NPASS Compound

Structure

NPC471417 OpenBabel07101718182D 23 24 0 0 0 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 2 0 0 0 0 11 22 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.09
Volume:	317.125
LogP:	2.849
LogD:	2.867
LogS:	-3.346
# Rotatable Bonds:	5
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	2.299
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.985
MDCK Permeability:	1.2927089301228989e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.741

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	99.5252914428711%
Volume Distribution (VD):	0.468
Pgp-substrate:	2.144054889678955%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.238
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.509
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.358
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.692
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	13.616
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.723
Rat Oral Acute Toxicity:	0.708
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.949
Carcinogencity:	0.527
Eye Corrosion:	0.007
Eye Irritation:	0.949
Respiratory Toxicity:	0.741

Download Data

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

Natural Product: NPC471417

Natural Product ID:	NPC471417
*Common Name:**	2',3,4-Trihydroxy-4',6'-Dimethoxychalcone
IUPAC Name:	(E)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	OLHMLJHXCUWPOE-GQCTYLIASA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-22-11-8-15(21)17(16(9-11)23-2)13(19)6-4-10-3-5-12(18)14(20)7-10/h3-9,18,20-21H,1-2H3/b6-4+
SMILES:	COc1cc(O)c(c(c1)OC)C(=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL244042
PubChem CID:	44428614
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
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11830162]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12809361]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	root	n.a.	n.a.	PMID[25597012]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26193	Piper methysticum	Species	Piperaceae	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	1
Others	1

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	<	20.0	%	PMID[530507]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	31600.0	nM	PMID[530508]

