NPASS Compound

Structure

NPC470544 OpenBabel07101719512D 38 40 0 0 1 0 0 0 0 0999 V2000 0.0000 -4.8363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4286 -4.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8399 1.6496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2684 0.8248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3160 -4.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4762 0.8248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7974 -2.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6372 -1.0847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9726 -2.5782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7974 -1.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8124 -0.6085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6372 -2.0371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1478 -2.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9726 -0.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9877 -1.0847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8124 -2.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4982 -0.1972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3381 -2.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4762 -4.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3160 0.8248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1478 -1.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9877 -2.0371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6734 -0.6734 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5133 -2.5133 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -3.1867 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8399 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9199 -1.5934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7598 -1.5934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9199 -3.4332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9199 0.2465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6734 -2.5133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5133 -0.6734 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8399 -3.1867 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 1.8723 -1.5934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7122 -1.5934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9199 -4.3856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9199 1.1989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 33 1 0 0 0 0 6 34 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 21 2 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 23 17 1 1 0 0 0 23 27 1 0 0 0 0 23 34 1 0 0 0 0 24 18 1 1 0 0 0 24 28 1 0 0 0 0 24 33 1 0 0 0 0 25 19 1 1 0 0 0 25 29 1 0 0 0 0 25 31 1 0 0 0 0 26 20 1 1 0 0 0 26 30 1 0 0 0 0 26 32 1 0 0 0 0 27 31 2 3 0 0 0 27 35 1 0 0 0 0 28 32 2 3 0 0 0 28 36 1 0 0 0 0 29 33 1 0 0 0 0 29 37 2 0 0 0 0 30 34 1 0 0 0 0 30 38 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.3
Volume:	554.55
LogP:	3.394
LogD:	3.362
LogS:	-4.082
# Rotatable Bonds:	6
TPSA:	98.82
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	4.106
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
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:	-4.99
MDCK Permeability:	0.00015767176228109747
Pgp-inhibitor:	0.99
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.073
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	94.28968048095703%
Volume Distribution (VD):	0.532
Pgp-substrate:	2.245142936706543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.29
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.552
CYP2C9-substrate:	0.244
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.936
