NPASS Compound

Structure

NPC199667 OpenBabel07101718332D 32 37 0 0 0 0 0 0 0 0999 V2000 -3.3412 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 -3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2916 0.6580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8794 -0.1511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2971 0.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4727 -1.0646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8904 -0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4781 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9393 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8904 -1.9781 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 0.1229 -2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 7 2 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 18 2 0 0 0 0 9 19 2 0 0 0 0 10 22 2 0 0 0 0 11 23 2 0 0 0 0 12 16 2 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 25 2 0 0 0 0 16 20 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 26 1 0 0 0 0 20 26 2 0 0 0 0 21 27 2 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 28 2 0 0 0 0 24 31 1 0 0 0 0 25 27 1 0 0 0 0 25 32 1 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 28 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	449.442
LogP:	6.616
LogD:	4.691
LogS:	-6.945
# Rotatable Bonds:	4
TPSA:	50.04
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	2.553
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.708
MDCK Permeability:	9.445303476240952e-06
Pgp-inhibitor:	0.992
Pgp-substrate:	0.532
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.542
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	98.02780151367188%
Volume Distribution (VD):	0.97
Pgp-substrate:	1.4643001556396484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.895
CYP2C19-substrate:	0.146
CYP2C9-inhibitor:	0.869
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.747
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.585
CYP3A4-substrate:	0.89

ADMET: Excretion

Clearance (CL):	5.255
Half-life (T1/2):	0.219

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.87
Rat Oral Acute Toxicity:	0.241
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.758
Carcinogencity:	0.896
Eye Corrosion:	0.003
Eye Irritation:	0.821
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC199667

Natural Product ID:	NPC199667
*Common Name:**	Sid506300
IUPAC Name:	1-methoxy-4-[(1-methoxy-9H-carbazol-3-yl)methyl]-3-methyl-9H-carbazole
Synonyms:
Standard InCHIKey:	DOOBXUMQHNVKJS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H24N2O2/c1-16-12-24(31-2)28-26(19-9-5-7-11-23(19)30-28)20(16)13-17-14-21-18-8-4-6-10-22(18)29-27(21)25(15-17)32-3/h4-12,14-15,29-30H,13H2,1-3H3
SMILES:	Cc1cc(c2c(c3ccccc3[nH]2)c1Cc1cc2c3ccccc3[nH]c2c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524067
PubChem CID:	375159
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	stem bark;fruit	n.a.	n.a.	PMID[10924160]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	root bark	Kuantaochi, Nantou Hsien, Taiwan	n.a.	PMID[10924160]
NPO33199	murraya tetramera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26327273]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	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
GI50	98
IC50	1

Activity Type	# Activity
Cell Line	91
NON-MOLECULAR	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	=	8511.38	nM	PMID[486274]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	7244.36	nM	PMID[486274]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	=	5754.4	nM	PMID[486274]
NPT385	Cell Line	SR	Homo sapiens	GI50	=	7762.47	nM	PMID[486274]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	5754.4	nM	PMID[486274]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	=	5495.41	nM	PMID[486274]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	=	7585.78	nM	PMID[486274]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	=	4677.35	nM	PMID[486274]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	=	7244.36	nM	PMID[486274]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	5128.61	nM	PMID[486274]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	5011.87	nM	PMID[486274]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	=	7585.78	nM	PMID[486274]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	=	12022.64	nM	PMID[486274]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	=	8912.51	nM	PMID[486274]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	=	5370.32	nM	PMID[486274]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	9120.11	nM	PMID[486274]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	6918.31	nM	PMID[486274]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	7762.47	nM	PMID[486274]
