NPASS Compound

Structure

NPC302235 OpenBabel07101719512D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9131 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6722 -1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 -2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0898 -2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 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 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 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 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5021 -3.0316 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 0.9135 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 22 1 0 0 0 0 3 23 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 9 1 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 12 20 2 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 13 21 2 0 0 0 0 14 17 1 0 0 0 0 14 22 1 1 0 0 0 15 8 1 6 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.07
Volume:	323.317
LogP:	1.796
LogD:	1.881
LogS:	-3.791
# Rotatable Bonds:	3
TPSA:	81.08
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.838
Synthetic Accessibility Score:	4.546
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.859
MDCK Permeability:	1.8157361409976147e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.222
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.851
Plasma Protein Binding (PPB):	88.50836181640625%
Volume Distribution (VD):	0.69
Pgp-substrate:	22.001922607421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.308
CYP2C19-inhibitor:	0.789
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.551
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.311
CYP3A4-substrate:	0.971

ADMET: Excretion

Clearance (CL):	8.359
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.271
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.608
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.003

Download Data

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

Natural Product: NPC302235

Natural Product ID:	NPC302235
*Common Name:**	Dehydrobis(Methylthio)Gliotoxin
IUPAC Name:	(3R,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-10H-pyrazino[1,2-a]indole-1,4-dione
Synonyms:	Dehydrobis(Methylthio)Gliotoxin
Standard InCHIKey:	BUSZSWVUELPPBM-HUUCEWRRSA-N
Standard InCHI:	InChI=1S/C15H18N2O4S2/c1-16-12(20)14(22-2)7-9-5-4-6-10(19)11(9)17(14)13(21)15(16,8-18)23-3/h4-6,18-19H,7-8H2,1-3H3/t14-,15-/m1/s1
SMILES:	CS[C@]12Cc3c(N2C(=O)[C@](N(C1=O)C)(SC)CO)c(O)ccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088849
PubChem CID:	13989139
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002013] Indolecarboxylic acids and derivatives

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	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
IC50	7
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	2
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT470	Individual Protein	Rhodesain	Trypanosoma brucei rhodesiense	IC50	=	19500.0	nM	PMID[491751]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	141000.0	nM	PMID[491751]
NPT168	Cell Line	P388	Mus musculus	IC50	=	110.0	nM	PMID[491752]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	58000.0	nM	PMID[491752]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	8500.0	nM	PMID[491751]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[491751]
NPT2	Others	Unspecified		Ratio IC50	=	16.6	uM	PMID[491751]
NPT2	Others	Unspecified		IC50	=	16900.0	nM	PMID[491751]

