NPASS Compound

Structure

NPC471742 OpenBabel07101718282D 23 25 0 0 0 0 0 0 0 0999 V2000 -0.0000 -1.0000 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 2.5981 0.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 1.7321 -0.0000 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 0.8660 1.5000 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 -0.8660 1.5000 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 -1.0000 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 0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 9 1 0 0 0 0 4 11 2 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 8 1 0 0 0 0 7 20 2 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	311.09
Volume:	304.046
LogP:	2.414
LogD:	0.744
LogS:	-4.468
# Rotatable Bonds:	3
TPSA:	112.73
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	2.882
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.566
MDCK Permeability:	3.6262383673602017e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	83.06230163574219%
Volume Distribution (VD):	0.923
Pgp-substrate:	15.137190818786621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.134
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.125
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	1.477
Half-life (T1/2):	0.737

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.796
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC471742

Natural Product ID:	NPC471742
*Common Name:**	Dermacozine H
IUPAC Name:	6-carbamoyl-3-formyl-5-methyl-10H-phenazine-1-carboxylic acid
Synonyms:
Standard InCHIKey:	GUKUCMIJKFLKKJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H13N3O4/c1-19-12-6-8(7-20)5-10(16(22)23)13(12)18-11-4-2-3-9(14(11)19)15(17)21/h2-7,18H,1H3,(H2,17,21)(H,22,23)
SMILES:	O=Cc1cc(C(=O)O)c2c(c1)n(C)c1c([nH]2)cccc1C(=N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109427
PubChem CID:	76310270
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	=	18800.0	nM	PMID[534524]

☑ 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 NPC471742 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	247
0.1-0.2	2172
0.2-0.3	10829
0.3-0.4	10860
0.4-0.5	13959
0.5-0.6	3931
0.6-0.7	654
0.7-0.8	40
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8895	High Similarity	NPC470317
0.8701	High Similarity	NPC313293
0.8391	Intermediate Similarity	NPC471743
0.8363	Intermediate Similarity	NPC182131
0.8129	Intermediate Similarity	NPC27904
0.7826	Intermediate Similarity	NPC90415
0.779	Intermediate Similarity	NPC256268
0.7778	Intermediate Similarity	NPC471741
0.776	Intermediate Similarity	NPC243058
0.7735	Intermediate Similarity	NPC219848
0.7717	Intermediate Similarity	NPC203635
0.7561	Intermediate Similarity	NPC253476
0.7551	Intermediate Similarity	NPC314648
0.7424	Intermediate Similarity	NPC313345
0.7424	Intermediate Similarity	NPC313796
0.7424	Intermediate Similarity	NPC315638
0.7424	Intermediate Similarity	NPC314855
0.7396	Intermediate Similarity	NPC43477
0.7387	Intermediate Similarity	NPC314297
0.7387	Intermediate Similarity	NPC315545
0.7333	Intermediate Similarity	NPC189116
0.7277	Intermediate Similarity	NPC314834
0.7202	Intermediate Similarity	NPC173295
0.72	Intermediate Similarity	NPC300596
0.72	Intermediate Similarity	NPC237649
0.7198	Intermediate Similarity	NPC471130
0.7182	Intermediate Similarity	NPC88970
0.7169	Intermediate Similarity	NPC314098
0.7151	Intermediate Similarity	NPC472241
0.7136	Intermediate Similarity	NPC471944
0.7135	Intermediate Similarity	NPC472243
0.7126	Intermediate Similarity	NPC472242
0.7086	Intermediate Similarity	NPC478039
0.7047	Intermediate Similarity	NPC473815
