NPASS Compound

Structure

NPC16659 OpenBabel07101718292D 21 23 0 0 0 0 0 0 0 0999 V2000 -3.0322 0.5862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2319 2.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0540 0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2773 2.2287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8651 1.4197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2828 2.1242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4584 0.5062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1160 1.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9250 -0.0984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9250 0.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8761 1.2106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4638 0.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 1.1215 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8761 -0.4074 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 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 1.6637 -0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 17 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 21 2 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.15
Volume:	293.945
LogP:	2.401
LogD:	1.594
LogS:	-4.196
# Rotatable Bonds:	2
TPSA:	51.7
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.859
Synthetic Accessibility Score:	2.977
Fsp3:	0.25
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:	-4.643
MDCK Permeability:	1.5136653928493615e-05
Pgp-inhibitor:	0.077
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.365

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.812
Plasma Protein Binding (PPB):	80.54749298095703%
Volume Distribution (VD):	1.197
Pgp-substrate:	24.920984268188477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.896
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.843
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.615
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.131
CYP2D6-substrate:	0.847
CYP3A4-inhibitor:	0.72
CYP3A4-substrate:	0.876

ADMET: Excretion

Clearance (CL):	6.341
Half-life (T1/2):	0.352

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.689
AMES Toxicity:	0.274
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.232
Skin Sensitization:	0.866
Carcinogencity:	0.755
Eye Corrosion:	0.013
Eye Irritation:	0.061
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC16659

Natural Product ID:	NPC16659
*Common Name:**	WPOIHWRJVKWRCZ-ZFCMMHTMSA-N
IUPAC Name:	n.a.
Synonyms:	N-3'-Ethylaplysinopsin
Standard InCHIKey:	WPOIHWRJVKWRCZ-ZFCMMHTMSA-N
Standard InCHI:	InChI=1S/C16H18N4O/c1-4-17-16-19(2)14(15(21)20(16)3)9-11-10-18-13-8-6-5-7-12(11)13/h5-10,18H,4H2,1-3H3/b14-9+,17-16-
SMILES:	CC/N=C1/N(C)/C(=C/c2c[nH]c3ccccc23)/C(=O)N1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463250
PubChem CID:	n.a.
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
NPO20958	Smenospongia aurea	Species	Thorectidae	Eukaryota	n.a.	Jamaican	n.a.	PMID[11975483]
NPO20958	Smenospongia aurea	Species	Thorectidae	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
Ki	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Ki	=	1700.0	nM	PMID[529423]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Ki	=	3500.0	nM	PMID[529423]