☑ 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 NPC302235 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	250
0.1-0.2	1684
0.2-0.3	10195
0.3-0.4	7866
0.4-0.5	17173
0.5-0.6	4890
0.6-0.7	619
0.7-0.8	17
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9458	High Similarity	NPC166169
0.8402	Intermediate Similarity	NPC475609
0.7598	Intermediate Similarity	NPC33507
0.75	Intermediate Similarity	NPC470301
0.743	Intermediate Similarity	NPC328270
0.7306	Intermediate Similarity	NPC470485
0.7273	Intermediate Similarity	NPC1464
0.7202	Intermediate Similarity	NPC470483
0.7173	Intermediate Similarity	NPC262725
0.7158	Intermediate Similarity	NPC472114
0.7158	Intermediate Similarity	NPC472115
0.7157	Intermediate Similarity	NPC265642
0.7157	Intermediate Similarity	NPC132874
0.7157	Intermediate Similarity	NPC138615
0.7157	Intermediate Similarity	NPC218733
0.709	Intermediate Similarity	NPC39822
0.6989	Remote Similarity	NPC146370
0.6978	Remote Similarity	NPC301163
0.6957	Remote Similarity	NPC470481
0.6957	Remote Similarity	NPC470482
0.6927	Remote Similarity	NPC470491
0.6919	Remote Similarity	NPC471124
0.6914	Remote Similarity	NPC471680
0.6912	Remote Similarity	NPC246140
0.6912	Remote Similarity	NPC195787
0.6904	Remote Similarity	NPC204970
0.6901	Remote Similarity	NPC478141
0.69	Remote Similarity	NPC112937
0.6884	Remote Similarity	NPC170333
0.6881	Remote Similarity	NPC469732
0.685	Remote Similarity	NPC316282
0.685	Remote Similarity	NPC161804
0.6842	Remote Similarity	NPC129624
0.6837	Remote Similarity	NPC477394
0.6836	Remote Similarity	NPC470824
0.68	Remote Similarity	NPC251439
0.6793	Remote Similarity	NPC471122
0.678	Remote Similarity	NPC470484
0.6774	Remote Similarity	NPC204867
0.6768	Remote Similarity	NPC302169
0.6759	Remote Similarity	NPC122886
0.6749	Remote Similarity	NPC138830
0.6734	Remote Similarity	NPC473004
0.6725	Remote Similarity	NPC257390
0.6724	Remote Similarity	NPC313694
0.6724	Remote Similarity	NPC242159
0.6722	Remote Similarity	NPC473491
0.672	Remote Similarity	NPC133470
0.672	Remote Similarity	NPC289776
0.672	Remote Similarity	NPC191863
0.6704	Remote Similarity	NPC189908
0.6701	Remote Similarity	NPC270301
0.6701	Remote Similarity	NPC197335
0.6701	Remote Similarity	NPC116096
0.6698	Remote Similarity	NPC234772
0.6697	Remote Similarity	NPC470480
0.6682	Remote Similarity	NPC222046
0.6682	Remote Similarity	NPC288110
0.6667	Remote Similarity	NPC476268
0.6667	Remote Similarity	NPC314659
0.6667	Remote Similarity	NPC148124
0.6667	Remote Similarity	NPC315388
0.6651	Remote Similarity	NPC266994
0.665	Remote Similarity	NPC476098
0.665	Remote Similarity	NPC477179
0.6648	Remote Similarity	NPC16188
0.6648	Remote Similarity	NPC262166
0.6648	Remote Similarity	NPC125852
0.6635	Remote Similarity	NPC270918
0.6635	Remote Similarity	NPC478075
0.6635	Remote Similarity	NPC212123
0.6633	Remote Similarity	NPC5630
0.6633	Remote Similarity	NPC174629
0.6631	Remote Similarity	NPC472117
0.6621	Remote Similarity	NPC471513
0.662	Remote Similarity	NPC99724
0.6618	Remote Similarity	NPC133156
0.6618	Remote Similarity	NPC477178
0.6618	Remote Similarity	NPC477181
0.6618	Remote Similarity	NPC254850
0.6618	Remote Similarity	NPC477180
0.6616	Remote Similarity	NPC21425
0.6603	Remote Similarity	NPC330683
0.6603	Remote Similarity	NPC329567
0.6591	Remote Similarity	NPC74216
0.6587	Remote Similarity	NPC477173
0.6587	Remote Similarity	NPC470490
0.6587	Remote Similarity	NPC477174
0.6585	Remote Similarity	NPC67904
0.6577	Remote Similarity	NPC477516
0.6571	Remote Similarity	NPC109580
0.6571	Remote Similarity	NPC477160
0.6569	Remote Similarity	NPC100863
0.6566	Remote Similarity	NPC150308
0.6562	Remote Similarity	NPC137627
