NPASS Compound

Structure

NPC296144 OpenBabel07101718192D 31 31 0 0 0 0 0 0 0 0999 V2000 -0.0000 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 19 2 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 22 2 0 0 0 0 12 13 1 0 0 0 0 12 21 2 0 0 0 0 13 24 1 0 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 16 26 2 0 0 0 0 17 24 2 0 0 0 0 17 26 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 0 0 0 0 23 27 2 0 0 0 0 24 27 1 0 0 0 0 25 29 2 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.28
Volume:	481.061
LogP:	3.676
LogD:	3.313
LogS:	-4.067
# Rotatable Bonds:	12
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	3.366
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.899
MDCK Permeability:	2.4606662918813527e-05
Pgp-inhibitor:	0.58
Pgp-substrate:	0.131
Human Intestinal Absorption (HIA):	0.663
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	99.03662872314453%
Volume Distribution (VD):	0.76
Pgp-substrate:	0.44202664494514465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.387
CYP1A2-substrate:	0.898
CYP2C19-inhibitor:	0.424
CYP2C19-substrate:	0.399
CYP2C9-inhibitor:	0.426
CYP2C9-substrate:	0.787
CYP2D6-inhibitor:	0.949
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.523
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	3.183
Half-life (T1/2):	0.972

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.004
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.977
Carcinogencity:	0.074
Eye Corrosion:	0.068
Eye Irritation:	0.922
Respiratory Toxicity:	0.469

Download Data

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

Natural Product: NPC296144

Natural Product ID:	NPC296144
*Common Name:**	(2E,6E,10E,14Z)-1-(2,5-Dihydroxy-3-Methylphenyl)-16-Hydroxy-3,7,11,15-Tetramethylhexadeca-2,6,10,14-Tetraen-5-One
IUPAC Name:	(2E,6E,10E,14Z)-1-(2,5-dihydroxy-3-methylphenyl)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-5-one
Synonyms:
Standard InCHIKey:	AUMNDJSQPDHCKI-XTMKDLMASA-N
Standard InCHI:	InChI=1S/C27H38O4/c1-19(9-7-11-22(4)18-28)8-6-10-20(2)14-25(29)15-21(3)12-13-24-17-26(30)16-23(5)27(24)31/h8,11-12,14,16-17,28,30-31H,6-7,9-10,13,15,18H2,1-5H3/b19-8+,20-14+,21-12+,22-11-
SMILES:	C/C(=CCC/C(=C/C(=O)C/C(=C/Cc1cc(cc(C)c1O)O)/C)/C)/CC/C=C(/C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453809
PubChem CID:	10093983
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO8863	Cystoseira crinita	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880316]
NPO8863	Cystoseira crinita	Species	Sargassaceae	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
GI50	3
Others	20

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	8
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	GI50	=	7.1	ug.mL-1	PMID[495534]
NPT65	Cell Line	HepG2	Homo sapiens	TGI	>	10.0	ug.mL-1	PMID[495534]
NPT65	Cell Line	HepG2	Homo sapiens	LC50	>	10.0	ug.mL-1	PMID[495534]
NPT83	Cell Line	MCF7	Homo sapiens	LC50	>	10.0	ug.mL-1	PMID[495534]
NPT83	Cell Line	MCF7	Homo sapiens	TGI	=	5.1	ug.mL-1	PMID[495534]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	2.2	ug.mL-1	PMID[495534]
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	86.0	%	PMID[495534]
NPT1	Others	Radical scavenging activity		Activity	=	12.3	%	PMID[495534]
NPT1	Others	Radical scavenging activity		Activity	=	8.0	%	PMID[495534]
NPT1	Others	Radical scavenging activity		Activity	=	25.1	%	PMID[495534]
NPT1	Others	Radical scavenging activity		Activity	=	64.8	%	PMID[495534]
NPT1	Others	Radical scavenging activity		Activity	=	96.1	%	PMID[495534]
NPT1	Others	Radical scavenging activity		Activity	=	96.4	%	PMID[495534]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	10.6	%	PMID[495534]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	14.8	%	PMID[495534]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	32.1	%	PMID[495534]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	67.2	%	PMID[495534]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	73.7	%	PMID[495534]
NPT35	Others	n.a.		Activity	=	0.09	mmol/L	PMID[495534]
NPT2	Others	Unspecified		Activity	=	0.59	mmol/L	PMID[495534]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	2.3	ug.mL-1	PMID[495534]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	7.4	ug.mL-1	PMID[495534]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	>	10.0	ug.mL-1	PMID[495534]