0.7043	Intermediate Similarity	NPC318183
0.7039	Intermediate Similarity	NPC244856
0.7035	Intermediate Similarity	NPC242933
0.7	Intermediate Similarity	NPC475685
0.6985	Remote Similarity	NPC474916
0.6947	Remote Similarity	NPC182057
0.6947	Remote Similarity	NPC147298
0.6947	Remote Similarity	NPC131450
0.6923	Remote Similarity	NPC236424
0.6923	Remote Similarity	NPC306644
0.6895	Remote Similarity	NPC14849
0.6893	Remote Similarity	NPC259678
0.689	Remote Similarity	NPC274842
0.6879	Remote Similarity	NPC181527
0.6878	Remote Similarity	NPC475594
0.6878	Remote Similarity	NPC470548
0.6871	Remote Similarity	NPC130931
0.6865	Remote Similarity	NPC204867
0.6862	Remote Similarity	NPC292265
0.6842	Remote Similarity	NPC475607
0.6837	Remote Similarity	NPC477998
0.6833	Remote Similarity	NPC314223
0.6821	Remote Similarity	NPC159722
0.6814	Remote Similarity	NPC165599
0.6811	Remote Similarity	NPC199737
0.6809	Remote Similarity	NPC472118
0.6806	Remote Similarity	NPC474081
0.6805	Remote Similarity	NPC472245
0.6796	Remote Similarity	NPC244741
0.6793	Remote Similarity	NPC36495
0.6789	Remote Similarity	NPC328611
0.6786	Remote Similarity	NPC278434
0.678	Remote Similarity	NPC314186
0.6778	Remote Similarity	NPC144691
0.6766	Remote Similarity	NPC141454
0.6766	Remote Similarity	NPC205946
0.6762	Remote Similarity	NPC31700
0.675	Remote Similarity	NPC220151
0.675	Remote Similarity	NPC19692
0.6748	Remote Similarity	NPC229353
0.6737	Remote Similarity	NPC177261
0.6735	Remote Similarity	NPC160381
0.672	Remote Similarity	NPC476231
0.672	Remote Similarity	NPC471778
0.6717	Remote Similarity	NPC83111
0.6707	Remote Similarity	NPC226794
0.6705	Remote Similarity	NPC2823
0.6702	Remote Similarity	NPC278887
0.67	Remote Similarity	NPC45850
0.6699	Remote Similarity	NPC309845
0.6687	Remote Similarity	NPC268534
0.6686	Remote Similarity	NPC319645
0.6685	Remote Similarity	NPC288445
0.6684	Remote Similarity	NPC474041
0.6684	Remote Similarity	NPC49184
0.6684	Remote Similarity	NPC475761
0.6682	Remote Similarity	NPC89508
0.6667	Remote Similarity	NPC470971
0.6667	Remote Similarity	NPC9894
0.6667	Remote Similarity	NPC150323
0.6667	Remote Similarity	NPC472244
0.6667	Remote Similarity	NPC470343
0.6667	Remote Similarity	NPC312645
0.6667	Remote Similarity	NPC84347
0.6649	Remote Similarity	NPC153694
0.6649	Remote Similarity	NPC191310
0.6649	Remote Similarity	NPC61013
0.6649	Remote Similarity	NPC211525
0.6647	Remote Similarity	NPC184437
0.6647	Remote Similarity	NPC150863
0.6636	Remote Similarity	NPC229893
0.6635	Remote Similarity	NPC243850
0.6634	Remote Similarity	NPC472539
0.6634	Remote Similarity	NPC470787
0.6634	Remote Similarity	NPC472540
0.6633	Remote Similarity	NPC97584
0.6618	Remote Similarity	NPC472297
0.6618	Remote Similarity	NPC472296
0.6616	Remote Similarity	NPC206186
0.6615	Remote Similarity	NPC248862
0.6614	Remote Similarity	NPC472115
0.6614	Remote Similarity	NPC472114
0.6608	Remote Similarity	NPC280807
0.6608	Remote Similarity	NPC314431
0.6606	Remote Similarity	NPC477112
0.6604	Remote Similarity	NPC250448
0.6601	Remote Similarity	NPC472542
0.6601	Remote Similarity	NPC472541
0.66	Remote Similarity	NPC92803
0.66	Remote Similarity	NPC138370
0.6598	Remote Similarity	NPC218594
0.6598	Remote Similarity	NPC99043
0.6597	Remote Similarity	NPC112336
0.6597	Remote Similarity	NPC474814
0.6583	Remote Similarity	NPC18890
0.6583	Remote Similarity	NPC183805
0.6579	Remote Similarity	NPC223595
0.6579	Remote Similarity	NPC167724
0.6579	Remote Similarity	NPC224970
0.6578	Remote Similarity	NPC322644
0.6578	Remote Similarity	NPC474058
0.6578	Remote Similarity	NPC248117