☑ 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 NPC16659 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	855
0.1-0.2	11158
0.2-0.3	20417
0.3-0.4	4580
0.4-0.5	2252
0.5-0.6	1804
0.6-0.7	1192
0.7-0.8	425
0.8-0.85	7
0.85-0.9	1
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC265710
0.9752	High Similarity	NPC240088
0.9752	High Similarity	NPC473380
0.9023	High Similarity	NPC474180
0.9023	High Similarity	NPC188821
0.8508	High Similarity	NPC474389
0.8402	Intermediate Similarity	NPC49217
0.8225	Intermediate Similarity	NPC470203
0.8193	Intermediate Similarity	NPC200214
0.8187	Intermediate Similarity	NPC73767
0.8167	Intermediate Similarity	NPC213629
0.8166	Intermediate Similarity	NPC470204
0.816	Intermediate Similarity	NPC314372
0.8148	Intermediate Similarity	NPC190296
0.8138	Intermediate Similarity	NPC473376
0.8137	Intermediate Similarity	NPC469767
0.8137	Intermediate Similarity	NPC469779
0.8137	Intermediate Similarity	NPC469768
0.8137	Intermediate Similarity	NPC469780
0.8137	Intermediate Similarity	NPC469784
0.8137	Intermediate Similarity	NPC469761
0.8137	Intermediate Similarity	NPC469783
0.811	Intermediate Similarity	NPC143872
0.8086	Intermediate Similarity	NPC469766
0.8075	Intermediate Similarity	NPC110126
0.8072	Intermediate Similarity	NPC24678
0.8072	Intermediate Similarity	NPC105818
0.8072	Intermediate Similarity	NPC53947
0.8068	Intermediate Similarity	NPC284775
0.8063	Intermediate Similarity	NPC84911
0.8056	Intermediate Similarity	NPC94752
0.8049	Intermediate Similarity	NPC470440
0.8045	Intermediate Similarity	NPC477003
0.8023	Intermediate Similarity	NPC11126
0.8011	Intermediate Similarity	NPC17059
0.8	Intermediate Similarity	NPC29886
0.8	Intermediate Similarity	NPC261195
0.8	Intermediate Similarity	NPC308931
0.8	Intermediate Similarity	NPC135141
0.8	Intermediate Similarity	NPC99939
0.8	Intermediate Similarity	NPC92796
0.8	Intermediate Similarity	NPC96102
0.8	Intermediate Similarity	NPC288838
0.7979	Intermediate Similarity	NPC54981
0.7978	Intermediate Similarity	NPC476460
0.7976	Intermediate Similarity	NPC259644
0.7976	Intermediate Similarity	NPC469765
0.7976	Intermediate Similarity	NPC469786
0.7976	Intermediate Similarity	NPC469763
0.7976	Intermediate Similarity	NPC25008
0.7976	Intermediate Similarity	NPC469760
0.7976	Intermediate Similarity	NPC73952
0.795	Intermediate Similarity	NPC105127
0.7944	Intermediate Similarity	NPC228835
0.7939	Intermediate Similarity	NPC204141
0.7939	Intermediate Similarity	NPC159856
0.7929	Intermediate Similarity	NPC212376
0.7929	Intermediate Similarity	NPC75540
0.7929	Intermediate Similarity	NPC70922
0.7929	Intermediate Similarity	NPC211572
0.7929	Intermediate Similarity	NPC80597
0.7917	Intermediate Similarity	NPC116555
0.7914	Intermediate Similarity	NPC171317
0.7898	Intermediate Similarity	NPC161861
0.7895	Intermediate Similarity	NPC317701
0.7887	Intermediate Similarity	NPC320968
0.7861	Intermediate Similarity	NPC478182
0.7857	Intermediate Similarity	NPC476527
0.7849	Intermediate Similarity	NPC122141
0.7844	Intermediate Similarity	NPC471957
0.7824	Intermediate Similarity	NPC71238
0.7819	Intermediate Similarity	NPC473640
0.7806	Intermediate Similarity	NPC54744
0.7805	Intermediate Similarity	NPC279081
0.7798	Intermediate Similarity	NPC321911
0.7778	Intermediate Similarity	NPC293917
0.7778	Intermediate Similarity	NPC469785
0.7778	Intermediate Similarity	NPC100321
0.776	Intermediate Similarity	NPC135601
0.776	Intermediate Similarity	NPC141612
0.776	Intermediate Similarity	NPC17273
0.775	Intermediate Similarity	NPC474195
0.775	Intermediate Similarity	NPC82295
0.7739	Intermediate Similarity	NPC475736
0.7738	Intermediate Similarity	NPC201380
0.7738	Intermediate Similarity	NPC469811
0.7738	Intermediate Similarity	NPC179787
0.7733	Intermediate Similarity	NPC469762
0.7733	Intermediate Similarity	NPC216643
0.7727	Intermediate Similarity	NPC470732
0.7727	Intermediate Similarity	NPC470731
0.7701	Intermediate Similarity	NPC326422
0.7697	Intermediate Similarity	NPC230002
0.7696	Intermediate Similarity	NPC475506
0.7692	Intermediate Similarity	NPC470205
0.7688	Intermediate Similarity	NPC293487
0.7688	Intermediate Similarity	NPC267811
