NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	276.379
LogP:	0.819
LogD:	0.607
LogS:	-2.071
# Rotatable Bonds:	4
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	2.735
Fsp3:	0.133
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:	-5.071
MDCK Permeability:	5.94793073105393e-06
Pgp-inhibitor:	0.036
Pgp-substrate:	0.522
Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	0.881
30% Bioavailability (F30%):	0.183

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	75.17974090576172%
Volume Distribution (VD):	0.774
Pgp-substrate:	30.854337692260742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.168
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.475
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.334
CYP2D6-substrate:	0.747
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	13.809
Half-life (T1/2):	0.933

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.569
AMES Toxicity:	0.403
Rat Oral Acute Toxicity:	0.274
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.856
Carcinogencity:	0.071
Eye Corrosion:	0.003
Eye Irritation:	0.805
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC102829

Natural Product ID:	NPC102829
*Common Name:**	(Alphas)-Alpha,2',4,4'-Tetrahydroxydihydrochalcone
IUPAC Name:	(2S)-1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(4-hydroxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	SLKHLLNCFGPWAZ-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C15H14O5/c16-10-3-1-9(2-4-10)7-14(19)15(20)12-6-5-11(17)8-13(12)18/h1-6,8,14,16-19H,7H2/t14-/m0/s1
SMILES:	Oc1ccc(cc1)C[C@@H](C(=O)c1ccc(cc1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252790
PubChem CID:	44446908
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003473] 2'-Hydroxy-dihydrochalcones

*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
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[17950610]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[18440233]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26938776]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32525315]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	7
Others	1

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	>	100.0	uM	PMID[465237]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[465238]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[465238]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[465238]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[465239]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[465238]

