NPASS Compound

Structure

NPC128244 OpenBabel07101719522D 22 26 0 0 0 0 0 0 0 0999 V2000 2.5981 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 -3.5709 0.6072 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 -2.8764 0.2728 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6285 1.3759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 0.7070 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 -2.2971 1.4757 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9916 1.8102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7517 -0.7160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 4 1 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 10 2 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 19 2 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	283.07
Volume:	289.881
LogP:	3.172
LogD:	2.829
LogS:	-6.122
# Rotatable Bonds:	0
TPSA:	55.74
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	2.413
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.893
MDCK Permeability:	2.338734338991344e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.178
30% Bioavailability (F30%):	0.557

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.755
Plasma Protein Binding (PPB):	97.2638168334961%
Volume Distribution (VD):	1.463
Pgp-substrate:	1.3282477855682373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.263
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.231
CYP2C9-substrate:	0.684
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.536
CYP3A4-inhibitor:	0.403
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	2.045
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.22
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.943
Rat Oral Acute Toxicity:	0.273
Maximum Recommended Daily Dose:	0.747
Skin Sensitization:	0.421
Carcinogencity:	0.757
Eye Corrosion:	0.004
Eye Irritation:	0.952
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC128244

Natural Product ID:	NPC128244
*Common Name:**	Ascididemin
IUPAC Name:	n.a.
Synonyms:	Ascididemin
Standard InCHIKey:	BTAIBIXHXSXUFN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H9N3O/c22-18-12-5-3-8-19-15(12)16-14-11(7-9-20-16)10-4-1-2-6-13(10)21-17(14)18/h1-9H
SMILES:	O=C1c2cccnc2c2c3c1nc1ccccc1c3ccn2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL340160
PubChem CID:	189219
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0002827] Pyrido[2,3,4-kl]acridines

*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
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812214]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20491501]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	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	59
IC50	25
MIC	5
Others	12

Activity Type	# Activity
Cell Line	84
Individual Protein	2
NON-MOLECULAR	1
Organism	12
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	400.0	nM	PMID[478468]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	300.0	nM	PMID[478468]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	300.0	nM	PMID[478468]
NPT1161	Cell Line	CHO	Cricetulus griseus	IC50	=	30.0	nM	PMID[478468]
NPT1161	Cell Line	CHO	Cricetulus griseus	HF	=	10.0	n.a.	PMID[478468]
NPT1161	Cell Line	CHO	Cricetulus griseus	IC50	=	300.0	nM	PMID[478468]
NPT1161	Cell Line	CHO	Cricetulus griseus	HF2	=	1.0	n.a.	PMID[478468]
NPT4754	Cell Line	BSC-1	Chlorocebus aethiops	Excess zone radius	=	4.5	mM	PMID[478468]
NPT1535	Cell Line	U-87 MG	Homo sapiens	IC50	=	70.0	nM	PMID[478469]
NPT933	Cell Line	U373 MG	Homo sapiens	IC50	=	500.0	nM	PMID[478469]
NPT550	Cell Line	T-24	Homo sapiens	IC50	=	800.0	nM	PMID[478469]
NPT1505	Cell Line	J82	Homo sapiens	IC50	=	300.0	nM	PMID[478469]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	6.0	nM	PMID[478469]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	900.0	nM	PMID[478469]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	70.0	nM	PMID[478469]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	600.0	nM	PMID[478469]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	200.0	nM	PMID[478469]
