NPASS Compound

Structure

NPC470323 OpenBabel07101719242D 26 30 0 0 0 0 0 0 0 0999 V2000 4.9409 0.6460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5287 -0.1630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9464 0.5415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1220 -1.0765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3305 -2.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4644 -2.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 -1.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5886 -1.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 -2.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5396 -0.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4644 -1.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5886 -0.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1274 -1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3305 -0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0625 -2.6303 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.5396 -1.9901 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1226 0.3478 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 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 1.8841 0.9013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 2 0 0 0 0 3 12 1 0 0 0 0 4 16 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 23 1 0 0 0 0 9 15 2 0 0 0 0 9 22 1 0 0 0 0 10 18 2 0 0 0 0 10 24 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 16 2 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 26 2 0 0 0 0 20 24 1 0 0 0 0 20 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.04
Volume:	357.39
LogP:	4.343
LogD:	3.687
LogS:	-4.129
# Rotatable Bonds:	3
TPSA:	80.49
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	3.329
Fsp3:	0.05
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.148
MDCK Permeability:	4.779477421834599e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.061
30% Bioavailability (F30%):	0.566

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	97.9762954711914%
Volume Distribution (VD):	0.908
Pgp-substrate:	1.47665274143219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.955
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.956
CYP2D6-substrate:	0.653
CYP3A4-inhibitor:	0.949
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	3.261
Half-life (T1/2):	0.519

ADMET: Toxicity

hERG Blockers:	0.685
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.598
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.185
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC470323

Natural Product ID:	NPC470323
*Common Name:**	[5-(6-Bromo-1H-Indol-3-Yl)-1H-Imidazol-2-Yl]-(4,5-Dihydro-1H-Indol-3-Yl)Methanone
IUPAC Name:	[5-(6-bromo-1H-indol-3-yl)-1H-imidazol-2-yl]-(4,5-dihydro-1H-indol-3-yl)methanone
Synonyms:
Standard InCHIKey:	JBAPNYOAPKFPKK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H15BrN4O/c21-11-5-6-13-14(8-23-17(13)7-11)18-10-24-20(25-18)19(26)15-9-22-16-4-2-1-3-12(15)16/h2,4-10,22-23H,1,3H2,(H,24,25)
SMILES:	C1CC2=C(C=C1)NC=C2C(=O)C3=NC=C(N3)C4=CNC5=C4C=CC(=C5)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL198074
PubChem CID:	44404473
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921415]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16154746]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253840]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	southern australian	n.a.	PMID[9599272]

☑ 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	1
MIC	1

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	100.0	ug.mL-1	PMID[508936]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[508936]

