NPASS Compound

Structure

NPC109447 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 -2.2142 5.6302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8615 5.0949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8907 2.6576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8833 4.8870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2435 3.1928 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9344 2.2418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.2216 3.4007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 2.0339 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 -3.6036 1.4986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 20 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 13 14 2 0 0 0 0 14 22 1 0 0 0 0 15 8 1 1 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 21 2 3 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	443.02
Volume:	352.641
LogP:	4.206
LogD:	3.997
LogS:	-3.89
# Rotatable Bonds:	8
TPSA:	56.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	2.977
Fsp3:	0.471
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:	-4.76
MDCK Permeability:	1.7682603356661275e-05
Pgp-inhibitor:	0.061
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.422
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983
Plasma Protein Binding (PPB):	93.43924713134766%
Volume Distribution (VD):	2.022
Pgp-substrate:	8.816597938537598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.905
CYP1A2-substrate:	0.857
CYP2C19-inhibitor:	0.905
CYP2C19-substrate:	0.563
CYP2C9-inhibitor:	0.528
CYP2C9-substrate:	0.714
CYP2D6-inhibitor:	0.784
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	2.955
Half-life (T1/2):	0.312

ADMET: Toxicity

hERG Blockers:	0.559
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.145
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.326
Carcinogencity:	0.407
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC109447

Natural Product ID:	NPC109447
*Common Name:**	Altematamide C
IUPAC Name:	(2S)-N-[2-(2,5-dibromo-1H-indol-3-yl)ethyl]-4-methyl-2-(methylamino)pentanamide
Synonyms:	Altematamide C
Standard InCHIKey:	NGOMPZFXFWQELT-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C17H23Br2N3O/c1-10(2)8-15(20-3)17(23)21-7-6-12-13-9-11(18)4-5-14(13)22-16(12)19/h4-5,9-10,15,20,22H,6-8H2,1-3H3,(H,21,23)/t15-/m0/s1
SMILES:	CN[C@H](C(=NCCc1c(Br)[nH]c2c1cc(Br)cc2)O)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511199
PubChem CID:	10049156
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 [CHEMONTID:0004329] Leucine 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
NPO19302	Amathia alternata	Species	Vesiculariidae	Eukaryota	n.a.	Atlantic	n.a.	PMID[9249973]
NPO19302	Amathia alternata	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	13

Activity Type	# Activity
Organism	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	4.0	ug.mL-1	PMID[531322]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	4.0	ug.mL-1	PMID[531322]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[531322]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[531322]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	4.0	ug.mL-1	PMID[531322]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	4.0	ug.mL-1	PMID[531322]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[531322]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	4.0	ug.mL-1	PMID[531323]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	4.0	ug.mL-1	PMID[531323]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[531323]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[531323]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	4.0	ug.mL-1	PMID[531323]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[531323]

☑ 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 NPC109447 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	451
0.1-0.2	6739
0.2-0.3	21953
0.3-0.4	7252
0.4-0.5	3044
0.5-0.6	1919
0.6-0.7	996
0.7-0.8	318
0.8-0.85	22
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.949	High Similarity	NPC64055
