NPASS Compound

Structure

CID201831 OpenBabel06191715592D 45 49 0 0 1 0 0 0 0 0999 V2000 1.9563 -0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2092 5.3507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 2.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7553 4.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 2.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 -0.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 3.8090 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 -3.7525 4.5643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 4.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1075 2.2967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8797 2.1104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0411 2.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2079 5.4030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2999 3.6210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.8781 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 -3.2985 3.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 3.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4538 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 4.9179 5.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6619 6.2940 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 4.3781 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.6036 0.1194 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7839 5.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 5.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 4.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6569 2.7398 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 4.1871 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 1.4538 2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8879 0.9592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 1 9 1 0 0 0 0 2 3 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 7 2 0 0 0 0 5 19 1 0 0 0 0 6 8 2 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 34 1 0 0 0 0 10 37 1 0 0 0 0 11 38 1 0 0 0 0 12 41 1 0 0 0 0 13 19 2 0 0 0 0 13 24 1 0 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 18 1 0 0 0 0 15 30 1 0 0 0 0 16 18 2 0 0 0 0 16 39 1 0 0 0 0 17 23 2 0 0 0 0 17 40 1 0 0 0 0 18 21 1 0 0 0 0 19 32 1 0 0 0 0 20 33 1 0 0 0 0 21 24 2 0 0 0 0 22 23 1 0 0 0 0 22 25 2 0 0 0 0 23 26 1 0 0 0 0 24 39 1 0 0 0 0 25 40 1 0 0 0 0 26 30 1 1 0 0 0 26 31 1 0 0 0 0 27 31 1 0 0 0 0 27 37 2 3 0 0 0 27 42 1 0 0 0 0 28 30 1 0 0 0 0 28 41 1 0 0 0 0 28 43 2 0 0 0 0 29 35 2 0 0 0 0 29 36 1 0 0 0 0 29 38 1 0 0 0 0 30 44 1 1 0 0 0 31 41 1 0 0 0 0 31 45 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	744.14
Volume:	634.651
LogP:	3.326
LogD:	1.583
LogS:	-3.312
# Rotatable Bonds:	15
TPSA:	209.37
# H-Bond Aceptor:	12
# H-Bond Donor:	11
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.057
Synthetic Accessibility Score:	4.459
Fsp3:	0.387
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.925
MDCK Permeability:	2.9051982437522383e-06
Pgp-inhibitor:	0.013
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.66
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	88.51617431640625%
Volume Distribution (VD):	1.58
Pgp-substrate:	27.3287410736084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.248
CYP1A2-substrate:	0.509
CYP2C19-inhibitor:	0.372
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.953
CYP2D6-substrate:	0.484
CYP3A4-inhibitor:	0.873
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	4.038
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.343
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.804
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.863
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.214
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC201831

Natural Product ID:	NPC201831
*Common Name:**	Eusynstyelamide F
IUPAC Name:	(2S,3R,4S)-1-(4-aminobutyl)-3-(6-bromo-1H-indol-3-yl)-4-[(6-bromo-1H-indol-3-yl)methyl]-N-[4-(diaminomethylideneamino)butyl]-2,4-dihydroxy-5-oxopyrrolidine-2-carboxamide
Synonyms:	Eusynstyelamide F
Standard InCHIKey:	RPGMNINLCSRHGB-JZRGNDHQSA-N
Standard InCHI:	InChI=1S/C31H38Br2N8O4/c32-19-5-7-21-18(16-39-24(21)13-19)15-30(44)26(23-17-40-25-14-20(33)6-8-22(23)25)31(45,41(28(30)43)12-4-1-9-34)27(42)37-10-2-3-11-38-29(35)36/h5-8,13-14,16-17,26,39-40,44-45H,1-4,9-12,15,34H2,(H,37,42)(H4,35,36,38)/t26-,30+,31+/m1/s1
