NPASS Compound

Structure

NPC473501 OpenBabel07101718332D 43 44 0 0 1 0 0 0 0 0999 V2000 6.0117 1.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6145 -6.5869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1800 0.7968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0003 -2.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1096 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1282 -5.2486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9901 2.3103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1868 -1.1561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2685 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8224 -5.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5922 1.6059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0058 -2.8786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3339 -1.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4679 -1.3116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3339 -2.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6019 -1.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4679 -3.3116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7359 -3.3116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3175 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0793 -4.9396 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4023 1.5013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5991 -1.9651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6019 -2.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8698 -2.8116 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5743 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2872 -3.9615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6045 -1.8605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2007 -3.5547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0743 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3736 -3.5547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 0.7957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1789 -1.8605 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2872 -3.9615 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7653 0.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2955 -2.8116 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7885 -4.3638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0254 -0.5570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2142 -4.3638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 1.7957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4511 -0.5570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 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 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 23 2 0 0 0 0 17 23 1 0 0 0 0 18 23 1 0 0 0 0 19 5 1 1 0 0 0 20 6 1 6 0 0 0 21 7 1 6 0 0 0 22 8 1 6 0 0 0 24 18 1 1 0 0 0 24 29 1 0 0 0 0 24 34 1 0 0 0 0 25 19 1 1 0 0 0 25 30 1 0 0 0 0 25 36 1 0 0 0 0 26 20 1 1 0 0 0 26 31 1 0 0 0 0 26 35 1 0 0 0 0 27 21 1 1 0 0 0 27 32 1 0 0 0 0 27 38 1 0 0 0 0 28 22 1 1 0 0 0 28 33 1 0 0 0 0 28 37 1 0 0 0 0 29 35 2 3 0 0 0 29 39 1 0 0 0 0 30 34 2 3 0 0 0 30 40 1 0 0 0 0 31 37 2 3 0 0 0 31 41 1 0 0 0 0 32 36 2 3 0 0 0 32 42 1 0 0 0 0 33 38 2 3 0 0 0 33 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	599.4
Volume:	640.054
LogP:	5.69
LogD:	5.325
LogS:	-5.09
# Rotatable Bonds:	10
TPSA:	145.5
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.281
Synthetic Accessibility Score:	4.844
Fsp3:	0.667
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:	-5.329
MDCK Permeability:	2.8762304282281548e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.954
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	94.66863250732422%
Volume Distribution (VD):	0.737
Pgp-substrate:	1.012978434562683%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.179
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.457
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.111

ADMET: Excretion

Clearance (CL):	4.39
Half-life (T1/2):	0.261

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.849
Drug-inuced Liver Injury (DILI):	0.357
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.064
Skin Sensitization:	0.024
Carcinogencity:	0.277
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.086

Download Data

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

Natural Product: NPC473501

Natural Product ID:	NPC473501
*Common Name:**	(3S,6S,9S,12S,15S)-3-Benzyl-6,9,12,15-Tetra-Sec-Butyl-1,4,7,10,13-Pentaazacyclopentadecane-2,5,8,11,14-Pentaone
IUPAC Name:	(3S,6S,9S,12S,15S)-3-benzyl-6,9,12,15-tetrakis[(2S)-butan-2-yl]-1,4,7,10,13-pentazacyclopentadecane-2,5,8,11,14-pentone
Synonyms:
Standard InCHIKey:	BKQUQGAKNSXOHH-PLDABBGUSA-N
Standard InCHI:	InChI=1S/C33H53N5O5/c1-9-19(5)25-30(40)34-24(18-23-16-14-13-15-17-23)29(39)35-26(20(6)10-2)31(41)37-28(22(8)12-4)33(43)38-27(21(7)11-3)32(42)36-25/h13-17,19-22,24-28H,9-12,18H2,1-8H3,(H,34,40)(H,35,39)(H,36,42)(H,37,41)(H,38,43)/t19-,20-,21-,22-,24-,25-,26-,27-,28-/m0/s1
SMILES:	CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CC2=CC=CC=C2)C(C)CC)C(C)CC)C(C)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443885
PubChem CID:	44572038
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:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO33240	nonomuraea sp. ta-0426	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19013063]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1125	Cell Line	T98G	Homo sapiens	IC50	=	655.0	nM	PMID[523671]

