NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	132.05
Volume:	120.832
LogP:	-3.446
LogD:	-1.237
LogS:	-0.984
# Rotatable Bonds:	3
TPSA:	106.41
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	0
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	2.516
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.156
MDCK Permeability:	0.0046182009391486645
Pgp-inhibitor:	0.001
Pgp-substrate:	0.843
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.68
Plasma Protein Binding (PPB):	7.861158847808838%
Volume Distribution (VD):	0.366
Pgp-substrate:	90.60143280029297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.199
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.021

ADMET: Excretion

Clearance (CL):	7.664
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.208
Carcinogencity:	0.026
Eye Corrosion:	0.004
Eye Irritation:	0.076
Respiratory Toxicity:	0.078

Download Data

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

Natural Product: NPC153370

Natural Product ID:	NPC153370
*Common Name:**	(2R)-4-Amino-2-Azaniumyl-4-Oxobutanoate
IUPAC Name:	(2R)-4-amino-2-azaniumyl-4-oxobutanoate
Synonyms:
Standard InCHIKey:	DCXYFEDJOCDNAF-UWTATZPHSA-N
Standard InCHI:	InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m1/s1
SMILES:	OC(=N)C[C@H](C(=O)O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1232369
PubChem CID:	6991971 439600
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004312] Asparagine and derivatives

*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
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0003-9861(62)90112-1]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11032480]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11035032]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12902239]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[13835567]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14389294]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1449509]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14607989]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987058]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15375647]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15744050]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16850348]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17439666]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22031445]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2405251]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24305546]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24678285]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24733517]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24831709]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24981409]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2687322]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3289762]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4266242]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4616942]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5764336]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6306574]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[767332]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7929110]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8017107]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8798704]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8852895]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8971708]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748245]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4802	Scrophularia ningpoensis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	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
Others	1
Potency	1

Activity Type	# Activity
Individual Protein	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT698	Individual Protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	37685.8	nM	PMID[455763]
NPT21123	SINGLE PROTEIN	Amino acid transporter	Rattus norvegicus	Inhibition	>=	25.0	%	PMID[455764]

