NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	267.589
LogP:	2.373
LogD:	2.436
LogS:	-2.839
# Rotatable Bonds:	4
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	1.97
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:	-4.689
MDCK Permeability:	1.2481197700253688e-05
Pgp-inhibitor:	0.05
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	86.22311401367188%
Volume Distribution (VD):	0.565
Pgp-substrate:	10.153499603271484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.903
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.821
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.702
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.828
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	15.294
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.333
Rat Oral Acute Toxicity:	0.759
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.919
Carcinogencity:	0.576
Eye Corrosion:	0.041
Eye Irritation:	0.955
Respiratory Toxicity:	0.047

Download Data

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

Natural Product: NPC159525

Natural Product ID:	NPC159525
*Common Name:**	2,4,4'-Trihydroxydihydrochalcone
IUPAC Name:	3-(2,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)propan-1-one
Synonyms:	2,4,4'-Trihydroxydihydrochalcone
Standard InCHIKey:	IVBQZFJZIGYXMK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O4/c16-12-5-1-10(2-6-12)14(18)8-4-11-3-7-13(17)9-15(11)19/h1-3,5-7,9,16-17,19H,4,8H2
SMILES:	c1cc(ccc1C(=O)CCc1ccc(cc1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253564
PubChem CID:	10801179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003475] Retro-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
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12016928]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	stems	Ningming County, Guangxi autonomous region, China	2006-Jan	PMID[17883259]
NPO20812	Soymida febrifuga	Species	Meliaceae	Eukaryota	n.a.	Myanmar	n.a.	PMID[19689125]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21661731]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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
IC50	5
MIC	1
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[490273]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[490273]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[490273]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[490273]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	248100.0	nM	PMID[490272]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[490273]

☑ 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 NPC159525 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	371
0.1-0.2	1754
0.2-0.3	4543
0.3-0.4	12521
0.4-0.5	5842
0.5-0.6	5421
0.6-0.7	7257
0.7-0.8	4222
0.8-0.85	539
0.85-0.9	168
0.9-0.95	44
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9911	High Similarity	NPC158222
0.9739	High Similarity	NPC32032
0.9739	High Similarity	NPC133909
0.9652	High Similarity	NPC143427
0.9652	High Similarity	NPC224273
0.9652	High Similarity	NPC73532
0.9652	High Similarity	NPC242895
0.9652	High Similarity	NPC19174
0.9652	High Similarity	NPC115159
0.9652	High Similarity	NPC45438
0.9652	High Similarity	NPC267552
0.9652	High Similarity	NPC156139
0.9565	High Similarity	NPC248363
0.9565	High Similarity	NPC297186
0.9412	High Similarity	NPC8745
0.9407	High Similarity	NPC13238
0.9333	High Similarity	NPC266689
0.9333	High Similarity	NPC30501
0.9333	High Similarity	NPC100067
0.9333	High Similarity	NPC169250
0.9333	High Similarity	NPC103356
