NPASS Compound

Structure

NPC262338 OpenBabel07101718272D 23 27 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 -2.2744 -2.3131 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 -1.8131 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 1.2855 -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 -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 3 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 4 2 0 0 0 0 1 11 1 0 0 0 0 2 5 2 0 0 0 0 2 11 1 0 0 0 0 3 7 1 0 0 0 0 3 10 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 6 8 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 2 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 11 22 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 19 2 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	305.12
Volume:	306.581
LogP:	2.305
LogD:	1.542
LogS:	-3.758
# Rotatable Bonds:	0
TPSA:	77.48
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	4.508
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:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.035
MDCK Permeability:	1.759157021297142e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.273
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.913
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	97.64196014404297%
Volume Distribution (VD):	0.308
Pgp-substrate:	2.4802229404449463%

ADMET: Metabolism

CYP1A2-inhibitor:	0.597
CYP1A2-substrate:	0.454
CYP2C19-inhibitor:	0.401
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.5
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.63
CYP2D6-substrate:	0.589
CYP3A4-inhibitor:	0.376
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	3.937
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.408
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.464
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.362
Carcinogencity:	0.92
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC262338

Natural Product ID:	NPC262338
*Common Name:**	Didebromodiscorhabdin C
IUPAC Name:	n.a.
Synonyms:	Didebromodiscorhabdin C
Standard InCHIKey:	AROYJUCVKLJDAK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H15N3O2/c22-11-1-4-18(5-2-11)6-8-20-16-13(18)14-12-10(3-7-19-14)9-21-15(12)17(16)23/h1-2,4-5,9,20-21H,3,6-8H2
SMILES:	C1=CC2(C=CC1=O)CCNC1=C2C2=NCCc3c[nH]c(c23)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087525
PubChem CID:	10828407
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
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	127400.0	nM	PMID[566538]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	21000.0	nM	PMID[566538]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	100.0	ug.mL-1	PMID[566538]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[566538]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[566538]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[566538]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[566538]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[566538]

☑ 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 NPC262338 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	492
0.1-0.2	3518
0.2-0.3	17329
0.3-0.4	15043
0.4-0.5	2929
0.5-0.6	2150
0.6-0.7	1025
0.7-0.8	174
0.8-0.85	19
0.85-0.9	12
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC79777
0.9503	High Similarity	NPC234403
0.9277	High Similarity	NPC23476
0.9277	High Similarity	NPC474259
0.9277	High Similarity	NPC477415
0.9146	High Similarity	NPC182940
0.8994	High Similarity	NPC473628
0.8941	High Similarity	NPC475874
0.8895	High Similarity	NPC477414
0.8895	High Similarity	NPC225622
0.8895	High Similarity	NPC221726
0.8846	High Similarity	NPC471655
0.875	High Similarity	NPC474492
0.8721	High Similarity	NPC268966
0.8675	High Similarity	NPC186068
