NPASS Compound

Structure

NPC470328 OpenBabel07101719252D 34 36 0 0 1 0 0 0 0 0999 V2000 4.3301 -3.5000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 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 5.1962 -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 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 -3.4641 -3.0000 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 0.0000 -2.0000 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 5.1962 -3.0000 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 -3.4641 -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 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 -2.5981 -1.5000 0.0000 C 0 0 3 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 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 0.0000 0.0000 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 -2.0000 0.0000 O 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 32 1 0 0 0 0 5 33 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 18 1 0 0 0 0 11 17 2 0 0 0 0 11 23 1 0 0 0 0 12 17 1 0 0 0 0 12 24 2 0 0 0 0 13 19 2 0 0 0 0 13 22 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 26 2 0 0 0 0 19 28 1 0 0 0 0 20 25 1 0 0 0 0 20 29 2 0 0 0 0 21 34 1 0 0 0 0 22 25 2 0 0 0 0 22 34 1 0 0 0 0 23 27 2 0 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.21
Volume:	487.682
LogP:	5.592
LogD:	3.742
LogS:	-4.353
# Rotatable Bonds:	8
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	3.494
Fsp3:	0.37
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:	-4.871
MDCK Permeability:	1.3448358004097827e-05
Pgp-inhibitor:	0.526
Pgp-substrate:	0.591
Human Intestinal Absorption (HIA):	0.126
20% Bioavailability (F20%):	0.168
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	94.86455535888672%
Volume Distribution (VD):	0.416
Pgp-substrate:	3.3216304779052734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.165
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.928
CYP2C19-substrate:	0.303
CYP2C9-inhibitor:	0.922
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.674
CYP2D6-substrate:	0.654
CYP3A4-inhibitor:	0.428
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	9.215
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.631
Drug-inuced Liver Injury (DILI):	0.418
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.417
Maximum Recommended Daily Dose:	0.486
Skin Sensitization:	0.942
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.653
Respiratory Toxicity:	0.804

Download Data

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

Natural Product: NPC470328

Natural Product ID:	NPC470328
*Common Name:**	6-Geranyl-4',5,7-Trihydroxy-3',5'-Dimethoxyflavanone
IUPAC Name:	6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	UPBJEHBYZUPVDF-CXUHLZMHSA-N
Standard InCHI:	InChI=1S/C27H32O7/c1-15(2)7-6-8-16(3)9-10-18-19(28)13-22-25(26(18)30)20(29)14-21(34-22)17-11-23(32-4)27(31)24(12-17)33-5/h7,9,11-13,21,28,30-31H,6,8,10,14H2,1-5H3/b16-9+
SMILES:	COc1cc(cc(c1O)OC)C1CC(=O)c2c(O1)cc(c(c2O)C/C=C(/CCC=C(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011406
PubChem CID:	70689406
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
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17625893]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[18293924]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192247]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21319773]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22445674]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23623680]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25735399]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28322565]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28968119]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	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	2
Ki	1
MIC	1

Activity Type	# Activity
Individual Protein	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	316300.0	nM	PMID[513219]
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	IC50	=	80000.0	nM	PMID[513219]
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	Ki	=	75200.0	nM	PMID[513219]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[513220]

☑ 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 NPC470328 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	406
0.1-0.2	1548
0.2-0.3	4055
0.3-0.4	9743
0.4-0.5	8522
0.5-0.6	3268
0.6-0.7	4597
0.7-0.8	5317
0.8-0.85	2881
0.85-0.9	1704
0.9-0.95	551
0.95-1	105

