NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.17
Volume:	243.025
LogP:	4.832
LogD:	4.333
LogS:	-4.599
# Rotatable Bonds:	2
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	2.015
Fsp3:	0.571
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:	-5.048
MDCK Permeability:	1.0667621609172784e-05
Pgp-inhibitor:	0.585
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.727
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.294
Plasma Protein Binding (PPB):	98.43366241455078%
Volume Distribution (VD):	4.896
Pgp-substrate:	4.953541278839111%

ADMET: Metabolism

CYP1A2-inhibitor:	0.907
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.77
CYP2C19-substrate:	0.779
CYP2C9-inhibitor:	0.633
CYP2C9-substrate:	0.872
CYP2D6-inhibitor:	0.885
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.429
CYP3A4-substrate:	0.669

ADMET: Excretion

Clearance (CL):	6.3
Half-life (T1/2):	0.324

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.744
Skin Sensitization:	0.739
Carcinogencity:	0.034
Eye Corrosion:	0.983
Eye Irritation:	0.986
Respiratory Toxicity:	0.699

Download Data

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

Natural Product: NPC252821

Natural Product ID:	NPC252821
*Common Name:**	2,4-Ditert-Butylphenol
IUPAC Name:	2,4-ditert-butylphenol
Synonyms:
Standard InCHIKey:	ICKWICRCANNIBI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H22O/c1-13(2,3)10-7-8-12(15)11(9-10)14(4,5)6/h7-9,15H,1-6H3
SMILES:	Oc1ccc(cc1C(C)(C)C)C(C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL29873
PubChem CID:	7311
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

☑ 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	3
LD50	1
Others	3
Potency	102

