NPASS Compound

Structure

NPC470546 OpenBabel07101719512D 40 42 0 0 1 0 0 0 0 0999 V2000 -4.6752 3.2503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4447 -4.0770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7661 3.2503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5098 -2.4236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6426 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9545 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1979 2.4236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9220 -3.2503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8862 -0.5098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2677 -5.2175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8862 0.4447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0596 -0.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4410 -4.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 -4.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0596 0.9220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2329 -0.5098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4410 -3.7857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 -3.7857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5796 1.3993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2677 -1.3993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2433 2.4236 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4447 -2.4236 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2329 0.4447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2677 -3.3084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2471 0.9220 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4410 -0.9220 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7661 1.5970 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9220 -1.5970 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9220 1.5970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7661 -1.5970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4410 0.9220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2471 -0.9220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8440 1.8440 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8440 -1.8440 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6881 0.0000 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 -0.4447 2.4236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2433 -2.4236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2677 1.3993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5796 -1.3993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 5 35 1 0 0 0 0 6 36 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 23 2 0 0 0 0 16 23 1 0 0 0 0 17 24 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 3 1 6 0 0 0 22 4 1 1 0 0 0 25 19 1 6 0 0 0 25 29 1 0 0 0 0 25 36 1 0 0 0 0 26 20 1 6 0 0 0 26 30 1 0 0 0 0 26 35 1 0 0 0 0 27 21 1 6 0 0 0 27 31 1 0 0 0 0 27 33 1 0 0 0 0 28 22 1 6 0 0 0 28 32 1 0 0 0 0 28 34 1 0 0 0 0 29 33 2 3 0 0 0 29 37 1 0 0 0 0 30 34 2 3 0 0 0 30 38 1 0 0 0 0 31 35 1 0 0 0 0 31 39 2 0 0 0 0 32 36 1 0 0 0 0 32 40 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.34
Volume:	589.142
LogP:	4.226
LogD:	4.173
LogS:	-4.539
# Rotatable Bonds:	8
TPSA:	98.82
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	4.447
Fsp3:	0.5
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:	-4.905
MDCK Permeability:	0.000128700296045281
Pgp-inhibitor:	0.999
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	95.80585479736328%
Volume Distribution (VD):	0.597
Pgp-substrate:	1.4382575750350952%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.418
