NPASS Compound

Structure

NPC91105 OpenBabel07101719242D 22 22 0 0 0 0 0 0 0 0999 V2000 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 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 5.1962 3.0000 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 -0.8660 -1.5000 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 -0.0000 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 -0.0000 -1.0000 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 -1.7321 -1.0000 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 0.8660 -2.5000 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.17
Volume:	330.67
LogP:	4.844
LogD:	3.249
LogS:	-3.265
# Rotatable Bonds:	6
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	2.85
Fsp3:	0.389
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:	-4.774
MDCK Permeability:	1.61599073180696e-05
Pgp-inhibitor:	0.603
Pgp-substrate:	0.13
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.124

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	99.11009216308594%
Volume Distribution (VD):	0.423
Pgp-substrate:	1.146916151046753%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.483
CYP2C19-inhibitor:	0.855
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.821
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.931
CYP2D6-substrate:	0.399
CYP3A4-inhibitor:	0.385
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	7.211
Half-life (T1/2):	0.678

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.483
Drug-inuced Liver Injury (DILI):	0.099
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.298
Skin Sensitization:	0.893
Carcinogencity:	0.092
Eye Corrosion:	0.004
Eye Irritation:	0.904
Respiratory Toxicity:	0.687

Download Data

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

Natural Product: NPC91105

Natural Product ID:	NPC91105
*Common Name:**	2,4,6-Trihydroxy-3-Geranylacetophenone
IUPAC Name:	1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4,6-trihydroxyphenyl]ethanone
Synonyms:
Standard InCHIKey:	RCOXTTLIGHDQHU-XYOKQWHBSA-N
Standard InCHI:	InChI=1S/C18H24O4/c1-11(2)6-5-7-12(3)8-9-14-15(20)10-16(21)17(13(4)19)18(14)22/h6,8,10,20-22H,5,7,9H2,1-4H3/b12-8+
SMILES:	CC(=CCC/C(=C/Cc1c(cc(c(C(=O)C)c1O)O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1242095
PubChem CID:	11808877
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
NPO16744	Melicope ptelefolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21958738]
NPO16744	Melicope ptelefolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
IC50	15
Others	19

Activity Type	# Activity
Cell Line	4
Individual Protein	20
NON-MOLECULAR	1
Organism	6
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	21000.0	nM	PMID[568324]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	20000.0	nM	PMID[568324]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	19000.0	nM	PMID[568324]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	19000.0	nM	PMID[568324]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	420.0	nM	PMID[568325]
NPT3806	Individual Protein	Arachidonate 5-lipoxygenase	Mus musculus	IC50	=	1800.0	nM	PMID[568325]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	6900.0	nM	PMID[568325]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	400.0	nM	PMID[568325]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	75.0	%	PMID[568325]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	60.0	%	PMID[568325]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	91.0	%	PMID[568325]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	102.0	%	PMID[568325]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	13.0	%	PMID[568325]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	6.0	%	PMID[568325]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	100.0	%	PMID[568325]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	28.0	%	PMID[568325]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	14.0	%	PMID[568325]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	-9.0	%	PMID[568325]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	-1.0	%	PMID[568325]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	-5.0	%	PMID[568325]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	<	50.0	%	PMID[568328]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	1400.0	nM	PMID[568328]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	1000.0	nM	PMID[568328]
NPT2	Others	Unspecified		IC50	=	20390.0	nM	PMID[568325]
NPT1	Others	Radical scavenging activity		IC50	=	46000.0	nM	PMID[568325]
NPT35	Others	n.a.		Ratio	=	1.0	n.a.	PMID[568326]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22500.0	nM	PMID[568326]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6600.0	nM	PMID[568327]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	32.0	%	PMID[568328]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	38.0	%	PMID[568328]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	5.0	10'6No_unit	PMID[568328]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	11.3	ng/ml	PMID[568328]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	57.3	ng/ml	PMID[568328]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	3500.0	nM	PMID[568328]

