NPASS Compound

Structure

NPC64055 OpenBabel07101718222D 24 25 0 0 1 0 0 0 0 0999 V2000 -1.8541 7.3244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5014 6.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5306 4.3518 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 -2.2142 5.6302 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 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5232 6.5812 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 2.6831 1.3090 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 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8833 4.8870 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 -2.5743 3.9360 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 3.5491 -0.1910 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 -3.8615 5.0949 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 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 -3.2435 3.1928 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 22 1 0 0 0 0 6 9 1 0 0 0 0 7 11 1 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 10 11 1 0 0 0 0 10 16 2 0 0 0 0 11 14 2 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 23 1 0 0 0 0 15 6 1 1 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 23 1 0 0 0 0 17 22 2 3 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.93
Volume:	371.924
LogP:	4.686
LogD:	4.123
LogS:	-5.116
# Rotatable Bonds:	8
TPSA:	56.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	3.223
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.894
MDCK Permeability:	1.6596535715507343e-05
Pgp-inhibitor:	0.397
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.802
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	96.77820587158203%
Volume Distribution (VD):	1.93
Pgp-substrate:	4.411960601806641%

ADMET: Metabolism

CYP1A2-inhibitor:	0.88
CYP1A2-substrate:	0.682
CYP2C19-inhibitor:	0.892
CYP2C19-substrate:	0.473
CYP2C9-inhibitor:	0.588
CYP2C9-substrate:	0.684
CYP2D6-inhibitor:	0.82
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	2.307
Half-life (T1/2):	0.19

ADMET: Toxicity

hERG Blockers:	0.744
Human Hepatotoxicity (H-HT):	0.284
Drug-inuced Liver Injury (DILI):	0.307
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.487
Carcinogencity:	0.212
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC64055

Natural Product ID:	NPC64055
*Common Name:**	Altematamide B
IUPAC Name:	(2S)-4-methyl-2-(methylamino)-N-[2-(2,5,6-tribromo-1H-indol-3-yl)ethyl]pentanamide
Synonyms:
Standard InCHIKey:	PDSLVIZPXNGMCO-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C17H22Br3N3O/c1-9(2)6-15(21-3)17(24)22-5-4-10-11-7-12(18)13(19)8-14(11)23-16(10)20/h7-9,15,21,23H,4-6H2,1-3H3,(H,22,24)/t15-/m0/s1
SMILES:	CC(C)C[C@@H](C(=NCCc1c2cc(c(cc2[nH]c1Br)Br)Br)O)NC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446275
PubChem CID:	10052501
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[546580]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	4.0	ug.mL-1	PMID[546580]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[546580]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[546580]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	4.0	ug.mL-1	PMID[546580]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	4.0	ug.mL-1	PMID[546580]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[546580]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	4.0	ug.mL-1	PMID[546581]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	4.0	ug.mL-1	PMID[546581]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[546581]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[546581]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	4.0	ug.mL-1	PMID[546581]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[546581]