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.874
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.968
CYP3A4-substrate:	0.835

ADMET: Excretion

Clearance (CL):	5.929
Half-life (T1/2):	0.602

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.68
Drug-inuced Liver Injury (DILI):	0.856
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.808
Maximum Recommended Daily Dose:	0.059
Skin Sensitization:	0.016
Carcinogencity:	0.011
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: NPC470546

Natural Product ID:	NPC470546
*Common Name:**	(3S,6S,9S,12S)-6,12-Dibenzyl-3,9-Di-Sec-Butyl-1,7-Dimethyl-1,4,7,10-Tetraazacyclododecane-2,5,8,11-Tetraone
IUPAC Name:	(3S,6S,9S,12S)-6,12-dibenzyl-3,9-bis[(2S)-butan-2-yl]-1,7-dimethyl-1,4,7,10-tetrazacyclododecane-2,5,8,11-tetrone
Synonyms:
Standard InCHIKey:	ZHRZJBVCMAGJJK-XGSSJENOSA-N
Standard InCHI:	InChI=1S/C32H44N4O4/c1-7-21(3)27-31(39)35(5)26(20-24-17-13-10-14-18-24)30(38)34-28(22(4)8-2)32(40)36(6)25(29(37)33-27)19-23-15-11-9-12-16-23/h9-18,21-22,25-28H,7-8,19-20H2,1-6H3,(H,33,37)(H,34,38)/t21-,22-,25-,26-,27-,28-/m0/s1
SMILES:	CC[C@@H]([C@@H]1N=C(O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H](N=C([C@@H](N(C1=O)C)Cc1ccccc1)O)[C@H](CC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063169
PubChem CID:	60155058
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	=	5000.0	nM	PMID[466513]
NPT98	Individual Protein	HERG	Homo sapiens	IC50	>	22700.0	nM	PMID[466513]
NPT27	Others	Unspecified		IC50	>	20000.0	nM	PMID[466513]

☑ 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 NPC470546 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	120
0.1-0.2	749
0.2-0.3	6176
0.3-0.4	18173
0.4-0.5	14048
0.5-0.6	2450
0.6-0.7	596
0.7-0.8	300
0.8-0.85	57
0.85-0.9	21
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC470545
0.9818	High Similarity	NPC470544
0.9224	High Similarity	NPC71684
0.9167	High Similarity	NPC473322
0.9016	High Similarity	NPC255447
0.9008	High Similarity	NPC111428
0.8974	High Similarity	NPC200964
0.8957	High Similarity	NPC239357
0.8917	High Similarity	NPC101719
0.8908	High Similarity	NPC6975
0.8833	High Similarity	NPC222466
0.8783	High Similarity	NPC33742
0.878	High Similarity	NPC200589
0.8739	High Similarity	NPC202521
0.8696	High Similarity	NPC35850
0.8696	High Similarity	NPC276949
0.8678	High Similarity	NPC22746
0.8655	High Similarity	NPC476990
0.8618	High Similarity	NPC319766
0.8595	High Similarity	NPC46427
0.8594	High Similarity	NPC132636
0.856	High Similarity	NPC130309
0.8516	High Similarity	NPC127741
0.8512	High Similarity	NPC252878
0.848	Intermediate Similarity	NPC300315
0.8397	Intermediate Similarity	NPC161069
0.8319	Intermediate Similarity	NPC285926
0.8319	Intermediate Similarity	NPC14672
0.8319	Intermediate Similarity	NPC315276
0.8281	Intermediate Similarity	NPC287401
0.8271	Intermediate Similarity	NPC209509
0.8244	Intermediate Similarity	NPC239762
0.8244	Intermediate Similarity	NPC163392
0.8231	Intermediate Similarity	NPC471265
0.8231	Intermediate Similarity	NPC471264
0.8182	Intermediate Similarity	NPC475439
0.8182	Intermediate Similarity	NPC473501
0.8148	Intermediate Similarity	NPC16188
0.8148	Intermediate Similarity	NPC138775
0.8106	Intermediate Similarity	NPC476259
0.8092	Intermediate Similarity	NPC68865
0.8091	Intermediate Similarity	NPC25565
0.8088	Intermediate Similarity	NPC105717
0.8077	Intermediate Similarity	NPC248283
0.8045	Intermediate Similarity	NPC168113
0.8045	Intermediate Similarity	NPC263493
0.8045	Intermediate Similarity	NPC269398
0.8045	Intermediate Similarity	NPC476989
0.8033	Intermediate Similarity	NPC220698
0.8029	Intermediate Similarity	NPC254798
0.7985	Intermediate Similarity	NPC176226
