NPASS Compound

Structure

CID328611 OpenBabel06191716202D 32 34 0 0 1 0 0 0 0 0999 V2000 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 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 3.4641 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 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 7.7942 -4.5000 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 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -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 6.9282 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 9 2 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 10 1 0 0 0 0 5 6 1 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 21 1 0 0 0 0 8 11 1 0 0 0 0 8 22 1 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 5 1 6 0 0 0 12 18 1 0 0 0 0 12 24 1 0 0 0 0 13 27 2 0 0 0 0 13 28 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 24 1 0 0 0 0 16 29 2 0 0 0 0 17 26 2 0 0 0 0 17 30 1 0 0 0 0 18 31 2 0 0 0 0 18 32 1 0 0 0 0 19 20 2 0 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	445.17
Volume:	417.501
LogP:	-2.256
LogD:	-0.46
LogS:	-4.642
# Rotatable Bonds:	10
TPSA:	212.29
# H-Bond Aceptor:	13
# H-Bond Donor:	9
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.244
Synthetic Accessibility Score:	3.779
Fsp3:	0.316
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.099
MDCK Permeability:	7.86820146458922e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.322
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	64.52574157714844%
Volume Distribution (VD):	0.212
Pgp-substrate:	47.56509017944336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.028
CYP2C9-inhibitor:	0.181
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	3.277
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.102
Skin Sensitization:	0.053
Carcinogencity:	0.291
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.348

Download Data

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

Natural Product: NPC328611

Natural Product ID:	NPC328611
*Common Name:**	2-{4-[(2-Amino-4-Oxo-1,4,5,6,7,8-Hexahydro-Pteridin-6-Ylmethyl)-Amino]-Benzoylamino}-Pentanedioic Acid
IUPAC Name:	(2S)-2-[[4-[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
Synonyms:
Standard InCHIKey:	MSTNYGQPCMXVAQ-KIYNQFGBSA-N
Standard InCHI:	InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1
SMILES:	OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NCC1CNc2c(N1)c(O)nc(=N)[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2021342
PubChem CID:	91443
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:0004323] Glutamic acid 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]
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]
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]
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]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	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	2
Kd	3
Others	21

Activity Type	# Activity
ORGANISM	5
Others	1
SINGLE PROTEIN	20

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24900	SINGLE PROTEIN	Folylpoly-gamma-glutamate synthetase	Mus musculus	Km	=	8000.0	nM	PMID[469805]
NPT24900	SINGLE PROTEIN	Folylpoly-gamma-glutamate synthetase	Mus musculus	Km	=	7100000000.0	nM	PMID[469806]
NPT24900	SINGLE PROTEIN	Folylpoly-gamma-glutamate synthetase	Mus musculus	Relative Km	=	0.051	n.a.	PMID[469806]
NPT24900	SINGLE PROTEIN	Folylpoly-gamma-glutamate synthetase	Mus musculus	Relative Vmax	=	1.31	n.a.	PMID[469806]
NPT24901	SINGLE PROTEIN	Folylpoly-gamma-glutamate synthetase	Homo sapiens	Km	=	4200.0	nM	PMID[469807]
NPT24901	SINGLE PROTEIN	Folylpoly-gamma-glutamate synthetase	Homo sapiens	Vmax	=	135.0	%	PMID[469807]
NPT2	Others	Unspecified		Ratio	=	32.1	n.a.	PMID[469807]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	Kd	=	60.0	nM	PMID[469808]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	Kd	=	300.0	nM	PMID[469808]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	k_off	=	1.4	s-1	PMID[469809]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	k_off	=	3.6	s-1	PMID[469809]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	k_off	=	14.0	s-1	PMID[469809]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	k_off	=	12.2	s-1	PMID[469809]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	Rate of hydride transfer	=	2.4	s-1	PMID[469809]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	Rate of hydride transfer	=	13.0	s-1	PMID[469809]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	Rate of hydride transfer	=	12.0	s-1	PMID[469809]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	Rate of hydride transfer	=	10.0	s-1	PMID[469809]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	Rate of hydride transfer	=	18.0	s-1	PMID[469809]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	Rate of hydride transfer	=	52.0	s-1	PMID[469809]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	28.84	%	PMID[469810]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-8.449	%	PMID[469811]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.03	%	PMID[469812]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[469813]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[469813]

