NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.1
Volume:	173.841
LogP:	3.088
LogD:	3.279
LogS:	-2.133
# 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:	0.652
Synthetic Accessibility Score:	1.705
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:	-4.394
MDCK Permeability:	2.441781180095859e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.78
Plasma Protein Binding (PPB):	93.91715240478516%
Volume Distribution (VD):	2.387
Pgp-substrate:	7.243838787078857%

ADMET: Metabolism

CYP1A2-inhibitor:	0.906
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.733
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.429
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.823
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.149
CYP3A4-substrate:	0.441

ADMET: Excretion

Clearance (CL):	9.397
Half-life (T1/2):	0.749

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.095
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.313
Maximum Recommended Daily Dose:	0.442
Skin Sensitization:	0.413
Carcinogencity:	0.312
Eye Corrosion:	0.914
Eye Irritation:	0.988
Respiratory Toxicity:	0.465

Download Data

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

Natural Product: NPC8392

Natural Product ID:	NPC8392
*Common Name:**	Isothymol
IUPAC Name:	4-methyl-2-propan-2-ylphenol
Synonyms:
Standard InCHIKey:	DSTPUJAJSXTJHM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H14O/c1-7(2)9-6-8(3)4-5-10(9)11/h4-7,11H,1-3H3
SMILES:	CC(C)c1cc(C)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2288299
PubChem CID:	78153
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000355] Cumenes

*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
NPO19134	Boronia bipinnata	Species	Rutaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18662038]
NPO28004	Pseudodistoma megalarva	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358640]
NPO18581	Pyrrosia davidii	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18581	Pyrrosia davidii	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22725	Cirsium microspicatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26523	Alicyclobacillus acidocaldarius	Species	Alicyclobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17285	Taraxacum udum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8147	Calea hispida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28004	Pseudodistoma megalarva	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16661	Duboisia myoporoides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15368	Trifolium medium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17194	Linum capitatum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13648	Phialocephala fortinii	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19134	Boronia bipinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18581	Pyrrosia davidii	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15676	Tricholoma scalpturatum	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18310	Pecten jacobaeus	Species	Pectinidae	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	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT724	Organism	Corticium	Corticium	GI	=	100.0	%	PMID[571515]
NPT724	Organism	Corticium	Corticium	GI	=	72.4	%	PMID[571515]
NPT723	Organism	Pythium	Pythium	GI	=	100.0	%	PMID[571515]
NPT723	Organism	Pythium	Pythium	GI	=	94.3	%	PMID[571515]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	GI	=	72.4	%	PMID[571516]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	GI	=	38.0	%	PMID[571516]
NPT723	Organism	Pythium	Pythium	GI	=	94.3	%	PMID[571516]
NPT723	Organism	Pythium	Pythium	GI	=	24.2	%	PMID[571516]

