NPASS Compound

Structure

NPC94157 OpenBabel07101718322D 32 37 0 0 0 0 0 0 0 0999 V2000 -1.4271 -3.7192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2038 3.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1254 -0.5387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5927 -1.8555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8052 -1.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4588 -1.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7007 -0.0269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7267 -1.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9962 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4588 -0.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 0.3799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1399 -2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 -2.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 1.9316 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 -1.1180 -2.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7267 -0.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 0.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5927 0.1445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8025 2.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3903 1.2271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3848 1.1226 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 -3.2093 2.9497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1473 -0.3308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 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 19 2 0 0 0 0 9 20 2 0 0 0 0 10 23 2 0 0 0 0 11 24 2 0 0 0 0 12 17 2 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 26 2 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 25 2 0 0 0 0 16 18 1 0 0 0 0 16 30 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 27 2 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 31 1 0 0 0 0 26 28 1 0 0 0 0 26 32 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:	6.444
LogD:	4.731
LogS:	-7.37
# Rotatable Bonds:	4
TPSA:	39.18
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.34
Synthetic Accessibility Score:	2.392
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:	-5.43
MDCK Permeability:	2.2916432499187067e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.592
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	96.67081451416016%
Volume Distribution (VD):	0.819
Pgp-substrate:	0.7041764855384827%

ADMET: Metabolism

CYP1A2-inhibitor:	0.856
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.195
CYP2C9-inhibitor:	0.887
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.915
CYP2D6-substrate:	0.943
CYP3A4-inhibitor:	0.766
CYP3A4-substrate:	0.623

ADMET: Excretion

Clearance (CL):	6.956
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.89
AMES Toxicity:	0.907
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.336
Carcinogencity:	0.904
Eye Corrosion:	0.003
Eye Irritation:	0.629
Respiratory Toxicity:	0.675

Download Data

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

Natural Product: NPC94157

Natural Product ID:	NPC94157
*Common Name:**	Sid506299
IUPAC Name:	1-methoxy-9-[(1-methoxy-9H-carbazol-3-yl)methyl]-3-methylcarbazole
Synonyms:
Standard InCHIKey:	BWIDIGNNLPIYNM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H24N2O2/c1-17-12-22-20-9-5-7-11-24(20)30(28(22)26(13-17)32-3)16-18-14-21-19-8-4-6-10-23(19)29-27(21)25(15-18)31-2/h4-15,29H,16H2,1-3H3
SMILES:	COc1cc(C)cc2c1n(Cc1cc(OC)c3c(c1)c1ccccc1[nH]3)c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496078
PubChem CID:	375158
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]
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

Activity Type	# Activity
Cell Line	91
NON-MOLECULAR	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	=	12022.64	nM	PMID[547825]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	9772.37	nM	PMID[547825]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	=	8511.38	nM	PMID[547825]
NPT385	Cell Line	SR	Homo sapiens	GI50	=	16595.87	nM	PMID[547825]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	23442.29	nM	PMID[547825]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	=	6606.93	nM	PMID[547825]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	=	5370.32	nM	PMID[547825]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	=	16982.44	nM	PMID[547825]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	10715.19	nM	PMID[547825]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	5370.32	nM	PMID[547825]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	=	15135.61	nM	PMID[547825]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	16982.44	nM	PMID[547825]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	16982.44	nM	PMID[547825]
NPT386	Cell Line	KM12	Homo sapiens	GI50	=	10232.93	nM	PMID[547825]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	15488.17	nM	PMID[547825]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	=	13489.63	nM	PMID[547825]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	17378.01	nM	PMID[547825]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	=	9772.37	nM	PMID[547825]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	=	22908.68	nM	PMID[547825]
NPT380	Cell Line	U-251	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT574	Cell Line	XF498	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	=	8128.31	nM	PMID[547825]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT387	Cell Line	M14	Homo sapiens	GI50	=	6309.57	nM	PMID[547825]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	=	15135.61	nM	PMID[547825]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT401	Cell Line	786-0	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	=	12302.69	nM	PMID[547825]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	=	25118.86	nM	PMID[547825]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	12189.9	nM	PMID[547826]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	12274.39	nM	PMID[547826]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	5395.11	nM	PMID[547826]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	9840.11	nM	PMID[547826]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	9705.1	nM	PMID[547826]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	10209.39	nM	PMID[547826]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	6622.17	nM	PMID[547826]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	8511.38	nM	PMID[547826]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	10495.42	nM	PMID[547826]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	15135.61	nM	PMID[547826]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	16634.13	nM	PMID[547826]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	13427.65	nM	PMID[547826]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	5432.5	nM	PMID[547826]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	6266.14	nM	PMID[547826]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	10232.93	nM	PMID[547826]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	8184.65	nM	PMID[547826]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	15417.0	nM	PMID[547826]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	23173.95	nM	PMID[547826]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	16788.04	nM	PMID[547826]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	17498.47	nM	PMID[547826]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	16943.38	nM	PMID[547826]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	19998.62	nM	PMID[547826]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	14996.85	nM	PMID[547826]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	10839.27	nM	PMID[547826]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	23120.65	nM	PMID[547826]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	11994.99	nM	PMID[547826]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	16982.44	nM	PMID[547826]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	16943.38	nM	PMID[547826]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[547826]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	12302.69	nM	PMID[547825]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	25118.86	nM	PMID[547825]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	16982.44	nM	PMID[547825]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	19952.62	nM	PMID[547825]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	10232.93	nM	PMID[547825]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	10471.29	nM	PMID[547825]