☑ 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 NPC470323 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	1019
0.1-0.2	14428
0.2-0.3	19120
0.3-0.4	3607
0.4-0.5	2033
0.5-0.6	1658
0.6-0.7	692
0.7-0.8	125
0.8-0.85	4
0.85-0.9	6
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9854	High Similarity	NPC935
0.9854	High Similarity	NPC267078
0.9807	High Similarity	NPC474357
0.9223	High Similarity	NPC267811
0.8756	High Similarity	NPC473218
0.8756	High Similarity	NPC470702
0.8744	High Similarity	NPC116555
0.8714	High Similarity	NPC470703
0.8494	Intermediate Similarity	NPC77101
0.8182	Intermediate Similarity	NPC237414
0.8044	Intermediate Similarity	NPC156003
0.795	Intermediate Similarity	NPC63109
0.7943	Intermediate Similarity	NPC326422
0.7857	Intermediate Similarity	NPC474180
0.7857	Intermediate Similarity	NPC188821
0.784	Intermediate Similarity	NPC477004
0.7793	Intermediate Similarity	NPC474389
0.7689	Intermediate Similarity	NPC304203
0.7633	Intermediate Similarity	NPC307191
0.7615	Intermediate Similarity	NPC317701
0.7593	Intermediate Similarity	NPC153123
0.7593	Intermediate Similarity	NPC474318
0.7593	Intermediate Similarity	NPC475914
0.7593	Intermediate Similarity	NPC220797
0.7593	Intermediate Similarity	NPC268744
0.7593	Intermediate Similarity	NPC201266
0.7573	Intermediate Similarity	NPC284775
0.756	Intermediate Similarity	NPC110158
0.7558	Intermediate Similarity	NPC77241
0.7558	Intermediate Similarity	NPC269203
0.7558	Intermediate Similarity	NPC166209
0.7558	Intermediate Similarity	NPC13456
0.7548	Intermediate Similarity	NPC191415
0.7467	Intermediate Similarity	NPC282247
0.743	Intermediate Similarity	NPC476460
0.7393	Intermediate Similarity	NPC108011
0.7346	Intermediate Similarity	NPC102755
0.7339	Intermediate Similarity	NPC167710
0.7339	Intermediate Similarity	NPC74619
0.7273	Intermediate Similarity	NPC19696
0.7273	Intermediate Similarity	NPC136957
0.7261	Intermediate Similarity	NPC475736
0.726	Intermediate Similarity	NPC174281
0.726	Intermediate Similarity	NPC475286
0.726	Intermediate Similarity	NPC477611
0.7251	Intermediate Similarity	NPC16659
0.7238	Intermediate Similarity	NPC473380
0.7238	Intermediate Similarity	NPC240088
0.723	Intermediate Similarity	NPC477003
0.7222	Intermediate Similarity	NPC231536
0.7204	Intermediate Similarity	NPC265710
0.7198	Intermediate Similarity	NPC474195
0.719	Intermediate Similarity	NPC474958
0.7184	Intermediate Similarity	NPC17751
0.7184	Intermediate Similarity	NPC274229
0.7149	Intermediate Similarity	NPC474196
0.7149	Intermediate Similarity	NPC37152
0.7129	Intermediate Similarity	NPC82331
0.7101	Intermediate Similarity	NPC69843
0.7064	Intermediate Similarity	NPC324091
0.7059	Intermediate Similarity	NPC476526
0.7059	Intermediate Similarity	NPC329765
0.7059	Intermediate Similarity	NPC48117
0.7042	Intermediate Similarity	NPC200553
0.7042	Intermediate Similarity	NPC279189
0.7034	Intermediate Similarity	NPC229893
0.7014	Intermediate Similarity	NPC252572
0.7005	Intermediate Similarity	NPC470203
0.7004	Intermediate Similarity	NPC82053
0.7	Intermediate Similarity	NPC477167
0.7	Intermediate Similarity	NPC54981
0.7	Intermediate Similarity	NPC304187
0.7	Intermediate Similarity	NPC477166
0.7	Intermediate Similarity	NPC473342
0.6983	Remote Similarity	NPC174489
0.6982	Remote Similarity	NPC128244
0.6971	Remote Similarity	NPC247987
0.6971	Remote Similarity	NPC317105
0.697	Remote Similarity	NPC471194
0.697	Remote Similarity	NPC471193
0.6968	Remote Similarity	NPC19342
0.6959	Remote Similarity	NPC99939
0.6959	Remote Similarity	NPC308931
0.6957	Remote Similarity	NPC470204
0.6955	Remote Similarity	NPC162002
0.6951	Remote Similarity	NPC201831
0.6951	Remote Similarity	NPC17487
0.6948	Remote Similarity	NPC151635
0.6938	Remote Similarity	NPC42372
0.6933	Remote Similarity	NPC106771