☑ 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 NPC473501 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	98
0.1-0.2	932
0.2-0.3	7211
0.3-0.4	19473
0.4-0.5	11592
0.5-0.6	2626
0.6-0.7	559
0.7-0.8	126
0.8-0.85	52
0.85-0.9	19
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475439
0.9889	High Similarity	NPC25565
0.9175	High Similarity	NPC224610
0.9175	High Similarity	NPC113326
0.9175	High Similarity	NPC88267
0.9175	High Similarity	NPC194390
0.914	High Similarity	NPC161972
0.914	High Similarity	NPC303045
0.8817	High Similarity	NPC226438
0.875	High Similarity	NPC311242
0.871	High Similarity	NPC159178
0.871	High Similarity	NPC471307
0.871	High Similarity	NPC74936
0.871	High Similarity	NPC121872
0.871	High Similarity	NPC141139
0.871	High Similarity	NPC78041
0.871	High Similarity	NPC209764
0.8602	High Similarity	NPC470877
0.8542	High Similarity	NPC58674
0.8476	Intermediate Similarity	NPC474584
0.8438	Intermediate Similarity	NPC471309
0.8387	Intermediate Similarity	NPC471638
0.8316	Intermediate Similarity	NPC172128
0.8316	Intermediate Similarity	NPC316108
0.8257	Intermediate Similarity	NPC169328
0.8252	Intermediate Similarity	NPC327481
0.8241	Intermediate Similarity	NPC317254
0.8182	Intermediate Similarity	NPC237420
0.8182	Intermediate Similarity	NPC470546
0.8182	Intermediate Similarity	NPC310467
0.8165	Intermediate Similarity	NPC470544
0.8105	Intermediate Similarity	NPC12429
0.8091	Intermediate Similarity	NPC470545
0.8091	Intermediate Similarity	NPC254088
0.8041	Intermediate Similarity	NPC245259
0.8036	Intermediate Similarity	NPC478016
0.8036	Intermediate Similarity	NPC478015
0.8036	Intermediate Similarity	NPC478014
0.8036	Intermediate Similarity	NPC45777
0.8036	Intermediate Similarity	NPC477061
0.802	Intermediate Similarity	NPC12730
0.7961	Intermediate Similarity	NPC471317
0.7946	Intermediate Similarity	NPC283760
0.7917	Intermediate Similarity	NPC325441
0.789	Intermediate Similarity	NPC276949
0.789	Intermediate Similarity	NPC35850
0.7876	Intermediate Similarity	NPC476990
0.7826	Intermediate Similarity	NPC46427
0.7818	Intermediate Similarity	NPC33742
0.781	Intermediate Similarity	NPC211551
0.7807	Intermediate Similarity	NPC202521
0.7788	Intermediate Similarity	NPC202613
0.7788	Intermediate Similarity	NPC164859
0.7788	Intermediate Similarity	NPC471310
0.7778	Intermediate Similarity	NPC319579
0.7755	Intermediate Similarity	NPC258627
0.7739	Intermediate Similarity	NPC252878
0.7719	Intermediate Similarity	NPC200964
0.7706	Intermediate Similarity	NPC329011
0.7699	Intermediate Similarity	NPC314992
0.7692	Intermediate Similarity	NPC47667
0.7692	Intermediate Similarity	NPC101719