0.7685	Intermediate Similarity	NPC474196
0.7679	Intermediate Similarity	NPC63545
0.767	Intermediate Similarity	NPC160105
0.7667	Intermediate Similarity	NPC84827
0.7667	Intermediate Similarity	NPC145885
0.7667	Intermediate Similarity	NPC14113
0.7665	Intermediate Similarity	NPC153980
0.7665	Intermediate Similarity	NPC471193
0.7665	Intermediate Similarity	NPC471194
0.7665	Intermediate Similarity	NPC6865
0.7661	Intermediate Similarity	NPC325903
0.7657	Intermediate Similarity	NPC311276
0.7657	Intermediate Similarity	NPC478184
0.7657	Intermediate Similarity	NPC317105
0.7656	Intermediate Similarity	NPC155143
0.765	Intermediate Similarity	NPC21429
0.7637	Intermediate Similarity	NPC191415
0.7637	Intermediate Similarity	NPC307191
0.7626	Intermediate Similarity	NPC282247
0.7622	Intermediate Similarity	NPC125746
0.7614	Intermediate Similarity	NPC72956
0.7614	Intermediate Similarity	NPC42372
0.7611	Intermediate Similarity	NPC280852
0.7609	Intermediate Similarity	NPC133003
0.7609	Intermediate Similarity	NPC280290
0.7607	Intermediate Similarity	NPC198988
0.7606	Intermediate Similarity	NPC304203
0.7602	Intermediate Similarity	NPC216713
0.7586	Intermediate Similarity	NPC56765
0.7586	Intermediate Similarity	NPC206819
0.7586	Intermediate Similarity	NPC318065
0.7584	Intermediate Similarity	NPC194411
0.7582	Intermediate Similarity	NPC91179
0.7576	Intermediate Similarity	NPC470702
0.7576	Intermediate Similarity	NPC473218
0.7571	Intermediate Similarity	NPC49954
0.7571	Intermediate Similarity	NPC474561
0.7571	Intermediate Similarity	NPC478183
0.7571	Intermediate Similarity	NPC470509
0.7569	Intermediate Similarity	NPC59269
0.7566	Intermediate Similarity	NPC294693
0.7561	Intermediate Similarity	NPC325252
0.7561	Intermediate Similarity	NPC218268
0.7557	Intermediate Similarity	NPC40779
0.7556	Intermediate Similarity	NPC293216
0.7554	Intermediate Similarity	NPC165495
0.7538	Intermediate Similarity	NPC470703
0.7536	Intermediate Similarity	NPC69843
0.7529	Intermediate Similarity	NPC286427
0.7529	Intermediate Similarity	NPC236711
0.7529	Intermediate Similarity	NPC299594
0.7515	Intermediate Similarity	NPC150259
0.7514	Intermediate Similarity	NPC15102
0.7514	Intermediate Similarity	NPC280864
0.7514	Intermediate Similarity	NPC17751
0.7514	Intermediate Similarity	NPC34844
0.75	Intermediate Similarity	NPC102755
0.75	Intermediate Similarity	NPC54420
0.75	Intermediate Similarity	NPC477004
0.75	Intermediate Similarity	NPC225018
0.75	Intermediate Similarity	NPC282231
0.75	Intermediate Similarity	NPC314603
0.75	Intermediate Similarity	NPC478185
0.75	Intermediate Similarity	NPC470823
0.75	Intermediate Similarity	NPC470233
0.7487	Intermediate Similarity	NPC475286
0.7487	Intermediate Similarity	NPC174281
0.7487	Intermediate Similarity	NPC321708
0.7486	Intermediate Similarity	NPC41257
0.7486	Intermediate Similarity	NPC475990
0.7486	Intermediate Similarity	NPC474880
0.7486	Intermediate Similarity	NPC221786
0.7463	Intermediate Similarity	NPC471192
0.7463	Intermediate Similarity	NPC476817
0.746	Intermediate Similarity	NPC47190
0.7459	Intermediate Similarity	NPC275305
0.7459	Intermediate Similarity	NPC37423
0.7458	Intermediate Similarity	NPC90723
0.7457	Intermediate Similarity	NPC141926
0.7457	Intermediate Similarity	NPC281094
0.7448	Intermediate Similarity	NPC470499
0.7444	Intermediate Similarity	NPC54214
0.7443	Intermediate Similarity	NPC279918
0.7443	Intermediate Similarity	NPC131718
0.7435	Intermediate Similarity	NPC329765
0.7435	Intermediate Similarity	NPC48117
0.7435	Intermediate Similarity	NPC476526
0.7432	Intermediate Similarity	NPC126709
0.7432	Intermediate Similarity	NPC276540
0.7432	Intermediate Similarity	NPC233050
0.7432	Intermediate Similarity	NPC248041
0.743	Intermediate Similarity	NPC201700
0.743	Intermediate Similarity	NPC63751
0.7425	Intermediate Similarity	NPC88097
0.7424	Intermediate Similarity	NPC162860
0.7424	Intermediate Similarity	NPC478158
0.7424	Intermediate Similarity	NPC223791
0.7424	Intermediate Similarity	NPC107077
0.7418	Intermediate Similarity	NPC267885
0.7414	Intermediate Similarity	NPC476219
0.7414	Intermediate Similarity	NPC476297
0.7409	Intermediate Similarity	NPC153123
0.7409	Intermediate Similarity	NPC475914

