NPASS Compound

Structure

NPC470326 OpenBabel07101719252D 34 36 0 0 1 0 0 0 0 0999 V2000 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -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 6.0622 0.5000 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 6.0622 1.5000 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 3.4641 2.0000 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 -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 6.9282 -1.0000 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 -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 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 -2.5981 -1.5000 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 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 2.0000 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 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 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 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 0.0000 3.0000 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 -4.3301 -1.5000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 33 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 27 1 0 0 0 0 18 26 2 0 0 0 0 18 28 1 0 0 0 0 19 26 1 0 0 0 0 19 29 1 0 0 0 0 20 21 2 0 0 0 0 20 34 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 31 2 0 0 0 0 24 25 1 0 0 0 0 24 32 1 1 0 0 0 25 34 1 0 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.19
Volume:	479.176
LogP:	4.989
LogD:	3.175
LogS:	-3.01
# Rotatable Bonds:	7
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	3.973
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:	-5.327
MDCK Permeability:	7.978464964253362e-06
Pgp-inhibitor:	0.293
Pgp-substrate:	0.116
Human Intestinal Absorption (HIA):	0.12
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	93.64368438720703%
Volume Distribution (VD):	0.661
Pgp-substrate:	6.414851665496826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.205
CYP1A2-substrate:	0.54
CYP2C19-inhibitor:	0.374
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.843
CYP2C9-substrate:	0.758
CYP2D6-inhibitor:	0.897
CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	0.394
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	7.114
Half-life (T1/2):	0.394

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.668
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.214
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.899
Carcinogencity:	0.062
Eye Corrosion:	0.003
Eye Irritation:	0.386
Respiratory Toxicity:	0.228

Download Data

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

Natural Product: NPC470326

Natural Product ID:	NPC470326
*Common Name:**	(3R)-2-(3,5-Dihydroxy-4-Methoxyphenyl)-6-((E)-3,7-Dimethylocta-2,6-Dienyl)-3,5,7-Trihydroxychroman-4-One
IUPAC Name:	(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	IZMSMYAPBBZFQP-IMTZNOAFSA-N
Standard InCHI:	InChI=1S/C26H30O8/c1-13(2)6-5-7-14(3)8-9-16-17(27)12-20-21(22(16)30)23(31)24(32)25(34-20)15-10-18(28)26(33-4)19(29)11-15/h6,8,10-12,24-25,27-30,32H,5,7,9H2,1-4H3/b14-8+/t24-,25?/m0/s1
SMILES:	CC(=CCCC(=CCC1=C(C2=C(C=C1O)OC(C(C2=O)O)C3=CC(=C(C(=C3)O)OC)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011403
PubChem CID:	70687354
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins [CHEMONTID:0001594] Epigallocatechins

*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	2
Others	2

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	15600.0	nM	PMID[486127]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ki	=	16900.0	nM	PMID[486127]
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	IC50	=	3800.0	nM	PMID[486127]
NPT2569	Individual Protein	Butyrylcholinesterase	Equus caballus	Ki	=	4500.0	nM	PMID[486127]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	KSV	=	0.0369	10'5L/M	PMID[486127]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ka	=	4.535	10'3L/M	PMID[486127]

☑ 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 NPC470326 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	410
0.1-0.2	1597
0.2-0.3	4030
0.3-0.4	9640
0.4-0.5	8582
0.5-0.6	3549
0.6-0.7	4668
0.7-0.8	5312
0.8-0.85	2782
0.85-0.9	1706
0.9-0.95	357
0.95-1	64

