NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.18
Volume:	260.321
LogP:	5.312
LogD:	4.68
LogS:	-4.823
# 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:	0.691
Synthetic Accessibility Score:	2.397
Fsp3:	0.6
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:	-5.209
MDCK Permeability:	9.413870429852977e-06
Pgp-inhibitor:	0.236
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.908
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.717
Plasma Protein Binding (PPB):	97.41995239257812%
Volume Distribution (VD):	4.891
Pgp-substrate:	5.004570484161377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.92
CYP2C19-inhibitor:	0.582
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.46
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.915
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.556
CYP3A4-substrate:	0.558

ADMET: Excretion

Clearance (CL):	7.817
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.612
Carcinogencity:	0.025
Eye Corrosion:	0.971
Eye Irritation:	0.985
Respiratory Toxicity:	0.718

Download Data

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

Natural Product: NPC211885

Natural Product ID:	NPC211885
*Common Name:**	3,5-Ditert-Butyl-4-Methylphenol
IUPAC Name:	3,5-ditert-butyl-4-methylphenol
Synonyms:
Standard InCHIKey:	SMNGQGWPUVVORF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H24O/c1-10-12(14(2,3)4)8-11(16)9-13(10)15(5,6)7/h8-9,16H,1-7H3
SMILES:	Cc1c(cc(cc1C(C)(C)C)O)C(C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3093613
PubChem CID:	10220096
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
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23628	Imperata cylindrica	Species	Poaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	0.0	%	PMID[513201]

☑ 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 NPC211885 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	313
0.1-0.2	1929
0.2-0.3	4667
0.3-0.4	12908
0.4-0.5	7534
0.5-0.6	9794
0.6-0.7	4312
0.7-0.8	951
0.8-0.85	198
0.85-0.9	74
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.957	High Similarity	NPC222146
0.9271	High Similarity	NPC252821
0.9271	High Similarity	NPC122005
0.9255	High Similarity	NPC27323
0.9255	High Similarity	NPC316301
0.9175	High Similarity	NPC225506
0.9158	High Similarity	NPC144682
0.9149	High Similarity	NPC55903
0.9118	High Similarity	NPC13482
0.91	High Similarity	NPC21594
0.9043	High Similarity	NPC155908
0.9029	High Similarity	NPC260323
0.9029	High Similarity	NPC176279
0.901	High Similarity	NPC151477
0.899	High Similarity	NPC269212
0.8969	High Similarity	NPC77492
0.8969	High Similarity	NPC225464
0.8942	High Similarity	NPC250323
0.8932	High Similarity	NPC141782
0.8925	High Similarity	NPC19680
0.8878	High Similarity	NPC299762
0.8878	High Similarity	NPC92730
0.8878	High Similarity	NPC33675
0.8866	High Similarity	NPC202986
0.8854	High Similarity	NPC152415
0.8854	High Similarity	NPC289769
0.8854	High Similarity	NPC245187
0.8846	High Similarity	NPC322753
0.8842	High Similarity	NPC304541
0.8835	High Similarity	NPC58865
0.883	High Similarity	NPC123273
0.883	High Similarity	NPC318325
0.883	High Similarity	NPC242240
0.8812	High Similarity	NPC117115
0.8776	High Similarity	NPC32674
0.8774	High Similarity	NPC195922
0.8763	High Similarity	NPC8392
0.875	High Similarity	NPC162314
0.875	High Similarity	NPC306884
0.875	High Similarity	NPC147284
0.875	High Similarity	NPC210497
0.875	High Similarity	NPC94139
0.875	High Similarity	NPC3358
0.8738	High Similarity	NPC11554
0.8737	High Similarity	NPC192
0.8725	High Similarity	NPC477814
0.8723	High Similarity	NPC27974
0.8723	High Similarity	NPC25493
0.8723	High Similarity	NPC113460
