NPASS Compound

Structure

NPC79777 OpenBabel07101719152D 24 28 0 0 1 0 0 0 0 0999 V2000 3.1404 0.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4683 3.9916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2744 0.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4084 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4097 3.6543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7042 -0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4084 1.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2855 3.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2946 3.3450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2744 2.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1404 1.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1160 2.3611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7042 1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8254 2.0237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9966 1.8872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7569 1.1102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4084 0.8131 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2744 3.3131 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.5882 2.6703 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 -1.7194 2.5783 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0065 2.3131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4900 0.4300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 11 1 0 0 0 0 2 5 1 0 0 0 0 2 9 1 0 0 0 0 4 6 1 0 0 0 0 4 18 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 10 2 0 0 0 0 7 18 1 0 0 0 0 8 9 2 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 23 2 0 0 0 0 12 14 1 0 0 0 0 12 15 2 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 13 18 1 0 0 0 0 14 20 2 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 24 2 0 0 0 0 18 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.03
Volume:	325.865
LogP:	2.664
LogD:	1.93
LogS:	-3.53
# Rotatable Bonds:	0
TPSA:	77.48
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.608
Synthetic Accessibility Score:	5.054
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.104
MDCK Permeability:	1.6772615708759986e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	97.18927001953125%
Volume Distribution (VD):	0.571
Pgp-substrate:	2.3663837909698486%

ADMET: Metabolism

CYP1A2-inhibitor:	0.88
CYP1A2-substrate:	0.572
CYP2C19-inhibitor:	0.744
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.87
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.695
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	3.955
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.187
Human Hepatotoxicity (H-HT):	0.772
Drug-inuced Liver Injury (DILI):	0.463
AMES Toxicity:	0.924
Rat Oral Acute Toxicity:	0.884
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.879
Carcinogencity:	0.967
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC79777

Natural Product ID:	NPC79777
*Common Name:**	JDWKHDMGELDYEC-GOSISDBHSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Discorhabdin E
Standard InCHIKey:	JDWKHDMGELDYEC-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C18H14BrN3O2/c19-10-7-18(3-1-11(10)23)4-6-21-16-13(18)14-12-9(2-5-20-14)8-22-15(12)17(16)24/h1,3,7-8,21-22H,2,4-6H2/t18-/m1/s1
SMILES:	O=C1C=C[C@]2(C=C1Br)CCNC1=C2C2=NCCc3c2c(C1=O)[nH]c3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086885
PubChem CID:	21773330
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO33184	sceptrella sp.	Species	Latrunculiidae	Eukaryota	n.a.	Korean	n.a.	PMID[20055495]

☑ 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
MIC	6

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1300.0	nM	PMID[529588]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	186100.0	nM	PMID[529588]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	50.0	ug.mL-1	PMID[529588]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	25.0	ug.mL-1	PMID[529588]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[529588]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[529588]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	50.0	ug.mL-1	PMID[529588]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[529588]