SMILES:	NCCCCN1C(=O)[C@]([C@H]([C@]1(O)C(=NCCCCNC(=N)N)O)c1c[nH]c2c1ccc(c2)Br)(O)Cc1c[nH]c2c1ccc(c2)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774254
PubChem CID:	52951298
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:0002309] Alpha amino acid amides

*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
NPO33659	Tegella cf. spitzbergensis	Species	Calloporidae	Eukaryota	n.a.	Bear Island in the North Atlantic (7414.534' N, 192.114' E), at 59 m depth	2007-MAY	PMID[21370896]
NPO29918	Tegella cf.	Species	Calloporidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21370896]

☑ 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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[518007]
NPT1382	Organism	Corynebacterium glutamicum	Corynebacterium glutamicum	MIC	=	6.25	ug.mL-1	PMID[518007]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[518007]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	12.5	ug.mL-1	PMID[518007]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	12.5	ug.mL-1	PMID[518007]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	50.0	ug.mL-1	PMID[518007]

☑ 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 NPC201831 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	511
0.1-0.2	3565
0.2-0.3	17551
0.3-0.4	14600
0.4-0.5	2644
0.5-0.6	2631
0.6-0.7	1013
0.7-0.8	172
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC17487
0.9953	High Similarity	NPC477107
0.9953	High Similarity	NPC477109
0.9953	High Similarity	NPC477108
0.9624	High Similarity	NPC63031
0.875	High Similarity	NPC477114
0.8455	Intermediate Similarity	NPC475736
0.8214	Intermediate Similarity	NPC474195
0.815	Intermediate Similarity	NPC474196
0.7831	Intermediate Similarity	NPC125181
0.7831	Intermediate Similarity	NPC263117
0.7831	Intermediate Similarity	NPC242872
0.7828	Intermediate Similarity	NPC473376
0.7787	Intermediate Similarity	NPC471536
0.7773	Intermediate Similarity	NPC475935
0.7773	Intermediate Similarity	NPC52909
0.7773	Intermediate Similarity	NPC94211
0.7768	Intermediate Similarity	NPC162860
0.7758	Intermediate Similarity	NPC54420
0.7756	Intermediate Similarity	NPC321939
0.7738	Intermediate Similarity	NPC117980
0.7731	Intermediate Similarity	NPC477167
0.7731	Intermediate Similarity	NPC473342
0.7727	Intermediate Similarity	NPC23420
0.7727	Intermediate Similarity	NPC303820
0.7727	Intermediate Similarity	NPC205254
0.7727	Intermediate Similarity	NPC106771
0.7709	Intermediate Similarity	NPC54744
0.7699	Intermediate Similarity	NPC320968
0.7665	Intermediate Similarity	NPC207020
0.7636	Intermediate Similarity	NPC171317
0.7627	Intermediate Similarity	NPC69843
0.759	Intermediate Similarity	NPC475746
0.7585	Intermediate Similarity	NPC156003
0.7578	Intermediate Similarity	NPC476073
0.7568	Intermediate Similarity	NPC269203
0.7568	Intermediate Similarity	NPC166209
0.7568	Intermediate Similarity	NPC13456
0.7568	Intermediate Similarity	NPC77241
0.7564	Intermediate Similarity	NPC64216
0.7557	Intermediate Similarity	NPC474389
0.7523	Intermediate Similarity	NPC474318
0.7523	Intermediate Similarity	NPC201266
0.7523	Intermediate Similarity	NPC268744
0.7523	Intermediate Similarity	NPC475914
0.7523	Intermediate Similarity	NPC153123
0.7523	Intermediate Similarity	NPC220797
0.7522	Intermediate Similarity	NPC478157
0.7511	Intermediate Similarity	NPC75634
0.75	Intermediate Similarity	NPC477714
0.75	Intermediate Similarity	NPC325976
0.749	Intermediate Similarity	NPC89987
0.7489	Intermediate Similarity	NPC477166
0.7489	Intermediate Similarity	NPC304187
0.7477	Intermediate Similarity	NPC131887
0.7457	Intermediate Similarity	NPC477715
0.7456	Intermediate Similarity	NPC478158
0.7448	Intermediate Similarity	NPC475969
0.7448	Intermediate Similarity	NPC474877
0.7448	Intermediate Similarity	NPC475859
0.7444	Intermediate Similarity	NPC293917
0.7432	Intermediate Similarity	NPC227582
0.7431	Intermediate Similarity	NPC213629
0.7431	Intermediate Similarity	NPC321708
0.7406	Intermediate Similarity	NPC477175
0.7406	Intermediate Similarity	NPC477176
0.7406	Intermediate Similarity	NPC470729
0.7406	Intermediate Similarity	NPC470730
0.7403	Intermediate Similarity	NPC477610
