NPASS Compound

Structure

CID65761 OpenBabel06191715402D 24 24 0 0 0 0 0 0 0 0999 V2000 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 7.0000 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 1.7321 -3.0000 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 4.5000 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 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 1.7321 1.0000 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 1.7321 -2.0000 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 1.0000 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 1.7321 -0.0000 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 -1.5000 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 12 2 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 13 19 1 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	365.262
LogP:	5.508
LogD:	3.94
LogS:	-3.586
# Rotatable Bonds:	7
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.491
Synthetic Accessibility Score:	2.961
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.781
MDCK Permeability:	1.8371834812569432e-05
Pgp-inhibitor:	0.714
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.078

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	100.01905822753906%
Volume Distribution (VD):	0.832
Pgp-substrate:	1.0249121189117432%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.549
CYP2C19-inhibitor:	0.836
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.871
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.944
CYP2D6-substrate:	0.48
CYP3A4-inhibitor:	0.432
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	6.097
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.402
Drug-inuced Liver Injury (DILI):	0.361
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.235
Skin Sensitization:	0.899
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.833
Respiratory Toxicity:	0.79

Download Data

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

Natural Product: NPC65761

Natural Product ID:	NPC65761
*Common Name:**	3-Geranyl-1-(3-Methylbutanoyl)-Phloroglucinol
IUPAC Name:	1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4,6-trihydroxyphenyl]-2-methylpropan-1-one
Synonyms:
Standard InCHIKey:	TXDNBNXWWCEVMG-NTEUORMPSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-12(2)7-6-8-14(5)9-10-15-16(21)11-17(22)18(20(15)24)19(23)13(3)4/h7,9,11,13,21-22,24H,6,8,10H2,1-5H3/b14-9+
SMILES:	C/C(=CCc1c(O)cc(c(c1O)C(=O)C(C)C)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524326
PubChem CID:	10426888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15165152]
NPO7800	Hypericum jovis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217276]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24930002]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26358281]
NPO40851	Garcinia dauphinensis	Species	Clusiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30354100]
NPO30921	Hypericum roeperianum	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[8862040]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2000	Helichrysum stenopterum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7800	Hypericum jovis	Species	Hypericaceae	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
EC50	1
IC50	8
MIC	6
Others	12

Activity Type	# Activity
Cell Line	4
Individual Protein	2
NON-MOLECULAR	5
Organism	6
Others	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25	Cell Line	MT4	Homo sapiens	CC50	>	100000.0	nM	PMID[504182]
NPT306	Cell Line	PC-3	Homo sapiens	GI	<	20.0	%	PMID[504182]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	6000000.0	nM	PMID[504184]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	29900000.0	nM	PMID[504184]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	16400.0	nM	PMID[504185]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.1	mM	PMID[504179]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.96	mM	PMID[504179]
NPT2	Others	Unspecified		Activity	=	79.4	%	PMID[504180]
NPT2	Others	Unspecified		Activity	=	50.8	%	PMID[504180]
NPT35	Others	n.a.		Ratio	=	0.8	n.a.	PMID[504181]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21000.0	nM	PMID[504181]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[504182]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	1.0	ug.mL-1	PMID[504182]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	1.0	ug.mL-1	PMID[504182]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	1.0	ug.mL-1	PMID[504182]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	Activity	=	0.7	%	PMID[504182]
NPT610	Others	Molecular identity unknown		MIC	=	1.0	ug.mL-1	PMID[504183]
NPT610	Others	Molecular identity unknown		MIC	=	1.7	ug.mL-1	PMID[504183]
NPT2	Others	Unspecified		Selectivity Index	=	13.2	n.a.	PMID[504183]
NPT2	Others	Unspecified		Selectivity Index	=	14.4	n.a.	PMID[504183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22.5	ug.mL-1	PMID[504183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24.5	ug.mL-1	PMID[504183]
NPT610	Others	Molecular identity unknown		GI	>	50.0	%	PMID[504183]
NPT2	Others	Unspecified		IC50	=	2200000.0	nM	PMID[504184]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	12500.0	nM	PMID[504185]