☑ 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 NPC91105 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	288
0.1-0.2	1538
0.2-0.3	4135
0.3-0.4	11983
0.4-0.5	7356
0.5-0.6	5621
0.6-0.7	6514
0.7-0.8	4106
0.8-0.85	833
0.85-0.9	227
0.9-0.95	63
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC65761
0.9914	High Similarity	NPC472029
0.9913	High Similarity	NPC215392
0.9826	High Similarity	NPC149246
0.9746	High Similarity	NPC475733
0.9664	High Similarity	NPC267846
0.9658	High Similarity	NPC309765
0.9583	High Similarity	NPC116513
0.9583	High Similarity	NPC162612
0.9583	High Similarity	NPC30501
0.9583	High Similarity	NPC23126
0.9583	High Similarity	NPC103356
0.9583	High Similarity	NPC169250
0.9583	High Similarity	NPC105157
0.9583	High Similarity	NPC190043
0.9583	High Similarity	NPC100067
0.9583	High Similarity	NPC98254
0.9583	High Similarity	NPC266689
0.9583	High Similarity	NPC72158
0.9573	High Similarity	NPC303737
0.9573	High Similarity	NPC226275
0.9569	High Similarity	NPC294037
0.9565	High Similarity	NPC209486
0.9565	High Similarity	NPC40649
0.9504	High Similarity	NPC21305
0.9504	High Similarity	NPC221777
0.9504	High Similarity	NPC473017
0.95	High Similarity	NPC62952
0.9487	High Similarity	NPC146642
0.9426	High Similarity	NPC474998
0.9316	High Similarity	NPC161617
0.931	High Similarity	NPC121259
0.9274	High Similarity	NPC475042
0.9256	High Similarity	NPC477454
0.9244	High Similarity	NPC242895
0.9244	High Similarity	NPC196976
0.918	High Similarity	NPC473691
0.918	High Similarity	NPC328983
0.9167	High Similarity	NPC32032
0.9167	High Similarity	NPC133909
0.916	High Similarity	NPC229649
0.9127	High Similarity	NPC40524
0.9127	High Similarity	NPC139074
0.9127	High Similarity	NPC213485
0.912	High Similarity	NPC275504
0.9113	High Similarity	NPC476119
0.9106	High Similarity	NPC316625
0.9106	High Similarity	NPC329205
0.9083	High Similarity	NPC115159
0.9083	High Similarity	NPC143427
0.9083	High Similarity	NPC45438
0.9083	High Similarity	NPC19174
0.9083	High Similarity	NPC224273
0.9083	High Similarity	NPC156139
0.9083	High Similarity	NPC73532
0.9083	High Similarity	NPC267552
0.9055	High Similarity	NPC166480
0.9055	High Similarity	NPC282780
0.9052	High Similarity	NPC118288
0.9052	High Similarity	NPC276111
0.9048	High Similarity	NPC175738
0.904	High Similarity	NPC84772
0.9032	High Similarity	NPC470981
0.9008	High Similarity	NPC66252
0.9008	High Similarity	NPC232708
0.9	High Similarity	NPC297186
0.8992	High Similarity	NPC188814
0.8992	High Similarity	NPC195262
0.8984	High Similarity	NPC61153
0.8984	High Similarity	NPC470210
0.8984	High Similarity	NPC130899
0.8984	High Similarity	NPC70859
0.8984	High Similarity	NPC283590
0.8976	High Similarity	NPC37299
0.8976	High Similarity	NPC180261
0.8968	High Similarity	NPC324482
0.896	High Similarity	NPC92624
0.896	High Similarity	NPC230818
0.8943	High Similarity	NPC10926
0.8917	High Similarity	NPC159525
0.8915	High Similarity	NPC191976
0.8915	High Similarity	NPC194764
0.8915	High Similarity	NPC131039
0.8915	High Similarity	NPC264112
0.8915	High Similarity	NPC13575
0.8915	High Similarity	NPC65005
0.8906	High Similarity	NPC475088
0.8898	High Similarity	NPC27490
0.8889	High Similarity	NPC247477
0.8889	High Similarity	NPC21378
0.8889	High Similarity	NPC259942
0.8889	High Similarity	NPC470987
0.8889	High Similarity	NPC17840
0.8871	High Similarity	NPC8745
0.8871	High Similarity	NPC473751
0.8862	High Similarity	NPC13238
