NPASS Compound

Structure

NPC474038 OpenBabel07101719522D 27 30 0 0 1 0 0 0 0 0999 V2000 0.2588 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -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 0.7934 0.3912 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 -6.9282 -2.0000 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 -0.8660 -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 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 0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7172 0.7739 0.0000 O 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 -0.0000 -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 20 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 20 1 0 0 0 0 4 10 2 0 0 0 0 4 11 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 17 2 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 20 1 0 0 0 0 9 21 1 0 0 0 0 10 19 1 0 0 0 0 12 22 1 0 0 0 0 13 18 2 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 24 2 0 0 0 0 15 19 2 0 0 0 0 15 25 1 0 0 0 0 16 11 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:	2.888
LogD:	2.483
LogS:	-4.322
# Rotatable Bonds:	2
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.642
Synthetic Accessibility Score:	3.96
Fsp3:	0.25
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:	-4.94
MDCK Permeability:	1.3707405742025003e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.888

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	95.66582489013672%
Volume Distribution (VD):	0.958
Pgp-substrate:	5.502551555633545%

ADMET: Metabolism

CYP1A2-inhibitor:	0.848
CYP1A2-substrate:	0.485
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.612
CYP2C9-substrate:	0.766
CYP2D6-inhibitor:	0.432
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	16.431
Half-life (T1/2):	0.686

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.155
Rat Oral Acute Toxicity:	0.885
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.938
Carcinogencity:	0.774
Eye Corrosion:	0.003
Eye Irritation:	0.263
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC474038

Natural Product ID:	NPC474038
*Common Name:**	(2S)-5,7,8'-Trihydroxy-2'-(Hydroxymethyl)-2'-Methyl-2,6'-Bichroman-4-One
IUPAC Name:	(2S)-5,7-dihydroxy-2-[8-hydroxy-2-(hydroxymethyl)-2-methylchromen-6-yl]-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	PNMOOGSNXGIKSQ-DJZRFWRSSA-N
Standard InCHI:	InChI=1S/C20H18O7/c1-20(9-21)3-2-10-4-11(5-15(25)19(10)27-20)16-8-14(24)18-13(23)6-12(22)7-17(18)26-16/h2-7,16,21-23,25H,8-9H2,1H3/t16-,20?/m0/s1
SMILES:	CC1(C=CC2=C(O1)C(=CC(=C2)C3CC(=O)C4=C(C=C(C=C4O3)O)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458937
PubChem CID:	44589107
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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[515685]

☑ 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 NPC474038 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	404
0.1-0.2	1607
0.2-0.3	3952
0.3-0.4	9751
0.4-0.5	8513
0.5-0.6	3392
0.6-0.7	4798
0.7-0.8	5434
0.8-0.85	2880
0.85-0.9	1525
0.9-0.95	363
0.95-1	78

