NPASS Compound

Structure

CID325479 OpenBabel06191716182D 28 31 0 0 1 0 0 0 0 0999 V2000 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3972 -3.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3944 -3.1472 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 -2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9577 -2.3209 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 1.7321 2.0000 0.0000 C 0 0 3 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 0.8660 -1.5000 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 0.8660 1.5000 0.0000 C 0 0 1 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6629 -1.3653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 8 1 0 0 0 0 7 11 2 0 0 0 0 8 12 2 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 28 1 0 0 0 0 13 15 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 13 1 6 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 14 1 1 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 23 2 0 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 27 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	377.17
Volume:	390.475
LogP:	4.281
LogD:	4.619
LogS:	-3.941
# Rotatable Bonds:	4
TPSA:	76.72
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	3.837
Fsp3:	0.318
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:	-4.744
MDCK Permeability:	3.168697003275156e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	98.10041046142578%
Volume Distribution (VD):	0.373
Pgp-substrate:	0.7971198558807373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.854
CYP1A2-substrate:	0.308
CYP2C19-inhibitor:	0.607
CYP2C19-substrate:	0.314
CYP2C9-inhibitor:	0.893
CYP2C9-substrate:	0.754
CYP2D6-inhibitor:	0.089
CYP2D6-substrate:	0.288
CYP3A4-inhibitor:	0.617
CYP3A4-substrate:	0.754

ADMET: Excretion

Clearance (CL):	6.329
Half-life (T1/2):	0.728

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.171
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.055
Carcinogencity:	0.964
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.351

Download Data

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

Natural Product: NPC325479

Natural Product ID:	NPC325479
*Common Name:**	Protuboxepin A
IUPAC Name:	n.a.
Synonyms:	Protuboxepin A
Standard InCHIKey:	UOBOWSHNMYJJFQ-QIWLAUOQSA-N
Standard InCHI:	InChI=1S/C22H23N3O3/c1-3-14(2)18-19-24-21-16(11-7-8-12-28-21)22(27)25(19)17(20(26)23-18)13-15-9-5-4-6-10-15/h4-12,14,17-18H,3,13H2,1-2H3,(H,23,26)/t14?,17-,18+/m1/s1
SMILES:	CCC(C)C1C2=NC3=C(C=CC=CO3)C(=O)N2C(C(=O)N1)CC4=CC=CC=C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1802135
PubChem CID:	53355697
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001346] Diazines [CHEMONTID:0000075] Pyrimidines and pyrimidine derivatives [CHEMONTID:0000291] Pyrimidones

*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	5
Kd	1
Others	18

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	20

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	75000.0	nM	PMID[480362]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	130000.0	nM	PMID[480362]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	250000.0	nM	PMID[480362]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	150000.0	nM	PMID[480362]
NPT27	Others	Unspecified		IC50	=	180000.0	nM	PMID[480362]
NPT610	Others	Molecular identity unknown		Activity	=	7.0	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	2.26	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	6.12	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	20.83	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	5.21	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	49.09	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	41.93	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	23.7	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	7.31	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	10.12	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	10.83	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	7.44	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	20.54	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	26.04	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	34.4	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	46.67	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	18.76	%	PMID[480363]
NPT610	Others	Molecular identity unknown		Activity	=	39.47	%	PMID[480363]
NPT2	Others	Unspecified		Kd	=	71300.0	nM	PMID[480363]

