NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	307.88
Volume:	182.747
LogP:	1.527
LogD:	1.87
LogS:	-2.026
# Rotatable Bonds:	0
TPSA:	54.26
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	3.898
Fsp3:	0.286
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:	-5.008
MDCK Permeability:	1.6952537407632917e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.216
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.958
Plasma Protein Binding (PPB):	90.8103256225586%
Volume Distribution (VD):	0.753
Pgp-substrate:	26.31998062133789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.549
CYP1A2-substrate:	0.213
CYP2C19-inhibitor:	0.467
CYP2C19-substrate:	0.615
CYP2C9-inhibitor:	0.217
CYP2C9-substrate:	0.4
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.283
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	5.753
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.499
Skin Sensitization:	0.239
Carcinogencity:	0.842
Eye Corrosion:	0.004
Eye Irritation:	0.065
Respiratory Toxicity:	0.41

Download Data

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

Natural Product: NPC474236

Natural Product ID:	NPC474236
*Common Name:**	Longamide
IUPAC Name:	6,7-dibromo-4-hydroxy-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one
Synonyms:	(+/-)-Longamide; Longamide
Standard InCHIKey:	NUVAABCZBKHWMX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H6Br2N2O2/c8-3-1-4-7(13)10-2-5(12)11(4)6(3)9/h1,5,12H,2H2,(H,10,13)
SMILES:	OC1CNC(=O)c2n1c(Br)c(c2)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463949
PubChem CID:	10902963
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0000475] Carboxylic acid amides [CHEMONTID:0004817] 2-heteroaryl carboxamides

*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
NPO32920	homaxinella sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16441084]
NPO32920	homaxinella sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9834174]

☑ 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
ED50	1
Others	6

Activity Type	# Activity
Cell Line	1
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	100.0	ug ml-1	PMID[448593]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	13.81	%	PMID[448595]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	12.05	%	PMID[448595]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	-0.47	%	PMID[448595]
NPT2	Others	Unspecified		Percent Effect	=	-12.72	%	PMID[448596]
NPT2	Others	Unspecified		Percent Effect	=	-16.24	%	PMID[448596]
NPT2	Others	Unspecified		Percent Effect	=	13.6	%	PMID[448596]

