NPASS Compound

Structure

NPC272458 OpenBabel07101719142D 23 27 0 0 0 0 0 0 0 0999 V2000 -3.1922 3.1410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1948 -0.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5745 -0.7315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 2.9781 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0496 0.5943 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 -2.2841 0.8686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2598 1.6814 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 -1.6638 0.3429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1474 2.1420 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8090 -0.4572 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 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 -3.8124 1.2409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 9 2 0 0 0 0 5 11 2 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 21 2 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 13 2 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 23 2 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.12
Volume:	306.151
LogP:	4.471
LogD:	3.13
LogS:	-5.391
# Rotatable Bonds:	0
TPSA:	79.96
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.256
Synthetic Accessibility Score:	3.327
Fsp3:	0.056
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.291
MDCK Permeability:	5.163407422514865e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.849
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	91.6589126586914%
Volume Distribution (VD):	0.874
Pgp-substrate:	8.252330780029297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.991
CYP1A2-substrate:	0.893
CYP2C19-inhibitor:	0.871
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.841
CYP2D6-inhibitor:	0.816
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.233
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	4.436
Half-life (T1/2):	0.561

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.895
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.739
Rat Oral Acute Toxicity:	0.984
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.951
Carcinogencity:	0.126
Eye Corrosion:	0.017
Eye Irritation:	0.941
Respiratory Toxicity:	0.992

Download Data

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

Natural Product: NPC272458

Natural Product ID:	NPC272458
*Common Name:**	Plakinidine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QENMGCRDNVDPEH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14N4O/c1-19-15-14-12(23)6-7-20-17(14)18-13-10(8-21-16(13)15)9-4-2-3-5-11(9)22-18/h2-5,8,19-20H,6-7H2,1H3
SMILES:	CNc1c2C(=O)CCNc2c2c3c(C=Nc13)c1ccccc1n2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL219248
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO6438	Plakortis quasiamphiaster	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253856]
NPO6438	Plakortis quasiamphiaster	Species	Plakinidae	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	56
Others	3

Activity Type	# Activity
Cell Line	56
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	7345.14	nM	PMID[546430]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	4216.97	nM	PMID[546430]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	2074.91	nM	PMID[546430]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	7128.53	nM	PMID[546430]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	3564.51	nM	PMID[546430]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	4508.17	nM	PMID[546430]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[546430]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	6546.36	nM	PMID[546430]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	3899.42	nM	PMID[546430]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	4645.15	nM	PMID[546430]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	2432.2	nM	PMID[546430]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	2673.01	nM	PMID[546430]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	8570.38	nM	PMID[546430]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	1318.26	nM	PMID[546430]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	2831.39	nM	PMID[546430]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	8590.14	nM	PMID[546430]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	5874.89	nM	PMID[546430]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	2376.84	nM	PMID[546430]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	5834.45	nM	PMID[546430]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[546430]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	3863.67	nM	PMID[546430]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	8511.38	nM	PMID[546430]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	2443.43	nM	PMID[546430]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	4786.3	nM	PMID[546430]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	3273.41	nM	PMID[546430]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[546430]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	4064.43	nM	PMID[546430]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	2570.4	nM	PMID[546430]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	7834.3	nM	PMID[546430]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	7744.62	nM	PMID[546430]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[546430]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	5081.59	nM	PMID[546430]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	3515.6	nM	PMID[546430]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	2870.78	nM	PMID[546430]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	1774.19	nM	PMID[546430]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	6397.35	nM	PMID[546430]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[546430]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	3326.6	nM	PMID[546430]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	3459.39	nM	PMID[546430]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	2660.73	nM	PMID[546430]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	8035.26	nM	PMID[546430]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	3784.43	nM	PMID[546430]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	3155.0	nM	PMID[546430]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	4688.13	nM	PMID[546430]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	4497.8	nM	PMID[546430]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	5794.29	nM	PMID[546430]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	4415.7	nM	PMID[546430]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	2409.91	nM	PMID[546430]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[546430]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[546430]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	1901.08	nM	PMID[546430]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	2233.57	nM	PMID[546430]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	7430.19	nM	PMID[546430]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	5407.54	nM	PMID[546430]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[546430]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	2824.88	nM	PMID[546430]
NPT27	Others	Unspecified		Activity	=	20.0	ug ml-1	PMID[546429]
NPT27	Others	Unspecified		Activity	=	1.5	ug ml-1	PMID[546429]
NPT27	Others	Unspecified		Activity	=	150.0	ng/ml	PMID[546429]

