NPASS Compound

Structure

NPC243782 OpenBabel07101718182D 59 64 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 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 -0.8660 -1.5000 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 -1.7321 0.0000 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 -1.7321 -1.0000 0.0000 C 0 0 2 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 2 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 -2.5981 -1.5000 0.0000 O 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 58 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 36 1 0 0 0 0 9 36 1 0 0 0 0 10 15 1 0 0 0 0 11 21 1 0 0 0 0 11 22 1 0 0 0 0 12 37 1 0 0 0 0 13 15 1 0 0 0 0 13 40 2 0 0 0 0 14 58 1 0 0 0 0 15 47 1 1 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 14 1 6 0 0 0 18 28 1 0 0 0 0 18 41 1 0 0 0 0 19 10 1 6 0 0 0 19 29 1 0 0 0 0 19 46 1 0 0 0 0 20 12 1 6 0 0 0 20 30 1 0 0 0 0 20 45 1 0 0 0 0 21 48 1 1 0 0 0 22 49 2 0 0 0 0 22 50 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 59 1 0 0 0 0 28 42 2 3 0 0 0 28 51 1 0 0 0 0 29 41 2 3 0 0 0 29 52 1 0 0 0 0 30 44 2 3 0 0 0 30 53 1 0 0 0 0 31 45 1 0 0 0 0 31 54 2 0 0 0 0 32 46 1 0 0 0 0 32 55 2 0 0 0 0 33 56 2 0 0 0 0 33 59 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 57 1 6 0 0 0 40 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	867.26
Volume:	789.841
LogP:	0.455
LogD:	0.441
LogS:	-2.097
# Rotatable Bonds:	7
TPSA:	285.83
# H-Bond Aceptor:	20
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	6.576
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:	-6.28
MDCK Permeability:	3.2987193208100507e-06
Pgp-inhibitor:	0.092
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.796
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	58.86545944213867%
Volume Distribution (VD):	0.306
Pgp-substrate:	42.66999435424805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.282
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	1.457
Half-life (T1/2):	0.557

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.573
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.139

Download Data

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

Natural Product: NPC243782

Natural Product ID:	NPC243782
*Common Name:**	Kutzneride 6
IUPAC Name:	n.a.
Synonyms:	Kutzneride 6
Standard InCHIKey:	ZIRIUMCQSORLJA-HDJMJMBUSA-N
Standard InCHI:	InChI=1S/C37H47Cl2N7O13/c1-35(2,3)27-32(55)46-19(10-15(47)13-40-46)29(52)41-18(14-58-5)28(51)42-25(21(48)11-22(49)50)31(54)45-20(30(53)44-26(33(56)59-27)36(4)8-9-36)12-37(57)16-6-7-17(38)23(39)24(16)43-34(37)45/h6-7,13,15,18-21,25-27,34,43,47-48,57H,8-12,14H2,1-5H3,(H,41,52)(H,42,51)(H,44,53)(H,49,50)/t15-,18+,19+,20+,21-,25-,26+,27-,34+,37-/m1/s1
SMILES:	COC[C@@H]1N=C(O)[C@@H]2C[C@@H](O)C=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:	CHEMBL504428
PubChem CID:	44566398
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
NPT1286	Organism	Pectobacterium carotovorum	Pectobacterium carotovorum	MIC	>	230000.0	nM	PMID[490327]
NPT1278	Organism	Fusarium culmorum	Fusarium culmorum	MIC	>	230000.0	nM	PMID[490327]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	230000.0	nM	PMID[490327]
NPT2647	Organism	Drechslera	Drechslera	MIC	>	400000.0	nM	PMID[490327]