0.6573	Remote Similarity	NPC477979
0.6566	Remote Similarity	NPC194040
0.6564	Remote Similarity	NPC298320
0.6555	Remote Similarity	NPC471155
0.6552	Remote Similarity	NPC245916
0.655	Remote Similarity	NPC473298
0.655	Remote Similarity	NPC122235
0.6543	Remote Similarity	NPC35510
0.6543	Remote Similarity	NPC253667
0.6542	Remote Similarity	NPC322064
0.654	Remote Similarity	NPC303951
0.6538	Remote Similarity	NPC132539
0.6534	Remote Similarity	NPC287358
0.6531	Remote Similarity	NPC475962
0.6528	Remote Similarity	NPC303225
0.6524	Remote Similarity	NPC263709
0.6524	Remote Similarity	NPC243673
0.6524	Remote Similarity	NPC270241
0.6524	Remote Similarity	NPC310403
0.6524	Remote Similarity	NPC148468
0.6524	Remote Similarity	NPC97380
0.6524	Remote Similarity	NPC63210
0.6524	Remote Similarity	NPC39679
0.6524	Remote Similarity	NPC193410
0.6522	Remote Similarity	NPC57398
0.6522	Remote Similarity	NPC107836
0.652	Remote Similarity	NPC316282
0.652	Remote Similarity	NPC90967
0.652	Remote Similarity	NPC90229
0.652	Remote Similarity	NPC198390
0.6513	Remote Similarity	NPC474815
0.6512	Remote Similarity	NPC194562
0.6509	Remote Similarity	NPC23294
0.6507	Remote Similarity	NPC225400
0.6502	Remote Similarity	NPC202812
0.6502	Remote Similarity	NPC34717
0.65	Remote Similarity	NPC221873
0.65	Remote Similarity	NPC316405
0.6497	Remote Similarity	NPC315224
0.6495	Remote Similarity	NPC203202
0.6495	Remote Similarity	NPC264482
0.6488	Remote Similarity	NPC112752
0.6488	Remote Similarity	NPC311054
0.6486	Remote Similarity	NPC116622
0.6484	Remote Similarity	NPC254798
0.6476	Remote Similarity	NPC472538
0.6476	Remote Similarity	NPC470786
0.6474	Remote Similarity	NPC470069
0.6474	Remote Similarity	NPC52059
0.6473	Remote Similarity	NPC232600
0.6471	Remote Similarity	NPC123241
0.6471	Remote Similarity	NPC472293
0.6471	Remote Similarity	NPC303214
0.6468	Remote Similarity	NPC471195
0.6468	Remote Similarity	NPC329858
0.6468	Remote Similarity	NPC5630
0.6468	Remote Similarity	NPC471196
0.6465	Remote Similarity	NPC469928
0.6462	Remote Similarity	NPC123839
0.6462	Remote Similarity	NPC186669
0.6459	Remote Similarity	NPC133156
0.6455	Remote Similarity	NPC472121
0.6455	Remote Similarity	NPC293458
0.6455	Remote Similarity	NPC282339

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 NPC471742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	608
0.2-0.3	1007
0.3-0.4	1113
0.4-0.5	3373
0.5-0.6	2358
0.6-0.7	507
0.7-0.8	29
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
0.7725	Intermediate Similarity	NPD1625	Approved
0.7709	Intermediate Similarity	NPD3776	Discontinued
0.7706	Intermediate Similarity	NPD4888	Discontinued
0.7665	Intermediate Similarity	NPD1189	Approved
0.7541	Intermediate Similarity	NPD3755	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7570	Approved
0.7526	Intermediate Similarity	NPD7569	Approved
0.7513	Intermediate Similarity	NPD5856	Discontinued
0.75	Intermediate Similarity	NPD212	Discontinued
0.7485	Intermediate Similarity	NPD1626	Approved
0.7474	Intermediate Similarity	NPD5504	Discontinued
0.7356	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD2836	Approved
0.7249	Intermediate Similarity	NPD5923	Phase 1
0.7232	Intermediate Similarity	NPD5086	Approved
0.7216	Intermediate Similarity	NPD1230	Approved
0.7211	Intermediate Similarity	NPD6163	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5042	Phase 1
0.7188	Intermediate Similarity	NPD7855	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4329	Approved
0.7181	Intermediate Similarity	NPD5445	Approved
0.7181	Intermediate Similarity	NPD4330	Approved