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472626
1.0	High Similarity	NPC209614
0.9932	High Similarity	NPC45849
0.9932	High Similarity	NPC200761
0.9932	High Similarity	NPC470327
0.9932	High Similarity	NPC477503
0.9866	High Similarity	NPC278778
0.9866	High Similarity	NPC195796
0.9866	High Similarity	NPC291878
0.9866	High Similarity	NPC35038
0.9865	High Similarity	NPC298692
0.9801	High Similarity	NPC472630
0.9801	High Similarity	NPC472631
0.98	High Similarity	NPC472598
0.98	High Similarity	NPC223787
0.98	High Similarity	NPC291508
0.98	High Similarity	NPC27337
0.98	High Similarity	NPC474055
0.9799	High Similarity	NPC226025
0.9797	High Similarity	NPC106976
0.9737	High Similarity	NPC472634
0.9737	High Similarity	NPC471211
0.9737	High Similarity	NPC471210
0.9737	High Similarity	NPC471212
0.9732	High Similarity	NPC192083
0.9732	High Similarity	NPC18727
0.9732	High Similarity	NPC74924
0.9732	High Similarity	NPC213896
0.9673	High Similarity	NPC201800
0.9671	High Similarity	NPC470326
0.9671	High Similarity	NPC282009
0.9671	High Similarity	NPC36217
0.9671	High Similarity	NPC119209
0.9671	High Similarity	NPC472624
0.9671	High Similarity	NPC192686
0.9671	High Similarity	NPC118256
0.9671	High Similarity	NPC287328
0.9671	High Similarity	NPC174953
0.9667	High Similarity	NPC321779
0.9664	High Similarity	NPC471982
0.9664	High Similarity	NPC219582
0.9664	High Similarity	NPC302950
0.9664	High Similarity	NPC236637
0.9662	High Similarity	NPC338131
0.9608	High Similarity	NPC26326
0.9608	High Similarity	NPC471499
0.9608	High Similarity	NPC472632
0.9608	High Similarity	NPC134783
0.9608	High Similarity	NPC474038
0.9605	High Similarity	NPC210459
0.9605	High Similarity	NPC95936
0.9605	High Similarity	NPC22192
0.9605	High Similarity	NPC473990
0.9605	High Similarity	NPC250214
0.9548	High Similarity	NPC293319
0.9548	High Similarity	NPC475888
0.9545	High Similarity	NPC474033
0.9545	High Similarity	NPC472635
0.9545	High Similarity	NPC474034
0.9545	High Similarity	NPC476247
0.9545	High Similarity	NPC211107
0.9542	High Similarity	NPC475784
0.9542	High Similarity	NPC299436
0.9542	High Similarity	NPC321399
0.9539	High Similarity	NPC78225
0.9539	High Similarity	NPC471209
0.9539	High Similarity	NPC36852
0.9539	High Similarity	NPC474836
0.9539	High Similarity	NPC162869
0.9539	High Similarity	NPC262286
0.9539	High Similarity	NPC48208
0.9539	High Similarity	NPC473272
0.9539	High Similarity	NPC471479
0.9539	High Similarity	NPC475267
0.9539	High Similarity	NPC474208
0.9539	High Similarity	NPC156057
0.9539	High Similarity	NPC52889
0.9539	High Similarity	NPC471515
0.9539	High Similarity	NPC284820
0.9536	High Similarity	NPC168247
0.9536	High Similarity	NPC117992
0.9536	High Similarity	NPC57674
0.9536	High Similarity	NPC152951
0.9536	High Similarity	NPC230149
0.9533	High Similarity	NPC472912
0.9487	High Similarity	NPC471213
0.9484	High Similarity	NPC124038
0.9484	High Similarity	NPC7483
0.9484	High Similarity	NPC186686
0.9484	High Similarity	NPC474240
0.9484	High Similarity	NPC18100
0.9484	High Similarity	NPC472625
0.9481	High Similarity	NPC40491
0.9481	High Similarity	NPC158188
0.9481	High Similarity	NPC474186
0.9481	High Similarity	NPC266314
0.9481	High Similarity	NPC142252
0.9481	High Similarity	NPC278052
0.9477	High Similarity	NPC85121
0.9477	High Similarity	NPC53545