0.858	High Similarity	NPC470680
0.858	High Similarity	NPC100104
0.8365	Intermediate Similarity	NPC100726
0.8364	Intermediate Similarity	NPC274981
0.8363	Intermediate Similarity	NPC477042
0.8333	Intermediate Similarity	NPC469359
0.8286	Intermediate Similarity	NPC473946
0.8276	Intermediate Similarity	NPC474258
0.8191	Intermediate Similarity	NPC477413
0.8172	Intermediate Similarity	NPC143075
0.8148	Intermediate Similarity	NPC473878
0.8098	Intermediate Similarity	NPC217021
0.8098	Intermediate Similarity	NPC470679
0.8086	Intermediate Similarity	NPC102664
0.8011	Intermediate Similarity	NPC88115
0.8	Intermediate Similarity	NPC106757
0.7923	Intermediate Similarity	NPC167710
0.788	Intermediate Similarity	NPC476143
0.7829	Intermediate Similarity	NPC284775
0.7826	Intermediate Similarity	NPC74153
0.7809	Intermediate Similarity	NPC477003
0.7802	Intermediate Similarity	NPC47190
0.7778	Intermediate Similarity	NPC71132
0.776	Intermediate Similarity	NPC473821
0.7688	Intermediate Similarity	NPC477044
0.7688	Intermediate Similarity	NPC477041
0.7651	Intermediate Similarity	NPC123906
0.7632	Intermediate Similarity	NPC469563
0.7619	Intermediate Similarity	NPC251391
0.7592	Intermediate Similarity	NPC175602
0.7579	Intermediate Similarity	NPC476252
0.7572	Intermediate Similarity	NPC233380
0.7568	Intermediate Similarity	NPC304203
0.7562	Intermediate Similarity	NPC291517
0.7554	Intermediate Similarity	NPC476460
0.7553	Intermediate Similarity	NPC477045
0.7552	Intermediate Similarity	NPC475410
0.7552	Intermediate Similarity	NPC469577
0.754	Intermediate Similarity	NPC473814
0.754	Intermediate Similarity	NPC78767
0.7514	Intermediate Similarity	NPC216550
0.7513	Intermediate Similarity	NPC469578
0.75	Intermediate Similarity	NPC191415
0.7474	Intermediate Similarity	NPC61038
0.7473	Intermediate Similarity	NPC326422
0.7471	Intermediate Similarity	NPC115232
0.747	Intermediate Similarity	NPC467188
0.7456	Intermediate Similarity	NPC70406
0.7448	Intermediate Similarity	NPC477043
0.7436	Intermediate Similarity	NPC469562
0.7436	Intermediate Similarity	NPC220594
0.7433	Intermediate Similarity	NPC93390
0.743	Intermediate Similarity	NPC157583
0.7386	Intermediate Similarity	NPC70949
0.7381	Intermediate Similarity	NPC105811
0.7371	Intermediate Similarity	NPC42372
0.7351	Intermediate Similarity	NPC103119
0.7341	Intermediate Similarity	NPC80681
0.7333	Intermediate Similarity	NPC237188
0.7323	Intermediate Similarity	NPC207866
0.7306	Intermediate Similarity	NPC317701
0.7303	Intermediate Similarity	NPC302647
0.7294	Intermediate Similarity	NPC313889
0.7277	Intermediate Similarity	NPC477004
0.7268	Intermediate Similarity	NPC102755
0.7267	Intermediate Similarity	NPC209362
0.7253	Intermediate Similarity	NPC73994
0.7249	Intermediate Similarity	NPC157828
0.7249	Intermediate Similarity	NPC195239
0.7239	Intermediate Similarity	NPC23215
0.7222	Intermediate Similarity	NPC293216
0.7214	Intermediate Similarity	NPC477416
0.7211	Intermediate Similarity	NPC11445
0.7211	Intermediate Similarity	NPC292361
0.7198	Intermediate Similarity	NPC11126
0.7189	Intermediate Similarity	NPC308931
0.7189	Intermediate Similarity	NPC133003
0.7189	Intermediate Similarity	NPC99939
0.7186	Intermediate Similarity	NPC471193
0.7186	Intermediate Similarity	NPC110182
0.7186	Intermediate Similarity	NPC471194
0.7184	Intermediate Similarity	NPC213914
0.7158	Intermediate Similarity	NPC202812
0.7151	Intermediate Similarity	NPC471943
0.715	Intermediate Similarity	NPC252338
0.7143	Intermediate Similarity	NPC83774
0.7135	Intermediate Similarity	NPC34837
0.7135	Intermediate Similarity	NPC228835
0.7128	Intermediate Similarity	NPC324091
0.7111	Intermediate Similarity	NPC6982
0.7104	Intermediate Similarity	NPC213468
0.71	Intermediate Similarity	NPC469544
