NPASS Compound

Structure

CID304659 OpenBabel06191716112D 22 26 0 0 1 0 0 0 0 0999 V2000 4.2224 -1.3882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6112 -0.4927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8026 -0.0400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1966 3.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9895 4.1120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3953 0.9078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5907 2.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6037 2.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9110 -0.0957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1919 2.7305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5867 1.3605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4075 -0.0188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7904 0.8866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7927 2.7336 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6028 1.3540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9852 2.2725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9923 1.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1905 0.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7828 3.6540 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2102 -0.4682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2836 0.7411 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 20 1 0 0 0 0 2 3 1 0 0 0 0 2 12 2 0 0 0 0 3 13 2 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 19 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 21 1 0 0 0 0 9 22 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 14 7 1 1 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	295.12
Volume:	298.651
LogP:	3.085
LogD:	2.718
LogS:	-3.075
# Rotatable Bonds:	1
TPSA:	39.72
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.878
Synthetic Accessibility Score:	3.142
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.977
MDCK Permeability:	1.937764864123892e-05
Pgp-inhibitor:	0.234
Pgp-substrate:	0.819
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	87.75929260253906%
Volume Distribution (VD):	2.622
Pgp-substrate:	5.955181121826172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.923
CYP1A2-substrate:	0.823
CYP2C19-inhibitor:	0.757
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.699
CYP2D6-inhibitor:	0.947
CYP2D6-substrate:	0.942
CYP3A4-inhibitor:	0.831
CYP3A4-substrate:	0.74

ADMET: Excretion

Clearance (CL):	12.797
Half-life (T1/2):	0.141

ADMET: Toxicity

hERG Blockers:	0.772
Human Hepatotoxicity (H-HT):	0.71
Drug-inuced Liver Injury (DILI):	0.548
AMES Toxicity:	0.801
Rat Oral Acute Toxicity:	0.758
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.292
Carcinogencity:	0.532
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC304659

Natural Product ID:	NPC304659
*Common Name:**	Xylopine
IUPAC Name:	n.a.
Synonyms:	Xylopine
Standard InCHIKey:	RFWCCZDSXIZJMF-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C18H17NO3/c1-20-12-2-3-13-11(6-12)7-14-16-10(4-5-19-14)8-15-18(17(13)16)22-9-21-15/h2-3,6,8,14,19H,4-5,7,9H2,1H3/p+1/t14-/m0/s1
SMILES:	COc1ccc2-c3c4c(CC[NH2+][C@H]4Cc2c1)cc1c3OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227689
PubChem CID:	44422616
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50053a043]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15286289]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[20947202]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253552]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277309]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Wax	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13097	Guatteria amplifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20124	Xylopia discreta	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13097	Guatteria amplifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20124	Xylopia discreta	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11043	Pisum sativum	Species	Fabaceae	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	2
Others	3

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1076	Cell Line	B-cells	IC50	=	8100.0	nM	PMID[486164]
NPT27	Others	Unspecified	CC50	=	64600.0	nM	PMID[486164]
NPT2	Others	Unspecified	IC50	=	5690.0	nM	PMID[486164]
NPT2	Others	Unspecified	Ratio CC50/IC50	=	11.0	n.a.	PMID[486164]
NPT2	Others	Unspecified	Ratio CC50/IC50	=	8.0	n.a.	PMID[486164]

