NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.04
Volume:	281.273
LogP:	2.4
LogD:	1.516
LogS:	-2.353
# Rotatable Bonds:	2
TPSA:	69.73
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	3.072
Fsp3:	0.214
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:	-5.104
MDCK Permeability:	1.1669285413518082e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.947
Human Intestinal Absorption (HIA):	0.314
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.641
Plasma Protein Binding (PPB):	68.0916976928711%
Volume Distribution (VD):	1.178
Pgp-substrate:	27.5366268157959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.685
CYP1A2-substrate:	0.803
CYP2C19-inhibitor:	0.346
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.297
CYP2C9-substrate:	0.363
CYP2D6-inhibitor:	0.928
CYP2D6-substrate:	0.76
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	2.842
Half-life (T1/2):	0.897

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.481
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.818
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.21
Carcinogencity:	0.859
Eye Corrosion:	0.003
Eye Irritation:	0.046
Respiratory Toxicity:	0.692

Download Data

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

Natural Product: NPC474389

Natural Product ID:	NPC474389
*Common Name:**	6-Bromo-1',8-Dihydroaplysinopsin
IUPAC Name:	5-[(6-bromo-1H-indol-3-yl)methyl]-2-imino-1,3-dimethylimidazolidin-4-one
Synonyms:
Standard InCHIKey:	CLSCJOFOBRTBCX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H15BrN4O/c1-18-12(13(20)19(2)14(18)16)5-8-7-17-11-6-9(15)3-4-10(8)11/h3-4,6-7,12,16-17H,5H2,1-2H3
SMILES:	Brc1ccc2c(c1)[nH]cc2CC1N(C)C(=N)N(C1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465826
PubChem CID:	44584279
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]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	25.0	ug.mL-1	PMID[486385]

☑ 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 NPC474389 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	758
0.1-0.2	13094
0.2-0.3	19703
0.3-0.4	3806
0.4-0.5	2445
0.5-0.6	1610
0.6-0.7	1013
0.7-0.8	241
0.8-0.85	17
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9438	High Similarity	NPC474180
0.9438	High Similarity	NPC188821
0.8969	High Similarity	NPC475736
0.8878	High Similarity	NPC474195
0.8708	High Similarity	NPC473380
0.8708	High Similarity	NPC240088
0.87	High Similarity	NPC474196
0.8571	High Similarity	NPC220797
0.8571	High Similarity	NPC268744
0.8571	High Similarity	NPC153123
0.8571	High Similarity	NPC474318
0.8571	High Similarity	NPC475914
0.8571	High Similarity	NPC201266
0.8556	High Similarity	NPC265710
0.8526	High Similarity	NPC13456
0.8526	High Similarity	NPC166209
0.8526	High Similarity	NPC77241
0.8526	High Similarity	NPC269203
0.8508	High Similarity	NPC16659
0.8258	Intermediate Similarity	NPC17751
0.8241	Intermediate Similarity	NPC473218
0.8241	Intermediate Similarity	NPC470702
0.82	Intermediate Similarity	NPC470703
0.8187	Intermediate Similarity	NPC477004
0.8162	Intermediate Similarity	NPC307191
0.8114	Intermediate Similarity	NPC141926
0.8101	Intermediate Similarity	NPC247987
0.8071	Intermediate Similarity	NPC473376
0.7969	Intermediate Similarity	NPC473342
0.7969	Intermediate Similarity	NPC304187
0.7969	Intermediate Similarity	NPC477167
0.7969	Intermediate Similarity	NPC477166
0.7957	Intermediate Similarity	NPC11126
0.7908	Intermediate Similarity	NPC237414
0.7892	Intermediate Similarity	NPC280297
0.7884	Intermediate Similarity	NPC108011
0.7884	Intermediate Similarity	NPC110158
0.7857	Intermediate Similarity	NPC280864
0.7853	Intermediate Similarity	NPC17059
