NPASS Compound

Structure

NPC471536 OpenBabel07101718232D 38 42 0 0 1 0 0 0 0 0999 V2000 -1.3500 2.5903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3054 2.3873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4352 -2.5593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5893 -2.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2031 -2.5358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5228 -3.1894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6964 1.8645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5893 -4.0244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2404 -3.0476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4352 -3.5360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7434 -2.5593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8145 -2.2574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4517 -2.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6072 1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7434 -3.5360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6548 -1.9321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 -1.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2108 -0.3995 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.9536 0.7325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8644 0.3263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5741 -0.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9126 1.3417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5127 -1.3285 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.2811 -4.0244 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.1776 -3.5411 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.8680 1.5448 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6108 0.4128 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2590 2.0676 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8145 -3.8378 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5626 1.2553 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2554 -0.1965 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 -0.3018 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9982 0.9355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8198 0.1232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5509 -0.7902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4416 -1.0267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 7 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 29 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 30 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 17 2 0 0 0 0 14 26 1 0 0 0 0 15 2 1 1 0 0 0 15 20 1 0 0 0 0 15 31 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 33 1 0 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 19 32 1 0 0 0 0 20 32 2 0 0 0 0 20 34 1 0 0 0 0 21 31 2 0 0 0 0 21 35 1 0 0 0 0 22 36 2 0 0 0 0 22 38 1 0 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 23 29 1 0 0 0 0 24 37 1 0 0 0 0 33 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	647.01
Volume:	511.372
LogP:	2.026
LogD:	1.075
LogS:	-4.376
# Rotatable Bonds:	8
TPSA:	202.12
# H-Bond Aceptor:	12
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.084
Synthetic Accessibility Score:	4.572
Fsp3:	0.25
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:	-5.85
MDCK Permeability:	3.5911534723709337e-06
Pgp-inhibitor:	0.216
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.078
30% Bioavailability (F30%):	0.861

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.591
Plasma Protein Binding (PPB):	94.00828552246094%
Volume Distribution (VD):	0.62
Pgp-substrate:	14.637955665588379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.47
CYP2C19-inhibitor:	0.568
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.501
CYP2C9-substrate:	0.361
CYP2D6-inhibitor:	0.847
CYP2D6-substrate:	0.261
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	1.579
Half-life (T1/2):	0.236

ADMET: Toxicity

hERG Blockers:	0.26
Human Hepatotoxicity (H-HT):	0.521
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.374
Carcinogencity:	0.754
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC471536

Natural Product ID:	NPC471536
*Common Name:**	(Cyclo[(6-Bromo-8-(6-Bromobenzioxazol-3(1H)-One)-8-Hydroxy)Tryptophan)]Arginine)
IUPAC Name:	2-[3-[(2S)-5-[(6-bromo-1H-indol-3-yl)-(6-bromo-3-oxo-1H-2,1-benzoxazol-7-yl)-hydroxymethyl]-3,6-dioxopiperazin-2-yl]propyl]guanidine
Synonyms:
Standard InCHIKey:	HHZVDLQSGVLYRE-NQDWNACJSA-N
Standard InCHI:	InChI=1S/C24H23Br2N7O5/c25-10-3-4-11-13(9-30-16(11)8-10)24(37,17-14(26)6-5-12-18(17)33-38-22(12)36)19-21(35)31-15(20(34)32-19)2-1-7-29-23(27)28/h3-6,8-9,15,19,30,33,37H,1-2,7H2,(H,31,35)(H,32,34)(H4,27,28,29)/t15-,19?,24?/m0/s1
SMILES:	NC(=N)NCCC[C@@H]1N=C(O)C(N=C1O)C(c1c(Br)ccc2c1[nH]oc2=O)(c1c[nH]c2c1ccc(c2)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255451
PubChem CID:	44448166
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

*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
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	collected at 50-60 m depth in the Kosterfjord on the Swedish west coast	2001-MAR	PMID[15043412]
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043412]
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067154]
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271554]
NPO5772	Geodia barretti	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222779]
NPO5772	Geodia barretti	Species	Geodiidae	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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5137	Organism	Balanus improvisus	Balanus improvisus	EC50	=	15.0	nM	PMID[456195]

