NPASS Compound

Structure

NPC470621 OpenBabel07101719512D 57 58 0 0 1 0 0 0 0 0999 V2000 -0.9135 -6.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6127 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1486 -4.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -5.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7467 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1486 -5.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 -4.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6127 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0147 -4.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8185 -6.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8807 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4166 -5.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5704 -2.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -5.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7467 -1.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2826 -6.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 -4.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5759 -2.5227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8807 -2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5506 -6.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6456 -1.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5116 -1.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3776 -1.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6637 -0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -2.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4788 1.5933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9771 -3.5408 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6127 -1.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2826 -7.4067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -3.4067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.0147 -3.4067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6845 -5.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -4.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 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 -1.7796 0.0933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -6.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0119 -3.3317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7467 -3.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5506 -7.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -3.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -2.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 0.2749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2514 -1.4476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -3.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 -1.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 5 1 0 0 0 0 2 8 1 0 0 0 0 3 6 1 0 0 0 0 3 9 1 0 0 0 0 4 7 1 0 0 0 0 4 10 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 8 34 1 0 0 0 0 9 39 1 0 0 0 0 10 40 1 0 0 0 0 11 17 1 0 0 0 0 11 22 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 20 1 0 0 0 0 14 35 1 0 0 0 0 15 46 1 0 0 0 0 16 41 2 3 0 0 0 16 47 1 0 0 0 0 17 36 1 6 0 0 0 18 37 1 6 0 0 0 19 7 1 6 0 0 0 19 41 1 0 0 0 0 20 48 1 1 0 0 0 21 15 1 1 0 0 0 21 29 1 0 0 0 0 21 56 1 0 0 0 0 22 39 2 3 0 0 0 22 49 1 0 0 0 0 23 40 2 3 0 0 0 23 50 1 0 0 0 0 24 42 2 3 0 0 0 24 51 1 0 0 0 0 25 20 1 1 0 0 0 25 26 1 0 0 0 0 25 43 1 0 0 0 0 26 31 1 6 0 0 0 26 44 1 0 0 0 0 27 28 1 0 0 0 0 27 30 1 0 0 0 0 27 42 1 6 0 0 0 28 29 1 0 0 0 0 28 52 1 6 0 0 0 29 57 1 1 0 0 0 30 45 1 1 0 0 0 30 56 1 0 0 0 0 31 53 2 0 0 0 0 31 54 1 0 0 0 0 32 38 2 0 0 0 0 32 55 1 0 0 0 0 32 57 1 0 0 0 0 33 43 2 0 0 0 0 33 44 1 0 0 0 0 33 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	818.46
Volume:	781.2
LogP:	-5.488
LogD:	-1.741
LogS:	-1.264
# Rotatable Bonds:	29
TPSA:	431.86
# H-Bond Aceptor:	24
# H-Bond Donor:	21
# Rings:	2
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.019
Synthetic Accessibility Score:	6.093
Fsp3:	0.758
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.994
MDCK Permeability:	0.0011144191958010197
Pgp-inhibitor:	0.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.992
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.906
Plasma Protein Binding (PPB):	18.0338077545166%
Volume Distribution (VD):	0.464
Pgp-substrate:	62.5284309387207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.022
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.0
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	0.94
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.107
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.801
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.792
Carcinogencity:	0.445
Eye Corrosion:	0.003
Eye Irritation:	0.071
Respiratory Toxicity:	0.606

Download Data

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

Natural Product: NPC470621

Natural Product ID:	NPC470621
*Common Name:**	Nbeta-Acetylstreptothricin D Acid
IUPAC Name:	(4S,5S)-2-[[(2R,3R,4S,5R,6R)-3-[[(3S)-3-acetamido-6-[[(3S)-3-amino-6-[[(3S)-3,6-diaminohexanoyl]amino]hexanoyl]amino]hexanoyl]amino]-5-carbamoyloxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-5-[(1R)-2-amino-1-hydroxyethyl]-4,5-dihydro-1H-imidazole-4-carboxylic acid
Synonyms:	N-Beta-Acetylstreptothricin D Acid
Standard InCHIKey:	JAVLRUXTMWRPQN-KJHZUQIMSA-N
Standard InCHI:	InChI=1S/C33H62N12O12/c1-16(47)41-19(7-4-10-40-23(50)12-18(37)6-3-9-39-22(49)11-17(36)5-2-8-34)13-24(51)42-27-28(52)29(57-32(38)55)21(15-46)56-30(27)45-33-43-25(20(48)14-35)26(44-33)31(53)54/h17-21,25-30,46,48,52H,2-15,34-37H2,1H3,(H2,38,55)(H,39,49)(H,40,50)(H,41,47)(H,42,51)(H,53,54)(H2,43,44,45)/t17-,18-,19-,20+,21+,25+,26-,27+,28-,29-,30+/m0/s1
SMILES:	NCCC[C@@H](CC(=NCCC[C@@H](CC(=NCCC[C@@H](CC(=N[C@H]1[C@H](NC2=N[C@@H]([C@H](N2)C(=O)O)[C@@H](CN)O)O[C@@H]([C@@H]([C@H]1O)OC(=N)O)CO)O)N=C(O)C)O)N)O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2088427
PubChem CID:	25187948
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002203] Glycosylamines

