NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	212.12
Volume:	243.855
LogP:	4.045
LogD:	3.91
LogS:	-3.766
# Rotatable Bonds:	2
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.804
Synthetic Accessibility Score:	1.68
Fsp3:	0.2
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:	-4.727
MDCK Permeability:	1.9201143004465848e-05
Pgp-inhibitor:	0.494
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.153

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.29
Plasma Protein Binding (PPB):	96.78888702392578%
Volume Distribution (VD):	1.854
Pgp-substrate:	1.954017162322998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.89
CYP1A2-substrate:	0.386
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.29
CYP2C9-inhibitor:	0.756
CYP2C9-substrate:	0.502
CYP2D6-inhibitor:	0.56
CYP2D6-substrate:	0.324
CYP3A4-inhibitor:	0.204
CYP3A4-substrate:	0.623

ADMET: Excretion

Clearance (CL):	7.147
Half-life (T1/2):	0.293

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.024
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.404
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.92
Carcinogencity:	0.271
Eye Corrosion:	0.972
Eye Irritation:	0.992
Respiratory Toxicity:	0.183

Download Data

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

Natural Product: NPC225464

Natural Product ID:	NPC225464
*Common Name:**	4-(2-Phenylpropan-2-Yl)Phenol
IUPAC Name:	4-(2-phenylpropan-2-yl)phenol
Synonyms:
Standard InCHIKey:	QBDSZLJBMIMQRS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O/c1-15(2,12-6-4-3-5-7-12)13-8-10-14(16)11-9-13/h3-11,16H,1-2H3
SMILES:	CC(C)(c1ccccc1)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL194805
PubChem CID:	11742
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
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	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
EC50	2
IC50	4
Others	5
Potency	92

Activity Type	# Activity
Cell Line	1
Individual Protein	27
Others	73
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT299	Individual Protein	Androgen Receptor	Rattus norvegicus	IC50	=	39810.72	nM	PMID[529540]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	19952.6	nM	PMID[529541]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	1778.3	nM	PMID[529541]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[529543]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[529541]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	74978.0	nM	PMID[529541]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	61130.6	nM	PMID[529543]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	38.0	nM	PMID[529544]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	34376.2	nM	PMID[529543]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	EC50	=	4400.0	nM	PMID[529546]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	=	24000.0	nM	PMID[529546]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	IC50	=	13000.0	nM	PMID[529546]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	Activity	=	38.0	%	PMID[529546]
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.	43289	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	54039.7	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	38570.8	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	60633.6	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	61147.4	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	48571.1	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	19952.6	nM	PMID[529541]
NPT98	Individual Protein	HERG	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[529541]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[529541]
NPT2	Others	Unspecified		Potency	n.a.	33491.5	nM	PMID[529541]
