NPASS Compound

Structure

CID226066 OpenBabel06191716022D 24 24 0 0 0 0 0 0 0 0999 V2000 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 -4.3301 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 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 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 -8.6603 -3.0000 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 0.0000 -0.0000 0.0000 C 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 -7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 9 1 0 0 0 0 7 10 2 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 17 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 22 1 0 0 0 0 16 24 1 0 0 0 0 19 21 2 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.24
Volume:	382.273
LogP:	4.339
LogD:	3.975
LogS:	-5.029
# Rotatable Bonds:	7
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	3.17
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.821
MDCK Permeability:	2.5982701117754914e-05
Pgp-inhibitor:	0.059
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	96.92984771728516%
Volume Distribution (VD):	2.11
Pgp-substrate:	6.355440616607666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.807
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.706
CYP2C9-substrate:	0.994
CYP2D6-inhibitor:	0.972
CYP2D6-substrate:	0.944
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	1.629
Half-life (T1/2):	0.41

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.239
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.744
Skin Sensitization:	0.424
Carcinogencity:	0.819
Eye Corrosion:	0.027
Eye Irritation:	0.878
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC226066

Natural Product ID:	NPC226066
*Common Name:**	Retinyl Acetate
IUPAC Name:	[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetate
Synonyms:	Retinyl Acetate
Standard InCHIKey:	QGNJRVVDBSJHIZ-QHLGVNSISA-N
Standard InCHI:	InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9+,18-14+
SMILES:	CC(=O)OC/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486193
PubChem CID:	638034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001606] Retinoids

*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
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	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
AC50	3
ED50	1
IC50	2
Ki	2
Others	12
Potency	123

Activity Type	# Activity
Cell Line	26
Individual Protein	53
ORGANISM	5
Others	57
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	79432.8	nM	PMID[496721]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	50118.7	nM	PMID[496721]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	39810.7	nM	PMID[496721]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	3548.1	nM	PMID[496721]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	35481.3	nM	PMID[496724]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	8912.5	nM	PMID[496723]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	63095.7	nM	PMID[496721]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	28183.8	nM	PMID[496723]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	31622.8	nM	PMID[496724]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[496724]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	6309.6	nM	PMID[496722]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	39810.7	nM	PMID[496721]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	25118.9	nM	PMID[496721]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[496724]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[496723]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[496723]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[496724]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[496725]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[496721]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[496725]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[496721]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	42163.2	nM	PMID[496721]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	54482.7	nM	PMID[496725]
NPT158	Individual Protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Potency	n.a.	44668.4	nM	PMID[496721]
NPT158	Individual Protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Potency	n.a.	44668.4	nM	PMID[496725]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	33498.3	nM	PMID[496726]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[496724]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29855.4	nM	PMID[496726]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[496724]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	66824.2	nM	PMID[496721]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	47794.3	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	66919	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	43646.5	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	59641.6	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	33488.9	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	53626.1	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	54947.7	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	53626.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		ED50	=	10.0	uM	PMID[496720]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	39810.7	nM	PMID[496721]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	25118.9	nM	PMID[496722]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	35481.3	nM	PMID[496723]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	14125.4	nM	PMID[496721]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	22387.2	nM	PMID[496724]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	18869.9	nM	PMID[496723]
NPT698	Individual Protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	1683.4	nM	PMID[496724]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	23.53	%	PMID[496727]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	IC50	=	5011.87	nM	PMID[496727]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Ki	=	3890.0	nM	PMID[496727]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	19.44	%	PMID[496727]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	IC50	=	2238.72	nM	PMID[496727]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Ki	=	1220.0	nM	PMID[496727]
NPT610	Others	Molecular identity unknown		Potency	n.a.	2238.7	nM	PMID[496725]
NPT610	Others	Molecular identity unknown		Potency	n.a.	14125.4	nM	PMID[496721]
NPT2	Others	Unspecified		AC50	n.a.	8912.5	nM	PMID[496728]
NPT2	Others	Unspecified		Ac50	n.a.	8.913	uM	PMID[496728]
NPT2	Others	Unspecified		Ac50	n.a.	15.85	uM	PMID[496728]
NPT2	Others	Unspecified		AC50	n.a.	15848.9	nM	PMID[496728]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-5.54	%	PMID[496729]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-42.04	%	PMID[496730]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	5.169	%	PMID[496731]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.48	%	PMID[496732]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.14	%	PMID[496733]
NPT2	Others	Unspecified		Potency	n.a.	33827.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	11882.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	53626.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54947.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48972.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	66919	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	29849.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	75084.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	37964.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	34669.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	298.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	47794.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	60169.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10699.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	59641.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	26832.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	16930.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43646.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	943.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	47375	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21875.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	23710.1	nM	PubChem BioAssay data set

