NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.07
Volume:	264.953
LogP:	3.206
LogD:	2.915
LogS:	-3.12
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	2.134
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.821
MDCK Permeability:	1.3478173059411347e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	99.68718719482422%
Volume Distribution (VD):	0.508
Pgp-substrate:	0.8190453052520752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.95
CYP1A2-substrate:	0.198
CYP2C19-inhibitor:	0.758
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.761
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.875
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.791
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	13.229
Half-life (T1/2):	0.911

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.607
AMES Toxicity:	0.798
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.444
Skin Sensitization:	0.948
Carcinogencity:	0.622
Eye Corrosion:	0.154
Eye Irritation:	0.974
Respiratory Toxicity:	0.337

Download Data

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

Natural Product: NPC224273

Natural Product ID:	NPC224273
*Common Name:**	2,2',4'-Trihydroxychalcone
IUPAC Name:	(E)-1-(2,4-dihydroxyphenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one
Synonyms:	2,2',4'-Trihydroxychalcone
Standard InCHIKey:	MACMAADVRVVHBD-VMPITWQZSA-N
Standard InCHI:	InChI=1S/C15H12O4/c16-11-6-7-12(15(19)9-11)14(18)8-5-10-3-1-2-4-13(10)17/h1-9,16-17,19H/b8-5+
SMILES:	Oc1ccc(c(c1)O)C(=O)/C=C/c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL148472
PubChem CID:	5811533
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO20812	Soymida febrifuga	Species	Meliaceae	Eukaryota	n.a.	Myanmar	n.a.	PMID[19689125]
NPO20812	Soymida febrifuga	Species	Meliaceae	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
EC50	1
IC50	10
Others	9

Activity Type	# Activity
Cell Line	4
Individual Protein	7
NON-MOLECULAR	2
Organism	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	4.8	uM	PMID[505644]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	53000.0	nM	PMID[505645]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	47000.0	nM	PMID[505645]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	89900.0	nM	PMID[505646]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	40400.0	nM	PMID[505646]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[505646]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	89100.0	nM	PMID[505646]
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	EC50	=	4000.0	nM	PMID[505648]
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	Ratio	=	2.6	n.a.	PMID[505648]
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	IC50	=	56800.0	nM	PMID[505650]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28900.0	nM	PMID[505646]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[505646]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	380.0	nM	PMID[505647]
NPT35	Others	n.a.		Activity	=	0.87	mmolequiv/mmol	PMID[505650]
NPT35	Others	n.a.		IC50	=	128000.0	nM	PMID[505650]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	5.21	mg/dl	PMID[505650]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	4.5	mg/dl	PMID[505650]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	73.2	U	PMID[505650]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	64.1	U	PMID[505650]
NPT32	Organism	Mus musculus	Mus musculus	MTD	<=	5000.0	mg kg-1	PMID[505650]

