NPASS Compound

Structure

NPC115595 OpenBabel07101718302D 30 32 0 0 0 0 0 0 0 0999 V2000 9.5263 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 4.5000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 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 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 6.0000 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 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 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 5.1962 2.0000 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 4.3301 3.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 14 1 0 0 0 0 6 23 1 0 0 0 0 7 27 1 0 0 0 0 8 30 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 24 2 0 0 0 0 11 25 1 0 0 0 0 12 26 2 0 0 0 0 12 28 1 0 0 0 0 13 27 1 0 0 0 0 13 29 2 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 0 0 0 0 19 26 1 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.03
Volume:	429.843
LogP:	2.732
LogD:	2.283
LogS:	-3.561
# Rotatable Bonds:	9
TPSA:	88.4
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	3.37
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.864
MDCK Permeability:	1.660703492234461e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.793
20% Bioavailability (F20%):	0.163
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.893
Plasma Protein Binding (PPB):	91.17546844482422%
Volume Distribution (VD):	1.438
Pgp-substrate:	16.688684463500977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.905
CYP1A2-substrate:	0.575
CYP2C19-inhibitor:	0.837
CYP2C19-substrate:	0.275
CYP2C9-inhibitor:	0.104
CYP2C9-substrate:	0.578
CYP2D6-inhibitor:	0.903
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.736

ADMET: Excretion

Clearance (CL):	3.312
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.651
Drug-inuced Liver Injury (DILI):	0.819
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.898
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.47
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.853

Download Data

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

Natural Product: NPC115595

Natural Product ID:	NPC115595
*Common Name:**	Aphrocallistin
IUPAC Name:	N-[2-[3,5-dibromo-4-[3-[(3-methylpurin-6-yl)amino]propoxy]phenyl]ethyl]-N-methylacetamide
Synonyms:	Aphrocallistin
Standard InCHIKey:	ONIZXWNHLRRDOK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H24Br2N6O2/c1-13(29)27(2)7-5-14-9-15(21)18(16(22)10-14)30-8-4-6-23-19-17-20(25-11-24-17)28(3)12-26-19/h9-12,23H,4-8H2,1-3H3
SMILES:	CC(=O)N(CCc1cc(Br)c(c(c1)Br)OCCCNc1ncn(c2c1ncn2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086155
PubChem CID:	25168594
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001797] Imidazopyrimidines [CHEMONTID:0000245] Purines and purine derivatives [CHEMONTID:0002987] 6-aminopurines [CHEMONTID:0003454] 6-alkylaminopurines

*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
NPO1486	Aphrocallistes beatrix	Species	Aphrocallistidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19459694]
NPO1486	Aphrocallistes beatrix	Species	Aphrocallistidae	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	8
MIC	3
Others	80

Activity Type	# Activity
Cell Line	61
NON-MOLECULAR	1
Organism	3
Others	11
Subcellular	3
Tissue	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2297	Cell Line	ASPC1	Homo sapiens	IC50	>	100000.0	nM	PMID[493251]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	15900.0	nM	PMID[493251]
