NPASS Compound

Structure

NPC471741 OpenBabel07101718282D 39 42 0 0 1 0 0 0 0 0999 V2000 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 3 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 32 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 20 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 18 1 0 0 0 0 12 39 1 0 0 0 0 13 30 2 3 0 0 0 13 33 1 0 0 0 0 14 24 1 0 0 0 0 15 24 1 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 18 30 1 0 0 0 0 19 21 1 0 0 0 0 19 32 1 0 0 0 0 20 22 2 0 0 0 0 20 39 1 0 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 34 2 0 0 0 0 25 28 2 0 0 0 0 25 35 1 0 0 0 0 26 29 2 0 0 0 0 26 36 1 0 0 0 0 27 37 2 0 0 0 0 27 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	547.15
Volume:	530.646
LogP:	1.294
LogD:	0.767
LogS:	-4.639
# Rotatable Bonds:	10
TPSA:	184.92
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	3.548
Fsp3:	0.148
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.317
MDCK Permeability:	5.5122172852861695e-06
Pgp-inhibitor:	0.042
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	90.1924057006836%
Volume Distribution (VD):	0.539
Pgp-substrate:	10.8500337600708%

ADMET: Metabolism

CYP1A2-inhibitor:	0.125
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.658
CYP2C9-substrate:	0.254
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.134
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	1.115
Half-life (T1/2):	0.533

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.311
Carcinogencity:	0.5
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.359

Download Data

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

Natural Product: NPC471741

Natural Product ID:	NPC471741
*Common Name:**	Dermacozine J
IUPAC Name:	2-acetamido-3-[(7-benzoyl-4,9-dicarbamoyl-5-methyl-10H-phenazin-1-yl)sulfanyl]propanoic acid
Synonyms:
Standard InCHIKey:	ZSWYLEPUUBUTJS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H25N5O6S/c1-13(33)30-18(27(37)38)12-39-20-9-8-16(25(28)35)23-22(20)31-21-17(26(29)36)10-15(11-19(21)32(23)2)24(34)14-6-4-3-5-7-14/h3-11,18,31H,12H2,1-2H3,(H2,28,35)(H2,29,36)(H,30,33)(H,37,38)
SMILES:	CC(=O)NC(CSC1=C2C(=C(C=C1)C(=O)N)N(C3=CC(=CC(=C3N2)C(=O)N)C(=O)C4=CC=CC=C4)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109425
PubChem CID:	76317496
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000486] Quinoxalines [CHEMONTID:0000416] Phenazines 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
NPO15561	Dermacoccus abyssi	Species	Dermacoccaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20448892]
NPO15561	Dermacoccus abyssi	Species	Dermacoccaceae	Bacteria	n.a.	Mariana Trench sediments	n.a.	PMID[24499261]
NPO15561	Dermacoccus abyssi	Species	Dermacoccaceae	Bacteria	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	19600.0	nM	PMID[558264]

