NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.07
Volume:	162.698
LogP:	0.981
LogD:	0.42
LogS:	-0.619
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	1.681
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.456
MDCK Permeability:	2.3947493900777772e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.882
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	46.63348388671875%
Volume Distribution (VD):	0.766
Pgp-substrate:	48.5277099609375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.269
CYP1A2-substrate:	0.705
CYP2C19-inhibitor:	0.606
CYP2C19-substrate:	0.595
CYP2C9-inhibitor:	0.194
CYP2C9-substrate:	0.897
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.843
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.363

ADMET: Excretion

Clearance (CL):	16.366
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.55
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.206
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.424
Carcinogencity:	0.444
Eye Corrosion:	0.531
Eye Irritation:	0.978
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC280869

Natural Product ID:	NPC280869
*Common Name:**	P-Hydroxyphenylacetone
IUPAC Name:	1-(4-hydroxyphenyl)propan-2-one
Synonyms:	P-Hydroxyphenylacetone
Standard InCHIKey:	VWMVAQHMFFZQGD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O2/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,11H,6H2,1H3
SMILES:	CC(=O)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1090553
PubChem CID:	7019274
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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	IC50	=	420000.0	nM	PMID[452133]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	IC50	=	416869.38	nM	PMID[452133]

☑ 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 NPC280869 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	224
0.1-0.2	1801
0.2-0.3	4754
0.3-0.4	12744
0.4-0.5	6345
0.5-0.6	9290
0.6-0.7	6050
0.7-0.8	1293
0.8-0.85	134
0.85-0.9	47
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC260000
0.9474	High Similarity	NPC52472
0.9368	High Similarity	NPC245561
0.9293	High Similarity	NPC226699
0.9286	High Similarity	NPC13495
0.9192	High Similarity	NPC6984
0.9184	High Similarity	NPC120693
0.9184	High Similarity	NPC8931
0.9184	High Similarity	NPC261573
0.9109	High Similarity	NPC95172
0.91	High Similarity	NPC228737
0.901	High Similarity	NPC317305
0.9	High Similarity	NPC188677
0.9	High Similarity	NPC70843
0.9	High Similarity	NPC29989
0.9	High Similarity	NPC69332
0.9	High Similarity	NPC95178
0.8913	High Similarity	NPC23167
0.8911	High Similarity	NPC34715
0.8889	High Similarity	NPC13426
0.8842	High Similarity	NPC181709
0.8835	High Similarity	NPC21162
0.8824	High Similarity	NPC17525
0.8824	High Similarity	NPC224584
0.8824	High Similarity	NPC31274
0.8817	High Similarity	NPC113460
0.8817	High Similarity	NPC25493
0.8804	High Similarity	NPC197783
0.8788	High Similarity	NPC472585
0.8762	High Similarity	NPC242136
0.8762	High Similarity	NPC11824
0.875	High Similarity	NPC212718
0.875	High Similarity	NPC114682
0.8738	High Similarity	NPC88141
0.8725	High Similarity	NPC141523
0.8723	High Similarity	NPC318325
0.8723	High Similarity	NPC258219
0.8723	High Similarity	NPC123273
0.8723	High Similarity	NPC177420
0.8723	High Similarity	NPC242240
0.8723	High Similarity	NPC280347
0.8696	High Similarity	NPC175313
0.8696	High Similarity	NPC248817
0.8667	High Similarity	NPC17693
0.8667	High Similarity	NPC231717
0.8654	High Similarity	NPC321252
0.8654	High Similarity	NPC252544
0.8654	High Similarity	NPC116842
0.8646	High Similarity	NPC138117
0.8646	High Similarity	NPC325292
0.8632	High Similarity	NPC300017
0.8632	High Similarity	NPC55561
