NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.16
Volume:	251.815
LogP:	4.208
LogD:	3.738
LogS:	-4.057
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	2.287
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.004
MDCK Permeability:	1.2832313586841337e-05
Pgp-inhibitor:	0.606
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.696
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.334
Plasma Protein Binding (PPB):	97.4056396484375%
Volume Distribution (VD):	4.385
Pgp-substrate:	5.435357093811035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.896
CYP1A2-substrate:	0.913
CYP2C19-inhibitor:	0.479
CYP2C19-substrate:	0.53
CYP2C9-inhibitor:	0.494
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.874
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.341
CYP3A4-substrate:	0.449

ADMET: Excretion

Clearance (CL):	8.294
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.13
Maximum Recommended Daily Dose:	0.845
Skin Sensitization:	0.919
Carcinogencity:	0.031
Eye Corrosion:	0.904
Eye Irritation:	0.954
Respiratory Toxicity:	0.751

Download Data

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

Natural Product: NPC269212

Natural Product ID:	NPC269212
*Common Name:**	2,5-Ditertbutylhydroquinone
IUPAC Name:	2,6-ditert-butylbenzene-1,4-diol
Synonyms:	2,5-Ditertbutylhydroquinone
Standard InCHIKey:	JFGVTUJBHHZRAB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H22O2/c1-13(2,3)10-7-9(15)8-11(12(10)16)14(4,5)6/h7-8,15-16H,1-6H3
SMILES:	CC(C)(C)c1cc(cc(c1O)C(C)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375695
PubChem CID:	75550
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
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	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
Others	13

Activity Type	# Activity
Cell Line	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	2.5	n.a.	PMID[557076]
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	4.16	n.a.	PMID[557076]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	118.42	%	PMID[557077]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	230.26	%	PMID[557077]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	269.36	%	PMID[557077]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	326.89	%	PMID[557077]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	30.41	%	PMID[557077]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	36.58	%	PMID[557077]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	25.02	%	PMID[557077]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	42.06	%	PMID[557077]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	95.76	%	PMID[557077]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	92.12	%	PMID[557077]
NPT2891	Cell Line	H4	Homo sapiens	Activity	=	108.45	%	PMID[557077]

