NPASS Compound

Structure

NPC472539 OpenBabel07101718312D 30 35 0 0 1 0 0 0 0 0999 V2000 1.7024 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4966 1.7508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9187 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4966 2.7508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3255 1.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6306 1.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9242 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6306 3.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7377 0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4670 1.7277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0325 2.7508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7645 1.7508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7645 2.7508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1665 1.2508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8985 1.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2297 0.4066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8985 3.2508 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0325 1.7508 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 -1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8985 0.2508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1606 0.0413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6224 2.4775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 22 1 0 0 0 0 11 23 2 0 0 0 0 11 24 1 0 0 0 0 12 1 1 1 0 0 0 12 18 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 17 10 1 1 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 18 27 2 0 0 0 0 19 24 1 0 0 0 0 19 28 2 0 0 0 0 20 25 1 0 0 0 0 20 29 2 0 0 0 0 21 22 1 6 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 22 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.13
Volume:	390.513
LogP:	1.104
LogD:	1.439
LogS:	-4.387
# Rotatable Bonds:	1
TPSA:	95.74
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.658
Synthetic Accessibility Score:	4.019
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.287
MDCK Permeability:	2.9749602617812343e-05
Pgp-inhibitor:	0.795
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.118
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	67.0201644897461%
Volume Distribution (VD):	0.862
Pgp-substrate:	40.98546600341797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.213
CYP2C19-substrate:	0.674
CYP2C9-inhibitor:	0.369
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.405
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	4.586
Half-life (T1/2):	0.308

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.209
Maximum Recommended Daily Dose:	0.076
Skin Sensitization:	0.848
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.333

Download Data

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

Natural Product: NPC472539

Natural Product ID:	NPC472539
*Common Name:**	GEURDGODABUDHB-ZFSUOAISSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GEURDGODABUDHB-ZFSUOAISSA-N
Standard InCHI:	InChI=1S/C22H18N4O4/c1-12-18(27)26-16-9-5-3-7-14(16)22(30)10-17(20(29)25(12)21(22)26)24-11-23-15-8-4-2-6-13(15)19(24)28/h2-9,11-12,17,21,30H,10H2,1H3/t12-,17+,21+,22+/m0/s1
SMILES:	C[C@H]1C(=O)N2[C@H]3N1C(=O)[C@@H](C[C@]3(c1c2cccc1)O)n1cnc2c(c1=O)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577057
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001374] Pyridoindolones

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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
IC50	3
MIC	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	21910.0	nM	PMID[525790]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	50390.0	nM	PMID[525790]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[525790]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	100.0	ug.mL-1	PMID[525790]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[525790]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[525790]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	100.0	ug.mL-1	PMID[525790]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[525790]
NPT2	Others	Unspecified		IC50	=	78070.0	nM	PMID[525790]