0.7846	Intermediate Similarity	NPC179701
0.7842	Intermediate Similarity	NPC308931
0.7842	Intermediate Similarity	NPC99939
0.784	Intermediate Similarity	NPC267078
0.784	Intermediate Similarity	NPC935
0.7838	Intermediate Similarity	NPC477611
0.7835	Intermediate Similarity	NPC88315
0.7806	Intermediate Similarity	NPC262898
0.7804	Intermediate Similarity	NPC474357
0.7802	Intermediate Similarity	NPC149265
0.7793	Intermediate Similarity	NPC470323
0.7789	Intermediate Similarity	NPC228835
0.7784	Intermediate Similarity	NPC82331
0.7784	Intermediate Similarity	NPC54214
0.7766	Intermediate Similarity	NPC276540
0.7766	Intermediate Similarity	NPC233050
0.7765	Intermediate Similarity	NPC34844
0.776	Intermediate Similarity	NPC274229
0.7756	Intermediate Similarity	NPC54744
0.7754	Intermediate Similarity	NPC474958
0.7742	Intermediate Similarity	NPC161861
0.77	Intermediate Similarity	NPC156003
0.7684	Intermediate Similarity	NPC243381
0.7684	Intermediate Similarity	NPC275292
0.7638	Intermediate Similarity	NPC136957
0.7638	Intermediate Similarity	NPC19696
0.7629	Intermediate Similarity	NPC213629
0.7626	Intermediate Similarity	NPC174281
0.7626	Intermediate Similarity	NPC475286
0.7622	Intermediate Similarity	NPC49217
0.7619	Intermediate Similarity	NPC84827
0.7619	Intermediate Similarity	NPC145885
0.7619	Intermediate Similarity	NPC14113
0.7617	Intermediate Similarity	NPC94752
0.759	Intermediate Similarity	NPC231536
0.7588	Intermediate Similarity	NPC171317
0.7576	Intermediate Similarity	NPC48117
0.7576	Intermediate Similarity	NPC476526
0.7576	Intermediate Similarity	NPC329765
0.7573	Intermediate Similarity	NPC320968
0.7557	Intermediate Similarity	NPC17487
0.7557	Intermediate Similarity	NPC201831
0.7542	Intermediate Similarity	NPC2272
0.7528	Intermediate Similarity	NPC143872
0.7526	Intermediate Similarity	NPC284775
0.7523	Intermediate Similarity	NPC477108
0.7523	Intermediate Similarity	NPC477107
0.7523	Intermediate Similarity	NPC477109
0.7513	Intermediate Similarity	NPC477003
0.7512	Intermediate Similarity	NPC116555
0.7512	Intermediate Similarity	NPC205254
0.7512	Intermediate Similarity	NPC470731
0.7512	Intermediate Similarity	NPC470732
0.7512	Intermediate Similarity	NPC106771
0.7512	Intermediate Similarity	NPC303820
0.7512	Intermediate Similarity	NPC23420
0.75	Intermediate Similarity	NPC470204
0.7487	Intermediate Similarity	NPC248041
0.7487	Intermediate Similarity	NPC126709
0.7475	Intermediate Similarity	NPC52909
0.7475	Intermediate Similarity	NPC94211
0.7475	Intermediate Similarity	NPC475935
0.7474	Intermediate Similarity	NPC267885
0.7462	Intermediate Similarity	NPC476460
0.7459	Intermediate Similarity	NPC470203
0.7458	Intermediate Similarity	NPC190296
0.7452	Intermediate Similarity	NPC207020
0.7448	Intermediate Similarity	NPC91179
0.743	Intermediate Similarity	NPC316069
0.7421	Intermediate Similarity	NPC149155
0.7421	Intermediate Similarity	NPC203468
0.7421	Intermediate Similarity	NPC110500
0.7418	Intermediate Similarity	NPC200214
0.7418	Intermediate Similarity	NPC232798
0.7402	Intermediate Similarity	NPC317701
0.7396	Intermediate Similarity	NPC283219
0.7386	Intermediate Similarity	NPC110126
0.7386	Intermediate Similarity	NPC73767
0.7379	Intermediate Similarity	NPC54420
0.7374	Intermediate Similarity	NPC204141
0.7374	Intermediate Similarity	NPC470440
0.7374	Intermediate Similarity	NPC314372
0.7371	Intermediate Similarity	NPC84911
0.736	Intermediate Similarity	NPC321708
0.7354	Intermediate Similarity	NPC97343
0.735	Intermediate Similarity	NPC294693
0.7343	Intermediate Similarity	NPC476525
0.733	Intermediate Similarity	NPC82053
