NPASS Compound

Structure

CID54647 OpenBabel06191715392D 23 24 0 0 0 0 0 0 0 0999 V2000 1.5731 2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0579 1.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 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 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 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 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 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 12 2 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.15
Volume:	336.773
LogP:	2.523
LogD:	0.278
LogS:	-3.032
# Rotatable Bonds:	4
TPSA:	68.28
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.801
Synthetic Accessibility Score:	2.589
Fsp3:	0.474
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.355
MDCK Permeability:	3.5892731830244884e-05
Pgp-inhibitor:	0.561
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.114

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	73.18997955322266%
Volume Distribution (VD):	0.629
Pgp-substrate:	28.25847053527832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.906
CYP2C19-inhibitor:	0.932
CYP2C19-substrate:	0.944
CYP2C9-inhibitor:	0.343
CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	1.82
Half-life (T1/2):	0.702

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.572
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.609
Rat Oral Acute Toxicity:	0.841
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.54
Carcinogencity:	0.45
Eye Corrosion:	0.937
Eye Irritation:	0.743
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC54647

Natural Product ID:	NPC54647
*Common Name:**	Grandiflorone
IUPAC Name:	5-hydroxy-2,2,6,6-tetramethyl-4-(3-phenylpropanoyl)cyclohex-4-ene-1,3-dione
Synonyms:
Standard InCHIKey:	KUWGTESSHWPSOB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H22O4/c1-18(2)15(21)14(16(22)19(3,4)17(18)23)13(20)11-10-12-8-6-5-7-9-12/h5-9,21H,10-11H2,1-4H3
SMILES:	O=C(C1=C(O)C(C)(C)C(=O)C(C1=O)(C)C)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3810189
PubChem CID:	3014646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002493] M-benzoquinones

*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
NPO634	Salvia divinorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510607]
NPO634	Salvia divinorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15987194]
NPO634	Salvia divinorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441078]
NPO634	Salvia divinorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16621556]
NPO634	Salvia divinorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16945525]
NPO634	Salvia divinorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190459]
NPO634	Salvia divinorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17580847]
NPO21258	Sinularia dura	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18630962]
NPO634	Salvia divinorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21338114]
NPO634	Salvia divinorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25193297]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26731565]
NPO10230	Trichilia connaroides	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31589431]
NPO9792	Leptospermum flavescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13871	Solanum aphyodendron	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO634	Salvia divinorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15073	Cystoseira spinosa	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5480	Mimosa aspera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21258	Sinularia dura	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14973	Ircinia felix	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10230	Trichilia connaroides	Species	Meliaceae	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	1