CYP3A4-substrate:	0.875

ADMET: Excretion

Clearance (CL):	5.243
Half-life (T1/2):	0.639

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.878
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.014
Carcinogencity:	0.01
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC470544

Natural Product ID:	NPC470544
*Common Name:**	(3S,6S,9S,12S)-6,12-Dibenzyl-3,9-Diisopropyl-1,7-Dimethyl-1,4,7,10-Tetraazacyclododecane-2,5,8,11-Tetraone
IUPAC Name:	(3S,6S,9S,12S)-6,12-dibenzyl-1,7-dimethyl-3,9-di(propan-2-yl)-1,4,7,10-tetrazacyclododecane-2,5,8,11-tetrone
Synonyms:
Standard InCHIKey:	YJHCFDOTTLDFSM-CQJMVLFOSA-N
Standard InCHI:	InChI=1S/C30H40N4O4/c1-19(2)25-29(37)33(5)24(18-22-15-11-8-12-16-22)28(36)32-26(20(3)4)30(38)34(6)23(27(35)31-25)17-21-13-9-7-10-14-21/h7-16,19-20,23-26H,17-18H2,1-6H3,(H,31,35)(H,32,36)/t23-,24-,25-,26-/m0/s1
SMILES:	CC(C)C1C(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)N1)CC2=CC=CC=C2)C)C(C)C)CC3=CC=CC=C3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063167
PubChem CID:	60155056
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
NPO32867	onychocola sclerotica	Species	Arachnomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22694270]

☑ 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	3

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	6200.0	nM	PMID[504285]
NPT98	Individual Protein	HERG	Homo sapiens	IC50	>	24000.0	nM	PMID[504285]
NPT27	Others	Unspecified		IC50	>	20000.0	nM	PMID[504285]

☑ 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 NPC470544 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	115
0.1-0.2	776
0.2-0.3	6696
0.3-0.4	18375
0.4-0.5	13395
0.5-0.6	2385
0.6-0.7	580
0.7-0.8	295
0.8-0.85	52
0.85-0.9	23
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC470545
0.9818	High Similarity	NPC470546
0.9217	High Similarity	NPC71684
0.9	High Similarity	NPC473322
0.8898	High Similarity	NPC6975
0.8889	High Similarity	NPC202521
0.8852	High Similarity	NPC255447
0.8843	High Similarity	NPC111428
0.8803	High Similarity	NPC200964
0.8803	High Similarity	NPC476990
0.8783	High Similarity	NPC239357
0.8772	High Similarity	NPC33742
0.875	High Similarity	NPC101719
0.8684	High Similarity	NPC276949
0.8684	High Similarity	NPC35850
0.8667	High Similarity	NPC22746
0.8667	High Similarity	NPC222466
0.8655	High Similarity	NPC252878
0.8618	High Similarity	NPC200589
0.8607	High Similarity	NPC319766
0.8583	High Similarity	NPC46427
0.8468	Intermediate Similarity	NPC300315
0.8438	Intermediate Similarity	NPC132636
0.84	Intermediate Similarity	NPC130309
0.8359	Intermediate Similarity	NPC127741
0.8305	Intermediate Similarity	NPC285926
0.8305	Intermediate Similarity	NPC14672
0.8305	Intermediate Similarity	NPC315276
0.8268	Intermediate Similarity	NPC287401
0.8244	Intermediate Similarity	NPC161069
0.8241	Intermediate Similarity	NPC25565
0.8165	Intermediate Similarity	NPC473501
0.8165	Intermediate Similarity	NPC475439
0.812	Intermediate Similarity	NPC209509
0.8092	Intermediate Similarity	NPC239762
0.8092	Intermediate Similarity	NPC163392
0.8077	Intermediate Similarity	NPC471265
0.8077	Intermediate Similarity	NPC471264
0.8077	Intermediate Similarity	NPC68865
0.8062	Intermediate Similarity	NPC248283
0.803	Intermediate Similarity	NPC476989
0.8017	Intermediate Similarity	NPC220698
0.8	Intermediate Similarity	NPC16188
0.8	Intermediate Similarity	NPC138775
0.7966	Intermediate Similarity	NPC474584
0.7955	Intermediate Similarity	NPC476259
0.7953	Intermediate Similarity	NPC469666
0.7941	Intermediate Similarity	NPC105717
0.7937	Intermediate Similarity	NPC477937
0.7907	Intermediate Similarity	NPC246079
0.7895	Intermediate Similarity	NPC263493