☑ 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 NPC94157 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	690
0.1-0.2	4621
0.2-0.3	12590
0.3-0.4	11521
0.4-0.5	8218
0.5-0.6	2892
0.6-0.7	1670
0.7-0.8	435
0.8-0.85	44
0.85-0.9	8
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9641	High Similarity	NPC132642
0.9353	High Similarity	NPC473185
0.9278	High Similarity	NPC199667
0.9227	High Similarity	NPC473181
0.9216	High Similarity	NPC475253
0.9184	High Similarity	NPC473180
0.9082	High Similarity	NPC39370
0.9078	High Similarity	NPC473186
0.9005	High Similarity	NPC473179
0.8995	High Similarity	NPC473183
0.89	High Similarity	NPC473184
0.8883	High Similarity	NPC242928
0.868	High Similarity	NPC475774
0.8667	High Similarity	NPC128823
0.8564	High Similarity	NPC474798
0.8502	High Similarity	NPC477533
0.8498	Intermediate Similarity	NPC473182
0.8451	Intermediate Similarity	NPC469554
0.8382	Intermediate Similarity	NPC208284
0.8364	Intermediate Similarity	NPC101543
0.8358	Intermediate Similarity	NPC470930
0.831	Intermediate Similarity	NPC314954
0.8308	Intermediate Similarity	NPC476138
0.8308	Intermediate Similarity	NPC245816
0.8302	Intermediate Similarity	NPC202503
0.825	Intermediate Similarity	NPC329793
0.8238	Intermediate Similarity	NPC473189
0.8229	Intermediate Similarity	NPC176127
0.8223	Intermediate Similarity	NPC475190
0.8182	Intermediate Similarity	NPC131017
0.8164	Intermediate Similarity	NPC26679
0.8157	Intermediate Similarity	NPC180504
0.8134	Intermediate Similarity	NPC170114
0.8131	Intermediate Similarity	NPC227908
0.8128	Intermediate Similarity	NPC162484
0.8125	Intermediate Similarity	NPC39500
0.8122	Intermediate Similarity	NPC92111
0.8116	Intermediate Similarity	NPC187501
0.8113	Intermediate Similarity	NPC477532
0.8107	Intermediate Similarity	NPC185782
0.8088	Intermediate Similarity	NPC285558
0.8086	Intermediate Similarity	NPC470549
0.8071	Intermediate Similarity	NPC76748
0.8069	Intermediate Similarity	NPC329747
0.8068	Intermediate Similarity	NPC471304
0.806	Intermediate Similarity	NPC72211
0.8056	Intermediate Similarity	NPC252251
0.804	Intermediate Similarity	NPC307963
0.8039	Intermediate Similarity	NPC223427
0.802	Intermediate Similarity	NPC296527
0.8019	Intermediate Similarity	NPC209769
0.801	Intermediate Similarity	NPC70956
0.801	Intermediate Similarity	NPC243834
0.7991	Intermediate Similarity	NPC144452
0.7982	Intermediate Similarity	NPC477531
0.7981	Intermediate Similarity	NPC225279
0.798	Intermediate Similarity	NPC19872
0.798	Intermediate Similarity	NPC176538
0.7972	Intermediate Similarity	NPC184408
0.796	Intermediate Similarity	NPC70259
0.7952	Intermediate Similarity	NPC478074
0.7952	Intermediate Similarity	NPC476287
0.7952	Intermediate Similarity	NPC469592
0.7952	Intermediate Similarity	NPC471080