☑ 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 NPC269212 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	270
0.1-0.2	1754
0.2-0.3	4377
0.3-0.4	13403
0.4-0.5	7187
0.5-0.6	10430
0.6-0.7	4129
0.7-0.8	829
0.8-0.85	212
0.85-0.9	76
0.9-0.95	28
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC47284
0.9388	High Similarity	NPC108497
0.9368	High Similarity	NPC222146
0.93	High Similarity	NPC53740
0.9293	High Similarity	NPC272029
0.9208	High Similarity	NPC320439
0.9184	High Similarity	NPC248396
0.9184	High Similarity	NPC129373
0.9184	High Similarity	NPC48730
0.9175	High Similarity	NPC152097
0.9135	High Similarity	NPC98372
0.9109	High Similarity	NPC469913
0.9109	High Similarity	NPC155072
0.9091	High Similarity	NPC477685
0.9082	High Similarity	NPC122005
0.9082	High Similarity	NPC299762
0.9082	High Similarity	NPC260775
0.9082	High Similarity	NPC33675
0.9082	High Similarity	NPC252821
0.9062	High Similarity	NPC152415
0.9062	High Similarity	NPC289769
0.9038	High Similarity	NPC470770
0.9038	High Similarity	NPC266937
0.9038	High Similarity	NPC77772
0.899	High Similarity	NPC12931
0.899	High Similarity	NPC211885
0.899	High Similarity	NPC70677
0.899	High Similarity	NPC130756
0.899	High Similarity	NPC225506
0.898	High Similarity	NPC475078
0.8969	High Similarity	NPC144682
0.8958	High Similarity	NPC55903
0.8958	High Similarity	NPC29373
0.8952	High Similarity	NPC62867
0.8952	High Similarity	NPC177962
0.8932	High Similarity	NPC279887
0.8932	High Similarity	NPC68260
0.8922	High Similarity	NPC54765
0.8911	High Similarity	NPC475580
0.89	High Similarity	NPC252105
0.89	High Similarity	NPC12221
0.8857	High Similarity	NPC469912
0.8857	High Similarity	NPC275627
0.8854	High Similarity	NPC306074
0.8846	High Similarity	NPC26013
0.8846	High Similarity	NPC282855
0.88	High Similarity	NPC72729
0.8788	High Similarity	NPC79241
0.8788	High Similarity	NPC6597
0.8788	High Similarity	NPC77492
0.8774	High Similarity	NPC302371
0.8762	High Similarity	NPC208229
0.875	High Similarity	NPC95344
0.8738	High Similarity	NPC310456
0.8737	High Similarity	NPC19680
0.8725	High Similarity	NPC475225
0.8713	High Similarity	NPC80800
0.8687	High Similarity	NPC312132
0.8687	High Similarity	NPC259512
0.8673	High Similarity	NPC245187
0.8673	High Similarity	NPC316301
0.8673	High Similarity	NPC27323
0.8641	High Similarity	NPC138942
0.8641	High Similarity	NPC117115
0.8627	High Similarity	NPC233827
0.8627	High Similarity	NPC471228
0.8627	High Similarity	NPC235762
0.8624	High Similarity	NPC141001
0.8614	High Similarity	NPC130103
0.8614	High Similarity	NPC174911
0.8611	High Similarity	NPC471534
0.86	High Similarity	NPC474073
0.8586	High Similarity	NPC8392
0.8585	High Similarity	NPC132720
0.8585	High Similarity	NPC13482
0.8571	High Similarity	NPC162314
0.8571	High Similarity	NPC306295
0.8571	High Similarity	NPC306884
0.8571	High Similarity	NPC94139
0.8571	High Similarity	NPC210497
0.8571	High Similarity	NPC147284
0.8571	High Similarity	NPC3358
0.8558	High Similarity	NPC21594
0.8557	High Similarity	NPC192
0.8544	High Similarity	NPC288411
0.8542	High Similarity	NPC27974
0.8519	High Similarity	NPC296144
0.8519	High Similarity	NPC28784
0.8515	High Similarity	NPC92730
0.8515	High Similarity	NPC128723
0.8505	High Similarity	NPC260323
0.8505	High Similarity	NPC176279
0.8505	High Similarity	NPC54373
0.8491	Intermediate Similarity	NPC473524
0.8476	Intermediate Similarity	NPC66834
0.8476	Intermediate Similarity	NPC151477
0.8476	Intermediate Similarity	NPC233320
0.8469	Intermediate Similarity	NPC155908
0.8469	Intermediate Similarity	NPC204210
0.8469	Intermediate Similarity	NPC231150
0.8462	Intermediate Similarity	NPC219286
0.8462	Intermediate Similarity	NPC99557
0.8454	Intermediate Similarity	NPC70436
0.8447	Intermediate Similarity	NPC168829
0.844	Intermediate Similarity	NPC474114
0.844	Intermediate Similarity	NPC473931
