NPASS Compound

Structure

CID200831 OpenBabel06191715592D 43 43 0 0 0 0 0 0 0 0999 V2000 0.0000 -18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -19.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -17.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -18.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -18.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -15.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 -1.5000 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 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 0.0000 -0.0000 0.0000 C 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 8 34 1 0 0 0 0 9 42 1 0 0 0 0 10 43 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 25 1 0 0 0 0 16 28 2 0 0 0 0 17 29 1 0 0 0 0 18 29 2 0 0 0 0 19 30 1 0 0 0 0 20 30 2 0 0 0 0 21 31 1 0 0 0 0 22 31 2 0 0 0 0 23 32 1 0 0 0 0 24 32 2 0 0 0 0 25 33 1 0 0 0 0 26 27 1 0 0 0 0 26 33 2 0 0 0 0 27 35 1 0 0 0 0 34 35 2 0 0 0 0 34 36 1 0 0 0 0 35 37 1 0 0 0 0 36 38 1 0 0 0 0 36 40 2 0 0 0 0 37 39 1 0 0 0 0 37 41 2 0 0 0 0 38 39 2 0 0 0 0 38 42 1 0 0 0 0 39 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	590.43
Volume:	683.34
LogP:	9.811
LogD:	6.53
LogS:	-4.534
# Rotatable Bonds:	18
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.101
Synthetic Accessibility Score:	3.719
Fsp3:	0.487
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.094
MDCK Permeability:	1.6677677194820717e-05
Pgp-inhibitor:	0.931
Pgp-substrate:	0.174
Human Intestinal Absorption (HIA):	0.399
20% Bioavailability (F20%):	0.797
30% Bioavailability (F30%):	0.678

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	99.1717758178711%
Volume Distribution (VD):	2.367
Pgp-substrate:	1.4505155086517334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.169
CYP1A2-substrate:	0.305
CYP2C19-inhibitor:	0.197
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.393
CYP2C9-substrate:	0.99
CYP2D6-inhibitor:	0.502
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.657
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	2.907
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.464
Human Hepatotoxicity (H-HT):	0.882
Drug-inuced Liver Injury (DILI):	0.001
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.989
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.659
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC200831

Natural Product ID:	NPC200831
*Common Name:**	Coenzyme Q6
IUPAC Name:	2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaenyl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	GXNFPEOUKFOTKY-LPHQIWJTSA-N
Standard InCHI:	InChI=1S/C39H58O4/c1-28(2)16-11-17-29(3)18-12-19-30(4)20-13-21-31(5)22-14-23-32(6)24-15-25-33(7)26-27-35-34(8)36(40)38(42-9)39(43-10)37(35)41/h16,18,20,22,24,26H,11-15,17,19,21,23,25,27H2,1-10H3/b29-18+,30-20+,31-22+,32-24+,33-26+
SMILES:	COC1=C(OC)C(=O)C(=C(C1=O)C/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CC/C=C(/CCC=C(C)C)C)C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2251232
PubChem CID:	5283544
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones [CHEMONTID:0001545] Ubiquinones

*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
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0003-9861(62)90112-1]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11035032]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12902239]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[13835567]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14389294]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1449509]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14607989]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15375647]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15744050]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16850348]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17439666]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22031445]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2405251]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24305546]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24678285]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24733517]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24831709]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24981409]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2687322]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3289762]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4266242]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4616942]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5764336]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6306574]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[767332]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7929110]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8017107]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8798704]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8852895]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8971708]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748245]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	Activity	=	97.3	mg	PMID[568108]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	18.3	%	PMID[568108]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	6.7	%	PMID[568108]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	1.7	%	PMID[568108]

