NPASS Compound

Structure

NPC288074 OpenBabel07101718312D 25 26 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 -0.9511 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 -2.8833 4.8870 0.0000 C 0 0 1 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 -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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 22 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 23 1 0 0 0 0 7 10 1 0 0 0 0 8 12 1 0 0 0 0 8 13 2 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 11 12 1 0 0 0 0 11 17 2 0 0 0 0 12 16 2 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 7 1 1 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 18 23 2 3 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.95
Volume:	389.22
LogP:	5.033
LogD:	4.257
LogS:	-5.952
# Rotatable Bonds:	8
TPSA:	46.06
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.535
Synthetic Accessibility Score:	3.314
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
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:	-4.819
MDCK Permeability:	1.9193472326151095e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.807
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997
Plasma Protein Binding (PPB):	96.21700286865234%
Volume Distribution (VD):	2.321
Pgp-substrate:	4.776148796081543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.879
CYP1A2-substrate:	0.812
CYP2C19-inhibitor:	0.916
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.622
CYP2C9-substrate:	0.671
CYP2D6-inhibitor:	0.926
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.869
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	3.31
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.686
Human Hepatotoxicity (H-HT):	0.422
Drug-inuced Liver Injury (DILI):	0.395
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.68
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.507
Carcinogencity:	0.106
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC288074

Natural Product ID:	NPC288074
*Common Name:**	Altematamide A
IUPAC Name:	(2S)-4-methyl-2-(methylamino)-N-[2-(2,5,6-tribromo-1-methylindol-3-yl)ethyl]pentanamide
Synonyms:
Standard InCHIKey:	KHRZQNJMQDSRQY-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C18H24Br3N3O/c1-10(2)7-15(22-3)18(25)23-6-5-11-12-8-13(19)14(20)9-16(12)24(4)17(11)21/h8-10,15,22H,5-7H2,1-4H3,(H,23,25)/t15-/m0/s1
SMILES:	CN[C@H](C(=NCCc1c(Br)n(c2c1cc(Br)c(c2)Br)C)O)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518674
PubChem CID:	10075903
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
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[533704]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	4.0	ug.mL-1	PMID[533704]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	4.0	ug.mL-1	PMID[533704]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[533704]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[533704]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	4.0	ug.mL-1	PMID[533704]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	4.0	ug.mL-1	PMID[533704]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	4.0	ug.mL-1	PMID[533705]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	4.0	ug.mL-1	PMID[533705]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[533705]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[533705]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	4.0	ug.mL-1	PMID[533705]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[533705]

☑ 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 NPC288074 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	492
0.1-0.2	9472
0.2-0.3	21775
0.3-0.4	5145
0.4-0.5	3029
0.5-0.6	1865
0.6-0.7	791
0.7-0.8	120
0.8-0.85	5
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	NPC64055
0.9125	High Similarity	NPC109447
0.8424	Intermediate Similarity	NPC149265
0.8148	Intermediate Similarity	NPC2272
