NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	164.12
Volume:	191.137
LogP:	3.705
LogD:	3.651
LogS:	-3.203
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	2.003
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.604
MDCK Permeability:	2.000727727136109e-05
Pgp-inhibitor:	0.338
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.674
Plasma Protein Binding (PPB):	94.61597442626953%
Volume Distribution (VD):	3.617
Pgp-substrate:	7.992111682891846%

ADMET: Metabolism

CYP1A2-inhibitor:	0.912
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.762
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.518
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.826
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.214
CYP3A4-substrate:	0.556

ADMET: Excretion

Clearance (CL):	9.741
Half-life (T1/2):	0.642

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.506
Skin Sensitization:	0.636
Carcinogencity:	0.068
Eye Corrosion:	0.981
Eye Irritation:	0.989
Respiratory Toxicity:	0.604

Download Data

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

Natural Product: NPC33675

Natural Product ID:	NPC33675
*Common Name:**	2-Tert-Butyl-5-Methylphenol
IUPAC Name:	2-tert-butyl-5-methylphenol
Synonyms:
Standard InCHIKey:	XOUQAVYLRNOXDO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H16O/c1-8-5-6-9(10(12)7-8)11(2,3)4/h5-7,12H,1-4H3
SMILES:	Cc1ccc(c(c1)O)C(C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1880057
PubChem CID:	6937
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5746	Pancratium trianthum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7393	Esenbeckia nesiotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5334	Rhodotypos scandens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2665	Andinobates fulguritus	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7237	Xanthostemon oppositifolius	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28409	Lens phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8532	Helipterum tenellum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6113	Piper pedicellosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5162	Comaster multifida	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4539	Ipomoea cristulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO490	Lophozonia menziesii	Species	0thofagaceae	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	1
Others	6
Potency	45