MIC	3

Activity Type	# Activity
Individual Protein	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3179	Individual Protein	4-hydroxyphenylpyruvate dioxygenase	Arabidopsis thaliana	IC50	=	750.0	nM	PMID[486364]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	6.0	ug.mL-1	PMID[486364]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.0	ug.mL-1	PMID[486364]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	512.0	ug.mL-1	PMID[486364]

☑ 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 NPC54647 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	196
0.1-0.2	1070
0.2-0.3	3011
0.3-0.4	10326
0.4-0.5	15100
0.5-0.6	10903
0.6-0.7	1855
0.7-0.8	212
0.8-0.85	15
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8913	High Similarity	NPC477693
0.8913	High Similarity	NPC477704
0.8846	High Similarity	NPC471481
0.8762	High Similarity	NPC130591
0.8762	High Similarity	NPC294458
0.8762	High Similarity	NPC234637
0.8571	High Similarity	NPC218855
0.8485	Intermediate Similarity	NPC476120
0.8384	Intermediate Similarity	NPC278228
0.8318	Intermediate Similarity	NPC477475
0.8318	Intermediate Similarity	NPC477476
0.8214	Intermediate Similarity	NPC474223
0.8214	Intermediate Similarity	NPC475827
0.82	Intermediate Similarity	NPC240042
0.8095	Intermediate Similarity	NPC244933
0.8095	Intermediate Similarity	NPC85560
0.8081	Intermediate Similarity	NPC34243
0.8061	Intermediate Similarity	NPC141607
0.8061	Intermediate Similarity	NPC187725
0.8	Intermediate Similarity	NPC474254
0.8	Intermediate Similarity	NPC474159
0.8	Intermediate Similarity	NPC215419
0.7946	Intermediate Similarity	NPC268930
0.7941	Intermediate Similarity	NPC179411
0.7928	Intermediate Similarity	NPC471616
0.7905	Intermediate Similarity	NPC329282
0.7895	Intermediate Similarity	NPC474222
0.7895	Intermediate Similarity	NPC475804
0.7863	Intermediate Similarity	NPC478108
0.7857	Intermediate Similarity	NPC231591
0.7857	Intermediate Similarity	NPC469843
0.785	Intermediate Similarity	NPC470007
0.7843	Intermediate Similarity	NPC477767
0.7822	Intermediate Similarity	NPC206764
0.7818	Intermediate Similarity	NPC93287
0.781	Intermediate Similarity	NPC274443
0.781	Intermediate Similarity	NPC247976
0.7789	Intermediate Similarity	NPC44830
0.7768	Intermediate Similarity	NPC260886
0.7767	Intermediate Similarity	NPC271475
0.7767	Intermediate Similarity	NPC145052
0.7757	Intermediate Similarity	NPC100767
0.7748	Intermediate Similarity	NPC471721
0.7739	Intermediate Similarity	NPC476225
0.7727	Intermediate Similarity	NPC292834
0.7719	Intermediate Similarity	NPC472698
0.7719	Intermediate Similarity	NPC472697
0.7714	Intermediate Similarity	NPC222390
0.7714	Intermediate Similarity	NPC244427
0.77	Intermediate Similarity	NPC86987
0.7699	Intermediate Similarity	NPC108532
0.767	Intermediate Similarity	NPC103048
0.7667	Intermediate Similarity	NPC316553
0.7664	Intermediate Similarity	NPC172483
0.766	Intermediate Similarity	NPC477703
0.7658	Intermediate Similarity	NPC143768
0.7647	Intermediate Similarity	NPC470649
0.7647	Intermediate Similarity	NPC478107
0.7636	Intermediate Similarity	NPC265513
0.7636	Intermediate Similarity	NPC222905
0.7632	Intermediate Similarity	NPC61651
0.7629	Intermediate Similarity	NPC123476