0.7895	Intermediate Similarity	NPC269398
0.7895	Intermediate Similarity	NPC469426
0.7895	Intermediate Similarity	NPC469427
0.7895	Intermediate Similarity	NPC168113
0.7883	Intermediate Similarity	NPC254798
0.784	Intermediate Similarity	NPC175726
0.784	Intermediate Similarity	NPC474082
0.7838	Intermediate Similarity	NPC311242
0.7836	Intermediate Similarity	NPC197682
0.7836	Intermediate Similarity	NPC176226
0.7836	Intermediate Similarity	NPC139326
0.7826	Intermediate Similarity	NPC473418
0.7818	Intermediate Similarity	NPC303045
0.7818	Intermediate Similarity	NPC161972
0.7797	Intermediate Similarity	NPC319579
0.7794	Intermediate Similarity	NPC262077
0.7786	Intermediate Similarity	NPC141050
0.7778	Intermediate Similarity	NPC476978
0.777	Intermediate Similarity	NPC233702
0.7769	Intermediate Similarity	NPC325479
0.7759	Intermediate Similarity	NPC45033
0.7759	Intermediate Similarity	NPC327481
0.7744	Intermediate Similarity	NPC476133
0.7744	Intermediate Similarity	NPC178662
0.7744	Intermediate Similarity	NPC92784
0.7744	Intermediate Similarity	NPC470884
0.7744	Intermediate Similarity	NPC89489
0.7744	Intermediate Similarity	NPC98424
0.7742	Intermediate Similarity	NPC45777
0.7742	Intermediate Similarity	NPC477061
0.7739	Intermediate Similarity	NPC224610
0.7739	Intermediate Similarity	NPC88267
0.7739	Intermediate Similarity	NPC113326
0.7739	Intermediate Similarity	NPC194390
0.7721	Intermediate Similarity	NPC316008
0.7721	Intermediate Similarity	NPC322878
0.7721	Intermediate Similarity	NPC315266
0.7721	Intermediate Similarity	NPC5620
0.7721	Intermediate Similarity	NPC313867
0.7714	Intermediate Similarity	NPC202198
0.7714	Intermediate Similarity	NPC122590
0.7714	Intermediate Similarity	NPC286551
0.7698	Intermediate Similarity	NPC473491
0.7687	Intermediate Similarity	NPC268841
0.7687	Intermediate Similarity	NPC46098
0.7687	Intermediate Similarity	NPC307357
0.7664	Intermediate Similarity	NPC314358
0.7647	Intermediate Similarity	NPC314388
0.7647	Intermediate Similarity	NPC315283
0.7642	Intermediate Similarity	NPC169328
0.7606	Intermediate Similarity	NPC469903
0.7581	Intermediate Similarity	NPC310467
0.7581	Intermediate Similarity	NPC237420
0.7578	Intermediate Similarity	NPC47667
0.7545	Intermediate Similarity	NPC226438
0.7544	Intermediate Similarity	NPC12730
0.7536	Intermediate Similarity	NPC81026
0.7518	Intermediate Similarity	NPC52748
0.75	Intermediate Similarity	NPC129666
0.75	Intermediate Similarity	NPC254088
0.75	Intermediate Similarity	NPC2501
0.7482	Intermediate Similarity	NPC329761
0.7482	Intermediate Similarity	NPC225648
0.7482	Intermediate Similarity	NPC135121
0.7465	Intermediate Similarity	NPC473341
0.7464	Intermediate Similarity	NPC477217
0.7464	Intermediate Similarity	NPC266741
0.7464	Intermediate Similarity	NPC201244
0.7462	Intermediate Similarity	NPC105114
0.7462	Intermediate Similarity	NPC89923
0.7462	Intermediate Similarity	NPC239990
0.7462	Intermediate Similarity	NPC152850
0.7462	Intermediate Similarity	NPC71933
0.746	Intermediate Similarity	NPC27833
0.7455	Intermediate Similarity	NPC172128
0.7448	Intermediate Similarity	NPC319320
0.7448	Intermediate Similarity	NPC287757
0.7447	Intermediate Similarity	NPC7817
0.7447	Intermediate Similarity	NPC475168
0.7445	Intermediate Similarity	NPC468984
0.7422	Intermediate Similarity	NPC35996
0.7413	Intermediate Similarity	NPC473002
0.7407	Intermediate Similarity	NPC43755
0.7397	Intermediate Similarity	NPC469902
0.7397	Intermediate Similarity	NPC471527
0.7397	Intermediate Similarity	NPC469243
0.7397	Intermediate Similarity	NPC473003
0.7385	Intermediate Similarity	NPC136453
0.7368	Intermediate Similarity	NPC257390