☑ 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 NPC472539 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	458
0.1-0.2	2759
0.2-0.3	13585
0.3-0.4	17419
0.4-0.5	3746
0.5-0.6	2999
0.6-0.7	1550
0.7-0.8	116
0.8-0.85	36
0.85-0.9	11
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472540
1.0	High Similarity	NPC470787
0.9943	High Similarity	NPC472541
0.9943	High Similarity	NPC472542
0.8978	High Similarity	NPC295548
0.8883	High Similarity	NPC225400
0.8836	High Similarity	NPC471155
0.8836	High Similarity	NPC472538
0.8836	High Similarity	NPC470786
0.8789	High Similarity	NPC270241
0.8594	High Similarity	NPC285192
0.8588	High Similarity	NPC470548
0.83	Intermediate Similarity	NPC248601
0.825	Intermediate Similarity	NPC244425
0.825	Intermediate Similarity	NPC15384
0.8168	Intermediate Similarity	NPC471199
0.8159	Intermediate Similarity	NPC471197
0.8138	Intermediate Similarity	NPC471196
0.8138	Intermediate Similarity	NPC471195
0.8132	Intermediate Similarity	NPC475607
0.8119	Intermediate Similarity	NPC471198
0.8087	Intermediate Similarity	NPC474081
0.8083	Intermediate Similarity	NPC106118
0.8077	Intermediate Similarity	NPC475594
0.8043	Intermediate Similarity	NPC474041
0.8043	Intermediate Similarity	NPC475761
0.7921	Intermediate Similarity	NPC471122
0.7845	Intermediate Similarity	NPC471124
0.7842	Intermediate Similarity	NPC473815
0.7772	Intermediate Similarity	NPC355
0.7747	Intermediate Similarity	NPC471130
0.7637	Intermediate Similarity	NPC88970
0.7619	Intermediate Similarity	NPC475685
0.76	Intermediate Similarity	NPC471436
0.7441	Intermediate Similarity	NPC272174
0.7406	Intermediate Similarity	NPC474896
0.7405	Intermediate Similarity	NPC138293
0.7405	Intermediate Similarity	NPC189116
0.7405	Intermediate Similarity	NPC113056
0.7371	Intermediate Similarity	NPC31097
0.736	Intermediate Similarity	NPC92803
0.7337	Intermediate Similarity	NPC154478
0.7263	Intermediate Similarity	NPC177261
0.7259	Intermediate Similarity	NPC18890
0.7245	Intermediate Similarity	NPC150308
0.7228	Intermediate Similarity	NPC84317
0.7166	Intermediate Similarity	NPC476231
0.7164	Intermediate Similarity	NPC198401
0.7158	Intermediate Similarity	NPC472118
0.715	Intermediate Similarity	NPC14849
0.7143	Intermediate Similarity	NPC472115
0.7143	Intermediate Similarity	NPC472114
0.712	Intermediate Similarity	NPC295021
0.7119	Intermediate Similarity	NPC207554
0.7112	Intermediate Similarity	NPC68650
0.7107	Intermediate Similarity	NPC307396
0.7104	Intermediate Similarity	NPC66936
0.7098	Intermediate Similarity	NPC471743
0.7075	Intermediate Similarity	NPC471663
0.7074	Intermediate Similarity	NPC472117
0.7065	Intermediate Similarity	NPC117032
0.7053	Intermediate Similarity	NPC477179
0.7047	Intermediate Similarity	NPC328611
0.7026	Intermediate Similarity	NPC131450
0.7026	Intermediate Similarity	NPC475094
0.7026	Intermediate Similarity	NPC182057
0.7026	Intermediate Similarity	NPC147298
0.7021	Intermediate Similarity	NPC27904
0.7019	Intermediate Similarity	NPC477181
0.7019	Intermediate Similarity	NPC477180
0.7019	Intermediate Similarity	NPC254850
0.7019	Intermediate Similarity	NPC477178
0.7015	Intermediate Similarity	NPC276430
0.6995	Remote Similarity	NPC300596
0.6995	Remote Similarity	NPC237649
0.6986	Remote Similarity	NPC477173
0.6986	Remote Similarity	NPC477174
0.6986	Remote Similarity	NPC470490
0.6978	Remote Similarity	NPC324445
0.6968	Remote Similarity	NPC276085
0.6957	Remote Similarity	NPC471944
0.6952	Remote Similarity	NPC470488
0.694	Remote Similarity	NPC254798
0.6934	Remote Similarity	NPC475359
0.6934	Remote Similarity	NPC191817
0.6919	Remote Similarity	NPC471945
0.6919	Remote Similarity	NPC470491
0.6919	Remote Similarity	NPC471950
0.6919	Remote Similarity	NPC475259
0.6919	Remote Similarity	NPC470317
0.6915	Remote Similarity	NPC222029
