NPASS Compound

Structure

CID107160 OpenBabel06191715452D 48 52 0 0 1 0 0 0 0 0999 V2000 9.6394 2.0197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1394 2.8857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6394 2.0197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6394 3.7517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7915 3.9735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6160 2.3554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4727 4.6236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6280 1.3184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6394 3.7517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6006 3.3857 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7024 1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2861 2.7965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6006 2.3857 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4945 0.9706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5516 2.0767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8739 3.6055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1394 4.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2916 2.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1394 2.8857 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0933 1.7796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8684 3.5010 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.6394 5.4838 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4672 4.5191 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1151 3.8146 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4941 1.8184 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.1394 2.8857 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 0.1151 1.9875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7915 1.7979 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1637 0.2274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8606 1.1256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1394 4.6177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2780 6.1436 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6748 6.3648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3237 3.1287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1025 4.5255 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 4.8961 4.9680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7205 3.3500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5516 3.6947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8364 2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4993 4.7468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 4.0871 5.5558 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 2.9115 3.9377 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 9 1 0 0 0 0 3 27 2 0 0 0 0 4 9 2 0 0 0 0 4 27 1 0 0 0 0 5 40 1 0 0 0 0 6 41 1 0 0 0 0 7 24 2 0 0 0 0 7 25 1 0 0 0 0 8 26 2 0 0 0 0 8 28 1 0 0 0 0 9 18 1 0 0 0 0 10 5 1 1 0 0 0 10 13 1 0 0 0 0 10 42 1 0 0 0 0 11 6 1 6 0 0 0 11 14 1 0 0 0 0 11 43 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 29 1 6 0 0 0 14 16 1 0 0 0 0 14 30 1 1 0 0 0 15 20 1 0 0 0 0 15 31 1 6 0 0 0 16 21 1 0 0 0 0 16 44 1 1 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 23 2 0 0 0 0 18 32 1 0 0 0 0 19 25 2 0 0 0 0 19 28 1 0 0 0 0 20 27 1 1 0 0 0 20 42 1 0 0 0 0 21 28 1 6 0 0 0 21 43 1 0 0 0 0 33 46 2 0 0 0 0 34 46 1 0 0 0 0 35 46 1 0 0 0 0 36 47 1 0 0 0 0 37 47 2 0 0 0 0 38 48 2 0 0 0 0 39 48 1 0 0 0 0 40 47 1 0 0 0 0 41 48 1 0 0 0 0 44 46 1 0 0 0 0 45 47 1 0 0 0 0 45 48 1 0 0 0 0 M CHG 2 27 1 39 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.09
Volume:	305.285
LogP:	2.171
LogD:	2.627
LogS:	-3.809
# Rotatable Bonds:	2
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.887
Synthetic Accessibility Score:	3.532
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	1.4445793567574583e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	97.13922882080078%
Volume Distribution (VD):	0.502
Pgp-substrate:	7.360510349273682%

ADMET: Metabolism

CYP1A2-inhibitor:	0.608
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.411
CYP2C19-substrate:	0.685
CYP2C9-inhibitor:	0.738
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.397
CYP2D6-substrate:	0.677
CYP3A4-inhibitor:	0.616
CYP3A4-substrate:	0.782

ADMET: Excretion

Clearance (CL):	4.342
Half-life (T1/2):	0.459

ADMET: Toxicity

hERG Blockers:	0.173
Human Hepatotoxicity (H-HT):	0.444
Drug-inuced Liver Injury (DILI):	0.662
AMES Toxicity:	0.323
Rat Oral Acute Toxicity:	0.549
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.931
Carcinogencity:	0.108
Eye Corrosion:	0.003
Eye Irritation:	0.792
Respiratory Toxicity:	0.533

Download Data

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

Natural Product: NPC107160

Natural Product ID:	NPC107160
*Common Name:**	Sodium Beta-Nicotinamide Adenine Dinucleotide Phosphate
IUPAC Name:	[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methyl [[(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphate
Synonyms:
Standard InCHIKey:	XJLXINKUBYWONI-NNYOXOHSSA-N
Standard InCHI:	InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
SMILES:	c1cc(c[n+](c1)[C@H]1[C@@H]([C@@H]([C@@H](COP(=O)(O)OP(=O)([O-])OC[C@@H]2[C@H]([C@H]([C@H](n3cnc4c(N)ncnc34)O2)OP(=O)(O)O)O)O1)O)O)C(=N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL295069
PubChem CID:	57525501 5885
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0003468] (5'->5')-dinucleotides