☑ 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 NPC296144 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	208
0.1-0.2	1132
0.2-0.3	3330
0.3-0.4	10049
0.4-0.5	10042
0.5-0.6	7997
0.6-0.7	8390
0.7-0.8	1407
0.8-0.85	100
0.85-0.9	30
0.9-0.95	2
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC28784
0.9906	High Similarity	NPC474050
0.9906	High Similarity	NPC474114
0.9906	High Similarity	NPC473931
0.9714	High Similarity	NPC208229
0.9619	High Similarity	NPC26013
0.9619	High Similarity	NPC282855
0.9524	High Similarity	NPC279887
0.9524	High Similarity	NPC68260
0.9286	High Similarity	NPC476020
0.9182	High Similarity	NPC114918
0.9009	High Similarity	NPC197513
0.8899	High Similarity	NPC98392
0.8818	High Similarity	NPC471535
0.875	High Similarity	NPC477214
0.875	High Similarity	NPC319422
0.875	High Similarity	NPC477211
0.875	High Similarity	NPC477212
0.8739	High Similarity	NPC228609
0.8692	High Similarity	NPC108497
0.8679	High Similarity	NPC248396
0.8679	High Similarity	NPC48730
0.8679	High Similarity	NPC129373
0.8644	High Similarity	NPC49441
0.8624	High Similarity	NPC469913
0.8607	High Similarity	NPC59654
0.8598	High Similarity	NPC477685
0.8585	High Similarity	NPC260775
0.8583	High Similarity	NPC477213
0.8545	High Similarity	NPC474352
0.8537	High Similarity	NPC163169
0.8537	High Similarity	NPC123
0.8519	High Similarity	NPC269212
0.8512	High Similarity	NPC474944
0.8505	High Similarity	NPC130756
0.8505	High Similarity	NPC12931
0.8505	High Similarity	NPC70677
0.8496	Intermediate Similarity	NPC302371
0.8491	Intermediate Similarity	NPC152097
0.8475	Intermediate Similarity	NPC474175
0.8455	Intermediate Similarity	NPC271832
0.8393	Intermediate Similarity	NPC473524
0.8374	Intermediate Similarity	NPC476024
0.8361	Intermediate Similarity	NPC476022
0.8361	Intermediate Similarity	NPC474945
0.8349	Intermediate Similarity	NPC235762
0.8349	Intermediate Similarity	NPC471228
0.8347	Intermediate Similarity	NPC276962
0.8347	Intermediate Similarity	NPC190086
0.8333	Intermediate Similarity	NPC174911
0.8333	Intermediate Similarity	NPC130103
0.8319	Intermediate Similarity	NPC132720
0.8318	Intermediate Similarity	NPC474073
0.8318	Intermediate Similarity	NPC475078
0.8305	Intermediate Similarity	NPC473767
0.8291	Intermediate Similarity	NPC269414
0.8288	Intermediate Similarity	NPC155072
0.8279	Intermediate Similarity	NPC131799
0.8273	Intermediate Similarity	NPC93831
0.8273	Intermediate Similarity	NPC272029
0.8273	Intermediate Similarity	NPC475225
0.8257	Intermediate Similarity	NPC80800
0.8246	Intermediate Similarity	NPC469912
0.8241	Intermediate Similarity	NPC128723
0.824	Intermediate Similarity	NPC475880
0.822	Intermediate Similarity	NPC41567
0.822	Intermediate Similarity	NPC206205
