NPASS Compound

Structure

NPC134783 OpenBabel07101719152D 27 30 0 0 1 0 0 0 0 0999 V2000 -1.1248 -0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 1.1088 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 2.5981 0.5000 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 6.0622 1.5000 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 -0.8660 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 6.9282 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 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 4.3301 3.5000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 1 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 5.1962 3.0000 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 0.5000 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 6.0622 4.5000 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 -1.0000 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 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 9 2 0 0 0 0 3 11 1 0 0 0 0 4 9 1 0 0 0 0 4 14 2 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 17 2 0 0 0 0 7 13 1 0 0 0 0 7 16 1 0 0 0 0 8 15 1 0 0 0 0 8 20 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 18 1 0 0 0 0 13 23 2 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 16 9 1 6 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 19 27 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.11
Volume:	360.69
LogP:	3.521
LogD:	2.851
LogS:	-5.725
# Rotatable Bonds:	1
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.706
Synthetic Accessibility Score:	3.478
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.782
MDCK Permeability:	1.8885884855990298e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	92.03860473632812%
Volume Distribution (VD):	0.84
Pgp-substrate:	6.212126731872559%

ADMET: Metabolism

CYP1A2-inhibitor:	0.64
CYP1A2-substrate:	0.265
CYP2C19-inhibitor:	0.692
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.852
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.63
CYP2D6-substrate:	0.243
CYP3A4-inhibitor:	0.727
CYP3A4-substrate:	0.142

ADMET: Excretion

Clearance (CL):	13.346
Half-life (T1/2):	0.492

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.279
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.857
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.851
Carcinogencity:	0.627
Eye Corrosion:	0.003
Eye Irritation:	0.471
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC134783

Natural Product ID:	NPC134783
*Common Name:**	(S)-5,7,8'-Trihydroxy-2',2'-Dimethyl-2,6'-Bichroman-4,4'-Dione
IUPAC Name:	6-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-8-hydroxy-2,2-dimethyl-3H-chromen-4-one
Synonyms:
Standard InCHIKey:	QVJWSGOMMDXZOF-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C20H18O7/c1-20(2)8-15(25)11-3-9(4-14(24)19(11)27-20)16-7-13(23)18-12(22)5-10(21)6-17(18)26-16/h3-6,16,21-22,24H,7-8H2,1-2H3/t16-/m0/s1
SMILES:	Oc1cc2O[C@@H](CC(=O)c2c(c1)O)c1cc(O)c2c(c1)C(=O)CC(O2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458813
PubChem CID:	44589231
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003643] 3'-prenylated flavans [CHEMONTID:0003506] 3'-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
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8526	Erythrina abyssinica	Species	Fabaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	60000.0	nM	PMID[507567]

☑ 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 NPC134783 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	414
0.1-0.2	1681
0.2-0.3	4163
0.3-0.4	9803
0.4-0.5	8314
0.5-0.6	3459
0.6-0.7	4749
0.7-0.8	5227
0.8-0.85	2803
0.85-0.9	1681
0.9-0.95	346
0.95-1	57