*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
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18071251]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	faeces	n.a.	PMID[18323202]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22874	Bombyx mori	Species	Bombycidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22874	Bombyx mori	Species	Bombycidae	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
Kd	7
Others	31

Activity Type	# Activity
Individual Protein	5
Organism	7
Others	21
SINGLE PROTEIN	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3582	Individual Protein	Ketopantoate reductase	Escherichia coli K-12	Kd	=	260.0	nM	PMID[523637]
NPT4221	Individual Protein	Squalene synthetase	Homo sapiens	Km	=	430000.0	nM	PMID[523638]
NPT4221	Individual Protein	Squalene synthetase	Homo sapiens	Vmax	=	3800.0	nmol/min/mg	PMID[523638]
NPT605	Organism	Homo sapiens	Homo sapiens	Kd	=	40.0	n.a.	PMID[523635]
NPT32	Organism	Mus musculus	Mus musculus	Kd	=	1.85	n.a.	PMID[523635]
NPT2	Others	Unspecified		Kd	=	0.05	n.a.	PMID[523635]
NPT605	Organism	Homo sapiens	Homo sapiens	Kd	=	25.0	n.a.	PMID[523635]
NPT32	Organism	Mus musculus	Mus musculus	Kd	=	1.4	n.a.	PMID[523635]
NPT605	Organism	Homo sapiens	Homo sapiens	Kd	=	0.6	n.a.	PMID[523635]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	k_off	=	3.5	s-1	PMID[523636]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	k_off	=	60.0	s-1	PMID[523636]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	k_off	=	56.0	s-1	PMID[523636]
NPT24902	SINGLE PROTEIN	Dihydrofolate reductase	Escherichia coli	k_off	=	28.0	s-1	PMID[523636]
NPT2	Others	Unspecified		Km	=	40000.0	nM	PMID[523638]
NPT2	Others	Unspecified		Vmax	=	0.43	nmol/min/mg	PMID[523638]
NPT2	Others	Unspecified		Km	=	33000.0	nM	PMID[523638]
NPT2	Others	Unspecified		Vmax	=	0.76	nmol/min/mg	PMID[523638]
NPT2	Others	Unspecified		Km	=	62000.0	nM	PMID[523638]
NPT2	Others	Unspecified		Vmax	=	0.58	nmol/min/mg	PMID[523638]
NPT2	Others	Unspecified		Km	=	57000.0	nM	PMID[523638]
NPT2	Others	Unspecified		Vmax	=	0.84	nmol/min/mg	PMID[523638]
NPT2	Others	Unspecified		Km	=	530000.0	nM	PMID[523638]
NPT2	Others	Unspecified		Km	=	23340.0	nM	PMID[523638]
NPT2	Others	Unspecified		Vmax	=	1853.24	nmol/min/mg	PMID[523638]
NPT2	Others	Unspecified		Km	=	38880.0	nM	PMID[523639]
NPT2	Others	Unspecified		Kcat	=	11.95	/s	PMID[523639]
NPT2	Others	Unspecified		Km	=	12900.0	nM	PMID[523639]
NPT2	Others	Unspecified		Kcat	=	22.6	/s	PMID[523639]
NPT2	Others	Unspecified		Km	=	70000.0	nM	PMID[523639]
NPT2	Others	Unspecified		Km	=	66000.0	nM	PMID[523639]
NPT2	Others	Unspecified		Km	=	80000.0	nM	PMID[523639]
NPT2	Others	Unspecified		Kcat/Km	=	322.35	/s/M	PMID[523639]
NPT2	Others	Unspecified		Kcat/Km	=	185.71	/s/M	PMID[523639]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	105.1	%	PMID[523640]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	190.03	%	PMID[523640]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	16.44	%	PMID[523641]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.03	%	PMID[523642]

