NPASS Compound

Structure

CID119209 OpenBabel06191715472D 32 35 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 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 -1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 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 -1.5000 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 1.5000 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 5.1962 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 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 2.5981 1.5000 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 0.5000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 30 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 26 1 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 21 2 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 28 2 0 0 0 0 20 15 1 1 0 0 0 20 31 1 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 25 2 0 0 0 0 23 29 1 0 0 0 0 24 32 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.19
Volume:	453.039
LogP:	6.589
LogD:	4.233
LogS:	-2.772
# Rotatable Bonds:	4
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	3.63
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.73
MDCK Permeability:	1.599317511136178e-05
Pgp-inhibitor:	0.795
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	96.62904357910156%
Volume Distribution (VD):	0.602
Pgp-substrate:	6.288102149963379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.209
CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.931
CYP2C19-substrate:	0.446
CYP2C9-inhibitor:	0.932
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.89
CYP2D6-substrate:	0.43
CYP3A4-inhibitor:	0.679
CYP3A4-substrate:	0.291

ADMET: Excretion

Clearance (CL):	7.926
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.812
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.893
Carcinogencity:	0.766
Eye Corrosion:	0.003
Eye Irritation:	0.193
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC119209

Natural Product ID:	NPC119209
*Common Name:**	(2S)-6-(Gamma,Gamma-Dimethylallyl)-5,4'-Dihydroxy-3'-Methoxy-6'',6''-Dimethylpyran[2'',3'':7,8]Flavanone
IUPAC Name:	(2S)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)-2,3-dihydropyrano[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	KCZWDIXZSAGPCD-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C26H28O6/c1-14(2)6-8-16-23(29)22-19(28)13-20(15-7-9-18(27)21(12-15)30-5)31-25(22)17-10-11-26(3,4)32-24(16)17/h6-7,9-12,20,27,29H,8,13H2,1-5H3/t20-/m0/s1
SMILES:	COc1cc(ccc1O)[C@@H]1CC(=O)c2c(O1)c1C=CC(Oc1c(c2O)CC=C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464609
PubChem CID:	44559077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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
NPO26220	Lonchocarpus utilis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10075742]
NPO4562	Lonchocarpus urucu	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10075742]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2671	Pedicularis semitorta	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26220	Lonchocarpus utilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12750	Cordia americana	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6147	Eupatorium riparium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3890	Scopolia japonica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5753	Glycosmis montana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4562	Lonchocarpus urucu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5368	Achillea cretica	Species	Asteraceae	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	4

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2680	Individual Protein	Ornithine decarboxylase	Homo sapiens	IC50	=	1100.0	nM	PMID[502069]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3000.0	nM	PMID[502069]
NPT2	Others	Unspecified		IC50	=	680.0	nM	PMID[502069]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3500.0	nM	PMID[502069]

☑ 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 NPC119209 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	411
0.1-0.2	1634
0.2-0.3	4030
0.3-0.4	10066
0.4-0.5	8124
0.5-0.6	3358
0.6-0.7	4758
0.7-0.8	5476
0.8-0.85	2796
0.85-0.9	1591
0.9-0.95	373
0.95-1	80