NPT386	Cell Line	KM12	Homo sapiens	GI50	=	5370.32	nM	PMID[486274]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	5248.07	nM	PMID[486274]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	=	8128.31	nM	PMID[486274]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	6918.31	nM	PMID[486274]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	=	4570.88	nM	PMID[486274]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	=	5888.44	nM	PMID[486274]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	=	5754.4	nM	PMID[486274]
NPT380	Cell Line	U-251	Homo sapiens	GI50	=	5011.87	nM	PMID[486274]
NPT574	Cell Line	XF498	Homo sapiens	GI50	=	6025.6	nM	PMID[486274]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	=	3890.45	nM	PMID[486274]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	=	4466.84	nM	PMID[486274]
NPT387	Cell Line	M14	Homo sapiens	GI50	=	5128.61	nM	PMID[486274]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	=	9772.37	nM	PMID[486274]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	=	3981.07	nM	PMID[486274]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	=	8709.64	nM	PMID[486274]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	=	3981.07	nM	PMID[486274]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	=	5623.41	nM	PMID[486274]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	=	9120.11	nM	PMID[486274]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	=	8709.64	nM	PMID[486274]
NPT401	Cell Line	786-0	Homo sapiens	GI50	=	5370.32	nM	PMID[486274]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	=	4677.35	nM	PMID[486274]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	=	6456.54	nM	PMID[486274]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	=	12022.64	nM	PMID[486274]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	=	6025.6	nM	PMID[486274]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	6397.35	nM	PMID[486275]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	4666.59	nM	PMID[486275]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	6053.41	nM	PMID[486275]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	7638.36	nM	PMID[486275]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	7961.59	nM	PMID[486275]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	4613.18	nM	PMID[486275]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	3944.57	nM	PMID[486275]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	4446.31	nM	PMID[486275]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	7311.39	nM	PMID[486275]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	5420.01	nM	PMID[486275]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	5482.77	nM	PMID[486275]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	5688.53	nM	PMID[486275]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	4954.5	nM	PMID[486275]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	4570.88	nM	PMID[486275]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	4988.84	nM	PMID[486275]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	8851.16	nM	PMID[486275]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	7638.36	nM	PMID[486275]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	7780.37	nM	PMID[486275]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	11994.99	nM	PMID[486275]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	8090.96	nM	PMID[486275]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	9660.51	nM	PMID[486275]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	5035.01	nM	PMID[486275]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	5116.82	nM	PMID[486275]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	5432.5	nM	PMID[486275]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	6025.6	nM	PMID[486275]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	7261.06	nM	PMID[486275]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	9954.05	nM	PMID[486275]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	3845.92	nM	PMID[486275]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	3971.92	nM	PMID[486275]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	5727.96	nM	PMID[486275]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	5272.3	nM	PMID[486275]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	5432.5	nM	PMID[486275]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	6886.52	nM	PMID[486275]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	9183.33	nM	