NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.1
Volume:	173.841
LogP:	3.36
LogD:	3.344
LogS:	-2.754
# 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:	0.603
Synthetic Accessibility Score:	1.736
Fsp3:	0.4
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:	-4.557
MDCK Permeability:	2.119646524079144e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.503
30% Bioavailability (F30%):	0.64

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.47
Plasma Protein Binding (PPB):	90.78087615966797%
Volume Distribution (VD):	3.412
Pgp-substrate:	13.561216354370117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.841
CYP2C19-inhibitor:	0.823
CYP2C19-substrate:	0.619
CYP2C9-inhibitor:	0.529
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.807
CYP2D6-substrate:	0.723
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.37

ADMET: Excretion

Clearance (CL):	11.363
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.248
Skin Sensitization:	0.817
Carcinogencity:	0.063
Eye Corrosion:	0.981
Eye Irritation:	0.991
Respiratory Toxicity:	0.363

Download Data

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

Natural Product: NPC55903

Natural Product ID:	NPC55903
*Common Name:**	3-Tert-Butylphenol
IUPAC Name:	3-tert-butylphenol
Synonyms:	3-Tert-Butylphenol
Standard InCHIKey:	CYEKUDPFXBLGHH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H14O/c1-10(2,3)8-5-4-6-9(11)7-8/h4-7,11H,1-3H3
SMILES:	CC(C)(C)c1cccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL224899
PubChem CID:	11450
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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	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	3
Potency	5