0.7985	Intermediate Similarity	NPC139326
0.7985	Intermediate Similarity	NPC197682
0.7983	Intermediate Similarity	NPC474584
0.7969	Intermediate Similarity	NPC469666
0.7953	Intermediate Similarity	NPC477937
0.7941	Intermediate Similarity	NPC262077
0.7926	Intermediate Similarity	NPC476978
0.7923	Intermediate Similarity	NPC246079
0.7914	Intermediate Similarity	NPC233702
0.791	Intermediate Similarity	NPC469427
0.791	Intermediate Similarity	NPC469426
0.7895	Intermediate Similarity	NPC178662
0.7895	Intermediate Similarity	NPC470884
0.7895	Intermediate Similarity	NPC89489
0.7895	Intermediate Similarity	NPC98424
0.7895	Intermediate Similarity	NPC476133
0.7895	Intermediate Similarity	NPC92784
0.7868	Intermediate Similarity	NPC322878
0.7868	Intermediate Similarity	NPC5620
0.7868	Intermediate Similarity	NPC316008
0.7868	Intermediate Similarity	NPC313867
0.7857	Intermediate Similarity	NPC175726
0.7857	Intermediate Similarity	NPC286551
0.7857	Intermediate Similarity	NPC202198
0.7857	Intermediate Similarity	NPC122590
0.7857	Intermediate Similarity	NPC474082
0.7845	Intermediate Similarity	NPC473418
0.7836	Intermediate Similarity	NPC46098
0.7836	Intermediate Similarity	NPC268841
0.7836	Intermediate Similarity	NPC307357
0.7815	Intermediate Similarity	NPC319579
0.781	Intermediate Similarity	NPC314358
0.7805	Intermediate Similarity	NPC169328
0.7803	Intermediate Similarity	NPC141050
0.7794	Intermediate Similarity	NPC315283
0.7794	Intermediate Similarity	NPC314388
0.7778	Intermediate Similarity	NPC327481
0.7778	Intermediate Similarity	NPC45033
0.776	Intermediate Similarity	NPC45777
0.776	Intermediate Similarity	NPC477061
0.7746	Intermediate Similarity	NPC469903
0.7742	Intermediate Similarity	NPC310467
0.7742	Intermediate Similarity	NPC237420
0.7737	Intermediate Similarity	NPC315266
0.7734	Intermediate Similarity	NPC47667
0.7714	Intermediate Similarity	NPC473491
0.7699	Intermediate Similarity	NPC311242
0.7679	Intermediate Similarity	NPC161972
0.7679	Intermediate Similarity	NPC303045
0.7664	Intermediate Similarity	NPC52748
0.7652	Intermediate Similarity	NPC325479
0.7643	Intermediate Similarity	NPC2501
0.7643	Intermediate Similarity	NPC129666
0.7626	Intermediate Similarity	NPC135121
0.7626	Intermediate Similarity	NPC225648
0.7626	Intermediate Similarity	NPC329761
0.7615	Intermediate Similarity	NPC89923
0.7615	Intermediate Similarity	NPC152850
0.7615	Intermediate Similarity	NPC105114
0.7615	Intermediate Similarity	NPC71933
0.7615	Intermediate Similarity	NPC239990
0.7609	Intermediate Similarity	NPC477217
0.7609	Intermediate Similarity	NPC201244
0.7607	Intermediate Similarity	NPC88267
0.7607	Intermediate Similarity	NPC224610
0.7607	Intermediate Similarity	NPC194390
0.7607	Intermediate Similarity	NPC113326
0.7606	Intermediate Similarity	NPC473341
0.7586	Intermediate Similarity	NPC319320
0.7586	Intermediate Similarity	NPC287757
0.7565	Intermediate Similarity	NPC12730
0.7556	Intermediate Similarity	NPC43755
0.7552	Intermediate Similarity	NPC473002
0.7538	Intermediate Similarity	NPC136453
0.7534	Intermediate Similarity	NPC473003
0.7534	Intermediate Similarity	NPC471527
0.7534	Intermediate Similarity	NPC469243
0.7534	Intermediate Similarity	NPC469902
0.75	Intermediate Similarity	NPC145113
0.7483	Intermediate Similarity	NPC261934
0.7483	Intermediate Similarity	NPC262166
0.7483	Intermediate Similarity	NPC241794
0.7483	Intermediate Similarity	NPC5194
0.7483	Intermediate Similarity	NPC56685
0.748	Intermediate Similarity	NPC478016
0.748	Intermediate Similarity	NPC478015
0.748	Intermediate Similarity	NPC27833
0.748	Intermediate Similarity	NPC478014
0.7465	Intermediate Similarity	NPC7817
0.7465	Intermediate Similarity	NPC475168
