NPASS Compound

Structure

NPC173344 OpenBabel07101719142D 26 30 0 0 0 0 0 0 0 0999 V2000 -1.6470 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4456 1.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3880 0.4163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8087 1.6192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6935 0.0818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7810 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1142 1.2847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0566 0.5160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -1.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4197 0.0818 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7810 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 12 2 0 0 0 0 5 15 2 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 23 2 0 0 0 0 10 26 1 0 0 0 0 11 21 2 3 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.1
Volume:	356.616
LogP:	2.7
LogD:	2.728
LogS:	-4.636
# Rotatable Bonds:	4
TPSA:	67.24
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.563
Synthetic Accessibility Score:	3.292
Fsp3:	0.2
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:	-5.076
MDCK Permeability:	3.546102379914373e-05
Pgp-inhibitor:	0.769
Pgp-substrate:	0.666
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.892
Plasma Protein Binding (PPB):	95.92342376708984%
Volume Distribution (VD):	1.23
Pgp-substrate:	2.3187220096588135%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.205
CYP2C19-substrate:	0.315
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.632
CYP2D6-inhibitor:	0.677
CYP2D6-substrate:	0.557
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.545

ADMET: Excretion

Clearance (CL):	1.694
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.114
Human Hepatotoxicity (H-HT):	0.633
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.92
Rat Oral Acute Toxicity:	0.494
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.307
Carcinogencity:	0.925
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC173344

Natural Product ID:	NPC173344
*Common Name:**	Kuanoniamine D
IUPAC Name:	n.a.
Synonyms:	Kuanoniamine D
Standard InCHIKey:	GUSIRVISUKPQFL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16N4OS/c1-11(25)21-8-7-14-17-16-13(12-4-2-3-5-15(12)24-17)6-9-22-18(16)19-20(14)26-10-23-19/h2-6,9-10,24H,7-8H2,1H3,(H,21,25)
SMILES:	CC(=NCCc1c2c3c(-c4ccccc4N2)ccnc3c2c1scn2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL127872
PubChem CID:	10067080
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0002827] Pyrido[2,3,4-kl]acridines

*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
NPO33149	oceanapia sp.	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843591]
NPO33149	oceanapia sp.	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921437]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812214]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20491501]
NPO32634	cystodytes sp. ascidian	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7525959]
NPO33149	oceanapia sp.	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7769396]
NPO33149	oceanapia sp.	Species	Phloeodictyidae	Eukaryota	n.a.	micronesian	n.a.	PMID[9514015]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Ki	2
MIC	3
Others	8

Activity Type	# Activity
Cell Line	3
Individual Protein	4
NON-MOLECULAR	1
Organism	5
Others	3
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	7800.0	nM	PMID[464879]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1.4	ug.mL-1	PMID[464880]
NPT2103	Cell Line	MONO-MAC-6	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[464880]
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Activity	=	68.0	%	PMID[464880]
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	Activity	=	56.0	%	PMID[464880]
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Ki	=	2940.0	nM	PMID[464880]
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	Ki	=	13700.0	nM	PMID[464880]
NPT27	Others	Unspecified		IC50	=	88900.0	nM	PMID[464879]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	2.0	n.a.	PMID[464879]
NPT320	Protein Family	DNA topoisomerase II	Homo sapiens	IC90	=	127000.0	nM	PMID[464879]
NPT2	Others	Unspecified		K	=	62.0	uM	PMID[464879]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LC50	=	59.0	ppm	PMID[464880]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	19.0	ug.mL-1	PMID[464880]
NPT2	Others	Unspecified		Activity	=	32.0	%	PMID[464880]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2200.0	nM	PMID[464881]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	17400.0	nM	PMID[464881]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	34000.0	nM	PMID[464882]

