NPASS Compound

Structure

CID69496 OpenBabel06191715402D 22 24 0 0 1 0 0 0 0 0999 V2000 0.4499 -0.2166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9254 -1.0851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9830 -1.8527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2894 -0.6514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4187 -2.3763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5538 -0.8783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9242 0.5536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8302 0.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1435 -1.0677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6889 -3.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5538 -1.8770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1435 1.1764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9243 -0.4451 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6889 -2.3763 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8301 -0.8455 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2635 0.0541 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8241 -1.8770 0.0000 C 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 3.5538 -3.8743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2168 0.0541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9592 -2.3763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8241 -0.8783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 12 7 1 6 0 0 0 12 18 1 0 0 0 0 13 22 1 6 0 0 0 14 10 1 1 0 0 0 14 17 1 0 0 0 0 15 9 1 6 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 1 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	305.16
Volume:	312.531
LogP:	0.553
LogD:	0.882
LogS:	-1.4
# Rotatable Bonds:	5
TPSA:	70.0
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.809
Synthetic Accessibility Score:	4.467
Fsp3:	0.588
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.092
MDCK Permeability:	0.00010713769006542861
Pgp-inhibitor:	0.012
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.069

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.182
Plasma Protein Binding (PPB):	15.622802734375%
Volume Distribution (VD):	2.153
Pgp-substrate:	78.51911163330078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.778
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.332
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.713
CYP3A4-inhibitor:	0.08
CYP3A4-substrate:	0.581

ADMET: Excretion

Clearance (CL):	8.25
Half-life (T1/2):	0.226

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.674
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.736
Carcinogencity:	0.154
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.896

Download Data

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

Natural Product: NPC69496

Natural Product ID:	NPC69496
*Common Name:**	Anisodamine
IUPAC Name:	[(1R,3S,5R,6S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate
Synonyms:	Anisodamine
Standard InCHIKey:	WTQYWNWRJNXDEG-RBZJEDDUSA-N
Standard InCHI:	InChI=1S/C17H23NO4/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3/t12-,13-,14+,15+,16-/m0/s1
SMILES:	OC[C@H](c1ccccc1)C(=O)O[C@H]1C[C@H]2C[C@@H]([C@@H](C1)N2C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2165224
PubChem CID:	6918612
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000492] Tropane alkaloids

*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
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11858758]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15374592]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	flowers	Yuxi Town, Fuqing City, Fujian Province, China	2005-SEP	PMID[17583953]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24417583]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[26923696]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25993	Atropa belladonna	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25993	Atropa belladonna	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25993	Atropa belladonna	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25993	Atropa belladonna	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25348	Metapochonia suchlasporia	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14522	Uvaria cuneifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26407	Deguelia rufescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25770	Dioncophyllum thollonii	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16093	Achillea atrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26452	Dermophis mexicanus	Species	Dermophiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28346	Phacelia minor	Species	Hydrophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25993	Atropa belladonna	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25950	Pinus apacheca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26320	Acer palmatum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26107	Montanoa speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	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
Others	9

Activity Type	# Activity
Individual Protein	2
ORGANISM	5
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	9.43	%	PMID[566410]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	8.08	%	PMID[566410]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	46.08	%	PMID[566411]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	21.72	%	PMID[566412]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	4.595	%	PMID[566413]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.03	%	PMID[566414]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.18	%	PMID[566415]

