NPASS Compound

Structure

CID99557 OpenBabel06191715442D 25 26 0 0 0 0 0 0 0 0999 V2000 2.5981 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 5.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 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 1.7321 -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 3.4641 -0.0000 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 0.8660 -1.5000 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 -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 0.0000 -1.0000 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 -0.8660 0.5000 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 0.0000 -0.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 23 1 0 0 0 0 8 23 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 12 15 1 0 0 0 0 12 19 2 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 16 20 2 0 0 0 0 17 21 2 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.24
Volume:	391.013
LogP:	6.22
LogD:	4.283
LogS:	-5.67
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.714
Synthetic Accessibility Score:	2.45
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.69
MDCK Permeability:	1.1954170076933224e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.954
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	100.45464324951172%
Volume Distribution (VD):	2.746
Pgp-substrate:	1.1371771097183228%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.683
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.318
CYP2C9-substrate:	0.749
CYP2D6-inhibitor:	0.735
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.317
CYP3A4-substrate:	0.873

ADMET: Excretion

Clearance (CL):	5.458
Half-life (T1/2):	0.501

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.939
Carcinogencity:	0.022
Eye Corrosion:	0.019
Eye Irritation:	0.934
Respiratory Toxicity:	0.524

Download Data

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

Natural Product: NPC99557

Natural Product ID:	NPC99557
*Common Name:**	2-Tert-Butyl-6-[(3-Tert-Butyl-2-Hydroxy-5-Methylphenyl)Methyl]-4-Methylphenol
IUPAC Name:	2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol
Synonyms:
Standard InCHIKey:	KGRVJHAUYBGFFP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H32O2/c1-14-9-16(20(24)18(11-14)22(3,4)5)13-17-10-15(2)12-19(21(17)25)23(6,7)8/h9-12,24-25H,13H2,1-8H3
SMILES:	Cc1cc(Cc2cc(C)cc(c2O)C(C)(C)C)c(c(c1)C(C)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460648
PubChem CID:	8398
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	2
Potency	134

Activity Type	# Activity
Individual Protein	37
Others	101

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	6195.4	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	55216.7	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	24541.2	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	21982.2	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	9819.1	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	19493.8	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	11017.2	nM	PubChem BioAssay data set
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[568442]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[568442]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[568442]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[568442]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[568442]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[568442]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[568442]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	63095.7	nM	PMID[568442]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[568442]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[568442]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[568442]
NPT546	Individual Protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[568442]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[568442]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[568442]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	48557.7	nM	PMID[568442]
NPT158	Individual Protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Potency	n.a.	7943.3	nM	PMID[568442]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-4.45	%	PMID[568443]
NPT2	Others	Unspecified		Potency	n.a.	39090.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	15484.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19493.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17461.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19591.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38570.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43497.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13800.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	12361.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13869.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13755	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1087.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	15433.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1225.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	12197.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21872.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	6893.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21982.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27535.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	8634.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55216.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17316.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	6164.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68938.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61441.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24541.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19331.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24664.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	9819.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	15355.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30793.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17228.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54759.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	9737.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	11017.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10962.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17373.9	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	12299.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19429.5	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	11017.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	12299.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21800.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	700.0	nM	PMID[568441]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[568442]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[568442]
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[568442]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	0.28	%	PMID[568443]
NPT610	Others	Molecular identity unknown		Potency	n.a.	5011.9	nM	PMID[568442]
NPT610	Others	Molecular identity unknown		Potency	n.a.	39810.7	nM	PMID[568442]
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	IC50	=	100000.0	nM	PMID[568444]