☑ 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 NPC272458 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	609
0.1-0.2	6514
0.2-0.3	15679
0.3-0.4	13956
0.4-0.5	2267
0.5-0.6	2336
0.6-0.7	1193
0.7-0.8	140
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.85	High Similarity	NPC467063
0.8245	Intermediate Similarity	NPC128244
0.8182	Intermediate Similarity	NPC216550
0.8105	Intermediate Similarity	NPC167710
0.7956	Intermediate Similarity	NPC252572
0.7892	Intermediate Similarity	NPC191415
0.7853	Intermediate Similarity	NPC326422
0.7826	Intermediate Similarity	NPC237188
0.7819	Intermediate Similarity	NPC135601
0.7819	Intermediate Similarity	NPC17273
0.7819	Intermediate Similarity	NPC141612
0.7789	Intermediate Similarity	NPC324091
0.7784	Intermediate Similarity	NPC34837
0.7737	Intermediate Similarity	NPC103119
0.773	Intermediate Similarity	NPC157583
0.7672	Intermediate Similarity	NPC133003
0.7634	Intermediate Similarity	NPC284775
0.7624	Intermediate Similarity	NPC271797
0.7624	Intermediate Similarity	NPC21174
0.7619	Intermediate Similarity	NPC21429
0.7588	Intermediate Similarity	NPC317701
0.7581	Intermediate Similarity	NPC151635
0.7566	Intermediate Similarity	NPC102755
0.7527	Intermediate Similarity	NPC297034
0.7435	Intermediate Similarity	NPC477003
0.7433	Intermediate Similarity	NPC293216
0.7411	Intermediate Similarity	NPC79356
0.7411	Intermediate Similarity	NPC102592
0.7398	Intermediate Similarity	NPC304203
0.7387	Intermediate Similarity	NPC237414
0.7382	Intermediate Similarity	NPC117027
0.7382	Intermediate Similarity	NPC470205
0.7371	Intermediate Similarity	NPC255909
0.7337	Intermediate Similarity	NPC265100
0.7321	Intermediate Similarity	NPC469727
0.7297	Intermediate Similarity	NPC42372
0.7296	Intermediate Similarity	NPC476460
0.7286	Intermediate Similarity	NPC134657
0.7282	Intermediate Similarity	NPC473666
0.7277	Intermediate Similarity	NPC73994
0.7277	Intermediate Similarity	NPC88110
0.7258	Intermediate Similarity	NPC56233
0.7255	Intermediate Similarity	NPC472064
0.724	Intermediate Similarity	NPC470677
0.7219	Intermediate Similarity	NPC70949
0.7204	Intermediate Similarity	NPC115232
0.7202	Intermediate Similarity	NPC243058
0.7189	Intermediate Similarity	NPC194881
0.7189	Intermediate Similarity	NPC214106
0.7184	Intermediate Similarity	NPC116555
0.7181	Intermediate Similarity	NPC471943
0.7171	Intermediate Similarity	NPC472065
0.7165	Intermediate Similarity	NPC203635
0.7156	Intermediate Similarity	NPC267811
0.7151	Intermediate Similarity	NPC478184
0.715	Intermediate Similarity	NPC472116
0.7129	Intermediate Similarity	NPC473218
0.7129	Intermediate Similarity	NPC470702
0.7128	Intermediate Similarity	NPC308931
0.7128	Intermediate Similarity	NPC99939
0.7105	Intermediate Similarity	NPC161861
0.7104	Intermediate Similarity	NPC476219
0.7097	Intermediate Similarity	NPC242116
0.7095	Intermediate Similarity	NPC470703
0.7092	Intermediate Similarity	NPC90415
0.7088	Intermediate Similarity	NPC70406
0.7083	Intermediate Similarity	NPC219848
0.7068	Intermediate Similarity	NPC469529
0.7062	Intermediate Similarity	NPC115611
0.7059	Intermediate Similarity	NPC317105
0.7053	Intermediate Similarity	NPC175916
0.7049	Intermediate Similarity	NPC325903
0.7049	Intermediate Similarity	NPC251391
0.7047	Intermediate Similarity	NPC256268
0.7044	Intermediate Similarity	NPC81535
0.7044	Intermediate Similarity	NPC284338
0.7031	Intermediate Similarity	NPC471743
0.7024	Intermediate Similarity	NPC472062
0.7024	Intermediate Similarity	NPC472063
0.7024	Intermediate Similarity	NPC472069
0.7019	Intermediate Similarity	NPC66699
0.7	Intermediate Similarity	NPC467188
0.7	Intermediate Similarity	NPC47190
0.7	Intermediate Similarity	NPC470440
0.6995	Remote Similarity	NPC83774
0.6995	Remote Similarity	NPC474916
0.6989	Remote Similarity	NPC474880
0.6989	Remote Similarity	NPC474492
0.6989	Remote Similarity	NPC221786