☑ 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 NPC69496 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	123
0.1-0.2	567
0.2-0.3	1458
0.3-0.4	4921
0.4-0.5	18584
0.5-0.6	14923
0.6-0.7	2005
0.7-0.8	98
0.8-0.85	7
0.85-0.9	0
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9758	High Similarity	NPC233910
0.9758	High Similarity	NPC245836
0.9421	High Similarity	NPC169485
0.9421	High Similarity	NPC291027
0.9421	High Similarity	NPC84281
0.9421	High Similarity	NPC213126
0.9421	High Similarity	NPC317474
0.935	High Similarity	NPC474847
0.8244	Intermediate Similarity	NPC65310
0.7914	Intermediate Similarity	NPC281104
0.7872	Intermediate Similarity	NPC57976
0.776	Intermediate Similarity	NPC158854
0.7669	Intermediate Similarity	NPC26285
0.7652	Intermediate Similarity	NPC80150
0.7518	Intermediate Similarity	NPC260045
0.7518	Intermediate Similarity	NPC475318
0.7518	Intermediate Similarity	NPC49577
0.7518	Intermediate Similarity	NPC474855
0.7518	Intermediate Similarity	NPC293377
0.7518	Intermediate Similarity	NPC151706
0.7518	Intermediate Similarity	NPC476102
0.7518	Intermediate Similarity	NPC273907
0.7518	Intermediate Similarity	NPC79465
0.7518	Intermediate Similarity	NPC475598
0.7518	Intermediate Similarity	NPC118099
0.7518	Intermediate Similarity	NPC90194
0.7518	Intermediate Similarity	NPC76785
0.7518	Intermediate Similarity	NPC9687
0.7518	Intermediate Similarity	NPC474787
0.7518	Intermediate Similarity	NPC474811
0.745	Intermediate Similarity	NPC162104
0.7426	Intermediate Similarity	NPC285394
0.7415	Intermediate Similarity	NPC145113
0.7388	Intermediate Similarity	NPC478016
0.7388	Intermediate Similarity	NPC478014
0.7388	Intermediate Similarity	NPC190663
0.7388	Intermediate Similarity	NPC478015
0.7379	Intermediate Similarity	NPC161069
0.7376	Intermediate Similarity	NPC313663
0.7372	Intermediate Similarity	NPC47667
0.7368	Intermediate Similarity	NPC310467
0.7329	Intermediate Similarity	NPC476978
0.731	Intermediate Similarity	NPC263493
0.731	Intermediate Similarity	NPC269398
0.7297	Intermediate Similarity	NPC225648
0.7297	Intermediate Similarity	NPC329761
0.7293	Intermediate Similarity	NPC169328
0.7279	Intermediate Similarity	NPC160493
0.7273	Intermediate Similarity	NPC188010
0.7246	Intermediate Similarity	NPC317163
0.7237	Intermediate Similarity	NPC68967
0.7226	Intermediate Similarity	NPC108286
0.7222	Intermediate Similarity	NPC19136
0.7209	Intermediate Similarity	NPC292758
0.7209	Intermediate Similarity	NPC65855
0.72	Intermediate Similarity	NPC94602
0.7181	Intermediate Similarity	NPC138775
0.7162	Intermediate Similarity	NPC5620
0.7162	Intermediate Similarity	NPC209509
0.7132	Intermediate Similarity	NPC477061
0.7132	Intermediate Similarity	NPC45777
0.7123	Intermediate Similarity	NPC239762
0.7123	Intermediate Similarity	NPC163392
0.7109	Intermediate Similarity	NPC329705
0.7109	Intermediate Similarity	NPC474111
0.7103	Intermediate Similarity	NPC471265
0.7103	Intermediate Similarity	NPC471264
0.7097	Intermediate Similarity	NPC322598
0.7092	Intermediate Similarity	NPC81092
0.7092	Intermediate Similarity	NPC103605
0.7086	Intermediate Similarity	NPC2501
0.7063	Intermediate Similarity	NPC246079
0.7059	Intermediate Similarity	NPC122590
0.7055	Intermediate Similarity	NPC98424
0.7055	Intermediate Similarity	NPC92784
0.7055	Intermediate Similarity	NPC470884
0.7055	Intermediate Similarity	NPC178662
0.7055	Intermediate Similarity	NPC476133
0.705	Intermediate Similarity	NPC138798
0.7031	Intermediate Similarity	NPC476198
0.7027	Intermediate Similarity	NPC251439
0.7021	Intermediate Similarity	NPC239990
0.7021	Intermediate Similarity	NPC152850
0.7021	Intermediate Similarity	NPC71933
0.7021	Intermediate Similarity	NPC89923
0.7021	Intermediate Similarity	NPC105114
0.7016	Intermediate Similarity	NPC477767
0.7007	Intermediate Similarity	NPC307357
0.7007	Intermediate Similarity	NPC46098