☑ 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 NPC107160 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	647
0.1-0.2	7025
0.2-0.3	20914
0.3-0.4	8416
0.4-0.5	3059
0.5-0.6	2262
0.6-0.7	348
0.7-0.8	23
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9014	High Similarity	NPC21461
0.8119	Intermediate Similarity	NPC250178
0.7974	Intermediate Similarity	NPC158055
0.7686	Intermediate Similarity	NPC160666
0.7562	Intermediate Similarity	NPC319456
0.7438	Intermediate Similarity	NPC222174
0.7426	Intermediate Similarity	NPC168702
0.7426	Intermediate Similarity	NPC125659
0.7246	Intermediate Similarity	NPC326529
0.7214	Intermediate Similarity	NPC138018
0.7212	Intermediate Similarity	NPC319100
0.7212	Intermediate Similarity	NPC324198
0.7149	Intermediate Similarity	NPC150447
0.7116	Intermediate Similarity	NPC472289
0.7053	Intermediate Similarity	NPC326082
0.703	Intermediate Similarity	NPC226245
0.7015	Intermediate Similarity	NPC174802
0.6965	Remote Similarity	NPC130586
0.6965	Remote Similarity	NPC164952
0.6965	Remote Similarity	NPC212551
0.6965	Remote Similarity	NPC302778
0.6942	Remote Similarity	NPC323091
0.6915	Remote Similarity	NPC207633
0.6913	Remote Similarity	NPC471603
0.6907	Remote Similarity	NPC130570
0.6897	Remote Similarity	NPC224076
0.6887	Remote Similarity	NPC189261
0.6875	Remote Similarity	NPC33382
0.6866	Remote Similarity	NPC85689
0.6866	Remote Similarity	NPC161224
0.6866	Remote Similarity	NPC211025
0.6866	Remote Similarity	NPC185991
0.6858	Remote Similarity	NPC103388
0.684	Remote Similarity	NPC317054
0.6832	Remote Similarity	NPC321814
0.678	Remote Similarity	NPC239737
0.678	Remote Similarity	NPC316618
0.6758	Remote Similarity	NPC313514
0.675	Remote Similarity	NPC476492
0.6743	Remote Similarity	NPC62510
0.6733	Remote Similarity	NPC150853
0.6716	Remote Similarity	NPC121222
0.6682	Remote Similarity	NPC324033
0.6682	Remote Similarity	NPC321458
0.6681	Remote Similarity	NPC474767
0.6635	Remote Similarity	NPC261595
0.6611	Remote Similarity	NPC471506
0.6596	Remote Similarity	NPC282247
0.6567	Remote Similarity	NPC107374
0.6567	Remote Similarity	NPC156461
0.6567	Remote Similarity	NPC21448
0.6561	Remote Similarity	NPC471564
0.656	Remote Similarity	NPC295452
0.656	Remote Similarity	NPC39092
0.656	Remote Similarity	NPC171393
0.6557	Remote Similarity	NPC69843
0.655	Remote Similarity	NPC54537
0.6535	Remote Similarity	NPC164665
0.6535	Remote Similarity	NPC189068
0.6513	Remote Similarity	NPC238945
0.6511	Remote Similarity	NPC242923
0.6504	Remote Similarity	NPC89987
0.6502	Remote Similarity	NPC219313
0.6502	Remote Similarity	NPC269827
0.6502	Remote Similarity	NPC309832
0.65	Remote Similarity	NPC48938
0.6484	Remote Similarity	NPC476493
0.6484	Remote Similarity	NPC317010
0.6471	Remote Similarity	NPC477633
0.6468	Remote Similarity	NPC477796
0.6468	Remote Similarity	NPC477795
0.6468	Remote Similarity	NPC477806
0.6468	Remote Similarity	NPC229974
0.6468	Remote Similarity	NPC477805
0.6454	Remote Similarity	NPC81175
0.6434	Remote Similarity	NPC103687
0.6434	Remote Similarity	NPC132631
0.6398	Remote Similarity	NPC5145
0.6395	Remote Similarity	NPC314882
0.6393	Remote Similarity	NPC313884
0.6393	Remote Similarity	NPC98371
0.6386	Remote Similarity	NPC223223
0.6385	Remote Similarity	NPC71079
0.6385	Remote Similarity	NPC63109
0.638	Remote Similarity	NPC314394
0.6368	Remote Similarity	NPC161659
0.6368	Remote Similarity	NPC209525
0.6355	Remote Similarity	NPC474217
0.6346	Remote Similarity	NPC472816
0.6342	Remote Similarity	NPC472031
0.6342	Remote Similarity	NPC472067
0.6342	Remote Similarity	NPC472066
0.6338	Remote Similarity	NPC14590
0.6328	Remote Similarity	NPC472068
0.6326	Remote Similarity	NPC85918