0.6989	Remote Similarity	NPC475990
0.6985	Remote Similarity	NPC472112
0.6984	Remote Similarity	NPC114637
0.6978	Remote Similarity	NPC321911
0.6968	Remote Similarity	NPC478182
0.6967	Remote Similarity	NPC6865
0.6967	Remote Similarity	NPC153980
0.6966	Remote Similarity	NPC284635
0.6963	Remote Similarity	NPC201634
0.6961	Remote Similarity	NPC477004
0.6952	Remote Similarity	NPC470680
0.6952	Remote Similarity	NPC100104
0.6948	Remote Similarity	NPC322064
0.6946	Remote Similarity	NPC106824
0.6942	Remote Similarity	NPC328596
0.6942	Remote Similarity	NPC328318
0.6935	Remote Similarity	NPC76982
0.6932	Remote Similarity	NPC325252
0.6923	Remote Similarity	NPC469811
0.6923	Remote Similarity	NPC105811
0.6923	Remote Similarity	NPC61011
0.6923	Remote Similarity	NPC201380
0.6923	Remote Similarity	NPC179787
0.6919	Remote Similarity	NPC124636
0.6919	Remote Similarity	NPC72956
0.6916	Remote Similarity	NPC27041
0.6915	Remote Similarity	NPC472113
0.691	Remote Similarity	NPC88097
0.69	Remote Similarity	NPC154339
0.6898	Remote Similarity	NPC293487
0.6898	Remote Similarity	NPC80681
0.6889	Remote Similarity	NPC136002
0.6887	Remote Similarity	NPC471194
0.6887	Remote Similarity	NPC471193
0.6887	Remote Similarity	NPC193370
0.6885	Remote Similarity	NPC123906
0.6881	Remote Similarity	NPC267343
0.6881	Remote Similarity	NPC229893
0.6875	Remote Similarity	NPC88115
0.6875	Remote Similarity	NPC327592
0.6875	Remote Similarity	NPC198988
0.6869	Remote Similarity	NPC476341
0.6868	Remote Similarity	NPC63545
0.6868	Remote Similarity	NPC478186
0.6865	Remote Similarity	NPC281094
0.6863	Remote Similarity	NPC227582
0.6862	Remote Similarity	NPC44773
0.6862	Remote Similarity	NPC215584
0.6862	Remote Similarity	NPC229173
0.686	Remote Similarity	NPC106757
0.6857	Remote Similarity	NPC266249
0.6856	Remote Similarity	NPC280852
0.6848	Remote Similarity	NPC473878
0.6848	Remote Similarity	NPC313889
0.6847	Remote Similarity	NPC157828
0.6847	Remote Similarity	NPC195239
0.6845	Remote Similarity	NPC121327
0.6842	Remote Similarity	NPC317373
0.6842	Remote Similarity	NPC471191
0.6837	Remote Similarity	NPC173344
0.6834	Remote Similarity	NPC62749
0.6828	Remote Similarity	NPC476297
0.6825	Remote Similarity	NPC472070
0.682	Remote Similarity	NPC323969
0.6818	Remote Similarity	NPC258480
0.6818	Remote Similarity	NPC46895
0.6818	Remote Similarity	NPC472294
0.6818	Remote Similarity	NPC110158
0.6814	Remote Similarity	NPC11445
0.6814	Remote Similarity	NPC245916
0.6811	Remote Similarity	NPC470679
0.6811	Remote Similarity	NPC117032
0.6811	Remote Similarity	NPC217021
0.681	Remote Similarity	NPC477065
0.6809	Remote Similarity	NPC56765
0.6806	Remote Similarity	NPC478183
0.6806	Remote Similarity	NPC149014
0.6804	Remote Similarity	NPC471579
0.6798	Remote Similarity	NPC269886
0.6798	Remote Similarity	NPC472295
0.6798	Remote Similarity	NPC81802
0.6798	Remote Similarity	NPC472210
0.6798	Remote Similarity	NPC247735
0.6796	Remote Similarity	NPC74413
0.6794	Remote Similarity	NPC314648
0.6792	Remote Similarity	NPC123839
0.6792	Remote Similarity	NPC147810
0.6791	Remote Similarity	NPC471192
0.6782	Remote Similarity	NPC138370
0.6779	Remote Similarity	NPC143977
0.6776	Remote Similarity	NPC31700
0.6774	Remote Similarity	NPC200743
0.6772	Remote Similarity	NPC122141
0.6766	Remote Similarity	NPC63199
0.6766	Remote Similarity	NPC111602
0.6766	Remote Similarity	NPC102338
0.6766	Remote Similarity	NPC196251
0.6763	Remote Similarity	NPC252338
0.6762	Remote Similarity	NPC313345
0.6762	Remote Similarity	NPC313796
0.6762	Remote Similarity	NPC315638
0.6762	Remote Similarity	NPC314855
0.6757	Remote Similarity	NPC40070
0.6757	Remote Similarity	NPC33421
0.6755	Remote Similarity	NPC236711
0.6751	Remote Similarity	NPC15840
0.675	Remote Similarity	NPC66210
0.6749	Remote Similarity	NPC471386
0.6743	Remote Similarity	NPC77022
0.6741	Remote Similarity	NPC267078
0.6741	Remote Similarity	NPC935