Activity Type	# Activity
Cell Line	1
Individual Protein	14
Organism	3
Others	89
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	4.24	n.a.	PMID[484291]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	13800.6	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	61396	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	30513.3	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	60882	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	54719.2	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	43465	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	43641.2	nM	PubChem BioAssay data set
NPT1007	Protein Complex	GABA-A receptor; alpha-1/beta-2/gamma-2	Homo sapiens	EC50	=	100000000.0	nM	PMID[484289]
NPT693	Organism	Xenopus laevis	Xenopus laevis	EC50	=	100000000.0	nM	PMID[484289]
NPT35	Others	n.a.		CLogP	=	5.1	n.a.	PMID[484289]
NPT32	Organism	Mus musculus	Mus musculus	HD50	=	40.0	mg kg-1	PMID[484290]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	100.0	mg.kg-1	PMID[484290]
NPT610	Others	Molecular identity unknown		Potency	n.a.	70794.6	nM	PMID[484292]
NPT2	Others	Unspecified		Potency	n.a.	27535.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24442.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38738.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43641.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	60882	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	385.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54719.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61396	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2719.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	3063.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27195	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54261.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30513.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68310.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17373.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	7760.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	34525.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30895.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43465	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38895.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1082.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48768.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48360.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24237.6	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	19415.1	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.	21784.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24541.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21872.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	15292.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	12197.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43101.1	nM	PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC252821 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	303
0.1-0.2	1887
0.2-0.3	4494
0.3-0.4	13191
0.4-0.5	7045
0.5-0.6	9729
0.6-0.7	4704
0.7-0.8	1033
0.8-0.85	194
0.85-0.9	86
0.9-0.95	23
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC122005
0.9892	High Similarity	NPC225506
0.9677	High Similarity	NPC77492
0.9674	High Similarity	NPC144682
0.9565	High Similarity	NPC289769
0.9565	High Similarity	NPC152415
0.9565	High Similarity	NPC27323
0.9565	High Similarity	NPC316301
0.9462	High Similarity	NPC8392
0.9348	High Similarity	NPC155908
0.9348	High Similarity	NPC306074
0.9348	High Similarity	NPC204210
0.9271	High Similarity	NPC211885
0.9263	High Similarity	NPC225464
0.9255	High Similarity	NPC222146
0.9167	High Similarity	NPC92730
0.9167	High Similarity	NPC33675
0.9167	High Similarity	NPC299762
0.9167	High Similarity	NPC128723
0.914	High Similarity	NPC304541
0.913	High Similarity	NPC242240
0.913	High Similarity	NPC318325
0.913	High Similarity	NPC123273
0.913	High Similarity	NPC70436
0.9091	High Similarity	NPC138942
0.9082	High Similarity	NPC269212
0.9082	High Similarity	NPC168829
0.9043	High Similarity	NPC55903
0.9022	High Similarity	NPC25493
0.9022	High Similarity	NPC113460
0.902	High Similarity	NPC13482
0.9	High Similarity	NPC271274
0.899	High Similarity	NPC288411
0.898	High Similarity	NPC252105
0.8925	High Similarity	NPC258219
0.8925	High Similarity	NPC280347
0.8925	High Similarity	NPC98772
0.8925	High Similarity	NPC177420
0.8913	High Similarity	NPC407
0.8913	High Similarity	NPC184169
0.8913	High Similarity	NPC307235
0.8913	High Similarity	NPC23167
0.89	High Similarity	NPC219286
0.89	High Similarity	NPC99557
0.8866	High Similarity	NPC79241
0.8866	High Similarity	NPC6597
0.8846	High Similarity	NPC250323
0.8846	High Similarity	NPC228425
0.8835	High Similarity	NPC141782
0.883	High Similarity	NPC55561
0.8824	High Similarity	NPC470039
0.8812	High Similarity	NPC21594
0.8804	High Similarity	NPC197783
0.8804	High Similarity	NPC155393
0.8763	High Similarity	NPC312132
0.8763	High Similarity	NPC259512
0.875	High Similarity	NPC260323
0.875	High Similarity	NPC128062
0.875	High Similarity	NPC176279
0.875	High Similarity	NPC245187
0.8738	High Similarity	NPC58865
0.8737	High Similarity	NPC270547