0.844	Intermediate Similarity	NPC474050
0.844	Intermediate Similarity	NPC114918
0.8438	Intermediate Similarity	NPC307235
0.8438	Intermediate Similarity	NPC407
0.8426	Intermediate Similarity	NPC250323
0.8426	Intermediate Similarity	NPC228425
0.8416	Intermediate Similarity	NPC88420
0.8416	Intermediate Similarity	NPC225464
0.8411	Intermediate Similarity	NPC141782
0.8407	Intermediate Similarity	NPC474175
0.8396	Intermediate Similarity	NPC64586
0.8393	Intermediate Similarity	NPC323074
0.8381	Intermediate Similarity	NPC477814
0.8381	Intermediate Similarity	NPC67250
0.8378	Intermediate Similarity	NPC320864
0.8365	Intermediate Similarity	NPC120719
0.8365	Intermediate Similarity	NPC227458
0.8365	Intermediate Similarity	NPC130817
0.8365	Intermediate Similarity	NPC238696
0.8365	Intermediate Similarity	NPC218879
0.8365	Intermediate Similarity	NPC244513
0.8364	Intermediate Similarity	NPC35797
0.8364	Intermediate Similarity	NPC192948
0.8333	Intermediate Similarity	NPC155393
0.8333	Intermediate Similarity	NPC95716
0.8333	Intermediate Similarity	NPC151537
0.8319	Intermediate Similarity	NPC325544
0.8319	Intermediate Similarity	NPC477037
0.8319	Intermediate Similarity	NPC318581
0.8318	Intermediate Similarity	NPC98392
0.8318	Intermediate Similarity	NPC58865
0.8302	Intermediate Similarity	NPC474352
0.83	Intermediate Similarity	NPC76938
0.8288	Intermediate Similarity	NPC38893
0.8288	Intermediate Similarity	NPC477137
0.8288	Intermediate Similarity	NPC469663
0.8288	Intermediate Similarity	NPC308828
0.8288	Intermediate Similarity	NPC471668
0.8288	Intermediate Similarity	NPC92
0.8288	Intermediate Similarity	NPC308311
0.8288	Intermediate Similarity	NPC69539
0.8286	Intermediate Similarity	NPC37802
0.8283	Intermediate Similarity	NPC304541
0.8273	Intermediate Similarity	NPC195922
0.8273	Intermediate Similarity	NPC268160
0.8265	Intermediate Similarity	NPC242240
0.8265	Intermediate Similarity	NPC123273
0.8265	Intermediate Similarity	NPC318325
0.8257	Intermediate Similarity	NPC46940
0.8241	Intermediate Similarity	NPC224870
0.8241	Intermediate Similarity	NPC296683
0.8235	Intermediate Similarity	NPC156313
0.823	Intermediate Similarity	NPC469644
0.823	Intermediate Similarity	NPC471449
0.8229	Intermediate Similarity	NPC286904
0.8229	Intermediate Similarity	NPC150837
0.8224	Intermediate Similarity	NPC470039
0.8224	Intermediate Similarity	NPC262365
0.8218	Intermediate Similarity	NPC32714
0.8218	Intermediate Similarity	NPC274678
0.8214	Intermediate Similarity	NPC304510
0.8214	Intermediate Similarity	NPC172219
0.8214	Intermediate Similarity	NPC477136
0.8214	Intermediate Similarity	NPC187993
0.8214	Intermediate Similarity	NPC238176
0.8208	Intermediate Similarity	NPC99836
0.8208	Intermediate Similarity	NPC12640
0.8208	Intermediate Similarity	NPC271274
0.8208	Intermediate Similarity	NPC201662
0.82	Intermediate Similarity	NPC271440
0.8198	Intermediate Similarity	NPC147179
0.8198	Intermediate Similarity	NPC473718
0.8198	Intermediate Similarity	NPC469719
0.819	Intermediate Similarity	NPC323810
0.819	Intermediate Similarity	NPC93831
0.8182	Intermediate Similarity	NPC312304
0.8182	Intermediate Similarity	NPC263753
0.8173	Intermediate Similarity	NPC11280
0.8173	Intermediate Similarity	NPC147310
0.8173	Intermediate Similarity	NPC192032
0.8173	Intermediate Similarity	NPC24407
0.8173	Intermediate Similarity	NPC294186
0.8173	Intermediate Similarity	NPC51015
0.8173	Intermediate Similarity	NPC137415
0.8173	Intermediate Similarity	NPC166313
0.8165	Intermediate Similarity	NPC225679
0.8165	Intermediate Similarity	NPC228609
0.8165	Intermediate Similarity	NPC165770
0.8165	Intermediate Similarity	NPC4493
0.8165	Intermediate Similarity	NPC476632
0.8163	Intermediate Similarity	NPC25493
0.8163	Intermediate Similarity	NPC113460
0.8158	Intermediate Similarity	NPC475245
0.8148	Intermediate Similarity	NPC186385

