NPASS Compound

Structure

NPC114096 OpenBabel07101719252D 39 42 0 0 1 0 0 0 0 0999 V2000 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 10 14 1 0 0 0 0 11 35 1 0 0 0 0 12 36 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 11 1 1 0 0 0 15 17 1 0 0 0 0 15 37 1 0 0 0 0 16 12 1 1 0 0 0 16 18 1 0 0 0 0 16 38 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 6 0 0 0 18 20 1 0 0 0 0 18 28 1 6 0 0 0 19 21 1 0 0 0 0 19 29 1 1 0 0 0 20 22 1 0 0 0 0 20 30 1 1 0 0 0 21 25 1 0 0 0 0 21 31 1 6 0 0 0 22 26 1 0 0 0 0 22 32 1 6 0 0 0 23 33 2 0 0 0 0 23 35 1 0 0 0 0 24 34 2 0 0 0 0 24 39 1 0 0 0 0 25 36 1 1 0 0 0 25 37 1 0 0 0 0 26 38 1 0 0 0 0 26 39 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	550.17
Volume:	517.208
LogP:	1.169
LogD:	0.72
LogS:	-2.847
# Rotatable Bonds:	10
TPSA:	201.67
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.204
Synthetic Accessibility Score:	4.178
Fsp3:	0.462
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.998
MDCK Permeability:	5.225033964961767e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.38
Human Intestinal Absorption (HIA):	0.938
20% Bioavailability (F20%):	0.081
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	72.8270492553711%
Volume Distribution (VD):	0.541
Pgp-substrate:	6.036650657653809%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	1.523
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.377
Human Hepatotoxicity (H-HT):	0.012
Drug-inuced Liver Injury (DILI):	0.773
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.452
Carcinogencity:	0.1
Eye Corrosion:	0.003
Eye Irritation:	0.71
Respiratory Toxicity:	0.003

Download Data

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

Natural Product: NPC114096

Natural Product ID:	NPC114096
*Common Name:**	Prupersin D
IUPAC Name:	[(2R,3S,4S,5R,6R)-6-[[(2R,3S,4S,5R,6S)-6-benzoyloxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl benzoate
Synonyms:
Standard InCHIKey:	NMJQZNCXSRWPAF-GXMBHZMLSA-N
Standard InCHI:	InChI=1S/C26H30O13/c27-17-15(11-35-23(33)13-7-3-1-4-8-13)37-25(21(31)19(17)29)36-12-16-18(28)20(30)22(32)26(38-16)39-24(34)14-9-5-2-6-10-14/h1-10,15-22,25-32H,11-12H2/t15-,16-,17-,18-,19+,20+,21-,22-,25-,26+/m1/s1
SMILES:	O[C@@H]1[C@@H](O)[C@H](OC[C@H]2O[C@@H](OC(=O)c3ccccc3)[C@@H]([C@H]([C@@H]2O)O)O)O[C@@H]([C@H]1O)COC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419611
PubChem CID:	73355242
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2045817]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	seeds	n.a.	n.a.	PMID[23985009]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4446	Prunus davidiana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	5
Others	3

Activity Type	# Activity
Cell Line	5
Subcellular	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[494198]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[494198]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[494198]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[494198]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[494198]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	Inhibition	=	56.0	%	PMID[494198]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	Inhibition	=	66.0	%	PMID[494198]