☑ 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 NPC325479 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	323
0.1-0.2	3138
0.2-0.3	13510
0.3-0.4	14347
0.4-0.5	8317
0.5-0.6	2848
0.6-0.7	194
0.7-0.8	13
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.7769	Intermediate Similarity	NPC470544
0.7752	Intermediate Similarity	NPC33742
0.771	Intermediate Similarity	NPC470545
0.7674	Intermediate Similarity	NPC35850
0.7674	Intermediate Similarity	NPC276949
0.7652	Intermediate Similarity	NPC470546
0.7612	Intermediate Similarity	NPC202521
0.7537	Intermediate Similarity	NPC476990
0.75	Intermediate Similarity	NPC6975
0.7481	Intermediate Similarity	NPC71684
0.7434	Intermediate Similarity	NPC471132
0.7426	Intermediate Similarity	NPC252878
0.7372	Intermediate Similarity	NPC46427
0.7368	Intermediate Similarity	NPC315276
0.7368	Intermediate Similarity	NPC14672
0.7368	Intermediate Similarity	NPC239357
0.7368	Intermediate Similarity	NPC285926
0.7338	Intermediate Similarity	NPC84317
0.7319	Intermediate Similarity	NPC22746
0.731	Intermediate Similarity	NPC77992
0.731	Intermediate Similarity	NPC132636
0.7286	Intermediate Similarity	NPC319766
0.7246	Intermediate Similarity	NPC474082
0.7246	Intermediate Similarity	NPC175726
0.7244	Intermediate Similarity	NPC154478
0.7234	Intermediate Similarity	NPC473322
0.7154	Intermediate Similarity	NPC161972
0.7154	Intermediate Similarity	NPC303045
0.7153	Intermediate Similarity	NPC200964
0.7143	Intermediate Similarity	NPC474479
0.7143	Intermediate Similarity	NPC101719
0.7133	Intermediate Similarity	NPC255447
0.7133	Intermediate Similarity	NPC130309
0.7132	Intermediate Similarity	NPC220698
0.7113	Intermediate Similarity	NPC111428
0.7083	Intermediate Similarity	NPC246079
0.7071	Intermediate Similarity	NPC222466
0.704	Intermediate Similarity	NPC311242
0.7034	Intermediate Similarity	NPC287401
0.7027	Intermediate Similarity	NPC239762
0.7027	Intermediate Similarity	NPC163392
0.7007	Intermediate Similarity	NPC68865
0.7007	Intermediate Similarity	NPC471264
0.7007	Intermediate Similarity	NPC471265
0.7007	Intermediate Similarity	NPC127741
0.6993	Remote Similarity	NPC469666
0.6986	Remote Similarity	NPC248283
0.6954	Remote Similarity	NPC471680
0.6944	Remote Similarity	NPC300315
0.6933	Remote Similarity	NPC161069
0.6911	Remote Similarity	NPC226438
0.687	Remote Similarity	NPC474973
0.687	Remote Similarity	NPC474804
0.687	Remote Similarity	NPC130898
0.6867	Remote Similarity	NPC469427
0.6867	Remote Similarity	NPC263493
0.6867	Remote Similarity	NPC168113
0.6867	Remote Similarity	NPC469426
0.6867	Remote Similarity	NPC269398
0.6853	Remote Similarity	NPC477937
0.6842	Remote Similarity	NPC266741
0.6842	Remote Similarity	NPC209509
0.6828	Remote Similarity	NPC200589
0.6825	Remote Similarity	NPC25565
0.6821	Remote Similarity	NPC176226
0.6821	Remote Similarity	NPC197682
0.6821	Remote Similarity	NPC139326
0.68	Remote Similarity	NPC476259
0.6797	Remote Similarity	NPC81026
0.6794	Remote Similarity	NPC143516
0.6776	Remote Similarity	NPC476978
0.6774	Remote Similarity	NPC13470
0.6772	Remote Similarity	NPC475439
0.6772	Remote Similarity	NPC473501
0.6757	Remote Similarity	NPC141050
0.6753	Remote Similarity	NPC138775
0.675	Remote Similarity	NPC62104
0.675	Remote Similarity	NPC1390
0.6733	Remote Similarity	NPC470884
0.6733	Remote Similarity	NPC178662
0.6733	Remote Similarity	NPC313694
0.6733	Remote Similarity	NPC476133
0.6733	Remote Similarity	NPC92784
0.6733	Remote Similarity	NPC98424
0.6733	Remote Similarity	NPC242159
0.6732	Remote Similarity	NPC5620
0.6732	Remote Similarity	NPC313867
0.6732	Remote Similarity	NPC316008
0.6718	Remote Similarity	NPC88267
0.6718	Remote Similarity	NPC224610
0.6718	Remote Similarity	NPC113326
0.6718	Remote Similarity	NPC194390