NPT2331	Cell Line	A-427	Homo sapiens	IC50	=	60.0	nM	PMID[478469]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	8.0	nM	PMID[478469]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	<	0.04	ug.mL-1	PMID[478470]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Selectivity	<	0.4	n.a.	PMID[478470]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	186.21	nM	PMID[478473]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	157.04	nM	PMID[478473]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	172.19	nM	PMID[478473]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	142.56	nM	PMID[478473]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	37.07	nM	PMID[478473]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100.23	nM	PMID[478473]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	489.78	nM	PMID[478473]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	62.09	nM	PMID[478473]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	189.23	nM	PMID[478473]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	58.34	nM	PMID[478473]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	230.67	nM	PMID[478473]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	269.77	nM	PMID[478473]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	165.96	nM	PMID[478473]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	31.84	nM	PMID[478473]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	691.83	nM	PMID[478473]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	97.05	nM	PMID[478473]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	84.53	nM	PMID[478473]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	55.08	nM	PMID[478473]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	475.34	nM	PMID[478473]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	50.47	nM	PMID[478473]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	281.19	nM	PMID[478473]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	105.44	nM	PMID[478473]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	187.5	nM	PMID[478473]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	70.47	nM	PMID[478473]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	1267.65	nM	PMID[478473]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	97.5	nM	PMID[478473]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	183.23	nM	PMID[478473]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	46.56	nM	PMID[478473]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	264.24	nM	PMID[478473]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	105.44	nM	PMID[478473]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	1025.65	nM	PMID[478473]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	51.17	nM	PMID[478473]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	168.66	nM	PMID[478473]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	184.5	nM	PMID[478473]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	255.27	nM	PMID[478473]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	389.05	nM	PMID[478473]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	36.98	nM	PMID[478473]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	108.64	nM	PMID[478473]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	35.16	nM	PMID[478473]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	912.01	nM	PMID[478473]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	70.79	nM	PMID[478473]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	188.36	nM	PMID[478473]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	272.27	nM	PMID[478473]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	290.4	nM	PMID[478473]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	87.9	nM	PMID[478473]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	223.87	nM	PMID[478473]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	189.67	nM	PMID[478473]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	214.78	nM	PMID[478473]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	309.74	nM	PMID[478473]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	79.8	nM	PMID[478473]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	636.8	nM	PMID[478473]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	320.63	nM	PMID[478473]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	751.62	nM	PMID[478473]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	501.19	nM	PMID[478473]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	209.89	nM	PMID[478473]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	320.63	nM	PMID[478473]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	1185.77	nM	PMID[478473]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	139.96	nM	PMID[478473]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	1986.09	nM	PMID[478473]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	140.0	nM	PMID[478474]