☑ 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 NPC173344 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	961
0.1-0.2	14566
0.2-0.3	18955
0.3-0.4	3792
0.4-0.5	2276
0.5-0.6	1748
0.6-0.7	389
0.7-0.8	1
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9948	High Similarity	NPC149014
0.9846	High Similarity	NPC77022
0.9796	High Similarity	NPC216221
0.9585	High Similarity	NPC147810
0.899	High Similarity	NPC66699
0.8939	High Similarity	NPC175916
0.8856	High Similarity	NPC124636
0.8812	High Similarity	NPC193370
0.734	Intermediate Similarity	NPC164228
0.7228	Intermediate Similarity	NPC297034
0.7128	Intermediate Similarity	NPC161108
0.705	Intermediate Similarity	NPC317105
0.7041	Intermediate Similarity	NPC325903
0.7035	Intermediate Similarity	NPC44773
0.7035	Intermediate Similarity	NPC215584
0.7024	Intermediate Similarity	NPC280852
0.6995	Remote Similarity	NPC91895
0.6934	Remote Similarity	NPC255909
0.6934	Remote Similarity	NPC103119
0.6923	Remote Similarity	NPC179787
0.6923	Remote Similarity	NPC201380
0.6904	Remote Similarity	NPC216713
0.6888	Remote Similarity	NPC321911
0.6872	Remote Similarity	NPC63545
0.6837	Remote Similarity	NPC470111
0.6837	Remote Similarity	NPC471957
0.6837	Remote Similarity	NPC469811
0.6837	Remote Similarity	NPC272458
0.6835	Remote Similarity	NPC24802
0.6835	Remote Similarity	NPC265576
0.6816	Remote Similarity	NPC474791
0.6812	Remote Similarity	NPC471579
0.6796	Remote Similarity	NPC201634
0.6768	Remote Similarity	NPC40070
0.6766	Remote Similarity	NPC236711
0.675	Remote Similarity	NPC476219
0.6749	Remote Similarity	NPC225018
0.6749	Remote Similarity	NPC470203
0.6748	Remote Similarity	NPC194411
0.6746	Remote Similarity	NPC248454
0.6745	Remote Similarity	NPC467063
0.6744	Remote Similarity	NPC231536
0.6742	Remote Similarity	NPC469308
0.6733	Remote Similarity	NPC135141
0.6733	Remote Similarity	NPC92796
0.6733	Remote Similarity	NPC56765
0.6716	Remote Similarity	NPC478184
0.6716	Remote Similarity	NPC478182
0.67	Remote Similarity	NPC122141
0.67	Remote Similarity	NPC470204
0.6667	Remote Similarity	NPC88121
0.6651	Remote Similarity	NPC275305
0.6651	Remote Similarity	NPC37423
0.665	Remote Similarity	NPC470233
0.665	Remote Similarity	NPC314372
0.665	Remote Similarity	NPC470823
0.6636	Remote Similarity	NPC272483
0.6634	Remote Similarity	NPC90723
0.6633	Remote Similarity	NPC190296
0.6632	Remote Similarity	NPC314102
0.6632	Remote Similarity	NPC251722
0.6622	Remote Similarity	NPC475288
0.662	Remote Similarity	NPC163055
0.6617	Remote Similarity	NPC200214
0.6615	Remote Similarity	NPC284635
0.66	Remote Similarity	NPC148592
0.66	Remote Similarity	NPC24678
0.66	Remote Similarity	NPC53947
0.66	Remote Similarity	NPC105818
0.6598	Remote Similarity	NPC169433
0.6593	Remote Similarity	NPC166492
0.6593	Remote Similarity	NPC473362
0.6588	Remote Similarity	NPC68354
0.657	Remote Similarity	NPC56233
0.6569	Remote Similarity	NPC318065
0.6569	Remote Similarity	NPC293487
0.6569	Remote Similarity	NPC206819
0.6558	Remote Similarity	NPC49051
0.6558	Remote Similarity	NPC15102
0.6557	Remote Similarity	NPC176199
0.6557	Remote Similarity	NPC215795
0.6555	Remote Similarity	NPC82331
0.6548	Remote Similarity	NPC320863
0.654	Remote Similarity	NPC474958
0.6537	Remote Similarity	NPC229173
0.6535	Remote Similarity	NPC469765
0.6535	Remote Similarity	NPC73952
0.6535	Remote Similarity	NPC469760
0.6535	Remote Similarity	NPC259644
0.6535	Remote Similarity	NPC469763
0.6535	Remote Similarity	NPC469786
0.6535	Remote Similarity	NPC25008
0.6533	Remote Similarity	NPC288838
0.6531	Remote Similarity	NPC115611
0.653	Remote Similarity	NPC324149
0.652	Remote Similarity	NPC286427