0.8211	Intermediate Similarity	NPC49647
0.8211	Intermediate Similarity	NPC136342
0.8211	Intermediate Similarity	NPC227741
0.8211	Intermediate Similarity	NPC295202
0.8198	Intermediate Similarity	NPC47284
0.8197	Intermediate Similarity	NPC147896
0.819	Intermediate Similarity	NPC41851
0.8182	Intermediate Similarity	NPC477151
0.8182	Intermediate Similarity	NPC132518
0.8175	Intermediate Similarity	NPC474143
0.8175	Intermediate Similarity	NPC474246
0.8151	Intermediate Similarity	NPC182240
0.8151	Intermediate Similarity	NPC32152
0.8148	Intermediate Similarity	NPC88420
0.8125	Intermediate Similarity	NPC53740
0.812	Intermediate Similarity	NPC240163
0.812	Intermediate Similarity	NPC474486
0.8115	Intermediate Similarity	NPC471187
0.8115	Intermediate Similarity	NPC477153
0.8113	Intermediate Similarity	NPC306884
0.8113	Intermediate Similarity	NPC3358
0.8113	Intermediate Similarity	NPC162314
0.8113	Intermediate Similarity	NPC29373
0.8113	Intermediate Similarity	NPC94139
0.8113	Intermediate Similarity	NPC147284
0.8113	Intermediate Similarity	NPC210497
0.811	Intermediate Similarity	NPC246693
0.811	Intermediate Similarity	NPC242358
0.811	Intermediate Similarity	NPC110609
0.811	Intermediate Similarity	NPC251549
0.8108	Intermediate Similarity	NPC323810
0.8103	Intermediate Similarity	NPC190212
0.8083	Intermediate Similarity	NPC232295
0.8083	Intermediate Similarity	NPC474131
0.8083	Intermediate Similarity	NPC473136
0.8065	Intermediate Similarity	NPC306765
0.8053	Intermediate Similarity	NPC320439
0.8053	Intermediate Similarity	NPC66834
0.8053	Intermediate Similarity	NPC228737
0.8051	Intermediate Similarity	NPC477453
0.8049	Intermediate Similarity	NPC68756
0.8049	Intermediate Similarity	NPC152525
0.8049	Intermediate Similarity	NPC474237
0.8036	Intermediate Similarity	NPC303141
0.8036	Intermediate Similarity	NPC243677
0.8033	Intermediate Similarity	NPC46586
0.8033	Intermediate Similarity	NPC204535
0.8033	Intermediate Similarity	NPC475192
0.8031	Intermediate Similarity	NPC85342
0.8017	Intermediate Similarity	NPC228425
0.8017	Intermediate Similarity	NPC26615
0.8017	Intermediate Similarity	NPC286222
0.8017	Intermediate Similarity	NPC98372
0.8017	Intermediate Similarity	NPC177962
0.8017	Intermediate Similarity	NPC228988
0.8017	Intermediate Similarity	NPC62867
0.8016	Intermediate Similarity	NPC474546
0.8	Intermediate Similarity	NPC95034
0.8	Intermediate Similarity	NPC64157
0.8	Intermediate Similarity	NPC323074
0.8	Intermediate Similarity	NPC142087
0.8	Intermediate Similarity	NPC278832
0.8	Intermediate Similarity	NPC151197
0.8	Intermediate Similarity	NPC294741
0.7984	Intermediate Similarity	NPC477210
0.7984	Intermediate Similarity	NPC240744
0.7984	Intermediate Similarity	NPC167055