0.8725	High Similarity	NPC228737
0.8725	High Similarity	NPC151477
0.8713	High Similarity	NPC303141
0.8713	High Similarity	NPC47284
0.87	High Similarity	NPC108497
0.8696	High Similarity	NPC286904
0.8696	High Similarity	NPC175313
0.8696	High Similarity	NPC248817
0.8687	High Similarity	NPC72729
0.8679	High Similarity	NPC195922
0.866	High Similarity	NPC26244
0.8654	High Similarity	NPC296683
0.8646	High Similarity	NPC3358
0.8646	High Similarity	NPC271440
0.8646	High Similarity	NPC147284
0.8646	High Similarity	NPC306884
0.8646	High Similarity	NPC162314
0.8646	High Similarity	NPC210497
0.8646	High Similarity	NPC94139
0.8641	High Similarity	NPC262365
0.8632	High Similarity	NPC192
0.8627	High Similarity	NPC310456
0.8627	High Similarity	NPC477814
0.8627	High Similarity	NPC54765
0.8627	High Similarity	NPC53740
0.8617	High Similarity	NPC19680
0.8617	High Similarity	NPC27974
0.8614	High Similarity	NPC120719
0.86	High Similarity	NPC51015
0.8587	High Similarity	NPC265146
0.8587	High Similarity	NPC124436
0.8571	High Similarity	NPC82664
0.8571	High Similarity	NPC216520
0.8571	High Similarity	NPC95716
0.8571	High Similarity	NPC132271
0.8571	High Similarity	NPC473388
0.8571	High Similarity	NPC292730
0.8557	High Similarity	NPC151715
0.8544	High Similarity	NPC320439
0.8542	High Similarity	NPC45040
0.8542	High Similarity	NPC231150
0.8529	High Similarity	NPC117115
0.8529	High Similarity	NPC243677
0.8515	High Similarity	NPC470202
0.8505	High Similarity	NPC268160
0.85	High Similarity	NPC48730
0.85	High Similarity	NPC248396
0.85	High Similarity	NPC129373
0.8491	Intermediate Similarity	NPC46940
0.8485	Intermediate Similarity	NPC152097
0.8476	Intermediate Similarity	NPC44732
0.8469	Intermediate Similarity	NPC274678
0.8462	Intermediate Similarity	NPC61885
0.8462	Intermediate Similarity	NPC95344
0.8462	Intermediate Similarity	NPC306295
0.8462	Intermediate Similarity	NPC64586
0.8462	Intermediate Similarity	NPC63698
0.8454	Intermediate Similarity	NPC325292
0.8454	Intermediate Similarity	NPC138117
0.8447	Intermediate Similarity	NPC155072
0.844	Intermediate Similarity	NPC477136
0.8438	Intermediate Similarity	NPC300017
0.8431	Intermediate Similarity	NPC475225
0.8431	Intermediate Similarity	NPC272029
0.8431	Intermediate Similarity	NPC238696
0.8426	Intermediate Similarity	NPC35797
0.8426	Intermediate Similarity	NPC192948
0.8426	Intermediate Similarity	NPC147179
0.8416	Intermediate Similarity	NPC471578
0.8416	Intermediate Similarity	NPC101025
0.8411	Intermediate Similarity	NPC35344
0.8411	Intermediate Similarity	NPC715
0.8411	Intermediate Similarity	NPC141003
0.84	Intermediate Similarity	NPC80027
0.84	Intermediate Similarity	NPC260775
0.8396	Intermediate Similarity	NPC151537
0.8396	Intermediate Similarity	NPC266937
0.8396	Intermediate Similarity	NPC225679
0.8396	Intermediate Similarity	NPC165770
0.8396	Intermediate Similarity	NPC308689
0.8396	Intermediate Similarity	NPC4493
0.8396	Intermediate Similarity	NPC322753
0.8396	Intermediate Similarity	NPC77772
0.8396	Intermediate Similarity	NPC476632
0.8396	Intermediate Similarity	NPC470770
0.8384	Intermediate Similarity	NPC202986
0.8381	Intermediate Similarity	NPC314187
0.8381	Intermediate Similarity	NPC75272
0.8381	Intermediate Similarity	NPC471954
0.8367	Intermediate Similarity	NPC76938
0.8349	Intermediate Similarity	NPC477137
0.8349	Intermediate Similarity	NPC38893
0.8349	Intermediate Similarity	NPC219112
0.8349	Intermediate Similarity	NPC308828
0.8349	Intermediate Similarity	NPC308311
0.8349	Intermediate Similarity	NPC471668
0.8333	Intermediate Similarity	NPC62351
0.8333	Intermediate Similarity	NPC471228
0.8333	Intermediate Similarity	NPC107240
0.8333	Intermediate Similarity	NPC12656
0.8333	Intermediate Similarity	NPC235762
0.8318	Intermediate Similarity	NPC98372
0.8318	Intermediate Similarity	NPC228988
0.8318	Intermediate Similarity	NPC62867
0.8318	Intermediate Similarity	NPC286222
0.8318	Intermediate Similarity	NPC43525
0.8318	Intermediate Similarity	NPC177962
0.8317	Intermediate Similarity	NPC130756
0.8317	Intermediate Similarity	NPC174911
0.8317	Intermediate Similarity	NPC12931
0.8317	Intermediate Similarity	NPC70677
0.8302	Intermediate Similarity	NPC224870
0.83	Intermediate Similarity	NPC156313
0.83	Intermediate Similarity	NPC475078
0.83	Intermediate Similarity	NPC32674
0.83	Intermediate Similarity	NPC474073
0.8298	Intermediate Similarity	NPC150837
0.8286	Intermediate Similarity	NPC11554
0.8283	Intermediate Similarity	NPC32714
0.8283	Intermediate Similarity	NPC313650
0.8273	Intermediate Similarity	NPC304510
0.8273	Intermediate Similarity	NPC172219
0.8273	Intermediate Similarity	NPC16030
0.8269	Intermediate Similarity	NPC469913
0.8269	Intermediate Similarity	NPC248904
0.8265	Intermediate Similarity	NPC29373
0.8257	Intermediate Similarity	NPC474486
0.8252	Intermediate Similarity	NPC119860
0.8252	Intermediate Similarity	NPC475580
0.8241	Intermediate Similarity	NPC117846
0.8241	Intermediate Similarity	NPC263753
0.8235	Intermediate Similarity	NPC12221
0.8235	Intermediate Similarity	NPC472585
0.8235	Intermediate Similarity	NPC477685
0.8229	Intermediate Similarity	NPC104216
0.8224	Intermediate Similarity	NPC275627
0.8218	Intermediate Similarity	NPC78119
0.8218	Intermediate Similarity	NPC51333

