NPASS Compound

Structure

CID26500 OpenBabel06191715352D 23 22 0 0 1 0 0 0 0 0999 V2000 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 0.0000 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 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -10.3923 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 3 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 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 2.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 7 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.22
Volume:	355.926
LogP:	1.458
LogD:	1.121
LogS:	-3.759
# Rotatable Bonds:	14
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	0
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	3.726
Fsp3:	0.722
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.615
MDCK Permeability:	0.00020030245650559664
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.949
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	90.97948455810547%
Volume Distribution (VD):	0.352
Pgp-substrate:	3.4343314170837402%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.32
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.199
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.284
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	2.313
Half-life (T1/2):	0.909

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.386
Maximum Recommended Daily Dose:	0.253
Skin Sensitization:	0.635
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.235

Download Data

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

Natural Product: NPC26500

Natural Product ID:	NPC26500
*Common Name:**	9,12,13-Trihydroxyoctadeca-10(E),15(Z)-Dienoic Acid
IUPAC Name:	(10E,15Z)-9,12,13-trihydroxyoctadeca-10,15-dienoic acid
Synonyms:
Standard InCHIKey:	MKYUCBXUUSZMQB-MKZMYESJSA-N
Standard InCHI:	InChI=1S/C18H32O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h3,7,13-17,19-21H,2,4-6,8-12H2,1H3,(H,22,23)/b7-3-,14-13+
SMILES:	CC/C=CCC(C(/C=C/C(CCCCCCCC(=O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469620
PubChem CID:	44559173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic 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
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO32690	salsola tetrandra	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989538]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19731587]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9658577]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3813	Chaenomeles speciosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3813	Chaenomeles speciosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3813	Chaenomeles speciosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3813	Chaenomeles speciosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	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
MIC	5
Others	3

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	700.0	ug.mL-1	PMID[459977]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	>	700.0	ug ml-1	PMID[459977]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	700.0	ug.mL-1	PMID[459977]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	500.0	ug.mL-1	PMID[459977]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	>	700.0	ug ml-1	PMID[459977]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MBC	=	500.0	ug ml-1	PMID[459977]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	600.0	ug.mL-1	PMID[459977]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	400.0	ug.mL-1	PMID[459977]