☑ 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 NPC471417 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	385
0.1-0.2	1703
0.2-0.3	4787
0.3-0.4	11422
0.4-0.5	6014
0.5-0.6	3602
0.6-0.7	4962
0.7-0.8	5993
0.8-0.85	2375
0.85-0.9	1213
0.9-0.95	221
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC284556
0.9926	High Similarity	NPC301178
0.971	High Similarity	NPC287722
0.971	High Similarity	NPC254659
0.971	High Similarity	NPC119663
0.964	High Similarity	NPC142165
0.9577	High Similarity	NPC102003
0.9577	High Similarity	NPC171916
0.9577	High Similarity	NPC92722
0.9577	High Similarity	NPC38545
0.9565	High Similarity	NPC110419
0.9559	High Similarity	NPC472364
0.9559	High Similarity	NPC473391
0.951	High Similarity	NPC85131
0.951	High Similarity	NPC472279
0.9507	High Similarity	NPC166036
0.9507	High Similarity	NPC203077
0.9507	High Similarity	NPC80710
0.9507	High Similarity	NPC203747
0.9507	High Similarity	NPC131451
0.9507	High Similarity	NPC139364
0.9507	High Similarity	NPC254702
0.9507	High Similarity	NPC15329
0.9507	High Similarity	NPC194653
0.9507	High Similarity	NPC238279
0.95	High Similarity	NPC242893
0.95	High Similarity	NPC38065
0.95	High Similarity	NPC105213
0.95	High Similarity	NPC207732
0.9496	High Similarity	NPC312256
0.9444	High Similarity	NPC256406
0.9441	High Similarity	NPC142876
0.9441	High Similarity	NPC40290
0.9441	High Similarity	NPC69430
0.9441	High Similarity	NPC264289
0.9441	High Similarity	NPC195763
0.9441	High Similarity	NPC200060
0.9441	High Similarity	NPC264550
0.9441	High Similarity	NPC333691
0.9441	High Similarity	NPC139293
0.9437	High Similarity	NPC108406
0.9437	High Similarity	NPC95864
0.9437	High Similarity	NPC93034
0.9437	High Similarity	NPC119660
0.9433	High Similarity	NPC157133
0.9379	High Similarity	NPC60972
0.9379	High Similarity	NPC324233
0.9379	High Similarity	NPC477231
0.9379	High Similarity	NPC39732
0.9379	High Similarity	NPC323626
0.9379	High Similarity	NPC257648
0.9375	High Similarity	NPC10467
0.9371	High Similarity	NPC287395
0.9371	High Similarity	NPC183655
0.9366	High Similarity	NPC165389
0.9366	High Similarity	NPC12377
0.9353	High Similarity	NPC50823
0.9348	High Similarity	NPC44573
0.9338	High Similarity	NPC56031
0.9338	High Similarity	NPC188646
0.9338	High Similarity	NPC192304
0.9338	High Similarity	NPC139813
0.9338	High Similarity	NPC175098
0.9338	High Similarity	NPC472365
0.9338	High Similarity	NPC242294
0.9338	High Similarity	NPC312318
0.9338	High Similarity	NPC263670
0.9338	High Similarity	NPC337373
0.9315	High Similarity	NPC124714
0.931	High Similarity	NPC260895
0.931	High Similarity	NPC154345
0.931	High Similarity	NPC31363
0.9306	High Similarity	NPC223579
0.9306	High Similarity	NPC105512
0.9306	High Similarity	NPC287101
0.9306	High Similarity	NPC183950
0.9306	High Similarity	NPC48479
0.9306	High Similarity	NPC270465
0.9306	High Similarity	NPC137062
0.9306	High Similarity	NPC52005
0.9306	High Similarity	NPC87125
0.9306	High Similarity	NPC177298
0.9301	High Similarity	NPC188074
0.9301	High Similarity	NPC125449
0.9296	High Similarity	NPC70136
0.927	High Similarity	NPC286336
0.9265	High Similarity	NPC257756
0.9265	High Similarity	NPC212631
0.9265	High Similarity	NPC129132
0.9265	High Similarity	NPC205468
0.9265	High Similarity	NPC87231
0.9252	High Similarity	NPC57674
0.9252	High Similarity	NPC20830
0.9252	High Similarity	NPC234255
0.9252	High Similarity	NPC117992
0.9252	High Similarity	NPC168247
