NPASS Compound

Structure

CID63031 OpenBabel06191715402D 42 46 0 0 1 0 0 0 0 0999 V2000 -4.9179 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 2.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 1.6942 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 -5.7839 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 2.8532 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 -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 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 -6.6500 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 3.8042 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 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 3 1 0 0 0 0 1 9 1 0 0 0 0 2 4 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 33 1 0 0 0 0 10 34 1 0 0 0 0 11 35 1 0 0 0 0 12 38 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 29 1 0 0 0 0 16 18 2 0 0 0 0 16 36 1 0 0 0 0 17 23 2 0 0 0 0 17 37 1 0 0 0 0 18 21 1 0 0 0 0 19 31 1 0 0 0 0 20 32 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 36 1 0 0 0 0 25 37 1 0 0 0 0 26 29 1 1 0 0 0 26 30 1 0 0 0 0 27 30 1 0 0 0 0 27 35 2 3 0 0 0 27 39 1 0 0 0 0 28 29 1 0 0 0 0 28 38 1 0 0 0 0 28 40 2 0 0 0 0 29 41 1 1 0 0 0 30 38 1 0 0 0 0 30 42 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	702.12
Volume:	597.998
LogP:	3.924
LogD:	2.678
LogS:	-3.534
# Rotatable Bonds:	13
TPSA:	173.49
# H-Bond Aceptor:	10
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.112
Synthetic Accessibility Score:	4.347
Fsp3:	0.4
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:	-5.894
MDCK Permeability:	2.92219192488119e-06
Pgp-inhibitor:	0.026
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.307
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	83.84224700927734%
Volume Distribution (VD):	1.601
Pgp-substrate:	40.1586799621582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.423
CYP1A2-substrate:	0.442
CYP2C19-inhibitor:	0.87
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.576
CYP2C9-substrate:	0.229
CYP2D6-inhibitor:	0.973
CYP2D6-substrate:	0.401
CYP3A4-inhibitor:	0.971
CYP3A4-substrate:	0.391

ADMET: Excretion

Clearance (CL):	4.303
Half-life (T1/2):	0.136

ADMET: Toxicity

hERG Blockers:	0.417
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.461
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.501
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.309
Carcinogencity:	0.081
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC63031

Natural Product ID:	NPC63031
*Common Name:**	Eusynstyelamide D
IUPAC Name:	(2S,3R,4S)-N,1-bis(4-aminobutyl)-3-(6-bromo-1H-indol-3-yl)-4-[(6-bromo-1H-indol-3-yl)methyl]-2,4-dihydroxy-5-oxopyrrolidine-2-carboxamide
Synonyms:	Eusynstyelamide D
Standard InCHIKey:	PIHIJDUVKHNVTR-POLDFPFKSA-N
Standard InCHI:	InChI=1S/C30H36Br2N6O4/c31-19-5-7-21-18(16-36-24(21)13-19)15-29(41)26(23-17-37-25-14-20(32)6-8-22(23)25)30(42,27(39)35-11-3-1-9-33)38(28(29)40)12-4-2-10-34/h5-8,13-14,16-17,26,36-37,41-42H,1-4,9-12,15,33-34H2,(H,35,39)/t26-,29+,30+/m1/s1
SMILES:	NCCCCN1C(=O)[C@]([C@H]([C@]1(O)C(=NCCCCN)O)c1c[nH]c2c1ccc(c2)Br)(O)Cc1c[nH]c2c1ccc(c2)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774252
PubChem CID:	52951296
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
IC50	1
MIC	6

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1383	Cell Line	A2058	Homo sapiens	IC50	=	57000.0	nM	PMID[501724]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[501724]
NPT1382	Organism	Corynebacterium glutamicum	Corynebacterium glutamicum	MIC	=	12.5	ug.mL-1	PMID[501724]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	20.0	ug.mL-1	PMID[501724]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	12.5	ug.mL-1	PMID[501724]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[501724]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	50.0	ug.mL-1	PMID[501724]