☑ 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 NPC79777 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	527
0.1-0.2	3972
0.2-0.3	18998
0.3-0.4	13377
0.4-0.5	2710
0.5-0.6	2096
0.6-0.7	874
0.7-0.8	112
0.8-0.85	15
0.85-0.9	6
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9876	High Similarity	NPC234403
0.9625	High Similarity	NPC262338
0.9512	High Similarity	NPC182940
0.9244	High Similarity	NPC225622
0.9244	High Similarity	NPC221726
0.9244	High Similarity	NPC477414
0.9235	High Similarity	NPC473628
0.9181	High Similarity	NPC475874
0.907	High Similarity	NPC268966
0.9036	High Similarity	NPC186068
0.8953	High Similarity	NPC23476
0.8953	High Similarity	NPC474259
0.8953	High Similarity	NPC477415
0.8727	High Similarity	NPC274981
0.8523	High Similarity	NPC473946
0.8519	High Similarity	NPC471655
0.8514	High Similarity	NPC474258
0.8511	High Similarity	NPC477413
0.8434	Intermediate Similarity	NPC474492
0.8396	Intermediate Similarity	NPC143075
0.8333	Intermediate Similarity	NPC88115
0.8324	Intermediate Similarity	NPC106757
0.8274	Intermediate Similarity	NPC100104
0.8274	Intermediate Similarity	NPC470680
0.8079	Intermediate Similarity	NPC477042
0.8061	Intermediate Similarity	NPC100726
0.8056	Intermediate Similarity	NPC469359
0.7857	Intermediate Similarity	NPC473878
0.7811	Intermediate Similarity	NPC217021
0.7811	Intermediate Similarity	NPC470679
0.7798	Intermediate Similarity	NPC102664
0.7672	Intermediate Similarity	NPC167710
0.7632	Intermediate Similarity	NPC476143
0.7579	Intermediate Similarity	NPC74153
0.7569	Intermediate Similarity	NPC284775
0.7554	Intermediate Similarity	NPC477003
0.7553	Intermediate Similarity	NPC47190
0.7514	Intermediate Similarity	NPC71132
0.7513	Intermediate Similarity	NPC473821
0.75	Intermediate Similarity	NPC477004
0.7448	Intermediate Similarity	NPC477044
0.7448	Intermediate Similarity	NPC477041
0.7398	Intermediate Similarity	NPC469563
0.7384	Intermediate Similarity	NPC123906
0.7371	Intermediate Similarity	NPC74357
0.736	Intermediate Similarity	NPC175602
0.7356	Intermediate Similarity	NPC251391
0.7347	Intermediate Similarity	NPC476252
0.733	Intermediate Similarity	NPC304203
0.7323	Intermediate Similarity	NPC475410
0.7323	Intermediate Similarity	NPC469577
0.732	Intermediate Similarity	NPC477045
0.7318	Intermediate Similarity	NPC233380
0.7316	Intermediate Similarity	NPC476460
0.7306	Intermediate Similarity	NPC473814
0.7306	Intermediate Similarity	NPC78767
0.7289	Intermediate Similarity	NPC291517
0.7286	Intermediate Similarity	NPC469578
0.7277	Intermediate Similarity	NPC216550
0.7258	Intermediate Similarity	NPC191415
0.725	Intermediate Similarity	NPC61038
0.724	Intermediate Similarity	NPC326422
0.7231	Intermediate Similarity	NPC237414
0.7222	Intermediate Similarity	NPC477043
0.7222	Intermediate Similarity	NPC115232
0.7214	Intermediate Similarity	NPC469562
0.7214	Intermediate Similarity	NPC220594
0.7209	Intermediate Similarity	NPC467188
0.7202	Intermediate Similarity	NPC93390
0.72	Intermediate Similarity	NPC70406
0.7189	Intermediate Similarity	NPC157583
0.7143	Intermediate Similarity	NPC70949
0.7127	Intermediate Similarity	NPC42372
0.7126	Intermediate Similarity	NPC105811
0.712	Intermediate Similarity	NPC103119
0.7108	Intermediate Similarity	NPC207866
0.7097	Intermediate Similarity	NPC237188
0.7095	Intermediate Similarity	NPC80681
0.709	Intermediate Similarity	NPC110158
0.7085	Intermediate Similarity	NPC317701
0.7065	Intermediate Similarity	NPC302647
0.7045	Intermediate Similarity	NPC313889
0.7037	Intermediate Similarity	NPC102755
0.7026	Intermediate Similarity	NPC195239
0.7026	Intermediate Similarity	NPC157828
0.7022	Intermediate Similarity	NPC209362
0.7021	Intermediate Similarity	NPC73994
0.7005	Intermediate Similarity	NPC477416
0.699	Remote Similarity	NPC11445
0.699	Remote Similarity	NPC292361