☑ 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 NPC65761 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	294
0.1-0.2	1484
0.2-0.3	3932
0.3-0.4	11484
0.4-0.5	8049
0.5-0.6	5553
0.6-0.7	6694
0.7-0.8	4096
0.8-0.85	827
0.85-0.9	203
0.9-0.95	62
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472029
0.9914	High Similarity	NPC91105
0.9831	High Similarity	NPC475733
0.9828	High Similarity	NPC215392
0.9741	High Similarity	NPC149246
0.9655	High Similarity	NPC294037
0.9587	High Similarity	NPC473017
0.9583	High Similarity	NPC267846
0.9576	High Similarity	NPC309765
0.9573	High Similarity	NPC146642
0.9504	High Similarity	NPC162612
0.9504	High Similarity	NPC30501
0.9504	High Similarity	NPC72158
0.9504	High Similarity	NPC266689
0.9504	High Similarity	NPC169250
0.9504	High Similarity	NPC23126
0.9504	High Similarity	NPC105157
0.9504	High Similarity	NPC103356
0.9504	High Similarity	NPC98254
0.9504	High Similarity	NPC190043
0.9504	High Similarity	NPC100067
0.9504	High Similarity	NPC116513
0.9492	High Similarity	NPC226275
0.9492	High Similarity	NPC303737
0.9483	High Similarity	NPC209486
0.9483	High Similarity	NPC40649
0.9426	High Similarity	NPC221777
0.9426	High Similarity	NPC21305
0.9421	High Similarity	NPC62952
0.935	High Similarity	NPC474998
0.9237	High Similarity	NPC161617
0.9231	High Similarity	NPC121259
0.92	High Similarity	NPC475042
0.918	High Similarity	NPC477454
0.9167	High Similarity	NPC242895
0.9167	High Similarity	NPC196976
0.9127	High Similarity	NPC175738
0.9106	High Similarity	NPC473691
0.9106	High Similarity	NPC328983
0.9091	High Similarity	NPC32032
0.9091	High Similarity	NPC133909
0.9083	High Similarity	NPC229649
0.9055	High Similarity	NPC213485
0.9055	High Similarity	NPC40524
0.9055	High Similarity	NPC139074
0.9048	High Similarity	NPC275504
0.9048	High Similarity	NPC324482
0.904	High Similarity	NPC476119
0.9032	High Similarity	NPC329205
0.9032	High Similarity	NPC316625
0.9008	High Similarity	NPC45438
0.9008	High Similarity	NPC143427
0.9008	High Similarity	NPC73532
0.9008	High Similarity	NPC19174
0.9008	High Similarity	NPC267552
0.9008	High Similarity	NPC224273
0.9008	High Similarity	NPC156139
0.9008	High Similarity	NPC115159
0.8984	High Similarity	NPC282780
0.8984	High Similarity	NPC475088
0.8984	High Similarity	NPC166480
0.8976	High Similarity	NPC27490
0.8974	High Similarity	NPC118288
0.8974	High Similarity	NPC276111
0.8968	High Similarity	NPC84772
0.896	High Similarity	NPC470981
0.8934	High Similarity	NPC66252
0.8934	High Similarity	NPC232708
0.8926	High Similarity	NPC297186
0.8923	High Similarity	NPC156910
0.8917	High Similarity	NPC195262
0.8917	High Similarity	NPC188814
0.8915	High Similarity	NPC70859
0.8915	High Similarity	NPC290803
0.8915	High Similarity	NPC61153
0.8915	High Similarity	NPC130899
0.8915	High Similarity	NPC470210
0.8915	High Similarity	NPC283590
0.8906	High Similarity	NPC180261
0.8906	High Similarity	NPC37299
0.8889	High Similarity	NPC109123
0.8889	High Similarity	NPC69235
0.8889	High Similarity	NPC212379
0.8889	High Similarity	NPC92624
0.8889	High Similarity	NPC230818
0.8871	High Similarity	NPC10926
0.8862	High Similarity	NPC306288
0.8855	High Similarity	NPC153979
0.8846	High Similarity	NPC65005
0.8846	High Similarity	NPC13575
0.8846	High Similarity	NPC191976
0.8846	High Similarity	NPC194764
0.8846	High Similarity	NPC264112
0.8846	High Similarity	NPC131039
0.8843	High Similarity	NPC159525
0.8828	High Similarity	NPC185624