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 NPC16659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	726
0.2-0.3	1197
0.3-0.4	1901
0.4-0.5	2024
0.5-0.6	1926
0.6-0.7	901
0.7-0.8	160
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8161	Intermediate Similarity	NPD4128	Approved
0.8095	Intermediate Similarity	NPD2008	Discontinued
0.8075	Intermediate Similarity	NPD786	Approved
0.8072	Intermediate Similarity	NPD2172	Phase 1
0.8068	Intermediate Similarity	NPD4181	Approved
0.8053	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD1707	Approved
0.8034	Intermediate Similarity	NPD1708	Approved
0.801	Intermediate Similarity	NPD2442	Approved
0.801	Intermediate Similarity	NPD2443	Approved
0.8	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD2880	Discontinued
0.7956	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1895	Discontinued
0.7912	Intermediate Similarity	NPD3961	Discontinued
0.791	Intermediate Similarity	NPD4075	Phase 2
0.7904	Intermediate Similarity	NPD3100	Discontinued
0.7889	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD1722	Approved
0.7857	Intermediate Similarity	NPD6217	Discontinued
0.7846	Intermediate Similarity	NPD2411	Approved
0.7814	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD2408	Discontinued
0.7778	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2639	Approved
0.7771	Intermediate Similarity	NPD2642	Approved
0.7766	Intermediate Similarity	NPD6664	Approved
0.776	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7026	Phase 2
0.7727	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5199	Approved
0.77	Intermediate Similarity	NPD5198	Approved
0.768	Intermediate Similarity	NPD6595	Phase 3
0.7677	Intermediate Similarity	NPD7970	Approved
0.7677	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7618	Phase 3
0.766	Intermediate Similarity	NPD7619	Phase 3
0.765	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7175	Phase 1
0.7571	Intermediate Similarity	NPD1248	Discontinued
0.7569	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2793	Discontinued
0.7563	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD2837	Discontinued
0.7543	Intermediate Similarity	NPD1404	Approved
0.7543	Intermediate Similarity	NPD1403	Approved
0.7541	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD1982	Phase 1
0.7528	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD1600	Suspended
0.7512	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD8256	Approved
0.7512	Intermediate Similarity	NPD8257	Approved
0.75	Intermediate Similarity	NPD6771	Discontinued
0.7486	Intermediate Similarity	NPD5508	Phase 1
0.7475	Intermediate Similarity	NPD6470	Phase 3
0.7473	Intermediate Similarity	NPD2144	Approved
0.746	Intermediate Similarity	NPD4922	Phase 2
0.746	Intermediate Similarity	NPD4615	Phase 2
0.7458	Intermediate Similarity	NPD3323	Discontinued
0.7449	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5686	Approved
0.7447	Intermediate Similarity	NPD5685	Approved
0.7447	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6828	Phase 2
0.7432	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD2641	Approved
0.743	Intermediate Similarity	NPD2640	Approved
0.7418	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7445	Phase 1
0.7411	Intermediate Similarity	NPD1506	Discontinued
0.7405	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD2879	Approved
0.7385	Intermediate Similarity	NPD3015	Discontinued
0.7385	Intermediate Similarity	NPD2881	Approved
0.7381	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7111	Discontinued
0.7377	Intermediate Similarity	NPD3506	Approved
0.7377	Intermediate Similarity	NPD3505	Approved
0.7371	Intermediate Similarity	NPD2580	Discontinued
0.7371	Intermediate Similarity	NPD2150	Discontinued
0.7366	Intermediate Similarity	NPD7564	Discontinued
0.7363	Intermediate Similarity	NPD482	Approved
0.7363	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5065	Approved
0.7356	Intermediate Similarity	NPD6164	Phase 2
0.7356	Intermediate Similarity	NPD6165	Phase 2