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 NPC272458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	687
0.2-0.3	1038
0.3-0.4	2132
0.4-0.5	2191
0.5-0.6	2020
0.6-0.7	704
0.7-0.8	56
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
0.8033	Intermediate Similarity	NPD2481	Approved
0.8033	Intermediate Similarity	NPD2479	Phase 3
0.7889	Intermediate Similarity	NPD4051	Discontinued
0.785	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5473	Discontinued
0.7632	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7564	Discontinued
0.7614	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5446	Phase 2
0.75	Intermediate Similarity	NPD7027	Phase 3
0.7486	Intermediate Similarity	NPD6285	Phase 2
0.7463	Intermediate Similarity	NPD7454	Approved
0.7463	Intermediate Similarity	NPD7455	Approved
0.7449	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD3320	Approved
0.7382	Intermediate Similarity	NPD3319	Phase 1
0.7382	Intermediate Similarity	NPD3318	Approved
0.7376	Intermediate Similarity	NPD7208	Approved
0.7376	Intermediate Similarity	NPD7209	Approved
0.7376	Intermediate Similarity	NPD7207	Approved
0.7368	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7406	Phase 2
0.7344	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD3076	Approved
0.7316	Intermediate Similarity	NPD3078	Approved
0.7316	Intermediate Similarity	NPD3077	Approved
0.7316	Intermediate Similarity	NPD3079	Approved
0.7312	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4922	Phase 2
0.7258	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6178	Phase 3
0.7251	Intermediate Similarity	NPD7404	Approved
0.7249	Intermediate Similarity	NPD4883	Approved
0.7212	Intermediate Similarity	NPD2411	Approved
0.7184	Intermediate Similarity	NPD2442	Approved
0.7184	Intermediate Similarity	NPD2443	Approved
0.7175	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6152	Phase 1
0.715	Intermediate Similarity	NPD4848	Phase 1
0.7136	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6954	Phase 2
0.7128	Intermediate Similarity	NPD1343	Approved
0.7111	Intermediate Similarity	NPD1270	Approved
0.7111	Intermediate Similarity	NPD3959	Phase 2
0.7111	Intermediate Similarity	NPD3962	Phase 2
0.7098	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5491	Phase 3
0.7087	Intermediate Similarity	NPD2008	Discontinued
0.7087	Intermediate Similarity	NPD5489	Phase 1
0.7081	Intermediate Similarity	NPD5475	Discontinued
0.7065	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3583	Phase 2
0.7053	Intermediate Similarity	NPD3905	Phase 3
0.7047	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8114	Approved
0.7039	Intermediate Similarity	NPD8115	Approved
0.7029	Intermediate Similarity	NPD1256	Approved
0.7029	Intermediate Similarity	NPD1253	Approved
0.7029	Intermediate Similarity	NPD1255	Approved
0.7029	Intermediate Similarity	NPD1254	Approved
0.7016	Intermediate Similarity	NPD3868	Phase 1
0.7015	Intermediate Similarity	NPD7619	Phase 3
0.7015	Intermediate Similarity	NPD7618	Phase 3
0.7014	Intermediate Similarity	NPD5888	Phase 2
0.7011	Intermediate Similarity	NPD975	Approved
0.7011	Intermediate Similarity	NPD976	Approved
0.7011	Intermediate Similarity	NPD977	Approved
0.6986	Remote Similarity	NPD2408	Discontinued
0.6977	Remote Similarity	NPD947	Approved
0.6971	Remote Similarity	NPD1506	Discontinued
0.6961	Remote Similarity	NPD5854	Approved
0.6961	Remote Similarity	NPD1683	Approved
0.695	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2336	Approved
0.695	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6664	Approved
0.6944	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5932	Phase 3
0.6944	Remote Similarity	NPD5933	Phase 3
0.6944	Remote Similarity	NPD5931	Phase 3
0.6942	Remote Similarity	NPD7187	Phase 2
0.6942	Remote Similarity	NPD2879	Approved
0.6942	Remote Similarity	NPD2881	Approved
0.6938	Remote Similarity	NPD6459	Phase 2
0.6935	Remote Similarity	NPD7175	Phase 1
0.693	Remote Similarity	NPD5198	Approved
0.693	Remote Similarity	NPD5199	Approved
0.6919	Remote Similarity	NPD7026	Phase 2