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 NPC269212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	1075
0.2-0.3	1522
0.3-0.4	2963
0.4-0.5	1862
0.5-0.6	1068
0.6-0.7	330
0.7-0.8	61
0.8-0.85	4
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9583	High Similarity	NPD289	Clinical (unspecified phase)
0.8969	High Similarity	NPD1809	Phase 2
0.8776	High Similarity	NPD844	Approved
0.8763	High Similarity	NPD845	Approved
0.8687	High Similarity	NPD288	Approved
0.8673	High Similarity	NPD1432	Clinical (unspecified phase)
0.8598	High Similarity	NPD7635	Approved
0.8155	Intermediate Similarity	NPD3020	Approved
0.8148	Intermediate Similarity	NPD4750	Phase 3
0.8039	Intermediate Similarity	NPD2860	Approved
0.8039	Intermediate Similarity	NPD2859	Approved
0.8036	Intermediate Similarity	NPD6671	Approved
0.8	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD846	Approved
0.8	Intermediate Similarity	NPD940	Approved
0.7966	Intermediate Similarity	NPD6696	Suspended
0.7963	Intermediate Similarity	NPD2342	Discontinued
0.7941	Intermediate Similarity	NPD2934	Approved
0.7941	Intermediate Similarity	NPD2933	Approved
0.787	Intermediate Similarity	NPD1445	Approved
0.787	Intermediate Similarity	NPD1444	Approved
0.7857	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD3021	Approved
0.7818	Intermediate Similarity	NPD3022	Approved
0.7788	Intermediate Similarity	NPD497	Approved
0.7757	Intermediate Similarity	NPD9500	Approved
0.7755	Intermediate Similarity	NPD111	Approved
0.7699	Intermediate Similarity	NPD495	Approved
0.7699	Intermediate Similarity	NPD498	Approved
0.7699	Intermediate Similarity	NPD496	Approved
0.7699	Intermediate Similarity	NPD1398	Phase 1
0.7672	Intermediate Similarity	NPD3091	Approved
0.7658	Intermediate Similarity	NPD1792	Phase 2
0.7632	Intermediate Similarity	NPD1793	Approved
0.7632	Intermediate Similarity	NPD1791	Approved
0.7542	Intermediate Similarity	NPD2932	Approved
0.7542	Intermediate Similarity	NPD3019	Approved
0.7542	Intermediate Similarity	NPD4589	Approved
0.7542	Intermediate Similarity	NPD4059	Approved
0.7521	Intermediate Similarity	NPD7330	Discontinued
0.75	Intermediate Similarity	NPD7340	Approved
0.7458	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3092	Approved
0.7407	Intermediate Similarity	NPD1242	Phase 1
0.7396	Intermediate Similarity	NPD9088	Approved
0.7395	Intermediate Similarity	NPD4626	Approved
0.7395	Intermediate Similarity	NPD1751	Approved
0.735	Intermediate Similarity	NPD7636	Approved
0.7333	Intermediate Similarity	NPD3143	Discontinued
0.7333	Intermediate Similarity	NPD3496	Discontinued
0.7317	Intermediate Similarity	NPD3094	Phase 2
0.7273	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3095	Discontinued
0.7241	Intermediate Similarity	NPD2234	Approved
0.7241	Intermediate Similarity	NPD2229	Approved
0.7241	Intermediate Similarity	NPD2228	Approved
0.7232	Intermediate Similarity	NPD968	Approved
0.7227	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5303	Approved
0.7227	Intermediate Similarity	NPD5304	Approved
0.7222	Intermediate Similarity	NPD9273	Approved
0.7217	Intermediate Similarity	NPD228	Approved
0.7213	Intermediate Similarity	NPD3070	Discontinued
0.7203	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2861	Phase 2
0.719	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9618	Approved
0.7179	Intermediate Similarity	NPD9614	Approved
0.7167	Intermediate Similarity	NPD4093	Discontinued
0.7165	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4749	Approved
0.7154	Intermediate Similarity	NPD1755	Approved
0.7131	Intermediate Similarity	NPD1611	Approved
0.7131	Intermediate Similarity	NPD1201	Approved
0.7107	Intermediate Similarity	NPD2286	Discontinued
0.7087	Intermediate Similarity	NPD4625	Phase 3
0.7073	Intermediate Similarity	NPD2230	Approved
0.7073	Intermediate Similarity	NPD2233	Approved
0.7073	Intermediate Similarity	NPD2232	Approved
0.7063	Intermediate Similarity	NPD5736	Approved
0.7059	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9610	Approved
0.7054	Intermediate Similarity	NPD9608	Approved
0.7034	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5691	Approved
0.7009	Intermediate Similarity	NPD9377	Approved
0.7009	Intermediate Similarity	NPD1138	Approved
0.7009	Intermediate Similarity	NPD9379	Approved
0.7	Intermediate Similarity	NPD9615	Approved
0.7	Intermediate Similarity	NPD9616	Approved
