NPASS Compound

Structure

NPC112839 OpenBabel07101718292D 58 63 0 0 1 0 0 0 0 0999 V2000 -0.1684 -3.4566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1081 -3.1146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -2.2981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8053 -2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8096 5.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0272 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8932 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5045 -4.0851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5197 -3.9115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3141 3.2981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6223 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5088 4.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1612 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8932 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 3.2057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6713 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3293 3.4718 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9569 4.0642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0272 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1612 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6865 2.7057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8204 -2.2057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9848 -1.7057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8356 3.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3420 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3293 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3293 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3420 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 -2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6223 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3420 -2.4718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1625 -3.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2101 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7593 2.3090 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -9.0272 3.3090 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 2.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8204 3.2057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.2101 2.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6865 -1.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6713 1.0000 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 -4.9872 4.4115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6148 5.0039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9417 3.8905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 4.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5240 2.4397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1953 -1.4397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1953 2.4397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5240 -1.4397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 -3.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7979 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1516 4.9115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 -2.2057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 35 1 0 0 0 0 2 35 1 0 0 0 0 3 35 1 0 0 0 0 4 36 1 0 0 0 0 5 57 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 36 1 0 0 0 0 11 36 1 0 0 0 0 12 40 2 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 14 37 1 0 0 0 0 15 57 1 0 0 0 0 16 24 2 0 0 0 0 16 37 1 0 0 0 0 17 23 2 0 0 0 0 17 38 1 0 0 0 0 18 15 1 6 0 0 0 18 28 1 0 0 0 0 18 41 1 0 0 0 0 19 7 1 6 0 0 0 19 29 1 0 0 0 0 19 46 1 0 0 0 0 20 14 1 6 0 0 0 20 30 1 0 0 0 0 20 45 1 0 0 0 0 21 47 1 6 0 0 0 22 48 2 0 0 0 0 22 49 1 0 0 0 0 23 24 1 0 0 0 0 23 39 1 0 0 0 0 24 43 1 0 0 0 0 25 21 1 1 0 0 0 25 31 1 0 0 0 0 25 42 1 0 0 0 0 26 33 1 0 0 0 0 26 36 1 1 0 0 0 26 44 1 0 0 0 0 27 32 1 0 0 0 0 27 35 1 6 0 0 0 27 58 1 0 0 0 0 28 42 2 3 0 0 0 28 50 1 0 0 0 0 29 41 2 3 0 0 0 29 51 1 0 0 0 0 30 44 2 3 0 0 0 30 52 1 0 0 0 0 31 45 1 0 0 0 0 31 53 2 0 0 0 0 32 46 1 0 0 0 0 32 54 2 0 0 0 0 33 55 2 0 0 0 0 33 58 1 0 0 0 0 34 37 1 1 0 0 0 34 43 1 0 0 0 0 34 45 1 0 0 0 0 37 56 1 6 0 0 0 40 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	851.27
Volume:	781.05
LogP:	0.821
LogD:	1.551
LogS:	-2.5
# Rotatable Bonds:	7
TPSA:	265.6
# H-Bond Aceptor:	19
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.189
Synthetic Accessibility Score:	6.431
Fsp3:	0.622
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:	-5.832
MDCK Permeability:	3.1580516406393144e-06
Pgp-inhibitor:	0.173
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.909
20% Bioavailability (F20%):	0.647
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	62.802268981933594%
Volume Distribution (VD):	0.322
Pgp-substrate:	38.362728118896484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.197
CYP3A4-substrate:	0.051

ADMET: Excretion

Clearance (CL):	1.853
Half-life (T1/2):	0.397

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.501
Skin Sensitization:	0.659
Carcinogencity:	0.093
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.165