☑ 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 NPC64055 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	495
0.1-0.2	9497
0.2-0.3	21830
0.3-0.4	5166
0.4-0.5	2967
0.5-0.6	1725
0.6-0.7	812
0.7-0.8	196
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC288074
0.949	High Similarity	NPC109447
0.8537	High Similarity	NPC149265
0.8491	Intermediate Similarity	NPC2272
0.811	Intermediate Similarity	NPC141926
0.8081	Intermediate Similarity	NPC280297
0.8061	Intermediate Similarity	NPC34844
0.7956	Intermediate Similarity	NPC477166
0.7956	Intermediate Similarity	NPC477167
0.7956	Intermediate Similarity	NPC473342
0.7956	Intermediate Similarity	NPC304187
0.7882	Intermediate Similarity	NPC247987
0.788	Intermediate Similarity	NPC262898
0.7829	Intermediate Similarity	NPC474958
0.7826	Intermediate Similarity	NPC179701
0.7816	Intermediate Similarity	NPC477611
0.7807	Intermediate Similarity	NPC52909
0.7807	Intermediate Similarity	NPC94211
0.7807	Intermediate Similarity	NPC475935
0.7805	Intermediate Similarity	NPC316069
0.7802	Intermediate Similarity	NPC243716
0.7784	Intermediate Similarity	NPC469765
0.7784	Intermediate Similarity	NPC259644
0.7784	Intermediate Similarity	NPC469786
0.7784	Intermediate Similarity	NPC469760
0.7784	Intermediate Similarity	NPC73952
0.7784	Intermediate Similarity	NPC25008
0.7784	Intermediate Similarity	NPC232798
0.7784	Intermediate Similarity	NPC469763
0.7754	Intermediate Similarity	NPC303820
0.7754	Intermediate Similarity	NPC106771
0.7754	Intermediate Similarity	NPC23420
0.7754	Intermediate Similarity	NPC205254
0.7744	Intermediate Similarity	NPC314372
0.7738	Intermediate Similarity	NPC75540
0.7738	Intermediate Similarity	NPC70922
0.7738	Intermediate Similarity	NPC80597
0.7738	Intermediate Similarity	NPC212376
0.7738	Intermediate Similarity	NPC211572
0.7727	Intermediate Similarity	NPC121903
0.7711	Intermediate Similarity	NPC37548
0.7692	Intermediate Similarity	NPC285469
0.7688	Intermediate Similarity	NPC49954
0.7688	Intermediate Similarity	NPC160105
0.7688	Intermediate Similarity	NPC474561
0.763	Intermediate Similarity	NPC17751
0.763	Intermediate Similarity	NPC280864
0.7622	Intermediate Similarity	NPC190296
0.7588	Intermediate Similarity	NPC469785
0.756	Intermediate Similarity	NPC24678
0.756	Intermediate Similarity	NPC105818
0.7557	Intermediate Similarity	NPC82331
0.7544	Intermediate Similarity	NPC469762
0.7542	Intermediate Similarity	NPC276540
0.7542	Intermediate Similarity	NPC233050
0.7529	Intermediate Similarity	NPC470507
0.7529	Intermediate Similarity	NPC38736
0.7529	Intermediate Similarity	NPC274229
0.7514	Intermediate Similarity	NPC16667
0.7514	Intermediate Similarity	NPC314603
0.7514	Intermediate Similarity	NPC282231
0.75	Intermediate Similarity	NPC187951
0.7471	Intermediate Similarity	NPC311276
0.747	Intermediate Similarity	NPC242556
0.7469	Intermediate Similarity	NPC325252
0.7469	Intermediate Similarity	NPC218268
0.7459	Intermediate Similarity	NPC275292
0.7459	Intermediate Similarity	NPC243381
0.7457	Intermediate Similarity	NPC279918
0.7455	Intermediate Similarity	NPC63157
0.7455	Intermediate Similarity	NPC473868
0.7443	Intermediate Similarity	NPC63751
0.7427	Intermediate Similarity	NPC207726
0.7425	Intermediate Similarity	NPC159856
0.7401	Intermediate Similarity	NPC97343
0.7394	Intermediate Similarity	NPC469780
0.7394	Intermediate Similarity	NPC469768
0.7394	Intermediate Similarity	NPC469779
0.7394	Intermediate Similarity	NPC469761
0.7394	Intermediate Similarity	NPC469784
0.7394	Intermediate Similarity	NPC469783
0.7394	Intermediate Similarity	NPC469767
0.7394	Intermediate Similarity	NPC59084
0.7384	Intermediate Similarity	NPC141353
0.7375	Intermediate Similarity	NPC22079
0.7371	Intermediate Similarity	NPC194640
0.7371	Intermediate Similarity	NPC40779
0.7363	Intermediate Similarity	NPC307191
0.7363	Intermediate Similarity	NPC233936
0.7349	Intermediate Similarity	NPC469766
0.7345	Intermediate Similarity	NPC317430
0.7345	Intermediate Similarity	NPC201700
0.7337	Intermediate Similarity	NPC471957
0.7333	Intermediate Similarity	NPC73767
0.7323	Intermediate Similarity	NPC207020
0.732	Intermediate Similarity	NPC470505
0.7318	Intermediate Similarity	NPC472123
