NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.17
Volume:	257.684
LogP:	5.235
LogD:	4.156
LogS:	-4.281
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	2.757
Fsp3:	0.467
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:	-4.598
MDCK Permeability:	1.6029282051022165e-05
Pgp-inhibitor:	0.62
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.287
Plasma Protein Binding (PPB):	99.01854705810547%
Volume Distribution (VD):	6.212
Pgp-substrate:	3.386273145675659%

ADMET: Metabolism

CYP1A2-inhibitor:	0.949
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.886
CYP2C19-substrate:	0.649
CYP2C9-inhibitor:	0.72
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.826
CYP2D6-substrate:	0.835
CYP3A4-inhibitor:	0.514
CYP3A4-substrate:	0.363

ADMET: Excretion

Clearance (CL):	13.941
Half-life (T1/2):	0.261

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.569
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.786
Skin Sensitization:	0.649
Carcinogencity:	0.096
Eye Corrosion:	0.698
Eye Irritation:	0.989
Respiratory Toxicity:	0.321

Download Data

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

Natural Product: NPC77492

Natural Product ID:	NPC77492
*Common Name:**	4-(1',5'-Dimethylhex-4'-Enyl)-2-Methylphenol
IUPAC Name:	2-methyl-4-[(2R)-6-methylhept-5-en-2-yl]phenol
Synonyms:
Standard InCHIKey:	AHRNUZBHBAHMHY-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C15H22O/c1-11(2)6-5-7-12(3)14-8-9-15(16)13(4)10-14/h6,8-10,12,16H,5,7H2,1-4H3/t12-/m1/s1
SMILES:	CC(=CCC[C@H](c1ccc(c(c1)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510595
PubChem CID:	10353348
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001272] Cresols [CHEMONTID:0001274] Ortho cresols

*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
NPO12175	Iostephane heterophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473422]
NPO12175	Iostephane heterophylla	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
MIC	12
Others	15

Activity Type	# Activity
Organism	27

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[505611]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[505611]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	16.0	ug.mL-1	PMID[505611]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16.0	ug.mL-1	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	32.0	ug.mL-1	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[505611]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	32.0	ug.mL-1	PMID[505611]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	128.0	ug.mL-1	PMID[505611]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	128.0	ug.mL-1	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	30.71	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	37.82	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	48.24	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	63.06	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	75.57	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	34.04	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	39.08	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	50.02	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	60.35	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	66.73	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	25.34	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	39.06	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	44.2	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	52.28	%	PMID[505611]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	=	68.0	%	PMID[505611]