☑ 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 NPC304659 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	393
0.1-0.2	2068
0.2-0.3	10361
0.3-0.4	7407
0.4-0.5	9054
0.5-0.6	10801
0.6-0.7	1849
0.7-0.8	513
0.8-0.85	139
0.85-0.9	68
0.9-0.95	33
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC86144
0.9869	High Similarity	NPC189470
0.9682	High Similarity	NPC6152
0.961	High Similarity	NPC477559
0.961	High Similarity	NPC306902
0.961	High Similarity	NPC160298
0.961	High Similarity	NPC232924
0.961	High Similarity	NPC266753
0.9557	High Similarity	NPC152212
0.9542	High Similarity	NPC170503
0.9542	High Similarity	NPC126519
0.9542	High Similarity	NPC203784
0.9444	High Similarity	NPC267408
0.9441	High Similarity	NPC112575
0.9427	High Similarity	NPC225774
0.9387	High Similarity	NPC32413
0.9387	High Similarity	NPC474506
0.9383	High Similarity	NPC23219
0.9379	High Similarity	NPC477558
0.9367	High Similarity	NPC476432
0.9367	High Similarity	NPC219341
0.9367	High Similarity	NPC24264
0.9325	High Similarity	NPC258695
0.9325	High Similarity	NPC470879
0.9308	High Similarity	NPC298979
0.9308	High Similarity	NPC247389
0.9304	High Similarity	NPC16805
0.9304	High Similarity	NPC302527
0.9304	High Similarity	NPC167546
0.9273	High Similarity	NPC135772
0.9268	High Similarity	NPC155442
0.9268	High Similarity	NPC477561
0.9268	High Similarity	NPC476574
0.9268	High Similarity	NPC312918
0.925	High Similarity	NPC241055
0.9187	High Similarity	NPC210918
0.9182	High Similarity	NPC168409
0.9156	High Similarity	NPC326316
0.9156	High Similarity	NPC81733
0.9125	High Similarity	NPC35627
0.9125	High Similarity	NPC476573
0.9125	High Similarity	NPC81247
0.9096	High Similarity	NPC476575
0.9048	High Similarity	NPC57036
0.9018	High Similarity	NPC149090
0.9018	High Similarity	NPC19520
0.8994	High Similarity	NPC476576
0.8994	High Similarity	NPC186546
0.8951	High Similarity	NPC204947
0.8916	High Similarity	NPC114364
0.8916	High Similarity	NPC320223
0.8909	High Similarity	NPC199465
0.8909	High Similarity	NPC229166
0.8909	High Similarity	NPC128560
0.8869	High Similarity	NPC275132
0.8868	High Similarity	NPC476572
0.8862	High Similarity	NPC126284
0.8861	High Similarity	NPC41178
0.8861	High Similarity	NPC325871
0.8861	High Similarity	NPC99659
0.8861	High Similarity	NPC138487
0.8861	High Similarity	NPC216459
0.8848	High Similarity	NPC192135
0.8848	High Similarity	NPC66341
0.8848	High Similarity	NPC477020
0.8841	High Similarity	NPC26240
0.8841	High Similarity	NPC69712
0.8841	High Similarity	NPC477562
0.8839	High Similarity	NPC475959
0.8837	High Similarity	NPC117717
0.8805	High Similarity	NPC146288
0.8779	High Similarity	NPC475754
0.8758	High Similarity	NPC166014
0.8758	High Similarity	NPC27410
0.8757	High Similarity	NPC248642
0.8742	High Similarity	NPC76079
0.8706	High Similarity	NPC156576
0.8696	High Similarity	NPC477080
0.8688	High Similarity	NPC31311
0.8688	High Similarity	NPC234392
0.8662	High Similarity	NPC219162
0.8647	High Similarity	NPC116284
0.8639	High Similarity	NPC474507
0.8631	High Similarity	NPC148709
0.8631	High Similarity	NPC173416
0.8631	High Similarity	NPC476577
0.8616	High Similarity	NPC233029
0.8616	High Similarity	NPC210148
0.8588	High Similarity	NPC212163
0.8588	High Similarity	NPC179704
0.858	High Similarity	NPC148693
0.858	High Similarity	NPC294790
0.858	High Similarity	NPC118633
0.8555	High Similarity	NPC237579
0.8544	High Similarity	NPC60538
0.8544	High Similarity	NPC207824
0.8538	High Similarity	NPC249405
0.8537	High Similarity	NPC324144
0.8535	High Similarity	NPC90844
0.8535	High Similarity	NPC95075
0.8535	High Similarity	NPC253883
0.8526	High Similarity	NPC145304
0.8521	High Similarity	NPC287588
0.8509	High Similarity	NPC93593
0.8509	High Similarity	NPC244112
0.8506	High Similarity	NPC470925
0.8497	Intermediate Similarity	NPC214116
