NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	406.03
Volume:	320.881
LogP:	3.857
LogD:	2.706
LogS:	-3.985
# Rotatable Bonds:	8
TPSA:	15.71
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	2.284
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.713
MDCK Permeability:	1.099388100556098e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.68

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	88.13336944580078%
Volume Distribution (VD):	2.132
Pgp-substrate:	17.620702743530273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.494
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.985
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.251
CYP2D6-inhibitor:	0.822
CYP2D6-substrate:	0.956
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.772

ADMET: Excretion

Clearance (CL):	3.615
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.3
Human Hepatotoxicity (H-HT):	0.269
Drug-inuced Liver Injury (DILI):	0.308
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.838
Maximum Recommended Daily Dose:	0.718
Skin Sensitization:	0.918
Carcinogencity:	0.127
Eye Corrosion:	0.046
Eye Irritation:	0.012
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC110131

Natural Product ID:	NPC110131
*Common Name:**	Aplysamine
IUPAC Name:	3-[2,6-dibromo-4-[2-(dimethylamino)ethyl]phenoxy]-N,N-dimethylpropan-1-amine
Synonyms:	Aplysamine; Aplysamine-1
Standard InCHIKey:	LWENJEAGCYZOBC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H24Br2N2O/c1-18(2)7-5-9-20-15-13(16)10-12(11-14(15)17)6-8-19(3)4/h10-11H,5-9H2,1-4H3
SMILES:	CN(CCCOc1c(Br)cc(cc1Br)CCN(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL380697
PubChem CID:	362025
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO32606	aplysinella sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425148]
NPO32712	suberea ianthelliformis	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22515429]
NPO32606	aplysinella sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24758268]

☑ 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
Ki	4
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4605	Cell Line	CCF-STTG1	Homo sapiens	FC	=	2.0	n.a.	PMID[528843]
NPT987	Individual Protein	Histamine H3 receptor	Homo sapiens	Ki	=	30.0	nM	PMID[528839]
NPT986	Individual Protein	Histamine H3 receptor	Rattus norvegicus	Ki	=	249.0	nM	PMID[528839]
NPT989	Individual Protein	Histamine H3 receptor	Cavia porcellus	IC50	=	500.0	nM	PMID[528840]
NPT987	Individual Protein	Histamine H3 receptor	Homo sapiens	Ki	=	30.0	nM	PMID[528841]
NPT987	Individual Protein	Histamine H3 receptor	Homo sapiens	Ki	=	30.0	nM	PMID[528844]

☑ 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 NPC110131 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	252
0.1-0.2	3172
0.2-0.3	13550
0.3-0.4	6057
0.4-0.5	13017
0.5-0.6	5992
0.6-0.7	593
0.7-0.8	41
0.8-0.85	14
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9262	High Similarity	NPC272463
0.8806	High Similarity	NPC135349
0.8647	High Similarity	NPC128877
0.8613	High Similarity	NPC296085
0.8613	High Similarity	NPC71629
0.8593	High Similarity	NPC308571
0.8489	Intermediate Similarity	NPC76412
0.8433	Intermediate Similarity	NPC474673
0.8429	Intermediate Similarity	NPC258222
0.8394	Intermediate Similarity	NPC78530
0.8369	Intermediate Similarity	NPC47672
0.8194	Intermediate Similarity	NPC233926
0.8169	Intermediate Similarity	NPC109968
0.8069	Intermediate Similarity	NPC156311
0.8015	Intermediate Similarity	NPC470471
0.7986	Intermediate Similarity	NPC469711
0.7899	Intermediate Similarity	NPC470470
0.7883	Intermediate Similarity	NPC235633
0.7842	Intermediate Similarity	NPC40321
0.7826	Intermediate Similarity	NPC470248
0.7826	Intermediate Similarity	NPC470249