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC192686
1.0	High Similarity	NPC118256
0.9934	High Similarity	NPC474038
0.9868	High Similarity	NPC27337
0.9868	High Similarity	NPC284820
0.9868	High Similarity	NPC475784
0.9868	High Similarity	NPC473272
0.9805	High Similarity	NPC186686
0.9805	High Similarity	NPC472625
0.9804	High Similarity	NPC471210
0.9804	High Similarity	NPC26326
0.9804	High Similarity	NPC472632
0.9801	High Similarity	NPC195796
0.9801	High Similarity	NPC35038
0.9801	High Similarity	NPC278778
0.9801	High Similarity	NPC291878
0.974	High Similarity	NPC474033
0.974	High Similarity	NPC474162
0.974	High Similarity	NPC474150
0.974	High Similarity	NPC474034
0.9739	High Similarity	NPC472624
0.9739	High Similarity	NPC174953
0.9737	High Similarity	NPC472598
0.9737	High Similarity	NPC52889
0.9737	High Similarity	NPC291508
0.9737	High Similarity	NPC474055
0.9737	High Similarity	NPC471209
0.9735	High Similarity	NPC200761
0.9735	High Similarity	NPC477503
0.9735	High Similarity	NPC45849
0.9735	High Similarity	NPC470327
0.9679	High Similarity	NPC43319
0.9675	High Similarity	NPC471212
0.9675	High Similarity	NPC134783
0.9675	High Similarity	NPC472634
0.9675	High Similarity	NPC471211
0.9673	High Similarity	NPC117418
0.9673	High Similarity	NPC53545
0.9673	High Similarity	NPC204879
0.9673	High Similarity	NPC74178
0.9673	High Similarity	NPC184755
0.9673	High Similarity	NPC473990
0.9671	High Similarity	NPC471985
0.9671	High Similarity	NPC470328
0.9671	High Similarity	NPC209614
0.9671	High Similarity	NPC472626
0.9669	High Similarity	NPC192083
0.9669	High Similarity	NPC18727
0.9669	High Similarity	NPC74924
0.9669	High Similarity	NPC213896
0.9618	High Similarity	NPC218226
0.9615	High Similarity	NPC293319
0.9615	High Similarity	NPC62261
0.9613	High Similarity	NPC472448
0.9613	High Similarity	NPC83922
0.9613	High Similarity	NPC472635
0.9613	High Similarity	NPC476247
0.961	High Similarity	NPC282009
0.961	High Similarity	NPC36217
0.961	High Similarity	NPC287328
0.961	High Similarity	NPC472631
0.961	High Similarity	NPC204290
0.961	High Similarity	NPC328102
0.961	High Similarity	NPC472630
0.9608	High Similarity	NPC218313
0.9608	High Similarity	NPC223787
0.9608	High Similarity	NPC474681
0.9605	High Similarity	NPC226025
0.9605	High Similarity	NPC321779
0.9605	High Similarity	NPC234255
0.9603	High Similarity	NPC471982
0.9603	High Similarity	NPC106976
0.9603	High Similarity	NPC302950
0.9603	High Similarity	NPC219582
0.9603	High Similarity	NPC236637
0.9557	High Similarity	NPC288813
0.9554	High Similarity	NPC471213
0.9551	High Similarity	NPC124038
0.9548	High Similarity	NPC29876
0.9548	High Similarity	NPC471499
0.9548	High Similarity	NPC167678
0.9548	High Similarity	NPC142252
0.9548	High Similarity	NPC289771
0.9545	High Similarity	NPC250214
0.9545	High Similarity	NPC95936
0.9545	High Similarity	NPC22192
0.9542	High Similarity	NPC6633
0.9542	High Similarity	NPC472455
0.9542	High Similarity	NPC170026
0.9542	High Similarity	NPC282307
0.9542	High Similarity	NPC5322
0.9542	High Similarity	NPC133970
0.9539	High Similarity	NPC298692
0.9539	High Similarity	NPC170492
0.949	High Similarity	NPC239752
0.949	High Similarity	NPC472450
0.949	High Similarity	NPC108433
0.949	High Similarity	NPC300053
0.949	High Similarity	NPC275780
0.9487	High Similarity	NPC194427