☑ 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 NPC226066 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	1795
0.2-0.3	11197
0.3-0.4	16791
0.4-0.5	8202
0.5-0.6	3877
0.6-0.7	594
0.7-0.8	69
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.873	High Similarity	NPC329698
0.8551	High Similarity	NPC228978
0.85	High Similarity	NPC96663
0.8125	Intermediate Similarity	NPC326645
0.8125	Intermediate Similarity	NPC329416
0.8125	Intermediate Similarity	NPC317025
0.8125	Intermediate Similarity	NPC317177
0.8116	Intermediate Similarity	NPC181587
0.8116	Intermediate Similarity	NPC257618
0.8	Intermediate Similarity	NPC476490
0.8	Intermediate Similarity	NPC16349
0.8	Intermediate Similarity	NPC222244
0.8	Intermediate Similarity	NPC476489
0.7917	Intermediate Similarity	NPC4509
0.791	Intermediate Similarity	NPC185587
0.7879	Intermediate Similarity	NPC34883
0.7794	Intermediate Similarity	NPC254886
0.7763	Intermediate Similarity	NPC324170
0.7746	Intermediate Similarity	NPC276336
0.7671	Intermediate Similarity	NPC27205
0.7619	Intermediate Similarity	NPC55412
0.7619	Intermediate Similarity	NPC249645
0.7581	Intermediate Similarity	NPC269615
0.7568	Intermediate Similarity	NPC262747
0.7568	Intermediate Similarity	NPC473756
0.7541	Intermediate Similarity	NPC106531
0.7532	Intermediate Similarity	NPC268122
0.75	Intermediate Similarity	NPC321568
0.75	Intermediate Similarity	NPC208749
0.75	Intermediate Similarity	NPC281986
0.75	Intermediate Similarity	NPC22019
0.75	Intermediate Similarity	NPC268827
0.7467	Intermediate Similarity	NPC474816
0.7467	Intermediate Similarity	NPC209135
0.7467	Intermediate Similarity	NPC474005
0.7465	Intermediate Similarity	NPC469660
0.7436	Intermediate Similarity	NPC118423
0.7424	Intermediate Similarity	NPC19241
0.7375	Intermediate Similarity	NPC211892
0.7368	Intermediate Similarity	NPC242767
0.7368	Intermediate Similarity	NPC471299
0.7342	Intermediate Similarity	NPC470800
0.7308	Intermediate Similarity	NPC16321
0.7308	Intermediate Similarity	NPC94200
0.7297	Intermediate Similarity	NPC65650
0.7288	Intermediate Similarity	NPC197467
0.7286	Intermediate Similarity	NPC472266
0.7273	Intermediate Similarity	NPC233332
0.725	Intermediate Similarity	NPC329630
0.7246	Intermediate Similarity	NPC182794
0.7237	Intermediate Similarity	NPC105197
0.7237	Intermediate Similarity	NPC471220
0.7222	Intermediate Similarity	NPC64234
0.7222	Intermediate Similarity	NPC37929
0.7215	Intermediate Similarity	NPC474809
0.7206	Intermediate Similarity	NPC210303
0.7206	Intermediate Similarity	NPC179087
0.7206	Intermediate Similarity	NPC155849
0.7206	Intermediate Similarity	NPC44343
0.7179	Intermediate Similarity	NPC25554
0.7179	Intermediate Similarity	NPC475944
0.7164	Intermediate Similarity	NPC299730
0.7164	Intermediate Similarity	NPC127824
0.716	Intermediate Similarity	NPC168248
0.7143	Intermediate Similarity	NPC242945
0.7143	Intermediate Similarity	NPC158565
0.7143	Intermediate Similarity	NPC191233
0.7143	Intermediate Similarity	NPC259156
0.7143	Intermediate Similarity	NPC190211
0.7125	Intermediate Similarity	NPC471301
0.7119	Intermediate Similarity	NPC26600
0.7119	Intermediate Similarity	NPC47946
0.7108	Intermediate Similarity	NPC284561
0.7105	Intermediate Similarity	NPC473825
0.7105	Intermediate Similarity	NPC54996
0.7089	Intermediate Similarity	NPC471298
0.7089	Intermediate Similarity	NPC471218
0.7089	Intermediate Similarity	NPC323251
0.7083	Intermediate Similarity	NPC269841
0.7083	Intermediate Similarity	NPC101622
0.7083	Intermediate Similarity	NPC232812
0.7073	Intermediate Similarity	NPC125925
0.7051	Intermediate Similarity	NPC469802
0.7031	Intermediate Similarity	NPC478120
0.7013	Intermediate Similarity	NPC184737
0.7013	Intermediate Similarity	NPC4827
0.7	Intermediate Similarity	NPC471297
0.7	Intermediate Similarity	NPC474790
0.7	Intermediate Similarity	NPC474193
0.7	Intermediate Similarity	NPC23748