0.8035	Intermediate Similarity	NPC121903
0.7952	Intermediate Similarity	NPC34844
0.7892	Intermediate Similarity	NPC141926
0.7874	Intermediate Similarity	NPC280297
0.7784	Intermediate Similarity	NPC262898
0.776	Intermediate Similarity	NPC477167
0.776	Intermediate Similarity	NPC304187
0.776	Intermediate Similarity	NPC473342
0.776	Intermediate Similarity	NPC477166
0.773	Intermediate Similarity	NPC179701
0.7627	Intermediate Similarity	NPC474958
0.7619	Intermediate Similarity	NPC94211
0.7619	Intermediate Similarity	NPC475935
0.7619	Intermediate Similarity	NPC52909
0.7614	Intermediate Similarity	NPC477611
0.7609	Intermediate Similarity	NPC243716
0.759	Intermediate Similarity	NPC316069
0.7574	Intermediate Similarity	NPC259644
0.7574	Intermediate Similarity	NPC469786
0.7574	Intermediate Similarity	NPC469760
0.7574	Intermediate Similarity	NPC469763
0.7574	Intermediate Similarity	NPC73952
0.7574	Intermediate Similarity	NPC469765
0.7574	Intermediate Similarity	NPC25008
0.7572	Intermediate Similarity	NPC247987
0.7566	Intermediate Similarity	NPC23420
0.7566	Intermediate Similarity	NPC106771
0.7566	Intermediate Similarity	NPC303820
0.7566	Intermediate Similarity	NPC205254
0.753	Intermediate Similarity	NPC314372
0.7529	Intermediate Similarity	NPC80597
0.7529	Intermediate Similarity	NPC2165
0.7529	Intermediate Similarity	NPC212376
0.7529	Intermediate Similarity	NPC195507
0.7529	Intermediate Similarity	NPC70922
0.7529	Intermediate Similarity	NPC211572
0.7529	Intermediate Similarity	NPC75540
0.7486	Intermediate Similarity	NPC474561
0.7486	Intermediate Similarity	NPC160105
0.7486	Intermediate Similarity	NPC49954
0.7471	Intermediate Similarity	NPC232798
0.7458	Intermediate Similarity	NPC82331
0.7429	Intermediate Similarity	NPC280864
0.7429	Intermediate Similarity	NPC17751
0.741	Intermediate Similarity	NPC190296
0.7399	Intermediate Similarity	NPC6436
0.7396	Intermediate Similarity	NPC37548
0.7384	Intermediate Similarity	NPC469785
0.7384	Intermediate Similarity	NPC285469
0.7353	Intermediate Similarity	NPC105818
0.7353	Intermediate Similarity	NPC24678
0.7348	Intermediate Similarity	NPC276540
0.7348	Intermediate Similarity	NPC233050
0.7341	Intermediate Similarity	NPC469762
0.733	Intermediate Similarity	NPC274229
0.7318	Intermediate Similarity	NPC314603
0.7314	Intermediate Similarity	NPC282231
0.7283	Intermediate Similarity	NPC108011
0.7273	Intermediate Similarity	NPC311276
0.7268	Intermediate Similarity	NPC233936
0.7268	Intermediate Similarity	NPC275292
0.7268	Intermediate Similarity	NPC243381
0.7257	Intermediate Similarity	NPC279918
0.7247	Intermediate Similarity	NPC63751
0.7246	Intermediate Similarity	NPC63157
0.7246	Intermediate Similarity	NPC473868
0.7229	Intermediate Similarity	NPC316811
0.7229	Intermediate Similarity	NPC73767
0.7225	Intermediate Similarity	NPC38736
0.7225	Intermediate Similarity	NPC470507
0.7219	Intermediate Similarity	NPC159856
0.7216	Intermediate Similarity	NPC16667
0.7207	Intermediate Similarity	NPC194411
0.7207	Intermediate Similarity	NPC97343
0.7193	Intermediate Similarity	NPC187951
0.7189	Intermediate Similarity	NPC228835
0.7186	Intermediate Similarity	NPC469767
0.7186	Intermediate Similarity	NPC59084
0.7186	Intermediate Similarity	NPC469761
0.7186	Intermediate Similarity	NPC469783
0.7186	Intermediate Similarity	NPC469779
0.7186	Intermediate Similarity	NPC469784
0.7186	Intermediate Similarity	NPC469768
0.7186	Intermediate Similarity	NPC469780
0.7175	Intermediate Similarity	NPC40779
0.7175	Intermediate Similarity	NPC194640
0.7174	Intermediate Similarity	NPC307191
0.716	Intermediate Similarity	NPC242556
0.7152	Intermediate Similarity	NPC218268
0.7152	Intermediate Similarity	NPC325252
0.7151	Intermediate Similarity	NPC201700
0.7151	Intermediate Similarity	NPC317430
0.715	Intermediate Similarity	NPC207020
0.7143	Intermediate Similarity	NPC470505
0.7143	Intermediate Similarity	NPC469766