0.6989	Remote Similarity	NPC293216
0.6982	Remote Similarity	NPC23215
0.6976	Remote Similarity	NPC471194
0.6976	Remote Similarity	NPC471193
0.6976	Remote Similarity	NPC473218
0.6976	Remote Similarity	NPC110182
0.6976	Remote Similarity	NPC470702
0.697	Remote Similarity	NPC475914
0.697	Remote Similarity	NPC201266
0.697	Remote Similarity	NPC268744
0.697	Remote Similarity	NPC153123
0.697	Remote Similarity	NPC220797
0.697	Remote Similarity	NPC474318
0.6968	Remote Similarity	NPC11126
0.6963	Remote Similarity	NPC308931
0.6963	Remote Similarity	NPC99939
0.6963	Remote Similarity	NPC133003
0.6944	Remote Similarity	NPC213914
0.6942	Remote Similarity	NPC470703
0.6939	Remote Similarity	NPC202812
0.6935	Remote Similarity	NPC252338
0.6935	Remote Similarity	NPC166209
0.6935	Remote Similarity	NPC77241
0.6935	Remote Similarity	NPC269203
0.6935	Remote Similarity	NPC13456
0.6919	Remote Similarity	NPC471943
0.6919	Remote Similarity	NPC34837
0.6915	Remote Similarity	NPC83774
0.6911	Remote Similarity	NPC228835
0.6907	Remote Similarity	NPC324091
0.6893	Remote Similarity	NPC469544
0.6882	Remote Similarity	NPC6982
0.6878	Remote Similarity	NPC213468
0.6869	Remote Similarity	NPC174281
0.6869	Remote Similarity	NPC227582
0.6869	Remote Similarity	NPC475286
0.6866	Remote Similarity	NPC260900
0.6856	Remote Similarity	NPC209917
0.6856	Remote Similarity	NPC255909
0.6848	Remote Similarity	NPC2414
0.6845	Remote Similarity	NPC252572
0.6845	Remote Similarity	NPC72956
0.6842	Remote Similarity	NPC61011
0.6839	Remote Similarity	NPC101130
0.6839	Remote Similarity	NPC58268
0.6839	Remote Similarity	NPC129412
0.6839	Remote Similarity	NPC114033
0.6837	Remote Similarity	NPC472292
0.6833	Remote Similarity	NPC229055
0.6825	Remote Similarity	NPC14113
0.6825	Remote Similarity	NPC84827
0.6825	Remote Similarity	NPC145885
0.6823	Remote Similarity	NPC467063
0.6821	Remote Similarity	NPC154339
0.6818	Remote Similarity	NPC472293
0.6812	Remote Similarity	NPC153980
0.6812	Remote Similarity	NPC6865
0.6809	Remote Similarity	NPC110500
0.6809	Remote Similarity	NPC149155
0.6809	Remote Similarity	NPC469529
0.6809	Remote Similarity	NPC203468
0.6806	Remote Similarity	NPC470677
0.6804	Remote Similarity	NPC17059
0.68	Remote Similarity	NPC74413
0.68	Remote Similarity	NPC136957
0.68	Remote Similarity	NPC19696
0.6789	Remote Similarity	NPC248041
0.6789	Remote Similarity	NPC126709
0.6789	Remote Similarity	NPC55772
0.6789	Remote Similarity	NPC283219
0.6786	Remote Similarity	NPC477418
0.6786	Remote Similarity	NPC477420
0.6774	Remote Similarity	NPC78020
0.6772	Remote Similarity	NPC151635
0.6772	Remote Similarity	NPC267885
0.6758	Remote Similarity	NPC475635
0.6758	Remote Similarity	NPC76982
0.6749	Remote Similarity	NPC98715
0.674	Remote Similarity	NPC75135
0.6739	Remote Similarity	NPC214106
0.6736	Remote Similarity	NPC21429
0.6736	Remote Similarity	NPC46895
0.6735	Remote Similarity	NPC83111
0.6734	Remote Similarity	NPC179701
0.6734	Remote Similarity	NPC79356
0.6734	Remote Similarity	NPC102592
0.6717	Remote Similarity	NPC267343
0.6716	Remote Similarity	NPC472296
0.6716	Remote Similarity	NPC472297
0.6714	Remote Similarity	NPC471192
0.6705	Remote Similarity	NPC190296
0.6705	Remote Similarity	NPC105127
0.6703	Remote Similarity	NPC265100
0.6702	Remote Similarity	NPC233050
0.6702	Remote Similarity	NPC276540
0.6702	Remote Similarity	NPC54214
0.67	Remote Similarity	NPC262898
0.6699	Remote Similarity	NPC116555
0.6698	Remote Similarity	NPC269270
0.6684	Remote Similarity	NPC117027
0.6683	Remote Similarity	NPC472065
0.6667	Remote Similarity	NPC14686
0.6667	Remote Similarity	NPC286427
0.6667	Remote Similarity	NPC235684
0.665	Remote Similarity	NPC48117
0.665	Remote Similarity	NPC329765
0.665	Remote Similarity	NPC300183
0.665	Remote Similarity	NPC225821
0.665	Remote Similarity	NPC476526
0.665	Remote Similarity	NPC46225