0.7326	Intermediate Similarity	NPC206148
0.732	Intermediate Similarity	NPC191415
0.7316	Intermediate Similarity	NPC469976
0.7314	Intermediate Similarity	NPC29886
0.7314	Intermediate Similarity	NPC261195
0.7314	Intermediate Similarity	NPC96102
0.7312	Intermediate Similarity	NPC122141
0.7311	Intermediate Similarity	NPC477114
0.7308	Intermediate Similarity	NPC162860
0.7308	Intermediate Similarity	NPC478158
0.7302	Intermediate Similarity	NPC78020
0.73	Intermediate Similarity	NPC19342
0.7291	Intermediate Similarity	NPC293917
0.7278	Intermediate Similarity	NPC159856
0.7273	Intermediate Similarity	NPC105127
0.7273	Intermediate Similarity	NPC63031
0.7273	Intermediate Similarity	NPC253687
0.7268	Intermediate Similarity	NPC473761
0.726	Intermediate Similarity	NPC69843
0.726	Intermediate Similarity	NPC476524
0.7259	Intermediate Similarity	NPC476527
0.7247	Intermediate Similarity	NPC469767
0.7247	Intermediate Similarity	NPC469768
0.7247	Intermediate Similarity	NPC469780
0.7247	Intermediate Similarity	NPC469779
0.7247	Intermediate Similarity	NPC469784
0.7247	Intermediate Similarity	NPC469783
0.7247	Intermediate Similarity	NPC469761
0.7241	Intermediate Similarity	NPC473640
0.7238	Intermediate Similarity	NPC288838
0.7234	Intermediate Similarity	NPC271797
0.7234	Intermediate Similarity	NPC21174
0.723	Intermediate Similarity	NPC267811
0.722	Intermediate Similarity	NPC475506
0.7214	Intermediate Similarity	NPC326422
0.7213	Intermediate Similarity	NPC53947
0.7213	Intermediate Similarity	NPC105818
0.7213	Intermediate Similarity	NPC24678
0.7207	Intermediate Similarity	NPC469766
0.7206	Intermediate Similarity	NPC100321
0.7204	Intermediate Similarity	NPC471193
0.7204	Intermediate Similarity	NPC471194
0.72	Intermediate Similarity	NPC243716
0.7198	Intermediate Similarity	NPC471957
0.7196	Intermediate Similarity	NPC2165
0.7196	Intermediate Similarity	NPC42372
0.7194	Intermediate Similarity	NPC470205
0.7194	Intermediate Similarity	NPC102755
0.7184	Intermediate Similarity	NPC155143
0.7172	Intermediate Similarity	NPC63571
0.7172	Intermediate Similarity	NPC17273
0.7172	Intermediate Similarity	NPC135601
0.7172	Intermediate Similarity	NPC235684
0.7172	Intermediate Similarity	NPC141612
0.7166	Intermediate Similarity	NPC135141
0.7166	Intermediate Similarity	NPC92796
0.7158	Intermediate Similarity	NPC56233
0.7158	Intermediate Similarity	NPC321911
0.7151	Intermediate Similarity	NPC279081
0.715	Intermediate Similarity	NPC293216
0.7143	Intermediate Similarity	NPC73687
0.7143	Intermediate Similarity	NPC184932
0.7143	Intermediate Similarity	NPC472861
0.7136	Intermediate Similarity	NPC310633
0.7136	Intermediate Similarity	NPC478157
0.7135	Intermediate Similarity	NPC73952
0.7135	Intermediate Similarity	NPC469760
0.7135	Intermediate Similarity	NPC227489
0.7135	Intermediate Similarity	NPC476421
0.7135	Intermediate Similarity	NPC25008
0.7135	Intermediate Similarity	NPC259644
0.7135	Intermediate Similarity	NPC469763
0.7135	Intermediate Similarity	NPC469786

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 NPC474389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	842
0.2-0.3	1217
0.3-0.4	2239
0.4-0.5	2173
0.5-0.6	1742
0.6-0.7	545
0.7-0.8	46
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
0.7811	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2880	Discontinued
0.7633	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7970	Approved
0.7598	Intermediate Similarity	NPD2442	Approved
0.7598	Intermediate Similarity	NPD2443	Approved
0.7586	Intermediate Similarity	NPD2008	Discontinued
0.7538	Intermediate Similarity	NPD6664	Approved
0.7525	Intermediate Similarity	NPD7619	Phase 3
