NPASS Compound

Structure

NPC76308 OpenBabel07101719142D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.9328 3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7248 2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8838 4.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4190 2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5388 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 -2.4680 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6270 3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5780 3.8344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 5.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 12 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 14 7 1 6 0 0 0 14 17 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 10 1 1 0 0 0 17 18 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.12
Volume:	310.921
LogP:	3.176
LogD:	2.972
LogS:	-3.075
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.852
Synthetic Accessibility Score:	3.117
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.789
MDCK Permeability:	1.5948984582792036e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	91.18923950195312%
Volume Distribution (VD):	1.054
Pgp-substrate:	14.495875358581543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.955
CYP2C19-substrate:	0.102
CYP2C9-inhibitor:	0.877
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.952
CYP2D6-substrate:	0.783
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	17.501
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.289
Human Hepatotoxicity (H-HT):	0.367
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.741
Skin Sensitization:	0.942
Carcinogencity:	0.31
Eye Corrosion:	0.005
Eye Irritation:	0.855
Respiratory Toxicity:	0.114

Download Data

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

Natural Product: NPC76308

Natural Product ID:	NPC76308
*Common Name:**	Enterolactone
IUPAC Name:	(3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
Synonyms:	Enterolactone
Standard InCHIKey:	HVDGDHBAMCBBLR-WMLDXEAASA-N
Standard InCHI:	InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m0/s1
SMILES:	c1cc(C[C@H]2COC(=O)[C@@H]2Cc2cccc(c2)O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471475
PubChem CID:	10685477
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

*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
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24417583]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[26923696]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25114	Linum usitatissimum	Species	Linaceae	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	8
Potency	7

Activity Type	# Activity
Cell Line	5
Individual Protein	2
Organism	2
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	FC	=	1.84	n.a.	PMID[527277]
NPT492	Cell Line	Caco-2	Homo sapiens	Ratio	=	0.8	n.a.	PMID[527278]
NPT492	Cell Line	Caco-2	Homo sapiens	Papp	=	10.6	ucm/s	PMID[527278]
NPT492	Cell Line	Caco-2	Homo sapiens	Papp	=	13.7	ucm/s	PMID[527278]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	23500.0	nM	PMID[527280]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	14791.1	nM	PMID[14640526]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	16.2	%	PMID[527276]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	4650.0	nmol	PMID[527276]
NPT35	Others	n.a.		Stability	>	95.0	%	PMID[527278]
NPT77	Individual Protein	Transthyretin	Homo sapiens	Inhibition	<	20.0	%	PMID[527279]
NPT2	Others	Unspecified		Potency	n.a.	8244.8	nM	PMID[18579783]