0.6516	Remote Similarity	NPC128244
0.6509	Remote Similarity	NPC59269
0.6509	Remote Similarity	NPC157583
0.6502	Remote Similarity	NPC212376
0.6502	Remote Similarity	NPC75540
0.6502	Remote Similarity	NPC80597
0.6502	Remote Similarity	NPC211572
0.6502	Remote Similarity	NPC476297
0.6502	Remote Similarity	NPC70922
0.6498	Remote Similarity	NPC317030
0.649	Remote Similarity	NPC478183
0.6488	Remote Similarity	NPC41257
0.6482	Remote Similarity	NPC285731
0.6482	Remote Similarity	NPC159856
0.6471	Remote Similarity	NPC294693
0.6471	Remote Similarity	NPC51054
0.6465	Remote Similarity	NPC48938
0.6463	Remote Similarity	NPC39092
0.6459	Remote Similarity	NPC63751
0.6452	Remote Similarity	NPC474707
0.6447	Remote Similarity	NPC469761
0.6447	Remote Similarity	NPC469767
0.6447	Remote Similarity	NPC469780
0.6447	Remote Similarity	NPC469779
0.6447	Remote Similarity	NPC469783
0.6447	Remote Similarity	NPC469768
0.6447	Remote Similarity	NPC469784
0.6442	Remote Similarity	NPC274229
0.6439	Remote Similarity	NPC216643
0.6438	Remote Similarity	NPC95783
0.6435	Remote Similarity	NPC108011
0.6432	Remote Similarity	NPC475070
0.6429	Remote Similarity	NPC19170
0.6425	Remote Similarity	NPC478185
0.6422	Remote Similarity	NPC204565
0.6419	Remote Similarity	NPC477111
0.6419	Remote Similarity	NPC314957
0.6419	Remote Similarity	NPC191415
0.6418	Remote Similarity	NPC21605
0.6414	Remote Similarity	NPC469766
0.6413	Remote Similarity	NPC229332
0.6413	Remote Similarity	NPC167710
0.6408	Remote Similarity	NPC221786
0.6408	Remote Similarity	NPC475990
0.6408	Remote Similarity	NPC474880
0.6406	Remote Similarity	NPC99939
0.6406	Remote Similarity	NPC308931
0.6402	Remote Similarity	NPC153467
0.64	Remote Similarity	NPC86288
0.6396	Remote Similarity	NPC110126
0.6396	Remote Similarity	NPC73767
0.6396	Remote Similarity	NPC88097
0.6395	Remote Similarity	NPC250835
0.6393	Remote Similarity	NPC65215
0.6393	Remote Similarity	NPC173028
0.639	Remote Similarity	NPC469785
0.6384	Remote Similarity	NPC34837
0.6382	Remote Similarity	NPC20144
0.6381	Remote Similarity	NPC201700
0.638	Remote Similarity	NPC216550
0.6378	Remote Similarity	NPC105127
0.6378	Remote Similarity	NPC84911
0.6376	Remote Similarity	NPC62749
0.6368	Remote Similarity	NPC251936
0.636	Remote Similarity	NPC88115
0.6359	Remote Similarity	NPC469897
0.6359	Remote Similarity	NPC469762
0.6359	Remote Similarity	NPC284678
0.6355	Remote Similarity	NPC237188
0.6355	Remote Similarity	NPC33421
0.6351	Remote Similarity	NPC326422
0.6351	Remote Similarity	NPC474897
0.6351	Remote Similarity	NPC97343
0.6351	Remote Similarity	NPC32534
0.6349	Remote Similarity	NPC297862
0.6343	Remote Similarity	NPC307191
0.6343	Remote Similarity	NPC233936
0.634	Remote Similarity	NPC304926
0.634	Remote Similarity	NPC476041
0.6333	Remote Similarity	NPC49954
0.6333	Remote Similarity	NPC160105
0.6333	Remote Similarity	NPC474561
0.6332	Remote Similarity	NPC477113
0.6329	Remote Similarity	NPC477591
0.6327	Remote Similarity	NPC96102
0.6327	Remote Similarity	NPC29886
0.6327	Remote Similarity	NPC261195
0.6323	Remote Similarity	NPC195314
0.6316	Remote Similarity	NPC317701
0.6316	Remote Similarity	NPC311276
0.6316	Remote Similarity	NPC194640
0.6314	Remote Similarity	NPC473310
0.6313	Remote Similarity	NPC102755
0.6309	Remote Similarity	NPC31385
0.6309	Remote Similarity	NPC75726
0.6309	Remote Similarity	NPC110602
0.6301	Remote Similarity	NPC94752
0.6296	Remote Similarity	NPC24864
0.6293	Remote Similarity	NPC138842
0.6291	Remote Similarity	NPC472123
0.6284	Remote Similarity	NPC472294
0.6282	Remote Similarity	NPC473757
0.628	Remote Similarity	NPC129721
0.628	Remote Similarity	NPC167635