NPT2	Others	Unspecified		Potency	n.a.	26603.2	nM	PMID[529541]
NPT35	Others	n.a.		LogP	=	4.31	n.a.	PMID[529544]
NPT610	Others	Molecular identity unknown		Potency	n.a.	11220.2	nM	PMID[529541]
NPT610	Others	Molecular identity unknown		Potency	n.a.	39810.7	nM	PMID[529543]
NPT1567	Protein Complex	DNA gyrase	Escherichia coli K-12	IC50	=	390000.0	nM	PMID[529545]
NPT1567	Protein Complex	DNA gyrase	Escherichia coli K-12	Inhibition	=	96.9	%	PMID[529545]
NPT35	Others	n.a.		LogP	=	4.2	n.a.	PMID[529546]
NPT35	Others	n.a.		pKa	=	10.59	n.a.	PMID[529546]
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68032	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61147.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54497.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	685.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1078.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	60633.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	3889.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	4328.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48163	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	3038.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	3857.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54039.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38581.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30895.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48571.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17228.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24343.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13685.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76333.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21689.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30388.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43289	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	54497.6	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	34096.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	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 NPC225464 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	353
0.1-0.2	2049
0.2-0.3	5145
0.3-0.4	12887
0.4-0.5	6635
0.5-0.6	9990
0.6-0.7	4353
0.7-0.8	1011
0.8-0.85	166
0.85-0.9	84
0.9-0.95	21
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC92730
0.967	High Similarity	NPC27323
0.967	High Similarity	NPC316301
0.9451	High Similarity	NPC155908
0.9355	High Similarity	NPC26244
0.9263	High Similarity	NPC122005
0.9263	High Similarity	NPC252821
0.9255	High Similarity	NPC473388
0.9255	High Similarity	NPC82664
0.9255	High Similarity	NPC292730
0.9255	High Similarity	NPC216520
0.9255	High Similarity	NPC132271
0.9247	High Similarity	NPC151715
0.9247	High Similarity	NPC152415
0.9239	High Similarity	NPC45040
0.9239	High Similarity	NPC304541
0.9231	High Similarity	NPC123273
0.9231	High Similarity	NPC242240
0.9231	High Similarity	NPC318325
0.9167	High Similarity	NPC225506
0.9149	High Similarity	NPC274678
0.914	High Similarity	NPC55903
0.9121	High Similarity	NPC113460
0.9121	High Similarity	NPC25493
0.9043	High Similarity	NPC76938
0.9043	High Similarity	NPC128062
0.9032	High Similarity	NPC306074
0.9022	High Similarity	NPC98772
0.9022	High Similarity	NPC258219
0.9022	High Similarity	NPC280347
0.9022	High Similarity	NPC177420
0.9011	High Similarity	NPC184169
0.9011	High Similarity	NPC23167
0.899	High Similarity	NPC138942
0.898	High Similarity	NPC168829
0.8969	High Similarity	NPC211885
0.8958	High Similarity	NPC32674
0.8958	High Similarity	NPC77492
0.8947	High Similarity	NPC32714
0.8947	High Similarity	NPC144682
0.8947	High Similarity	NPC222146
0.8936	High Similarity	NPC271440