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	1376.0	nM	PMID[478475]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	380.0	nM	PMID[478476]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	100.0	nM	PMID[478476]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	250.0	nM	PMID[478476]
NPT144	Individual Protein	Telomerase reverse transcriptase	Homo sapiens	IC50	>	80.0	ug.mL-1	PMID[478478]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Excess zone radius	=	14.0	mM	PMID[478468]
NPT19	Organism	Escherichia coli	Escherichia coli	Excess zone radius	=	10.0	mM	PMID[478468]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Excess zone radius	=	0.0	mM	PMID[478468]
NPT20	Organism	Candida albicans	Candida albicans	Excess zone radius	=	11.0	mM	PMID[478468]
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	Excess zone radius	=	0.0	mM	PMID[478468]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	Excess zone radius	=	10.0	mM	PMID[478468]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	600.0	nM	PMID[478469]
NPT2	Others	Unspecified		MTD	=	20.0	mg kg-1	PMID[478469]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	0.1	ug.mL-1	PMID[478470]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	200.0	nM	PMID[478471]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	300.0	nM	PMID[478471]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	32.0	nM	PMID[478472]
NPT2	Others	Unspecified		Selectivity Index	<	1.0	n.a.	PMID[478474]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	350.0	nM	PMID[478474]
NPT5246	Organism	Mycobacterium aurum	Mycobacterium aurum	MIC	=	0.25	ug.mL-1	PMID[478477]

☑ 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 NPC128244 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	900
0.1-0.2	7836
0.2-0.3	16294
0.3-0.4	12602
0.4-0.5	1731
0.5-0.6	2164
0.6-0.7	1010
0.7-0.8	144
0.8-0.85	12
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8846	High Similarity	NPC216550
0.8701	High Similarity	NPC237188
0.8462	Intermediate Similarity	NPC467063
0.8396	Intermediate Similarity	NPC326422
0.8389	Intermediate Similarity	NPC157583
0.836	Intermediate Similarity	NPC167710
0.8245	Intermediate Similarity	NPC272458
0.8152	Intermediate Similarity	NPC191415
0.8125	Intermediate Similarity	NPC34837
0.8103	Intermediate Similarity	NPC317701
0.8056	Intermediate Similarity	NPC70949
0.7989	Intermediate Similarity	NPC255909
0.7989	Intermediate Similarity	NPC103119
0.7978	Intermediate Similarity	NPC297034
0.7923	Intermediate Similarity	NPC252572
0.7914	Intermediate Similarity	NPC102755
0.7901	Intermediate Similarity	NPC56233
0.7853	Intermediate Similarity	NPC324091
0.7824	Intermediate Similarity	NPC304203
0.775	Intermediate Similarity	NPC472065
0.772	Intermediate Similarity	NPC476460
0.7716	Intermediate Similarity	NPC81535
0.7713	Intermediate Similarity	NPC73994
0.7707	Intermediate Similarity	NPC237740
0.7701	Intermediate Similarity	NPC284775
0.7692	Intermediate Similarity	NPC265100
0.7662	Intermediate Similarity	NPC472064
0.7647	Intermediate Similarity	NPC151635
0.7626	Intermediate Similarity	NPC237414
0.7592	Intermediate Similarity	NPC477003
0.7586	Intermediate Similarity	NPC116555
0.7576	Intermediate Similarity	NPC474916
0.7548	Intermediate Similarity	NPC267811
0.7527	Intermediate Similarity	NPC80681
0.7525	Intermediate Similarity	NPC106824
0.7512	Intermediate Similarity	NPC328318
0.7512	Intermediate Similarity	NPC328596
0.75	Intermediate Similarity	NPC229893
0.7475	Intermediate Similarity	NPC79356
0.7475	Intermediate Similarity	NPC472116
0.7475	Intermediate Similarity	NPC102592
0.7461	Intermediate Similarity	NPC133003
0.745	Intermediate Similarity	NPC284338
0.7444	Intermediate Similarity	NPC70406
0.7438	Intermediate Similarity	NPC327592
0.7432	Intermediate Similarity	NPC293487
0.7426	Intermediate Similarity	NPC472062
0.7426	Intermediate Similarity	NPC472063
0.7426	Intermediate Similarity	NPC472069
0.7421	Intermediate Similarity	NPC83774
0.7405	Intermediate Similarity	NPC478184
0.7405	Intermediate Similarity	NPC478182
0.7403	Intermediate Similarity	NPC251391
0.7402	Intermediate Similarity	NPC317373
0.7381	Intermediate Similarity	NPC27041
0.7351	Intermediate Similarity	NPC242116
0.7348	Intermediate Similarity	NPC470679
0.7348	Intermediate Similarity	NPC217021
0.7344	Intermediate Similarity	NPC61011