0.9477	High Similarity	NPC469658
0.9477	High Similarity	NPC117418
0.9474	High Similarity	NPC471500
0.9474	High Similarity	NPC235165
0.9474	High Similarity	NPC138243
0.9474	High Similarity	NPC191146
0.9474	High Similarity	NPC320825
0.9474	High Similarity	NPC255106
0.9474	High Similarity	NPC326037
0.9474	High Similarity	NPC13858
0.9474	High Similarity	NPC68093
0.9474	High Similarity	NPC250922
0.947	High Similarity	NPC49402
0.947	High Similarity	NPC33051
0.947	High Similarity	NPC273462
0.947	High Similarity	NPC227337
0.947	High Similarity	NPC70433
0.9463	High Similarity	NPC48479
0.9463	High Similarity	NPC177298
0.9427	High Similarity	NPC218226
0.9423	High Similarity	NPC300053
0.9423	High Similarity	NPC108433
0.9423	High Similarity	NPC326520
0.9423	High Similarity	NPC472277
0.9423	High Similarity	NPC62261
0.9419	High Similarity	NPC81679
0.9419	High Similarity	NPC474162
0.9419	High Similarity	NPC472964
0.9419	High Similarity	NPC474150
0.9416	High Similarity	NPC14353
0.9416	High Similarity	NPC328102
0.9416	High Similarity	NPC228785
0.9416	High Similarity	NPC474287
0.9416	High Similarity	NPC56085
0.9416	High Similarity	NPC475886
0.9416	High Similarity	NPC470183
0.9416	High Similarity	NPC320359
0.9412	High Similarity	NPC52530
0.9412	High Similarity	NPC472910
0.9412	High Similarity	NPC67876
0.9412	High Similarity	NPC469584
0.9412	High Similarity	NPC129684
0.9412	High Similarity	NPC222814
0.9412	High Similarity	NPC472913
0.9412	High Similarity	NPC472914
0.9412	High Similarity	NPC99597
0.9412	High Similarity	NPC245758
0.9412	High Similarity	NPC96167
0.9412	High Similarity	NPC299520
0.9412	High Similarity	NPC472911
0.9412	High Similarity	NPC210084
0.9408	High Similarity	NPC37392
0.9408	High Similarity	NPC256925
0.9408	High Similarity	NPC67396
0.9408	High Similarity	NPC113906
0.9408	High Similarity	NPC234255
0.9404	High Similarity	NPC249570
0.9404	High Similarity	NPC257648
0.9404	High Similarity	NPC477231
0.9404	High Similarity	NPC260979
0.94	High Similarity	NPC3825
0.94	High Similarity	NPC88804
0.9396	High Similarity	NPC120464
0.9396	High Similarity	NPC294852
0.9396	High Similarity	NPC476342
0.9396	High Similarity	NPC321011
0.9396	High Similarity	NPC188679
0.9392	High Similarity	NPC24136
0.9392	High Similarity	NPC290133
0.9392	High Similarity	NPC187282
0.9363	High Similarity	NPC170245
0.9363	High Similarity	NPC43319
0.9359	High Similarity	NPC236132
0.9359	High Similarity	NPC472281
0.9359	High Similarity	NPC41301
0.9359	High Similarity	NPC205265
0.9355	High Similarity	NPC474187
0.9355	High Similarity	NPC474351
0.9355	High Similarity	NPC61010
0.9355	High Similarity	NPC289771
0.9355	High Similarity	NPC474239
0.9355	High Similarity	NPC475883
0.9351	High Similarity	NPC204879
0.9351	High Similarity	NPC74178
0.9351	High Similarity	NPC184755
0.9351	High Similarity	NPC100123
0.9346	High Similarity	NPC24640
0.9346	High Similarity	NPC472455
0.9346	High Similarity	NPC472916
0.9346	High Similarity	NPC471985
0.9342	High Similarity	NPC476631
0.9342	High Similarity	NPC469550
0.9338	High Similarity	NPC471677
0.9338	High Similarity	NPC31363
0.9338	High Similarity	NPC205046
0.9338	High Similarity	NPC59162
0.9338	High Similarity	NPC304295
0.9338	High Similarity	NPC256406
0.9333	High Similarity	NPC137062
0.9333	High Similarity	NPC183950