Activity Type	# Activity
Individual Protein	10
Organism	1
Others	41

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	1.8	nM	PMID[566603]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	66363.7	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	27535.7	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.	61130.6	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	59696.6	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT1	Others	Radical scavenging activity		Activity	=	28.55	%	PMID[566604]
NPT1	Others	Radical scavenging activity		Activity	=	19.65	%	PMID[566604]
NPT1	Others	Radical scavenging activity		Activity	=	11.3	%	PMID[566604]
NPT1	Others	Radical scavenging activity		Activity	=	4.69	%	PMID[566604]
NPT1	Others	Radical scavenging activity		Activity	=	3.29	%	PMID[566604]
NPT1	Others	Radical scavenging activity		IC50	=	173.95	ug.mL-1	PMID[566604]
NPT610	Others	Molecular identity unknown		Potency	n.a.	70794.6	nM	PMID[566603]
NPT21	Organism	Aspergillus niger	Aspergillus niger	log(1/C)	=	3.7	n.a.	PMID[566605]
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43651.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	74461.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	26419.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17228.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43641.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	59696.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	66363.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	18703.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	59146.7	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	47418.7	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	38895.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	47418.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	9374.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	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 NPC33675 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	309
0.1-0.2	2012
0.2-0.3	5084
0.3-0.4	13294
0.4-0.5	6935
0.5-0.6	10009
0.6-0.7	3837
0.7-0.8	893
0.8-0.85	191
0.85-0.9	97
0.9-0.95	28
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC299762
0.9787	High Similarity	NPC252105
0.9677	High Similarity	NPC79241
0.9677	High Similarity	NPC6597
0.957	High Similarity	NPC312132
0.957	High Similarity	NPC259512
0.9565	High Similarity	NPC152415
0.9485	High Similarity	NPC47284
0.9474	High Similarity	NPC72729
0.9457	High Similarity	NPC55903
0.9388	High Similarity	NPC310456
0.9388	High Similarity	NPC53740
0.9348	High Similarity	NPC306074
0.9348	High Similarity	NPC231150
0.9255	High Similarity	NPC222146
0.92	High Similarity	NPC64586
0.92	High Similarity	NPC306295
0.9184	High Similarity	NPC475225
0.9167	High Similarity	NPC122005
0.9167	High Similarity	NPC252821
0.9149	High Similarity	NPC289769
0.9149	High Similarity	NPC316301
0.9149	High Similarity	NPC245187
0.9149	High Similarity	NPC27323
0.9082	High Similarity	NPC269212
0.9082	High Similarity	NPC471228
0.9082	High Similarity	NPC235762
0.9072	High Similarity	NPC225506
0.9072	High Similarity	NPC174911
0.9043	High Similarity	NPC3358
0.9043	High Similarity	NPC147284
0.9043	High Similarity	NPC162314
0.9043	High Similarity	NPC94139
0.9043	High Similarity	NPC210497
0.9043	High Similarity	NPC306884
0.9032	High Similarity	NPC192
0.9022	High Similarity	NPC27974
0.898	High Similarity	NPC477685
0.8936	High Similarity	NPC155908
0.8913	High Similarity	NPC407
0.8913	High Similarity	NPC307235
0.8911	High Similarity	NPC320439
0.8911	High Similarity	NPC66834
0.89	High Similarity	NPC117115
0.8878	High Similarity	NPC129373
0.8878	High Similarity	NPC248396
0.8878	High Similarity	NPC48730
0.8878	High Similarity	NPC211885
0.8866	High Similarity	NPC225464
0.8866	High Similarity	NPC152097
0.8866	High Similarity	NPC77492
0.8854	High Similarity	NPC144682
0.8846	High Similarity	NPC250323
0.8812	High Similarity	NPC21594
0.8812	High Similarity	NPC155072
0.8804	High Similarity	NPC155393
0.88	High Similarity	NPC218879
0.88	High Similarity	NPC238696
0.88	High Similarity	NPC272029
0.88	High Similarity	NPC227458
0.88	High Similarity	NPC244513
0.8788	High Similarity	NPC80800
0.8776	High Similarity	NPC92730
0.8776	High Similarity	NPC260775
0.875	High Similarity	NPC260323
0.875	High Similarity	NPC176279
0.875	High Similarity	NPC77772
0.875	High Similarity	NPC76938
0.875	High Similarity	NPC470770
0.875	High Similarity	NPC266937
0.8738	High Similarity	NPC58865
0.8737	High Similarity	NPC304541
0.8725	High Similarity	NPC158253
0.8725	High Similarity	NPC232523
0.8725	High Similarity	NPC204901
0.8725	High Similarity	NPC151477
0.8723	High Similarity	NPC318325