☑ 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 NPC8392 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	289
0.1-0.2	1971
0.2-0.3	5511
0.3-0.4	13258
0.4-0.5	6487
0.5-0.6	9343
0.6-0.7	4501
0.7-0.8	1064
0.8-0.85	148
0.85-0.9	89
0.9-0.95	32
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC77492
0.9663	High Similarity	NPC204210
0.9462	High Similarity	NPC122005
0.9462	High Similarity	NPC252821
0.9444	High Similarity	NPC304541
0.9438	High Similarity	NPC258219
0.9438	High Similarity	NPC70436
0.9362	High Similarity	NPC225506
0.9348	High Similarity	NPC144682
0.9255	High Similarity	NPC128723
0.9239	High Similarity	NPC289769
0.9231	High Similarity	NPC306074
0.9222	High Similarity	NPC242240
0.9222	High Similarity	NPC318325
0.9222	High Similarity	NPC123273
0.9213	High Similarity	NPC307235
0.9213	High Similarity	NPC23167
0.9213	High Similarity	NPC407
0.9111	High Similarity	NPC113460
0.9111	High Similarity	NPC25493
0.9101	High Similarity	NPC197783
0.9101	High Similarity	NPC155393
0.9082	High Similarity	NPC271274
0.9043	High Similarity	NPC312132
0.9043	High Similarity	NPC259512
0.9032	High Similarity	NPC27323
0.9032	High Similarity	NPC128062
0.9032	High Similarity	NPC316301
0.9032	High Similarity	NPC152415
0.9022	High Similarity	NPC155908
0.9011	High Similarity	NPC280347
0.9011	High Similarity	NPC177420
0.899	High Similarity	NPC228737
0.8989	High Similarity	NPC286904
0.8989	High Similarity	NPC175313
0.8989	High Similarity	NPC248817
0.898	High Similarity	NPC138942
0.8969	High Similarity	NPC168829
0.8947	High Similarity	NPC79241
0.8947	High Similarity	NPC6597
0.8925	High Similarity	NPC271440
0.8913	High Similarity	NPC55561
0.8889	High Similarity	NPC21594
0.8878	High Similarity	NPC288411
0.8876	High Similarity	NPC124436
0.8876	High Similarity	NPC265146
0.8866	High Similarity	NPC51015
0.8842	High Similarity	NPC473388
0.883	High Similarity	NPC245187
0.8817	High Similarity	NPC45040
0.8812	High Similarity	NPC58865
0.88	High Similarity	NPC151477
0.8791	High Similarity	NPC184169
0.8788	High Similarity	NPC303141
0.8776	High Similarity	NPC470202
0.8763	High Similarity	NPC211885
0.8763	High Similarity	NPC72729
0.875	High Similarity	NPC225464
0.8737	High Similarity	NPC222146
0.8737	High Similarity	NPC26244
0.8725	High Similarity	NPC13482
0.8725	High Similarity	NPC296683
0.8723	High Similarity	NPC138117
0.8723	High Similarity	NPC55903
0.8723	High Similarity	NPC325292
0.871	High Similarity	NPC300017
0.87	High Similarity	NPC54765
0.8696	High Similarity	NPC19680
0.8696	High Similarity	NPC27974
0.866	High Similarity	NPC299762
0.866	High Similarity	NPC33675
0.866	High Similarity	NPC80027
0.866	High Similarity	NPC92730
0.8646	High Similarity	NPC82664
0.8646	High Similarity	NPC292730
0.8646	High Similarity	NPC132271
0.8646	High Similarity	NPC216520
0.8632	High Similarity	NPC151715
0.8617	High Similarity	NPC231150
0.8602	High Similarity	NPC98772
0.86	High Similarity	NPC99557
0.86	High Similarity	NPC219286
0.86	High Similarity	NPC243677
0.86	High Similarity	NPC117115
0.8586	High Similarity	NPC108497
0.8586	High Similarity	NPC269212
0.8558	High Similarity	NPC250323
0.8558	High Similarity	NPC228425
0.8544	High Similarity	NPC141782
0.8542	High Similarity	NPC274678
0.8542	High Similarity	NPC313650
0.8529	High Similarity	NPC95344
0.8529	High Similarity	NPC63698
0.8529	High Similarity	NPC470039
0.8529	High Similarity	NPC262365
0.8529	High Similarity	NPC61885
0.8526	High Similarity	NPC147284
0.8526	High Similarity	NPC3358
0.8526	High Similarity	NPC210497
0.8526	High Similarity	NPC162314
0.8526	High Similarity	NPC94139
0.8526	High Similarity	NPC306884
0.8515	High Similarity	NPC248904
0.8511	High Similarity	NPC192
0.85	High Similarity	NPC238696
0.85	High Similarity	NPC272029
0.85	High Similarity	NPC475225