Download Data

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

Natural Product: NPC112839

Natural Product ID:	NPC112839
*Common Name:**	Kutzneride 9
IUPAC Name:	n.a.
Synonyms:	Kutzneride 9
Standard InCHIKey:	IURQCOHKGOZHQD-DGKNJCPKSA-N
Standard InCHI:	InChI=1S/C37H47Cl2N7O12/c1-35(2,3)27-32(54)46-19(7-6-12-40-46)29(51)41-18(15-57-5)28(50)42-25(21(47)13-22(48)49)31(53)45-20(30(52)44-26(33(55)58-27)36(4)10-11-36)14-37(56)16-8-9-17(38)23(39)24(16)43-34(37)45/h8-9,12,18-21,25-27,34,43,47,56H,6-7,10-11,13-15H2,1-5H3,(H,41,51)(H,42,50)(H,44,52)(H,48,49)/t18-,19-,20-,21-,25+,26-,27+,34-,37+/m0/s1
SMILES:	COC[C@@H]1N=C(O)[C@@H]2CCC=NN2C(=O)[C@@H](OC(=O)[C@H](N=C([C@H]2N(C(=O)[C@H](N=C1O)[C@H](CC(=O)O)O)[C@@H]1Nc3c([C@@]1(C2)O)ccc(c3Cl)Cl)O)C1(C)CC1)C(C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503540
PubChem CID:	16099521
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO32896	Kutzneria sp. 744	Species	Pseudonocardiaceae	Bacteria	mycorrhizal roots of Picea abies seedlings	n.a.	n.a.	PMID[16441076]
NPO32896	Kutzneria sp. 744	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17190458]

☑ 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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	60000.0	nM	PMID[535860]
NPT1286	Organism	Pectobacterium carotovorum	Pectobacterium carotovorum	MIC	=	230000.0	nM	PMID[535860]
NPT2647	Organism	Drechslera	Drechslera	MIC	>	230000.0	nM	PMID[535860]
NPT1278	Organism	Fusarium culmorum	Fusarium culmorum	MIC	>	230000.0	nM	PMID[535860]