0.7464	Intermediate Similarity	NPC77905
0.7447	Intermediate Similarity	NPC471821
0.7447	Intermediate Similarity	NPC471820
0.7444	Intermediate Similarity	NPC157311
0.7442	Intermediate Similarity	NPC35996
0.7432	Intermediate Similarity	NPC471051
0.7432	Intermediate Similarity	NPC133470
0.7432	Intermediate Similarity	NPC191863
0.7432	Intermediate Similarity	NPC471052
0.7432	Intermediate Similarity	NPC471053
0.7432	Intermediate Similarity	NPC289776
0.7429	Intermediate Similarity	NPC81026
0.7415	Intermediate Similarity	NPC475544
0.7413	Intermediate Similarity	NPC162104
0.7411	Intermediate Similarity	NPC226438
0.7397	Intermediate Similarity	NPC324850
0.7394	Intermediate Similarity	NPC283783
0.7388	Intermediate Similarity	NPC257390
0.7388	Intermediate Similarity	NPC8761
0.7388	Intermediate Similarity	NPC44805
0.7383	Intermediate Similarity	NPC223207
0.7381	Intermediate Similarity	NPC254088
0.7376	Intermediate Similarity	NPC311658
0.7373	Intermediate Similarity	NPC164859
0.7373	Intermediate Similarity	NPC471317
0.7372	Intermediate Similarity	NPC313694
0.7372	Intermediate Similarity	NPC242159
0.7357	Intermediate Similarity	NPC266741
0.7347	Intermediate Similarity	NPC244336
0.7347	Intermediate Similarity	NPC1390
0.7347	Intermediate Similarity	NPC62104
0.7338	Intermediate Similarity	NPC468984
0.7333	Intermediate Similarity	NPC290755
0.7333	Intermediate Similarity	NPC304074
0.7333	Intermediate Similarity	NPC471771
0.7333	Intermediate Similarity	NPC61004
0.7328	Intermediate Similarity	NPC322598
0.7324	Intermediate Similarity	NPC240848
0.7323	Intermediate Similarity	NPC314992
0.7321	Intermediate Similarity	NPC172128
0.7317	Intermediate Similarity	NPC329011
0.731	Intermediate Similarity	NPC470902
0.7305	Intermediate Similarity	NPC314114
0.7285	Intermediate Similarity	NPC294516
0.7285	Intermediate Similarity	NPC141957
0.7285	Intermediate Similarity	NPC107938
0.7285	Intermediate Similarity	NPC328649
0.7285	Intermediate Similarity	NPC302597
0.7279	Intermediate Similarity	NPC297145
0.7279	Intermediate Similarity	NPC197743
0.7267	Intermediate Similarity	NPC63931
0.7267	Intermediate Similarity	NPC189116
0.726	Intermediate Similarity	NPC473580
0.726	Intermediate Similarity	NPC476268
0.7259	Intermediate Similarity	NPC326966
0.7237	Intermediate Similarity	NPC469904
0.7234	Intermediate Similarity	NPC471680
0.723	Intermediate Similarity	NPC469898
0.7227	Intermediate Similarity	NPC202613

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 NPC470546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	101
0.1-0.2	337
0.2-0.3	763
0.3-0.4	1877
0.4-0.5	3470
0.5-0.6	1910
0.6-0.7	564
0.7-0.8	122
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8468	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD8172	Phase 2
0.8231	Intermediate Similarity	NPD8173	Phase 2
0.8154	Intermediate Similarity	NPD8643	Discontinued
0.8148	Intermediate Similarity	NPD8323	Discontinued
0.8125	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD7720	Phase 2
0.8095	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD8076	Discontinued
0.7967	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD4677	Discontinued
0.7931	Intermediate Similarity	NPD7130	Phase 3
0.7907	Intermediate Similarity	NPD4125	Approved
0.7868	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2584	Suspended
0.7815	Intermediate Similarity	NPD3644	Approved
0.7815	Intermediate Similarity	NPD3643	Approved
0.7815	Intermediate Similarity	NPD3642	Approved
0.7803	Intermediate Similarity	NPD8265	Approved
0.7803	Intermediate Similarity	NPD8416	Discontinued
0.7803	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD6901	Phase 3
0.7754	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD5367	Discontinued