☑ 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 NPC471741 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	332
0.1-0.2	2719
0.2-0.3	13594
0.3-0.4	14130
0.4-0.5	8298
0.5-0.6	3466
0.6-0.7	153
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC470317
0.785	Intermediate Similarity	NPC313293
0.7778	Intermediate Similarity	NPC471742
0.7744	Intermediate Similarity	NPC471743
0.7143	Intermediate Similarity	NPC27904
0.6957	Remote Similarity	NPC243058
0.6927	Remote Similarity	NPC478039
0.6923	Remote Similarity	NPC203635
0.6857	Remote Similarity	NPC90415
0.6832	Remote Similarity	NPC182131
0.6816	Remote Similarity	NPC189116
0.6812	Remote Similarity	NPC256268
0.6763	Remote Similarity	NPC219848
0.6742	Remote Similarity	NPC314648
0.671	Remote Similarity	NPC478141
0.6637	Remote Similarity	NPC315638
0.6637	Remote Similarity	NPC314855
0.6637	Remote Similarity	NPC313345
0.6637	Remote Similarity	NPC313796
0.6624	Remote Similarity	NPC477516
0.6615	Remote Similarity	NPC472243
0.6608	Remote Similarity	NPC193370
0.6607	Remote Similarity	NPC314297
0.6607	Remote Similarity	NPC315545
0.6564	Remote Similarity	NPC124636
0.6548	Remote Similarity	NPC254798
0.6546	Remote Similarity	NPC472241
0.6545	Remote Similarity	NPC248782
0.6532	Remote Similarity	NPC98864
0.6531	Remote Similarity	NPC472242
0.652	Remote Similarity	NPC476231
0.652	Remote Similarity	NPC314834
0.6457	Remote Similarity	NPC471944
0.6445	Remote Similarity	NPC14849
0.6432	Remote Similarity	NPC66699
0.6429	Remote Similarity	NPC478040
0.6426	Remote Similarity	NPC315893
0.6426	Remote Similarity	NPC313587
0.6426	Remote Similarity	NPC316110
0.6411	Remote Similarity	NPC318183
0.6396	Remote Similarity	NPC314186
0.638	Remote Similarity	NPC472539
0.638	Remote Similarity	NPC470787
0.638	Remote Similarity	NPC472540
0.6377	Remote Similarity	NPC471130
0.6364	Remote Similarity	NPC250448
0.6359	Remote Similarity	NPC199737
0.6351	Remote Similarity	NPC472542
0.6351	Remote Similarity	NPC472541
0.6351	Remote Similarity	NPC141454
0.6351	Remote Similarity	NPC328611
0.635	Remote Similarity	NPC300596
0.635	Remote Similarity	NPC237649
0.6346	Remote Similarity	NPC472114
0.6346	Remote Similarity	NPC472115
0.6338	Remote Similarity	NPC131450
0.6338	Remote Similarity	NPC182057
0.6338	Remote Similarity	NPC474041
0.6338	Remote Similarity	NPC147298
0.6327	Remote Similarity	NPC43477
0.6327	Remote Similarity	NPC165599
0.6323	Remote Similarity	NPC474916
0.632	Remote Similarity	NPC244856
0.6316	Remote Similarity	NPC471155
0.6316	Remote Similarity	NPC472245
0.6316	Remote Similarity	NPC244741
0.6316	Remote Similarity	NPC175916
0.6308	Remote Similarity	NPC475685
0.6306	Remote Similarity	NPC108847
0.6305	Remote Similarity	NPC107836
0.6293	Remote Similarity	NPC31700
0.6288	Remote Similarity	NPC270241
0.6283	Remote Similarity	NPC57398
0.6282	Remote Similarity	NPC312645
0.628	Remote Similarity	NPC289776
0.628	Remote Similarity	NPC133470
0.628	Remote Similarity	NPC191863
0.628	Remote Similarity	NPC88970
0.6274	Remote Similarity	NPC248862
0.6272	Remote Similarity	NPC225400
0.6263	Remote Similarity	NPC150863
0.6261	Remote Similarity	NPC229893
0.6245	Remote Similarity	NPC472538
0.6245	Remote Similarity	NPC470786
0.6244	Remote Similarity	NPC475607
0.624	Remote Similarity	NPC218388
0.6228	Remote Similarity	NPC473239
0.6227	Remote Similarity	NPC471195
0.6227	Remote Similarity	NPC471196
0.6223	Remote Similarity	NPC89508
0.6223	Remote Similarity	NPC236424
0.6223	Remote Similarity	NPC306644
0.6222	Remote Similarity	NPC317727
0.6215	Remote Similarity	NPC474081
0.621	Remote Similarity	NPC473815
0.6198	Remote Similarity	NPC314098