0.7317	Intermediate Similarity	NPC84911
0.7303	Intermediate Similarity	NPC194411
0.7303	Intermediate Similarity	NPC280548
0.7301	Intermediate Similarity	NPC198988
0.7299	Intermediate Similarity	NPC67056
0.7299	Intermediate Similarity	NPC6436
0.7294	Intermediate Similarity	NPC124005
0.7289	Intermediate Similarity	NPC2949
0.7288	Intermediate Similarity	NPC54988
0.7283	Intermediate Similarity	NPC228835
0.7278	Intermediate Similarity	NPC329688
0.7278	Intermediate Similarity	NPC189812
0.7257	Intermediate Similarity	NPC131718
0.7256	Intermediate Similarity	NPC29886
0.7256	Intermediate Similarity	NPC261195
0.7256	Intermediate Similarity	NPC96102
0.7249	Intermediate Similarity	NPC88315
0.7235	Intermediate Similarity	NPC21605
0.7232	Intermediate Similarity	NPC2165
0.7232	Intermediate Similarity	NPC195507
0.7229	Intermediate Similarity	NPC88097
0.7229	Intermediate Similarity	NPC110126
0.7225	Intermediate Similarity	NPC471458
0.7222	Intermediate Similarity	NPC34508
0.7222	Intermediate Similarity	NPC475450
0.7219	Intermediate Similarity	NPC470440
0.7213	Intermediate Similarity	NPC91179
0.7212	Intermediate Similarity	NPC105127
0.7204	Intermediate Similarity	NPC94752
0.72	Intermediate Similarity	NPC230869
0.72	Intermediate Similarity	NPC135141
0.72	Intermediate Similarity	NPC92796
0.7198	Intermediate Similarity	NPC59269
0.7198	Intermediate Similarity	NPC68354
0.7198	Intermediate Similarity	NPC248454
0.7197	Intermediate Similarity	NPC41174
0.7189	Intermediate Similarity	NPC110158
0.7189	Intermediate Similarity	NPC108011
0.7182	Intermediate Similarity	NPC37423
0.7182	Intermediate Similarity	NPC275305
0.7181	Intermediate Similarity	NPC231536
0.7167	Intermediate Similarity	NPC6982
0.7166	Intermediate Similarity	NPC317030
0.716	Intermediate Similarity	NPC475428
0.7158	Intermediate Similarity	NPC474180
0.7158	Intermediate Similarity	NPC126709
0.7158	Intermediate Similarity	NPC248041
0.7158	Intermediate Similarity	NPC188821
0.7158	Intermediate Similarity	NPC219336
0.7151	Intermediate Similarity	NPC33421
0.7151	Intermediate Similarity	NPC53947
0.7143	Intermediate Similarity	NPC267885
0.7143	Intermediate Similarity	NPC288785
0.7143	Intermediate Similarity	NPC299594
0.7135	Intermediate Similarity	NPC470508
0.7128	Intermediate Similarity	NPC473761
0.7128	Intermediate Similarity	NPC213629
0.7125	Intermediate Similarity	NPC250361
0.7118	Intermediate Similarity	NPC204141
0.7114	Intermediate Similarity	NPC477610
0.7113	Intermediate Similarity	NPC166209
0.7113	Intermediate Similarity	NPC13456
0.7113	Intermediate Similarity	NPC77241
0.7113	Intermediate Similarity	NPC269203
0.7112	Intermediate Similarity	NPC474707
0.711	Intermediate Similarity	NPC216713
0.7104	Intermediate Similarity	NPC15573
0.7104	Intermediate Similarity	NPC151939
0.7104	Intermediate Similarity	NPC183662
0.7104	Intermediate Similarity	NPC217372
0.7099	Intermediate Similarity	NPC473587
0.7098	Intermediate Similarity	NPC474389
0.7097	Intermediate Similarity	NPC472294
0.7095	Intermediate Similarity	NPC49217
0.7094	Intermediate Similarity	NPC477114
0.7088	Intermediate Similarity	NPC149155
0.7088	Intermediate Similarity	NPC110500
0.7088	Intermediate Similarity	NPC203468
0.7086	Intermediate Similarity	NPC184476
0.7083	Intermediate Similarity	NPC115611
0.7083	Intermediate Similarity	NPC222018
0.7083	Intermediate Similarity	NPC279081
0.7079	Intermediate Similarity	NPC271797
0.7079	Intermediate Similarity	NPC472587
0.7079	Intermediate Similarity	NPC21174
0.7079	Intermediate Similarity	NPC102423
0.7076	Intermediate Similarity	NPC129042
0.7074	Intermediate Similarity	NPC204565
0.7069	Intermediate Similarity	NPC200214
0.7065	Intermediate Similarity	NPC213468
0.7065	Intermediate Similarity	NPC215795
0.7065	Intermediate Similarity	NPC176199
0.7065	Intermediate Similarity	NPC283219
0.7065	Intermediate Similarity	NPC11126
0.7065	Intermediate Similarity	NPC270009
0.7062	Intermediate Similarity	NPC474318
0.7062	Intermediate Similarity	NPC153123
0.7062	Intermediate Similarity	NPC477004
0.7062	Intermediate Similarity	NPC201266
0.7062	Intermediate Similarity	NPC237414
0.7062	Intermediate Similarity	NPC268744
0.7062	Intermediate Similarity	NPC475914
0.7062	Intermediate Similarity	NPC220797

