NPASS Compound

Structure

CID75179 OpenBabel06191715412D 48 53 0 0 1 0 0 0 0 0999 V2000 1.5739 -9.3442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0739 -8.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -8.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8682 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8682 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0021 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4174 0.5959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7264 -0.3551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0021 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1361 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4392 0.8038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0573 -1.0983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2701 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7701 0.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -5.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1361 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7701 0.0607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 -3.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5380 -5.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0791 -0.8904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -5.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4611 -0.8904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2701 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4041 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -6.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -8.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2701 -2.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -7.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -4.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -5.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 -5.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5100 -1.1994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 -2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -7.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 38 1 0 0 0 0 2 38 1 0 0 0 0 3 38 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 25 2 0 0 0 0 10 25 1 0 0 0 0 11 27 2 0 0 0 0 12 31 2 0 0 0 0 13 16 2 0 0 0 0 13 28 1 0 0 0 0 14 15 1 0 0 0 0 14 42 1 0 0 0 0 15 43 1 0 0 0 0 16 48 1 0 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 19 30 1 0 0 0 0 20 27 1 0 0 0 0 20 33 1 0 0 0 0 21 26 1 0 0 0 0 21 39 2 0 0 0 0 22 26 1 0 0 0 0 22 42 1 0 0 0 0 23 30 1 0 0 0 0 23 43 1 0 0 0 0 24 32 1 0 0 0 0 24 42 1 0 0 0 0 27 31 1 0 0 0 0 28 37 2 0 0 0 0 29 17 1 6 0 0 0 29 35 1 0 0 0 0 30 44 1 6 0 0 0 31 34 1 0 0 0 0 32 36 1 6 0 0 0 32 43 1 0 0 0 0 33 34 1 0 0 0 0 33 45 1 6 0 0 0 34 40 1 6 0 0 0 35 40 2 3 0 0 0 35 46 1 0 0 0 0 36 41 2 3 0 0 0 36 47 1 0 0 0 0 37 39 1 0 0 0 0 37 48 1 0 0 0 0 38 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	653.36
Volume:	681.763
LogP:	3.755
LogD:	3.891
LogS:	-4.081
# Rotatable Bonds:	14
TPSA:	131.17
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.193
Synthetic Accessibility Score:	4.391
Fsp3:	0.447
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:	-5.612
MDCK Permeability:	2.080166268569883e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.971
20% Bioavailability (F20%):	0.214
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.652
Plasma Protein Binding (PPB):	97.0699691772461%
Volume Distribution (VD):	1.827
Pgp-substrate:	1.7685933113098145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.727
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.5
CYP2C9-substrate:	0.778
CYP2D6-inhibitor:	0.73
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.77
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	8.771
Half-life (T1/2):	0.458

ADMET: Toxicity

hERG Blockers:	0.727
Human Hepatotoxicity (H-HT):	0.911
Drug-inuced Liver Injury (DILI):	0.465
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.867
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.029
Carcinogencity:	0.187
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.822

Download Data

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

Natural Product: NPC75179

Natural Product ID:	NPC75179
*Common Name:**	L-754394
IUPAC Name:	(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-5-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-5-oxopentyl]-N-tert-butyl-4-(furo[2,3-b]pyridin-5-ylmethyl)piperazine-2-carboxamide
Synonyms:	L-754394
Standard InCHIKey:	UBUFVRJUGFJQSI-PPJSLLJVSA-N
Standard InCHI:	InChI=1S/C38H47N5O5/c1-38(2,3)41-36(47)32-24-42(22-26-18-28-13-16-48-37(28)39-21-26)14-15-43(32)23-30(44)19-29(17-25-9-5-4-6-10-25)35(46)40-34-31-12-8-7-11-27(31)20-33(34)45/h4-13,16,18,21,29-30,32-34,44-45H,14-15,17,19-20,22-24H2,1-3H3,(H,40,46)(H,41,47)/t29-,30+,32+,33-,34+/m1/s1
SMILES:	O[C@@H](C[C@H](C(=N[C@@H]1[C@H](O)Cc2c1cccc2)O)Cc1ccccc1)CN1CCN(C[C@H]1C(=NC(C)(C)C)O)Cc1cnc2c(c1)cco2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2062137
PubChem CID:	5481990
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:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0002309] Alpha amino acid amides

*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
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[25442304]
NPO41789	Starmerella bombicola EG1 [eg1]	Strain	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[33006017]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Ki	2
MIC	8
Others	10