0.8925	High Similarity	NPC55561
0.8901	High Similarity	NPC197783
0.89	High Similarity	NPC271274
0.8889	High Similarity	NPC288411
0.8866	High Similarity	NPC216468
0.8866	High Similarity	NPC33675
0.8866	High Similarity	NPC78119
0.8866	High Similarity	NPC132078
0.8866	High Similarity	NPC51333
0.8866	High Similarity	NPC299762
0.8842	High Similarity	NPC289769
0.883	High Similarity	NPC270547
0.88	High Similarity	NPC219286
0.88	High Similarity	NPC99557
0.8791	High Similarity	NPC175313
0.8791	High Similarity	NPC248817
0.8776	High Similarity	NPC213730
0.875	High Similarity	NPC8392
0.8738	High Similarity	NPC13482
0.8737	High Similarity	NPC162314
0.8737	High Similarity	NPC210497
0.8737	High Similarity	NPC147284
0.8737	High Similarity	NPC94139
0.8737	High Similarity	NPC3358
0.8737	High Similarity	NPC306884
0.8725	High Similarity	NPC11554
0.8723	High Similarity	NPC192
0.8713	High Similarity	NPC477814
0.871	High Similarity	NPC27974
0.87	High Similarity	NPC120719
0.87	High Similarity	NPC254965
0.87	High Similarity	NPC327811
0.8687	High Similarity	NPC7686
0.8687	High Similarity	NPC252105
0.8687	High Similarity	NPC40258
0.8687	High Similarity	NPC91461
0.8681	High Similarity	NPC265146
0.8681	High Similarity	NPC124436
0.8654	High Similarity	NPC322753
0.8641	High Similarity	NPC228343
0.8641	High Similarity	NPC254833
0.8641	High Similarity	NPC58865
0.8632	High Similarity	NPC204210
0.8627	High Similarity	NPC320439
0.8614	High Similarity	NPC154899
0.8614	High Similarity	NPC233396
0.8614	High Similarity	NPC239291
0.8602	High Similarity	NPC407
0.8602	High Similarity	NPC307235
0.8586	High Similarity	NPC294741
0.8585	High Similarity	NPC195922
0.8571	High Similarity	NPC250323
0.8571	High Similarity	NPC156313
0.8571	High Similarity	NPC228425
0.8571	High Similarity	NPC79241
0.8571	High Similarity	NPC6597
0.8558	High Similarity	NPC141782
0.8558	High Similarity	NPC296683
0.8544	High Similarity	NPC75440
0.8544	High Similarity	NPC201959
0.8544	High Similarity	NPC262365
0.8542	High Similarity	NPC325292
0.8542	High Similarity	NPC138117
0.8529	High Similarity	NPC135464
0.8529	High Similarity	NPC54765
0.8529	High Similarity	NPC92623
0.8529	High Similarity	NPC113457
0.8529	High Similarity	NPC248904
0.8526	High Similarity	NPC300017
0.8515	High Similarity	NPC471511
0.8515	High Similarity	NPC323810
0.8515	High Similarity	NPC8931
0.8515	High Similarity	NPC119860
0.8515	High Similarity	NPC120693
0.8515	High Similarity	NPC30506
0.8515	High Similarity	NPC261573
0.85	High Similarity	NPC471578
0.85	High Similarity	NPC101025
0.85	High Similarity	NPC51015
0.85	High Similarity	NPC12221
0.8495	Intermediate Similarity	NPC155393
0.8485	Intermediate Similarity	NPC128723
0.8476	Intermediate Similarity	NPC260323
0.8476	Intermediate Similarity	NPC95716
0.8476	Intermediate Similarity	NPC176279
0.8469	Intermediate Similarity	NPC312132
0.8469	Intermediate Similarity	NPC259512
0.8469	Intermediate Similarity	NPC202986
0.8454	Intermediate Similarity	NPC245187
0.8447	Intermediate Similarity	NPC151477
0.8431	Intermediate Similarity	NPC47284
0.8431	Intermediate Similarity	NPC474839
0.8421	Intermediate Similarity	NPC70436
0.8416	Intermediate Similarity	NPC62351
0.8416	Intermediate Similarity	NPC269212
0.8416	Intermediate Similarity	NPC135784
0.84	Intermediate Similarity	NPC72729
0.8396	Intermediate Similarity	NPC46940
0.8387	Intermediate Similarity	NPC286904
0.8387	Intermediate Similarity	NPC150837
0.8384	Intermediate Similarity	NPC474073
0.8384	Intermediate Similarity	NPC201967
0.8381	Intermediate Similarity	NPC44732
0.8367	Intermediate Similarity	NPC313650
0.8365	Intermediate Similarity	NPC95344
0.8365	Intermediate Similarity	NPC61885