☑ 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 NPC153370 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	2076
0.1-0.2	32163
0.2-0.3	6833
0.3-0.4	1040
0.4-0.5	316
0.5-0.6	119
0.6-0.7	89
0.7-0.8	55
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.88	High Similarity	NPC327831
0.8511	High Similarity	NPC136159
0.8298	Intermediate Similarity	NPC297220
0.8085	Intermediate Similarity	NPC285322
0.8085	Intermediate Similarity	NPC208793
0.8039	Intermediate Similarity	NPC197087
0.8039	Intermediate Similarity	NPC190184
0.8	Intermediate Similarity	NPC121517
0.8	Intermediate Similarity	NPC168375
0.8	Intermediate Similarity	NPC326992
0.7885	Intermediate Similarity	NPC316889
0.7885	Intermediate Similarity	NPC321118
0.7885	Intermediate Similarity	NPC322091
0.7885	Intermediate Similarity	NPC60672
0.78	Intermediate Similarity	NPC328378
0.7708	Intermediate Similarity	NPC329263
0.766	Intermediate Similarity	NPC291186
0.766	Intermediate Similarity	NPC167986
0.7609	Intermediate Similarity	NPC326212
0.7609	Intermediate Similarity	NPC237525
0.7609	Intermediate Similarity	NPC66043
0.76	Intermediate Similarity	NPC227850
0.7593	Intermediate Similarity	NPC38463
0.7593	Intermediate Similarity	NPC325985
0.75	Intermediate Similarity	NPC325097
0.75	Intermediate Similarity	NPC132307
0.75	Intermediate Similarity	NPC126925
0.7358	Intermediate Similarity	NPC329495
0.7347	Intermediate Similarity	NPC327698
0.7347	Intermediate Similarity	NPC118459
0.7308	Intermediate Similarity	NPC319175
0.7255	Intermediate Similarity	NPC140872
0.7255	Intermediate Similarity	NPC93081
0.7234	Intermediate Similarity	NPC53449
0.72	Intermediate Similarity	NPC136476
0.72	Intermediate Similarity	NPC49952
0.72	Intermediate Similarity	NPC309658
0.7193	Intermediate Similarity	NPC321468
0.7193	Intermediate Similarity	NPC321536
0.7193	Intermediate Similarity	NPC316826
0.7193	Intermediate Similarity	NPC317143
0.7193	Intermediate Similarity	NPC320598
0.7193	Intermediate Similarity	NPC327748
0.7193	Intermediate Similarity	NPC254541
0.7115	Intermediate Similarity	NPC112890
0.7115	Intermediate Similarity	NPC316231
0.7115	Intermediate Similarity	NPC324825
0.7111	Intermediate Similarity	NPC116709
0.7111	Intermediate Similarity	NPC272614
0.7111	Intermediate Similarity	NPC21290
0.7091	Intermediate Similarity	NPC322573
0.7069	Intermediate Similarity	NPC321419
0.7069	Intermediate Similarity	NPC143722
0.7069	Intermediate Similarity	NPC327170
0.7069	Intermediate Similarity	NPC329564
0.7018	Intermediate Similarity	NPC176164
0.7018	Intermediate Similarity	NPC189301
0.6981	Remote Similarity	NPC125736
0.6957	Remote Similarity	NPC63621
0.6957	Remote Similarity	NPC69179
0.6949	Remote Similarity	NPC322206
0.6863	Remote Similarity	NPC213876
0.6863	Remote Similarity	NPC185755
0.6842	Remote Similarity	NPC317147
0.6842	Remote Similarity	NPC318260
0.6809	Remote Similarity	NPC18188
0.68	Remote Similarity	NPC198301
0.68	Remote Similarity	NPC43264
0.6792	Remote Similarity	NPC152451
0.6792	Remote Similarity	NPC162620
0.6792	Remote Similarity	NPC270805
0.6792	Remote Similarity	NPC62045
0.6792	Remote Similarity	NPC245027
0.6792	Remote Similarity	NPC226027
0.6792	Remote Similarity	NPC193989
0.6792	Remote Similarity	NPC174246
0.6792	Remote Similarity	NPC170739
0.6792	Remote Similarity	NPC84636
0.6792	Remote Similarity	NPC93888
0.6792	Remote Similarity	NPC43204
0.6774	Remote Similarity	NPC470108
0.6731	Remote Similarity	NPC181588