0.9125	High Similarity	NPC288074
0.8491	Intermediate Similarity	NPC34844
0.8471	Intermediate Similarity	NPC2272
0.8258	Intermediate Similarity	NPC262898
0.8228	Intermediate Similarity	NPC316069
0.8202	Intermediate Similarity	NPC179701
0.8199	Intermediate Similarity	NPC232798
0.8199	Intermediate Similarity	NPC469765
0.8199	Intermediate Similarity	NPC25008
0.8199	Intermediate Similarity	NPC469786
0.8199	Intermediate Similarity	NPC259644
0.8199	Intermediate Similarity	NPC469760
0.8199	Intermediate Similarity	NPC469763
0.8199	Intermediate Similarity	NPC73952
0.8182	Intermediate Similarity	NPC149265
0.8182	Intermediate Similarity	NPC243716
0.8165	Intermediate Similarity	NPC314372
0.8148	Intermediate Similarity	NPC80597
0.8148	Intermediate Similarity	NPC212376
0.8148	Intermediate Similarity	NPC70922
0.8148	Intermediate Similarity	NPC211572
0.8148	Intermediate Similarity	NPC75540
0.8125	Intermediate Similarity	NPC37548
0.8098	Intermediate Similarity	NPC285469
0.8086	Intermediate Similarity	NPC141926
0.8084	Intermediate Similarity	NPC474561
0.8084	Intermediate Similarity	NPC49954
0.8084	Intermediate Similarity	NPC160105
0.8038	Intermediate Similarity	NPC190296
0.8024	Intermediate Similarity	NPC280864
0.7988	Intermediate Similarity	NPC469785
0.7963	Intermediate Similarity	NPC105818
0.7963	Intermediate Similarity	NPC24678
0.7939	Intermediate Similarity	NPC469762
0.7933	Intermediate Similarity	NPC477166
0.7933	Intermediate Similarity	NPC477167
0.7933	Intermediate Similarity	NPC473342
0.7933	Intermediate Similarity	NPC304187
0.7927	Intermediate Similarity	NPC38736
0.7927	Intermediate Similarity	NPC470507
0.7904	Intermediate Similarity	NPC16667
0.7904	Intermediate Similarity	NPC282231
0.7901	Intermediate Similarity	NPC187951
0.7895	Intermediate Similarity	NPC314603
0.7885	Intermediate Similarity	NPC325252
0.7885	Intermediate Similarity	NPC218268
0.7875	Intermediate Similarity	NPC242556
0.7862	Intermediate Similarity	NPC63157
0.7862	Intermediate Similarity	NPC473868
0.7857	Intermediate Similarity	NPC311276
0.7857	Intermediate Similarity	NPC247987
0.7844	Intermediate Similarity	NPC279918
0.7826	Intermediate Similarity	NPC159856
0.7824	Intermediate Similarity	NPC63751
0.7818	Intermediate Similarity	NPC207726
0.7803	Intermediate Similarity	NPC474958
0.7799	Intermediate Similarity	NPC469768
0.7799	Intermediate Similarity	NPC469761
0.7799	Intermediate Similarity	NPC469783
0.7799	Intermediate Similarity	NPC469784
0.7799	Intermediate Similarity	NPC469767
0.7799	Intermediate Similarity	NPC469779
0.7799	Intermediate Similarity	NPC59084
0.7799	Intermediate Similarity	NPC469780
0.7792	Intermediate Similarity	NPC22079
0.7791	Intermediate Similarity	NPC477611
0.7784	Intermediate Similarity	NPC475935
0.7784	Intermediate Similarity	NPC94211
0.7784	Intermediate Similarity	NPC52909
0.7778	Intermediate Similarity	NPC97343
0.7771	Intermediate Similarity	NPC141353
0.7751	Intermediate Similarity	NPC40779
0.7751	Intermediate Similarity	NPC194640
0.775	Intermediate Similarity	NPC469766
0.7746	Intermediate Similarity	NPC280297
0.7736	Intermediate Similarity	NPC73767
0.773	Intermediate Similarity	NPC205254
0.773	Intermediate Similarity	NPC23420
0.773	Intermediate Similarity	NPC106771
0.773	Intermediate Similarity	NPC303820
0.773	Intermediate Similarity	NPC471957
0.7727	Intermediate Similarity	NPC233936
0.7722	Intermediate Similarity	NPC84911
0.7719	Intermediate Similarity	NPC317430
0.7719	Intermediate Similarity	NPC201700
0.7707	Intermediate Similarity	NPC198988
0.7701	Intermediate Similarity	NPC121903
0.7688	Intermediate Similarity	NPC2949
0.7688	Intermediate Similarity	NPC472123
0.7683	Intermediate Similarity	NPC124005
0.7679	Intermediate Similarity	NPC67056
0.7679	Intermediate Similarity	NPC6436
0.7674	Intermediate Similarity	NPC194411
0.7674	Intermediate Similarity	NPC280548
0.7661	Intermediate Similarity	NPC54988
0.766	Intermediate Similarity	NPC470505
0.7658	Intermediate Similarity	NPC29886
0.7658	Intermediate Similarity	NPC261195