☑ 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 NPC200831 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	151
0.1-0.2	4332
0.2-0.3	18847
0.3-0.4	12967
0.4-0.5	5190
0.5-0.6	1064
0.6-0.7	93
0.7-0.8	35
0.8-0.85	8
0.85-0.9	2
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC224103
1.0	High Similarity	NPC299369
0.9434	High Similarity	NPC317796
0.8889	High Similarity	NPC474805
0.8519	High Similarity	NPC22329
0.8333	Intermediate Similarity	NPC220191
0.8254	Intermediate Similarity	NPC474619
0.8226	Intermediate Similarity	NPC98897
0.8136	Intermediate Similarity	NPC139056
0.8095	Intermediate Similarity	NPC16119
0.807	Intermediate Similarity	NPC129710
0.8065	Intermediate Similarity	NPC474400
0.8065	Intermediate Similarity	NPC34622
0.8	Intermediate Similarity	NPC473494
0.7903	Intermediate Similarity	NPC151728
0.7903	Intermediate Similarity	NPC57463
0.7879	Intermediate Similarity	NPC291062
0.7879	Intermediate Similarity	NPC94743
0.7846	Intermediate Similarity	NPC125578
0.7846	Intermediate Similarity	NPC263382
0.7846	Intermediate Similarity	NPC146376
0.7761	Intermediate Similarity	NPC474539
0.7727	Intermediate Similarity	NPC262673
0.7719	Intermediate Similarity	NPC137396
0.7692	Intermediate Similarity	NPC243272
0.7576	Intermediate Similarity	NPC134385
0.7536	Intermediate Similarity	NPC264178
0.7463	Intermediate Similarity	NPC94488
0.7407	Intermediate Similarity	NPC477686
0.7407	Intermediate Similarity	NPC106547
0.7313	Intermediate Similarity	NPC134593
0.7302	Intermediate Similarity	NPC79756
0.7288	Intermediate Similarity	NPC168521
0.7286	Intermediate Similarity	NPC147438
0.7273	Intermediate Similarity	NPC191337
0.7273	Intermediate Similarity	NPC110396
0.7231	Intermediate Similarity	NPC7029
0.7164	Intermediate Similarity	NPC298249
0.7164	Intermediate Similarity	NPC251429
0.7097	Intermediate Similarity	NPC268185
0.7083	Intermediate Similarity	NPC26504
0.7077	Intermediate Similarity	NPC477830
0.7077	Intermediate Similarity	NPC143168
0.7077	Intermediate Similarity	NPC53109
0.7	Intermediate Similarity	NPC66365
0.6984	Remote Similarity	NPC320421
0.6912	Remote Similarity	NPC203335
0.678	Remote Similarity	NPC15325
0.678	Remote Similarity	NPC118788
0.678	Remote Similarity	NPC225974
0.6757	Remote Similarity	NPC473536
0.6667	Remote Similarity	NPC111474
0.6667	Remote Similarity	NPC166788
0.6622	Remote Similarity	NPC477708
0.6615	Remote Similarity	NPC38455
0.6604	Remote Similarity	NPC180840
0.6567	Remote Similarity	NPC477707
0.6562	Remote Similarity	NPC283502
0.6552	Remote Similarity	NPC8610
0.6552	Remote Similarity	NPC262558
0.6533	Remote Similarity	NPC471225
0.6533	Remote Similarity	NPC283087
0.6522	Remote Similarity	NPC137163
0.6491	Remote Similarity	NPC25771
0.6462	Remote Similarity	NPC281195
0.6418	Remote Similarity	NPC151648
0.6418	Remote Similarity	NPC68044
0.6415	Remote Similarity	NPC185839
0.641	Remote Similarity	NPC474085
0.6377	Remote Similarity	NPC7940
0.6377	Remote Similarity	NPC101670
0.6364	Remote Similarity	NPC203233
0.6364	Remote Similarity	NPC133600
0.6324	Remote Similarity	NPC474774
0.6316	Remote Similarity	NPC301972
0.6316	Remote Similarity	NPC292463
0.6308	Remote Similarity	NPC474825
0.6296	Remote Similarity	NPC8518
0.6296	Remote Similarity	NPC77971
0.6296	Remote Similarity	NPC132228
0.6296	Remote Similarity	NPC263997
0.6296	Remote Similarity	NPC6185
0.6296	Remote Similarity	NPC241512
0.6282	Remote Similarity	NPC74086
0.625	Remote Similarity	NPC288281
0.625	Remote Similarity	NPC25038
0.625	Remote Similarity	NPC473603
0.625	Remote Similarity	NPC476059
0.6232	Remote Similarity	NPC477457
0.6232	Remote Similarity	NPC477456
0.6232	Remote Similarity	NPC475618
0.623	Remote Similarity	NPC228776
0.623	Remote Similarity	NPC288381
0.623	Remote Similarity	NPC32351
0.623	Remote Similarity	NPC20934
0.6226	Remote Similarity	NPC38497
0.622	Remote Similarity	NPC291712
0.6203	Remote Similarity	NPC99308
0.6197	Remote Similarity	NPC473213
0.619	Remote Similarity	NPC217188
0.6164	Remote Similarity	NPC203819
0.6154	Remote Similarity	NPC221763
0.6154	Remote Similarity	NPC471740
0.6143	Remote Similarity	NPC471566
0.6143	Remote Similarity	NPC471556
0.6143	Remote Similarity	NPC471565
0.6133	Remote Similarity	NPC160540
0.6129	Remote Similarity	NPC477458
0.6125	Remote Similarity	NPC123908
