173413
0.8649	High Similarity	NPC95289
0.863	High Similarity	NPC311343
0.8608	High Similarity	NPC17408
0.8608	High Similarity	NPC95868
0.8608	High Similarity	NPC285716
0.859	High Similarity	NPC137847
0.859	High Similarity	NPC76455
0.8588	High Similarity	NPC284475
0.8588	High Similarity	NPC133461
0.8571	High Similarity	NPC78500
0.8537	High Similarity	NPC252067
0.8488	Intermediate Similarity	NPC59677
0.8488	Intermediate Similarity	NPC188844
0.8488	Intermediate Similarity	NPC153885
0.8488	Intermediate Similarity	NPC1682
0.8488	Intermediate Similarity	NPC155232
0.8471	Intermediate Similarity	NPC277277
0.8471	Intermediate Similarity	NPC19256
0.8462	Intermediate Similarity	NPC329318
0.8452	Intermediate Similarity	NPC473345
0.8452	Intermediate Similarity	NPC267262
0.8391	Intermediate Similarity	NPC289883
0.8391	Intermediate Similarity	NPC238219
0.8354	Intermediate Similarity	NPC103488
0.8353	Intermediate Similarity	NPC113307
0.8353	Intermediate Similarity	NPC418308
0.8312	Intermediate Similarity	NPC208075
0.8295	Intermediate Similarity	NPC260233
0.8293	Intermediate Similarity	NPC149263
0.825	Intermediate Similarity	NPC272260
0.8235	Intermediate Similarity	NPC153308
0.8228	Intermediate Similarity	NPC9796
0.8228	Intermediate Similarity	NPC179726
0.8182	Intermediate Similarity	NPC246757
0.8182	Intermediate Similarity	NPC271437
0.8182	Intermediate Similarity	NPC291070
0.8161	Intermediate Similarity	NPC110704
0.8148	Intermediate Similarity	NPC477703
0.8111	Intermediate Similarity	NPC240042
0.8111	Intermediate Similarity	NPC239185
0.8095	Intermediate Similarity	NPC123476
0.8068	Intermediate Similarity	NPC323420
0.8052	Intermediate Similarity	NPC326200
0.8046	Intermediate Similarity	NPC303967
0.8046	Intermediate Similarity	NPC67585
0.8046	Intermediate Similarity	NPC58872
0.8046	Intermediate Similarity	NPC110420
0.8022	Intermediate Similarity	NPC49994
0.8022	Intermediate Similarity	NPC134882
0.8022	Intermediate Similarity	NPC75724
0.8	Intermediate Similarity	NPC185208
0.8	Intermediate Similarity	NPC164526
0.8	Intermediate Similarity	NPC219573
0.8	Intermediate Similarity	NPC298023
0.7955	Intermediate Similarity	NPC476484
0.7931	Intermediate Similarity	NPC325709
0.7912	Intermediate Similarity	NPC265220
0.7889	Intermediate Similarity	NPC472880
0.7882	Intermediate Similarity	NPC95965
0.7857	Intermediate Similarity	NPC288903
0.7849	Intermediate Similarity	NPC476993
0.7849	Intermediate Similarity	NPC109514
0.7849	Intermediate Similarity	NPC112552
0.7816	Intermediate Similarity	NPC477704
0.7816	Intermediate Similarity	NPC477693
0.7802	Intermediate Similarity	NPC12695
0.7792	Intermediate Similarity	NPC235059
0.7792	Intermediate Similarity	NPC169222
0.7792	Intermediate Similarity	NPC16190
0.7791	Intermediate Similarity	NPC318107
0.7766	Intermediate Similarity	NPC222390
0.7766	Intermediate Similarity	NPC244427
0.7766	Intermediate Similarity	NPC25458
0.7753	Intermediate Similarity	NPC103346
0.7717	Intermediate Similarity	NPC156021
0.7711	Intermediate Similarity	NPC127343
0.7711	Intermediate Similarity	NPC157055
0.7701	Intermediate Similarity	NPC194326
0.7692	Intermediate Similarity	NPC130398
0.7684	Intermediate Similarity	NPC329556
0.7684	Intermediate Similarity	NPC247976
0.7684	Intermediate Similarity	NPC475939
0.7684	Intermediate Similarity	NPC474866
0.7684	Intermediate Similarity	NPC274443
0.7684	Intermediate Similarity	NPC471829
0.7684	Intermediate Similarity	NPC472691
0.7674	Intermediate Similarity	NPC294134
0.7667	Intermediate Similarity	NPC77273
0.766	Intermediate Similarity	NPC472879
0.7647	Intermediate Similarity	NPC285773
0.7634	Intermediate Similarity	NPC229242
0.7604	Intermediate Similarity	NPC329282
0.7582	Intermediate Similarity	NPC34243
0.7582	Intermediate Similarity	NPC261181
0.7561	Intermediate Similarity	NPC287790
0.7561	Intermediate Similarity	NPC3672
0.7553	Intermediate Similarity	NPC325497