0.7658	Intermediate Similarity	NPC96102
0.7644	Intermediate Similarity	NPC329688
0.7644	Intermediate Similarity	NPC189812
0.764	Intermediate Similarity	NPC228835
0.7633	Intermediate Similarity	NPC131718
0.7628	Intermediate Similarity	NPC475450
0.7625	Intermediate Similarity	NPC110126
0.7625	Intermediate Similarity	NPC88097
0.7622	Intermediate Similarity	NPC21605
0.7616	Intermediate Similarity	NPC41174
0.761	Intermediate Similarity	NPC105127
0.7607	Intermediate Similarity	NPC470440
0.7605	Intermediate Similarity	NPC471458
0.7602	Intermediate Similarity	NPC195507
0.7602	Intermediate Similarity	NPC17751
0.7586	Intermediate Similarity	NPC34508
0.7574	Intermediate Similarity	NPC230869
0.7574	Intermediate Similarity	NPC135141
0.7574	Intermediate Similarity	NPC92796
0.7571	Intermediate Similarity	NPC91179
0.7564	Intermediate Similarity	NPC475428
0.7557	Intermediate Similarity	NPC248454
0.7557	Intermediate Similarity	NPC68354
0.7557	Intermediate Similarity	NPC59269
0.7556	Intermediate Similarity	NPC94752
0.7543	Intermediate Similarity	NPC275305
0.7543	Intermediate Similarity	NPC37423
0.7532	Intermediate Similarity	NPC250361
0.753	Intermediate Similarity	NPC33421
0.753	Intermediate Similarity	NPC53947
0.7529	Intermediate Similarity	NPC82331
0.7529	Intermediate Similarity	NPC6982
0.7515	Intermediate Similarity	NPC299594
0.7514	Intermediate Similarity	NPC276540
0.7514	Intermediate Similarity	NPC317030
0.7514	Intermediate Similarity	NPC233050
0.7514	Intermediate Similarity	NPC248041
0.7514	Intermediate Similarity	NPC219336
0.7514	Intermediate Similarity	NPC126709
0.75	Intermediate Similarity	NPC204141
0.75	Intermediate Similarity	NPC274229
0.75	Intermediate Similarity	NPC470508
0.75	Intermediate Similarity	NPC288785
0.75	Intermediate Similarity	NPC473587
0.75	Intermediate Similarity	NPC267885
0.7485	Intermediate Similarity	NPC216713
0.7473	Intermediate Similarity	NPC213629
0.7469	Intermediate Similarity	NPC279081
0.7469	Intermediate Similarity	NPC115611
0.7459	Intermediate Similarity	NPC474707
0.7458	Intermediate Similarity	NPC151939
0.7458	Intermediate Similarity	NPC15573
0.7458	Intermediate Similarity	NPC217372
0.7458	Intermediate Similarity	NPC183662
0.7457	Intermediate Similarity	NPC49217
0.7456	Intermediate Similarity	NPC184476
0.7455	Intermediate Similarity	NPC129042
0.7444	Intermediate Similarity	NPC472294
0.7443	Intermediate Similarity	NPC203468
0.7443	Intermediate Similarity	NPC149155
0.7443	Intermediate Similarity	NPC110500
0.7442	Intermediate Similarity	NPC21174
0.7442	Intermediate Similarity	NPC271797
0.7442	Intermediate Similarity	NPC472587
0.7442	Intermediate Similarity	NPC102423
0.744	Intermediate Similarity	NPC200214
0.7436	Intermediate Similarity	NPC473762
0.743	Intermediate Similarity	NPC243381
0.743	Intermediate Similarity	NPC275292
0.7427	Intermediate Similarity	NPC473320
0.7418	Intermediate Similarity	NPC204565
0.7416	Intermediate Similarity	NPC176199
0.7416	Intermediate Similarity	NPC283219
0.7416	Intermediate Similarity	NPC11126
0.7416	Intermediate Similarity	NPC215795
0.7416	Intermediate Similarity	NPC213468
0.7416	Intermediate Similarity	NPC270009
0.7405	Intermediate Similarity	NPC82295
0.7405	Intermediate Similarity	NPC179365
0.7403	Intermediate Similarity	NPC15102
0.7391	Intermediate Similarity	NPC125746
0.7389	Intermediate Similarity	NPC472108
0.7389	Intermediate Similarity	NPC139291
0.7389	Intermediate Similarity	NPC19679
0.7389	Intermediate Similarity	NPC163055
0.7386	Intermediate Similarity	NPC313791
0.7377	Intermediate Similarity	NPC173028
0.7377	Intermediate Similarity	NPC65215
0.7374	Intermediate Similarity	NPC300688
0.7368	Intermediate Similarity	NPC56765
0.7368	Intermediate Similarity	NPC221786
0.7368	Intermediate Similarity	NPC206819
0.7368	Intermediate Similarity	NPC318065
0.7368	Intermediate Similarity	NPC475990
0.7368	Intermediate Similarity	NPC474880
0.7368	Intermediate Similarity	NPC41257
0.7363	Intermediate Similarity	NPC235684
0.7362	Intermediate Similarity	NPC230002
0.736	Intermediate Similarity	NPC14113