0.7083	Intermediate Similarity	NPC114033
0.7083	Intermediate Similarity	NPC101130
0.7083	Intermediate Similarity	NPC58268
0.7083	Intermediate Similarity	NPC129412
0.7083	Intermediate Similarity	NPC227582
0.7077	Intermediate Similarity	NPC260900
0.7074	Intermediate Similarity	NPC255909
0.7074	Intermediate Similarity	NPC209917
0.7072	Intermediate Similarity	NPC252572
0.7069	Intermediate Similarity	NPC229055
0.7065	Intermediate Similarity	NPC61011
0.7053	Intermediate Similarity	NPC472292
0.705	Intermediate Similarity	NPC72956
0.7049	Intermediate Similarity	NPC145885
0.7049	Intermediate Similarity	NPC14113
0.7049	Intermediate Similarity	NPC84827
0.7043	Intermediate Similarity	NPC467063
0.7037	Intermediate Similarity	NPC154339
0.7033	Intermediate Similarity	NPC203468
0.7033	Intermediate Similarity	NPC469529
0.7033	Intermediate Similarity	NPC110500
0.7033	Intermediate Similarity	NPC149155
0.7031	Intermediate Similarity	NPC472293
0.7029	Intermediate Similarity	NPC74357
0.7027	Intermediate Similarity	NPC470677
0.7021	Intermediate Similarity	NPC17059
0.7015	Intermediate Similarity	NPC153980
0.7015	Intermediate Similarity	NPC6865
0.7011	Intermediate Similarity	NPC126709
0.7011	Intermediate Similarity	NPC248041
0.7011	Intermediate Similarity	NPC283219
0.7011	Intermediate Similarity	NPC55772
0.701	Intermediate Similarity	NPC237414
0.701	Intermediate Similarity	NPC74413
0.7	Intermediate Similarity	NPC78020
0.6995	Remote Similarity	NPC267885
0.6995	Remote Similarity	NPC151635
0.6989	Remote Similarity	NPC76982
0.6972	Remote Similarity	NPC477418
0.6972	Remote Similarity	NPC477420
0.6966	Remote Similarity	NPC214106
0.6954	Remote Similarity	NPC98715
0.6952	Remote Similarity	NPC21429
0.6952	Remote Similarity	NPC46895
0.6947	Remote Similarity	NPC83111
0.6946	Remote Similarity	NPC105127
0.6943	Remote Similarity	NPC102592
0.6943	Remote Similarity	NPC79356
0.6941	Remote Similarity	NPC190296
0.6927	Remote Similarity	NPC265100
0.6927	Remote Similarity	NPC267343
0.6923	Remote Similarity	NPC472297
0.6923	Remote Similarity	NPC472296
0.6912	Remote Similarity	NPC471192
0.69	Remote Similarity	NPC116555
0.6898	Remote Similarity	NPC117027
0.6893	Remote Similarity	NPC286427
0.6893	Remote Similarity	NPC269270
0.6886	Remote Similarity	NPC195704
0.6886	Remote Similarity	NPC96102
0.6886	Remote Similarity	NPC200397
0.6886	Remote Similarity	NPC98156
0.6886	Remote Similarity	NPC167200
0.6886	Remote Similarity	NPC292434
0.6886	Remote Similarity	NPC64661
0.6886	Remote Similarity	NPC138596
0.6886	Remote Similarity	NPC14448
0.6884	Remote Similarity	NPC472065
0.6878	Remote Similarity	NPC235684
0.6872	Remote Similarity	NPC242116
0.6868	Remote Similarity	NPC194411
0.6865	Remote Similarity	NPC111275
0.6864	Remote Similarity	NPC110126
0.6862	Remote Similarity	NPC110158
0.686	Remote Similarity	NPC14686
0.686	Remote Similarity	NPC159856
0.686	Remote Similarity	NPC314372
0.6857	Remote Similarity	NPC472260
0.6854	Remote Similarity	NPC206819
0.6854	Remote Similarity	NPC318065
0.6853	Remote Similarity	NPC300183
0.685	Remote Similarity	NPC46225
0.685	Remote Similarity	NPC225821
0.6845	Remote Similarity	NPC84911
0.6842	Remote Similarity	NPC278434
0.6833	Remote Similarity	NPC194640
0.6833	Remote Similarity	NPC21174
0.6833	Remote Similarity	NPC271797
0.6825	Remote Similarity	NPC311282
0.6824	Remote Similarity	NPC48171
0.6824	Remote Similarity	NPC469783
0.6824	Remote Similarity	NPC469784
0.6824	Remote Similarity	NPC77582

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 NPC262338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	547
0.2-0.3	1052
0.3-0.4	2268
0.4-0.5	2801
0.5-0.6	1725
0.6-0.7	461
0.7-0.8	35
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
0.7709	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5473	Discontinued