0.7778	Intermediate Similarity	NPC135173
0.7714	Intermediate Similarity	NPC470250
0.766	Intermediate Similarity	NPC470709
0.7638	Intermediate Similarity	NPC115803
0.7622	Intermediate Similarity	NPC470472
0.7606	Intermediate Similarity	NPC474128
0.7559	Intermediate Similarity	NPC26524
0.7552	Intermediate Similarity	NPC470247
0.7548	Intermediate Similarity	NPC477255
0.75	Intermediate Similarity	NPC280736
0.7407	Intermediate Similarity	NPC236265
0.7394	Intermediate Similarity	NPC213471
0.7391	Intermediate Similarity	NPC195902
0.7388	Intermediate Similarity	NPC116562
0.7339	Intermediate Similarity	NPC42383
0.7338	Intermediate Similarity	NPC70485
0.7333	Intermediate Similarity	NPC328267
0.7293	Intermediate Similarity	NPC321133
0.7293	Intermediate Similarity	NPC263835
0.7287	Intermediate Similarity	NPC59387
0.7239	Intermediate Similarity	NPC477254
0.7183	Intermediate Similarity	NPC303993
0.7165	Intermediate Similarity	NPC97811
0.7092	Intermediate Similarity	NPC11449
0.7073	Intermediate Similarity	NPC471576
0.7048	Intermediate Similarity	NPC77435
0.7048	Intermediate Similarity	NPC121571
0.7048	Intermediate Similarity	NPC8093
0.7048	Intermediate Similarity	NPC259071
0.6992	Remote Similarity	NPC313918
0.6984	Remote Similarity	NPC108875
0.6984	Remote Similarity	NPC38079
0.6978	Remote Similarity	NPC320242
0.6972	Remote Similarity	NPC475735
0.6972	Remote Similarity	NPC473724
0.696	Remote Similarity	NPC51633
0.6957	Remote Similarity	NPC255253
0.6953	Remote Similarity	NPC186469
0.695	Remote Similarity	NPC283079
0.6929	Remote Similarity	NPC470393
0.6929	Remote Similarity	NPC473855
0.6917	Remote Similarity	NPC71853
0.6913	Remote Similarity	NPC79076
0.6912	Remote Similarity	NPC180207
0.6905	Remote Similarity	NPC192596
0.6905	Remote Similarity	NPC319933
0.6901	Remote Similarity	NPC474091
0.6901	Remote Similarity	NPC474087
0.6901	Remote Similarity	NPC99280
0.6884	Remote Similarity	NPC298486
0.688	Remote Similarity	NPC289381
0.688	Remote Similarity	NPC155847
0.6879	Remote Similarity	NPC78061
0.6879	Remote Similarity	NPC159987
0.6879	Remote Similarity	NPC122359
0.6875	Remote Similarity	NPC243404
0.687	Remote Similarity	NPC166837
0.686	Remote Similarity	NPC321956
0.6857	Remote Similarity	NPC124776
0.6849	Remote Similarity	NPC307682
0.6846	Remote Similarity	NPC54543
0.6838	Remote Similarity	NPC43275
0.6838	Remote Similarity	NPC256369
0.6833	Remote Similarity	NPC8002
0.6833	Remote Similarity	NPC259134
0.6833	Remote Similarity	NPC177844
0.6833	Remote Similarity	NPC99886
0.6829	Remote Similarity	NPC143450
0.6824	Remote Similarity	NPC212850
0.6824	Remote Similarity	NPC83289
0.6824	Remote Similarity	NPC189724
0.6809	Remote Similarity	NPC218323
0.6807	Remote Similarity	NPC475396
0.6806	Remote Similarity	NPC274732
0.6806	Remote Similarity	NPC247018
0.6806	Remote Similarity	NPC307123
0.6806	Remote Similarity	NPC97870
0.6802	Remote Similarity	NPC474678
0.6802	Remote Similarity	NPC471338
0.6802	Remote Similarity	NPC227953
0.6794	Remote Similarity	NPC473358
0.6769	Remote Similarity	NPC146530
0.6763	Remote Similarity	NPC202866
0.6763	Remote Similarity	NPC475843
0.6761	Remote Similarity	NPC172403
0.6748	Remote Similarity	NPC471581
0.6744	Remote Similarity	NPC176971
0.6742	Remote Similarity	NPC21890
0.6738	Remote Similarity	NPC141739
0.6738	Remote Similarity	NPC136112
0.6727	Remote Similarity	NPC469979
0.6727	Remote Similarity	NPC226001
0.672	Remote Similarity	NPC95755
0.6719	Remote Similarity	NPC283546
0.6716	Remote Similarity	NPC221301
0.6714	Remote Similarity	NPC105999
0.6714	Remote Similarity	NPC217277
0.6714	Remote Similarity	NPC211218
0.6706	Remote Similarity	NPC473892
0.6706	Remote Similarity	NPC475658
0.6693	Remote Similarity	NPC307425