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 NPC252821 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	1060
0.2-0.3	1366
0.3-0.4	2890
0.4-0.5	1897
0.5-0.6	1116
0.6-0.7	410
0.7-0.8	78
0.8-0.85	8
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9674	High Similarity	NPD1809	Phase 2
0.9565	High Similarity	NPD1432	Clinical (unspecified phase)
0.9247	High Similarity	NPD845	Approved
0.8878	High Similarity	NPD289	Clinical (unspecified phase)
0.8854	High Similarity	NPD844	Approved
0.8776	High Similarity	NPD3020	Approved
0.8763	High Similarity	NPD288	Approved
0.866	High Similarity	NPD2859	Approved
0.866	High Similarity	NPD2860	Approved
0.86	High Similarity	NPD940	Approved
0.86	High Similarity	NPD846	Approved
0.8587	High Similarity	NPD111	Approved
0.8557	High Similarity	NPD2934	Approved
0.8557	High Similarity	NPD2933	Approved
0.8396	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.8241	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD4589	Approved
0.8037	Intermediate Similarity	NPD3022	Approved
0.8037	Intermediate Similarity	NPD3021	Approved
0.8019	Intermediate Similarity	NPD2342	Discontinued
0.7982	Intermediate Similarity	NPD7635	Approved
0.7925	Intermediate Similarity	NPD1444	Approved
0.7925	Intermediate Similarity	NPD1445	Approved
0.7876	Intermediate Similarity	NPD5304	Approved
0.7876	Intermediate Similarity	NPD3091	Approved
0.7876	Intermediate Similarity	NPD5303	Approved
0.787	Intermediate Similarity	NPD4750	Phase 3
0.7807	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2228	Approved
0.7748	Intermediate Similarity	NPD2234	Approved
0.7748	Intermediate Similarity	NPD2229	Approved
0.7739	Intermediate Similarity	NPD2932	Approved
0.7739	Intermediate Similarity	NPD3019	Approved
0.7739	Intermediate Similarity	NPD4059	Approved
0.7739	Intermediate Similarity	NPD1751	Approved
0.7736	Intermediate Similarity	NPD9610	Approved
0.7736	Intermediate Similarity	NPD9608	Approved
0.7706	Intermediate Similarity	NPD1792	Phase 2
0.7679	Intermediate Similarity	NPD1793	Approved
0.7679	Intermediate Similarity	NPD1791	Approved
0.7672	Intermediate Similarity	NPD3143	Discontinued
0.7672	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD9500	Approved
0.7627	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1242	Phase 1
0.7607	Intermediate Similarity	NPD3092	Approved
0.7586	Intermediate Similarity	NPD4626	Approved
0.7565	Intermediate Similarity	NPD7330	Discontinued
0.7542	Intermediate Similarity	NPD3070	Discontinued
0.75	Intermediate Similarity	NPD4093	Discontinued
0.7456	Intermediate Similarity	NPD6671	Approved
0.7456	Intermediate Similarity	NPD7157	Approved
0.7453	Intermediate Similarity	NPD3028	Approved
0.7436	Intermediate Similarity	NPD3095	Discontinued
0.7429	Intermediate Similarity	NPD9273	Approved
0.7411	Intermediate Similarity	NPD228	Approved
0.7391	Intermediate Similarity	NPD9087	Approved
0.7391	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7636	Approved
0.7355	Intermediate Similarity	NPD3094	Phase 2
0.7297	Intermediate Similarity	NPD2684	Approved
0.7295	Intermediate Similarity	NPD2194	Approved
0.7295	Intermediate Similarity	NPD2195	Approved
0.7288	Intermediate Similarity	NPD2286	Discontinued
0.7273	Intermediate Similarity	NPD6696	Suspended
0.7265	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3635	Approved
0.7236	Intermediate Similarity	NPD3637	Approved
0.7236	Intermediate Similarity	NPD4212	Discontinued
0.7236	Intermediate Similarity	NPD4208	Discontinued
0.7236	Intermediate Similarity	NPD3636	Approved
0.7236	Intermediate Similarity	NPD5736	Approved
0.7232	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD497	Approved
0.7217	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD475	Phase 2
0.7213	Intermediate Similarity	NPD1135	Approved
0.7213	Intermediate Similarity	NPD1164	Approved
0.7213	Intermediate Similarity	NPD1133	Approved
0.7213	Intermediate Similarity	NPD1134	Approved
0.7213	Intermediate Similarity	NPD1131	Approved
0.7213	Intermediate Similarity	NPD1129	Approved
0.7203	Intermediate Similarity	NPD5691	Approved
0.72	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD9377	Approved
0.7193	Intermediate Similarity	NPD1138	Approved
0.7193	Intermediate Similarity	NPD9379	Approved
0.7177	Intermediate Similarity	NPD2606	Approved
0.7177	Intermediate Similarity	NPD2605	Approved
0.7177	Intermediate Similarity	NPD4207	Discontinued
