NPASS Compound

Structure

NPC226025 OpenBabel07101719152D 33 35 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 6.9282 3.0000 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 -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 4.3301 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 5.1962 2.0000 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 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 5.1962 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 1 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 0.8660 1.5000 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 -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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 13 18 2 0 0 0 0 13 24 1 0 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 15 23 1 0 0 0 0 19 20 1 0 0 0 0 19 27 2 0 0 0 0 20 28 1 0 0 0 0 21 26 1 0 0 0 0 21 29 2 0 0 0 0 22 24 2 0 0 0 0 22 31 1 0 0 0 0 23 18 1 6 0 0 0 23 33 1 0 0 0 0 24 32 1 0 0 0 0 25 26 2 0 0 0 0 25 33 1 0 0 0 0 26 27 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.22
Volume:	478.892
LogP:	6.171
LogD:	4.029
LogS:	-4.173
# Rotatable Bonds:	8
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	3.352
Fsp3:	0.37
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.767
MDCK Permeability:	1.867469836724922e-05
Pgp-inhibitor:	0.613
Pgp-substrate:	0.367
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	95.06385803222656%
Volume Distribution (VD):	0.404
Pgp-substrate:	3.8744311332702637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.478
CYP2C9-inhibitor:	0.939
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.743
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.608
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	11.263
Half-life (T1/2):	0.187

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.777
Drug-inuced Liver Injury (DILI):	0.733
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.431
Skin Sensitization:	0.798
Carcinogencity:	0.061
Eye Corrosion:	0.003
Eye Irritation:	0.272
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC226025

Natural Product ID:	NPC226025
*Common Name:**	6-Geranyl-5,7-Dihydroxy-3',4'-Dimethoxyflavanone
IUPAC Name:	(2S)-2-(3,4-dimethoxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	XMWZSFFOJPSCLZ-VAPFXODJSA-N
Standard InCHI:	InChI=1S/C27H32O6/c1-16(2)7-6-8-17(3)9-11-19-20(28)14-25-26(27(19)30)21(29)15-23(33-25)18-10-12-22(31-4)24(13-18)32-5/h7,9-10,12-14,23,28,30H,6,8,11,15H2,1-5H3/b17-9+/t23-/m0/s1
SMILES:	CC(=CCC/C(=C/Cc1c(cc2c(C(=O)C[C@@H](c3ccc(c(c3)OC)OC)O2)c1O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581355
PubChem CID:	24854121
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	<	10000.0	nM	PMID[544999]

☑ 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 NPC226025 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	399
0.1-0.2	1536
0.2-0.3	3911
0.3-0.4	9618
0.4-0.5	8606
0.5-0.6	3177
0.6-0.7	4737
0.7-0.8	5370
0.8-0.85	2792
0.85-0.9	1871
0.9-0.95	601
0.95-1	79

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC472626
0.9799	High Similarity	NPC35038
0.9799	High Similarity	NPC195796
0.9799	High Similarity	NPC209614
0.9799	High Similarity	NPC278778
0.9799	High Similarity	NPC291878
0.9799	High Similarity	NPC470328
0.9735	High Similarity	NPC299436
0.9733	High Similarity	NPC472598
0.9733	High Similarity	NPC473272
0.9733	High Similarity	NPC27337
0.9733	High Similarity	NPC291508
0.9733	High Similarity	NPC284820
0.9733	High Similarity	NPC474055
0.9732	High Similarity	NPC200761
0.9732	High Similarity	NPC45849
0.9732	High Similarity	NPC477503
0.9732	High Similarity	NPC470327