0.671	Remote Similarity	NPC105717
0.671	Remote Similarity	NPC9373
0.6689	Remote Similarity	NPC46098
0.6689	Remote Similarity	NPC307357
0.6689	Remote Similarity	NPC268841
0.6688	Remote Similarity	NPC314358
0.6688	Remote Similarity	NPC314114
0.6667	Remote Similarity	NPC254798
0.6667	Remote Similarity	NPC315283
0.6667	Remote Similarity	NPC73655
0.6667	Remote Similarity	NPC235421
0.6667	Remote Similarity	NPC314388
0.6646	Remote Similarity	NPC471130
0.6646	Remote Similarity	NPC473341
0.6645	Remote Similarity	NPC135121
0.6645	Remote Similarity	NPC311658
0.6645	Remote Similarity	NPC476989
0.6629	Remote Similarity	NPC471196
0.6629	Remote Similarity	NPC471195
0.6624	Remote Similarity	NPC7817
0.6624	Remote Similarity	NPC475168
0.6624	Remote Similarity	NPC473491
0.6623	Remote Similarity	NPC322878
0.6623	Remote Similarity	NPC315266
0.6623	Remote Similarity	NPC477217
0.6623	Remote Similarity	NPC201244
0.6617	Remote Similarity	NPC471447
0.6617	Remote Similarity	NPC327481
0.6614	Remote Similarity	NPC58674
0.6605	Remote Similarity	NPC469243
0.6604	Remote Similarity	NPC39431
0.6603	Remote Similarity	NPC324445
0.66	Remote Similarity	NPC314835
0.6591	Remote Similarity	NPC275467
0.6585	Remote Similarity	NPC223207
0.6585	Remote Similarity	NPC22883
0.6585	Remote Similarity	NPC217804
0.6585	Remote Similarity	NPC5719
0.6585	Remote Similarity	NPC210377
0.6582	Remote Similarity	NPC300443
0.6581	Remote Similarity	NPC262077
0.6571	Remote Similarity	NPC169328
0.6562	Remote Similarity	NPC473580
0.6562	Remote Similarity	NPC469903
0.6561	Remote Similarity	NPC129666
0.6561	Remote Similarity	NPC2501
0.6558	Remote Similarity	NPC52748
0.655	Remote Similarity	NPC472999
0.6549	Remote Similarity	NPC477061
0.6549	Remote Similarity	NPC45777
0.6545	Remote Similarity	NPC304074
0.6545	Remote Similarity	NPC471771
0.6545	Remote Similarity	NPC15068
0.6545	Remote Similarity	NPC290755
0.6543	Remote Similarity	NPC24617
0.6543	Remote Similarity	NPC469898
0.6541	Remote Similarity	NPC286551
0.6541	Remote Similarity	NPC473418
0.6541	Remote Similarity	NPC122590
0.6538	Remote Similarity	NPC145113
0.6538	Remote Similarity	NPC329761
0.6538	Remote Similarity	NPC225648
0.6538	Remote Similarity	NPC16188
0.6525	Remote Similarity	NPC310467
0.6525	Remote Similarity	NPC237420
0.6524	Remote Similarity	NPC88970
0.6519	Remote Similarity	NPC324081
0.6512	Remote Similarity	NPC472258
0.6506	Remote Similarity	NPC63040
0.6503	Remote Similarity	NPC473003
0.6503	Remote Similarity	NPC475544
0.6503	Remote Similarity	NPC114806
0.65	Remote Similarity	NPC470902
0.6494	Remote Similarity	NPC468984
0.6493	Remote Similarity	NPC45033
0.6481	Remote Similarity	NPC94167
0.6481	Remote Similarity	NPC324850
0.6481	Remote Similarity	NPC172937
0.648	Remote Similarity	NPC470877
0.6478	Remote Similarity	NPC233702
0.6463	Remote Similarity	NPC152850
0.6463	Remote Similarity	NPC68650
0.6463	Remote Similarity	NPC105114
0.6463	Remote Similarity	NPC89923
0.6463	Remote Similarity	NPC239990
0.6463	Remote Similarity	NPC71933
0.645	Remote Similarity	NPC248670
0.6449	Remote Similarity	NPC474584
0.6446	Remote Similarity	NPC254700
0.6442	Remote Similarity	NPC287757
0.6442	Remote Similarity	NPC319320
0.6439	Remote Similarity	NPC329375
0.6438	Remote Similarity	NPC262166
0.6434	Remote Similarity	NPC27833
0.6429	Remote Similarity	NPC141139
0.6429	Remote Similarity	NPC209764
0.6429	Remote Similarity	NPC159178
0.6429	Remote Similarity	NPC78041
0.6429	Remote Similarity	NPC471307
0.6429	Remote Similarity	NPC74936
0.6429	Remote Similarity	NPC121872
0.6424	Remote Similarity	NPC471053
0.6424	Remote Similarity	NPC471052
0.6424	Remote Similarity	NPC471051
0.6423	Remote Similarity	NPC319579
0.6419	Remote Similarity	NPC81092
0.6419	Remote Similarity	NPC103605
0.6414	Remote Similarity	NPC283130