☑ 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 NPC328611 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	486
0.1-0.2	6049
0.2-0.3	13675
0.3-0.4	15835
0.4-0.5	3631
0.5-0.6	2689
0.6-0.7	312
0.7-0.8	10
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC14849
0.9811	High Similarity	NPC131450
0.9811	High Similarity	NPC182057
0.9811	High Similarity	NPC147298
0.9747	High Similarity	NPC248862
0.7979	Intermediate Similarity	NPC177996
0.7979	Intermediate Similarity	NPC147983
0.7751	Intermediate Similarity	NPC84317
0.7697	Intermediate Similarity	NPC478039
0.7661	Intermediate Similarity	NPC154478
0.7564	Intermediate Similarity	NPC322433
0.7296	Intermediate Similarity	NPC471155
0.7259	Intermediate Similarity	NPC270241
0.7245	Intermediate Similarity	NPC225400
0.7232	Intermediate Similarity	NPC138293
0.7232	Intermediate Similarity	NPC113056
0.7208	Intermediate Similarity	NPC470786
0.7208	Intermediate Similarity	NPC472538
0.7135	Intermediate Similarity	NPC189116
0.7113	Intermediate Similarity	NPC106118
0.7047	Intermediate Similarity	NPC472540
0.7047	Intermediate Similarity	NPC472539
0.7047	Intermediate Similarity	NPC470787
0.701	Intermediate Similarity	NPC472541
0.701	Intermediate Similarity	NPC472542
0.6982	Remote Similarity	NPC43477
0.6982	Remote Similarity	NPC2823
0.6941	Remote Similarity	NPC472241
0.6923	Remote Similarity	NPC471199
0.6923	Remote Similarity	NPC242933
0.6919	Remote Similarity	NPC472242
0.6915	Remote Similarity	NPC285192
0.6914	Remote Similarity	NPC314223
0.6905	Remote Similarity	NPC287358
0.6884	Remote Similarity	NPC295548
0.686	Remote Similarity	NPC314186
0.6848	Remote Similarity	NPC292265
0.6813	Remote Similarity	NPC471130
0.6796	Remote Similarity	NPC88970
0.6789	Remote Similarity	NPC471742
0.6788	Remote Similarity	NPC194562
0.6788	Remote Similarity	NPC472245
0.6788	Remote Similarity	NPC471195
0.6788	Remote Similarity	NPC471196
0.678	Remote Similarity	NPC117032
0.6779	Remote Similarity	NPC248601
0.674	Remote Similarity	NPC68650
0.674	Remote Similarity	NPC27904
0.6731	Remote Similarity	NPC471197
0.6727	Remote Similarity	NPC150863
0.6725	Remote Similarity	NPC472243
0.6699	Remote Similarity	NPC471198
0.6686	Remote Similarity	NPC471164
0.6667	Remote Similarity	NPC276430
0.6667	Remote Similarity	NPC307396
0.6649	Remote Similarity	NPC470317
0.6646	Remote Similarity	NPC472244
0.6646	Remote Similarity	NPC470343
0.6627	Remote Similarity	NPC316104
0.6627	Remote Similarity	NPC162417
0.6598	Remote Similarity	NPC473815
0.6595	Remote Similarity	NPC182131
0.6587	Remote Similarity	NPC314431
0.6587	Remote Similarity	NPC280807
0.6573	Remote Similarity	NPC473329
0.657	Remote Similarity	NPC83214
0.6561	Remote Similarity	NPC475607
0.6559	Remote Similarity	NPC66490
0.6556	Remote Similarity	NPC295021
0.6548	Remote Similarity	NPC314098
0.6545	Remote Similarity	NPC475685
0.6538	Remote Similarity	NPC24617
0.6538	Remote Similarity	NPC471193
0.6538	Remote Similarity	NPC471194
0.6535	Remote Similarity	NPC471944
0.6534	Remote Similarity	NPC311658
0.6531	Remote Similarity	NPC313293
0.6529	Remote Similarity	NPC253476
0.6526	Remote Similarity	NPC474081
0.6517	Remote Similarity	NPC300596
0.6517	Remote Similarity	NPC237649
0.6512	Remote Similarity	NPC132636
0.6512	Remote Similarity	NPC122553
0.6508	Remote Similarity	NPC470548
0.6508	Remote Similarity	NPC475594
0.6503	Remote Similarity	NPC114806
0.6497	Remote Similarity	NPC324445
0.6495	Remote Similarity	NPC235194
0.6492	Remote Similarity	NPC475761
0.6492	Remote Similarity	NPC475094
0.6492	Remote Similarity	NPC474041
0.6491	Remote Similarity	NPC300299
0.649	Remote Similarity	NPC72956
0.6489	Remote Similarity	NPC355
0.6489	Remote Similarity	NPC318183