0.8494	Intermediate Similarity	NPC205421
0.8494	Intermediate Similarity	NPC12053
0.8494	Intermediate Similarity	NPC474931
0.8494	Intermediate Similarity	NPC81218
0.8494	Intermediate Similarity	NPC145832
0.8494	Intermediate Similarity	NPC158376
0.8494	Intermediate Similarity	NPC117188
0.8494	Intermediate Similarity	NPC306555
0.8492	Intermediate Similarity	NPC295676
0.8485	Intermediate Similarity	NPC96603
0.8485	Intermediate Similarity	NPC238530
0.8485	Intermediate Similarity	NPC13504
0.8485	Intermediate Similarity	NPC276944
0.8485	Intermediate Similarity	NPC306843
0.8485	Intermediate Similarity	NPC78222
0.8485	Intermediate Similarity	NPC212794
0.8485	Intermediate Similarity	NPC232514
0.8485	Intermediate Similarity	NPC253043
0.8485	Intermediate Similarity	NPC196447
0.8485	Intermediate Similarity	NPC477563
0.8485	Intermediate Similarity	NPC136508
0.8481	Intermediate Similarity	NPC130941
0.8448	Intermediate Similarity	NPC474904
0.8447	Intermediate Similarity	NPC2295
0.8447	Intermediate Similarity	NPC477564
0.8442	Intermediate Similarity	NPC314682
0.8438	Intermediate Similarity	NPC76213
0.8438	Intermediate Similarity	NPC277669
0.8431	Intermediate Similarity	NPC253429
0.8428	Intermediate Similarity	NPC92541
0.8424	Intermediate Similarity	NPC1229
0.8418	Intermediate Similarity	NPC51957
0.8418	Intermediate Similarity	NPC16107
0.8418	Intermediate Similarity	NPC476144
0.8418	Intermediate Similarity	NPC106295
0.8418	Intermediate Similarity	NPC210437
0.84	Intermediate Similarity	NPC82763
0.8387	Intermediate Similarity	NPC474915
0.8387	Intermediate Similarity	NPC213206
0.8387	Intermediate Similarity	NPC188163
0.8387	Intermediate Similarity	NPC328750
0.8385	Intermediate Similarity	NPC470924
0.8365	Intermediate Similarity	NPC7467
0.8354	Intermediate Similarity	NPC111485
0.8352	Intermediate Similarity	NPC244606
0.8352	Intermediate Similarity	NPC156728
0.8343	Intermediate Similarity	NPC312531
0.8313	Intermediate Similarity	NPC211296
0.8302	Intermediate Similarity	NPC144863
0.8295	Intermediate Similarity	NPC281581
0.8293	Intermediate Similarity	NPC79328
0.8284	Intermediate Similarity	NPC168753
0.8284	Intermediate Similarity	NPC118274
0.8282	Intermediate Similarity	NPC78733
0.8282	Intermediate Similarity	NPC187022
0.8282	Intermediate Similarity	NPC80129
0.828	Intermediate Similarity	NPC128019
0.828	Intermediate Similarity	NPC476567
0.828	Intermediate Similarity	NPC136860
0.8272	Intermediate Similarity	NPC26601
0.8272	Intermediate Similarity	NPC148898
0.827	Intermediate Similarity	NPC46990
0.8263	Intermediate Similarity	NPC39103
0.8263	Intermediate Similarity	NPC2770
0.8247	Intermediate Similarity	NPC7018
0.8242	Intermediate Similarity	NPC7393
0.8235	Intermediate Similarity	NPC239775
0.8208	Intermediate Similarity	NPC220961
0.8204	Intermediate Similarity	NPC233650
0.8204	Intermediate Similarity	NPC475393
0.8202	Intermediate Similarity	NPC302001
0.8187	Intermediate Similarity	NPC2314
0.8187	Intermediate Similarity	NPC476151
0.8187	Intermediate Similarity	NPC285941
0.8176	Intermediate Similarity	NPC185838
0.817	Intermediate Similarity	NPC160692
0.8155	Intermediate Similarity	NPC134858
0.815	Intermediate Similarity	NPC477560
0.8144	Intermediate Similarity	NPC24954
0.8122	Intermediate Similarity	NPC23080
0.8122	Intermediate Similarity	NPC193906
0.8121	Intermediate Similarity	NPC29647
0.8121	Intermediate Similarity	NPC186063
0.8121	Intermediate Similarity	NPC323443
0.8121	Intermediate Similarity	NPC180756
0.8086	Intermediate Similarity	NPC103379
0.8086	Intermediate Similarity	NPC477565
0.8075	Intermediate Similarity	NPC191376
0.8075	Intermediate Similarity	NPC179825
0.8075	Intermediate Similarity	NPC321505
0.8061	Intermediate Similarity	NPC172765
0.8061	Intermediate Similarity	NPC54379
0.8061	Intermediate Similarity	NPC39701

