NPASS Compound

Structure

NPC119225 OpenBabel07101718222D 45 48 0 0 1 0 0 0 0 0999 V2000 12.1244 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 C 0 0 0 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 -2.5981 2.5000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 0.0000 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 12.9904 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5263 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 0 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 11.2583 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.9904 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2583 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 13.8564 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 5 1 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 19 29 1 0 0 0 0 20 34 1 0 0 0 0 24 38 1 0 0 0 0 25 27 1 0 0 0 0 25 36 1 0 0 0 0 26 28 1 0 0 0 0 26 37 1 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 43 1 0 0 0 0 30 34 2 0 0 0 0 30 35 1 0 0 0 0 31 34 1 0 0 0 0 31 43 1 0 0 0 0 32 1 1 1 0 0 0 32 39 1 0 0 0 0 32 41 1 0 0 0 0 33 2 1 1 0 0 0 33 40 1 0 0 0 0 33 42 1 0 0 0 0 35 21 1 6 0 0 0 35 38 1 0 0 0 0 36 22 1 1 0 0 0 36 41 1 0 0 0 0 37 23 1 1 0 0 0 37 42 1 0 0 0 0 38 43 1 1 0 0 0 39 44 1 1 0 0 0 40 45 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	629.59
Volume:	714.104
LogP:	9.029
LogD:	5.192
LogS:	-7.053
# Rotatable Bonds:	22
TPSA:	67.76
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.071
Synthetic Accessibility Score:	4.966
Fsp3:	0.95
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.513
MDCK Permeability:	7.663960786885582e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.753
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.256

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	94.5780258178711%
Volume Distribution (VD):	0.574
Pgp-substrate:	3.899658203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.464
CYP2C19-inhibitor:	0.157
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.995
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.158
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	2.694
Half-life (T1/2):	0.012

ADMET: Toxicity

hERG Blockers:	0.929
Human Hepatotoxicity (H-HT):	0.981
Drug-inuced Liver Injury (DILI):	0.815
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.963
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.687

Download Data

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

Natural Product: NPC119225

Natural Product ID:	NPC119225
*Common Name:**	Juliprosopine
IUPAC Name:	(2R,3R,6S)-6-[10-[(8R,8aS)-6-[10-[(2S,5R,6R)-5-hydroxy-6-methylpiperidin-2-yl]decyl]-1,2,3,5,8,8a-hexahydroindolizin-8-yl]decyl]-2-methylpiperidin-3-ol
Synonyms:	Juliprosopine
Standard InCHIKey:	JOTBJXJGDRSICD-LLZHOJKQSA-N
Standard InCHI:	InChI=1S/C40H75N3O2/c1-32-39(44)27-25-36(41-32)22-17-13-9-5-3-7-11-15-20-34-30-35(38-24-19-29-43(38)31-34)21-16-12-8-4-6-10-14-18-23-37-26-28-40(45)33(2)42-37/h30,32-33,35-42,44-45H,3-29,31H2,1-2H3/t32-,33-,35-,36+,37+,38+,39-,40-/m1/s1
SMILES:	C[C@@H]1[C@@H](CC[C@H](CCCCCCCCCCC2=C[C@@H](CCCCCCCCCC[C@H]3CC[C@H]([C@@H](C)N3)O)[C@@H]3CCCN3C2)N1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL540975
PubChem CID:	45270562
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives

*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
NPO24830.1	Prosopis glandulosa	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19105653]