NPT2	Others	Unspecified		Potency	n.a.	16620.2	nM	PMID[10654415]
NPT2	Others	Unspecified		Potency	n.a.	741.3	nM	PMID[18293924]
NPT2	Others	Unspecified		Potency	n.a.	16595.9	nM	DOI[10.6019/CHEMBL1201861]
NPT2	Others	Unspecified		Potency	n.a.	1862.1	nM	PMID[17067158]
NPT2	Others	Unspecified		Potency	n.a.	18457.8	nM	PMID[18183025]

☑ 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 NPC76308 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	234
0.1-0.2	1035
0.2-0.3	2447
0.3-0.4	6450
0.4-0.5	12637
0.5-0.6	7859
0.6-0.7	10333
0.7-0.8	1642
0.8-0.85	57
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC325295
0.8583	High Similarity	NPC472271
0.8583	High Similarity	NPC5310
0.8583	High Similarity	NPC300776
0.8583	High Similarity	NPC176814
0.8583	High Similarity	NPC4982
0.8583	High Similarity	NPC68779
0.8547	High Similarity	NPC128249
0.8496	Intermediate Similarity	NPC31274
0.8468	Intermediate Similarity	NPC323810
0.843	Intermediate Similarity	NPC322332
0.8417	Intermediate Similarity	NPC478121
0.8385	Intermediate Similarity	NPC308976
0.8374	Intermediate Similarity	NPC85565
0.8374	Intermediate Similarity	NPC288945
0.8361	Intermediate Similarity	NPC121168
0.8359	Intermediate Similarity	NPC472591
0.8348	Intermediate Similarity	NPC63345
0.8347	Intermediate Similarity	NPC164852
0.8333	Intermediate Similarity	NPC42657
0.8333	Intermediate Similarity	NPC472593
0.8333	Intermediate Similarity	NPC214246
0.832	Intermediate Similarity	NPC223807
0.8319	Intermediate Similarity	NPC188677
0.8319	Intermediate Similarity	NPC175799
0.8319	Intermediate Similarity	NPC610
0.8319	Intermediate Similarity	NPC200988
0.8319	Intermediate Similarity	NPC145023
0.8308	Intermediate Similarity	NPC90431
0.8306	Intermediate Similarity	NPC137416
0.8304	Intermediate Similarity	NPC8931
0.8304	Intermediate Similarity	NPC120693
0.8304	Intermediate Similarity	NPC261573
0.8293	Intermediate Similarity	NPC236981
0.8291	Intermediate Similarity	NPC190212
0.8276	Intermediate Similarity	NPC177576
0.825	Intermediate Similarity	NPC328694
0.825	Intermediate Similarity	NPC86198
0.8235	Intermediate Similarity	NPC471924
0.8235	Intermediate Similarity	NPC471925
0.8235	Intermediate Similarity	NPC471928
0.8211	Intermediate Similarity	NPC469927
0.8205	Intermediate Similarity	NPC26615
0.8203	Intermediate Similarity	NPC318799
0.8198	Intermediate Similarity	NPC294741
0.8197	Intermediate Similarity	NPC241001
0.8197	Intermediate Similarity	NPC98305
0.8195	Intermediate Similarity	NPC29599
0.8195	Intermediate Similarity	NPC100675
0.8195	Intermediate Similarity	NPC282291
0.8195	Intermediate Similarity	NPC166137
0.819	Intermediate Similarity	NPC252544
0.819	Intermediate Similarity	NPC321252
0.819	Intermediate Similarity	NPC183700
0.8189	Intermediate Similarity	NPC131684
0.8182	Intermediate Similarity	NPC70084
0.8182	Intermediate Similarity	NPC160235
0.8182	Intermediate Similarity	NPC470215
0.8182	Intermediate Similarity	NPC470214
0.8182	Intermediate Similarity	NPC109371
0.8167	Intermediate Similarity	NPC471926
0.8158	Intermediate Similarity	NPC70843
0.8158	Intermediate Similarity	NPC317592
0.8151	Intermediate Similarity	NPC23402
0.8145	Intermediate Similarity	NPC14141
0.8136	Intermediate Similarity	NPC148969
0.8134	Intermediate Similarity	NPC253481
0.8134	Intermediate Similarity	NPC253722
0.8134	Intermediate Similarity	NPC31751
0.8115	Intermediate Similarity	NPC34634
0.8115	Intermediate Similarity	NPC265454
0.811	Intermediate Similarity	NPC79332
0.8108	Intermediate Similarity	NPC245561