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 NPC173344 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	412
0.1-0.2	936
0.2-0.3	1232
0.3-0.4	2579
0.4-0.5	2138
0.5-0.6	1564
0.6-0.7	283
0.7-0.8	6
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
0.7606	Intermediate Similarity	NPD2815	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3348	Phase 2
0.7352	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4865	Approved
0.7194	Intermediate Similarity	NPD1648	Phase 1
0.7194	Intermediate Similarity	NPD1647	Phase 1
0.7156	Intermediate Similarity	NPD7127	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2717	Phase 2
0.7116	Intermediate Similarity	NPD5828	Phase 2
0.71	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD2720	Phase 1
0.7097	Intermediate Similarity	NPD3015	Discontinued
0.7048	Intermediate Similarity	NPD7394	Phase 2
0.7044	Intermediate Similarity	NPD3609	Approved
0.7044	Intermediate Similarity	NPD3610	Approved
0.7027	Intermediate Similarity	NPD3843	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4547	Phase 3
0.7005	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD5105	Approved
0.6938	Remote Similarity	NPD5106	Approved
0.6919	Remote Similarity	NPD1597	Phase 1
0.6915	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5315	Discontinued
0.6909	Remote Similarity	NPD4886	Phase 2
0.6908	Remote Similarity	NPD4181	Approved
0.6887	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6224	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4050	Phase 1
0.6834	Remote Similarity	NPD975	Approved
0.6834	Remote Similarity	NPD976	Approved
0.6834	Remote Similarity	NPD977	Approved
0.6812	Remote Similarity	NPD4128	Approved
0.6808	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3323	Discontinued
0.6789	Remote Similarity	NPD5462	Discontinued
0.6786	Remote Similarity	NPD1683	Approved
0.6784	Remote Similarity	NPD2837	Discontinued
0.678	Remote Similarity	NPD2640	Approved
0.678	Remote Similarity	NPD2641	Approved
0.6779	Remote Similarity	NPD2771	Approved
0.6769	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4902	Discontinued
0.6756	Remote Similarity	NPD4471	Approved
0.6756	Remote Similarity	NPD4472	Approved
0.675	Remote Similarity	NPD6285	Phase 2
0.6744	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD3961	Discontinued
0.6717	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6044	Discontinued
0.6698	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6816	Phase 3
0.6697	Remote Similarity	NPD5904	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7423	Phase 2
0.6684	Remote Similarity	NPD4509	Discontinued
0.6682	Remote Similarity	NPD2409	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD3404	Approved
0.6667	Remote Similarity	NPD5412	Discontinued
0.6667	Remote Similarity	NPD2735	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1661	Suspended
0.6667	Remote Similarity	NPD7027	Phase 3
0.6667	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6957	Approved
0.6652	Remote Similarity	NPD6958	Approved
0.6651	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5428	Discontinued
0.6637	Remote Similarity	NPD6132	Phase 1
0.6636	Remote Similarity	NPD1235	Phase 3
0.6636	Remote Similarity	NPD5438	Approved
0.6636	Remote Similarity	NPD5439	Approved
0.6633	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3100	Discontinued
0.6618	Remote Similarity	NPD5021	Discontinued
0.6618	Remote Similarity	NPD1404	Approved
0.6618	Remote Similarity	NPD1403	Approved
0.6616	Remote Similarity	NPD7469	Discontinued
0.6616	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3469	Phase 3
0.6606	Remote Similarity	NPD4615	Phase 2
0.6606	Remote Similarity	NPD4470	Phase 2
0.6605	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD649	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6969	Phase 2
0.6597	Remote Similarity	NPD6968	Phase 2
0.6593	Remote Similarity	NPD5864	Phase 2
0.659	Remote Similarity	NPD2818	Discontinued
0.6589	Remote Similarity	NPD4957	Phase 2
0.6588	Remote Similarity	NPD7111	Discontinued
0.6588	Remote Similarity	NPD3506	Approved