PMID[486275]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	6966.27	nM	PMID[486275]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	4120.98	nM	PMID[486275]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	10471.29	nM	PMID[486275]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	8790.23	nM	PMID[486275]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	5610.48	nM	PMID[486275]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	5128.61	nM	PMID[486275]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	9036.49	nM	PMID[486275]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	5794.29	nM	PMID[486275]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	5382.7	nM	PMID[486275]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	8590.14	nM	PMID[486275]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	8994.98	nM	PMID[486275]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	4666.59	nM	PMID[486275]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	7834.3	nM	PMID[486275]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	8609.94	nM	PMID[486275]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	12022.64	nM	PMID[486275]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	7943.28	nM	PMID[486274]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	10000.0	nM	PMID[486274]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4168.69	nM	PMID[486274]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	10471.29	nM	PMID[486274]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	5370.32	nM	PMID[486274]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	5011.87	nM	PMID[486274]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4570.88	nM	PMID[486274]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18600.0	nM	PMID[486276]

☑ 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 NPC199667 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	734
0.1-0.2	4305
0.2-0.3	13148
0.3-0.4	7920
0.4-0.5	11807
0.5-0.6	3048
0.6-0.7	1376
0.7-0.8	301
0.8-0.85	42
0.85-0.9	10
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9946	High Similarity	NPC473181
0.9684	High Similarity	NPC473180
0.9278	High Similarity	NPC94157
0.9192	High Similarity	NPC473179
0.9029	High Similarity	NPC473182
0.8978	High Similarity	NPC242928
0.8955	High Similarity	NPC132642
0.8878	High Similarity	NPC473185
0.8829	High Similarity	NPC202503
0.875	High Similarity	NPC475253
0.866	High Similarity	NPC128823
0.8656	High Similarity	NPC474798
0.8585	High Similarity	NPC225279
0.8545	High Similarity	NPC473183
0.8538	High Similarity	NPC473184
0.8535	High Similarity	NPC470930
0.8531	High Similarity	NPC473186
0.8502	High Similarity	NPC144452
0.8476	Intermediate Similarity	NPC252251
0.8451	Intermediate Similarity	NPC39370
0.8396	Intermediate Similarity	NPC477531
0.8366	Intermediate Similarity	NPC201697
0.8358	Intermediate Similarity	NPC193777
0.8349	Intermediate Similarity	NPC209174
0.831	Intermediate Similarity	NPC474688
0.8308	Intermediate Similarity	NPC475190
0.8302	Intermediate Similarity	NPC274640
0.8284	Intermediate Similarity	NPC208284
0.8265	Intermediate Similarity	NPC131017
0.8232	Intermediate Similarity	NPC72211
0.8229	Intermediate Similarity	NPC473189
0.8209	Intermediate Similarity	NPC162484
0.82	Intermediate Similarity	NPC267423
0.8195	Intermediate Similarity	NPC187501
0.819	Intermediate Similarity	NPC477532
0.8186	Intermediate Similarity	NPC209769
0.8182	Intermediate Similarity	NPC70956
0.8182	Intermediate Similarity	NPC243834
0.8155	Intermediate Similarity	NPC48353
0.8143	Intermediate Similarity	NPC86078
0.8143	Intermediate Similarity	NPC477533
0.8131	Intermediate Similarity	NPC70259
0.8119	Intermediate Similarity	NPC475774
0.8119	Intermediate Similarity	NPC223427
0.8116	Intermediate Similarity	NPC39500
0.8095	Intermediate Similarity	NPC208084
0.8081	Intermediate Similarity	NPC205934
0.8081	Intermediate Similarity	NPC43787
0.803	Intermediate Similarity	NPC245816
0.803	Intermediate Similarity	NPC476138
0.8028	Intermediate Similarity	NPC51388
0.8018	Intermediate Similarity	NPC101543
0.8018	Intermediate Similarity	NPC469554
0.8009	Intermediate Similarity	NPC475844
0.798	Intermediate Similarity	NPC475085
0.798	Intermediate Similarity	NPC475112
0.798	Intermediate Similarity	NPC291535
0.7962	Intermediate Similarity	NPC184408
0.7953	Intermediate Similarity	NPC227908
0.7938	Intermediate Similarity	NPC176127
0.7931	Intermediate Similarity	NPC476044
0.7921	Intermediate Similarity	NPC18487
0.7919	Intermediate Similarity	NPC246700
0.7915	Intermediate Similarity	NPC293151
0.791	Intermediate Similarity	NPC153042
0.7902	Intermediate Similarity	NPC285558
