NPASS Compound

Structure

NPC222905 OpenBabel07101719142D 34 35 0 0 0 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -6.0622 0.5000 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -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 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 -2.5981 0.5000 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 -7.7942 -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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 11 1 0 0 0 0 7 20 2 0 0 0 0 8 12 1 0 0 0 0 8 23 2 0 0 0 0 9 13 2 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 25 2 0 0 0 0 13 25 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 30 1 0 0 0 0 18 30 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 24 28 1 0 0 0 0 25 31 1 0 0 0 0 26 27 2 0 0 0 0 26 29 1 0 0 0 0 27 32 1 0 0 0 0 28 30 1 0 0 0 0 28 33 2 0 0 0 0 29 30 1 0 0 0 0 29 34 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.26
Volume:	516.483
LogP:	6.661
LogD:	4.82
LogS:	-4.462
# Rotatable Bonds:	9
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.252
Synthetic Accessibility Score:	4.029
Fsp3:	0.367
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.674
MDCK Permeability:	2.4236238459707238e-05
Pgp-inhibitor:	0.853
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.622
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	94.42133331298828%
Volume Distribution (VD):	1.822
Pgp-substrate:	4.73115873336792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.342
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.871
CYP2C19-substrate:	0.376
CYP2C9-inhibitor:	0.915
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.545
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	16.939
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.95
Drug-inuced Liver Injury (DILI):	0.156
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.562
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.264
Carcinogencity:	0.611
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC222905

Natural Product ID:	NPC222905
*Common Name:**	Munchiwarin
IUPAC Name:	(6Z)-6-[(E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-enylidene]-2,2,4-tris(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Synonyms:	Munchiwarin
Standard InCHIKey:	HBTGYTAWTFVIRO-QKOOUZAASA-N
Standard InCHI:	InChI=1S/C30H36O4/c1-20(2)7-11-24-19-26(27(32)14-10-23-8-12-25(31)13-9-23)29(34)30(28(24)33,17-15-21(3)4)18-16-22(5)6/h7-10,12-16,19,31-32H,11,17-18H2,1-6H3/b14-10+,27-26-
SMILES:	CC(=CCC1=C/C(=C(C=Cc2ccc(cc2)O)/O)/C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463750
PubChem CID:	6536697
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO25782	Crotalaria trifoliastrum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784166]
NPO25782	Crotalaria trifoliastrum	Species	Fabaceae	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

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	11.0	ug.mL-1	PMID[515918]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	13.0	ug.mL-1	PMID[515918]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	14.0	ug.mL-1	PMID[515918]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	=	9.0	ug.mL-1	PMID[515918]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9.0	ug.mL-1	PMID[515918]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	MIC	=	4340.0	nM	PMID[515919]

☑ 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 NPC222905 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	222
0.1-0.2	1320
0.2-0.3	3549
0.3-0.4	10491
0.4-0.5	9285
0.5-0.6	10011
0.6-0.7	6516
0.7-0.8	1223
0.8-0.85	61
0.85-0.9	17
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9029	High Similarity	NPC472585
0.8972	High Similarity	NPC88141
0.8942	High Similarity	NPC68269
0.8868	High Similarity	NPC95178
0.8868	High Similarity	NPC70843
0.8868	High Similarity	NPC29989
0.8868	High Similarity	NPC69332
0.8692	High Similarity	NPC188677
0.8654	High Similarity	NPC130193
0.8558	High Similarity	NPC260000
0.8558	High Similarity	NPC201967