☑ 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 NPC77492 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	298
0.1-0.2	1824
0.2-0.3	4542
0.3-0.4	13482
0.4-0.5	6654
0.5-0.6	9381
0.6-0.7	5001
0.7-0.8	1177
0.8-0.85	199
0.85-0.9	101
0.9-0.95	33
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC8392
0.9677	High Similarity	NPC122005
0.9677	High Similarity	NPC252821
0.9574	High Similarity	NPC225506
0.9451	High Similarity	NPC204210
0.9451	High Similarity	NPC304541
0.9355	High Similarity	NPC144682
0.9286	High Similarity	NPC271274
0.9263	High Similarity	NPC128723
0.9247	High Similarity	NPC316301
0.9247	High Similarity	NPC289769
0.9247	High Similarity	NPC27323
0.9247	High Similarity	NPC152415
0.9231	High Similarity	NPC123273
0.9231	High Similarity	NPC70436
0.9231	High Similarity	NPC258219
0.9231	High Similarity	NPC242240
0.9231	High Similarity	NPC318325
0.9184	High Similarity	NPC138942
0.9175	High Similarity	NPC168829
0.9158	High Similarity	NPC79241
0.9158	High Similarity	NPC6597
0.9121	High Similarity	NPC113460
0.9121	High Similarity	NPC25493
0.9091	High Similarity	NPC21594
0.9082	High Similarity	NPC288411
0.9053	High Similarity	NPC312132
0.9053	High Similarity	NPC259512
0.9032	High Similarity	NPC306074
0.9032	High Similarity	NPC155908
0.9022	High Similarity	NPC280347
0.9022	High Similarity	NPC177420
0.9011	High Similarity	NPC407
0.9011	High Similarity	NPC23167
0.9011	High Similarity	NPC307235
0.901	High Similarity	NPC58865
0.9	High Similarity	NPC228737
0.9	High Similarity	NPC151477
0.8969	High Similarity	NPC72729
0.8969	High Similarity	NPC211885
0.8958	High Similarity	NPC225464
0.8947	High Similarity	NPC222146
0.8925	High Similarity	NPC55561
0.8922	High Similarity	NPC296683
0.8922	High Similarity	NPC13482
0.8901	High Similarity	NPC155393
0.8901	High Similarity	NPC197783
0.8878	High Similarity	NPC51015
0.8866	High Similarity	NPC33675
0.8866	High Similarity	NPC92730
0.8866	High Similarity	NPC299762
0.8854	High Similarity	NPC82664
0.8854	High Similarity	NPC473388
0.8854	High Similarity	NPC132271
0.8854	High Similarity	NPC216520
0.8854	High Similarity	NPC292730
0.8842	High Similarity	NPC128062
0.8842	High Similarity	NPC245187
0.8804	High Similarity	NPC184169
0.88	High Similarity	NPC303141
0.88	High Similarity	NPC117115
0.8791	High Similarity	NPC175313
0.8791	High Similarity	NPC286904
0.8791	High Similarity	NPC248817
0.8788	High Similarity	NPC108497
0.8788	High Similarity	NPC269212
0.875	High Similarity	NPC250323
0.875	High Similarity	NPC26244
0.875	High Similarity	NPC228425
0.8738	High Similarity	NPC141782
0.8737	High Similarity	NPC162314
0.8737	High Similarity	NPC210497
0.8737	High Similarity	NPC147284
0.8737	High Similarity	NPC271440
0.8737	High Similarity	NPC94139
0.8737	High Similarity	NPC3358
0.8737	High Similarity	NPC55903
0.8737	High Similarity	NPC306884
0.8725	High Similarity	NPC262365
0.8723	High Similarity	NPC192
0.8713	High Similarity	NPC54765
0.871	High Similarity	NPC19680
0.871	High Similarity	NPC27974
0.87	High Similarity	NPC475225
0.8687	High Similarity	NPC252105
0.8681	High Similarity	NPC265146
0.8681	High Similarity	NPC124436
0.8667	High Similarity	NPC715
0.8654	High Similarity	NPC260323
0.8654	High Similarity	NPC176279
0.8654	High Similarity	NPC151537
0.8654	High Similarity	NPC95716
0.8646	High Similarity	NPC151715
0.8632	High Similarity	NPC45040
0.8632	High Similarity	NPC231150
0.8617	High Similarity	NPC98772
0.8614	High Similarity	NPC243677
0.8614	High Similarity	NPC219286
0.8614	High Similarity	NPC99557
0.86	High Similarity	NPC470202
0.86	High Similarity	NPC235762
0.86	High Similarity	NPC471228
0.8586	High Similarity	NPC248396
0.8586	High Similarity	NPC129373
0.8586	High Similarity	NPC48730