☑ 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 NPC99557 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	265
0.1-0.2	1643
0.2-0.3	3864
0.3-0.4	12965
0.4-0.5	7313
0.5-0.6	9559
0.6-0.7	5652
0.7-0.8	1209
0.8-0.85	166
0.85-0.9	53
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC219286
0.9175	High Similarity	NPC144682
0.902	High Similarity	NPC138942
0.901	High Similarity	NPC168829
0.9	High Similarity	NPC225506
0.8942	High Similarity	NPC63698
0.8942	High Similarity	NPC61885
0.8922	High Similarity	NPC288411
0.89	High Similarity	NPC252821
0.89	High Similarity	NPC122005
0.89	High Similarity	NPC92730
0.8878	High Similarity	NPC289769
0.88	High Similarity	NPC225464
0.8788	High Similarity	NPC26244
0.8785	High Similarity	NPC228425
0.8774	High Similarity	NPC296683
0.875	High Similarity	NPC271274
0.8725	High Similarity	NPC51015
0.87	High Similarity	NPC473388
0.8692	High Similarity	NPC4493
0.8692	High Similarity	NPC476632
0.8692	High Similarity	NPC225679
0.8692	High Similarity	NPC151537
0.8692	High Similarity	NPC165770
0.8687	High Similarity	NPC128062
0.8687	High Similarity	NPC151715
0.8661	High Similarity	NPC475245
0.866	High Similarity	NPC70436
0.8654	High Similarity	NPC474839
0.8624	High Similarity	NPC107240
0.8624	High Similarity	NPC12656
0.8614	High Similarity	NPC77492
0.8611	High Similarity	NPC43525
0.86	High Similarity	NPC8392
0.8598	High Similarity	NPC13482
0.8585	High Similarity	NPC470039
0.8585	High Similarity	NPC95344
0.8585	High Similarity	NPC262365
0.8559	High Similarity	NPC172219
0.8559	High Similarity	NPC304510
0.8558	High Similarity	NPC119860
0.8532	High Similarity	NPC117846
0.8529	High Similarity	NPC128723
0.8519	High Similarity	NPC260323
0.8519	High Similarity	NPC95716
0.8519	High Similarity	NPC176279
0.8515	High Similarity	NPC82664
0.8515	High Similarity	NPC132271
0.8515	High Similarity	NPC292730
0.8515	High Similarity	NPC216520
0.85	High Similarity	NPC316301
0.85	High Similarity	NPC152415
0.85	High Similarity	NPC27323
0.8491	Intermediate Similarity	NPC151477
0.8485	Intermediate Similarity	NPC45040
0.8485	Intermediate Similarity	NPC204210
0.8485	Intermediate Similarity	NPC306074
0.8482	Intermediate Similarity	NPC471671
0.8468	Intermediate Similarity	NPC471668
0.8468	Intermediate Similarity	NPC141001
0.8462	Intermediate Similarity	NPC269212
0.8455	Intermediate Similarity	NPC473137
0.8455	Intermediate Similarity	NPC195922
0.8447	Intermediate Similarity	NPC211885
0.844	Intermediate Similarity	NPC250323
0.844	Intermediate Similarity	NPC46940
0.844	Intermediate Similarity	NPC166995
0.8426	Intermediate Similarity	NPC141782
0.8426	Intermediate Similarity	NPC44732