0.6692	Remote Similarity	NPC157473
0.6692	Remote Similarity	NPC258171
0.6692	Remote Similarity	NPC151530
0.6691	Remote Similarity	NPC120075
0.669	Remote Similarity	NPC475361
0.669	Remote Similarity	NPC474753
0.669	Remote Similarity	NPC470392
0.6687	Remote Similarity	NPC126128
0.6687	Remote Similarity	NPC110454
0.6687	Remote Similarity	NPC298981
0.6687	Remote Similarity	NPC473462
0.6687	Remote Similarity	NPC207819
0.6667	Remote Similarity	NPC213414
0.6667	Remote Similarity	NPC95733
0.6667	Remote Similarity	NPC162294
0.6667	Remote Similarity	NPC62101
0.6667	Remote Similarity	NPC95977
0.6667	Remote Similarity	NPC147847
0.6667	Remote Similarity	NPC160193
0.6667	Remote Similarity	NPC128730
0.6667	Remote Similarity	NPC100870
0.6645	Remote Similarity	NPC247298
0.6644	Remote Similarity	NPC163810
0.6641	Remote Similarity	NPC309982
0.6641	Remote Similarity	NPC471495
0.662	Remote Similarity	NPC29477
0.6619	Remote Similarity	NPC318357
0.6618	Remote Similarity	NPC264379
0.6614	Remote Similarity	NPC107101
0.6608	Remote Similarity	NPC174607
0.6608	Remote Similarity	NPC471591
0.6601	Remote Similarity	NPC189908
0.6597	Remote Similarity	NPC281499
0.6596	Remote Similarity	NPC474169
0.6596	Remote Similarity	NPC473572
0.6575	Remote Similarity	NPC118419
0.6573	Remote Similarity	NPC123140
0.6573	Remote Similarity	NPC471337
0.657	Remote Similarity	NPC473409
0.657	Remote Similarity	NPC141405
0.657	Remote Similarity	NPC82741
0.6568	Remote Similarity	NPC214188
0.6568	Remote Similarity	NPC74618
0.6568	Remote Similarity	NPC301941
0.6566	Remote Similarity	NPC225130
0.6558	Remote Similarity	NPC245974
0.6552	Remote Similarity	NPC262641
0.6547	Remote Similarity	NPC471308
0.6547	Remote Similarity	NPC289330
0.6547	Remote Similarity	NPC53596
0.6547	Remote Similarity	NPC160120
0.6547	Remote Similarity	NPC17388
0.6544	Remote Similarity	NPC303370
0.6541	Remote Similarity	NPC25067
0.6541	Remote Similarity	NPC88868
0.6541	Remote Similarity	NPC46844
0.6541	Remote Similarity	NPC231251
0.6538	Remote Similarity	NPC473393
0.6538	Remote Similarity	NPC8302
0.6531	Remote Similarity	NPC325568
0.6531	Remote Similarity	NPC266425
0.6531	Remote Similarity	NPC132308
0.6528	Remote Similarity	NPC474147
0.6528	Remote Similarity	NPC473708
0.6525	Remote Similarity	NPC229213
0.6525	Remote Similarity	NPC296202
0.6522	Remote Similarity	NPC71186
0.6515	Remote Similarity	NPC291837
0.6512	Remote Similarity	NPC179686
0.651	Remote Similarity	NPC167944
0.651	Remote Similarity	NPC42793
0.651	Remote Similarity	NPC231884
0.651	Remote Similarity	NPC309667
0.6507	Remote Similarity	NPC476570
0.6493	Remote Similarity	NPC55300
0.6489	Remote Similarity	NPC326447
0.6489	Remote Similarity	NPC326801
0.6488	Remote Similarity	NPC475615

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 NPC110131 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1003
0.2-0.3	1388
0.3-0.4	2669
0.4-0.5	2417
0.5-0.6	1137
0.6-0.7	320
0.7-0.8	28
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
0.7385	Intermediate Similarity	NPD3596	Phase 2
0.7348	Intermediate Similarity	NPD2595	Approved
0.7348	Intermediate Similarity	NPD2594	Approved
0.7333	Intermediate Similarity	NPD2428	Approved
0.7333	Intermediate Similarity	NPD2429	Approved
0.7293	Intermediate Similarity	NPD2668	Approved
0.7293	Intermediate Similarity	NPD2667	Approved
0.7293	Intermediate Similarity	NPD2556	Approved
0.7293	Intermediate Similarity	NPD2554	Approved
0.7273	Intermediate Similarity	NPD6581	Approved
0.7273	Intermediate Similarity	NPD6580	Approved
0.7273	Intermediate Similarity	NPD2486	Discontinued
0.7266	Intermediate Similarity	NPD5746	Approved
0.7222	Intermediate Similarity	NPD5374	Approved
0.7222	Intermediate Similarity	NPD5373	Approved