0.7941	Intermediate Similarity	NPC267423
0.7936	Intermediate Similarity	NPC209174
0.7934	Intermediate Similarity	NPC208084
0.7933	Intermediate Similarity	NPC201697
0.793	Intermediate Similarity	NPC26543
0.7923	Intermediate Similarity	NPC193777
0.791	Intermediate Similarity	NPC43787
0.791	Intermediate Similarity	NPC205934
0.7908	Intermediate Similarity	NPC84478
0.7897	Intermediate Similarity	NPC86078
0.7877	Intermediate Similarity	NPC8022
0.7877	Intermediate Similarity	NPC470799
0.7876	Intermediate Similarity	NPC56618
0.7871	Intermediate Similarity	NPC251090
0.7861	Intermediate Similarity	NPC473178
0.7818	Intermediate Similarity	NPC474688
0.7816	Intermediate Similarity	NPC475112
0.7816	Intermediate Similarity	NPC291535
0.7816	Intermediate Similarity	NPC475085
0.781	Intermediate Similarity	NPC167860
0.781	Intermediate Similarity	NPC123976
0.7808	Intermediate Similarity	NPC274640
0.7804	Intermediate Similarity	NPC96321
0.7804	Intermediate Similarity	NPC469594
0.7799	Intermediate Similarity	NPC475910
0.7795	Intermediate Similarity	NPC88363
0.7788	Intermediate Similarity	NPC300156
0.7788	Intermediate Similarity	NPC45190
0.7778	Intermediate Similarity	NPC477066
0.7767	Intermediate Similarity	NPC476044
0.7756	Intermediate Similarity	NPC18487
0.7743	Intermediate Similarity	NPC478081
0.7739	Intermediate Similarity	NPC473188
0.7737	Intermediate Similarity	NPC118511
0.7736	Intermediate Similarity	NPC48353
0.7703	Intermediate Similarity	NPC476106
0.77	Intermediate Similarity	NPC266931
0.7689	Intermediate Similarity	NPC11408
0.7685	Intermediate Similarity	NPC292958
0.7685	Intermediate Similarity	NPC213530
0.7685	Intermediate Similarity	NPC193267
0.7682	Intermediate Similarity	NPC53534
0.7681	Intermediate Similarity	NPC232727
0.7679	Intermediate Similarity	NPC473187
0.7678	Intermediate Similarity	NPC469589
0.7671	Intermediate Similarity	NPC179287
0.7668	Intermediate Similarity	NPC329631
0.7665	Intermediate Similarity	NPC477067
0.7665	Intermediate Similarity	NPC478082
0.7664	Intermediate Similarity	NPC118228
0.7662	Intermediate Similarity	NPC246700
0.7661	Intermediate Similarity	NPC280272
0.7642	Intermediate Similarity	NPC5145
0.7639	Intermediate Similarity	NPC303658
0.763	Intermediate Similarity	NPC477111
0.7623	Intermediate Similarity	NPC49547
0.7621	Intermediate Similarity	NPC217554
0.7619	Intermediate Similarity	NPC472111
0.761	Intermediate Similarity	NPC13880
0.7609	Intermediate Similarity	NPC471891
0.7593	Intermediate Similarity	NPC305984
0.7588	Intermediate Similarity	NPC473540
0.7585	Intermediate Similarity	NPC476167
0.7578	Intermediate Similarity	NPC476451
0.7573	Intermediate Similarity	NPC267928
0.7571	Intermediate Similarity	NPC475070
0.7565	Intermediate Similarity	NPC475666
0.7563	Intermediate Similarity	NPC152620