0.6588	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3505	Approved
0.6587	Remote Similarity	NPD5436	Phase 1
0.658	Remote Similarity	NPD6711	Approved
0.6571	Remote Similarity	NPD5065	Approved
0.657	Remote Similarity	NPD2639	Approved
0.657	Remote Similarity	NPD2642	Approved
0.6561	Remote Similarity	NPD4473	Clinical (unspecified phase)
0.656	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4079	Approved
0.6557	Remote Similarity	NPD4076	Approved
0.6552	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2430	Phase 2
0.6548	Remote Similarity	NPD2006	Phase 2
0.654	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.654	Remote Similarity	NPD4075	Phase 2
0.6538	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2021	Discontinued
0.6522	Remote Similarity	NPD6749	Phase 1
0.6517	Remote Similarity	NPD2172	Phase 1
0.6512	Remote Similarity	NPD6178	Phase 3
0.6512	Remote Similarity	NPD7564	Discontinued
0.6507	Remote Similarity	NPD4051	Discontinued
0.6502	Remote Similarity	NPD1315	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD8431	Approved
0.6497	Remote Similarity	NPD1722	Approved
0.6496	Remote Similarity	NPD5270	Discontinued
0.6495	Remote Similarity	NPD1253	Approved
0.6495	Remote Similarity	NPD1255	Approved
0.6495	Remote Similarity	NPD1254	Approved
0.6495	Remote Similarity	NPD7867	Phase 1
0.6495	Remote Similarity	NPD1256	Approved
0.6488	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD5615	Phase 2
0.6478	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6156	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD754	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD2849	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6149	Phase 2
0.6471	Remote Similarity	NPD4999	Phase 3
0.6471	Remote Similarity	NPD4998	Phase 3
0.6462	Remote Similarity	NPD45	Approved
0.6462	Remote Similarity	NPD2406	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6554	Approved
0.6459	Remote Similarity	NPD4640	Approved
0.6459	Remote Similarity	NPD4638	Approved
0.6459	Remote Similarity	NPD4639	Approved
0.6456	Remote Similarity	NPD5094	Approved
0.6455	Remote Similarity	NPD6577	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6595	Phase 3
0.6449	Remote Similarity	NPD1928	Discontinued
0.6447	Remote Similarity	NPD7135	Phase 2
0.6445	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD917	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2058	Phase 2
0.6429	Remote Similarity	NPD2059	Approved
0.6429	Remote Similarity	NPD2057	Approved
0.6425	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6771	Discontinued
0.6422	Remote Similarity	NPD7264	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6664	Approved
0.6413	Remote Similarity	NPD3830	Phase 1
0.6409	Remote Similarity	NPD4949	Discontinued
0.6408	Remote Similarity	NPD5418	Discontinued
0.6407	Remote Similarity	NPD3265	Phase 1
0.6406	Remote Similarity	NPD715	Phase 3
0.6406	Remote Similarity	NPD3279	Phase 2
0.6402	Remote Similarity	NPD6352	Phase 2
0.6396	Remote Similarity	NPD786	Approved
0.6396	Remote Similarity	NPD7619	Phase 3
0.6396	Remote Similarity	NPD7618	Phase 3
0.6393	Remote Similarity	NPD4992	Phase 1
0.6392	Remote Similarity	NPD3385	Approved
0.6389	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD6139	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD2751	Phase 1
0.6384	Remote Similarity	NPD6469	Phase 3
0.6384	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5885	Approved
0.6382	Remote Similarity	NPD4510	Discontinued
0.6381	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4320	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD2793	Discontinued
0.6376	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7026	Phase 2
0.6375	Remote Similarity	NPD6170	Phase 2
0.6372	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD1556	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6281	Approved
0.6364	Remote Similarity	NPD6133	Discontinued
0.636	Remote Similarity	NPD7209	Approved
0.636	Remote Similarity	NPD7207	Approved
0.636	Remote Similarity	NPD7208	Approved
0.6359	Remote Similarity	NPD3607	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