0.8819	High Similarity	NPC17840
0.8819	High Similarity	NPC470987
0.8819	High Similarity	NPC247477
0.8819	High Similarity	NPC259942
0.8819	High Similarity	NPC21378
0.88	High Similarity	NPC8745
0.88	High Similarity	NPC473751
0.879	High Similarity	NPC13238
0.8788	High Similarity	NPC474504
0.8788	High Similarity	NPC470672
0.8788	High Similarity	NPC470671
0.8788	High Similarity	NPC470668
0.8788	High Similarity	NPC470669
0.8788	High Similarity	NPC474487
0.8788	High Similarity	NPC162939
0.878	High Similarity	NPC218333
0.8779	High Similarity	NPC1486
0.8779	High Similarity	NPC477244
0.8779	High Similarity	NPC168105
0.8779	High Similarity	NPC98115
0.8779	High Similarity	NPC150399
0.8779	High Similarity	NPC66349
0.8779	High Similarity	NPC174999
0.8779	High Similarity	NPC41461
0.8779	High Similarity	NPC25287
0.8779	High Similarity	NPC477243
0.8779	High Similarity	NPC249606
0.8779	High Similarity	NPC274109
0.8779	High Similarity	NPC477242
0.8779	High Similarity	NPC12165
0.8779	High Similarity	NPC186838
0.8769	High Similarity	NPC164136
0.8769	High Similarity	NPC103842
0.8769	High Similarity	NPC236974
0.8769	High Similarity	NPC144027
0.876	High Similarity	NPC285054
0.876	High Similarity	NPC267205
0.876	High Similarity	NPC470988
0.876	High Similarity	NPC158222
0.876	High Similarity	NPC48036
0.875	High Similarity	NPC230349
0.873	High Similarity	NPC305518
0.873	High Similarity	NPC128428
0.8729	High Similarity	NPC242136
0.8722	High Similarity	NPC169452
0.8722	High Similarity	NPC477956
0.8722	High Similarity	NPC181560
0.872	High Similarity	NPC262671
0.872	High Similarity	NPC290466
0.872	High Similarity	NPC201728
0.8712	High Similarity	NPC473622
0.8712	High Similarity	NPC472419
0.8712	High Similarity	NPC317119
0.8702	High Similarity	NPC84699
0.8702	High Similarity	NPC474726
0.8702	High Similarity	NPC475955
0.8702	High Similarity	NPC156092
0.8702	High Similarity	NPC118919
0.8692	High Similarity	NPC18877
0.8692	High Similarity	NPC294593
0.8692	High Similarity	NPC470984
0.8692	High Similarity	NPC20560
0.8692	High Similarity	NPC82225
0.8692	High Similarity	NPC159623
0.8692	High Similarity	NPC108113
0.8692	High Similarity	NPC144051
0.8692	High Similarity	NPC28753
0.8692	High Similarity	NPC93756
0.8692	High Similarity	NPC204960
0.8692	High Similarity	NPC474519
0.8678	High Similarity	NPC474890
0.8678	High Similarity	NPC161943
0.8678	High Similarity	NPC273282
0.8678	High Similarity	NPC241089
0.8672	High Similarity	NPC62219
0.8667	High Similarity	NPC83718
0.8661	High Similarity	NPC41263
0.8657	High Similarity	NPC477272
0.8647	High Similarity	NPC243528
0.8647	High Similarity	NPC477055
0.8647	High Similarity	NPC138099
0.8647	High Similarity	NPC477056
0.8647	High Similarity	NPC21350
0.8647	High Similarity	NPC251681
0.8647	High Similarity	NPC242994
0.8647	High Similarity	NPC112789
0.8647	High Similarity	NPC131130
0.8647	High Similarity	NPC19622
0.8636	High Similarity	NPC44960
0.8636	High Similarity	NPC474110
0.8636	High Similarity	NPC213603
0.8636	High Similarity	NPC470397
0.8636	High Similarity	NPC187826
0.8636	High Similarity	NPC470398
0.8636	High Similarity	NPC194579
0.8636	High Similarity	NPC471905
0.8626	High Similarity	NPC286336
0.8626	High Similarity	NPC125920
0.8615	High Similarity	NPC10971
0.8615	High Similarity	NPC215875
0.8615	High Similarity	NPC15834
0.8615	High Similarity	NPC203817
0.8594	High Similarity	NPC102829
0.8594	High Similarity	NPC73203