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC471499
0.9868	High Similarity	NPC282009
0.9868	High Similarity	NPC287328
0.9803	High Similarity	NPC22192
0.9801	High Similarity	NPC250922
0.9739	High Similarity	NPC472630
0.9739	High Similarity	NPC472631
0.9737	High Similarity	NPC472598
0.9737	High Similarity	NPC474055
0.9735	High Similarity	NPC200761
0.9735	High Similarity	NPC477503
0.9735	High Similarity	NPC45849
0.9735	High Similarity	NPC470327
0.9679	High Similarity	NPC471213
0.9677	High Similarity	NPC472625
0.9675	High Similarity	NPC289771
0.9675	High Similarity	NPC472634
0.9675	High Similarity	NPC26326
0.9671	High Similarity	NPC13858
0.9671	High Similarity	NPC326037
0.9671	High Similarity	NPC35038
0.9671	High Similarity	NPC195796
0.9671	High Similarity	NPC470328
0.9671	High Similarity	NPC209614
0.9671	High Similarity	NPC278778
0.9671	High Similarity	NPC291878
0.9671	High Similarity	NPC320825
0.9671	High Similarity	NPC472626
0.9615	High Similarity	NPC475888
0.9615	High Similarity	NPC470457
0.9613	High Similarity	NPC211107
0.9613	High Similarity	NPC472635
0.961	High Similarity	NPC174953
0.9608	High Similarity	NPC471479
0.9608	High Similarity	NPC291508
0.9608	High Similarity	NPC52530
0.9608	High Similarity	NPC471515
0.9608	High Similarity	NPC27337
0.9608	High Similarity	NPC223787
0.9605	High Similarity	NPC321779
0.9603	High Similarity	NPC106976
0.9603	High Similarity	NPC19721
0.9551	High Similarity	NPC474240
0.9551	High Similarity	NPC470459
0.9551	High Similarity	NPC41301
0.9548	High Similarity	NPC142252
0.9548	High Similarity	NPC471211
0.9548	High Similarity	NPC472632
0.9548	High Similarity	NPC474038
0.9548	High Similarity	NPC471212
0.9545	High Similarity	NPC473990
0.9545	High Similarity	NPC53545
0.9545	High Similarity	NPC117418
0.9542	High Similarity	NPC471500
0.9539	High Similarity	NPC74924
0.9539	High Similarity	NPC298692
0.9539	High Similarity	NPC213896
0.9539	High Similarity	NPC192083
0.9539	High Similarity	NPC18727
0.9497	High Similarity	NPC102277
0.9497	High Similarity	NPC279209
0.9494	High Similarity	NPC158761
0.9494	High Similarity	NPC470456
0.949	High Similarity	NPC36916
0.949	High Similarity	NPC58223
0.949	High Similarity	NPC36
0.949	High Similarity	NPC62261
0.949	High Similarity	NPC72787
0.949	High Similarity	NPC7154
0.949	High Similarity	NPC7688
0.949	High Similarity	NPC125039
0.9487	High Similarity	NPC474034
0.9487	High Similarity	NPC474033
0.9487	High Similarity	NPC476247
0.9484	High Similarity	NPC36217
0.9484	High Similarity	NPC118256
0.9484	High Similarity	NPC475784
0.9484	High Similarity	NPC470183
0.9484	High Similarity	NPC472624
0.9484	High Similarity	NPC192686
0.9484	High Similarity	NPC263449
0.9484	High Similarity	NPC119209
0.9481	High Similarity	NPC67876
0.9477	High Similarity	NPC226025
0.9474	High Similarity	NPC246162
0.9474	High Similarity	NPC471982
0.9474	High Similarity	NPC61506
0.9474	High Similarity	NPC240476
0.9474	High Similarity	NPC9743
0.9474	High Similarity	NPC302950
0.9474	High Similarity	NPC219582
0.9474	High Similarity	NPC260491
0.9474	High Similarity	NPC36835
0.9474	High Similarity	NPC236637
0.947	High Similarity	NPC338131
0.943	High Similarity	NPC470462
0.9427	High Similarity	NPC124038
0.9423	High Similarity	NPC471210
0.9423	High Similarity	NPC308992
0.9423	High Similarity	NPC134783
