NPASS Compound

Structure

CID250448 OpenBabel06191716052D 26 29 0 0 0 0 0 0 0 0999 V2000 4.3301 -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 -0.0000 3.0000 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 4.3301 2.5000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 3.4641 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 0.8660 1.5000 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 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 3.4641 0.0000 0.0000 N 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 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 2 0 0 0 0 7 17 2 0 0 0 0 8 10 1 0 0 0 0 8 12 2 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 11 13 1 0 0 0 0 12 20 1 0 0 0 0 13 23 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 20 25 1 0 0 0 0 20 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	345.11
Volume:	350.61
LogP:	3.88
LogD:	2.69
LogS:	-3.733
# Rotatable Bonds:	3
TPSA:	86.55
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	2.409
Fsp3:	0.05
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.05
MDCK Permeability:	1.5876530596869998e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	96.82200622558594%
Volume Distribution (VD):	0.334
Pgp-substrate:	1.7408287525177002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.255
CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.682
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.08
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	1.311
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.137
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.356
Rat Oral Acute Toxicity:	0.318
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.072
Carcinogencity:	0.188
Eye Corrosion:	0.003
Eye Irritation:	0.063
Respiratory Toxicity:	0.848

Download Data

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

Natural Product: NPC250448

Natural Product ID:	NPC250448
*Common Name:**	Izumiphenazine C
IUPAC Name:	n.a.
Synonyms:	Izumiphenazine C
Standard InCHIKey:	REOKRAKOSOITAV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H15N3O3/c1-23(13-10-8-12(9-11-13)20(25)26)16-6-2-4-14-18(16)21-15-5-3-7-17(24)19(15)22-14/h2-11,24H,1H3,(H,25,26)
SMILES:	CN(c1cccc2c1nc1cccc(c1n2)O)c1ccc(cc1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651327
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000486] Quinoxalines [CHEMONTID:0000416] Phenazines 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
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10344559]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10344578]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10348041]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10604756]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10695669]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10724004]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10994816]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11099231]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11132958]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374972]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473415]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14738393]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Australian	n.a.	PMID[15497950]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15813185]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15844966]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15974616]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16180833]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1666120]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724845]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16830891]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16872146]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125235]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17315965]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17551212]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17608531]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17844998]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17887721]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17917237]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18044841]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Indonesian	n.a.	