0.7553	Intermediate Similarity	NPC217621
0.7531	Intermediate Similarity	NPC32203
0.7531	Intermediate Similarity	NPC206800
0.7529	Intermediate Similarity	NPC230068
0.7528	Intermediate Similarity	NPC231591
0.7527	Intermediate Similarity	NPC249912
0.7527	Intermediate Similarity	NPC92754
0.7527	Intermediate Similarity	NPC253423
0.7527	Intermediate Similarity	NPC103048
0.7527	Intermediate Similarity	NPC276775
0.7526	Intermediate Similarity	NPC474910
0.7526	Intermediate Similarity	NPC172483
0.7526	Intermediate Similarity	NPC167336
0.75	Intermediate Similarity	NPC474365
0.75	Intermediate Similarity	NPC322387
0.75	Intermediate Similarity	NPC301943
0.747	Intermediate Similarity	NPC50192
0.7449	Intermediate Similarity	NPC472700
0.7449	Intermediate Similarity	NPC472699
0.7449	Intermediate Similarity	NPC100767
0.7449	Intermediate Similarity	NPC6984
0.7447	Intermediate Similarity	NPC35448
0.7447	Intermediate Similarity	NPC78701
0.7447	Intermediate Similarity	NPC145052
0.7447	Intermediate Similarity	NPC225060
0.7444	Intermediate Similarity	NPC62765
0.7442	Intermediate Similarity	NPC44830
0.7423	Intermediate Similarity	NPC249067
0.7416	Intermediate Similarity	NPC329064
0.7412	Intermediate Similarity	NPC89950
0.7397	Intermediate Similarity	NPC65873
0.7397	Intermediate Similarity	NPC120441
0.7397	Intermediate Similarity	NPC212114
0.7397	Intermediate Similarity	NPC300345
0.7396	Intermediate Similarity	NPC320891
0.7396	Intermediate Similarity	NPC304873
0.7381	Intermediate Similarity	NPC78517
0.7381	Intermediate Similarity	NPC167577
0.7375	Intermediate Similarity	NPC155429
0.7374	Intermediate Similarity	NPC472696
0.7374	Intermediate Similarity	NPC226699
0.7374	Intermediate Similarity	NPC472683
0.7374	Intermediate Similarity	NPC472701
0.7374	Intermediate Similarity	NPC34715
0.7374	Intermediate Similarity	NPC472695
0.7374	Intermediate Similarity	NPC203732
0.7374	Intermediate Similarity	NPC470391
0.7368	Intermediate Similarity	NPC203925
0.7368	Intermediate Similarity	NPC146351
0.7347	Intermediate Similarity	NPC209632
0.7347	Intermediate Similarity	NPC134120
0.734	Intermediate Similarity	NPC289201
0.7333	Intermediate Similarity	NPC298115
0.73	Intermediate Similarity	NPC192577
0.73	Intermediate Similarity	NPC224584
0.73	Intermediate Similarity	NPC470252
0.7292	Intermediate Similarity	NPC70624
0.7292	Intermediate Similarity	NPC42211
0.7292	Intermediate Similarity	NPC473325
0.7273	Intermediate Similarity	NPC30594
0.7273	Intermediate Similarity	NPC37622
0.7263	Intermediate Similarity	NPC317280
0.7263	Intermediate Similarity	NPC329387
0.7262	Intermediate Similarity	NPC176228
0.726	Intermediate Similarity	NPC269586
0.726	Intermediate Similarity	NPC198841
0.7253	Intermediate Similarity	NPC86670
0.7253	Intermediate Similarity	NPC70940
0.7253	Intermediate Similarity	NPC274455
0.7253	Intermediate Similarity	NPC84288
0.7245	Intermediate Similarity	NPC114594
0.7245	Intermediate Similarity	NPC31786
0.7234	Intermediate Similarity	NPC61944
0.7228	Intermediate Similarity	NPC95172
0.7216	Intermediate Similarity	NPC188895

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 NPC300205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	1117
0.2-0.3	1768
0.3-0.4	3393
0.4-0.5	1804
0.5-0.6	633
0.6-0.7	101
0.7-0.8	41
0.8-0.85	4
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9221	High Similarity	NPD942	Approved
0.9012	High Similarity	NPD650	Approved
0.878	High Similarity	NPD506	Clinical (unspecified phase)
0.8608	High Similarity	NPD1507	Clinical (unspecified phase)
0.8588	High Similarity	NPD7609	Phase 3
0.8488	Intermediate Similarity	NPD7631	Approved
0.8276	Intermediate Similarity	NPD1508	Approved
0.8111	Intermediate Similarity	NPD3495	Discontinued
0.8	Intermediate Similarity	NPD1843	Approved
0.7912	Intermediate Similarity	NPD1099	Approved
0.7912	Intermediate Similarity	NPD1100	Approved
0.7901	Intermediate Similarity	NPD227	Approved