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 NPC65761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	957
0.2-0.3	1621
0.3-0.4	2880
0.4-0.5	1960
0.5-0.6	1025
0.6-0.7	313
0.7-0.8	88
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8561	High Similarity	NPD1509	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD943	Approved
0.8397	Intermediate Similarity	NPD1240	Approved
0.8333	Intermediate Similarity	NPD7390	Discontinued
0.8306	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD1607	Approved
0.8271	Intermediate Similarity	NPD6651	Approved
0.8148	Intermediate Similarity	NPD1510	Phase 2
0.8143	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1549	Phase 2
0.7949	Intermediate Similarity	NPD846	Approved
0.7949	Intermediate Similarity	NPD940	Approved
0.7914	Intermediate Similarity	NPD2800	Approved
0.7891	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD1164	Approved
0.7862	Intermediate Similarity	NPD4380	Phase 2
0.7851	Intermediate Similarity	NPD9266	Approved
0.7851	Intermediate Similarity	NPD74	Approved
0.7829	Intermediate Similarity	NPD1201	Approved
0.7823	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD9493	Approved
0.7769	Intermediate Similarity	NPD9267	Approved
0.7769	Intermediate Similarity	NPD9264	Approved
0.7769	Intermediate Similarity	NPD9263	Approved
0.7769	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD2534	Approved
0.7762	Intermediate Similarity	NPD2532	Approved
0.7762	Intermediate Similarity	NPD2533	Approved
0.7727	Intermediate Similarity	NPD1470	Approved
0.7698	Intermediate Similarity	NPD5408	Approved
0.7698	Intermediate Similarity	NPD2935	Discontinued
0.7698	Intermediate Similarity	NPD5405	Approved
0.7698	Intermediate Similarity	NPD5406	Approved
0.7698	Intermediate Similarity	NPD2796	Approved
0.7698	Intermediate Similarity	NPD5404	Approved
0.7667	Intermediate Similarity	NPD7075	Discontinued
0.7634	Intermediate Similarity	NPD9269	Phase 2
0.7597	Intermediate Similarity	NPD9268	Approved
0.7584	Intermediate Similarity	NPD7819	Suspended
0.7584	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6799	Approved
0.7569	Intermediate Similarity	NPD1511	Approved
0.7535	Intermediate Similarity	NPD1243	Approved
0.7535	Intermediate Similarity	NPD2654	Approved
0.7519	Intermediate Similarity	NPD9545	Approved
0.7517	Intermediate Similarity	NPD1934	Approved
0.7517	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9281	Approved
0.7467	Intermediate Similarity	NPD2801	Approved
0.7466	Intermediate Similarity	NPD1512	Approved
0.7438	Intermediate Similarity	NPD9261	Approved
0.7436	Intermediate Similarity	NPD7473	Discontinued
0.7413	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD230	Phase 1
0.7403	Intermediate Similarity	NPD6959	Discontinued
0.7383	Intermediate Similarity	NPD6599	Discontinued
0.7372	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3882	Suspended
0.7368	Intermediate Similarity	NPD9717	Approved
0.7368	Intermediate Similarity	NPD7768	Phase 2
0.7361	Intermediate Similarity	NPD3750	Approved
0.7355	Intermediate Similarity	NPD6232	Discontinued
0.732	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2798	Approved
0.7279	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2344	Approved
0.7233	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1809	Phase 2
0.7208	Intermediate Similarity	NPD3749	Approved
0.7206	Intermediate Similarity	NPD1203	Approved
0.7203	Intermediate Similarity	NPD6100	Approved
0.7203	Intermediate Similarity	NPD6099	Approved
0.7203	Intermediate Similarity	NPD845	Approved
0.7203	Intermediate Similarity	NPD1551	Phase 2
0.7181	Intermediate Similarity	NPD920	Approved
0.716	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6166	Phase 2
0.7152	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD3019	Approved
0.7143	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3300	Phase 2
0.7125	Intermediate Similarity	NPD6020	Phase 2
0.7125	Intermediate Similarity	NPD7286	Phase 2