0.736	Intermediate Similarity	NPC145885
0.736	Intermediate Similarity	NPC84827

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 NPC109447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	615
0.2-0.3	1203
0.3-0.4	1782
0.4-0.5	2950
0.5-0.6	1853
0.6-0.7	448
0.7-0.8	62
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
0.7988	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD4462	Approved
0.7963	Intermediate Similarity	NPD4463	Approved
0.7848	Intermediate Similarity	NPD786	Approved
0.7811	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1183	Approved
0.7674	Intermediate Similarity	NPD1325	Approved
0.7674	Intermediate Similarity	NPD1326	Approved
0.7658	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1722	Approved
0.7614	Intermediate Similarity	NPD4076	Approved
0.7614	Intermediate Similarity	NPD4079	Approved
0.7571	Intermediate Similarity	NPD6595	Phase 3
0.7557	Intermediate Similarity	NPD3506	Approved
0.7557	Intermediate Similarity	NPD3505	Approved
0.7557	Intermediate Similarity	NPD2144	Approved
0.7546	Intermediate Similarity	NPD5254	Discontinued
0.7543	Intermediate Similarity	NPD5065	Approved
0.7531	Intermediate Similarity	NPD1592	Phase 3
0.7528	Intermediate Similarity	NPD3038	Discontinued
0.7514	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3100	Discontinued
0.7453	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD482	Approved
0.7425	Intermediate Similarity	NPD2172	Phase 1
0.7416	Intermediate Similarity	NPD8386	Phase 2
0.7414	Intermediate Similarity	NPD5021	Discontinued
0.7403	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3654	Approved
0.7389	Intermediate Similarity	NPD2092	Phase 2
0.7389	Intermediate Similarity	NPD2094	Phase 2
0.7389	Intermediate Similarity	NPD2095	Phase 2
0.7377	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD2091	Phase 2
0.7348	Intermediate Similarity	NPD2096	Phase 2
0.7341	Intermediate Similarity	NPD5138	Approved
0.7341	Intermediate Similarity	NPD5140	Approved
0.7322	Intermediate Similarity	NPD8431	Approved
0.7283	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4181	Approved
0.7247	Intermediate Similarity	NPD4128	Approved
0.7246	Intermediate Similarity	NPD1683	Approved
0.7241	Intermediate Similarity	NPD3323	Discontinued
0.7228	Intermediate Similarity	NPD3961	Discontinued
0.7228	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3835	Phase 3
0.7219	Intermediate Similarity	NPD3833	Phase 3
0.7207	Intermediate Similarity	NPD4075	Phase 2
0.7205	Intermediate Similarity	NPD3385	Approved
0.7195	Intermediate Similarity	NPD2069	Approved
0.7195	Intermediate Similarity	NPD2070	Approved
0.7195	Intermediate Similarity	NPD2071	Approved
0.7195	Intermediate Similarity	NPD2068	Approved
0.7191	Intermediate Similarity	NPD750	Phase 2
0.7178	Intermediate Similarity	NPD1262	Discovery
0.7135	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2837	Discontinued
0.7126	Intermediate Similarity	NPD1404	Approved
0.7126	Intermediate Similarity	NPD1403	Approved
0.712	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2641	Approved
0.7119	Intermediate Similarity	NPD4638	Approved
0.7119	Intermediate Similarity	NPD4639	Approved
0.7119	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2640	Approved
0.7119	Intermediate Similarity	NPD4640	Approved
0.7111	Intermediate Similarity	NPD2380	Approved
0.7111	Intermediate Similarity	NPD2381	Approved
0.7111	Intermediate Similarity	NPD2382	Approved
0.711	Intermediate Similarity	NPD4326	Phase 2
0.7076	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6158	Phase 2
0.7062	Intermediate Similarity	NPD2639	Approved
0.7062	Intermediate Similarity	NPD2642	Approved
0.7039	Intermediate Similarity	NPD3609	Approved
0.7039	Intermediate Similarity	NPD3610	Approved
0.7024	Intermediate Similarity	NPD7716	Approved
0.7024	Intermediate Similarity	NPD7717	Approved
0.7021	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5596	Phase 2
0.7006	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4703	Approved
0.7	Intermediate Similarity	NPD4702	Approved