☑ 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	14
MIC	4
Others	6

Activity Type	# Activity
Cell Line	7
Organism	15
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	4.7	ug.mL-1	PMID[537051]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	6.0	ug.mL-1	PMID[537051]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.2	ug.mL-1	PMID[537051]
NPT916	Cell Line	SK-MEL	Homo sapiens	IC50	=	2.4	ug.mL-1	PMID[537051]
NPT857	Cell Line	LLC-PK1	Sus scrofa	IC50	=	1.8	ug.mL-1	PMID[537051]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	5.0	ug.mL-1	PMID[537051]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	2.4	ug.mL-1	PMID[537051]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	0.75	ug.mL-1	PMID[537051]
NPT2	Others	Unspecified		Ratio IC50	=	13.0	n.a.	PMID[537051]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.38	ug.mL-1	PMID[537051]
NPT2	Others	Unspecified		Ratio IC50	=	23.0	n.a.	PMID[537051]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.22	ug.mL-1	PMID[537051]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MFC	=	1.25	ug ml-1	PMID[537051]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	1.25	ug.mL-1	PMID[537051]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC50	=	0.9	ug.mL-1	PMID[537051]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MBC	=	20.0	ug ml-1	PMID[537051]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	=	20.0	ug.mL-1	PMID[537051]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	6.0	ug.mL-1	PMID[537051]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5.0	ug.mL-1	PMID[537051]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	3.5	ug.mL-1	PMID[537051]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MFC	=	5.0	ug ml-1	PMID[537051]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	5.0	ug.mL-1	PMID[537051]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	1.5	ug.mL-1	PMID[537051]