0.8545	High Similarity	NPC21162
0.8545	High Similarity	NPC116842
0.8529	High Similarity	NPC181709
0.8519	High Similarity	NPC6984
0.8505	High Similarity	NPC120693
0.8505	High Similarity	NPC261573
0.8505	High Similarity	NPC8931
0.8496	Intermediate Similarity	NPC23402
0.8476	Intermediate Similarity	NPC280869
0.8455	Intermediate Similarity	NPC95172
0.844	Intermediate Similarity	NPC226699
0.8421	Intermediate Similarity	NPC325646
0.8421	Intermediate Similarity	NPC28951
0.8411	Intermediate Similarity	NPC135784
0.8407	Intermediate Similarity	NPC285350
0.8364	Intermediate Similarity	NPC17525
0.8319	Intermediate Similarity	NPC242136
0.8319	Intermediate Similarity	NPC174991
0.8304	Intermediate Similarity	NPC470355
0.8273	Intermediate Similarity	NPC228737
0.8261	Intermediate Similarity	NPC19290
0.8261	Intermediate Similarity	NPC61062
0.8261	Intermediate Similarity	NPC299252
0.8261	Intermediate Similarity	NPC277394
0.8252	Intermediate Similarity	NPC270547
0.8235	Intermediate Similarity	NPC98772
0.823	Intermediate Similarity	NPC51698
0.8205	Intermediate Similarity	NPC258366
0.8205	Intermediate Similarity	NPC473974
0.8205	Intermediate Similarity	NPC79933
0.8205	Intermediate Similarity	NPC31296
0.8198	Intermediate Similarity	NPC317305
0.8198	Intermediate Similarity	NPC470039
0.8198	Intermediate Similarity	NPC31274
0.8182	Intermediate Similarity	NPC137416
0.8174	Intermediate Similarity	NPC322197
0.8155	Intermediate Similarity	NPC55561
0.8151	Intermediate Similarity	NPC154696
0.8142	Intermediate Similarity	NPC177576
0.8142	Intermediate Similarity	NPC139946
0.8142	Intermediate Similarity	NPC268388
0.8131	Intermediate Similarity	NPC245561
0.8108	Intermediate Similarity	NPC34715
0.8108	Intermediate Similarity	NPC141523
0.8099	Intermediate Similarity	NPC474766
0.8095	Intermediate Similarity	NPC32977
0.8095	Intermediate Similarity	NPC81010
0.8091	Intermediate Similarity	NPC303141
0.8091	Intermediate Similarity	NPC243677
0.8091	Intermediate Similarity	NPC13495
0.8083	Intermediate Similarity	NPC139171
0.807	Intermediate Similarity	NPC231717
0.807	Intermediate Similarity	NPC286222
0.8067	Intermediate Similarity	NPC32322
0.8067	Intermediate Similarity	NPC259703
0.8065	Intermediate Similarity	NPC25736
0.8058	Intermediate Similarity	NPC280347
0.8058	Intermediate Similarity	NPC177420
0.8056	Intermediate Similarity	NPC52472
0.8053	Intermediate Similarity	NPC252544
0.8053	Intermediate Similarity	NPC321252
0.8053	Intermediate Similarity	NPC208229
0.8039	Intermediate Similarity	NPC184169
0.8036	Intermediate Similarity	NPC224584
0.8019	Intermediate Similarity	NPC286006
0.8019	Intermediate Similarity	NPC26244
0.8	Intermediate Similarity	NPC11824
0.7984	Intermediate Similarity	NPC193203
0.7983	Intermediate Similarity	NPC318552
0.7983	Intermediate Similarity	NPC190501
0.7982	Intermediate Similarity	NPC228609
0.7982	Intermediate Similarity	NPC212718
0.7982	Intermediate Similarity	NPC114682
0.7982	Intermediate Similarity	NPC297657
0.7967	Intermediate Similarity	NPC254492
0.7967	Intermediate Similarity	NPC15837
0.7967	Intermediate Similarity	NPC71610
0.7966	Intermediate Similarity	NPC273282
0.7966	Intermediate Similarity	NPC249435
0.7966	Intermediate Similarity	NPC474890
0.7966	Intermediate Similarity	NPC161943
0.7965	Intermediate Similarity	NPC282855
0.7965	Intermediate Similarity	NPC26013
0.7963	Intermediate Similarity	NPC92730
0.7961	Intermediate Similarity	NPC25493
0.7961	Intermediate Similarity	NPC113460
0.7953	Intermediate Similarity	NPC18982
0.7953	Intermediate Similarity	NPC475627
0.7953	Intermediate Similarity	NPC475457
0.7953	Intermediate Similarity	NPC475346
0.7951	Intermediate Similarity	NPC474803
0.7944	Intermediate Similarity	NPC473388
0.7941	Intermediate Similarity	NPC197783
0.7934	Intermediate Similarity	NPC164947
0.7931	Intermediate Similarity	NPC114918
0.7931	Intermediate Similarity	NPC114144
0.7925	Intermediate Similarity	NPC151715
0.7925	Intermediate Similarity	NPC316301
0.7925	Intermediate Similarity	NPC27323
