NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.12
Volume:	259.353
LogP:	2.288
LogD:	1.879
LogS:	-3.89
# Rotatable Bonds:	1
TPSA:	63.19
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.763
Synthetic Accessibility Score:	2.768
Fsp3:	0.143
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:	-5.073
MDCK Permeability:	1.1304324289085343e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.932
Human Intestinal Absorption (HIA):	0.131
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.203

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	70.36384582519531%
Volume Distribution (VD):	0.908
Pgp-substrate:	34.478084564208984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.614
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.486
CYP2C19-substrate:	0.42
CYP2C9-inhibitor:	0.676
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.204
CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.408
CYP3A4-substrate:	0.7

ADMET: Excretion

Clearance (CL):	3.781
Half-life (T1/2):	0.759

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.874
Drug-inuced Liver Injury (DILI):	0.889
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.165
Skin Sensitization:	0.865
Carcinogencity:	0.546
Eye Corrosion:	0.007
Eye Irritation:	0.073
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC473380

Natural Product ID:	NPC473380
*Common Name:**	Aplysinopsin
IUPAC Name:	(5E)-2-imino-5-(1H-indol-3-ylmethylidene)-1,3-dimethylimidazolidin-4-one
Synonyms:	Aplysinopsin
Standard InCHIKey:	AZGOVLGMSGAOMP-FZYUQVBKSA-N
Standard InCHI:	InChI=1S/C14H14N4O/c1-17-12(13(19)18(2)14(17)15)7-9-8-16-11-6-4-3-5-10(9)11/h3-8,15-16H,1-2H3/b12-7+,15-14?
SMILES:	N=C1N(C)C(=O)/C(=Cc2c[nH]c3c2cccc3)/N1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404232
PubChem CID:	5359000
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids 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
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374971]
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975486]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO33153	thorectandra sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO33044	florida sponges	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18217716]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]
NPO33297	aplysina sp.	Species	Aplysinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[7964781]

☑ 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	6
Ki	8
MIC	1
Others	9

Activity Type	# Activity
Cell Line	2
Individual Protein	14
Organism	1
Others	6
SELECTIVITY GROUP	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.4	ug.mL-1	PMID[450509]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2.3	ug.mL-1	PMID[450509]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Ki	=	14451.0	nM	PMID[450510]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Ki	=	598.0	nM	PMID[450510]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Activity	=	0.0	%	PMID[450510]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Activity	=	47.0	%	PMID[450510]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	10017.0	nM	PMID[450511]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	35.0	nM	PMID[450511]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	10017.0	nM	PMID[450512]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Ki	=	10000.0	nM	PMID[450512]
NPT294	Individual Protein	Serotonin 6 (5-HT6) receptor	Homo sapiens	Ki	=	8768.0	nM	PMID[450512]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Ki	=	4449.0	nM	PMID[450512]
NPT425	Individual Protein	Serotonin 3a (5-HT3a) receptor	Homo sapiens	Ki	=	3029.0	nM	PMID[450512]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	35.0	nM	PMID[450512]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	25.0	ug.mL-1	PMID[450508]
NPT22130	SELECTIVITY GROUP	Serotonin 2 receptors; 5-HT2a & 5-HT2c	Homo sapiens	Ki	=	0.041	nM	PMID[450510]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Activity	=	0.0	%	PMID[450510]
NPT2	Others	Unspecified		Ratio IC50	=	290.34	n.a.	PMID[450511]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[450512]
NPT2	Others	Unspecified		Ratio IC50	=	290.34	n.a.	PMID[450512]
NPT35	Others	n.a.		-log(solubility)	=	4.5	n.a.	PMID[450513]
NPT35	Others	n.a.		-log(solubility)	=	4.25	n.a.	PMID[450513]
NPT35	Others	n.a.		-log(solubility)	=	4.1	n.a.	PMID[450513]
NPT35	Others	n.a.		-log(solubility)	=	6.41	n.a.	PMID[450513]