0.9728	High Similarity	NPC338131
0.9671	High Similarity	NPC472634
0.9671	High Similarity	NPC471210
0.9664	High Similarity	NPC18727
0.9664	High Similarity	NPC213896
0.9664	High Similarity	NPC298692
0.9664	High Similarity	NPC192083
0.9608	High Similarity	NPC201800
0.9605	High Similarity	NPC475784
0.9605	High Similarity	NPC192686
0.9605	High Similarity	NPC287328
0.9605	High Similarity	NPC472630
0.9605	High Similarity	NPC282009
0.9605	High Similarity	NPC118256
0.9605	High Similarity	NPC472631
0.9605	High Similarity	NPC472624
0.9605	High Similarity	NPC119209
0.9605	High Similarity	NPC36217
0.9603	High Similarity	NPC223787
0.96	High Similarity	NPC321779
0.96	High Similarity	NPC37392
0.9597	High Similarity	NPC106976
0.9597	High Similarity	NPC236637
0.9597	High Similarity	NPC302950
0.9597	High Similarity	NPC219582
0.9592	High Similarity	NPC476342
0.9542	High Similarity	NPC26326
0.9542	High Similarity	NPC474186
0.9542	High Similarity	NPC471499
0.9542	High Similarity	NPC474187
0.9542	High Similarity	NPC472632
0.9542	High Similarity	NPC471211
0.9542	High Similarity	NPC474038
0.9542	High Similarity	NPC471212
0.9539	High Similarity	NPC95936
0.9539	High Similarity	NPC22192
0.9539	High Similarity	NPC473990
0.9539	High Similarity	NPC250214
0.9539	High Similarity	NPC210459
0.9533	High Similarity	NPC74924
0.9484	High Similarity	NPC293319
0.9481	High Similarity	NPC474034
0.9481	High Similarity	NPC472635
0.9481	High Similarity	NPC474033
0.9481	High Similarity	NPC476247
0.9477	High Similarity	NPC475886
0.9477	High Similarity	NPC174953
0.9477	High Similarity	NPC474287
0.9477	High Similarity	NPC321399
0.9477	High Similarity	NPC470326
0.9474	High Similarity	NPC474836
0.9474	High Similarity	NPC78225
0.9474	High Similarity	NPC471515
0.9474	High Similarity	NPC48208
0.9474	High Similarity	NPC471209
0.9474	High Similarity	NPC108456
0.9474	High Similarity	NPC162869
0.9474	High Similarity	NPC156057
0.9474	High Similarity	NPC474208
0.9474	High Similarity	NPC471479
0.9474	High Similarity	NPC475267
0.947	High Similarity	NPC117992
0.947	High Similarity	NPC168247
0.947	High Similarity	NPC152951
0.947	High Similarity	NPC255807
0.947	High Similarity	NPC472909
0.947	High Similarity	NPC31018
0.947	High Similarity	NPC57674
0.947	High Similarity	NPC230149
0.9467	High Similarity	NPC472912
0.9467	High Similarity	NPC471982
0.9459	High Similarity	NPC195202
0.9456	High Similarity	NPC24136
0.9456	High Similarity	NPC187282
0.9456	High Similarity	NPC290133
0.9423	High Similarity	NPC471213
0.9419	High Similarity	NPC472625
0.9419	High Similarity	NPC186686
0.9419	High Similarity	NPC474240
0.9419	High Similarity	NPC124038
0.9416	High Similarity	NPC266314
0.9416	High Similarity	NPC142252
0.9416	High Similarity	NPC134783
0.9416	High Similarity	NPC474351
0.9416	High Similarity	NPC475883
0.9416	High Similarity	NPC158188
0.9412	High Similarity	NPC117418
0.9412	High Similarity	NPC53545
0.9408	High Similarity	NPC13858
0.9408	High Similarity	NPC68093
0.9408	High Similarity	NPC255106
0.9408	High Similarity	NPC235165
0.9408	High Similarity	NPC471500
0.9408	High Similarity	NPC326037
0.9408	High Similarity	NPC191146
0.9408	High Similarity	NPC320825
0.9404	High Similarity	NPC49402
0.9404	High Similarity	NPC70433
0.9404	High Similarity	NPC33051
0.9404	High Similarity	NPC227337
0.9404	High Similarity	NPC472915
0.9404	High Similarity	NPC273462
0.94	High Similarity	NPC117579
0.94	High Similarity	NPC471677
0.9392	High Similarity	NPC12200
0.9392	High Similarity	NPC33265
0.9392	High Similarity	NPC62536
0.9363	High Similarity	NPC218226
0.9359	High Similarity	NPC62261
0.9359	High Similarity	NPC300053