0.8365	Intermediate Similarity	NPC63698
0.835	Intermediate Similarity	NPC310456
0.835	Intermediate Similarity	NPC155072
0.835	Intermediate Similarity	NPC21594
0.835	Intermediate Similarity	NPC188677
0.835	Intermediate Similarity	NPC53740
0.8333	Intermediate Similarity	NPC241891
0.8333	Intermediate Similarity	NPC238696
0.8318	Intermediate Similarity	NPC715
0.8318	Intermediate Similarity	NPC141003
0.8318	Intermediate Similarity	NPC176730
0.8318	Intermediate Similarity	NPC35344
0.8318	Intermediate Similarity	NPC123175
0.8317	Intermediate Similarity	NPC472585
0.8317	Intermediate Similarity	NPC100340
0.8317	Intermediate Similarity	NPC143659
0.8316	Intermediate Similarity	NPC104216
0.8316	Intermediate Similarity	NPC19680
0.8302	Intermediate Similarity	NPC308689
0.8302	Intermediate Similarity	NPC4493
0.8302	Intermediate Similarity	NPC77772
0.8302	Intermediate Similarity	NPC476632
0.8302	Intermediate Similarity	NPC225679
0.8302	Intermediate Similarity	NPC151537
0.8302	Intermediate Similarity	NPC470770
0.8302	Intermediate Similarity	NPC165770
0.8302	Intermediate Similarity	NPC266937
0.83	Intermediate Similarity	NPC130193
0.8286	Intermediate Similarity	NPC62258
0.8286	Intermediate Similarity	NPC314187
0.8286	Intermediate Similarity	NPC55617
0.8257	Intermediate Similarity	NPC474358
0.8257	Intermediate Similarity	NPC257540
0.8257	Intermediate Similarity	NPC474387
0.8257	Intermediate Similarity	NPC154511
0.8257	Intermediate Similarity	NPC247858
0.8257	Intermediate Similarity	NPC137496
0.8252	Intermediate Similarity	NPC117115
0.8252	Intermediate Similarity	NPC134829
0.8247	Intermediate Similarity	NPC231150
0.8241	Intermediate Similarity	NPC107240
0.8241	Intermediate Similarity	NPC12656
0.8241	Intermediate Similarity	NPC268160
0.8235	Intermediate Similarity	NPC233827
0.8235	Intermediate Similarity	NPC168393
0.8235	Intermediate Similarity	NPC196479
0.8224	Intermediate Similarity	NPC177962
0.8224	Intermediate Similarity	NPC286222
0.8224	Intermediate Similarity	NPC166995
0.8224	Intermediate Similarity	NPC43525
0.8224	Intermediate Similarity	NPC228988
0.8224	Intermediate Similarity	NPC62867

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 NPC225464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	1032
0.2-0.3	1116
0.3-0.4	2923
0.4-0.5	1988
0.5-0.6	1150
0.6-0.7	448
0.7-0.8	87
0.8-0.85	5
0.85-0.9	5
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.967	High Similarity	NPD1432	Clinical (unspecified phase)
0.9468	High Similarity	NPD3020	Approved
0.9355	High Similarity	NPD2860	Approved
0.9355	High Similarity	NPD2859	Approved
0.9247	High Similarity	NPD2934	Approved
0.9247	High Similarity	NPD2933	Approved
0.8947	High Similarity	NPD1809	Phase 2
0.8681	High Similarity	NPD111	Approved
0.8641	High Similarity	NPD3022	Approved
0.8641	High Similarity	NPD3021	Approved
0.8586	High Similarity	NPD289	Clinical (unspecified phase)
0.8557	High Similarity	NPD844	Approved
0.8542	High Similarity	NPD845	Approved
0.8469	Intermediate Similarity	NPD288	Approved
0.8317	Intermediate Similarity	NPD846	Approved
0.8317	Intermediate Similarity	NPD940	Approved
0.8218	Intermediate Similarity	NPD1242	Phase 1
0.8148	Intermediate Similarity	NPD2234	Approved
0.8148	Intermediate Similarity	NPD2228	Approved
0.8148	Intermediate Similarity	NPD2229	Approved
0.8125	Intermediate Similarity	NPD4589	Approved
0.8113	Intermediate Similarity	NPD1792	Phase 2
0.8108	Intermediate Similarity	NPD3091	Approved
0.8039	Intermediate Similarity	NPD3028	Approved
0.8	Intermediate Similarity	NPD1445	Approved
0.8	Intermediate Similarity	NPD1444	Approved
0.7965	Intermediate Similarity	NPD3019	Approved
0.7965	Intermediate Similarity	NPD4059	Approved
0.7965	Intermediate Similarity	NPD1751	Approved