0.6979	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2882	Phase 1
0.6971	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD8272	Phase 2
0.6927	Remote Similarity	NPD2844	Phase 3
0.6927	Remote Similarity	NPD7948	Phase 1
0.6923	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7619	Phase 3
0.6911	Remote Similarity	NPD7618	Phase 3
0.6902	Remote Similarity	NPD5473	Discontinued
0.6898	Remote Similarity	NPD6217	Discontinued
0.6888	Remote Similarity	NPD6991	Approved
0.6888	Remote Similarity	NPD8072	Approved
0.6882	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4499	Approved
0.6869	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2150	Discontinued
0.6851	Remote Similarity	NPD3116	Approved
0.6851	Remote Similarity	NPD3117	Approved
0.6851	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4880	Discontinued
0.6837	Remote Similarity	NPD8073	Approved
0.6833	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1995	Approved
0.6829	Remote Similarity	NPD1993	Approved
0.6829	Remote Similarity	NPD1994	Approved
0.6828	Remote Similarity	NPD3320	Approved
0.6828	Remote Similarity	NPD3318	Approved
0.6828	Remote Similarity	NPD3319	Phase 1
0.6821	Remote Similarity	NPD4601	Approved
0.6821	Remote Similarity	NPD4600	Approved
0.6818	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7957	Phase 1
0.6816	Remote Similarity	NPD2915	Discontinued
0.6809	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5020	Approved
0.68	Remote Similarity	NPD4520	Approved
0.6798	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8322	Phase 2
0.6774	Remote Similarity	NPD4399	Phase 2
0.6771	Remote Similarity	NPD1038	Approved
0.6766	Remote Similarity	NPD6554	Approved
0.6766	Remote Similarity	NPD45	Approved
0.6765	Remote Similarity	NPD4047	Discontinued
0.6765	Remote Similarity	NPD3717	Discontinued
0.6761	Remote Similarity	NPD2580	Discontinued
0.6754	Remote Similarity	NPD5913	Phase 3
0.6754	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6664	Approved
0.675	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7671	Approved
0.675	Remote Similarity	NPD7672	Approved
0.6744	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5106	Approved
0.6738	Remote Similarity	NPD5105	Approved
0.6737	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD3003	Approved
0.6733	Remote Similarity	NPD7470	Discontinued
0.6728	Remote Similarity	NPD2119	Approved
0.6728	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD991	Phase 2
0.6728	Remote Similarity	NPD2118	Approved
0.672	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3404	Approved
0.6707	Remote Similarity	NPD1254	Approved
0.6707	Remote Similarity	NPD3476	Approved
0.6707	Remote Similarity	NPD1253	Approved
0.6707	Remote Similarity	NPD1256	Approved
0.6707	Remote Similarity	NPD1255	Approved
0.6707	Remote Similarity	NPD3475	Approved
0.6705	Remote Similarity	NPD1661	Suspended
0.6705	Remote Similarity	NPD4547	Phase 3
0.6701	Remote Similarity	NPD4511	Phase 1
0.6689	Remote Similarity	NPD1108	Approved
0.6689	Remote Similarity	NPD1107	Approved
0.6685	Remote Similarity	NPD6492	Phase 2
0.6685	Remote Similarity	NPD5255	Approved
0.6684	Remote Similarity	NPD1768	Approved
0.6684	Remote Similarity	NPD802	Phase 2
0.6684	Remote Similarity	NPD2383	Phase 1
0.6684	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2006	Phase 2
0.6667	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2430	Phase 2
0.6667	Remote Similarity	NPD6828	Phase 2
0.6667	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5003	Discontinued
0.665	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.665	Remote Similarity	NPD484	Approved
0.665	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD947	Approved
0.6632	Remote Similarity	NPD4615	Phase 2
0.6631	Remote Similarity	NPD5899	Approved
0.6631	Remote Similarity	NPD5897	Approved
0.6631	Remote Similarity	NPD6452	Discontinued
0.6631	Remote Similarity	NPD5898	Approved
0.663	Remote Similarity	NPD509	Phase 3
0.6618	Remote Similarity	NPD8093	Discontinued
0.6616	Remote Similarity	NPD7903	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