0.8723	High Similarity	NPC123273
0.8723	High Similarity	NPC242240
0.8713	High Similarity	NPC37802
0.87	High Similarity	NPC108497
0.8696	High Similarity	NPC286904
0.8696	High Similarity	NPC150837
0.8687	High Similarity	NPC130756
0.8687	High Similarity	NPC12931
0.8687	High Similarity	NPC70677
0.8679	High Similarity	NPC195922
0.8673	High Similarity	NPC156313
0.8673	High Similarity	NPC474073
0.8673	High Similarity	NPC475078
0.8667	High Similarity	NPC62867
0.8667	High Similarity	NPC177962
0.866	High Similarity	NPC32714
0.866	High Similarity	NPC8392
0.8654	High Similarity	NPC13482
0.8654	High Similarity	NPC141782
0.8646	High Similarity	NPC271440
0.8646	High Similarity	NPC29373
0.8641	High Similarity	NPC174981
0.8627	High Similarity	NPC99836
0.8627	High Similarity	NPC12640
0.8627	High Similarity	NPC201662
0.8627	High Similarity	NPC477814
0.8617	High Similarity	NPC113460
0.8617	High Similarity	NPC19680
0.8617	High Similarity	NPC25493
0.8614	High Similarity	NPC475580
0.8614	High Similarity	NPC120719
0.86	High Similarity	NPC12221
0.8571	High Similarity	NPC275627
0.8571	High Similarity	NPC224527
0.8558	High Similarity	NPC186385
0.8558	High Similarity	NPC299568
0.8558	High Similarity	NPC33728
0.8558	High Similarity	NPC19808
0.8542	High Similarity	NPC204210
0.8526	High Similarity	NPC98772
0.8526	High Similarity	NPC177420
0.8526	High Similarity	NPC280347
0.8526	High Similarity	NPC258219
0.8511	High Similarity	NPC184169
0.8511	High Similarity	NPC23167
0.8491	Intermediate Similarity	NPC46940
0.8491	Intermediate Similarity	NPC302371
0.8491	Intermediate Similarity	NPC228452
0.8476	Intermediate Similarity	NPC132720
0.8469	Intermediate Similarity	NPC274678
0.844	Intermediate Similarity	NPC477136
0.844	Intermediate Similarity	NPC320864
0.8438	Intermediate Similarity	NPC55561
0.8426	Intermediate Similarity	NPC35797
0.8426	Intermediate Similarity	NPC192948
0.8426	Intermediate Similarity	NPC469719
0.8411	Intermediate Similarity	NPC715
0.8404	Intermediate Similarity	NPC197783
0.84	Intermediate Similarity	NPC128723
0.8396	Intermediate Similarity	NPC151537
0.8396	Intermediate Similarity	NPC54373
0.8396	Intermediate Similarity	NPC95716
0.8396	Intermediate Similarity	NPC469912
0.8396	Intermediate Similarity	NPC322753
0.8387	Intermediate Similarity	NPC474354
0.8384	Intermediate Similarity	NPC202986
0.8381	Intermediate Similarity	NPC314187
0.8367	Intermediate Similarity	NPC128062
0.8365	Intermediate Similarity	NPC474352
0.8351	Intermediate Similarity	NPC270547
0.835	Intermediate Similarity	NPC138942
0.835	Intermediate Similarity	NPC471350
0.8349	Intermediate Similarity	NPC477137
0.8349	Intermediate Similarity	NPC38893
0.8349	Intermediate Similarity	NPC219112
0.8349	Intermediate Similarity	NPC308311
0.8349	Intermediate Similarity	NPC471668
0.8349	Intermediate Similarity	NPC92
0.8349	Intermediate Similarity	NPC141001
0.8349	Intermediate Similarity	NPC469663
0.8333	Intermediate Similarity	NPC146798
0.8333	Intermediate Similarity	NPC12870
0.8333	Intermediate Similarity	NPC53051
0.8333	Intermediate Similarity	NPC24327
0.8333	Intermediate Similarity	NPC249828
0.8333	Intermediate Similarity	NPC313030
0.8333	Intermediate Similarity	NPC24404
0.8333	Intermediate Similarity	NPC268160
0.8333	Intermediate Similarity	NPC71002
0.8333	Intermediate Similarity	NPC94351
0.8333	Intermediate Similarity	NPC222522
0.8333	Intermediate Similarity	NPC85479
0.8333	Intermediate Similarity	NPC168393
0.8333	Intermediate Similarity	NPC106396
0.8333	Intermediate Similarity	NPC168303
0.8333	Intermediate Similarity	NPC70436
0.8333	Intermediate Similarity	NPC233827
0.8333	Intermediate Similarity	NPC471534
0.8333	Intermediate Similarity	NPC242342
0.8333	Intermediate Similarity	NPC302219
0.8333	Intermediate Similarity	NPC168829
0.8318	Intermediate Similarity	NPC228425
0.8318	Intermediate Similarity	NPC98372
0.8318	Intermediate Similarity	NPC26615
0.8318	Intermediate Similarity	NPC166995
0.8317	Intermediate Similarity	NPC166761
0.8317	Intermediate Similarity	NPC10588
0.8317	Intermediate Similarity	NPC294741
0.8317	Intermediate Similarity	NPC130103
0.8302	Intermediate Similarity	NPC224870
0.83	Intermediate Similarity	NPC32674
0.8298	Intermediate Similarity	NPC474211
0.8298	Intermediate Similarity	NPC248817
0.8298	Intermediate Similarity	NPC175313
0.8288	Intermediate Similarity	NPC471449
0.8286	Intermediate Similarity	NPC11554
0.8283	Intermediate Similarity	NPC26244
0.828	Intermediate Similarity	NPC168855
0.8273	Intermediate Similarity	NPC304510
0.8273	Intermediate Similarity	NPC172219
0.8269	Intermediate Similarity	NPC469913
0.8269	Intermediate Similarity	NPC271274
0.8269	Intermediate Similarity	NPC54765