0.8416	Intermediate Similarity	NPC222146
0.8407	Intermediate Similarity	NPC469644
0.84	Intermediate Similarity	NPC271440
0.8396	Intermediate Similarity	NPC248904
0.8396	Intermediate Similarity	NPC469913
0.8396	Intermediate Similarity	NPC54765
0.8384	Intermediate Similarity	NPC55561
0.8378	Intermediate Similarity	NPC192948
0.8378	Intermediate Similarity	NPC35797
0.8365	Intermediate Similarity	NPC252105
0.8364	Intermediate Similarity	NPC141003
0.8364	Intermediate Similarity	NPC263753
0.8364	Intermediate Similarity	NPC35344
0.8362	Intermediate Similarity	NPC53567
0.835	Intermediate Similarity	NPC51333
0.835	Intermediate Similarity	NPC132078
0.835	Intermediate Similarity	NPC78119
0.835	Intermediate Similarity	NPC216468
0.8349	Intermediate Similarity	NPC308689
0.8333	Intermediate Similarity	NPC58865
0.8319	Intermediate Similarity	NPC154030
0.8319	Intermediate Similarity	NPC206
0.8319	Intermediate Similarity	NPC469609
0.8318	Intermediate Similarity	NPC320439
0.8304	Intermediate Similarity	NPC477137
0.8304	Intermediate Similarity	NPC308311
0.8304	Intermediate Similarity	NPC38893
0.8302	Intermediate Similarity	NPC117115
0.8302	Intermediate Similarity	NPC243677
0.83	Intermediate Similarity	NPC270547
0.83	Intermediate Similarity	NPC155908
0.8288	Intermediate Similarity	NPC268160
0.8283	Intermediate Similarity	NPC177420
0.8283	Intermediate Similarity	NPC318325
0.8283	Intermediate Similarity	NPC98772
0.8283	Intermediate Similarity	NPC280347
0.8283	Intermediate Similarity	NPC242240
0.8283	Intermediate Similarity	NPC123273
0.8273	Intermediate Similarity	NPC177962
0.8273	Intermediate Similarity	NPC228988
0.8273	Intermediate Similarity	NPC62867
0.8273	Intermediate Similarity	NPC286222
0.8269	Intermediate Similarity	NPC213730
0.8257	Intermediate Similarity	NPC475018
0.8246	Intermediate Similarity	NPC93071
0.8246	Intermediate Similarity	NPC126002
0.8241	Intermediate Similarity	NPC11554
0.8235	Intermediate Similarity	NPC32714
0.8235	Intermediate Similarity	NPC274678
0.823	Intermediate Similarity	NPC477136
0.823	Intermediate Similarity	NPC277588
0.8224	Intermediate Similarity	NPC21594
0.8224	Intermediate Similarity	NPC155072
0.8214	Intermediate Similarity	NPC147179
0.8208	Intermediate Similarity	NPC238696
0.8198	Intermediate Similarity	NPC23804
0.8198	Intermediate Similarity	NPC715
0.819	Intermediate Similarity	NPC40258
0.819	Intermediate Similarity	NPC237667
0.819	Intermediate Similarity	NPC91461
0.819	Intermediate Similarity	NPC7686
0.8182	Intermediate Similarity	NPC25493
0.8182	Intermediate Similarity	NPC469912
0.8182	Intermediate Similarity	NPC224527
0.8182	Intermediate Similarity	NPC113460
0.8182	Intermediate Similarity	NPC77772