0.7166	Intermediate Similarity	NPD3792	Approved
0.7159	Intermediate Similarity	NPD5748	Phase 2
0.7135	Intermediate Similarity	NPD3824	Phase 1
0.7135	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5727	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4161	Discontinued
0.7097	Intermediate Similarity	NPD5997	Discontinued
0.709	Intermediate Similarity	NPD7014	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD1210	Approved
0.7074	Intermediate Similarity	NPD5498	Phase 2
0.7059	Intermediate Similarity	NPD5919	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5466	Approved
0.7027	Intermediate Similarity	NPD2037	Approved
0.7017	Intermediate Similarity	NPD7735	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1514	Discontinued
0.6977	Remote Similarity	NPD3170	Approved
0.6973	Remote Similarity	NPD3587	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5918	Discontinued
0.6968	Remote Similarity	NPD2359	Approved
0.6964	Remote Similarity	NPD1619	Phase 3
0.6959	Remote Similarity	NPD6483	Approved
0.6959	Remote Similarity	NPD4948	Discontinued
0.6959	Remote Similarity	NPD6484	Approved
0.6952	Remote Similarity	NPD4150	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1801	Approved
0.6949	Remote Similarity	NPD1802	Approved
0.6947	Remote Similarity	NPD3997	Approved
0.6947	Remote Similarity	NPD3998	Approved
0.6947	Remote Similarity	NPD3782	Discontinued
0.6947	Remote Similarity	NPD3999	Approved
0.6931	Remote Similarity	NPD2361	Approved
0.6919	Remote Similarity	NPD5430	Discontinued
0.6911	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7528	Approved
0.6904	Remote Similarity	NPD5937	Approved
0.6904	Remote Similarity	NPD8146	Phase 2
0.69	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3996	Approved
0.6895	Remote Similarity	NPD3992	Approved
0.6895	Remote Similarity	NPD3993	Approved
0.6895	Remote Similarity	NPD3994	Approved
0.6895	Remote Similarity	NPD3991	Approved
0.6895	Remote Similarity	NPD3995	Approved
0.6895	Remote Similarity	NPD4092	Approved
0.6875	Remote Similarity	NPD3470	Approved
0.6875	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3471	Approved
0.6875	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1208	Approved
0.6863	Remote Similarity	NPD5901	Discontinued
0.6862	Remote Similarity	NPD2432	Approved
0.6862	Remote Similarity	NPD2431	Approved
0.6848	Remote Similarity	NPD2506	Approved
0.6845	Remote Similarity	NPD2455	Approved
0.6845	Remote Similarity	NPD2454	Approved
0.6842	Remote Similarity	NPD4091	Approved
0.6842	Remote Similarity	NPD3794	Approved
0.6842	Remote Similarity	NPD5185	Approved
0.6842	Remote Similarity	NPD3795	Approved
0.6842	Remote Similarity	NPD5184	Approved
0.6842	Remote Similarity	NPD5182	Approved
0.6834	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3377	Discontinued
0.6821	Remote Similarity	NPD2670	Approved
0.6804	Remote Similarity	NPD4412	Phase 2
0.68	Remote Similarity	NPD2010	Phase 3
0.68	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3522	Approved
0.6789	Remote Similarity	NPD3422	Phase 3
0.6789	Remote Similarity	NPD3423	Phase 2
0.6784	Remote Similarity	NPD1527	Phase 2
0.678	Remote Similarity	NPD3947	Discontinued
0.6771	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2336	Approved
0.6766	Remote Similarity	NPD1574	Approved
0.6761	Remote Similarity	NPD2365	Approved
0.6761	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6770	Approved
0.6753	Remote Similarity	NPD8281	Discontinued
0.6748	Remote Similarity	NPD7010	Phase 3
0.6739	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4376	Phase 3
0.6732	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1593	Approved