0.6933	Remote Similarity	NPC23420
0.6933	Remote Similarity	NPC303820
0.6933	Remote Similarity	NPC205254
0.6932	Remote Similarity	NPC471536
0.6926	Remote Similarity	NPC26641
0.6923	Remote Similarity	NPC477108
0.6923	Remote Similarity	NPC477109
0.6923	Remote Similarity	NPC253687
0.6923	Remote Similarity	NPC477107
0.6923	Remote Similarity	NPC216550
0.6912	Remote Similarity	NPC21429
0.6906	Remote Similarity	NPC79356
0.6906	Remote Similarity	NPC102592
0.6903	Remote Similarity	NPC94211
0.6903	Remote Similarity	NPC52909
0.6903	Remote Similarity	NPC475935
0.6901	Remote Similarity	NPC280297
0.6884	Remote Similarity	NPC233050
0.6884	Remote Similarity	NPC276540
0.6878	Remote Similarity	NPC141926
0.687	Remote Similarity	NPC476525
0.687	Remote Similarity	NPC476524
0.687	Remote Similarity	NPC71238
0.6857	Remote Similarity	NPC280864
0.6853	Remote Similarity	NPC72956
0.6852	Remote Similarity	NPC88110
0.6851	Remote Similarity	NPC477114
0.6844	Remote Similarity	NPC97902
0.684	Remote Similarity	NPC97343
0.6835	Remote Similarity	NPC467063
0.6831	Remote Similarity	NPC207686
0.6824	Remote Similarity	NPC153980
0.6824	Remote Similarity	NPC6865
0.6822	Remote Similarity	NPC293216
0.6822	Remote Similarity	NPC317054
0.682	Remote Similarity	NPC243381
0.682	Remote Similarity	NPC275292
0.6815	Remote Similarity	NPC171393
0.6815	Remote Similarity	NPC295452
0.6808	Remote Similarity	NPC54214
0.6798	Remote Similarity	NPC473761
0.6794	Remote Similarity	NPC122141
0.6789	Remote Similarity	NPC117027
0.678	Remote Similarity	NPC27041
0.6773	Remote Similarity	NPC135601
0.6773	Remote Similarity	NPC63571
0.6773	Remote Similarity	NPC476527
0.6773	Remote Similarity	NPC17273
0.6773	Remote Similarity	NPC141612
0.6751	Remote Similarity	NPC469717
0.6742	Remote Similarity	NPC310633
0.6741	Remote Similarity	NPC88315
0.6737	Remote Similarity	NPC471192
0.673	Remote Similarity	NPC274981
0.6727	Remote Similarity	NPC133003
0.6727	Remote Similarity	NPC476341
0.6726	Remote Similarity	NPC227582
0.6721	Remote Similarity	NPC235685
0.6718	Remote Similarity	NPC117980
0.6712	Remote Similarity	NPC103119
0.6709	Remote Similarity	NPC82370
0.6699	Remote Similarity	NPC216643
0.6698	Remote Similarity	NPC115232
0.6697	Remote Similarity	NPC111566
0.6694	Remote Similarity	NPC63031
0.6694	Remote Similarity	NPC101350
0.6682	Remote Similarity	NPC471943
0.6682	Remote Similarity	NPC157583
0.6681	Remote Similarity	NPC477413
0.668	Remote Similarity	NPC130570
0.6667	Remote Similarity	NPC474492
0.6667	Remote Similarity	NPC88115
0.6667	Remote Similarity	NPC74413
0.6667	Remote Similarity	NPC470677
0.6652	Remote Similarity	NPC266249
0.6652	Remote Similarity	NPC210123
0.6652	Remote Similarity	NPC106757
0.6638	Remote Similarity	NPC252338
0.6637	Remote Similarity	NPC473666
0.6636	Remote Similarity	NPC270834
0.6635	Remote Similarity	NPC325903
0.6634	Remote Similarity	NPC288838
0.6622	Remote Similarity	NPC272458
0.6621	Remote Similarity	NPC314281
0.6621	Remote Similarity	NPC40530
0.6607	Remote Similarity	NPC154339
0.6602	Remote Similarity	NPC469811
0.6597	Remote Similarity	NPC36405
0.6596	Remote Similarity	NPC123839
0.6594	Remote Similarity	NPC81535
0.6588	Remote Similarity	NPC135141
0.6588	Remote Similarity	NPC92796
0.658	Remote Similarity	NPC260900
0.6574	Remote Similarity	NPC227489
0.6574	Remote Similarity	NPC476421
0.6574	Remote Similarity	NPC28096
0.6573	Remote Similarity	NPC206148
0.6573	Remote Similarity	NPC149265
0.657	Remote Similarity	NPC321911
0.6562	Remote Similarity	NPC321708
0.6561	Remote Similarity	NPC470205
0.6557	Remote Similarity	NPC470680
0.6557	Remote Similarity	NPC100104
0.6553	Remote Similarity	NPC143872
0.6553	Remote Similarity	NPC63545
0.655	Remote Similarity	NPC131887
0.655	Remote Similarity	NPC67288
0.6549	Remote Similarity	NPC47190
0.6545	Remote Similarity	NPC73994
0.6545	Remote Similarity	NPC79777