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
Individual Protein	7
Organism	10
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT609	Individual Protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	IC50	=	0.35	nM	PMID[486663]
NPT609	Individual Protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	IC95	=	6.0	nM	PMID[486663]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Ki	=	32000.0	nM	PMID[486664]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Kinact	=	0.18	min-1	PMID[486664]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	7500.0	nM	PMID[486664]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Kinact	=	1.62	min-1	PMID[486664]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Partition ratio	=	1.4	n.a.	PMID[486664]
NPT71	Cell Line	HEK293	Homo sapiens	CC50	>	20000.0	nM	PMID[486665]
NPT35	Others	n.a.		S	=	9.1	n.a.	PMID[486663]
NPT35	Others	n.a.		CLogP	=	3.246	n.a.	PMID[486663]
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	Cmax	=	14990.0	nM	PMID[486663]
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	C8h	=	9.428	uM	PMID[486663]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	20000.0	nM	PMID[486665]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	20000.0	nM	PMID[486665]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	20000.0	nM	PMID[486665]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	20000.0	nM	PMID[486665]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	20000.0	nM	PMID[486665]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	20000.0	nM	PMID[486665]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	MIC	>	20000.0	nM	PMID[486665]
NPT20950	CELL-LINE	Erythrocyte	n.a.	HC10	>	20.0	uM	PMID[486665]