☑ 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 NPC471536 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	585
0.1-0.2	4009
0.2-0.3	13437
0.3-0.4	16820
0.4-0.5	4029
0.5-0.6	2568
0.6-0.7	1180
0.7-0.8	68
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7879	Intermediate Similarity	NPC477114
0.7787	Intermediate Similarity	NPC201831
0.7787	Intermediate Similarity	NPC17487
0.7755	Intermediate Similarity	NPC477107
0.7755	Intermediate Similarity	NPC477108
0.7755	Intermediate Similarity	NPC477109
0.7738	Intermediate Similarity	NPC216369
0.7692	Intermediate Similarity	NPC477167
0.7692	Intermediate Similarity	NPC473342
0.7692	Intermediate Similarity	NPC304187
0.7692	Intermediate Similarity	NPC477166
0.7675	Intermediate Similarity	NPC82053
0.7629	Intermediate Similarity	NPC207020
0.7577	Intermediate Similarity	NPC475935
0.7577	Intermediate Similarity	NPC94211
0.7577	Intermediate Similarity	NPC52909
0.7542	Intermediate Similarity	NPC475736
0.7533	Intermediate Similarity	NPC303820
0.7533	Intermediate Similarity	NPC205254
0.7533	Intermediate Similarity	NPC23420
0.7533	Intermediate Similarity	NPC106771
0.7531	Intermediate Similarity	NPC63031
0.7479	Intermediate Similarity	NPC156003
0.7458	Intermediate Similarity	NPC229893
0.7452	Intermediate Similarity	NPC77101
0.7447	Intermediate Similarity	NPC470703
0.7436	Intermediate Similarity	NPC82370
0.7432	Intermediate Similarity	NPC278434
0.7406	Intermediate Similarity	NPC276657
0.7404	Intermediate Similarity	NPC473218
0.7404	Intermediate Similarity	NPC470702
0.7362	Intermediate Similarity	NPC72956
0.7349	Intermediate Similarity	NPC37152
0.7333	Intermediate Similarity	NPC474195
0.7331	Intermediate Similarity	NPC153980
0.7331	Intermediate Similarity	NPC6865
0.7331	Intermediate Similarity	NPC128084
0.7321	Intermediate Similarity	NPC321939
0.73	Intermediate Similarity	NPC477610
0.7289	Intermediate Similarity	NPC83111
0.7284	Intermediate Similarity	NPC476818
0.7284	Intermediate Similarity	NPC474196
0.728	Intermediate Similarity	NPC472285
0.7269	Intermediate Similarity	NPC88315
0.7258	Intermediate Similarity	NPC97902
0.7257	Intermediate Similarity	NPC471193
0.7257	Intermediate Similarity	NPC471194
0.7244	Intermediate Similarity	NPC321708
0.7238	Intermediate Similarity	NPC471192
0.7235	Intermediate Similarity	NPC117980
0.7231	Intermediate Similarity	NPC473317
0.722	Intermediate Similarity	NPC74360
0.722	Intermediate Similarity	NPC475746
0.7192	Intermediate Similarity	NPC74619
0.7189	Intermediate Similarity	NPC174489
0.7179	Intermediate Similarity	NPC473376
0.7177	Intermediate Similarity	NPC279189
0.7177	Intermediate Similarity	NPC200553
0.7177	Intermediate Similarity	NPC207686
0.7167	Intermediate Similarity	NPC193761
0.7162	Intermediate Similarity	NPC202812
0.716	Intermediate Similarity	NPC162002
0.7143	Intermediate Similarity	NPC125597
0.7143	Intermediate Similarity	NPC131887
0.7131	Intermediate Similarity	NPC26641
0.7124	Intermediate Similarity	NPC471944
0.712	Intermediate Similarity	NPC245055
0.7112	Intermediate Similarity	NPC477004
0.7107	Intermediate Similarity	NPC477609
0.7105	Intermediate Similarity	NPC138370
0.71	Intermediate Similarity	NPC262898
0.7095	Intermediate Similarity	NPC36405
0.7095	Intermediate Similarity	NPC74969
0.7094	Intermediate Similarity	NPC476874
0.7083	Intermediate Similarity	NPC54744
0.7082	Intermediate Similarity	NPC166209
0.7082	Intermediate Similarity	NPC77241
0.7082	Intermediate Similarity	NPC13456
0.7082	Intermediate Similarity	NPC269203
0.708	Intermediate Similarity	NPC474357
0.7069	Intermediate Similarity	NPC67288
0.7061	Intermediate Similarity	NPC154339
0.7057	Intermediate Similarity	NPC263117
0.7057	Intermediate Similarity	NPC242872
0.7057	Intermediate Similarity	NPC125181
0.7056	Intermediate Similarity	NPC179701
0.7056	Intermediate Similarity	NPC477607
0.7056	Intermediate Similarity	NPC477608
0.7042	Intermediate Similarity	NPC219087
0.704	Intermediate Similarity	NPC89987