0.7333	Intermediate Similarity	NPC118084
0.7326	Intermediate Similarity	NPC478183
0.7316	Intermediate Similarity	NPC469529
0.7299	Intermediate Similarity	NPC469727
0.7293	Intermediate Similarity	NPC313889
0.7263	Intermediate Similarity	NPC467188
0.7258	Intermediate Similarity	NPC194881
0.7258	Intermediate Similarity	NPC478185
0.7255	Intermediate Similarity	NPC57398
0.7245	Intermediate Similarity	NPC135601
0.7245	Intermediate Similarity	NPC17273
0.7245	Intermediate Similarity	NPC141612
0.7241	Intermediate Similarity	NPC121327
0.7238	Intermediate Similarity	NPC123906
0.7234	Intermediate Similarity	NPC114637
0.7231	Intermediate Similarity	NPC46895
0.7219	Intermediate Similarity	NPC317105
0.7212	Intermediate Similarity	NPC472070
0.7209	Intermediate Similarity	NPC216612
0.7198	Intermediate Similarity	NPC473878
0.7194	Intermediate Similarity	NPC99939
0.7194	Intermediate Similarity	NPC308931
0.719	Intermediate Similarity	NPC318299
0.7188	Intermediate Similarity	NPC280852
0.7182	Intermediate Similarity	NPC105811
0.7181	Intermediate Similarity	NPC42372
0.7176	Intermediate Similarity	NPC322482
0.7171	Intermediate Similarity	NPC106757
0.7171	Intermediate Similarity	NPC143977
0.7158	Intermediate Similarity	NPC32534
0.7156	Intermediate Similarity	NPC317752
0.7151	Intermediate Similarity	NPC474492
0.7143	Intermediate Similarity	NPC21429
0.7135	Intermediate Similarity	NPC293216
0.7128	Intermediate Similarity	NPC271797
0.7128	Intermediate Similarity	NPC21174
0.712	Intermediate Similarity	NPC325903
0.7112	Intermediate Similarity	NPC100104
0.7112	Intermediate Similarity	NPC470680
0.7109	Intermediate Similarity	NPC470702
0.7109	Intermediate Similarity	NPC473218
0.7108	Intermediate Similarity	NPC477004
0.7104	Intermediate Similarity	NPC207686
0.7104	Intermediate Similarity	NPC935
0.7104	Intermediate Similarity	NPC267078
0.7101	Intermediate Similarity	NPC88115
0.709	Intermediate Similarity	NPC115232
0.7081	Intermediate Similarity	NPC266249
0.7075	Intermediate Similarity	NPC470703
0.7072	Intermediate Similarity	NPC474357
0.7071	Intermediate Similarity	NPC62749
0.7068	Intermediate Similarity	NPC91895
0.7067	Intermediate Similarity	NPC238457
0.7047	Intermediate Similarity	NPC471579
0.7031	Intermediate Similarity	NPC201634
0.7026	Intermediate Similarity	NPC12649
0.7019	Intermediate Similarity	NPC472259
0.7014	Intermediate Similarity	NPC123839
0.7011	Intermediate Similarity	NPC40070
0.7009	Intermediate Similarity	NPC322064
0.7005	Intermediate Similarity	NPC243058
0.6995	Remote Similarity	NPC470111
0.699	Remote Similarity	NPC24864
0.6989	Remote Similarity	NPC209362
0.6982	Remote Similarity	NPC470323
0.698	Remote Similarity	NPC47190
0.6978	Remote Similarity	NPC86288
0.6978	Remote Similarity	NPC235685
0.6974	Remote Similarity	NPC219848
0.697	Remote Similarity	NPC203635
0.6966	Remote Similarity	NPC251722
0.6966	Remote Similarity	NPC314102
0.6954	Remote Similarity	NPC470677
0.6951	Remote Similarity	NPC279189
0.6951	Remote Similarity	NPC200553
0.6948	Remote Similarity	NPC118940
0.6947	Remote Similarity	NPC101350
0.694	Remote Similarity	NPC63545
0.6939	Remote Similarity	NPC256268
0.6927	Remote Similarity	NPC134657
0.6927	Remote Similarity	NPC227582
0.6919	Remote Similarity	NPC143533
0.6919	Remote Similarity	NPC117027
0.6915	Remote Similarity	NPC213914
0.6902	Remote Similarity	NPC201380
0.6902	Remote Similarity	NPC469811
0.6902	Remote Similarity	NPC179787
0.6902	Remote Similarity	NPC100726
0.69	Remote Similarity	NPC90415
0.6898	Remote Similarity	NPC229055
0.6891	Remote Similarity	NPC471943
0.6889	Remote Similarity	NPC174489
0.6884	Remote Similarity	NPC258480
0.6881	Remote Similarity	NPC323969
0.6869	Remote Similarity	NPC471193
0.6869	Remote Similarity	NPC471194
0.6865	Remote Similarity	NPC321911
0.6862	Remote Similarity	NPC74357
0.686	Remote Similarity	NPC74413
0.6858	Remote Similarity	NPC162002
0.6848	Remote Similarity	NPC478186
0.6845	Remote Similarity	NPC281094
0.6845	Remote Similarity	NPC138842
0.684	Remote Similarity	NPC178858
0.6837	Remote Similarity	NPC234078
0.6837	Remote Similarity	NPC221100
0.6834	Remote Similarity	NPC470205
0.6833	Remote Similarity	NPC169433
0.683	Remote Similarity	NPC477112
0.6828	Remote Similarity	NPC26641
0.6828	Remote Similarity	NPC471655
0.6827	Remote Similarity	NPC252338
0.6822	Remote Similarity	NPC53534
0.6821	Remote Similarity	NPC161861
0.6818	Remote Similarity	NPC88110
0.6818	Remote Similarity	NPC477042
0.6814	Remote Similarity	NPC471386