☑ 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 NPC243782 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	367
0.1-0.2	1967
0.2-0.3	12142
0.3-0.4	21095
0.4-0.5	5313
0.5-0.6	1775
0.6-0.7	28
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
0.9953	High Similarity	NPC137437
0.9953	High Similarity	NPC112839
0.9406	High Similarity	NPC44357
0.9406	High Similarity	NPC24661
0.9364	High Similarity	NPC265592
0.9364	High Similarity	NPC275134
0.9321	High Similarity	NPC256007
0.9321	High Similarity	NPC473702
0.7403	Intermediate Similarity	NPC471663
0.6531	Remote Similarity	NPC471197
0.6514	Remote Similarity	NPC68650
0.6504	Remote Similarity	NPC471198
0.6502	Remote Similarity	NPC285622
0.6432	Remote Similarity	NPC470786
0.6391	Remote Similarity	NPC307396
0.639	Remote Similarity	NPC225400
0.6364	Remote Similarity	NPC472538
0.6364	Remote Similarity	NPC471155
0.6337	Remote Similarity	NPC285192
0.6337	Remote Similarity	NPC270241
0.6331	Remote Similarity	NPC15384
0.6331	Remote Similarity	NPC244425
0.6305	Remote Similarity	NPC248601
0.6304	Remote Similarity	NPC323198
0.6265	Remote Similarity	NPC89987
0.625	Remote Similarity	NPC469443
0.6205	Remote Similarity	NPC471124
0.6204	Remote Similarity	NPC470491
0.6204	Remote Similarity	NPC475259
0.6186	Remote Similarity	NPC276430
0.6181	Remote Similarity	NPC64216
0.6178	Remote Similarity	NPC220852
0.6173	Remote Similarity	NPC295548
0.6171	Remote Similarity	NPC314882
0.6157	Remote Similarity	NPC129624
0.6157	Remote Similarity	NPC14812
0.6151	Remote Similarity	NPC473371
0.6138	Remote Similarity	NPC471945
0.6138	Remote Similarity	NPC471950
0.6132	Remote Similarity	NPC471436
0.6122	Remote Similarity	NPC470490
0.612	Remote Similarity	NPC478157
0.6113	Remote Similarity	NPC471951
0.6113	Remote Similarity	NPC478158
0.6113	Remote Similarity	NPC471946
0.6111	Remote Similarity	NPC259626
0.6107	Remote Similarity	NPC285343
0.6107	Remote Similarity	NPC28945
0.6098	Remote Similarity	NPC220060
0.6098	Remote Similarity	NPC470488
0.6089	Remote Similarity	NPC475359
0.6089	Remote Similarity	NPC191817
0.6087	Remote Similarity	NPC219397
0.6085	Remote Similarity	NPC282092
0.6083	Remote Similarity	NPC472540
0.6083	Remote Similarity	NPC470787
0.6083	Remote Similarity	NPC472539
0.6082	Remote Similarity	NPC477181
0.6082	Remote Similarity	NPC254850
0.6082	Remote Similarity	NPC477180
0.6082	Remote Similarity	NPC477178
0.608	Remote Similarity	NPC54744
0.6073	Remote Similarity	NPC469444
0.6068	Remote Similarity	NPC2933
0.6058	Remote Similarity	NPC472542
0.6058	Remote Similarity	NPC472541
0.6057	Remote Similarity	NPC477174
0.6057	Remote Similarity	NPC477173
0.6043	Remote Similarity	NPC477462
0.6041	Remote Similarity	NPC477179
0.6032	Remote Similarity	NPC219350
0.6032	Remote Similarity	NPC194699
0.6027	Remote Similarity	NPC114806
0.6027	Remote Similarity	NPC471122
0.6026	Remote Similarity	NPC256288
0.6022	Remote Similarity	NPC478006
0.6016	Remote Similarity	NPC470489
0.6009	Remote Similarity	NPC297145
0.6009	Remote Similarity	NPC197743
0.6	Remote Similarity	NPC274268
0.6	Remote Similarity	NPC245741
0.6	Remote Similarity	NPC155143
0.6	Remote Similarity	NPC469445
0.6	Remote Similarity	NPC162104
0.5992	Remote Similarity	NPC90967
0.5992	Remote Similarity	NPC66191
0.5992	Remote Similarity	NPC316297
0.5992	Remote Similarity	NPC314817
0.5992	Remote Similarity	NPC323752
0.5992	Remote Similarity	NPC229484
0.5991	Remote Similarity	NPC314358
0.5984	Remote Similarity	NPC281049
0.5983	Remote Similarity	NPC475123
0.5983	Remote Similarity	NPC475204
0.5982	Remote Similarity	NPC24617
0.5975	Remote Similarity	NPC299806
0.5972	Remote Similarity	NPC315283