0.7685	Intermediate Similarity	NPC258056
0.7679	Intermediate Similarity	NPC239357
0.7679	Intermediate Similarity	NPC2265
0.7672	Intermediate Similarity	NPC6975
0.766	Intermediate Similarity	NPC14326
0.7658	Intermediate Similarity	NPC118202
0.7647	Intermediate Similarity	NPC33168
0.7636	Intermediate Similarity	NPC273814
0.7629	Intermediate Similarity	NPC473031
0.7615	Intermediate Similarity	NPC474149
0.7607	Intermediate Similarity	NPC22746
0.7607	Intermediate Similarity	NPC222466
0.7604	Intermediate Similarity	NPC3210
0.7596	Intermediate Similarity	NPC469457
0.7589	Intermediate Similarity	NPC197470
0.7565	Intermediate Similarity	NPC190663
0.7563	Intermediate Similarity	NPC319766
0.7526	Intermediate Similarity	NPC203076
0.75	Intermediate Similarity	NPC473322
0.75	Intermediate Similarity	NPC71684
0.7479	Intermediate Similarity	NPC477937
0.7456	Intermediate Similarity	NPC38458
0.7456	Intermediate Similarity	NPC311737
0.7447	Intermediate Similarity	NPC192623
0.7438	Intermediate Similarity	NPC300315
0.7436	Intermediate Similarity	NPC160493
0.7411	Intermediate Similarity	NPC1986
0.7411	Intermediate Similarity	NPC474544
0.7407	Intermediate Similarity	NPC231705
0.7377	Intermediate Similarity	NPC255447
0.7377	Intermediate Similarity	NPC130309
0.7373	Intermediate Similarity	NPC35996
0.7368	Intermediate Similarity	NPC82963
0.7355	Intermediate Similarity	NPC111428
0.7339	Intermediate Similarity	NPC142297
0.7281	Intermediate Similarity	NPC188010
0.7273	Intermediate Similarity	NPC198747
0.7265	Intermediate Similarity	NPC80150
0.7264	Intermediate Similarity	NPC228400
0.7264	Intermediate Similarity	NPC214200
0.7258	Intermediate Similarity	NPC287401
0.7255	Intermediate Similarity	NPC265521
0.7248	Intermediate Similarity	NPC191215
0.7248	Intermediate Similarity	NPC274089
0.7193	Intermediate Similarity	NPC471318
0.7177	Intermediate Similarity	NPC326966
0.7167	Intermediate Similarity	NPC476260
0.7167	Intermediate Similarity	NPC476241
0.7154	Intermediate Similarity	NPC200589
0.7143	Intermediate Similarity	NPC293628
0.7143	Intermediate Similarity	NPC474862
0.7143	Intermediate Similarity	NPC10781
0.7143	Intermediate Similarity	NPC122493
0.713	Intermediate Similarity	NPC178902
0.7119	Intermediate Similarity	NPC476183
0.7107	Intermediate Similarity	NPC476179
0.7107	Intermediate Similarity	NPC4974
0.7107	Intermediate Similarity	NPC476125
0.7087	Intermediate Similarity	NPC471264
0.7087	Intermediate Similarity	NPC471265
0.7083	Intermediate Similarity	NPC472415
0.7075	Intermediate Similarity	NPC164514
0.7075	Intermediate Similarity	NPC108606
0.7075	Intermediate Similarity	NPC303611
0.7075	Intermediate Similarity	NPC290515