PMID[18081255]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18081255]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18205372]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Northwest Territories, Canada	1995	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18666798]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18776684]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19007176]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19129624]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19191549]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19856955]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19883065]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20092333]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20545334]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20836523]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028889]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028891]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21090727]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21314175]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21639131]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21728289]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	latex	n.a.	PMID[21751787]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21807523]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21873059]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	latex	n.a.	PMID[21879726]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[22145663]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22574670]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22583058]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22591466]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22758660]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22775474]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23387796]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23662937]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24592993]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24754815]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24878306]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24964393]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25211234]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25455147]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25495422]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25537064]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25918793]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25934225]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26035239]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26465675]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26798949]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26905826]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31013087]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31298537]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31894983]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32298122]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8501018]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[8784423]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8931733]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8982334]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031666]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031676]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9066767]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9066768]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9186568]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9531983]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[9711246]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	26.0	%	PMID[490357]

☑ 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 NPC250448 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	461
0.1-0.2	4376
0.2-0.3	12815
0.3-0.4	10854
0.4-0.5	10045
0.5-0.6	2783
0.6-0.7	1258
0.7-0.8	104
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
0.797	Intermediate Similarity	NPC314573
0.7885	Intermediate Similarity	NPC218388
0.7831	Intermediate Similarity	NPC79911
0.7778	Intermediate Similarity	NPC120798
0.7673	Intermediate Similarity	NPC144381
0.76	Intermediate Similarity	NPC203635
0.7561	Intermediate Similarity	NPC230403
0.755	Intermediate Similarity	NPC243058
0.7525	Intermediate Similarity	NPC219848
0.7522	Intermediate Similarity	NPC291609
0.7513	Intermediate Similarity	NPC95898
0.7487	Intermediate Similarity	NPC256268
0.7478	Intermediate Similarity	NPC124300
0.7467	Intermediate Similarity	NPC477112
0.7465	Intermediate Similarity	NPC118228
0.7451	Intermediate Similarity	NPC110741
0.7438	Intermediate Similarity	NPC90415
0.7393	Intermediate Similarity	NPC470586
0.7385	Intermediate Similarity	NPC237740
0.7382	Intermediate Similarity	NPC310618
0.7371	Intermediate Similarity	NPC472259
0.7371	Intermediate Similarity	NPC314648
0.7366	Intermediate Similarity	NPC183805
0.7358	Intermediate Similarity	NPC57398