0.6325	Remote Similarity	NPC470500
0.6322	Remote Similarity	NPC308906
0.6314	Remote Similarity	NPC472434
0.6305	Remote Similarity	NPC314152
0.6303	Remote Similarity	NPC311197
0.6303	Remote Similarity	NPC54320
0.6303	Remote Similarity	NPC320968
0.6303	Remote Similarity	NPC313754
0.6298	Remote Similarity	NPC478006
0.6298	Remote Similarity	NPC74619
0.6296	Remote Similarity	NPC278366
0.6296	Remote Similarity	NPC477634
0.6296	Remote Similarity	NPC127730
0.629	Remote Similarity	NPC116622
0.6287	Remote Similarity	NPC317821
0.6278	Remote Similarity	NPC315467
0.6277	Remote Similarity	NPC149708
0.6273	Remote Similarity	NPC203754
0.6273	Remote Similarity	NPC150048
0.6271	Remote Similarity	NPC166492
0.6271	Remote Similarity	NPC473362
0.6266	Remote Similarity	NPC472027
0.6265	Remote Similarity	NPC314774
0.6265	Remote Similarity	NPC475859
0.6265	Remote Similarity	NPC315126
0.6265	Remote Similarity	NPC475969
0.6256	Remote Similarity	NPC52238
0.6255	Remote Similarity	NPC478009
0.6255	Remote Similarity	NPC478010
0.625	Remote Similarity	NPC156003
0.6245	Remote Similarity	NPC30540
0.6245	Remote Similarity	NPC314957
0.624	Remote Similarity	NPC472285
0.6239	Remote Similarity	NPC164664
0.6238	Remote Similarity	NPC129756
0.6234	Remote Similarity	NPC54981
0.6233	Remote Similarity	NPC161887
0.6233	Remote Similarity	NPC219963
0.6233	Remote Similarity	NPC477891
0.6225	Remote Similarity	NPC477175
0.6225	Remote Similarity	NPC470730
0.6224	Remote Similarity	NPC50511
0.622	Remote Similarity	NPC64216
0.622	Remote Similarity	NPC477861
0.6214	Remote Similarity	NPC64705
0.6214	Remote Similarity	NPC232408
0.6211	Remote Similarity	NPC75544
0.621	Remote Similarity	NPC110151
0.621	Remote Similarity	NPC244536
0.6209	Remote Similarity	NPC469975
0.6207	Remote Similarity	NPC212213
0.6207	Remote Similarity	NPC265576
0.6202	Remote Similarity	NPC471891
0.6202	Remote Similarity	NPC324815
0.6188	Remote Similarity	NPC30326
0.6186	Remote Similarity	NPC470505
0.6185	Remote Similarity	NPC314954
0.6183	Remote Similarity	NPC473757
0.618	Remote Similarity	NPC314056
0.6178	Remote Similarity	NPC284559
0.6178	Remote Similarity	NPC284678
0.6175	Remote Similarity	NPC165743
0.6174	Remote Similarity	NPC226202
0.6173	Remote Similarity	NPC267811
0.6173	Remote Similarity	NPC304926
0.6173	Remote Similarity	NPC476041
0.6165	Remote Similarity	NPC177169
0.6165	Remote Similarity	NPC89147
0.6165	Remote Similarity	NPC274384
0.6165	Remote Similarity	NPC317746
0.6164	Remote Similarity	NPC256828
0.616	Remote Similarity	NPC115595
0.6157	Remote Similarity	NPC313640
0.6157	Remote Similarity	NPC250835
0.6154	Remote Similarity	NPC313897
0.6151	Remote Similarity	NPC220852
0.6151	Remote Similarity	NPC469589
0.615	Remote Similarity	NPC188387
0.615	Remote Similarity	NPC163421
0.6145	Remote Similarity	NPC6215
0.6143	Remote Similarity	NPC141377
0.6143	Remote Similarity	NPC133261
0.6142	Remote Similarity	NPC28945
0.614	Remote Similarity	NPC478011
0.614	Remote Similarity	NPC478012
0.6139	Remote Similarity	NPC107836
0.6136	Remote Similarity	NPC105758
0.6136	Remote Similarity	NPC476686
0.6136	Remote Similarity	NPC476688
0.6135	Remote Similarity	NPC474877
0.6133	Remote Similarity	NPC472110
0.6133	Remote Similarity	NPC99891
0.6133	Remote Similarity	NPC472109
0.6132	Remote Similarity	NPC147983
0.6132	Remote Similarity	NPC177996
0.613	Remote Similarity	NPC56271
0.6129	Remote Similarity	NPC162268
0.6126	Remote Similarity	NPC472122
0.6126	Remote Similarity	NPC24594
0.6121	Remote Similarity	NPC292361
0.6119	Remote Similarity	NPC278874
0.6118	Remote Similarity	NPC475070
0.6117	Remote Similarity	NPC211820
0.6117	Remote Similarity	NPC251233
0.6117	Remote Similarity	NPC314176