0.6555	Remote Similarity	NPC470488
0.6555	Remote Similarity	NPC53344
0.6545	Remote Similarity	NPC475123
0.6545	Remote Similarity	NPC248903
0.6545	Remote Similarity	NPC469915
0.6545	Remote Similarity	NPC475204
0.6544	Remote Similarity	NPC46259
0.6528	Remote Similarity	NPC219397
0.6528	Remote Similarity	NPC470548
0.6524	Remote Similarity	NPC475259
0.6524	Remote Similarity	NPC471945
0.6524	Remote Similarity	NPC471950
0.6522	Remote Similarity	NPC68967
0.6517	Remote Similarity	NPC203628
0.6517	Remote Similarity	NPC92803
0.6515	Remote Similarity	NPC473007
0.6514	Remote Similarity	NPC71539
0.6514	Remote Similarity	NPC250960
0.651	Remote Similarity	NPC89831
0.6505	Remote Similarity	NPC29285
0.6504	Remote Similarity	NPC470784
0.6504	Remote Similarity	NPC474183
0.6503	Remote Similarity	NPC144691
0.6503	Remote Similarity	NPC233702
0.6502	Remote Similarity	NPC230313
0.65	Remote Similarity	NPC18890
0.65	Remote Similarity	NPC284706
0.65	Remote Similarity	NPC26928
0.6498	Remote Similarity	NPC478007
0.6495	Remote Similarity	NPC476441
0.6493	Remote Similarity	NPC471946
0.6493	Remote Similarity	NPC471951
0.6489	Remote Similarity	NPC309531
0.6489	Remote Similarity	NPC472102
0.6486	Remote Similarity	NPC244509
0.6486	Remote Similarity	NPC477397
0.6484	Remote Similarity	NPC315829
0.6482	Remote Similarity	NPC87391
0.6471	Remote Similarity	NPC244336
0.6471	Remote Similarity	NPC473458
0.6468	Remote Similarity	NPC45389
0.6468	Remote Similarity	NPC474059
0.6468	Remote Similarity	NPC473008
0.6467	Remote Similarity	NPC202198
0.6462	Remote Similarity	NPC475359
0.6462	Remote Similarity	NPC191817
0.6459	Remote Similarity	NPC470489
0.6455	Remote Similarity	NPC476231
0.6455	Remote Similarity	NPC472120
0.6455	Remote Similarity	NPC472101
0.6452	Remote Similarity	NPC37957
0.6452	Remote Similarity	NPC315804
0.6452	Remote Similarity	NPC313804
0.645	Remote Similarity	NPC329731
0.6443	Remote Similarity	NPC279871
0.6443	Remote Similarity	NPC136797
0.6443	Remote Similarity	NPC476227
0.6442	Remote Similarity	NPC471436
0.6438	Remote Similarity	NPC478008
0.6429	Remote Similarity	NPC474815
0.6429	Remote Similarity	NPC287152
0.6425	Remote Similarity	NPC127178
0.6422	Remote Similarity	NPC318525
0.6422	Remote Similarity	NPC10653
0.6422	Remote Similarity	NPC243626
0.6421	Remote Similarity	NPC313757
0.6419	Remote Similarity	NPC477395
0.6417	Remote Similarity	NPC323336
0.6417	Remote Similarity	NPC326349
0.6414	Remote Similarity	NPC477159
0.6413	Remote Similarity	NPC470821
0.6413	Remote Similarity	NPC241392
0.6402	Remote Similarity	NPC305542
0.6402	Remote Similarity	NPC10732
0.6402	Remote Similarity	NPC127996
0.6402	Remote Similarity	NPC159815
0.6402	Remote Similarity	NPC474058
0.6396	Remote Similarity	NPC298320
0.6394	Remote Similarity	NPC232600
0.639	Remote Similarity	NPC303214
0.6388	Remote Similarity	NPC184680
0.6387	Remote Similarity	NPC472106
0.6386	Remote Similarity	NPC473569
0.6386	Remote Similarity	NPC22689
0.6386	Remote Similarity	NPC105055
0.6384	Remote Similarity	NPC14288
0.6383	Remote Similarity	NPC211525
0.6383	Remote Similarity	NPC153694
0.6383	Remote Similarity	NPC113946
0.6381	Remote Similarity	NPC14339
0.6381	Remote Similarity	NPC163829
0.6381	Remote Similarity	NPC473422
0.6381	Remote Similarity	NPC268077
0.6378	Remote Similarity	NPC261934
0.6378	Remote Similarity	NPC5194
0.6373	Remote Similarity	NPC254957
0.6372	Remote Similarity	NPC151781
0.6372	Remote Similarity	NPC74562
0.6372	Remote Similarity	NPC316181
0.6372	Remote Similarity	NPC30749
0.6369	Remote Similarity	NPC476989
0.6369	Remote Similarity	NPC204156
0.636	Remote Similarity	NPC470785
0.6359	Remote Similarity	NPC26108
0.6358	Remote Similarity	NPC469666