0.7357	Intermediate Similarity	NPC145113
0.7357	Intermediate Similarity	NPC311658
0.7353	Intermediate Similarity	NPC313694
0.7353	Intermediate Similarity	NPC242159
0.735	Intermediate Similarity	NPC471317
0.735	Intermediate Similarity	NPC164859
0.7347	Intermediate Similarity	NPC241794
0.7343	Intermediate Similarity	NPC5194
0.7343	Intermediate Similarity	NPC56685
0.7343	Intermediate Similarity	NPC262166
0.7343	Intermediate Similarity	NPC261934
0.7329	Intermediate Similarity	NPC244336
0.7323	Intermediate Similarity	NPC478014
0.7323	Intermediate Similarity	NPC478015
0.7323	Intermediate Similarity	NPC478016
0.7319	Intermediate Similarity	NPC77905
0.7311	Intermediate Similarity	NPC474804
0.7311	Intermediate Similarity	NPC474973
0.7311	Intermediate Similarity	NPC130898
0.7305	Intermediate Similarity	NPC471821
0.7305	Intermediate Similarity	NPC471820
0.7304	Intermediate Similarity	NPC322598
0.7302	Intermediate Similarity	NPC314992
0.7297	Intermediate Similarity	NPC471053
0.7297	Intermediate Similarity	NPC209764
0.7297	Intermediate Similarity	NPC471051
0.7297	Intermediate Similarity	NPC74936
0.7297	Intermediate Similarity	NPC471307
0.7297	Intermediate Similarity	NPC133470
0.7297	Intermediate Similarity	NPC289776
0.7297	Intermediate Similarity	NPC141139
0.7297	Intermediate Similarity	NPC159178
0.7297	Intermediate Similarity	NPC121872
0.7297	Intermediate Similarity	NPC191863
0.7297	Intermediate Similarity	NPC78041
0.7297	Intermediate Similarity	NPC471052
0.7295	Intermediate Similarity	NPC329011
0.7293	Intermediate Similarity	NPC157311
0.7292	Intermediate Similarity	NPC470902
0.7286	Intermediate Similarity	NPC314114
0.728	Intermediate Similarity	NPC2265
0.7279	Intermediate Similarity	NPC475544
0.7273	Intermediate Similarity	NPC162104
0.726	Intermediate Similarity	NPC324850
0.7254	Intermediate Similarity	NPC283783
0.7248	Intermediate Similarity	NPC189116
0.7248	Intermediate Similarity	NPC223207
0.7241	Intermediate Similarity	NPC476268
0.7239	Intermediate Similarity	NPC8761
0.7239	Intermediate Similarity	NPC326966
0.7239	Intermediate Similarity	NPC44805
0.7236	Intermediate Similarity	NPC273814
0.7227	Intermediate Similarity	NPC143516
0.7214	Intermediate Similarity	NPC471680
0.7211	Intermediate Similarity	NPC62104
0.7211	Intermediate Similarity	NPC1390
0.7207	Intermediate Similarity	NPC470877
0.7203	Intermediate Similarity	NPC324081
0.7203	Intermediate Similarity	NPC202613
0.72	Intermediate Similarity	NPC471771

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 NPC470544 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	99
0.1-0.2	352
0.2-0.3	765
0.3-0.4	1888
0.4-0.5	3453
0.5-0.6	1912
0.6-0.7	557
0.7-0.8	120
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8455	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.808	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD8172	Phase 2
0.8077	Intermediate Similarity	NPD8173	Phase 2
0.807	Intermediate Similarity	NPD7130	Phase 3
0.8016	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8643	Discontinued
0.8	Intermediate Similarity	NPD8323	Discontinued
0.797	Intermediate Similarity	NPD7720	Phase 2
0.7951	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD4677	Discontinued
0.7891	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD4125	Approved
0.7857	Intermediate Similarity	NPD5367	Discontinued
0.7852	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD2584	Suspended
0.7836	Intermediate Similarity	NPD8076	Discontinued
0.781	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD3643	Approved
0.7797	Intermediate Similarity	NPD3644	Approved
0.7797	Intermediate Similarity	NPD3642	Approved
0.7786	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6901	Phase 3