0.7901	Intermediate Similarity	NPD225	Approved
0.7805	Intermediate Similarity	NPD9490	Approved
0.7791	Intermediate Similarity	NPD9257	Approved
0.7791	Intermediate Similarity	NPD9259	Approved
0.7684	Intermediate Similarity	NPD1929	Approved
0.7684	Intermediate Similarity	NPD1930	Approved
0.7684	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD9491	Approved
0.7619	Intermediate Similarity	NPD226	Approved
0.7582	Intermediate Similarity	NPD1202	Approved
0.7582	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD2196	Discontinued
0.7579	Intermediate Similarity	NPD1932	Approved
0.7579	Intermediate Similarity	NPD2648	Phase 3
0.7579	Intermediate Similarity	NPD2171	Approved
0.7579	Intermediate Similarity	NPD2193	Phase 2
0.7553	Intermediate Similarity	NPD2066	Phase 3
0.7531	Intermediate Similarity	NPD9716	Approved
0.75	Intermediate Similarity	NPD1087	Approved
0.7444	Intermediate Similarity	NPD9256	Approved
0.7444	Intermediate Similarity	NPD9258	Approved
0.7423	Intermediate Similarity	NPD1237	Approved
0.7347	Intermediate Similarity	NPD1677	Discontinued
0.7347	Intermediate Similarity	NPD2192	Approved
0.7347	Intermediate Similarity	NPD2197	Approved
0.7333	Intermediate Similarity	NPD800	Approved
0.7312	Intermediate Similarity	NPD1693	Approved
0.73	Intermediate Similarity	NPD2329	Discontinued
0.7253	Intermediate Similarity	NPD1090	Approved
0.7253	Intermediate Similarity	NPD1089	Approved
0.7253	Intermediate Similarity	NPD1086	Approved
0.7245	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD164	Approved
0.7228	Intermediate Similarity	NPD1317	Discontinued
0.7188	Intermediate Similarity	NPD1238	Approved
0.7174	Intermediate Similarity	NPD1007	Discontinued
0.7157	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5346	Phase 2
0.7143	Intermediate Similarity	NPD5347	Phase 2
0.7128	Intermediate Similarity	NPD4094	Approved
0.7128	Intermediate Similarity	NPD9260	Approved
0.7111	Intermediate Similarity	NPD4793	Discontinued
0.7097	Intermediate Similarity	NPD1088	Approved
0.7087	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3672	Approved
0.7065	Intermediate Similarity	NPD3673	Approved
0.7059	Intermediate Similarity	NPD664	Approved
0.7045	Intermediate Similarity	NPD3971	Phase 1
0.7041	Intermediate Similarity	NPD813	Approved
0.7021	Intermediate Similarity	NPD1563	Approved
0.699	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1239	Approved
0.6979	Remote Similarity	NPD4657	Approved
0.6979	Remote Similarity	NPD4655	Approved
0.697	Remote Similarity	NPD3357	Discontinued
0.6961	Remote Similarity	NPD2182	Approved
0.6961	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1246	Approved
0.6875	Remote Similarity	NPD1989	Approved
0.6804	Remote Similarity	NPD1565	Approved
0.6804	Remote Similarity	NPD1564	Approved
0.6804	Remote Similarity	NPD1566	Phase 3
0.68	Remote Similarity	NPD6647	Phase 2
0.68	Remote Similarity	NPD9261	Approved
0.6771	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1282	Approved
0.6735	Remote Similarity	NPD9495	Approved
0.6735	Remote Similarity	NPD466	Approved
0.6733	Remote Similarity	NPD5909	Discontinued
0.6729	Remote Similarity	NPD1073	Approved
0.6729	Remote Similarity	NPD1075	Approved
0.6729	Remote Similarity	NPD1074	Approved
0.6709	Remote Similarity	NPD675	Discontinued
0.6707	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6027	Approved
0.67	Remote Similarity	NPD6024	Approved
0.6697	Remote Similarity	NPD7610	Discontinued
0.6667	Remote Similarity	NPD742	Approved
0.6636	Remote Similarity	NPD7009	Phase 2
0.6636	Remote Similarity	NPD1241	Discontinued
0.6625	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1245	Approved
0.6574	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5951	Approved
0.6542	Remote Similarity	NPD5277	Phase 2
0.6538	Remote Similarity	NPD9264	Approved
0.6538	Remote Similarity	NPD9267	Approved
0.6538	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD9263	Approved