0.9333	High Similarity	NPC23126
0.9333	High Similarity	NPC98254
0.9333	High Similarity	NPC162612
0.9333	High Similarity	NPC190043
0.9333	High Similarity	NPC72158
0.9333	High Similarity	NPC105157
0.9328	High Similarity	NPC10926
0.9316	High Similarity	NPC196976
0.9256	High Similarity	NPC221777
0.9256	High Similarity	NPC21305
0.9256	High Similarity	NPC473017
0.925	High Similarity	NPC267846
0.925	High Similarity	NPC62952
0.9224	High Similarity	NPC161617
0.918	High Similarity	NPC120488
0.918	High Similarity	NPC102829
0.918	High Similarity	NPC474998
0.9174	High Similarity	NPC116513
0.9145	High Similarity	NPC294037
0.9138	High Similarity	NPC40649
0.9138	High Similarity	NPC209486
0.9076	High Similarity	NPC309765
0.9068	High Similarity	NPC149246
0.9068	High Similarity	NPC146642
0.906	High Similarity	NPC188814
0.906	High Similarity	NPC195262
0.9032	High Similarity	NPC475042
0.9024	High Similarity	NPC476119
0.9016	High Similarity	NPC107672
0.8992	High Similarity	NPC215392
0.8992	High Similarity	NPC303737
0.896	High Similarity	NPC164236
0.896	High Similarity	NPC135801
0.896	High Similarity	NPC112192
0.896	High Similarity	NPC189106
0.896	High Similarity	NPC309717
0.896	High Similarity	NPC66384
0.896	High Similarity	NPC128348
0.8952	High Similarity	NPC247779
0.8952	High Similarity	NPC233056
0.8952	High Similarity	NPC26697
0.8929	High Similarity	NPC17525
0.8917	High Similarity	NPC91105
0.8889	High Similarity	NPC40524
0.8889	High Similarity	NPC213485
0.8889	High Similarity	NPC139074
0.888	High Similarity	NPC469526
0.888	High Similarity	NPC34070
0.8871	High Similarity	NPC92624
0.8871	High Similarity	NPC109123
0.8843	High Similarity	NPC472029
0.8843	High Similarity	NPC65761
0.8839	High Similarity	NPC141523
0.8833	High Similarity	NPC226275
0.8819	High Similarity	NPC282780
0.8819	High Similarity	NPC166480
0.8819	High Similarity	NPC27643
0.8819	High Similarity	NPC44437
0.8814	High Similarity	NPC241089
0.881	High Similarity	NPC313618
0.881	High Similarity	NPC175738
0.881	High Similarity	NPC262359
0.88	High Similarity	NPC259942
0.8793	High Similarity	NPC118288
0.8793	High Similarity	NPC276111
0.8772	High Similarity	NPC116842
0.875	High Similarity	NPC283590
0.875	High Similarity	NPC70859
0.875	High Similarity	NPC286336
0.875	High Similarity	NPC470210
0.875	High Similarity	NPC61153
0.875	High Similarity	NPC130899
0.874	High Similarity	NPC212631
0.874	High Similarity	NPC257756
0.874	High Similarity	NPC129132
0.874	High Similarity	NPC205468
0.874	High Similarity	NPC87231
0.873	High Similarity	NPC275504
0.8729	High Similarity	NPC121259
0.8718	High Similarity	NPC322197
0.8707	High Similarity	NPC242136
0.8699	High Similarity	NPC475733
0.8696	High Similarity	NPC268388
0.8684	High Similarity	NPC95172
0.8682	High Similarity	NPC194764
0.8682	High Similarity	NPC264112
0.8682	High Similarity	NPC65005
0.8682	High Similarity	NPC131039
0.8682	High Similarity	NPC234560
0.8682	High Similarity	NPC239495
0.8682	High Similarity	NPC9985
0.8682	High Similarity	NPC39426
0.8673	High Similarity	NPC226699
0.8672	High Similarity	NPC294593
0.8672	High Similarity	NPC159623
0.8672	High Similarity	NPC337373
0.8672	High Similarity	NPC312318
0.8672	High Similarity	NPC82225
0.8672	High Similarity	NPC204960
0.8672	High Similarity	NPC175098
0.8672	High Similarity	NPC20560
0.8672	High Similarity	NPC188646
0.8672	High Similarity	NPC263670
0.8672	High Similarity	NPC144051
0.8672	High Similarity	NPC18877
0.8672	High Similarity	NPC28753
0.8672	High Similarity	NPC242294
0.8672	High Similarity	NPC472365