0.8103	Intermediate Similarity	NPC88141
0.8099	Intermediate Similarity	NPC471033
0.8099	Intermediate Similarity	NPC311091
0.8092	Intermediate Similarity	NPC113295
0.808	Intermediate Similarity	NPC117794
0.808	Intermediate Similarity	NPC471927
0.8077	Intermediate Similarity	NPC471749
0.8074	Intermediate Similarity	NPC273657
0.8074	Intermediate Similarity	NPC106920
0.8073	Intermediate Similarity	NPC76938
0.8067	Intermediate Similarity	NPC285350
0.8067	Intermediate Similarity	NPC197513
0.8065	Intermediate Similarity	NPC244351
0.8062	Intermediate Similarity	NPC7012
0.8053	Intermediate Similarity	NPC13426
0.8051	Intermediate Similarity	NPC286222
0.8051	Intermediate Similarity	NPC17693
0.8047	Intermediate Similarity	NPC241354
0.8036	Intermediate Similarity	NPC52472
0.8034	Intermediate Similarity	NPC222084
0.8033	Intermediate Similarity	NPC473974
0.8033	Intermediate Similarity	NPC182240
0.8033	Intermediate Similarity	NPC263386
0.8033	Intermediate Similarity	NPC31296
0.8033	Intermediate Similarity	NPC141791
0.8033	Intermediate Similarity	NPC258366
0.8033	Intermediate Similarity	NPC79933
0.8017	Intermediate Similarity	NPC160199
0.8016	Intermediate Similarity	NPC472592
0.8015	Intermediate Similarity	NPC194970
0.8	Intermediate Similarity	NPC52664
0.8	Intermediate Similarity	NPC322197
0.8	Intermediate Similarity	NPC275145
0.8	Intermediate Similarity	NPC32714
0.8	Intermediate Similarity	NPC29989
0.8	Intermediate Similarity	NPC69332
0.8	Intermediate Similarity	NPC95178
0.8	Intermediate Similarity	NPC51345
0.7984	Intermediate Similarity	NPC162935
0.7984	Intermediate Similarity	NPC25168
0.7984	Intermediate Similarity	NPC249340
0.7984	Intermediate Similarity	NPC31936
0.7983	Intermediate Similarity	NPC176730
0.7983	Intermediate Similarity	NPC123175
0.7969	Intermediate Similarity	NPC217431
0.7967	Intermediate Similarity	NPC473136
0.7967	Intermediate Similarity	NPC328485
0.7967	Intermediate Similarity	NPC318552
0.7967	Intermediate Similarity	NPC190501
0.7966	Intermediate Similarity	NPC228609
0.7956	Intermediate Similarity	NPC223185
0.7955	Intermediate Similarity	NPC279463
0.7953	Intermediate Similarity	NPC471930
0.7953	Intermediate Similarity	NPC474944
0.7953	Intermediate Similarity	NPC471929
0.7953	Intermediate Similarity	NPC471935
0.7949	Intermediate Similarity	NPC326187
0.7949	Intermediate Similarity	NPC79543
0.7941	Intermediate Similarity	NPC477696
0.7941	Intermediate Similarity	NPC470811
0.7941	Intermediate Similarity	NPC477697
0.7939	Intermediate Similarity	NPC205915
0.7934	Intermediate Similarity	NPC277394
0.7934	Intermediate Similarity	NPC28951
0.7934	Intermediate Similarity	NPC61062
0.7934	Intermediate Similarity	NPC299252
0.7934	Intermediate Similarity	NPC325646
0.7934	Intermediate Similarity	NPC123559
0.7931	Intermediate Similarity	NPC260952
0.7928	Intermediate Similarity	NPC292730
0.7928	Intermediate Similarity	NPC216520
0.7928	Intermediate Similarity	NPC82664
0.7928	Intermediate Similarity	NPC132271
0.7926	Intermediate Similarity	NPC9218
0.7923	Intermediate Similarity	NPC108553
0.7923	Intermediate Similarity	NPC198388
0.792	Intermediate Similarity	NPC132518
0.792	Intermediate Similarity	NPC68167
0.792	Intermediate Similarity	NPC283514
0.792	Intermediate Similarity	NPC86900
0.792	Intermediate Similarity	NPC477151
0.792	Intermediate Similarity	NPC478058
0.7917	Intermediate Similarity	NPC41851
0.7917	Intermediate Similarity	NPC81808
0.7913	Intermediate Similarity	NPC13495
0.7903	Intermediate Similarity	NPC165197
0.7903	Intermediate Similarity	NPC470848