0.7167	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1610	Phase 2
0.7167	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD9294	Approved
0.7156	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD256	Approved
0.7155	Intermediate Similarity	NPD255	Approved
0.7131	Intermediate Similarity	NPD8651	Approved
0.713	Intermediate Similarity	NPD498	Approved
0.713	Intermediate Similarity	NPD495	Approved
0.713	Intermediate Similarity	NPD496	Approved
0.712	Intermediate Similarity	NPD5156	Approved
0.712	Intermediate Similarity	NPD5155	Approved
0.7109	Intermediate Similarity	NPD4097	Suspended
0.7105	Intermediate Similarity	NPD1139	Approved
0.7105	Intermediate Similarity	NPD1137	Approved
0.7087	Intermediate Similarity	NPD4060	Phase 1
0.7083	Intermediate Similarity	NPD9088	Approved
0.7083	Intermediate Similarity	NPD3026	Approved
0.7083	Intermediate Similarity	NPD3023	Approved
0.7059	Intermediate Similarity	NPD3025	Approved
0.7059	Intermediate Similarity	NPD3024	Approved
0.7054	Intermediate Similarity	NPD290	Approved
0.7049	Intermediate Similarity	NPD1755	Approved
0.7043	Intermediate Similarity	NPD7843	Approved
0.7043	Intermediate Similarity	NPD821	Approved
0.704	Intermediate Similarity	NPD3594	Approved
0.704	Intermediate Similarity	NPD3595	Approved
0.704	Intermediate Similarity	NPD4908	Phase 1
0.7034	Intermediate Similarity	NPD856	Approved
0.7034	Intermediate Similarity	NPD16	Approved
0.7025	Intermediate Similarity	NPD1201	Approved
0.7016	Intermediate Similarity	NPD3690	Phase 2
0.7016	Intermediate Similarity	NPD3691	Phase 2
0.7016	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4624	Approved
0.7008	Intermediate Similarity	NPD6663	Approved
0.7	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2668	Approved
0.7	Intermediate Similarity	NPD2667	Approved
0.6984	Remote Similarity	NPD4625	Phase 3
0.6983	Remote Similarity	NPD1398	Phase 1
0.6983	Remote Similarity	NPD5283	Phase 1
0.6975	Remote Similarity	NPD1548	Phase 1
0.6964	Remote Similarity	NPD968	Approved
0.696	Remote Similarity	NPD2861	Phase 2
0.6949	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5451	Approved
0.6929	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9618	Approved
0.6923	Remote Similarity	NPD9614	Approved
0.6917	Remote Similarity	NPD1357	Approved
0.6917	Remote Similarity	NPD1651	Approved
0.6911	Remote Similarity	NPD1669	Approved
0.6911	Remote Similarity	NPD4749	Approved
0.6903	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD317	Approved
0.6891	Remote Similarity	NPD318	Approved
0.6885	Remote Similarity	NPD422	Phase 1
0.6875	Remote Similarity	NPD6407	Approved
0.6875	Remote Similarity	NPD6405	Approved
0.687	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD709	Approved
0.6864	Remote Similarity	NPD6387	Discontinued
0.686	Remote Similarity	NPD1778	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
0.6829	Remote Similarity	NPD2230	Approved
0.6829	Remote Similarity	NPD2233	Approved
0.6829	Remote Similarity	NPD2232	Approved
0.6822	Remote Similarity	NPD3620	Phase 2
0.6822	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1616	Discontinued
0.6807	Remote Similarity	NPD9493	Approved
0.6807	Remote Similarity	NPD7340	Approved
0.6807	Remote Similarity	NPD9568	Approved
0.6803	Remote Similarity	NPD3496	Discontinued
0.68	Remote Similarity	NPD9089	Approved
0.68	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1470	Approved
0.68	Remote Similarity	NPD4103	Phase 2
0.6792	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4659	Approved
0.6774	Remote Similarity	NPD6583	Phase 3
0.6774	Remote Similarity	NPD6582	Phase 2
0.6774	Remote Similarity	NPD5327	Phase 3
0.6765	Remote Similarity	NPD5734	Clinical (unspecified phase)
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	NPD5535	Approved
0.675	Remote Similarity	NPD1758	Phase 1
0.675	Remote Similarity	NPD9616	Approved
0.675	Remote Similarity	NPD9613	Approved
0.675	Remote Similarity	NPD9615	Approved
0.6746	Remote Similarity	NPD6584	Phase 3
0.6744	Remote Similarity	NPD4248	Discontinued
0.6742	Remote Similarity	NPD7742	Approved
0.6742	Remote Similarity	NPD7743	Approved
0.6741	Remote Similarity	NPD7003	Approved
0.6721	Remote Similarity	NPD9381	Approved
0.6721	Remote Similarity	NPD9384	Approved
0.6719	Remote Similarity	NPD7095	Approved
0.6718	Remote Similarity	NPD2157	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