0.7007	Intermediate Similarity	NPC268841
0.6987	Remote Similarity	NPC297145
0.6987	Remote Similarity	NPC197743
0.6986	Remote Similarity	NPC127741
0.6986	Remote Similarity	NPC478140
0.698	Remote Similarity	NPC471516
0.6978	Remote Similarity	NPC175726
0.6978	Remote Similarity	NPC6975
0.6978	Remote Similarity	NPC474082
0.6978	Remote Similarity	NPC35996
0.6974	Remote Similarity	NPC129666
0.6966	Remote Similarity	NPC248283
0.6954	Remote Similarity	NPC260194
0.695	Remote Similarity	NPC136453
0.6929	Remote Similarity	NPC474112
0.6929	Remote Similarity	NPC475978
0.6929	Remote Similarity	NPC307020
0.6929	Remote Similarity	NPC474820
0.6914	Remote Similarity	NPC474858
0.6913	Remote Similarity	NPC139326
0.6906	Remote Similarity	NPC252878
0.6901	Remote Similarity	NPC319766
0.6899	Remote Similarity	NPC67043
0.6897	Remote Similarity	NPC287401
0.689	Remote Similarity	NPC477462
0.6889	Remote Similarity	NPC210531
0.6887	Remote Similarity	NPC314358
0.6886	Remote Similarity	NPC329816
0.6883	Remote Similarity	NPC214239
0.6879	Remote Similarity	NPC477249
0.6879	Remote Similarity	NPC477248
0.6875	Remote Similarity	NPC157311
0.6867	Remote Similarity	NPC475128
0.6867	Remote Similarity	NPC52748
0.6866	Remote Similarity	NPC87069
0.6861	Remote Similarity	NPC314992
0.6861	Remote Similarity	NPC237420
0.6857	Remote Similarity	NPC46427
0.6853	Remote Similarity	NPC469666
0.6852	Remote Similarity	NPC35345
0.685	Remote Similarity	NPC228400
0.685	Remote Similarity	NPC214200
0.685	Remote Similarity	NPC94487
0.6849	Remote Similarity	NPC477680
0.6848	Remote Similarity	NPC475427
0.6842	Remote Similarity	NPC135121
0.6835	Remote Similarity	NPC202521
0.6831	Remote Similarity	NPC476033
0.6831	Remote Similarity	NPC79608
0.6829	Remote Similarity	NPC298851
0.6829	Remote Similarity	NPC181138
0.6829	Remote Similarity	NPC21752
0.6829	Remote Similarity	NPC210415
0.6829	Remote Similarity	NPC276993
0.6829	Remote Similarity	NPC293255
0.6828	Remote Similarity	NPC8761
0.6828	Remote Similarity	NPC44805
0.6828	Remote Similarity	NPC246913
0.6825	Remote Similarity	NPC271475
0.6821	Remote Similarity	NPC316008
0.6821	Remote Similarity	NPC313867
0.6805	Remote Similarity	NPC473562
0.68	Remote Similarity	NPC176226
0.6797	Remote Similarity	NPC471820
0.6797	Remote Similarity	NPC471821
0.6797	Remote Similarity	NPC473541
0.6797	Remote Similarity	NPC240848
0.6792	Remote Similarity	NPC476194
0.6779	Remote Similarity	NPC476259
0.6776	Remote Similarity	NPC262077
0.6772	Remote Similarity	NPC12730
0.6769	Remote Similarity	NPC474307
0.6769	Remote Similarity	NPC321670
0.6765	Remote Similarity	NPC197470
0.6763	Remote Similarity	NPC476990
0.6761	Remote Similarity	NPC244454
0.6761	Remote Similarity	NPC4974
0.6757	Remote Similarity	NPC68865
0.6755	Remote Similarity	NPC315283
0.6755	Remote Similarity	NPC314388
0.675	Remote Similarity	NPC73644
0.6747	Remote Similarity	NPC476441
0.6747	Remote Similarity	NPC129624
0.6746	Remote Similarity	NPC477159
0.6741	Remote Similarity	NPC172525
0.6738	Remote Similarity	NPC223351
0.6736	Remote Similarity	NPC213969
0.6736	Remote Similarity	NPC165726
0.6733	Remote Similarity	NPC469427
0.6733	Remote Similarity	NPC469426
0.6731	Remote Similarity	NPC473341
0.673	Remote Similarity	NPC211525
0.673	Remote Similarity	NPC153694
0.6728	Remote Similarity	NPC469479
0.6728	Remote Similarity	NPC472106
0.6727	Remote Similarity	NPC137627
0.6716	Remote Similarity	NPC269340
0.6715	Remote Similarity	NPC2265
0.6713	Remote Similarity	NPC470816
0.6711	Remote Similarity	NPC315266
0.6711	Remote Similarity	NPC473052
0.6711	Remote Similarity	NPC201244
0.6711	Remote Similarity	NPC473055
0.6711	Remote Similarity	NPC477217
0.6708	Remote Similarity	NPC472120
0.6708	Remote Similarity	NPC472101
0.6707	Remote Similarity	NPC475204
0.6707	Remote Similarity	NPC475123
0.6694	Remote Similarity	NPC322387
0.6692	Remote Similarity	NPC224610
0.6692	Remote Similarity	NPC194390