0.6531	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD2345	Approved
0.6518	Remote Similarity	NPD1727	Approved
0.65	Remote Similarity	NPD7798	Approved
0.6481	Remote Similarity	NPD7076	Approved
0.6481	Remote Similarity	NPD7077	Approved
0.6476	Remote Similarity	NPD74	Approved
0.6476	Remote Similarity	NPD9266	Approved
0.6465	Remote Similarity	NPD9566	Approved
0.646	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD9493	Approved
0.6449	Remote Similarity	NPD9508	Approved
0.6436	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD2067	Discontinued
0.6404	Remote Similarity	NPD6287	Discontinued
0.64	Remote Similarity	NPD253	Approved
0.6396	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6858	Approved
0.6389	Remote Similarity	NPD7094	Approved
0.6373	Remote Similarity	NPD4803	Discontinued
0.6372	Remote Similarity	NPD5836	Discontinued
0.6372	Remote Similarity	NPD4733	Approved
0.6364	Remote Similarity	NPD1323	Discontinued
0.6364	Remote Similarity	NPD1025	Discontinued
0.6353	Remote Similarity	NPD294	Approved
0.6353	Remote Similarity	NPD292	Approved
0.6348	Remote Similarity	NPD1077	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD3972	Approved
0.6346	Remote Similarity	NPD1018	Approved
0.6339	Remote Similarity	NPD9545	Approved
0.6337	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD1066	Discontinued
0.6316	Remote Similarity	NPD4879	Approved
0.6293	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5159	Phase 2
0.6293	Remote Similarity	NPD5157	Phase 1
0.6283	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD853	Approved
0.6273	Remote Similarity	NPD851	Approved
0.6263	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6049	Phase 2
0.6261	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.625	Remote Similarity	NPD689	Discontinued
0.6239	Remote Similarity	NPD1876	Approved
0.6239	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5926	Approved
0.6228	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD9594	Approved
0.6207	Remote Similarity	NPD9590	Approved
0.6207	Remote Similarity	NPD9592	Approved
0.6207	Remote Similarity	NPD9588	Approved
0.6207	Remote Similarity	NPD4878	Approved
0.6207	Remote Similarity	NPD9589	Approved
0.6207	Remote Similarity	NPD9593	Approved
0.6207	Remote Similarity	NPD80	Approved
0.6207	Remote Similarity	NPD9591	Approved
0.619	Remote Similarity	NPD1765	Approved
0.619	Remote Similarity	NPD1761	Approved
0.619	Remote Similarity	NPD1767	Approved
0.619	Remote Similarity	NPD5048	Discontinued
0.619	Remote Similarity	NPD1763	Approved
0.619	Remote Similarity	NPD1766	Approved
0.6182	Remote Similarity	NPD1175	Approved
0.6134	Remote Similarity	NPD2798	Approved
0.6132	Remote Similarity	NPD467	Phase 1
0.6126	Remote Similarity	NPD9281	Approved
0.6121	Remote Similarity	NPD1201	Approved
0.6121	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1673	Approved
0.6111	Remote Similarity	NPD4233	Approved
0.6111	Remote Similarity	NPD4234	Approved
0.6111	Remote Similarity	NPD1752	Approved
0.6111	Remote Similarity	NPD1756	Approved
0.6102	Remote Similarity	NPD2056	Discontinued
0.6102	Remote Similarity	NPD1574	Approved
0.6092	Remote Similarity	NPD9728	Phase 1
0.6087	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD1104	Approved
0.6068	Remote Similarity	NPD3355	Approved
0.6068	Remote Similarity	NPD3356	Approved
0.6068	Remote Similarity	NPD9717	Approved
0.605	Remote Similarity	NPD1593	Approved
0.605	Remote Similarity	NPD1470	Approved
0.6036	Remote Similarity	NPD2650	Approved
0.6036	Remote Similarity	NPD2652	Approved
0.6034	Remote Similarity	NPD1079	Discontinued
0.6023	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5765	Approved
0.6	Remote Similarity	NPD753	Approved
0.6	Remote Similarity	NPD4147	Approved
0.6	Remote Similarity	NPD9294	Approved
0.6	Remote Similarity	NPD2124	Approved
0.6	Remote Similarity	NPD4144	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