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 NPC325479 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	597
0.2-0.3	846
0.3-0.4	1235
0.4-0.5	3430
0.5-0.6	2398
0.6-0.7	423
0.7-0.8	23
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
0.7214	Intermediate Similarity	NPD3029	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2583	Phase 2
0.7153	Intermediate Similarity	NPD7342	Discontinued
0.7133	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD8173	Phase 2
0.7007	Intermediate Similarity	NPD8172	Phase 2
0.7007	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2584	Suspended
0.6993	Remote Similarity	NPD3626	Phase 3
0.694	Remote Similarity	NPD480	Approved
0.6939	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD8076	Discontinued
0.6923	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3588	Discontinued
0.6883	Remote Similarity	NPD5614	Approved
0.6883	Remote Similarity	NPD5613	Approved
0.6871	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5272	Discontinued
0.687	Remote Similarity	NPD7130	Phase 3
0.6863	Remote Similarity	NPD8323	Discontinued
0.6853	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6901	Phase 3
0.6835	Remote Similarity	NPD2891	Approved
0.6821	Remote Similarity	NPD7720	Phase 2
0.6818	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7522	Discontinued
0.68	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1967	Approved
0.6797	Remote Similarity	NPD1968	Approved
0.6795	Remote Similarity	NPD3821	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3820	Approved
0.6795	Remote Similarity	NPD3822	Approved
0.6794	Remote Similarity	NPD999	Phase 2
0.6776	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2016	Approved
0.6774	Remote Similarity	NPD3988	Approved
0.6774	Remote Similarity	NPD3283	Phase 3
0.6774	Remote Similarity	NPD3987	Approved
0.6774	Remote Similarity	NPD2014	Approved
0.6774	Remote Similarity	NPD6088	Approved
0.6774	Remote Similarity	NPD3282	Phase 1
0.6774	Remote Similarity	NPD2013	Approved
0.6739	Remote Similarity	NPD3123	Discovery
0.6732	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5423	Phase 2
0.6726	Remote Similarity	NPD5681	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4677	Discontinued
0.6712	Remote Similarity	NPD4125	Approved
0.6692	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6792	Phase 3
0.6667	Remote Similarity	NPD5578	Approved
0.6645	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4172	Approved
0.6645	Remote Similarity	NPD4173	Approved
0.6645	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD8416	Discontinued
0.6623	Remote Similarity	NPD6294	Approved
0.6623	Remote Similarity	NPD6295	Approved
0.6615	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8315	Phase 1
0.6603	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4152	Approved
0.66	Remote Similarity	NPD3908	Approved
0.66	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6557	Phase 2
0.6587	Remote Similarity	NPD6690	Approved
0.6581	Remote Similarity	NPD5481	Discontinued
0.6573	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1001	Discontinued
0.6552	Remote Similarity	NPD5367	Discontinued
0.6547	Remote Similarity	NPD2589	Approved
0.6547	Remote Similarity	NPD2588	Approved
0.6544	Remote Similarity	NPD3642	Approved
0.6544	Remote Similarity	NPD3643	Approved
0.6544	Remote Similarity	NPD3644	Approved
0.6541	Remote Similarity	NPD7131	Phase 3
0.6541	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1080	Approved
0.6533	Remote Similarity	NPD8265	Approved
0.6531	Remote Similarity	NPD4175	Approved
0.6531	Remote Similarity	NPD4177	Approved
0.6525	Remote Similarity	NPD998	Approved
0.6524	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3149	Approved
0.6522	Remote Similarity	NPD3148	Approved
0.6522	Remote Similarity	NPD3150	Approved
0.6522	Remote Similarity	NPD2659	Approved
0.6522	Remote Similarity	NPD2658	Approved
0.6522	Remote Similarity	NPD3147	Approved
0.6513	Remote Similarity	NPD4214	Discontinued
0.651	Remote Similarity	NPD5581	Approved
0.6503	Remote Similarity	NPD7599	Phase 2