☑ 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 NPC26500 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	164
0.1-0.2	1666
0.2-0.3	7244
0.3-0.4	17791
0.4-0.5	8865
0.5-0.6	5065
0.6-0.7	1523
0.7-0.8	332
0.8-0.85	19
0.85-0.9	20
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC99619
0.9194	High Similarity	NPC321838
0.9062	High Similarity	NPC255863
0.9062	High Similarity	NPC245947
0.9062	High Similarity	NPC136164
0.9032	High Similarity	NPC243532
0.8971	High Similarity	NPC325627
0.8906	High Similarity	NPC470320
0.8889	High Similarity	NPC201939
0.8788	High Similarity	NPC271921
0.8788	High Similarity	NPC104537
0.8788	High Similarity	NPC127091
0.8788	High Similarity	NPC148192
0.8788	High Similarity	NPC22101
0.8788	High Similarity	NPC330426
0.8769	High Similarity	NPC326268
0.8769	High Similarity	NPC318420
0.8657	High Similarity	NPC324981
0.8657	High Similarity	NPC48218
0.8657	High Similarity	NPC141481
0.8657	High Similarity	NPC473559
0.8615	High Similarity	NPC226592
0.8548	High Similarity	NPC323436
0.8529	High Similarity	NPC143396
0.8507	High Similarity	NPC473829
0.8507	High Similarity	NPC475443
0.8438	Intermediate Similarity	NPC327112
0.8429	Intermediate Similarity	NPC470435
0.8406	Intermediate Similarity	NPC42526
0.8406	Intermediate Similarity	NPC476660
0.8333	Intermediate Similarity	NPC328089
0.8333	Intermediate Similarity	NPC68343
0.831	Intermediate Similarity	NPC227396
0.8308	Intermediate Similarity	NPC477829
0.8281	Intermediate Similarity	NPC322186
0.8261	Intermediate Similarity	NPC473772
0.8235	Intermediate Similarity	NPC49863
0.8235	Intermediate Similarity	NPC478097
0.8235	Intermediate Similarity	NPC25298
0.8154	Intermediate Similarity	NPC328311
0.8095	Intermediate Similarity	NPC477201
0.8088	Intermediate Similarity	NPC328653
0.8082	Intermediate Similarity	NPC279537
0.8065	Intermediate Similarity	NPC261831
0.8065	Intermediate Similarity	NPC87564
0.8065	Intermediate Similarity	NPC6095
0.8065	Intermediate Similarity	NPC32467
0.8065	Intermediate Similarity	NPC25417
0.8065	Intermediate Similarity	NPC85813
0.8065	Intermediate Similarity	NPC154245
0.8065	Intermediate Similarity	NPC290563
0.8065	Intermediate Similarity	NPC88966
0.8065	Intermediate Similarity	NPC281972
0.8065	Intermediate Similarity	NPC424
0.8056	Intermediate Similarity	NPC474321
0.803	Intermediate Similarity	NPC475984
0.803	Intermediate Similarity	NPC328776
0.803	Intermediate Similarity	NPC320305
0.8	Intermediate Similarity	NPC130618
0.8	Intermediate Similarity	NPC470436
0.8	Intermediate Similarity	NPC329249
0.7971	Intermediate Similarity	NPC478100
0.7941	Intermediate Similarity	NPC478099
0.7941	Intermediate Similarity	NPC323477
0.7941	Intermediate Similarity	NPC317881
0.7941	Intermediate Similarity	NPC476655
0.7941	Intermediate Similarity	NPC476657
0.7941	Intermediate Similarity	NPC323045
0.7941	Intermediate Similarity	NPC478098
0.7941	Intermediate Similarity	NPC476654
0.7937	Intermediate Similarity	NPC52264
0.791	Intermediate Similarity	NPC470965
0.791	Intermediate Similarity	NPC29697
0.791	Intermediate Similarity	NPC54925
0.7903	Intermediate Similarity	NPC70387
0.7903	Intermediate Similarity	NPC139029
0.7903	Intermediate Similarity	NPC36061
0.7903	Intermediate Similarity	NPC294548
0.7903	Intermediate Similarity	NPC1813
0.7903	Intermediate Similarity	NPC321062
0.7879	Intermediate Similarity	NPC81896
0.7879	Intermediate Similarity	NPC321919
0.7867	Intermediate Similarity	NPC192006
0.7846	Intermediate Similarity	NPC34416
0.7838	Intermediate Similarity	NPC190400
0.7838	Intermediate Similarity	NPC49392
0.7826	Intermediate Similarity	NPC476659
0.7826	Intermediate Similarity	NPC478101
0.7826	Intermediate Similarity	NPC476656
0.7812	Intermediate Similarity	NPC18951
0.7792	Intermediate Similarity	NPC88735
0.7778	Intermediate Similarity	NPC137538
0.7761	Intermediate Similarity	NPC113293
0.7761	Intermediate Similarity	NPC271282
0.7761	Intermediate Similarity	NPC66460
0.7761	Intermediate Similarity	NPC325929
0.7746	Intermediate Similarity	NPC236208
0.7746	Intermediate Similarity	NPC317583
0.7742	Intermediate Similarity	NPC281245