☑ 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 NPC112839 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	357
0.1-0.2	1942
0.2-0.3	11989
0.3-0.4	21156
0.4-0.5	5392
0.5-0.6	1820
0.6-0.7	31
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC137437
0.9953	High Similarity	NPC243782
0.945	High Similarity	NPC44357
0.945	High Similarity	NPC24661
0.9406	High Similarity	NPC265592
0.9406	High Similarity	NPC275134
0.9364	High Similarity	NPC473702
0.9364	High Similarity	NPC256007
0.7435	Intermediate Similarity	NPC471663
0.6544	Remote Similarity	NPC68650
0.6532	Remote Similarity	NPC285622
0.649	Remote Similarity	NPC471197
0.6463	Remote Similarity	NPC471198
0.6419	Remote Similarity	NPC307396
0.6417	Remote Similarity	NPC225400
0.639	Remote Similarity	NPC471155
0.639	Remote Similarity	NPC470786
0.639	Remote Similarity	NPC472538
0.6364	Remote Similarity	NPC285192
0.6364	Remote Similarity	NPC270241
0.6328	Remote Similarity	NPC323198
0.629	Remote Similarity	NPC15384
0.629	Remote Similarity	NPC244425
0.6289	Remote Similarity	NPC89987
0.6265	Remote Similarity	NPC248601
0.6233	Remote Similarity	NPC471124
0.623	Remote Similarity	NPC475259
0.623	Remote Similarity	NPC470491
0.6213	Remote Similarity	NPC276430
0.6208	Remote Similarity	NPC469443
0.6206	Remote Similarity	NPC64216
0.6202	Remote Similarity	NPC220852
0.6198	Remote Similarity	NPC295548
0.6194	Remote Similarity	NPC314882
0.6184	Remote Similarity	NPC129624
0.618	Remote Similarity	NPC14812
0.6163	Remote Similarity	NPC471950
0.6163	Remote Similarity	NPC471945
0.6157	Remote Similarity	NPC471436
0.6148	Remote Similarity	NPC470490
0.6145	Remote Similarity	NPC478157
0.6138	Remote Similarity	NPC471946
0.6138	Remote Similarity	NPC471951
0.6138	Remote Similarity	NPC478158
0.6137	Remote Similarity	NPC259626
0.613	Remote Similarity	NPC285343
0.613	Remote Similarity	NPC28945
0.6122	Remote Similarity	NPC470488
0.6113	Remote Similarity	NPC475359
0.6113	Remote Similarity	NPC191817
0.6111	Remote Similarity	NPC219397
0.6109	Remote Similarity	NPC473371
0.6109	Remote Similarity	NPC470787
0.6109	Remote Similarity	NPC472540
0.6109	Remote Similarity	NPC472539
0.6107	Remote Similarity	NPC477180
0.6107	Remote Similarity	NPC477181
0.6107	Remote Similarity	NPC254850
0.6107	Remote Similarity	NPC477178
0.6104	Remote Similarity	NPC54744
0.6094	Remote Similarity	NPC2933
0.6083	Remote Similarity	NPC472542
0.6083	Remote Similarity	NPC472541
0.6082	Remote Similarity	NPC477174
0.6082	Remote Similarity	NPC477173
0.6066	Remote Similarity	NPC477179
0.6057	Remote Similarity	NPC220060
0.6054	Remote Similarity	NPC114806
0.6054	Remote Similarity	NPC471122
0.6052	Remote Similarity	NPC256288
0.6044	Remote Similarity	NPC478006
0.6043	Remote Similarity	NPC282092
0.6041	Remote Similarity	NPC470489
0.6032	Remote Similarity	NPC469444
0.6027	Remote Similarity	NPC162104
0.6025	Remote Similarity	NPC155143
0.6024	Remote Similarity	NPC274268
0.6019	Remote Similarity	NPC314358
0.6017	Remote Similarity	NPC90967
0.6017	Remote Similarity	NPC229484
0.6015	Remote Similarity	NPC323752
0.6009	Remote Similarity	NPC24617
0.6009	Remote Similarity	NPC475123
0.6009	Remote Similarity	NPC475204
0.6008	Remote Similarity	NPC281049
0.6	Remote Similarity	NPC477462
0.6	Remote Similarity	NPC299806
0.6	Remote Similarity	NPC315283
0.6	Remote Similarity	NPC314388
0.5992	Remote Similarity	NPC219350
0.5992	Remote Similarity	NPC194699
0.5992	Remote Similarity	NPC292675
0.5984	Remote Similarity	NPC475609
0.5984	Remote Similarity	NPC475506
0.5983	Remote Similarity	NPC167763
0.5983	Remote Similarity	NPC470112
0.5983	Remote Similarity	NPC470903