0.7	Intermediate Similarity	NPC474976
0.7	Intermediate Similarity	NPC107258
0.7	Intermediate Similarity	NPC477124
0.7	Intermediate Similarity	NPC220766
0.7	Intermediate Similarity	NPC49208
0.7	Intermediate Similarity	NPC12283
0.7	Intermediate Similarity	NPC472440
0.6988	Remote Similarity	NPC196407
0.6988	Remote Similarity	NPC24816
0.6988	Remote Similarity	NPC473879
0.6986	Remote Similarity	NPC4299
0.6986	Remote Similarity	NPC329904
0.6986	Remote Similarity	NPC473361
0.6974	Remote Similarity	NPC301525
0.697	Remote Similarity	NPC471277
0.697	Remote Similarity	NPC471279
0.6962	Remote Similarity	NPC14203
0.6962	Remote Similarity	NPC229584
0.6957	Remote Similarity	NPC217940
0.6944	Remote Similarity	NPC276290
0.6944	Remote Similarity	NPC476945
0.6933	Remote Similarity	NPC477204
0.6933	Remote Similarity	NPC306928
0.6933	Remote Similarity	NPC104644
0.6933	Remote Similarity	NPC20025
0.6923	Remote Similarity	NPC471537
0.6923	Remote Similarity	NPC478117
0.6914	Remote Similarity	NPC126518
0.6914	Remote Similarity	NPC474865
0.6914	Remote Similarity	NPC31086
0.6905	Remote Similarity	NPC471654
0.6905	Remote Similarity	NPC474844
0.6901	Remote Similarity	NPC255781
0.6892	Remote Similarity	NPC472254
0.6892	Remote Similarity	NPC477084
0.6875	Remote Similarity	NPC295777
0.6875	Remote Similarity	NPC69898
0.6867	Remote Similarity	NPC199382
0.6857	Remote Similarity	NPC4638
0.6857	Remote Similarity	NPC469723
0.6849	Remote Similarity	NPC470693
0.6849	Remote Similarity	NPC151481
0.6842	Remote Similarity	NPC68624
0.6835	Remote Similarity	NPC269791
0.6835	Remote Similarity	NPC160582
0.6835	Remote Similarity	NPC195424
0.6829	Remote Similarity	NPC474860
0.6829	Remote Similarity	NPC163606
0.6829	Remote Similarity	NPC35933
0.6829	Remote Similarity	NPC471300
0.6829	Remote Similarity	NPC472442
0.6806	Remote Similarity	NPC21998
0.6806	Remote Similarity	NPC225272
0.68	Remote Similarity	NPC135703
0.679	Remote Similarity	NPC42476
0.679	Remote Similarity	NPC30502
0.679	Remote Similarity	NPC469
0.679	Remote Similarity	NPC16488
0.679	Remote Similarity	NPC193198
0.6786	Remote Similarity	NPC471956
0.6782	Remote Similarity	NPC471994
0.6782	Remote Similarity	NPC120351
0.6782	Remote Similarity	NPC88507
0.6782	Remote Similarity	NPC166143
0.6774	Remote Similarity	NPC15912
0.6774	Remote Similarity	NPC135698
0.6774	Remote Similarity	NPC17810
0.6765	Remote Similarity	NPC222852
0.6761	Remote Similarity	NPC133904
0.6757	Remote Similarity	NPC316029
0.6753	Remote Similarity	NPC476317
0.6753	Remote Similarity	NPC899
0.6753	Remote Similarity	NPC40353
0.6753	Remote Similarity	NPC477202
0.675	Remote Similarity	NPC474955
0.6747	Remote Similarity	NPC61527
0.6747	Remote Similarity	NPC118266
0.6747	Remote Similarity	NPC198314
0.6747	Remote Similarity	NPC220478
0.6721	Remote Similarity	NPC128280
0.6716	Remote Similarity	NPC11130
0.6716	Remote Similarity	NPC129150
0.6716	Remote Similarity	NPC294938
0.6711	Remote Similarity	NPC166797
0.6711	Remote Similarity	NPC470686
0.6709	Remote Similarity	NPC325869
0.6709	Remote Similarity	NPC100906
0.6707	Remote Similarity	NPC474359
0.6707	Remote Similarity	NPC318515
0.6707	Remote Similarity	NPC96055
0.6707	Remote Similarity	NPC471302
0.6706	Remote Similarity	NPC177141
0.6667	Remote Similarity	NPC176621
0.6667	Remote Similarity	NPC474913
0.6667	Remote Similarity	NPC116013
0.6667	Remote Similarity	NPC471278
0.6667	Remote Similarity	NPC469939
0.6667	Remote Similarity	NPC131329
0.6667	Remote Similarity	NPC316185
0.6667	Remote Similarity	NPC476439
0.6667	Remote Similarity	NPC242069
0.6667	Remote Similarity	NPC79756
0.6667	Remote Similarity	NPC315394
0.6667	Remote Similarity	NPC289388
0.6667	Remote Similarity	NPC15910
0.6667	Remote Similarity	NPC327815
0.6667	Remote Similarity	NPC477203
0.6667	Remote Similarity	NPC200513
0.6667	Remote Similarity	NPC75315
0.6667	Remote Similarity	NPC163016