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC474033
0.9805	High Similarity	NPC474034
0.9804	High Similarity	NPC174953
0.974	High Similarity	NPC471210
0.974	High Similarity	NPC471211
0.974	High Similarity	NPC471212
0.974	High Similarity	NPC472632
0.9739	High Similarity	NPC473990
0.9679	High Similarity	NPC62261
0.9675	High Similarity	NPC119209
0.9675	High Similarity	NPC192686
0.9675	High Similarity	NPC118256
0.9673	High Similarity	NPC52889
0.9673	High Similarity	NPC27337
0.9673	High Similarity	NPC291508
0.9673	High Similarity	NPC471209
0.9671	High Similarity	NPC477503
0.9671	High Similarity	NPC45849
0.9671	High Similarity	NPC200761
0.9671	High Similarity	NPC470327
0.9615	High Similarity	NPC124038
0.9613	High Similarity	NPC474038
0.961	High Similarity	NPC204879
0.9608	High Similarity	NPC209614
0.9608	High Similarity	NPC470328
0.9608	High Similarity	NPC291878
0.9608	High Similarity	NPC195796
0.9608	High Similarity	NPC472626
0.9608	High Similarity	NPC278778
0.9608	High Similarity	NPC470600
0.9608	High Similarity	NPC35038
0.9605	High Similarity	NPC74924
0.9557	High Similarity	NPC6588
0.9557	High Similarity	NPC477154
0.9557	High Similarity	NPC117854
0.9554	High Similarity	NPC300053
0.9554	High Similarity	NPC293319
0.9554	High Similarity	NPC108433
0.9551	High Similarity	NPC472448
0.9551	High Similarity	NPC474150
0.9551	High Similarity	NPC83922
0.9551	High Similarity	NPC474162
0.9551	High Similarity	NPC220912
0.9551	High Similarity	NPC476247
0.9548	High Similarity	NPC472624
0.9548	High Similarity	NPC472630
0.9548	High Similarity	NPC475784
0.9548	High Similarity	NPC472631
0.9545	High Similarity	NPC472598
0.9545	High Similarity	NPC262286
0.9545	High Similarity	NPC218313
0.9545	High Similarity	NPC474055
0.9545	High Similarity	NPC474681
0.9545	High Similarity	NPC284820
0.9545	High Similarity	NPC36852
0.9545	High Similarity	NPC473272
0.9545	High Similarity	NPC223787
0.9542	High Similarity	NPC230149
0.9542	High Similarity	NPC57674
0.9542	High Similarity	NPC152951
0.9542	High Similarity	NPC117992
0.9542	High Similarity	NPC168247
0.9542	High Similarity	NPC256925
0.9539	High Similarity	NPC106976
0.9497	High Similarity	NPC288813
0.9494	High Similarity	NPC471213
0.949	High Similarity	NPC248638
0.949	High Similarity	NPC152659
0.949	High Similarity	NPC186686
0.949	High Similarity	NPC18100
0.949	High Similarity	NPC236521
0.949	High Similarity	NPC472625
0.9487	High Similarity	NPC228383
0.9487	High Similarity	NPC167678
0.9487	High Similarity	NPC26326
0.9487	High Similarity	NPC29876
0.9487	High Similarity	NPC472634
0.9487	High Similarity	NPC173137
0.9484	High Similarity	NPC74178
0.9484	High Similarity	NPC250214
0.9484	High Similarity	NPC95936
0.9484	High Similarity	NPC184755
0.9481	High Similarity	NPC5322
0.9481	High Similarity	NPC472455
0.9481	High Similarity	NPC6633
0.9481	High Similarity	NPC133970
0.9481	High Similarity	NPC138243
0.9477	High Similarity	NPC227337
0.9477	High Similarity	NPC298692
0.9477	High Similarity	NPC273462
0.9477	High Similarity	NPC18727
0.9477	High Similarity	NPC70433
0.9477	High Similarity	NPC49402
0.9477	High Similarity	NPC192083
0.9477	High Similarity	NPC33051
0.9477	High Similarity	NPC213896
0.9434	High Similarity	NPC474024
0.943	High Similarity	NPC224280
0.943	High Similarity	NPC234052