0.5983	Remote Similarity	NPC477159
0.5982	Remote Similarity	NPC7817
0.5982	Remote Similarity	NPC475168
0.5975	Remote Similarity	NPC473615
0.5973	Remote Similarity	NPC470902
0.5972	Remote Similarity	NPC316008
0.5972	Remote Similarity	NPC313867
0.5966	Remote Similarity	NPC39822
0.5964	Remote Similarity	NPC197743
0.5964	Remote Similarity	NPC297145
0.5963	Remote Similarity	NPC477635
0.5963	Remote Similarity	NPC477630
0.5962	Remote Similarity	NPC49583
0.596	Remote Similarity	NPC469445
0.596	Remote Similarity	NPC320968
0.5957	Remote Similarity	NPC321939
0.5957	Remote Similarity	NPC245741
0.5952	Remote Similarity	NPC66191
0.5952	Remote Similarity	NPC316297
0.5952	Remote Similarity	NPC314817
0.594	Remote Similarity	NPC473404
0.5939	Remote Similarity	NPC475969
0.5939	Remote Similarity	NPC475859
0.5939	Remote Similarity	NPC474877
0.5939	Remote Similarity	NPC300114
0.5938	Remote Similarity	NPC474896
0.5936	Remote Similarity	NPC75634
0.5935	Remote Similarity	NPC314056
0.5934	Remote Similarity	NPC477638
0.5934	Remote Similarity	NPC477632
0.5928	Remote Similarity	NPC473341
0.5917	Remote Similarity	NPC472842
0.5914	Remote Similarity	NPC31097
0.5914	Remote Similarity	NPC315467
0.5913	Remote Similarity	NPC328494
0.5909	Remote Similarity	NPC473375
0.5909	Remote Similarity	NPC97100
0.5907	Remote Similarity	NPC319232
0.5907	Remote Similarity	NPC24370
0.5902	Remote Similarity	NPC106118
0.59	Remote Similarity	NPC470729
0.59	Remote Similarity	NPC470730
0.59	Remote Similarity	NPC477176
0.59	Remote Similarity	NPC477175
0.59	Remote Similarity	NPC51047
0.5899	Remote Similarity	NPC5620
0.5898	Remote Similarity	NPC272174
0.5896	Remote Similarity	NPC277306
0.5896	Remote Similarity	NPC469442
0.5895	Remote Similarity	NPC473000
0.5894	Remote Similarity	NPC63279
0.5893	Remote Similarity	NPC478009
0.5893	Remote Similarity	NPC478010
0.5891	Remote Similarity	NPC476514
0.5887	Remote Similarity	NPC104712
0.5887	Remote Similarity	NPC277350
0.5887	Remote Similarity	NPC177056
0.5885	Remote Similarity	NPC302548
0.5882	Remote Similarity	NPC476515
0.5882	Remote Similarity	NPC473815
0.5882	Remote Similarity	NPC77777
0.588	Remote Similarity	NPC107077
0.588	Remote Similarity	NPC223791
0.5878	Remote Similarity	NPC477177
0.5878	Remote Similarity	NPC477551
0.5875	Remote Similarity	NPC470728
0.5872	Remote Similarity	NPC478013
0.5871	Remote Similarity	NPC297642
0.587	Remote Similarity	NPC46009
0.5863	Remote Similarity	NPC1203
0.5862	Remote Similarity	NPC13367
0.5862	Remote Similarity	NPC471165
0.5861	Remote Similarity	NPC473640
0.5859	Remote Similarity	NPC286871
0.5858	Remote Similarity	NPC284706
0.5856	Remote Similarity	NPC165743
0.5855	Remote Similarity	NPC475421
0.5853	Remote Similarity	NPC476978
0.5852	Remote Similarity	NPC472114
0.5852	Remote Similarity	NPC472115
0.5851	Remote Similarity	NPC477631
0.585	Remote Similarity	NPC25539
0.5845	Remote Similarity	NPC145113
0.5833	Remote Similarity	NPC240130
0.5833	Remote Similarity	NPC473298
0.5833	Remote Similarity	NPC61332
0.5826	Remote Similarity	NPC328763
0.5824	Remote Similarity	NPC244536
0.5823	Remote Similarity	NPC97584
0.5822	Remote Similarity	NPC324850
0.582	Remote Similarity	NPC475559
0.5817	Remote Similarity	NPC162860
0.5817	Remote Similarity	NPC14288
0.5815	Remote Similarity	NPC309531
0.5815	Remote Similarity	NPC472102
0.5813	Remote Similarity	NPC475489
0.581	Remote Similarity	NPC127996
0.5808	Remote Similarity	NPC125597
0.5805	Remote Similarity	NPC478029
0.5798	Remote Similarity	NPC222046
0.5798	Remote Similarity	NPC52262
0.5798	Remote Similarity	NPC316141
0.5796	Remote Similarity	NPC477552