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 NPC107160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	794
0.2-0.3	1292
0.3-0.4	2626
0.4-0.5	1751
0.5-0.6	1877
0.6-0.7	529
0.7-0.8	45
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
0.8111	Intermediate Similarity	NPD5080	Phase 2
0.8066	Intermediate Similarity	NPD2877	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD2876	Phase 3
0.8065	Intermediate Similarity	NPD5079	Phase 2
0.8037	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD2965	Clinical (unspecified phase)
0.7991	Intermediate Similarity	NPD2824	Phase 2
0.7974	Intermediate Similarity	NPD6840	Approved
0.7833	Intermediate Similarity	NPD4744	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4187	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD8250	Phase 2
0.7783	Intermediate Similarity	NPD4716	Approved
0.7763	Intermediate Similarity	NPD2902	Phase 2
0.7763	Intermediate Similarity	NPD2903	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4612	Discontinued
0.774	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD1915	Phase 1
0.7674	Intermediate Similarity	NPD5486	Discontinued
0.7605	Intermediate Similarity	NPD6351	Discovery
0.7586	Intermediate Similarity	NPD7502	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD5458	Discontinued
0.7546	Intermediate Similarity	NPD4458	Phase 2
0.7546	Intermediate Similarity	NPD4459	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD2152	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD796	Phase 2
0.7389	Intermediate Similarity	NPD9582	Phase 3
0.7358	Intermediate Similarity	NPD207	Discontinued
0.7297	Intermediate Similarity	NPD2451	Phase 2
0.7297	Intermediate Similarity	NPD2452	Phase 2
0.7297	Intermediate Similarity	NPD2450	Phase 2
0.7297	Intermediate Similarity	NPD2453	Phase 2
0.7264	Intermediate Similarity	NPD1063	Phase 2
0.7261	Intermediate Similarity	NPD6381	Phase 2
0.7249	Intermediate Similarity	NPD534	Phase 2
0.7249	Intermediate Similarity	NPD537	Phase 2
0.7238	Intermediate Similarity	NPD6992	Phase 2
0.7212	Intermediate Similarity	NPD4171	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8321	Discontinued
0.72	Intermediate Similarity	NPD4495	Phase 1
0.7183	Intermediate Similarity	NPD3913	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD2536	Discontinued
0.7176	Intermediate Similarity	NPD2127	Suspended
0.7118	Intermediate Similarity	NPD6957	Approved
0.7118	Intermediate Similarity	NPD6958	Approved
0.7118	Intermediate Similarity	NPD6711	Approved
0.7067	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4654	Phase 1
0.7033	Intermediate Similarity	NPD1599	Approved
0.7033	Intermediate Similarity	NPD5171	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4306	Phase 1
0.7018	Intermediate Similarity	NPD4563	Phase 2
0.7015	Intermediate Similarity	NPD339	Approved
0.7009	Intermediate Similarity	NPD1692	Approved
0.7008	Intermediate Similarity	NPD7273	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6307	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD1197	Approved
0.6981	Remote Similarity	NPD1046	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4414	Discontinued
0.6965	Remote Similarity	NPD338	Approved
0.6951	Remote Similarity	NPD8375	Approved
0.6946	Remote Similarity	NPD8004	Discontinued
0.6944	Remote Similarity	NPD2591	Phase 2
0.6943	Remote Similarity	NPD3265	Phase 1
0.6941	Remote Similarity	NPD4615	Phase 2
0.6941	Remote Similarity	NPD1234	Discontinued
0.6936	Remote Similarity	NPD6036	Suspended
0.6933	Remote Similarity	NPD4714	Approved
0.6933	Remote Similarity	NPD34	Approved
0.6933	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6970	Phase 2
0.691	Remote Similarity	NPD1623	Approved
0.6909	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD169	Phase 2
0.6895	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3830	Phase 1
0.6883	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7504	Discontinued
0.6878	Remote Similarity	NPD5703	Discontinued
0.6878	Remote Similarity	NPD4999	Phase 3
0.6878	Remote Similarity	NPD4998	Phase 3
0.6875	Remote Similarity	NPD2062	Phase 2
0.6866	Remote Similarity	NPD706	Phase 1
0.6866	Remote Similarity	NPD5757	Discontinued
0.6866	Remote Similarity	NPD283	Approved
0.6866	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6721	Phase 1