0.6724	Remote Similarity	NPC190385
0.6721	Remote Similarity	NPC289691
0.6667	Remote Similarity	NPC137958
0.6667	Remote Similarity	NPC315977
0.6667	Remote Similarity	NPC273330
0.6667	Remote Similarity	NPC470109
0.6667	Remote Similarity	NPC313263
0.6613	Remote Similarity	NPC174304
0.6613	Remote Similarity	NPC325597
0.6562	Remote Similarity	NPC470110
0.6557	Remote Similarity	NPC327252
0.6491	Remote Similarity	NPC10915
0.6452	Remote Similarity	NPC315744
0.6444	Remote Similarity	NPC114517
0.6441	Remote Similarity	NPC43169
0.6441	Remote Similarity	NPC112224
0.6441	Remote Similarity	NPC327895
0.6441	Remote Similarity	NPC93861
0.6429	Remote Similarity	NPC317815
0.6415	Remote Similarity	NPC204364
0.6415	Remote Similarity	NPC316168
0.6406	Remote Similarity	NPC118524
0.64	Remote Similarity	NPC317691
0.64	Remote Similarity	NPC326808
0.64	Remote Similarity	NPC254482
0.64	Remote Similarity	NPC226265
0.64	Remote Similarity	NPC219143
0.64	Remote Similarity	NPC110533
0.6383	Remote Similarity	NPC9294
0.6364	Remote Similarity	NPC114990
0.6364	Remote Similarity	NPC327239
0.6333	Remote Similarity	NPC473599
0.6327	Remote Similarity	NPC327250
0.6316	Remote Similarity	NPC183845
0.6316	Remote Similarity	NPC279661
0.6308	Remote Similarity	NPC319046
0.6275	Remote Similarity	NPC276294
0.6271	Remote Similarity	NPC278209
0.625	Remote Similarity	NPC322946
0.625	Remote Similarity	NPC19576
0.625	Remote Similarity	NPC200550
0.625	Remote Similarity	NPC29950
0.625	Remote Similarity	NPC155156
0.6226	Remote Similarity	NPC306238
0.6226	Remote Similarity	NPC198196
0.6226	Remote Similarity	NPC248970
0.6212	Remote Similarity	NPC126779
0.6207	Remote Similarity	NPC2801
0.6207	Remote Similarity	NPC102815
0.619	Remote Similarity	NPC88898
0.619	Remote Similarity	NPC106216
0.6154	Remote Similarity	NPC323974
0.614	Remote Similarity	NPC189178
0.614	Remote Similarity	NPC263065
0.6129	Remote Similarity	NPC118429
0.6129	Remote Similarity	NPC477644
0.6111	Remote Similarity	NPC101249
0.6061	Remote Similarity	NPC81647
0.6029	Remote Similarity	NPC328457
0.6	Remote Similarity	NPC327542
0.5968	Remote Similarity	NPC177191
0.5968	Remote Similarity	NPC68974
0.5965	Remote Similarity	NPC202525
0.5946	Remote Similarity	NPC314466
0.5942	Remote Similarity	NPC315897
0.5938	Remote Similarity	NPC145658
0.5938	Remote Similarity	NPC103130
0.5938	Remote Similarity	NPC226453
0.5926	Remote Similarity	NPC228932
0.5909	Remote Similarity	NPC126681
0.5909	Remote Similarity	NPC221764
0.5909	Remote Similarity	NPC135539
0.5909	Remote Similarity	NPC78312
0.5909	Remote Similarity	NPC196359
0.5902	Remote Similarity	NPC302003
0.5902	Remote Similarity	NPC245346
0.5902	Remote Similarity	NPC11433
0.5893	Remote Similarity	NPC17244
0.5893	Remote Similarity	NPC286989
0.5862	Remote Similarity	NPC245768
0.5857	Remote Similarity	NPC476248
0.5846	Remote Similarity	NPC278881
0.5821	Remote Similarity	NPC107224
0.5818	Remote Similarity	NPC118187
0.5806	Remote Similarity	NPC64250
0.5806	Remote Similarity	NPC268927
0.5806	Remote Similarity	NPC276928
0.5769	Remote Similarity	NPC105488
0.5763	Remote Similarity	NPC145235
0.5758	Remote Similarity	NPC325534
0.5758	Remote Similarity	NPC327985
0.5745	Remote Similarity	NPC260324
0.5741	Remote Similarity	NPC191136
0.5735	Remote Similarity	NPC472579
0.5714	Remote Similarity	NPC55274
0.5714	Remote Similarity	NPC318523
0.566	Remote Similarity	NPC107645
0.5625	Remote Similarity	NPC273037
0.56	Remote Similarity	NPC25237