0.9487	High Similarity	NPC201800
0.9487	High Similarity	NPC261470
0.9484	High Similarity	NPC470326
0.9484	High Similarity	NPC471973
0.9484	High Similarity	NPC476980
0.9484	High Similarity	NPC474960
0.9481	High Similarity	NPC162869
0.9481	High Similarity	NPC156057
0.9481	High Similarity	NPC474208
0.9481	High Similarity	NPC78225
0.9481	High Similarity	NPC471479
0.9481	High Similarity	NPC471515
0.9481	High Similarity	NPC78071
0.9481	High Similarity	NPC475267
0.9481	High Similarity	NPC474836
0.9481	High Similarity	NPC67876
0.9481	High Similarity	NPC48208
0.9477	High Similarity	NPC117992
0.9477	High Similarity	NPC230149
0.9477	High Similarity	NPC168247
0.9477	High Similarity	NPC472280
0.9477	High Similarity	NPC200246
0.9477	High Similarity	NPC57674
0.9477	High Similarity	NPC256925
0.9477	High Similarity	NPC152951
0.9474	High Similarity	NPC40033
0.9474	High Similarity	NPC237994
0.9474	High Similarity	NPC472912
0.947	High Similarity	NPC338131
0.947	High Similarity	NPC3825
0.947	High Similarity	NPC88804
0.947	High Similarity	NPC472633
0.9434	High Similarity	NPC475212
0.9434	High Similarity	NPC165456
0.943	High Similarity	NPC39091
0.943	High Similarity	NPC272502
0.943	High Similarity	NPC120593
0.9427	High Similarity	NPC23298
0.9427	High Similarity	NPC189473
0.9423	High Similarity	NPC165970
0.9423	High Similarity	NPC173137
0.9423	High Similarity	NPC158188
0.9423	High Similarity	NPC234644
0.9423	High Similarity	NPC57715
0.9423	High Similarity	NPC113163
0.9423	High Similarity	NPC259456
0.9423	High Similarity	NPC266314
0.9423	High Similarity	NPC305987
0.9423	High Similarity	NPC84324
0.9423	High Similarity	NPC66618
0.9423	High Similarity	NPC288131
0.9423	High Similarity	NPC198829
0.9419	High Similarity	NPC187792
0.9419	High Similarity	NPC210459
0.9419	High Similarity	NPC172202
0.9419	High Similarity	NPC284127
0.9419	High Similarity	NPC469658
0.9419	High Similarity	NPC476410
0.9416	High Similarity	NPC276444
0.9416	High Similarity	NPC471500
0.9416	High Similarity	NPC326037
0.9416	High Similarity	NPC470600
0.9416	High Similarity	NPC320825
0.9416	High Similarity	NPC191146
0.9416	High Similarity	NPC13858
0.9416	High Similarity	NPC68093
0.9416	High Similarity	NPC235165
0.9416	High Similarity	NPC255106
0.9416	High Similarity	NPC24640
0.9412	High Similarity	NPC70433
0.9412	High Similarity	NPC227337
0.9412	High Similarity	NPC223701
0.9412	High Similarity	NPC7989
0.9412	High Similarity	NPC273462
0.9412	High Similarity	NPC49402
0.9412	High Similarity	NPC472583
0.9412	High Similarity	NPC33051
0.9408	High Similarity	NPC154345
0.9408	High Similarity	NPC256406
0.9404	High Similarity	NPC52005
0.9404	High Similarity	NPC48479
0.9404	High Similarity	NPC223579
0.9404	High Similarity	NPC183950
0.9404	High Similarity	NPC137062
0.9404	High Similarity	NPC177298
0.9404	High Similarity	NPC287101
0.9375	High Similarity	NPC472276
0.9371	High Similarity	NPC474024
0.9371	High Similarity	NPC477154
0.9371	High Similarity	NPC117854
0.9371	High Similarity	NPC6588
0.9367	High Similarity	NPC303174
0.9367	High Similarity	NPC472277
0.9367	High Similarity	NPC50960
0.9367	High Similarity	NPC224280
0.9363	High Similarity	NPC229632
0.9363	High Similarity	NPC219927
0.9363	High Similarity	NPC81679
0.9363	High Similarity	NPC472964
0.9363	High Similarity	NPC78332