☑ 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 NPC114096 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	282
0.1-0.2	1117
0.2-0.3	2600
0.3-0.4	6919
0.4-0.5	11650
0.5-0.6	11489
0.6-0.7	6903
0.7-0.8	1638
0.8-0.85	85
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC148026
0.9512	High Similarity	NPC301857
0.8931	High Similarity	NPC471345
0.888	High Similarity	NPC57607
0.8862	High Similarity	NPC229600
0.8828	High Similarity	NPC27712
0.875	High Similarity	NPC471028
0.8672	High Similarity	NPC471025
0.8605	High Similarity	NPC471024
0.8603	High Similarity	NPC245219
0.8603	High Similarity	NPC31081
0.8603	High Similarity	NPC65833
0.8583	High Similarity	NPC244454
0.8583	High Similarity	NPC87153
0.8583	High Similarity	NPC162925
0.8571	High Similarity	NPC140561
0.8571	High Similarity	NPC141970
0.854	High Similarity	NPC478250
0.8538	High Similarity	NPC11025
0.8529	High Similarity	NPC80098
0.8516	High Similarity	NPC77651
0.8516	High Similarity	NPC28069
0.85	High Similarity	NPC470825
0.8487	Intermediate Similarity	NPC474148
0.8487	Intermediate Similarity	NPC276061
0.8473	Intermediate Similarity	NPC319995
0.8473	Intermediate Similarity	NPC289415
0.845	Intermediate Similarity	NPC10883
0.845	Intermediate Similarity	NPC231888
0.845	Intermediate Similarity	NPC35338
0.845	Intermediate Similarity	NPC204214
0.845	Intermediate Similarity	NPC198918
0.845	Intermediate Similarity	NPC10121
0.845	Intermediate Similarity	NPC290276
0.845	Intermediate Similarity	NPC124878
0.845	Intermediate Similarity	NPC63404
0.845	Intermediate Similarity	NPC92283
0.8421	Intermediate Similarity	NPC136608
0.8421	Intermediate Similarity	NPC38420
0.8421	Intermediate Similarity	NPC114116
0.8417	Intermediate Similarity	NPC30563
0.8409	Intermediate Similarity	NPC225384
0.8409	Intermediate Similarity	NPC246869
0.8409	Intermediate Similarity	NPC138777
0.8403	Intermediate Similarity	NPC184633
0.8387	Intermediate Similarity	NPC469574
0.838	Intermediate Similarity	NPC182350
0.8369	Intermediate Similarity	NPC469448
0.8347	Intermediate Similarity	NPC158282
0.8333	Intermediate Similarity	NPC475478
0.831	Intermediate Similarity	NPC22137
0.8309	Intermediate Similarity	NPC475195
0.8271	Intermediate Similarity	NPC46137
0.8271	Intermediate Similarity	NPC235294
0.8264	Intermediate Similarity	NPC469422
0.8244	Intermediate Similarity	NPC231627
0.8244	Intermediate Similarity	NPC288416
0.8239	Intermediate Similarity	NPC92054
0.8239	Intermediate Similarity	NPC140722
0.8239	Intermediate Similarity	NPC4958
0.8227	Intermediate Similarity	NPC291153
0.8214	Intermediate Similarity	NPC473281
0.8214	Intermediate Similarity	NPC77922
0.8211	Intermediate Similarity	NPC474641
0.8195	Intermediate Similarity	NPC17567
0.8194	Intermediate Similarity	NPC131874
0.8194	Intermediate Similarity	NPC93619
0.8182	Intermediate Similarity	NPC111785
0.8182	Intermediate Similarity	NPC237182
0.8182	Intermediate Similarity	NPC226101
0.8168	Intermediate Similarity	NPC147032
0.8151	Intermediate Similarity	NPC269457
0.8151	Intermediate Similarity	NPC37714
0.8151	Intermediate Similarity	NPC152384
0.8143	Intermediate Similarity	NPC242756
0.8138	Intermediate Similarity	NPC34066
0.8129	Intermediate Similarity	NPC79908
0.8115	Intermediate Similarity	NPC43584
0.8115	Intermediate Similarity	NPC264784
0.8112	Intermediate Similarity	NPC302989
0.8112	Intermediate Similarity	NPC303429
0.8112	Intermediate Similarity	NPC222102
0.811	Intermediate Similarity	NPC476096
0.8092	Intermediate Similarity	NPC126991
0.8092	Intermediate Similarity	NPC476033
0.8092	Intermediate Similarity	NPC83218
0.8077	Intermediate Similarity	NPC138798
0.8071	Intermediate Similarity	NPC148080
0.8071	Intermediate Similarity	NPC469623
0.8069	Intermediate Similarity	NPC140151
0.8065	Intermediate Similarity	NPC474363
0.8058	Intermediate Similarity	NPC77493
0.8056	Intermediate Similarity	NPC92117
0.8056	Intermediate Similarity	NPC469415
0.8045	Intermediate Similarity	NPC225307
0.8043	Intermediate Similarity	NPC78363
0.8042	Intermediate Similarity	NPC473149
0.8041	Intermediate Similarity	NPC477623
0.803	Intermediate Similarity	NPC471157