0.792	Intermediate Similarity	NPC117899
0.7917	Intermediate Similarity	NPC164852
0.7913	Intermediate Similarity	NPC17693
0.7909	Intermediate Similarity	NPC470202
0.7907	Intermediate Similarity	NPC7464
0.7905	Intermediate Similarity	NPC155908
0.7903	Intermediate Similarity	NPC72667
0.7899	Intermediate Similarity	NPC42657
0.7899	Intermediate Similarity	NPC473767
0.7895	Intermediate Similarity	NPC183700
0.789	Intermediate Similarity	NPC253746
0.789	Intermediate Similarity	NPC225506
0.7885	Intermediate Similarity	NPC318325
0.7885	Intermediate Similarity	NPC123273
0.7885	Intermediate Similarity	NPC242240
0.7881	Intermediate Similarity	NPC174087
0.7881	Intermediate Similarity	NPC122117
0.7876	Intermediate Similarity	NPC68260
0.7876	Intermediate Similarity	NPC279887
0.787	Intermediate Similarity	NPC225464
0.787	Intermediate Similarity	NPC476120
0.7864	Intermediate Similarity	NPC23167
0.7845	Intermediate Similarity	NPC28784
0.7845	Intermediate Similarity	NPC296144
0.7843	Intermediate Similarity	NPC175313
0.7843	Intermediate Similarity	NPC248817
0.784	Intermediate Similarity	NPC229894
0.784	Intermediate Similarity	NPC221777
0.7838	Intermediate Similarity	NPC79672
0.7838	Intermediate Similarity	NPC52087
0.7833	Intermediate Similarity	NPC473136
0.7829	Intermediate Similarity	NPC43353
0.7823	Intermediate Similarity	NPC328983
0.7823	Intermediate Similarity	NPC204579
0.7807	Intermediate Similarity	NPC471954
0.7807	Intermediate Similarity	NPC75272
0.7805	Intermediate Similarity	NPC474532
0.7798	Intermediate Similarity	NPC122005
0.7798	Intermediate Similarity	NPC252821
0.7797	Intermediate Similarity	NPC83718
0.7797	Intermediate Similarity	NPC128249
0.7795	Intermediate Similarity	NPC18798
0.7788	Intermediate Similarity	NPC260952
0.7787	Intermediate Similarity	NPC176208
0.7787	Intermediate Similarity	NPC282577
0.7787	Intermediate Similarity	NPC68167
0.7787	Intermediate Similarity	NPC86900
0.7786	Intermediate Similarity	NPC5014
0.7786	Intermediate Similarity	NPC149773
0.7786	Intermediate Similarity	NPC245760
0.7786	Intermediate Similarity	NPC289358
0.7786	Intermediate Similarity	NPC51531
0.7786	Intermediate Similarity	NPC297797
0.7786	Intermediate Similarity	NPC46242
0.7786	Intermediate Similarity	NPC165191
0.7786	Intermediate Similarity	NPC114333
0.7786	Intermediate Similarity	NPC91887
0.7786	Intermediate Similarity	NPC28592
0.7786	Intermediate Similarity	NPC23667
0.7786	Intermediate Similarity	NPC477849
0.7786	Intermediate Similarity	NPC469857
0.7786	Intermediate Similarity	NPC42384
0.7786	Intermediate Similarity	NPC157284
0.7786	Intermediate Similarity	NPC50615
0.7786	Intermediate Similarity	NPC473779
0.7786	Intermediate Similarity	NPC473479
0.7778	Intermediate Similarity	NPC474050
0.7778	Intermediate Similarity	NPC292730
0.7778	Intermediate Similarity	NPC216520
0.7778	Intermediate Similarity	NPC82664
0.7778	Intermediate Similarity	NPC473931
0.7778	Intermediate Similarity	NPC197513
0.7778	Intermediate Similarity	NPC278228
0.7778	Intermediate Similarity	NPC171460
0.7778	Intermediate Similarity	NPC240042
0.7778	Intermediate Similarity	NPC132271
0.7778	Intermediate Similarity	NPC474114
0.7769	Intermediate Similarity	NPC236520
0.7769	Intermediate Similarity	NPC294361
0.7769	Intermediate Similarity	NPC241001
0.7768	Intermediate Similarity	NPC127676
0.7768	Intermediate Similarity	NPC99557
0.7768	Intermediate Similarity	NPC219913
0.7768	Intermediate Similarity	NPC219286
0.776	Intermediate Similarity	NPC78364
0.776	Intermediate Similarity	NPC103356
0.776	Intermediate Similarity	NPC84672
0.776	Intermediate Similarity	NPC116513
0.776	Intermediate Similarity	NPC266689
0.776	Intermediate Similarity	NPC23126

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 NPC222905 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	940
0.2-0.3	1225
0.3-0.4	2751
0.4-0.5	2330
0.5-0.6	1256
0.6-0.7	378
0.7-0.8	50
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8136	Intermediate Similarity	NPD2932	Approved