NPT1081	Cell Line	BXPC-3	Homo sapiens	IC50	=	70900.0	nM	PMID[493251]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	7500.0	nM	PMID[493251]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	26600.0	nM	PMID[493251]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	IC50	=	34300.0	nM	PMID[493251]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	22800.0	nM	PMID[493251]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	76100.0	nM	PMID[493251]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	80.24	%	PMID[493251]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	39.94	%	PMID[493251]
NPT112	Cell Line	MOLT-4	Homo sapiens	Activity	=	50.93	%	PMID[493251]
NPT385	Cell Line	SR	Homo sapiens	Activity	=	10.72	%	PMID[493251]
NPT394	Cell Line	EKVX	Homo sapiens	Activity	=	45.38	%	PMID[493251]
NPT379	Cell Line	HOP-62	Homo sapiens	Activity	=	71.38	%	PMID[493251]
NPT372	Cell Line	HOP-92	Homo sapiens	Activity	=	75.25	%	PMID[493251]
NPT405	Cell Line	NCI-H226	Homo sapiens	Activity	=	44.72	%	PMID[493251]
NPT370	Cell Line	NCI-H23	Homo sapiens	Activity	=	42.18	%	PMID[493251]
NPT388	Cell Line	NCI-H322M	Homo sapiens	Activity	=	76.48	%	PMID[493251]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	60.08	%	PMID[493251]
NPT455	Cell Line	NCI-H522	Homo sapiens	Activity	=	36.6	%	PMID[493251]
NPT407	Cell Line	COLO 205	Homo sapiens	Activity	=	104.32	%	PMID[493251]
NPT391	Cell Line	HCC 2998	Homo sapiens	Activity	=	65.57	%	PMID[493251]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	28.57	%	PMID[493251]
NPT148	Cell Line	HCT-15	Homo sapiens	Activity	=	99.13	%	PMID[493251]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	88.11	%	PMID[493251]
NPT386	Cell Line	KM12	Homo sapiens	Activity	=	88.97	%	PMID[493251]
NPT323	Cell Line	SW-620	Homo sapiens	Activity	=	89.87	%	PMID[493251]
NPT395	Cell Line	SF-268	Homo sapiens	Activity	=	97.87	%	PMID[493251]
NPT399	Cell Line	SF-295	Homo sapiens	Activity	=	50.01	%	PMID[493251]
NPT374	Cell Line	SF-539	Homo sapiens	Activity	=	80.09	%	PMID[493251]
NPT383	Cell Line	SNB-19	Homo sapiens	Activity	=	71.64	%	PMID[493251]
NPT392	Cell Line	SNB-75	Homo sapiens	Activity	=	81.17	%	PMID[493251]
NPT380	Cell Line	U-251	Homo sapiens	Activity	=	79.39	%	PMID[493251]
NPT390	Cell Line	LOX IMVI	Homo sapiens	Activity	=	55.23	%	PMID[493251]
NPT387	Cell Line	M14	Homo sapiens	Activity	=	73.49	%	PMID[493251]
NPT375	Cell Line	Malme-3M	Homo sapiens	Activity	=	76.4	%	PMID[493251]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	Activity	=	62.57	%	PMID[493251]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	Activity	=	71.47	%	PMID[493251]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	Activity	=	84.58	%	PMID[493251]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	Activity	=	20.0	%	PMID[493251]
NPT398	Cell Line	UACC-62	Homo sapiens	Activity	=	79.32	%	PMID[493251]
NPT458	Cell Line	IGROV-1	Homo sapiens	Activity	=	64.84	%	PMID[493251]
NPT377	Cell Line	OVCAR-3	Homo sapiens	Activity	=	87.3	%	PMID[493251]
NPT456	Cell Line	OVCAR-4	Homo sapiens	Activity	=	33.32	%	PMID[493251]
NPT382	Cell Line	OVCAR-5	Homo sapiens	Activity	=	88.65	%	PMID[493251]
NPT146	Cell Line	SK-OV-3	Homo sapiens	Activity	=	94.44	%	PMID[493251]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	Activity	=	72.89	%	PMID[493251]
NPT401	Cell Line	786-0	Homo sapiens	Activity	=	70.65	%	PMID[493251]
NPT376	Cell Line	A498	Homo sapiens	Activity	=	71.71	%	PMID[493251]
NPT369	Cell Line	ACHN	Homo sapiens	Activity	=	69.23	%	PMID[493251]
NPT368	Cell Line	SN12C	Homo sapiens	Activity	=	92.68	%	PMID[493251]
NPT384	Cell Line	TK-10	Homo sapiens	Activity	=	89.47	%	PMID[493251]
NPT371	Cell Line	UO-31	Homo sapiens	Activity	=	79.45	%	PMID[493251]
NPT90	Cell Line	DU-145	Homo sapiens	Activity	=	102.31	%	PMID[493251]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	39.83	%	PMID[493251]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	74.94	%	PMID[493251]