0.756	Intermediate Similarity	NPC199277
0.756	Intermediate Similarity	NPC135887
0.7559	Intermediate Similarity	NPC11464
0.7558	Intermediate Similarity	NPC473041
0.7557	Intermediate Similarity	NPC470018
0.7556	Intermediate Similarity	NPC277351
0.7549	Intermediate Similarity	NPC99666
0.7548	Intermediate Similarity	NPC11017
0.7548	Intermediate Similarity	NPC249040
0.7547	Intermediate Similarity	NPC476465
0.7545	Intermediate Similarity	NPC51388
0.7544	Intermediate Similarity	NPC475844
0.7536	Intermediate Similarity	NPC192315
0.7534	Intermediate Similarity	NPC280799
0.7532	Intermediate Similarity	NPC17437
0.7525	Intermediate Similarity	NPC473177
0.7523	Intermediate Similarity	NPC74575
0.7523	Intermediate Similarity	NPC257851
0.7522	Intermediate Similarity	NPC81939
0.7522	Intermediate Similarity	NPC208522
0.7522	Intermediate Similarity	NPC295228
0.7522	Intermediate Similarity	NPC284141
0.7512	Intermediate Similarity	NPC94943
0.7512	Intermediate Similarity	NPC84853
0.7512	Intermediate Similarity	NPC476041
0.7512	Intermediate Similarity	NPC304926
0.7512	Intermediate Similarity	NPC476116
0.75	Intermediate Similarity	NPC4687
0.75	Intermediate Similarity	NPC249583
0.7489	Intermediate Similarity	NPC15801
0.7489	Intermediate Similarity	NPC472099
0.7488	Intermediate Similarity	NPC472098
0.7488	Intermediate Similarity	NPC153042
0.7488	Intermediate Similarity	NPC128751
0.7488	Intermediate Similarity	NPC294620
0.7487	Intermediate Similarity	NPC478032
0.7478	Intermediate Similarity	NPC24802
0.7475	Intermediate Similarity	NPC171171
0.7465	Intermediate Similarity	NPC470931
0.7465	Intermediate Similarity	NPC287208
0.7465	Intermediate Similarity	NPC82548
0.7465	Intermediate Similarity	NPC477110
0.7463	Intermediate Similarity	NPC190007
0.7455	Intermediate Similarity	NPC310118
0.7454	Intermediate Similarity	NPC271215
0.7454	Intermediate Similarity	NPC149471
0.7453	Intermediate Similarity	NPC477113
0.7451	Intermediate Similarity	NPC469497
0.7451	Intermediate Similarity	NPC106833
0.7444	Intermediate Similarity	NPC478078
0.7444	Intermediate Similarity	NPC157931
0.7442	Intermediate Similarity	NPC294375
0.7426	Intermediate Similarity	NPC314002
0.7426	Intermediate Similarity	NPC42591
0.7424	Intermediate Similarity	NPC477861
0.7418	Intermediate Similarity	NPC283117
0.7416	Intermediate Similarity	NPC476582
0.7416	Intermediate Similarity	NPC4071
0.7416	Intermediate Similarity	NPC476578
0.7415	Intermediate Similarity	NPC478080
0.7413	Intermediate Similarity	NPC212535
0.7411	Intermediate Similarity	NPC253580
0.7411	Intermediate Similarity	NPC311906
0.7407	Intermediate Similarity	NPC316981
0.7404	Intermediate Similarity	NPC77555
0.7399	Intermediate Similarity	NPC103687
0.7399	Intermediate Similarity	NPC132631
0.7397	Intermediate Similarity	NPC46561