0.8585	High Similarity	NPC195922
0.8571	High Similarity	NPC46940
0.8571	High Similarity	NPC152097
0.8558	High Similarity	NPC44732
0.8557	High Similarity	NPC274678
0.8544	High Similarity	NPC95344
0.8544	High Similarity	NPC63698
0.8544	High Similarity	NPC470039
0.8544	High Similarity	NPC61885
0.8544	High Similarity	NPC11554
0.8542	High Similarity	NPC325292
0.8542	High Similarity	NPC138117
0.8529	High Similarity	NPC469913
0.8529	High Similarity	NPC248904
0.8526	High Similarity	NPC300017
0.8515	High Similarity	NPC238696
0.8515	High Similarity	NPC475580
0.8515	High Similarity	NPC272029
0.85	High Similarity	NPC12221
0.8491	Intermediate Similarity	NPC141003
0.8491	Intermediate Similarity	NPC35344
0.8485	Intermediate Similarity	NPC80027
0.8485	Intermediate Similarity	NPC260775
0.8476	Intermediate Similarity	NPC476632
0.8476	Intermediate Similarity	NPC225679
0.8476	Intermediate Similarity	NPC165770
0.8476	Intermediate Similarity	NPC4493
0.8476	Intermediate Similarity	NPC308689
0.8469	Intermediate Similarity	NPC202986
0.8462	Intermediate Similarity	NPC471954
0.8462	Intermediate Similarity	NPC75272
0.8462	Intermediate Similarity	NPC314187
0.8454	Intermediate Similarity	NPC76938
0.8447	Intermediate Similarity	NPC320439
0.8447	Intermediate Similarity	NPC66834
0.8438	Intermediate Similarity	NPC270547
0.8431	Intermediate Similarity	NPC47284
0.8411	Intermediate Similarity	NPC107240
0.8411	Intermediate Similarity	NPC12656
0.8411	Intermediate Similarity	NPC268160
0.84	Intermediate Similarity	NPC70677
0.84	Intermediate Similarity	NPC130756
0.84	Intermediate Similarity	NPC12931
0.84	Intermediate Similarity	NPC174911
0.8396	Intermediate Similarity	NPC43525
0.8396	Intermediate Similarity	NPC228988
0.8396	Intermediate Similarity	NPC471179
0.8396	Intermediate Similarity	NPC286222
0.8387	Intermediate Similarity	NPC150837
0.8384	Intermediate Similarity	NPC32674
0.8384	Intermediate Similarity	NPC475078
0.8384	Intermediate Similarity	NPC156313
0.8384	Intermediate Similarity	NPC474073
0.8381	Intermediate Similarity	NPC224870
0.8381	Intermediate Similarity	NPC132720
0.8367	Intermediate Similarity	NPC32714
0.8367	Intermediate Similarity	NPC313650
0.8365	Intermediate Similarity	NPC64586
0.8351	Intermediate Similarity	NPC29373
0.835	Intermediate Similarity	NPC310456
0.835	Intermediate Similarity	NPC477814
0.835	Intermediate Similarity	NPC53740
0.8349	Intermediate Similarity	NPC477136
0.8333	Intermediate Similarity	NPC119860
0.8333	Intermediate Similarity	NPC147179
0.8333	Intermediate Similarity	NPC192948
0.8333	Intermediate Similarity	NPC474486
0.8333	Intermediate Similarity	NPC120719
0.8333	Intermediate Similarity	NPC35797
0.8318	Intermediate Similarity	NPC117846
0.8318	Intermediate Similarity	NPC263753
0.8317	Intermediate Similarity	NPC477685
0.8316	Intermediate Similarity	NPC104216
0.8302	Intermediate Similarity	NPC77772
0.8302	Intermediate Similarity	NPC470770
0.8302	Intermediate Similarity	NPC469912
0.8302	Intermediate Similarity	NPC266937
0.8302	Intermediate Similarity	NPC322753
0.83	Intermediate Similarity	NPC51333
0.83	Intermediate Similarity	NPC216468
0.83	Intermediate Similarity	NPC132078
0.83	Intermediate Similarity	NPC78119
0.8286	Intermediate Similarity	NPC228343
0.8286	Intermediate Similarity	NPC254833
0.8257	Intermediate Similarity	NPC308828
0.8257	Intermediate Similarity	NPC308311
0.8257	Intermediate Similarity	NPC219112
0.8257	Intermediate Similarity	NPC477137
0.8257	Intermediate Similarity	NPC38893
0.8257	Intermediate Similarity	NPC471668
0.8252	Intermediate Similarity	NPC474839
0.8252	Intermediate Similarity	NPC239291
0.8241	Intermediate Similarity	NPC473137
0.8235	Intermediate Similarity	NPC196479
0.8224	Intermediate Similarity	NPC473521