0.7983	Intermediate Similarity	NPC320864
0.7982	Intermediate Similarity	NPC262365
0.7982	Intermediate Similarity	NPC317305
0.7969	Intermediate Similarity	NPC329427
0.7969	Intermediate Similarity	NPC317601
0.7967	Intermediate Similarity	NPC477152
0.7967	Intermediate Similarity	NPC474130
0.7965	Intermediate Similarity	NPC54765
0.7963	Intermediate Similarity	NPC222146
0.7953	Intermediate Similarity	NPC196621
0.7951	Intermediate Similarity	NPC31936
0.7951	Intermediate Similarity	NPC154696
0.7949	Intermediate Similarity	NPC242136
0.7946	Intermediate Similarity	NPC475580
0.7946	Intermediate Similarity	NPC130817
0.7934	Intermediate Similarity	NPC318581
0.7934	Intermediate Similarity	NPC325544
0.7934	Intermediate Similarity	NPC477037
0.7931	Intermediate Similarity	NPC470770
0.7931	Intermediate Similarity	NPC308689
0.7931	Intermediate Similarity	NPC77772
0.7931	Intermediate Similarity	NPC266937
0.7931	Intermediate Similarity	NPC54373
0.7928	Intermediate Similarity	NPC252105
0.7928	Intermediate Similarity	NPC12221
0.7925	Intermediate Similarity	NPC312304
0.7925	Intermediate Similarity	NPC192
0.792	Intermediate Similarity	NPC71610
0.7913	Intermediate Similarity	NPC471954
0.7913	Intermediate Similarity	NPC75272
0.7905	Intermediate Similarity	NPC19680
0.7903	Intermediate Similarity	NPC74507
0.7903	Intermediate Similarity	NPC234890
0.7903	Intermediate Similarity	NPC181334
0.7903	Intermediate Similarity	NPC474803
0.7903	Intermediate Similarity	NPC117794
0.7899	Intermediate Similarity	NPC69539
0.7895	Intermediate Similarity	NPC34715
0.7895	Intermediate Similarity	NPC305603
0.7895	Intermediate Similarity	NPC61033
0.7895	Intermediate Similarity	NPC233320
0.7891	Intermediate Similarity	NPC471851
0.789	Intermediate Similarity	NPC283711
0.7886	Intermediate Similarity	NPC325301
0.7886	Intermediate Similarity	NPC327070
0.7881	Intermediate Similarity	NPC285350
0.7881	Intermediate Similarity	NPC12656
0.7876	Intermediate Similarity	NPC138942
0.7876	Intermediate Similarity	NPC117115
0.7863	Intermediate Similarity	NPC228452
0.7857	Intermediate Similarity	NPC471530
0.7857	Intermediate Similarity	NPC470202
0.7851	Intermediate Similarity	NPC160235
0.7846	Intermediate Similarity	NPC202225
0.7846	Intermediate Similarity	NPC204582
0.7845	Intermediate Similarity	NPC44732
0.7845	Intermediate Similarity	NPC222905
0.784	Intermediate Similarity	NPC472592
0.7838	Intermediate Similarity	NPC225506
0.7838	Intermediate Similarity	NPC72729
0.7833	Intermediate Similarity	NPC238176
0.7833	Intermediate Similarity	NPC187993
0.7833	Intermediate Similarity	NPC160199
0.7826	Intermediate Similarity	NPC95344
0.7826	Intermediate Similarity	NPC470039
0.7823	Intermediate Similarity	NPC198014