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 NPC226066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	2046
0.2-0.3	4335
0.3-0.4	2038
0.4-0.5	462
0.5-0.6	106
0.6-0.7	6
0.7-0.8	3
0.8-0.85	5
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	NPD5325	Clinical (unspecified phase)
0.8551	High Similarity	NPD8039	Approved
0.8125	Intermediate Similarity	NPD4191	Approved
0.8125	Intermediate Similarity	NPD4194	Approved
0.8125	Intermediate Similarity	NPD4193	Approved
0.8125	Intermediate Similarity	NPD4192	Approved
0.7619	Intermediate Similarity	NPD4219	Approved
0.7246	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6927	Phase 3
0.6914	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8262	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6051	Approved
0.641	Remote Similarity	NPD8264	Approved
0.6364	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD4220	Pre-registration
0.6235	Remote Similarity	NPD1694	Approved
0.618	Remote Similarity	NPD6411	Approved
0.6129	Remote Similarity	NPD6096	Approved
0.6129	Remote Similarity	NPD6097	Approved
0.6111	Remote Similarity	NPD5779	Approved
0.6111	Remote Similarity	NPD5778	Approved
0.6094	Remote Similarity	NPD5343	Approved
0.6067	Remote Similarity	NPD7838	Discovery
0.6024	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7521	Approved
0.5977	Remote Similarity	NPD6409	Approved
0.5977	Remote Similarity	NPD5330	Approved
0.5977	Remote Similarity	NPD7146	Approved
0.5977	Remote Similarity	NPD6684	Approved
0.5977	Remote Similarity	NPD7334	Approved
0.5976	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD6101	Approved
0.5897	Remote Similarity	NPD7144	Approved
0.5897	Remote Similarity	NPD7143	Approved
0.5895	Remote Similarity	NPD6648	Approved
0.5875	Remote Similarity	NPD4687	Approved
0.5875	Remote Similarity	NPD4058	Approved
0.5875	Remote Similarity	NPD5733	Approved
0.5862	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6672	Approved
0.5843	Remote Similarity	NPD5737	Approved
0.5843	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6903	Approved
0.5833	Remote Similarity	NPD7514	Phase 3
0.5833	Remote Similarity	NPD7332	Phase 2
0.5823	Remote Similarity	NPD7152	Approved
0.5823	Remote Similarity	NPD7151	Approved
0.5823	Remote Similarity	NPD5276	Approved
0.5823	Remote Similarity	NPD7150	Approved
0.5814	Remote Similarity	NPD7154	Phase 3
0.5789	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7638	Approved
0.5783	Remote Similarity	NPD7145	Approved
0.5769	Remote Similarity	NPD6923	Approved
0.5769	Remote Similarity	NPD6922	Approved
0.5765	Remote Similarity	NPD6902	Approved
0.5729	Remote Similarity	NPD7640	Approved
0.5729	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD5785	Approved
0.5714	Remote Similarity	NPD6698	Approved
0.5714	Remote Similarity	NPD5207	Approved
0.5714	Remote Similarity	NPD46	Approved
0.5679	Remote Similarity	NPD6924	Approved
0.5679	Remote Similarity	NPD6926	Approved
0.5663	Remote Similarity	NPD6932	Approved
0.5663	Remote Similarity	NPD5776	Phase 2
0.5663	Remote Similarity	NPD6925	Approved
0.5652	Remote Similarity	NPD7983	Approved
0.5652	Remote Similarity	NPD5693	Phase 1
0.5652	Remote Similarity	NPD5694	Approved
0.5652	Remote Similarity	NPD6050	Approved
0.5647	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD5362	Discontinued
0.5632	Remote Similarity	NPD6695	Phase 3
0.5625	Remote Similarity	NPD4225	Approved
0.5625	Remote Similarity	NPD5926	Approved
0.5618	Remote Similarity	NPD6098	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