☑ 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 NPC473380 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	896
0.1-0.2	12260
0.2-0.3	19582
0.3-0.4	4379
0.4-0.5	2181
0.5-0.6	1816
0.6-0.7	1151
0.7-0.8	414
0.8-0.85	11
0.85-0.9	1
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC240088
0.9812	High Similarity	NPC265710
0.9752	High Similarity	NPC16659
0.924	High Similarity	NPC474180
0.924	High Similarity	NPC188821
0.8708	High Similarity	NPC474389
0.8393	Intermediate Similarity	NPC49217
0.8323	Intermediate Similarity	NPC143872
0.8263	Intermediate Similarity	NPC470204
0.825	Intermediate Similarity	NPC190296
0.8214	Intermediate Similarity	NPC470203
0.8182	Intermediate Similarity	NPC200214
0.8176	Intermediate Similarity	NPC73767
0.8176	Intermediate Similarity	NPC110126
0.8165	Intermediate Similarity	NPC84911
0.8148	Intermediate Similarity	NPC314372
0.8148	Intermediate Similarity	NPC470440
0.8128	Intermediate Similarity	NPC473376
0.8101	Intermediate Similarity	NPC96102
0.8101	Intermediate Similarity	NPC29886
0.8101	Intermediate Similarity	NPC261195
0.8057	Intermediate Similarity	NPC284775
0.8056	Intermediate Similarity	NPC213629
0.805	Intermediate Similarity	NPC105127
0.8047	Intermediate Similarity	NPC122141
0.8037	Intermediate Similarity	NPC204141
0.8037	Intermediate Similarity	NPC159856
0.8012	Intermediate Similarity	NPC469783
0.8012	Intermediate Similarity	NPC469768
0.8012	Intermediate Similarity	NPC469761
0.8012	Intermediate Similarity	NPC469779
0.8012	Intermediate Similarity	NPC469780
0.8012	Intermediate Similarity	NPC469767
0.8012	Intermediate Similarity	NPC469784
0.8011	Intermediate Similarity	NPC11126
0.8	Intermediate Similarity	NPC116555
0.7988	Intermediate Similarity	NPC288838
0.7963	Intermediate Similarity	NPC469766
0.7952	Intermediate Similarity	NPC53947
0.7952	Intermediate Similarity	NPC105818
0.7952	Intermediate Similarity	NPC24678
0.7944	Intermediate Similarity	NPC94752
0.7939	Intermediate Similarity	NPC471957
0.7933	Intermediate Similarity	NPC477003
0.7908	Intermediate Similarity	NPC475736
0.7901	Intermediate Similarity	NPC279081
0.7901	Intermediate Similarity	NPC17059
0.7892	Intermediate Similarity	NPC321911
0.7889	Intermediate Similarity	NPC308931
0.7889	Intermediate Similarity	NPC99939
0.7882	Intermediate Similarity	NPC135141
0.7882	Intermediate Similarity	NPC92796
0.7876	Intermediate Similarity	NPC54981
0.7876	Intermediate Similarity	NPC320968
0.7869	Intermediate Similarity	NPC476460
0.7857	Intermediate Similarity	NPC25008
0.7857	Intermediate Similarity	NPC469786
0.7857	Intermediate Similarity	NPC469760
0.7857	Intermediate Similarity	NPC73952
0.7857	Intermediate Similarity	NPC469765
0.7857	Intermediate Similarity	NPC469763
0.7857	Intermediate Similarity	NPC259644
0.7848	Intermediate Similarity	NPC82295
0.7845	Intermediate Similarity	NPC476527
0.7833	Intermediate Similarity	NPC228835
0.7831	Intermediate Similarity	NPC469811
0.7831	Intermediate Similarity	NPC201380
0.7831	Intermediate Similarity	NPC179787
0.7828	Intermediate Similarity	NPC474195
0.7826	Intermediate Similarity	NPC125746
0.7811	Intermediate Similarity	NPC211572
0.7811	Intermediate Similarity	NPC212376
0.7811	Intermediate Similarity	NPC70922
0.7811	Intermediate Similarity	NPC80597
0.7811	Intermediate Similarity	NPC75540
0.7807	Intermediate Similarity	NPC171317
0.7795	Intermediate Similarity	NPC54744
0.7791	Intermediate Similarity	NPC230002
0.7789	Intermediate Similarity	NPC317701
0.7784	Intermediate Similarity	NPC161861
0.7778	Intermediate Similarity	NPC293487
0.7771	Intermediate Similarity	NPC63545
0.7746	Intermediate Similarity	NPC478184
0.7746	Intermediate Similarity	NPC478182
0.7722	Intermediate Similarity	NPC191415
0.772	Intermediate Similarity	NPC71238
0.7713	Intermediate Similarity	NPC473640
0.7704	Intermediate Similarity	NPC282247
0.7702	Intermediate Similarity	NPC198988
0.7701	Intermediate Similarity	NPC42372
0.7701	Intermediate Similarity	NPC280864
0.7701	Intermediate Similarity	NPC17751
0.7692	Intermediate Similarity	NPC216713
0.7688	Intermediate Similarity	NPC326422
0.7688	Intermediate Similarity	NPC225018
0.7677	Intermediate Similarity	NPC267811
0.7673	Intermediate Similarity	NPC474196