0.8672	High Similarity	NPC56031
0.8672	High Similarity	NPC139813
0.8672	High Similarity	NPC192304
0.8661	High Similarity	NPC64359
0.8661	High Similarity	NPC308037
0.8655	High Similarity	NPC283844
0.8651	High Similarity	NPC244441
0.8615	High Similarity	NPC44960
0.8615	High Similarity	NPC168105
0.8615	High Similarity	NPC87545
0.8615	High Similarity	NPC474110
0.8615	High Similarity	NPC150399
0.8615	High Similarity	NPC186838
0.8615	High Similarity	NPC41461
0.8615	High Similarity	NPC25287
0.8615	High Similarity	NPC477242
0.8615	High Similarity	NPC477244
0.8615	High Similarity	NPC53206
0.8615	High Similarity	NPC213603
0.8615	High Similarity	NPC290030
0.8615	High Similarity	NPC98115
0.8615	High Similarity	NPC249606
0.8615	High Similarity	NPC274109
0.8615	High Similarity	NPC12165
0.8615	High Similarity	NPC24394
0.8615	High Similarity	NPC53414
0.8615	High Similarity	NPC66349
0.8615	High Similarity	NPC477243
0.8615	High Similarity	NPC235428
0.8615	High Similarity	NPC1486
0.8605	High Similarity	NPC172262
0.8595	High Similarity	NPC229649
0.8594	High Similarity	NPC267205
0.8584	High Similarity	NPC6984
0.8571	High Similarity	NPC230349
0.855	High Similarity	NPC294409
0.855	High Similarity	NPC162680
0.855	High Similarity	NPC212767
0.855	High Similarity	NPC116632
0.855	High Similarity	NPC472419
0.855	High Similarity	NPC303644
0.855	High Similarity	NPC317119
0.855	High Similarity	NPC209560
0.855	High Similarity	NPC7013
0.855	High Similarity	NPC181124
0.855	High Similarity	NPC23870
0.855	High Similarity	NPC153979
0.855	High Similarity	NPC175552
0.855	High Similarity	NPC20210
0.8548	High Similarity	NPC477454
0.8538	High Similarity	NPC13575
0.8538	High Similarity	NPC254847
0.8538	High Similarity	NPC156092
0.8527	High Similarity	NPC274121
0.8527	High Similarity	NPC57601
0.8527	High Similarity	NPC50898
0.8527	High Similarity	NPC213216
0.8527	High Similarity	NPC78540
0.8527	High Similarity	NPC475088
0.8522	High Similarity	NPC88141
0.8516	High Similarity	NPC475008
0.8516	High Similarity	NPC186097
0.8516	High Similarity	NPC475009
0.8504	High Similarity	NPC185497
0.8504	High Similarity	NPC147757
0.85	High Similarity	NPC249435
0.85	High Similarity	NPC273282
0.85	High Similarity	NPC474890
0.85	High Similarity	NPC161943
0.8492	Intermediate Similarity	NPC95537
0.8492	Intermediate Similarity	NPC80694

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 NPC159525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	970
0.2-0.3	1389
0.3-0.4	2868
0.4-0.5	1966
0.5-0.6	1134
0.6-0.7	350
0.7-0.8	93
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.896	High Similarity	NPD943	Approved
0.881	High Similarity	NPD1240	Approved
0.8682	High Similarity	NPD1510	Phase 2
0.8672	High Similarity	NPD1607	Approved
0.8538	High Similarity	NPD1509	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD1549	Phase 2
0.8409	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8348	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD1470	Approved
0.811	Intermediate Similarity	NPD1164	Approved
0.8088	Intermediate Similarity	NPD3750	Approved
0.808	Intermediate Similarity	NPD1201	Approved
0.807	Intermediate Similarity	NPD846	Approved
0.807	Intermediate Similarity	NPD940	Approved
0.8016	Intermediate Similarity	NPD9269	Phase 2
0.7986	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD9268	Approved
0.7966	Intermediate Similarity	NPD74	Approved
0.7966	Intermediate Similarity	NPD9266	Approved
0.7914	Intermediate Similarity	NPD7390	Discontinued
0.7914	Intermediate Similarity	NPD1511	Approved