0.85	High Similarity	NPC475580
0.8495	Intermediate Similarity	NPC104216
0.8485	Intermediate Similarity	NPC12221
0.8485	Intermediate Similarity	NPC252105
0.8476	Intermediate Similarity	NPC715
0.8462	Intermediate Similarity	NPC151537
0.8462	Intermediate Similarity	NPC260323
0.8462	Intermediate Similarity	NPC176279
0.8462	Intermediate Similarity	NPC95716
0.8454	Intermediate Similarity	NPC202986
0.8447	Intermediate Similarity	NPC75272
0.8447	Intermediate Similarity	NPC471954
0.8447	Intermediate Similarity	NPC314187
0.8421	Intermediate Similarity	NPC270547
0.84	Intermediate Similarity	NPC235762
0.84	Intermediate Similarity	NPC471228
0.8396	Intermediate Similarity	NPC195922
0.8384	Intermediate Similarity	NPC48730
0.8384	Intermediate Similarity	NPC129373
0.8384	Intermediate Similarity	NPC174911
0.8384	Intermediate Similarity	NPC248396
0.8381	Intermediate Similarity	NPC46940
0.837	Intermediate Similarity	NPC150837
0.8367	Intermediate Similarity	NPC156313
0.8367	Intermediate Similarity	NPC260000
0.8367	Intermediate Similarity	NPC32674
0.8367	Intermediate Similarity	NPC152097
0.8365	Intermediate Similarity	NPC224870
0.8365	Intermediate Similarity	NPC44732
0.835	Intermediate Similarity	NPC11554
0.8333	Intermediate Similarity	NPC29373
0.8333	Intermediate Similarity	NPC181709
0.8333	Intermediate Similarity	NPC469913
0.8317	Intermediate Similarity	NPC120719
0.8317	Intermediate Similarity	NPC119860
0.8316	Intermediate Similarity	NPC300478
0.8316	Intermediate Similarity	NPC47950
0.8302	Intermediate Similarity	NPC141003
0.8302	Intermediate Similarity	NPC35344
0.8286	Intermediate Similarity	NPC165770
0.8286	Intermediate Similarity	NPC308689
0.8286	Intermediate Similarity	NPC225679
0.8286	Intermediate Similarity	NPC476632
0.8286	Intermediate Similarity	NPC4493
0.8283	Intermediate Similarity	NPC132078
0.8283	Intermediate Similarity	NPC280869
0.8283	Intermediate Similarity	NPC216468
0.8283	Intermediate Similarity	NPC260775
0.8283	Intermediate Similarity	NPC78119
0.8283	Intermediate Similarity	NPC51333
0.8252	Intermediate Similarity	NPC66834
0.8252	Intermediate Similarity	NPC320439
0.8247	Intermediate Similarity	NPC76938
0.8235	Intermediate Similarity	NPC239291
0.8235	Intermediate Similarity	NPC47284
0.8235	Intermediate Similarity	NPC474839
0.8224	Intermediate Similarity	NPC268160
0.8224	Intermediate Similarity	NPC107240
0.8224	Intermediate Similarity	NPC12656
0.8222	Intermediate Similarity	NPC133050
0.8208	Intermediate Similarity	NPC471179
0.8208	Intermediate Similarity	NPC286222
0.8208	Intermediate Similarity	NPC43525
0.8208	Intermediate Similarity	NPC228988
0.82	Intermediate Similarity	NPC70677
0.82	Intermediate Similarity	NPC130756
0.82	Intermediate Similarity	NPC12931
0.82	Intermediate Similarity	NPC213730
0.819	Intermediate Similarity	NPC132720
0.8182	Intermediate Similarity	NPC475078
0.8182	Intermediate Similarity	NPC107619
0.8182	Intermediate Similarity	NPC474073
0.8182	Intermediate Similarity	NPC109955
0.8173	Intermediate Similarity	NPC64586
0.8165	Intermediate Similarity	NPC477136
0.8163	Intermediate Similarity	NPC246679
0.8163	Intermediate Similarity	NPC32714
0.8155	Intermediate Similarity	NPC477814
0.8155	Intermediate Similarity	NPC53740
0.8155	Intermediate Similarity	NPC310456
0.8148	Intermediate Similarity	NPC474486
0.8148	Intermediate Similarity	NPC147179
0.8148	Intermediate Similarity	NPC35797
0.8148	Intermediate Similarity	NPC192948
0.8137	Intermediate Similarity	NPC254965
0.8137	Intermediate Similarity	NPC327811
0.8131	Intermediate Similarity	NPC263753
0.8131	Intermediate Similarity	NPC322239
0.8131	Intermediate Similarity	NPC117846
0.8131	Intermediate Similarity	NPC242136
0.8119	Intermediate Similarity	NPC477685
0.8119	Intermediate Similarity	NPC91461
0.8119	Intermediate Similarity	NPC7686