0.8095	Intermediate Similarity	NPD2934	Approved
0.8095	Intermediate Similarity	NPD2933	Approved
0.8051	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD2859	Approved
0.8019	Intermediate Similarity	NPD2860	Approved
0.7983	Intermediate Similarity	NPD3019	Approved
0.7925	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD3020	Approved
0.7745	Intermediate Similarity	NPD111	Approved
0.7685	Intermediate Similarity	NPD1809	Phase 2
0.7632	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD8166	Discontinued
0.748	Intermediate Similarity	NPD3023	Approved
0.748	Intermediate Similarity	NPD3026	Approved
0.7459	Intermediate Similarity	NPD3025	Approved
0.7459	Intermediate Similarity	NPD3024	Approved
0.7377	Intermediate Similarity	NPD9545	Approved
0.7373	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD3022	Approved
0.735	Intermediate Similarity	NPD3021	Approved
0.7345	Intermediate Similarity	NPD940	Approved
0.7345	Intermediate Similarity	NPD846	Approved
0.7344	Intermediate Similarity	NPD5736	Approved
0.7339	Intermediate Similarity	NPD845	Approved
0.7295	Intermediate Similarity	NPD5536	Phase 2
0.7273	Intermediate Similarity	NPD256	Approved
0.7273	Intermediate Similarity	NPD255	Approved
0.7265	Intermediate Similarity	NPD74	Approved
0.7265	Intermediate Similarity	NPD9266	Approved
0.7257	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3028	Approved
0.7252	Intermediate Similarity	NPD6663	Approved
0.725	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD9493	Approved
0.7209	Intermediate Similarity	NPD4208	Discontinued
0.7207	Intermediate Similarity	NPD844	Approved
0.7188	Intermediate Similarity	NPD1470	Approved
0.7188	Intermediate Similarity	NPD1164	Approved
0.7182	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9263	Approved
0.7179	Intermediate Similarity	NPD9267	Approved
0.7179	Intermediate Similarity	NPD9264	Approved
0.7165	Intermediate Similarity	NPD1755	Approved
0.7143	Intermediate Similarity	NPD1201	Approved
0.7111	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1242	Phase 1
0.7097	Intermediate Similarity	NPD3091	Approved
0.7094	Intermediate Similarity	NPD3134	Approved
0.7073	Intermediate Similarity	NPD9568	Approved
0.7069	Intermediate Similarity	NPD1237	Approved
0.7063	Intermediate Similarity	NPD3847	Discontinued
0.7059	Intermediate Similarity	NPD2935	Discontinued
0.7049	Intermediate Similarity	NPD5951	Approved
0.7045	Intermediate Similarity	NPD3764	Approved
0.7034	Intermediate Similarity	NPD1358	Approved
0.7023	Intermediate Similarity	NPD4207	Discontinued
0.7018	Intermediate Similarity	NPD2066	Phase 3
0.7008	Intermediate Similarity	NPD1535	Discovery
0.6991	Remote Similarity	NPD288	Approved
0.6985	Remote Similarity	NPD2799	Discontinued
0.6984	Remote Similarity	NPD4059	Approved
0.6983	Remote Similarity	NPD6647	Phase 2
0.6978	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1876	Approved
0.6967	Remote Similarity	NPD2228	Approved
0.6967	Remote Similarity	NPD2229	Approved
0.6967	Remote Similarity	NPD2234	Approved
0.6963	Remote Similarity	NPD6651	Approved
0.696	Remote Similarity	NPD1759	Phase 1
0.6953	Remote Similarity	NPD1481	Phase 2
0.694	Remote Similarity	NPD1240	Approved
0.694	Remote Similarity	NPD943	Approved
0.6923	Remote Similarity	NPD2797	Approved
0.6923	Remote Similarity	NPD9610	Approved
0.6923	Remote Similarity	NPD9608	Approved
0.6917	Remote Similarity	NPD4750	Phase 3
0.6917	Remote Similarity	NPD3268	Approved
0.6911	Remote Similarity	NPD9281	Approved
0.6909	Remote Similarity	NPD9256	Approved
0.6909	Remote Similarity	NPD9258	Approved
0.6906	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1651	Approved
0.6885	Remote Similarity	NPD7635	Approved
0.6884	Remote Similarity	NPD2344	Approved
0.688	Remote Similarity	NPD1758	Phase 1
0.6875	Remote Similarity	NPD3092	Approved
0.687	Remote Similarity	NPD2798	Approved
0.6861	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7003	Approved
0.6857	Remote Similarity	NPD4628	Phase 3
0.6855	Remote Similarity	NPD7157	Approved