0.9252	High Similarity	NPC256612
0.9252	High Similarity	NPC152951
0.9252	High Similarity	NPC230149
0.9247	High Similarity	NPC304954
0.9247	High Similarity	NPC100263
0.9247	High Similarity	NPC209487
0.9247	High Similarity	NPC35763
0.9247	High Similarity	NPC269451
0.9247	High Similarity	NPC181209
0.9247	High Similarity	NPC216769
0.9247	High Similarity	NPC245382
0.9247	High Similarity	NPC121522
0.9247	High Similarity	NPC131266
0.9247	High Similarity	NPC55205
0.9247	High Similarity	NPC472912
0.9247	High Similarity	NPC100971
0.9247	High Similarity	NPC291802
0.9241	High Similarity	NPC29231
0.9241	High Similarity	NPC286342
0.9241	High Similarity	NPC88804
0.9241	High Similarity	NPC188871
0.9241	High Similarity	NPC149127
0.9241	High Similarity	NPC3825
0.9241	High Similarity	NPC184136
0.9236	High Similarity	NPC119059
0.9236	High Similarity	NPC120464
0.9236	High Similarity	NPC474903
0.9236	High Similarity	NPC195202
0.9236	High Similarity	NPC3036
0.9236	High Similarity	NPC218490
0.9225	High Similarity	NPC279121
0.922	High Similarity	NPC49108
0.9214	High Similarity	NPC109232
0.9197	High Similarity	NPC159623
0.9197	High Similarity	NPC82225
0.9197	High Similarity	NPC294593
0.9197	High Similarity	NPC204960
0.9197	High Similarity	NPC20560
0.9197	High Similarity	NPC18877
0.9197	High Similarity	NPC144051
0.9197	High Similarity	NPC28753
0.9191	High Similarity	NPC308037
0.9191	High Similarity	NPC262359
0.9191	High Similarity	NPC64359
0.9189	High Similarity	NPC282307
0.9189	High Similarity	NPC265511
0.9189	High Similarity	NPC170026
0.9189	High Similarity	NPC472455
0.9189	High Similarity	NPC472916
0.9184	High Similarity	NPC227337
0.9184	High Similarity	NPC93552
0.9184	High Similarity	NPC189130
0.9184	High Similarity	NPC69394
0.9184	High Similarity	NPC213896
0.9184	High Similarity	NPC70433
0.9184	High Similarity	NPC273462
0.9184	High Similarity	NPC270620
0.9184	High Similarity	NPC236223
0.9184	High Similarity	NPC231018
0.9184	High Similarity	NPC47781
0.9184	High Similarity	NPC49402
0.9184	High Similarity	NPC255350
0.9184	High Similarity	NPC179126
0.9184	High Similarity	NPC22519
0.9184	High Similarity	NPC18727
0.9184	High Similarity	NPC469550
0.9184	High Similarity	NPC176775
0.9184	High Similarity	NPC33051
0.9184	High Similarity	NPC250557
0.9184	High Similarity	NPC192083
0.9184	High Similarity	NPC78326
0.9184	High Similarity	NPC274327
0.9184	High Similarity	NPC183878
0.9184	High Similarity	NPC160951
0.9184	High Similarity	NPC145379
0.9178	High Similarity	NPC54394
0.9178	High Similarity	NPC252933
0.9178	High Similarity	NPC45291
0.9178	High Similarity	NPC19980
0.9178	High Similarity	NPC200740
0.9178	High Similarity	NPC308451
0.9178	High Similarity	NPC125062
0.9178	High Similarity	NPC262623
0.9172	High Similarity	NPC1612
0.9172	High Similarity	NPC183959
0.9167	High Similarity	NPC86847
0.9167	High Similarity	NPC33265
0.9167	High Similarity	NPC168803
0.9167	High Similarity	NPC62536
0.9167	High Similarity	NPC51443
0.9167	High Similarity	NPC12200
0.9167	High Similarity	NPC74881
0.9167	High Similarity	NPC140840
0.9155	High Similarity	NPC175013
0.9143	High Similarity	NPC21350
0.9137	High Similarity	NPC66349
0.9137	High Similarity	NPC477242
0.9137	High Similarity	NPC477244
0.9137	High Similarity	NPC98115
0.9137	High Similarity	NPC150399
0.9137	High Similarity	NPC1486
0.9137	High Similarity	NPC249606
0.9137	High Similarity	NPC213603
0.9137	High Similarity	NPC41461