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 NPC304659 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	791
0.2-0.3	1087
0.3-0.4	1918
0.4-0.5	2855
0.5-0.6	1617
0.6-0.7	549
0.7-0.8	114
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8418	Intermediate Similarity	NPD4584	Approved
0.8387	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7298	Approved
0.8228	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6030	Approved
0.8199	Intermediate Similarity	NPD4727	Phase 1
0.8199	Intermediate Similarity	NPD6031	Approved
0.8105	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2421	Approved
0.8012	Intermediate Similarity	NPD2420	Approved
0.8	Intermediate Similarity	NPD3051	Approved
0.795	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3845	Phase 1
0.7907	Intermediate Similarity	NPD4481	Phase 3
0.7879	Intermediate Similarity	NPD4017	Approved
0.7849	Intermediate Similarity	NPD2969	Approved
0.7849	Intermediate Similarity	NPD2970	Approved
0.7811	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD2489	Approved
0.7803	Intermediate Similarity	NPD27	Approved
0.7778	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD3109	Approved
0.7707	Intermediate Similarity	NPD3110	Approved
0.7692	Intermediate Similarity	NPD2977	Approved
0.7692	Intermediate Similarity	NPD2978	Approved
0.7688	Intermediate Similarity	NPD4166	Phase 2
0.7683	Intermediate Similarity	NPD7598	Phase 2
0.7669	Intermediate Similarity	NPD5241	Discontinued
0.7651	Intermediate Similarity	NPD5976	Discontinued
0.7651	Intermediate Similarity	NPD3640	Phase 3
0.7651	Intermediate Similarity	NPD3641	Approved
0.7651	Intermediate Similarity	NPD3639	Approved
0.7644	Intermediate Similarity	NPD4859	Phase 1
0.763	Intermediate Similarity	NPD6107	Approved
0.7625	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8099	Discontinued
0.7614	Intermediate Similarity	NPD8251	Approved
0.7614	Intermediate Similarity	NPD8252	Approved
0.7602	Intermediate Similarity	NPD6788	Approved
0.76	Intermediate Similarity	NPD2898	Approved
0.7584	Intermediate Similarity	NPD6297	Approved
0.7571	Intermediate Similarity	NPD8156	Discontinued
0.7558	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7833	Phase 2
0.7558	Intermediate Similarity	NPD7831	Phase 2
0.7556	Intermediate Similarity	NPD2971	Approved
0.7556	Intermediate Similarity	NPD2968	Approved
0.753	Intermediate Similarity	NPD1424	Approved
0.7516	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5754	Discontinued
0.75	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7906	Approved
0.7471	Intermediate Similarity	NPD4773	Phase 2
0.7471	Intermediate Similarity	NPD4772	Phase 2
0.7468	Intermediate Similarity	NPD5718	Phase 2
0.7459	Intermediate Similarity	NPD4578	Approved
0.7459	Intermediate Similarity	NPD4577	Approved
0.7455	Intermediate Similarity	NPD5160	Discontinued
0.7418	Intermediate Similarity	NPD6851	Approved
0.7418	Intermediate Similarity	NPD6853	Approved
0.7391	Intermediate Similarity	NPD3349	Phase 2
0.7384	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7311	Approved
0.7363	Intermediate Similarity	NPD7310	Approved
0.7363	Intermediate Similarity	NPD7312	Approved
0.7363	Intermediate Similarity	NPD7313	Approved
0.7362	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD4420	Approved
0.7337	Intermediate Similarity	NPD4663	Approved
0.733	Intermediate Similarity	NPD7802	Discontinued
0.7322	Intermediate Similarity	NPD8054	Approved
0.7322	Intermediate Similarity	NPD7309	Approved
0.7322	Intermediate Similarity	NPD8053	Approved
0.7314	Intermediate Similarity	NPD7400	Phase 3
0.7312	Intermediate Similarity	NPD2490	Approved
0.7312	Intermediate Similarity	NPD4475	Approved
0.7312	Intermediate Similarity	NPD4474	Approved
0.7312	Intermediate Similarity	NPD2488	Approved
0.7288	Intermediate Similarity	NPD4010	Discontinued
0.7288	Intermediate Similarity	NPD6071	Discontinued
0.7277	Intermediate Similarity	NPD5457	Discontinued
0.7273	Intermediate Similarity	NPD6037	Discontinued
0.7263	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3124	Discontinued
0.7258	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2563	Approved
0.7241	Intermediate Similarity	NPD2560	Approved
0.7233	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3060	Approved
0.7229	Intermediate Similarity	NPD4162	Approved
0.7225	Intermediate Similarity	NPD3383	Approved
