NPASS Compound

Structure

CID246967 OpenBabel06191716052D 30 30 0 0 0 0 0 0 0 0999 V2000 -2.5981 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -8.5000 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 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 -0.8660 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 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 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -8.5000 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 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 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 -1.7321 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -9.0000 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 -0.0000 -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 1.7321 -1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 20 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 30 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 21 2 0 0 0 0 13 22 1 0 0 0 0 14 22 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 17 24 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 24 27 1 0 0 0 0 25 28 1 0 0 0 0 26 27 2 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.3
Volume:	474.907
LogP:	7.153
LogD:	5.437
LogS:	-3.614
# Rotatable Bonds:	12
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	3.089
Fsp3:	0.481
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.952
MDCK Permeability:	2.4789025701466016e-05
Pgp-inhibitor:	0.291
Pgp-substrate:	0.19
Human Intestinal Absorption (HIA):	0.289
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	96.70650482177734%
Volume Distribution (VD):	1.29
Pgp-substrate:	1.0398509502410889%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.71
CYP2C19-substrate:	0.222
CYP2C9-inhibitor:	0.735
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.96
CYP2D6-substrate:	0.735
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	5.732
Half-life (T1/2):	0.599

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.003
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.968
Carcinogencity:	0.016
Eye Corrosion:	0.013
Eye Irritation:	0.901
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC246967

Natural Product ID:	NPC246967
*Common Name:**	6-Geranylgeranyl-2,4-Dihydroxy-1-Methoxybenzene
IUPAC Name:	4-methoxy-5-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	IYYFMQHGUZBMKD-MLAGYPMBSA-N
Standard InCHI:	InChI=1S/C27H40O3/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-15-23(5)16-17-24-18-25(28)19-26(29)27(24)30-6/h10,12,14,16,18-19,28-29H,7-9,11,13,15,17H2,1-6H3/b21-12+,22-14+,23-16+
SMILES:	CC(=CCC/C(=C/CC/C(=C/CC/C(=C/Cc1cc(cc(c1OC)O)O)/C)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484444
PubChem CID:	14487957
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
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575963]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1294697]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607355]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2809609]
NPO17408	Derris amazonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17795	Corydalis montana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17408	Derris amazonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17408	Derris amazonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19221	Echinopsis terscheckii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19582	Sarothamnus patens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18683	Diospyros cornii	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2678	Synadenium pereskiifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19025	Pemphis acidula	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17795	Corydalis montana	Species	Papaveraceae	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
IC50	3
MIC	8

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[533174]