0.7672	Intermediate Similarity	NPC100321
0.7672	Intermediate Similarity	NPC293917
0.7661	Intermediate Similarity	NPC469785
0.7654	Intermediate Similarity	NPC325252
0.7654	Intermediate Similarity	NPC145885
0.7654	Intermediate Similarity	NPC84827
0.7654	Intermediate Similarity	NPC14113
0.765	Intermediate Similarity	NPC135601
0.765	Intermediate Similarity	NPC17273
0.765	Intermediate Similarity	NPC141612
0.7647	Intermediate Similarity	NPC325903
0.7644	Intermediate Similarity	NPC317105
0.764	Intermediate Similarity	NPC293216
0.7627	Intermediate Similarity	NPC54214
0.7626	Intermediate Similarity	NPC470731
0.7626	Intermediate Similarity	NPC470732
0.7624	Intermediate Similarity	NPC307191
0.7616	Intermediate Similarity	NPC236711
0.7616	Intermediate Similarity	NPC469762
0.7616	Intermediate Similarity	NPC216643
0.7602	Intermediate Similarity	NPC34844
0.7592	Intermediate Similarity	NPC475506
0.7588	Intermediate Similarity	NPC470823
0.7586	Intermediate Similarity	NPC478185
0.7586	Intermediate Similarity	NPC282231
0.7582	Intermediate Similarity	NPC470205
0.7582	Intermediate Similarity	NPC102755
0.7563	Intermediate Similarity	NPC471194
0.7563	Intermediate Similarity	NPC471193
0.7557	Intermediate Similarity	NPC160105
0.7557	Intermediate Similarity	NPC478183
0.7552	Intermediate Similarity	NPC155143
0.7546	Intermediate Similarity	NPC218268
0.7544	Intermediate Similarity	NPC281094
0.7544	Intermediate Similarity	NPC141926
0.7543	Intermediate Similarity	NPC311276
0.7541	Intermediate Similarity	NPC21429
0.7529	Intermediate Similarity	NPC279918
0.7529	Intermediate Similarity	NPC131718
0.7514	Intermediate Similarity	NPC126709
0.7514	Intermediate Similarity	NPC276540
0.7514	Intermediate Similarity	NPC233050
0.7514	Intermediate Similarity	NPC248041
0.75	Intermediate Similarity	NPC280852
0.75	Intermediate Similarity	NPC304203
0.75	Intermediate Similarity	NPC133003
0.75	Intermediate Similarity	NPC280290
0.75	Intermediate Similarity	NPC267885
0.7475	Intermediate Similarity	NPC153980
0.7475	Intermediate Similarity	NPC6865
0.7475	Intermediate Similarity	NPC470702
0.7475	Intermediate Similarity	NPC473218
0.7474	Intermediate Similarity	NPC174281
0.7474	Intermediate Similarity	NPC475286
0.7473	Intermediate Similarity	NPC91179
0.7472	Intermediate Similarity	NPC91895
0.7472	Intermediate Similarity	NPC194411
0.7472	Intermediate Similarity	NPC32534
0.7471	Intermediate Similarity	NPC318065
0.7471	Intermediate Similarity	NPC56765
0.7471	Intermediate Similarity	NPC230869
0.7471	Intermediate Similarity	NPC206819
0.746	Intermediate Similarity	NPC294693
0.7459	Intermediate Similarity	NPC59269
0.7458	Intermediate Similarity	NPC470509
0.7458	Intermediate Similarity	NPC49954
0.7458	Intermediate Similarity	NPC114637
0.7458	Intermediate Similarity	NPC474561
0.7453	Intermediate Similarity	NPC22079
0.7446	Intermediate Similarity	NPC165495
0.7444	Intermediate Similarity	NPC203468
0.7444	Intermediate Similarity	NPC149155
0.7444	Intermediate Similarity	NPC110500
0.7443	Intermediate Similarity	NPC40779
0.7443	Intermediate Similarity	NPC247987
0.744	Intermediate Similarity	NPC69843
0.7437	Intermediate Similarity	NPC470703
0.7432	Intermediate Similarity	NPC275292
0.7432	Intermediate Similarity	NPC470677
0.7432	Intermediate Similarity	NPC243381
0.7424	Intermediate Similarity	NPC72956
0.7421	Intermediate Similarity	NPC329765
0.7421	Intermediate Similarity	NPC48117
0.7421	Intermediate Similarity	NPC476526
0.7418	Intermediate Similarity	NPC283219
0.7416	Intermediate Similarity	NPC78020
0.7414	Intermediate Similarity	NPC299594
0.7414	Intermediate Similarity	NPC286427
0.741	Intermediate Similarity	NPC88097
0.7405	Intermediate Similarity	NPC15102
0.7398	Intermediate Similarity	NPC54420
0.7396	Intermediate Similarity	NPC153123
0.7396	Intermediate Similarity	NPC19696
0.7396	Intermediate Similarity	NPC475914
0.7396	Intermediate Similarity	NPC136957
0.7396	Intermediate Similarity	NPC477004
0.7396	Intermediate Similarity	NPC220797
0.7396	Intermediate Similarity	NPC474318
0.7396	Intermediate Similarity	NPC201266
0.7396	Intermediate Similarity	NPC268744
0.7394	Intermediate Similarity	NPC150259
0.7389	Intermediate Similarity	NPC314603
0.7384	Intermediate Similarity	NPC472260