0.7135	Intermediate Similarity	NPC471957
0.7135	Intermediate Similarity	NPC472109
0.7135	Intermediate Similarity	NPC472110
0.7127	Intermediate Similarity	NPC472123
0.7126	Intermediate Similarity	NPC104483
0.7126	Intermediate Similarity	NPC207726
0.7126	Intermediate Similarity	NPC110126
0.7112	Intermediate Similarity	NPC94752
0.7108	Intermediate Similarity	NPC84911
0.7104	Intermediate Similarity	NPC68354
0.7095	Intermediate Similarity	NPC54988
0.7091	Intermediate Similarity	NPC198988
0.709	Intermediate Similarity	NPC231536
0.7088	Intermediate Similarity	NPC329688
0.7088	Intermediate Similarity	NPC37423
0.7088	Intermediate Similarity	NPC275305
0.7088	Intermediate Similarity	NPC189812
0.7086	Intermediate Similarity	NPC141353
0.7083	Intermediate Similarity	NPC2949
0.7068	Intermediate Similarity	NPC88315
0.7068	Intermediate Similarity	NPC188821
0.7068	Intermediate Similarity	NPC474180
0.7062	Intermediate Similarity	NPC131718
0.7055	Intermediate Similarity	NPC22079
0.7048	Intermediate Similarity	NPC96102
0.7048	Intermediate Similarity	NPC261195
0.7048	Intermediate Similarity	NPC29886
0.7045	Intermediate Similarity	NPC129721
0.7037	Intermediate Similarity	NPC213629
0.7035	Intermediate Similarity	NPC21605
0.7027	Intermediate Similarity	NPC91179
0.7024	Intermediate Similarity	NPC88097
0.7021	Intermediate Similarity	NPC474707
0.7018	Intermediate Similarity	NPC470440
0.7017	Intermediate Similarity	NPC280548
0.7011	Intermediate Similarity	NPC248454
0.7011	Intermediate Similarity	NPC59269
0.701	Intermediate Similarity	NPC474389
0.7006	Intermediate Similarity	NPC230869
0.7006	Intermediate Similarity	NPC67056
0.7006	Intermediate Similarity	NPC150259
0.7006	Intermediate Similarity	NPC92796
0.7006	Intermediate Similarity	NPC135141
0.7006	Intermediate Similarity	NPC105127
0.7005	Intermediate Similarity	NPC110158
0.7	Intermediate Similarity	NPC49217
0.6994	Remote Similarity	NPC124005
0.6984	Remote Similarity	NPC317030
0.6984	Remote Similarity	NPC204565
0.6973	Remote Similarity	NPC176199
0.6973	Remote Similarity	NPC215795
0.6973	Remote Similarity	NPC11126
0.6973	Remote Similarity	NPC248041
0.6973	Remote Similarity	NPC126709
0.6971	Remote Similarity	NPC200214
0.6957	Remote Similarity	NPC267885
0.6954	Remote Similarity	NPC33421
0.6954	Remote Similarity	NPC473761
0.6954	Remote Similarity	NPC53947
0.6947	Remote Similarity	NPC65215
0.6947	Remote Similarity	NPC173028
0.6946	Remote Similarity	NPC477610
0.694	Remote Similarity	NPC34508
0.6939	Remote Similarity	NPC166209
0.6939	Remote Similarity	NPC77241
0.6939	Remote Similarity	NPC13456
0.6939	Remote Similarity	NPC269203
0.6932	Remote Similarity	NPC471458
0.6932	Remote Similarity	NPC476219
0.6932	Remote Similarity	NPC476297
0.6927	Remote Similarity	NPC477114
0.6919	Remote Similarity	NPC14113
0.6919	Remote Similarity	NPC84827
0.6919	Remote Similarity	NPC151939
0.6919	Remote Similarity	NPC145885
0.6915	Remote Similarity	NPC472294
0.6914	Remote Similarity	NPC216713
0.691	Remote Similarity	NPC318065
0.691	Remote Similarity	NPC206819
0.691	Remote Similarity	NPC56765
0.6909	Remote Similarity	NPC475450
0.6907	Remote Similarity	NPC222018
0.6902	Remote Similarity	NPC110500
0.6902	Remote Similarity	NPC149155
0.6902	Remote Similarity	NPC203468
0.6902	Remote Similarity	NPC469938
0.6901	Remote Similarity	NPC20144
0.6895	Remote Similarity	NPC17059
0.6893	Remote Similarity	NPC475736
0.6889	Remote Similarity	NPC271797
0.6889	Remote Similarity	NPC21174
0.6889	Remote Similarity	NPC102423
0.6888	Remote Similarity	NPC474318
0.6888	Remote Similarity	NPC201266
0.6888	Remote Similarity	NPC220797
0.6888	Remote Similarity	NPC477004
0.6888	Remote Similarity	NPC475914
0.6888	Remote Similarity	NPC153123
0.6888	Remote Similarity	NPC268744
0.6888	Remote Similarity	NPC237414
0.6885	Remote Similarity	NPC158129

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 NPC288074 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	674