0.685	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3095	Discontinued
0.685	Remote Similarity	NPD4626	Approved
0.685	Remote Similarity	NPD4589	Approved
0.6842	Remote Similarity	NPD7095	Approved
0.6838	Remote Similarity	NPD1607	Approved
0.6838	Remote Similarity	NPD1929	Approved
0.6838	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9261	Approved
0.6838	Remote Similarity	NPD1930	Approved
0.6828	Remote Similarity	NPD7458	Discontinued
0.6825	Remote Similarity	NPD1894	Discontinued
0.6822	Remote Similarity	NPD9717	Approved
0.6818	Remote Similarity	NPD4212	Discontinued
0.6818	Remote Similarity	NPD9494	Approved
0.6812	Remote Similarity	NPD5408	Approved
0.6812	Remote Similarity	NPD5405	Approved
0.6812	Remote Similarity	NPD5404	Approved
0.6812	Remote Similarity	NPD5406	Approved
0.6794	Remote Similarity	NPD1203	Approved
0.6794	Remote Similarity	NPD3094	Phase 2
0.6791	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2629	Approved
0.6759	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7843	Approved
0.6748	Remote Similarity	NPD5535	Approved
0.6744	Remote Similarity	NPD422	Phase 1
0.6742	Remote Similarity	NPD257	Approved
0.6742	Remote Similarity	NPD258	Approved
0.6741	Remote Similarity	NPD8032	Phase 2
0.6739	Remote Similarity	NPD1510	Phase 2
0.6738	Remote Similarity	NPD3750	Approved
0.6726	Remote Similarity	NPD1202	Approved
0.672	Remote Similarity	NPD6671	Approved
0.6719	Remote Similarity	NPD1751	Approved
0.6718	Remote Similarity	NPD1283	Approved
0.6716	Remote Similarity	NPD3136	Phase 2
0.6696	Remote Similarity	NPD7609	Phase 3
0.6694	Remote Similarity	NPD2684	Approved
0.6693	Remote Similarity	NPD5303	Approved
0.6693	Remote Similarity	NPD7330	Discontinued
0.6693	Remote Similarity	NPD5304	Approved
0.6692	Remote Similarity	NPD9269	Phase 2
0.6691	Remote Similarity	NPD7450	Phase 2
0.669	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD1444	Approved
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD7636	Approved
0.6667	Remote Similarity	NPD1445	Approved
0.6667	Remote Similarity	NPD228	Approved
0.6667	Remote Similarity	NPD9087	Approved
0.6667	Remote Similarity	NPD2800	Approved
0.6642	Remote Similarity	NPD6355	Discontinued
0.6642	Remote Similarity	NPD2614	Approved
0.6642	Remote Similarity	NPD6832	Phase 2
0.6641	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4093	Discontinued
0.6641	Remote Similarity	NPD9268	Approved
0.6641	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.664	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1792	Phase 2
0.6639	Remote Similarity	NPD5909	Discontinued
0.6639	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD9495	Approved
0.6637	Remote Similarity	NPD1088	Approved
0.6637	Remote Similarity	NPD7631	Approved
0.6619	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4062	Phase 3
0.6618	Remote Similarity	NPD6233	Phase 2
0.6615	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD2342	Discontinued
0.6597	Remote Similarity	NPD7390	Discontinued
0.6596	Remote Similarity	NPD1549	Phase 2
0.6591	Remote Similarity	NPD3225	Approved
0.6589	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD1778	Approved
0.6585	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD9491	Approved
0.6571	Remote Similarity	NPD6099	Approved
0.6571	Remote Similarity	NPD9088	Approved
0.6571	Remote Similarity	NPD6100	Approved
0.6569	Remote Similarity	NPD3140	Approved
0.6569	Remote Similarity	NPD3142	Approved
0.6569	Remote Similarity	NPD826	Approved
0.6569	Remote Similarity	NPD825	Approved
0.6567	Remote Similarity	NPD9569	Approved
0.6565	Remote Similarity	NPD4878	Approved
0.6555	Remote Similarity	NPD9500	Approved
0.6554	Remote Similarity	NPD7028	Phase 2
0.6552	Remote Similarity	NPD3495	Discontinued
0.6545	Remote Similarity	NPD9259	Approved
0.6545	Remote Similarity	NPD9257	Approved
0.6541	Remote Similarity	NPD3266	Approved
0.6541	Remote Similarity	NPD3267	Approved
0.6538	Remote Similarity	NPD3421	Phase 3
0.6538	Remote Similarity	NPD3143	Discontinued

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