0.7619	Intermediate Similarity	NPC264728
0.7619	Intermediate Similarity	NPC94487
0.7619	Intermediate Similarity	NPC225079
0.7615	Intermediate Similarity	NPC475282
0.7596	Intermediate Similarity	NPC329387
0.7596	Intermediate Similarity	NPC317280
0.7553	Intermediate Similarity	NPC272260
0.7547	Intermediate Similarity	NPC475978
0.7547	Intermediate Similarity	NPC474820
0.7541	Intermediate Similarity	NPC25736
0.7525	Intermediate Similarity	NPC476484
0.7524	Intermediate Similarity	NPC476042
0.7524	Intermediate Similarity	NPC474308
0.7521	Intermediate Similarity	NPC268607
0.7521	Intermediate Similarity	NPC476234
0.75	Intermediate Similarity	NPC470253
0.75	Intermediate Similarity	NPC204784
0.75	Intermediate Similarity	NPC156021
0.75	Intermediate Similarity	NPC294050
0.75	Intermediate Similarity	NPC328997
0.75	Intermediate Similarity	NPC289201
0.75	Intermediate Similarity	NPC471186
0.7478	Intermediate Similarity	NPC222968
0.7478	Intermediate Similarity	NPC80605
0.7478	Intermediate Similarity	NPC471553
0.7478	Intermediate Similarity	NPC323440
0.7477	Intermediate Similarity	NPC329556
0.7477	Intermediate Similarity	NPC472691
0.7477	Intermediate Similarity	NPC471829
0.7477	Intermediate Similarity	NPC475939
0.7477	Intermediate Similarity	NPC474866
0.7475	Intermediate Similarity	NPC194326
0.7474	Intermediate Similarity	NPC127343
0.7453	Intermediate Similarity	NPC109514
0.7453	Intermediate Similarity	NPC136810
0.7453	Intermediate Similarity	NPC158623
0.7453	Intermediate Similarity	NPC133809
0.7453	Intermediate Similarity	NPC128248
0.7451	Intermediate Similarity	NPC59677
0.7449	Intermediate Similarity	NPC95965
0.7438	Intermediate Similarity	NPC146239
0.7438	Intermediate Similarity	NPC470648
0.7436	Intermediate Similarity	NPC472680
0.7436	Intermediate Similarity	NPC472679
0.7431	Intermediate Similarity	NPC193640
0.7431	Intermediate Similarity	NPC25385
0.7431	Intermediate Similarity	NPC475905
0.7429	Intermediate Similarity	NPC120393
0.7411	Intermediate Similarity	NPC280789
0.7411	Intermediate Similarity	NPC474689
0.7404	Intermediate Similarity	NPC469893
0.7404	Intermediate Similarity	NPC12695
0.74	Intermediate Similarity	NPC329064
0.7387	Intermediate Similarity	NPC88141
0.7377	Intermediate Similarity	NPC472678
0.7368	Intermediate Similarity	NPC93181
0.7368	Intermediate Similarity	NPC151405
0.7368	Intermediate Similarity	NPC139901
0.7364	Intermediate Similarity	NPC20485
0.7353	Intermediate Similarity	NPC284475
0.734	Intermediate Similarity	NPC9796
0.7339	Intermediate Similarity	NPC134120
0.7333	Intermediate Similarity	NPC469892
0.7333	Intermediate Similarity	NPC469891
0.7333	Intermediate Similarity	NPC239185
0.7333	Intermediate Similarity	NPC469890
0.7333	Intermediate Similarity	NPC472681
0.7333	Intermediate Similarity	NPC325740
0.7328	Intermediate Similarity	NPC94425
0.7311	Intermediate Similarity	NPC167323
0.7311	Intermediate Similarity	NPC269923
0.7304	Intermediate Similarity	NPC23402
0.73	Intermediate Similarity	NPC69057
0.73	Intermediate Similarity	NPC322387
0.7297	Intermediate Similarity	NPC469511
0.7295	Intermediate Similarity	NPC474106
0.7292	Intermediate Similarity	NPC17408
0.7292	Intermediate Similarity	NPC285716
0.7292	Intermediate Similarity	NPC164086
0.7282	Intermediate Similarity	NPC155232
0.7282	Intermediate Similarity	NPC188844
0.7282	Intermediate Similarity	NPC153885
0.7282	Intermediate Similarity	NPC1682
0.7281	Intermediate Similarity	NPC326664
0.7273	Intermediate Similarity	NPC70843
0.7273	Intermediate Similarity	NPC472700