0.7354	Intermediate Similarity	NPD3871	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD3870	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3038	Discontinued
0.7346	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD4462	Approved
0.7341	Intermediate Similarity	NPD4463	Approved
0.734	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4076	Approved
0.7337	Intermediate Similarity	NPD4079	Approved
0.7333	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2333	Discontinued
0.733	Intermediate Similarity	NPD460	Discontinued
0.7322	Intermediate Similarity	NPD6044	Discontinued
0.732	Intermediate Similarity	NPD2405	Phase 3
0.7318	Intermediate Similarity	NPD1313	Approved
0.7312	Intermediate Similarity	NPD5106	Approved
0.7312	Intermediate Similarity	NPD2092	Phase 2
0.7312	Intermediate Similarity	NPD2094	Phase 2
0.7312	Intermediate Similarity	NPD2095	Phase 2
0.7312	Intermediate Similarity	NPD5105	Approved
0.731	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8272	Phase 2
0.7297	Intermediate Similarity	NPD5962	Phase 2
0.7296	Intermediate Similarity	NPD6268	Phase 1
0.7296	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4047	Discontinued
0.7286	Intermediate Similarity	NPD6459	Phase 2
0.7278	Intermediate Similarity	NPD5611	Phase 2
0.7277	Intermediate Similarity	NPD3431	Approved
0.7277	Intermediate Similarity	NPD3430	Approved
0.7273	Intermediate Similarity	NPD2091	Phase 2
0.7273	Intermediate Similarity	NPD2096	Phase 2
0.7263	Intermediate Similarity	NPD3583	Phase 2
0.7254	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD3610	Approved
0.7253	Intermediate Similarity	NPD3609	Approved
0.7251	Intermediate Similarity	NPD5254	Discontinued
0.7243	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3905	Phase 3
0.7228	Intermediate Similarity	NPD7402	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1658	Discontinued
0.7222	Intermediate Similarity	NPD7207	Approved
0.7222	Intermediate Similarity	NPD7209	Approved
0.7222	Intermediate Similarity	NPD7208	Approved
0.7219	Intermediate Similarity	NPD3320	Approved
0.7219	Intermediate Similarity	NPD3318	Approved
0.7219	Intermediate Similarity	NPD3319	Phase 1
0.7216	Intermediate Similarity	NPD3830	Phase 1
0.7216	Intermediate Similarity	NPD5446	Phase 2
0.7213	Intermediate Similarity	NPD750	Phase 2
0.7212	Intermediate Similarity	NPD6850	Phase 2
0.7212	Intermediate Similarity	NPD6849	Phase 2
0.7198	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4024	Phase 3
0.7196	Intermediate Similarity	NPD4902	Discontinued
0.7195	Intermediate Similarity	NPD3654	Approved
0.7168	Intermediate Similarity	NPD1683	Approved
0.7165	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7394	Phase 2
0.7158	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4988	Discontinued
0.7157	Intermediate Similarity	NPD5017	Discontinued
0.7152	Intermediate Similarity	NPD3475	Approved
0.7152	Intermediate Similarity	NPD3476	Approved
0.7151	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1327	Discontinued
0.715	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6328	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7657	Approved
0.7143	Intermediate Similarity	NPD1030	Approved
0.7143	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7656	Approved
0.7143	Intermediate Similarity	NPD5854	Approved
0.7143	Intermediate Similarity	NPD1027	Approved
0.7143	Intermediate Similarity	NPD7164	Discontinued
0.7129	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD1952	Discontinued
0.7127	Intermediate Similarity	NPD2915	Discontinued
0.7127	Intermediate Similarity	NPD509	Phase 3
0.7127	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4547	Phase 3
0.712	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2510	Approved
0.7114	Intermediate Similarity	NPD2509	Approved
0.7113	Intermediate Similarity	NPD5855	Phase 3
0.7113	Intermediate Similarity	NPD5853	Phase 3
0.7111	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD803	Phase 1
0.7108	Intermediate Similarity	NPD8094	Discontinued
0.7101	Intermediate Similarity	NPD1262	Discovery
0.71	Intermediate Similarity	NPD6271	Approved
0.7097	Intermediate Similarity	NPD3041	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