NPT168	Cell Line	P388	Mus musculus	IC50	=	2.1	ug.mL-1	PMID[533174]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[533173]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[533173]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	>	100.0	ug.mL-1	PMID[533173]
NPT4678	Organism	Hafnia alvei	Hafnia alvei	MIC	>	100.0	ug.mL-1	PMID[533173]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	100.0	ug.mL-1	PMID[533173]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	6.25	ug.mL-1	PMID[533173]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1.56	ug.mL-1	PMID[533173]
NPT1843	Organism	Aeromonas hydrophila	Aeromonas hydrophila	MIC	=	0.78	ug.mL-1	PMID[533173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.2	ug.mL-1	PMID[533174]

☑ 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 NPC246967 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	354
0.1-0.2	1690
0.2-0.3	6017
0.3-0.4	13799
0.4-0.5	3761
0.5-0.6	5334
0.6-0.7	7964
0.7-0.8	3074
0.8-0.85	468
0.85-0.9	208
0.9-0.95	23
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC135414
0.9664	High Similarity	NPC112596
0.9658	High Similarity	NPC474864
0.9426	High Similarity	NPC158477
0.935	High Similarity	NPC220935
0.9344	High Similarity	NPC266691
0.9339	High Similarity	NPC245060
0.9333	High Similarity	NPC183446
0.9268	High Similarity	NPC58164
0.9268	High Similarity	NPC10225
0.9244	High Similarity	NPC285289
0.9231	High Similarity	NPC474612
0.9194	High Similarity	NPC51840
0.9194	High Similarity	NPC311680
0.9194	High Similarity	NPC234488
0.9194	High Similarity	NPC299221
0.912	High Similarity	NPC12275
0.912	High Similarity	NPC147317
0.912	High Similarity	NPC232275
0.912	High Similarity	NPC82503
0.912	High Similarity	NPC474356
0.912	High Similarity	NPC45715
0.9106	High Similarity	NPC216836
0.9098	High Similarity	NPC234400
0.9098	High Similarity	NPC60885
0.9091	High Similarity	NPC121115
0.9091	High Similarity	NPC95168
0.9048	High Similarity	NPC6451
0.904	High Similarity	NPC214860
0.9032	High Similarity	NPC19694
0.9024	High Similarity	NPC18924
0.9024	High Similarity	NPC476006
0.9024	High Similarity	NPC214406
0.9024	High Similarity	NPC103823
0.9024	High Similarity	NPC44748
0.9024	High Similarity	NPC28730
0.9024	High Similarity	NPC78974
0.9024	High Similarity	NPC223136
0.8992	High Similarity	NPC20674
0.8976	High Similarity	NPC474810
0.896	High Similarity	NPC45824
0.896	High Similarity	NPC190144
0.8952	High Similarity	NPC236760
0.8952	High Similarity	NPC169474
0.8952	High Similarity	NPC82679
0.8952	High Similarity	NPC246620
0.8952	High Similarity	NPC293054
0.8952	High Similarity	NPC124452
0.8952	High Similarity	NPC324112
0.8952	High Similarity	NPC252131
0.8952	High Similarity	NPC159968
0.8952	High Similarity	NPC236791
0.8952	High Similarity	NPC282000
0.8952	High Similarity	NPC74817
0.8943	High Similarity	NPC299584
0.8943	High Similarity	NPC265483
0.8943	High Similarity	NPC82483
0.8934	High Similarity	NPC220598
0.8934	High Similarity	NPC165375
0.8926	High Similarity	NPC75713
0.8926	High Similarity	NPC49341
0.8906	High Similarity	NPC103967
0.8898	High Similarity	NPC193067
0.8889	High Similarity	NPC224157
0.8889	High Similarity	NPC192687
0.888	High Similarity	NPC28765
0.8852	High Similarity	NPC270326
0.8852	High Similarity	NPC41562
0.8837	High Similarity	NPC255147
0.8837	High Similarity	NPC261873
0.8837	High Similarity	NPC283009
0.8837	High Similarity	NPC201357
0.8837	High Similarity	NPC472337
0.8837	High Similarity	NPC134968
0.8837	High Similarity	NPC252095
0.8837	High Similarity	NPC281521
0.8833	High Similarity	NPC308217
0.8828	High Similarity	NPC37196
0.8828	High Similarity	NPC94236
0.8824	High Similarity	NPC259638
0.8824	High Similarity	NPC52464
0.8824	High Similarity	NPC304208
0.8819	High Similarity	NPC142530
0.881	High Similarity	NPC212015
0.88	High Similarity	NPC50368
0.8793	High Similarity	NPC195873
0.879	High Similarity	NPC233410
0.879	High Similarity	NPC193544
0.879	High Similarity	NPC472093
0.879	High Similarity	NPC105925
0.879	High Similarity	NPC17943
0.879	High Similarity	NPC117214
0.879	High Similarity	NPC208950