0.5972	Remote Similarity	NPC314388
0.5966	Remote Similarity	NPC292675
0.5961	Remote Similarity	NPC475609
0.5959	Remote Similarity	NPC475506
0.5957	Remote Similarity	NPC470112
0.5957	Remote Similarity	NPC470903
0.5957	Remote Similarity	NPC477159
0.5957	Remote Similarity	NPC167763
0.5955	Remote Similarity	NPC475168
0.5955	Remote Similarity	NPC7817
0.5949	Remote Similarity	NPC473615
0.5946	Remote Similarity	NPC470902
0.5945	Remote Similarity	NPC313867
0.5945	Remote Similarity	NPC316008
0.5941	Remote Similarity	NPC51047
0.5941	Remote Similarity	NPC477635
0.5941	Remote Similarity	NPC477630
0.594	Remote Similarity	NPC39822
0.594	Remote Similarity	NPC49583
0.5936	Remote Similarity	NPC321939
0.5936	Remote Similarity	NPC277306
0.5936	Remote Similarity	NPC320968
0.5936	Remote Similarity	NPC469442
0.5925	Remote Similarity	NPC104712
0.5924	Remote Similarity	NPC473815
0.5918	Remote Similarity	NPC477551
0.5917	Remote Similarity	NPC470728
0.5916	Remote Similarity	NPC474877
0.5916	Remote Similarity	NPC300114
0.5916	Remote Similarity	NPC475859
0.5916	Remote Similarity	NPC475969
0.5915	Remote Similarity	NPC473404
0.5914	Remote Similarity	NPC474896
0.5914	Remote Similarity	NPC314056
0.5913	Remote Similarity	NPC75634
0.5909	Remote Similarity	NPC477638
0.5909	Remote Similarity	NPC477632
0.5905	Remote Similarity	NPC471165
0.5901	Remote Similarity	NPC473341
0.5897	Remote Similarity	NPC472842
0.5893	Remote Similarity	NPC315467
0.5891	Remote Similarity	NPC31097
0.5889	Remote Similarity	NPC25539
0.5887	Remote Similarity	NPC328494
0.5885	Remote Similarity	NPC319232
0.5885	Remote Similarity	NPC473375
0.5885	Remote Similarity	NPC24370
0.5885	Remote Similarity	NPC97100
0.5878	Remote Similarity	NPC470730
0.5878	Remote Similarity	NPC470729
0.5878	Remote Similarity	NPC106118
0.5878	Remote Similarity	NPC477175
0.5878	Remote Similarity	NPC477176
0.5875	Remote Similarity	NPC272174
0.5872	Remote Similarity	NPC478009
0.5872	Remote Similarity	NPC478010
0.5872	Remote Similarity	NPC5620
0.5871	Remote Similarity	NPC63279
0.587	Remote Similarity	NPC473000
0.587	Remote Similarity	NPC476514
0.5865	Remote Similarity	NPC177056
0.5863	Remote Similarity	NPC277350
0.5862	Remote Similarity	NPC244536
0.5861	Remote Similarity	NPC476515
0.5861	Remote Similarity	NPC302548
0.5859	Remote Similarity	NPC77777
0.5857	Remote Similarity	NPC107077
0.5857	Remote Similarity	NPC223791
0.5856	Remote Similarity	NPC477177
0.5851	Remote Similarity	NPC478013
0.5849	Remote Similarity	NPC297642
0.5844	Remote Similarity	NPC46009
0.5842	Remote Similarity	NPC1203
0.5841	Remote Similarity	NPC62104
0.5841	Remote Similarity	NPC1390
0.5837	Remote Similarity	NPC473640
0.5837	Remote Similarity	NPC323662
0.5837	Remote Similarity	NPC13367
0.5837	Remote Similarity	NPC477552
0.5837	Remote Similarity	NPC477550
0.5833	Remote Similarity	NPC284706
0.5833	Remote Similarity	NPC286871
0.5833	Remote Similarity	NPC165743
0.583	Remote Similarity	NPC475421
0.5826	Remote Similarity	NPC476978
0.5826	Remote Similarity	NPC477631
0.5826	Remote Similarity	NPC472115
0.5826	Remote Similarity	NPC472114
0.5818	Remote Similarity	NPC145113
0.5816	Remote Similarity	NPC291759
0.5812	Remote Similarity	NPC50016
0.5809	Remote Similarity	NPC473298
0.5809	Remote Similarity	NPC240130
0.5809	Remote Similarity	NPC61332
0.5802	Remote Similarity	NPC328763
0.5799	Remote Similarity	NPC315266
0.5798	Remote Similarity	NPC97584
0.5796	Remote Similarity	NPC475559
0.5796	Remote Similarity	NPC324850
0.5795	Remote Similarity	NPC14288
0.5794	Remote Similarity	NPC162860
0.5789	Remote Similarity	NPC309531
0.5789	Remote Similarity	NPC475489