0.7386	Intermediate Similarity	NPC63279
0.738	Intermediate Similarity	NPC223791
0.738	Intermediate Similarity	NPC107077
0.7376	Intermediate Similarity	NPC88315
0.7375	Intermediate Similarity	NPC477177
0.7355	Intermediate Similarity	NPC297642
0.7345	Intermediate Similarity	NPC155143
0.7344	Intermediate Similarity	NPC165743
0.7333	Intermediate Similarity	NPC252338
0.7333	Intermediate Similarity	NPC326363
0.7316	Intermediate Similarity	NPC82370
0.7306	Intermediate Similarity	NPC17059
0.7301	Intermediate Similarity	NPC475506
0.7292	Intermediate Similarity	NPC477608
0.7292	Intermediate Similarity	NPC477607
0.7277	Intermediate Similarity	NPC262898
0.7277	Intermediate Similarity	NPC281049
0.726	Intermediate Similarity	NPC94752
0.7253	Intermediate Similarity	NPC470703
0.7244	Intermediate Similarity	NPC473640
0.7238	Intermediate Similarity	NPC476818
0.7234	Intermediate Similarity	NPC472285
0.7232	Intermediate Similarity	NPC179701
0.7222	Intermediate Similarity	NPC474412
0.722	Intermediate Similarity	NPC188821
0.722	Intermediate Similarity	NPC474180
0.7216	Intermediate Similarity	NPC478006
0.7213	Intermediate Similarity	NPC245055
0.7212	Intermediate Similarity	NPC100321
0.7212	Intermediate Similarity	NPC74413
0.721	Intermediate Similarity	NPC473218
0.721	Intermediate Similarity	NPC470702
0.7203	Intermediate Similarity	NPC477609
0.7196	Intermediate Similarity	NPC477611
0.7194	Intermediate Similarity	NPC314882
0.7193	Intermediate Similarity	NPC260900
0.7193	Intermediate Similarity	NPC193761
0.7186	Intermediate Similarity	NPC314957
0.7184	Intermediate Similarity	NPC478028
0.7183	Intermediate Similarity	NPC14812
0.7182	Intermediate Similarity	NPC315555
0.7154	Intermediate Similarity	NPC153400
0.7149	Intermediate Similarity	NPC191382
0.7149	Intermediate Similarity	NPC56109
0.7148	Intermediate Similarity	NPC77101
0.7143	Intermediate Similarity	NPC272174
0.7137	Intermediate Similarity	NPC477004
0.7137	Intermediate Similarity	NPC75726
0.7137	Intermediate Similarity	NPC31385
0.7137	Intermediate Similarity	NPC110602
0.7136	Intermediate Similarity	NPC15102
0.7131	Intermediate Similarity	NPC264285
0.713	Intermediate Similarity	NPC243716
0.7126	Intermediate Similarity	NPC478029
0.7118	Intermediate Similarity	NPC476874
0.7113	Intermediate Similarity	NPC474896
0.7113	Intermediate Similarity	NPC473317
0.7112	Intermediate Similarity	NPC476524
0.7105	Intermediate Similarity	NPC470497
0.7102	Intermediate Similarity	NPC474357
0.7097	Intermediate Similarity	NPC59269
0.7094	Intermediate Similarity	NPC72956
0.7093	Intermediate Similarity	NPC470499
0.7093	Intermediate Similarity	NPC67288
0.7091	Intermediate Similarity	NPC228835
0.7089	Intermediate Similarity	NPC238945
0.7085	Intermediate Similarity	NPC28945
0.7083	Intermediate Similarity	NPC16352
0.7083	Intermediate Similarity	NPC31097
0.7083	Intermediate Similarity	NPC155444
0.7064	Intermediate Similarity	NPC128084
0.7064	Intermediate Similarity	NPC6865
0.7064	Intermediate Similarity	NPC153980
0.7061	Intermediate Similarity	NPC935
0.7061	Intermediate Similarity	NPC267078
0.705	Intermediate Similarity	NPC315467
0.7046	Intermediate Similarity	NPC471192
0.7046	Intermediate Similarity	NPC36405
0.7037	Intermediate Similarity	NPC314603
0.7037	Intermediate Similarity	NPC476491
0.7036	Intermediate Similarity	NPC66642
0.7034	Intermediate Similarity	NPC282247
0.7034	Intermediate Similarity	NPC229348
0.7033	Intermediate Similarity	NPC323752
0.7027	Intermediate Similarity	NPC235684
0.7025	Intermediate Similarity	NPC125597
0.7023	Intermediate Similarity	NPC478010
0.7023	Intermediate Similarity	NPC478009
0.7018	Intermediate Similarity	NPC111275
0.7011	Intermediate Similarity	NPC314056
0.7008	Intermediate Similarity	NPC477630
0.7008	Intermediate Similarity	NPC477635
0.7	Intermediate Similarity	NPC307191
0.6996	Remote Similarity	NPC24370
0.6996	Remote Similarity	NPC319232
0.6996	Remote Similarity	NPC214142
0.6992	Remote Similarity	NPC471194
0.6992	Remote Similarity	NPC471193
0.6987	Remote Similarity	NPC469717
0.6986	Remote Similarity	NPC55772
0.6986	Remote Similarity	NPC283219
0.6982	Remote Similarity	NPC308931
0.6982	Remote Similarity	NPC99939
0.698	Remote Similarity	NPC95240
0.698	Remote Similarity	NPC322135
0.6975	Remote Similarity	NPC470731