*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
NPO31206	Streptomyces sp. i08a 1776	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21510638]
NPO31206	Streptomyces sp. i08a 1776	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22939698]

☑ 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	9

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	256.0	ug.mL-1	PMID[498312]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	256.0	ug.mL-1	PMID[498312]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	64.0	ug.mL-1	PMID[498312]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>	256.0	ug.mL-1	PMID[498312]
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	MIC	>	256.0	ug.mL-1	PMID[498312]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	256.0	ug.mL-1	PMID[498312]
NPT3495	Organism	Morganella morganii	Morganella morganii	MIC	>	256.0	ug.mL-1	PMID[498312]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64.0	ug.mL-1	PMID[498312]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	256.0	ug.mL-1	PMID[498312]

☑ 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 NPC470621 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	334
0.1-0.2	12276
0.2-0.3	22871
0.3-0.4	5612
0.4-0.5	1260
0.5-0.6	307
0.6-0.7	22
0.7-0.8	1
0.8-0.85	4
0.85-0.9	7
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC222481
0.9906	High Similarity	NPC259586
0.8624	High Similarity	NPC325900
0.8624	High Similarity	NPC10897
0.8532	High Similarity	NPC189854
0.8532	High Similarity	NPC92874
0.8532	High Similarity	NPC62845
0.8532	High Similarity	NPC322449
0.8532	High Similarity	NPC166242
0.844	Intermediate Similarity	NPC314413
0.844	Intermediate Similarity	NPC314398
0.844	Intermediate Similarity	NPC239705
0.6538	Remote Similarity	NPC477237
0.6439	Remote Similarity	NPC477238
0.6391	Remote Similarity	NPC94319
0.6372	Remote Similarity	NPC469363
0.6343	Remote Similarity	NPC325750
0.6299	Remote Similarity	NPC57436
0.6299	Remote Similarity	NPC121479
0.6296	Remote Similarity	NPC477518
0.6269	Remote Similarity	NPC471262
0.6186	Remote Similarity	NPC208537
0.6186	Remote Similarity	NPC270005
0.617	Remote Similarity	NPC318142
0.6134	Remote Similarity	NPC216278
0.6131	Remote Similarity	NPC471263
0.6127	Remote Similarity	NPC471256
0.6068	Remote Similarity	NPC292345
0.605	Remote Similarity	NPC328646
0.6016	Remote Similarity	NPC475440
0.5981	Remote Similarity	NPC328457
0.5962	Remote Similarity	NPC316244
0.594	Remote Similarity	NPC313813
0.5932	Remote Similarity	NPC275715
0.5929	Remote Similarity	NPC314466
0.5924	Remote Similarity	NPC321485
0.5924	Remote Similarity	NPC327517
0.5924	Remote Similarity	NPC319334
0.5924	Remote Similarity	NPC322372
0.5924	Remote Similarity	NPC317377
0.5909	Remote Similarity	NPC63191
0.5909	Remote Similarity	NPC471202
0.5906	Remote Similarity	NPC128303
0.5882	Remote Similarity	NPC477729
0.587	Remote Similarity	NPC471255
0.5859	Remote Similarity	NPC241394
0.5845	Remote Similarity	NPC313657
0.5828	Remote Similarity	NPC477519
0.5814	Remote Similarity	NPC59589
0.5812	Remote Similarity	NPC83839
0.5794	Remote Similarity	NPC188453
0.5794	Remote Similarity	NPC42320
0.5776	Remote Similarity	NPC95478
0.5776	Remote Similarity	NPC145748
0.5776	Remote Similarity	NPC155670
0.5772	Remote Similarity	NPC330590
0.5763	Remote Similarity	NPC477728
0.5736	Remote Similarity	NPC475637
0.5726	Remote Similarity	NPC227051
0.5725	Remote Similarity	NPC245534
0.5702	Remote Similarity	NPC474576
0.5695	Remote Similarity	NPC142761
0.5693	Remote Similarity	NPC471261
0.5664	Remote Similarity	NPC314772
0.5664	Remote Similarity	NPC314968
0.5664	Remote Similarity	NPC191774
0.5656	Remote Similarity	NPC471098
0.5656	Remote Similarity	NPC62263
0.5656	Remote Similarity	NPC173763
0.5648	Remote Similarity	NPC133183
0.5635	Remote Similarity	NPC220234
0.563	Remote Similarity	NPC306838
0.562	Remote Similarity	NPC475801
0.562	Remote Similarity	NPC474593
0.5615	Remote Similarity	NPC475918
0.5614	Remote Similarity	NPC316807