0.6864	Remote Similarity	NPD2839	Phase 2
0.6861	Remote Similarity	NPD5885	Approved
0.6858	Remote Similarity	NPD2364	Suspended
0.6836	Remote Similarity	NPD5949	Phase 3
0.6835	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6829	Phase 2
0.6833	Remote Similarity	NPD5428	Discontinued
0.6833	Remote Similarity	NPD3403	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6192	Phase 3
0.6826	Remote Similarity	NPD3013	Phase 3
0.682	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4080	Discontinued
0.6802	Remote Similarity	NPD5534	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5584	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD242	Approved
0.6798	Remote Similarity	NPD7323	Phase 2
0.6794	Remote Similarity	NPD1333	Phase 3
0.6789	Remote Similarity	NPD2872	Phase 2
0.6783	Remote Similarity	NPD6023	Discontinued
0.6778	Remote Similarity	NPD6352	Phase 2
0.6776	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD2386	Approved
0.6766	Remote Similarity	NPD3521	Phase 2
0.6762	Remote Similarity	NPD1215	Discontinued
0.6761	Remote Similarity	NPD7856	Phase 2
0.6761	Remote Similarity	NPD7857	Phase 3
0.6759	Remote Similarity	NPD8442	Discontinued
0.6758	Remote Similarity	NPD7706	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7138	Phase 2
0.6756	Remote Similarity	NPD6175	Phase 3
0.6753	Remote Similarity	NPD4990	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6626	Approved
0.6738	Remote Similarity	NPD5679	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD6573	Phase 3
0.6734	Remote Similarity	NPD6572	Phase 2
0.6732	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6763	Discontinued
0.6722	Remote Similarity	NPD1571	Phase 2
0.6712	Remote Similarity	NPD3406	Suspended
0.671	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7188	Phase 3
0.6709	Remote Similarity	NPD6856	Discontinued
0.6708	Remote Similarity	NPD1273	Discontinued
0.6707	Remote Similarity	NPD6605	Phase 3
0.6705	Remote Similarity	NPD6754	Phase 3
0.6699	Remote Similarity	NPD1015	Phase 2
0.6699	Remote Similarity	NPD1016	Phase 2
0.6696	Remote Similarity	NPD4533	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4683	Phase 3
0.6681	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7486	Phase 1
0.668	Remote Similarity	NPD2349	Phase 3
0.668	Remote Similarity	NPD6326	Phase 2
0.668	Remote Similarity	NPD3343	Phase 3
0.6667	Remote Similarity	NPD2993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5802	Phase 2
0.6667	Remote Similarity	NPD5925	Phase 1
0.6667	Remote Similarity	NPD7067	Approved
0.6667	Remote Similarity	NPD7068	Approved
0.6667	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD1912	Approved
0.6651	Remote Similarity	NPD2333	Discontinued
0.664	Remote Similarity	NPD5172	Phase 2
0.664	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5827	Discontinued
0.6639	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5627	Approved
0.6639	Remote Similarity	NPD1572	Phase 2
0.6637	Remote Similarity	NPD7722	Suspended
0.6636	Remote Similarity	NPD6417	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD247	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5644	Phase 1
0.6622	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3439	Approved
0.6612	Remote Similarity	NPD6164	Phase 2
0.6612	Remote Similarity	NPD6327	Phase 1
0.6612	Remote Similarity	NPD6165	Phase 2
0.6612	Remote Similarity	NPD7415	Suspended
0.661	Remote Similarity	NPD7112	Discontinued
0.6609	Remote Similarity	NPD5520	Phase 2
0.6604	Remote Similarity	NPD2647	Phase 3
0.6604	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7851	Phase 1
0.6601	Remote Similarity	NPD7850	Discontinued
0.6598	Remote Similarity	NPD4401	Phase 2
0.6598	Remote Similarity	NPD4403	Phase 3
0.6595	Remote Similarity	NPD2357	Approved
0.6594	Remote Similarity	NPD2807	Discontinued
0.6594	Remote Similarity	NPD4872	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6132	Phase 1
0.6593	Remote Similarity	NPD691	Discontinued
0.6592	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2757	Phase 2
0.6582	Remote Similarity	NPD7423	Phase 2
0.6582	Remote Similarity	NPD5465	Phase 2
0.658	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6816	Phase 3
0.6574	Remote Similarity	NPD2751	Phase 1

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