0.65	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD753	Approved
0.6494	Remote Similarity	NPD2088	Approved
0.6494	Remote Similarity	NPD2022	Approved
0.6494	Remote Similarity	NPD2087	Approved
0.649	Remote Similarity	NPD8643	Discontinued
0.6486	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD2527	Approved
0.6479	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4540	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD941	Approved
0.6463	Remote Similarity	NPD6259	Discontinued
0.6463	Remote Similarity	NPD7600	Phase 2
0.6458	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1812	Approved
0.6457	Remote Similarity	NPD1814	Approved
0.6456	Remote Similarity	NPD1582	Approved
0.6456	Remote Similarity	NPD1581	Approved
0.6452	Remote Similarity	NPD6681	Discovery
0.6449	Remote Similarity	NPD1764	Approved
0.6449	Remote Similarity	NPD1762	Approved
0.6447	Remote Similarity	NPD6073	Approved
0.6446	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD3901	Approved
0.6443	Remote Similarity	NPD2044	Approved
0.6443	Remote Similarity	NPD2046	Approved
0.6443	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD2048	Approved
0.6443	Remote Similarity	NPD2045	Approved
0.6443	Remote Similarity	NPD2047	Approved
0.6443	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD2043	Approved
0.6443	Remote Similarity	NPD2051	Approved
0.6443	Remote Similarity	NPD21	Approved
0.6438	Remote Similarity	NPD3125	Approved
0.6438	Remote Similarity	NPD2031	Discontinued
0.6429	Remote Similarity	NPD7508	Discontinued
0.6424	Remote Similarity	NPD6623	Phase 3
0.6424	Remote Similarity	NPD3900	Approved
0.6424	Remote Similarity	NPD3902	Approved
0.6424	Remote Similarity	NPD4153	Approved
0.6424	Remote Similarity	NPD5296	Approved
0.6415	Remote Similarity	NPD4432	Discontinued
0.6414	Remote Similarity	NPD3071	Approved
0.6414	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD478	Approved
0.6414	Remote Similarity	NPD3072	Approved
0.6414	Remote Similarity	NPD3073	Approved
0.6408	Remote Similarity	NPD2218	Phase 2
0.6408	Remote Similarity	NPD2217	Approved
0.6404	Remote Similarity	NPD5042	Phase 1
0.6402	Remote Similarity	NPD4566	Approved
0.6402	Remote Similarity	NPD4567	Approved
0.64	Remote Similarity	NPD6075	Approved
0.64	Remote Similarity	NPD6076	Approved
0.6398	Remote Similarity	NPD4646	Approved
0.6398	Remote Similarity	NPD4648	Approved
0.6398	Remote Similarity	NPD4647	Approved
0.6397	Remote Similarity	NPD2678	Approved
0.6397	Remote Similarity	NPD2679	Approved
0.6391	Remote Similarity	NPD5655	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD1344	Phase 2
0.6376	Remote Similarity	NPD5263	Approved
0.6375	Remote Similarity	NPD5230	Approved
0.6375	Remote Similarity	NPD5229	Approved
0.6369	Remote Similarity	NPD6676	Phase 2
0.6364	Remote Similarity	NPD3480	Approved
0.6364	Remote Similarity	NPD5981	Approved
0.6358	Remote Similarity	NPD8118	Discontinued
0.6357	Remote Similarity	NPD4814	Discontinued
0.6352	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD4762	Approved
0.6345	Remote Similarity	NPD3624	Phase 2
0.6345	Remote Similarity	NPD4761	Approved
0.6341	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.634	Remote Similarity	NPD5725	Approved
0.6327	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD2962	Approved
0.6327	Remote Similarity	NPD2961	Approved
0.6325	Remote Similarity	NPD8351	Phase 2
0.6319	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD854	Approved
0.6316	Remote Similarity	NPD855	Approved
0.6312	Remote Similarity	NPD1348	Approved
0.6312	Remote Similarity	NPD4942	Approved
0.6312	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD3040	Approved
0.6304	Remote Similarity	NPD4254	Approved
0.6304	Remote Similarity	NPD4253	Approved
0.6301	Remote Similarity	NPD5335	Discontinued
0.6299	Remote Similarity	NPD8154	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5717	Approved
0.6296	Remote Similarity	NPD1018	Approved
0.6294	Remote Similarity	NPD6343	Approved
0.6294	Remote Similarity	NPD6345	Approved
0.6289	Remote Similarity	NPD3519	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