☑ 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 NPC63031 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	452
0.1-0.2	3090
0.2-0.3	16062
0.3-0.4	16338
0.4-0.5	2733
0.5-0.6	2635
0.6-0.7	1120
0.7-0.8	259
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9624	High Similarity	NPC201831
0.9624	High Similarity	NPC17487
0.9579	High Similarity	NPC477109
0.9579	High Similarity	NPC477107
0.9579	High Similarity	NPC477108
0.838	Intermediate Similarity	NPC477114
0.8174	Intermediate Similarity	NPC475736
0.8066	Intermediate Similarity	NPC52909
0.8066	Intermediate Similarity	NPC475935
0.8066	Intermediate Similarity	NPC94211
0.8019	Intermediate Similarity	NPC205254
0.8019	Intermediate Similarity	NPC303820
0.8019	Intermediate Similarity	NPC23420
0.8019	Intermediate Similarity	NPC106771
0.7972	Intermediate Similarity	NPC162860
0.7963	Intermediate Similarity	NPC54420
0.7945	Intermediate Similarity	NPC207020
0.7937	Intermediate Similarity	NPC474195
0.7876	Intermediate Similarity	NPC474196
0.786	Intermediate Similarity	NPC476073
0.785	Intermediate Similarity	NPC166209
0.785	Intermediate Similarity	NPC13456
0.785	Intermediate Similarity	NPC77241
0.785	Intermediate Similarity	NPC269203
0.784	Intermediate Similarity	NPC171317
0.7804	Intermediate Similarity	NPC220797
0.7804	Intermediate Similarity	NPC474318
0.7804	Intermediate Similarity	NPC268744
0.7804	Intermediate Similarity	NPC201266
0.7804	Intermediate Similarity	NPC153123
0.7804	Intermediate Similarity	NPC475914
0.7793	Intermediate Similarity	NPC478157
0.7768	Intermediate Similarity	NPC477714
0.7757	Intermediate Similarity	NPC131887
0.7727	Intermediate Similarity	NPC478158
0.7723	Intermediate Similarity	NPC477715
0.7721	Intermediate Similarity	NPC293917
0.7714	Intermediate Similarity	NPC213629
0.7714	Intermediate Similarity	NPC321708
0.771	Intermediate Similarity	NPC227582
0.7703	Intermediate Similarity	NPC75634
0.7682	Intermediate Similarity	NPC325976
0.7668	Intermediate Similarity	NPC477610
0.7653	Intermediate Similarity	NPC88315
0.7623	Intermediate Similarity	NPC475746
0.7604	Intermediate Similarity	NPC252338
0.7583	Intermediate Similarity	NPC17059
0.7578	Intermediate Similarity	NPC82370
0.7568	Intermediate Similarity	NPC107077
0.7568	Intermediate Similarity	NPC223791
0.7546	Intermediate Similarity	NPC262898
0.7545	Intermediate Similarity	NPC473376
0.7543	Intermediate Similarity	NPC477608
0.7543	Intermediate Similarity	NPC477607
0.7536	Intermediate Similarity	NPC94752
0.7534	Intermediate Similarity	NPC155143
0.7531	Intermediate Similarity	NPC471536
0.7511	Intermediate Similarity	NPC326363
0.751	Intermediate Similarity	NPC125181
0.751	Intermediate Similarity	NPC242872
0.751	Intermediate Similarity	NPC263117
0.75	Intermediate Similarity	NPC179701
0.749	Intermediate Similarity	NPC117980
0.7489	Intermediate Similarity	NPC472285
0.7489	Intermediate Similarity	NPC475506
0.7489	Intermediate Similarity	NPC476818
0.7479	Intermediate Similarity	NPC474877
0.7479	Intermediate Similarity	NPC475969
0.7479	Intermediate Similarity	NPC475859
0.7478	Intermediate Similarity	NPC474412
0.7477	Intermediate Similarity	NPC74413
0.7476	Intermediate Similarity	NPC477611
0.7458	Intermediate Similarity	NPC245055
0.7456	Intermediate Similarity	NPC281049
0.7456	Intermediate Similarity	NPC477609
0.7455	Intermediate Similarity	NPC260900
0.7455	Intermediate Similarity	NPC193761
0.7453	Intermediate Similarity	NPC315555
0.7444	Intermediate Similarity	NPC314957
0.7442	Intermediate Similarity	NPC473342
0.7442	Intermediate Similarity	NPC477167
0.7441	Intermediate Similarity	NPC321939
0.7436	Intermediate Similarity	NPC470730
0.7436	Intermediate Similarity	NPC470729
0.7436	Intermediate Similarity	NPC477176
0.7436	Intermediate Similarity	NPC477175
0.7434	Intermediate Similarity	NPC54744
0.7431	Intermediate Similarity	NPC473640
0.7415	Intermediate Similarity	NPC63279
0.7406	Intermediate Similarity	NPC15102
0.7404	Intermediate Similarity	NPC477177
0.7397	Intermediate Similarity	NPC100321
0.7397	Intermediate Similarity	NPC477004
0.7395	Intermediate Similarity	NPC243716
0.7393	Intermediate Similarity	NPC191382
0.7393	Intermediate Similarity	NPC56109
0.7384	Intermediate Similarity	NPC297642