0.2-0.3	1309
0.3-0.4	2072
0.4-0.5	2936
0.5-0.6	1606
0.6-0.7	291
0.7-0.8	15
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
0.741	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1183	Approved
0.7345	Intermediate Similarity	NPD5021	Discontinued
0.7312	Intermediate Similarity	NPD3654	Approved
0.7251	Intermediate Similarity	NPD4463	Approved
0.7251	Intermediate Similarity	NPD4462	Approved
0.7232	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2070	Approved
0.7229	Intermediate Similarity	NPD2071	Approved
0.7229	Intermediate Similarity	NPD2068	Approved
0.7229	Intermediate Similarity	NPD2069	Approved
0.7229	Intermediate Similarity	NPD786	Approved
0.7198	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1683	Approved
0.7158	Intermediate Similarity	NPD4079	Approved
0.7158	Intermediate Similarity	NPD4076	Approved
0.7134	Intermediate Similarity	NPD3385	Approved
0.7127	Intermediate Similarity	NPD750	Phase 2
0.7104	Intermediate Similarity	NPD3505	Approved
0.7104	Intermediate Similarity	NPD2144	Approved
0.7104	Intermediate Similarity	NPD3506	Approved
0.7088	Intermediate Similarity	NPD5065	Approved
0.7083	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3038	Discontinued
0.7066	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4638	Approved
0.7056	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4639	Approved
0.7056	Intermediate Similarity	NPD4640	Approved
0.7048	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4326	Phase 2
0.7041	Intermediate Similarity	NPD1722	Approved
0.7027	Intermediate Similarity	NPD6595	Phase 3
0.7017	Intermediate Similarity	NPD1326	Approved
0.7017	Intermediate Similarity	NPD1325	Approved
0.7	Intermediate Similarity	NPD4520	Approved
0.6994	Remote Similarity	NPD3100	Discontinued
0.6968	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5254	Discontinued
0.6952	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD482	Approved
0.6867	Remote Similarity	NPD1993	Approved
0.6867	Remote Similarity	NPD1995	Approved
0.6867	Remote Similarity	NPD1994	Approved
0.6865	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD2094	Phase 2
0.6862	Remote Similarity	NPD2095	Phase 2
0.6862	Remote Similarity	NPD2092	Phase 2
0.6859	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2172	Phase 1
0.6845	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1592	Phase 3
0.6839	Remote Similarity	NPD4703	Approved
0.6839	Remote Similarity	NPD4702	Approved
0.6828	Remote Similarity	NPD4181	Approved
0.6825	Remote Similarity	NPD2096	Phase 2
0.6825	Remote Similarity	NPD2091	Phase 2
0.6811	Remote Similarity	NPD4128	Approved
0.6806	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8431	Approved
0.6806	Remote Similarity	NPD3961	Discontinued
0.68	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2150	Discontinued
0.6796	Remote Similarity	NPD3323	Discontinued
0.6796	Remote Similarity	NPD5138	Approved
0.6796	Remote Similarity	NPD5140	Approved
0.6793	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8386	Phase 2
0.6776	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2382	Approved
0.6774	Remote Similarity	NPD2380	Approved
0.6774	Remote Similarity	NPD2381	Approved
0.6774	Remote Similarity	NPD4075	Phase 2
0.6723	Remote Similarity	NPD6158	Phase 2
0.6723	Remote Similarity	NPD2882	Phase 1
0.6723	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4399	Phase 2
0.6717	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6554	Approved
0.6706	Remote Similarity	NPD45	Approved
0.6705	Remote Similarity	NPD4047	Discontinued
0.6704	Remote Similarity	NPD2580	Discontinued
0.6703	Remote Similarity	NPD3117	Approved
0.6703	Remote Similarity	NPD3116	Approved
0.6685	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2641	Approved
0.6685	Remote Similarity	NPD2640	Approved
0.6685	Remote Similarity	NPD1403	Approved