0.879	High Similarity	NPC203133
0.879	High Similarity	NPC298757
0.879	High Similarity	NPC116907
0.879	High Similarity	NPC221077
0.879	High Similarity	NPC57490
0.879	High Similarity	NPC251855
0.879	High Similarity	NPC475169
0.878	High Similarity	NPC197757
0.878	High Similarity	NPC228922
0.8779	High Similarity	NPC19869
0.8769	High Similarity	NPC472336
0.8769	High Similarity	NPC114155
0.8769	High Similarity	NPC300846
0.8769	High Similarity	NPC476639
0.8769	High Similarity	NPC472334
0.876	High Similarity	NPC106215
0.875	High Similarity	NPC161203
0.875	High Similarity	NPC218884
0.875	High Similarity	NPC127624
0.874	High Similarity	NPC126836
0.873	High Similarity	NPC63179
0.873	High Similarity	NPC154866
0.872	High Similarity	NPC76451
0.8702	High Similarity	NPC105493
0.8702	High Similarity	NPC474282
0.8702	High Similarity	NPC201145
0.8702	High Similarity	NPC103976
0.8702	High Similarity	NPC6262
0.8702	High Similarity	NPC326797
0.8702	High Similarity	NPC107551
0.8702	High Similarity	NPC276490
0.8702	High Similarity	NPC272157
0.8702	High Similarity	NPC102904
0.8702	High Similarity	NPC176051
0.8702	High Similarity	NPC90615
0.8702	High Similarity	NPC73535
0.8702	High Similarity	NPC25111
0.8699	High Similarity	NPC473411
0.8699	High Similarity	NPC71579
0.8699	High Similarity	NPC262253
0.8682	High Similarity	NPC168059
0.8682	High Similarity	NPC269528
0.8682	High Similarity	NPC229442
0.8672	High Similarity	NPC470096
0.8672	High Similarity	NPC469907
0.8672	High Similarity	NPC470095
0.8661	High Similarity	NPC476968
0.8661	High Similarity	NPC170844
0.8651	High Similarity	NPC210355
0.8651	High Similarity	NPC127587
0.8651	High Similarity	NPC266555
0.864	High Similarity	NPC33654
0.8636	High Similarity	NPC79622
0.8636	High Similarity	NPC29868
0.8636	High Similarity	NPC6369
0.8636	High Similarity	NPC212942
0.8636	High Similarity	NPC292882
0.8636	High Similarity	NPC127218
0.8636	High Similarity	NPC245207
0.8636	High Similarity	NPC30951
0.8636	High Similarity	NPC319647
0.8636	High Similarity	NPC25966
0.8629	High Similarity	NPC282496
0.8629	High Similarity	NPC233526
0.8629	High Similarity	NPC136319
0.8615	High Similarity	NPC289258
0.8615	High Similarity	NPC276026
0.8615	High Similarity	NPC555
0.8615	High Similarity	NPC56764
0.8615	High Similarity	NPC188378
0.8615	High Similarity	NPC206737
0.8615	High Similarity	NPC7515
0.8615	High Similarity	NPC469659
0.8615	High Similarity	NPC310854
0.8607	High Similarity	NPC232084
0.8607	High Similarity	NPC61516
0.8607	High Similarity	NPC474565
0.8607	High Similarity	NPC247364
0.8607	High Similarity	NPC229401
0.8607	High Similarity	NPC10932
0.8605	High Similarity	NPC474635
0.8605	High Similarity	NPC202762
0.8605	High Similarity	NPC86655
0.8595	High Similarity	NPC63083
0.8594	High Similarity	NPC229231
0.8583	High Similarity	NPC186843
0.8583	High Similarity	NPC470213
0.8583	High Similarity	NPC206615
0.8583	High Similarity	NPC98631
0.8571	High Similarity	NPC295719
0.8571	High Similarity	NPC165026
0.8571	High Similarity	NPC34431
0.8571	High Similarity	NPC160283
0.8571	High Similarity	NPC284464
0.8571	High Similarity	NPC254759
0.8571	High Similarity	NPC259519
0.8571	High Similarity	NPC181361
0.8571	High Similarity	NPC73505
0.8571	High Similarity	NPC223953
0.856	High Similarity	NPC228972
0.856	High Similarity	NPC5796
0.856	High Similarity	NPC206487
0.856	High Similarity	NPC122792
0.855	High Similarity	NPC112246
0.855	High Similarity	NPC327382
0.855	High Similarity	NPC121812
0.855	High Similarity	NPC234333

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 NPC246967 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	967
0.2-0.3	2175
0.3-0.4	2782
0.4-0.5	1432
0.5-0.6	914
0.6-0.7	467
0.7-0.8	66
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8661	High Similarity	NPD3027	Phase 3
0.8475	Intermediate Similarity	NPD228	Approved
0.8359	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1613	Approved
0.8182	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6671	Approved