0.8627	High Similarity	NPC317592
0.8614	High Similarity	NPC38209
0.8587	High Similarity	NPC265146
0.8587	High Similarity	NPC124436
0.8571	High Similarity	NPC177576
0.8571	High Similarity	NPC268388
0.8558	High Similarity	NPC234639
0.8558	High Similarity	NPC326187
0.8542	High Similarity	NPC304541
0.8542	High Similarity	NPC45040
0.8515	High Similarity	NPC298224
0.8511	High Similarity	NPC407
0.8511	High Similarity	NPC184169
0.8511	High Similarity	NPC307235
0.8491	Intermediate Similarity	NPC286222
0.8491	Intermediate Similarity	NPC48525
0.8476	Intermediate Similarity	NPC222905
0.8476	Intermediate Similarity	NPC222084
0.8469	Intermediate Similarity	NPC26244
0.8469	Intermediate Similarity	NPC313650
0.844	Intermediate Similarity	NPC150919
0.8426	Intermediate Similarity	NPC322197
0.8426	Intermediate Similarity	NPC23402
0.8421	Intermediate Similarity	NPC104216
0.8421	Intermediate Similarity	NPC27974
0.8411	Intermediate Similarity	NPC148969
0.8404	Intermediate Similarity	NPC155393
0.8384	Intermediate Similarity	NPC473388
0.8367	Intermediate Similarity	NPC27323
0.8367	Intermediate Similarity	NPC151715
0.8367	Intermediate Similarity	NPC32977
0.8367	Intermediate Similarity	NPC81010
0.8367	Intermediate Similarity	NPC316301
0.8367	Intermediate Similarity	NPC128062
0.8365	Intermediate Similarity	NPC29883
0.8351	Intermediate Similarity	NPC270547
0.8351	Intermediate Similarity	NPC155908
0.8351	Intermediate Similarity	NPC204210
0.835	Intermediate Similarity	NPC219913
0.8349	Intermediate Similarity	NPC325646
0.8349	Intermediate Similarity	NPC19290
0.8349	Intermediate Similarity	NPC28951
0.8333	Intermediate Similarity	NPC135784
0.8333	Intermediate Similarity	NPC118288
0.8333	Intermediate Similarity	NPC68269
0.8333	Intermediate Similarity	NPC285350
0.8333	Intermediate Similarity	NPC98772
0.8333	Intermediate Similarity	NPC276111
0.83	Intermediate Similarity	NPC201967
0.8298	Intermediate Similarity	NPC286904
0.8288	Intermediate Similarity	NPC161617
0.8288	Intermediate Similarity	NPC473767
0.8283	Intermediate Similarity	NPC286006
0.8283	Intermediate Similarity	NPC274678
0.8283	Intermediate Similarity	NPC8392
0.8269	Intermediate Similarity	NPC1065
0.8269	Intermediate Similarity	NPC184658
0.8257	Intermediate Similarity	NPC240163
0.8257	Intermediate Similarity	NPC4665
0.8257	Intermediate Similarity	NPC161304
0.8247	Intermediate Similarity	NPC300478
0.8241	Intermediate Similarity	NPC309808
0.8241	Intermediate Similarity	NPC162113
0.8241	Intermediate Similarity	NPC62546
0.8241	Intermediate Similarity	NPC109241
0.8218	Intermediate Similarity	NPC171843
0.8218	Intermediate Similarity	NPC128723
0.8218	Intermediate Similarity	NPC130193
0.8218	Intermediate Similarity	NPC92730
0.8218	Intermediate Similarity	NPC80027
0.8198	Intermediate Similarity	NPC249435
0.8198	Intermediate Similarity	NPC474890
0.8198	Intermediate Similarity	NPC161943
0.8198	Intermediate Similarity	NPC40649
0.8198	Intermediate Similarity	NPC328694
0.8198	Intermediate Similarity	NPC273282
0.8198	Intermediate Similarity	NPC209486
0.8182	Intermediate Similarity	NPC277394
0.8182	Intermediate Similarity	NPC477453
0.8182	Intermediate Similarity	NPC61062
0.8182	Intermediate Similarity	NPC131192
0.8182	Intermediate Similarity	NPC299252
0.8182	Intermediate Similarity	NPC128249
0.8173	Intermediate Similarity	NPC303141
0.8165	Intermediate Similarity	NPC221870
0.8163	Intermediate Similarity	NPC306074
0.8155	Intermediate Similarity	NPC470202
0.8144	Intermediate Similarity	NPC70436
0.8142	Intermediate Similarity	NPC190971
0.8137	Intermediate Similarity	NPC253746
0.8125	Intermediate Similarity	NPC258366
0.8125	Intermediate Similarity	NPC31296
0.8125	Intermediate Similarity	NPC473974