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 NPC296144 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	876
0.2-0.3	1514
0.3-0.4	2765
0.4-0.5	2080
0.5-0.6	1251
0.6-0.7	434
0.7-0.8	33
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8165	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD7635	Approved
0.7963	Intermediate Similarity	NPD844	Approved
0.7778	Intermediate Similarity	NPD845	Approved
0.7727	Intermediate Similarity	NPD288	Approved
0.7724	Intermediate Similarity	NPD3496	Discontinued
0.7667	Intermediate Similarity	NPD6671	Approved
0.7636	Intermediate Similarity	NPD1809	Phase 2
0.7627	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD2859	Approved
0.7477	Intermediate Similarity	NPD2860	Approved
0.7458	Intermediate Similarity	NPD4750	Phase 3
0.7434	Intermediate Similarity	NPD3020	Approved
0.7387	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD2934	Approved
0.7387	Intermediate Similarity	NPD2933	Approved
0.7381	Intermediate Similarity	NPD1201	Approved
0.736	Intermediate Similarity	NPD2932	Approved
0.736	Intermediate Similarity	NPD3019	Approved
0.7317	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD3022	Approved
0.7311	Intermediate Similarity	NPD3021	Approved
0.7304	Intermediate Similarity	NPD846	Approved
0.7304	Intermediate Similarity	NPD940	Approved
0.7288	Intermediate Similarity	NPD2342	Discontinued
0.7287	Intermediate Similarity	NPD1470	Approved
0.728	Intermediate Similarity	NPD5691	Approved
0.7209	Intermediate Similarity	NPD6696	Suspended
0.72	Intermediate Similarity	NPD3091	Approved
0.7176	Intermediate Similarity	NPD4208	Discontinued
0.7176	Intermediate Similarity	NPD5736	Approved
0.7154	Intermediate Similarity	NPD497	Approved
0.7132	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD9500	Approved
0.7073	Intermediate Similarity	NPD498	Approved
0.7073	Intermediate Similarity	NPD495	Approved
0.7073	Intermediate Similarity	NPD496	Approved
0.7059	Intermediate Similarity	NPD1445	Approved
0.7059	Intermediate Similarity	NPD1444	Approved
0.705	Intermediate Similarity	NPD2424	Discontinued
0.704	Intermediate Similarity	NPD7340	Approved
0.704	Intermediate Similarity	NPD9493	Approved
0.7037	Intermediate Similarity	NPD111	Approved
0.7037	Intermediate Similarity	NPD4060	Phase 1
0.7023	Intermediate Similarity	NPD3094	Phase 2
0.7016	Intermediate Similarity	NPD9614	Approved
0.7016	Intermediate Similarity	NPD9618	Approved
0.6992	Remote Similarity	NPD4207	Discontinued
0.6977	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3092	Approved
0.6977	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6663	Approved
0.6957	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD3095	Discontinued
0.6953	Remote Similarity	NPD1778	Approved
0.695	Remote Similarity	NPD8166	Discontinued
0.6949	Remote Similarity	NPD6647	Phase 2
0.6942	Remote Similarity	NPD74	Approved
0.6942	Remote Similarity	NPD9266	Approved
0.6942	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1398	Phase 1
0.6923	Remote Similarity	NPD7390	Discontinued
0.6917	Remote Similarity	NPD968	Approved
0.6917	Remote Similarity	NPD2861	Phase 2
0.6905	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3023	Approved
0.6899	Remote Similarity	NPD3026	Approved
0.6894	Remote Similarity	NPD1164	Approved
0.6891	Remote Similarity	NPD1237	Approved
0.6889	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7985	Registered
0.6885	Remote Similarity	NPD1792	Phase 2
0.6875	Remote Similarity	NPD3025	Approved
0.6875	Remote Similarity	NPD1651	Approved
0.6875	Remote Similarity	NPD3024	Approved
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1755	Approved
0.686	Remote Similarity	NPD9264	Approved
0.686	Remote Similarity	NPD9263	Approved
0.686	Remote Similarity	NPD9267	Approved
0.6855	Remote Similarity	NPD7843	Approved
0.6853	Remote Similarity	NPD3300	Phase 2
0.685	Remote Similarity	NPD9615	Approved
0.685	Remote Similarity	NPD9613	Approved
0.685	Remote Similarity	NPD9616	Approved
0.685	Remote Similarity	NPD5536	Phase 2
0.6846	Remote Similarity	NPD1611	Approved
0.6831	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7157	Approved