☑ 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 NPC224273 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	390
0.1-0.2	1933
0.2-0.3	4994
0.3-0.4	12610
0.4-0.5	5443
0.5-0.6	5695
0.6-0.7	6399
0.7-0.8	4209
0.8-0.85	716
0.85-0.9	207
0.9-0.95	85
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC267552
1.0	High Similarity	NPC45438
1.0	High Similarity	NPC143427
1.0	High Similarity	NPC73532
1.0	High Similarity	NPC19174
1.0	High Similarity	NPC115159
0.9913	High Similarity	NPC133909
0.9913	High Similarity	NPC32032
0.9912	High Similarity	NPC297186
0.9826	High Similarity	NPC156139
0.9826	High Similarity	NPC242895
0.9744	High Similarity	NPC13238
0.9737	High Similarity	NPC158222
0.9652	High Similarity	NPC159525
0.958	High Similarity	NPC8745
0.9565	High Similarity	NPC161617
0.95	High Similarity	NPC103356
0.95	High Similarity	NPC72158
0.95	High Similarity	NPC162612
0.95	High Similarity	NPC30501
0.95	High Similarity	NPC100067
0.95	High Similarity	NPC266689
0.95	High Similarity	NPC98254
0.95	High Similarity	NPC190043
0.95	High Similarity	NPC23126
0.95	High Similarity	NPC169250
0.95	High Similarity	NPC105157
0.9496	High Similarity	NPC10926
0.9487	High Similarity	NPC196976
0.9478	High Similarity	NPC209486
0.9478	High Similarity	NPC40649
0.9421	High Similarity	NPC221777
0.9421	High Similarity	NPC473017
0.9421	High Similarity	NPC21305
0.9417	High Similarity	NPC267846
0.9417	High Similarity	NPC62952
0.9344	High Similarity	NPC102829
0.9344	High Similarity	NPC474998
0.9344	High Similarity	NPC120488
0.9339	High Similarity	NPC116513
0.9316	High Similarity	NPC294037
0.9268	High Similarity	NPC26697
0.9244	High Similarity	NPC309765
0.9237	High Similarity	NPC146642
0.9237	High Similarity	NPC248363
0.9237	High Similarity	NPC149246
0.9231	High Similarity	NPC195262
0.9231	High Similarity	NPC188814
0.9194	High Similarity	NPC475042
0.9194	High Similarity	NPC34070
0.9194	High Similarity	NPC469526
0.9187	High Similarity	NPC476119
0.916	High Similarity	NPC215392
0.916	High Similarity	NPC303737
0.9145	High Similarity	NPC241089
0.913	High Similarity	NPC276111
0.913	High Similarity	NPC118288
0.912	High Similarity	NPC135801
0.912	High Similarity	NPC262359
0.9113	High Similarity	NPC233056
0.9083	High Similarity	NPC91105
0.9048	High Similarity	NPC129132
0.9048	High Similarity	NPC139074
0.9048	High Similarity	NPC205468
0.9048	High Similarity	NPC257756
0.9048	High Similarity	NPC212631
0.9048	High Similarity	NPC213485
0.9048	High Similarity	NPC40524
0.9048	High Similarity	NPC87231
0.9032	High Similarity	NPC109123
0.9032	High Similarity	NPC92624
0.9008	High Similarity	NPC65761
0.9008	High Similarity	NPC472029
0.9	High Similarity	NPC226275
0.8983	High Similarity	NPC283844
0.8976	High Similarity	NPC56031
0.8976	High Similarity	NPC282780
0.8976	High Similarity	NPC242294
0.8976	High Similarity	NPC192304
0.8976	High Similarity	NPC263670
0.8976	High Similarity	NPC312318
0.8976	High Similarity	NPC472365
0.8976	High Similarity	NPC44437
0.8976	High Similarity	NPC166480
0.8976	High Similarity	NPC337373
0.8976	High Similarity	NPC139813
0.8976	High Similarity	NPC175098
0.8976	High Similarity	NPC188646
0.8968	High Similarity	NPC175738
0.8968	High Similarity	NPC308037
0.8968	High Similarity	NPC64359
0.8968	High Similarity	NPC313618
0.896	High Similarity	NPC259942
0.8906	High Similarity	NPC286336
0.8906	High Similarity	NPC470210
0.8906	High Similarity	NPC283590