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 NPC8392 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	1079
0.2-0.3	1335
0.3-0.4	2931
0.4-0.5	1858
0.5-0.6	1114
0.6-0.7	419
0.7-0.8	74
0.8-0.85	6
0.85-0.9	7
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9556	High Similarity	NPD845	Approved
0.9348	High Similarity	NPD1809	Phase 2
0.9043	High Similarity	NPD288	Approved
0.9032	High Similarity	NPD1432	Clinical (unspecified phase)
0.8876	High Similarity	NPD111	Approved
0.8854	High Similarity	NPD3020	Approved
0.8737	High Similarity	NPD2859	Approved
0.8737	High Similarity	NPD844	Approved
0.8737	High Similarity	NPD2860	Approved
0.8673	High Similarity	NPD940	Approved
0.8673	High Similarity	NPD846	Approved
0.8632	High Similarity	NPD2934	Approved
0.8632	High Similarity	NPD2933	Approved
0.8571	High Similarity	NPD289	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD3021	Approved
0.8095	Intermediate Similarity	NPD3022	Approved
0.8091	Intermediate Similarity	NPD5303	Approved
0.8091	Intermediate Similarity	NPD5304	Approved
0.8077	Intermediate Similarity	NPD2342	Discontinued
0.8037	Intermediate Similarity	NPD7635	Approved
0.7981	Intermediate Similarity	NPD1445	Approved
0.7981	Intermediate Similarity	NPD1444	Approved
0.7963	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD9608	Approved
0.7961	Intermediate Similarity	NPD9610	Approved
0.7925	Intermediate Similarity	NPD4750	Phase 3
0.7798	Intermediate Similarity	NPD2229	Approved
0.7798	Intermediate Similarity	NPD2228	Approved
0.7798	Intermediate Similarity	NPD2234	Approved
0.7788	Intermediate Similarity	NPD4589	Approved
0.7757	Intermediate Similarity	NPD1792	Phase 2
0.7692	Intermediate Similarity	NPD9500	Approved
0.7672	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD1242	Phase 1
0.7647	Intermediate Similarity	NPD9273	Approved
0.764	Intermediate Similarity	NPD9087	Approved
0.7611	Intermediate Similarity	NPD3091	Approved
0.7568	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4093	Discontinued
0.7544	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3028	Approved
0.7478	Intermediate Similarity	NPD4626	Approved
0.7478	Intermediate Similarity	NPD1751	Approved
0.7478	Intermediate Similarity	NPD3019	Approved
0.7478	Intermediate Similarity	NPD4059	Approved
0.7478	Intermediate Similarity	NPD2932	Approved
0.7455	Intermediate Similarity	NPD228	Approved
0.7434	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3143	Discontinued
0.7411	Intermediate Similarity	NPD475	Phase 2
0.7391	Intermediate Similarity	NPD9294	Approved
0.7387	Intermediate Similarity	NPD1138	Approved
0.735	Intermediate Similarity	NPD1610	Phase 2
0.735	Intermediate Similarity	NPD3092	Approved
0.7345	Intermediate Similarity	NPD6671	Approved
0.7345	Intermediate Similarity	NPD256	Approved
0.7345	Intermediate Similarity	NPD255	Approved
0.7339	Intermediate Similarity	NPD2684	Approved
0.7328	Intermediate Similarity	NPD2286	Discontinued
0.7312	Intermediate Similarity	NPD9088	Approved
0.7304	Intermediate Similarity	NPD7330	Discontinued
0.7297	Intermediate Similarity	NPD1137	Approved
0.7297	Intermediate Similarity	NPD1139	Approved
0.7288	Intermediate Similarity	NPD3070	Discontinued
0.7257	Intermediate Similarity	NPD497	Approved
0.7257	Intermediate Similarity	NPD1791	Approved
0.7257	Intermediate Similarity	NPD1793	Approved
0.725	Intermediate Similarity	NPD1129	Approved
0.725	Intermediate Similarity	NPD1135	Approved
0.725	Intermediate Similarity	NPD1131	Approved
0.725	Intermediate Similarity	NPD1134	Approved
0.725	Intermediate Similarity	NPD1133	Approved
0.725	Intermediate Similarity	NPD1164	Approved
0.7248	Intermediate Similarity	NPD290	Approved
0.7236	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD9379	Approved
0.7232	Intermediate Similarity	NPD9377	Approved
0.7196	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3095	Discontinued
0.7179	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD496	Approved
0.7168	Intermediate Similarity	NPD495	Approved
0.7168	Intermediate Similarity	NPD498	Approved
0.7156	Intermediate Similarity	NPD968	Approved
0.7155	Intermediate Similarity	NPD1548	Phase 1
0.7155	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7636	Approved
0.712	Intermediate Similarity	NPD4060	Phase 1
0.7107	Intermediate Similarity	NPD3094	Phase 2
0.7094	Intermediate Similarity	NPD5691	Approved
0.7091	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD821	Approved