☑ 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 NPC474236 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	1148
0.1-0.2	15005
0.2-0.3	18403
0.3-0.4	3455
0.4-0.5	2871
0.5-0.6	1516
0.6-0.7	235
0.7-0.8	38
0.8-0.85	17
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC473706
0.8903	High Similarity	NPC474383
0.8824	High Similarity	NPC27296
0.86	High Similarity	NPC260041
0.8599	High Similarity	NPC476418
0.8509	High Similarity	NPC80528
0.8481	Intermediate Similarity	NPC306160
0.8425	Intermediate Similarity	NPC150592
0.8405	Intermediate Similarity	NPC136441
0.8333	Intermediate Similarity	NPC476421
0.8333	Intermediate Similarity	NPC28096
0.8333	Intermediate Similarity	NPC227489
0.8231	Intermediate Similarity	NPC20021
0.8221	Intermediate Similarity	NPC226835
0.8214	Intermediate Similarity	NPC469814
0.8121	Intermediate Similarity	NPC97106
0.8012	Intermediate Similarity	NPC46022
0.8012	Intermediate Similarity	NPC112489
0.7914	Intermediate Similarity	NPC206148
0.7849	Intermediate Similarity	NPC476423
0.7797	Intermediate Similarity	NPC46811
0.7784	Intermediate Similarity	NPC476413
0.7758	Intermediate Similarity	NPC2414
0.775	Intermediate Similarity	NPC109158
0.774	Intermediate Similarity	NPC476414
0.7692	Intermediate Similarity	NPC37268
0.7578	Intermediate Similarity	NPC52110
0.7574	Intermediate Similarity	NPC54214
0.7572	Intermediate Similarity	NPC184932
0.7572	Intermediate Similarity	NPC472861
0.7546	Intermediate Similarity	NPC298288
0.7446	Intermediate Similarity	NPC9635
0.7396	Intermediate Similarity	NPC474696
0.7394	Intermediate Similarity	NPC142688
0.7325	Intermediate Similarity	NPC472288
0.7317	Intermediate Similarity	NPC472260
0.7308	Intermediate Similarity	NPC23215
0.7303	Intermediate Similarity	NPC63571
0.7303	Intermediate Similarity	NPC111566
0.7278	Intermediate Similarity	NPC73687
0.7263	Intermediate Similarity	NPC310633
0.7225	Intermediate Similarity	NPC271927
0.7208	Intermediate Similarity	NPC71236
0.7158	Intermediate Similarity	NPC19342
0.7119	Intermediate Similarity	NPC40530
0.7119	Intermediate Similarity	NPC314281
0.7089	Intermediate Similarity	NPC291517
0.7081	Intermediate Similarity	NPC77061
0.7059	Intermediate Similarity	NPC136957
0.7059	Intermediate Similarity	NPC19696
0.7039	Intermediate Similarity	NPC270834
0.6971	Remote Similarity	NPC469976
0.6952	Remote Similarity	NPC475286
0.6952	Remote Similarity	NPC174281
0.6941	Remote Similarity	NPC213914
0.6936	Remote Similarity	NPC233380
0.6923	Remote Similarity	NPC209362
0.6923	Remote Similarity	NPC313823
0.6923	Remote Similarity	NPC33229
0.6898	Remote Similarity	NPC48117
0.6898	Remote Similarity	NPC329765
0.6898	Remote Similarity	NPC476526
0.6886	Remote Similarity	NPC13432
0.6859	Remote Similarity	NPC469716
0.68	Remote Similarity	NPC469717
0.6784	Remote Similarity	NPC74357
0.6774	Remote Similarity	NPC210123
0.6734	Remote Similarity	NPC50562
0.6728	Remote Similarity	NPC98156
0.6728	Remote Similarity	NPC195704
0.6728	Remote Similarity	NPC14448
0.6728	Remote Similarity	NPC167200
0.6728	Remote Similarity	NPC292434
0.6728	Remote Similarity	NPC138596
0.6728	Remote Similarity	NPC200397
0.6728	Remote Similarity	NPC64661
0.67	Remote Similarity	NPC67658
0.6685	Remote Similarity	NPC474258
0.6685	Remote Similarity	NPC133003
0.6684	Remote Similarity	NPC243716
0.6684	Remote Similarity	NPC476524
0.6667	Remote Similarity	NPC12831
0.6667	Remote Similarity	NPC59839
0.6667	Remote Similarity	NPC48171
0.6667	Remote Similarity	NPC129753
0.6667	Remote Similarity	NPC169308
0.6667	Remote Similarity	NPC244087
0.6667	Remote Similarity	NPC77582
0.6667	Remote Similarity	NPC97230
0.6667	Remote Similarity	NPC74928
0.6667	Remote Similarity	NPC205604
0.6667	Remote Similarity	NPC3698
0.6667	Remote Similarity	NPC476419