0.7273	Intermediate Similarity	NPC472699
0.7273	Intermediate Similarity	NPC188677
0.7265	Intermediate Similarity	NPC318173
0.7264	Intermediate Similarity	NPC75724
0.7264	Intermediate Similarity	NPC134882
0.7258	Intermediate Similarity	NPC471832
0.7255	Intermediate Similarity	NPC303967
0.7255	Intermediate Similarity	NPC67585
0.7255	Intermediate Similarity	NPC86670
0.7255	Intermediate Similarity	NPC70940
0.7255	Intermediate Similarity	NPC274455
0.7255	Intermediate Similarity	NPC110420
0.7245	Intermediate Similarity	NPC285773
0.7245	Intermediate Similarity	NPC273758
0.7228	Intermediate Similarity	NPC157778
0.7217	Intermediate Similarity	NPC285350
0.7216	Intermediate Similarity	NPC189237
0.7212	Intermediate Similarity	NPC238219
0.7207	Intermediate Similarity	NPC472701
0.7207	Intermediate Similarity	NPC472695
0.7207	Intermediate Similarity	NPC112903
0.7207	Intermediate Similarity	NPC472696
0.7207	Intermediate Similarity	NPC472683
0.7203	Intermediate Similarity	NPC202015
0.72	Intermediate Similarity	NPC471334
0.72	Intermediate Similarity	NPC472682
0.72	Intermediate Similarity	NPC472692
0.719	Intermediate Similarity	NPC85511
0.719	Intermediate Similarity	NPC328107
0.7188	Intermediate Similarity	NPC300205
0.7184	Intermediate Similarity	NPC133461
0.7184	Intermediate Similarity	NPC110704
0.7174	Intermediate Similarity	NPC74458
0.717	Intermediate Similarity	NPC226041
0.717	Intermediate Similarity	NPC265220
0.7168	Intermediate Similarity	NPC474057
0.7168	Intermediate Similarity	NPC137315
0.7158	Intermediate Similarity	NPC179726
0.7157	Intermediate Similarity	NPC298115
0.7143	Intermediate Similarity	NPC475006
0.7143	Intermediate Similarity	NPC260233
0.7143	Intermediate Similarity	NPC40178
0.7143	Intermediate Similarity	NPC317305
0.7143	Intermediate Similarity	NPC470252
0.7131	Intermediate Similarity	NPC472694
0.7131	Intermediate Similarity	NPC295664
0.7131	Intermediate Similarity	NPC472693
0.713	Intermediate Similarity	NPC476993
0.713	Intermediate Similarity	NPC112552
0.7129	Intermediate Similarity	NPC43945
0.7117	Intermediate Similarity	NPC142326
0.7117	Intermediate Similarity	NPC94751

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 NPC54647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	865
0.2-0.3	1418
0.3-0.4	3068
0.4-0.5	2437
0.5-0.6	977
0.6-0.7	169
0.7-0.8	26
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
0.8454	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2066	Phase 3
0.7615	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5346	Phase 2
0.75	Intermediate Similarity	NPD5347	Phase 2
0.7477	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1929	Approved
0.7477	Intermediate Similarity	NPD1930	Approved
0.7477	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4793	Discontinued
0.7451	Intermediate Similarity	NPD1088	Approved
0.7396	Intermediate Similarity	NPD226	Approved
0.7353	Intermediate Similarity	NPD7609	Phase 3
0.7333	Intermediate Similarity	NPD3495	Discontinued
0.7327	Intermediate Similarity	NPD800	Approved
0.7308	Intermediate Similarity	NPD1693	Approved
0.7282	Intermediate Similarity	NPD7631	Approved
0.7255	Intermediate Similarity	NPD1090	Approved
0.7255	Intermediate Similarity	NPD1086	Approved
0.7255	Intermediate Similarity	NPD1089	Approved
0.7248	Intermediate Similarity	NPD5909	Discontinued
0.7245	Intermediate Similarity	NPD9491	Approved
0.7222	Intermediate Similarity	NPD1932	Approved
0.7182	Intermediate Similarity	NPD5048	Discontinued
0.713	Intermediate Similarity	NPD6010	Discontinued
0.7129	Intermediate Similarity	NPD650	Approved