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 NPC94157 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	689
0.2-0.3	837
0.3-0.4	1530
0.4-0.5	2629
0.5-0.6	2144
0.6-0.7	816
0.7-0.8	151
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8384	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8186	Intermediate Similarity	NPD7222	Phase 2
0.816	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7452	Approved
0.8098	Intermediate Similarity	NPD7453	Approved
0.8058	Intermediate Similarity	NPD5658	Approved
0.804	Intermediate Similarity	NPD1038	Approved
0.804	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.794	Intermediate Similarity	NPD5913	Phase 3
0.794	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7915	Intermediate Similarity	NPD5903	Approved
0.7915	Intermediate Similarity	NPD5902	Approved
0.7874	Intermediate Similarity	NPD3003	Approved
0.7822	Intermediate Similarity	NPD4418	Discontinued
0.7788	Intermediate Similarity	NPD8403	Phase 1
0.7778	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7773	Intermediate Similarity	NPD4502	Phase 2
0.7756	Intermediate Similarity	NPD3825	Phase 3
0.7727	Intermediate Similarity	NPD5559	Phase 2
0.7721	Intermediate Similarity	NPD6985	Discontinued
0.771	Intermediate Similarity	NPD5612	Discontinued
0.7685	Intermediate Similarity	NPD7194	Discontinued
0.7685	Intermediate Similarity	NPD3402	Phase 1
0.7685	Intermediate Similarity	NPD3875	Discontinued
0.7668	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD6242	Discontinued
0.765	Intermediate Similarity	NPD5256	Discontinued
0.7619	Intermediate Similarity	NPD5530	Phase 1
0.7598	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7585	Intermediate Similarity	NPD8396	Approved
0.7585	Intermediate Similarity	NPD1768	Approved
0.7585	Intermediate Similarity	NPD8395	Approved
0.7547	Intermediate Similarity	NPD2189	Approved
0.7547	Intermediate Similarity	NPD2187	Approved
0.7545	Intermediate Similarity	NPD4885	Approved
0.7532	Intermediate Similarity	NPD8358	Approved
0.7512	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD7558	Phase 2
0.7488	Intermediate Similarity	NPD7948	Phase 1
0.7477	Intermediate Similarity	NPD4429	Discontinued
0.7476	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5479	Discontinued
0.7446	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD3006	Discontinued
0.7442	Intermediate Similarity	NPD5066	Phase 2
0.7442	Intermediate Similarity	NPD5067	Phase 2
0.7442	Intermediate Similarity	NPD5936	Approved
0.7442	Intermediate Similarity	NPD5939	Approved
0.7429	Intermediate Similarity	NPD4511	Phase 1
0.7419	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD1392	Approved
0.7411	Intermediate Similarity	NPD7555	Discontinued
0.7406	Intermediate Similarity	NPD4795	Phase 2
0.7404	Intermediate Similarity	NPD7659	Discontinued
0.7398	Intermediate Similarity	NPD1326	Approved
0.7398	Intermediate Similarity	NPD1325	Approved
0.7397	Intermediate Similarity	NPD5632	Approved
0.7387	Intermediate Similarity	NPD6159	Phase 2
0.7364	Intermediate Similarity	NPD3763	Approved
0.7364	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3477	Phase 2
0.7352	Intermediate Similarity	NPD5164	Discontinued
0.735	Intermediate Similarity	NPD3920	Phase 2
0.7349	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2175	Phase 3
0.7333	Intermediate Similarity	NPD5999	Phase 2
0.7333	Intermediate Similarity	NPD2176	Approved
0.7333	Intermediate Similarity	NPD2177	Approved
0.7333	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6961	Discontinued
0.7302	Intermediate Similarity	NPD7672	Approved
0.7302	Intermediate Similarity	NPD7671	Approved
0.7296	Intermediate Similarity	NPD5044	Phase 2
0.7295	Intermediate Similarity	NPD3923	Approved
0.7295	Intermediate Similarity	NPD3924	Approved
0.7295	Intermediate Similarity	NPD3922	Approved
0.7295	Intermediate Similarity	NPD3921	Approved
0.7295	Intermediate Similarity	NPD8363	Approved
0.7295	Intermediate Similarity	NPD8364	Approved
0.7294	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4454	Phase 2
0.7289	Intermediate Similarity	NPD7994	Phase 2
0.7284	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6220	Phase 3
0.7281	Intermediate Similarity	NPD6494	Phase 2
0.7277	Intermediate Similarity	NPD4204	Approved