0.8713	High Similarity	NPC120719
0.8713	High Similarity	NPC272029
0.87	High Similarity	NPC252105
0.8692	High Similarity	NPC35797
0.8692	High Similarity	NPC192948
0.8667	High Similarity	NPC151537
0.8667	High Similarity	NPC95716
0.8646	High Similarity	NPC306074
0.8646	High Similarity	NPC204210
0.8632	High Similarity	NPC177420
0.8632	High Similarity	NPC70436
0.8632	High Similarity	NPC258219
0.8632	High Similarity	NPC280347
0.8632	High Similarity	NPC98772
0.8617	High Similarity	NPC184169
0.8617	High Similarity	NPC23167
0.8611	High Similarity	NPC38893
0.8611	High Similarity	NPC471668
0.8611	High Similarity	NPC477137
0.8611	High Similarity	NPC308311
0.8598	High Similarity	NPC268160
0.8586	High Similarity	NPC79241
0.8586	High Similarity	NPC6597
0.8585	High Similarity	NPC228425
0.8585	High Similarity	NPC46940
0.8571	High Similarity	NPC224870
0.8571	High Similarity	NPC274678
0.8542	High Similarity	NPC55561
0.8532	High Similarity	NPC477136
0.8532	High Similarity	NPC172219
0.8532	High Similarity	NPC304510
0.8529	High Similarity	NPC327811
0.8529	High Similarity	NPC238696
0.8529	High Similarity	NPC254965
0.8519	High Similarity	NPC147179
0.8511	High Similarity	NPC197783
0.8505	High Similarity	NPC715
0.8505	High Similarity	NPC263753
0.85	High Similarity	NPC128723
0.8485	Intermediate Similarity	NPC312132
0.8485	Intermediate Similarity	NPC259512
0.8476	Intermediate Similarity	NPC314187
0.8469	Intermediate Similarity	NPC76938
0.8462	Intermediate Similarity	NPC320439
0.8455	Intermediate Similarity	NPC471671
0.8455	Intermediate Similarity	NPC154030
0.8454	Intermediate Similarity	NPC270547
0.8447	Intermediate Similarity	NPC219286
0.8447	Intermediate Similarity	NPC138942
0.8447	Intermediate Similarity	NPC99557
0.8447	Intermediate Similarity	NPC47284
0.844	Intermediate Similarity	NPC247858
0.844	Intermediate Similarity	NPC474387
0.844	Intermediate Similarity	NPC154511
0.844	Intermediate Similarity	NPC474358
0.844	Intermediate Similarity	NPC219112
0.844	Intermediate Similarity	NPC257540
0.844	Intermediate Similarity	NPC308828
0.844	Intermediate Similarity	NPC137496
0.8431	Intermediate Similarity	NPC168829
0.8431	Intermediate Similarity	NPC108497
0.8426	Intermediate Similarity	NPC107240
0.8416	Intermediate Similarity	NPC72729
0.8411	Intermediate Similarity	NPC471179
0.8404	Intermediate Similarity	NPC175313
0.8404	Intermediate Similarity	NPC150837
0.8404	Intermediate Similarity	NPC248817
0.84	Intermediate Similarity	NPC156313
0.84	Intermediate Similarity	NPC474073
0.8396	Intermediate Similarity	NPC132720
0.8384	Intermediate Similarity	NPC32714
0.8384	Intermediate Similarity	NPC26244
0.8381	Intermediate Similarity	NPC64586
0.8378	Intermediate Similarity	NPC126002
0.8378	Intermediate Similarity	NPC469644
0.8378	Intermediate Similarity	NPC93071
0.8365	Intermediate Similarity	NPC271274
0.8365	Intermediate Similarity	NPC310456
0.8365	Intermediate Similarity	NPC54765
0.8365	Intermediate Similarity	NPC155072
0.8365	Intermediate Similarity	NPC53740
0.8364	Intermediate Similarity	NPC16030
0.835	Intermediate Similarity	NPC288411
0.835	Intermediate Similarity	NPC475580
0.8349	Intermediate Similarity	NPC474486
0.8318	Intermediate Similarity	NPC469912
0.8318	Intermediate Similarity	NPC266937
0.8318	Intermediate Similarity	NPC77772
0.8318	Intermediate Similarity	NPC470770
0.83	Intermediate Similarity	NPC132271
0.83	Intermediate Similarity	NPC292730
0.83	Intermediate Similarity	NPC473388
0.83	Intermediate Similarity	NPC216520
0.83	Intermediate Similarity	NPC82664
0.8298	Intermediate Similarity	NPC124436
0.8298	Intermediate Similarity	NPC265146
0.8288	Intermediate Similarity	NPC48342