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 NPC302235 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	579
0.2-0.3	870
0.3-0.4	1368
0.4-0.5	3312
0.5-0.6	2619
0.6-0.7	234
0.7-0.8	1
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
0.6968	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD2098	Approved
0.6862	Remote Similarity	NPD5137	Approved
0.6859	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4652	Approved
0.6793	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4465	Phase 2
0.678	Remote Similarity	NPD4467	Phase 2
0.6776	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2097	Approved
0.6754	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD3479	Discontinued
0.6716	Remote Similarity	NPD6321	Discontinued
0.6715	Remote Similarity	NPD6518	Discontinued
0.6702	Remote Similarity	NPD5823	Approved
0.6702	Remote Similarity	NPD7324	Discontinued
0.6701	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5860	Discontinued
0.6667	Remote Similarity	NPD2889	Approved
0.6667	Remote Similarity	NPD2888	Approved
0.6667	Remote Similarity	NPD2017	Approved
0.6667	Remote Similarity	NPD2890	Approved
0.6667	Remote Similarity	NPD1544	Phase 1
0.6635	Remote Similarity	NPD4492	Approved
0.6635	Remote Similarity	NPD4494	Approved
0.6632	Remote Similarity	NPD3449	Discontinued
0.6611	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4082	Approved
0.6603	Remote Similarity	NPD2906	Approved
0.6603	Remote Similarity	NPD2907	Approved
0.66	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7603	Discontinued
0.6564	Remote Similarity	NPD6879	Phase 2
0.6564	Remote Similarity	NPD6878	Phase 2
0.655	Remote Similarity	NPD5112	Approved
0.655	Remote Similarity	NPD5113	Approved
0.655	Remote Similarity	NPD5114	Approved
0.6524	Remote Similarity	NPD4022	Approved
0.6524	Remote Similarity	NPD3472	Approved
0.6522	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3141	Discontinued
0.6517	Remote Similarity	NPD5994	Discontinued
0.6507	Remote Similarity	NPD6260	Discontinued
0.65	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5194	Approved
0.6488	Remote Similarity	NPD5196	Approved
0.6488	Remote Similarity	NPD5197	Approved
0.6486	Remote Similarity	NPD5639	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5445	Approved
0.648	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3888	Discontinued
0.6471	Remote Similarity	NPD1769	Discontinued
0.6462	Remote Similarity	NPD3372	Discontinued
0.6459	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD6644	Discontinued
0.645	Remote Similarity	NPD4515	Suspended
0.6449	Remote Similarity	NPD4455	Discontinued
0.6448	Remote Similarity	NPD4432	Discontinued
0.6445	Remote Similarity	NPD6376	Discontinued
0.6444	Remote Similarity	NPD4127	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5077	Approved
0.6436	Remote Similarity	NPD5076	Approved
0.6432	Remote Similarity	NPD4493	Discontinued
0.642	Remote Similarity	NPD2791	Discontinued
0.6417	Remote Similarity	NPD6395	Phase 2
0.6417	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4596	Phase 1
0.6396	Remote Similarity	NPD6297	Approved
0.6394	Remote Similarity	NPD6238	Discontinued
0.6385	Remote Similarity	NPD3893	Discontinued
0.6385	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD3391	Approved
0.6368	Remote Similarity	NPD3351	Approved
0.6368	Remote Similarity	NPD6891	Phase 2
0.6364	Remote Similarity	NPD3684	Discontinued
0.6359	Remote Similarity	NPD5938	Phase 3
0.6359	Remote Similarity	NPD5942	Approved
0.6359	Remote Similarity	NPD5941	Approved
0.6355	Remote Similarity	NPD1945	Phase 1
0.6355	Remote Similarity	NPD6659	Phase 2
0.6354	Remote Similarity	NPD5024	Approved
0.6354	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6851	Approved
0.635	Remote Similarity	NPD6853	Approved
0.6349	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6805	Discontinued
0.6343	Remote Similarity	NPD4897	Phase 2
0.6335	Remote Similarity	NPD7820	Phase 3
0.6333	Remote Similarity	NPD3802	Phase 3
0.6332	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD5071	Phase 2
0.6327	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD3350	Approved