0.8906	High Similarity	NPC70859
0.8906	High Similarity	NPC172262
0.8906	High Similarity	NPC61153
0.8906	High Similarity	NPC130899
0.8898	High Similarity	NPC121259
0.8898	High Similarity	NPC230349
0.8889	High Similarity	NPC275504
0.8862	High Similarity	NPC475733
0.8837	High Similarity	NPC65005
0.8837	High Similarity	NPC39426
0.8837	High Similarity	NPC131039
0.8837	High Similarity	NPC9985
0.8837	High Similarity	NPC239495
0.8837	High Similarity	NPC234560
0.8837	High Similarity	NPC264112
0.8837	High Similarity	NPC194764
0.8828	High Similarity	NPC82225
0.8828	High Similarity	NPC78540
0.8828	High Similarity	NPC274121
0.8828	High Similarity	NPC213216
0.8828	High Similarity	NPC18877
0.8828	High Similarity	NPC159623
0.8828	High Similarity	NPC20560
0.8828	High Similarity	NPC50898
0.8828	High Similarity	NPC204960
0.8828	High Similarity	NPC144051
0.8828	High Similarity	NPC57601
0.8828	High Similarity	NPC294593
0.8828	High Similarity	NPC28753
0.881	High Similarity	NPC244441
0.881	High Similarity	NPC185497
0.881	High Similarity	NPC247779
0.881	High Similarity	NPC147757
0.88	High Similarity	NPC80694
0.88	High Similarity	NPC186098
0.88	High Similarity	NPC179898
0.879	High Similarity	NPC95309
0.8772	High Similarity	NPC17525
0.8769	High Similarity	NPC213603
0.8769	High Similarity	NPC41461
0.8769	High Similarity	NPC53414
0.8769	High Similarity	NPC25287
0.8769	High Similarity	NPC66349
0.8769	High Similarity	NPC290030
0.8769	High Similarity	NPC473391
0.8769	High Similarity	NPC249606
0.8769	High Similarity	NPC274109
0.8769	High Similarity	NPC235428
0.8769	High Similarity	NPC186838
0.8769	High Similarity	NPC12165
0.8769	High Similarity	NPC472367
0.8769	High Similarity	NPC472364
0.8769	High Similarity	NPC1486
0.8769	High Similarity	NPC477244
0.8769	High Similarity	NPC168105
0.8769	High Similarity	NPC53206
0.8769	High Similarity	NPC98115
0.8769	High Similarity	NPC476333
0.8769	High Similarity	NPC474110
0.8769	High Similarity	NPC477243
0.8769	High Similarity	NPC44960
0.8769	High Similarity	NPC150399
0.8769	High Similarity	NPC477242
0.8769	High Similarity	NPC87545
0.876	High Similarity	NPC229649
0.875	High Similarity	NPC267205
0.874	High Similarity	NPC198249
0.873	High Similarity	NPC60558
0.872	High Similarity	NPC305518
0.872	High Similarity	NPC128428
0.872	High Similarity	NPC107672
0.8718	High Similarity	NPC223004
0.871	High Similarity	NPC262671
0.871	High Similarity	NPC201728
0.871	High Similarity	NPC477454
0.8702	High Similarity	NPC209560
0.8702	High Similarity	NPC294409
0.8702	High Similarity	NPC181124
0.8702	High Similarity	NPC153979
0.8702	High Similarity	NPC250266
0.8702	High Similarity	NPC7013
0.8702	High Similarity	NPC275055
0.8702	High Similarity	NPC116632
0.8702	High Similarity	NPC317119
0.8702	High Similarity	NPC212767
0.8702	High Similarity	NPC254841
0.8702	High Similarity	NPC299379
0.8702	High Similarity	NPC303644
0.8702	High Similarity	NPC266597
0.8702	High Similarity	NPC290291
0.8702	High Similarity	NPC188879
0.8702	High Similarity	NPC162680
0.8702	High Similarity	NPC472419
0.8702	High Similarity	NPC175552
0.8692	High Similarity	NPC156092
0.8692	High Similarity	NPC254847
0.8692	High Similarity	NPC13575
0.8684	High Similarity	NPC141523
0.8682	High Similarity	NPC475088
0.8672	High Similarity	NPC475008
0.8672	High Similarity	NPC164236
0.8672	High Similarity	NPC113006
0.8672	High Similarity	NPC128348
0.8672	High Similarity	NPC186097