0.8029	Intermediate Similarity	NPC263829
0.8028	Intermediate Similarity	NPC477737
0.8027	Intermediate Similarity	NPC469417
0.8027	Intermediate Similarity	NPC477735
0.8027	Intermediate Similarity	NPC92153
0.8027	Intermediate Similarity	NPC279281
0.8027	Intermediate Similarity	NPC230439
0.8027	Intermediate Similarity	NPC299761
0.8014	Intermediate Similarity	NPC134905
0.8014	Intermediate Similarity	NPC36130
0.8014	Intermediate Similarity	NPC469398
0.8	Intermediate Similarity	NPC29607
0.8	Intermediate Similarity	NPC52097
0.8	Intermediate Similarity	NPC478255
0.7986	Intermediate Similarity	NPC120621
0.7986	Intermediate Similarity	NPC248257
0.7984	Intermediate Similarity	NPC265002
0.7983	Intermediate Similarity	NPC469527
0.7973	Intermediate Similarity	NPC477736
0.7973	Intermediate Similarity	NPC469399
0.7973	Intermediate Similarity	NPC476784
0.7972	Intermediate Similarity	NPC473867
0.7971	Intermediate Similarity	NPC472132
0.797	Intermediate Similarity	NPC106677
0.7959	Intermediate Similarity	NPC215811
0.7959	Intermediate Similarity	NPC44260
0.7959	Intermediate Similarity	NPC16024
0.7959	Intermediate Similarity	NPC61152
0.7959	Intermediate Similarity	NPC205037
0.7959	Intermediate Similarity	NPC137813
0.7959	Intermediate Similarity	NPC3746
0.7955	Intermediate Similarity	NPC79608
0.7953	Intermediate Similarity	NPC216605
0.7953	Intermediate Similarity	NPC266389
0.7953	Intermediate Similarity	NPC122245
0.7945	Intermediate Similarity	NPC469477
0.7945	Intermediate Similarity	NPC472658
0.7945	Intermediate Similarity	NPC133430
0.7945	Intermediate Similarity	NPC472657
0.7931	Intermediate Similarity	NPC478236
0.7931	Intermediate Similarity	NPC478234
0.7926	Intermediate Similarity	NPC469519
0.7923	Intermediate Similarity	NPC11724
0.792	Intermediate Similarity	NPC172525
0.7914	Intermediate Similarity	NPC101686
0.7914	Intermediate Similarity	NPC65262
0.7914	Intermediate Similarity	NPC469364
0.7914	Intermediate Similarity	NPC260425
0.7914	Intermediate Similarity	NPC473301
0.7905	Intermediate Similarity	NPC327032
0.7905	Intermediate Similarity	NPC191046
0.7905	Intermediate Similarity	NPC194095
0.7905	Intermediate Similarity	NPC472128
0.7905	Intermediate Similarity	NPC472127
0.7903	Intermediate Similarity	NPC234376
0.7903	Intermediate Similarity	NPC474314
0.7899	Intermediate Similarity	NPC123988
0.7899	Intermediate Similarity	NPC212729
0.7895	Intermediate Similarity	NPC252114
0.7895	Intermediate Similarity	NPC471026
0.7891	Intermediate Similarity	NPC5115
0.7891	Intermediate Similarity	NPC478235
0.7891	Intermediate Similarity	NPC469456
0.7887	Intermediate Similarity	NPC475759
0.7887	Intermediate Similarity	NPC241951
0.7887	Intermediate Similarity	NPC470152
0.7883	Intermediate Similarity	NPC28637
0.7879	Intermediate Similarity	NPC125053
0.7877	Intermediate Similarity	NPC100818
0.7872	Intermediate Similarity	NPC134405
0.7872	Intermediate Similarity	NPC476385
0.7868	Intermediate Similarity	NPC281798
0.7868	Intermediate Similarity	NPC239358
0.7867	Intermediate Similarity	NPC474441
0.7867	Intermediate Similarity	NPC187205
0.7867	Intermediate Similarity	NPC476026
0.7867	Intermediate Similarity	NPC133984
0.7867	Intermediate Similarity	NPC474398
0.7867	Intermediate Similarity	NPC474401
0.7862	Intermediate Similarity	NPC476173
0.7862	Intermediate Similarity	NPC472339
0.7857	Intermediate Similarity	NPC81515
0.7857	Intermediate Similarity	NPC205195
0.7857	Intermediate Similarity	NPC472547
0.7857	Intermediate Similarity	NPC89105
0.7857	Intermediate Similarity	NPC68092
0.7857	Intermediate Similarity	NPC64141
0.7857	Intermediate Similarity	NPC197316
0.7857	Intermediate Similarity	NPC476383
0.7857	Intermediate Similarity	NPC472350
0.7852	Intermediate Similarity	NPC319404
0.7852	Intermediate Similarity	NPC10205
0.7846	Intermediate Similarity	NPC476872
0.7842	Intermediate Similarity	NPC294470
0.7842	Intermediate Similarity	NPC166180
0.7838	Intermediate Similarity	NPC157898
0.7838	Intermediate Similarity	NPC229354
0.7838	Intermediate Similarity	NPC257847
0.7832	Intermediate Similarity	NPC471104
0.7832	Intermediate Similarity	NPC29704
0.7832	Intermediate Similarity	NPC158663