0.7737	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3626	Phase 3
0.7672	Intermediate Similarity	NPD999	Phase 2
0.7652	Intermediate Similarity	NPD8265	Approved
0.7652	Intermediate Similarity	NPD8416	Discontinued
0.7647	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5581	Approved
0.7632	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5263	Approved
0.7609	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3125	Approved
0.7574	Intermediate Similarity	NPD2022	Approved
0.7559	Intermediate Similarity	NPD3071	Approved
0.7559	Intermediate Similarity	NPD3072	Approved
0.7559	Intermediate Similarity	NPD3073	Approved
0.7557	Intermediate Similarity	NPD2043	Approved
0.7557	Intermediate Similarity	NPD2047	Approved
0.7557	Intermediate Similarity	NPD2051	Approved
0.7557	Intermediate Similarity	NPD2046	Approved
0.7557	Intermediate Similarity	NPD2044	Approved
0.7557	Intermediate Similarity	NPD21	Approved
0.7557	Intermediate Similarity	NPD2045	Approved
0.7557	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD2048	Approved
0.7556	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD8315	Phase 1
0.7521	Intermediate Similarity	NPD5717	Approved
0.7519	Intermediate Similarity	NPD6623	Phase 3
0.75	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7522	Discontinued
0.748	Intermediate Similarity	NPD4761	Approved
0.748	Intermediate Similarity	NPD4762	Approved
0.7477	Intermediate Similarity	NPD6690	Approved
0.746	Intermediate Similarity	NPD7342	Discontinued
0.7445	Intermediate Similarity	NPD2088	Approved
0.7445	Intermediate Similarity	NPD2087	Approved
0.7422	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3123	Discovery
0.7407	Intermediate Similarity	NPD6073	Approved
0.7394	Intermediate Similarity	NPD7303	Discontinued
0.7391	Intermediate Similarity	NPD6681	Discovery
0.7376	Intermediate Similarity	NPD5613	Approved
0.7376	Intermediate Similarity	NPD6088	Approved
0.7376	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5614	Approved
0.7353	Intermediate Similarity	NPD6294	Approved
0.7353	Intermediate Similarity	NPD6295	Approved
0.7348	Intermediate Similarity	NPD4676	Approved
0.7339	Intermediate Similarity	NPD7508	Discontinued
0.7328	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4432	Discontinued
0.7321	Intermediate Similarity	NPD1814	Approved
0.7321	Intermediate Similarity	NPD1812	Approved
0.7308	Intermediate Similarity	NPD5578	Approved
0.7308	Intermediate Similarity	NPD6792	Phase 3
0.7308	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2218	Phase 2
0.7302	Intermediate Similarity	NPD2217	Approved
0.7286	Intermediate Similarity	NPD1968	Approved
0.7286	Intermediate Similarity	NPD1967	Approved
0.7273	Intermediate Similarity	NPD5759	Approved
0.7273	Intermediate Similarity	NPD4177	Approved
0.7273	Intermediate Similarity	NPD3040	Approved
0.7273	Intermediate Similarity	NPD7828	Discontinued
0.7273	Intermediate Similarity	NPD4175	Approved
0.7273	Intermediate Similarity	NPD7613	Discontinued
0.7266	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5716	Approved
0.7265	Intermediate Similarity	NPD4119	Approved
0.7259	Intermediate Similarity	NPD5323	Approved
0.7254	Intermediate Similarity	NPD3988	Approved
0.7254	Intermediate Similarity	NPD3987	Approved
0.7244	Intermediate Similarity	NPD5981	Approved
0.7239	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1330	Phase 2
0.7236	Intermediate Similarity	NPD480	Approved
0.7227	Intermediate Similarity	NPD1040	Phase 2
0.7226	Intermediate Similarity	NPD6852	Discontinued
0.7222	Intermediate Similarity	NPD7131	Phase 3
0.7222	Intermediate Similarity	NPD6360	Discontinued
0.7213	Intermediate Similarity	NPD4253	Approved