0.7903	Intermediate Similarity	NPC470849
0.7899	Intermediate Similarity	NPC48525
0.7886	Intermediate Similarity	NPC233165
0.7886	Intermediate Similarity	NPC184579
0.7879	Intermediate Similarity	NPC110958
0.7879	Intermediate Similarity	NPC19890
0.7874	Intermediate Similarity	NPC167055
0.7874	Intermediate Similarity	NPC240744
0.7874	Intermediate Similarity	NPC280767
0.7869	Intermediate Similarity	NPC476266
0.7868	Intermediate Similarity	NPC272907
0.7868	Intermediate Similarity	NPC2681
0.7863	Intermediate Similarity	NPC5419
0.7863	Intermediate Similarity	NPC206341
0.7863	Intermediate Similarity	NPC18074
0.7863	Intermediate Similarity	NPC61
0.7863	Intermediate Similarity	NPC25581
0.7863	Intermediate Similarity	NPC317305
0.7857	Intermediate Similarity	NPC477153
0.7845	Intermediate Similarity	NPC187913
0.784	Intermediate Similarity	NPC198336
0.784	Intermediate Similarity	NPC253627
0.784	Intermediate Similarity	NPC147654
0.7838	Intermediate Similarity	NPC274678
0.7836	Intermediate Similarity	NPC279676
0.7836	Intermediate Similarity	NPC67349
0.7836	Intermediate Similarity	NPC471152
0.7836	Intermediate Similarity	NPC281780
0.7833	Intermediate Similarity	NPC109241
0.7829	Intermediate Similarity	NPC476024
0.782	Intermediate Similarity	NPC211386
0.782	Intermediate Similarity	NPC472804
0.782	Intermediate Similarity	NPC173569
0.782	Intermediate Similarity	NPC477874
0.7812	Intermediate Similarity	NPC474945
0.7812	Intermediate Similarity	NPC476022
0.7812	Intermediate Similarity	NPC269598
0.781	Intermediate Similarity	NPC89317
0.7807	Intermediate Similarity	NPC91461
0.7807	Intermediate Similarity	NPC12221

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 NPC76308 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	753
0.2-0.3	1171
0.3-0.4	2370
0.4-0.5	2483
0.5-0.6	1424
0.6-0.7	652
0.7-0.8	101
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8203	Intermediate Similarity	NPD6663	Approved
0.8175	Intermediate Similarity	NPD5736	Approved
0.7984	Intermediate Similarity	NPD3764	Approved
0.7967	Intermediate Similarity	NPD3019	Approved
0.7967	Intermediate Similarity	NPD2932	Approved
0.7946	Intermediate Similarity	NPD3020	Approved
0.792	Intermediate Similarity	NPD1608	Approved
0.7803	Intermediate Similarity	NPD6355	Discontinued
0.7797	Intermediate Similarity	NPD3021	Approved
0.7797	Intermediate Similarity	NPD3022	Approved
0.7795	Intermediate Similarity	NPD1283	Approved
0.7769	Intermediate Similarity	NPD2629	Approved
0.7742	Intermediate Similarity	NPD5585	Approved
0.7734	Intermediate Similarity	NPD2797	Approved
0.768	Intermediate Similarity	NPD17	Approved
0.7679	Intermediate Similarity	NPD2860	Approved
0.7679	Intermediate Similarity	NPD2859	Approved
0.7661	Intermediate Similarity	NPD1894	Discontinued
0.7609	Intermediate Similarity	NPD8166	Discontinued
0.7594	Intermediate Similarity	NPD2979	Phase 3
0.7594	Intermediate Similarity	NPD4060	Phase 1
0.7589	Intermediate Similarity	NPD2934	Approved
0.7589	Intermediate Similarity	NPD2933	Approved
0.7576	Intermediate Similarity	NPD3268	Approved
0.7559	Intermediate Similarity	NPD1535	Discovery
0.7559	Intermediate Similarity	NPD1281	Approved
0.7521	Intermediate Similarity	NPD5909	Discontinued
0.7518	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1481	Phase 2
0.7482	Intermediate Similarity	NPD4110	Phase 3
0.7482	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD3847	Discontinued
0.748	Intermediate Similarity	NPD3023	Approved
0.748	Intermediate Similarity	NPD3026	Approved
0.7463	Intermediate Similarity	NPD825	Approved