0.7903	Intermediate Similarity	NPD9545	Approved
0.7881	Intermediate Similarity	NPD9264	Approved
0.7881	Intermediate Similarity	NPD9263	Approved
0.7881	Intermediate Similarity	NPD9267	Approved
0.7832	Intermediate Similarity	NPD4380	Phase 2
0.7826	Intermediate Similarity	NPD1242	Phase 1
0.7801	Intermediate Similarity	NPD1512	Approved
0.7794	Intermediate Similarity	NPD2796	Approved
0.7742	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD9493	Approved
0.7721	Intermediate Similarity	NPD3748	Approved
0.7692	Intermediate Similarity	NPD1203	Approved
0.7681	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3764	Approved
0.7669	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD5406	Approved
0.7664	Intermediate Similarity	NPD5404	Approved
0.7664	Intermediate Similarity	NPD1551	Phase 2
0.7664	Intermediate Similarity	NPD5408	Approved
0.7664	Intermediate Similarity	NPD5405	Approved
0.766	Intermediate Similarity	NPD6799	Approved
0.7655	Intermediate Similarity	NPD7411	Suspended
0.763	Intermediate Similarity	NPD230	Phase 1
0.7627	Intermediate Similarity	NPD1237	Approved
0.7626	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1934	Approved
0.7581	Intermediate Similarity	NPD9281	Approved
0.7551	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD9261	Approved
0.7536	Intermediate Similarity	NPD2935	Discontinued
0.7517	Intermediate Similarity	NPD3749	Approved
0.7517	Intermediate Similarity	NPD7075	Discontinued
0.7517	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2344	Approved
0.7478	Intermediate Similarity	NPD2859	Approved
0.7478	Intermediate Similarity	NPD2860	Approved
0.7466	Intermediate Similarity	NPD6599	Discontinued
0.7462	Intermediate Similarity	NPD3972	Approved
0.745	Intermediate Similarity	NPD3882	Suspended
0.7447	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD6651	Approved
0.7432	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2801	Approved
0.7432	Intermediate Similarity	NPD7819	Suspended
0.7391	Intermediate Similarity	NPD2933	Approved
0.7391	Intermediate Similarity	NPD2934	Approved
0.7385	Intermediate Similarity	NPD422	Phase 1
0.7376	Intermediate Similarity	NPD1243	Approved
0.7376	Intermediate Similarity	NPD2800	Approved
0.7365	Intermediate Similarity	NPD6801	Discontinued
0.7344	Intermediate Similarity	NPD1548	Phase 1
0.7333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD9717	Approved
0.7317	Intermediate Similarity	NPD4750	Phase 3
0.7288	Intermediate Similarity	NPD3020	Approved
0.7279	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD2309	Approved
0.7252	Intermediate Similarity	NPD1610	Phase 2
0.7252	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2798	Approved
0.7226	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7768	Phase 2
0.7214	Intermediate Similarity	NPD4308	Phase 3
0.7214	Intermediate Similarity	NPD2799	Discontinued
0.7203	Intermediate Similarity	NPD4628	Phase 3
0.72	Intermediate Similarity	NPD1465	Phase 2
0.7164	Intermediate Similarity	NPD2797	Approved
0.7163	Intermediate Similarity	NPD6099	Approved
0.7163	Intermediate Similarity	NPD6100	Approved
0.7155	Intermediate Similarity	NPD1202	Approved
0.7153	Intermediate Similarity	NPD1296	Phase 2
0.7153	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3818	Discontinued
0.7123	Intermediate Similarity	NPD5401	Approved
0.7123	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6166	Phase 2
0.7115	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD520	Approved
0.7099	Intermediate Similarity	NPD2932	Approved
0.7099	Intermediate Similarity	NPD3019	Approved