0.7075	Intermediate Similarity	NPC322598
0.7075	Intermediate Similarity	NPC226096
0.7059	Intermediate Similarity	NPC476281
0.7059	Intermediate Similarity	NPC476184
0.7048	Intermediate Similarity	NPC3371
0.7041	Intermediate Similarity	NPC477770
0.704	Intermediate Similarity	NPC246079
0.704	Intermediate Similarity	NPC246913
0.7037	Intermediate Similarity	NPC318154
0.7031	Intermediate Similarity	NPC132636
0.7019	Intermediate Similarity	NPC476483
0.7008	Intermediate Similarity	NPC314835
0.7	Intermediate Similarity	NPC67043
0.6984	Remote Similarity	NPC244866
0.6981	Remote Similarity	NPC324569
0.6977	Remote Similarity	NPC476259
0.6977	Remote Similarity	NPC163392
0.6977	Remote Similarity	NPC239762
0.6967	Remote Similarity	NPC472414
0.6964	Remote Similarity	NPC24101
0.6964	Remote Similarity	NPC96224
0.6953	Remote Similarity	NPC68865
0.6953	Remote Similarity	NPC64205
0.6953	Remote Similarity	NPC127741
0.6953	Remote Similarity	NPC6570
0.6942	Remote Similarity	NPC476278
0.6937	Remote Similarity	NPC474973
0.6937	Remote Similarity	NPC130898
0.6937	Remote Similarity	NPC474804
0.6935	Remote Similarity	NPC296712
0.6929	Remote Similarity	NPC248283
0.6929	Remote Similarity	NPC141050
0.6923	Remote Similarity	NPC14672
0.6923	Remote Similarity	NPC197921
0.6923	Remote Similarity	NPC315276
0.6923	Remote Similarity	NPC263493
0.6923	Remote Similarity	NPC469427
0.6923	Remote Similarity	NPC323164
0.6923	Remote Similarity	NPC469426
0.6923	Remote Similarity	NPC285926
0.6923	Remote Similarity	NPC476989
0.6923	Remote Similarity	NPC269398
0.6923	Remote Similarity	NPC168113
0.6911	Remote Similarity	NPC278097
0.6909	Remote Similarity	NPC150254
0.6909	Remote Similarity	NPC304761
0.6909	Remote Similarity	NPC226778
0.6909	Remote Similarity	NPC147000
0.6891	Remote Similarity	NPC319950
0.6887	Remote Similarity	NPC471320
0.6887	Remote Similarity	NPC471319
0.6882	Remote Similarity	NPC244738
0.688	Remote Similarity	NPC478147
0.687	Remote Similarity	NPC469360
0.687	Remote Similarity	NPC316202
0.687	Remote Similarity	NPC91953
0.687	Remote Similarity	NPC176226
0.687	Remote Similarity	NPC139326
0.687	Remote Similarity	NPC161069
0.687	Remote Similarity	NPC197682
0.686	Remote Similarity	NPC109151
0.6855	Remote Similarity	NPC210950
0.6855	Remote Similarity	NPC199738
0.6847	Remote Similarity	NPC143516
0.6837	Remote Similarity	NPC231986
0.6833	Remote Similarity	NPC17388
0.6833	Remote Similarity	NPC289330
0.6833	Remote Similarity	NPC53596
0.6833	Remote Similarity	NPC471308
0.6833	Remote Similarity	NPC160120
0.6818	Remote Similarity	NPC476978
0.6818	Remote Similarity	NPC178681
0.6814	Remote Similarity	NPC153690