0.7897	Intermediate Similarity	NPC84478
0.7882	Intermediate Similarity	NPC329747
0.7867	Intermediate Similarity	NPC170114
0.7865	Intermediate Similarity	NPC56618
0.7864	Intermediate Similarity	NPC476106
0.7824	Intermediate Similarity	NPC179287
0.782	Intermediate Similarity	NPC470549
0.7819	Intermediate Similarity	NPC118511
0.781	Intermediate Similarity	NPC26679
0.7808	Intermediate Similarity	NPC474701
0.7807	Intermediate Similarity	NPC473188
0.7794	Intermediate Similarity	NPC329793
0.7773	Intermediate Similarity	NPC49547
0.7767	Intermediate Similarity	NPC280799
0.7751	Intermediate Similarity	NPC185782
0.7748	Intermediate Similarity	NPC473187
0.7746	Intermediate Similarity	NPC314552
0.7739	Intermediate Similarity	NPC128751
0.7738	Intermediate Similarity	NPC180504
0.7725	Intermediate Similarity	NPC294620
0.7717	Intermediate Similarity	NPC314954
0.7706	Intermediate Similarity	NPC470018
0.77	Intermediate Similarity	NPC106833
0.77	Intermediate Similarity	NPC469497
0.7692	Intermediate Similarity	NPC300156
0.7692	Intermediate Similarity	NPC45190
0.7692	Intermediate Similarity	NPC88363
0.7689	Intermediate Similarity	NPC469592
0.7689	Intermediate Similarity	NPC478074
0.7689	Intermediate Similarity	NPC476287
0.7689	Intermediate Similarity	NPC471080
0.7677	Intermediate Similarity	NPC94943
0.7671	Intermediate Similarity	NPC74575
0.7665	Intermediate Similarity	NPC208522
0.7656	Intermediate Similarity	NPC249583
0.7656	Intermediate Similarity	NPC4687
0.7653	Intermediate Similarity	NPC118228
0.7633	Intermediate Similarity	NPC135887
0.7633	Intermediate Similarity	NPC199277
0.763	Intermediate Similarity	NPC471304
0.763	Intermediate Similarity	NPC123976
0.763	Intermediate Similarity	NPC167860
0.7629	Intermediate Similarity	NPC312872
0.7626	Intermediate Similarity	NPC190007
0.7623	Intermediate Similarity	NPC277351
0.7621	Intermediate Similarity	NPC11017
0.7621	Intermediate Similarity	NPC19872
0.7619	Intermediate Similarity	NPC475910
0.7612	Intermediate Similarity	NPC76748
0.76	Intermediate Similarity	NPC11408
0.7586	Intermediate Similarity	NPC307963
0.7576	Intermediate Similarity	NPC212535
0.7574	Intermediate Similarity	NPC89549
0.7574	Intermediate Similarity	NPC92111
0.7569	Intermediate Similarity	NPC280272
0.7562	Intermediate Similarity	NPC296527
0.7546	Intermediate Similarity	NPC469594
0.7545	Intermediate Similarity	NPC200888
0.7537	Intermediate Similarity	NPC280964
0.7537	Intermediate Similarity	NPC114335
0.7537	Intermediate Similarity	NPC141915
0.7536	Intermediate Similarity	NPC470931
0.7536	Intermediate Similarity	NPC176538
0.7535	Intermediate Similarity	NPC8022
0.7535	Intermediate Similarity	NPC470799
0.7533	Intermediate Similarity	NPC477066
0.7533	Intermediate Similarity	NPC217554
0.7512	Intermediate Similarity	NPC473177
0.7512	Intermediate Similarity	NPC87413
0.75	Intermediate Similarity	NPC42591
0.75	Intermediate Similarity	NPC478081
0.75	Intermediate Similarity	NPC232727
0.7488	Intermediate Similarity	NPC283117
0.7477	Intermediate Similarity	NPC308137
0.7477	Intermediate Similarity	NPC310211
0.7475	Intermediate Similarity	NPC478032
0.7465	Intermediate Similarity	NPC303658
0.7465	Intermediate Similarity	NPC46561
0.7463	Intermediate Similarity	NPC204385
0.7457	Intermediate Similarity	NPC26543
0.7443	Intermediate Similarity	NPC198503
0.7442	Intermediate Similarity	NPC266931
0.7441	Intermediate Similarity	NPC304183
0.7437	Intermediate Similarity	NPC206201
0.7435	Intermediate Similarity	NPC284141
0.7431	Intermediate Similarity	NPC213530
0.7431	Intermediate Similarity	NPC193267
0.7431	Intermediate Similarity	NPC292958
0.7427	Intermediate Similarity	NPC251090
0.7424	Intermediate Similarity	NPC477067
0.7424	Intermediate Similarity	NPC478082
0.7421	Intermediate Similarity	NPC26850
0.7419	Intermediate Similarity	NPC169402
0.7419	Intermediate Similarity	NPC305984
0.7407	Intermediate Similarity	NPC116238
0.7401	Intermediate Similarity	NPC6786
0.7397	Intermediate Similarity	NPC150239
0.7393	Intermediate Similarity	NPC137929
0.7393	Intermediate Similarity	NPC164374
0.7385	Intermediate Similarity	NPC473041
0.7385	Intermediate Similarity	NPC96321
0.7383	Intermediate Similarity	NPC188420
0.7379	Intermediate Similarity	NPC195314
0.7373	Intermediate Similarity	NPC53534
0.7361	Intermediate Similarity	NPC162530
0.7361	Intermediate Similarity	NPC149471
0.7361	Intermediate Similarity	NPC271215
0.7357	Intermediate Similarity	NPC295228
0.7349	Intermediate Similarity	NPC9894
0.7349	Intermediate Similarity	NPC294375
0.7348	Intermediate Similarity	NPC473540
0.7345	Intermediate Similarity	NPC329631
0.7333	Intermediate Similarity	NPC470586