0.7119	Intermediate Similarity	NPD7009	Phase 2
0.7113	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD225	Approved
0.7083	Intermediate Similarity	NPD227	Approved
0.7043	Intermediate Similarity	NPD7094	Approved
0.7043	Intermediate Similarity	NPD6858	Approved
0.7041	Intermediate Similarity	NPD942	Approved
0.7034	Intermediate Similarity	NPD7610	Discontinued
0.7019	Intermediate Similarity	NPD1239	Approved
0.7	Intermediate Similarity	NPD6647	Phase 2
0.6991	Remote Similarity	NPD2329	Discontinued
0.6981	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1087	Approved
0.6937	Remote Similarity	NPD1237	Approved
0.6931	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.693	Remote Similarity	NPD1317	Discontinued
0.6923	Remote Similarity	NPD5951	Approved
0.6923	Remote Similarity	NPD3673	Approved
0.6923	Remote Similarity	NPD3672	Approved
0.6917	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1018	Approved
0.686	Remote Similarity	NPD2932	Approved
0.6852	Remote Similarity	NPD1565	Approved
0.6852	Remote Similarity	NPD1566	Phase 3
0.6852	Remote Similarity	NPD1564	Approved
0.6837	Remote Similarity	NPD9490	Approved
0.6803	Remote Similarity	NPD4879	Approved
0.678	Remote Similarity	NPD2629	Approved
0.6759	Remote Similarity	NPD1989	Approved
0.6727	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3019	Approved
0.6721	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4094	Approved
0.6667	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD2067	Discontinued
0.6638	Remote Similarity	NPD5278	Discontinued
0.6636	Remote Similarity	NPD1508	Approved
0.6604	Remote Similarity	NPD9258	Approved
0.6604	Remote Similarity	NPD9256	Approved
0.6583	Remote Similarity	NPD3317	Approved
0.6577	Remote Similarity	NPD7798	Approved
0.6574	Remote Similarity	NPD1563	Approved
0.6574	Remote Similarity	NPD1202	Approved
0.6569	Remote Similarity	NPD3971	Phase 1
0.656	Remote Similarity	NPD3972	Approved
0.656	Remote Similarity	NPD4878	Approved
0.6555	Remote Similarity	NPD2650	Approved
0.6555	Remote Similarity	NPD2652	Approved
0.6549	Remote Similarity	NPD5765	Approved
0.6545	Remote Similarity	NPD4657	Approved
0.6545	Remote Similarity	NPD4655	Approved
0.6538	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3268	Approved
0.6532	Remote Similarity	NPD3026	Approved
0.6532	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3023	Approved
0.6529	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6685	Approved
0.6522	Remote Similarity	NPD467	Phase 1
0.6514	Remote Similarity	NPD6049	Phase 2
0.6514	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD3025	Approved
0.6504	Remote Similarity	NPD3024	Approved
0.65	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD9495	Approved
0.6486	Remote Similarity	NPD253	Approved
0.648	Remote Similarity	NPD1201	Approved
0.6476	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1843	Approved
0.6455	Remote Similarity	NPD2860	Approved
0.6455	Remote Similarity	NPD2859	Approved
0.6452	Remote Similarity	NPD2345	Approved
0.6441	Remote Similarity	NPD3644	Approved
0.6441	Remote Similarity	NPD3642	Approved
0.6441	Remote Similarity	NPD3643	Approved
0.6434	Remote Similarity	NPD7084	Phase 3
0.6422	Remote Similarity	NPD1066	Discontinued
0.6422	Remote Similarity	NPD719	Approved
0.6422	Remote Similarity	NPD720	Approved
0.6406	Remote Similarity	NPD1470	Approved
0.6404	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD9566	Approved
0.6381	Remote Similarity	NPD9257	Approved
0.6381	Remote Similarity	NPD9259	Approved
0.6378	Remote Similarity	NPD1755	Approved