NPT457	Cell Line	BT-549	Homo sapiens	Activity	=	56.49	%	PMID[493251]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	26.91	%	PMID[493251]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	Activity	=	25.48	%	PMID[493251]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Ratio IC50	=	3.0	n.a.	PMID[493251]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Ratio IC50	=	10.0	n.a.	PMID[493251]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	250.0	ug.mL-1	PMID[493251]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	250.0	ug.mL-1	PMID[493251]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	500.0	ug.mL-1	PMID[493251]
NPT35	Others	n.a.		Solubility	>	267.0	ug.mL-1	PMID[493251]
NPT27	Others	Unspecified		permeability	=	33.0	10'-6 cm/s	PMID[493251]
NPT27	Others	Unspecified		permeability	=	201.0	10'-6 cm/s	PMID[493251]
NPT27	Others	Unspecified		permeability	=	321.0	10'-6 cm/s	PMID[493251]
NPT614	Tissue	Plasma	Rattus norvegicus	Fu	=	0.103	n.a.	PMID[493251]
NPT614	Tissue	Plasma	Rattus norvegicus	Fu	=	0.044	n.a.	PMID[493251]
NPT624	Tissue	Plasma	Mus musculus	Fu	=	0.309	n.a.	PMID[493251]
NPT624	Tissue	Plasma	Mus musculus	Fu	=	0.15	n.a.	PMID[493251]
NPT614	Tissue	Plasma	Rattus norvegicus	PPB	=	89.7	%	PMID[493251]
NPT614	Tissue	Plasma	Rattus norvegicus	PPB	=	95.6	%	PMID[493251]
NPT624	Tissue	Plasma	Mus musculus	PPB	=	69.1	%	PMID[493251]
NPT624	Tissue	Plasma	Mus musculus	PPB	=	85.0	%	PMID[493251]
NPT614	Tissue	Plasma	Rattus norvegicus	Stability	=	103.1	%	PMID[493251]
NPT624	Tissue	Plasma	Mus musculus	Stability	=	96.3	%	PMID[493251]
NPT614	Tissue	Plasma	Rattus norvegicus	Stability	=	76.6	%	PMID[493251]
NPT624	Tissue	Plasma	Mus musculus	Activity	=	79.6	%	PMID[493251]
NPT35	Others	n.a.		Stability	=	76.5	%	PMID[493251]
NPT35	Others	n.a.		Stability	=	99.7	%	PMID[493251]
NPT433	Subcellular	Liver microsomes	Homo sapiens	Stability	=	117.73	%	PMID[493251]
NPT433	Subcellular	Liver microsomes	Homo sapiens	Stability	=	3.08	%	PMID[493251]
NPT27	Others	Unspecified		Stability	=	1.44	%	PMID[493251]
NPT27	Others	Unspecified		Stability	=	103.32	%	PMID[493251]
NPT433	Subcellular	Liver microsomes	Homo sapiens	Activity	=	96.92	%	PMID[493251]
NPT27	Others	Unspecified		Activity	=	98.56	%	PMID[493251]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	52.48	%	PMID[493251]

☑ 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 NPC115595 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	537
0.1-0.2	9189
0.2-0.3	8893
0.3-0.4	16100
0.4-0.5	6080
0.5-0.6	1776
0.6-0.7	112
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7773	Intermediate Similarity	NPC160666
0.7444	Intermediate Similarity	NPC113369
0.7412	Intermediate Similarity	NPC250178
0.7241	Intermediate Similarity	NPC243633
0.7241	Intermediate Similarity	NPC175150
0.7181	Intermediate Similarity	NPC242923
0.713	Intermediate Similarity	NPC67658
0.7045	Intermediate Similarity	NPC280638
0.6966	Remote Similarity	NPC308906
0.6894	Remote Similarity	NPC168209
0.689	Remote Similarity	NPC150447
0.6867	Remote Similarity	NPC50562
0.6795	Remote Similarity	NPC50511
0.6763	Remote Similarity	NPC187145
0.6695	Remote Similarity	NPC17305
0.6667	Remote Similarity	NPC223223
0.6638	Remote Similarity	NPC471603
0.6625	Remote Similarity	NPC470502
0.6586	Remote Similarity	NPC30540
0.657	Remote Similarity	NPC470503
0.6569	Remote Similarity	NPC467439
0.656	Remote Similarity	NPC471614
0.6527	Remote Similarity	NPC12100
0.6523	Remote Similarity	NPC56271
0.6511	Remote Similarity	NPC174758
0.6484	Remote Similarity	NPC472067
0.6484	Remote Similarity	NPC472066
0.6484	Remote Similarity	NPC472031
0.6475	Remote Similarity	NPC35761