0.7965	Intermediate Similarity	NPD2932	Approved
0.7925	Intermediate Similarity	NPD2342	Discontinued
0.789	Intermediate Similarity	NPD7635	Approved
0.7876	Intermediate Similarity	NPD4093	Discontinued
0.7826	Intermediate Similarity	NPD3092	Approved
0.781	Intermediate Similarity	NPD9610	Approved
0.781	Intermediate Similarity	NPD9608	Approved
0.7798	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD5303	Approved
0.7788	Intermediate Similarity	NPD5304	Approved
0.7778	Intermediate Similarity	NPD4750	Phase 3
0.7748	Intermediate Similarity	NPD1791	Approved
0.7748	Intermediate Similarity	NPD1793	Approved
0.7658	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD3095	Discontinued
0.7563	Intermediate Similarity	NPD3094	Phase 2
0.7542	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD7157	Approved
0.7521	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2195	Approved
0.75	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD2194	Approved
0.75	Intermediate Similarity	NPD5283	Phase 1
0.75	Intermediate Similarity	NPD2286	Discontinued
0.75	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD7330	Discontinued
0.7477	Intermediate Similarity	NPD228	Approved
0.7473	Intermediate Similarity	NPD9087	Approved
0.7459	Intermediate Similarity	NPD5156	Approved
0.7459	Intermediate Similarity	NPD5155	Approved
0.7455	Intermediate Similarity	NPD5451	Approved
0.7438	Intermediate Similarity	NPD3636	Approved
0.7438	Intermediate Similarity	NPD5736	Approved
0.7438	Intermediate Similarity	NPD3635	Approved
0.7438	Intermediate Similarity	NPD3637	Approved
0.7434	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD9500	Approved
0.7383	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD2606	Approved
0.7377	Intermediate Similarity	NPD2605	Approved
0.7373	Intermediate Similarity	NPD1610	Phase 2
0.7368	Intermediate Similarity	NPD6671	Approved
0.7364	Intermediate Similarity	NPD2684	Approved
0.7358	Intermediate Similarity	NPD1616	Discontinued
0.735	Intermediate Similarity	NPD2668	Approved
0.735	Intermediate Similarity	NPD2667	Approved
0.7328	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3023	Approved
0.7288	Intermediate Similarity	NPD3026	Approved
0.7281	Intermediate Similarity	NPD475	Phase 2
0.7273	Intermediate Similarity	NPD4103	Phase 2
0.7273	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD3025	Approved
0.7265	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD3024	Approved
0.7265	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD9379	Approved
0.7257	Intermediate Similarity	NPD9377	Approved
0.7257	Intermediate Similarity	NPD5535	Approved
0.725	Intermediate Similarity	NPD4659	Approved
0.725	Intermediate Similarity	NPD6582	Phase 2
0.725	Intermediate Similarity	NPD1755	Approved
0.725	Intermediate Similarity	NPD6583	Phase 3
0.7236	Intermediate Similarity	NPD4908	Phase 1
0.7236	Intermediate Similarity	NPD3594	Approved
0.7236	Intermediate Similarity	NPD3595	Approved
0.7234	Intermediate Similarity	NPD9294	Approved
0.7217	Intermediate Similarity	NPD255	Approved
0.7217	Intermediate Similarity	NPD256	Approved
0.7213	Intermediate Similarity	NPD6584	Phase 3
0.7213	Intermediate Similarity	NPD4624	Approved
0.72	Intermediate Similarity	NPD6663	Approved
0.7179	Intermediate Similarity	NPD1548	Phase 1
0.7177	Intermediate Similarity	NPD7095	Approved
0.717	Intermediate Similarity	NPD9273	Approved
0.7167	Intermediate Similarity	NPD2561	Approved
0.7167	Intermediate Similarity	NPD2562	Approved
0.7158	Intermediate Similarity	NPD9088	Approved
0.7154	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3421	Phase 3
0.7143	Intermediate Similarity	NPD3143	Discontinued
0.7143	Intermediate Similarity	NPD3847	Discontinued