0.704	Intermediate Similarity	NPC267078
0.704	Intermediate Similarity	NPC935
0.7039	Intermediate Similarity	NPC201266
0.7039	Intermediate Similarity	NPC153123
0.7039	Intermediate Similarity	NPC475914
0.7039	Intermediate Similarity	NPC268744
0.7039	Intermediate Similarity	NPC220797
0.7039	Intermediate Similarity	NPC474318
0.7038	Intermediate Similarity	NPC314882
0.7026	Intermediate Similarity	NPC227582
0.7021	Intermediate Similarity	NPC473761
0.702	Intermediate Similarity	NPC295452
0.702	Intermediate Similarity	NPC171393
0.7017	Intermediate Similarity	NPC171787
0.7016	Intermediate Similarity	NPC476491
0.7012	Intermediate Similarity	NPC70155
0.7012	Intermediate Similarity	NPC229348
0.7004	Intermediate Similarity	NPC235684
0.7004	Intermediate Similarity	NPC178858
0.6996	Remote Similarity	NPC59269
0.6996	Remote Similarity	NPC478006
0.6996	Remote Similarity	NPC474389
0.6996	Remote Similarity	NPC15801
0.6996	Remote Similarity	NPC474916
0.6991	Remote Similarity	NPC110158
0.6983	Remote Similarity	NPC478157
0.697	Remote Similarity	NPC267343
0.6967	Remote Similarity	NPC264285
0.696	Remote Similarity	NPC15102
0.6958	Remote Similarity	NPC63109
0.6957	Remote Similarity	NPC477549
0.6944	Remote Similarity	NPC284888
0.6942	Remote Similarity	NPC282247
0.6936	Remote Similarity	NPC315491
0.6936	Remote Similarity	NPC45459
0.6936	Remote Similarity	NPC252338
0.6933	Remote Similarity	NPC471191
0.6932	Remote Similarity	NPC470323
0.6929	Remote Similarity	NPC320968
0.6926	Remote Similarity	NPC27041
0.6923	Remote Similarity	NPC16352
0.6923	Remote Similarity	NPC220851
0.692	Remote Similarity	NPC111275
0.692	Remote Similarity	NPC284775
0.692	Remote Similarity	NPC33949
0.6917	Remote Similarity	NPC80596
0.6917	Remote Similarity	NPC478158
0.6908	Remote Similarity	NPC214142
0.6908	Remote Similarity	NPC24370
0.6908	Remote Similarity	NPC319232
0.6906	Remote Similarity	NPC110500
0.6906	Remote Similarity	NPC149155
0.6906	Remote Similarity	NPC203468
0.6905	Remote Similarity	NPC321592
0.6905	Remote Similarity	NPC54803
0.6904	Remote Similarity	NPC183777
0.6897	Remote Similarity	NPC188821
0.6897	Remote Similarity	NPC474180
0.6894	Remote Similarity	NPC237414
0.6892	Remote Similarity	NPC326363
0.6892	Remote Similarity	NPC322135
0.6892	Remote Similarity	NPC223409
0.6889	Remote Similarity	NPC283219
0.6886	Remote Similarity	NPC282103
0.688	Remote Similarity	NPC261251
0.688	Remote Similarity	NPC34580
0.688	Remote Similarity	NPC124920
0.688	Remote Similarity	NPC118559
0.688	Remote Similarity	NPC304307
0.6878	Remote Similarity	NPC63751
0.6875	Remote Similarity	NPC267885
0.6875	Remote Similarity	NPC476524
0.6867	Remote Similarity	NPC141428
0.6866	Remote Similarity	NPC314056
0.6864	Remote Similarity	NPC213308
0.6857	Remote Similarity	NPC477715
0.6853	Remote Similarity	NPC100547
0.6851	Remote Similarity	NPC470499
0.685	Remote Similarity	NPC33064
0.685	Remote Similarity	NPC182222
0.6842	Remote Similarity	NPC272174
0.684	Remote Similarity	NPC315467
0.6838	Remote Similarity	NPC242209
0.6831	Remote Similarity	NPC75634
0.6829	Remote Similarity	NPC477714
0.6828	Remote Similarity	NPC71037
0.6827	Remote Similarity	NPC64216
0.6825	Remote Similarity	NPC95240
0.6825	Remote Similarity	NPC116622
0.6822	Remote Similarity	NPC74413
0.6822	Remote Similarity	NPC293917
0.6818	Remote Similarity	NPC309845
0.6815	Remote Similarity	NPC478009
0.6815	Remote Similarity	NPC478010
0.6814	Remote Similarity	NPC213468
0.6814	Remote Similarity	NPC126709
0.6814	Remote Similarity	NPC248041
0.6814	Remote Similarity	NPC233050
0.6814	Remote Similarity	NPC276540
0.6813	Remote Similarity	NPC57690
0.6809	Remote Similarity	NPC156704
0.6807	Remote Similarity	NPC260900
0.6805	Remote Similarity	NPC266249
0.6802	Remote Similarity	NPC78020
0.6798	Remote Similarity	NPC14288
0.6797	Remote Similarity	NPC28945
0.6797	Remote Similarity	NPC221873
0.6795	Remote Similarity	NPC276517
0.6793	Remote Similarity	NPC470497
0.6792	Remote Similarity	NPC175602