0.8288	Intermediate Similarity	NPC469609
0.8288	Intermediate Similarity	NPC164649
0.8283	Intermediate Similarity	NPC151715
0.8273	Intermediate Similarity	NPC92
0.8273	Intermediate Similarity	NPC469663
0.8265	Intermediate Similarity	NPC231150
0.8265	Intermediate Similarity	NPC45040
0.8252	Intermediate Similarity	NPC196479
0.8241	Intermediate Similarity	NPC62867
0.8241	Intermediate Similarity	NPC473521
0.8241	Intermediate Similarity	NPC177962
0.8241	Intermediate Similarity	NPC98372
0.8241	Intermediate Similarity	NPC302371
0.8235	Intermediate Similarity	NPC248396
0.8235	Intermediate Similarity	NPC129373
0.8235	Intermediate Similarity	NPC48730
0.823	Intermediate Similarity	NPC259703
0.823	Intermediate Similarity	NPC32322
0.823	Intermediate Similarity	NPC241001
0.8229	Intermediate Similarity	NPC407
0.8229	Intermediate Similarity	NPC307235
0.8218	Intermediate Similarity	NPC109955
0.8218	Intermediate Similarity	NPC152097
0.8214	Intermediate Similarity	NPC473974
0.8214	Intermediate Similarity	NPC79933
0.8214	Intermediate Similarity	NPC31296
0.8214	Intermediate Similarity	NPC42657
0.8214	Intermediate Similarity	NPC258366
0.8208	Intermediate Similarity	NPC470039
0.8208	Intermediate Similarity	NPC95344
0.8208	Intermediate Similarity	NPC306295
0.819	Intermediate Similarity	NPC469913
0.8182	Intermediate Similarity	NPC469719
0.8182	Intermediate Similarity	NPC325292
0.8182	Intermediate Similarity	NPC138117
0.8173	Intermediate Similarity	NPC475225
0.8165	Intermediate Similarity	NPC321589
0.8165	Intermediate Similarity	NPC322239
0.8163	Intermediate Similarity	NPC300017
0.8158	Intermediate Similarity	NPC249340
0.8158	Intermediate Similarity	NPC162935
0.8158	Intermediate Similarity	NPC154696
0.8155	Intermediate Similarity	NPC192032
0.8155	Intermediate Similarity	NPC11280
0.8155	Intermediate Similarity	NPC477685
0.8155	Intermediate Similarity	NPC147310
0.8155	Intermediate Similarity	NPC471578
0.8155	Intermediate Similarity	NPC294186
0.8155	Intermediate Similarity	NPC137415
0.8155	Intermediate Similarity	NPC101025
0.8155	Intermediate Similarity	NPC166313
0.8155	Intermediate Similarity	NPC24407
0.8148	Intermediate Similarity	NPC225679
0.8148	Intermediate Similarity	NPC165770

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 NPC211885 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	1062
0.2-0.3	1439
0.3-0.4	2963
0.4-0.5	1856
0.5-0.6	1053
0.6-0.7	349
0.7-0.8	78
0.8-0.85	14
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9255	High Similarity	NPD1432	Clinical (unspecified phase)
0.9158	High Similarity	NPD1809	Phase 2
0.86	High Similarity	NPD289	Clinical (unspecified phase)
0.8571	High Similarity	NPD844	Approved
0.8557	High Similarity	NPD845	Approved
0.85	High Similarity	NPD3020	Approved
0.8485	Intermediate Similarity	NPD288	Approved
0.8384	Intermediate Similarity	NPD2860	Approved
0.8384	Intermediate Similarity	NPD2859	Approved
0.8298	Intermediate Similarity	NPD111	Approved
0.8288	Intermediate Similarity	NPD3091	Approved
0.8283	Intermediate Similarity	NPD2933	Approved
0.8283	Intermediate Similarity	NPD2934	Approved
0.8142	Intermediate Similarity	NPD2932	Approved
0.8142	Intermediate Similarity	NPD3019	Approved
0.8142	Intermediate Similarity	NPD4059	Approved
0.8142	Intermediate Similarity	NPD1751	Approved
0.8131	Intermediate Similarity	NPD3022	Approved
0.8131	Intermediate Similarity	NPD3021	Approved
0.8113	Intermediate Similarity	NPD2342	Discontinued
0.8073	Intermediate Similarity	NPD7635	Approved
0.8019	Intermediate Similarity	NPD1444	Approved
0.8019	Intermediate Similarity	NPD1445	Approved
0.8	Intermediate Similarity	NPD3092	Approved
0.7982	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD940	Approved