0.7939	Intermediate Similarity	NPD3018	Phase 2
0.7907	Intermediate Similarity	NPD4749	Approved
0.7863	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD2983	Phase 2
0.7769	Intermediate Similarity	NPD2982	Phase 2
0.7761	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2801	Approved
0.7705	Intermediate Similarity	NPD4750	Phase 3
0.7692	Intermediate Similarity	NPD2981	Phase 2
0.7655	Intermediate Similarity	NPD1653	Approved
0.7634	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5283	Phase 1
0.7578	Intermediate Similarity	NPD1548	Phase 1
0.7576	Intermediate Similarity	NPD6696	Suspended
0.7563	Intermediate Similarity	NPD940	Approved
0.7563	Intermediate Similarity	NPD846	Approved
0.7556	Intermediate Similarity	NPD4625	Phase 3
0.7541	Intermediate Similarity	NPD290	Approved
0.75	Intermediate Similarity	NPD9296	Approved
0.7481	Intermediate Similarity	NPD1610	Phase 2
0.7481	Intermediate Similarity	NPD4908	Phase 1
0.7481	Intermediate Similarity	NPD3705	Approved
0.745	Intermediate Similarity	NPD1934	Approved
0.7445	Intermediate Similarity	NPD2674	Phase 3
0.7407	Intermediate Similarity	NPD2861	Phase 2
0.7405	Intermediate Similarity	NPD3496	Discontinued
0.7391	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3620	Phase 2
0.7385	Intermediate Similarity	NPD1357	Approved
0.7372	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2219	Phase 1
0.7357	Intermediate Similarity	NPD6111	Discontinued
0.7348	Intermediate Similarity	NPD422	Phase 1
0.7348	Intermediate Similarity	NPD1091	Approved
0.7339	Intermediate Similarity	NPD2684	Approved
0.7333	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3540	Phase 1
0.7317	Intermediate Similarity	NPD968	Approved
0.7303	Intermediate Similarity	NPD3882	Suspended
0.7285	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD3022	Approved
0.728	Intermediate Similarity	NPD3021	Approved
0.7266	Intermediate Similarity	NPD1558	Phase 1
0.726	Intermediate Similarity	NPD1511	Approved
0.7254	Intermediate Similarity	NPD6099	Approved
0.7254	Intermediate Similarity	NPD6100	Approved
0.7254	Intermediate Similarity	NPD3539	Phase 1
0.7246	Intermediate Similarity	NPD3144	Approved
0.7246	Intermediate Similarity	NPD3145	Approved
0.7244	Intermediate Similarity	NPD7843	Approved
0.7226	Intermediate Similarity	NPD596	Approved
0.7226	Intermediate Similarity	NPD600	Approved
0.7222	Intermediate Similarity	NPD5177	Phase 3
0.7214	Intermediate Similarity	NPD230	Phase 1
0.7209	Intermediate Similarity	NPD7157	Approved
0.7208	Intermediate Similarity	NPD6234	Discontinued
0.719	Intermediate Similarity	NPD1242	Phase 1
0.719	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1512	Approved
0.7154	Intermediate Similarity	NPD7340	Approved
0.7153	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD844	Approved
0.7122	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD37	Approved
0.7099	Intermediate Similarity	NPD5536	Phase 2
0.7092	Intermediate Similarity	NPD447	Suspended
0.7089	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6166	Phase 2
0.7071	Intermediate Similarity	NPD840	Approved
0.7071	Intermediate Similarity	NPD839	Approved
0.7069	Intermediate Similarity	NPD9295	Approved
0.7068	Intermediate Similarity	NPD4626	Approved
0.7063	Intermediate Similarity	NPD7054	Approved
0.7059	Intermediate Similarity	NPD2922	Phase 1
0.7055	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1398	Phase 1
0.7047	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2230	Approved
0.7037	Intermediate Similarity	NPD2233	Approved
0.7037	Intermediate Similarity	NPD2232	Approved
0.7032	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4357	Discontinued
0.7021	Intermediate Similarity	NPD4060	Phase 1
0.7021	Intermediate Similarity	NPD2238	Phase 2
0.7019	Intermediate Similarity	NPD7074	Phase 3
0.7019	Intermediate Similarity	NPD7472	Approved
0.7014	Intermediate Similarity	NPD2935	Discontinued
0.7013	Intermediate Similarity	NPD3817	Phase 2
0.7007	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7228	Approved
0.6992	Remote Similarity	NPD291	Approved