0.8125	Intermediate Similarity	NPC79933
0.8125	Intermediate Similarity	NPC299406
0.8125	Intermediate Similarity	NPC158222
0.8119	Intermediate Similarity	NPC109955
0.8119	Intermediate Similarity	NPC107619
0.8119	Intermediate Similarity	NPC77492
0.8119	Intermediate Similarity	NPC225464
0.8108	Intermediate Similarity	NPC269414
0.8108	Intermediate Similarity	NPC121259
0.8105	Intermediate Similarity	NPC150837
0.81	Intermediate Similarity	NPC246679
0.8095	Intermediate Similarity	NPC187913
0.8081	Intermediate Similarity	NPC306884
0.8081	Intermediate Similarity	NPC94139
0.8081	Intermediate Similarity	NPC147284
0.8081	Intermediate Similarity	NPC162314
0.8081	Intermediate Similarity	NPC55903
0.8081	Intermediate Similarity	NPC3358
0.8081	Intermediate Similarity	NPC210497
0.8077	Intermediate Similarity	NPC52087
0.8077	Intermediate Similarity	NPC79672
0.8061	Intermediate Similarity	NPC192
0.8056	Intermediate Similarity	NPC23332
0.8053	Intermediate Similarity	NPC318552
0.8053	Intermediate Similarity	NPC294037
0.8053	Intermediate Similarity	NPC190501
0.8053	Intermediate Similarity	NPC159525
0.8039	Intermediate Similarity	NPC132078
0.8039	Intermediate Similarity	NPC78119
0.8039	Intermediate Similarity	NPC216468
0.8039	Intermediate Similarity	NPC252821
0.8039	Intermediate Similarity	NPC122005
0.8039	Intermediate Similarity	NPC51333
0.8037	Intermediate Similarity	NPC259554
0.8036	Intermediate Similarity	NPC94298
0.8036	Intermediate Similarity	NPC184527
0.8036	Intermediate Similarity	NPC41567
0.8036	Intermediate Similarity	NPC471033
0.8036	Intermediate Similarity	NPC311091
0.8036	Intermediate Similarity	NPC27633
0.802	Intermediate Similarity	NPC82664
0.802	Intermediate Similarity	NPC202986
0.802	Intermediate Similarity	NPC216520
0.802	Intermediate Similarity	NPC132271
0.802	Intermediate Similarity	NPC292730
0.802	Intermediate Similarity	NPC283711
0.8019	Intermediate Similarity	NPC303264
0.8018	Intermediate Similarity	NPC83718
0.8018	Intermediate Similarity	NPC471925
0.8018	Intermediate Similarity	NPC106551
0.8018	Intermediate Similarity	NPC281686
0.8018	Intermediate Similarity	NPC188867
0.8018	Intermediate Similarity	NPC471924
0.8018	Intermediate Similarity	NPC471928
0.8	Intermediate Similarity	NPC164947

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 NPC280869 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	995
0.2-0.3	1276
0.3-0.4	2839
0.4-0.5	2055
0.5-0.6	1180
0.6-0.7	448
0.7-0.8	88
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8587	High Similarity	NPD111	Approved
0.8557	High Similarity	NPD2934	Approved
0.8557	High Similarity	NPD2933	Approved
0.8469	Intermediate Similarity	NPD2859	Approved
0.8469	Intermediate Similarity	NPD2860	Approved
0.8367	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8257	Intermediate Similarity	NPD255	Approved
0.8257	Intermediate Similarity	NPD256	Approved
0.8218	Intermediate Similarity	NPD3020	Approved
0.8058	Intermediate Similarity	NPD940	Approved
0.8058	Intermediate Similarity	NPD846	Approved
0.8053	Intermediate Similarity	NPD2932	Approved
0.8053	Intermediate Similarity	NPD3019	Approved
0.8036	Intermediate Similarity	NPD9545	Approved
0.8018	Intermediate Similarity	NPD9568	Approved
0.7965	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD74	Approved
0.7944	Intermediate Similarity	NPD9266	Approved
0.7921	Intermediate Similarity	NPD844	Approved
0.7921	Intermediate Similarity	NPD1809	Phase 2
0.7909	Intermediate Similarity	NPD1241	Discontinued
0.79	Intermediate Similarity	NPD845	Approved
0.7857	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD9493	Approved
0.785	Intermediate Similarity	NPD9267	Approved
0.785	Intermediate Similarity	NPD9263	Approved
0.785	Intermediate Similarity	NPD9264	Approved