☑ 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 NPC119225 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	69
0.1-0.2	617
0.2-0.3	13420
0.3-0.4	15975
0.4-0.5	10584
0.5-0.6	1859
0.6-0.7	150
0.7-0.8	18
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476261
1.0	High Similarity	NPC471635
1.0	High Similarity	NPC25033
1.0	High Similarity	NPC470382
0.7282	Intermediate Similarity	NPC91036
0.717	Intermediate Similarity	NPC176012
0.7115	Intermediate Similarity	NPC474164
0.7075	Intermediate Similarity	NPC100810
0.7075	Intermediate Similarity	NPC144714
0.7053	Intermediate Similarity	NPC476560
0.7033	Intermediate Similarity	NPC26932
0.7021	Intermediate Similarity	NPC473971
0.7021	Intermediate Similarity	NPC475363
0.7021	Intermediate Similarity	NPC473972
0.7	Intermediate Similarity	NPC159367
0.6882	Remote Similarity	NPC477002
0.6881	Remote Similarity	NPC477001
0.6881	Remote Similarity	NPC477000
0.687	Remote Similarity	NPC304646
0.687	Remote Similarity	NPC28280
0.6842	Remote Similarity	NPC473446
0.6842	Remote Similarity	NPC473695
0.6822	Remote Similarity	NPC135799
0.6818	Remote Similarity	NPC472856
0.6796	Remote Similarity	NPC145707
0.6786	Remote Similarity	NPC95920
0.6786	Remote Similarity	NPC147835
0.6786	Remote Similarity	NPC253645
0.6786	Remote Similarity	NPC85001
0.6729	Remote Similarity	NPC91604
0.6698	Remote Similarity	NPC476903
0.6698	Remote Similarity	NPC289140
0.6636	Remote Similarity	NPC473254
0.6609	Remote Similarity	NPC474452
0.6607	Remote Similarity	NPC46981
0.6606	Remote Similarity	NPC118275
0.6596	Remote Similarity	NPC78562
0.6596	Remote Similarity	NPC473588
0.6593	Remote Similarity	NPC23721
0.6556	Remote Similarity	NPC113224
0.6552	Remote Similarity	NPC478137
0.6538	Remote Similarity	NPC84171
0.6529	Remote Similarity	NPC478138
0.6522	Remote Similarity	NPC474459
0.6435	Remote Similarity	NPC472313
0.6429	Remote Similarity	NPC212874
0.6421	Remote Similarity	NPC470993
0.6421	Remote Similarity	NPC470992
0.6396	Remote Similarity	NPC50815
0.6396	Remote Similarity	NPC247060
0.6379	Remote Similarity	NPC79238
0.6372	Remote Similarity	NPC477292
0.633	Remote Similarity	NPC140300
0.632	Remote Similarity	NPC317654
0.632	Remote Similarity	NPC96010
0.629	Remote Similarity	NPC296686
0.6283	Remote Similarity	NPC87919
0.6283	Remote Similarity	NPC475239
0.625	Remote Similarity	NPC473289
0.625	Remote Similarity	NPC471083
0.625	Remote Similarity	NPC471258
0.6228	Remote Similarity	NPC55462
0.62	Remote Similarity	NPC207657
0.62	Remote Similarity	NPC209232
0.6195	Remote Similarity	NPC241879
0.6186	Remote Similarity	NPC3094
0.6183	Remote Similarity	NPC297058
0.6182	Remote Similarity	NPC475646
0.6165	Remote Similarity	NPC473955
0.6147	Remote Similarity	NPC272732
0.6147	Remote Similarity	NPC311164
0.6131	Remote Similarity	NPC477519
0.6124	Remote Similarity	NPC261730
0.6117	Remote Similarity	NPC116881
0.6117	Remote Similarity	NPC57163
0.6111	Remote Similarity	NPC47333
0.61	Remote Similarity	NPC90839
0.6098	Remote Similarity	NPC13351
0.6095	Remote Similarity	NPC324506
0.6091	Remote Similarity	NPC475503
0.6087	Remote Similarity	NPC471259
0.6068	Remote Similarity	NPC274895
0.6058	Remote Similarity	NPC75810
0.6053	Remote Similarity	NPC476877
0.6053	Remote Similarity	NPC55336
0.605	Remote Similarity	NPC314306
0.6038	Remote Similarity	NPC316186
0.6036	Remote Similarity	NPC240650
0.6034	Remote Similarity	NPC319537
0.6034	Remote Similarity	NPC25340
0.6034	Remote Similarity	NPC176773
0.6034	Remote Similarity	NPC315426
0.6034	Remote Similarity	NPC313272
0.6033	Remote Similarity	NPC288629
0.6	Remote Similarity	NPC25455
0.6	Remote Similarity	NPC40488
0.6	Remote Similarity	NPC15249
0.6	Remote Similarity	NPC133420
0.5985	Remote Similarity	NPC142761
0.5984	Remote Similarity	NPC101139
0.5982	Remote Similarity	NPC315170
0.598	Remote Similarity	NPC152039
0.598	Remote Similarity	NPC118329
0.598	Remote Similarity	NPC474122
0.5978	Remote Similarity	NPC476559
0.5963	Remote Similarity	NPC93027
0.5962	Remote Similarity	NPC477199
0.5954	Remote Similarity	NPC122819
0.5948	Remote Similarity	NPC476876
0.5948	Remote Similarity	NPC233256
0.5948	Remote Similarity	NPC195841
0.5948	Remote Similarity	NPC86906