0.6798	Remote Similarity	NPC154339
0.6794	Remote Similarity	NPC471944
0.6791	Remote Similarity	NPC472260
0.6787	Remote Similarity	NPC122436
0.6783	Remote Similarity	NPC72905
0.6779	Remote Similarity	NPC201266
0.6779	Remote Similarity	NPC220797
0.6779	Remote Similarity	NPC474318
0.6779	Remote Similarity	NPC268744
0.6779	Remote Similarity	NPC153123
0.6779	Remote Similarity	NPC475914
0.6777	Remote Similarity	NPC314648
0.6777	Remote Similarity	NPC132539
0.6771	Remote Similarity	NPC274981
0.6769	Remote Similarity	NPC262338
0.6769	Remote Similarity	NPC37152
0.6766	Remote Similarity	NPC282103
0.6762	Remote Similarity	NPC260900
0.6753	Remote Similarity	NPC142385
0.675	Remote Similarity	NPC159125
0.6749	Remote Similarity	NPC473666
0.6748	Remote Similarity	NPC202812
0.6746	Remote Similarity	NPC269203
0.6746	Remote Similarity	NPC13456

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 NPC128244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	468
0.1-0.2	733
0.2-0.3	1192
0.3-0.4	2565
0.4-0.5	2002
0.5-0.6	1602
0.6-0.7	536
0.7-0.8	52
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
0.7871	Intermediate Similarity	NPD6954	Phase 2
0.7857	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD2479	Phase 3
0.7807	Intermediate Similarity	NPD2481	Approved
0.7684	Intermediate Similarity	NPD7564	Discontinued
0.767	Intermediate Similarity	NPD1270	Approved
0.7609	Intermediate Similarity	NPD6446	Discontinued
0.7579	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD3905	Phase 3
0.7525	Intermediate Similarity	NPD7209	Approved
0.7525	Intermediate Similarity	NPD7208	Approved
0.7525	Intermediate Similarity	NPD7207	Approved
0.7512	Intermediate Similarity	NPD4051	Discontinued
0.7486	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD5446	Phase 2
0.7426	Intermediate Similarity	NPD2881	Approved
0.7426	Intermediate Similarity	NPD2879	Approved
0.7387	Intermediate Similarity	NPD4848	Phase 1
0.7387	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4988	Discontinued
0.738	Intermediate Similarity	NPD1343	Approved
0.7379	Intermediate Similarity	NPD2295	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2411	Approved
0.7344	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6152	Phase 1
0.7282	Intermediate Similarity	NPD1506	Discontinued
0.7273	Intermediate Similarity	NPD1658	Discontinued
0.7273	Intermediate Similarity	NPD2336	Approved
0.7245	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6787	Phase 2
0.7233	Intermediate Similarity	NPD2008	Discontinued
0.7231	Intermediate Similarity	NPD6178	Phase 3
0.7231	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7404	Approved
0.7184	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD5400	Approved
0.7165	Intermediate Similarity	NPD5473	Discontinued
0.7163	Intermediate Similarity	NPD7665	Phase 2
0.7163	Intermediate Similarity	NPD7666	Phase 3
0.7163	Intermediate Similarity	NPD6459	Phase 2
0.715	Intermediate Similarity	NPD4922	Phase 2
0.715	Intermediate Similarity	NPD2753	Discontinued
0.7136	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD2307	Discontinued
0.7129	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3839	Phase 2
0.7115	Intermediate Similarity	NPD3840	Phase 2
0.7111	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6987	Phase 1
0.7098	Intermediate Similarity	NPD3238	Discontinued
0.7089	Intermediate Similarity	NPD3389	Approved
0.7089	Intermediate Similarity	NPD3393	Approved
0.7089	Intermediate Similarity	NPD3394	Approved
0.7089	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5418	Discontinued
0.7059	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4883	Approved
0.7039	Intermediate Similarity	NPD5017	Discontinued
0.7035	Intermediate Similarity	NPD7394	Phase 2
0.7014	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD715	Phase 3
0.701	Intermediate Similarity	NPD2751	Phase 1
0.701	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5888	Phase 2
0.6995	Remote Similarity	NPD7216	Approved
0.6995	Remote Similarity	NPD7217	Approved
0.6991	Remote Similarity	NPD5198	Approved
0.6991	Remote Similarity	NPD5199	Approved
0.6985	Remote Similarity	NPD5809	Phase 3
0.6977	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7027	Phase 3
0.6955	Remote Similarity	NPD8289	Discontinued
0.6948	Remote Similarity	NPD7454	Approved
0.6948	Remote Similarity	NPD7455	Approved
0.6947	Remote Similarity	NPD3583	Phase 2
0.6946	Remote Similarity	NPD460	Discontinued