0.7213	Intermediate Similarity	NPD4254	Approved
0.7206	Intermediate Similarity	NPD3908	Approved
0.7206	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1348	Approved
0.7197	Intermediate Similarity	NPD4151	Approved
0.7181	Intermediate Similarity	NPD8351	Phase 2
0.7177	Intermediate Similarity	NPD3598	Phase 3
0.7176	Intermediate Similarity	NPD2031	Discontinued
0.7174	Intermediate Similarity	NPD3480	Approved
0.7172	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7599	Phase 2
0.7154	Intermediate Similarity	NPD5335	Discontinued
0.7153	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5725	Approved
0.7153	Intermediate Similarity	NPD8125	Discontinued
0.7143	Intermediate Similarity	NPD2437	Approved
0.7143	Intermediate Similarity	NPD2436	Approved
0.7133	Intermediate Similarity	NPD2016	Approved
0.7133	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2013	Approved
0.7133	Intermediate Similarity	NPD2014	Approved
0.7122	Intermediate Similarity	NPD7450	Phase 2
0.7121	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3551	Approved
0.7114	Intermediate Similarity	NPD7600	Phase 2
0.7111	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5299	Approved
0.7105	Intermediate Similarity	NPD7484	Phase 3
0.7105	Intermediate Similarity	NPD7485	Phase 3
0.7073	Intermediate Similarity	NPD2583	Phase 2
0.7068	Intermediate Similarity	NPD3588	Discontinued
0.7059	Intermediate Similarity	NPD941	Approved
0.7059	Intermediate Similarity	NPD8118	Discontinued
0.7045	Intermediate Similarity	NPD6325	Discontinued
0.7043	Intermediate Similarity	NPD4814	Discontinued
0.7042	Intermediate Similarity	NPD6676	Phase 2
0.704	Intermediate Similarity	NPD3149	Approved
0.704	Intermediate Similarity	NPD2659	Approved
0.704	Intermediate Similarity	NPD3150	Approved
0.704	Intermediate Similarity	NPD2658	Approved
0.704	Intermediate Similarity	NPD3148	Approved
0.704	Intermediate Similarity	NPD3147	Approved
0.7037	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5230	Approved
0.7034	Intermediate Similarity	NPD5229	Approved
0.7031	Intermediate Similarity	NPD6345	Approved
0.7031	Intermediate Similarity	NPD6343	Approved
0.7031	Intermediate Similarity	NPD998	Approved
0.7027	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6624	Discontinued
0.7009	Intermediate Similarity	NPD4117	Approved
0.7008	Intermediate Similarity	NPD7679	Phase 2
0.7008	Intermediate Similarity	NPD1344	Phase 2
0.7007	Intermediate Similarity	NPD5296	Approved
0.7007	Intermediate Similarity	NPD4153	Approved
0.7	Intermediate Similarity	NPD7080	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7908	Discontinued
0.6978	Remote Similarity	NPD4214	Discontinued
0.6975	Remote Similarity	NPD4803	Discontinued
0.6972	Remote Similarity	NPD5024	Approved
0.696	Remote Similarity	NPD1762	Approved
0.696	Remote Similarity	NPD1764	Approved
0.6959	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8417	Discontinued
0.6953	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1018	Approved
0.6939	Remote Similarity	NPD4646	Approved
0.6939	Remote Similarity	NPD4648	Approved
0.6939	Remote Similarity	NPD4647	Approved
0.6937	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7086	Phase 2
0.6923	Remote Similarity	NPD6806	Phase 1
0.6923	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD2679	Approved
0.6911	Remote Similarity	NPD2678	Approved
0.6899	Remote Similarity	NPD6093	Discontinued
0.6899	Remote Similarity	NPD4479	Discontinued
0.6891	Remote Similarity	NPD5630	Phase 1
0.6884	Remote Similarity	NPD6346	Approved
0.6879	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7512	Approved
0.6879	Remote Similarity	NPD7511	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