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 NPC471536 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	654
0.2-0.3	1043
0.3-0.4	2325
0.4-0.5	2584
0.5-0.6	1893
0.6-0.7	378
0.7-0.8	5
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
0.7788	Intermediate Similarity	NPD5901	Discontinued
0.7308	Intermediate Similarity	NPD2510	Approved
0.7308	Intermediate Similarity	NPD2509	Approved
0.72	Intermediate Similarity	NPD4948	Discontinued
0.7175	Intermediate Similarity	NPD2094	Phase 2
0.7175	Intermediate Similarity	NPD2095	Phase 2
0.7175	Intermediate Similarity	NPD2092	Phase 2
0.7143	Intermediate Similarity	NPD7470	Discontinued
0.7143	Intermediate Similarity	NPD2096	Phase 2
0.7143	Intermediate Similarity	NPD2091	Phase 2
0.7137	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3918	Approved
0.7113	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3917	Approved
0.7101	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3915	Approved
0.7054	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3394	Approved
0.7025	Intermediate Similarity	NPD3393	Approved
0.7025	Intermediate Similarity	NPD3389	Approved
0.7024	Intermediate Similarity	NPD5891	Approved
0.702	Intermediate Similarity	NPD7860	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD8094	Discontinued
0.7004	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6458	Discontinued
0.6962	Remote Similarity	NPD5426	Phase 3
0.6948	Remote Similarity	NPD6164	Phase 2
0.6948	Remote Similarity	NPD6165	Phase 2
0.6947	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3794	Approved
0.6942	Remote Similarity	NPD3795	Approved
0.6936	Remote Similarity	NPD484	Approved
0.6914	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7970	Approved
0.6911	Remote Similarity	NPD1996	Discontinued
0.6906	Remote Similarity	NPD482	Approved
0.6905	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8093	Discontinued
0.6898	Remote Similarity	NPD7878	Phase 2
0.6891	Remote Similarity	NPD6987	Phase 1
0.688	Remote Similarity	NPD4845	Discontinued
0.6875	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3006	Discontinued
0.6822	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7948	Phase 1
0.6807	Remote Similarity	NPD8073	Approved
0.6802	Remote Similarity	NPD6770	Approved
0.68	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2813	Phase 3
0.6784	Remote Similarity	NPD6595	Phase 3
0.6777	Remote Similarity	NPD6529	Discontinued
0.6774	Remote Similarity	NPD6242	Discontinued
0.6763	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD8097	Phase 3
0.6762	Remote Similarity	NPD8096	Phase 3
0.6761	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6752	Phase 1
0.676	Remote Similarity	NPD6753	Phase 1
0.6756	Remote Similarity	NPD5065	Approved
0.6754	Remote Similarity	NPD3178	Discontinued
0.6752	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6999	Discontinued
0.6748	Remote Similarity	NPD6733	Discontinued
0.6739	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7001	Phase 3
0.6721	Remote Similarity	NPD5475	Discontinued
0.6719	Remote Similarity	NPD6142	Phase 3
0.6705	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD2803	Discontinued
0.6693	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD3222	Phase 2
0.668	Remote Similarity	NPD3947	Discontinued
0.6667	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5003	Discontinued
0.6667	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD2008	Discontinued
0.6653	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7957	Phase 1
0.6642	Remote Similarity	NPD5050	Approved
0.6639	Remote Similarity	NPD7778	Approved
0.6639	Remote Similarity	NPD7777	Approved
0.6639	Remote Similarity	NPD8072	Approved
0.6639	Remote Similarity	NPD4506	Discontinued
0.6639	Remote Similarity	NPD53	Approved
0.6637	Remote Similarity	NPD750	Phase 2
0.6626	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2411	Approved
0.6626	Remote Similarity	NPD4852	Phase 2