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 NPC473380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	779
0.2-0.3	1168
0.3-0.4	1945
0.4-0.5	2010
0.5-0.6	1938
0.6-0.7	848
0.7-0.8	145
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
0.8101	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD786	Approved
0.8042	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD2008	Discontinued
0.7952	Intermediate Similarity	NPD2172	Phase 1
0.7943	Intermediate Similarity	NPD4128	Approved
0.7921	Intermediate Similarity	NPD1708	Approved
0.7921	Intermediate Similarity	NPD1895	Discontinued
0.7921	Intermediate Similarity	NPD1707	Approved
0.7906	Intermediate Similarity	NPD2442	Approved
0.7906	Intermediate Similarity	NPD2443	Approved
0.7853	Intermediate Similarity	NPD1722	Approved
0.7853	Intermediate Similarity	NPD4181	Approved
0.7849	Intermediate Similarity	NPD2880	Discontinued
0.7845	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD3961	Discontinued
0.7797	Intermediate Similarity	NPD4075	Phase 2
0.7784	Intermediate Similarity	NPD3100	Discontinued
0.7778	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD6217	Discontinued
0.7744	Intermediate Similarity	NPD2411	Approved
0.7705	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD2408	Discontinued
0.7679	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7970	Approved
0.7665	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD2639	Approved
0.7657	Intermediate Similarity	NPD2642	Approved
0.765	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1600	Suspended
0.7569	Intermediate Similarity	NPD6595	Phase 3
0.7566	Intermediate Similarity	NPD6664	Approved
0.7557	Intermediate Similarity	NPD1248	Discontinued
0.7554	Intermediate Similarity	NPD7026	Phase 2
0.7553	Intermediate Similarity	NPD7618	Phase 3
0.7553	Intermediate Similarity	NPD7619	Phase 3
0.7551	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1404	Approved
0.7529	Intermediate Similarity	NPD1403	Approved
0.7528	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5199	Approved
0.7512	Intermediate Similarity	NPD5198	Approved
0.75	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD1506	Discontinued
0.7473	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD2793	Discontinued
0.7444	Intermediate Similarity	NPD482	Approved
0.7442	Intermediate Similarity	NPD2837	Discontinued
0.7435	Intermediate Similarity	NPD1982	Phase 1
0.7432	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD8256	Approved
0.7413	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD8257	Approved
0.7409	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD460	Discontinued
0.7405	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6771	Discontinued
0.7381	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7175	Phase 1
0.7363	Intermediate Similarity	NPD2144	Approved
0.7356	Intermediate Similarity	NPD2150	Discontinued
0.7354	Intermediate Similarity	NPD4922	Phase 2
0.7345	Intermediate Similarity	NPD3323	Discontinued
0.7337	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6828	Phase 2
0.7318	Intermediate Similarity	NPD2640	Approved
0.7318	Intermediate Similarity	NPD2641	Approved
0.731	Intermediate Similarity	NPD7445	Phase 1
0.7306	Intermediate Similarity	NPD2405	Phase 3
0.7303	Intermediate Similarity	NPD1313	Approved
0.73	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD750	Phase 2
0.7291	Intermediate Similarity	NPD6470	Phase 3
0.7289	Intermediate Similarity	NPD1262	Discovery
0.7283	Intermediate Similarity	NPD5508	Phase 1
0.7278	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3505	Approved
0.7268	Intermediate Similarity	NPD3506	Approved
0.7264	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4615	Phase 2
0.7262	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7564	Discontinued
0.7257	Intermediate Similarity	NPD2580	Discontinued
0.7253	Intermediate Similarity	NPD5065	Approved
0.7249	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD5685	Approved
0.7249	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD5686	Approved