0.6488	Remote Similarity	NPC471191
0.6459	Remote Similarity	NPC6865
0.6459	Remote Similarity	NPC153980
0.6448	Remote Similarity	NPC104345
0.6437	Remote Similarity	NPC207554
0.642	Remote Similarity	NPC220698
0.642	Remote Similarity	NPC478040
0.6415	Remote Similarity	NPC244425
0.6415	Remote Similarity	NPC15384
0.6413	Remote Similarity	NPC36495
0.6412	Remote Similarity	NPC207428
0.6396	Remote Similarity	NPC316405
0.6373	Remote Similarity	NPC91179
0.6369	Remote Similarity	NPC254798
0.6368	Remote Similarity	NPC471192
0.6359	Remote Similarity	NPC473376
0.6351	Remote Similarity	NPC471741
0.6347	Remote Similarity	NPC205946
0.6332	Remote Similarity	NPC92803
0.6324	Remote Similarity	NPC276085
0.6316	Remote Similarity	NPC476687
0.6316	Remote Similarity	NPC476689
0.6316	Remote Similarity	NPC476685
0.6313	Remote Similarity	NPC18890
0.6292	Remote Similarity	NPC314114
0.6292	Remote Similarity	NPC130797
0.6292	Remote Similarity	NPC136002
0.6287	Remote Similarity	NPC192533
0.6286	Remote Similarity	NPC319645
0.6286	Remote Similarity	NPC315224
0.6284	Remote Similarity	NPC469903
0.6283	Remote Similarity	NPC177261
0.6283	Remote Similarity	NPC285622
0.628	Remote Similarity	NPC226143
0.6278	Remote Similarity	NPC13470
0.6276	Remote Similarity	NPC228835
0.6272	Remote Similarity	NPC58827
0.6272	Remote Similarity	NPC307437
0.6272	Remote Similarity	NPC72473
0.627	Remote Similarity	NPC62104
0.627	Remote Similarity	NPC1390
0.627	Remote Similarity	NPC123241
0.627	Remote Similarity	NPC222029
0.6264	Remote Similarity	NPC473341
0.6263	Remote Similarity	NPC472118
0.6257	Remote Similarity	NPC35510
0.6257	Remote Similarity	NPC253667
0.625	Remote Similarity	NPC474926
0.6244	Remote Similarity	NPC133003
0.6243	Remote Similarity	NPC214960
0.6243	Remote Similarity	NPC279527
0.6242	Remote Similarity	NPC150323
0.6242	Remote Similarity	NPC27833
0.6242	Remote Similarity	NPC279385
0.6242	Remote Similarity	NPC179605
0.6237	Remote Similarity	NPC469902
0.623	Remote Similarity	NPC285381
0.6228	Remote Similarity	NPC254698
0.6218	Remote Similarity	NPC471743
0.6216	Remote Similarity	NPC94167
0.6216	Remote Similarity	NPC172937
0.6213	Remote Similarity	NPC477937
0.6211	Remote Similarity	NPC470971
0.6209	Remote Similarity	NPC300443
0.6207	Remote Similarity	NPC314835
0.6205	Remote Similarity	NPC103292
0.6196	Remote Similarity	NPC239357
0.6193	Remote Similarity	NPC285923
0.6193	Remote Similarity	NPC469560
0.6193	Remote Similarity	NPC97584
0.6193	Remote Similarity	NPC238412
0.619	Remote Similarity	NPC471124
0.6186	Remote Similarity	NPC217372
0.6186	Remote Similarity	NPC183662
0.6186	Remote Similarity	NPC15573
0.6181	Remote Similarity	NPC17059
0.6178	Remote Similarity	NPC198254
0.6178	Remote Similarity	NPC274198
0.6176	Remote Similarity	NPC316282
0.6175	Remote Similarity	NPC272174
0.6173	Remote Similarity	NPC472861
0.6173	Remote Similarity	NPC184932
0.617	Remote Similarity	NPC293458
0.6162	Remote Similarity	NPC316141
0.6158	Remote Similarity	NPC202812
0.6154	Remote Similarity	NPC219336
0.6154	Remote Similarity	NPC11126
0.615	Remote Similarity	NPC469901
0.615	Remote Similarity	NPC471122
0.6149	Remote Similarity	NPC474473
0.6141	Remote Similarity	NPC473002
0.614	Remote Similarity	NPC111428
0.6138	Remote Similarity	NPC217804
0.6138	Remote Similarity	NPC22883
0.6138	Remote Similarity	NPC5719
0.6138	Remote Similarity	NPC210377
0.6135	Remote Similarity	NPC98864
0.6134	Remote Similarity	NPC196243
0.6133	Remote Similarity	NPC259678
0.6129	Remote Similarity	NPC63370
0.6129	Remote Similarity	NPC36836
0.6129	Remote Similarity	NPC324850
0.6127	Remote Similarity	NPC472293
0.6126	Remote Similarity	NPC473000
0.6126	Remote Similarity	NPC469904