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 NPC77492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	1037
0.2-0.3	1329
0.3-0.4	2910
0.4-0.5	1895
0.5-0.6	1136
0.6-0.7	427
0.7-0.8	83
0.8-0.85	10
0.85-0.9	7
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.956	High Similarity	NPD845	Approved
0.9355	High Similarity	NPD1809	Phase 2
0.9247	High Similarity	NPD1432	Clinical (unspecified phase)
0.9062	High Similarity	NPD3020	Approved
0.9053	High Similarity	NPD288	Approved
0.8947	High Similarity	NPD844	Approved
0.875	High Similarity	NPD2859	Approved
0.875	High Similarity	NPD2860	Approved
0.8687	High Similarity	NPD940	Approved
0.8687	High Similarity	NPD846	Approved
0.8681	High Similarity	NPD111	Approved
0.8646	High Similarity	NPD2934	Approved
0.8646	High Similarity	NPD2933	Approved
0.8586	High Similarity	NPD289	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD3021	Approved
0.8286	Intermediate Similarity	NPD3022	Approved
0.8224	Intermediate Similarity	NPD7635	Approved
0.8173	Intermediate Similarity	NPD1444	Approved
0.8173	Intermediate Similarity	NPD1445	Approved
0.8131	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD4750	Phase 3
0.8108	Intermediate Similarity	NPD5303	Approved
0.8108	Intermediate Similarity	NPD5304	Approved
0.8095	Intermediate Similarity	NPD2342	Discontinued
0.7982	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD2229	Approved
0.7982	Intermediate Similarity	NPD2228	Approved
0.7982	Intermediate Similarity	NPD2234	Approved
0.7965	Intermediate Similarity	NPD4589	Approved
0.7944	Intermediate Similarity	NPD1792	Phase 2
0.7845	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD9610	Approved
0.781	Intermediate Similarity	NPD9608	Approved
0.7788	Intermediate Similarity	NPD3091	Approved
0.7719	Intermediate Similarity	NPD4093	Discontinued
0.7714	Intermediate Similarity	NPD9500	Approved
0.7692	Intermediate Similarity	NPD1242	Phase 1
0.7652	Intermediate Similarity	NPD3019	Approved
0.7652	Intermediate Similarity	NPD4626	Approved
0.7652	Intermediate Similarity	NPD2932	Approved
0.7652	Intermediate Similarity	NPD1751	Approved
0.7652	Intermediate Similarity	NPD4059	Approved
0.7611	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD3028	Approved
0.7522	Intermediate Similarity	NPD6671	Approved
0.7521	Intermediate Similarity	NPD3092	Approved
0.75	Intermediate Similarity	NPD9273	Approved
0.7477	Intermediate Similarity	NPD228	Approved
0.7473	Intermediate Similarity	NPD9087	Approved
0.7436	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3143	Discontinued
0.7434	Intermediate Similarity	NPD1791	Approved
0.7434	Intermediate Similarity	NPD1793	Approved
0.7434	Intermediate Similarity	NPD475	Phase 2
0.7434	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD1138	Approved
0.7398	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1610	Phase 2
0.7364	Intermediate Similarity	NPD2684	Approved
0.735	Intermediate Similarity	NPD3095	Discontinued
0.735	Intermediate Similarity	NPD2286	Discontinued
0.7328	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7330	Discontinued
0.7321	Intermediate Similarity	NPD1139	Approved
0.7321	Intermediate Similarity	NPD1137	Approved
0.7311	Intermediate Similarity	NPD3070	Discontinued
0.7297	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD497	Approved
0.728	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD1164	Approved
0.7273	Intermediate Similarity	NPD1135	Approved
0.7273	Intermediate Similarity	NPD1131	Approved
0.7273	Intermediate Similarity	NPD1129	Approved
0.7273	Intermediate Similarity	NPD1133	Approved
0.7273	Intermediate Similarity	NPD3094	Phase 2
0.7273	Intermediate Similarity	NPD1134	Approved
0.7265	Intermediate Similarity	NPD5691	Approved
0.7257	Intermediate Similarity	NPD9377	Approved
0.7257	Intermediate Similarity	NPD9379	Approved
0.7236	Intermediate Similarity	NPD4908	Phase 1
0.7234	Intermediate Similarity	NPD9294	Approved
0.7217	Intermediate Similarity	NPD255	Approved
0.7217	Intermediate Similarity	NPD256	Approved
0.7217	Intermediate Similarity	NPD7157	Approved
0.7213	Intermediate Similarity	NPD2194	Approved
0.7213	Intermediate Similarity	NPD2195	Approved
0.7203	Intermediate Similarity	NPD2668	Approved
0.7203	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2667	Approved
0.7193	Intermediate Similarity	NPD498	Approved
0.7193	Intermediate Similarity	NPD495	Approved
0.7193	Intermediate Similarity	NPD5283	Phase 1
0.7193	Intermediate Similarity	NPD496	Approved
0.7158	Intermediate Similarity	NPD9088	Approved