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 NPC473501 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	87
0.1-0.2	466
0.2-0.3	915
0.3-0.4	2728
0.4-0.5	3009
0.5-0.6	1486
0.6-0.7	378
0.7-0.8	76
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9062	High Similarity	NPD4760	Clinical (unspecified phase)
0.8925	High Similarity	NPD6690	Approved
0.8723	High Similarity	NPD1814	Approved
0.8723	High Similarity	NPD1812	Approved
0.8351	Intermediate Similarity	NPD4814	Discontinued
0.8061	Intermediate Similarity	NPD1080	Approved
0.8	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD3642	Approved
0.7944	Intermediate Similarity	NPD3644	Approved
0.7944	Intermediate Similarity	NPD3643	Approved
0.7928	Intermediate Similarity	NPD6360	Discontinued
0.7876	Intermediate Similarity	NPD7342	Discontinued
0.7706	Intermediate Similarity	NPD3651	Discontinued
0.7699	Intermediate Similarity	NPD2218	Phase 2
0.7699	Intermediate Similarity	NPD2217	Approved
0.7677	Intermediate Similarity	NPD530	Approved
0.7647	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD5717	Approved
0.7642	Intermediate Similarity	NPD1040	Phase 2
0.7629	Intermediate Similarity	NPD9538	Approved
0.7624	Intermediate Similarity	NPD1081	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7522	Discontinued
0.7589	Intermediate Similarity	NPD1348	Approved
0.7551	Intermediate Similarity	NPD1101	Approved
0.7549	Intermediate Similarity	NPD2895	Discontinued
0.7549	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6406	Approved
0.7477	Intermediate Similarity	NPD999	Phase 2
0.7434	Intermediate Similarity	NPD7508	Discontinued
0.7426	Intermediate Similarity	NPD752	Approved
0.7395	Intermediate Similarity	NPD5367	Discontinued
0.7373	Intermediate Similarity	NPD5702	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4119	Approved
0.7358	Intermediate Similarity	NPD5716	Approved
0.7355	Intermediate Similarity	NPD7828	Discontinued
0.7353	Intermediate Similarity	NPD3718	Approved
0.7353	Intermediate Similarity	NPD3719	Approved
0.7333	Intermediate Similarity	NPD1067	Discontinued
0.7328	Intermediate Similarity	NPD5981	Approved
0.7328	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4165	Phase 2
0.7321	Intermediate Similarity	NPD3066	Phase 2
0.7311	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1542	Approved
0.7273	Intermediate Similarity	NPD187	Approved
0.7273	Intermediate Similarity	NPD7451	Discontinued
0.7273	Intermediate Similarity	NPD2678	Approved
0.7273	Intermediate Similarity	NPD2679	Approved
0.7258	Intermediate Similarity	NPD8118	Discontinued
0.7257	Intermediate Similarity	NPD2658	Approved
0.7257	Intermediate Similarity	NPD3148	Approved
0.7257	Intermediate Similarity	NPD3150	Approved
0.7257	Intermediate Similarity	NPD3147	Approved
0.7257	Intermediate Similarity	NPD2659	Approved
0.7257	Intermediate Similarity	NPD3149	Approved
0.7241	Intermediate Similarity	NPD6093	Discontinued
0.7203	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8265	Approved
0.7196	Intermediate Similarity	NPD854	Approved
0.7196	Intermediate Similarity	NPD855	Approved
0.7196	Intermediate Similarity	NPD1540	Approved
0.7184	Intermediate Similarity	NPD1066	Discontinued
0.7184	Intermediate Similarity	NPD719	Approved
0.7184	Intermediate Similarity	NPD1409	Phase 3
0.7184	Intermediate Similarity	NPD720	Approved
0.7177	Intermediate Similarity	NPD7908	Discontinued
0.7168	Intermediate Similarity	NPD1762	Approved
0.7168	Intermediate Similarity	NPD1764	Approved
0.7156	Intermediate Similarity	NPD563	Approved
0.7156	Intermediate Similarity	NPD564	Approved
0.7154	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9566	Approved
0.712	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6325	Discontinued
0.7103	Intermediate Similarity	NPD1275	Phase 2
0.7097	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8172	Phase 2
0.7087	Intermediate Similarity	NPD8173	Phase 2
0.7075	Intermediate Similarity	NPD9612	Approved
0.7075	Intermediate Similarity	NPD9609	Approved
0.7075	Intermediate Similarity	NPD9611	Approved
0.7075	Intermediate Similarity	NPD4117	Approved
0.7069	Intermediate Similarity	NPD3123	Discovery
0.7064	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD8416	Discontinued
0.7049	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8011	Discontinued
0.7037	Intermediate Similarity	NPD4719	Phase 2
0.7037	Intermediate Similarity	NPD4818	Approved