0.7349	Intermediate Similarity	NPC39679
0.7306	Intermediate Similarity	NPC116573
0.7302	Intermediate Similarity	NPC283117
0.7286	Intermediate Similarity	NPC141454
0.7277	Intermediate Similarity	NPC51388
0.7256	Intermediate Similarity	NPC313345
0.7256	Intermediate Similarity	NPC313796
0.7256	Intermediate Similarity	NPC314855
0.7256	Intermediate Similarity	NPC315638
0.7254	Intermediate Similarity	NPC227824
0.725	Intermediate Similarity	NPC303225
0.7248	Intermediate Similarity	NPC294375
0.7244	Intermediate Similarity	NPC179287
0.7243	Intermediate Similarity	NPC165599
0.724	Intermediate Similarity	NPC36168
0.7237	Intermediate Similarity	NPC474701
0.7234	Intermediate Similarity	NPC178858
0.7222	Intermediate Similarity	NPC314297
0.7222	Intermediate Similarity	NPC315545
0.7207	Intermediate Similarity	NPC184408
0.7205	Intermediate Similarity	NPC132329
0.7202	Intermediate Similarity	NPC309845
0.7195	Intermediate Similarity	NPC330009
0.7192	Intermediate Similarity	NPC478032
0.717	Intermediate Similarity	NPC474916
0.7169	Intermediate Similarity	NPC87413
0.7163	Intermediate Similarity	NPC317572
0.7162	Intermediate Similarity	NPC293151
0.7157	Intermediate Similarity	NPC118776
0.7156	Intermediate Similarity	NPC220851
0.7143	Intermediate Similarity	NPC45850
0.7136	Intermediate Similarity	NPC1527
0.7136	Intermediate Similarity	NPC241025
0.7123	Intermediate Similarity	NPC314834
0.7117	Intermediate Similarity	NPC3207
0.7117	Intermediate Similarity	NPC322064
0.711	Intermediate Similarity	NPC477111
0.7108	Intermediate Similarity	NPC478023
0.7101	Intermediate Similarity	NPC194040
0.7094	Intermediate Similarity	NPC41501
0.7091	Intermediate Similarity	NPC23294
0.7089	Intermediate Similarity	NPC306376
0.7089	Intermediate Similarity	NPC472284
0.7083	Intermediate Similarity	NPC476098
0.7083	Intermediate Similarity	NPC53144
0.7083	Intermediate Similarity	NPC200836
0.708	Intermediate Similarity	NPC478141
0.7067	Intermediate Similarity	NPC206186
0.7064	Intermediate Similarity	NPC244741
0.7056	Intermediate Similarity	NPC322644
0.7045	Intermediate Similarity	NPC303951
0.704	Intermediate Similarity	NPC477110
0.7032	Intermediate Similarity	NPC210828
0.7032	Intermediate Similarity	NPC86834
0.7031	Intermediate Similarity	NPC186351
0.7027	Intermediate Similarity	NPC39500
0.7018	Intermediate Similarity	NPC477113
0.7017	Intermediate Similarity	NPC469734
0.7005	Intermediate Similarity	NPC207851
0.6996	Remote Similarity	NPC182222
0.6987	Remote Similarity	NPC161801
0.6986	Remote Similarity	NPC4687
0.6986	Remote Similarity	NPC53344
0.6983	Remote Similarity	NPC477516
0.6974	Remote Similarity	NPC229893
0.6964	Remote Similarity	NPC469928
0.6963	Remote Similarity	NPC474188
0.6951	Remote Similarity	NPC89508
0.6947	Remote Similarity	NPC208084
0.6943	Remote Similarity	NPC257142
0.6941	Remote Similarity	NPC472286
0.6941	Remote Similarity	NPC472287
0.6937	Remote Similarity	NPC146418
0.6936	Remote Similarity	NPC472061
0.6933	Remote Similarity	NPC312645
0.6933	Remote Similarity	NPC27041
0.6926	Remote Similarity	NPC274640
0.6923	Remote Similarity	NPC39370
0.6923	Remote Similarity	NPC325297
0.6916	Remote Similarity	NPC174760
0.6913	Remote Similarity	NPC470018
0.691	Remote Similarity	NPC473186
0.6909	Remote Similarity	NPC270918
0.6904	Remote Similarity	NPC160898
0.6898	Remote Similarity	NPC476167
0.6898	Remote Similarity	NPC280714
0.6892	Remote Similarity	NPC85273
0.6889	Remote Similarity	NPC152768
0.6889	Remote Similarity	NPC148183
0.6886	Remote Similarity	NPC60621
0.6884	Remote Similarity	NPC90229
0.688	Remote Similarity	NPC329631
0.6867	Remote Similarity	NPC260434
0.686	Remote Similarity	NPC165964
0.6856	Remote Similarity	NPC144452
0.6856	Remote Similarity	NPC216612
0.6852	Remote Similarity	NPC192315
0.6842	Remote Similarity	NPC150239
0.6842	Remote Similarity	NPC128115
0.6842	Remote Similarity	NPC320394
0.684	Remote Similarity	NPC132631
0.684	Remote Similarity	NPC103687
0.6837	Remote Similarity	NPC284348
0.6833	Remote Similarity	NPC208522
0.6833	Remote Similarity	NPC321428
0.6832	Remote Similarity	NPC41717
0.683	Remote Similarity	NPC264176
0.683	Remote Similarity	NPC244856
0.6828	Remote Similarity	NPC247803
0.6828	Remote Similarity	NPC174576
0.6826	Remote Similarity	NPC322482
0.682	Remote Similarity	NPC473312
0.6818	Remote Similarity	NPC132539
0.6804	Remote Similarity	NPC328318
0.6804	Remote Similarity	NPC328596
0.6804	Remote Similarity	NPC211813
0.6798	Remote Similarity	NPC313804
0.6798	Remote Similarity	NPC315804
0.6797	Remote Similarity	NPC279589
0.6795	Remote Similarity	NPC474688
0.6795	Remote Similarity	NPC119006
0.6791	Remote Similarity	NPC276517
0.6787	Remote Similarity	NPC471736
0.6786	Remote Similarity	NPC187501
0.6786	Remote Similarity	NPC9894