0.6893	Remote Similarity	NPC300299
0.6887	Remote Similarity	NPC471946
0.6887	Remote Similarity	NPC471951
0.6875	Remote Similarity	NPC182131
0.6872	Remote Similarity	NPC248862
0.6869	Remote Similarity	NPC471194
0.6869	Remote Similarity	NPC471193
0.6869	Remote Similarity	NPC6865
0.6869	Remote Similarity	NPC153980
0.6828	Remote Similarity	NPC154602
0.6825	Remote Similarity	NPC471191
0.6822	Remote Similarity	NPC72956
0.6821	Remote Similarity	NPC242269
0.6818	Remote Similarity	NPC220851
0.6818	Remote Similarity	NPC39822
0.6798	Remote Similarity	NPC128582
0.6798	Remote Similarity	NPC313293
0.6796	Remote Similarity	NPC43477
0.6792	Remote Similarity	NPC243850
0.6778	Remote Similarity	NPC83214
0.6778	Remote Similarity	NPC469560
0.6774	Remote Similarity	NPC144691
0.6771	Remote Similarity	NPC313757
0.6769	Remote Similarity	NPC318183
0.676	Remote Similarity	NPC471123
0.6758	Remote Similarity	NPC219397
0.6757	Remote Similarity	NPC122886
0.6751	Remote Similarity	NPC129624
0.6737	Remote Similarity	NPC104345
0.6736	Remote Similarity	NPC472106
0.6735	Remote Similarity	NPC285622
0.6733	Remote Similarity	NPC473615
0.6723	Remote Similarity	NPC14812
0.6723	Remote Similarity	NPC207428
0.6719	Remote Similarity	NPC472120
0.6719	Remote Similarity	NPC472101
0.6703	Remote Similarity	NPC22082
0.6703	Remote Similarity	NPC471164
0.6703	Remote Similarity	NPC186284
0.6702	Remote Similarity	NPC36495
0.6701	Remote Similarity	NPC279527
0.6701	Remote Similarity	NPC214960
0.67	Remote Similarity	NPC229484
0.6698	Remote Similarity	NPC470489
0.6697	Remote Similarity	NPC471192
0.6683	Remote Similarity	NPC259626
0.6683	Remote Similarity	NPC322621
0.6667	Remote Similarity	NPC472102
0.6667	Remote Similarity	NPC471132
0.6667	Remote Similarity	NPC292675
0.6667	Remote Similarity	NPC309531
0.665	Remote Similarity	NPC135601
0.665	Remote Similarity	NPC141612
0.665	Remote Similarity	NPC17273
0.665	Remote Similarity	NPC286994
0.6649	Remote Similarity	NPC113946
0.6648	Remote Similarity	NPC315051
0.6636	Remote Similarity	NPC478075
0.6634	Remote Similarity	NPC21429
0.6634	Remote Similarity	NPC2933
0.6634	Remote Similarity	NPC471742
0.6632	Remote Similarity	NPC191863
0.6632	Remote Similarity	NPC289776
0.6632	Remote Similarity	NPC133470
0.663	Remote Similarity	NPC122553
0.6622	Remote Similarity	NPC257851
0.6621	Remote Similarity	NPC147983
0.6621	Remote Similarity	NPC177996
0.6614	Remote Similarity	NPC285381
0.6612	Remote Similarity	NPC471574
0.6598	Remote Similarity	NPC204867
0.6584	Remote Similarity	NPC256288
0.6582	Remote Similarity	NPC33507
0.6571	Remote Similarity	NPC474916
0.657	Remote Similarity	NPC204970
0.6558	Remote Similarity	NPC16249
0.6557	Remote Similarity	NPC130251
0.6553	Remote Similarity	NPC174629
0.6549	Remote Similarity	NPC157931
0.6545	Remote Similarity	NPC322064
0.6543	Remote Similarity	NPC242000
0.6542	Remote Similarity	NPC329833
0.6541	Remote Similarity	NPC308197
0.6535	Remote Similarity	NPC475969
0.6535	Remote Similarity	NPC475859
0.6531	Remote Similarity	NPC278887
0.6528	Remote Similarity	NPC71238
0.652	Remote Similarity	NPC471762
0.6505	Remote Similarity	NPC136002
0.6497	Remote Similarity	NPC63047
0.6497	Remote Similarity	NPC475248
0.6495	Remote Similarity	NPC225319
0.6493	Remote Similarity	NPC100863
0.6491	Remote Similarity	NPC470730
0.6491	Remote Similarity	NPC477175
0.6489	Remote Similarity	NPC476817
0.6477	Remote Similarity	NPC211525
0.6477	Remote Similarity	NPC153694
0.6474	Remote Similarity	NPC243756
0.6473	Remote Similarity	NPC22689
0.6473	Remote Similarity	NPC5630
0.6473	Remote Similarity	NPC105055
0.6473	Remote Similarity	NPC473569
0.6471	Remote Similarity	NPC203635
0.6471	Remote Similarity	NPC97584
0.6467	Remote Similarity	NPC472243
0.6464	Remote Similarity	NPC162417
0.6464	Remote Similarity	NPC316104
0.6464	Remote Similarity	NPC253476