0.6975	Remote Similarity	NPC470732
0.6974	Remote Similarity	NPC477633
0.697	Remote Similarity	NPC473761
0.6967	Remote Similarity	NPC304307
0.6967	Remote Similarity	NPC118559
0.6967	Remote Similarity	NPC261251
0.6967	Remote Similarity	NPC34580
0.6967	Remote Similarity	NPC124920
0.6964	Remote Similarity	NPC284888
0.6964	Remote Similarity	NPC220852
0.6955	Remote Similarity	NPC141428
0.6951	Remote Similarity	NPC470323
0.6948	Remote Similarity	NPC285343
0.6943	Remote Similarity	NPC149708
0.6939	Remote Similarity	NPC100547
0.6935	Remote Similarity	NPC33064
0.6932	Remote Similarity	NPC478013
0.693	Remote Similarity	NPC160105
0.6927	Remote Similarity	NPC110500
0.6927	Remote Similarity	NPC149155
0.6927	Remote Similarity	NPC203468
0.6923	Remote Similarity	NPC54803
0.6923	Remote Similarity	NPC321592
0.692	Remote Similarity	NPC82472
0.6917	Remote Similarity	NPC473310

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 NPC201831 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	608
0.2-0.3	1108
0.3-0.4	2383
0.4-0.5	2479
0.5-0.6	1965
0.6-0.7	333
0.7-0.8	30
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
0.7919	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD5426	Phase 3
0.7621	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7970	Approved
0.7457	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7470	Discontinued
0.7284	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7953	Approved
0.7243	Intermediate Similarity	NPD7952	Approved
0.7243	Intermediate Similarity	NPD7950	Approved
0.7243	Intermediate Similarity	NPD7951	Approved
0.7243	Intermediate Similarity	NPD7790	Approved
0.7243	Intermediate Similarity	NPD7789	Approved
0.7243	Intermediate Similarity	NPD7791	Approved
0.721	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7730	Approved
0.7178	Intermediate Similarity	NPD7731	Approved
0.7174	Intermediate Similarity	NPD7001	Phase 3
0.7174	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2091	Phase 2
0.7169	Intermediate Similarity	NPD2096	Phase 2
0.7167	Intermediate Similarity	NPD7271	Approved
0.7149	Intermediate Similarity	NPD7780	Approved
0.7149	Intermediate Similarity	NPD7781	Approved
0.7137	Intermediate Similarity	NPD7711	Discontinued
0.7137	Intermediate Similarity	NPD6999	Discontinued
0.7137	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2092	Phase 2
0.7123	Intermediate Similarity	NPD2095	Phase 2
0.7123	Intermediate Similarity	NPD2094	Phase 2
0.7119	Intermediate Similarity	NPD7824	Approved
0.711	Intermediate Similarity	NPD6595	Phase 3
0.7106	Intermediate Similarity	NPD8094	Discontinued
0.7066	Intermediate Similarity	NPD7603	Discontinued
0.7054	Intermediate Similarity	NPD7716	Approved
0.7054	Intermediate Similarity	NPD7717	Approved
0.7051	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6164	Phase 2
0.7037	Intermediate Similarity	NPD6165	Phase 2
0.7032	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8322	Phase 2
0.6992	Remote Similarity	NPD8093	Discontinued
0.6983	Remote Similarity	NPD8272	Phase 2
0.696	Remote Similarity	NPD7944	Discontinued
0.6933	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD482	Approved
0.6906	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6664	Approved
0.6897	Remote Similarity	NPD8073	Approved
0.6895	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7666	Phase 3
0.6822	Remote Similarity	NPD7665	Phase 2
0.6812	Remote Similarity	NPD7618	Phase 3
0.6812	Remote Similarity	NPD7619	Phase 3
0.6805	Remote Similarity	NPD8257	Approved
0.6805	Remote Similarity	NPD8256	Approved
0.6805	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6665	Discontinued
0.6795	Remote Similarity	NPD8072	Approved
0.6787	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4852	Phase 2
0.677	Remote Similarity	NPD8431	Approved
0.6766	Remote Similarity	NPD5901	Discontinued
0.6757	Remote Similarity	NPD8386	Phase 2
0.6753	Remote Similarity	NPD2880	Discontinued
0.6737	Remote Similarity	NPD7957	Phase 1
0.6737	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD750	Phase 2
0.6723	Remote Similarity	NPD4520	Approved
0.671	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7948	Phase 1
0.6679	Remote Similarity	NPD6458	Discontinued
0.6653	Remote Similarity	NPD8119	Discontinued
0.6641	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7415	Suspended