0.9359	High Similarity	NPC108433
0.9359	High Similarity	NPC472277
0.9359	High Similarity	NPC475888
0.9355	High Similarity	NPC474162
0.9355	High Similarity	NPC472964
0.9355	High Similarity	NPC474150
0.9355	High Similarity	NPC211107
0.9355	High Similarity	NPC125991
0.9351	High Similarity	NPC328102
0.9351	High Similarity	NPC470183
0.9346	High Similarity	NPC472914
0.9346	High Similarity	NPC52889
0.9346	High Similarity	NPC245758
0.9346	High Similarity	NPC165977
0.9346	High Similarity	NPC99597
0.9346	High Similarity	NPC472911
0.9346	High Similarity	NPC96167
0.9346	High Similarity	NPC36852
0.9346	High Similarity	NPC472913
0.9346	High Similarity	NPC222814
0.9346	High Similarity	NPC217677
0.9346	High Similarity	NPC210084
0.9346	High Similarity	NPC472910
0.9346	High Similarity	NPC67876
0.9346	High Similarity	NPC181960
0.9346	High Similarity	NPC52530
0.9346	High Similarity	NPC299520
0.9346	High Similarity	NPC262286
0.9346	High Similarity	NPC476981
0.9346	High Similarity	NPC129684
0.9342	High Similarity	NPC67396
0.9342	High Similarity	NPC256925
0.9342	High Similarity	NPC234255
0.9338	High Similarity	NPC477231
0.9338	High Similarity	NPC138288
0.9338	High Similarity	NPC40033
0.9338	High Similarity	NPC260979
0.9338	High Similarity	NPC257648
0.9333	High Similarity	NPC50728
0.9333	High Similarity	NPC472633
0.9333	High Similarity	NPC3825
0.9333	High Similarity	NPC88804
0.9333	High Similarity	NPC166753
0.9329	High Similarity	NPC188679
0.9329	High Similarity	NPC321011
0.9329	High Similarity	NPC294852
0.9324	High Similarity	NPC472629
0.932	High Similarity	NPC185276
0.9299	High Similarity	NPC120593
0.9299	High Similarity	NPC43319
0.9299	High Similarity	NPC272502
0.9299	High Similarity	NPC119589
0.9295	High Similarity	NPC472281
0.9295	High Similarity	NPC18100
0.9295	High Similarity	NPC273959
0.9295	High Similarity	NPC197168
0.9295	High Similarity	NPC7483
0.9295	High Similarity	NPC205265
0.929	High Similarity	NPC40491
0.929	High Similarity	NPC289771
0.929	High Similarity	NPC278052
0.929	High Similarity	NPC474239
0.9286	High Similarity	NPC74178
0.9286	High Similarity	NPC469658
0.9286	High Similarity	NPC204879
0.9286	High Similarity	NPC85121
0.9286	High Similarity	NPC184755
0.9286	High Similarity	NPC152904
0.9281	High Similarity	NPC78492
0.9281	High Similarity	NPC250922
0.9281	High Similarity	NPC471985
0.9281	High Similarity	NPC138243

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 NPC226025 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	922
0.2-0.3	1687
0.3-0.4	2593
0.4-0.5	1800
0.5-0.6	1041
0.6-0.7	537
0.7-0.8	154
0.8-0.85	39
0.85-0.9	20
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9664	High Similarity	NPD2393	Clinical (unspecified phase)
0.9597	High Similarity	NPD1934	Approved
0.915	High Similarity	NPD2801	Approved
0.9114	High Similarity	NPD6167	Clinical (unspecified phase)
0.9114	High Similarity	NPD6168	Clinical (unspecified phase)
0.9114	High Similarity	NPD6166	Phase 2
0.9006	High Similarity	NPD7074	Phase 3
0.9	High Similarity	NPD4378	Clinical (unspecified phase)
0.8981	High Similarity	NPD5494	Approved
0.8974	High Similarity	NPD7075	Discontinued
0.8954	High Similarity	NPD4380	Phase 2
0.8944	High Similarity	NPD7054	Approved
0.8933	High Similarity	NPD1511	Approved
0.8912	High Similarity	NPD1552	Clinical (unspecified phase)
0.8912	High Similarity	NPD1550	Clinical (unspecified phase)
0.891	High Similarity	NPD3882	Suspended
0.8903	High Similarity	NPD7096	Clinical (unspecified phase)
0.8889	High Similarity	NPD7472	Approved
0.8851	High Similarity	NPD1549	Phase 2
0.8846	High Similarity	NPD8443	Clinical (unspecified phase)
0.8846	High Similarity	NPD3817	Phase 2