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 NPC472539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	567
0.2-0.3	865
0.3-0.4	1672
0.4-0.5	2347
0.5-0.6	2063
0.6-0.7	1185
0.7-0.8	204
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7968	Intermediate Similarity	NPD5923	Phase 1
0.772	Intermediate Similarity	NPD5042	Phase 1
0.7644	Intermediate Similarity	NPD6557	Phase 2
0.7565	Intermediate Similarity	NPD4515	Suspended
0.75	Intermediate Similarity	NPD6017	Discontinued
0.74	Intermediate Similarity	NPD5856	Discontinued
0.7374	Intermediate Similarity	NPD4942	Approved
0.7374	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6855	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3780	Phase 2
0.7306	Intermediate Similarity	NPD3990	Phase 3
0.7259	Intermediate Similarity	NPD7855	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3989	Phase 3
0.7233	Intermediate Similarity	NPD6260	Discontinued
0.715	Intermediate Similarity	NPD4092	Approved
0.7121	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4091	Approved
0.7095	Intermediate Similarity	NPD4430	Phase 2
0.7086	Intermediate Similarity	NPD2791	Discontinued
0.7065	Intermediate Similarity	NPD3248	Phase 1
0.7065	Intermediate Similarity	NPD7569	Approved
0.7065	Intermediate Similarity	NPD7570	Approved
0.7047	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3522	Approved
0.7026	Intermediate Similarity	NPD3999	Approved
0.7026	Intermediate Similarity	NPD3997	Approved
0.7026	Intermediate Similarity	NPD3998	Approved
0.7015	Intermediate Similarity	NPD8240	Discontinued
0.7005	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3993	Approved
0.6974	Remote Similarity	NPD3995	Approved
0.6974	Remote Similarity	NPD3991	Approved
0.6974	Remote Similarity	NPD3992	Approved
0.6974	Remote Similarity	NPD3994	Approved
0.6974	Remote Similarity	NPD3996	Approved
0.6943	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2813	Phase 3
0.6898	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD33	Approved
0.6878	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4393	Approved
0.6875	Remote Similarity	NPD5552	Discontinued
0.6864	Remote Similarity	NPD6753	Phase 1
0.6864	Remote Similarity	NPD6752	Phase 1
0.6862	Remote Similarity	NPD951	Approved
0.6847	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5515	Phase 2
0.684	Remote Similarity	NPD7232	Discontinued
0.6827	Remote Similarity	NPD6805	Discontinued
0.6825	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1920	Approved
0.6818	Remote Similarity	NPD1919	Approved
0.6813	Remote Similarity	NPD2820	Phase 3
0.6794	Remote Similarity	NPD7817	Phase 1
0.6791	Remote Similarity	NPD3917	Approved
0.6791	Remote Similarity	NPD7225	Discontinued
0.6791	Remote Similarity	NPD3918	Approved
0.6791	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5748	Phase 2
0.6771	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD2365	Approved
0.6757	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD7568	Phase 1
0.6744	Remote Similarity	NPD3915	Approved
0.6736	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5997	Discontinued
0.6734	Remote Similarity	NPD6878	Phase 2
0.6734	Remote Similarity	NPD6879	Phase 2
0.673	Remote Similarity	NPD7205	Discontinued
0.6721	Remote Similarity	NPD6301	Phase 2
0.672	Remote Similarity	NPD979	Approved
0.6718	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7599	Phase 2
0.67	Remote Similarity	NPD4988	Discontinued
0.6695	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1527	Phase 2
0.6684	Remote Similarity	NPD6395	Phase 2
0.6684	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6486	Approved
0.6682	Remote Similarity	NPD6487	Approved
0.6667	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8025	Phase 2
0.6667	Remote Similarity	NPD2790	Discontinued
0.6651	Remote Similarity	NPD3802	Phase 3
0.665	Remote Similarity	NPD4330	Approved