0.8846	High Similarity	NPC168105
0.8846	High Similarity	NPC1486
0.8846	High Similarity	NPC249606
0.8846	High Similarity	NPC477244
0.8846	High Similarity	NPC98115
0.8846	High Similarity	NPC12165
0.8846	High Similarity	NPC174999
0.8846	High Similarity	NPC477243
0.8846	High Similarity	NPC25287
0.8846	High Similarity	NPC150399
0.8846	High Similarity	NPC274109
0.8846	High Similarity	NPC66349
0.8846	High Similarity	NPC477242
0.8846	High Similarity	NPC156910
0.8846	High Similarity	NPC186838
0.8846	High Similarity	NPC41461
0.8837	High Similarity	NPC290803
0.8837	High Similarity	NPC103842
0.8837	High Similarity	NPC164136
0.8833	High Similarity	NPC158222
0.8828	High Similarity	NPC267205
0.8828	High Similarity	NPC48036
0.8824	High Similarity	NPC230349
0.881	High Similarity	NPC109123
0.881	High Similarity	NPC69235
0.881	High Similarity	NPC212379
0.8803	High Similarity	NPC242136
0.88	High Similarity	NPC128428
0.88	High Similarity	NPC305518
0.879	High Similarity	NPC262671
0.879	High Similarity	NPC290466
0.879	High Similarity	NPC201728
0.878	High Similarity	NPC306288
0.8779	High Similarity	NPC153979
0.8779	High Similarity	NPC317119
0.8779	High Similarity	NPC472419
0.8769	High Similarity	NPC84699
0.8769	High Similarity	NPC118919
0.8769	High Similarity	NPC156092
0.876	High Similarity	NPC28753
0.876	High Similarity	NPC159623
0.876	High Similarity	NPC108113
0.876	High Similarity	NPC144051
0.876	High Similarity	NPC204960
0.876	High Similarity	NPC20560
0.876	High Similarity	NPC93756
0.876	High Similarity	NPC82225
0.876	High Similarity	NPC294593
0.876	High Similarity	NPC18877
0.876	High Similarity	NPC474519
0.875	High Similarity	NPC185624
0.875	High Similarity	NPC241089
0.875	High Similarity	NPC273282
0.875	High Similarity	NPC474890
0.875	High Similarity	NPC161943
0.874	High Similarity	NPC62219
0.8739	High Similarity	NPC83718
0.873	High Similarity	NPC41263
0.8712	High Similarity	NPC470671
0.8712	High Similarity	NPC21350
0.8712	High Similarity	NPC477056
0.8712	High Similarity	NPC474504
0.8712	High Similarity	NPC470669
0.8712	High Similarity	NPC138099
0.8712	High Similarity	NPC19622
0.8712	High Similarity	NPC474487
0.8712	High Similarity	NPC131130
0.8712	High Similarity	NPC470672
0.8712	High Similarity	NPC112789
0.8712	High Similarity	NPC162939
0.8712	High Similarity	NPC470668
0.8712	High Similarity	NPC243528
0.8712	High Similarity	NPC251681
0.8712	High Similarity	NPC477055
0.8712	High Similarity	NPC242994
0.8702	High Similarity	NPC471905
0.8702	High Similarity	NPC194579
0.8702	High Similarity	NPC44960
0.8702	High Similarity	NPC474110
0.8699	High Similarity	NPC218333
0.8692	High Similarity	NPC125920
0.8692	High Similarity	NPC286336
0.8692	High Similarity	NPC144027
0.8692	High Similarity	NPC236974
0.8682	High Similarity	NPC285054
0.8682	High Similarity	NPC203817
0.8682	High Similarity	NPC15834
0.8682	High Similarity	NPC215875
0.8682	High Similarity	NPC470988
0.8682	High Similarity	NPC10971
0.8661	High Similarity	NPC102829
0.8661	High Similarity	NPC120488
0.8647	High Similarity	NPC472366
0.8647	High Similarity	NPC216978
0.8647	High Similarity	NPC470211
0.8647	High Similarity	NPC169452
0.8647	High Similarity	NPC23257
0.8647	High Similarity	NPC181560
0.8647	High Similarity	NPC303633
0.8647	High Similarity	NPC96565
0.8647	High Similarity	NPC55018
0.8647	High Similarity	NPC477956
0.8647	High Similarity	NPC220062
0.8647	High Similarity	NPC301217