0.6667	Remote Similarity	NPC286529
0.6667	Remote Similarity	NPC209281
0.6667	Remote Similarity	NPC302717
0.6633	Remote Similarity	NPC469715
0.6615	Remote Similarity	NPC477004
0.6613	Remote Similarity	NPC473946
0.6611	Remote Similarity	NPC186068
0.6599	Remote Similarity	NPC476525
0.6568	Remote Similarity	NPC302159
0.6527	Remote Similarity	NPC114033
0.6527	Remote Similarity	NPC101130
0.6527	Remote Similarity	NPC129412
0.6527	Remote Similarity	NPC58268
0.6509	Remote Similarity	NPC467188
0.6505	Remote Similarity	NPC243633
0.6505	Remote Similarity	NPC175150
0.6497	Remote Similarity	NPC274981
0.6455	Remote Similarity	NPC324091
0.6453	Remote Similarity	NPC473878
0.6452	Remote Similarity	NPC110158
0.6439	Remote Similarity	NPC168209
0.6437	Remote Similarity	NPC75135
0.6433	Remote Similarity	NPC100726
0.6433	Remote Similarity	NPC105811
0.6413	Remote Similarity	NPC11126
0.6407	Remote Similarity	NPC85443
0.6398	Remote Similarity	NPC470205
0.6383	Remote Similarity	NPC476527
0.6379	Remote Similarity	NPC251391
0.6378	Remote Similarity	NPC182940
0.6374	Remote Similarity	NPC288074
0.6359	Remote Similarity	NPC237414
0.6358	Remote Similarity	NPC471655
0.6328	Remote Similarity	NPC474492
0.6316	Remote Similarity	NPC470440
0.6316	Remote Similarity	NPC473628
0.631	Remote Similarity	NPC159125
0.6304	Remote Similarity	NPC151635
0.6301	Remote Similarity	NPC123906
0.6296	Remote Similarity	NPC471589
0.6292	Remote Similarity	NPC100104
0.6292	Remote Similarity	NPC470680
0.6289	Remote Similarity	NPC179701
0.6289	Remote Similarity	NPC102592
0.6289	Remote Similarity	NPC79356
0.6284	Remote Similarity	NPC161861
0.6283	Remote Similarity	NPC475874
0.6277	Remote Similarity	NPC228835
0.6277	Remote Similarity	NPC477003
0.6276	Remote Similarity	NPC474767
0.6269	Remote Similarity	NPC188821
0.6269	Remote Similarity	NPC474180
0.6261	Remote Similarity	NPC66642
0.6256	Remote Similarity	NPC262898
0.625	Remote Similarity	NPC263455
0.625	Remote Similarity	NPC469529
0.625	Remote Similarity	NPC229055
0.6243	Remote Similarity	NPC109447
0.6243	Remote Similarity	NPC311282
0.6243	Remote Similarity	NPC114637
0.6243	Remote Similarity	NPC241025
0.6242	Remote Similarity	NPC330326
0.6237	Remote Similarity	NPC294693
0.6229	Remote Similarity	NPC70406
0.6229	Remote Similarity	NPC470679
0.6229	Remote Similarity	NPC217021
0.6224	Remote Similarity	NPC474389
0.6223	Remote Similarity	NPC102755
0.6211	Remote Similarity	NPC94752
0.6205	Remote Similarity	NPC292361
0.6203	Remote Similarity	NPC234403
0.6203	Remote Similarity	NPC91179
0.62	Remote Similarity	NPC88115
0.6193	Remote Similarity	NPC312860
0.619	Remote Similarity	NPC21429
0.6183	Remote Similarity	NPC217372
0.6183	Remote Similarity	NPC183662
0.6183	Remote Similarity	NPC15573
0.6181	Remote Similarity	NPC106757
0.6178	Remote Similarity	NPC17059
0.6171	Remote Similarity	NPC313889
0.6162	Remote Similarity	NPC77241
0.6162	Remote Similarity	NPC13456
0.6162	Remote Similarity	NPC166209
0.6162	Remote Similarity	NPC269203
0.615	Remote Similarity	NPC317701
0.615	Remote Similarity	NPC219336
0.6146	Remote Similarity	NPC209917
0.6131	Remote Similarity	NPC471944
0.6129	Remote Similarity	NPC121903
0.6126	Remote Similarity	NPC141612
0.6126	Remote Similarity	NPC135601
0.6126	Remote Similarity	NPC17273
0.6117	Remote Similarity	NPC79777
0.6117	Remote Similarity	NPC24864
0.6111	Remote Similarity	NPC220797
0.6111	Remote Similarity	NPC153123
0.6111	Remote Similarity	NPC474318
0.6111	Remote Similarity	NPC268744
0.6111	Remote Similarity	NPC475914
0.6111	Remote Similarity	NPC201266
0.6108	Remote Similarity	NPC252572
0.6108	Remote Similarity	NPC64055
0.6102	Remote Similarity	NPC281094
0.6099	Remote Similarity	NPC42372
0.6096	Remote Similarity	NPC83774
0.6095	Remote Similarity	NPC65408