0.6784	Remote Similarity	NPC169402
0.6781	Remote Similarity	NPC471762
0.6778	Remote Similarity	NPC475844
0.6773	Remote Similarity	NPC134848
0.677	Remote Similarity	NPC45048
0.677	Remote Similarity	NPC116238
0.6766	Remote Similarity	NPC207686
0.6765	Remote Similarity	NPC473764
0.6765	Remote Similarity	NPC314940
0.6762	Remote Similarity	NPC313587
0.6762	Remote Similarity	NPC473800
0.6762	Remote Similarity	NPC316110
0.6762	Remote Similarity	NPC315893
0.6758	Remote Similarity	NPC471944
0.6757	Remote Similarity	NPC249583
0.6756	Remote Similarity	NPC294620
0.6754	Remote Similarity	NPC264285
0.6754	Remote Similarity	NPC473041
0.6753	Remote Similarity	NPC205372
0.6747	Remote Similarity	NPC215837
0.674	Remote Similarity	NPC476161
0.6738	Remote Similarity	NPC74575
0.6735	Remote Similarity	NPC288445
0.6733	Remote Similarity	NPC204867
0.673	Remote Similarity	NPC42591
0.6726	Remote Similarity	NPC306644
0.6726	Remote Similarity	NPC31700
0.6726	Remote Similarity	NPC317752
0.6726	Remote Similarity	NPC236424
0.6725	Remote Similarity	NPC17565
0.6724	Remote Similarity	NPC21638
0.6718	Remote Similarity	NPC315829
0.6716	Remote Similarity	NPC44161
0.6716	Remote Similarity	NPC285635
0.6715	Remote Similarity	NPC84347
0.6713	Remote Similarity	NPC93390
0.6712	Remote Similarity	NPC317373
0.6712	Remote Similarity	NPC472064
0.6712	Remote Similarity	NPC300156
0.6709	Remote Similarity	NPC194740
0.6709	Remote Similarity	NPC66777
0.6696	Remote Similarity	NPC274842
0.6696	Remote Similarity	NPC472099
0.6695	Remote Similarity	NPC49547
0.6693	Remote Similarity	NPC473639
0.6693	Remote Similarity	NPC132385
0.6681	Remote Similarity	NPC318299
0.6681	Remote Similarity	NPC35042
0.6681	Remote Similarity	NPC118940
0.6681	Remote Similarity	NPC477549
0.6681	Remote Similarity	NPC65277

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 NPC250448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	684
0.2-0.3	910
0.3-0.4	1558
0.4-0.5	2911
0.5-0.6	2151
0.6-0.7	629
0.7-0.8	35
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
0.7609	Intermediate Similarity	NPD5488	Discontinued
0.7546	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3986	Discontinued
0.7376	Intermediate Similarity	NPD5850	Phase 3
0.7281	Intermediate Similarity	NPD3746	Discontinued
0.7281	Intermediate Similarity	NPD1572	Phase 2
0.7227	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1571	Phase 2
0.7179	Intermediate Similarity	NPD6716	Phase 1
0.7178	Intermediate Similarity	NPD6159	Phase 2
0.7175	Intermediate Similarity	NPD4312	Approved
0.7169	Intermediate Similarity	NPD5416	Discontinued
0.713	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5445	Approved
0.7097	Intermediate Similarity	NPD5530	Phase 1
0.7085	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD4368	Phase 2
0.7059	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6795	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2916	Discontinued
0.7031	Intermediate Similarity	NPD8430	Approved
0.7027	Intermediate Similarity	NPD3243	Approved
0.7009	Intermediate Similarity	NPD772	Phase 3
0.6987	Remote Similarity	NPD7603	Discontinued
0.6978	Remote Similarity	NPD7395	Discontinued
0.6978	Remote Similarity	NPD4429	Discontinued
0.6964	Remote Similarity	NPD6456	Discontinued
0.6937	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8356	Approved
0.6923	Remote Similarity	NPD2951	Discontinued
0.6919	Remote Similarity	NPD5316	Approved
0.6917	Remote Similarity	NPD7996	Phase 2
0.6886	Remote Similarity	NPD7726	Phase 1
0.6883	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7924	Phase 2
0.688	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7925	Phase 2
0.6878	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5482	Discontinued
0.686	Remote Similarity	NPD3809	Discontinued
0.6852	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD8463	Approved
0.6842	Remote Similarity	NPD7180	Phase 3
0.684	Remote Similarity	NPD3263	Phase 3
0.6833	Remote Similarity	NPD3962	Phase 2
0.6833	Remote Similarity	NPD3959	Phase 2
0.6828	Remote Similarity	NPD5632	Approved
0.6824	Remote Similarity	NPD5022	Discontinued
0.6818	Remote Similarity	NPD5901	Discontinued
0.6816	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7694	Discontinued
0.6797	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD1838	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6209	Approved
0.6774	Remote Similarity	NPD7923	Phase 2
0.6767	Remote Similarity	NPD7426	Phase 1
0.6763	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5512	Phase 3
0.6757	Remote Similarity	NPD5429	Discontinued
0.6756	Remote Similarity	NPD5866	Approved
0.6753	Remote Similarity	NPD6752	Phase 1
0.6753	Remote Similarity	NPD6753	Phase 1
0.6752	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5479	Discontinued