0.8816	High Similarity	NPD1512	Approved
0.8782	High Similarity	NPD7819	Suspended
0.8765	High Similarity	NPD3818	Discontinued
0.8727	High Similarity	NPD7808	Phase 3
0.8704	High Similarity	NPD7473	Discontinued
0.8671	High Similarity	NPD4868	Clinical (unspecified phase)
0.8667	High Similarity	NPD7251	Discontinued
0.8634	High Similarity	NPD6232	Discontinued
0.8616	High Similarity	NPD4381	Clinical (unspecified phase)
0.8606	High Similarity	NPD6797	Phase 2
0.8598	High Similarity	NPD5844	Phase 1
0.8598	High Similarity	NPD7804	Clinical (unspecified phase)
0.8591	High Similarity	NPD2796	Approved
0.8571	High Similarity	NPD6959	Discontinued
0.8535	High Similarity	NPD7411	Suspended
0.8523	High Similarity	NPD1510	Phase 2
0.8506	High Similarity	NPD7410	Clinical (unspecified phase)
0.8503	High Similarity	NPD4338	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6801	Discontinued
0.8378	Intermediate Similarity	NPD1240	Approved
0.8333	Intermediate Similarity	NPD6559	Discontinued
0.8323	Intermediate Similarity	NPD6799	Approved
0.8267	Intermediate Similarity	NPD1607	Approved
0.8232	Intermediate Similarity	NPD1247	Approved
0.8221	Intermediate Similarity	NPD919	Approved
0.821	Intermediate Similarity	NPD7768	Phase 2
0.8193	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1613	Approved
0.8133	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6599	Discontinued
0.8105	Intermediate Similarity	NPD2935	Discontinued
0.8086	Intermediate Similarity	NPD1465	Phase 2
0.8065	Intermediate Similarity	NPD2800	Approved
0.8065	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2533	Approved
0.8038	Intermediate Similarity	NPD2534	Approved
0.8038	Intermediate Similarity	NPD2532	Approved
0.8037	Intermediate Similarity	NPD5402	Approved
0.8024	Intermediate Similarity	NPD3926	Phase 2
0.8013	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD5403	Approved
0.7933	Intermediate Similarity	NPD3027	Phase 3
0.7919	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD6651	Approved
0.7898	Intermediate Similarity	NPD3750	Approved
0.7871	Intermediate Similarity	NPD6100	Approved
0.7871	Intermediate Similarity	NPD6099	Approved
0.7871	Intermediate Similarity	NPD1551	Phase 2
0.7843	Intermediate Similarity	NPD447	Suspended
0.7836	Intermediate Similarity	NPD7286	Phase 2
0.7831	Intermediate Similarity	NPD3749	Approved
0.7826	Intermediate Similarity	NPD920	Approved
0.7812	Intermediate Similarity	NPD5401	Approved
0.7797	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4628	Phase 3
0.7763	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5953	Discontinued
0.773	Intermediate Similarity	NPD3226	Approved
0.7727	Intermediate Similarity	NPD1933	Approved
0.7727	Intermediate Similarity	NPD230	Phase 1
0.7722	Intermediate Similarity	NPD1243	Approved
0.7709	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2346	Discontinued
0.7702	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD37	Approved
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7692	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6234	Discontinued
0.7673	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4966	Approved
0.7665	Intermediate Similarity	NPD4967	Phase 2
0.7665	Intermediate Similarity	NPD4965	Approved
0.7647	Intermediate Similarity	NPD2313	Discontinued
0.764	Intermediate Similarity	NPD7390	Discontinued
0.7636	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4908	Phase 1
0.7627	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD4360	Phase 2
0.7624	Intermediate Similarity	NPD4363	Phase 3
0.7614	Intermediate Similarity	NPD8312	Approved
0.7614	Intermediate Similarity	NPD8313	Approved