0.7037	Intermediate Similarity	NPD4817	Approved
0.7034	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1394	Approved
0.7016	Intermediate Similarity	NPD4125	Approved
0.701	Intermediate Similarity	NPD472	Approved
0.7008	Intermediate Similarity	NPD8643	Discontinued
0.7	Intermediate Similarity	NPD1018	Approved
0.6992	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4253	Approved
0.6991	Remote Similarity	NPD2583	Phase 2
0.6991	Remote Similarity	NPD4254	Approved
0.6981	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1875	Phase 1
0.6977	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4738	Phase 2
0.696	Remote Similarity	NPD3136	Phase 2
0.6952	Remote Similarity	NPD7344	Phase 1
0.6952	Remote Similarity	NPD7343	Discovery
0.6942	Remote Similarity	NPD6624	Discontinued
0.6942	Remote Similarity	NPD2584	Suspended
0.6923	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3407	Phase 3
0.6909	Remote Similarity	NPD314	Approved
0.6909	Remote Similarity	NPD315	Approved
0.6909	Remote Similarity	NPD10	Approved
0.6909	Remote Similarity	NPD309	Approved
0.6909	Remote Similarity	NPD310	Approved
0.6909	Remote Similarity	NPD311	Approved
0.6903	Remote Similarity	NPD1107	Approved
0.6903	Remote Similarity	NPD1108	Approved
0.6899	Remote Similarity	NPD8154	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2212	Approved
0.6891	Remote Similarity	NPD2210	Approved
0.6882	Remote Similarity	NPD9728	Phase 1
0.6881	Remote Similarity	NPD1735	Approved
0.6881	Remote Similarity	NPD1417	Approved
0.6881	Remote Similarity	NPD1419	Approved
0.6881	Remote Similarity	NPD1737	Approved
0.6881	Remote Similarity	NPD1736	Approved
0.688	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8076	Discontinued
0.6864	Remote Similarity	NPD1359	Approved
0.6855	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD9712	Approved
0.6838	Remote Similarity	NPD4031	Approved
0.6838	Remote Similarity	NPD4032	Approved
0.6838	Remote Similarity	NPD2622	Approved
0.6837	Remote Similarity	NPD3035	Approved
0.681	Remote Similarity	NPD23	Approved
0.6809	Remote Similarity	NPD9588	Approved
0.6809	Remote Similarity	NPD9592	Approved
0.6809	Remote Similarity	NPD9590	Approved
0.6809	Remote Similarity	NPD9589	Approved
0.6809	Remote Similarity	NPD9594	Approved
0.6809	Remote Similarity	NPD80	Approved
0.6809	Remote Similarity	NPD9591	Approved
0.6809	Remote Similarity	NPD9593	Approved
0.6807	Remote Similarity	NPD4479	Discontinued
0.6804	Remote Similarity	NPD1053	Approved
0.6804	Remote Similarity	NPD1051	Approved
0.6804	Remote Similarity	NPD1052	Approved
0.68	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5323	Approved
0.6768	Remote Similarity	NPD4169	Approved
0.6768	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4170	Approved
0.6759	Remote Similarity	NPD9711	Approved
0.6759	Remote Similarity	NPD1724	Approved
0.6759	Remote Similarity	NPD253	Approved
0.6759	Remote Similarity	NPD9710	Approved
0.6742	Remote Similarity	NPD7978	Discontinued
0.6735	Remote Similarity	NPD5371	Approved
0.6735	Remote Similarity	NPD5372	Approved
0.6733	Remote Similarity	NPD2208	Approved
0.6733	Remote Similarity	NPD2205	Approved
0.6721	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD293	Approved
0.6701	Remote Similarity	NPD295	Approved
0.6701	Remote Similarity	NPD296	Approved
0.6699	Remote Similarity	NPD531	Approved
0.6694	Remote Similarity	NPD3098	Discontinued
0.6667	Remote Similarity	NPD3626	Phase 3
0.6667	Remote Similarity	NPD6854	Phase 3
0.6667	Remote Similarity	NPD3680	Approved
0.6667	Remote Similarity	NPD7450	Phase 2
0.6667	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1415	Approved
0.6667	Remote Similarity	NPD8323	Discontinued
0.6667	Remote Similarity	NPD1682	Approved
0.6667	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1681	Approved
0.6667	Remote Similarity	NPD4231	Approved
0.6667	Remote Similarity	NPD3681	Approved
0.6667	Remote Similarity	NPD3682	Approved
0.6667	Remote Similarity	NPD5335	Discontinued
0.6667	Remote Similarity	NPD4229	Approved
0.6667	Remote Similarity	NPD3683	Approved
0.6667	Remote Similarity	NPD5103	Approved
0.6667	Remote Similarity	NPD1680	Approved
0.6641	Remote Similarity	NPD5299	Approved
0.6641	Remote Similarity	NPD6852	Discontinued
0.6641	Remote Similarity	NPD6901	Phase 3
0.6639	Remote Similarity	NPD4651	Clinical (unspecified phase)

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