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 NPC471417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	977
0.2-0.3	1667
0.3-0.4	2707
0.4-0.5	1759
0.5-0.6	1070
0.6-0.7	435
0.7-0.8	136
0.8-0.85	25
0.85-0.9	14
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9225	High Similarity	NPD1511	Approved
0.9189	High Similarity	NPD3882	Suspended
0.9184	High Similarity	NPD2393	Clinical (unspecified phase)
0.9184	High Similarity	NPD2801	Approved
0.9116	High Similarity	NPD1934	Approved
0.9097	High Similarity	NPD1512	Approved
0.9051	High Similarity	NPD1240	Approved
0.8929	High Similarity	NPD1510	Phase 2
0.8921	High Similarity	NPD1607	Approved
0.8913	High Similarity	NPD943	Approved
0.8654	High Similarity	NPD6168	Clinical (unspecified phase)
0.8654	High Similarity	NPD6167	Clinical (unspecified phase)
0.8654	High Similarity	NPD6166	Phase 2
0.8639	High Similarity	NPD4378	Clinical (unspecified phase)
0.8618	High Similarity	NPD3817	Phase 2
0.8611	High Similarity	NPD1549	Phase 2
0.86	High Similarity	NPD4380	Phase 2
0.8571	High Similarity	NPD6799	Approved
0.8544	High Similarity	NPD3818	Discontinued
0.8542	High Similarity	NPD1552	Clinical (unspecified phase)
0.8542	High Similarity	NPD1550	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD7054	Approved
0.8483	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD2796	Approved
0.8442	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7472	Approved
0.8438	Intermediate Similarity	NPD7074	Phase 3
0.8408	Intermediate Similarity	NPD6232	Discontinued
0.8389	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD7075	Discontinued
0.8385	Intermediate Similarity	NPD6797	Phase 2
0.8365	Intermediate Similarity	NPD7473	Discontinued
0.8345	Intermediate Similarity	NPD2935	Discontinued
0.8333	Intermediate Similarity	NPD7251	Discontinued
0.8322	Intermediate Similarity	NPD230	Phase 1
0.8312	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD7819	Suspended
0.8276	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6599	Discontinued
0.8182	Intermediate Similarity	NPD7411	Suspended
0.8171	Intermediate Similarity	NPD7808	Phase 3
0.8171	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5494	Approved
0.8158	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD6801	Discontinued
0.8129	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1551	Phase 2
0.8042	Intermediate Similarity	NPD3027	Phase 3
0.8028	Intermediate Similarity	NPD9494	Approved
0.8014	Intermediate Similarity	NPD6651	Approved
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD3750	Approved
0.7986	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1465	Phase 2
0.7939	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD5403	Approved
0.7911	Intermediate Similarity	NPD5402	Approved
0.7908	Intermediate Similarity	NPD2532	Approved
0.7908	Intermediate Similarity	NPD2534	Approved
0.7908	Intermediate Similarity	NPD2533	Approved
0.7905	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6959	Discontinued
0.7875	Intermediate Similarity	NPD919	Approved
0.7862	Intermediate Similarity	NPD7768	Phase 2
0.7853	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD447	Suspended
0.7818	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5844	Phase 1
0.7815	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2800	Approved
0.7812	Intermediate Similarity	NPD3749	Approved
0.7801	Intermediate Similarity	NPD9269	Phase 2
0.78	Intermediate Similarity	NPD2344	Approved
0.7792	Intermediate Similarity	NPD5401	Approved
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD1247	Approved
0.7778	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD4628	Phase 3
0.7762	Intermediate Similarity	NPD1203	Approved
0.7755	Intermediate Similarity	NPD1613	Approved
0.7755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD2798	Approved
0.7697	Intermediate Similarity	NPD1243	Approved
0.7697	Intermediate Similarity	NPD2654	Approved
0.7667	Intermediate Similarity	NPD3748	Approved
0.7667	Intermediate Similarity	NPD2799	Discontinued
0.7626	Intermediate Similarity	NPD5536	Phase 2
0.7619	Intermediate Similarity	NPD5953	Discontinued
0.7616	Intermediate Similarity	NPD6099	Approved
0.7616	Intermediate Similarity	NPD6100	Approved
0.7613	Intermediate Similarity	NPD7390	Discontinued
0.7603	Intermediate Similarity	NPD6832	Phase 2
0.7597	Intermediate Similarity	NPD2309	Approved
0.7597	Intermediate Similarity	NPD6190	Approved