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 NPC64055 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	698
0.2-0.3	1326
0.3-0.4	2151
0.4-0.5	2989
0.5-0.6	1445
0.6-0.7	272
0.7-0.8	21
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
0.76	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4462	Approved
0.756	Intermediate Similarity	NPD4463	Approved
0.7439	Intermediate Similarity	NPD786	Approved
0.7429	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1326	Approved
0.7303	Intermediate Similarity	NPD1325	Approved
0.7294	Intermediate Similarity	NPD1183	Approved
0.7293	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4076	Approved
0.7253	Intermediate Similarity	NPD4079	Approved
0.7246	Intermediate Similarity	NPD1722	Approved
0.7213	Intermediate Similarity	NPD6595	Phase 3
0.7198	Intermediate Similarity	NPD2144	Approved
0.7198	Intermediate Similarity	NPD3505	Approved
0.7198	Intermediate Similarity	NPD3506	Approved
0.7182	Intermediate Similarity	NPD5065	Approved
0.7174	Intermediate Similarity	NPD3038	Discontinued
0.716	Intermediate Similarity	NPD5254	Discontinued
0.7151	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1592	Phase 3
0.7135	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3100	Discontinued
0.7088	Intermediate Similarity	NPD482	Approved
0.7066	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8386	Phase 2
0.7059	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5021	Discontinued
0.7052	Intermediate Similarity	NPD2172	Phase 1
0.7049	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD2095	Phase 2
0.7043	Intermediate Similarity	NPD2092	Phase 2
0.7043	Intermediate Similarity	NPD2094	Phase 2
0.7037	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2071	Approved
0.7024	Intermediate Similarity	NPD2070	Approved
0.7024	Intermediate Similarity	NPD2069	Approved
0.7024	Intermediate Similarity	NPD2068	Approved
0.7005	Intermediate Similarity	NPD2091	Phase 2
0.7005	Intermediate Similarity	NPD2096	Phase 2
0.6994	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3654	Approved
0.6984	Remote Similarity	NPD8431	Approved
0.6983	Remote Similarity	NPD5140	Approved
0.6983	Remote Similarity	NPD5138	Approved
0.6927	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4181	Approved
0.6902	Remote Similarity	NPD4128	Approved
0.6895	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3961	Discontinued
0.6889	Remote Similarity	NPD3323	Discontinued
0.6879	Remote Similarity	NPD1683	Approved
0.6865	Remote Similarity	NPD4075	Phase 2
0.6857	Remote Similarity	NPD3833	Phase 3
0.6857	Remote Similarity	NPD3835	Phase 3
0.6848	Remote Similarity	NPD750	Phase 2
0.6832	Remote Similarity	NPD4520	Approved
0.6826	Remote Similarity	NPD3385	Approved
0.6806	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1262	Discovery
0.6802	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2837	Discontinued
0.6778	Remote Similarity	NPD1403	Approved
0.6778	Remote Similarity	NPD1404	Approved
0.6776	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4639	Approved
0.6776	Remote Similarity	NPD4640	Approved
0.6776	Remote Similarity	NPD4638	Approved
0.6776	Remote Similarity	NPD2640	Approved
0.6776	Remote Similarity	NPD2641	Approved
0.6774	Remote Similarity	NPD2382	Approved
0.6774	Remote Similarity	NPD2380	Approved
0.6774	Remote Similarity	NPD2381	Approved
0.676	Remote Similarity	NPD4326	Phase 2
0.673	Remote Similarity	NPD7717	Approved
0.673	Remote Similarity	NPD7716	Approved
0.6723	Remote Similarity	NPD6158	Phase 2
0.6723	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2642	Approved
0.6721	Remote Similarity	NPD2639	Approved
0.6703	Remote Similarity	NPD3610	Approved
0.6703	Remote Similarity	NPD3609	Approved
0.6701	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5596	Phase 2
0.6667	Remote Similarity	NPD1995	Approved
0.6667	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1994	Approved
0.6667	Remote Similarity	NPD1993	Approved