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 NPC114096 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	715
0.2-0.3	1388
0.3-0.4	2905
0.4-0.5	2544
0.5-0.6	1064
0.6-0.7	282
0.7-0.8	21
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
0.7857	Intermediate Similarity	NPD7266	Discontinued
0.7731	Intermediate Similarity	NPD1238	Approved
0.7721	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD969	Suspended
0.755	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD5126	Approved
0.75	Intermediate Similarity	NPD5125	Phase 3
0.75	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5403	Approved
0.7381	Intermediate Similarity	NPD2182	Approved
0.7365	Intermediate Similarity	NPD5401	Approved
0.7329	Intermediate Similarity	NPD4628	Phase 3
0.7312	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD8313	Approved
0.7301	Intermediate Similarity	NPD8312	Approved
0.7284	Intermediate Similarity	NPD7685	Pre-registration
0.7279	Intermediate Similarity	NPD6190	Approved
0.7266	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4380	Phase 2
0.7218	Intermediate Similarity	NPD9545	Approved
0.7205	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7054	Approved
0.72	Intermediate Similarity	NPD1237	Approved
0.7176	Intermediate Similarity	NPD2629	Approved
0.7167	Intermediate Similarity	NPD1202	Approved
0.7161	Intermediate Similarity	NPD5402	Approved
0.716	Intermediate Similarity	NPD7472	Approved
0.716	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD7799	Discontinued
0.7134	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1933	Approved
0.7132	Intermediate Similarity	NPD1091	Approved
0.7117	Intermediate Similarity	NPD6797	Phase 2
0.7115	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7008	Discontinued
0.7073	Intermediate Similarity	NPD6559	Discontinued
0.7073	Intermediate Similarity	NPD7251	Discontinued
0.7073	Intermediate Similarity	NPD9495	Approved
0.7063	Intermediate Similarity	NPD164	Approved
0.7042	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD3818	Discontinued
0.7034	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7808	Phase 3
0.7008	Intermediate Similarity	NPD5048	Discontinued
0.7007	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6233	Phase 2
0.6987	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7075	Discontinued
0.6954	Remote Similarity	NPD6799	Approved
0.6954	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2067	Discontinued
0.6923	Remote Similarity	NPD6801	Discontinued
0.6917	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9256	Approved
0.6917	Remote Similarity	NPD9258	Approved
0.6913	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6832	Phase 2
0.6897	Remote Similarity	NPD230	Phase 1
0.6887	Remote Similarity	NPD7236	Approved
0.6884	Remote Similarity	NPD6287	Discontinued
0.6883	Remote Similarity	NPD1653	Approved
0.688	Remote Similarity	NPD7798	Approved
0.6867	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4198	Discontinued
0.6859	Remote Similarity	NPD7411	Suspended
0.6846	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7458	Discontinued
0.6839	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7228	Approved
0.6824	Remote Similarity	NPD1551	Phase 2
0.6815	Remote Similarity	NPD9493	Approved
0.6809	Remote Similarity	NPD1203	Approved
0.6807	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2313	Discontinued
0.6806	Remote Similarity	NPD6798	Discontinued
0.6797	Remote Similarity	NPD5909	Discontinued
0.6791	Remote Similarity	NPD5951	Approved
0.6774	Remote Similarity	NPD7239	Suspended
0.6766	Remote Similarity	NPD8368	Discontinued
0.6755	Remote Similarity	NPD3750	Approved
0.6738	Remote Similarity	NPD3225	Approved
0.6738	Remote Similarity	NPD5667	Approved
0.6738	Remote Similarity	NPD2199	Approved
0.6738	Remote Similarity	NPD2198	Approved
0.6735	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1549	Phase 2
0.6731	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3817	Phase 2
0.6723	Remote Similarity	NPD9257	Approved
0.6723	Remote Similarity	NPD9259	Approved
0.6719	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1929	Approved