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 NPC470621 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	95
0.1-0.2	1843
0.2-0.3	5164
0.3-0.4	1583
0.4-0.5	328
0.5-0.6	111
0.6-0.7	25
0.7-0.8	1
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
0.7179	Intermediate Similarity	NPD8045	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6428	Approved
0.6726	Remote Similarity	NPD3716	Discontinued
0.6545	Remote Similarity	NPD4829	Discontinued
0.6522	Remote Similarity	NPD4261	Phase 1
0.6391	Remote Similarity	NPD4826	Approved
0.6391	Remote Similarity	NPD4828	Approved
0.6391	Remote Similarity	NPD4827	Approved
0.637	Remote Similarity	NPD4816	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD8394	Approved
0.6356	Remote Similarity	NPD6424	Approved
0.6349	Remote Similarity	NPD6941	Approved
0.6303	Remote Similarity	NPD7844	Discontinued
0.6299	Remote Similarity	NPD4833	Approved
0.6299	Remote Similarity	NPD35	Approved
0.6231	Remote Similarity	NPD3204	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6120	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6122	Discontinued
0.6172	Remote Similarity	NPD1804	Phase 2
0.6172	Remote Similarity	NPD1805	Phase 2
0.6168	Remote Similarity	NPD366	Approved
0.6134	Remote Similarity	NPD6423	Approved
0.6134	Remote Similarity	NPD6426	Approved
0.6134	Remote Similarity	NPD6425	Approved
0.6134	Remote Similarity	NPD6427	Approved
0.6111	Remote Similarity	NPD1428	Phase 2
0.6102	Remote Similarity	NPD6432	Approved
0.6102	Remote Similarity	NPD6433	Approved
0.6102	Remote Similarity	NPD6431	Approved
0.6102	Remote Similarity	NPD6434	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD618	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8175	Discontinued
0.6061	Remote Similarity	NPD869	Approved
0.5984	Remote Similarity	NPD5376	Approved
0.5982	Remote Similarity	NPD9429	Discontinued
0.5969	Remote Similarity	NPD284	Phase 1
0.5935	Remote Similarity	NPD8038	Phase 2
0.5902	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8346	Approved
0.5882	Remote Similarity	NPD8347	Approved
0.5882	Remote Similarity	NPD8345	Approved
0.5877	Remote Similarity	NPD2691	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD1385	Discontinued
0.5814	Remote Similarity	NPD1827	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD1829	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD1828	Approved
0.5781	Remote Similarity	NPD2700	Approved
0.5772	Remote Similarity	NPD5381	Approved
0.5772	Remote Similarity	NPD5378	Approved
0.5772	Remote Similarity	NPD5377	Approved
0.576	Remote Similarity	NPD4825	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD7139	Approved
0.5748	Remote Similarity	NPD7140	Approved
0.5738	Remote Similarity	NPD1447	Phase 3
0.5738	Remote Similarity	NPD1446	Phase 3
0.5714	Remote Similarity	NPD3177	Phase 3
0.5703	Remote Similarity	NPD4743	Phase 2
0.5703	Remote Similarity	NPD3161	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD8087	Discontinued
0.5667	Remote Similarity	NPD6077	Discontinued
0.5664	Remote Similarity	NPD3160	Suspended
0.5664	Remote Similarity	NPD9435	Approved
0.5664	Remote Similarity	NPD9434	Approved
0.5664	Remote Similarity	NPD4278	Clinical (unspecified phase)
0.5662	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.5662	Remote Similarity	NPD6935	Phase 3
0.5641	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD2255	Approved
0.563	Remote Similarity	NPD7915	Approved
0.563	Remote Similarity	NPD7916	Approved
0.5607	Remote Similarity	NPD9231	Phase 3
0.5607	Remote Similarity	NPD9232	Phase 2
0.5607	Remote Similarity	NPD9233	Phase 3

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