0.6197	Remote Similarity	NPC475594
0.6197	Remote Similarity	NPC477979
0.6197	Remote Similarity	NPC274842
0.619	Remote Similarity	NPC278887
0.6186	Remote Similarity	NPC253476
0.6186	Remote Similarity	NPC474815
0.6184	Remote Similarity	NPC143325
0.6182	Remote Similarity	NPC255909
0.6182	Remote Similarity	NPC477998
0.6179	Remote Similarity	NPC292265
0.6179	Remote Similarity	NPC474814
0.6179	Remote Similarity	NPC112336
0.6176	Remote Similarity	NPC216221
0.617	Remote Similarity	NPC322064
0.6168	Remote Similarity	NPC84347
0.6154	Remote Similarity	NPC322644
0.6154	Remote Similarity	NPC83111
0.6154	Remote Similarity	NPC317752
0.6146	Remote Similarity	NPC314431
0.6146	Remote Similarity	NPC280807
0.6143	Remote Similarity	NPC45850
0.614	Remote Similarity	NPC328596
0.614	Remote Similarity	NPC328318
0.6134	Remote Similarity	NPC77022
0.6134	Remote Similarity	NPC272174
0.6133	Remote Similarity	NPC272483
0.6121	Remote Similarity	NPC470548
0.6114	Remote Similarity	NPC295548
0.6111	Remote Similarity	NPC475761
0.6111	Remote Similarity	NPC318299
0.6109	Remote Similarity	NPC474896
0.6109	Remote Similarity	NPC183805
0.6106	Remote Similarity	NPC36495
0.6105	Remote Similarity	NPC472244
0.6105	Remote Similarity	NPC470343
0.6091	Remote Similarity	NPC287358
0.6091	Remote Similarity	NPC33949
0.6091	Remote Similarity	NPC160381
0.6089	Remote Similarity	NPC472116
0.6089	Remote Similarity	NPC259678
0.6089	Remote Similarity	NPC245916
0.6083	Remote Similarity	NPC31097
0.6082	Remote Similarity	NPC132329
0.6078	Remote Similarity	NPC288445
0.6071	Remote Similarity	NPC247735
0.6071	Remote Similarity	NPC472295
0.6071	Remote Similarity	NPC472210
0.6071	Remote Similarity	NPC81802
0.6071	Remote Similarity	NPC269886
0.6063	Remote Similarity	NPC472323
0.6063	Remote Similarity	NPC206186
0.6061	Remote Similarity	NPC317373
0.6059	Remote Similarity	NPC13470
0.6058	Remote Similarity	NPC153694
0.6058	Remote Similarity	NPC211525
0.6056	Remote Similarity	NPC472118
0.6054	Remote Similarity	NPC92803
0.605	Remote Similarity	NPC149014
0.6049	Remote Similarity	NPC476491
0.6043	Remote Similarity	NPC476098
0.6036	Remote Similarity	NPC103119
0.6034	Remote Similarity	NPC147983
0.6034	Remote Similarity	NPC469928
0.6034	Remote Similarity	NPC177996
0.6033	Remote Similarity	NPC476818
0.603	Remote Similarity	NPC242933
0.6026	Remote Similarity	NPC309845
0.6021	Remote Similarity	NPC205946
0.602	Remote Similarity	NPC184437
0.6019	Remote Similarity	NPC204867
0.6018	Remote Similarity	NPC472293
0.6017	Remote Similarity	NPC327592
0.6017	Remote Similarity	NPC132539
0.6016	Remote Similarity	NPC153400
0.6015	Remote Similarity	NPC313966
0.6015	Remote Similarity	NPC314254
0.6009	Remote Similarity	NPC39679
0.6008	Remote Similarity	NPC27041
0.6008	Remote Similarity	NPC173344
0.6008	Remote Similarity	NPC470018
0.6	Remote Similarity	NPC9894
0.6	Remote Similarity	NPC207851
0.6	Remote Similarity	NPC472207
0.5992	Remote Similarity	NPC298449
0.5991	Remote Similarity	NPC278434
0.5991	Remote Similarity	NPC90967
0.5991	Remote Similarity	NPC52059
0.5991	Remote Similarity	NPC470069
0.5982	Remote Similarity	NPC475962
0.5981	Remote Similarity	NPC471778
0.5972	Remote Similarity	NPC253667
0.5972	Remote Similarity	NPC35510
0.5972	Remote Similarity	NPC303225
0.5972	Remote Similarity	NPC472121
0.5968	Remote Similarity	NPC208522
0.5966	Remote Similarity	NPC330009
0.5964	Remote Similarity	NPC18890
0.5964	Remote Similarity	NPC221873
0.5964	Remote Similarity	NPC316405
0.5963	Remote Similarity	NPC219336
0.5963	Remote Similarity	NPC45048
0.5962	Remote Similarity	NPC41717
0.5956	Remote Similarity	NPC472292
0.5952	Remote Similarity	NPC243673