0.6685	Remote Similarity	NPD2837	Discontinued
0.6685	Remote Similarity	NPD1404	Approved
0.6667	Remote Similarity	NPD6991	Approved
0.6667	Remote Similarity	NPD2915	Discontinued
0.6648	Remote Similarity	NPD4547	Phase 3
0.6648	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1253	Approved
0.6647	Remote Similarity	NPD1254	Approved
0.6647	Remote Similarity	NPD1256	Approved
0.6647	Remote Similarity	NPD1255	Approved
0.6632	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2639	Approved
0.663	Remote Similarity	NPD2642	Approved
0.6613	Remote Similarity	NPD3609	Approved
0.6613	Remote Similarity	NPD3610	Approved
0.6609	Remote Similarity	NPD3717	Discontinued
0.6582	Remote Similarity	NPD4615	Phase 2
0.6579	Remote Similarity	NPD5899	Approved
0.6579	Remote Similarity	NPD6452	Discontinued
0.6579	Remote Similarity	NPD5897	Approved
0.6579	Remote Similarity	NPD5898	Approved
0.6576	Remote Similarity	NPD509	Phase 3
0.6575	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7716	Approved
0.6573	Remote Similarity	NPD7717	Approved
0.6573	Remote Similarity	NPD3835	Phase 3
0.6573	Remote Similarity	NPD3833	Phase 3
0.6567	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2118	Approved
0.6566	Remote Similarity	NPD2119	Approved
0.6561	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8272	Phase 2
0.6552	Remote Similarity	NPD5020	Approved
0.6548	Remote Similarity	NPD3475	Approved
0.6548	Remote Similarity	NPD3476	Approved
0.6542	Remote Similarity	NPD4890	Phase 2
0.6538	Remote Similarity	NPD5255	Approved
0.6537	Remote Similarity	NPD7672	Approved
0.6537	Remote Similarity	NPD7671	Approved
0.6531	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7619	Phase 3
0.6515	Remote Similarity	NPD7618	Phase 3
0.6512	Remote Similarity	NPD1262	Discovery
0.651	Remote Similarity	NPD5596	Phase 2
0.6497	Remote Similarity	NPD3404	Approved
0.6495	Remote Similarity	NPD6217	Discontinued
0.6488	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD991	Phase 2
0.6467	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5315	Discontinued
0.6465	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD2383	Phase 1
0.6461	Remote Similarity	NPD1661	Suspended
0.6458	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5495	Phase 2
0.645	Remote Similarity	NPD7948	Phase 1
0.6443	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5995	Clinical (unspecified phase)
0.644	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.644	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4028	Approved
0.6433	Remote Similarity	NPD4029	Approved
0.6433	Remote Similarity	NPD4030	Approved
0.6429	Remote Similarity	NPD3114	Approved
0.6429	Remote Similarity	NPD3113	Approved
0.6429	Remote Similarity	NPD3115	Approved
0.6429	Remote Similarity	NPD3112	Approved
0.6429	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2430	Phase 2
0.6422	Remote Similarity	NPD8072	Approved
0.6421	Remote Similarity	NPD5104	Approved
0.6421	Remote Similarity	NPD2367	Phase 2
0.642	Remote Similarity	NPD2006	Phase 2
0.642	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2591	Phase 2
0.6409	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5473	Discontinued
0.64	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7935	Phase 2
0.6396	Remote Similarity	NPD6281	Approved
0.6396	Remote Similarity	NPD4499	Approved
0.6393	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2165	Phase 1
0.6373	Remote Similarity	NPD8073	Approved
0.6368	Remote Similarity	NPD6492	Phase 2
0.6368	Remote Similarity	NPD6664	Approved
0.6364	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7470	Discontinued
0.6364	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7957	Phase 1
0.6359	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4601	Approved
0.6355	Remote Similarity	NPD4600	Approved
0.635	Remote Similarity	NPD7944	Discontinued
0.635	Remote Similarity	NPD4602	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