0.7525	Intermediate Similarity	NPD7618	Phase 3
0.7524	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD482	Approved
0.7398	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2408	Discontinued
0.7389	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD786	Approved
0.7382	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2411	Approved
0.733	Intermediate Similarity	NPD4128	Approved
0.7321	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4075	Phase 2
0.7291	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD750	Phase 2
0.7254	Intermediate Similarity	NPD4181	Approved
0.7245	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD5199	Approved
0.7243	Intermediate Similarity	NPD5198	Approved
0.7231	Intermediate Similarity	NPD1708	Approved
0.7231	Intermediate Similarity	NPD1707	Approved
0.7231	Intermediate Similarity	NPD1895	Discontinued
0.7225	Intermediate Similarity	NPD1600	Suspended
0.7222	Intermediate Similarity	NPD3961	Discontinued
0.7213	Intermediate Similarity	NPD2172	Phase 1
0.7212	Intermediate Similarity	NPD1506	Discontinued
0.7204	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2092	Phase 2
0.7194	Intermediate Similarity	NPD2095	Phase 2
0.7194	Intermediate Similarity	NPD2094	Phase 2
0.7172	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6217	Discontinued
0.7162	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD2091	Phase 2
0.7157	Intermediate Similarity	NPD2096	Phase 2
0.7136	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1722	Approved
0.7107	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7175	Phase 1
0.7085	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1982	Phase 1
0.707	Intermediate Similarity	NPD8257	Approved
0.707	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8256	Approved
0.7065	Intermediate Similarity	NPD3100	Discontinued
0.7053	Intermediate Similarity	NPD3583	Phase 2
0.7031	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6595	Phase 3
0.7	Intermediate Similarity	NPD7026	Phase 2
0.6995	Remote Similarity	NPD7470	Discontinued
0.6979	Remote Similarity	NPD2639	Approved
0.6979	Remote Similarity	NPD2642	Approved
0.6973	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6470	Phase 3
0.6952	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2367	Phase 2
0.6938	Remote Similarity	NPD2879	Approved
0.6938	Remote Similarity	NPD6268	Phase 1
0.6938	Remote Similarity	NPD2881	Approved
0.6938	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6165	Phase 2
0.6937	Remote Similarity	NPD6164	Phase 2
0.693	Remote Similarity	NPD8094	Discontinued
0.693	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD2793	Discontinued
0.6912	Remote Similarity	NPD3431	Approved
0.6912	Remote Similarity	NPD4922	Phase 2
0.6912	Remote Similarity	NPD3430	Approved
0.6907	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2071	Approved
0.6906	Remote Similarity	NPD2068	Approved
0.6906	Remote Similarity	NPD2070	Approved
0.6906	Remote Similarity	NPD2069	Approved
0.6904	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7564	Discontinued
0.6893	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1248	Discontinued
0.6889	Remote Similarity	NPD200	Phase 2
0.6889	Remote Similarity	NPD201	Phase 2
0.6884	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5426	Phase 3
0.6872	Remote Similarity	NPD8272	Phase 2
0.6866	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1658	Discontinued
0.6859	Remote Similarity	NPD1404	Approved
0.6859	Remote Similarity	NPD1403	Approved
0.6856	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD6771	Discontinued
0.6818	Remote Similarity	NPD2144	Approved
0.6814	Remote Similarity	NPD5686	Approved