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 NPC328611 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	639
0.2-0.3	967
0.3-0.4	2002
0.4-0.5	2720
0.5-0.6	2141
0.6-0.7	406
0.7-0.8	24
0.8-0.85	5
0.85-0.9	3
0.9-0.95	1
0.95-1	13

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3522	Approved
0.9873	High Similarity	NPD4092	Approved
0.9811	High Similarity	NPD3998	Approved
0.9811	High Similarity	NPD3999	Approved
0.9811	High Similarity	NPD3997	Approved
0.981	High Similarity	NPD4091	Approved
0.9748	High Similarity	NPD3991	Approved
0.9748	High Similarity	NPD3994	Approved
0.9748	High Similarity	NPD3992	Approved
0.9748	High Similarity	NPD3996	Approved
0.9748	High Similarity	NPD3993	Approved
0.9748	High Similarity	NPD3995	Approved
0.9689	High Similarity	NPD3990	Phase 3
0.9627	High Similarity	NPD3989	Phase 3
0.8313	Intermediate Similarity	NPD4564	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD4565	Clinical (unspecified phase)
0.8287	Intermediate Similarity	NPD5856	Discontinued
0.7979	Intermediate Similarity	NPD3353	Approved
0.7937	Intermediate Similarity	NPD3410	Approved
0.7937	Intermediate Similarity	NPD3411	Phase 2
0.7917	Intermediate Similarity	NPD4517	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3968	Approved
0.7696	Intermediate Similarity	NPD3967	Approved
0.7663	Intermediate Similarity	NPD5042	Phase 1
0.7654	Intermediate Similarity	NPD7014	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD9540	Approved
0.756	Intermediate Similarity	NPD5748	Phase 2
0.7514	Intermediate Similarity	NPD5727	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD9539	Approved
0.7436	Intermediate Similarity	NPD9541	Approved
0.7363	Intermediate Similarity	NPD3518	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1781	Discontinued
0.7322	Intermediate Similarity	NPD4087	Phase 2
0.7299	Intermediate Similarity	NPD212	Discontinued
0.7289	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7855	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD2966	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2603	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5510	Approved
0.7202	Intermediate Similarity	NPD5024	Approved
0.7202	Intermediate Similarity	NPD4464	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD979	Approved
0.7186	Intermediate Similarity	NPD3625	Discontinued
0.7174	Intermediate Similarity	NPD5445	Approved
0.7143	Intermediate Similarity	NPD6613	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2360	Approved
0.7101	Intermediate Similarity	NPD6753	Phase 1
0.7101	Intermediate Similarity	NPD6752	Phase 1
0.7076	Intermediate Similarity	NPD3519	Discontinued
0.7073	Intermediate Similarity	NPD3137	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1619	Phase 3
0.7045	Intermediate Similarity	NPD951	Approved
0.703	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3917	Approved
0.703	Intermediate Similarity	NPD3918	Approved
0.7025	Intermediate Similarity	NPD1123	Approved
0.7025	Intermediate Similarity	NPD1124	Approved
0.7021	Intermediate Similarity	NPD6557	Phase 2
0.7006	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3915	Approved
0.6964	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7105	Phase 1
0.6919	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1079	Discontinued
0.6905	Remote Similarity	NPD4214	Discontinued
0.6897	Remote Similarity	NPD5941	Approved
0.6897	Remote Similarity	NPD5942	Approved
0.6891	Remote Similarity	NPD7570	Approved
0.6891	Remote Similarity	NPD7569	Approved
0.6878	Remote Similarity	NPD5923	Phase 1
0.6864	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7142	Discontinued
0.686	Remote Similarity	NPD3016	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5918	Discontinued
0.6848	Remote Similarity	NPD2431	Approved
0.6848	Remote Similarity	NPD2432	Approved
0.6845	Remote Similarity	NPD5774	Approved
0.6845	Remote Similarity	NPD5775	Approved
0.6842	Remote Similarity	NPD6768	Approved
0.6831	Remote Similarity	NPD2037	Approved
0.6821	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4329	Approved
0.6809	Remote Similarity	NPD4330	Approved
0.68	Remote Similarity	NPD4432	Discontinued
0.68	Remote Similarity	NPD4161	Discontinued
0.6791	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3792	Approved