0.7843	Intermediate Similarity	NPD288	Approved
0.7789	Intermediate Similarity	NPD9491	Approved
0.7788	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD9495	Approved
0.7736	Intermediate Similarity	NPD9610	Approved
0.7736	Intermediate Similarity	NPD9608	Approved
0.7692	Intermediate Similarity	NPD1481	Phase 2
0.7627	Intermediate Similarity	NPD1755	Approved
0.7619	Intermediate Similarity	NPD1242	Phase 1
0.7607	Intermediate Similarity	NPD1535	Discovery
0.7607	Intermediate Similarity	NPD1201	Approved
0.76	Intermediate Similarity	NPD9258	Approved
0.76	Intermediate Similarity	NPD9256	Approved
0.757	Intermediate Similarity	NPD1237	Approved
0.7565	Intermediate Similarity	NPD1759	Phase 1
0.7545	Intermediate Similarity	NPD3022	Approved
0.7545	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD1164	Approved
0.75	Intermediate Similarity	NPD800	Approved
0.7478	Intermediate Similarity	NPD1758	Phase 1
0.7477	Intermediate Similarity	NPD9261	Approved
0.7476	Intermediate Similarity	NPD1693	Approved
0.7453	Intermediate Similarity	NPD3028	Approved
0.7438	Intermediate Similarity	NPD257	Approved
0.7438	Intermediate Similarity	NPD258	Approved
0.7426	Intermediate Similarity	NPD1089	Approved
0.7426	Intermediate Similarity	NPD1090	Approved
0.7426	Intermediate Similarity	NPD1086	Approved
0.7417	Intermediate Similarity	NPD1283	Approved
0.7414	Intermediate Similarity	NPD1894	Discontinued
0.7411	Intermediate Similarity	NPD228	Approved
0.7396	Intermediate Similarity	NPD226	Approved
0.7391	Intermediate Similarity	NPD9087	Approved
0.7387	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD3026	Approved
0.7373	Intermediate Similarity	NPD3023	Approved
0.7368	Intermediate Similarity	NPD9281	Approved
0.7368	Intermediate Similarity	NPD9490	Approved
0.736	Intermediate Similarity	NPD1240	Approved
0.7355	Intermediate Similarity	NPD1470	Approved
0.735	Intermediate Similarity	NPD1651	Approved
0.735	Intermediate Similarity	NPD3025	Approved
0.735	Intermediate Similarity	NPD3024	Approved
0.7282	Intermediate Similarity	NPD1088	Approved
0.7281	Intermediate Similarity	NPD2234	Approved
0.7281	Intermediate Similarity	NPD2228	Approved
0.7281	Intermediate Similarity	NPD2229	Approved
0.7273	Intermediate Similarity	NPD1444	Approved
0.7273	Intermediate Similarity	NPD1445	Approved
0.7264	Intermediate Similarity	NPD9273	Approved
0.7263	Intermediate Similarity	NPD9088	Approved
0.725	Intermediate Similarity	NPD1608	Approved
0.725	Intermediate Similarity	NPD3972	Approved
0.725	Intermediate Similarity	NPD9717	Approved
0.7244	Intermediate Similarity	NPD1607	Approved
0.7236	Intermediate Similarity	NPD9569	Approved
0.7236	Intermediate Similarity	NPD9494	Approved
0.7227	Intermediate Similarity	NPD3847	Discontinued
0.7222	Intermediate Similarity	NPD943	Approved
0.72	Intermediate Similarity	NPD9257	Approved
0.72	Intermediate Similarity	NPD3764	Approved
0.72	Intermediate Similarity	NPD9259	Approved
0.7196	Intermediate Similarity	NPD2066	Phase 3
0.7193	Intermediate Similarity	NPD9379	Approved
0.7193	Intermediate Similarity	NPD9377	Approved
0.7184	Intermediate Similarity	NPD1239	Approved
0.7167	Intermediate Similarity	NPD1281	Approved
0.7158	Intermediate Similarity	NPD9294	Approved
0.7143	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD259	Phase 1
0.7143	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD1876	Approved
0.7131	Intermediate Similarity	NPD196	Phase 1
0.7129	Intermediate Similarity	NPD1087	Approved
0.7117	Intermediate Similarity	NPD968	Approved
0.7107	Intermediate Similarity	NPD9269	Phase 2
0.7105	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD454	Approved
0.7097	Intermediate Similarity	NPD5736	Approved