0.733	Intermediate Similarity	NPC473178
0.7328	Intermediate Similarity	NPC475666
0.7327	Intermediate Similarity	NPC476319
0.7321	Intermediate Similarity	NPC476167
0.7315	Intermediate Similarity	NPC251160
0.7306	Intermediate Similarity	NPC247803
0.7302	Intermediate Similarity	NPC11464
0.7297	Intermediate Similarity	NPC167908
0.7296	Intermediate Similarity	NPC17437
0.729	Intermediate Similarity	NPC477111
0.729	Intermediate Similarity	NPC39679
0.7284	Intermediate Similarity	NPC81939
0.7282	Intermediate Similarity	NPC99666
0.7281	Intermediate Similarity	NPC470017
0.7273	Intermediate Similarity	NPC192315
0.7273	Intermediate Similarity	NPC46451
0.7263	Intermediate Similarity	NPC26872
0.7256	Intermediate Similarity	NPC469589
0.725	Intermediate Similarity	NPC72980
0.7249	Intermediate Similarity	NPC470022
0.7248	Intermediate Similarity	NPC235076

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 NPC199667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	422
0.1-0.2	715
0.2-0.3	875
0.3-0.4	1595
0.4-0.5	2900
0.5-0.6	1957
0.6-0.7	593
0.7-0.8	92
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8152	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD4502	Phase 2
0.7921	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD5658	Approved
0.7746	Intermediate Similarity	NPD5164	Discontinued
0.774	Intermediate Similarity	NPD7222	Phase 2
0.7723	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8403	Phase 1
0.7678	Intermediate Similarity	NPD5939	Approved
0.7678	Intermediate Similarity	NPD5936	Approved
0.767	Intermediate Similarity	NPD4511	Phase 1
0.7662	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD5913	Phase 3
0.7656	Intermediate Similarity	NPD5429	Discontinued
0.7656	Intermediate Similarity	NPD7452	Approved
0.7656	Intermediate Similarity	NPD7453	Approved
0.7652	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3920	Phase 2
0.7586	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1038	Approved
0.7573	Intermediate Similarity	NPD2176	Approved
0.7573	Intermediate Similarity	NPD8396	Approved
0.7573	Intermediate Similarity	NPD8395	Approved
0.7573	Intermediate Similarity	NPD2175	Phase 3
0.7573	Intermediate Similarity	NPD2177	Approved
0.757	Intermediate Similarity	NPD5903	Approved
0.757	Intermediate Similarity	NPD5902	Approved
0.7538	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5530	Phase 1
0.7524	Intermediate Similarity	NPD3003	Approved
0.7488	Intermediate Similarity	NPD6290	Phase 2
0.7465	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD5612	Discontinued
0.7431	Intermediate Similarity	NPD3875	Discontinued
0.7427	Intermediate Similarity	NPD6550	Discontinued
0.7404	Intermediate Similarity	NPD3825	Phase 3
0.7385	Intermediate Similarity	NPD7395	Discontinued
0.7379	Intermediate Similarity	NPD4418	Discontinued
0.7379	Intermediate Similarity	NPD6590	Discontinued
0.7378	Intermediate Similarity	NPD3746	Discontinued
0.7345	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4548	Discontinued
0.7308	Intermediate Similarity	NPD7948	Phase 1
0.7308	Intermediate Similarity	NPD6988	Phase 1
0.7306	Intermediate Similarity	NPD6985	Discontinued
0.7301	Intermediate Similarity	NPD4885	Approved
0.73	Intermediate Similarity	NPD8244	Phase 2
0.7296	Intermediate Similarity	NPD8358	Approved
0.7295	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD5256	Discontinued
0.7289	Intermediate Similarity	NPD5479	Discontinued
0.7277	Intermediate Similarity	NPD6150	Discontinued
0.7273	Intermediate Similarity	NPD3763	Approved
0.7273	Intermediate Similarity	NPD3402	Phase 1
0.7273	Intermediate Similarity	NPD7194	Discontinued
0.7269	Intermediate Similarity	NPD7558	Phase 2
0.726	Intermediate Similarity	NPD5512	Phase 3
0.7256	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD3835	Phase 3
0.7249	Intermediate Similarity	NPD3833	Phase 3
0.7244	Intermediate Similarity	NPD5559	Phase 2
0.7244	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1768	Approved
0.7208	Intermediate Similarity	NPD1325	Approved
0.7208	Intermediate Similarity	NPD1326	Approved
0.72	Intermediate Similarity	NPD6159	Phase 2
0.7198	Intermediate Similarity	NPD3923	Approved
0.7198	Intermediate Similarity	NPD3922	Approved
0.7198	Intermediate Similarity	NPD3924	Approved
0.7198	Intermediate Similarity	NPD3921	Approved
0.7193	Intermediate Similarity	NPD6494	Phase 2
0.7189	Intermediate Similarity	NPD5066	Phase 2
0.7189	Intermediate Similarity	NPD5067	Phase 2
0.7182	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD1856	Discontinued
0.7162	Intermediate Similarity	NPD6242	Discontinued
0.7156	Intermediate Similarity	NPD4927	Discontinued
0.7149	Intermediate Similarity	NPD4429	Discontinued