0.6944	Remote Similarity	NPD6470	Phase 3
0.6942	Remote Similarity	NPD5854	Approved
0.6941	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD1952	Discontinued
0.6923	Remote Similarity	NPD7187	Phase 2
0.6919	Remote Similarity	NPD2443	Approved
0.6919	Remote Similarity	NPD2442	Approved
0.6912	Remote Similarity	NPD7406	Phase 2
0.6907	Remote Similarity	NPD4524	Discontinued
0.6905	Remote Similarity	NPD7568	Phase 1
0.6902	Remote Similarity	NPD4547	Phase 3
0.6901	Remote Similarity	NPD5475	Discontinued
0.69	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3430	Approved
0.6897	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3431	Approved
0.6897	Remote Similarity	NPD5505	Discontinued
0.6895	Remote Similarity	NPD6771	Discontinued
0.6887	Remote Similarity	NPD1600	Suspended
0.6882	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2770	Discontinued
0.686	Remote Similarity	NPD6999	Discontinued
0.686	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7469	Discontinued
0.6847	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6474	Phase 2
0.6837	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5016	Approved
0.6829	Remote Similarity	NPD7619	Phase 3
0.6829	Remote Similarity	NPD7618	Phase 3
0.6825	Remote Similarity	NPD5489	Phase 1
0.6825	Remote Similarity	NPD5491	Phase 3
0.6822	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4429	Discontinued
0.6789	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2405	Phase 3
0.6777	Remote Similarity	NPD8114	Approved
0.6777	Remote Similarity	NPD8115	Approved
0.6776	Remote Similarity	NPD2006	Phase 2
0.6774	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2430	Phase 2
0.6768	Remote Similarity	NPD3076	Approved
0.6768	Remote Similarity	NPD3077	Approved
0.6768	Remote Similarity	NPD3079	Approved
0.6768	Remote Similarity	NPD3078	Approved
0.6761	Remote Similarity	NPD7191	Phase 2
0.676	Remote Similarity	NPD272	Approved
0.6759	Remote Similarity	NPD3794	Approved
0.6759	Remote Similarity	NPD3795	Approved
0.6755	Remote Similarity	NPD2837	Discontinued
0.6753	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3319	Phase 1
0.675	Remote Similarity	NPD3318	Approved
0.675	Remote Similarity	NPD3320	Approved
0.6749	Remote Similarity	NPD7175	Phase 1
0.6748	Remote Similarity	NPD5855	Phase 3
0.6748	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5853	Phase 3
0.6743	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2720	Phase 1
0.6734	Remote Similarity	NPD3927	Phase 2
0.6733	Remote Similarity	NPD7026	Phase 2
0.673	Remote Similarity	NPD4912	Phase 3
0.6729	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD2408	Discontinued
0.672	Remote Similarity	NPD1661	Suspended
0.672	Remote Similarity	NPD6285	Phase 2
0.672	Remote Similarity	NPD975	Approved
0.672	Remote Similarity	NPD976	Approved
0.672	Remote Similarity	NPD977	Approved
0.6714	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD1630	Approved
0.6699	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6164	Phase 2
0.6696	Remote Similarity	NPD6165	Phase 2
0.6683	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6664	Approved
0.6667	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6271	Approved
0.6667	Remote Similarity	NPD4863	Approved
0.6652	Remote Similarity	NPD6210	Phase 3
0.6651	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4940	Approved
0.665	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4326	Phase 2
0.6638	Remote Similarity	NPD6986	Phase 1
0.6637	Remote Similarity	NPD3222	Phase 2
0.6636	Remote Similarity	NPD4913	Phase 3
0.662	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6507	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD3859	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD3942	Approved
0.6611	Remote Similarity	NPD3944	Approved
0.6611	Remote Similarity	NPD3385	Approved
0.6605	Remote Similarity	NPD5421	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2509	Approved
0.6605	Remote Similarity	NPD2510	Approved
0.6602	Remote Similarity	NPD7434	Approved
0.6601	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5555	Phase 1
0.66	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD1631	Approved
0.6597	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6479	Discontinued
0.6587	Remote Similarity	NPD4602	Approved
0.6587	Remote Similarity	NPD7944	Discontinued
0.6583	Remote Similarity	NPD3348	Phase 2
0.6579	Remote Similarity	NPD180	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