0.6461	Remote Similarity	NPC470501
0.6422	Remote Similarity	NPC232727
0.6413	Remote Similarity	NPC477254
0.6406	Remote Similarity	NPC472068
0.6405	Remote Similarity	NPC136924
0.6398	Remote Similarity	NPC287208
0.6397	Remote Similarity	NPC237978
0.639	Remote Similarity	NPC308571
0.6371	Remote Similarity	NPC174672
0.6367	Remote Similarity	NPC130570
0.6349	Remote Similarity	NPC274982
0.6335	Remote Similarity	NPC33064
0.6335	Remote Similarity	NPC143450
0.6333	Remote Similarity	NPC77101
0.6331	Remote Similarity	NPC66777
0.6331	Remote Similarity	NPC315822
0.6331	Remote Similarity	NPC471762
0.6329	Remote Similarity	NPC82548
0.6327	Remote Similarity	NPC46970
0.6311	Remote Similarity	NPC265111
0.6311	Remote Similarity	NPC323969
0.6309	Remote Similarity	NPC19872
0.63	Remote Similarity	NPC472289
0.629	Remote Similarity	NPC323244
0.6289	Remote Similarity	NPC477796
0.6289	Remote Similarity	NPC477806
0.6289	Remote Similarity	NPC477805
0.6289	Remote Similarity	NPC477795
0.6276	Remote Similarity	NPC167860
0.6276	Remote Similarity	NPC123976
0.6275	Remote Similarity	NPC471615
0.627	Remote Similarity	NPC292958
0.627	Remote Similarity	NPC174489
0.6255	Remote Similarity	NPC328924
0.6244	Remote Similarity	NPC128877
0.6244	Remote Similarity	NPC317054
0.6239	Remote Similarity	NPC176538
0.6227	Remote Similarity	NPC477255
0.6224	Remote Similarity	NPC26679
0.622	Remote Similarity	NPC26641
0.6215	Remote Similarity	NPC21461
0.6209	Remote Similarity	NPC76412
0.62	Remote Similarity	NPC156003
0.6198	Remote Similarity	NPC476287
0.619	Remote Similarity	NPC198673
0.619	Remote Similarity	NPC296085
0.619	Remote Similarity	NPC71629
0.618	Remote Similarity	NPC267928
0.6178	Remote Similarity	NPC144114
0.6172	Remote Similarity	NPC37152
0.617	Remote Similarity	NPC121772
0.616	Remote Similarity	NPC157931
0.616	Remote Similarity	NPC257851
0.616	Remote Similarity	NPC107160
0.6154	Remote Similarity	NPC60621
0.6154	Remote Similarity	NPC168911
0.615	Remote Similarity	NPC469975
0.615	Remote Similarity	NPC47672
0.6148	Remote Similarity	NPC99891
0.6142	Remote Similarity	NPC158055
0.614	Remote Similarity	NPC156311
0.614	Remote Similarity	NPC233926
0.6139	Remote Similarity	NPC470504
0.6138	Remote Similarity	NPC193267
0.6138	Remote Similarity	NPC213530
0.6135	Remote Similarity	NPC314954
0.6134	Remote Similarity	NPC285558
0.6133	Remote Similarity	NPC473585
0.6126	Remote Similarity	NPC200553
0.6124	Remote Similarity	NPC295452
0.6124	Remote Similarity	NPC39092
0.6124	Remote Similarity	NPC171393
0.6122	Remote Similarity	NPC305984
0.6118	Remote Similarity	NPC162002
0.6107	Remote Similarity	NPC51854
0.6104	Remote Similarity	NPC122436
0.6102	Remote Similarity	NPC141053
0.61	Remote Similarity	NPC185782
0.6096	Remote Similarity	NPC124920
0.6096	Remote Similarity	NPC118559
0.6096	Remote Similarity	NPC34580
0.6096	Remote Similarity	NPC304307
0.6092	Remote Similarity	NPC245816
0.6092	Remote Similarity	NPC476138
0.609	Remote Similarity	NPC63109
0.6085	Remote Similarity	NPC239954
0.6083	Remote Similarity	NPC243850
0.6078	Remote Similarity	NPC245055
0.6076	Remote Similarity	NPC98685
0.6071	Remote Similarity	NPC100547
0.6069	Remote Similarity	NPC9729
0.6067	Remote Similarity	NPC470505
0.6058	Remote Similarity	NPC476465
0.6048	Remote Similarity	NPC78530
0.6047	Remote Similarity	NPC223409
0.6047	Remote Similarity	NPC95240
0.6047	Remote Similarity	NPC322135
0.6042	Remote Similarity	NPC476121
0.6042	Remote Similarity	NPC476124
0.6036	Remote Similarity	NPC164664
0.6035	Remote Similarity	NPC477891
0.6034	Remote Similarity	NPC315957
0.6032	Remote Similarity	NPC261251
0.6025	Remote Similarity	NPC223427
0.6024	Remote Similarity	NPC310118