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 NPC69496 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	98
0.1-0.2	309
0.2-0.3	746
0.3-0.4	1961
0.4-0.5	3228
0.5-0.6	2115
0.6-0.7	555
0.7-0.8	97
0.8-0.85	10
0.85-0.9	1
0.9-0.95	14
0.95-1	16

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD2613	Approved
0.9758	High Similarity	NPD4746	Phase 3
0.9758	High Similarity	NPD3615	Approved
0.9758	High Similarity	NPD2574	Discontinued
0.9758	High Similarity	NPD3089	Approved
0.9758	High Similarity	NPD2573	Approved
0.9758	High Similarity	NPD3088	Approved
0.9758	High Similarity	NPD3090	Approved
0.9758	High Similarity	NPD2572	Clinical (unspecified phase)
0.9758	High Similarity	NPD2570	Approved
0.9758	High Similarity	NPD4745	Approved
0.9758	High Similarity	NPD2566	Approved
0.9758	High Similarity	NPD2571	Approved
0.9758	High Similarity	NPD3614	Approved
0.9758	High Similarity	NPD3616	Approved
0.9758	High Similarity	NPD3087	Approved
0.9603	High Similarity	NPD4684	Phase 3
0.9603	High Similarity	NPD4685	Phase 3
0.9603	High Similarity	NPD4686	Approved
0.9421	High Similarity	NPD2609	Approved
0.9421	High Similarity	NPD4216	Approved
0.9421	High Similarity	NPD4217	Approved
0.9421	High Similarity	NPD2610	Approved
0.9421	High Similarity	NPD4218	Approved
0.9421	High Similarity	NPD3132	Approved
0.9421	High Similarity	NPD2608	Approved
0.9421	High Similarity	NPD3131	Approved
0.9421	High Similarity	NPD4215	Approved
0.9421	High Similarity	NPD2612	Approved
0.9421	High Similarity	NPD2611	Approved
0.8889	High Similarity	NPD2575	Approved
0.8244	Intermediate Similarity	NPD2160	Approved
0.8244	Intermediate Similarity	NPD2627	Approved
0.8244	Intermediate Similarity	NPD2625	Approved
0.8244	Intermediate Similarity	NPD2626	Approved
0.8244	Intermediate Similarity	NPD2628	Approved
0.8244	Intermediate Similarity	NPD2159	Approved
0.8226	Intermediate Similarity	NPD2652	Approved
0.8226	Intermediate Similarity	NPD2650	Approved
0.8175	Intermediate Similarity	NPD4574	Approved
0.8175	Intermediate Similarity	NPD4576	Approved
0.7986	Intermediate Similarity	NPD3648	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2569	Approved
0.7914	Intermediate Similarity	NPD2567	Approved
0.7862	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3664	Approved
0.7852	Intermediate Similarity	NPD5204	Approved
0.7852	Intermediate Similarity	NPD3661	Approved
0.7852	Intermediate Similarity	NPD3662	Phase 3
0.7852	Intermediate Similarity	NPD3663	Approved
0.7826	Intermediate Similarity	NPD6310	Approved
0.7826	Intermediate Similarity	NPD6311	Approved
0.7826	Intermediate Similarity	NPD6309	Approved
0.781	Intermediate Similarity	NPD4621	Approved
0.781	Intermediate Similarity	NPD4619	Approved
0.7794	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD1752	Approved
0.776	Intermediate Similarity	NPD1756	Approved
0.7717	Intermediate Similarity	NPD2607	Approved
0.7692	Intermediate Similarity	NPD2117	Pre-registration
0.7692	Intermediate Similarity	NPD2116	Approved
0.7692	Intermediate Similarity	NPD2115	Approved
0.7664	Intermediate Similarity	NPD5201	Approved
0.7664	Intermediate Similarity	NPD4617	Approved