0.6812	Remote Similarity	NPD6653	Approved
0.6803	Remote Similarity	NPD2684	Approved
0.6797	Remote Similarity	NPD316	Approved
0.6797	Remote Similarity	NPD9545	Approved
0.6797	Remote Similarity	NPD1759	Phase 1
0.6797	Remote Similarity	NPD7330	Discontinued
0.6788	Remote Similarity	NPD943	Approved
0.6786	Remote Similarity	NPD5406	Approved
0.6786	Remote Similarity	NPD5408	Approved
0.6786	Remote Similarity	NPD5404	Approved
0.6786	Remote Similarity	NPD5405	Approved
0.678	Remote Similarity	NPD1242	Phase 1
0.6774	Remote Similarity	NPD228	Approved
0.6767	Remote Similarity	NPD2797	Approved
0.6765	Remote Similarity	NPD2313	Discontinued
0.6765	Remote Similarity	NPD3268	Approved
0.6761	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2629	Approved
0.6741	Remote Similarity	NPD600	Approved
0.6741	Remote Similarity	NPD596	Approved
0.6738	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6005	Phase 3
0.6738	Remote Similarity	NPD6004	Phase 3
0.6738	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7266	Discontinued
0.6738	Remote Similarity	NPD2346	Discontinued
0.6738	Remote Similarity	NPD6002	Phase 3
0.6733	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD290	Approved
0.6721	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1758	Phase 1
0.6716	Remote Similarity	NPD2798	Approved
0.6715	Remote Similarity	NPD6407	Approved
0.6715	Remote Similarity	NPD6405	Approved
0.6715	Remote Similarity	NPD839	Approved
0.6715	Remote Similarity	NPD4248	Discontinued
0.6715	Remote Similarity	NPD840	Approved
0.6714	Remote Similarity	NPD2799	Discontinued
0.6713	Remote Similarity	NPD3400	Discontinued
0.6698	Remote Similarity	NPD9088	Approved
0.6693	Remote Similarity	NPD255	Approved
0.6693	Remote Similarity	NPD256	Approved
0.6692	Remote Similarity	NPD4059	Approved
0.6692	Remote Similarity	NPD1283	Approved
0.6692	Remote Similarity	NPD4589	Approved
0.6691	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD6032	Approved
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2230	Approved
0.6667	Remote Similarity	NPD2228	Approved
0.6667	Remote Similarity	NPD2237	Approved
0.6667	Remote Similarity	NPD2232	Approved
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD6844	Discontinued
0.6667	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD4212	Discontinued
0.6667	Remote Similarity	NPD5303	Approved
0.6667	Remote Similarity	NPD2234	Approved
0.6667	Remote Similarity	NPD2229	Approved
0.6667	Remote Similarity	NPD2233	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.6667	Remote Similarity	NPD5304	Approved
0.6644	Remote Similarity	NPD4380	Phase 2
0.6644	Remote Similarity	NPD2534	Approved
0.6644	Remote Similarity	NPD2532	Approved
0.6644	Remote Similarity	NPD2533	Approved
0.6642	Remote Similarity	NPD1134	Approved
0.6642	Remote Similarity	NPD1131	Approved
0.6642	Remote Similarity	NPD1133	Approved
0.6642	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1135	Approved
0.6642	Remote Similarity	NPD1129	Approved
0.6641	Remote Similarity	NPD7636	Approved
0.6641	Remote Similarity	NPD3847	Discontinued
0.6639	Remote Similarity	NPD3134	Approved
0.6639	Remote Similarity	NPD3028	Approved
0.662	Remote Similarity	NPD5762	Approved
0.662	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5763	Approved
0.6619	Remote Similarity	NPD230	Phase 1
0.6619	Remote Similarity	NPD6355	Discontinued
0.6617	Remote Similarity	NPD4749	Approved
0.6615	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5585	Approved
0.6615	Remote Similarity	NPD4093	Discontinued
0.6614	Remote Similarity	NPD1791	Approved
0.6614	Remote Similarity	NPD9281	Approved
0.6614	Remote Similarity	NPD1793	Approved
0.6613	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.661	Remote Similarity	NPD9273	Approved
0.661	Remote Similarity	NPD9495	Approved
0.6604	Remote Similarity	NPD9294	Approved
0.6599	Remote Similarity	NPD6090	Discontinued
0.6597	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1510	Phase 2
0.6596	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3690	Phase 2

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