☑ 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 NPC102829 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	364
0.1-0.2	1511
0.2-0.3	4059
0.3-0.4	11055
0.4-0.5	8096
0.5-0.6	4890
0.6-0.7	6554
0.7-0.8	5204
0.8-0.85	760
0.85-0.9	152
0.9-0.95	44
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC120488
0.9531	High Similarity	NPC70859
0.9531	High Similarity	NPC61153
0.9531	High Similarity	NPC283590
0.9531	High Similarity	NPC130899
0.9426	High Similarity	NPC32032
0.9426	High Similarity	NPC133909
0.9375	High Similarity	NPC213485
0.9375	High Similarity	NPC40524
0.9375	High Similarity	NPC139074
0.937	High Similarity	NPC475042
0.9344	High Similarity	NPC115159
0.9344	High Similarity	NPC224273
0.9344	High Similarity	NPC143427
0.9344	High Similarity	NPC19174
0.9344	High Similarity	NPC73532
0.9344	High Similarity	NPC267552
0.9344	High Similarity	NPC156139
0.9344	High Similarity	NPC45438
0.9344	High Similarity	NPC242895
0.9313	High Similarity	NPC175552
0.9262	High Similarity	NPC297186
0.918	High Similarity	NPC159525
0.9147	High Similarity	NPC478190
0.9127	High Similarity	NPC8745
0.912	High Similarity	NPC13238
0.9098	High Similarity	NPC158222
0.9091	High Similarity	NPC170742
0.9062	High Similarity	NPC476119
0.9055	High Similarity	NPC30501
0.9055	High Similarity	NPC105157
0.9055	High Similarity	NPC169250
0.9055	High Similarity	NPC103356
0.9055	High Similarity	NPC100067
0.9055	High Similarity	NPC72158
0.9055	High Similarity	NPC190043
0.9055	High Similarity	NPC266689
0.9055	High Similarity	NPC23126
0.9055	High Similarity	NPC162612
0.9055	High Similarity	NPC98254
0.9048	High Similarity	NPC10926
0.9032	High Similarity	NPC196976
0.8992	High Similarity	NPC147757
0.8984	High Similarity	NPC21305
0.8984	High Similarity	NPC221777
0.8984	High Similarity	NPC473017
0.8976	High Similarity	NPC267846
0.8976	High Similarity	NPC62952
0.8971	High Similarity	NPC148545
0.8943	High Similarity	NPC161617
0.8923	High Similarity	NPC198249
0.8915	High Similarity	NPC474998
0.8906	High Similarity	NPC116513
0.8905	High Similarity	NPC245482
0.8905	High Similarity	NPC301751
0.8871	High Similarity	NPC294037
0.8862	High Similarity	NPC40649
0.8862	High Similarity	NPC209486
0.881	High Similarity	NPC309765
0.88	High Similarity	NPC146642
0.88	High Similarity	NPC149246
0.88	High Similarity	NPC248363
0.8797	High Similarity	NPC470210
0.879	High Similarity	NPC195262
0.879	High Similarity	NPC188814
0.8779	High Similarity	NPC275504
0.8777	High Similarity	NPC148011
0.8777	High Similarity	NPC1940
0.8768	High Similarity	NPC471906
0.8759	High Similarity	NPC137649
0.8759	High Similarity	NPC321980
0.8759	High Similarity	NPC470087
0.875	High Similarity	NPC470211
0.8731	High Similarity	NPC234560
0.8731	High Similarity	NPC39426
0.873	High Similarity	NPC215392
0.873	High Similarity	NPC303737
0.8712	High Similarity	NPC135801
0.8712	High Similarity	NPC262359
0.8712	High Similarity	NPC65060
0.8712	High Similarity	NPC17843
0.8712	High Similarity	NPC313618
0.871	High Similarity	NPC283844
0.871	High Similarity	NPC249435
0.8705	High Similarity	NPC279417
0.8705	High Similarity	NPC49130
0.8705	High Similarity	NPC4152
0.8705	High Similarity	NPC326506
0.8705	High Similarity	NPC142731
0.8705	High Similarity	NPC208176
0.8705	High Similarity	NPC306607
0.8705	High Similarity	NPC62290
0.8702	High Similarity	NPC233056
0.8702	High Similarity	NPC26697
0.8676	High Similarity	NPC147686
0.8676	High Similarity	NPC329225