0.708	Intermediate Similarity	NPD7843	Approved
0.7073	Intermediate Similarity	NPD4908	Phase 1
0.7069	Intermediate Similarity	NPD317	Approved
0.7069	Intermediate Similarity	NPD318	Approved
0.7069	Intermediate Similarity	NPD856	Approved
0.7069	Intermediate Similarity	NPD16	Approved
0.7059	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD422	Phase 1
0.7049	Intermediate Similarity	NPD2194	Approved
0.7049	Intermediate Similarity	NPD2195	Approved
0.7043	Intermediate Similarity	NPD6387	Discontinued
0.7043	Intermediate Similarity	NPD7157	Approved
0.7034	Intermediate Similarity	NPD2667	Approved
0.7034	Intermediate Similarity	NPD2668	Approved
0.7027	Intermediate Similarity	NPD9266	Approved
0.7027	Intermediate Similarity	NPD74	Approved
0.7025	Intermediate Similarity	NPD1283	Approved
0.7018	Intermediate Similarity	NPD5283	Phase 1
0.701	Intermediate Similarity	NPD9089	Approved
0.6992	Remote Similarity	NPD4212	Discontinued
0.6992	Remote Similarity	NPD4208	Discontinued
0.6992	Remote Similarity	NPD3635	Approved
0.6992	Remote Similarity	NPD3637	Approved
0.6992	Remote Similarity	NPD2861	Phase 2
0.6992	Remote Similarity	NPD3636	Approved
0.6992	Remote Similarity	NPD5736	Approved
0.699	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD9568	Approved
0.6983	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD9493	Approved
0.6964	Remote Similarity	NPD5451	Approved
0.6957	Remote Similarity	NPD9618	Approved
0.6957	Remote Similarity	NPD9614	Approved
0.6944	Remote Similarity	NPD4817	Approved
0.6944	Remote Similarity	NPD4818	Approved
0.6942	Remote Similarity	NPD4659	Approved
0.6942	Remote Similarity	NPD4749	Approved
0.6937	Remote Similarity	NPD9267	Approved
0.6937	Remote Similarity	NPD9263	Approved
0.6937	Remote Similarity	NPD9264	Approved
0.6935	Remote Similarity	NPD2606	Approved
0.6935	Remote Similarity	NPD4207	Discontinued
0.6935	Remote Similarity	NPD2605	Approved
0.6917	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD3690	Phase 2
0.6911	Remote Similarity	NPD3691	Phase 2
0.6907	Remote Similarity	NPD9093	Approved
0.6903	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD709	Approved
0.6885	Remote Similarity	NPD6696	Suspended
0.688	Remote Similarity	NPD4625	Phase 3
0.688	Remote Similarity	NPD5155	Approved
0.688	Remote Similarity	NPD5156	Approved
0.6875	Remote Similarity	NPD4097	Suspended
0.687	Remote Similarity	NPD1398	Phase 1
0.6864	Remote Similarity	NPD9545	Approved
0.6864	Remote Similarity	NPD1759	Phase 1
0.6863	Remote Similarity	NPD9295	Approved
0.686	Remote Similarity	NPD2232	Approved
0.686	Remote Similarity	NPD2230	Approved
0.686	Remote Similarity	NPD2233	Approved
0.6852	Remote Similarity	NPD1616	Discontinued
0.6847	Remote Similarity	NPD3134	Approved
0.6838	Remote Similarity	NPD7340	Approved
0.6833	Remote Similarity	NPD3023	Approved
0.6833	Remote Similarity	NPD3026	Approved
0.6829	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1470	Approved
0.6829	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4103	Phase 2
0.6829	Remote Similarity	NPD2797	Approved
0.6818	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3025	Approved
0.6807	Remote Similarity	NPD1651	Approved
0.6807	Remote Similarity	NPD3024	Approved
0.6803	Remote Similarity	NPD6582	Phase 2
0.6803	Remote Similarity	NPD6583	Phase 3
0.6803	Remote Similarity	NPD1669	Approved
0.68	Remote Similarity	NPD3595	Approved
0.68	Remote Similarity	NPD9073	Approved
0.68	Remote Similarity	NPD3594	Approved
0.6783	Remote Similarity	NPD5535	Approved
0.678	Remote Similarity	NPD1758	Phase 1
0.678	Remote Similarity	NPD9615	Approved
0.678	Remote Similarity	NPD9613	Approved
0.678	Remote Similarity	NPD9616	Approved
0.6777	Remote Similarity	NPD1281	Approved
0.6774	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4624	Approved
0.6772	Remote Similarity	NPD6663	Approved
0.6772	Remote Similarity	NPD6405	Approved
0.6772	Remote Similarity	NPD6407	Approved
0.6765	Remote Similarity	NPD1101	Approved
0.675	Remote Similarity	NPD9381	Approved
0.675	Remote Similarity	NPD9384	Approved
0.6748	Remote Similarity	NPD8651	Approved
0.6744	Remote Similarity	NPD2157	Approved
0.6727	Remote Similarity	NPD3681	Approved
0.6727	Remote Similarity	NPD3683	Approved
0.6727	Remote Similarity	NPD4229	Approved
0.6727	Remote Similarity	NPD3682	Approved
0.6727	Remote Similarity	NPD4231	Approved
0.6727	Remote Similarity	NPD3680	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