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 NPC153370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	6382
0.2-0.3	1677
0.3-0.4	453
0.4-0.5	165
0.5-0.6	66
0.6-0.7	46
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8614	Approved
0.8085	Intermediate Similarity	NPD8610	Approved
0.8039	Intermediate Similarity	NPD8785	Approved
0.766	Intermediate Similarity	NPD8805	Approved
0.766	Intermediate Similarity	NPD8804	Approved
0.75	Intermediate Similarity	NPD8798	Approved
0.7447	Intermediate Similarity	NPD8609	Approved
0.7321	Intermediate Similarity	NPD9433	Approved
0.7255	Intermediate Similarity	NPD8809	Approved
0.7255	Intermediate Similarity	NPD8808	Approved
0.7213	Intermediate Similarity	NPD1429	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD9044	Approved
0.7111	Intermediate Similarity	NPD8211	Approved
0.7111	Intermediate Similarity	NPD8210	Phase 3
0.6909	Remote Similarity	NPD9419	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD8982	Approved
0.6863	Remote Similarity	NPD8801	Approved
0.6809	Remote Similarity	NPD8623	Phase 1
0.6792	Remote Similarity	NPD9016	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8624	Approved
0.6792	Remote Similarity	NPD9017	Approved
0.6792	Remote Similarity	NPD8803	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD9018	Approved
0.6792	Remote Similarity	NPD8802	Approved
0.6792	Remote Similarity	NPD9021	Approved
0.6731	Remote Similarity	NPD8810	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD9023	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8871	Approved
0.6667	Remote Similarity	NPD8872	Phase 3
0.6667	Remote Similarity	NPD574	Approved
0.6613	Remote Similarity	NPD348	Approved
0.6557	Remote Similarity	NPD575	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8849	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8851	Phase 1
0.6415	Remote Similarity	NPD8209	Phase 2
0.6415	Remote Similarity	NPD8208	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD886	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8214	Approved
0.64	Remote Similarity	NPD8215	Approved
0.64	Remote Similarity	NPD8217	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8216	Approved
0.6324	Remote Similarity	NPD366	Approved
0.6308	Remote Similarity	NPD4241	Registered
0.6308	Remote Similarity	NPD337	Discontinued
0.6296	Remote Similarity	NPD8873	Approved
0.625	Remote Similarity	NPD8846	Approved
0.625	Remote Similarity	NPD8847	Approved
0.625	Remote Similarity	NPD61	Approved
0.625	Remote Similarity	NPD9441	Phase 2
0.6226	Remote Similarity	NPD9020	Approved
0.6226	Remote Similarity	NPD8870	Approved
0.6212	Remote Similarity	NPD4242	Approved
0.6154	Remote Similarity	NPD8842	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD9019	Approved
0.614	Remote Similarity	NPD9204	Approved
0.614	Remote Similarity	NPD9205	Approved
0.6129	Remote Similarity	NPD9014	Approved
0.6111	Remote Similarity	NPD8866	Approved
0.6111	Remote Similarity	NPD8867	Approved
0.6102	Remote Similarity	NPD8980	Approved
0.6102	Remote Similarity	NPD8981	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD8979	Approved
0.6071	Remote Similarity	NPD9025	Approved
0.6071	Remote Similarity	NPD329	Discontinued
0.6061	Remote Similarity	NPD9451	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD9452	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD2262	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9213	Approved
0.6	Remote Similarity	NPD9214	Phase 3
0.5942	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD1825	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD9047	Approved
0.5938	Remote Similarity	NPD9048	Approved
0.5938	Remote Similarity	NPD9045	Approved
0.5938	Remote Similarity	NPD9046	Phase 3
0.5909	Remote Similarity	NPD7371	Approved
0.5909	Remote Similarity	NPD8868	Approved
0.5902	Remote Similarity	NPD8865	Approved
0.5893	Remote Similarity	NPD9230	Discontinued
0.5849	Remote Similarity	NPD8869	Approved
0.5818	Remote Similarity	NPD8850	Approved
0.5789	Remote Similarity	NPD7643	Phase 1
0.5789	Remote Similarity	NPD4829	Discontinued
0.5769	Remote Similarity	NPD8197	Approved
0.5769	Remote Similarity	NPD8198	Approved
0.5758	Remote Similarity	NPD8952	Approved
0.5741	Remote Similarity	NPD9658	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD9425	Approved
0.5714	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1147	Phase 2
0.5672	Remote Similarity	NPD9231	Phase 3
0.5672	Remote Similarity	NPD9233	Phase 3
0.5672	Remote Similarity	NPD9232	Phase 2
0.5672	Remote Similarity	NPD2263	Discontinued
0.5667	Remote Similarity	NPD8971	Approved
0.5614	Remote Similarity	NPD8947	Approved
0.5614	Remote Similarity	NPD8946	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