0.7981	Intermediate Similarity	NPD846	Approved
0.7963	Intermediate Similarity	NPD1792	Phase 2
0.7905	Intermediate Similarity	NPD9500	Approved
0.7895	Intermediate Similarity	NPD4093	Discontinued
0.7838	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3095	Discontinued
0.7798	Intermediate Similarity	NPD4750	Phase 3
0.7768	Intermediate Similarity	NPD1791	Approved
0.7768	Intermediate Similarity	NPD1793	Approved
0.7731	Intermediate Similarity	NPD3094	Phase 2
0.7714	Intermediate Similarity	NPD1242	Phase 1
0.7712	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD2286	Discontinued
0.7672	Intermediate Similarity	NPD4626	Approved
0.7672	Intermediate Similarity	NPD4589	Approved
0.7667	Intermediate Similarity	NPD2195	Approved
0.7667	Intermediate Similarity	NPD2194	Approved
0.7603	Intermediate Similarity	NPD3637	Approved
0.7603	Intermediate Similarity	NPD3635	Approved
0.7603	Intermediate Similarity	NPD3636	Approved
0.7603	Intermediate Similarity	NPD5736	Approved
0.7541	Intermediate Similarity	NPD2605	Approved
0.7541	Intermediate Similarity	NPD2606	Approved
0.7522	Intermediate Similarity	NPD2229	Approved
0.7522	Intermediate Similarity	NPD2234	Approved
0.7522	Intermediate Similarity	NPD2228	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD6696	Suspended
0.75	Intermediate Similarity	NPD9610	Approved
0.75	Intermediate Similarity	NPD9608	Approved
0.748	Intermediate Similarity	NPD5156	Approved
0.748	Intermediate Similarity	NPD5155	Approved
0.7458	Intermediate Similarity	NPD3026	Approved
0.7458	Intermediate Similarity	NPD3023	Approved
0.7436	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3024	Approved
0.7436	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3025	Approved
0.7398	Intermediate Similarity	NPD3595	Approved
0.7398	Intermediate Similarity	NPD3594	Approved
0.7377	Intermediate Similarity	NPD4624	Approved
0.736	Intermediate Similarity	NPD6663	Approved
0.735	Intermediate Similarity	NPD5304	Approved
0.735	Intermediate Similarity	NPD5303	Approved
0.735	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD3143	Discontinued
0.7304	Intermediate Similarity	NPD497	Approved
0.7302	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3620	Phase 2
0.7295	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1651	Approved
0.7288	Intermediate Similarity	NPD5691	Approved
0.7281	Intermediate Similarity	NPD9379	Approved
0.7281	Intermediate Similarity	NPD9377	Approved
0.7273	Intermediate Similarity	NPD1669	Approved
0.725	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6671	Approved
0.7241	Intermediate Similarity	NPD7157	Approved
0.7222	Intermediate Similarity	NPD3028	Approved
0.7217	Intermediate Similarity	NPD498	Approved
0.7217	Intermediate Similarity	NPD1398	Phase 1
0.7217	Intermediate Similarity	NPD495	Approved
0.7217	Intermediate Similarity	NPD496	Approved
0.7213	Intermediate Similarity	NPD1283	Approved
0.7203	Intermediate Similarity	NPD7330	Discontinued
0.719	Intermediate Similarity	NPD3070	Discontinued
0.7188	Intermediate Similarity	NPD4097	Suspended
0.7179	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4060	Phase 1
0.7131	Intermediate Similarity	NPD5327	Phase 3
0.7131	Intermediate Similarity	NPD1755	Approved
0.7128	Intermediate Similarity	NPD9087	Approved
0.7107	Intermediate Similarity	NPD1201	Approved
0.7097	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2684	Approved
0.7077	Intermediate Similarity	NPD7743	Approved
0.7077	Intermediate Similarity	NPD7742	Approved
0.7069	Intermediate Similarity	NPD5283	Phase 1
0.7063	Intermediate Similarity	NPD4625	Phase 3
0.7034	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7636	Approved