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 NPC224273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	995
0.2-0.3	1471
0.3-0.4	2945
0.4-0.5	1937
0.5-0.6	1042
0.6-0.7	274
0.7-0.8	96
0.8-0.85	13
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.912	High Similarity	NPD943	Approved
0.8968	High Similarity	NPD1240	Approved
0.8837	High Similarity	NPD1510	Phase 2
0.8828	High Similarity	NPD1607	Approved
0.8692	High Similarity	NPD1509	Clinical (unspecified phase)
0.8636	High Similarity	NPD1549	Phase 2
0.8561	High Similarity	NPD1550	Clinical (unspecified phase)
0.8561	High Similarity	NPD1552	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD74	Approved
0.8291	Intermediate Similarity	NPD9266	Approved
0.8268	Intermediate Similarity	NPD1470	Approved
0.8268	Intermediate Similarity	NPD1164	Approved
0.824	Intermediate Similarity	NPD1201	Approved
0.8205	Intermediate Similarity	NPD9267	Approved
0.8205	Intermediate Similarity	NPD9263	Approved
0.8205	Intermediate Similarity	NPD9264	Approved
0.8205	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1511	Approved
0.8129	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1512	Approved
0.8058	Intermediate Similarity	NPD7390	Discontinued
0.8049	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD9493	Approved
0.7984	Intermediate Similarity	NPD1203	Approved
0.7972	Intermediate Similarity	NPD4380	Phase 2
0.7956	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD2796	Approved
0.7941	Intermediate Similarity	NPD1551	Phase 2
0.7929	Intermediate Similarity	NPD6799	Approved
0.7891	Intermediate Similarity	NPD9269	Phase 2
0.7886	Intermediate Similarity	NPD9281	Approved
0.7863	Intermediate Similarity	NPD9261	Approved
0.7857	Intermediate Similarity	NPD9268	Approved
0.7842	Intermediate Similarity	NPD3750	Approved
0.781	Intermediate Similarity	NPD5406	Approved
0.781	Intermediate Similarity	NPD5408	Approved
0.781	Intermediate Similarity	NPD5405	Approved
0.781	Intermediate Similarity	NPD5404	Approved
0.7793	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD9545	Approved
0.7778	Intermediate Similarity	NPD940	Approved
0.7778	Intermediate Similarity	NPD846	Approved
0.774	Intermediate Similarity	NPD1934	Approved
0.7717	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD3882	Suspended
0.7692	Intermediate Similarity	NPD1242	Phase 1
0.7687	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2801	Approved
0.7681	Intermediate Similarity	NPD2935	Discontinued
0.7651	Intermediate Similarity	NPD7075	Discontinued
0.7651	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3749	Approved
0.7635	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD2344	Approved
0.7615	Intermediate Similarity	NPD9717	Approved
0.7603	Intermediate Similarity	NPD6599	Discontinued
0.7591	Intermediate Similarity	NPD6651	Approved
0.7568	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7819	Suspended
0.7556	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1243	Approved
0.7518	Intermediate Similarity	NPD2800	Approved
0.7518	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD6801	Discontinued
0.7482	Intermediate Similarity	NPD3748	Approved
0.7426	Intermediate Similarity	NPD3764	Approved
0.7413	Intermediate Similarity	NPD2309	Approved
0.7405	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5403	Approved
0.7394	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2798	Approved
0.7379	Intermediate Similarity	NPD5401	Approved
0.7372	Intermediate Similarity	NPD520	Approved
0.7361	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2799	Discontinued
0.7355	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1237	Approved
0.7351	Intermediate Similarity	NPD7768	Phase 2
0.7299	Intermediate Similarity	NPD2313	Discontinued
0.7285	Intermediate Similarity	NPD3817	Phase 2
0.7279	Intermediate Similarity	NPD6832	Phase 2
0.7279	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD2654	Approved
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7265	Intermediate Similarity	NPD2934	Approved
0.7265	Intermediate Similarity	NPD2933	Approved
0.7261	Intermediate Similarity	NPD3818	Discontinued
0.726	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6166	Phase 2
0.7244	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1548	Phase 1