Activity Type	# Activity
Cell Line	2
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	log(1/ID50)	=	3.88	n.a.	PMID[518761]
NPT137	Cell Line	L1210	Mus musculus	Activity	<	15.0	%	PMID[518761]
NPT27	Others	Unspecified		log Ks	=	4.41	n.a.	PMID[518762]
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	4896.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	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 NPC55903 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	275
0.1-0.2	1940
0.2-0.3	4901
0.3-0.4	13263
0.4-0.5	7450
0.5-0.6	9917
0.6-0.7	3722
0.7-0.8	923
0.8-0.85	165
0.85-0.9	100
0.9-0.95	30
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC222146
0.954	High Similarity	NPC27974
0.9457	High Similarity	NPC299762
0.9457	High Similarity	NPC33675
0.9444	High Similarity	NPC27323
0.9444	High Similarity	NPC316301
0.9444	High Similarity	NPC152415
0.9438	High Similarity	NPC155908
0.9438	High Similarity	NPC306074
0.9333	High Similarity	NPC94139
0.9333	High Similarity	NPC306884
0.9333	High Similarity	NPC210497
0.9333	High Similarity	NPC162314
0.9333	High Similarity	NPC147284
0.9333	High Similarity	NPC3358
0.9326	High Similarity	NPC192
0.9255	High Similarity	NPC252105
0.9239	High Similarity	NPC312132
0.9239	High Similarity	NPC259512
0.9231	High Similarity	NPC245187
0.9222	High Similarity	NPC304541
0.9195	High Similarity	NPC150837
0.9149	High Similarity	NPC211885
0.914	High Similarity	NPC225464
0.914	High Similarity	NPC6597
0.914	High Similarity	NPC79241
0.9101	High Similarity	NPC19680
0.9062	High Similarity	NPC120719
0.9043	High Similarity	NPC122005
0.9043	High Similarity	NPC92730
0.9043	High Similarity	NPC252821
0.9022	High Similarity	NPC76938
0.9022	High Similarity	NPC289769
0.9011	High Similarity	NPC231150
0.9	High Similarity	NPC242240
0.9	High Similarity	NPC318325
0.9	High Similarity	NPC123273
0.9	High Similarity	NPC258219
0.8989	High Similarity	NPC407
0.8989	High Similarity	NPC307235
0.8989	High Similarity	NPC23167
0.8969	High Similarity	NPC47284
0.8958	High Similarity	NPC269212
0.8947	High Similarity	NPC72729
0.8947	High Similarity	NPC225506
0.8936	High Similarity	NPC474073
0.8925	High Similarity	NPC274678
0.8925	High Similarity	NPC32714
0.8889	High Similarity	NPC25493
0.8889	High Similarity	NPC113460
0.8878	High Similarity	NPC310456
0.8878	High Similarity	NPC477814
0.8878	High Similarity	NPC53740
0.8876	High Similarity	NPC197783
0.8876	High Similarity	NPC155393
0.883	High Similarity	NPC202986
0.8791	High Similarity	NPC177420
0.8791	High Similarity	NPC98772
0.8791	High Similarity	NPC280347
0.8788	High Similarity	NPC320439
0.8778	High Similarity	NPC184169
0.8764	High Similarity	NPC248817
0.8764	High Similarity	NPC175313
0.8764	High Similarity	NPC286904
0.875	High Similarity	NPC248396
0.875	High Similarity	NPC174911
0.875	High Similarity	NPC48730
0.875	High Similarity	NPC129373
0.8737	High Similarity	NPC32674
0.8737	High Similarity	NPC156313
0.8737	High Similarity	NPC77492
0.8737	High Similarity	NPC152097
0.8723	High Similarity	NPC8392
0.8723	High Similarity	NPC144682
0.871	High Similarity	NPC271440
0.871	High Similarity	NPC29373
0.87	High Similarity	NPC306295
0.87	High Similarity	NPC64586
0.8696	High Similarity	NPC312304
0.8696	High Similarity	NPC55561
0.8687	High Similarity	NPC155072
0.8673	High Similarity	NPC475580
0.8673	High Similarity	NPC475225
0.866	High Similarity	NPC12221
0.8652	High Similarity	NPC265146
0.8652	High Similarity	NPC124436
0.8646	High Similarity	NPC260775
0.8602	High Similarity	NPC270547
0.8602	High Similarity	NPC204210
0.8602	High Similarity	NPC45040
0.8571	High Similarity	NPC471228
0.8571	High Similarity	NPC168303
0.8571	High Similarity	NPC71002
0.8571	High Similarity	NPC53051
0.8571	High Similarity	NPC106396
0.8571	High Similarity	NPC235762
0.8571	High Similarity	NPC242342
0.8571	High Similarity	NPC108497
0.8571	High Similarity	NPC302219
0.8571	High Similarity	NPC222522