0.7742	Intermediate Similarity	NPC92114
0.7727	Intermediate Similarity	NPC274927
0.7727	Intermediate Similarity	NPC322002
0.7727	Intermediate Similarity	NPC106851
0.7703	Intermediate Similarity	NPC260396
0.7692	Intermediate Similarity	NPC7414
0.7692	Intermediate Similarity	NPC474252
0.7681	Intermediate Similarity	NPC320642
0.7662	Intermediate Similarity	NPC115418
0.7656	Intermediate Similarity	NPC128061
0.7656	Intermediate Similarity	NPC10316
0.7656	Intermediate Similarity	NPC28779
0.7656	Intermediate Similarity	NPC223677
0.7656	Intermediate Similarity	NPC200845
0.7632	Intermediate Similarity	NPC260814
0.7632	Intermediate Similarity	NPC39547
0.7632	Intermediate Similarity	NPC27949
0.7632	Intermediate Similarity	NPC323249
0.7619	Intermediate Similarity	NPC139545
0.7619	Intermediate Similarity	NPC39633
0.7619	Intermediate Similarity	NPC309606
0.7606	Intermediate Similarity	NPC209327
0.7606	Intermediate Similarity	NPC273508
0.7595	Intermediate Similarity	NPC253801
0.7581	Intermediate Similarity	NPC262968
0.7564	Intermediate Similarity	NPC47031
0.7538	Intermediate Similarity	NPC187777
0.7538	Intermediate Similarity	NPC179764
0.7536	Intermediate Similarity	NPC476658
0.7532	Intermediate Similarity	NPC201225
0.7531	Intermediate Similarity	NPC279267
0.7531	Intermediate Similarity	NPC69082
0.75	Intermediate Similarity	NPC475982
0.75	Intermediate Similarity	NPC281296
0.75	Intermediate Similarity	NPC474776
0.75	Intermediate Similarity	NPC40082
0.7468	Intermediate Similarity	NPC73310
0.7468	Intermediate Similarity	NPC65930
0.7468	Intermediate Similarity	NPC475159
0.7468	Intermediate Similarity	NPC329829
0.7468	Intermediate Similarity	NPC180363
0.7468	Intermediate Similarity	NPC145914
0.7468	Intermediate Similarity	NPC473529
0.7468	Intermediate Similarity	NPC94875
0.7468	Intermediate Similarity	NPC131002
0.7468	Intermediate Similarity	NPC473780
0.7468	Intermediate Similarity	NPC473712
0.7468	Intermediate Similarity	NPC11332
0.7463	Intermediate Similarity	NPC318306
0.7439	Intermediate Similarity	NPC179659
0.7432	Intermediate Similarity	NPC329890
0.7429	Intermediate Similarity	NPC176215
0.7429	Intermediate Similarity	NPC296436
0.7424	Intermediate Similarity	NPC225929
0.7424	Intermediate Similarity	NPC323498
0.7424	Intermediate Similarity	NPC211752
0.7424	Intermediate Similarity	NPC323597
0.7419	Intermediate Similarity	NPC59051
0.7419	Intermediate Similarity	NPC224227
0.7407	Intermediate Similarity	NPC82795
0.7407	Intermediate Similarity	NPC223871
0.7407	Intermediate Similarity	NPC283085
0.7407	Intermediate Similarity	NPC473669
0.7407	Intermediate Similarity	NPC473478
0.7407	Intermediate Similarity	NPC107986
0.7407	Intermediate Similarity	NPC286338
0.7407	Intermediate Similarity	NPC1083
0.7407	Intermediate Similarity	NPC66346
0.7407	Intermediate Similarity	NPC231009
0.7407	Intermediate Similarity	NPC473651
0.7407	Intermediate Similarity	NPC110710
0.7407	Intermediate Similarity	NPC132496
0.7407	Intermediate Similarity	NPC322529
0.7407	Intermediate Similarity	NPC103284
0.7407	Intermediate Similarity	NPC137033
0.7407	Intermediate Similarity	NPC182383
0.7403	Intermediate Similarity	NPC248775
0.7403	Intermediate Similarity	NPC218817
0.7403	Intermediate Similarity	NPC121200
0.7403	Intermediate Similarity	NPC11796
0.7397	Intermediate Similarity	NPC4299
0.7385	Intermediate Similarity	NPC228473
0.7385	Intermediate Similarity	NPC274290
0.7385	Intermediate Similarity	NPC54766
0.7385	Intermediate Similarity	NPC473863
0.7381	Intermediate Similarity	NPC313670
0.7375	Intermediate Similarity	NPC477786
0.7375	Intermediate Similarity	NPC477785
0.7375	Intermediate Similarity	NPC144415
0.7375	Intermediate Similarity	NPC477784
0.7353	Intermediate Similarity	NPC174447
0.7353	Intermediate Similarity	NPC143857
0.7353	Intermediate Similarity	NPC122521
0.7353	Intermediate Similarity	NPC235242
0.7353	Intermediate Similarity	NPC251042
0.7353	Intermediate Similarity	NPC229252
0.7344	Intermediate Similarity	NPC71761
0.7342	Intermediate Similarity	NPC316844
0.7342	Intermediate Similarity	NPC236649
0.7342	Intermediate Similarity	NPC21693
0.7333	Intermediate Similarity	NPC92558