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 NPC471741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	591
0.2-0.3	1093
0.3-0.4	1391
0.4-0.5	3402
0.5-0.6	2253
0.6-0.7	223
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7259	Intermediate Similarity	NPD3587	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5663	Discontinued
0.7177	Intermediate Similarity	NPD7570	Approved
0.7177	Intermediate Similarity	NPD7569	Approved
0.715	Intermediate Similarity	NPD4150	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3481	Approved
0.709	Intermediate Similarity	NPD4043	Approved
0.709	Intermediate Similarity	NPD4046	Approved
0.7041	Intermediate Similarity	NPD6019	Approved
0.7041	Intermediate Similarity	NPD5659	Approved
0.7041	Intermediate Similarity	NPD6018	Approved
0.7041	Intermediate Similarity	NPD5660	Approved
0.7024	Intermediate Similarity	NPD6833	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5856	Discontinued
0.698	Remote Similarity	NPD3776	Discontinued
0.697	Remote Similarity	NPD5992	Approved
0.6952	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5445	Approved
0.6939	Remote Similarity	NPD4045	Phase 2
0.6939	Remote Similarity	NPD4042	Phase 2
0.6915	Remote Similarity	NPD4645	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3482	Approved
0.6845	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5046	Discontinued
0.6808	Remote Similarity	NPD5504	Discontinued
0.6804	Remote Similarity	NPD7316	Discontinued
0.674	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.67	Remote Similarity	NPD212	Discontinued
0.6699	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4888	Discontinued
0.6683	Remote Similarity	NPD3487	Phase 1
0.6667	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5077	Approved
0.6651	Remote Similarity	NPD5076	Approved
0.6604	Remote Similarity	NPD5923	Phase 1
0.6587	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5466	Approved
0.6569	Remote Similarity	NPD7734	Approved
0.6566	Remote Similarity	NPD5748	Phase 2
0.6552	Remote Similarity	NPD7275	Approved
0.654	Remote Similarity	NPD4330	Approved
0.654	Remote Similarity	NPD4329	Approved
0.6538	Remote Similarity	NPD5997	Discontinued
0.6535	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5488	Discontinued
0.6524	Remote Similarity	NPD5498	Phase 2
0.6517	Remote Similarity	NPD1397	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7664	Discontinued
0.648	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5918	Discontinued
0.6471	Remote Similarity	NPD4397	Phase 1
0.6468	Remote Similarity	NPD7786	Discontinued
0.6468	Remote Similarity	NPD6173	Approved
0.6468	Remote Similarity	NPD5086	Approved
0.6447	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD4092	Approved
0.6445	Remote Similarity	NPD3792	Approved
0.6444	Remote Similarity	NPD5901	Discontinued
0.6444	Remote Similarity	NPD7552	Discontinued
0.6435	Remote Similarity	NPD6891	Phase 2
0.6432	Remote Similarity	NPD4432	Discontinued
0.6429	Remote Similarity	NPD1625	Approved
0.6422	Remote Similarity	NPD5871	Discontinued
0.6422	Remote Similarity	NPD5042	Phase 1
0.6422	Remote Similarity	NPD6659	Phase 2
0.6419	Remote Similarity	NPD7595	Discontinued
0.6415	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD4438	Approved
0.64	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4091	Approved
0.6384	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.636	Remote Similarity	NPD7300	Phase 3
0.636	Remote Similarity	NPD7302	Phase 3
0.6359	Remote Similarity	NPD6484	Approved
0.6359	Remote Similarity	NPD6483	Approved
0.6359	Remote Similarity	NPD4948	Discontinued
0.6351	Remote Similarity	NPD3522	Approved
0.6351	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6492	Phase 2
0.6348	Remote Similarity	NPD4417	Approved
0.6348	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD4918	Discontinued
0.6347	Remote Similarity	NPD1235	Phase 3
0.6345	Remote Similarity	NPD6301	Phase 2
0.6344	Remote Similarity	NPD6260	Discontinued
0.6338	Remote Similarity	NPD3997	Approved
0.6338	Remote Similarity	NPD3998	Approved
0.6338	Remote Similarity	NPD3999	Approved
0.6333	Remote Similarity	NPD5633	Discontinued