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 NPC243782 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	543
0.2-0.3	957
0.3-0.4	2735
0.4-0.5	3939
0.5-0.6	790
0.6-0.7	9
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
0.6681	Remote Similarity	NPD6058	Phase 2
0.6509	Remote Similarity	NPD5214	Phase 2
0.6409	Remote Similarity	NPD7576	Discontinued
0.6336	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4731	Phase 3
0.6186	Remote Similarity	NPD8240	Discontinued
0.618	Remote Similarity	NPD6557	Phase 2
0.6157	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7805	Phase 3
0.6087	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5449	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6052	Remote Similarity	NPD8463	Approved
0.6032	Remote Similarity	NPD5054	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6154	Approved
0.6009	Remote Similarity	NPD6878	Phase 2
0.6009	Remote Similarity	NPD3227	Phase 2
0.6009	Remote Similarity	NPD6879	Phase 2
0.5947	Remote Similarity	NPD6735	Approved
0.5947	Remote Similarity	NPD3790	Phase 2
0.5934	Remote Similarity	NPD7963	Phase 3
0.5925	Remote Similarity	NPD6982	Phase 2
0.5921	Remote Similarity	NPD4976	Discontinued
0.5917	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5856	Discontinued
0.588	Remote Similarity	NPD8027	Approved
0.5878	Remote Similarity	NPD6035	Phase 2
0.5873	Remote Similarity	NPD7470	Discontinued
0.5862	Remote Similarity	NPD4086	Phase 1
0.5854	Remote Similarity	NPD6519	Phase 2
0.5833	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD4485	Approved
0.5815	Remote Similarity	NPD7599	Phase 2
0.5804	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.5801	Remote Similarity	NPD5830	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD8329	Phase 3
0.5789	Remote Similarity	NPD7600	Phase 2
0.5787	Remote Similarity	NPD5498	Phase 2
0.5785	Remote Similarity	NPD3304	Phase 2
0.5785	Remote Similarity	NPD5042	Phase 1
0.5783	Remote Similarity	NPD6445	Discontinued
0.5783	Remote Similarity	NPD1702	Phase 3
0.5783	Remote Similarity	NPD3363	Clinical (unspecified phase)
0.5774	Remote Similarity	NPD2397	Discontinued
0.5765	Remote Similarity	NPD3780	Phase 2
0.5763	Remote Similarity	NPD7574	Phase 2
0.5761	Remote Similarity	NPD6665	Discontinued
0.576	Remote Similarity	NPD2723	Phase 3
0.5755	Remote Similarity	NPD5411	Discontinued
0.5749	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7161	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.572	Remote Similarity	NPD3884	Discontinued
0.572	Remote Similarity	NPD5487	Phase 1
0.5714	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3990	Phase 3
0.5714	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5807	Phase 2
0.5714	Remote Similarity	NPD8303	Discontinued
0.5709	Remote Similarity	NPD4454	Phase 2
0.5699	Remote Similarity	NPD7772	Phase 3
0.5698	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.5697	Remote Similarity	NPD5587	Approved
0.5687	Remote Similarity	NPD4070	Clinical (unspecified phase)
0.5685	Remote Similarity	NPD6248	Phase 2
0.5685	Remote Similarity	NPD6249	Phase 2
0.5683	Remote Similarity	NPD7432	Phase 2
0.5682	Remote Similarity	NPD7412	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4529	Approved
0.5673	Remote Similarity	NPD4526	Approved
0.5673	Remote Similarity	NPD4528	Approved
0.5672	Remote Similarity	NPD3989	Phase 3
0.5668	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.5668	Remote Similarity	NPD8173	Phase 2
0.5668	Remote Similarity	NPD8172	Phase 2
0.5661	Remote Similarity	NPD6483	Approved
0.5661	Remote Similarity	NPD6484	Approved
0.566	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.566	Remote Similarity	NPD8124	Phase 3
0.5659	Remote Similarity	NPD6596	Phase 2
0.5658	Remote Similarity	NPD7105	Phase 1
0.5658	Remote Similarity	NPD1663	Discontinued
0.5656	Remote Similarity	NPD5077	Approved
0.5656	Remote Similarity	NPD5076	Approved
0.5652	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.565	Remote Similarity	NPD4771	Phase 2
0.5647	Remote Similarity	NPD2783	Phase 2
0.5647	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5642	Remote Similarity	NPD7616	Discontinued
0.564	Remote Similarity	NPD6238	Discontinued
0.5639	Remote Similarity	NPD7824	Approved
0.5639	Remote Similarity	NPD8374	Phase 3
0.5637	Remote Similarity	NPD8271	Discontinued
0.5637	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD1968	Approved
0.5631	Remote Similarity	NPD1967	Approved
0.5627	Remote Similarity	NPD7542	Phase 3
0.562	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.562	Remote Similarity	NPD7970	Approved
0.5618	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD2565	Phase 2
0.5615	Remote Similarity	NPD2564	Approved
0.5603	Remote Similarity	NPD3918	Approved
0.5603	Remote Similarity	NPD3917	Approved
0.5603	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6805	Discontinued
0.56	Remote Similarity	NPD5941	Approved
0.56	Remote Similarity	NPD5942	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