0.6745	Remote Similarity	NPD4948	Discontinued
0.6744	Remote Similarity	NPD9695	Approved
0.6741	Remote Similarity	NPD5860	Discontinued
0.6738	Remote Similarity	NPD3259	Approved
0.6737	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6376	Discontinued
0.6725	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1467	Approved
0.6723	Remote Similarity	NPD1867	Approved
0.6723	Remote Similarity	NPD1466	Phase 3
0.6714	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6452	Discontinued
0.6695	Remote Similarity	NPD4938	Phase 2
0.6694	Remote Similarity	NPD7921	Approved
0.6682	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7878	Phase 2
0.6667	Remote Similarity	NPD2882	Phase 1
0.6667	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6987	Phase 1
0.6667	Remote Similarity	NPD7867	Phase 1
0.6653	Remote Similarity	NPD6962	Phase 2
0.6653	Remote Similarity	NPD1505	Phase 2
0.6651	Remote Similarity	NPD2762	Phase 2
0.665	Remote Similarity	NPD1631	Approved
0.6641	Remote Similarity	NPD7181	Phase 3
0.6639	Remote Similarity	NPD7417	Discontinued
0.6638	Remote Similarity	NPD7767	Approved
0.6636	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5640	Discontinued
0.6624	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4897	Phase 2
0.662	Remote Similarity	NPD4376	Phase 3
0.6619	Remote Similarity	NPD9510	Approved
0.6611	Remote Similarity	NPD7853	Phase 2
0.6609	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4373	Phase 2
0.6593	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2175	Phase 3
0.6591	Remote Similarity	NPD2176	Approved
0.6591	Remote Similarity	NPD2177	Approved
0.659	Remote Similarity	NPD4539	Phase 1
0.6587	Remote Similarity	NPD9690	Approved
0.6587	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.658	Remote Similarity	NPD3258	Approved
0.658	Remote Similarity	NPD7404	Approved
0.6579	Remote Similarity	NPD3945	Discontinued
0.6578	Remote Similarity	NPD7467	Discontinued
0.6578	Remote Similarity	NPD7666	Phase 3
0.6578	Remote Similarity	NPD7665	Phase 2
0.6577	Remote Similarity	NPD2779	Approved
0.6577	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD2336	Approved
0.657	Remote Similarity	NPD3776	Discontinued
0.6565	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4894	Discontinued
0.656	Remote Similarity	NPD8091	Phase 3
0.656	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5827	Discontinued
0.6545	Remote Similarity	NPD7777	Approved
0.6545	Remote Similarity	NPD7778	Approved
0.6545	Remote Similarity	NPD53	Approved
0.6545	Remote Similarity	NPD8102	Discontinued
0.6544	Remote Similarity	NPD4372	Phase 1
0.654	Remote Similarity	NPD4952	Phase 3
0.654	Remote Similarity	NPD6199	Discontinued
0.6535	Remote Similarity	NPD5450	Discontinued
0.6533	Remote Similarity	NPD7222	Phase 2
0.6533	Remote Similarity	NPD6290	Phase 2
0.6528	Remote Similarity	NPD3321	Discontinued
0.6527	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD3947	Discontinued
0.6516	Remote Similarity	NPD7068	Approved
0.6516	Remote Similarity	NPD7067	Approved
0.6516	Remote Similarity	NPD6999	Discontinued
0.6516	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2383	Phase 1
0.6511	Remote Similarity	NPD4403	Phase 3
0.6511	Remote Similarity	NPD4401	Phase 2
0.6509	Remote Similarity	NPD6974	Phase 3
0.6507	Remote Similarity	NPD6492	Phase 2
0.6502	Remote Similarity	NPD1630	Approved
0.6502	Remote Similarity	NPD6790	Phase 1
0.65	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6158	Phase 2
0.6496	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6227	Discontinued
0.6491	Remote Similarity	NPD5939	Approved
0.6491	Remote Similarity	NPD5936	Approved
0.6491	Remote Similarity	NPD1468	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4502	Phase 2
0.6489	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD484	Approved
0.6486	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4602	Approved
0.6478	Remote Similarity	NPD3257	Approved
0.6475	Remote Similarity	NPD7022	Phase 2
0.6473	Remote Similarity	NPD5922	Phase 3
0.6471	Remote Similarity	NPD712	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4397	Phase 1
0.6471	Remote Similarity	NPD9705	Discontinued
0.6471	Remote Similarity	NPD112	Approved
0.6468	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5809	Phase 3
0.6465	Remote Similarity	NPD3315	Phase 3
0.6463	Remote Similarity	NPD4852	Phase 2
0.6459	Remote Similarity	NPD8364	Approved
0.6459	Remote Similarity	NPD8363	Approved
0.6456	Remote Similarity	NPD4845	Discontinued
0.6455	Remote Similarity	NPD2307	Discontinued
0.6455	Remote Similarity	NPD6550	Discontinued
0.6454	Remote Similarity	NPD6458	Discontinued
0.6453	Remote Similarity	NPD5506	Approved
0.6453	Remote Similarity	NPD5507	Approved
0.6449	Remote Similarity	NPD721	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