0.8571	High Similarity	NPC94351
0.8571	High Similarity	NPC85479
0.8571	High Similarity	NPC313030
0.8571	High Similarity	NPC24404
0.8571	High Similarity	NPC146798
0.8571	High Similarity	NPC249828
0.8557	High Similarity	NPC70677
0.8557	High Similarity	NPC10588
0.8557	High Similarity	NPC130756
0.8557	High Similarity	NPC12931
0.8557	High Similarity	NPC166761
0.8557	High Similarity	NPC294741
0.8542	High Similarity	NPC109955
0.8542	High Similarity	NPC475078
0.8529	High Similarity	NPC13482
0.8526	High Similarity	NPC26244
0.8511	High Similarity	NPC325292
0.8511	High Similarity	NPC138117
0.8495	Intermediate Similarity	NPC300017
0.8485	Intermediate Similarity	NPC323810
0.8485	Intermediate Similarity	NPC327811
0.8485	Intermediate Similarity	NPC272029
0.8485	Intermediate Similarity	NPC254965
0.8485	Intermediate Similarity	NPC238696
0.8469	Intermediate Similarity	NPC100340
0.8469	Intermediate Similarity	NPC11280
0.8469	Intermediate Similarity	NPC284011
0.8469	Intermediate Similarity	NPC143659
0.8469	Intermediate Similarity	NPC166313
0.8469	Intermediate Similarity	NPC24407
0.8469	Intermediate Similarity	NPC294186
0.8469	Intermediate Similarity	NPC192032
0.8469	Intermediate Similarity	NPC137415
0.8469	Intermediate Similarity	NPC147310
0.8469	Intermediate Similarity	NPC72947
0.8469	Intermediate Similarity	NPC477685
0.8447	Intermediate Similarity	NPC77772
0.8447	Intermediate Similarity	NPC266937
0.8447	Intermediate Similarity	NPC470770
0.8447	Intermediate Similarity	NPC322753
0.8447	Intermediate Similarity	NPC275627
0.8438	Intermediate Similarity	NPC473388
0.8438	Intermediate Similarity	NPC216520
0.8438	Intermediate Similarity	NPC82664
0.8438	Intermediate Similarity	NPC292730
0.8438	Intermediate Similarity	NPC132271
0.8421	Intermediate Similarity	NPC128062
0.8421	Intermediate Similarity	NPC151715
0.8416	Intermediate Similarity	NPC66834
0.8409	Intermediate Similarity	NPC133050
0.84	Intermediate Similarity	NPC239291
0.84	Intermediate Similarity	NPC117115
0.84	Intermediate Similarity	NPC471350
0.8387	Intermediate Similarity	NPC70436
0.8384	Intermediate Similarity	NPC168393
0.8384	Intermediate Similarity	NPC196479
0.8384	Intermediate Similarity	NPC233827
0.8367	Intermediate Similarity	NPC130103
0.8365	Intermediate Similarity	NPC62867
0.8365	Intermediate Similarity	NPC250323
0.8365	Intermediate Similarity	NPC177962
0.835	Intermediate Similarity	NPC141782
0.8333	Intermediate Similarity	NPC257182
0.8333	Intermediate Similarity	NPC11554
0.8333	Intermediate Similarity	NPC168855
0.8333	Intermediate Similarity	NPC313650
0.8333	Intermediate Similarity	NPC107522
0.8317	Intermediate Similarity	NPC54765
0.8317	Intermediate Similarity	NPC21594
0.8316	Intermediate Similarity	NPC295295
0.83	Intermediate Similarity	NPC241891
0.83	Intermediate Similarity	NPC227458
0.83	Intermediate Similarity	NPC218879
0.83	Intermediate Similarity	NPC102216
0.83	Intermediate Similarity	NPC471511
0.83	Intermediate Similarity	NPC30506
0.83	Intermediate Similarity	NPC244513
0.8283	Intermediate Similarity	NPC471578
0.8283	Intermediate Similarity	NPC101025
0.8283	Intermediate Similarity	NPC80800
0.8283	Intermediate Similarity	NPC110764
0.828	Intermediate Similarity	NPC104216
0.8269	Intermediate Similarity	NPC176279
0.8269	Intermediate Similarity	NPC260323
0.8265	Intermediate Similarity	NPC128723
0.8252	Intermediate Similarity	NPC58865
0.8252	Intermediate Similarity	NPC228343
0.8252	Intermediate Similarity	NPC254833
0.8242	Intermediate Similarity	NPC474354
0.8235	Intermediate Similarity	NPC232523
0.8235	Intermediate Similarity	NPC305603
0.8235	Intermediate Similarity	NPC158253
0.8235	Intermediate Similarity	NPC61033
0.8235	Intermediate Similarity	NPC204901
0.8235	Intermediate Similarity	NPC151477
0.8218	Intermediate Similarity	NPC138942
0.8218	Intermediate Similarity	NPC37802
0.8218	Intermediate Similarity	NPC134829
0.8208	Intermediate Similarity	NPC195922
0.82	Intermediate Similarity	NPC68055