0.7226	Intermediate Similarity	NPD6232	Discontinued
0.7218	Intermediate Similarity	NPD3972	Approved
0.7203	Intermediate Similarity	NPD2859	Approved
0.7203	Intermediate Similarity	NPD2860	Approved
0.7197	Intermediate Similarity	NPD7473	Discontinued
0.7161	Intermediate Similarity	NPD6959	Discontinued
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7125	Intermediate Similarity	NPD5953	Discontinued
0.7124	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7054	Approved
0.7107	Intermediate Similarity	NPD7286	Phase 2
0.7103	Intermediate Similarity	NPD1196	Approved
0.7075	Intermediate Similarity	NPD1543	Discontinued
0.7063	Intermediate Similarity	NPD4750	Phase 3
0.7063	Intermediate Similarity	NPD7074	Phase 3
0.7063	Intermediate Similarity	NPD7472	Approved
0.7059	Intermediate Similarity	NPD5402	Approved
0.705	Intermediate Similarity	NPD3268	Approved
0.705	Intermediate Similarity	NPD411	Approved
0.7034	Intermediate Similarity	NPD1202	Approved
0.7034	Intermediate Similarity	NPD1195	Approved
0.7025	Intermediate Similarity	NPD3020	Approved
0.7021	Intermediate Similarity	NPD447	Suspended
0.7019	Intermediate Similarity	NPD6797	Phase 2
0.7015	Intermediate Similarity	NPD1610	Phase 2
0.7007	Intermediate Similarity	NPD3300	Phase 2
0.7	Intermediate Similarity	NPD6020	Phase 2
0.6993	Remote Similarity	NPD4308	Phase 3
0.6993	Remote Similarity	NPD1465	Phase 2
0.6987	Remote Similarity	NPD5494	Approved
0.6986	Remote Similarity	NPD4628	Phase 3
0.6985	Remote Similarity	NPD3225	Approved
0.6977	Remote Similarity	NPD1241	Discontinued
0.6975	Remote Similarity	NPD7251	Discontinued
0.697	Remote Similarity	NPD1759	Phase 1
0.6963	Remote Similarity	NPD1481	Phase 2
0.6954	Remote Similarity	NPD3226	Approved
0.6944	Remote Similarity	NPD6099	Approved
0.6944	Remote Similarity	NPD6100	Approved
0.6934	Remote Similarity	NPD2797	Approved
0.6933	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7808	Phase 3
0.6933	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1296	Phase 2
0.6923	Remote Similarity	NPD9258	Approved
0.6923	Remote Similarity	NPD919	Approved
0.6923	Remote Similarity	NPD9256	Approved
0.6913	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1933	Approved
0.6901	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2346	Discontinued
0.6894	Remote Similarity	NPD1758	Phase 1
0.6889	Remote Similarity	NPD1535	Discovery
0.6884	Remote Similarity	NPD1019	Discontinued
0.6871	Remote Similarity	NPD6559	Discontinued
0.6866	Remote Similarity	NPD2932	Approved
0.6866	Remote Similarity	NPD3019	Approved
0.6861	Remote Similarity	NPD1876	Approved
0.6855	Remote Similarity	NPD3926	Phase 2
0.6839	Remote Similarity	NPD2296	Approved
0.6839	Remote Similarity	NPD4288	Approved
0.6838	Remote Similarity	NPD1608	Approved
0.6835	Remote Similarity	NPD9494	Approved
0.6835	Remote Similarity	NPD1247	Approved
0.6824	Remote Similarity	NPD6190	Approved
0.6812	Remote Similarity	NPD3266	Approved
0.6812	Remote Similarity	NPD3267	Approved
0.6786	Remote Similarity	NPD4908	Phase 1
0.6786	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD111	Approved
0.6781	Remote Similarity	NPD1471	Phase 3
0.6759	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7033	Discontinued
0.6757	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3400	Discontinued
0.6748	Remote Similarity	NPD1729	Discontinued
0.6742	Remote Similarity	NPD256	Approved
0.6742	Remote Similarity	NPD255	Approved
0.6732	Remote Similarity	NPD7458	Discontinued
0.672	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1929	Approved
0.672	Remote Similarity	NPD1930	Approved
0.6719	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4307	Phase 2
0.6711	Remote Similarity	NPD2354	Approved
0.6707	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD9568	Approved
0.669	Remote Similarity	NPD9279	Approved
0.669	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5844	Phase 1
0.6686	Remote Similarity	NPD4287	Approved
0.6667	Remote Similarity	NPD3021	Approved
0.6667	Remote Similarity	NPD9089	Approved
0.6667	Remote Similarity	NPD1755	Approved
0.6667	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3022	Approved
0.6644	Remote Similarity	NPD7003	Approved
0.6639	Remote Similarity	NPD844	Approved
0.6639	Remote Similarity	NPD1809	Phase 2

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