0.943	High Similarity	NPC472277
0.9427	High Similarity	NPC25152
0.9427	High Similarity	NPC472635
0.9427	High Similarity	NPC81679
0.9427	High Similarity	NPC261470
0.9423	High Similarity	NPC470326
0.9423	High Similarity	NPC287328
0.9423	High Similarity	NPC476980
0.9423	High Similarity	NPC204290
0.9423	High Similarity	NPC471976
0.9423	High Similarity	NPC328102
0.9423	High Similarity	NPC282009
0.9423	High Similarity	NPC36217
0.9419	High Similarity	NPC78225
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC67876
0.9419	High Similarity	NPC129684
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC99597
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC299520
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC475267
0.9419	High Similarity	NPC210084
0.9416	High Similarity	NPC234255
0.9416	High Similarity	NPC321779
0.9416	High Similarity	NPC113906
0.9416	High Similarity	NPC472280
0.9416	High Similarity	NPC200246
0.9416	High Similarity	NPC226025
0.9412	High Similarity	NPC471982
0.9412	High Similarity	NPC477231
0.9412	High Similarity	NPC236637
0.9412	High Similarity	NPC219582
0.9412	High Similarity	NPC302950
0.9412	High Similarity	NPC257648
0.9408	High Similarity	NPC338131
0.9375	High Similarity	NPC152477
0.9371	High Similarity	NPC170245
0.9371	High Similarity	NPC13481
0.9371	High Similarity	NPC120593
0.9371	High Similarity	NPC477517
0.9371	High Similarity	NPC119589
0.9371	High Similarity	NPC207575
0.9371	High Similarity	NPC235610
0.9371	High Similarity	NPC43319
0.9371	High Similarity	NPC173292
0.9367	High Similarity	NPC205265
0.9367	High Similarity	NPC273959
0.9367	High Similarity	NPC472281
0.9367	High Similarity	NPC41301
0.9363	High Similarity	NPC142252
0.9363	High Similarity	NPC266314
0.9363	High Similarity	NPC57715
0.9363	High Similarity	NPC234644
0.9363	High Similarity	NPC259456
0.9363	High Similarity	NPC61010
0.9363	High Similarity	NPC471499
0.9363	High Similarity	NPC3629
0.9359	High Similarity	NPC53545
0.9359	High Similarity	NPC55738
0.9359	High Similarity	NPC117418
0.9359	High Similarity	NPC22192
0.9355	High Similarity	NPC472916
0.9355	High Similarity	NPC191146
0.9355	High Similarity	NPC255106
0.9355	High Similarity	NPC471985
0.9355	High Similarity	NPC282307
0.9355	High Similarity	NPC474638
0.9355	High Similarity	NPC235165
0.9355	High Similarity	NPC68093
0.9355	High Similarity	NPC170026
0.9351	High Similarity	NPC469405
0.9346	High Similarity	NPC474021
0.9346	High Similarity	NPC474023
0.9346	High Similarity	NPC31363
0.9317	High Similarity	NPC103307
0.9317	High Similarity	NPC472276
0.9313	High Similarity	NPC477502
0.9313	High Similarity	NPC8965
0.9313	High Similarity	NPC218226
0.9313	High Similarity	NPC14662
0.9308	High Similarity	NPC239752
0.9308	High Similarity	NPC326520
0.9308	High Similarity	NPC472450
0.9308	High Similarity	NPC275780
0.9308	High Similarity	NPC50960
0.9304	High Similarity	NPC201800
0.9304	High Similarity	NPC472964
0.9299	High Similarity	NPC472902
0.9299	High Similarity	NPC200746
0.9299	High Similarity	NPC56085
0.9299	High Similarity	NPC471973
0.9299	High Similarity	NPC474960
0.9299	High Similarity	NPC14353
0.9299	High Similarity	NPC228785
0.9299	High Similarity	NPC188433
0.9295	High Similarity	NPC471479
0.9295	High Similarity	NPC469584
0.9295	High Similarity	NPC52530