0.7727	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD999	Phase 2
0.7692	Intermediate Similarity	NPD3626	Phase 3
0.7664	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD5581	Approved
0.7638	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5263	Approved
0.7626	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3125	Approved
0.7578	Intermediate Similarity	NPD3071	Approved
0.7578	Intermediate Similarity	NPD3073	Approved
0.7578	Intermediate Similarity	NPD3072	Approved
0.7574	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD8315	Phase 1
0.7537	Intermediate Similarity	NPD6623	Phase 3
0.7518	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4762	Approved
0.75	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4761	Approved
0.7464	Intermediate Similarity	NPD2022	Approved
0.7444	Intermediate Similarity	NPD2045	Approved
0.7444	Intermediate Similarity	NPD21	Approved
0.7444	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2051	Approved
0.7444	Intermediate Similarity	NPD2043	Approved
0.7444	Intermediate Similarity	NPD2046	Approved
0.7444	Intermediate Similarity	NPD2048	Approved
0.7444	Intermediate Similarity	NPD2047	Approved
0.7444	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2044	Approved
0.7442	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3123	Discovery
0.7426	Intermediate Similarity	NPD6073	Approved
0.7424	Intermediate Similarity	NPD7828	Discontinued
0.741	Intermediate Similarity	NPD6681	Discovery
0.7395	Intermediate Similarity	NPD5717	Approved
0.7394	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6088	Approved
0.7381	Intermediate Similarity	NPD7522	Discontinued
0.7372	Intermediate Similarity	NPD6294	Approved
0.7372	Intermediate Similarity	NPD6295	Approved
0.7368	Intermediate Similarity	NPD4676	Approved
0.7348	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6690	Approved
0.7344	Intermediate Similarity	NPD7342	Discontinued
0.7343	Intermediate Similarity	NPD4432	Discontinued
0.7338	Intermediate Similarity	NPD2087	Approved
0.7338	Intermediate Similarity	NPD2088	Approved
0.7328	Intermediate Similarity	NPD6792	Phase 3
0.7328	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5578	Approved
0.7323	Intermediate Similarity	NPD2218	Phase 2
0.7323	Intermediate Similarity	NPD2217	Approved
0.7305	Intermediate Similarity	NPD1967	Approved
0.7305	Intermediate Similarity	NPD1968	Approved
0.7293	Intermediate Similarity	NPD5759	Approved
0.7293	Intermediate Similarity	NPD4177	Approved
0.7293	Intermediate Similarity	NPD3040	Approved
0.7293	Intermediate Similarity	NPD4175	Approved
0.7292	Intermediate Similarity	NPD7613	Discontinued
0.7292	Intermediate Similarity	NPD7303	Discontinued
0.7287	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5323	Approved
0.7273	Intermediate Similarity	NPD5613	Approved
0.7273	Intermediate Similarity	NPD5614	Approved
0.7266	Intermediate Similarity	NPD5981	Approved
0.7259	Intermediate Similarity	NPD1330	Phase 2
0.7259	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD480	Approved
0.725	Intermediate Similarity	NPD1040	Phase 2
0.7246	Intermediate Similarity	NPD6852	Discontinued
0.7241	Intermediate Similarity	NPD7131	Phase 3
0.7226	Intermediate Similarity	NPD3908	Approved
0.7226	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7508	Discontinued
0.7222	Intermediate Similarity	NPD1348	Approved
0.7218	Intermediate Similarity	NPD4151	Approved
0.72	Intermediate Similarity	NPD8351	Phase 2
0.72	Intermediate Similarity	NPD3598	Phase 3
0.7197	Intermediate Similarity	NPD2031	Discontinued
0.7193	Intermediate Similarity	NPD1814	Approved
0.7193	Intermediate Similarity	NPD1812	Approved