0.8182	Intermediate Similarity	NPC266937
0.8182	Intermediate Similarity	NPC470770
0.8174	Intermediate Similarity	NPC68339
0.8173	Intermediate Similarity	NPC299762
0.8173	Intermediate Similarity	NPC33675
0.8173	Intermediate Similarity	NPC80027
0.8165	Intermediate Similarity	NPC19808
0.8165	Intermediate Similarity	NPC33728
0.8158	Intermediate Similarity	NPC131118
0.8148	Intermediate Similarity	NPC228737
0.8142	Intermediate Similarity	NPC247858
0.8142	Intermediate Similarity	NPC92
0.8142	Intermediate Similarity	NPC469663
0.8142	Intermediate Similarity	NPC115808
0.8142	Intermediate Similarity	NPC308828
0.8142	Intermediate Similarity	NPC154511
0.8142	Intermediate Similarity	NPC474358
0.8142	Intermediate Similarity	NPC257540
0.8142	Intermediate Similarity	NPC137496
0.8142	Intermediate Similarity	NPC219112
0.8142	Intermediate Similarity	NPC474387
0.8137	Intermediate Similarity	NPC76938
0.8131	Intermediate Similarity	NPC303141
0.8131	Intermediate Similarity	NPC154899
0.8131	Intermediate Similarity	NPC134829
0.8131	Intermediate Similarity	NPC233396
0.8131	Intermediate Similarity	NPC246056
0.8131	Intermediate Similarity	NPC47284
0.8125	Intermediate Similarity	NPC471534
0.812	Intermediate Similarity	NPC297057
0.8119	Intermediate Similarity	NPC304541
0.8113	Intermediate Similarity	NPC108497
0.8108	Intermediate Similarity	NPC471179
0.8103	Intermediate Similarity	NPC24125
0.81	Intermediate Similarity	NPC258219
0.8095	Intermediate Similarity	NPC248396
0.8095	Intermediate Similarity	NPC129373
0.8095	Intermediate Similarity	NPC48730
0.8091	Intermediate Similarity	NPC132720
0.8091	Intermediate Similarity	NPC224870
0.8087	Intermediate Similarity	NPC191866
0.8087	Intermediate Similarity	NPC151197
0.8081	Intermediate Similarity	NPC307235
0.8081	Intermediate Similarity	NPC23167
0.8081	Intermediate Similarity	NPC407
0.8081	Intermediate Similarity	NPC184169
0.8073	Intermediate Similarity	NPC174981
0.8073	Intermediate Similarity	NPC306295
0.807	Intermediate Similarity	NPC16030
0.807	Intermediate Similarity	NPC470760
0.8058	Intermediate Similarity	NPC313650
0.8056	Intermediate Similarity	NPC92623
0.8056	Intermediate Similarity	NPC53740
0.8056	Intermediate Similarity	NPC201662
0.8056	Intermediate Similarity	NPC109691
0.8056	Intermediate Similarity	NPC302681
0.8056	Intermediate Similarity	NPC99836
0.8056	Intermediate Similarity	NPC477814
0.8056	Intermediate Similarity	NPC470700
0.8056	Intermediate Similarity	NPC39664
0.8056	Intermediate Similarity	NPC12640
0.8056	Intermediate Similarity	NPC118286
0.8056	Intermediate Similarity	NPC39097
0.8056	Intermediate Similarity	NPC113457
0.8056	Intermediate Similarity	NPC135464