0.6624	Remote Similarity	NPD6226	Phase 3
0.6624	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3013	Phase 3
0.6609	Remote Similarity	NPD8431	Approved
0.6598	Remote Similarity	NPD7665	Phase 2
0.6598	Remote Similarity	NPD7666	Phase 3
0.6596	Remote Similarity	NPD2336	Approved
0.6594	Remote Similarity	NPD8386	Phase 2
0.6593	Remote Similarity	NPD6531	Approved
0.6593	Remote Similarity	NPD6530	Approved
0.6586	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD3280	Approved
0.6573	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5856	Discontinued
0.6569	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6173	Approved
0.6558	Remote Similarity	NPD7689	Approved
0.6553	Remote Similarity	NPD4499	Approved
0.6552	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD1326	Approved
0.6549	Remote Similarity	NPD1325	Approved
0.6543	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD8098	Approved
0.6542	Remote Similarity	NPD3814	Phase 1
0.654	Remote Similarity	NPD1173	Approved
0.6531	Remote Similarity	NPD6487	Approved
0.6531	Remote Similarity	NPD7232	Discontinued
0.6531	Remote Similarity	NPD6486	Approved
0.6516	Remote Similarity	NPD2317	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6154	Approved
0.651	Remote Similarity	NPD7603	Discontinued
0.6508	Remote Similarity	NPD5827	Discontinued
0.6504	Remote Similarity	NPD2844	Phase 3
0.6502	Remote Similarity	NPD6176	Phase 1
0.6498	Remote Similarity	NPD3404	Approved
0.6498	Remote Similarity	NPD6665	Discontinued
0.6496	Remote Similarity	NPD706	Phase 1
0.6493	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7415	Suspended
0.6485	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD2307	Discontinued
0.6484	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD2564	Approved
0.6483	Remote Similarity	NPD2565	Phase 2
0.6482	Remote Similarity	NPD4301	Approved
0.648	Remote Similarity	NPD5490	Discontinued
0.648	Remote Similarity	NPD3353	Approved
0.6479	Remote Similarity	NPD5482	Discontinued
0.6471	Remote Similarity	NPD4890	Phase 2
0.6466	Remote Similarity	NPD3243	Approved
0.6464	Remote Similarity	NPD7576	Discontinued
0.6459	Remote Similarity	NPD7780	Approved
0.6459	Remote Similarity	NPD7781	Approved
0.6459	Remote Similarity	NPD7767	Approved
0.6457	Remote Similarity	NPD6995	Phase 1
0.6453	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4500	Approved
0.6446	Remote Similarity	NPD4501	Approved
0.6446	Remote Similarity	NPD6479	Discontinued
0.6441	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7951	Approved
0.6423	Remote Similarity	NPD7950	Approved
0.6423	Remote Similarity	NPD7789	Approved
0.6423	Remote Similarity	NPD7791	Approved
0.6423	Remote Similarity	NPD7790	Approved
0.6423	Remote Similarity	NPD7953	Approved
0.6423	Remote Similarity	NPD7952	Approved
0.6422	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6452	Discontinued
0.6411	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD8321	Discontinued
0.6409	Remote Similarity	NPD7688	Phase 1
0.6409	Remote Similarity	NPD8106	Phase 2
0.6408	Remote Similarity	NPD944	Approved
0.6405	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD7404	Approved
0.6397	Remote Similarity	NPD2442	Approved
0.6397	Remote Similarity	NPD2443	Approved
0.6393	Remote Similarity	NPD3775	Approved
0.6393	Remote Similarity	NPD3773	Approved
0.6393	Remote Similarity	NPD3774	Approved
0.6392	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD3959	Phase 2
0.6391	Remote Similarity	NPD3962	Phase 2
0.639	Remote Similarity	NPD6664	Approved
0.6382	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7010	Phase 3
0.6381	Remote Similarity	NPD4558	Phase 2
0.6381	Remote Similarity	NPD7711	Discontinued
0.6379	Remote Similarity	NPD4079	Approved
0.6379	Remote Similarity	NPD4076	Approved
0.6377	Remote Similarity	NPD7857	Phase 3
0.6377	Remote Similarity	NPD7856	Phase 2
0.6377	Remote Similarity	NPD5821	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