0.5946	Remote Similarity	NPC476449
0.5938	Remote Similarity	NPC476694
0.5938	Remote Similarity	NPC476695
0.5938	Remote Similarity	NPC306973
0.5938	Remote Similarity	NPC475610
0.5938	Remote Similarity	NPC476696
0.5922	Remote Similarity	NPC93630
0.5922	Remote Similarity	NPC472312
0.5917	Remote Similarity	NPC124358
0.5917	Remote Similarity	NPC56796
0.5917	Remote Similarity	NPC477291
0.5913	Remote Similarity	NPC98765
0.5913	Remote Similarity	NPC471260
0.5909	Remote Similarity	NPC147753
0.5909	Remote Similarity	NPC243985
0.5909	Remote Similarity	NPC150057
0.5909	Remote Similarity	NPC280710
0.59	Remote Similarity	NPC308050
0.5897	Remote Similarity	NPC244982
0.5897	Remote Similarity	NPC476756
0.589	Remote Similarity	NPC327517
0.589	Remote Similarity	NPC322372
0.589	Remote Similarity	NPC319334
0.589	Remote Similarity	NPC317377
0.589	Remote Similarity	NPC321485
0.5889	Remote Similarity	NPC82919
0.5888	Remote Similarity	NPC34754
0.5887	Remote Similarity	NPC35037
0.5882	Remote Similarity	NPC79367
0.5882	Remote Similarity	NPC472359
0.5882	Remote Similarity	NPC12035
0.5877	Remote Similarity	NPC77703
0.5873	Remote Similarity	NPC471262
0.5873	Remote Similarity	NPC20035
0.5868	Remote Similarity	NPC241597
0.5862	Remote Similarity	NPC75523
0.5859	Remote Similarity	NPC94881
0.5859	Remote Similarity	NPC48886
0.5859	Remote Similarity	NPC265275
0.5849	Remote Similarity	NPC322672
0.5847	Remote Similarity	NPC207820
0.5843	Remote Similarity	NPC302569
0.5843	Remote Similarity	NPC168308
0.5841	Remote Similarity	NPC270813
0.5825	Remote Similarity	NPC288415
0.5825	Remote Similarity	NPC329782
0.5825	Remote Similarity	NPC45906
0.5825	Remote Similarity	NPC31313
0.5825	Remote Similarity	NPC149908
0.5824	Remote Similarity	NPC112398
0.581	Remote Similarity	NPC475975
0.5802	Remote Similarity	NPC478139
0.5794	Remote Similarity	NPC315188
0.5794	Remote Similarity	NPC473525
0.5789	Remote Similarity	NPC313348
0.5789	Remote Similarity	NPC475987
0.5785	Remote Similarity	NPC474995
0.5785	Remote Similarity	NPC478024
0.5784	Remote Similarity	NPC211322
0.5784	Remote Similarity	NPC120699
0.5784	Remote Similarity	NPC127430
0.5778	Remote Similarity	NPC231129
0.5776	Remote Similarity	NPC474583
0.5769	Remote Similarity	NPC224072
0.5769	Remote Similarity	NPC478136
0.5763	Remote Similarity	NPC271562
0.5758	Remote Similarity	NPC470994
0.5755	Remote Similarity	NPC76283
0.5755	Remote Similarity	NPC319913
0.5739	Remote Similarity	NPC188785
0.5736	Remote Similarity	NPC237286
0.5736	Remote Similarity	NPC471263
0.5735	Remote Similarity	NPC287885
0.5729	Remote Similarity	NPC268922
0.5726	Remote Similarity	NPC44514
0.5725	Remote Similarity	NPC311244
0.5725	Remote Similarity	NPC198644
0.5725	Remote Similarity	NPC324722
0.5714	Remote Similarity	NPC155985
0.5714	Remote Similarity	NPC15413
0.5714	Remote Similarity	NPC40663
0.5714	Remote Similarity	NPC476276
0.5714	Remote Similarity	NPC475150
0.5702	Remote Similarity	NPC476875
0.57	Remote Similarity	NPC212008
0.57	Remote Similarity	NPC51055
0.57	Remote Similarity	NPC34672
0.57	Remote Similarity	NPC62293

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 NPC119225 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	75
0.1-0.2	279
0.2-0.3	2555
0.3-0.4	4235
0.4-0.5	1692
0.5-0.6	297
0.6-0.7	17
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6239	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7335	Phase 2
0.6186	Remote Similarity	NPD7336	Phase 2
0.605	Remote Similarity	NPD6430	Approved
0.605	Remote Similarity	NPD6429	Approved
0.6042	Remote Similarity	NPD5365	Phase 2
0.6016	Remote Similarity	NPD7522	Discontinued
0.5954	Remote Similarity	NPD8449	Approved
0.5909	Remote Similarity	NPD8450	Suspended
0.5902	Remote Similarity	NPD4832	Approved
0.5902	Remote Similarity	NPD4830	Approved
0.5902	Remote Similarity	NPD4831	Approved
0.5868	Remote Similarity	NPD3731	Phase 3
0.5854	Remote Similarity	NPD7508	Discontinued
0.5812	Remote Similarity	NPD7333	Discontinued
0.5772	Remote Similarity	NPD7755	Approved
0.5772	Remote Similarity	NPD7754	Approved
0.5699	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6436	Phase 3
0.5625	Remote Similarity	NPD7342	Discontinued

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