0.7181	Intermediate Similarity	NPD7599	Phase 2
0.7174	Intermediate Similarity	NPD5725	Approved
0.7174	Intermediate Similarity	NPD8125	Discontinued
0.7165	Intermediate Similarity	NPD7679	Phase 2
0.7163	Intermediate Similarity	NPD2436	Approved
0.7163	Intermediate Similarity	NPD2437	Approved
0.7153	Intermediate Similarity	NPD3987	Approved
0.7153	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3988	Approved
0.7143	Intermediate Similarity	NPD4119	Approved
0.7143	Intermediate Similarity	NPD7450	Phase 2
0.7143	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5716	Approved
0.7143	Intermediate Similarity	NPD3551	Approved
0.7133	Intermediate Similarity	NPD7600	Phase 2
0.7132	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5299	Approved
0.7124	Intermediate Similarity	NPD7484	Phase 3
0.7124	Intermediate Similarity	NPD7485	Phase 3
0.7109	Intermediate Similarity	NPD6360	Discontinued
0.7097	Intermediate Similarity	NPD4254	Approved
0.7097	Intermediate Similarity	NPD4253	Approved
0.7095	Intermediate Similarity	NPD8417	Discontinued
0.709	Intermediate Similarity	NPD3588	Discontinued
0.708	Intermediate Similarity	NPD941	Approved
0.708	Intermediate Similarity	NPD8118	Discontinued
0.7075	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3480	Approved
0.7068	Intermediate Similarity	NPD6325	Discontinued
0.7059	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6345	Approved
0.7054	Intermediate Similarity	NPD6343	Approved
0.7054	Intermediate Similarity	NPD998	Approved
0.7047	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5335	Discontinued
0.7045	Intermediate Similarity	NPD6624	Discontinued
0.7034	Intermediate Similarity	NPD2013	Approved
0.7034	Intermediate Similarity	NPD2016	Approved
0.7034	Intermediate Similarity	NPD2014	Approved
0.7029	Intermediate Similarity	NPD5296	Approved
0.7029	Intermediate Similarity	NPD4153	Approved
0.702	Intermediate Similarity	NPD7080	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2846	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7908	Discontinued
0.7006	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4803	Discontinued
0.7	Intermediate Similarity	NPD4214	Discontinued
0.6993	Remote Similarity	NPD8303	Discontinued
0.6993	Remote Similarity	NPD5024	Approved
0.698	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1018	Approved
0.696	Remote Similarity	NPD2583	Phase 2
0.6957	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7086	Phase 2
0.6947	Remote Similarity	NPD6806	Phase 1
0.6944	Remote Similarity	NPD6676	Phase 2
0.6939	Remote Similarity	NPD5229	Approved
0.6939	Remote Similarity	NPD5230	Approved
0.6929	Remote Similarity	NPD2659	Approved
0.6929	Remote Similarity	NPD3148	Approved
0.6929	Remote Similarity	NPD3147	Approved
0.6929	Remote Similarity	NPD2658	Approved
0.6929	Remote Similarity	NPD3150	Approved
0.6929	Remote Similarity	NPD3149	Approved
0.6923	Remote Similarity	NPD4814	Discontinued
0.6923	Remote Similarity	NPD4479	Discontinued
0.6901	Remote Similarity	NPD7511	Approved
0.6901	Remote Similarity	NPD7512	Approved
0.6899	Remote Similarity	NPD1344	Phase 2
0.6891	Remote Similarity	NPD4117	Approved
0.6889	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.688	Remote Similarity	NPD3581	Discontinued
0.6879	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4126	Approved
0.6855	Remote Similarity	NPD8362	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4152	Approved
0.685	Remote Similarity	NPD1762	Approved
0.685	Remote Similarity	NPD1764	Approved
0.6846	Remote Similarity	NPD4648	Approved
0.6846	Remote Similarity	NPD4647	Approved
0.6846	Remote Similarity	NPD5991	Approved
0.6846	Remote Similarity	NPD4646	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