0.7584	Intermediate Similarity	NPD1933	Approved
0.758	Intermediate Similarity	NPD920	Approved
0.7554	Intermediate Similarity	NPD9493	Approved
0.7552	Intermediate Similarity	NPD3972	Approved
0.7552	Intermediate Similarity	NPD9717	Approved
0.7548	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3018	Phase 2
0.7518	Intermediate Similarity	NPD9268	Approved
0.75	Intermediate Similarity	NPD4357	Discontinued
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD3226	Approved
0.7471	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7199	Phase 2
0.7452	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD9545	Approved
0.7439	Intermediate Similarity	NPD6234	Discontinued
0.7427	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1470	Approved
0.7389	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD411	Approved
0.7383	Intermediate Similarity	NPD2313	Discontinued
0.7379	Intermediate Similarity	NPD2983	Phase 2
0.7379	Intermediate Similarity	NPD2982	Phase 2
0.7365	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4908	Phase 1
0.7365	Intermediate Similarity	NPD5242	Approved
0.7361	Intermediate Similarity	NPD422	Phase 1
0.7361	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1201	Approved
0.7346	Intermediate Similarity	NPD37	Approved
0.7342	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2346	Discontinued
0.7337	Intermediate Similarity	NPD3751	Discontinued
0.7324	Intermediate Similarity	NPD1548	Phase 1
0.7319	Intermediate Similarity	NPD228	Approved
0.7312	Intermediate Similarity	NPD1653	Approved
0.731	Intermediate Similarity	NPD2981	Phase 2
0.731	Intermediate Similarity	NPD1608	Approved
0.7305	Intermediate Similarity	NPD5710	Approved
0.7305	Intermediate Similarity	NPD5711	Approved
0.7299	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6386	Approved
0.7284	Intermediate Similarity	NPD6385	Approved
0.7273	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD5404	Approved
0.7273	Intermediate Similarity	NPD5405	Approved
0.7273	Intermediate Similarity	NPD5408	Approved
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7685	Pre-registration
0.7267	Intermediate Similarity	NPD3268	Approved
0.7256	Intermediate Similarity	NPD5353	Approved
0.7241	Intermediate Similarity	NPD1610	Phase 2
0.7212	Intermediate Similarity	NPD4966	Approved
0.7212	Intermediate Similarity	NPD4965	Approved
0.7212	Intermediate Similarity	NPD4967	Phase 2
0.7211	Intermediate Similarity	NPD1876	Approved
0.7208	Intermediate Similarity	NPD7033	Discontinued
0.7208	Intermediate Similarity	NPD4308	Phase 3
0.7202	Intermediate Similarity	NPD3787	Discontinued
0.7183	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2797	Approved
0.7162	Intermediate Similarity	NPD1164	Approved
0.716	Intermediate Similarity	NPD3455	Phase 2
0.7152	Intermediate Similarity	NPD3764	Approved
0.7135	Intermediate Similarity	NPD7228	Approved
0.7127	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7266	Discontinued
0.7103	Intermediate Similarity	NPD17	Approved
0.7095	Intermediate Similarity	NPD3225	Approved
0.7092	Intermediate Similarity	NPD5283	Phase 1
0.7092	Intermediate Similarity	NPD1241	Discontinued
0.7089	Intermediate Similarity	NPD7003	Approved
0.7089	Intermediate Similarity	NPD8166	Discontinued
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.7066	Intermediate Similarity	NPD6971	Discontinued
0.7055	Intermediate Similarity	NPD824	Approved
0.7052	Intermediate Similarity	NPD1729	Discontinued
0.705	Intermediate Similarity	NPD3021	Approved
0.705	Intermediate Similarity	NPD3022	Approved
0.7048	Intermediate Similarity	NPD2296	Approved
0.7048	Intermediate Similarity	NPD4288	Approved
0.7044	Intermediate Similarity	NPD2354	Approved
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7034	Intermediate Similarity	NPD1651	Approved
0.703	Intermediate Similarity	NPD6844	Discontinued
0.7027	Intermediate Similarity	NPD4749	Approved
0.7019	Intermediate Similarity	NPD4662	Approved
0.7019	Intermediate Similarity	NPD4661	Approved
0.7018	Intermediate Similarity	NPD2403	Approved
0.7017	Intermediate Similarity	NPD4360	Phase 2
0.7017	Intermediate Similarity	NPD4363	Phase 3
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7011	Intermediate Similarity	NPD6778	Approved
0.7011	Intermediate Similarity	NPD6776	Approved
0.7011	Intermediate Similarity	NPD6782	Approved
0.7011	Intermediate Similarity	NPD6780	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data