0.7034	Intermediate Similarity	NPD7340	Approved
0.7031	Intermediate Similarity	NPD4140	Approved
0.7018	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD9618	Approved
0.7009	Intermediate Similarity	NPD475	Phase 2
0.7009	Intermediate Similarity	NPD9614	Approved
0.7	Intermediate Similarity	NPD1357	Approved
0.6977	Remote Similarity	NPD5735	Approved
0.6967	Remote Similarity	NPD1281	Approved
0.6957	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD255	Approved
0.6949	Remote Similarity	NPD709	Approved
0.6949	Remote Similarity	NPD256	Approved
0.6923	Remote Similarity	NPD6353	Approved
0.6911	Remote Similarity	NPD2230	Approved
0.6911	Remote Similarity	NPD2233	Approved
0.6911	Remote Similarity	NPD2232	Approved
0.6907	Remote Similarity	NPD9294	Approved
0.6905	Remote Similarity	NPD4208	Discontinued
0.6905	Remote Similarity	NPD4212	Discontinued
0.6881	Remote Similarity	NPD9273	Approved
0.688	Remote Similarity	NPD1470	Approved
0.6875	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2209	Approved
0.6866	Remote Similarity	NPD3638	Discontinued
0.6866	Remote Similarity	NPD2211	Approved
0.6855	Remote Similarity	NPD4749	Approved
0.685	Remote Similarity	NPD4207	Discontinued
0.6842	Remote Similarity	NPD4725	Approved
0.6842	Remote Similarity	NPD4726	Approved
0.6842	Remote Similarity	NPD4721	Approved
0.6838	Remote Similarity	NPD7843	Approved
0.6838	Remote Similarity	NPD821	Approved
0.6837	Remote Similarity	NPD9088	Approved
0.6833	Remote Similarity	NPD9616	Approved
0.6833	Remote Similarity	NPD16	Approved
0.6833	Remote Similarity	NPD856	Approved
0.6833	Remote Similarity	NPD9615	Approved
0.6833	Remote Similarity	NPD9613	Approved
0.6825	Remote Similarity	NPD6584	Phase 3
0.6818	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9381	Approved
0.6803	Remote Similarity	NPD2667	Approved
0.6803	Remote Similarity	NPD9384	Approved
0.6803	Remote Similarity	NPD2668	Approved
0.6803	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7095	Approved
0.6794	Remote Similarity	NPD2157	Approved
0.678	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD316	Approved
0.6772	Remote Similarity	NPD2861	Phase 2
0.6765	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD968	Approved
0.6746	Remote Similarity	NPD3055	Approved
0.6746	Remote Similarity	NPD1135	Approved
0.6746	Remote Similarity	NPD1131	Approved
0.6746	Remote Similarity	NPD3053	Approved
0.6746	Remote Similarity	NPD1164	Approved
0.6746	Remote Similarity	NPD1129	Approved
0.6746	Remote Similarity	NPD1134	Approved
0.6746	Remote Similarity	NPD1133	Approved
0.6744	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD9244	Approved
0.6726	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5451	Approved
0.6723	Remote Similarity	NPD5951	Approved
0.6723	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.672	Remote Similarity	NPD9622	Approved
0.6696	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1138	Approved
0.6694	Remote Similarity	NPD3705	Approved
0.6694	Remote Similarity	NPD1611	Approved
0.6694	Remote Similarity	NPD317	Approved
0.6694	Remote Similarity	NPD1610	Phase 2
0.6694	Remote Similarity	NPD318	Approved
0.6693	Remote Similarity	NPD257	Approved
0.6693	Remote Similarity	NPD258	Approved
0.6692	Remote Similarity	NPD8032	Phase 2
0.6691	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD5310	Approved
0.6667	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD5311	Approved
0.6667	Remote Similarity	NPD8651	Approved
0.6642	Remote Similarity	NPD5404	Approved
0.6642	Remote Similarity	NPD5405	Approved
0.6642	Remote Similarity	NPD5408	Approved
0.6642	Remote Similarity	NPD5406	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