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 NPC119209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	931
0.2-0.3	1748
0.3-0.4	2629
0.4-0.5	1808
0.5-0.6	992
0.6-0.7	492
0.7-0.8	134
0.8-0.85	30
0.85-0.9	17
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9669	High Similarity	NPD2393	Clinical (unspecified phase)
0.9603	High Similarity	NPD1934	Approved
0.9286	High Similarity	NPD2801	Approved
0.9245	High Similarity	NPD6166	Phase 2
0.9245	High Similarity	NPD6168	Clinical (unspecified phase)
0.9245	High Similarity	NPD6167	Clinical (unspecified phase)
0.9091	High Similarity	NPD4380	Phase 2
0.9074	High Similarity	NPD7054	Approved
0.9073	High Similarity	NPD1511	Approved
0.9018	High Similarity	NPD7074	Phase 3
0.9018	High Similarity	NPD7472	Approved
0.8954	High Similarity	NPD1512	Approved
0.8924	High Similarity	NPD3882	Suspended
0.8896	High Similarity	NPD3818	Discontinued
0.8889	High Similarity	NPD4378	Clinical (unspecified phase)
0.8875	High Similarity	NPD5494	Approved
0.8861	High Similarity	NPD3817	Phase 2
0.8848	High Similarity	NPD6797	Phase 2
0.8805	High Similarity	NPD4868	Clinical (unspecified phase)
0.8795	High Similarity	NPD7251	Discontinued
0.875	High Similarity	NPD4381	Clinical (unspecified phase)
0.875	High Similarity	NPD7075	Discontinued
0.8743	High Similarity	NPD4338	Clinical (unspecified phase)
0.8743	High Similarity	NPD7808	Phase 3
0.8679	High Similarity	NPD7096	Clinical (unspecified phase)
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8645	High Similarity	NPD7410	Clinical (unspecified phase)
0.8625	High Similarity	NPD8443	Clinical (unspecified phase)
0.8618	High Similarity	NPD1549	Phase 2
0.8614	High Similarity	NPD7804	Clinical (unspecified phase)
0.8503	High Similarity	NPD5844	Phase 1
0.85	High Similarity	NPD6801	Discontinued
0.8487	Intermediate Similarity	NPD2796	Approved
0.8476	Intermediate Similarity	NPD6959	Discontinued
0.8447	Intermediate Similarity	NPD7819	Suspended
0.8438	Intermediate Similarity	NPD7411	Suspended
0.8424	Intermediate Similarity	NPD6232	Discontinued
0.8421	Intermediate Similarity	NPD1510	Phase 2
0.8383	Intermediate Similarity	NPD7473	Discontinued
0.8294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD6559	Discontinued
0.8228	Intermediate Similarity	NPD6799	Approved
0.8221	Intermediate Similarity	NPD1465	Phase 2
0.8171	Intermediate Similarity	NPD5402	Approved
0.8158	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1240	Approved
0.8158	Intermediate Similarity	NPD1613	Approved
0.8144	Intermediate Similarity	NPD1247	Approved
0.8133	Intermediate Similarity	NPD919	Approved
0.8107	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD5403	Approved
0.8052	Intermediate Similarity	NPD1607	Approved
0.8039	Intermediate Similarity	NPD943	Approved
0.8037	Intermediate Similarity	NPD6599	Discontinued
0.8013	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.7961	Intermediate Similarity	NPD3027	Phase 3
0.795	Intermediate Similarity	NPD5401	Approved
0.7947	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD3750	Approved
0.7911	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2800	Approved
0.7857	Intermediate Similarity	NPD3749	Approved
0.784	Intermediate Similarity	NPD2533	Approved
0.784	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD2534	Approved
0.7836	Intermediate Similarity	NPD3926	Phase 2
0.7821	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD230	Phase 1
0.7753	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD920	Approved
0.7735	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6234	Discontinued
0.7702	Intermediate Similarity	NPD4628	Phase 3
0.7701	Intermediate Similarity	NPD3751	Discontinued
0.7697	Intermediate Similarity	NPD1653	Approved
0.7684	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3787	Discontinued
0.7673	Intermediate Similarity	NPD6099	Approved
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7673	Intermediate Similarity	NPD6100	Approved
0.765	Intermediate Similarity	NPD4363	Phase 3
0.765	Intermediate Similarity	NPD4360	Phase 2
0.7643	Intermediate Similarity	NPD447	Suspended
0.764	Intermediate Similarity	NPD1243	Approved