0.9423	High Similarity	NPC158188
0.9423	High Similarity	NPC474239
0.9423	High Similarity	NPC266314
0.9423	High Similarity	NPC112418
0.9419	High Similarity	NPC95936
0.9419	High Similarity	NPC250214
0.9412	High Similarity	NPC325028
0.9412	High Similarity	NPC27532
0.9412	High Similarity	NPC58382
0.9412	High Similarity	NPC246328
0.9412	High Similarity	NPC162351
0.9412	High Similarity	NPC256346
0.9408	High Similarity	NPC278476
0.9408	High Similarity	NPC319910
0.9408	High Similarity	NPC304295
0.9408	High Similarity	NPC50403
0.9408	High Similarity	NPC28274
0.9408	High Similarity	NPC254412
0.9408	High Similarity	NPC205046
0.9408	High Similarity	NPC133953
0.9408	High Similarity	NPC59162
0.9408	High Similarity	NPC262038
0.9408	High Similarity	NPC262039
0.9371	High Similarity	NPC474024
0.9371	High Similarity	NPC260266
0.9371	High Similarity	NPC477502
0.9363	High Similarity	NPC201800
0.9363	High Similarity	NPC220912
0.9363	High Similarity	NPC471745
0.9359	High Similarity	NPC471744
0.9359	High Similarity	NPC321399
0.9359	High Similarity	NPC246478
0.9359	High Similarity	NPC101731
0.9355	High Similarity	NPC475267
0.9355	High Similarity	NPC48208
0.9355	High Similarity	NPC474208
0.9355	High Similarity	NPC262286
0.9355	High Similarity	NPC473272
0.9355	High Similarity	NPC36852
0.9355	High Similarity	NPC471209
0.9355	High Similarity	NPC474836
0.9355	High Similarity	NPC52889
0.9355	High Similarity	NPC162869
0.9355	High Similarity	NPC156057
0.9355	High Similarity	NPC284820
0.9355	High Similarity	NPC78225
0.9351	High Similarity	NPC133392
0.9351	High Similarity	NPC152951
0.9351	High Similarity	NPC117992
0.9351	High Similarity	NPC168247
0.9351	High Similarity	NPC304745
0.9351	High Similarity	NPC111341
0.9351	High Similarity	NPC57674
0.9351	High Similarity	NPC230149
0.9346	High Similarity	NPC243171
0.9346	High Similarity	NPC157784
0.9346	High Similarity	NPC35567
0.9346	High Similarity	NPC123886
0.9346	High Similarity	NPC63187
0.9346	High Similarity	NPC37684
0.9346	High Similarity	NPC216035
0.9346	High Similarity	NPC217149
0.9346	High Similarity	NPC171651
0.9346	High Similarity	NPC472912
0.9346	High Similarity	NPC138288
0.9342	High Similarity	NPC105136
0.9342	High Similarity	NPC219330
0.9313	High Similarity	NPC326877
0.9313	High Similarity	NPC475212
0.9308	High Similarity	NPC119589
0.9308	High Similarity	NPC207575
0.9308	High Similarity	NPC13481
0.9304	High Similarity	NPC18100
0.9304	High Similarity	NPC7483
0.9304	High Similarity	NPC186686
0.9299	High Similarity	NPC66618
0.9299	High Similarity	NPC173137
0.9299	High Similarity	NPC187354
0.9299	High Similarity	NPC84324
0.9299	High Similarity	NPC305987
0.9299	High Similarity	NPC165970
0.9299	High Similarity	NPC113163
0.9299	High Similarity	NPC288131
0.9299	High Similarity	NPC228383
0.9295	High Similarity	NPC55738
0.9295	High Similarity	NPC172202
0.9295	High Similarity	NPC476410
0.9295	High Similarity	NPC210459
0.9295	High Similarity	NPC152904
0.9295	High Similarity	NPC85121
0.9295	High Similarity	NPC284127
0.929	High Similarity	NPC138243
0.929	High Similarity	NPC255106
0.929	High Similarity	NPC20530
0.929	High Similarity	NPC215917
0.929	High Similarity	NPC235165
0.929	High Similarity	NPC474520
0.929	High Similarity	NPC474638
0.929	High Similarity	NPC55619
0.929	High Similarity	NPC100916