0.6024	Remote Similarity	NPC14288
0.6009	Remote Similarity	NPC324149
0.6009	Remote Similarity	NPC105758
0.6009	Remote Similarity	NPC476686
0.6009	Remote Similarity	NPC476688
0.6008	Remote Similarity	NPC101350
0.6008	Remote Similarity	NPC48317
0.6	Remote Similarity	NPC77435
0.6	Remote Similarity	NPC54803
0.6	Remote Similarity	NPC279189
0.6	Remote Similarity	NPC321592
0.6	Remote Similarity	NPC259071
0.5992	Remote Similarity	NPC60006
0.5992	Remote Similarity	NPC18487
0.5992	Remote Similarity	NPC214142
0.5992	Remote Similarity	NPC272549
0.5991	Remote Similarity	NPC278874
0.5985	Remote Similarity	NPC26543
0.5984	Remote Similarity	NPC472099
0.5983	Remote Similarity	NPC84853
0.5983	Remote Similarity	NPC295898
0.5983	Remote Similarity	NPC473761
0.5983	Remote Similarity	NPC108011
0.5983	Remote Similarity	NPC284678
0.5982	Remote Similarity	NPC208060
0.5977	Remote Similarity	NPC474357
0.5977	Remote Similarity	NPC284888
0.5972	Remote Similarity	NPC135349
0.5969	Remote Similarity	NPC235685
0.5968	Remote Similarity	NPC110151
0.5968	Remote Similarity	NPC303658
0.5966	Remote Similarity	NPC92111
0.5966	Remote Similarity	NPC329747
0.5965	Remote Similarity	NPC307191
0.5964	Remote Similarity	NPC476518
0.5961	Remote Similarity	NPC260434
0.5961	Remote Similarity	NPC470323
0.5959	Remote Similarity	NPC264176
0.5959	Remote Similarity	NPC179896
0.5958	Remote Similarity	NPC53144
0.5954	Remote Similarity	NPC472434
0.5953	Remote Similarity	NPC258222
0.5952	Remote Similarity	NPC474196
0.5952	Remote Similarity	NPC245348
0.5951	Remote Similarity	NPC470799
0.5951	Remote Similarity	NPC170114
0.5951	Remote Similarity	NPC8022
0.5948	Remote Similarity	NPC246591
0.5944	Remote Similarity	NPC17565
0.5938	Remote Similarity	NPC935
0.5938	Remote Similarity	NPC121658
0.5938	Remote Similarity	NPC469554
0.5938	Remote Similarity	NPC267078
0.5938	Remote Similarity	NPC14651
0.5935	Remote Similarity	NPC282247
0.5934	Remote Similarity	NPC470500
0.5931	Remote Similarity	NPC8093
0.5931	Remote Similarity	NPC121571
0.5929	Remote Similarity	NPC24370
0.5929	Remote Similarity	NPC319232
0.5927	Remote Similarity	NPC223189
0.5926	Remote Similarity	NPC475910
0.5926	Remote Similarity	NPC469711
0.5926	Remote Similarity	NPC71238
0.5924	Remote Similarity	NPC187558
0.5923	Remote Similarity	NPC76748

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 NPC115595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	933
0.2-0.3	663
0.3-0.4	1971
0.4-0.5	3274
0.5-0.6	1720
0.6-0.7	314
0.7-0.8	7
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
0.8027	Intermediate Similarity	NPD5703	Discontinued
0.7689	Intermediate Similarity	NPD3590	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6186	Approved
0.7446	Intermediate Similarity	NPD1273	Discontinued
0.7357	Intermediate Similarity	NPD6643	Discontinued
0.7339	Intermediate Similarity	NPD5116	Phase 1
0.7333	Intermediate Similarity	NPD5051	Phase 1
0.7303	Intermediate Similarity	NPD6573	Phase 3
0.7303	Intermediate Similarity	NPD6572	Phase 2
0.7288	Intermediate Similarity	NPD4847	Phase 1
0.7273	Intermediate Similarity	NPD3255	Phase 1
0.7273	Intermediate Similarity	NPD3254	Phase 1
0.7257	Intermediate Similarity	NPD4306	Phase 1
0.7246	Intermediate Similarity	NPD5139	Phase 1
0.7227	Intermediate Similarity	NPD6760	Discontinued
0.7225	Intermediate Similarity	NPD6202	Discontinued
0.72	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5529	Phase 1
0.7184	Intermediate Similarity	NPD5007	Approved
0.7137	Intermediate Similarity	NPD4048	Approved
0.7106	Intermediate Similarity	NPD4132	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7198	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD34	Approved