0.7627	Intermediate Similarity	NPD7685	Pre-registration
0.7622	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7199	Phase 2
0.761	Intermediate Similarity	NPD3748	Approved
0.7607	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7228	Approved
0.7595	Intermediate Similarity	NPD6651	Approved
0.7579	Intermediate Similarity	NPD7584	Approved
0.7571	Intermediate Similarity	NPD5953	Discontinued
0.7568	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2313	Discontinued
0.7561	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7390	Discontinued
0.7557	Intermediate Similarity	NPD7286	Phase 2
0.7548	Intermediate Similarity	NPD4908	Phase 1
0.7546	Intermediate Similarity	NPD6190	Approved
0.7545	Intermediate Similarity	NPD3226	Approved
0.7542	Intermediate Similarity	NPD8312	Approved
0.7542	Intermediate Similarity	NPD8313	Approved
0.7532	Intermediate Similarity	NPD5124	Phase 1
0.7532	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1933	Approved
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7515	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD9494	Approved
0.7451	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6782	Approved
0.7447	Intermediate Similarity	NPD6778	Approved
0.7447	Intermediate Similarity	NPD6776	Approved
0.7447	Intermediate Similarity	NPD6781	Approved
0.7447	Intermediate Similarity	NPD6777	Approved
0.7447	Intermediate Similarity	NPD6780	Approved
0.7447	Intermediate Similarity	NPD6779	Approved
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8150	Discontinued
0.741	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2344	Approved
0.7389	Intermediate Similarity	NPD4625	Phase 3
0.7371	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD5711	Approved
0.7362	Intermediate Similarity	NPD2424	Discontinued
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7435	Discontinued
0.7322	Intermediate Similarity	NPD8434	Phase 2
0.732	Intermediate Similarity	NPD1610	Phase 2
0.732	Intermediate Similarity	NPD8151	Discontinued
0.731	Intermediate Similarity	NPD6844	Discontinued
0.7285	Intermediate Similarity	NPD1548	Phase 1
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7245	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7783	Phase 2
0.7244	Intermediate Similarity	NPD1203	Approved
0.724	Intermediate Similarity	NPD7698	Approved
0.724	Intermediate Similarity	NPD7697	Approved
0.724	Intermediate Similarity	NPD7696	Phase 3
0.7235	Intermediate Similarity	NPD7458	Discontinued
0.7234	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4361	Phase 2
0.7233	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD6798	Discontinued
0.7232	Intermediate Similarity	NPD5242	Approved
0.7229	Intermediate Similarity	NPD2309	Approved
0.7225	Intermediate Similarity	NPD5353	Approved
0.7215	Intermediate Similarity	NPD6832	Phase 2
0.7212	Intermediate Similarity	NPD1652	Phase 2
0.7205	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7870	Phase 2
0.7202	Intermediate Similarity	NPD7871	Phase 2
0.7198	Intermediate Similarity	NPD7549	Discontinued
0.7197	Intermediate Similarity	NPD2798	Approved
0.7195	Intermediate Similarity	NPD7266	Discontinued
0.7188	Intermediate Similarity	NPD6823	Phase 2
0.7182	Intermediate Similarity	NPD3823	Discontinued
0.7181	Intermediate Similarity	NPD6534	Approved
0.7181	Intermediate Similarity	NPD6535	Approved
0.7179	Intermediate Similarity	NPD7701	Phase 2
0.7179	Intermediate Similarity	NPD7585	Approved
0.7178	Intermediate Similarity	NPD4308	Phase 3
0.7175	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7135	Intermediate Similarity	NPD2494	Approved
0.7135	Intermediate Similarity	NPD2493	Approved
0.7134	Intermediate Similarity	NPD2797	Approved
0.7128	Intermediate Similarity	NPD7583	Approved
0.7125	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7115	Intermediate Similarity	NPD4749	Approved
0.7108	Intermediate Similarity	NPD6674	Discontinued
0.7108	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7874	Approved
0.7107	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6355	Discontinued
0.7097	Intermediate Similarity	NPD422	Phase 1
0.7095	Intermediate Similarity	NPD2403	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