0.7225	Intermediate Similarity	NPD5720	Discontinued
0.7225	Intermediate Similarity	NPD3382	Approved
0.7225	Intermediate Similarity	NPD3384	Approved
0.7222	Intermediate Similarity	NPD7827	Phase 1
0.7202	Intermediate Similarity	NPD5005	Approved
0.7202	Intermediate Similarity	NPD5006	Approved
0.7178	Intermediate Similarity	NPD2492	Phase 1
0.7178	Intermediate Similarity	NPD3763	Approved
0.7174	Intermediate Similarity	NPD7280	Phase 3
0.7174	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7281	Phase 3
0.7169	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5977	Approved
0.7143	Intermediate Similarity	NPD5978	Approved
0.7143	Intermediate Similarity	NPD7479	Phase 2
0.7143	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6618	Phase 2
0.7134	Intermediate Similarity	NPD6895	Approved
0.7134	Intermediate Similarity	NPD6896	Approved
0.7127	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2973	Approved
0.712	Intermediate Similarity	NPD2974	Approved
0.712	Intermediate Similarity	NPD2975	Approved
0.7119	Intermediate Similarity	NPD5709	Phase 3
0.7118	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2120	Phase 2
0.7099	Intermediate Similarity	NPD3530	Approved
0.7099	Intermediate Similarity	NPD3531	Approved
0.7099	Intermediate Similarity	NPD3532	Approved
0.7098	Intermediate Similarity	NPD6612	Phase 2
0.7094	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2154	Approved
0.7091	Intermediate Similarity	NPD2156	Approved
0.7091	Intermediate Similarity	NPD4108	Discontinued
0.7091	Intermediate Similarity	NPD2155	Approved
0.7088	Intermediate Similarity	NPD4873	Discontinued
0.7088	Intermediate Similarity	NPD6042	Phase 2
0.7088	Intermediate Similarity	NPD42	Phase 2
0.7086	Intermediate Similarity	NPD4585	Approved
0.7083	Intermediate Similarity	NPD6748	Discontinued
0.7079	Intermediate Similarity	NPD4666	Phase 3
0.7073	Intermediate Similarity	NPD2986	Phase 2
0.7073	Intermediate Similarity	NPD2653	Approved
0.7073	Intermediate Similarity	NPD2989	Phase 2
0.7068	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4256	Phase 2
0.7066	Intermediate Similarity	NPD4257	Approved
0.7062	Intermediate Similarity	NPD4055	Discovery
0.7062	Intermediate Similarity	NPD5604	Discontinued
0.7041	Intermediate Similarity	NPD4040	Phase 1
0.7037	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5177	Phase 3
0.7018	Intermediate Similarity	NPD2874	Phase 2
0.701	Intermediate Similarity	NPD4580	Approved
0.6995	Remote Similarity	NPD5313	Approved
0.6995	Remote Similarity	NPD5312	Approved
0.6984	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5155	Approved
0.6975	Remote Similarity	NPD5156	Approved
0.6974	Remote Similarity	NPD2493	Approved
0.6974	Remote Similarity	NPD3450	Approved
0.6974	Remote Similarity	NPD2494	Approved
0.6974	Remote Similarity	NPD3452	Approved
0.697	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD3816	Phase 1
0.6965	Remote Similarity	NPD3815	Phase 1
0.6961	Remote Similarity	NPD6687	Approved
0.6961	Remote Similarity	NPD6688	Approved
0.6961	Remote Similarity	NPD4083	Discontinued
0.6943	Remote Similarity	NPD7034	Discontinued
0.6941	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3055	Approved
0.6937	Remote Similarity	NPD3053	Approved
0.6936	Remote Similarity	NPD1914	Approved
0.6935	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6723	Discontinued
0.6933	Remote Similarity	NPD1336	Approved
0.6932	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7291	Discontinued
0.6928	Remote Similarity	NPD593	Approved
0.6928	Remote Similarity	NPD595	Approved
0.6923	Remote Similarity	NPD4107	Approved
0.6919	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7020	Approved
0.6919	Remote Similarity	NPD7019	Approved
0.6918	Remote Similarity	NPD1669	Approved
0.6914	Remote Similarity	NPD3595	Approved
0.6914	Remote Similarity	NPD2606	Approved
0.6914	Remote Similarity	NPD2605	Approved
0.6914	Remote Similarity	NPD3594	Approved
0.6902	Remote Similarity	NPD5096	Phase 3
0.6902	Remote Similarity	NPD5095	Phase 3
0.6894	Remote Similarity	NPD7247	Discontinued
0.6886	Remote Similarity	NPD1753	Discontinued
0.6882	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6331	Phase 2
0.6875	Remote Similarity	NPD7110	Phase 1
0.6875	Remote Similarity	NPD7262	Phase 1
0.6875	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7258	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