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 NPC470326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	928
0.2-0.3	1887
0.3-0.4	2593
0.4-0.5	1769
0.5-0.6	957
0.6-0.7	465
0.7-0.8	135
0.8-0.85	31
0.85-0.9	17
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9539	High Similarity	NPD2393	Clinical (unspecified phase)
0.949	High Similarity	NPD6167	Clinical (unspecified phase)
0.949	High Similarity	NPD6168	Clinical (unspecified phase)
0.949	High Similarity	NPD6166	Phase 2
0.9474	High Similarity	NPD1934	Approved
0.9045	High Similarity	NPD3882	Suspended
0.9038	High Similarity	NPD2801	Approved
0.9018	High Similarity	NPD7074	Phase 3
0.8987	High Similarity	NPD7075	Discontinued
0.8981	High Similarity	NPD3817	Phase 2
0.8968	High Similarity	NPD4380	Phase 2
0.8963	High Similarity	NPD6797	Phase 2
0.8957	High Similarity	NPD7054	Approved
0.8954	High Similarity	NPD1512	Approved
0.8909	High Similarity	NPD7251	Discontinued
0.8902	High Similarity	NPD7472	Approved
0.8896	High Similarity	NPD3818	Discontinued
0.8889	High Similarity	NPD4378	Clinical (unspecified phase)
0.8855	High Similarity	NPD7808	Phase 3
0.8855	High Similarity	NPD4338	Clinical (unspecified phase)
0.8824	High Similarity	NPD1511	Approved
0.8805	High Similarity	NPD4868	Clinical (unspecified phase)
0.8797	High Similarity	NPD7096	Clinical (unspecified phase)
0.8734	High Similarity	NPD6801	Discontinued
0.8727	High Similarity	NPD7804	Clinical (unspecified phase)
0.8642	High Similarity	NPD5494	Approved
0.8634	High Similarity	NPD4381	Clinical (unspecified phase)
0.8623	High Similarity	NPD7993	Clinical (unspecified phase)
0.8553	High Similarity	NPD1552	Clinical (unspecified phase)
0.8553	High Similarity	NPD1550	Clinical (unspecified phase)
0.8509	High Similarity	NPD8443	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1549	Phase 2
0.8476	Intermediate Similarity	NPD6959	Discontinued
0.8447	Intermediate Similarity	NPD7819	Suspended
0.8424	Intermediate Similarity	NPD6232	Discontinued
0.8393	Intermediate Similarity	NPD5844	Phase 1
0.8383	Intermediate Similarity	NPD7473	Discontinued
0.8353	Intermediate Similarity	NPD6559	Discontinued
0.8344	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8291	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD5402	Approved
0.8247	Intermediate Similarity	NPD2796	Approved
0.8221	Intermediate Similarity	NPD1465	Phase 2
0.8187	Intermediate Similarity	NPD5403	Approved
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8158	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1613	Approved
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.8144	Intermediate Similarity	NPD1247	Approved
0.8133	Intermediate Similarity	NPD919	Approved
0.8063	Intermediate Similarity	NPD5401	Approved
0.8047	Intermediate Similarity	NPD3926	Phase 2
0.8039	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD3027	Phase 3
0.7947	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1607	Approved
0.7922	Intermediate Similarity	NPD943	Approved
0.7895	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2800	Approved
0.784	Intermediate Similarity	NPD2533	Approved
0.784	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD2534	Approved
0.7833	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6234	Discontinued
0.7799	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7768	Phase 2
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7764	Intermediate Similarity	NPD6190	Approved
0.7756	Intermediate Similarity	NPD230	Phase 1
0.7753	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD37	Approved
0.7722	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7199	Phase 2
0.7707	Intermediate Similarity	NPD6651	Approved
0.7702	Intermediate Similarity	NPD4628	Phase 3
0.7701	Intermediate Similarity	NPD3751	Discontinued
0.7701	Intermediate Similarity	NPD7228	Approved
0.7697	Intermediate Similarity	NPD1653	Approved
0.7692	Intermediate Similarity	NPD4966	Approved
0.7692	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD4967	Phase 2
0.7674	Intermediate Similarity	NPD3787	Discontinued
0.7663	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3750	Approved
0.7584	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5953	Discontinued
0.7564	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1551	Phase 2