0.7463	Intermediate Similarity	NPD826	Approved
0.7462	Intermediate Similarity	NPD1470	Approved
0.746	Intermediate Similarity	NPD3024	Approved
0.746	Intermediate Similarity	NPD3025	Approved
0.7456	Intermediate Similarity	NPD288	Approved
0.7445	Intermediate Similarity	NPD2935	Discontinued
0.7444	Intermediate Similarity	NPD6798	Discontinued
0.7442	Intermediate Similarity	NPD4359	Approved
0.7422	Intermediate Similarity	NPD1201	Approved
0.7405	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5647	Approved
0.7391	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD9545	Approved
0.7381	Intermediate Similarity	NPD3091	Approved
0.7372	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD844	Approved
0.7368	Intermediate Similarity	NPD7095	Approved
0.7368	Intermediate Similarity	NPD1989	Approved
0.736	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6653	Approved
0.7338	Intermediate Similarity	NPD5958	Discontinued
0.7328	Intermediate Similarity	NPD1164	Approved
0.7324	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD1651	Approved
0.7319	Intermediate Similarity	NPD2531	Phase 2
0.7319	Intermediate Similarity	NPD2438	Suspended
0.7317	Intermediate Similarity	NPD7635	Approved
0.7313	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6190	Approved
0.7295	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2614	Approved
0.7288	Intermediate Similarity	NPD6647	Phase 2
0.7281	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD256	Approved
0.728	Intermediate Similarity	NPD255	Approved
0.7266	Intermediate Similarity	NPD6002	Phase 3
0.7266	Intermediate Similarity	NPD5305	Approved
0.7266	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6004	Phase 3
0.7266	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6005	Phase 3
0.7266	Intermediate Similarity	NPD5306	Approved
0.7266	Intermediate Similarity	NPD1778	Approved
0.7265	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD8032	Phase 2
0.7259	Intermediate Similarity	NPD6233	Phase 2
0.7259	Intermediate Similarity	NPD4062	Phase 3
0.7246	Intermediate Similarity	NPD7033	Discontinued
0.7244	Intermediate Similarity	NPD1759	Phase 1
0.7241	Intermediate Similarity	NPD9495	Approved
0.7239	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD6273	Approved
0.7222	Intermediate Similarity	NPD9493	Approved
0.7218	Intermediate Similarity	NPD2861	Phase 2
0.7213	Intermediate Similarity	NPD4750	Phase 3
0.7213	Intermediate Similarity	NPD1792	Phase 2
0.7209	Intermediate Similarity	NPD3496	Discontinued
0.7209	Intermediate Similarity	NPD4136	Approved
0.7209	Intermediate Similarity	NPD4106	Approved
0.7209	Intermediate Similarity	NPD4135	Approved
0.7206	Intermediate Similarity	NPD4140	Approved
0.7197	Intermediate Similarity	NPD1203	Approved
0.7197	Intermediate Similarity	NPD3267	Approved
0.7197	Intermediate Similarity	NPD3266	Approved
0.7194	Intermediate Similarity	NPD4477	Approved
0.7194	Intermediate Similarity	NPD5408	Approved
0.7194	Intermediate Similarity	NPD6032	Approved
0.7194	Intermediate Similarity	NPD5406	Approved
0.7194	Intermediate Similarity	NPD5405	Approved
0.7194	Intermediate Similarity	NPD5404	Approved
0.7194	Intermediate Similarity	NPD4476	Approved
0.7193	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD845	Approved
0.7192	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2342	Discontinued
0.719	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2313	Discontinued
0.7179	Intermediate Similarity	NPD2066	Phase 3
0.7177	Intermediate Similarity	NPD5535	Approved
0.7176	Intermediate Similarity	NPD1755	Approved