0.6724	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2820	Phase 3
0.672	Remote Similarity	NPD2369	Discontinued
0.672	Remote Similarity	NPD7795	Phase 2
0.6714	Remote Similarity	NPD7878	Phase 2
0.6707	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2427	Approved
0.6701	Remote Similarity	NPD3990	Phase 3
0.67	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1109	Approved
0.6686	Remote Similarity	NPD1110	Approved
0.6684	Remote Similarity	NPD1913	Phase 1
0.6683	Remote Similarity	NPD7572	Phase 2
0.6683	Remote Similarity	NPD5871	Discontinued
0.6683	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2509	Approved
0.6683	Remote Similarity	NPD2510	Approved
0.6667	Remote Similarity	NPD5475	Discontinued
0.6667	Remote Similarity	NPD1553	Approved
0.6667	Remote Similarity	NPD6142	Phase 3
0.6667	Remote Similarity	NPD9272	Approved
0.6667	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4311	Approved
0.6652	Remote Similarity	NPD4938	Phase 2
0.6651	Remote Similarity	NPD4506	Discontinued
0.6649	Remote Similarity	NPD3989	Phase 3
0.6648	Remote Similarity	NPD6017	Discontinued
0.6647	Remote Similarity	NPD656	Approved
0.6647	Remote Similarity	NPD659	Approved
0.6647	Remote Similarity	NPD663	Approved
0.6647	Remote Similarity	NPD662	Approved
0.6647	Remote Similarity	NPD658	Approved
0.6634	Remote Similarity	NPD2307	Discontinued
0.6633	Remote Similarity	NPD5928	Phase 1
0.6629	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6301	Phase 2
0.6623	Remote Similarity	NPD5488	Discontinued
0.6621	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD4539	Phase 1
0.6613	Remote Similarity	NPD33	Approved
0.6613	Remote Similarity	NPD4393	Approved
0.6612	Remote Similarity	NPD2882	Phase 1
0.6611	Remote Similarity	NPD6416	Phase 2
0.661	Remote Similarity	NPD9477	Approved
0.6609	Remote Similarity	NPD2791	Discontinued
0.6605	Remote Similarity	NPD7404	Approved
0.6601	Remote Similarity	NPD3828	Approved
0.659	Remote Similarity	NPD2950	Approved
0.659	Remote Similarity	NPD2949	Approved
0.6588	Remote Similarity	NPD5416	Discontinued
0.6579	Remote Similarity	NPD3468	Approved
0.6576	Remote Similarity	NPD2360	Approved
0.6573	Remote Similarity	NPD1908	Phase 2
0.6573	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6529	Discontinued
0.6569	Remote Similarity	NPD5194	Approved
0.6569	Remote Similarity	NPD5197	Approved
0.6569	Remote Similarity	NPD5196	Approved
0.6555	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1839	Phase 1
0.6545	Remote Similarity	NPD5183	Approved
0.6545	Remote Similarity	NPD5186	Approved
0.6541	Remote Similarity	NPD4045	Phase 2
0.6541	Remote Similarity	NPD4042	Phase 2
0.6538	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1294	Discontinued
0.6538	Remote Similarity	NPD6987	Phase 1
0.6536	Remote Similarity	NPD4430	Phase 2
0.6535	Remote Similarity	NPD1173	Approved
0.6534	Remote Similarity	NPD6342	Discontinued
0.6531	Remote Similarity	NPD7867	Phase 1
0.653	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD9567	Approved
0.6529	Remote Similarity	NPD552	Approved
0.6529	Remote Similarity	NPD553	Approved
0.6526	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4082	Approved
0.6524	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.652	Remote Similarity	NPD6161	Approved
0.652	Remote Similarity	NPD6162	Approved
0.6517	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD1228	Phase 2
0.6513	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7105	Phase 1
0.6505	Remote Similarity	NPD951	Approved
0.65	Remote Similarity	NPD2387	Approved
0.6497	Remote Similarity	NPD699	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