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 NPC470323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	999
0.2-0.3	1501
0.3-0.4	2398
0.4-0.5	1826
0.5-0.6	1493
0.6-0.7	472
0.7-0.8	31
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8294	Intermediate Similarity	NPD2008	Discontinued
0.8148	Intermediate Similarity	NPD2411	Approved
0.7963	Intermediate Similarity	NPD2443	Approved
0.7963	Intermediate Similarity	NPD2442	Approved
0.7844	Intermediate Similarity	NPD1600	Suspended
0.7834	Intermediate Similarity	NPD1506	Discontinued
0.7814	Intermediate Similarity	NPD2879	Approved
0.7814	Intermediate Similarity	NPD2881	Approved
0.7763	Intermediate Similarity	NPD2408	Discontinued
0.7689	Intermediate Similarity	NPD460	Discontinued
0.7671	Intermediate Similarity	NPD3905	Phase 3
0.7489	Intermediate Similarity	NPD6470	Phase 3
0.7465	Intermediate Similarity	NPD1982	Phase 1
0.7464	Intermediate Similarity	NPD1895	Discontinued
0.7455	Intermediate Similarity	NPD4863	Approved
0.7419	Intermediate Similarity	NPD2880	Discontinued
0.7366	Intermediate Similarity	NPD2295	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD8256	Approved
0.7217	Intermediate Similarity	NPD8257	Approved
0.7193	Intermediate Similarity	NPD7657	Approved
0.7193	Intermediate Similarity	NPD7656	Approved
0.7189	Intermediate Similarity	NPD1658	Discontinued
0.7182	Intermediate Similarity	NPD1952	Discontinued
0.7182	Intermediate Similarity	NPD5446	Phase 2
0.7143	Intermediate Similarity	NPD2364	Suspended
0.7129	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6579	Phase 2
0.7119	Intermediate Similarity	NPD6715	Discontinued
0.7083	Intermediate Similarity	NPD2793	Discontinued
0.7082	Intermediate Similarity	NPD5199	Approved
0.7082	Intermediate Similarity	NPD5198	Approved
0.7078	Intermediate Similarity	NPD3431	Approved
0.7078	Intermediate Similarity	NPD3430	Approved
0.7069	Intermediate Similarity	NPD5643	Phase 2
0.7059	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4541	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4299	Phase 1
0.7035	Intermediate Similarity	NPD6229	Phase 2
0.7025	Intermediate Similarity	NPD6986	Phase 1
0.7017	Intermediate Similarity	NPD6164	Phase 2
0.7017	Intermediate Similarity	NPD6165	Phase 2
0.7013	Intermediate Similarity	NPD4341	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2363	Discontinued
0.7012	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5962	Phase 2
0.6987	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4395	Phase 1
0.6979	Remote Similarity	NPD6210	Phase 3
0.6978	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3840	Phase 2
0.6974	Remote Similarity	NPD3839	Phase 2
0.6972	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7209	Approved
0.696	Remote Similarity	NPD7208	Approved
0.696	Remote Similarity	NPD7207	Approved
0.6951	Remote Similarity	NPD5831	Discontinued
0.6947	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6271	Approved
0.69	Remote Similarity	NPD7445	Phase 1
0.6889	Remote Similarity	NPD5854	Approved
0.688	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4854	Phase 3
0.6872	Remote Similarity	NPD2333	Discontinued
0.686	Remote Similarity	NPD8317	Phase 2
0.686	Remote Similarity	NPD8316	Phase 2
0.6856	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD1896	Approved
0.6846	Remote Similarity	NPD5415	Approved
0.6844	Remote Similarity	NPD7459	Phase 2
0.6844	Remote Similarity	NPD6465	Phase 2
0.6806	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4872	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6459	Phase 2
0.6786	Remote Similarity	NPD5853	Phase 3
0.6786	Remote Similarity	NPD5855	Phase 3
0.6777	Remote Similarity	NPD1313	Approved
0.6766	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD1871	Approved
0.6756	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD2316	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7857	Phase 3
0.6747	Remote Similarity	NPD7856	Phase 2
0.6743	Remote Similarity	NPD1707	Approved
0.6743	Remote Similarity	NPD1708	Approved
