NPASS Compound

Structure

NPC484569 OpenBabel06302215402D 27 28 0 0 1 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -0.8660 2.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 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 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 1.7321 -2.0000 0.0000 C 0 0 2 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 -2.0000 0.0000 C 0 0 1 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 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 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 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 -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 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 10 26 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 25 2 0 0 0 0 14 13 1 6 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 1 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.1
Volume:	296.495
LogP:	3.267
LogD:	3.236
LogS:	-4.422
# Rotatable Bonds:	2
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.924
Synthetic Accessibility Score:	2.897
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.005
MDCK Permeability:	2.5971605282393284e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	98.55516815185547%
Volume Distribution (VD):	0.917
Pgp-substrate:	2.0835390090942383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.702
CYP2C19-inhibitor:	0.971
CYP2C19-substrate:	0.5
CYP2C9-inhibitor:	0.743
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.969
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.537

ADMET: Excretion

Clearance (CL):	15.038
Half-life (T1/2):	0.381

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.237
Drug-inuced Liver Injury (DILI):	0.569
AMES Toxicity:	0.75
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.855
Carcinogencity:	0.905
Eye Corrosion:	0.003
Eye Irritation:	0.481
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC484569

Natural Product ID:	NPC484569
*Common Name:**	YNZFFALZMRAPHQ-SYYKKAFVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YNZFFALZMRAPHQ-SYYKKAFVSA-N
Standard InCHI:	InChI=1S/C24H40O3/c1-4-5-6-7-14-24(2,3)19-11-13-21(23(27)16-19)22-17-20(26)12-10-18(22)9-8-15-25/h11,13,16,18,20,22,25-27H,4-10,12,14-15,17H2,1-3H3/t18-,20-,22-/m1/s1
SMILES:	CCCCCCC(C)(C)c1ccc([C@@H]2C[C@@H](CC[C@H]2CCCO)O)c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	104895
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002099] Cyclohexylphenols

*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
NPO41029	Perovskia atriplicifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26035635]
NPO40469	Cannabis sativa variety (FM2)	Strain	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31891265]

☑ 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
EC50	95
ED50	2
IC50	26
Kd	2
Ki	56
Others	35