0.7097	Intermediate Similarity	NPD6232	Discontinued
0.709	Intermediate Similarity	NPD3225	Approved
0.709	Intermediate Similarity	NPD1876	Approved
0.7087	Intermediate Similarity	NPD1241	Discontinued
0.7077	Intermediate Similarity	NPD1759	Phase 1
0.707	Intermediate Similarity	NPD7473	Discontinued
0.7068	Intermediate Similarity	NPD1608	Approved
0.7068	Intermediate Similarity	NPD1481	Phase 2
0.7043	Intermediate Similarity	NPD9256	Approved
0.7043	Intermediate Similarity	NPD9258	Approved
0.7039	Intermediate Similarity	NPD4288	Approved
0.7039	Intermediate Similarity	NPD3817	Phase 2
0.7037	Intermediate Similarity	NPD3266	Approved
0.7037	Intermediate Similarity	NPD3267	Approved
0.7032	Intermediate Similarity	NPD6959	Discontinued
0.7014	Intermediate Similarity	NPD2654	Approved
0.7007	Intermediate Similarity	NPD2532	Approved
0.7007	Intermediate Similarity	NPD2533	Approved
0.7007	Intermediate Similarity	NPD2534	Approved
0.7007	Intermediate Similarity	NPD6832	Phase 2
0.7007	Intermediate Similarity	NPD4908	Phase 1
0.7007	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD1758	Phase 1
0.6992	Remote Similarity	NPD1535	Discovery
0.6981	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7286	Phase 2
0.6977	Remote Similarity	NPD256	Approved
0.6977	Remote Similarity	NPD255	Approved
0.6972	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1930	Approved
0.6967	Remote Similarity	NPD1929	Approved
0.6967	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7074	Phase 3
0.6934	Remote Similarity	NPD9494	Approved
0.6934	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7458	Discontinued
0.6929	Remote Similarity	NPD4307	Phase 2
0.6918	Remote Similarity	NPD2354	Approved
0.6918	Remote Similarity	NPD6190	Approved
0.6906	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3022	Approved
0.6905	Remote Similarity	NPD3021	Approved
0.6903	Remote Similarity	NPD111	Approved
0.6894	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD844	Approved
0.6891	Remote Similarity	NPD1809	Phase 2
0.6889	Remote Similarity	NPD1755	Approved
0.6875	Remote Similarity	NPD7054	Approved
0.6875	Remote Similarity	NPD5844	Phase 1
0.6875	Remote Similarity	NPD6020	Phase 2
0.6871	Remote Similarity	NPD3300	Phase 2
0.6864	Remote Similarity	NPD845	Approved
0.6859	Remote Similarity	NPD5494	Approved
0.6849	Remote Similarity	NPD7003	Approved
0.6849	Remote Similarity	NPD1196	Approved
0.6842	Remote Similarity	NPD17	Approved
0.6833	Remote Similarity	NPD288	Approved
0.6832	Remote Similarity	NPD7472	Approved
0.6824	Remote Similarity	NPD1543	Discontinued
0.6821	Remote Similarity	NPD3226	Approved
0.6818	Remote Similarity	NPD5402	Approved
0.6815	Remote Similarity	NPD4878	Approved
0.681	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1613	Approved
0.6803	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD919	Approved
0.6794	Remote Similarity	NPD9568	Approved
0.679	Remote Similarity	NPD6797	Phase 2
0.6786	Remote Similarity	NPD9089	Approved
0.6786	Remote Similarity	NPD411	Approved
0.6781	Remote Similarity	NPD1195	Approved
0.6779	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5951	Approved
0.6769	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD447	Suspended
0.6759	Remote Similarity	NPD2346	Discontinued
0.6759	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2353	Approved
0.6748	Remote Similarity	NPD1932	Approved
0.6748	Remote Similarity	NPD7251	Discontinued
0.6748	Remote Similarity	NPD6559	Discontinued
0.6739	Remote Similarity	NPD6007	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