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 NPC91105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	979
0.2-0.3	1616
0.3-0.4	2894
0.4-0.5	1941
0.5-0.6	997
0.6-0.7	330
0.7-0.8	87
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8626	High Similarity	NPD1509	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1240	Approved
0.8462	Intermediate Similarity	NPD943	Approved
0.8394	Intermediate Similarity	NPD7390	Discontinued
0.8374	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1607	Approved
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1510	Phase 2
0.8201	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD6651	Approved
0.8088	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD1549	Phase 2
0.8017	Intermediate Similarity	NPD940	Approved
0.8017	Intermediate Similarity	NPD846	Approved
0.7971	Intermediate Similarity	NPD2800	Approved
0.7923	Intermediate Similarity	NPD1164	Approved
0.7917	Intermediate Similarity	NPD74	Approved
0.7917	Intermediate Similarity	NPD9266	Approved
0.7917	Intermediate Similarity	NPD4380	Phase 2
0.7899	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1201	Approved
0.7877	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7411	Suspended
0.784	Intermediate Similarity	NPD9493	Approved
0.7833	Intermediate Similarity	NPD9264	Approved
0.7833	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD9263	Approved
0.7833	Intermediate Similarity	NPD9267	Approved
0.7823	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2533	Approved
0.7817	Intermediate Similarity	NPD2532	Approved
0.7817	Intermediate Similarity	NPD2534	Approved
0.7786	Intermediate Similarity	NPD1470	Approved
0.7754	Intermediate Similarity	NPD5408	Approved
0.7754	Intermediate Similarity	NPD5406	Approved
0.7754	Intermediate Similarity	NPD2796	Approved
0.7754	Intermediate Similarity	NPD5404	Approved
0.7754	Intermediate Similarity	NPD2935	Discontinued
0.7754	Intermediate Similarity	NPD5405	Approved
0.7718	Intermediate Similarity	NPD7075	Discontinued
0.7692	Intermediate Similarity	NPD9269	Phase 2
0.7656	Intermediate Similarity	NPD9268	Approved
0.7635	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD7819	Suspended
0.7622	Intermediate Similarity	NPD1511	Approved
0.7622	Intermediate Similarity	NPD6799	Approved
0.7589	Intermediate Similarity	NPD2654	Approved
0.7589	Intermediate Similarity	NPD1243	Approved
0.7578	Intermediate Similarity	NPD9545	Approved
0.7568	Intermediate Similarity	NPD1934	Approved
0.7568	Intermediate Similarity	NPD6801	Discontinued
0.7559	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD9281	Approved
0.7535	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1512	Approved
0.7517	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD9261	Approved
0.7465	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD230	Phase 1
0.7451	Intermediate Similarity	NPD6959	Discontinued
0.7432	Intermediate Similarity	NPD6599	Discontinued
0.7429	Intermediate Similarity	NPD2799	Discontinued
0.7424	Intermediate Similarity	NPD9717	Approved
0.7419	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4750	Phase 3
0.7417	Intermediate Similarity	NPD7768	Phase 2
0.7417	Intermediate Similarity	NPD3882	Suspended
0.7413	Intermediate Similarity	NPD3750	Approved
0.7403	Intermediate Similarity	NPD6232	Discontinued
0.7372	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7473	Discontinued
0.7368	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2344	Approved
0.7288	Intermediate Similarity	NPD1809	Phase 2
0.7278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1203	Approved
0.7255	Intermediate Similarity	NPD3749	Approved
0.7254	Intermediate Similarity	NPD1551	Phase 2
0.723	Intermediate Similarity	NPD920	Approved
0.7211	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD2798	Approved
0.7197	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6166	Phase 2
0.7192	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5953	Discontinued
0.717	Intermediate Similarity	NPD7286	Phase 2
0.7143	Intermediate Similarity	NPD2859	Approved
0.7143	Intermediate Similarity	NPD2860	Approved
0.7133	Intermediate Similarity	NPD6099	Approved
0.7133	Intermediate Similarity	NPD6100	Approved
0.7124	Intermediate Similarity	NPD3817	Phase 2