Activity Type	# Activity
Cell Line	3
Individual Protein	191
Organism	11
Others	9
Protein Family	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	5.2	nM	PMID[11960486]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	5.2	nM	PMID[10465552]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	14.4	nM	PMID[10465552]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	27.5	nM	PMID[10465552]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	Ki	=	1.3	nM	PMID[11741470]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.15	nM	PMID[11741470]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	Ki	=	1.4	nM	PMID[16078824]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	13.0	nM	PMID[16213718]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.7	nM	PMID[16213718]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	15.4	nM	PMID[16392793]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	=	145.6	%	PMID[16392793]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	6.1	nM	PMID[16392793]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	EC50	=	100.0	nM	PMID[16420041]
NPT1169	Individual Protein	Cannabinoid CB2 receptor	Mus musculus	Ki	=	1.11	nM	PMID[17149879]
NPT1170	Individual Protein	Cannabinoid CB1 receptor	Mus musculus	Ki	=	1.5	nM	PMID[17149879]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	=	103.0	%	PMID[17149879]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	0.77	nM	PMID[17630726]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	IC50	=	1.3	nM	PMID[17630726]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	0.35	nM	PMID[17630726]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	0.28	nM	PMID[17630726]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	=	230.5	%	PMID[17915849]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	2.512	nM	PMID[17027269]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	158.49	nM	PMID[17027269]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	2.1	nM	PMID[17884496]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	IC50	=	0.82	nM	PMID[17884496]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	0.86	nM	PMID[17884496]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	Ki	=	0.58	nM	PMID[17919913]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.69	nM	PMID[17919913]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	0.69	nM	PMID[17919913]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	IC50	=	0.82	nM	PMID[18006322]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	2.1	nM	PMID[18006322]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	0.86	nM	PMID[18006322]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	5.0	nM	PMID[18666769]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	2.7	nM	PMID[18666769]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	1.8	nM	PMID[18666769]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	2.28	nM	PMID[18680277]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	0.43	nM	PMID[18680277]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	0.26	nM	PMID[18680277]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	0.88	nM	PMID[18680277]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	EC50	=	0.16	nM	PMID[18680277]
NPT3955	Individual Protein	Cannabinoid CB2 receptor	Rattus norvegicus	EC50	=	0.34	nM	PMID[18680277]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	10.3	nM	PMID[19115816]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	8.66	nM	PMID[19115816]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	1.2	nM	PMID[18983139]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	1.4	nM	PMID[18983139]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.439	nM	PMID[19278853]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	Ki	=	1.24	nM	PMID[19278853]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	=	228.0	%	PMID[19278853]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	1.37	nM	PMID[19278853]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	Activity	=	169.0	%	PMID[19278853]
NPT472	Individual Protein	Vanilloid receptor	Homo sapiens	EC50	=	10.0	nM	PMID[19361197]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	=	100.0	%	PMID[19500981]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	0.13	nM	PMID[20047779]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.68	nM	PMID[20218623]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.58	nM	PMID[20218623]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	1.36	nM	PMID[20688519]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	1.259	nM	PMID[20688519]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.62	nM	PMID[20688519]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	19.95	nM	PMID[21074434]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.3162	nM	PMID[21074434]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.3162	nM	PMID[21074434]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	15.4	nM	PMID[20979417]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	6.1	nM	PMID[20979417]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.6	nM	PMID[21183257]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.6	nM	PMID[21183257]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	19.95	nM	PMID[21316962]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.3162	nM	PMID[21316962]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.3162	nM	PMID[21316962]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	=	104.3	%	PMID[21667972]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	=	102.6	%	PMID[21667972]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	1.259	nM	PMID[21885167]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.5012	nM	PMID[21885167]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	0.631	nM	PMID[21885167]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	0.7943	nM	PMID[21885167]
NPT492	Cell Line	Caco-2	Homo sapiens	Ratio	=	1.92	n.a.	PMID[21885167]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	IC50	=	4.0	nM	PMID[21962575]
NPT1170	Individual Protein	Cannabinoid CB1 receptor	Mus musculus	EC50	=	42.0	nM	PMID[22044209]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	25.12	nM	PMID[22421020]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	7.4	nM	PMID[23085772]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	0.7	nM	PMID[23085772]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	1.0	nM	PMID[22916707]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	2.28	nM	PMID[22916707]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	1.42	nM	PMID[22916707]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	1.28	nM	PMID[22916707]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC	=	23.29	nM	PMID[23072339]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	Ki	=	7.7	nM	DOI[10.1007/s00044-012-9991-3]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	47.1	nM	PMID[23406429]
NPT4120	Individual Protein	G-protein coupled receptor 55	Homo sapiens	Kb	=	1890.0	nM	PMID[24900561]
NPT4120	Individual Protein	G-protein coupled receptor 55	Homo sapiens	Inhibition	=	92.0	%	PMID[24900561]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	1.0	nM	PMID[24900561]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	2.28	nM	PMID[24900561]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	1.42	nM	PMID[24900561]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	1.28	nM	PMID[24900561]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	11.0	nM	PMID[24729834]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Inhibition	=	90.3	%	PMID[23659286]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Inhibition	=	88.8	%	PMID[23659286]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Inhibition	=	37.0	%	PMID[23631463]
NPT1170	Individual Protein	Cannabinoid CB1 receptor	Mus musculus	Inhibition	=	45.0	%	PMID[23631463]
NPT4119	Individual Protein	N-arachidonyl glycine receptor	Homo sapiens	IC50	=	5990.0	nM	PMID[23679955]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	0.21	nM	PMID[23582449]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.27	nM	PMID[23466604]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	0.31	nM	PMID[23466604]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	1.3	nM	PMID[23849204]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	15.4	nM	PMID[23849204]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	4.21	nM	PMID[23855811]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	4.13	nM	PMID[24125850]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	27.0	nM	PMID[24139843]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	=	156.0	%	DOI[10.1039/C3MD00394A]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	Activity	=	132.0	%	DOI[10.1039/C3MD00394A]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	=	161.0	%	DOI[10.1039/C3MD00394A]