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 NPC79777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	600
0.2-0.3	1120
0.3-0.4	2440
0.4-0.5	2836
0.5-0.6	1552
0.6-0.7	325
0.7-0.8	8
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
0.7459	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5473	Discontinued
0.7074	Intermediate Similarity	NPD3178	Discontinued
0.7016	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2753	Discontinued
0.699	Remote Similarity	NPD4848	Phase 1
0.6979	Remote Similarity	NPD4988	Discontinued
0.6979	Remote Similarity	NPD3961	Discontinued
0.6965	Remote Similarity	NPD5901	Discontinued
0.6952	Remote Similarity	NPD3238	Discontinued
0.6923	Remote Similarity	NPD4922	Phase 2
0.6906	Remote Similarity	NPD2214	Approved
0.6906	Remote Similarity	NPD2213	Approved
0.6864	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4075	Phase 2
0.6842	Remote Similarity	NPD2479	Phase 3
0.6842	Remote Similarity	NPD2481	Approved
0.6836	Remote Similarity	NPD1270	Approved
0.6823	Remote Similarity	NPD7564	Discontinued
0.6809	Remote Similarity	NPD482	Approved
0.6798	Remote Similarity	NPD3100	Discontinued
0.6796	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7619	Phase 3
0.6768	Remote Similarity	NPD7618	Phase 3
0.672	Remote Similarity	NPD6446	Discontinued
0.6716	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2094	Phase 2
0.6684	Remote Similarity	NPD2092	Phase 2
0.6684	Remote Similarity	NPD2095	Phase 2
0.6684	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2172	Phase 1
0.6667	Remote Similarity	NPD1996	Discontinued
0.6667	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4524	Discontinued
0.6649	Remote Similarity	NPD2096	Phase 2
0.6649	Remote Similarity	NPD2091	Phase 2
0.6649	Remote Similarity	NPD5400	Approved
0.6647	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3393	Approved
0.6635	Remote Similarity	NPD3394	Approved
0.6635	Remote Similarity	NPD3389	Approved
0.6633	Remote Similarity	NPD460	Discontinued
0.6632	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6664	Approved
0.6596	Remote Similarity	NPD1343	Approved
0.6595	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3505	Approved
0.6562	Remote Similarity	NPD3506	Approved
0.6554	Remote Similarity	NPD1722	Approved
0.6546	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1630	Approved
0.6534	Remote Similarity	NPD786	Approved
0.6528	Remote Similarity	NPD4076	Approved
0.6528	Remote Similarity	NPD4079	Approved
0.6524	Remote Similarity	NPD3583	Phase 2
0.6522	Remote Similarity	NPD2008	Discontinued
0.6517	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD3319	Phase 1
0.6513	Remote Similarity	NPD3320	Approved
0.6513	Remote Similarity	NPD3318	Approved
0.6509	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD1600	Suspended
0.6505	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2411	Approved
0.6492	Remote Similarity	NPD750	Phase 2
0.6485	Remote Similarity	NPD2290	Phase 3
0.6485	Remote Similarity	NPD2289	Phase 3
0.6482	Remote Similarity	NPD4499	Approved
0.6482	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD2509	Approved
0.6459	Remote Similarity	NPD2510	Approved
0.6459	Remote Similarity	NPD6376	Discontinued
0.6458	Remote Similarity	NPD4128	Approved
0.6456	Remote Similarity	NPD7187	Phase 2
0.644	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5855	Phase 3
0.6436	Remote Similarity	NPD5853	Phase 3
0.6436	Remote Similarity	NPD1631	Approved
0.6436	Remote Similarity	NPD3323	Discontinued
0.6435	Remote Similarity	NPD6242	Discontinued
0.6422	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD1982	Phase 1
0.642	Remote Similarity	NPD201	Phase 2
0.642	Remote Similarity	NPD200	Phase 2
0.6418	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7455	Approved
0.6415	Remote Similarity	NPD7454	Approved
0.6413	Remote Similarity	NPD2837	Discontinued
0.6398	Remote Similarity	NPD4051	Discontinued