0.7308	Intermediate Similarity	NPD3178	Discontinued
0.7243	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD2753	Discontinued
0.7211	Intermediate Similarity	NPD4848	Phase 1
0.7204	Intermediate Similarity	NPD3961	Discontinued
0.7204	Intermediate Similarity	NPD4988	Discontinued
0.7182	Intermediate Similarity	NPD3238	Discontinued
0.7179	Intermediate Similarity	NPD5901	Discontinued
0.7143	Intermediate Similarity	NPD4922	Phase 2
0.7143	Intermediate Similarity	NPD2213	Approved
0.7143	Intermediate Similarity	NPD2214	Approved
0.7117	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD4075	Phase 2
0.7076	Intermediate Similarity	NPD1270	Approved
0.7065	Intermediate Similarity	NPD2479	Phase 3
0.7065	Intermediate Similarity	NPD2481	Approved
0.7043	Intermediate Similarity	NPD7564	Discontinued
0.7035	Intermediate Similarity	NPD3100	Discontinued
0.7033	Intermediate Similarity	NPD482	Approved
0.7029	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7618	Phase 3
0.6979	Remote Similarity	NPD7619	Phase 3
0.6944	Remote Similarity	NPD6446	Discontinued
0.6936	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2095	Phase 2
0.6898	Remote Similarity	NPD2094	Phase 2
0.6898	Remote Similarity	NPD2092	Phase 2
0.6898	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2172	Phase 1
0.6888	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4524	Discontinued
0.6878	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5400	Approved
0.6862	Remote Similarity	NPD2096	Phase 2
0.6862	Remote Similarity	NPD2091	Phase 2
0.6851	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD460	Discontinued
0.6829	Remote Similarity	NPD3393	Approved
0.6829	Remote Similarity	NPD3389	Approved
0.6829	Remote Similarity	NPD3394	Approved
0.6821	Remote Similarity	NPD6664	Approved
0.6816	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1343	Approved
0.6796	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1722	Approved
0.6774	Remote Similarity	NPD3505	Approved
0.6774	Remote Similarity	NPD3506	Approved
0.6765	Remote Similarity	NPD786	Approved
0.676	Remote Similarity	NPD1630	Approved
0.6755	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3583	Phase 2
0.6738	Remote Similarity	NPD4076	Approved
0.6738	Remote Similarity	NPD4079	Approved
0.672	Remote Similarity	NPD3318	Approved
0.672	Remote Similarity	NPD3319	Phase 1
0.672	Remote Similarity	NPD3320	Approved
0.6718	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2008	Discontinued
0.6703	Remote Similarity	NPD750	Phase 2
0.67	Remote Similarity	NPD1600	Suspended
0.67	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4499	Approved
0.6683	Remote Similarity	NPD2411	Approved
0.6667	Remote Similarity	NPD4128	Approved
0.665	Remote Similarity	NPD7187	Phase 2
0.665	Remote Similarity	NPD2510	Approved
0.665	Remote Similarity	NPD2509	Approved
0.665	Remote Similarity	NPD6376	Discontinued
0.6649	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1631	Approved
0.6648	Remote Similarity	NPD3323	Discontinued
0.6647	Remote Similarity	NPD201	Phase 2
0.6647	Remote Similarity	NPD200	Phase 2
0.6633	Remote Similarity	NPD5855	Phase 3
0.6633	Remote Similarity	NPD5853	Phase 3
0.6629	Remote Similarity	NPD2837	Discontinued
0.6619	Remote Similarity	NPD6242	Discontinued
0.6616	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD1982	Phase 1
0.6606	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD991	Phase 2
0.6602	Remote Similarity	NPD7454	Approved
0.6602	Remote Similarity	NPD7455	Approved
0.6595	Remote Similarity	NPD1573	Approved
0.6595	Remote Similarity	NPD1575	Approved
0.6585	Remote Similarity	NPD4051	Discontinued
0.6584	Remote Similarity	NPD4299	Phase 1
0.6584	Remote Similarity	NPD6987	Phase 1
0.6584	Remote Similarity	NPD3947	Discontinued