0.7098	Intermediate Similarity	NPD4713	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4715	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4714	Approved
0.709	Intermediate Similarity	NPD7620	Phase 2
0.7087	Intermediate Similarity	NPD6528	Phase 1
0.7087	Intermediate Similarity	NPD5052	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6772	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5802	Phase 2
0.7013	Intermediate Similarity	NPD4358	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2984	Phase 2
0.6986	Remote Similarity	NPD1286	Suspended
0.6983	Remote Similarity	NPD4654	Phase 1
0.6979	Remote Similarity	NPD6589	Phase 1
0.6959	Remote Similarity	NPD7757	Approved
0.6959	Remote Similarity	NPD7758	Approved
0.6951	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7051	Phase 3
0.6933	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7705	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD6023	Discontinued
0.692	Remote Similarity	NPD983	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1259	Discontinued
0.6908	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3765	Approved
0.6901	Remote Similarity	NPD4080	Discontinued
0.6894	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5509	Phase 1
0.688	Remote Similarity	NPD6482	Phase 1
0.6842	Remote Similarity	NPD1287	Phase 2
0.6842	Remote Similarity	NPD6473	Phase 1
0.6842	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.683	Remote Similarity	NPD4673	Phase 2
0.6827	Remote Similarity	NPD5118	Phase 2
0.682	Remote Similarity	NPD1258	Discontinued
0.682	Remote Similarity	NPD4890	Phase 2
0.682	Remote Similarity	NPD3042	Approved
0.682	Remote Similarity	NPD3043	Approved
0.6811	Remote Similarity	NPD8049	Phase 2
0.6805	Remote Similarity	NPD1624	Phase 2
0.6795	Remote Similarity	NPD429	Approved
0.6789	Remote Similarity	NPD6605	Phase 3
0.6787	Remote Similarity	NPD2410	Phase 2
0.6773	Remote Similarity	NPD4558	Phase 2
0.6768	Remote Similarity	NPD4935	Phase 2
0.6761	Remote Similarity	NPD7117	Phase 2
0.6753	Remote Similarity	NPD4612	Discontinued
0.6752	Remote Similarity	NPD4457	Phase 2
0.6752	Remote Similarity	NPD5868	Approved
0.675	Remote Similarity	NPD3938	Phase 1
0.675	Remote Similarity	NPD2954	Approved
0.675	Remote Similarity	NPD2955	Approved
0.6749	Remote Similarity	NPD4995	Approved
0.6749	Remote Similarity	NPD4996	Approved
0.6749	Remote Similarity	NPD2062	Phase 2
0.6747	Remote Similarity	NPD7068	Approved
0.6747	Remote Similarity	NPD7067	Approved
0.6746	Remote Similarity	NPD6244	Phase 3
0.6746	Remote Similarity	NPD6243	Phase 3
0.6741	Remote Similarity	NPD978	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3602	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2876	Phase 3
0.6735	Remote Similarity	NPD3838	Phase 3
0.6735	Remote Similarity	NPD2757	Phase 2
0.6723	Remote Similarity	NPD6856	Discontinued
0.672	Remote Similarity	NPD5044	Phase 2
0.6716	Remote Similarity	NPD7407	Discontinued
0.6713	Remote Similarity	NPD3041	Approved
0.6711	Remote Similarity	NPD4142	Discontinued
0.671	Remote Similarity	NPD2450	Phase 2
0.671	Remote Similarity	NPD2452	Phase 2
0.671	Remote Similarity	NPD2451	Phase 2
0.671	Remote Similarity	NPD2453	Phase 2
0.6708	Remote Similarity	NPD4925	Approved
0.6705	Remote Similarity	NPD7706	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5567	Approved
0.6681	Remote Similarity	NPD2824	Phase 2
0.668	Remote Similarity	NPD7588	Discontinued
0.668	Remote Similarity	NPD8106	Phase 2
0.6667	Remote Similarity	NPD7323	Phase 2
0.6667	Remote Similarity	NPD6848	Phase 1
0.6667	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1571	Phase 2
0.6654	Remote Similarity	NPD5949	Phase 3
0.6654	Remote Similarity	NPD5875	Approved