0.738	Intermediate Similarity	NPC264285
0.7373	Intermediate Similarity	NPC165743
0.7368	Intermediate Similarity	NPC59269
0.7364	Intermediate Similarity	NPC470497
0.7358	Intermediate Similarity	NPC228835
0.7353	Intermediate Similarity	NPC478028
0.7352	Intermediate Similarity	NPC67288
0.7352	Intermediate Similarity	NPC470499
0.7345	Intermediate Similarity	NPC320968
0.7328	Intermediate Similarity	NPC16352
0.7328	Intermediate Similarity	NPC155444
0.7319	Intermediate Similarity	NPC156003
0.7317	Intermediate Similarity	NPC153400
0.7313	Intermediate Similarity	NPC31385
0.7313	Intermediate Similarity	NPC110602
0.7313	Intermediate Similarity	NPC75726
0.7297	Intermediate Similarity	NPC476874
0.7293	Intermediate Similarity	NPC36405
0.7292	Intermediate Similarity	NPC478029
0.729	Intermediate Similarity	NPC235684
0.7288	Intermediate Similarity	NPC69843
0.7286	Intermediate Similarity	NPC111275
0.7281	Intermediate Similarity	NPC229348
0.7277	Intermediate Similarity	NPC476491
0.7273	Intermediate Similarity	NPC474389
0.7269	Intermediate Similarity	NPC323752
0.7251	Intermediate Similarity	NPC55772
0.7251	Intermediate Similarity	NPC283219
0.7243	Intermediate Similarity	NPC99939
0.7243	Intermediate Similarity	NPC308931
0.7234	Intermediate Similarity	NPC24370
0.7234	Intermediate Similarity	NPC214142
0.7234	Intermediate Similarity	NPC319232
0.7227	Intermediate Similarity	NPC89987
0.7225	Intermediate Similarity	NPC314603
0.7222	Intermediate Similarity	NPC64216
0.722	Intermediate Similarity	NPC473761
0.7215	Intermediate Similarity	NPC322135
0.7215	Intermediate Similarity	NPC95240
0.7206	Intermediate Similarity	NPC14812
0.7205	Intermediate Similarity	NPC470703
0.7203	Intermediate Similarity	NPC124920
0.7203	Intermediate Similarity	NPC34580
0.7203	Intermediate Similarity	NPC261251
0.7203	Intermediate Similarity	NPC118559
0.7203	Intermediate Similarity	NPC304307
0.7202	Intermediate Similarity	NPC304187
0.7202	Intermediate Similarity	NPC477166
0.7198	Intermediate Similarity	NPC160105
0.7197	Intermediate Similarity	NPC284888
0.7195	Intermediate Similarity	NPC149708
0.7191	Intermediate Similarity	NPC141428
0.719	Intermediate Similarity	NPC149155
0.719	Intermediate Similarity	NPC203468
0.719	Intermediate Similarity	NPC110500
0.7173	Intermediate Similarity	NPC100547
0.717	Intermediate Similarity	NPC11126
0.717	Intermediate Similarity	NPC248041
0.717	Intermediate Similarity	NPC126709
0.7167	Intermediate Similarity	NPC33064
0.7167	Intermediate Similarity	NPC272174
0.7163	Intermediate Similarity	NPC78020
0.7162	Intermediate Similarity	NPC473218
0.7162	Intermediate Similarity	NPC470702
0.7156	Intermediate Similarity	NPC473763
0.7156	Intermediate Similarity	NPC267885
0.7156	Intermediate Similarity	NPC476460
0.7156	Intermediate Similarity	NPC117244
0.7155	Intermediate Similarity	NPC54803
0.7155	Intermediate Similarity	NPC321592
0.7155	Intermediate Similarity	NPC473310
0.7149	Intermediate Similarity	NPC82472
0.7143	Intermediate Similarity	NPC203614
0.7143	Intermediate Similarity	NPC204491
0.7143	Intermediate Similarity	NPC223409
0.7137	Intermediate Similarity	NPC474896
0.7136	Intermediate Similarity	NPC91179
0.713	Intermediate Similarity	NPC62749
0.7125	Intermediate Similarity	NPC70155
0.7124	Intermediate Similarity	NPC277350
0.7123	Intermediate Similarity	NPC14113
0.7123	Intermediate Similarity	NPC64436
0.7123	Intermediate Similarity	NPC145885
0.7123	Intermediate Similarity	NPC84827
0.7113	Intermediate Similarity	NPC14288
0.711	Intermediate Similarity	NPC154339
0.7107	Intermediate Similarity	NPC15801
0.7106	Intermediate Similarity	NPC31097
0.7098	Intermediate Similarity	NPC300183
0.7094	Intermediate Similarity	NPC276657
0.7091	Intermediate Similarity	NPC267343
0.7089	Intermediate Similarity	NPC475338
0.7089	Intermediate Similarity	NPC213468
0.7089	Intermediate Similarity	NPC909
0.7087	Intermediate Similarity	NPC151976
0.7087	Intermediate Similarity	NPC87856
0.7081	Intermediate Similarity	NPC63751
0.708	Intermediate Similarity	NPC470505
0.7076	Intermediate Similarity	NPC147446
0.7076	Intermediate Similarity	NPC229893
0.7069	Intermediate Similarity	NPC132211
0.7048	Intermediate Similarity	NPC82053
0.7043	Intermediate Similarity	NPC72956