0.6394	Remote Similarity	NPD6987	Phase 1
0.6394	Remote Similarity	NPD3947	Discontinued
0.6394	Remote Similarity	NPD4299	Phase 1
0.6387	Remote Similarity	NPD1575	Approved
0.6387	Remote Similarity	NPD1573	Approved
0.6382	Remote Similarity	NPD2770	Discontinued
0.6381	Remote Similarity	NPD6459	Phase 2
0.6374	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD991	Phase 2
0.6373	Remote Similarity	NPD4883	Approved
0.6368	Remote Similarity	NPD6152	Phase 1
0.6368	Remote Similarity	NPD3915	Approved
0.6368	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7175	Phase 1
0.6346	Remote Similarity	NPD4304	Discovery
0.634	Remote Similarity	NPD6044	Discontinued
0.634	Remote Similarity	NPD7402	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD3917	Approved
0.6338	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD3918	Approved
0.6335	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2641	Approved
0.6335	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2640	Approved
0.6333	Remote Similarity	NPD1506	Discontinued
0.6332	Remote Similarity	NPD7026	Phase 2
0.6332	Remote Similarity	NPD5809	Phase 3
0.633	Remote Similarity	NPD1404	Approved
0.633	Remote Similarity	NPD1403	Approved
0.6327	Remote Similarity	NPD3927	Phase 2
0.6324	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5685	Approved
0.6318	Remote Similarity	NPD5686	Approved
0.6316	Remote Similarity	NPD5426	Phase 3
0.6313	Remote Similarity	NPD5198	Approved
0.6313	Remote Similarity	NPD5199	Approved
0.6311	Remote Similarity	NPD2405	Phase 3
0.6308	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5888	Phase 2
0.6303	Remote Similarity	NPD7191	Phase 2
0.63	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3246	Discontinued
0.6298	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6771	Discontinued
0.6294	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.629	Remote Similarity	NPD2061	Approved
0.6289	Remote Similarity	NPD5065	Approved
0.6287	Remote Similarity	NPD2336	Approved
0.6286	Remote Similarity	NPD3967	Approved
0.6286	Remote Similarity	NPD7010	Phase 3
0.6283	Remote Similarity	NPD2639	Approved
0.6283	Remote Similarity	NPD2642	Approved
0.6274	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD6068	Discontinued
0.6256	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD3411	Phase 2
0.6256	Remote Similarity	NPD3410	Approved
0.625	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3890	Phase 2
0.625	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6217	Discontinued
0.625	Remote Similarity	NPD5017	Discontinued
0.625	Remote Similarity	NPD3891	Phase 2
0.6238	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD6787	Phase 2
0.6232	Remote Similarity	NPD5854	Approved
0.6232	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD1096	Discontinued
0.6224	Remote Similarity	NPD4181	Approved
0.6224	Remote Similarity	NPD2144	Approved
0.6222	Remote Similarity	NPD9599	Approved
0.6218	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD272	Approved
0.6211	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD1586	Approved
0.6203	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD484	Approved
0.62	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD3968	Approved
0.6195	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6176	Phase 1
0.6186	Remote Similarity	NPD3609	Approved
0.6186	Remote Similarity	NPD3610	Approved
0.6172	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD3476	Approved
0.6171	Remote Similarity	NPD3475	Approved
0.6168	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD2071	Approved
0.6167	Remote Similarity	NPD2070	Approved
0.6167	Remote Similarity	NPD2068	Approved
0.6167	Remote Similarity	NPD2069	Approved
0.6165	Remote Similarity	NPD7027	Phase 3
0.6165	Remote Similarity	NPD6226	Phase 3
0.6165	Remote Similarity	NPD2307	Discontinued
0.6161	Remote Similarity	NPD6323	Clinical (unspecified phase)

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