☑ 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 NPC75179 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	399
0.1-0.2	1815
0.2-0.3	9972
0.3-0.4	8681
0.4-0.5	15685
0.5-0.6	4474
0.6-0.7	1628
0.7-0.8	42
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7441	Intermediate Similarity	NPC328928
0.7314	Intermediate Similarity	NPC471004
0.7273	Intermediate Similarity	NPC475301
0.7273	Intermediate Similarity	NPC326930
0.7269	Intermediate Similarity	NPC475533
0.724	Intermediate Similarity	NPC475315
0.724	Intermediate Similarity	NPC324619
0.7229	Intermediate Similarity	NPC148896
0.7229	Intermediate Similarity	NPC471013
0.7229	Intermediate Similarity	NPC180668
0.7213	Intermediate Similarity	NPC329631
0.7183	Intermediate Similarity	NPC10904
0.7176	Intermediate Similarity	NPC13603
0.7174	Intermediate Similarity	NPC289086
0.7165	Intermediate Similarity	NPC471015
0.716	Intermediate Similarity	NPC473833
0.7154	Intermediate Similarity	NPC477549
0.7137	Intermediate Similarity	NPC85879
0.7137	Intermediate Similarity	NPC53255
0.7104	Intermediate Similarity	NPC471978
0.7071	Intermediate Similarity	NPC315804
0.7071	Intermediate Similarity	NPC313804
0.7054	Intermediate Similarity	NPC216612
0.7054	Intermediate Similarity	NPC472436
0.704	Intermediate Similarity	NPC99891
0.7034	Intermediate Similarity	NPC264176
0.7025	Intermediate Similarity	NPC322482
0.7024	Intermediate Similarity	NPC472434
0.7023	Intermediate Similarity	NPC471979
0.7021	Intermediate Similarity	NPC290689
0.7021	Intermediate Similarity	NPC269367
0.7008	Intermediate Similarity	NPC186351
0.7004	Intermediate Similarity	NPC472435
0.7	Intermediate Similarity	NPC477586
0.7	Intermediate Similarity	NPC477590
0.7	Intermediate Similarity	NPC477588
0.7	Intermediate Similarity	NPC477585
0.6976	Remote Similarity	NPC170751
0.6976	Remote Similarity	NPC327769
0.6969	Remote Similarity	NPC161801
0.6967	Remote Similarity	NPC319232
0.6967	Remote Similarity	NPC24370
0.696	Remote Similarity	NPC474183
0.6958	Remote Similarity	NPC315467
0.6955	Remote Similarity	NPC205372
0.6951	Remote Similarity	NPC326363
0.6949	Remote Similarity	NPC470020
0.6933	Remote Similarity	NPC165837
0.6933	Remote Similarity	NPC236668
0.6926	Remote Similarity	NPC97746
0.6926	Remote Similarity	NPC470279
0.692	Remote Similarity	NPC285343
0.692	Remote Similarity	NPC477589
0.692	Remote Similarity	NPC477587
0.6916	Remote Similarity	NPC471448
0.6908	Remote Similarity	NPC325976
0.6904	Remote Similarity	NPC146976
0.6904	Remote Similarity	NPC16066
0.69	Remote Similarity	NPC473053
0.6898	Remote Similarity	NPC473506
0.6895	Remote Similarity	NPC196718
0.6895	Remote Similarity	NPC102593
0.6891	Remote Similarity	NPC472098
0.6891	Remote Similarity	NPC476467
0.6888	Remote Similarity	NPC314270
0.6888	Remote Similarity	NPC131885
0.6883	Remote Similarity	NPC287437
0.688	Remote Similarity	NPC274291
0.688	Remote Similarity	NPC329708
0.688	Remote Similarity	NPC165349
0.688	Remote Similarity	NPC118832
0.688	Remote Similarity	NPC264166
0.688	Remote Similarity	NPC47059
0.6877	Remote Similarity	NPC72905
0.6868	Remote Similarity	NPC478010
0.6868	Remote Similarity	NPC478009
0.6867	Remote Similarity	NPC220852
0.6867	Remote Similarity	NPC141053
0.6864	Remote Similarity	NPC287208
0.6864	Remote Similarity	NPC82548
0.6862	Remote Similarity	NPC317752
0.686	Remote Similarity	NPC472555
0.686	Remote Similarity	NPC298436
0.6851	Remote Similarity	NPC472111
0.685	Remote Similarity	NPC188400
0.685	Remote Similarity	NPC316224
0.6846	Remote Similarity	NPC477908
0.6846	Remote Similarity	NPC206343
0.6844	Remote Similarity	NPC477911
0.6842	Remote Similarity	NPC471977
0.6842	Remote Similarity	NPC475644
0.6842	Remote Similarity	NPC471190
0.6842	Remote Similarity	NPC470486