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 NPC474236 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	1039
0.2-0.3	1535
0.3-0.4	2543
0.4-0.5	2771
0.5-0.6	959
0.6-0.7	47
0.7-0.8	3
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
0.7108	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2290	Phase 3
0.7081	Intermediate Similarity	NPD2289	Phase 3
0.7019	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1096	Discontinued
0.6796	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7459	Phase 2
0.6704	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD1618	Phase 2
0.6545	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5685	Approved
0.6543	Remote Similarity	NPD5686	Approved
0.6463	Remote Similarity	NPD272	Approved
0.6462	Remote Similarity	NPD7817	Phase 1
0.6398	Remote Similarity	NPD1031	Discontinued
0.6383	Remote Similarity	NPD5809	Phase 3
0.6378	Remote Similarity	NPD5017	Discontinued
0.6378	Remote Similarity	NPD7727	Phase 2
0.6369	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8115	Approved
0.6364	Remote Similarity	NPD8114	Approved
0.6302	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD9599	Approved
0.6257	Remote Similarity	NPD3178	Discontinued
0.6242	Remote Similarity	NPD9100	Approved
0.6229	Remote Similarity	NPD510	Phase 1
0.6223	Remote Similarity	NPD1745	Approved
0.6222	Remote Similarity	NPD1631	Approved
0.6221	Remote Similarity	NPD175	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD1573	Approved
0.6175	Remote Similarity	NPD1575	Approved
0.6171	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD9598	Discontinued
0.6162	Remote Similarity	NPD4883	Approved
0.615	Remote Similarity	NPD3078	Approved
0.615	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.615	Remote Similarity	NPD3077	Approved
0.615	Remote Similarity	NPD3076	Approved
0.615	Remote Similarity	NPD3079	Approved
0.6145	Remote Similarity	NPD1630	Approved
0.6136	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.612	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD3927	Phase 2
0.6095	Remote Similarity	NPD201	Phase 2
0.6095	Remote Similarity	NPD200	Phase 2
0.6077	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7618	Phase 3
0.6071	Remote Similarity	NPD7619	Phase 3
0.6067	Remote Similarity	NPD2061	Approved
0.6066	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD2214	Approved
0.6056	Remote Similarity	NPD2213	Approved
0.6047	Remote Similarity	NPD5020	Approved
0.6043	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD7483	Phase 2
0.6021	Remote Similarity	NPD7482	Phase 2
0.602	Remote Similarity	NPD460	Discontinued
0.6019	Remote Similarity	NPD1996	Discontinued
0.6013	Remote Similarity	NPD9396	Approved
0.6013	Remote Similarity	NPD9392	Approved
0.6011	Remote Similarity	NPD2915	Discontinued
0.6	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4811	Discontinued
0.598	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD3319	Phase 1
0.5969	Remote Similarity	NPD3318	Approved
0.5969	Remote Similarity	NPD3320	Approved
0.5965	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD4805	Approved
0.5949	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD1643	Phase 3
0.5942	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD1781	Discontinued
0.5938	Remote Similarity	NPD7564	Discontinued
0.5936	Remote Similarity	NPD750	Phase 2
0.5936	Remote Similarity	NPD4524	Discontinued
0.5935	Remote Similarity	NPD7716	Approved
0.5935	Remote Similarity	NPD7717	Approved
0.5935	Remote Similarity	NPD6173	Approved
0.5932	Remote Similarity	NPD1183	Approved
0.5928	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5787	Discontinued
0.5922	Remote Similarity	NPD4520	Approved
0.5922	Remote Similarity	NPD3968	Approved
0.5918	Remote Similarity	NPD1658	Discontinued
0.5918	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD4326	Phase 2
0.5902	Remote Similarity	NPD3411	Phase 2
0.5902	Remote Similarity	NPD6771	Discontinued
0.5902	Remote Similarity	NPD3410	Approved
0.59	Remote Similarity	NPD772	Phase 3
0.5895	Remote Similarity	NPD1587	Approved