0.7155	Intermediate Similarity	NPD7636	Approved
0.7154	Intermediate Similarity	NPD5736	Approved
0.7154	Intermediate Similarity	NPD3636	Approved
0.7154	Intermediate Similarity	NPD3637	Approved
0.7154	Intermediate Similarity	NPD3635	Approved
0.7154	Intermediate Similarity	NPD2861	Phase 2
0.7117	Intermediate Similarity	NPD290	Approved
0.7107	Intermediate Similarity	NPD4749	Approved
0.7105	Intermediate Similarity	NPD7843	Approved
0.7105	Intermediate Similarity	NPD821	Approved
0.7097	Intermediate Similarity	NPD2605	Approved
0.7097	Intermediate Similarity	NPD2606	Approved
0.7094	Intermediate Similarity	NPD856	Approved
0.7094	Intermediate Similarity	NPD16	Approved
0.7083	Intermediate Similarity	NPD1201	Approved
0.7083	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3691	Phase 2
0.7073	Intermediate Similarity	NPD3690	Phase 2
0.7069	Intermediate Similarity	NPD6387	Discontinued
0.7049	Intermediate Similarity	NPD1283	Approved
0.7049	Intermediate Similarity	NPD6696	Suspended
0.7043	Intermediate Similarity	NPD1398	Phase 1
0.704	Intermediate Similarity	NPD5156	Approved
0.704	Intermediate Similarity	NPD4625	Phase 3
0.704	Intermediate Similarity	NPD5155	Approved
0.7034	Intermediate Similarity	NPD1548	Phase 1
0.7031	Intermediate Similarity	NPD4097	Suspended
0.7027	Intermediate Similarity	NPD968	Approved
0.7025	Intermediate Similarity	NPD2232	Approved
0.7025	Intermediate Similarity	NPD2233	Approved
0.7025	Intermediate Similarity	NPD2230	Approved
0.7016	Intermediate Similarity	NPD4212	Discontinued
0.7016	Intermediate Similarity	NPD4208	Discontinued
0.7009	Intermediate Similarity	NPD7340	Approved
0.7009	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3023	Approved
0.7	Intermediate Similarity	NPD3026	Approved
0.6992	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5451	Approved
0.6983	Remote Similarity	NPD9618	Approved
0.6983	Remote Similarity	NPD9614	Approved
0.6975	Remote Similarity	NPD3025	Approved
0.6975	Remote Similarity	NPD1651	Approved
0.6975	Remote Similarity	NPD3024	Approved
0.6972	Remote Similarity	NPD4817	Approved
0.6972	Remote Similarity	NPD4818	Approved
0.6967	Remote Similarity	NPD4659	Approved
0.6967	Remote Similarity	NPD1669	Approved
0.6964	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.696	Remote Similarity	NPD3594	Approved
0.696	Remote Similarity	NPD3595	Approved
0.696	Remote Similarity	NPD4207	Discontinued
0.6949	Remote Similarity	NPD317	Approved
0.6949	Remote Similarity	NPD318	Approved
0.6942	Remote Similarity	NPD422	Phase 1
0.6935	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4624	Approved
0.693	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6407	Approved
0.6929	Remote Similarity	NPD6405	Approved
0.6929	Remote Similarity	NPD6663	Approved
0.6923	Remote Similarity	NPD709	Approved
0.6911	Remote Similarity	NPD8651	Approved
0.6903	Remote Similarity	NPD9266	Approved
0.6903	Remote Similarity	NPD74	Approved
0.6899	Remote Similarity	NPD2157	Approved
0.6891	Remote Similarity	NPD1759	Phase 1
0.6881	Remote Similarity	NPD1616	Discontinued
0.6875	Remote Similarity	NPD3134	Approved
0.6869	Remote Similarity	NPD9089	Approved
0.6864	Remote Similarity	NPD9568	Approved
0.6864	Remote Similarity	NPD9493	Approved
0.6857	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1470	Approved
0.6855	Remote Similarity	NPD2797	Approved
0.6855	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4103	Phase 2
0.685	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6582	Phase 2
0.6829	Remote Similarity	NPD6583	Phase 3
0.6829	Remote Similarity	NPD1755	Approved
0.6814	Remote Similarity	NPD9264	Approved
0.6814	Remote Similarity	NPD9263	Approved
0.6814	Remote Similarity	NPD9267	Approved
0.681	Remote Similarity	NPD5535	Approved
0.6807	Remote Similarity	NPD1758	Phase 1
0.6807	Remote Similarity	NPD9615	Approved
0.6807	Remote Similarity	NPD9613	Approved
0.6807	Remote Similarity	NPD9616	Approved
0.6803	Remote Similarity	NPD1281	Approved
0.68	Remote Similarity	NPD6584	Phase 3
0.6796	Remote Similarity	NPD1101	Approved
0.6794	Remote Similarity	NPD2799	Discontinued
0.6777	Remote Similarity	NPD9381	Approved
0.6777	Remote Similarity	NPD9384	Approved
0.6768	Remote Similarity	NPD9093	Approved
0.6757	Remote Similarity	NPD4229	Approved
0.6757	Remote Similarity	NPD3680	Approved
0.6757	Remote Similarity	NPD4231	Approved
0.6757	Remote Similarity	NPD3683	Approved
0.6757	Remote Similarity	NPD3682	Approved
0.6757	Remote Similarity	NPD3681	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