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 NPC33675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	1071
0.2-0.3	1368
0.3-0.4	2958
0.4-0.5	1883
0.5-0.6	1057
0.6-0.7	384
0.7-0.8	69
0.8-0.85	13
0.85-0.9	3
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9674	High Similarity	NPD844	Approved
0.957	High Similarity	NPD288	Approved
0.9271	High Similarity	NPD289	Clinical (unspecified phase)
0.9149	High Similarity	NPD1432	Clinical (unspecified phase)
0.8854	High Similarity	NPD1809	Phase 2
0.8842	High Similarity	NPD845	Approved
0.8558	High Similarity	NPD4750	Phase 3
0.84	Intermediate Similarity	NPD3020	Approved
0.8365	Intermediate Similarity	NPD2342	Discontinued
0.8318	Intermediate Similarity	NPD7635	Approved
0.8283	Intermediate Similarity	NPD2859	Approved
0.8283	Intermediate Similarity	NPD2860	Approved
0.8269	Intermediate Similarity	NPD1444	Approved
0.8269	Intermediate Similarity	NPD1445	Approved
0.8235	Intermediate Similarity	NPD846	Approved
0.8235	Intermediate Similarity	NPD940	Approved
0.8191	Intermediate Similarity	NPD111	Approved
0.8182	Intermediate Similarity	NPD2934	Approved
0.8182	Intermediate Similarity	NPD2933	Approved
0.8037	Intermediate Similarity	NPD1792	Phase 2
0.8037	Intermediate Similarity	NPD3022	Approved
0.8037	Intermediate Similarity	NPD3021	Approved
0.8	Intermediate Similarity	NPD1793	Approved
0.8	Intermediate Similarity	NPD1791	Approved
0.7876	Intermediate Similarity	NPD3091	Approved
0.7768	Intermediate Similarity	NPD6671	Approved
0.7739	Intermediate Similarity	NPD4059	Approved
0.7739	Intermediate Similarity	NPD2932	Approved
0.7739	Intermediate Similarity	NPD3019	Approved
0.7739	Intermediate Similarity	NPD1751	Approved
0.7727	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD9500	Approved
0.7619	Intermediate Similarity	NPD1242	Phase 1
0.7607	Intermediate Similarity	NPD3092	Approved
0.7589	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4626	Approved
0.7586	Intermediate Similarity	NPD4589	Approved
0.7565	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD6696	Suspended
0.7522	Intermediate Similarity	NPD497	Approved
0.7479	Intermediate Similarity	NPD4749	Approved
0.7458	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1778	Approved
0.7436	Intermediate Similarity	NPD3095	Discontinued
0.7434	Intermediate Similarity	NPD2228	Approved
0.7434	Intermediate Similarity	NPD498	Approved
0.7434	Intermediate Similarity	NPD496	Approved
0.7434	Intermediate Similarity	NPD2229	Approved
0.7434	Intermediate Similarity	NPD2234	Approved
0.7434	Intermediate Similarity	NPD495	Approved
0.7429	Intermediate Similarity	NPD9273	Approved
0.7411	Intermediate Similarity	NPD228	Approved
0.7407	Intermediate Similarity	NPD9610	Approved
0.7407	Intermediate Similarity	NPD9608	Approved
0.7391	Intermediate Similarity	NPD9087	Approved
0.7391	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3094	Phase 2
0.735	Intermediate Similarity	NPD4093	Discontinued
0.7339	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1755	Approved
0.7333	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1201	Approved
0.7295	Intermediate Similarity	NPD2194	Approved
0.7295	Intermediate Similarity	NPD2195	Approved
0.7288	Intermediate Similarity	NPD2286	Discontinued
0.7281	Intermediate Similarity	NPD1398	Phase 1
0.7265	Intermediate Similarity	NPD5303	Approved
0.7265	Intermediate Similarity	NPD7330	Discontinued
0.7265	Intermediate Similarity	NPD5304	Approved
0.7258	Intermediate Similarity	NPD4625	Phase 3
0.7241	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3637	Approved
0.7236	Intermediate Similarity	NPD3636	Approved
0.7236	Intermediate Similarity	NPD3635	Approved
0.7236	Intermediate Similarity	NPD5736	Approved
0.7227	Intermediate Similarity	NPD1980	Approved
0.7227	Intermediate Similarity	NPD1981	Approved
0.7227	Intermediate Similarity	NPD1983	Approved
0.7217	Intermediate Similarity	NPD9618	Approved
0.7217	Intermediate Similarity	NPD9614	Approved
0.7217	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5691	Approved
0.7203	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD9377	Approved
0.7193	Intermediate Similarity	NPD9379	Approved
0.7177	Intermediate Similarity	NPD2606	Approved
0.7177	Intermediate Similarity	NPD2605	Approved
0.7158	Intermediate Similarity	NPD9294	Approved
0.7156	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7157	Approved
0.7155	Intermediate Similarity	NPD709	Approved
0.713	Intermediate Similarity	NPD3028	Approved
0.713	Intermediate Similarity	NPD1616	Discontinued