0.8676	High Similarity	NPC190457
0.8676	High Similarity	NPC472460
0.8667	High Similarity	NPC87545
0.8667	High Similarity	NPC235428
0.8661	High Similarity	NPC91105
0.8657	High Similarity	NPC286336
0.8647	High Similarity	NPC205468
0.8647	High Similarity	NPC257756
0.8647	High Similarity	NPC87231
0.8647	High Similarity	NPC212631
0.8647	High Similarity	NPC129132
0.8636	High Similarity	NPC469526
0.8636	High Similarity	NPC34070
0.8633	High Similarity	NPC51887
0.8633	High Similarity	NPC117836
0.8633	High Similarity	NPC475705
0.8633	High Similarity	NPC476178
0.8629	High Similarity	NPC230349
0.8626	High Similarity	NPC92624
0.8626	High Similarity	NPC109123
0.8623	High Similarity	NPC470089
0.8623	High Similarity	NPC150023
0.8613	High Similarity	NPC201541
0.8603	High Similarity	NPC296490
0.8603	High Similarity	NPC294409
0.8603	High Similarity	NPC7013
0.8603	High Similarity	NPC116632
0.8603	High Similarity	NPC12296
0.8603	High Similarity	NPC295261
0.8603	High Similarity	NPC243083
0.8603	High Similarity	NPC181124
0.8603	High Similarity	NPC84585
0.8603	High Similarity	NPC107586
0.8603	High Similarity	NPC287246
0.8603	High Similarity	NPC162680
0.8603	High Similarity	NPC209560
0.8603	High Similarity	NPC212767
0.8603	High Similarity	NPC79943
0.8603	High Similarity	NPC476480
0.8603	High Similarity	NPC303644
0.8603	High Similarity	NPC32441
0.8603	High Similarity	NPC299379
0.8603	High Similarity	NPC13768
0.8594	High Similarity	NPC65761
0.8594	High Similarity	NPC472029
0.8593	High Similarity	NPC131039
0.8583	High Similarity	NPC226275
0.8582	High Similarity	NPC139813
0.8582	High Similarity	NPC122828
0.8582	High Similarity	NPC312318
0.8582	High Similarity	NPC40086
0.8582	High Similarity	NPC263670
0.8582	High Similarity	NPC20560
0.8582	High Similarity	NPC18877
0.8582	High Similarity	NPC56031
0.8582	High Similarity	NPC192304
0.8582	High Similarity	NPC3779
0.8582	High Similarity	NPC175098
0.8582	High Similarity	NPC44721
0.8582	High Similarity	NPC144051
0.8582	High Similarity	NPC282780
0.8582	High Similarity	NPC472365
0.8582	High Similarity	NPC242294
0.8582	High Similarity	NPC82225
0.8582	High Similarity	NPC337373
0.8582	High Similarity	NPC211466
0.8582	High Similarity	NPC476182
0.8582	High Similarity	NPC204960
0.8582	High Similarity	NPC166480
0.8582	High Similarity	NPC28753
0.8582	High Similarity	NPC159623
0.8582	High Similarity	NPC188646
0.8582	High Similarity	NPC44437
0.8582	High Similarity	NPC294593
0.8582	High Similarity	NPC176869
0.8571	High Similarity	NPC175738
0.8571	High Similarity	NPC308037
0.8571	High Similarity	NPC64359
0.8561	High Similarity	NPC185497
0.8561	High Similarity	NPC259942
0.856	High Similarity	NPC241089
0.8551	High Similarity	NPC281207
0.8551	High Similarity	NPC305845
0.8551	High Similarity	NPC204045
0.8551	High Similarity	NPC269652
0.855	High Similarity	NPC179898
0.854	High Similarity	NPC19622
0.854	High Similarity	NPC112789
0.854	High Similarity	NPC55162
0.854	High Similarity	NPC12175
0.854	High Similarity	NPC90665
0.854	High Similarity	NPC278323
0.854	High Similarity	NPC279668
0.854	High Similarity	NPC124269
0.854	High Similarity	NPC309154
0.8537	High Similarity	NPC276111
0.8537	High Similarity	NPC118288
0.8531	High Similarity	NPC61258
0.8529	High Similarity	NPC281917
0.8529	High Similarity	NPC116775
0.8529	High Similarity	NPC187432
0.8529	High Similarity	NPC186838
0.8529	High Similarity	NPC1486
0.8529	High Similarity	NPC44960