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 NPC99557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	1026
0.2-0.3	1242
0.3-0.4	2968
0.4-0.5	1957
0.5-0.6	1196
0.6-0.7	425
0.7-0.8	59
0.8-0.85	10
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9175	High Similarity	NPD1809	Phase 2
0.8788	High Similarity	NPD2859	Approved
0.8788	High Similarity	NPD2860	Approved
0.8713	High Similarity	NPD3020	Approved
0.8687	High Similarity	NPD2933	Approved
0.8687	High Similarity	NPD2934	Approved
0.8586	High Similarity	NPD845	Approved
0.8519	High Similarity	NPD6124	Clinical (unspecified phase)
0.85	High Similarity	NPD1432	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD846	Approved
0.8365	Intermediate Similarity	NPD940	Approved
0.8364	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD7635	Approved
0.8158	Intermediate Similarity	NPD7330	Discontinued
0.8095	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD4589	Approved
0.8	Intermediate Similarity	NPD4750	Phase 3
0.8	Intermediate Similarity	NPD3021	Approved
0.8	Intermediate Similarity	NPD3022	Approved
0.7982	Intermediate Similarity	NPD2342	Discontinued
0.7885	Intermediate Similarity	NPD844	Approved
0.7845	Intermediate Similarity	NPD5304	Approved
0.7845	Intermediate Similarity	NPD5303	Approved
0.781	Intermediate Similarity	NPD288	Approved
0.7778	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD111	Approved
0.7778	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD1242	Phase 1
0.7692	Intermediate Similarity	NPD3091	Approved
0.7672	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD7636	Approved
0.7647	Intermediate Similarity	NPD3143	Discontinued
0.7603	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3028	Approved
0.7583	Intermediate Similarity	NPD3092	Approved
0.7565	Intermediate Similarity	NPD2234	Approved
0.7565	Intermediate Similarity	NPD2229	Approved
0.7565	Intermediate Similarity	NPD2228	Approved
0.7563	Intermediate Similarity	NPD3019	Approved
0.7563	Intermediate Similarity	NPD4059	Approved
0.7563	Intermediate Similarity	NPD2932	Approved
0.7521	Intermediate Similarity	NPD3070	Discontinued
0.75	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6696	Suspended
0.736	Intermediate Similarity	NPD4208	Discontinued
0.7339	Intermediate Similarity	NPD3094	Phase 2
0.7333	Intermediate Similarity	NPD4093	Discontinued
0.7302	Intermediate Similarity	NPD4908	Phase 1
0.7295	Intermediate Similarity	NPD1610	Phase 2
0.7288	Intermediate Similarity	NPD6387	Discontinued
0.7288	Intermediate Similarity	NPD6671	Approved
0.728	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2286	Discontinued
0.7273	Intermediate Similarity	NPD3095	Discontinued
0.7273	Intermediate Similarity	NPD1751	Approved
0.7266	Intermediate Similarity	NPD6407	Approved
0.7266	Intermediate Similarity	NPD6405	Approved
0.7258	Intermediate Similarity	NPD8651	Approved
0.725	Intermediate Similarity	NPD1548	Phase 1
0.7244	Intermediate Similarity	NPD4625	Phase 3
0.7222	Intermediate Similarity	NPD2861	Phase 2
0.7222	Intermediate Similarity	NPD4212	Discontinued
0.7222	Intermediate Similarity	NPD5736	Approved
0.7217	Intermediate Similarity	NPD1792	Phase 2
0.72	Intermediate Similarity	NPD4103	Phase 2
0.72	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD4659	Approved
0.7165	Intermediate Similarity	NPD4207	Discontinued
0.7154	Intermediate Similarity	NPD1201	Approved
0.7154	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4626	Approved
0.7105	Intermediate Similarity	NPD1445	Approved
0.7105	Intermediate Similarity	NPD1444	Approved
0.7097	Intermediate Similarity	NPD2561	Approved
0.7097	Intermediate Similarity	NPD2562	Approved
0.708	Intermediate Similarity	NPD9610	Approved
0.708	Intermediate Similarity	NPD9608	Approved
0.7077	Intermediate Similarity	NPD4060	Phase 1
0.7069	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5451	Approved
0.7063	Intermediate Similarity	NPD1164	Approved
0.7063	Intermediate Similarity	NPD1131	Approved
0.7063	Intermediate Similarity	NPD1133	Approved
0.7063	Intermediate Similarity	NPD1135	Approved
0.7063	Intermediate Similarity	NPD1134	Approved
0.7063	Intermediate Similarity	NPD1129	Approved
0.7059	Intermediate Similarity	NPD497	Approved
0.7045	Intermediate Similarity	NPD3552	Approved
0.7045	Intermediate Similarity	NPD3555	Approved