0.633	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD6753	Phase 1
0.6329	Remote Similarity	NPD6752	Phase 1
0.6323	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7301	Phase 3
0.6318	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2413	Phase 2
0.6308	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4906	Approved
0.63	Remote Similarity	NPD4905	Approved
0.63	Remote Similarity	NPD4903	Approved
0.6298	Remote Similarity	NPD6369	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4412	Phase 2
0.6294	Remote Similarity	NPD1189	Approved
0.6292	Remote Similarity	NPD7767	Approved
0.6291	Remote Similarity	NPD3995	Approved
0.6291	Remote Similarity	NPD3994	Approved
0.6291	Remote Similarity	NPD3991	Approved
0.6291	Remote Similarity	NPD3992	Approved
0.6291	Remote Similarity	NPD3996	Approved
0.6291	Remote Similarity	NPD3993	Approved
0.6286	Remote Similarity	NPD7795	Phase 2
0.6286	Remote Similarity	NPD7677	Discontinued
0.6284	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7017	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6017	Discontinued
0.6279	Remote Similarity	NPD3990	Phase 3
0.6279	Remote Similarity	NPD7867	Phase 1
0.6278	Remote Similarity	NPD6162	Approved
0.6278	Remote Similarity	NPD6161	Approved
0.6274	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6274	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD4904	Approved
0.6262	Remote Similarity	NPD3782	Discontinued
0.6261	Remote Similarity	NPD5947	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD2882	Phase 1
0.625	Remote Similarity	NPD6846	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7091	Discontinued
0.6244	Remote Similarity	NPD1222	Discontinued
0.6244	Remote Similarity	NPD5937	Approved
0.6239	Remote Similarity	NPD8015	Phase 3
0.6239	Remote Similarity	NPD8149	Discontinued
0.6238	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD2037	Approved
0.6233	Remote Similarity	NPD3989	Phase 3
0.6228	Remote Similarity	NPD8115	Approved
0.6228	Remote Similarity	NPD8114	Approved
0.6228	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6987	Phase 1
0.6227	Remote Similarity	NPD5928	Phase 1
0.6226	Remote Similarity	NPD1660	Phase 2
0.6226	Remote Similarity	NPD3377	Discontinued
0.6225	Remote Similarity	NPD7921	Approved
0.6224	Remote Similarity	NPD1626	Approved
0.6223	Remote Similarity	NPD8314	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5609	Approved
0.6222	Remote Similarity	NPD5608	Approved
0.6214	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7770	Phase 3
0.6209	Remote Similarity	NPD2369	Discontinued
0.6207	Remote Similarity	NPD7272	Discontinued
0.6207	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD3471	Approved
0.6204	Remote Similarity	NPD3470	Approved
0.6201	Remote Similarity	NPD7010	Phase 3
0.62	Remote Similarity	NPD5933	Phase 3
0.62	Remote Similarity	NPD5932	Phase 3
0.62	Remote Similarity	NPD5931	Phase 3
0.6199	Remote Similarity	NPD2336	Approved
0.6199	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD4370	Phase 3
0.6197	Remote Similarity	NPD7324	Discontinued
0.619	Remote Similarity	NPD3874	Discontinued
0.619	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD4161	Discontinued
0.6186	Remote Similarity	NPD7292	Approved
0.6184	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD2431	Approved
0.6179	Remote Similarity	NPD3824	Phase 1
0.6179	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD2432	Approved
0.6175	Remote Similarity	NPD8281	Discontinued
0.6173	Remote Similarity	NPD7688	Phase 1
0.6171	Remote Similarity	NPD4376	Phase 3
0.6171	Remote Similarity	NPD8146	Phase 2
0.6171	Remote Similarity	NPD3479	Discontinued
0.6168	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7817	Phase 1
0.6167	Remote Similarity	NPD7934	Discovery
0.6167	Remote Similarity	NPD7931	Approved
0.6167	Remote Similarity	NPD7933	Approved
0.6167	Remote Similarity	NPD7727	Phase 2
0.6167	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6142	Phase 3
0.6162	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD2455	Approved
0.6161	Remote Similarity	NPD2454	Approved
0.616	Remote Similarity	NPD7404	Approved
0.6157	Remote Similarity	NPD6878	Phase 2

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