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 NPC102829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	905
0.2-0.3	1568
0.3-0.4	2872
0.4-0.5	2016
0.5-0.6	1017
0.6-0.7	309
0.7-0.8	108
0.8-0.85	4
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8731	High Similarity	NPD1510	Phase 2
0.8712	High Similarity	NPD1240	Approved
0.8712	High Similarity	NPD943	Approved
0.8676	High Similarity	NPD1549	Phase 2
0.8603	High Similarity	NPD1550	Clinical (unspecified phase)
0.8603	High Similarity	NPD1552	Clinical (unspecified phase)
0.8582	High Similarity	NPD1607	Approved
0.8321	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD1512	Approved
0.7986	Intermediate Similarity	NPD6799	Approved
0.7947	Intermediate Similarity	NPD7075	Discontinued
0.7947	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6801	Discontinued
0.7919	Intermediate Similarity	NPD1934	Approved
0.791	Intermediate Similarity	NPD1164	Approved
0.791	Intermediate Similarity	NPD1470	Approved
0.7879	Intermediate Similarity	NPD1201	Approved
0.7869	Intermediate Similarity	NPD1237	Approved
0.7867	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7390	Discontinued
0.7862	Intermediate Similarity	NPD1511	Approved
0.7808	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6599	Discontinued
0.7763	Intermediate Similarity	NPD3882	Suspended
0.776	Intermediate Similarity	NPD9266	Approved
0.776	Intermediate Similarity	NPD74	Approved
0.7756	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6166	Phase 2
0.7756	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1551	Phase 2
0.7733	Intermediate Similarity	NPD7411	Suspended
0.7703	Intermediate Similarity	NPD5403	Approved
0.7697	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9493	Approved
0.7687	Intermediate Similarity	NPD5401	Approved
0.768	Intermediate Similarity	NPD9267	Approved
0.768	Intermediate Similarity	NPD9264	Approved
0.768	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD9263	Approved
0.7655	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2935	Discontinued
0.761	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD9545	Approved
0.7557	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD9269	Phase 2
0.7547	Intermediate Similarity	NPD3818	Discontinued
0.7534	Intermediate Similarity	NPD3750	Approved
0.7519	Intermediate Similarity	NPD9268	Approved
0.7518	Intermediate Similarity	NPD1203	Approved
0.7516	Intermediate Similarity	NPD7819	Suspended
0.7516	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7481	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5402	Approved
0.7468	Intermediate Similarity	NPD3817	Phase 2
0.7465	Intermediate Similarity	NPD230	Phase 1
0.7419	Intermediate Similarity	NPD940	Approved
0.7419	Intermediate Similarity	NPD846	Approved
0.7413	Intermediate Similarity	NPD6651	Approved
0.7407	Intermediate Similarity	NPD6797	Phase 2
0.7405	Intermediate Similarity	NPD9281	Approved
0.7388	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3749	Approved
0.7362	Intermediate Similarity	NPD7251	Discontinued
0.736	Intermediate Similarity	NPD9261	Approved
0.7351	Intermediate Similarity	NPD920	Approved
0.7347	Intermediate Similarity	NPD2800	Approved
0.7347	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7074	Phase 3
0.7342	Intermediate Similarity	NPD6959	Discontinued
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2344	Approved
0.7317	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7808	Phase 3
0.7315	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7768	Phase 2
0.7308	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7054	Approved
0.7248	Intermediate Similarity	NPD6190	Approved
0.7239	Intermediate Similarity	NPD7472	Approved
0.723	Intermediate Similarity	NPD1243	Approved
0.7219	Intermediate Similarity	NPD2533	Approved
0.7219	Intermediate Similarity	NPD2532	Approved
0.7219	Intermediate Similarity	NPD2534	Approved
0.7203	Intermediate Similarity	NPD520	Approved
0.72	Intermediate Similarity	NPD1242	Phase 1
0.7195	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3748	Approved
0.7188	Intermediate Similarity	NPD6232	Discontinued
0.7181	Intermediate Similarity	NPD4628	Phase 3
0.7178	Intermediate Similarity	NPD7286	Phase 2
0.7174	Intermediate Similarity	NPD9717	Approved
0.717	Intermediate Similarity	NPD5494	Approved
0.716	Intermediate Similarity	NPD7473	Discontinued
0.7152	Intermediate Similarity	NPD6559	Discontinued
0.7133	Intermediate Similarity	NPD2313	Discontinued
0.7133	Intermediate Similarity	NPD2309	Approved
0.7133	Intermediate Similarity	NPD3764	Approved
0.7125	Intermediate Similarity	NPD1247	Approved
0.7113	Intermediate Similarity	NPD6832	Phase 2
0.7107	Intermediate Similarity	NPD919	Approved
0.7092	Intermediate Similarity	NPD2798	Approved
0.7091	Intermediate Similarity	NPD5953	Discontinued
0.7086	Intermediate Similarity	NPD3300	Phase 2
0.7075	Intermediate Similarity	NPD2799	Discontinued
0.7067	Intermediate Similarity	NPD3400	Discontinued
0.7059	Intermediate Similarity	NPD1548	Phase 1
0.705	Intermediate Similarity	NPD3972	Approved
0.7006	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2654	Approved
0.6993	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1610	Phase 2
0.697	Remote Similarity	NPD5844	Phase 1
0.6959	Remote Similarity	NPD7033	Discontinued
0.6933	Remote Similarity	NPD3926	Phase 2
0.6918	Remote Similarity	NPD1613	Approved
0.6918	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3751	Discontinued
0.688	Remote Similarity	NPD2860	Approved
0.688	Remote Similarity	NPD2859	Approved
0.6879	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD422	Phase 1
0.6855	Remote Similarity	NPD1465	Phase 2
0.6853	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1019	Discontinued
0.6846	Remote Similarity	NPD5048	Discontinued
0.6842	Remote Similarity	NPD8150	Discontinued
0.6828	Remote Similarity	NPD3027	Phase 3
0.6815	Remote Similarity	NPD1241	Discontinued
0.6815	Remote Similarity	NPD3226	Approved
0.68	Remote Similarity	NPD4360	Phase 2
0.68	Remote Similarity	NPD2933	Approved
0.68	Remote Similarity	NPD2934	Approved
0.68	Remote Similarity	NPD4363	Phase 3
0.6795	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3268	Approved
0.6781	Remote Similarity	NPD6798	Discontinued
0.6772	Remote Similarity	NPD9495	Approved
0.6767	Remote Similarity	NPD4750	Phase 3
0.6766	Remote Similarity	NPD6020	Phase 2
0.6759	Remote Similarity	NPD4908	Phase 1
0.6757	Remote Similarity	NPD447	Suspended
0.6755	Remote Similarity	NPD2346	Discontinued
0.6755	Remote Similarity	NPD1471	Phase 3
0.6733	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4308	Phase 3
0.6732	Remote Similarity	NPD1196	Approved
0.6726	Remote Similarity	NPD1729	Discontinued
0.6719	Remote Similarity	NPD3020	Approved
0.6713	Remote Similarity	NPD1876	Approved
0.671	Remote Similarity	NPD1543	Discontinued
0.6709	Remote Similarity	NPD7458	Discontinued
0.6705	Remote Similarity	NPD6534	Approved
0.6705	Remote Similarity	NPD6535	Approved
0.669	Remote Similarity	NPD1481	Phase 2
0.669	Remote Similarity	NPD9494	Approved
0.6689	Remote Similarity	NPD6100	Approved
0.6689	Remote Similarity	NPD6099	Approved
0.6688	Remote Similarity	NPD2354	Approved
0.6688	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD1195	Approved
0.6667	Remote Similarity	NPD4661	Approved
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3787	Discontinued
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD1296	Phase 2
0.6667	Remote Similarity	NPD4662	Approved
0.6667	Remote Similarity	NPD411	Approved
0.6667	Remote Similarity	NPD5711	Approved
0.6667	Remote Similarity	NPD5710	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6355	Discontinued
0.6644	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1933	Approved
0.6625	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6233	Phase 2
0.662	Remote Similarity	NPD1535	Discovery
0.6611	Remote Similarity	NPD6778	Approved
0.6611	Remote Similarity	NPD6780	Approved
0.6611	Remote Similarity	NPD6782	Approved
0.6611	Remote Similarity	NPD6781	Approved
0.6611	Remote Similarity	NPD6777	Approved
0.6611	Remote Similarity	NPD6776	Approved
0.6611	Remote Similarity	NPD6779	Approved
0.6605	Remote Similarity	NPD2296	Approved
0.6605	Remote Similarity	NPD4288	Approved
0.6604	Remote Similarity	NPD5808	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