0.6654	Remote Similarity	NPD5878	Approved
0.6651	Remote Similarity	NPD2600	Approved
0.6651	Remote Similarity	NPD2601	Approved
0.6651	Remote Similarity	NPD2599	Approved
0.664	Remote Similarity	NPD5644	Phase 1
0.664	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5107	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4858	Phase 2
0.6627	Remote Similarity	NPD6992	Phase 2
0.6627	Remote Similarity	NPD5905	Phase 1
0.6626	Remote Similarity	NPD1911	Approved
0.6626	Remote Similarity	NPD1910	Approved
0.6624	Remote Similarity	NPD5079	Phase 2
0.6624	Remote Similarity	NPD5287	Discontinued
0.6623	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2130	Discontinued
0.6613	Remote Similarity	NPD4316	Phase 3
0.6612	Remote Similarity	NPD5829	Phase 2
0.661	Remote Similarity	NPD2894	Phase 2
0.661	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3467	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD1954	Phase 1
0.6597	Remote Similarity	NPD5080	Phase 2
0.6592	Remote Similarity	NPD6153	Approved
0.6586	Remote Similarity	NPD3331	Phase 3
0.6586	Remote Similarity	NPD6750	Phase 2
0.6585	Remote Similarity	NPD1572	Phase 2
0.6581	Remote Similarity	NPD8525	Approved
0.6577	Remote Similarity	NPD2591	Phase 2
0.6576	Remote Similarity	NPD8442	Discontinued
0.6571	Remote Similarity	NPD6969	Phase 2
0.6571	Remote Similarity	NPD6968	Phase 2
0.657	Remote Similarity	NPD5045	Phase 2
0.6568	Remote Similarity	NPD2902	Phase 2
0.6568	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7226	Phase 3
0.6566	Remote Similarity	NPD7227	Phase 3
0.6562	Remote Similarity	NPD6742	Phase 2
0.6562	Remote Similarity	NPD6743	Phase 2
0.6561	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6536	Approved
0.656	Remote Similarity	NPD6537	Approved
0.6559	Remote Similarity	NPD2471	Approved
0.6559	Remote Similarity	NPD2472	Approved
0.6557	Remote Similarity	NPD6326	Phase 2
0.6557	Remote Similarity	NPD6327	Phase 1
0.6552	Remote Similarity	NPD3500	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4560	Suspended
0.654	Remote Similarity	NPD5447	Phase 2
0.6535	Remote Similarity	NPD5876	Phase 3
0.6535	Remote Similarity	NPD7898	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5877	Phase 3
0.6535	Remote Similarity	NPD7897	Phase 3
0.6531	Remote Similarity	NPD5014	Discontinued
0.6527	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2060	Approved
0.6523	Remote Similarity	NPD5008	Approved
0.652	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.652	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.652	Remote Similarity	NPD2769	Approved
0.6508	Remote Similarity	NPD5883	Phase 2
0.6504	Remote Similarity	NPD7689	Approved
0.6504	Remote Similarity	NPD4372	Phase 1
0.6502	Remote Similarity	NPD8288	Phase 2
0.6502	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD8287	Phase 1
0.6502	Remote Similarity	NPD1964	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5508	Phase 1
0.65	Remote Similarity	NPD5948	Phase 2
0.6496	Remote Similarity	NPD2886	Approved
0.6496	Remote Similarity	NPD2885	Approved
0.649	Remote Similarity	NPD2349	Phase 3
0.649	Remote Similarity	NPD1882	Phase 2
0.6484	Remote Similarity	NPD4916	Discontinued
0.6482	Remote Similarity	NPD5732	Approved
0.6482	Remote Similarity	NPD5731	Approved
0.648	Remote Similarity	NPD5920	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4442	Phase 2
0.6476	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5539	Phase 2
0.6473	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD3501	Phase 2
0.6473	Remote Similarity	NPD4353	Phase 2
0.6471	Remote Similarity	NPD6450	Phase 2
0.6468	Remote Similarity	NPD6366	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