0.6741	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD2446	Approved
0.6741	Remote Similarity	NPD2445	Approved
0.6732	Remote Similarity	NPD3811	Discontinued
0.6726	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6458	Discontinued
0.6712	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5016	Approved
0.6708	Remote Similarity	NPD7887	Approved
0.6708	Remote Similarity	NPD7888	Approved
0.6707	Remote Similarity	NPD6970	Phase 2
0.6697	Remote Similarity	NPD4940	Approved
0.6696	Remote Similarity	NPD4615	Phase 2
0.6695	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1996	Discontinued
0.6694	Remote Similarity	NPD3786	Phase 3
0.6682	Remote Similarity	NPD5685	Approved
0.6682	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5686	Approved
0.6682	Remote Similarity	NPD2457	Phase 2
0.6682	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2456	Phase 2
0.668	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.668	Remote Similarity	NPD2400	Phase 2
0.6667	Remote Similarity	NPD4988	Discontinued
0.6667	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4446	Approved
0.6653	Remote Similarity	NPD5985	Phase 2
0.6652	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5462	Discontinued
0.6652	Remote Similarity	NPD6268	Phase 1
0.664	Remote Similarity	NPD8159	Discontinued
0.6639	Remote Similarity	NPD5465	Phase 2
0.6638	Remote Similarity	NPD5491	Phase 3
0.6638	Remote Similarity	NPD5489	Phase 1
0.6638	Remote Similarity	NPD3265	Phase 1
0.6637	Remote Similarity	NPD7406	Phase 2
0.6637	Remote Similarity	NPD8641	Approved
0.6627	Remote Similarity	NPD3962	Phase 2
0.6627	Remote Similarity	NPD3959	Phase 2
0.6625	Remote Similarity	NPD5827	Discontinued
0.6624	Remote Similarity	NPD3860	Discontinued
0.6623	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6469	Phase 3
0.6622	Remote Similarity	NPD4922	Phase 2
0.6622	Remote Similarity	NPD2591	Phase 2
0.6621	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD5508	Phase 1
0.662	Remote Similarity	NPD1333	Phase 3
0.6612	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1016	Phase 2
0.6604	Remote Similarity	NPD1015	Phase 2
0.6596	Remote Similarity	NPD4051	Discontinued
0.6589	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8484	Phase 2
0.6581	Remote Similarity	NPD6520	Phase 3
0.6581	Remote Similarity	NPD6521	Phase 3
0.6579	Remote Similarity	NPD3830	Phase 1
0.6575	Remote Similarity	NPD3432	Approved
0.6568	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD6816	Phase 3
0.6559	Remote Similarity	NPD7172	Approved
0.6559	Remote Similarity	NPD7173	Approved
0.655	Remote Similarity	NPD465	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD2872	Phase 2
0.6547	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6721	Phase 1
0.6547	Remote Similarity	NPD4902	Discontinued
0.654	Remote Similarity	NPD4352	Phase 1
0.6538	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD4142	Discontinued
0.6535	Remote Similarity	NPD3362	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4848	Phase 1
0.653	Remote Similarity	NPD3041	Approved
0.6528	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5072	Discontinued
0.6524	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.652	Remote Similarity	NPD6265	Discontinued
0.6518	Remote Similarity	NPD3246	Discontinued
0.6515	Remote Similarity	NPD5270	Discontinued
0.6512	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD2510	Approved
0.6511	Remote Similarity	NPD2509	Approved
0.6504	Remote Similarity	NPD7709	Discontinued
0.6502	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2813	Phase 3
0.65	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4558	Phase 2
0.6484	Remote Similarity	NPD2367	Phase 2
0.6484	Remote Similarity	NPD8523	Approved
0.6478	Remote Similarity	NPD1249	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5973	Phase 2
0.6476	Remote Similarity	NPD5974	Approved
0.6475	Remote Similarity	NPD6849	Phase 2
0.6475	Remote Similarity	NPD6850	Phase 2
0.6473	Remote Similarity	NPD5642	Approved
0.6473	Remote Similarity	NPD5820	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