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 NPC55903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	1076
0.2-0.3	1297
0.3-0.4	2933
0.4-0.5	1911
0.5-0.6	1114
0.6-0.7	418
0.7-0.8	72
0.8-0.85	9
0.85-0.9	7
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9444	High Similarity	NPD1432	Clinical (unspecified phase)
0.9355	High Similarity	NPD289	Clinical (unspecified phase)
0.9239	High Similarity	NPD288	Approved
0.913	High Similarity	NPD844	Approved
0.8723	High Similarity	NPD1809	Phase 2
0.871	High Similarity	NPD845	Approved
0.8652	High Similarity	NPD111	Approved
0.8646	High Similarity	NPD3020	Approved
0.8526	High Similarity	NPD2859	Approved
0.8526	High Similarity	NPD2860	Approved
0.85	High Similarity	NPD1445	Approved
0.85	High Similarity	NPD1444	Approved
0.8421	Intermediate Similarity	NPD2933	Approved
0.8421	Intermediate Similarity	NPD2934	Approved
0.8252	Intermediate Similarity	NPD3021	Approved
0.8252	Intermediate Similarity	NPD3022	Approved
0.8252	Intermediate Similarity	NPD1792	Phase 2
0.8208	Intermediate Similarity	NPD1791	Approved
0.8208	Intermediate Similarity	NPD1793	Approved
0.81	Intermediate Similarity	NPD940	Approved
0.81	Intermediate Similarity	NPD846	Approved
0.8077	Intermediate Similarity	NPD4750	Phase 3
0.8058	Intermediate Similarity	NPD2342	Discontinued
0.802	Intermediate Similarity	NPD9500	Approved
0.8	Intermediate Similarity	NPD1242	Phase 1
0.7909	Intermediate Similarity	NPD3091	Approved
0.785	Intermediate Similarity	NPD7635	Approved
0.7816	Intermediate Similarity	NPD9087	Approved
0.7768	Intermediate Similarity	NPD3019	Approved
0.7768	Intermediate Similarity	NPD2932	Approved
0.7768	Intermediate Similarity	NPD4059	Approved
0.7768	Intermediate Similarity	NPD1751	Approved
0.7767	Intermediate Similarity	NPD9608	Approved
0.7767	Intermediate Similarity	NPD9610	Approved
0.7757	Intermediate Similarity	NPD228	Approved
0.7636	Intermediate Similarity	NPD6671	Approved
0.7632	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3092	Approved
0.7632	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2228	Approved
0.7615	Intermediate Similarity	NPD2229	Approved
0.7615	Intermediate Similarity	NPD2234	Approved
0.7593	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD9294	Approved
0.7545	Intermediate Similarity	NPD9614	Approved
0.7545	Intermediate Similarity	NPD9618	Approved
0.7523	Intermediate Similarity	NPD9377	Approved
0.7523	Intermediate Similarity	NPD9379	Approved
0.7522	Intermediate Similarity	NPD4093	Discontinued
0.75	Intermediate Similarity	NPD1755	Approved
0.7473	Intermediate Similarity	NPD9088	Approved
0.7456	Intermediate Similarity	NPD3095	Discontinued
0.7456	Intermediate Similarity	NPD4589	Approved
0.7455	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD9273	Approved
0.7434	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD3094	Phase 2
0.7345	Intermediate Similarity	NPD9615	Approved
0.7345	Intermediate Similarity	NPD9613	Approved
0.7345	Intermediate Similarity	NPD9616	Approved
0.7321	Intermediate Similarity	NPD7157	Approved
0.7311	Intermediate Similarity	NPD2194	Approved
0.7311	Intermediate Similarity	NPD2195	Approved
0.7308	Intermediate Similarity	NPD3028	Approved
0.7304	Intermediate Similarity	NPD2286	Discontinued
0.729	Intermediate Similarity	NPD968	Approved
0.7281	Intermediate Similarity	NPD316	Approved
0.7257	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3635	Approved
0.725	Intermediate Similarity	NPD3637	Approved
0.725	Intermediate Similarity	NPD5736	Approved
0.725	Intermediate Similarity	NPD3636	Approved
0.7248	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD475	Phase 2
0.7232	Intermediate Similarity	NPD497	Approved
0.7203	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2605	Approved
0.719	Intermediate Similarity	NPD2606	Approved
0.7182	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1201	Approved
0.7168	Intermediate Similarity	NPD709	Approved
0.7168	Intermediate Similarity	NPD256	Approved
0.7168	Intermediate Similarity	NPD255	Approved
0.7158	Intermediate Similarity	NPD9089	Approved
0.7156	Intermediate Similarity	NPD2684	Approved
0.7155	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD6696	Suspended
0.7143	Intermediate Similarity	NPD495	Approved
0.7143	Intermediate Similarity	NPD1616	Discontinued
0.7143	Intermediate Similarity	NPD498	Approved
0.7143	Intermediate Similarity	NPD496	Approved
0.7143	Intermediate Similarity	NPD5283	Phase 1
0.7131	Intermediate Similarity	NPD5156	Approved