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 NPC26500 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	2502
0.2-0.3	3727
0.3-0.4	1978
0.4-0.5	619
0.5-0.6	127
0.6-0.7	38
0.7-0.8	24
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8906	High Similarity	NPD3197	Phase 1
0.8438	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3195	Phase 2
0.8065	Intermediate Similarity	NPD3194	Approved
0.8065	Intermediate Similarity	NPD3196	Approved
0.8065	Intermediate Similarity	NPD4266	Approved
0.7903	Intermediate Similarity	NPD3172	Approved
0.7692	Intermediate Similarity	NPD4269	Approved
0.7692	Intermediate Similarity	NPD4270	Approved
0.7662	Intermediate Similarity	NPD4252	Approved
0.7632	Intermediate Similarity	NPD4268	Approved
0.7632	Intermediate Similarity	NPD4271	Approved
0.7632	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5362	Discontinued
0.7595	Intermediate Similarity	NPD7154	Phase 3
0.7581	Intermediate Similarity	NPD28	Approved
0.7581	Intermediate Similarity	NPD29	Approved
0.7436	Intermediate Similarity	NPD4820	Approved
0.7436	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4819	Approved
0.7436	Intermediate Similarity	NPD4821	Approved
0.7436	Intermediate Similarity	NPD4822	Approved
0.7407	Intermediate Similarity	NPD5363	Approved
0.7317	Intermediate Similarity	NPD5786	Approved
0.7294	Intermediate Similarity	NPD7983	Approved
0.7258	Intermediate Similarity	NPD3173	Approved
0.716	Intermediate Similarity	NPD5331	Approved
0.716	Intermediate Similarity	NPD5332	Approved
0.7125	Intermediate Similarity	NPD5369	Approved
0.7125	Intermediate Similarity	NPD4790	Discontinued
0.7097	Intermediate Similarity	NPD622	Approved
0.7059	Intermediate Similarity	NPD6109	Phase 1
0.7051	Intermediate Similarity	NPD4756	Discovery
0.7	Intermediate Similarity	NPD5368	Approved
0.6977	Remote Similarity	NPD6698	Approved
0.6977	Remote Similarity	NPD5785	Approved
0.6977	Remote Similarity	NPD46	Approved
0.697	Remote Similarity	NPD3728	Approved
0.697	Remote Similarity	NPD3730	Approved
0.686	Remote Similarity	NPD5370	Suspended
0.6829	Remote Similarity	NPD6435	Approved
0.6824	Remote Similarity	NPD4251	Approved
0.6824	Remote Similarity	NPD4250	Approved
0.6818	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5779	Approved
0.6774	Remote Similarity	NPD39	Approved
0.6774	Remote Similarity	NPD4222	Approved
0.6774	Remote Similarity	NPD3174	Discontinued
0.6706	Remote Similarity	NPD4249	Approved
0.6705	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7839	Suspended
0.6562	Remote Similarity	NPD5343	Approved
0.6543	Remote Similarity	NPD3732	Approved
0.6477	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6101	Approved
0.6471	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5326	Phase 3
0.6438	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7838	Discovery
0.64	Remote Similarity	NPD3704	Approved
0.6375	Remote Similarity	NPD8039	Approved
0.6333	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD4265	Approved
0.6207	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7331	Phase 2
0.6184	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7637	Suspended
0.6136	Remote Similarity	NPD6422	Discontinued
0.6133	Remote Similarity	NPD7909	Approved
0.6129	Remote Similarity	NPD2270	Approved
0.6111	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD2699	Approved
0.6094	Remote Similarity	NPD6096	Approved
0.6094	Remote Similarity	NPD6097	Approved
0.6092	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD6927	Phase 3
0.6	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6371	Approved
0.598	Remote Similarity	NPD6421	Discontinued
0.5978	Remote Similarity	NPD7515	Phase 2
0.5977	Remote Similarity	NPD6110	Phase 1
0.5957	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4225	Approved
0.5938	Remote Similarity	NPD9495	Approved
0.5914	Remote Similarity	NPD6399	Phase 3
0.5909	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4786	Approved
0.5862	Remote Similarity	NPD3667	Approved
0.5846	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6420	Discontinued
0.5816	Remote Similarity	NPD5344	Discontinued
0.5811	Remote Similarity	NPD3198	Approved
0.5806	Remote Similarity	NPD9448	Phase 2
0.5806	Remote Similarity	NPD633	Phase 3
0.5806	Remote Similarity	NPD9655	Approved
0.5794	Remote Similarity	NPD7115	Discovery
0.5784	Remote Similarity	NPD6686	Approved
0.5783	Remote Similarity	NPD8264	Approved
0.5769	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD4220	Pre-registration
0.5714	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD7640	Approved
0.57	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.57	Remote Similarity	NPD6647	Phase 2
0.5694	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD342	Phase 1
0.5684	Remote Similarity	NPD7748	Approved
0.5682	Remote Similarity	NPD5209	Approved
0.5682	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD368	Approved
0.5645	Remote Similarity	NPD3206	Approved
0.5641	Remote Similarity	NPD7341	Phase 2
0.5612	Remote Similarity	NPD7638	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