0.7	Intermediate Similarity	NPD9613	Approved
0.6984	Remote Similarity	NPD2194	Approved
0.6984	Remote Similarity	NPD2195	Approved
0.6979	Remote Similarity	NPD9087	Approved
0.6975	Remote Similarity	NPD7157	Approved
0.6975	Remote Similarity	NPD709	Approved
0.6967	Remote Similarity	NPD1778	Approved
0.6952	Remote Similarity	NPD9295	Approved
0.6947	Remote Similarity	NPD4097	Suspended
0.6942	Remote Similarity	NPD316	Approved
0.6937	Remote Similarity	NPD3028	Approved
0.6929	Remote Similarity	NPD3636	Approved
0.6929	Remote Similarity	NPD4208	Discontinued
0.6929	Remote Similarity	NPD3637	Approved
0.6929	Remote Similarity	NPD4212	Discontinued
0.6929	Remote Similarity	NPD3635	Approved
0.6923	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD1137	Approved
0.6923	Remote Similarity	NPD1139	Approved
0.6917	Remote Similarity	NPD2935	Discontinued
0.6911	Remote Similarity	NPD3026	Approved
0.6911	Remote Similarity	NPD3023	Approved
0.6905	Remote Similarity	NPD1470	Approved
0.6885	Remote Similarity	NPD3024	Approved
0.6885	Remote Similarity	NPD3025	Approved
0.6875	Remote Similarity	NPD596	Approved
0.6875	Remote Similarity	NPD4207	Discontinued
0.6875	Remote Similarity	NPD2606	Approved
0.6875	Remote Similarity	NPD2605	Approved
0.6875	Remote Similarity	NPD600	Approved
0.687	Remote Similarity	NPD290	Approved
0.685	Remote Similarity	NPD4624	Approved
0.6846	Remote Similarity	NPD6663	Approved
0.6838	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5156	Approved
0.6822	Remote Similarity	NPD5155	Approved
0.6814	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2684	Approved
0.6807	Remote Similarity	NPD5283	Phase 1
0.6794	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3620	Phase 2
0.6772	Remote Similarity	NPD1135	Approved
0.6772	Remote Similarity	NPD1129	Approved
0.6772	Remote Similarity	NPD1131	Approved
0.6772	Remote Similarity	NPD1164	Approved
0.6772	Remote Similarity	NPD1133	Approved
0.6772	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1134	Approved
0.6769	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD9294	Approved
0.6752	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.675	Remote Similarity	NPD475	Phase 2
0.6748	Remote Similarity	NPD1651	Approved
0.6748	Remote Similarity	NPD1357	Approved
0.6746	Remote Similarity	NPD1669	Approved
0.6744	Remote Similarity	NPD3594	Approved
0.6744	Remote Similarity	NPD3595	Approved
0.6721	Remote Similarity	NPD7644	Approved
0.672	Remote Similarity	NPD1610	Phase 2
0.6718	Remote Similarity	NPD839	Approved
0.6718	Remote Similarity	NPD4248	Discontinued
0.6718	Remote Similarity	NPD840	Approved
0.6694	Remote Similarity	NPD255	Approved
0.6694	Remote Similarity	NPD256	Approved
0.6694	Remote Similarity	NPD9384	Approved
0.6694	Remote Similarity	NPD6387	Discontinued
0.6694	Remote Similarity	NPD9381	Approved
0.6693	Remote Similarity	NPD8651	Approved
0.6693	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD1759	Phase 1
0.6667	Remote Similarity	NPD1712	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2237	Approved
0.6667	Remote Similarity	NPD9093	Approved
0.6667	Remote Similarity	NPD74	Approved
0.6667	Remote Similarity	NPD6346	Approved
0.6667	Remote Similarity	NPD9266	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.664	Remote Similarity	NPD1983	Approved
0.664	Remote Similarity	NPD1980	Approved
0.664	Remote Similarity	NPD1981	Approved
0.6639	Remote Similarity	NPD9493	Approved
0.6615	Remote Similarity	NPD4908	Phase 1
0.6615	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5327	Phase 3
0.6614	Remote Similarity	NPD9622	Approved
0.6613	Remote Similarity	NPD5585	Approved
0.6609	Remote Similarity	NPD9244	Approved
0.6606	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD9089	Approved
0.6596	Remote Similarity	NPD6090	Discontinued
0.6594	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7743	Approved
0.6593	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7742	Approved
0.6589	Remote Similarity	NPD3690	Phase 2
0.6589	Remote Similarity	NPD858	Approved
0.6589	Remote Similarity	NPD3691	Phase 2
0.6589	Remote Similarity	NPD859	Approved
0.6589	Remote Similarity	NPD599	Approved
0.6589	Remote Similarity	NPD602	Approved
0.6589	Remote Similarity	NPD6584	Phase 3
0.6585	Remote Similarity	NPD1758	Phase 1
0.6585	Remote Similarity	NPD856	Approved
0.6585	Remote Similarity	NPD16	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