0.684	Remote Similarity	NPC253675
0.6838	Remote Similarity	NPC196449
0.6838	Remote Similarity	NPC314222
0.6835	Remote Similarity	NPC174758
0.6835	Remote Similarity	NPC469589
0.6835	Remote Similarity	NPC174672
0.6831	Remote Similarity	NPC472099
0.6827	Remote Similarity	NPC30456
0.6825	Remote Similarity	NPC470784
0.6822	Remote Similarity	NPC137353
0.682	Remote Similarity	NPC323551
0.682	Remote Similarity	NPC280473
0.682	Remote Similarity	NPC258048
0.682	Remote Similarity	NPC318299
0.6818	Remote Similarity	NPC144779
0.6818	Remote Similarity	NPC294579
0.6818	Remote Similarity	NPC152620
0.6816	Remote Similarity	NPC471980
0.6802	Remote Similarity	NPC476110
0.6802	Remote Similarity	NPC475631
0.6802	Remote Similarity	NPC87152
0.6802	Remote Similarity	NPC475600
0.68	Remote Similarity	NPC96584
0.68	Remote Similarity	NPC255800
0.68	Remote Similarity	NPC323752
0.6797	Remote Similarity	NPC58209
0.6794	Remote Similarity	NPC478006
0.6792	Remote Similarity	NPC41724
0.6792	Remote Similarity	NPC51008
0.679	Remote Similarity	NPC84815
0.679	Remote Similarity	NPC301368
0.6789	Remote Similarity	NPC477899
0.6789	Remote Similarity	NPC477900
0.6789	Remote Similarity	NPC475137
0.6789	Remote Similarity	NPC477902
0.6789	Remote Similarity	NPC475498
0.6787	Remote Similarity	NPC201508
0.6787	Remote Similarity	NPC477906
0.6787	Remote Similarity	NPC475596
0.6787	Remote Similarity	NPC475303
0.6786	Remote Similarity	NPC28945
0.6786	Remote Similarity	NPC184680
0.6784	Remote Similarity	NPC44354
0.6782	Remote Similarity	NPC53534
0.678	Remote Similarity	NPC323345
0.678	Remote Similarity	NPC317373
0.678	Remote Similarity	NPC470164
0.6777	Remote Similarity	NPC471014
0.6777	Remote Similarity	NPC475408
0.6777	Remote Similarity	NPC6981
0.6776	Remote Similarity	NPC127026
0.6776	Remote Similarity	NPC127720
0.6774	Remote Similarity	NPC246381
0.6774	Remote Similarity	NPC194740
0.6771	Remote Similarity	NPC271792
0.6769	Remote Similarity	NPC244543
0.6762	Remote Similarity	NPC477901
0.6761	Remote Similarity	NPC470018
0.6761	Remote Similarity	NPC148860
0.6759	Remote Similarity	NPC101350
0.6759	Remote Similarity	NPC470785
0.6758	Remote Similarity	NPC208522
0.675	Remote Similarity	NPC111732
0.6749	Remote Similarity	NPC62367
0.6748	Remote Similarity	NPC76565
0.6741	Remote Similarity	NPC470474
0.6738	Remote Similarity	NPC123395
0.6737	Remote Similarity	NPC327592
0.6736	Remote Similarity	NPC42678
0.6736	Remote Similarity	NPC477907
0.6736	Remote Similarity	NPC470306
0.6736	Remote Similarity	NPC207531
0.6736	Remote Similarity	NPC477909
0.6735	Remote Similarity	NPC477912
0.6734	Remote Similarity	NPC140296
0.6734	Remote Similarity	NPC110151
0.6734	Remote Similarity	NPC211920
0.6734	Remote Similarity	NPC124029
0.6731	Remote Similarity	NPC189079
0.6723	Remote Similarity	NPC328318
0.6723	Remote Similarity	NPC328596
0.6721	Remote Similarity	NPC216428
0.6719	Remote Similarity	NPC235685
0.6719	Remote Similarity	NPC142385
0.6716	Remote Similarity	NPC314176
0.6708	Remote Similarity	NPC471016
0.6707	Remote Similarity	NPC314954
0.6707	Remote Similarity	NPC235364
0.6705	Remote Similarity	NPC314882
0.6694	Remote Similarity	NPC4421
0.6694	Remote Similarity	NPC478157
0.6693	Remote Similarity	NPC49547
0.6693	Remote Similarity	NPC78609
0.6692	Remote Similarity	NPC133609
0.6681	Remote Similarity	NPC193238
0.6681	Remote Similarity	NPC31930
0.6681	Remote Similarity	NPC316403
0.668	Remote Similarity	NPC295228
0.668	Remote Similarity	NPC63971
0.668	Remote Similarity	NPC473115
0.668	Remote Similarity	NPC212768
0.668	Remote Similarity	NPC75600
0.668	Remote Similarity	NPC473089
0.668	Remote Similarity	NPC202605
0.668	Remote Similarity	NPC112206
0.668	Remote Similarity	NPC281049
0.668	Remote Similarity	NPC6576