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 NPC470328 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	930
0.2-0.3	1809
0.3-0.4	2608
0.4-0.5	1763
0.5-0.6	987
0.6-0.7	506
0.7-0.8	135
0.8-0.85	33
0.85-0.9	20
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9732	High Similarity	NPD2393	Clinical (unspecified phase)
0.9664	High Similarity	NPD1934	Approved
0.9216	High Similarity	NPD2801	Approved
0.9177	High Similarity	NPD6168	Clinical (unspecified phase)
0.9177	High Similarity	NPD6166	Phase 2
0.9177	High Similarity	NPD6167	Clinical (unspecified phase)
0.9068	High Similarity	NPD7074	Phase 3
0.9006	High Similarity	NPD7054	Approved
0.9	High Similarity	NPD1511	Approved
0.8974	High Similarity	NPD3882	Suspended
0.8951	High Similarity	NPD7472	Approved
0.8917	High Similarity	NPD7075	Discontinued
0.8896	High Similarity	NPD4380	Phase 2
0.8882	High Similarity	NPD1512	Approved
0.8854	High Similarity	NPD4868	Clinical (unspecified phase)
0.8846	High Similarity	NPD7096	Clinical (unspecified phase)
0.8827	High Similarity	NPD3818	Discontinued
0.8816	High Similarity	NPD4378	Clinical (unspecified phase)
0.8805	High Similarity	NPD5494	Approved
0.879	High Similarity	NPD3817	Phase 2
0.8727	High Similarity	NPD7251	Discontinued
0.8725	High Similarity	NPD1552	Clinical (unspecified phase)
0.8725	High Similarity	NPD1550	Clinical (unspecified phase)
0.8675	High Similarity	NPD7808	Phase 3
0.8671	High Similarity	NPD8443	Clinical (unspecified phase)
0.8667	High Similarity	NPD1549	Phase 2
0.8667	High Similarity	NPD6797	Phase 2
0.8608	High Similarity	NPD7819	Suspended
0.8563	High Similarity	NPD4338	Clinical (unspecified phase)
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8545	High Similarity	NPD7804	Clinical (unspecified phase)
0.8537	High Similarity	NPD7473	Discontinued
0.8519	High Similarity	NPD6959	Discontinued
0.8466	Intermediate Similarity	NPD6232	Discontinued
0.8434	Intermediate Similarity	NPD5844	Phase 1
0.8428	Intermediate Similarity	NPD6801	Discontinued
0.8411	Intermediate Similarity	NPD2796	Approved
0.8365	Intermediate Similarity	NPD7411	Suspended
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8333	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD6559	Discontinued
0.8269	Intermediate Similarity	NPD6799	Approved
0.8261	Intermediate Similarity	NPD1465	Phase 2
0.82	Intermediate Similarity	NPD1613	Approved
0.82	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD1240	Approved
0.8108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1607	Approved
0.8079	Intermediate Similarity	NPD943	Approved
0.8075	Intermediate Similarity	NPD6599	Discontinued
0.8072	Intermediate Similarity	NPD1247	Approved
0.8061	Intermediate Similarity	NPD919	Approved
0.8054	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7768	Phase 2
0.8036	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2800	Approved
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7988	Intermediate Similarity	NPD5402	Approved
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD2532	Approved
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD230	Phase 1
0.7898	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5403	Approved
0.787	Intermediate Similarity	NPD3926	Phase 2
0.7857	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6651	Approved
0.7853	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6234	Discontinued
0.7829	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6099	Approved
0.7821	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5401	Approved
0.7736	Intermediate Similarity	NPD3750	Approved
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD7228	Approved
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7688	Intermediate Similarity	NPD7286	Phase 2
0.7684	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3749	Approved
0.7677	Intermediate Similarity	NPD447	Suspended
0.7673	Intermediate Similarity	NPD1243	Approved
0.7669	Intermediate Similarity	NPD920	Approved
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD37	Approved
0.7647	Intermediate Similarity	NPD7199	Phase 2
0.7643	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1653	Approved
0.7619	Intermediate Similarity	NPD4967	Phase 2
0.7619	Intermediate Similarity	NPD4965	Approved
0.7619	Intermediate Similarity	NPD4966	Approved
0.7614	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5953	Discontinued
0.7597	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7390	Discontinued
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3226	Approved
0.7571	Intermediate Similarity	NPD8313	Approved
0.7571	Intermediate Similarity	NPD8312	Approved
0.7564	Intermediate Similarity	NPD1933	Approved
0.7558	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.7532	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4363	Phase 3
0.7486	Intermediate Similarity	NPD4360	Phase 2
0.7485	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6190	Approved
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.7467	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7456	Intermediate Similarity	NPD5353	Approved
0.7439	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2344	Approved
0.7435	Intermediate Similarity	NPD8151	Discontinued
0.7421	Intermediate Similarity	NPD7584	Approved
0.7421	Intermediate Similarity	NPD3748	Approved
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6832	Phase 2
0.7351	Intermediate Similarity	NPD1610	Phase 2
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7308	Intermediate Similarity	NPD4625	Phase 3
0.7299	Intermediate Similarity	NPD7229	Phase 3
0.7294	Intermediate Similarity	NPD8455	Phase 2
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7284	Intermediate Similarity	NPD2424	Discontinued
0.7273	Intermediate Similarity	NPD1203	Approved
0.7263	Intermediate Similarity	NPD7240	Approved
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7262	Intermediate Similarity	NPD7458	Discontinued
0.7262	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6798	Discontinued
0.7257	Intermediate Similarity	NPD5242	Approved
0.7256	Intermediate Similarity	NPD2309	Approved
0.7239	Intermediate Similarity	NPD6674	Discontinued
0.7235	Intermediate Similarity	NPD6844	Discontinued
0.7233	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6355	Discontinued
0.7233	Intermediate Similarity	NPD5124	Phase 1
0.7233	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7266	Discontinued
0.72	Intermediate Similarity	NPD1548	Phase 1
0.719	Intermediate Similarity	NPD9269	Phase 2
0.7179	Intermediate Similarity	NPD2861	Phase 2
0.7179	Intermediate Similarity	NPD7783	Phase 2
0.7179	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6386	Approved
0.7176	Intermediate Similarity	NPD6385	Approved
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.717	Intermediate Similarity	NPD4060	Phase 1
0.7166	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4361	Phase 2
0.7152	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD4749	Approved
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7134	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7134	Intermediate Similarity	NPD2654	Approved
0.712	Intermediate Similarity	NPD6823	Phase 2
0.7119	Intermediate Similarity	NPD2403	Approved
0.7115	Intermediate Similarity	NPD2798	Approved
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7111	Intermediate Similarity	NPD3823	Discontinued
0.7107	Intermediate Similarity	NPD6233	Phase 2
0.7078	Intermediate Similarity	NPD9717	Approved
0.7078	Intermediate Similarity	NPD1608	Approved
0.707	Intermediate Similarity	NPD3018	Phase 2
0.7056	Intermediate Similarity	NPD1729	Discontinued
0.7051	Intermediate Similarity	NPD2797	Approved
0.7049	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7874	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