0.7664	Intermediate Similarity	NPD4620	Approved
0.7664	Intermediate Similarity	NPD5203	Approved
0.7656	Intermediate Similarity	NPD1374	Approved
0.7656	Intermediate Similarity	NPD1370	Approved
0.7656	Intermediate Similarity	NPD1371	Approved
0.7656	Intermediate Similarity	NPD1373	Approved
0.7634	Intermediate Similarity	NPD2994	Approved
0.7619	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3030	Approved
0.7576	Intermediate Similarity	NPD3031	Approved
0.7576	Intermediate Similarity	NPD3032	Approved
0.7571	Intermediate Similarity	NPD5121	Approved
0.7571	Intermediate Similarity	NPD5120	Approved
0.7571	Intermediate Similarity	NPD5119	Approved
0.748	Intermediate Similarity	NPD4233	Approved
0.748	Intermediate Similarity	NPD4234	Approved
0.7466	Intermediate Similarity	NPD7488	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD2946	Phase 2
0.7426	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5159	Phase 2
0.7426	Intermediate Similarity	NPD5157	Phase 1
0.7424	Intermediate Similarity	NPD6065	Approved
0.7417	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4806	Approved
0.7407	Intermediate Similarity	NPD4807	Approved
0.7381	Intermediate Similarity	NPD5706	Approved
0.7381	Intermediate Similarity	NPD5704	Approved
0.7381	Intermediate Similarity	NPD5705	Approved
0.7376	Intermediate Similarity	NPD7715	Approved
0.7376	Intermediate Similarity	NPD7714	Approved
0.7372	Intermediate Similarity	NPD5667	Approved
0.7357	Intermediate Similarity	NPD4738	Phase 2
0.7353	Intermediate Similarity	NPD2584	Suspended
0.7343	Intermediate Similarity	NPD8173	Phase 2
0.7343	Intermediate Similarity	NPD8172	Phase 2
0.7333	Intermediate Similarity	NPD4135	Approved
0.7333	Intermediate Similarity	NPD4136	Approved
0.7333	Intermediate Similarity	NPD4106	Approved
0.7328	Intermediate Similarity	NPD4766	Approved
0.7287	Intermediate Similarity	NPD2201	Approved
0.7279	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5305	Approved
0.7259	Intermediate Similarity	NPD5306	Approved
0.7252	Intermediate Similarity	NPD3598	Phase 3
0.7246	Intermediate Similarity	NPD6792	Phase 3
0.7214	Intermediate Similarity	NPD4177	Approved
0.7214	Intermediate Similarity	NPD4175	Approved
0.7203	Intermediate Similarity	NPD8416	Discontinued
0.7197	Intermediate Similarity	NPD1711	Phase 2
0.7194	Intermediate Similarity	NPD6564	Approved
0.7194	Intermediate Similarity	NPD6563	Approved
0.7194	Intermediate Similarity	NPD6565	Approved
0.7192	Intermediate Similarity	NPD7511	Approved
0.7192	Intermediate Similarity	NPD7512	Approved
0.7185	Intermediate Similarity	NPD5981	Approved
0.7185	Intermediate Similarity	NPD4102	Approved
0.7185	Intermediate Similarity	NPD4105	Approved
0.7172	Intermediate Similarity	NPD6852	Discontinued
0.7153	Intermediate Similarity	NPD7437	Approved
0.7153	Intermediate Similarity	NPD7436	Approved
0.7143	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4152	Approved
0.7111	Intermediate Similarity	NPD6345	Approved
0.7111	Intermediate Similarity	NPD6343	Approved
0.7111	Intermediate Similarity	NPD4479	Discontinued
0.7109	Intermediate Similarity	NPD6685	Approved