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 NPC63031 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	587
0.2-0.3	1068
0.3-0.4	2364
0.4-0.5	2734
0.5-0.6	1773
0.6-0.7	346
0.7-0.8	49
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
0.7953	Intermediate Similarity	NPD5426	Phase 3
0.7721	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7470	Discontinued
0.7578	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD7790	Approved
0.7489	Intermediate Similarity	NPD7791	Approved
0.7489	Intermediate Similarity	NPD7953	Approved
0.7489	Intermediate Similarity	NPD7952	Approved
0.7489	Intermediate Similarity	NPD7789	Approved
0.7489	Intermediate Similarity	NPD7951	Approved
0.7489	Intermediate Similarity	NPD7950	Approved
0.7455	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7441	Intermediate Similarity	NPD2096	Phase 2
0.7441	Intermediate Similarity	NPD2091	Phase 2
0.7432	Intermediate Similarity	NPD7001	Phase 3
0.7432	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7731	Approved
0.7425	Intermediate Similarity	NPD7730	Approved
0.7414	Intermediate Similarity	NPD7271	Approved
0.7397	Intermediate Similarity	NPD6999	Discontinued
0.7397	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD7781	Approved
0.7393	Intermediate Similarity	NPD2095	Phase 2
0.7393	Intermediate Similarity	NPD7780	Approved
0.7393	Intermediate Similarity	NPD2094	Phase 2
0.7393	Intermediate Similarity	NPD2092	Phase 2
0.7382	Intermediate Similarity	NPD7711	Discontinued
0.738	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7824	Approved
0.7336	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7603	Discontinued
0.7301	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6595	Phase 3
0.7296	Intermediate Similarity	NPD7716	Approved
0.7296	Intermediate Similarity	NPD7717	Approved
0.7249	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7970	Approved
0.7237	Intermediate Similarity	NPD8093	Discontinued
0.7217	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7944	Discontinued
0.719	Intermediate Similarity	NPD482	Approved
0.7168	Intermediate Similarity	NPD8322	Phase 2
0.7163	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8272	Phase 2
0.7143	Intermediate Similarity	NPD8073	Approved
0.713	Intermediate Similarity	NPD8094	Discontinued
0.7129	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7666	Phase 3
0.7061	Intermediate Similarity	NPD7665	Phase 2
0.7059	Intermediate Similarity	NPD7619	Phase 3
0.7059	Intermediate Similarity	NPD7618	Phase 3
0.7045	Intermediate Similarity	NPD6665	Discontinued
0.7042	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8072	Approved
0.7013	Intermediate Similarity	NPD4852	Phase 2
0.7004	Intermediate Similarity	NPD5901	Discontinued
0.6981	Remote Similarity	NPD750	Phase 2
0.6974	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7957	Phase 1
0.6957	Remote Similarity	NPD4520	Approved
0.6941	Remote Similarity	NPD8431	Approved
0.693	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7948	Phase 1
0.691	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD8098	Approved
0.6846	Remote Similarity	NPD6164	Phase 2
0.6846	Remote Similarity	NPD6165	Phase 2
0.6844	Remote Similarity	NPD6664	Approved
0.6844	Remote Similarity	NPD5003	Discontinued
0.6828	Remote Similarity	NPD484	Approved
0.6826	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5065	Approved
0.6723	Remote Similarity	NPD8097	Phase 3
0.6723	Remote Similarity	NPD8096	Phase 3
0.6711	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6987	Phase 1
0.6696	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD2510	Approved
0.6695	Remote Similarity	NPD2509	Approved
0.6694	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4427	Phase 2
0.668	Remote Similarity	NPD6995	Phase 1
0.6667	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8289	Discontinued