0.7123	Intermediate Similarity	NPD2309	Approved
0.7122	Intermediate Similarity	NPD2313	Discontinued
0.7119	Intermediate Similarity	NPD845	Approved
0.7099	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD422	Phase 1
0.7075	Intermediate Similarity	NPD3300	Phase 2
0.707	Intermediate Similarity	NPD5710	Approved
0.707	Intermediate Similarity	NPD5711	Approved
0.7068	Intermediate Similarity	NPD2932	Approved
0.7068	Intermediate Similarity	NPD3019	Approved
0.7063	Intermediate Similarity	NPD6020	Phase 2
0.7063	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3748	Approved
0.7059	Intermediate Similarity	NPD2933	Approved
0.7059	Intermediate Similarity	NPD2934	Approved
0.7055	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5494	Approved
0.7049	Intermediate Similarity	NPD1242	Phase 1
0.7037	Intermediate Similarity	NPD3972	Approved
0.7019	Intermediate Similarity	NPD7074	Phase 3
0.7	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD3268	Approved
0.7	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD3764	Approved
0.6978	Remote Similarity	NPD6832	Phase 2
0.6968	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3020	Approved
0.6957	Remote Similarity	NPD7054	Approved
0.695	Remote Similarity	NPD520	Approved
0.6933	Remote Similarity	NPD6559	Discontinued
0.6917	Remote Similarity	NPD1759	Phase 1
0.6917	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7472	Approved
0.6914	Remote Similarity	NPD1729	Discontinued
0.6908	Remote Similarity	NPD3226	Approved
0.6899	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2797	Approved
0.6879	Remote Similarity	NPD411	Approved
0.6879	Remote Similarity	NPD919	Approved
0.6879	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6797	Phase 2
0.6867	Remote Similarity	NPD5401	Approved
0.686	Remote Similarity	NPD844	Approved
0.6853	Remote Similarity	NPD447	Suspended
0.6849	Remote Similarity	NPD2346	Discontinued
0.6842	Remote Similarity	NPD1758	Phase 1
0.6838	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7251	Discontinued
0.6828	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4628	Phase 3
0.6824	Remote Similarity	NPD3400	Discontinued
0.6818	Remote Similarity	NPD256	Approved
0.6818	Remote Similarity	NPD255	Approved
0.6797	Remote Similarity	NPD7458	Discontinued
0.6795	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1247	Approved
0.6788	Remote Similarity	NPD7808	Phase 3
0.6776	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1296	Phase 2
0.6748	Remote Similarity	NPD5844	Phase 1
0.6746	Remote Similarity	NPD1237	Approved
0.6739	Remote Similarity	NPD1755	Approved
0.6738	Remote Similarity	NPD4908	Phase 1
0.6736	Remote Similarity	NPD5124	Phase 1
0.6736	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD111	Approved
0.6714	Remote Similarity	NPD1019	Discontinued
0.6712	Remote Similarity	NPD4308	Phase 3
0.6712	Remote Similarity	NPD7033	Discontinued
0.6711	Remote Similarity	NPD7003	Approved
0.6708	Remote Similarity	NPD3926	Phase 2
0.6691	Remote Similarity	NPD4626	Approved
0.6688	Remote Similarity	NPD5402	Approved
0.6687	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4360	Phase 2
0.6686	Remote Similarity	NPD4363	Phase 3
0.6667	Remote Similarity	NPD1930	Approved
0.6667	Remote Similarity	NPD1929	Approved
0.6667	Remote Similarity	NPD288	Approved
0.6667	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4208	Discontinued
0.6667	Remote Similarity	NPD1548	Phase 1
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD1241	Discontinued
0.6647	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4361	Phase 2
0.6643	Remote Similarity	NPD3267	Approved
0.6643	Remote Similarity	NPD3266	Approved
0.6642	Remote Similarity	NPD3023	Approved
0.6642	Remote Similarity	NPD3026	Approved
0.664	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6104	Discontinued
0.6624	Remote Similarity	NPD1465	Phase 2
0.662	Remote Similarity	NPD4207	Discontinued
0.6619	Remote Similarity	NPD4749	Approved
0.6618	Remote Similarity	NPD3025	Approved
0.6618	Remote Similarity	NPD3024	Approved
0.6617	Remote Similarity	NPD5951	Approved
0.6615	Remote Similarity	NPD3022	Approved
0.6615	Remote Similarity	NPD3021	Approved
0.6609	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD1610	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