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 NPC75179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	587
0.2-0.3	754
0.3-0.4	1568
0.4-0.5	2767
0.5-0.6	2378
0.6-0.7	820
0.7-0.8	50
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
0.7758	Intermediate Similarity	NPD8161	Suspended
0.7692	Intermediate Similarity	NPD8247	Approved
0.7692	Intermediate Similarity	NPD8246	Approved
0.7617	Intermediate Similarity	NPD8289	Discontinued
0.7593	Intermediate Similarity	NPD8021	Approved
0.7593	Intermediate Similarity	NPD8020	Approved
0.7542	Intermediate Similarity	NPD7426	Phase 1
0.7542	Intermediate Similarity	NPD7807	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD4923	Phase 1
0.7489	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5640	Discontinued
0.7425	Intermediate Similarity	NPD4989	Phase 2
0.7331	Intermediate Similarity	NPD8479	Phase 2
0.732	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6568	Discontinued
0.7304	Intermediate Similarity	NPD7467	Discontinued
0.7303	Intermediate Similarity	NPD1659	Phase 1
0.7298	Intermediate Similarity	NPD7967	Discontinued
0.7287	Intermediate Similarity	NPD5883	Phase 2
0.7277	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7660	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6569	Phase 2
0.7213	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD7180	Phase 3
0.7165	Intermediate Similarity	NPD8463	Approved
0.716	Intermediate Similarity	NPD5116	Phase 1
0.716	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6716	Phase 1
0.7143	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5601	Phase 2
0.7143	Intermediate Similarity	NPD3507	Phase 2
0.7137	Intermediate Similarity	NPD7885	Phase 2
0.7137	Intermediate Similarity	NPD7886	Phase 2
0.7137	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD8356	Approved
0.7098	Intermediate Similarity	NPD7963	Phase 3
0.7092	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD8091	Phase 3
0.7078	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4491	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5228	Phase 3
0.7066	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7925	Phase 2
0.7061	Intermediate Similarity	NPD7924	Phase 2
0.7059	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD8063	Discontinued
0.7047	Intermediate Similarity	NPD8101	Phase 3
0.7046	Intermediate Similarity	NPD5293	Phase 2
0.7037	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7675	Phase 3
0.7037	Intermediate Similarity	NPD7674	Phase 3
0.7034	Intermediate Similarity	NPD7069	Discontinued
0.7031	Intermediate Similarity	NPD4353	Phase 2
0.7025	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7053	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD8430	Approved
0.7008	Intermediate Similarity	NPD6172	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD4369	Phase 2
0.6996	Remote Similarity	NPD8359	Phase 2
0.6991	Remote Similarity	NPD4372	Phase 1
0.698	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5482	Discontinued
0.6975	Remote Similarity	NPD5149	Phase 2
0.6975	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7853	Phase 2
0.6942	Remote Similarity	NPD5041	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD8442	Discontinued
0.6936	Remote Similarity	NPD7666	Phase 3
0.6936	Remote Similarity	NPD7665	Phase 2
0.6935	Remote Similarity	NPD7558	Phase 2
0.6932	Remote Similarity	NPD8016	Phase 3
0.6932	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8100	Phase 3
0.6926	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5922	Phase 3
0.6914	Remote Similarity	NPD6475	Phase 2
0.6911	Remote Similarity	NPD6961	Discontinued
0.6909	Remote Similarity	NPD1032	Phase 2
0.6905	Remote Similarity	NPD6790	Phase 1
0.6898	Remote Similarity	NPD3263	Phase 3
0.6897	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7796	Approved
0.6895	Remote Similarity	NPD7797	Approved
0.6888	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD5948	Phase 2
0.6883	Remote Similarity	NPD5022	Discontinued
0.688	Remote Similarity	NPD4038	Approved
0.688	Remote Similarity	NPD8115	Approved
0.688	Remote Similarity	NPD4122	Approved
0.688	Remote Similarity	NPD31	Approved
0.688	Remote Similarity	NPD4037	Approved
0.688	Remote Similarity	NPD4039	Approved
0.688	Remote Similarity	NPD4036	Approved
0.688	Remote Similarity	NPD4034	Approved
0.688	Remote Similarity	NPD4033	Approved
0.688	Remote Similarity	NPD32	Approved
0.688	Remote Similarity	NPD4035	Approved
0.688	Remote Similarity	NPD8114	Approved
0.6875	Remote Similarity	NPD8102	Discontinued
0.6858	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7944	Discontinued
0.6851	Remote Similarity	NPD7001	Phase 3
0.6846	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD6209	Approved
0.6838	Remote Similarity	NPD5513	Phase 2
0.6834	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7603	Discontinued
0.6828	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7031	Phase 1
0.6826	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3477	Phase 2
0.6825	Remote Similarity	NPD6825	Phase 1
0.6824	Remote Similarity	NPD7921	Approved
0.6824	Remote Similarity	NPD7792	Phase 1
0.6818	Remote Similarity	NPD7395	Discontinued
0.6815	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5479	Discontinued
0.6812	Remote Similarity	NPD4551	Phase 2
0.6809	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7012	Phase 3
0.6809	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7013	Phase 3
0.6809	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5147	Discontinued
0.68	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7859	Phase 2
0.679	Remote Similarity	NPD6974	Phase 3
0.6784	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7470	Discontinued
0.6776	Remote Similarity	NPD6995	Phase 1
0.6774	Remote Similarity	NPD5559	Phase 2
0.677	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4919	Phase 3
0.677	Remote Similarity	NPD4921	Phase 3
0.6768	Remote Similarity	NPD6531	Approved
0.6768	Remote Similarity	NPD6530	Approved
0.6763	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6242	Discontinued
0.6751	Remote Similarity	NPD7222	Phase 2
0.6747	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5891	Approved
0.6746	Remote Similarity	NPD3006	Discontinued
0.6744	Remote Similarity	NPD4558	Phase 2
0.6742	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8468	Phase 2
0.6729	Remote Similarity	NPD5450	Discontinued
0.6726	Remote Similarity	NPD4889	Approved
0.6723	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2779	Approved
0.6723	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD3945	Discontinued
0.6722	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6501	Approved
0.6721	Remote Similarity	NPD6500	Approved
0.6721	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4560	Suspended
0.672	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4316	Phase 3
0.6709	Remote Similarity	NPD7010	Phase 3
0.6709	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7417	Discontinued
0.6694	Remote Similarity	NPD5850	Phase 3
0.6694	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6321	Discontinued
0.6681	Remote Similarity	NPD7483	Phase 2
0.6681	Remote Similarity	NPD5512	Phase 3
0.6681	Remote Similarity	NPD7482	Phase 2
0.6681	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4429	Discontinued
0.668	Remote Similarity	NPD5866	Approved
0.668	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7811	Phase 3
0.6667	Remote Similarity	NPD4203	Approved
0.6667	Remote Similarity	NPD6999	Discontinued
0.6667	Remote Similarity	NPD4204	Approved
0.6667	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7810	Phase 3
0.6667	Remote Similarity	NPD1034	Phase 3
0.6667	Remote Similarity	NPD6857	Phase 3
0.6667	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6655	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD8049	Phase 2
0.6654	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7168	Phase 3
0.6653	Remote Similarity	NPD7688	Phase 1
0.6643	Remote Similarity	NPD7403	Phase 1

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