0.7218	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2557	Approved
0.7163	Intermediate Similarity	NPD5745	Approved
0.7111	Intermediate Similarity	NPD3294	Phase 2
0.7101	Intermediate Similarity	NPD4098	Discontinued
0.7099	Intermediate Similarity	NPD595	Approved
0.7099	Intermediate Similarity	NPD593	Approved
0.7092	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6382	Discontinued
0.709	Intermediate Similarity	NPD3049	Approved
0.709	Intermediate Similarity	NPD3445	Approved
0.709	Intermediate Similarity	NPD3444	Approved
0.709	Intermediate Similarity	NPD3443	Approved
0.705	Intermediate Similarity	NPD7018	Phase 2
0.7029	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1820	Approved
0.6978	Remote Similarity	NPD1819	Approved
0.6978	Remote Similarity	NPD1817	Approved
0.6978	Remote Similarity	NPD1818	Approved
0.6972	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6583	Phase 3
0.6957	Remote Similarity	NPD6539	Approved
0.6957	Remote Similarity	NPD6540	Phase 3
0.6957	Remote Similarity	NPD6582	Phase 2
0.6957	Remote Similarity	NPD6543	Approved
0.6957	Remote Similarity	NPD6542	Approved
0.6947	Remote Similarity	NPD2496	Approved
0.6947	Remote Similarity	NPD2497	Approved
0.6947	Remote Similarity	NPD821	Approved
0.6929	Remote Similarity	NPD2987	Approved
0.6929	Remote Similarity	NPD2990	Approved
0.6923	Remote Similarity	NPD4475	Approved
0.6923	Remote Similarity	NPD4474	Approved
0.6923	Remote Similarity	NPD2245	Discovery
0.6908	Remote Similarity	NPD2184	Approved
0.6908	Remote Similarity	NPD2183	Approved
0.6906	Remote Similarity	NPD6538	Approved
0.6906	Remote Similarity	NPD6541	Approved
0.6875	Remote Similarity	NPD3142	Approved
0.6875	Remote Similarity	NPD3140	Approved
0.6871	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6584	Phase 3
0.6806	Remote Similarity	NPD1423	Approved
0.6803	Remote Similarity	NPD6380	Phase 1
0.6783	Remote Similarity	NPD5163	Phase 2
0.6783	Remote Similarity	NPD3164	Approved
0.6783	Remote Similarity	NPD9718	Approved
0.6783	Remote Similarity	NPD3167	Approved
0.6783	Remote Similarity	NPD3166	Approved
0.6783	Remote Similarity	NPD3165	Approved
0.6781	Remote Similarity	NPD3052	Approved
0.6781	Remote Similarity	NPD3054	Approved
0.6769	Remote Similarity	NPD2684	Approved
0.6767	Remote Similarity	NPD592	Approved
0.6767	Remote Similarity	NPD594	Approved
0.6763	Remote Similarity	NPD2232	Approved
0.6763	Remote Similarity	NPD2230	Approved
0.6763	Remote Similarity	NPD2233	Approved
0.6761	Remote Similarity	NPD4993	Discontinued
0.6757	Remote Similarity	NPD1725	Approved
0.6738	Remote Similarity	NPD1794	Approved
0.6736	Remote Similarity	NPD5718	Phase 2
0.6736	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3685	Discontinued
0.6714	Remote Similarity	NPD1420	Approved
0.6714	Remote Similarity	NPD1421	Approved
0.6711	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3530	Approved
0.669	Remote Similarity	NPD3531	Approved
0.669	Remote Similarity	NPD7905	Discontinued
0.669	Remote Similarity	NPD3532	Approved
0.6689	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2671	Approved
0.6667	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2673	Approved
0.6667	Remote Similarity	NPD3180	Approved
0.6667	Remote Similarity	NPD3179	Approved
0.6644	Remote Similarity	NPD6225	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3156	Discontinued
0.6643	Remote Similarity	NPD2231	Phase 2
0.6643	Remote Similarity	NPD2235	Phase 2
0.6623	Remote Similarity	NPD6364	Approved
0.6623	Remote Similarity	NPD44	Approved
0.6623	Remote Similarity	NPD4162	Approved
0.6622	Remote Similarity	NPD2200	Suspended
0.6621	Remote Similarity	NPD7294	Phase 1
0.6615	Remote Similarity	NPD3524	Approved
0.6615	Remote Similarity	NPD3526	Approved
0.6615	Remote Similarity	NPD812	Approved