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 NPC112839 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	539
0.2-0.3	950
0.3-0.4	2688
0.4-0.5	3962
0.5-0.6	826
0.6-0.7	10
0.7-0.8	0
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
0.6711	Remote Similarity	NPD6058	Phase 2
0.6537	Remote Similarity	NPD5214	Phase 2
0.6434	Remote Similarity	NPD7576	Discontinued
0.6364	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD4731	Phase 3
0.6213	Remote Similarity	NPD8240	Discontinued
0.6207	Remote Similarity	NPD6557	Phase 2
0.6186	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7805	Phase 3
0.6114	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD5449	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD8463	Approved
0.6057	Remote Similarity	NPD5054	Clinical (unspecified phase)
0.6046	Remote Similarity	NPD6154	Approved
0.6034	Remote Similarity	NPD6878	Phase 2
0.6034	Remote Similarity	NPD6879	Phase 2
0.6034	Remote Similarity	NPD3227	Phase 2
0.5973	Remote Similarity	NPD3790	Phase 2
0.597	Remote Similarity	NPD6735	Approved
0.5947	Remote Similarity	NPD4976	Discontinued
0.5947	Remote Similarity	NPD6982	Phase 2
0.5941	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5856	Discontinued
0.5904	Remote Similarity	NPD8027	Approved
0.5897	Remote Similarity	NPD7963	Phase 3
0.5896	Remote Similarity	NPD7470	Discontinued
0.5878	Remote Similarity	NPD6519	Phase 2
0.5857	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7599	Phase 2
0.5841	Remote Similarity	NPD4485	Approved
0.584	Remote Similarity	NPD6035	Phase 2
0.5826	Remote Similarity	NPD5830	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4086	Phase 1
0.5823	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD7600	Phase 2
0.5812	Remote Similarity	NPD5498	Phase 2
0.5811	Remote Similarity	NPD8329	Phase 3
0.5809	Remote Similarity	NPD3304	Phase 2
0.5809	Remote Similarity	NPD5042	Phase 1
0.5808	Remote Similarity	NPD1702	Phase 3
0.5808	Remote Similarity	NPD3363	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6445	Discontinued
0.5798	Remote Similarity	NPD2397	Discontinued
0.5787	Remote Similarity	NPD7574	Phase 2
0.5787	Remote Similarity	NPD3780	Phase 2
0.5785	Remote Similarity	NPD6665	Discontinued
0.5783	Remote Similarity	NPD2723	Phase 3
0.5779	Remote Similarity	NPD5411	Discontinued
0.5772	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.5744	Remote Similarity	NPD3884	Discontinued
0.5743	Remote Similarity	NPD5487	Phase 1
0.574	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD8303	Discontinued
0.5738	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD3990	Phase 3
0.5735	Remote Similarity	NPD5807	Phase 2
0.572	Remote Similarity	NPD5587	Approved
0.572	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.5719	Remote Similarity	NPD7772	Phase 3
0.5709	Remote Similarity	NPD6249	Phase 2
0.5709	Remote Similarity	NPD6248	Phase 2
0.5709	Remote Similarity	NPD4070	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD7432	Phase 2
0.5703	Remote Similarity	NPD7161	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD7412	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD3989	Phase 3
0.5694	Remote Similarity	NPD8173	Phase 2
0.5694	Remote Similarity	NPD8172	Phase 2
0.5691	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.5685	Remote Similarity	NPD6484	Approved
0.5685	Remote Similarity	NPD6483	Approved
0.5684	Remote Similarity	NPD8124	Phase 3
0.5684	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.5683	Remote Similarity	NPD7105	Phase 1
0.5681	Remote Similarity	NPD6596	Phase 2
0.5679	Remote Similarity	NPD5076	Approved
0.5679	Remote Similarity	NPD5077	Approved
0.5675	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4771	Phase 2
0.5672	Remote Similarity	NPD4454	Phase 2
0.5669	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5668	Remote Similarity	NPD2783	Phase 2
0.5664	Remote Similarity	NPD7616	Discontinued
0.5663	Remote Similarity	NPD6238	Discontinued
0.566	Remote Similarity	NPD7824	Approved
0.566	Remote Similarity	NPD8374	Phase 3
0.5659	Remote Similarity	NPD8271	Discontinued
0.5659	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD1968	Approved
0.5656	Remote Similarity	NPD1967	Approved
0.5649	Remote Similarity	NPD7542	Phase 3
0.5642	Remote Similarity	NPD7970	Approved
0.5642	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.5633	Remote Similarity	NPD4526	Approved
0.5633	Remote Similarity	NPD4528	Approved
0.5633	Remote Similarity	NPD4529	Approved
0.5625	Remote Similarity	NPD3918	Approved
0.5625	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD3917	Approved
0.5625	Remote Similarity	NPD5941	Approved
0.5625	Remote Similarity	NPD5942	Approved
0.5622	Remote Similarity	NPD6805	Discontinued
0.5619	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD3306	Approved
0.5615	Remote Similarity	NPD4699	Discontinued
0.5614	Remote Similarity	NPD1663	Discontinued
0.5612	Remote Similarity	NPD4092	Approved
0.5609	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD3243	Approved
0.5602	Remote Similarity	NPD3414	Approved
0.5602	Remote Similarity	NPD3413	Approved
0.56	Remote Similarity	NPD3416	Discontinued
0.56	Remote Similarity	NPD7613	Discontinued
0.56	Remote Similarity	NPD7903	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