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 NPC134783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	959
0.2-0.3	1857
0.3-0.4	2611
0.4-0.5	1763
0.5-0.6	966
0.6-0.7	436
0.7-0.8	138
0.8-0.85	30
0.85-0.9	17
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9477	High Similarity	NPD2393	Clinical (unspecified phase)
0.9412	High Similarity	NPD1934	Approved
0.9187	High Similarity	NPD6168	Clinical (unspecified phase)
0.9187	High Similarity	NPD6166	Phase 2
0.9187	High Similarity	NPD6167	Clinical (unspecified phase)
0.9103	High Similarity	NPD2801	Approved
0.9057	High Similarity	NPD5494	Approved
0.8987	High Similarity	NPD4868	Clinical (unspecified phase)
0.8987	High Similarity	NPD3882	Suspended
0.8963	High Similarity	NPD7074	Phase 3
0.891	High Similarity	NPD4380	Phase 2
0.8902	High Similarity	NPD7054	Approved
0.8848	High Similarity	NPD7472	Approved
0.8841	High Similarity	NPD3818	Discontinued
0.8766	High Similarity	NPD1511	Approved
0.8696	High Similarity	NPD7075	Discontinued
0.8683	High Similarity	NPD6797	Phase 2
0.8654	High Similarity	NPD1512	Approved
0.8631	High Similarity	NPD7251	Discontinued
0.8625	High Similarity	NPD7096	Clinical (unspecified phase)
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.858	High Similarity	NPD4381	Clinical (unspecified phase)
0.858	High Similarity	NPD7808	Phase 3
0.858	High Similarity	NPD4338	Clinical (unspecified phase)
0.8571	High Similarity	NPD7993	Clinical (unspecified phase)
0.8571	High Similarity	NPD3817	Phase 2
0.8562	High Similarity	NPD1549	Phase 2
0.8537	High Similarity	NPD6959	Discontinued
0.8509	High Similarity	NPD1465	Phase 2
0.8497	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD5844	Phase 1
0.8452	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD7819	Suspended
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8373	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8312	Intermediate Similarity	NPD2796	Approved
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8198	Intermediate Similarity	NPD6559	Discontinued
0.8176	Intermediate Similarity	NPD6799	Approved
0.8121	Intermediate Similarity	NPD5402	Approved
0.8105	Intermediate Similarity	NPD1240	Approved
0.8105	Intermediate Similarity	NPD943	Approved
0.8095	Intermediate Similarity	NPD1247	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1607	Approved
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD919	Approved
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7935	Intermediate Similarity	NPD230	Phase 1
0.7925	Intermediate Similarity	NPD2800	Approved
0.7917	Intermediate Similarity	NPD3749	Approved
0.7914	Intermediate Similarity	NPD5403	Approved
0.7901	Intermediate Similarity	NPD2532	Approved
0.7901	Intermediate Similarity	NPD2534	Approved
0.7901	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3926	Phase 2
0.7877	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7843	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3027	Phase 3
0.7791	Intermediate Similarity	NPD5401	Approved
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6234	Discontinued
0.7764	Intermediate Similarity	NPD3750	Approved
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.7759	Intermediate Similarity	NPD7228	Approved
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD447	Suspended
0.7697	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD920	Approved
0.7697	Intermediate Similarity	NPD8313	Approved
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4628	Phase 3
0.763	Intermediate Similarity	NPD3787	Discontinued
0.7627	Intermediate Similarity	NPD5953	Discontinued
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7625	Intermediate Similarity	NPD6099	Approved
0.7625	Intermediate Similarity	NPD6100	Approved
0.7614	Intermediate Similarity	NPD7286	Phase 2
0.7607	Intermediate Similarity	NPD6190	Approved
0.7605	Intermediate Similarity	NPD3226	Approved
0.7593	Intermediate Similarity	NPD1243	Approved
0.7584	Intermediate Similarity	NPD7685	Pre-registration
0.7578	Intermediate Similarity	NPD2346	Discontinued
0.7576	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD37	Approved
0.7562	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2799	Discontinued
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7548	Intermediate Similarity	NPD9494	Approved
0.7547	Intermediate Similarity	NPD6651	Approved
0.7546	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1653	Approved
0.7544	Intermediate Similarity	NPD4967	Phase 2
0.7544	Intermediate Similarity	NPD4966	Approved
0.7544	Intermediate Similarity	NPD4965	Approved
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.747	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2344	Approved
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3748	Approved
0.7448	Intermediate Similarity	NPD7584	Approved
0.7444	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5711	Approved
0.7429	Intermediate Similarity	NPD5710	Approved
0.7419	Intermediate Similarity	NPD4363	Phase 3
0.7419	Intermediate Similarity	NPD4360	Phase 2
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7386	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5353	Approved
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7435	Discontinued
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.732	Intermediate Similarity	NPD7701	Phase 2
0.7317	Intermediate Similarity	NPD2424	Discontinued
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7783	Phase 2
0.7296	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7240	Approved
0.7289	Intermediate Similarity	NPD2309	Approved
0.7288	Intermediate Similarity	NPD5242	Approved
0.7267	Intermediate Similarity	NPD5124	Phase 1
0.7267	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7266	Discontinued
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7239	Intermediate Similarity	NPD7033	Discontinued
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7233	Intermediate Similarity	NPD4625	Phase 3
0.7226	Intermediate Similarity	NPD9269	Phase 2
0.7225	Intermediate Similarity	NPD8455	Phase 2
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7197	Intermediate Similarity	NPD1203	Approved
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7161	Intermediate Similarity	NPD1610	Phase 2
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7874	Approved
0.7151	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD3823	Discontinued
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7121	Intermediate Similarity	NPD7801	Approved
0.711	Intermediate Similarity	NPD6386	Approved
0.711	Intermediate Similarity	NPD6385	Approved
0.7098	Intermediate Similarity	NPD2494	Approved
0.7098	Intermediate Similarity	NPD2493	Approved
0.7081	Intermediate Similarity	NPD6798	Discontinued
0.7081	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8127	Discontinued
0.7077	Intermediate Similarity	NPD8320	Phase 1
0.7077	Intermediate Similarity	NPD8319	Approved
0.707	Intermediate Similarity	NPD4749	Approved
0.7066	Intermediate Similarity	NPD6674	Discontinued
0.7065	Intermediate Similarity	NPD7549	Discontinued
0.7059	Intermediate Similarity	NPD7907	Approved
0.7056	Intermediate Similarity	NPD7585	Approved
0.7044	Intermediate Similarity	NPD4111	Phase 1
0.7044	Intermediate Similarity	NPD2798	Approved
0.7044	Intermediate Similarity	NPD4665	Approved
0.703	Intermediate Similarity	NPD4308	Phase 3
0.7029	Intermediate Similarity	NPD5760	Phase 2

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