0.665	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4329	Approved
0.6649	Remote Similarity	NPD3277	Phase 3
0.6637	Remote Similarity	NPD6199	Discontinued
0.6633	Remote Similarity	NPD5840	Discontinued
0.6631	Remote Similarity	NPD4888	Discontinued
0.6622	Remote Similarity	NPD6164	Phase 2
0.6622	Remote Similarity	NPD6165	Phase 2
0.6621	Remote Similarity	NPD3353	Approved
0.662	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4946	Phase 2
0.6605	Remote Similarity	NPD7666	Phase 3
0.6605	Remote Similarity	NPD7665	Phase 2
0.6602	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6142	Phase 3
0.6593	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.658	Remote Similarity	NPD4938	Phase 2
0.658	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.658	Remote Similarity	NPD2506	Approved
0.6579	Remote Similarity	NPD5639	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5593	Approved
0.6574	Remote Similarity	NPD5594	Approved
0.6571	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3227	Phase 2
0.6562	Remote Similarity	NPD7011	Discontinued
0.6559	Remote Similarity	NPD5932	Phase 3
0.6559	Remote Similarity	NPD5931	Phase 3
0.6559	Remote Similarity	NPD5933	Phase 3
0.6553	Remote Similarity	NPD3439	Approved
0.6552	Remote Similarity	NPD8241	Phase 2
0.655	Remote Similarity	NPD3792	Approved
0.6548	Remote Similarity	NPD7795	Phase 2
0.6545	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4432	Discontinued
0.6541	Remote Similarity	NPD5024	Approved
0.6541	Remote Similarity	NPD1625	Approved
0.6535	Remote Similarity	NPD7552	Discontinued
0.6528	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3774	Approved
0.6526	Remote Similarity	NPD3775	Approved
0.6526	Remote Similarity	NPD3773	Approved
0.6524	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3625	Discontinued
0.6522	Remote Similarity	NPD1658	Discontinued
0.6522	Remote Similarity	NPD5504	Discontinued
0.6516	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5918	Discontinued
0.6504	Remote Similarity	NPD7186	Phase 3
0.6502	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2950	Approved
0.65	Remote Similarity	NPD2949	Approved
0.6495	Remote Similarity	NPD7600	Phase 2
0.6493	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7786	Discontinued
0.6488	Remote Similarity	NPD3315	Phase 3
0.6486	Remote Similarity	NPD6566	Discontinued
0.6485	Remote Similarity	NPD5445	Approved
0.6482	Remote Similarity	NPD3377	Discontinued
0.6481	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7560	Approved
0.6477	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7617	Discontinued
0.6471	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8149	Discontinued
0.6468	Remote Similarity	NPD5860	Discontinued
0.6468	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD8114	Approved
0.6465	Remote Similarity	NPD8115	Approved
0.6462	Remote Similarity	NPD6999	Discontinued
0.6462	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7072	Phase 2
0.6457	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6484	Approved
0.6456	Remote Similarity	NPD6483	Approved
0.6452	Remote Similarity	NPD2442	Approved
0.6452	Remote Similarity	NPD2443	Approved
0.6449	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7767	Approved
0.6445	Remote Similarity	NPD7572	Phase 2
0.6445	Remote Similarity	NPD5591	Approved
0.6444	Remote Similarity	NPD8311	Discontinued
0.6443	Remote Similarity	NPD2427	Approved
0.6441	Remote Similarity	NPD3962	Phase 2
0.6441	Remote Similarity	NPD3959	Phase 2
0.6439	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD3782	Discontinued
0.6436	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1524	Phase 1
0.6435	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD8289	Discontinued
0.6429	Remote Similarity	NPD3790	Phase 2
0.6426	Remote Similarity	NPD5821	Approved
0.6425	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4334	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