0.7103	Intermediate Similarity	NPD6073	Approved
0.7103	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4573	Approved
0.7099	Intermediate Similarity	NPD4572	Approved
0.7099	Intermediate Similarity	NPD4571	Approved
0.7092	Intermediate Similarity	NPD5759	Approved
0.7083	Intermediate Similarity	NPD4153	Approved
0.7068	Intermediate Similarity	NPD747	Discontinued
0.7063	Intermediate Similarity	NPD4719	Phase 2
0.7059	Intermediate Similarity	NPD6993	Approved
0.7059	Intermediate Similarity	NPD6994	Approved
0.705	Intermediate Similarity	NPD4677	Discontinued
0.7037	Intermediate Similarity	NPD7522	Discontinued
0.7037	Intermediate Similarity	NPD5991	Approved
0.7037	Intermediate Similarity	NPD5990	Approved
0.7034	Intermediate Similarity	NPD8643	Discontinued
0.7032	Intermediate Similarity	NPD8417	Discontinued
0.7031	Intermediate Similarity	NPD5048	Discontinued
0.7023	Intermediate Similarity	NPD3642	Approved
0.7023	Intermediate Similarity	NPD3644	Approved
0.7023	Intermediate Similarity	NPD3643	Approved
0.7	Intermediate Similarity	NPD2199	Approved
0.7	Intermediate Similarity	NPD6676	Phase 2
0.7	Intermediate Similarity	NPD2198	Approved
0.6987	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5725	Approved
0.6986	Remote Similarity	NPD7510	Approved
0.698	Remote Similarity	NPD2437	Approved
0.698	Remote Similarity	NPD2436	Approved
0.6978	Remote Similarity	NPD3072	Approved
0.6978	Remote Similarity	NPD3071	Approved
0.6978	Remote Similarity	NPD3073	Approved
0.6966	Remote Similarity	NPD8265	Approved
0.6963	Remote Similarity	NPD5292	Approved
0.6963	Remote Similarity	NPD5291	Approved
0.6954	Remote Similarity	NPD8323	Discontinued
0.695	Remote Similarity	NPD4103	Phase 2
0.695	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5235	Approved
0.6947	Remote Similarity	NPD5237	Approved
0.6947	Remote Similarity	NPD5236	Approved
0.6947	Remote Similarity	NPD5240	Approved
0.6947	Remote Similarity	NPD5239	Approved
0.6939	Remote Similarity	NPD6294	Approved
0.6939	Remote Similarity	NPD6295	Approved
0.6929	Remote Similarity	NPD854	Approved
0.6929	Remote Similarity	NPD4659	Approved
0.6929	Remote Similarity	NPD855	Approved
0.6923	Remote Similarity	NPD5263	Approved
0.6918	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4762	Approved
0.6906	Remote Similarity	NPD4761	Approved
0.6906	Remote Similarity	NPD5618	Discontinued
0.6901	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7086	Phase 2
0.6894	Remote Similarity	NPD5927	Discontinued
0.6887	Remote Similarity	NPD3400	Discontinued
0.6883	Remote Similarity	NPD7613	Discontinued
0.6875	Remote Similarity	NPD6039	Approved
0.6875	Remote Similarity	NPD5765	Approved
0.6875	Remote Similarity	NPD3681	Approved
0.6875	Remote Similarity	NPD3683	Approved
0.6875	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3680	Approved
0.6875	Remote Similarity	NPD3682	Approved
0.6871	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2217	Approved
0.6861	Remote Similarity	NPD2218	Phase 2
0.6853	Remote Similarity	NPD3040	Approved
0.6849	Remote Similarity	NPD6623	Phase 3

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