0.6615	Remote Similarity	NPD810	Approved
0.6615	Remote Similarity	NPD811	Approved
0.66	Remote Similarity	NPD3656	Approved
0.66	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1669	Approved
0.6596	Remote Similarity	NPD4129	Approved
0.6577	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7265	Discontinued
0.6567	Remote Similarity	NPD7843	Approved
0.6554	Remote Similarity	NPD2653	Approved
0.6531	Remote Similarity	NPD2238	Phase 2
0.6531	Remote Similarity	NPD3109	Approved
0.6531	Remote Similarity	NPD3110	Approved
0.6529	Remote Similarity	NPD3337	Discontinued
0.6528	Remote Similarity	NPD2237	Approved
0.6528	Remote Similarity	NPD1712	Approved
0.6528	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2228	Approved
0.6519	Remote Similarity	NPD2234	Approved
0.6519	Remote Similarity	NPD2229	Approved
0.6519	Remote Similarity	NPD1009	Approved
0.6513	Remote Similarity	NPD2459	Approved
0.6513	Remote Similarity	NPD2458	Approved
0.6513	Remote Similarity	NPD2460	Phase 3
0.651	Remote Similarity	NPD6896	Approved
0.651	Remote Similarity	NPD6895	Approved
0.6507	Remote Similarity	NPD1039	Discontinued
0.6503	Remote Similarity	NPD3568	Approved
0.6503	Remote Similarity	NPD3567	Approved
0.6503	Remote Similarity	NPD1318	Phase 2
0.6494	Remote Similarity	NPD5295	Discontinued
0.6489	Remote Similarity	NPD3134	Approved
0.6485	Remote Similarity	NPD6687	Approved
0.6485	Remote Similarity	NPD6688	Approved
0.6471	Remote Similarity	NPD6748	Discontinued
0.6463	Remote Similarity	NPD3163	Approved
0.6463	Remote Similarity	NPD7477	Discontinued
0.6463	Remote Similarity	NPD3162	Approved
0.6458	Remote Similarity	NPD558	Phase 2
0.6458	Remote Similarity	NPD3691	Phase 2
0.6458	Remote Similarity	NPD3690	Phase 2
0.6456	Remote Similarity	NPD6357	Discontinued
0.6454	Remote Similarity	NPD776	Approved
0.6447	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7153	Discontinued
0.6443	Remote Similarity	NPD2157	Approved
0.6439	Remote Similarity	NPD1358	Approved
0.6438	Remote Similarity	NPD6179	Discontinued
0.6433	Remote Similarity	NPD7131	Phase 3
0.6429	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3692	Discontinued
0.6424	Remote Similarity	NPD2239	Approved
0.6424	Remote Similarity	NPD4477	Approved
0.6424	Remote Similarity	NPD2161	Phase 2
0.6424	Remote Similarity	NPD2240	Approved
0.6424	Remote Similarity	NPD4476	Approved
0.6423	Remote Similarity	NPD7157	Approved
0.6419	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD455	Discontinued
0.641	Remote Similarity	NPD7020	Approved
0.641	Remote Similarity	NPD7019	Approved
0.641	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6419	Discontinued
0.6405	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD4236	Phase 3
0.6405	Remote Similarity	NPD4237	Approved
0.64	Remote Similarity	NPD6111	Discontinued
0.6397	Remote Similarity	NPD1241	Discontinued
0.6395	Remote Similarity	NPD1336	Approved
0.6392	Remote Similarity	NPD4210	Discontinued
0.6387	Remote Similarity	NPD6666	Approved
0.6387	Remote Similarity	NPD6667	Approved
0.6383	Remote Similarity	NPD3447	Discontinued
0.6382	Remote Similarity	NPD1375	Discontinued
0.6382	Remote Similarity	NPD7030	Discontinued
0.637	Remote Similarity	NPD4571	Approved
0.637	Remote Similarity	NPD4572	Approved
0.637	Remote Similarity	NPD4573	Approved
0.6364	Remote Similarity	NPD7466	Approved
0.6364	Remote Similarity	NPD1445	Approved
0.6364	Remote Similarity	NPD1444	Approved
0.6358	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD2558	Approved
0.6357	Remote Similarity	NPD2550	Approved
0.6357	Remote Similarity	NPD2552	Approved
0.6357	Remote Similarity	NPD2553	Approved
0.6357	Remote Similarity	NPD2555	Approved
0.6357	Remote Similarity	NPD2549	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