0.6624	Remote Similarity	NPD8098	Approved
0.6623	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD2443	Approved
0.6611	Remote Similarity	NPD2442	Approved
0.6609	Remote Similarity	NPD5003	Discontinued
0.6598	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8271	Discontinued
0.6597	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD484	Approved
0.6571	Remote Similarity	NPD8349	Phase 1
0.657	Remote Similarity	NPD2411	Approved
0.6569	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD8321	Discontinued
0.6555	Remote Similarity	NPD8169	Discontinued
0.6547	Remote Similarity	NPD5065	Approved
0.6538	Remote Similarity	NPD8250	Phase 2
0.6531	Remote Similarity	NPD2813	Phase 3
0.6531	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3915	Approved
0.6527	Remote Similarity	NPD2008	Discontinued
0.6506	Remote Similarity	NPD8284	Discontinued
0.6502	Remote Similarity	NPD8097	Phase 3
0.6502	Remote Similarity	NPD3917	Approved
0.6502	Remote Similarity	NPD3918	Approved
0.6502	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD8096	Phase 3
0.6498	Remote Similarity	NPD7817	Phase 1
0.6485	Remote Similarity	NPD6987	Phase 1
0.6484	Remote Similarity	NPD8026	Phase 1
0.6482	Remote Similarity	NPD8316	Phase 2
0.6482	Remote Similarity	NPD8106	Phase 2
0.6482	Remote Similarity	NPD8317	Phase 2
0.6482	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD2510	Approved
0.6473	Remote Similarity	NPD2509	Approved
0.6471	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6995	Phase 1
0.6458	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD8289	Discontinued
0.6453	Remote Similarity	NPD8641	Approved
0.6453	Remote Similarity	NPD4427	Phase 2
0.6446	Remote Similarity	NPD2408	Discontinued
0.6444	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD706	Phase 1
0.6435	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8292	Phase 2
0.642	Remote Similarity	NPD3013	Phase 3
0.642	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7465	Suspended
0.6418	Remote Similarity	NPD6530	Approved
0.6418	Remote Similarity	NPD6531	Approved
0.6417	Remote Similarity	NPD8283	Approved
0.6417	Remote Similarity	NPD8282	Approved
0.6417	Remote Similarity	NPD56	Approved
0.6406	Remote Similarity	NPD6970	Phase 2
0.6405	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD5818	Discontinued
0.6397	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD4079	Approved
0.6388	Remote Similarity	NPD4076	Approved
0.6387	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD1996	Discontinued
0.6381	Remote Similarity	NPD5891	Approved
0.6375	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6753	Phase 1
0.6375	Remote Similarity	NPD6752	Phase 1
0.6372	Remote Similarity	NPD4075	Phase 2
0.6368	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2844	Phase 3
0.6364	Remote Similarity	NPD6217	Discontinued
0.6356	Remote Similarity	NPD5612	Discontinued
0.6353	Remote Similarity	NPD7688	Phase 1
0.6349	Remote Similarity	NPD4890	Phase 2
0.6346	Remote Similarity	NPD7576	Discontinued
0.6344	Remote Similarity	NPD3505	Approved
0.6344	Remote Similarity	NPD3506	Approved
0.6341	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD8524	Approved
0.6341	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD3961	Discontinued
0.6332	Remote Similarity	NPD8408	Discontinued
0.6327	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD4558	Phase 2
0.6322	Remote Similarity	NPD7568	Phase 1
0.6322	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8460	Approved
0.6321	Remote Similarity	NPD8459	Approved
0.6318	Remote Similarity	NPD4600	Approved
0.6318	Remote Similarity	NPD6986	Phase 1
0.6318	Remote Similarity	NPD4601	Approved
0.6316	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD8364	Approved
0.6314	Remote Similarity	NPD8363	Approved
0.6312	Remote Similarity	NPD8375	Approved
0.6311	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7181	Phase 3
0.6305	Remote Similarity	NPD7878	Phase 2
0.6303	Remote Similarity	NPD7778	Approved
0.6303	Remote Similarity	NPD7459	Phase 2
0.6303	Remote Similarity	NPD7777	Approved
0.6303	Remote Similarity	NPD53	Approved
0.6301	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD4086	Phase 1
0.6292	Remote Similarity	NPD5017	Discontinued
0.629	Remote Similarity	NPD8525	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