0.7562	Intermediate Similarity	NPD6099	Approved
0.7562	Intermediate Similarity	NPD6100	Approved
0.7561	Intermediate Similarity	NPD7390	Discontinued
0.7545	Intermediate Similarity	NPD3226	Approved
0.7544	Intermediate Similarity	NPD3749	Approved
0.7542	Intermediate Similarity	NPD8313	Approved
0.7542	Intermediate Similarity	NPD8312	Approved
0.754	Intermediate Similarity	NPD6782	Approved
0.754	Intermediate Similarity	NPD6777	Approved
0.754	Intermediate Similarity	NPD6781	Approved
0.754	Intermediate Similarity	NPD6780	Approved
0.754	Intermediate Similarity	NPD6776	Approved
0.754	Intermediate Similarity	NPD6779	Approved
0.754	Intermediate Similarity	NPD6778	Approved
0.7532	Intermediate Similarity	NPD447	Suspended
0.7531	Intermediate Similarity	NPD1243	Approved
0.753	Intermediate Similarity	NPD920	Approved
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4360	Phase 2
0.7459	Intermediate Similarity	NPD4363	Phase 3
0.7458	Intermediate Similarity	NPD7286	Phase 2
0.7455	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7685	Pre-registration
0.7421	Intermediate Similarity	NPD1933	Approved
0.7421	Intermediate Similarity	NPD7435	Discontinued
0.741	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD8151	Discontinued
0.7407	Intermediate Similarity	NPD2346	Discontinued
0.7396	Intermediate Similarity	NPD7584	Approved
0.7394	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2799	Discontinued
0.7378	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD9494	Approved
0.7371	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD5711	Approved
0.7342	Intermediate Similarity	NPD2313	Discontinued
0.7342	Intermediate Similarity	NPD6798	Discontinued
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7696	Phase 3
0.733	Intermediate Similarity	NPD7697	Approved
0.733	Intermediate Similarity	NPD7698	Approved
0.7325	Intermediate Similarity	NPD4908	Phase 1
0.732	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2344	Approved
0.7292	Intermediate Similarity	NPD7871	Phase 2
0.7292	Intermediate Similarity	NPD7870	Phase 2
0.7284	Intermediate Similarity	NPD7033	Discontinued
0.7284	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7268	Intermediate Similarity	NPD7701	Phase 2
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7256	Intermediate Similarity	NPD2424	Discontinued
0.7251	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4060	Phase 1
0.7238	Intermediate Similarity	NPD7240	Approved
0.7235	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5353	Approved
0.7215	Intermediate Similarity	NPD6832	Phase 2
0.7208	Intermediate Similarity	NPD1610	Phase 2
0.7205	Intermediate Similarity	NPD5124	Phase 1
0.7205	Intermediate Similarity	NPD6355	Discontinued
0.7205	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7266	Discontinued
0.7194	Intermediate Similarity	NPD7874	Approved
0.7194	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2403	Approved
0.7188	Intermediate Similarity	NPD6233	Phase 2
0.717	Intermediate Similarity	NPD4625	Phase 3
0.7158	Intermediate Similarity	NPD7699	Phase 2
0.7158	Intermediate Similarity	NPD7700	Phase 2
0.7157	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7783	Phase 2
0.7157	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD5242	Approved
0.7134	Intermediate Similarity	NPD1203	Approved
0.7126	Intermediate Similarity	NPD2309	Approved
0.7125	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7111	Intermediate Similarity	NPD2163	Approved
0.711	Intermediate Similarity	NPD6844	Discontinued
0.7108	Intermediate Similarity	NPD6674	Discontinued
0.7108	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1652	Phase 2
0.7099	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6823	Phase 2
0.7095	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD3823	Discontinued
0.7079	Intermediate Similarity	NPD7229	Phase 3
0.7059	Intermediate Similarity	NPD1548	Phase 1
0.7051	Intermediate Similarity	NPD9269	Phase 2
0.7047	Intermediate Similarity	NPD2493	Approved
0.7047	Intermediate Similarity	NPD2494	Approved
0.7044	Intermediate Similarity	NPD2861	Phase 2
0.7044	Intermediate Similarity	NPD3018	Phase 2
0.7035	Intermediate Similarity	NPD7458	Discontinued
0.7026	Intermediate Similarity	NPD8320	Phase 1

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