0.6814	Remote Similarity	NPD5685	Approved
0.6812	Remote Similarity	NPD2289	Phase 3
0.6812	Remote Similarity	NPD2290	Phase 3
0.6812	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD3905	Phase 3
0.6806	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD460	Discontinued
0.6794	Remote Similarity	NPD2405	Phase 3
0.6791	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2150	Discontinued
0.6788	Remote Similarity	NPD3323	Discontinued
0.6786	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6828	Phase 2
0.6784	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2837	Discontinued
0.6769	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6044	Discontinued
0.6766	Remote Similarity	NPD3320	Approved
0.6766	Remote Similarity	NPD3318	Approved
0.6766	Remote Similarity	NPD3319	Phase 1
0.6763	Remote Similarity	NPD7944	Discontinued
0.6756	Remote Similarity	NPD7780	Approved
0.6756	Remote Similarity	NPD7781	Approved
0.6744	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD3506	Approved
0.6734	Remote Similarity	NPD3505	Approved
0.673	Remote Similarity	NPD5017	Discontinued
0.6729	Remote Similarity	NPD7445	Phase 1
0.6728	Remote Similarity	NPD8093	Discontinued
0.6728	Remote Similarity	NPD7656	Approved
0.6728	Remote Similarity	NPD7657	Approved
0.6727	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7716	Approved
0.6726	Remote Similarity	NPD7717	Approved
0.6718	Remote Similarity	NPD5611	Phase 2
0.6717	Remote Similarity	NPD5065	Approved
0.6716	Remote Similarity	NPD3038	Discontinued
0.6703	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD2580	Discontinued
0.6702	Remote Similarity	NPD1183	Approved
0.6701	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4079	Approved
0.67	Remote Similarity	NPD4076	Approved
0.6698	Remote Similarity	NPD2510	Approved
0.6698	Remote Similarity	NPD2509	Approved
0.6696	Remote Similarity	NPD8316	Phase 2
0.6696	Remote Similarity	NPD8317	Phase 2
0.6684	Remote Similarity	NPD2640	Approved
0.6684	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2641	Approved
0.6683	Remote Similarity	NPD5105	Approved
0.6683	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8641	Approved
0.6683	Remote Similarity	NPD5106	Approved
0.6682	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4863	Approved
0.6682	Remote Similarity	NPD484	Approved
0.6667	Remote Similarity	NPD1995	Approved
0.6667	Remote Similarity	NPD1996	Discontinued
0.6667	Remote Similarity	NPD5508	Phase 1
0.6667	Remote Similarity	NPD1994	Approved
0.6667	Remote Similarity	NPD4615	Phase 2
0.6667	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4520	Approved
0.6667	Remote Similarity	NPD1993	Approved
0.6667	Remote Similarity	NPD1313	Approved
0.6667	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4364	Phase 1
0.6651	Remote Similarity	NPD4848	Phase 1
0.6651	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2316	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7789	Approved
0.6638	Remote Similarity	NPD7790	Approved
0.6638	Remote Similarity	NPD7953	Approved
0.6638	Remote Similarity	NPD7950	Approved
0.6638	Remote Similarity	NPD7951	Approved
0.6638	Remote Similarity	NPD7952	Approved
0.6638	Remote Similarity	NPD7791	Approved
0.6637	Remote Similarity	NPD7731	Approved
0.6637	Remote Similarity	NPD7730	Approved
0.6636	Remote Similarity	NPD7208	Approved
0.6636	Remote Similarity	NPD7209	Approved
0.6636	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7207	Approved
0.6634	Remote Similarity	NPD4988	Discontinued
0.6633	Remote Similarity	NPD438	Approved
0.6633	Remote Similarity	NPD439	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