0.7087	Intermediate Similarity	NPD825	Approved
0.7087	Intermediate Similarity	NPD826	Approved
0.7083	Intermediate Similarity	NPD227	Approved
0.7083	Intermediate Similarity	NPD225	Approved
0.708	Intermediate Similarity	NPD4750	Phase 3
0.708	Intermediate Similarity	NPD1792	Phase 2
0.7073	Intermediate Similarity	NPD1203	Approved
0.7073	Intermediate Similarity	NPD2797	Approved
0.7069	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9268	Approved
0.7049	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1202	Approved
0.7048	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD821	Approved
0.7034	Intermediate Similarity	NPD318	Approved
0.7034	Intermediate Similarity	NPD16	Approved
0.7034	Intermediate Similarity	NPD317	Approved
0.7034	Intermediate Similarity	NPD856	Approved
0.7031	Intermediate Similarity	NPD555	Phase 2
0.7031	Intermediate Similarity	NPD274	Approved
0.7031	Intermediate Similarity	NPD275	Approved
0.7025	Intermediate Similarity	NPD422	Phase 1
0.7023	Intermediate Similarity	NPD2344	Approved
0.7016	Intermediate Similarity	NPD2798	Approved
0.7009	Intermediate Similarity	NPD1564	Approved
0.7009	Intermediate Similarity	NPD1565	Approved
0.7009	Intermediate Similarity	NPD1566	Phase 3
0.7	Intermediate Similarity	NPD9500	Approved
0.7	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1930	Approved
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD1510	Phase 2
0.7	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1929	Approved
0.699	Remote Similarity	NPD5346	Phase 2
0.699	Remote Similarity	NPD5347	Phase 2
0.6984	Remote Similarity	NPD3136	Phase 2
0.6984	Remote Similarity	NPD9537	Phase 1
0.6984	Remote Similarity	NPD9536	Phase 1
0.6983	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3091	Approved
0.697	Remote Similarity	NPD9089	Approved
0.6964	Remote Similarity	NPD3134	Approved
0.6961	Remote Similarity	NPD4793	Discontinued
0.6947	Remote Similarity	NPD2935	Discontinued
0.6929	Remote Similarity	NPD6798	Discontinued
0.6929	Remote Similarity	NPD3268	Approved
0.6929	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9618	Approved
0.6923	Remote Similarity	NPD2629	Approved
0.6923	Remote Similarity	NPD475	Phase 2
0.6923	Remote Similarity	NPD9614	Approved
0.6905	Remote Similarity	NPD2614	Approved
0.6903	Remote Similarity	NPD1358	Approved
0.6903	Remote Similarity	NPD290	Approved
0.6903	Remote Similarity	NPD2342	Discontinued
0.6899	Remote Similarity	NPD230	Phase 1
0.6897	Remote Similarity	NPD5535	Approved
0.6897	Remote Similarity	NPD7843	Approved
0.6897	Remote Similarity	NPD7635	Approved
0.6894	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4062	Phase 3
0.6875	Remote Similarity	NPD6233	Phase 2
0.687	Remote Similarity	NPD2799	Discontinued
0.687	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD9093	Approved
0.6864	Remote Similarity	NPD6671	Approved
0.686	Remote Similarity	NPD1778	Approved
0.686	Remote Similarity	NPD4059	Approved
0.686	Remote Similarity	NPD4626	Approved
0.686	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.685	Remote Similarity	NPD9718	Approved
0.6842	Remote Similarity	NPD1549	Phase 2
0.6833	Remote Similarity	NPD1548	Phase 1
0.6833	Remote Similarity	NPD5304	Approved
0.6833	Remote Similarity	NPD5303	Approved
0.6827	Remote Similarity	NPD9295	Approved
0.6818	Remote Similarity	NPD7450	Phase 2
0.6815	Remote Similarity	NPD2309	Approved
0.681	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD164	Approved
0.6786	Remote Similarity	NPD5909	Discontinued
0.6783	Remote Similarity	NPD5451	Approved
0.678	Remote Similarity	NPD1791	Approved
0.678	Remote Similarity	NPD1793	Approved
0.678	Remote Similarity	NPD5951	Approved
0.678	Remote Similarity	NPD1476	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