0.7045	Intermediate Similarity	NPD3554	Approved
0.7045	Intermediate Similarity	NPD3553	Approved
0.704	Intermediate Similarity	NPD4749	Approved
0.7008	Intermediate Similarity	NPD2195	Approved
0.7008	Intermediate Similarity	NPD2194	Approved
0.7	Intermediate Similarity	NPD6663	Approved
0.6991	Remote Similarity	NPD9500	Approved
0.6983	Remote Similarity	NPD2684	Approved
0.6977	Remote Similarity	NPD5155	Approved
0.6977	Remote Similarity	NPD5156	Approved
0.6975	Remote Similarity	NPD495	Approved
0.6975	Remote Similarity	NPD496	Approved
0.6975	Remote Similarity	NPD498	Approved
0.6975	Remote Similarity	NPD5283	Phase 1
0.697	Remote Similarity	NPD4097	Suspended
0.6967	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7741	Discontinued
0.6957	Remote Similarity	NPD968	Approved
0.6953	Remote Similarity	NPD3636	Approved
0.6953	Remote Similarity	NPD3635	Approved
0.6953	Remote Similarity	NPD3637	Approved
0.6942	Remote Similarity	NPD7340	Approved
0.694	Remote Similarity	NPD5404	Approved
0.694	Remote Similarity	NPD5406	Approved
0.694	Remote Similarity	NPD5408	Approved
0.694	Remote Similarity	NPD5405	Approved
0.6937	Remote Similarity	NPD9273	Approved
0.6935	Remote Similarity	NPD3026	Approved
0.6935	Remote Similarity	NPD3023	Approved
0.6929	Remote Similarity	NPD1470	Approved
0.6917	Remote Similarity	NPD1791	Approved
0.6917	Remote Similarity	NPD1793	Approved
0.6911	Remote Similarity	NPD3025	Approved
0.6911	Remote Similarity	NPD3024	Approved
0.6905	Remote Similarity	NPD6582	Phase 2
0.6905	Remote Similarity	NPD6583	Phase 3
0.6903	Remote Similarity	NPD4818	Approved
0.6903	Remote Similarity	NPD4817	Approved
0.6899	Remote Similarity	NPD2606	Approved
0.6899	Remote Similarity	NPD2605	Approved
0.6891	Remote Similarity	NPD5535	Approved
0.6891	Remote Similarity	NPD7843	Approved
0.6891	Remote Similarity	NPD1138	Approved
0.6885	Remote Similarity	NPD856	Approved
0.6885	Remote Similarity	NPD16	Approved
0.688	Remote Similarity	NPD422	Phase 1
0.6875	Remote Similarity	NPD4624	Approved
0.687	Remote Similarity	NPD4248	Discontinued
0.6866	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2668	Approved
0.6855	Remote Similarity	NPD2667	Approved
0.6846	Remote Similarity	NPD7095	Approved
0.6846	Remote Similarity	NPD3027	Phase 3
0.6838	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1398	Phase 1
0.6833	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3620	Phase 2
0.6818	Remote Similarity	NPD1555	Discontinued
0.6818	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6099	Approved
0.6815	Remote Similarity	NPD6100	Approved
0.6807	Remote Similarity	NPD1137	Approved
0.6807	Remote Similarity	NPD1139	Approved
0.6807	Remote Similarity	NPD228	Approved
0.68	Remote Similarity	NPD3421	Phase 3
0.68	Remote Similarity	NPD3847	Discontinued
0.6797	Remote Similarity	NPD2797	Approved
0.6794	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5951	Approved
0.6774	Remote Similarity	NPD5691	Approved
0.6774	Remote Similarity	NPD1651	Approved
0.6772	Remote Similarity	NPD1669	Approved
0.6772	Remote Similarity	NPD5327	Phase 3
0.6769	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3594	Approved
0.6769	Remote Similarity	NPD3595	Approved
0.6767	Remote Similarity	NPD5735	Approved
0.6765	Remote Similarity	NPD4725	Approved
0.6765	Remote Similarity	NPD4726	Approved
0.6765	Remote Similarity	NPD4721	Approved
0.6763	Remote Similarity	NPD6667	Approved
0.6763	Remote Similarity	NPD6666	Approved
0.6762	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD318	Approved
0.6748	Remote Similarity	NPD317	Approved
0.6744	Remote Similarity	NPD7451	Discontinued
0.6744	Remote Similarity	NPD6584	Phase 3
0.6741	Remote Similarity	NPD7742	Approved
0.6741	Remote Similarity	NPD7743	Approved
0.6739	Remote Similarity	NPD3400	Discontinued
0.6739	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7003	Approved
0.6721	Remote Similarity	NPD255	Approved
0.6721	Remote Similarity	NPD709	Approved
0.6721	Remote Similarity	NPD256	Approved
0.6719	Remote Similarity	NPD1283	Approved
0.6719	Remote Similarity	NPD5310	Approved
0.6719	Remote Similarity	NPD5311	Approved
0.6714	Remote Similarity	NPD7390	Discontinued
0.6699	Remote Similarity	NPD9093	Approved
0.6696	Remote Similarity	NPD4656	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