0.6789	Remote Similarity	NPD4412	Phase 2
0.678	Remote Similarity	NPD3248	Phase 1
0.6774	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3782	Discontinued
0.6749	Remote Similarity	NPD7232	Discontinued
0.6743	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2454	Approved
0.6739	Remote Similarity	NPD2455	Approved
0.6733	Remote Similarity	NPD6260	Discontinued
0.6727	Remote Similarity	NPD4549	Discontinued
0.6724	Remote Similarity	NPD6017	Discontinued
0.6705	Remote Similarity	NPD2820	Phase 3
0.6705	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5840	Discontinued
0.67	Remote Similarity	NPD7817	Phase 1
0.6687	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD33	Approved
0.6685	Remote Similarity	NPD4393	Approved
0.6667	Remote Similarity	NPD3790	Phase 2
0.6667	Remote Similarity	NPD8240	Discontinued
0.6667	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1967	Approved
0.6667	Remote Similarity	NPD7552	Discontinued
0.6667	Remote Similarity	NPD1968	Approved
0.6667	Remote Similarity	NPD3776	Discontinued
0.6667	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7600	Phase 2
0.6648	Remote Similarity	NPD1802	Approved
0.6648	Remote Similarity	NPD1801	Approved
0.6647	Remote Similarity	NPD2365	Approved
0.6647	Remote Similarity	NPD1069	Approved
0.6647	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1070	Approved
0.6629	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4942	Approved
0.661	Remote Similarity	NPD5423	Phase 2
0.6608	Remote Similarity	NPD6901	Phase 3
0.6601	Remote Similarity	NPD2723	Phase 3
0.6599	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3470	Approved
0.6597	Remote Similarity	NPD3471	Approved
0.6596	Remote Similarity	NPD5466	Approved
0.6596	Remote Similarity	NPD2359	Approved
0.659	Remote Similarity	NPD2010	Phase 3
0.6588	Remote Similarity	NPD3908	Approved
0.6588	Remote Similarity	NPD2331	Discontinued
0.6587	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6487	Approved
0.6585	Remote Similarity	NPD6486	Approved
0.6585	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD941	Approved
0.6561	Remote Similarity	NPD2361	Approved
0.6561	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD2413	Phase 2
0.6559	Remote Similarity	NPD2404	Discontinued
0.6559	Remote Similarity	NPD3468	Approved
0.6557	Remote Similarity	NPD4311	Approved
0.6557	Remote Similarity	NPD2506	Approved
0.6556	Remote Similarity	NPD5086	Approved
0.6535	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7727	Phase 2
0.6526	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2350	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7072	Phase 2
0.6517	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4682	Phase 2
0.6517	Remote Similarity	NPD7528	Approved
0.6512	Remote Similarity	NPD3096	Phase 2
0.6509	Remote Similarity	NPD1919	Approved
0.6509	Remote Similarity	NPD5581	Approved
0.6509	Remote Similarity	NPD1920	Approved
0.6503	Remote Similarity	NPD7599	Phase 2
0.6502	Remote Similarity	NPD3775	Approved
0.6502	Remote Similarity	NPD3773	Approved
0.6502	Remote Similarity	NPD3774	Approved
0.65	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1524	Phase 1
0.6497	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7677	Discontinued
0.648	Remote Similarity	NPD2356	Phase 1
0.648	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7205	Discontinued
0.6467	Remote Similarity	NPD5993	Phase 1
0.6465	Remote Similarity	NPD6665	Discontinued
0.6461	Remote Similarity	NPD6088	Approved
0.6456	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7854	Phase 2
0.6453	Remote Similarity	NPD3891	Phase 2
0.6453	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD3890	Phase 2
0.6448	Remote Similarity	NPD8630	Approved
0.6447	Remote Similarity	NPD7617	Discontinued
0.6444	Remote Similarity	NPD5982	Phase 2
0.6443	Remote Similarity	NPD1096	Discontinued
0.6433	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4185	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4888	Discontinued
0.6422	Remote Similarity	NPD7724	Phase 2
0.6421	Remote Similarity	NPD2461	Phase 1
0.6416	Remote Similarity	NPD6358	Phase 2
0.6414	Remote Similarity	NPD5076	Approved
0.6414	Remote Similarity	NPD5504	Discontinued
0.6414	Remote Similarity	NPD5077	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