0.6667	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4702	Approved
0.6648	Remote Similarity	NPD4703	Approved
0.6647	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD8272	Phase 2
0.663	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD2882	Phase 1
0.6616	Remote Similarity	NPD7948	Phase 1
0.6599	Remote Similarity	NPD7619	Phase 3
0.6599	Remote Similarity	NPD7618	Phase 3
0.6596	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD2844	Phase 3
0.6584	Remote Similarity	NPD6991	Approved
0.6584	Remote Similarity	NPD8072	Approved
0.658	Remote Similarity	NPD6217	Discontinued
0.6579	Remote Similarity	NPD5473	Discontinued
0.6575	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4499	Approved
0.6562	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8073	Approved
0.6524	Remote Similarity	NPD3116	Approved
0.6524	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3117	Approved
0.652	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7957	Phase 1
0.6519	Remote Similarity	NPD2150	Discontinued
0.6517	Remote Similarity	NPD4600	Approved
0.6517	Remote Similarity	NPD4601	Approved
0.651	Remote Similarity	NPD3318	Approved
0.651	Remote Similarity	NPD3320	Approved
0.651	Remote Similarity	NPD3319	Phase 1
0.6505	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4880	Discontinued
0.6488	Remote Similarity	NPD8322	Phase 2
0.6486	Remote Similarity	NPD2915	Discontinued
0.6482	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD1038	Approved
0.6458	Remote Similarity	NPD4399	Phase 2
0.6457	Remote Similarity	NPD5020	Approved
0.6456	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7672	Approved
0.6456	Remote Similarity	NPD7671	Approved
0.6453	Remote Similarity	NPD5495	Phase 2
0.645	Remote Similarity	NPD6664	Approved
0.6447	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5913	Phase 3
0.6442	Remote Similarity	NPD7470	Discontinued
0.6439	Remote Similarity	NPD3003	Approved
0.6429	Remote Similarity	NPD2580	Discontinued
0.6429	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5105	Approved
0.6425	Remote Similarity	NPD5106	Approved
0.642	Remote Similarity	NPD3717	Discontinued
0.642	Remote Similarity	NPD4047	Discontinued
0.6416	Remote Similarity	NPD6554	Approved
0.6416	Remote Similarity	NPD45	Approved
0.6414	Remote Similarity	NPD3404	Approved
0.6406	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4511	Phase 1
0.6394	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD1768	Approved
0.6382	Remote Similarity	NPD802	Phase 2
0.6378	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD2383	Phase 1
0.6369	Remote Similarity	NPD2118	Approved
0.6369	Remote Similarity	NPD991	Phase 2
0.6369	Remote Similarity	NPD1661	Suspended
0.6369	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4547	Phase 3
0.6369	Remote Similarity	NPD2119	Approved
0.6368	Remote Similarity	NPD6492	Phase 2
0.6368	Remote Similarity	NPD5003	Discontinued
0.6364	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5255	Approved
0.6359	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1253	Approved
0.6358	Remote Similarity	NPD1254	Approved
0.6358	Remote Similarity	NPD1255	Approved
0.6358	Remote Similarity	NPD1256	Approved
0.6355	Remote Similarity	NPD484	Approved
0.6353	Remote Similarity	NPD3476	Approved
0.6353	Remote Similarity	NPD3475	Approved
0.635	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6828	Phase 2
0.6349	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8093	Discontinued
0.6333	Remote Similarity	NPD2430	Phase 2
0.6332	Remote Similarity	NPD4615	Phase 2
0.6328	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD2006	Phase 2
0.6324	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6452	Discontinued
0.6321	Remote Similarity	NPD5897	Approved
0.6321	Remote Similarity	NPD5899	Approved
0.6321	Remote Similarity	NPD5898	Approved
0.6319	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD4890	Phase 2

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