0.6919	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4863	Approved
0.6915	Remote Similarity	NPD6771	Discontinued
0.6912	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7257	Phase 1
0.6895	Remote Similarity	NPD6446	Discontinued
0.6887	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4988	Discontinued
0.6884	Remote Similarity	NPD6470	Phase 3
0.6878	Remote Similarity	NPD3323	Discontinued
0.6875	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6448	Phase 1
0.6869	Remote Similarity	NPD3393	Approved
0.6869	Remote Similarity	NPD3389	Approved
0.6869	Remote Similarity	NPD3394	Approved
0.6864	Remote Similarity	NPD6164	Phase 2
0.6864	Remote Similarity	NPD6165	Phase 2
0.6859	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7665	Phase 2
0.6857	Remote Similarity	NPD7666	Phase 3
0.6856	Remote Similarity	NPD4075	Phase 2
0.6856	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD3348	Phase 2
0.6851	Remote Similarity	NPD5254	Discontinued
0.685	Remote Similarity	NPD5016	Approved
0.6848	Remote Similarity	NPD4462	Approved
0.6848	Remote Similarity	NPD4463	Approved
0.6845	Remote Similarity	NPD6479	Discontinued
0.6842	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4181	Approved
0.6818	Remote Similarity	NPD3385	Approved
0.6816	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD2307	Discontinued
0.6814	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7727	Phase 2
0.6812	Remote Similarity	NPD7817	Phase 1
0.6811	Remote Similarity	NPD3248	Phase 1
0.6802	Remote Similarity	NPD7867	Phase 1
0.68	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6986	Phase 1
0.68	Remote Similarity	NPD6507	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7308	Discontinued
0.6792	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7694	Discontinued
0.6786	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1658	Discontinued
0.6777	Remote Similarity	NPD2509	Approved
0.6777	Remote Similarity	NPD2510	Approved
0.6777	Remote Similarity	NPD7191	Phase 2
0.6776	Remote Similarity	NPD6787	Phase 2
0.6774	Remote Similarity	NPD2837	Discontinued
0.6768	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5855	Phase 3
0.6765	Remote Similarity	NPD5853	Phase 3
0.6762	Remote Similarity	NPD7010	Phase 3
0.6761	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD3927	Phase 2
0.675	Remote Similarity	NPD4940	Approved
0.675	Remote Similarity	NPD5809	Phase 3
0.6749	Remote Similarity	NPD4376	Phase 3
0.6749	Remote Similarity	NPD1896	Approved
0.6748	Remote Similarity	NPD1982	Phase 1
0.6746	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6342	Discontinued
0.6737	Remote Similarity	NPD5400	Approved
0.6735	Remote Similarity	NPD2753	Discontinued
0.6729	Remote Similarity	NPD7656	Approved
0.6729	Remote Similarity	NPD7657	Approved
0.6727	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3961	Discontinued
0.6716	Remote Similarity	NPD7394	Phase 2
0.6715	Remote Similarity	NPD2405	Phase 3
0.6714	Remote Similarity	NPD6987	Phase 1
0.6704	Remote Similarity	NPD6554	Approved
0.6704	Remote Similarity	NPD1262	Discovery
0.6704	Remote Similarity	NPD45	Approved
0.67	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3794	Approved
0.6698	Remote Similarity	NPD3795	Approved
0.6685	Remote Similarity	NPD7469	Discontinued
0.6684	Remote Similarity	NPD3238	Discontinued
0.6683	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7568	Phase 1
0.6682	Remote Similarity	NPD6271	Approved
0.6667	Remote Similarity	NPD3430	Approved
0.6667	Remote Similarity	NPD5293	Phase 2
0.6667	Remote Similarity	NPD3431	Approved
0.6667	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5146	Suspended
0.6667	Remote Similarity	NPD6210	Phase 3
0.6651	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4429	Discontinued
0.665	Remote Similarity	NPD1871	Approved
0.665	Remote Similarity	NPD6226	Phase 3
0.6649	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4547	Phase 3
0.6648	Remote Similarity	NPD1722	Approved
0.6636	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6999	Discontinued
0.6634	Remote Similarity	NPD3246	Discontinued

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