0.6667	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8284	Discontinued
0.664	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD56	Approved
0.6638	Remote Similarity	NPD8283	Approved
0.6638	Remote Similarity	NPD8282	Approved
0.6637	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4076	Approved
0.6621	Remote Similarity	NPD4079	Approved
0.6615	Remote Similarity	NPD6531	Approved
0.6615	Remote Similarity	NPD6530	Approved
0.6611	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD5818	Discontinued
0.6609	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4075	Phase 2
0.6605	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2844	Phase 3
0.6598	Remote Similarity	NPD1996	Discontinued
0.6592	Remote Similarity	NPD6217	Discontinued
0.6586	Remote Similarity	NPD5891	Approved
0.6575	Remote Similarity	NPD3505	Approved
0.6575	Remote Similarity	NPD3506	Approved
0.6569	Remote Similarity	NPD5612	Discontinued
0.6562	Remote Similarity	NPD3961	Discontinued
0.656	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7688	Phase 1
0.6548	Remote Similarity	NPD7576	Discontinued
0.654	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD4601	Approved
0.6537	Remote Similarity	NPD4600	Approved
0.6522	Remote Similarity	NPD7777	Approved
0.6522	Remote Similarity	NPD53	Approved
0.6522	Remote Similarity	NPD7778	Approved
0.6522	Remote Similarity	NPD8349	Phase 1
0.6515	Remote Similarity	NPD7878	Phase 2
0.6509	Remote Similarity	NPD5017	Discontinued
0.6507	Remote Similarity	NPD8460	Approved
0.6507	Remote Similarity	NPD8459	Approved
0.6507	Remote Similarity	NPD2289	Phase 3
0.6507	Remote Similarity	NPD2290	Phase 3
0.6504	Remote Similarity	NPD8364	Approved
0.6504	Remote Similarity	NPD8363	Approved
0.6504	Remote Similarity	NPD2565	Phase 2
0.6504	Remote Similarity	NPD4499	Approved
0.6504	Remote Similarity	NPD2564	Approved
0.6502	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6458	Discontinued
0.65	Remote Similarity	NPD2144	Approved
0.65	Remote Similarity	NPD7865	Approved
0.6496	Remote Similarity	NPD8114	Approved
0.6496	Remote Similarity	NPD8115	Approved
0.6494	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7181	Phase 3
0.6491	Remote Similarity	NPD802	Phase 2
0.6486	Remote Similarity	NPD3038	Discontinued
0.6483	Remote Similarity	NPD2916	Discontinued
0.6478	Remote Similarity	NPD2880	Discontinued
0.6478	Remote Similarity	NPD5559	Phase 2
0.6476	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD8256	Approved
0.6473	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD8257	Approved
0.6471	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6242	Discontinued
0.646	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6176	Phase 1
0.6449	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD2511	Approved
0.6447	Remote Similarity	NPD3404	Approved
0.6441	Remote Similarity	NPD6452	Discontinued
0.644	Remote Similarity	NPD7558	Phase 2
0.6438	Remote Similarity	NPD7817	Phase 1
0.6437	Remote Similarity	NPD4845	Discontinued
0.6432	Remote Similarity	NPD3389	Approved
0.6432	Remote Similarity	NPD3394	Approved
0.6432	Remote Similarity	NPD3393	Approved
0.6429	Remote Similarity	NPD6178	Phase 3
0.6429	Remote Similarity	NPD7564	Discontinued
0.6426	Remote Similarity	NPD3947	Discontinued
0.6426	Remote Similarity	NPD8169	Discontinued
0.6422	Remote Similarity	NPD1325	Approved
0.6422	Remote Similarity	NPD1326	Approved
0.6422	Remote Similarity	NPD8396	Approved
0.6422	Remote Similarity	NPD8395	Approved
0.6421	Remote Similarity	NPD8465	Approved
0.6421	Remote Similarity	NPD8427	Approved
0.6421	Remote Similarity	NPD8466	Approved
0.6421	Remote Similarity	NPD8429	Approved
0.6421	Remote Similarity	NPD8428	Approved
0.6421	Remote Similarity	NPD8467	Approved
0.6414	Remote Similarity	NPD8329	Phase 3
0.6414	Remote Similarity	NPD8399	Phase 1
0.6414	Remote Similarity	NPD8423	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