0.5894	Remote Similarity	NPD4051	Discontinued
0.5894	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD803	Phase 1
0.5892	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4376	Phase 3
0.5882	Remote Similarity	NPD8169	Discontinued
0.588	Remote Similarity	NPD8289	Discontinued
0.5873	Remote Similarity	NPD2367	Phase 2
0.5873	Remote Similarity	NPD5104	Approved
0.5871	Remote Similarity	NPD6248	Phase 2
0.5871	Remote Similarity	NPD7308	Discontinued
0.5871	Remote Similarity	NPD6249	Phase 2
0.587	Remote Similarity	NPD3583	Phase 2
0.5862	Remote Similarity	NPD6268	Phase 1
0.5862	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.586	Remote Similarity	NPD5021	Discontinued
0.5859	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3967	Approved
0.5854	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD9075	Approved
0.5852	Remote Similarity	NPD9074	Approved
0.585	Remote Similarity	NPD1174	Phase 2
0.585	Remote Similarity	NPD1952	Discontinued
0.5849	Remote Similarity	NPD1623	Approved
0.5848	Remote Similarity	NPD206	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD3246	Discontinued
0.5842	Remote Similarity	NPD4155	Approved
0.5838	Remote Similarity	NPD4804	Approved
0.5837	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD1506	Discontinued
0.5822	Remote Similarity	NPD5198	Approved
0.5822	Remote Similarity	NPD5199	Approved
0.582	Remote Similarity	NPD482	Approved
0.582	Remote Similarity	NPD1586	Approved
0.5816	Remote Similarity	NPD4334	Discontinued
0.5815	Remote Similarity	NPD5400	Approved
0.5808	Remote Similarity	NPD4922	Phase 2
0.5808	Remote Similarity	NPD6665	Discontinued
0.5805	Remote Similarity	NPD107	Approved
0.5805	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD8272	Phase 2
0.5802	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.5801	Remote Similarity	NPD4436	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4848	Phase 1
0.5797	Remote Similarity	NPD2442	Approved
0.5797	Remote Similarity	NPD6376	Discontinued
0.5797	Remote Similarity	NPD2443	Approved
0.5795	Remote Similarity	NPD7026	Phase 2
0.5794	Remote Similarity	NPD6210	Phase 3
0.5792	Remote Similarity	NPD2405	Phase 3
0.5792	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6044	Discontinued
0.5789	Remote Similarity	NPD749	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD5473	Discontinued
0.5781	Remote Similarity	NPD2479	Phase 3
0.5781	Remote Similarity	NPD2481	Approved
0.5779	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.5779	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.5779	Remote Similarity	NPD9098	Phase 3
0.5775	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD2416	Approved
0.5773	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD2417	Approved
0.5771	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD276	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD3961	Discontinued
0.5765	Remote Similarity	NPD4988	Discontinued
0.5761	Remote Similarity	NPD2511	Approved
0.5756	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.5756	Remote Similarity	NPD5487	Phase 1
0.5754	Remote Similarity	NPD5748	Phase 2
0.575	Remote Similarity	NPD7944	Discontinued
0.5747	Remote Similarity	NPD2070	Approved
0.5747	Remote Similarity	NPD2071	Approved
0.5747	Remote Similarity	NPD2068	Approved
0.5747	Remote Similarity	NPD2069	Approved
0.5746	Remote Similarity	NPD737	Phase 2
0.5744	Remote Similarity	NPD5555	Phase 1
0.5737	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD5016	Approved
0.5736	Remote Similarity	NPD6068	Discontinued
0.573	Remote Similarity	NPD1683	Approved
0.5729	Remote Similarity	NPD4315	Phase 2
0.5728	Remote Similarity	NPD5643	Phase 2
0.5728	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD3947	Discontinued
0.5728	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD1659	Phase 1
0.5723	Remote Similarity	NPD9540	Approved
0.5722	Remote Similarity	NPD438	Approved
0.5722	Remote Similarity	NPD971	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD439	Approved
0.5722	Remote Similarity	NPD5728	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