NPT4119	Individual Protein	N-arachidonyl glycine receptor	Homo sapiens	EC50	=	5990.0	nM	DOI[10.1039/C3MD00394A]
NPT4120	Individual Protein	G-protein coupled receptor 55	Homo sapiens	EC50	=	1610.0	nM	DOI[10.1039/C3MD00394A]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.58	nM	PMID[23865723]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.69	nM	PMID[23865723]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.3162	nM	DOI[10.1039/C0MD00022A]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.3162	nM	DOI[10.1039/C0MD00022A]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	19.95	nM	DOI[10.1039/C0MD00022A]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.52	nM	PMID[25072877]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.89	nM	PMID[25072877]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	9.3	nM	PMID[25072877]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	3.9	nM	PMID[25072877]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	12.88	nM	PMID[25096297]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	8.0	nM	PMID[25096297]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	40.74	nM	PMID[24984935]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	12.88	nM	PMID[24984935]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	1.43	nM	PMID[25065940]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	2.37	nM	PMID[25065940]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	7.0	nM	PMID[25644673]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	26.0	nM	PMID[25644673]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	=	102.6	%	PMID[26035635]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	=	104.3	%	PMID[26035635]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	30.7	nM	PMID[26151231]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	7.93	nM	PMID[26151231]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	0.576	nM	PMID[26203658]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	0.437	nM	PMID[26203658]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	4.9	nM	PMID[26529344]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	0.9	nM	PMID[26988801]
NPT1170	Individual Protein	Cannabinoid CB1 receptor	Mus musculus	Ki	=	0.62	nM	PMID[27240274]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	9.73	nM	PMID[27240274]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	0.9	nM	PMID[27876250]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	30.02	nM	PMID[28626532]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	28.62	nM	PMID[28626532]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Kd	=	0.5	nM	PMID[28284861]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Kd	=	0.59	nM	PMID[28284861]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	30.02	nM	PMID[28651225]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	28.62	nM	PMID[28651225]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	0.9	nM	PMID[29856219]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	1.73	nM	PMID[29856219]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	5.5	nM	PMID[29793210]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	5.5	nM	PMID[29793210]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	2.0	nM	PMID[30122284]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	EC50	=	3.0	nM	PMID[30122284]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.5	nM	PMID[29232588]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.69	nM	PMID[29232588]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.7	nM	PMID[29232588]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	0.2	nM	PMID[29232588]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	5.6	nM	PMID[29407590]
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	98.0	%	PMID[29407590]
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	99.2	%	PMID[29407590]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ki	=	8.44	nM	PMID[30108881]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	9.26	nM	PMID[30108881]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	1.7	nM	PMID[31891265]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ki	=	0.93	nM	PMID[31891265]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	21.88	nM	PMID[31319265]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	22.0	nM	PMID[31319265]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	63.0	nM	PMID[31319265]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	63.1	nM	PMID[31319265]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	3.0	nM	PMID[29939744]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	3.2	nM	PMID[29939744]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ratio EC50	=	1.0	n.a.	PMID[29939744]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	20.0	nM	PMID[32904145]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	55.0	nM	PMID[32904145]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	EC50	=	18.0	nM	PMID[31756109]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	1.4	nM	PMID[31756109]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	IC50	=	8.3	nM	PMID[27309150]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	1.66	nM	PMID[32340793]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	EC50	=	7.3	nM	PMID[33636308]
NPT1361	Individual Protein	Cannabinoid CB1 receptor	Rattus norvegicus	EC50	=	73.0	nM	PMID[33636308]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	1.4	nM	PMID[33636308]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	1.995	nM	PMID[33550084]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	6.31	nM	PMID[33550084]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	5.754	nM	PMID[33550084]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Ratio	=	4.51	n.a.	PMID[33550084]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	37.15	nM	PMID[33550084]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Ratio	=	3.7	n.a.	PMID[33550084]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	22.0	nM	PMID[33321261]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	21.38	nM	PMID[33321261]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	56.0	nM	PMID[33321261]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	56.23	nM	PMID[33321261]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	42.0	nM	PMID[33382613]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	35.0	nM	PMID[33382613]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	16.3	nM	PMID[33382613]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	EC50	=	0.3	nM	PMID[33382613]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	EC50	=	9.8	nM	PMID[33382613]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	EC50	=	100.0	nM	PMID[9876105]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	EC50	=	19952623.15	nM	PMID[9876105]
NPT1362	Protein Family	Cannabinoid receptor	Homo sapiens	Ki	=	0.924	nM	DOI[10.1016/S0960-894X(01)80155-4]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	0.55	umol.kg-1	DOI[10.1016/S0960-894X(01)80155-4]
NPT2	Others	Unspecified		Ki	=	2.6	nM	PMID[16078824]
NPT5404	Protein Family	Cannabinoid receptor	Mus musculus	Ratio Ki	=	1.4	n.a.	PMID[17149879]
NPT2	Others	Unspecified		Ratio Ki	=	0.8	n.a.	PMID[17919913]
NPT2	Others	Unspecified		Ratio Ki	=	0.46	n.a.	PMID[20688519]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7943.28	nM	PMID[19734910]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6309.57	nM	PMID[19734910]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5011.87	nM	PMID[19734910]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2511.89	nM	PMID[19734910]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1995.26	nM	PMID[19734910]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	0.00011	umol.kg-1	PMID[21074434]
NPT2	Others	Unspecified		Ratio Ki	=	0.4	n.a.	PMID[21885167]
NPT2	Others	Unspecified		Ratio Ki	=	0.84	n.a.	PMID[23865723]
NPT2	Others	Unspecified		Ratio EC50	=	0.3	n.a.	PMID[25644673]
NPT2	Others	Unspecified		Ratio EC50	=	0.258	n.a.	PMID[26151231]
NPT2	Others	Unspecified		Ratio EC50	=	1.0	n.a.	PMID[28626532]
NPT2	Others	Unspecified		Ratio EC50	=	1.6	n.a.	PMID[28651225]

☑ 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 NPC484569 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	269
0.1-0.2	1280
0.2-0.3	2621
0.3-0.4	8199
0.4-0.5	11064
0.5-0.6	10572
0.6-0.7	6916
0.7-0.8	1512
0.8-0.85	186
0.85-0.9	55
0.9-0.95	22
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID

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 NPC484569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	828
0.2-0.3	1361
0.3-0.4	2766
0.4-0.5	2070
0.5-0.6	1291
0.6-0.7	474
0.7-0.8	86
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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