0.6719	Remote Similarity	NPD1930	Approved
0.6719	Remote Similarity	NPD6647	Phase 2
0.6712	Remote Similarity	NPD5119	Approved
0.6712	Remote Similarity	NPD5121	Approved
0.6712	Remote Similarity	NPD5120	Approved
0.6709	Remote Similarity	NPD37	Approved
0.6707	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6166	Phase 2
0.6691	Remote Similarity	NPD4106	Approved
0.6691	Remote Similarity	NPD4136	Approved
0.6691	Remote Similarity	NPD4135	Approved
0.669	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7097	Phase 1
0.6688	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6599	Discontinued
0.6687	Remote Similarity	NPD4965	Approved
0.6687	Remote Similarity	NPD4966	Approved
0.6687	Remote Similarity	NPD4967	Phase 2
0.6687	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD5157	Phase 1
0.6667	Remote Similarity	NPD4617	Approved
0.6667	Remote Similarity	NPD5159	Phase 2
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7240	Approved
0.6667	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4620	Approved
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5201	Approved
0.6667	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD5203	Approved
0.6667	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8407	Phase 2
0.6644	Remote Similarity	NPD7033	Discontinued
0.6644	Remote Similarity	NPD3748	Approved
0.6644	Remote Similarity	NPD4062	Phase 3
0.6643	Remote Similarity	NPD2798	Approved
0.6643	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6535	Approved
0.6629	Remote Similarity	NPD6534	Approved
0.6619	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD5305	Approved
0.6619	Remote Similarity	NPD5306	Approved
0.6614	Remote Similarity	NPD2066	Phase 3
0.661	Remote Similarity	NPD7699	Phase 2
0.661	Remote Similarity	NPD7700	Phase 2
0.6608	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6234	Discontinued
0.6604	Remote Similarity	NPD1934	Approved
0.66	Remote Similarity	NPD2935	Discontinued
0.6596	Remote Similarity	NPD9717	Approved
0.6594	Remote Similarity	NPD1894	Discontinued
0.659	Remote Similarity	NPD8360	Approved
0.659	Remote Similarity	NPD8435	Approved
0.659	Remote Similarity	NPD8361	Approved
0.6575	Remote Similarity	NPD8320	Phase 1
0.6575	Remote Similarity	NPD8319	Approved
0.6573	Remote Similarity	NPD2625	Approved
0.6573	Remote Similarity	NPD2797	Approved
0.6573	Remote Similarity	NPD2160	Approved
0.6573	Remote Similarity	NPD2626	Approved
0.6573	Remote Similarity	NPD2627	Approved
0.6573	Remote Similarity	NPD2159	Approved
0.6573	Remote Similarity	NPD2628	Approved
0.6571	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6213	Phase 3
0.6571	Remote Similarity	NPD6212	Phase 3
0.657	Remote Similarity	NPD8150	Discontinued
0.6569	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1465	Phase 2
0.6558	Remote Similarity	NPD7440	Discontinued
0.6557	Remote Similarity	NPD689	Discontinued
0.6556	Remote Similarity	NPD2346	Discontinued
0.6554	Remote Similarity	NPD6355	Discontinued
0.6554	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD4105	Approved
0.6547	Remote Similarity	NPD4102	Approved
0.6538	Remote Similarity	NPD6273	Approved
0.6536	Remote Similarity	NPD2575	Approved
0.6533	Remote Similarity	NPD1510	Phase 2
0.6533	Remote Similarity	NPD4308	Phase 3
0.6531	Remote Similarity	NPD7713	Phase 3
0.6527	Remote Similarity	NPD3751	Discontinued
0.6525	Remote Similarity	NPD4806	Approved
0.6525	Remote Similarity	NPD4807	Approved
0.6524	Remote Similarity	NPD7199	Phase 2
0.6519	Remote Similarity	NPD3455	Phase 2
0.6519	Remote Similarity	NPD7435	Discontinued
0.6515	Remote Similarity	NPD6686	Approved
0.6515	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD1932	Approved
0.6508	Remote Similarity	NPD1989	Approved
0.6507	Remote Similarity	NPD6039	Approved
0.6494	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2796	Approved
0.6486	Remote Similarity	NPD6311	Approved
0.6486	Remote Similarity	NPD6310	Approved
0.6486	Remote Similarity	NPD6309	Approved
0.6485	Remote Similarity	NPD3787	Discontinued
0.6483	Remote Similarity	NPD5204	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data