0.7176	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1239	Approved
0.7167	Intermediate Similarity	NPD5048	Discontinued
0.7165	Intermediate Similarity	NPD1758	Phase 1
0.7162	Intermediate Similarity	NPD37	Approved
0.7154	Intermediate Similarity	NPD3092	Approved
0.7154	Intermediate Similarity	NPD4806	Approved
0.7154	Intermediate Similarity	NPD4807	Approved
0.7153	Intermediate Similarity	NPD4622	Approved
0.7153	Intermediate Similarity	NPD4618	Approved
0.7153	Intermediate Similarity	NPD555	Phase 2
0.7152	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD257	Approved
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1929	Approved
0.7143	Intermediate Similarity	NPD258	Approved
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1930	Approved
0.7133	Intermediate Similarity	NPD4965	Approved
0.7133	Intermediate Similarity	NPD4967	Phase 2
0.7133	Intermediate Similarity	NPD4966	Approved
0.7132	Intermediate Similarity	NPD3095	Discontinued
0.7132	Intermediate Similarity	NPD4870	Approved
0.7132	Intermediate Similarity	NPD4626	Approved
0.7131	Intermediate Similarity	NPD9266	Approved
0.7131	Intermediate Similarity	NPD74	Approved
0.713	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1693	Approved
0.7123	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5283	Phase 1
0.7119	Intermediate Similarity	NPD1242	Phase 1
0.7113	Intermediate Similarity	NPD3400	Discontinued
0.7113	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1444	Approved
0.7107	Intermediate Similarity	NPD968	Approved
0.7107	Intermediate Similarity	NPD1445	Approved
0.7092	Intermediate Similarity	NPD4534	Discontinued
0.709	Intermediate Similarity	NPD5204	Approved
0.7087	Intermediate Similarity	NPD9568	Approved
0.7083	Intermediate Similarity	NPD1237	Approved
0.708	Intermediate Similarity	NPD1089	Approved
0.708	Intermediate Similarity	NPD6346	Approved
0.708	Intermediate Similarity	NPD3672	Approved
0.708	Intermediate Similarity	NPD1090	Approved
0.708	Intermediate Similarity	NPD3673	Approved
0.708	Intermediate Similarity	NPD1086	Approved
0.7073	Intermediate Similarity	NPD2067	Discontinued
0.7068	Intermediate Similarity	NPD6362	Approved
0.7068	Intermediate Similarity	NPD3094	Phase 2
0.7063	Intermediate Similarity	NPD5951	Approved
0.7054	Intermediate Similarity	NPD4105	Approved
0.7054	Intermediate Similarity	NPD4102	Approved
0.7054	Intermediate Similarity	NPD5691	Approved
0.705	Intermediate Similarity	NPD5688	Approved
0.705	Intermediate Similarity	NPD5689	Approved
0.7049	Intermediate Similarity	NPD9263	Approved
0.7049	Intermediate Similarity	NPD9267	Approved
0.7049	Intermediate Similarity	NPD9264	Approved
0.7045	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7034	Intermediate Similarity	NPD7798	Approved
0.7034	Intermediate Similarity	NPD1238	Approved
0.7029	Intermediate Similarity	NPD230	Phase 1
0.7023	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2344	Approved
0.7021	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5763	Approved
0.7021	Intermediate Similarity	NPD5762	Approved
0.7015	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6085	Phase 2
0.7009	Intermediate Similarity	NPD1564	Approved
0.7009	Intermediate Similarity	NPD1566	Phase 3
0.7009	Intermediate Similarity	NPD1565	Approved
0.7008	Intermediate Similarity	NPD4198	Discontinued
0.7008	Intermediate Similarity	NPD6671	Approved
0.7007	Intermediate Similarity	NPD259	Phase 1
0.7	Intermediate Similarity	NPD4308	Phase 3
0.7	Intermediate Similarity	NPD4059	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