0.712	Intermediate Similarity	NPD5156	Approved
0.712	Intermediate Similarity	NPD5155	Approved
0.7109	Intermediate Similarity	NPD4097	Suspended
0.7107	Intermediate Similarity	NPD2230	Approved
0.7107	Intermediate Similarity	NPD2233	Approved
0.7107	Intermediate Similarity	NPD2232	Approved
0.7094	Intermediate Similarity	NPD7636	Approved
0.7094	Intermediate Similarity	NPD7340	Approved
0.7083	Intermediate Similarity	NPD9088	Approved
0.7083	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3143	Discontinued
0.7083	Intermediate Similarity	NPD3496	Discontinued
0.7083	Intermediate Similarity	NPD3026	Approved
0.7083	Intermediate Similarity	NPD3023	Approved
0.7073	Intermediate Similarity	NPD1470	Approved
0.7059	Intermediate Similarity	NPD3025	Approved
0.7059	Intermediate Similarity	NPD3024	Approved
0.7054	Intermediate Similarity	NPD290	Approved
0.704	Intermediate Similarity	NPD3594	Approved
0.704	Intermediate Similarity	NPD3595	Approved
0.7034	Intermediate Similarity	NPD9613	Approved
0.7034	Intermediate Similarity	NPD9616	Approved
0.7034	Intermediate Similarity	NPD9615	Approved
0.7016	Intermediate Similarity	NPD4624	Approved
0.7008	Intermediate Similarity	NPD6663	Approved
0.6991	Remote Similarity	NPD2684	Approved
0.6983	Remote Similarity	NPD5283	Phase 1
0.6975	Remote Similarity	NPD316	Approved
0.6967	Remote Similarity	NPD3070	Discontinued
0.6964	Remote Similarity	NPD968	Approved
0.696	Remote Similarity	NPD2861	Phase 2
0.6952	Remote Similarity	NPD1088	Approved
0.6947	Remote Similarity	NPD6099	Approved
0.6947	Remote Similarity	NPD6100	Approved
0.6935	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.693	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD475	Phase 2
0.6917	Remote Similarity	NPD1357	Approved
0.6917	Remote Similarity	NPD1651	Approved
0.6897	Remote Similarity	NPD1138	Approved
0.6893	Remote Similarity	NPD1101	Approved
0.6885	Remote Similarity	NPD1611	Approved
0.6885	Remote Similarity	NPD1610	Phase 2
0.687	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD255	Approved
0.6864	Remote Similarity	NPD256	Approved
0.6855	Remote Similarity	NPD1283	Approved
0.6842	Remote Similarity	NPD9266	Approved
0.6842	Remote Similarity	NPD74	Approved
0.6833	Remote Similarity	NPD1759	Phase 1
0.6825	Remote Similarity	NPD1712	Approved
0.6822	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4060	Phase 1
0.6822	Remote Similarity	NPD3620	Phase 2
0.6822	Remote Similarity	NPD6346	Approved
0.681	Remote Similarity	NPD1137	Approved
0.681	Remote Similarity	NPD1139	Approved
0.6807	Remote Similarity	NPD9493	Approved
0.68	Remote Similarity	NPD9089	Approved
0.6786	Remote Similarity	NPD9244	Approved
0.6774	Remote Similarity	NPD5327	Phase 3
0.6772	Remote Similarity	NPD4908	Phase 1
0.6762	Remote Similarity	NPD1089	Approved
0.6762	Remote Similarity	NPD1086	Approved
0.6762	Remote Similarity	NPD1090	Approved
0.6757	Remote Similarity	NPD4818	Approved
0.6757	Remote Similarity	NPD4817	Approved
0.6754	Remote Similarity	NPD9267	Approved
0.6754	Remote Similarity	NPD9263	Approved
0.6754	Remote Similarity	NPD9264	Approved
0.6752	Remote Similarity	NPD821	Approved
0.6752	Remote Similarity	NPD7843	Approved
0.675	Remote Similarity	NPD1758	Phase 1
0.675	Remote Similarity	NPD16	Approved
0.675	Remote Similarity	NPD856	Approved
0.6746	Remote Similarity	NPD6584	Phase 3
0.6742	Remote Similarity	NPD7742	Approved
0.6742	Remote Similarity	NPD7743	Approved
0.6741	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2667	Approved
0.6721	Remote Similarity	NPD2668	Approved
0.6721	Remote Similarity	NPD9381	Approved
0.6721	Remote Similarity	NPD9384	Approved
0.6721	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7095	Approved
0.67	Remote Similarity	NPD9093	Approved
0.6695	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1608	Approved
0.6694	Remote Similarity	NPD1548	Phase 1
0.6693	Remote Similarity	NPD4208	Discontinued
0.6693	Remote Similarity	NPD4212	Discontinued
0.6692	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD1131	Approved
0.6667	Remote Similarity	NPD3055	Approved
0.6667	Remote Similarity	NPD1133	Approved
0.6667	Remote Similarity	NPD800	Approved
0.6667	Remote Similarity	NPD1693	Approved
0.6667	Remote Similarity	NPD2209	Approved
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1129	Approved
0.6667	Remote Similarity	NPD1135	Approved
0.6667	Remote Similarity	NPD3053	Approved
0.6667	Remote Similarity	NPD1164	Approved
0.6667	Remote Similarity	NPD9295	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