0.7131	Intermediate Similarity	NPD1164	Approved
0.7131	Intermediate Similarity	NPD3055	Approved
0.7131	Intermediate Similarity	NPD3053	Approved
0.713	Intermediate Similarity	NPD497	Approved
0.713	Intermediate Similarity	NPD4817	Approved
0.713	Intermediate Similarity	NPD4818	Approved
0.712	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1651	Approved
0.7107	Intermediate Similarity	NPD1669	Approved
0.7105	Intermediate Similarity	NPD7843	Approved
0.7105	Intermediate Similarity	NPD821	Approved
0.7094	Intermediate Similarity	NPD16	Approved
0.7094	Intermediate Similarity	NPD856	Approved
0.7083	Intermediate Similarity	NPD1201	Approved
0.7069	Intermediate Similarity	NPD709	Approved
0.7064	Intermediate Similarity	NPD4658	Approved
0.7064	Intermediate Similarity	NPD4656	Approved
0.7059	Intermediate Similarity	NPD4626	Approved
0.7049	Intermediate Similarity	NPD1283	Approved
0.7049	Intermediate Similarity	NPD5311	Approved
0.7049	Intermediate Similarity	NPD5310	Approved
0.7043	Intermediate Similarity	NPD498	Approved
0.7043	Intermediate Similarity	NPD495	Approved
0.7043	Intermediate Similarity	NPD496	Approved
0.704	Intermediate Similarity	NPD3027	Phase 3
0.7025	Intermediate Similarity	NPD2232	Approved
0.7025	Intermediate Similarity	NPD3070	Discontinued
0.7025	Intermediate Similarity	NPD2233	Approved
0.7025	Intermediate Similarity	NPD3972	Approved
0.7025	Intermediate Similarity	NPD2230	Approved
0.7009	Intermediate Similarity	NPD3596	Phase 2
0.7009	Intermediate Similarity	NPD7636	Approved
0.7008	Intermediate Similarity	NPD4060	Phase 1
0.7008	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6346	Approved
0.7008	Intermediate Similarity	NPD3620	Phase 2
0.6984	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD9618	Approved
0.6983	Remote Similarity	NPD9614	Approved
0.6975	Remote Similarity	NPD1357	Approved
0.6967	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5327	Phase 3
0.6964	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD317	Approved
0.6949	Remote Similarity	NPD318	Approved
0.6942	Remote Similarity	NPD1535	Discovery
0.6935	Remote Similarity	NPD7451	Discontinued
0.693	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7743	Approved
0.6923	Remote Similarity	NPD7742	Approved
0.6917	Remote Similarity	NPD6516	Phase 2
0.6917	Remote Similarity	NPD5846	Approved
0.6909	Remote Similarity	NPD4229	Approved
0.6909	Remote Similarity	NPD3682	Approved
0.6909	Remote Similarity	NPD4231	Approved
0.6909	Remote Similarity	NPD3680	Approved
0.6905	Remote Similarity	NPD4625	Phase 3
0.6899	Remote Similarity	NPD4097	Suspended
0.6891	Remote Similarity	NPD6581	Approved
0.6891	Remote Similarity	NPD6580	Approved
0.6885	Remote Similarity	NPD1608	Approved
0.6885	Remote Similarity	NPD1481	Phase 2
0.688	Remote Similarity	NPD4208	Discontinued
0.6875	Remote Similarity	NPD4140	Approved
0.6869	Remote Similarity	NPD9089	Approved
0.6864	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9568	Approved
0.686	Remote Similarity	NPD1981	Approved
0.686	Remote Similarity	NPD1980	Approved
0.686	Remote Similarity	NPD1983	Approved
0.6855	Remote Similarity	NPD2797	Approved
0.6855	Remote Similarity	NPD1470	Approved
0.685	Remote Similarity	NPD3764	Approved
0.6838	Remote Similarity	NPD5951	Approved
0.6833	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3443	Approved
0.6833	Remote Similarity	NPD5585	Approved
0.6833	Remote Similarity	NPD3444	Approved
0.6833	Remote Similarity	NPD3445	Approved
0.6829	Remote Similarity	NPD4749	Approved
0.6825	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5735	Approved
0.6818	Remote Similarity	NPD4719	Phase 2
0.6814	Remote Similarity	NPD290	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