0.7249	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD3038	Discontinued
0.7228	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4076	Approved
0.7228	Intermediate Similarity	NPD4079	Approved
0.7225	Intermediate Similarity	NPD4463	Approved
0.7225	Intermediate Similarity	NPD4462	Approved
0.7222	Intermediate Similarity	NPD2333	Discontinued
0.7222	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7402	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6044	Discontinued
0.7208	Intermediate Similarity	NPD8272	Phase 2
0.7208	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD2095	Phase 2
0.7204	Intermediate Similarity	NPD2092	Phase 2
0.7204	Intermediate Similarity	NPD5106	Approved
0.7204	Intermediate Similarity	NPD2094	Phase 2
0.7204	Intermediate Similarity	NPD5105	Approved
0.7194	Intermediate Similarity	NPD2881	Approved
0.7194	Intermediate Similarity	NPD3015	Discontinued
0.7194	Intermediate Similarity	NPD2879	Approved
0.7189	Intermediate Similarity	NPD5962	Phase 2
0.7186	Intermediate Similarity	NPD6459	Phase 2
0.7181	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6165	Phase 2
0.7177	Intermediate Similarity	NPD6164	Phase 2
0.7174	Intermediate Similarity	NPD7111	Discontinued
0.717	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD2096	Phase 2
0.7166	Intermediate Similarity	NPD2091	Phase 2
0.7159	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1683	Approved
0.7151	Intermediate Similarity	NPD3583	Phase 2
0.715	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3609	Approved
0.7143	Intermediate Similarity	NPD3610	Approved
0.7135	Intermediate Similarity	NPD5254	Discontinued
0.7135	Intermediate Similarity	NPD1327	Discontinued
0.7135	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1030	Approved
0.7126	Intermediate Similarity	NPD1027	Approved
0.7126	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1658	Discontinued
0.7115	Intermediate Similarity	NPD6849	Phase 2
0.7115	Intermediate Similarity	NPD6850	Phase 2
0.7112	Intermediate Similarity	NPD3318	Approved
0.7112	Intermediate Similarity	NPD3319	Phase 1
0.7112	Intermediate Similarity	NPD3320	Approved
0.7111	Intermediate Similarity	NPD509	Phase 3
0.7107	Intermediate Similarity	NPD6268	Phase 1
0.7107	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD803	Phase 1
0.709	Intermediate Similarity	NPD706	Phase 1
0.7088	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3431	Approved
0.7083	Intermediate Similarity	NPD3430	Approved
0.7081	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4047	Discontinued
0.7073	Intermediate Similarity	NPD3654	Approved
0.7072	Intermediate Similarity	NPD5611	Phase 2
0.7071	Intermediate Similarity	NPD2364	Suspended
0.7065	Intermediate Similarity	NPD7704	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5017	Discontinued
0.7055	Intermediate Similarity	NPD991	Phase 2
0.7055	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7394	Phase 2
0.705	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6328	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3905	Phase 3
0.7047	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1303	Phase 1
0.7044	Intermediate Similarity	NPD7657	Approved
0.7044	Intermediate Similarity	NPD7656	Approved
0.7043	Intermediate Similarity	NPD8386	Phase 2
0.7043	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7208	Approved
0.7035	Intermediate Similarity	NPD7207	Approved
0.7035	Intermediate Similarity	NPD7209	Approved
0.703	Intermediate Similarity	NPD3475	Approved
0.703	Intermediate Similarity	NPD3476	Approved
0.703	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3830	Phase 1
0.7026	Intermediate Similarity	NPD1952	Discontinued
0.7026	Intermediate Similarity	NPD5446	Phase 2
0.7017	Intermediate Similarity	NPD2915	Discontinued
0.7017	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2510	Approved
0.7015	Intermediate Similarity	NPD2509	Approved
0.7011	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4547	Phase 3
0.701	Intermediate Similarity	NPD8094	Discontinued

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