0.7602	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2344	Approved
0.758	Intermediate Similarity	NPD3748	Approved
0.7572	Intermediate Similarity	NPD7228	Approved
0.7572	Intermediate Similarity	NPD3751	Discontinued
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1653	Approved
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7544	Intermediate Similarity	NPD5711	Approved
0.7541	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD5353	Approved
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7468	Intermediate Similarity	NPD4625	Phase 3
0.7468	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7584	Approved
0.7451	Intermediate Similarity	NPD9494	Approved
0.7442	Intermediate Similarity	NPD7229	Phase 3
0.7434	Intermediate Similarity	NPD1203	Approved
0.7417	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7458	Discontinued
0.741	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6190	Approved
0.7407	Intermediate Similarity	NPD2309	Approved
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.7399	Intermediate Similarity	NPD5242	Approved
0.7389	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8150	Discontinued
0.7389	Intermediate Similarity	NPD8434	Phase 2
0.7389	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5124	Phase 1
0.7382	Intermediate Similarity	NPD8151	Discontinued
0.7381	Intermediate Similarity	NPD6844	Discontinued
0.7365	Intermediate Similarity	NPD1548	Phase 1
0.7338	Intermediate Similarity	NPD2861	Phase 2
0.7337	Intermediate Similarity	NPD8455	Phase 2
0.7329	Intermediate Similarity	NPD2424	Discontinued
0.7326	Intermediate Similarity	NPD6776	Approved
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.7326	Intermediate Similarity	NPD6779	Approved
0.7326	Intermediate Similarity	NPD6780	Approved
0.7321	Intermediate Similarity	NPD6386	Approved
0.7321	Intermediate Similarity	NPD6385	Approved
0.7308	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6798	Discontinued
0.7308	Intermediate Similarity	NPD3268	Approved
0.7302	Intermediate Similarity	NPD7698	Approved
0.7302	Intermediate Similarity	NPD7696	Phase 3
0.7302	Intermediate Similarity	NPD7435	Discontinued
0.7302	Intermediate Similarity	NPD7697	Approved
0.7297	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4361	Phase 2
0.7283	Intermediate Similarity	NPD8127	Discontinued
0.7278	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD2798	Approved
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7870	Phase 2
0.7263	Intermediate Similarity	NPD7871	Phase 2
0.7237	Intermediate Similarity	NPD9717	Approved
0.7237	Intermediate Similarity	NPD1608	Approved
0.7226	Intermediate Similarity	NPD3018	Phase 2
0.7216	Intermediate Similarity	NPD7783	Phase 2
0.7216	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7208	Intermediate Similarity	NPD2797	Approved
0.7207	Intermediate Similarity	NPD7240	Approved
0.7191	Intermediate Similarity	NPD1729	Discontinued
0.719	Intermediate Similarity	NPD4749	Approved
0.7181	Intermediate Similarity	NPD5536	Phase 2
0.7178	Intermediate Similarity	NPD6674	Discontinued
0.7178	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1652	Phase 2
0.7178	Intermediate Similarity	NPD2654	Approved
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7171	Intermediate Similarity	NPD1201	Approved
0.716	Intermediate Similarity	NPD7266	Discontinued
0.7159	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2403	Approved
0.7158	Intermediate Similarity	NPD6823	Phase 2
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7151	Intermediate Similarity	NPD5019	Clinical (unspecified phase)

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