0.6986	Remote Similarity	NPD3060	Approved
0.6986	Remote Similarity	NPD6674	Discontinued
0.6983	Remote Similarity	NPD9094	Approved
0.6977	Remote Similarity	NPD7635	Approved
0.6974	Remote Similarity	NPD4675	Approved
0.6974	Remote Similarity	NPD4678	Approved
0.6968	Remote Similarity	NPD4965	Approved
0.6968	Remote Similarity	NPD4967	Phase 2
0.6968	Remote Similarity	NPD4966	Approved
0.6966	Remote Similarity	NPD7266	Discontinued
0.6962	Remote Similarity	NPD6232	Discontinued
0.6959	Remote Similarity	NPD7124	Phase 2
0.6942	Remote Similarity	NPD288	Approved
0.694	Remote Similarity	NPD1778	Approved
0.6937	Remote Similarity	NPD7473	Discontinued
0.6934	Remote Similarity	NPD8651	Approved
0.6928	Remote Similarity	NPD5089	Approved
0.6928	Remote Similarity	NPD5090	Approved
0.6923	Remote Similarity	NPD6653	Approved
0.6918	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4005	Discontinued
0.6901	Remote Similarity	NPD1240	Approved
0.6894	Remote Similarity	NPD3818	Discontinued
0.689	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1652	Phase 2
0.6867	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5844	Phase 1
0.6849	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5763	Approved
0.6849	Remote Similarity	NPD5762	Approved
0.6839	Remote Similarity	NPD1465	Phase 2
0.6829	Remote Similarity	NPD7251	Discontinued
0.6822	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD709	Approved
0.6815	Remote Similarity	NPD9384	Approved
0.6815	Remote Similarity	NPD9381	Approved
0.6806	Remote Similarity	NPD1607	Approved
0.68	Remote Similarity	NPD1774	Approved
0.6797	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5402	Approved
0.6795	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7199	Phase 2
0.6791	Remote Similarity	NPD7533	Approved
0.6791	Remote Similarity	NPD7534	Approved
0.6788	Remote Similarity	NPD2231	Phase 2
0.6788	Remote Similarity	NPD7808	Phase 3
0.6788	Remote Similarity	NPD2235	Phase 2
0.6788	Remote Similarity	NPD9269	Phase 2
0.6783	Remote Similarity	NPD943	Approved
0.6779	Remote Similarity	NPD2677	Approved
0.6777	Remote Similarity	NPD2933	Approved
0.6777	Remote Similarity	NPD2934	Approved
0.6768	Remote Similarity	NPD6797	Phase 2
0.6761	Remote Similarity	NPD5718	Phase 2
0.6757	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4236	Phase 3
0.6757	Remote Similarity	NPD4237	Approved
0.6755	Remote Similarity	NPD7447	Phase 1
0.6755	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1424	Approved
0.6753	Remote Similarity	NPD4380	Phase 2
0.6741	Remote Similarity	NPD5691	Approved
0.6739	Remote Similarity	NPD9622	Approved
0.6735	Remote Similarity	NPD1375	Discontinued
0.6731	Remote Similarity	NPD2978	Approved
0.6731	Remote Similarity	NPD2977	Approved
0.673	Remote Similarity	NPD5494	Approved
0.6721	Remote Similarity	NPD2860	Approved
0.6721	Remote Similarity	NPD2859	Approved
0.6718	Remote Similarity	NPD9379	Approved
0.6718	Remote Similarity	NPD821	Approved
0.6718	Remote Similarity	NPD9377	Approved
0.6714	Remote Similarity	NPD6584	Phase 3
0.6713	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6233	Phase 2
0.6712	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1510	Phase 2
0.6711	Remote Similarity	NPD3892	Phase 2
0.6711	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4055	Discovery
0.6708	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8053	Approved
0.6707	Remote Similarity	NPD8054	Approved
0.6694	Remote Similarity	NPD845	Approved
0.6694	Remote Similarity	NPD3020	Approved
0.669	Remote Similarity	NPD4097	Suspended
0.669	Remote Similarity	NPD7095	Approved
0.669	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7153	Discontinued
0.6689	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3111	Phase 1
0.6687	Remote Similarity	NPD7549	Discontinued
0.6667	Remote Similarity	NPD2161	Phase 2
0.6667	Remote Similarity	NPD2237	Approved
0.6667	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3158	Phase 1
0.6645	Remote Similarity	NPD2532	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