0.7277	Intermediate Similarity	NPD4203	Approved
0.7277	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD7219	Approved
0.7265	Intermediate Similarity	NPD7221	Approved
0.7256	Intermediate Similarity	NPD5429	Discontinued
0.7256	Intermediate Similarity	NPD6290	Phase 2
0.7253	Intermediate Similarity	NPD7068	Approved
0.7253	Intermediate Similarity	NPD7067	Approved
0.7251	Intermediate Similarity	NPD4548	Discontinued
0.7248	Intermediate Similarity	NPD3815	Phase 1
0.7248	Intermediate Similarity	NPD3330	Phase 1
0.7248	Intermediate Similarity	NPD3816	Phase 1
0.7244	Intermediate Similarity	NPD7603	Discontinued
0.7243	Intermediate Similarity	NPD32	Approved
0.7243	Intermediate Similarity	NPD31	Approved
0.7243	Intermediate Similarity	NPD4034	Approved
0.7243	Intermediate Similarity	NPD4035	Approved
0.7243	Intermediate Similarity	NPD4037	Approved
0.7243	Intermediate Similarity	NPD4036	Approved
0.7243	Intermediate Similarity	NPD4039	Approved
0.7243	Intermediate Similarity	NPD4038	Approved
0.7243	Intermediate Similarity	NPD4033	Approved
0.7243	Intermediate Similarity	NPD4122	Approved
0.7238	Intermediate Similarity	NPD5003	Discontinued
0.7236	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6643	Discontinued
0.7225	Intermediate Similarity	NPD6969	Phase 2
0.7225	Intermediate Similarity	NPD6968	Phase 2
0.7217	Intermediate Similarity	NPD1739	Approved
0.7217	Intermediate Similarity	NPD1740	Approved
0.7212	Intermediate Similarity	NPD6978	Phase 2
0.7212	Intermediate Similarity	NPD6569	Phase 2
0.7212	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6991	Approved
0.719	Intermediate Similarity	NPD6550	Discontinued
0.7188	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD802	Phase 2
0.7173	Intermediate Similarity	NPD3835	Phase 3
0.7173	Intermediate Similarity	NPD6243	Phase 3
0.7173	Intermediate Similarity	NPD6244	Phase 3
0.7173	Intermediate Similarity	NPD5482	Discontinued
0.7173	Intermediate Similarity	NPD3833	Phase 3
0.7167	Intermediate Similarity	NPD8244	Phase 2
0.7163	Intermediate Similarity	NPD3397	Phase 2
0.7162	Intermediate Similarity	NPD3746	Discontinued
0.7162	Intermediate Similarity	NPD7395	Discontinued
0.7157	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD5022	Discontinued
0.7143	Intermediate Similarity	NPD4442	Phase 2
0.7143	Intermediate Similarity	NPD6590	Discontinued
0.7143	Intermediate Similarity	NPD6595	Phase 3
0.7143	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3945	Discontinued
0.7131	Intermediate Similarity	NPD6456	Discontinued
0.713	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4890	Phase 2
0.7124	Intermediate Similarity	NPD8016	Phase 3
0.7124	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7719	Discontinued
0.7119	Intermediate Similarity	NPD8100	Phase 3
0.7108	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7106	Intermediate Similarity	NPD7592	Phase 2
0.7104	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1034	Phase 3
0.71	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD5930	Phase 3
0.7093	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7051	Phase 3
0.7092	Intermediate Similarity	NPD112	Approved
0.7092	Intermediate Similarity	NPD9705	Discontinued
0.7091	Intermediate Similarity	NPD6202	Discontinued
0.7089	Intermediate Similarity	NPD7868	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD6750	Phase 2
0.7075	Intermediate Similarity	NPD6988	Phase 1
0.7074	Intermediate Similarity	NPD7567	Approved
0.7074	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7726	Phase 1
0.7064	Intermediate Similarity	NPD6517	Phase 3
0.7062	Intermediate Similarity	NPD6251	Discontinued
0.7052	Intermediate Similarity	NPD8465	Approved
0.7052	Intermediate Similarity	NPD8429	Approved
0.7052	Intermediate Similarity	NPD8467	Approved
0.7052	Intermediate Similarity	NPD8428	Approved
0.7052	Intermediate Similarity	NPD8466	Approved
0.7052	Intermediate Similarity	NPD8427	Approved
0.7051	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6150	Discontinued
0.7048	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7470	Discontinued
0.7045	Intermediate Similarity	NPD5416	Discontinued
0.7043	Intermediate Similarity	NPD7688	Phase 1
0.704	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4344	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