0.658	Remote Similarity	NPD2770	Discontinued
0.6578	Remote Similarity	NPD4883	Approved
0.6573	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6459	Phase 2
0.6553	Remote Similarity	NPD6152	Phase 1
0.6553	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD3915	Approved
0.6546	Remote Similarity	NPD7175	Phase 1
0.6543	Remote Similarity	NPD6044	Discontinued
0.6543	Remote Similarity	NPD7402	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2640	Approved
0.6541	Remote Similarity	NPD2641	Approved
0.6541	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1403	Approved
0.6538	Remote Similarity	NPD1404	Approved
0.6536	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4304	Discovery
0.6528	Remote Similarity	NPD5809	Phase 3
0.6528	Remote Similarity	NPD7026	Phase 2
0.6526	Remote Similarity	NPD3927	Phase 2
0.6522	Remote Similarity	NPD3918	Approved
0.6522	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3917	Approved
0.652	Remote Similarity	NPD1506	Discontinued
0.6515	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5685	Approved
0.6513	Remote Similarity	NPD5686	Approved
0.6508	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6771	Discontinued
0.6502	Remote Similarity	NPD5426	Phase 3
0.65	Remote Similarity	NPD2405	Phase 3
0.65	Remote Similarity	NPD2061	Approved
0.6495	Remote Similarity	NPD3246	Discontinued
0.6495	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD5198	Approved
0.6493	Remote Similarity	NPD5199	Approved
0.6492	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5888	Phase 2
0.6489	Remote Similarity	NPD5065	Approved
0.6488	Remote Similarity	NPD7191	Phase 2
0.6486	Remote Similarity	NPD2639	Approved
0.6486	Remote Similarity	NPD2642	Approved
0.648	Remote Similarity	NPD2336	Approved
0.6471	Remote Similarity	NPD3967	Approved
0.6471	Remote Similarity	NPD7010	Phase 3
0.6462	Remote Similarity	NPD6068	Discontinued
0.6462	Remote Similarity	NPD1996	Discontinued
0.6456	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6217	Discontinued
0.6439	Remote Similarity	NPD3410	Approved
0.6439	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3411	Phase 2
0.6437	Remote Similarity	NPD9599	Approved
0.6436	Remote Similarity	NPD3890	Phase 2
0.6436	Remote Similarity	NPD3891	Phase 2
0.6436	Remote Similarity	NPD5017	Discontinued
0.6433	Remote Similarity	NPD272	Approved
0.6429	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD1096	Discontinued
0.6422	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD2144	Approved
0.6421	Remote Similarity	NPD4181	Approved
0.6418	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5854	Approved
0.6417	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD6787	Phase 2
0.6409	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD1586	Approved
0.6396	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD3476	Approved
0.6391	Remote Similarity	NPD3475	Approved
0.639	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.639	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD484	Approved
0.6383	Remote Similarity	NPD3609	Approved
0.6383	Remote Similarity	NPD3610	Approved
0.6382	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD3968	Approved
0.6373	Remote Similarity	NPD6176	Phase 1
0.6364	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.635	Remote Similarity	NPD2307	Discontinued
0.635	Remote Similarity	NPD6226	Phase 3
0.635	Remote Similarity	NPD7027	Phase 3
0.6349	Remote Similarity	NPD1958	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6178	Phase 3
0.6333	Remote Similarity	NPD4463	Approved
0.6333	Remote Similarity	NPD4462	Approved
0.6329	Remote Similarity	NPD2442	Approved
0.6329	Remote Similarity	NPD2443	Approved
0.6327	Remote Similarity	NPD8431	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