0.7143	Intermediate Similarity	NPD5003	Discontinued
0.7136	Intermediate Similarity	NPD6208	Discontinued
0.713	Intermediate Similarity	NPD2189	Approved
0.713	Intermediate Similarity	NPD7671	Approved
0.713	Intermediate Similarity	NPD7672	Approved
0.713	Intermediate Similarity	NPD2187	Approved
0.7129	Intermediate Similarity	NPD6251	Discontinued
0.7116	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5810	Discontinued
0.711	Intermediate Similarity	NPD6220	Phase 3
0.7098	Intermediate Similarity	NPD7219	Approved
0.7098	Intermediate Similarity	NPD6736	Discontinued
0.7098	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7221	Approved
0.7094	Intermediate Similarity	NPD7592	Phase 2
0.7091	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8363	Approved
0.7073	Intermediate Similarity	NPD8364	Approved
0.7072	Intermediate Similarity	NPD5632	Approved
0.707	Intermediate Similarity	NPD4795	Phase 2
0.7065	Intermediate Similarity	NPD4354	Approved
0.7064	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD6968	Phase 2
0.7061	Intermediate Similarity	NPD6969	Phase 2
0.7059	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4454	Phase 2
0.7056	Intermediate Similarity	NPD3006	Discontinued
0.7054	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7994	Phase 2
0.7048	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3945	Discontinued
0.7039	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8016	Phase 3
0.7035	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6569	Phase 2
0.7032	Intermediate Similarity	NPD5416	Discontinued
0.7022	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6760	Discontinued
0.7005	Intermediate Similarity	NPD1392	Approved
0.7	Intermediate Similarity	NPD3815	Phase 1
0.7	Intermediate Similarity	NPD3816	Phase 1
0.6995	Remote Similarity	NPD5999	Phase 2
0.6992	Remote Similarity	NPD4442	Phase 2
0.6983	Remote Similarity	NPD7853	Phase 2
0.6982	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6716	Phase 1
0.6977	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6978	Phase 2
0.6974	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1739	Approved
0.6963	Remote Similarity	NPD1740	Approved
0.6961	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD7659	Discontinued
0.6944	Remote Similarity	NPD2920	Discontinued
0.6943	Remote Similarity	NPD7555	Discontinued
0.6938	Remote Similarity	NPD2565	Phase 2
0.6938	Remote Similarity	NPD2564	Approved
0.6934	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3477	Phase 2
0.6933	Remote Similarity	NPD5930	Phase 3
0.6933	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7603	Discontinued
0.6927	Remote Similarity	NPD4203	Approved
0.6927	Remote Similarity	NPD4204	Approved
0.6923	Remote Similarity	NPD6750	Phase 2
0.6923	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.692	Remote Similarity	NPD5044	Phase 2
0.6911	Remote Similarity	NPD6456	Discontinued
0.6908	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6517	Phase 3
0.69	Remote Similarity	NPD5021	Discontinued
0.6898	Remote Similarity	NPD6975	Discontinued
0.6892	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7688	Phase 1
0.6881	Remote Similarity	NPD6245	Phase 2
0.6878	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6243	Phase 3
0.6875	Remote Similarity	NPD6244	Phase 3
0.6875	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6995	Phase 1
0.6872	Remote Similarity	NPD6961	Discontinued
0.6869	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2951	Discontinued
0.6866	Remote Similarity	NPD6991	Approved
0.6866	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6281	Approved
0.6847	Remote Similarity	NPD6202	Discontinued
0.6847	Remote Similarity	NPD3330	Phase 1
0.6844	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8431	Approved
0.684	Remote Similarity	NPD5022	Discontinued
0.6838	Remote Similarity	NPD8465	Approved
0.6838	Remote Similarity	NPD8466	Approved
0.6838	Remote Similarity	NPD8427	Approved
0.6838	Remote Similarity	NPD8467	Approved
0.6838	Remote Similarity	NPD8428	Approved
0.6838	Remote Similarity	NPD8429	Approved
0.6835	Remote Similarity	NPD4122	Approved
0.6835	Remote Similarity	NPD3397	Phase 2
0.6835	Remote Similarity	NPD31	Approved
0.6835	Remote Similarity	NPD4033	Approved
0.6835	Remote Similarity	NPD6473	Phase 1
0.6835	Remote Similarity	NPD32	Approved
0.6835	Remote Similarity	NPD4039	Approved
0.6835	Remote Similarity	NPD4036	Approved
0.6835	Remote Similarity	NPD4037	Approved
0.6835	Remote Similarity	NPD4038	Approved
0.6835	Remote Similarity	NPD4034	Approved
0.6835	Remote Similarity	NPD4035	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