0.6125	Remote Similarity	NPC10080
0.6098	Remote Similarity	NPC281172
0.6098	Remote Similarity	NPC133652
0.6087	Remote Similarity	NPC474658
0.6066	Remote Similarity	NPC267110
0.6061	Remote Similarity	NPC281230
0.6061	Remote Similarity	NPC192843
0.6056	Remote Similarity	NPC248125
0.6056	Remote Similarity	NPC469446
0.6053	Remote Similarity	NPC315552
0.6034	Remote Similarity	NPC216921
0.6029	Remote Similarity	NPC143857
0.6029	Remote Similarity	NPC309408
0.6029	Remote Similarity	NPC229252
0.6027	Remote Similarity	NPC88877
0.6027	Remote Similarity	NPC474060
0.6027	Remote Similarity	NPC476591
0.6026	Remote Similarity	NPC478247
0.6026	Remote Similarity	NPC469510
0.6026	Remote Similarity	NPC23778
0.6026	Remote Similarity	NPC478246
0.6026	Remote Similarity	NPC478122
0.6024	Remote Similarity	NPC472009
0.6024	Remote Similarity	NPC203795
0.6	Remote Similarity	NPC95364
0.6	Remote Similarity	NPC297280
0.6	Remote Similarity	NPC475833
0.6	Remote Similarity	NPC100380
0.6	Remote Similarity	NPC287878
0.6	Remote Similarity	NPC128280
0.6	Remote Similarity	NPC316851
0.6	Remote Similarity	NPC286229
0.6	Remote Similarity	NPC142159
0.6	Remote Similarity	NPC471752
0.6	Remote Similarity	NPC173157
0.6	Remote Similarity	NPC4638
0.5977	Remote Similarity	NPC248193
0.5976	Remote Similarity	NPC469884
0.5974	Remote Similarity	NPC205615
0.5974	Remote Similarity	NPC110725
0.5974	Remote Similarity	NPC16279
0.5974	Remote Similarity	NPC256640
0.5972	Remote Similarity	NPC122627
0.5972	Remote Similarity	NPC106613
0.5968	Remote Similarity	NPC176819
0.5968	Remote Similarity	NPC107703
0.5968	Remote Similarity	NPC163984
0.5968	Remote Similarity	NPC58970
0.5955	Remote Similarity	NPC318082
0.5952	Remote Similarity	NPC472007
0.5952	Remote Similarity	NPC471739
0.5949	Remote Similarity	NPC291260
0.5949	Remote Similarity	NPC471299
0.5946	Remote Similarity	NPC477455
0.5942	Remote Similarity	NPC15193
0.5942	Remote Similarity	NPC64971
0.5938	Remote Similarity	NPC268564
0.5938	Remote Similarity	NPC37644
0.5932	Remote Similarity	NPC471753
0.593	Remote Similarity	NPC471399
0.593	Remote Similarity	NPC224270
0.593	Remote Similarity	NPC223093
0.5921	Remote Similarity	NPC122244
0.5915	Remote Similarity	NPC182794
0.5915	Remote Similarity	NPC282760
0.5909	Remote Similarity	NPC150717
0.5909	Remote Similarity	NPC473733
0.5904	Remote Similarity	NPC470177
0.5904	Remote Similarity	NPC242233
0.5904	Remote Similarity	NPC67081
0.5904	Remote Similarity	NPC471223
0.5897	Remote Similarity	NPC82666
0.5897	Remote Similarity	NPC97173
0.589	Remote Similarity	NPC470256
0.5882	Remote Similarity	NPC278202
0.5882	Remote Similarity	NPC472008
0.5882	Remote Similarity	NPC53454
0.5875	Remote Similarity	NPC91332
0.5875	Remote Similarity	NPC162741
0.5873	Remote Similarity	NPC64866
0.5873	Remote Similarity	NPC234829
0.5867	Remote Similarity	NPC133098
0.5867	Remote Similarity	NPC5734
0.5862	Remote Similarity	NPC146852
0.5862	Remote Similarity	NPC32944
0.5862	Remote Similarity	NPC166110
0.5862	Remote Similarity	NPC32552
0.5862	Remote Similarity	NPC193396
0.5857	Remote Similarity	NPC155849
0.5857	Remote Similarity	NPC68110
0.5854	Remote Similarity	NPC8091

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 NPC200831 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	3958
0.2-0.3	4058
0.3-0.4	721
0.4-0.5	224
0.5-0.6	33
0.6-0.7	5
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8779	Phase 3
0.8095	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3704	Approved
0.7077	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4756	Discovery
0.6792	Remote Similarity	NPD5783	Phase 3
0.6456	Remote Similarity	NPD6110	Phase 1
0.6282	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6109	Phase 1
0.6167	Remote Similarity	NPD5343	Approved
0.614	Remote Similarity	NPD9297	Discontinued
0.614	Remote Similarity	NPD9091	Suspended
0.6129	Remote Similarity	NPD6927	Phase 3
0.6056	Remote Similarity	NPD7331	Phase 2
0.5932	Remote Similarity	NPD6096	Approved
0.5932	Remote Similarity	NPD6097	Approved
0.5875	Remote Similarity	NPD4695	Discontinued
0.5833	Remote Similarity	NPD9090	Phase 3
0.5802	Remote Similarity	NPD5115	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD5737	Approved
0.5698	Remote Similarity	NPD6672	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