0.6321	Remote Similarity	NPD7126	Discontinued
0.6316	Remote Similarity	NPD6982	Phase 2
0.6316	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6255	Approved
0.6316	Remote Similarity	NPD6256	Approved
0.6316	Remote Similarity	NPD6254	Approved
0.6313	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD5025	Approved
0.6306	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD7617	Discontinued
0.6305	Remote Similarity	NPD7628	Phase 3
0.6305	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD7630	Phase 3
0.63	Remote Similarity	NPD7281	Phase 3
0.63	Remote Similarity	NPD7280	Phase 3
0.6296	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3793	Phase 3
0.6294	Remote Similarity	NPD6020	Phase 2
0.6289	Remote Similarity	NPD5186	Approved
0.6289	Remote Similarity	NPD5183	Approved
0.6289	Remote Similarity	NPD5847	Phase 1
0.6283	Remote Similarity	NPD7664	Discontinued
0.6278	Remote Similarity	NPD7186	Phase 3
0.6275	Remote Similarity	NPD4370	Phase 3
0.6274	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD6557	Phase 2
0.6268	Remote Similarity	NPD6253	Approved
0.6264	Remote Similarity	NPD5265	Approved
0.6264	Remote Similarity	NPD5264	Approved
0.6264	Remote Similarity	NPD4430	Phase 2
0.6263	Remote Similarity	NPD4514	Approved
0.6263	Remote Similarity	NPD6283	Phase 2
0.6257	Remote Similarity	NPD4126	Approved
0.6256	Remote Similarity	NPD3975	Discontinued
0.6256	Remote Similarity	NPD7205	Discontinued
0.625	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4668	Phase 2
0.625	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7167	Discontinued
0.6238	Remote Similarity	NPD3416	Discontinued
0.6237	Remote Similarity	NPD7303	Discontinued
0.623	Remote Similarity	NPD5967	Approved
0.623	Remote Similarity	NPD7600	Phase 2
0.6226	Remote Similarity	NPD1294	Discontinued
0.6225	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD4428	Discontinued
0.6216	Remote Similarity	NPD8356	Approved
0.6216	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD2916	Discontinued
0.6214	Remote Similarity	NPD5610	Approved
0.6212	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD7224	Discontinued
0.6205	Remote Similarity	NPD1293	Approved
0.6205	Remote Similarity	NPD7223	Discontinued
0.6202	Remote Similarity	NPD5195	Discontinued
0.62	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6199	Discontinued
0.6193	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7133	Discontinued
0.6184	Remote Similarity	NPD6493	Phase 3
0.6182	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7692	Discontinued
0.6181	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD5485	Approved
0.6181	Remote Similarity	NPD5484	Approved
0.6179	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD7599	Phase 2
0.6178	Remote Similarity	NPD8430	Approved
0.6176	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD8025	Phase 2
0.6171	Remote Similarity	NPD7805	Phase 3
0.6171	Remote Similarity	NPD5506	Approved
0.6171	Remote Similarity	NPD5507	Approved
0.6169	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD6665	Discontinued
0.6164	Remote Similarity	NPD7432	Phase 2
0.6162	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6457	Approved
0.6154	Remote Similarity	NPD2680	Approved
0.6154	Remote Similarity	NPD2681	Approved
0.6154	Remote Similarity	NPD5582	Discontinued
0.6154	Remote Similarity	NPD2899	Discontinued
0.615	Remote Similarity	NPD5055	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD6874	Approved
0.6142	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.614	Remote Similarity	NPD8027	Approved
0.614	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD3229	Phase 2
0.6136	Remote Similarity	NPD5263	Approved
0.6132	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD5600	Discontinued
0.6131	Remote Similarity	NPD5313	Approved
0.6131	Remote Similarity	NPD5312	Approved
0.6129	Remote Similarity	NPD5613	Approved
0.6129	Remote Similarity	NPD5614	Approved
0.6127	Remote Similarity	NPD2383	Phase 1
0.6127	Remote Similarity	NPD1755	Approved

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