0.7131	Intermediate Similarity	NPD5155	Approved
0.713	Intermediate Similarity	NPD5304	Approved
0.713	Intermediate Similarity	NPD5303	Approved
0.713	Intermediate Similarity	NPD7330	Discontinued
0.7119	Intermediate Similarity	NPD2232	Approved
0.7119	Intermediate Similarity	NPD2233	Approved
0.7119	Intermediate Similarity	NPD2230	Approved
0.7103	Intermediate Similarity	NPD9244	Approved
0.7094	Intermediate Similarity	NPD3023	Approved
0.7094	Intermediate Similarity	NPD3026	Approved
0.7083	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3024	Approved
0.7069	Intermediate Similarity	NPD3025	Approved
0.7069	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1357	Approved
0.7069	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD290	Approved
0.7059	Intermediate Similarity	NPD4749	Approved
0.7053	Intermediate Similarity	NPD9093	Approved
0.7049	Intermediate Similarity	NPD3595	Approved
0.7049	Intermediate Similarity	NPD3594	Approved
0.7025	Intermediate Similarity	NPD4624	Approved
0.7025	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6663	Approved
0.7009	Intermediate Similarity	NPD9381	Approved
0.7009	Intermediate Similarity	NPD1778	Approved
0.7009	Intermediate Similarity	NPD9384	Approved
0.7009	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9295	Approved
0.6975	Remote Similarity	NPD1608	Approved
0.696	Remote Similarity	NPD6346	Approved
0.6957	Remote Similarity	NPD7636	Approved
0.6957	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3143	Discontinued
0.6949	Remote Similarity	NPD3496	Discontinued
0.6942	Remote Similarity	NPD1470	Approved
0.6939	Remote Similarity	NPD9073	Approved
0.6935	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9622	Approved
0.6916	Remote Similarity	NPD4817	Approved
0.6916	Remote Similarity	NPD4818	Approved
0.6909	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD821	Approved
0.6903	Remote Similarity	NPD7843	Approved
0.6897	Remote Similarity	NPD856	Approved
0.6897	Remote Similarity	NPD317	Approved
0.6897	Remote Similarity	NPD16	Approved
0.6897	Remote Similarity	NPD318	Approved
0.6891	Remote Similarity	NPD1610	Phase 2
0.6885	Remote Similarity	NPD258	Approved
0.6885	Remote Similarity	NPD6584	Phase 3
0.6885	Remote Similarity	NPD257	Approved
0.6864	Remote Similarity	NPD2668	Approved
0.6864	Remote Similarity	NPD2667	Approved
0.6864	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1283	Approved
0.686	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4625	Phase 3
0.6855	Remote Similarity	NPD7095	Approved
0.6847	Remote Similarity	NPD9266	Approved
0.6847	Remote Similarity	NPD74	Approved
0.6842	Remote Similarity	NPD1398	Phase 1
0.6833	Remote Similarity	NPD3070	Discontinued
0.6829	Remote Similarity	NPD2861	Phase 2
0.6825	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3620	Phase 2
0.681	Remote Similarity	NPD9568	Approved
0.681	Remote Similarity	NPD9493	Approved
0.6807	Remote Similarity	NPD1980	Approved
0.6807	Remote Similarity	NPD1981	Approved
0.6807	Remote Similarity	NPD1983	Approved
0.6803	Remote Similarity	NPD3053	Approved
0.6803	Remote Similarity	NPD3055	Approved
0.6796	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD752	Approved
0.6796	Remote Similarity	NPD1088	Approved
0.6792	Remote Similarity	NPD9609	Approved
0.6792	Remote Similarity	NPD9612	Approved
0.6792	Remote Similarity	NPD9611	Approved
0.6786	Remote Similarity	NPD5451	Approved
0.678	Remote Similarity	NPD5691	Approved
0.678	Remote Similarity	NPD1651	Approved
0.678	Remote Similarity	NPD5585	Approved
0.6777	Remote Similarity	NPD5327	Phase 3
0.6777	Remote Similarity	NPD1669	Approved
0.6757	Remote Similarity	NPD9264	Approved
0.6757	Remote Similarity	NPD9267	Approved
0.6757	Remote Similarity	NPD9263	Approved
0.6754	Remote Similarity	NPD1138	Approved
0.6748	Remote Similarity	NPD9620	Approved
0.6748	Remote Similarity	NPD9621	Approved
0.6748	Remote Similarity	NPD9619	Approved
0.6744	Remote Similarity	NPD7742	Approved
0.6744	Remote Similarity	NPD7743	Approved
0.6733	Remote Similarity	NPD9094	Approved
0.6733	Remote Similarity	NPD1101	Approved
0.6731	Remote Similarity	NPD719	Approved
0.6731	Remote Similarity	NPD720	Approved
0.6723	Remote Similarity	NPD17	Approved
0.6721	Remote Similarity	NPD5310	Approved
0.6721	Remote Similarity	NPD5311	Approved
0.672	Remote Similarity	NPD3027	Phase 3
0.6719	Remote Similarity	NPD4097	Suspended
0.6697	Remote Similarity	NPD3682	Approved
0.6697	Remote Similarity	NPD4656	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