0.7123	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5494	Approved
0.7083	Intermediate Similarity	NPD2860	Approved
0.7083	Intermediate Similarity	NPD2859	Approved
0.7078	Intermediate Similarity	NPD3817	Phase 2
0.7075	Intermediate Similarity	NPD2309	Approved
0.7071	Intermediate Similarity	NPD2313	Discontinued
0.7071	Intermediate Similarity	NPD3268	Approved
0.7049	Intermediate Similarity	NPD3020	Approved
0.7047	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD422	Phase 1
0.7025	Intermediate Similarity	NPD5710	Approved
0.7025	Intermediate Similarity	NPD5711	Approved
0.7014	Intermediate Similarity	NPD3748	Approved
0.7008	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2934	Approved
0.7	Intermediate Similarity	NPD2933	Approved
0.6992	Remote Similarity	NPD1242	Phase 1
0.6985	Remote Similarity	NPD3972	Approved
0.6975	Remote Similarity	NPD7074	Phase 3
0.6957	Remote Similarity	NPD3818	Discontinued
0.6957	Remote Similarity	NPD2797	Approved
0.6954	Remote Similarity	NPD5403	Approved
0.695	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3764	Approved
0.6929	Remote Similarity	NPD6832	Phase 2
0.6923	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7054	Approved
0.6901	Remote Similarity	NPD520	Approved
0.6897	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6559	Discontinued
0.6871	Remote Similarity	NPD1729	Discontinued
0.6871	Remote Similarity	NPD7472	Approved
0.6866	Remote Similarity	NPD1759	Phase 1
0.6863	Remote Similarity	NPD7458	Discontinued
0.6863	Remote Similarity	NPD3226	Approved
0.686	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD919	Approved
0.6831	Remote Similarity	NPD411	Approved
0.6829	Remote Similarity	NPD6797	Phase 2
0.6821	Remote Similarity	NPD5401	Approved
0.6809	Remote Similarity	NPD4908	Phase 1
0.6806	Remote Similarity	NPD447	Suspended
0.6806	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5124	Phase 1
0.6803	Remote Similarity	NPD2346	Discontinued
0.6803	Remote Similarity	NPD844	Approved
0.6791	Remote Similarity	NPD1758	Phase 1
0.6788	Remote Similarity	NPD7251	Discontinued
0.6788	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4628	Phase 3
0.6779	Remote Similarity	NPD3400	Discontinued
0.6779	Remote Similarity	NPD7003	Approved
0.6767	Remote Similarity	NPD255	Approved
0.6767	Remote Similarity	NPD256	Approved
0.675	Remote Similarity	NPD1247	Approved
0.6748	Remote Similarity	NPD288	Approved
0.6747	Remote Similarity	NPD7808	Phase 3
0.6746	Remote Similarity	NPD1930	Approved
0.6746	Remote Similarity	NPD1929	Approved
0.6746	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4363	Phase 3
0.6744	Remote Similarity	NPD4360	Phase 2
0.6742	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3026	Approved
0.6715	Remote Similarity	NPD3023	Approved
0.6714	Remote Similarity	NPD3266	Approved
0.6714	Remote Similarity	NPD3267	Approved
0.6713	Remote Similarity	NPD1296	Phase 2
0.6707	Remote Similarity	NPD5844	Phase 1
0.6705	Remote Similarity	NPD4361	Phase 2
0.6705	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1237	Approved
0.6692	Remote Similarity	NPD3022	Approved
0.6692	Remote Similarity	NPD3021	Approved
0.6691	Remote Similarity	NPD1755	Approved
0.6691	Remote Similarity	NPD3025	Approved
0.6691	Remote Similarity	NPD3024	Approved
0.6691	Remote Similarity	NPD4749	Approved
0.6667	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1019	Discontinued
0.6647	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5402	Approved
0.6643	Remote Similarity	NPD1876	Approved
0.6642	Remote Similarity	NPD4626	Approved
0.6626	Remote Similarity	NPD2403	Approved
0.662	Remote Similarity	NPD9494	Approved
0.662	Remote Similarity	NPD4208	Discontinued
0.6619	Remote Similarity	NPD1608	Approved
0.6618	Remote Similarity	NPD1548	Phase 1
0.6617	Remote Similarity	NPD1241	Discontinued
0.6587	Remote Similarity	NPD6104	Discontinued
0.6587	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1465	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