0.637	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1246	Approved
0.6364	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2933	Approved
0.6364	Remote Similarity	NPD2934	Approved
0.6364	Remote Similarity	NPD1711	Phase 2
0.6364	Remote Similarity	NPD7961	Discontinued
0.6357	Remote Similarity	NPD2798	Approved
0.6349	Remote Similarity	NPD6287	Discontinued
0.6336	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2607	Approved
0.633	Remote Similarity	NPD752	Approved
0.6325	Remote Similarity	NPD9267	Approved
0.6325	Remote Similarity	NPD9263	Approved
0.6325	Remote Similarity	NPD9264	Approved
0.632	Remote Similarity	NPD4199	Phase 3
0.6316	Remote Similarity	NPD2648	Phase 3
0.6316	Remote Similarity	NPD6027	Approved
0.6316	Remote Similarity	NPD2193	Phase 2
0.6316	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6024	Approved
0.6306	Remote Similarity	NPD1809	Phase 2
0.6303	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.629	Remote Similarity	NPD998	Approved
0.6288	Remote Similarity	NPD2313	Discontinued
0.6283	Remote Similarity	NPD3020	Approved
0.6281	Remote Similarity	NPD7076	Approved
0.6281	Remote Similarity	NPD1241	Discontinued
0.6281	Remote Similarity	NPD7077	Approved
0.6279	Remote Similarity	NPD3266	Approved
0.6279	Remote Similarity	NPD3267	Approved
0.6275	Remote Similarity	NPD4695	Discontinued
0.6273	Remote Similarity	NPD845	Approved
0.6271	Remote Similarity	NPD74	Approved
0.6271	Remote Similarity	NPD2182	Approved
0.6271	Remote Similarity	NPD9266	Approved
0.6263	Remote Similarity	NPD9716	Approved
0.6262	Remote Similarity	NPD1101	Approved
0.626	Remote Similarity	NPD9493	Approved
0.625	Remote Similarity	NPD5157	Phase 1
0.625	Remote Similarity	NPD2799	Discontinued
0.625	Remote Similarity	NPD1875	Phase 1
0.625	Remote Similarity	NPD5159	Phase 2
0.625	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6085	Phase 2
0.6222	Remote Similarity	NPD6651	Approved
0.622	Remote Similarity	NPD2609	Approved
0.622	Remote Similarity	NPD3132	Approved
0.622	Remote Similarity	NPD4218	Approved
0.622	Remote Similarity	NPD4216	Approved
0.622	Remote Similarity	NPD4215	Approved
0.622	Remote Similarity	NPD2610	Approved
0.622	Remote Similarity	NPD3131	Approved
0.622	Remote Similarity	NPD4217	Approved
0.622	Remote Similarity	NPD2608	Approved
0.622	Remote Similarity	NPD2611	Approved
0.622	Remote Similarity	NPD2612	Approved
0.6218	Remote Similarity	NPD4233	Approved
0.6218	Remote Similarity	NPD1756	Approved
0.6218	Remote Similarity	NPD4234	Approved
0.6218	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD1752	Approved
0.6212	Remote Similarity	NPD7008	Discontinued
0.6207	Remote Similarity	NPD164	Approved
0.6198	Remote Similarity	NPD5277	Phase 2
0.6195	Remote Similarity	NPD5926	Approved
0.6187	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD4198	Discontinued
0.6174	Remote Similarity	NPD4719	Phase 2
0.6174	Remote Similarity	NPD2196	Discontinued
0.6174	Remote Similarity	NPD2171	Approved
0.6172	Remote Similarity	NPD6637	Approved
0.6154	Remote Similarity	NPD2797	Approved
0.6154	Remote Similarity	NPD1164	Approved
0.6148	Remote Similarity	NPD3598	Phase 3
0.6143	Remote Similarity	NPD8166	Discontinued
0.614	Remote Similarity	NPD1238	Approved
0.6136	Remote Similarity	NPD7055	Discontinued
0.6126	Remote Similarity	NPD3718	Approved
0.6126	Remote Similarity	NPD3719	Approved
0.6121	Remote Similarity	NPD3357	Discontinued
0.6121	Remote Similarity	NPD9261	Approved
0.6116	Remote Similarity	NPD6912	Phase 3

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