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC119209
0.9934	High Similarity	NPC118256
0.9934	High Similarity	NPC475784
0.9934	High Similarity	NPC192686
0.987	High Similarity	NPC472625
0.9869	High Similarity	NPC26326
0.9869	High Similarity	NPC472632
0.9805	High Similarity	NPC474034
0.9805	High Similarity	NPC474033
0.9804	High Similarity	NPC174953
0.9803	High Similarity	NPC27337
0.9803	High Similarity	NPC284820
0.9803	High Similarity	NPC473272
0.9803	High Similarity	NPC472598
0.9803	High Similarity	NPC474055
0.9742	High Similarity	NPC186686
0.974	High Similarity	NPC471210
0.974	High Similarity	NPC472634
0.9739	High Similarity	NPC473990
0.9739	High Similarity	NPC117418
0.9739	High Similarity	NPC53545
0.9737	High Similarity	NPC35038
0.9737	High Similarity	NPC195796
0.9737	High Similarity	NPC278778
0.9737	High Similarity	NPC291878
0.9677	High Similarity	NPC472635
0.9677	High Similarity	NPC474150
0.9677	High Similarity	NPC474162
0.9677	High Similarity	NPC476247
0.9675	High Similarity	NPC282009
0.9675	High Similarity	NPC287328
0.9675	High Similarity	NPC472631
0.9675	High Similarity	NPC472624
0.9675	High Similarity	NPC472630
0.9673	High Similarity	NPC52889
0.9673	High Similarity	NPC291508
0.9673	High Similarity	NPC471209
0.9671	High Similarity	NPC200761
0.9671	High Similarity	NPC470327
0.9671	High Similarity	NPC477503
0.9671	High Similarity	NPC45849
0.9671	High Similarity	NPC321779
0.9618	High Similarity	NPC471213
0.9618	High Similarity	NPC43319
0.9615	High Similarity	NPC124038
0.9613	High Similarity	NPC471499
0.9613	High Similarity	NPC471212
0.9613	High Similarity	NPC134783
0.9613	High Similarity	NPC289771
0.9613	High Similarity	NPC142252
0.9613	High Similarity	NPC471211
0.961	High Similarity	NPC22192
0.961	High Similarity	NPC184755
0.961	High Similarity	NPC74178
0.961	High Similarity	NPC204879
0.9608	High Similarity	NPC471985
0.9608	High Similarity	NPC209614
0.9608	High Similarity	NPC470328
0.9608	High Similarity	NPC472626
0.9605	High Similarity	NPC192083
0.9605	High Similarity	NPC74924
0.9605	High Similarity	NPC18727
0.9605	High Similarity	NPC213896
0.9557	High Similarity	NPC218226
0.9554	High Similarity	NPC62261
0.9554	High Similarity	NPC293319
0.9551	High Similarity	NPC472448
0.9551	High Similarity	NPC83922
0.9548	High Similarity	NPC204290
0.9548	High Similarity	NPC470326
0.9548	High Similarity	NPC328102
0.9548	High Similarity	NPC36217
0.9545	High Similarity	NPC474681
0.9545	High Similarity	NPC218313
0.9545	High Similarity	NPC78071
0.9545	High Similarity	NPC223787
0.9542	High Similarity	NPC234255
0.9542	High Similarity	NPC226025
0.9539	High Similarity	NPC106976
0.9539	High Similarity	NPC302950
0.9539	High Similarity	NPC219582
0.9539	High Similarity	NPC236637
0.9539	High Similarity	NPC471982
0.9497	High Similarity	NPC288813
0.9497	High Similarity	NPC475212
0.9487	High Similarity	NPC305987
0.9487	High Similarity	NPC288131
0.9487	High Similarity	NPC165970
0.9487	High Similarity	NPC198829
0.9487	High Similarity	NPC158188
0.9487	High Similarity	NPC167678
0.9487	High Similarity	NPC113163
0.9487	High Similarity	NPC84324
0.9487	High Similarity	NPC29876
0.9487	High Similarity	NPC66618
0.9484	High Similarity	NPC476410
0.9484	High Similarity	NPC250214
0.9484	High Similarity	NPC187792
0.9484	High Similarity	NPC95936
0.9484	High Similarity	NPC284127
0.9484	High Similarity	NPC172202
0.9481	High Similarity	NPC5322
0.9481	High Similarity	NPC13858
0.9481	High Similarity	NPC472455
0.9481	High Similarity	NPC282307
0.9481	High Similarity	NPC6633
0.9481	High Similarity	NPC320825
0.9481	High Similarity	NPC133970
0.9481	High Similarity	NPC326037
0.9481	High Similarity	NPC170026
0.9477	High Similarity	NPC7989
0.9477	High Similarity	NPC223701
0.9477	High Similarity	NPC170492
0.9477	High Similarity	NPC298692
0.9477	High Similarity	NPC472583
0.9434	High Similarity	NPC474024
0.9434	High Similarity	NPC6588
0.9434	High Similarity	NPC117854
0.9434	High Similarity	NPC477154
0.943	High Similarity	NPC108433
0.943	High Similarity	NPC239752
0.943	High Similarity	NPC472450
0.943	High Similarity	NPC275780
0.943	High Similarity	NPC50960
0.943	High Similarity	NPC300053
0.9427	High Similarity	NPC201800
0.9427	High Similarity	NPC194427
0.9427	High Similarity	NPC261470
0.9427	High Similarity	NPC472964
0.9423	High Similarity	NPC472902
0.9423	High Similarity	NPC321399
0.9423	High Similarity	NPC101731
0.9423	High Similarity	NPC471973
0.9423	High Similarity	NPC476980
0.9423	High Similarity	NPC470183
0.9423	High Similarity	NPC474960
0.9419	High Similarity	NPC471479
0.9419	High Similarity	NPC78225
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC471515
0.9419	High Similarity	NPC183851
0.9419	High Similarity	NPC63454
0.9419	High Similarity	NPC67876
0.9419	High Similarity	NPC52530
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC470402
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC475267
0.9416	High Similarity	NPC117992
0.9416	High Similarity	NPC259710
0.9416	High Similarity	NPC230149
0.9416	High Similarity	NPC48579
0.9416	High Similarity	NPC304207
0.9416	High Similarity	NPC217706
0.9416	High Similarity	NPC472280
0.9416	High Similarity	NPC200246
0.9416	High Similarity	NPC256925
0.9416	High Similarity	NPC57674
0.9416	High Similarity	NPC168247
0.9416	High Similarity	NPC152951
0.9416	High Similarity	NPC207809
0.9412	High Similarity	NPC244583
0.9412	High Similarity	NPC56232
0.9412	High Similarity	NPC323626
0.9412	High Similarity	NPC237994
0.9412	High Similarity	NPC40033
0.9412	High Similarity	NPC150123
0.9412	High Similarity	NPC475790
0.9412	High Similarity	NPC472912
0.9412	High Similarity	NPC161881
0.9412	High Similarity	NPC10807
0.9412	High Similarity	NPC324233
0.9408	High Similarity	NPC472633
0.9408	High Similarity	NPC88804
0.9408	High Similarity	NPC338131
0.9408	High Similarity	NPC3825
0.9379	High Similarity	NPC256760
0.9375	High Similarity	NPC165456
0.9371	High Similarity	NPC13481
0.9371	High Similarity	NPC120593
0.9371	High Similarity	NPC119589
0.9371	High Similarity	NPC207575
0.9371	High Similarity	NPC39091
0.9371	High Similarity	NPC272502
0.9367	High Similarity	NPC189473
0.9367	High Similarity	NPC476295
0.9367	High Similarity	NPC23298
0.9363	High Similarity	NPC349525
0.9363	High Similarity	NPC173137
0.9363	High Similarity	NPC266314
0.9363	High Similarity	NPC57715
0.9363	High Similarity	NPC259456
0.9363	High Similarity	NPC234644
0.9359	High Similarity	NPC469658
0.9359	High Similarity	NPC210459
0.9355	High Similarity	NPC191146
0.9355	High Similarity	NPC24640
0.9355	High Similarity	NPC208152

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 NPC474038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	913
0.2-0.3	1781
0.3-0.4	2617
0.4-0.5	1813
0.5-0.6	993
0.6-0.7	482
0.7-0.8	142
0.8-0.85	28
0.85-0.9	17
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD2393	Clinical (unspecified phase)
0.9539	High Similarity	NPD1934	Approved
0.9308	High Similarity	NPD6166	Phase 2
0.9308	High Similarity	NPD6167	Clinical (unspecified phase)
0.9308	High Similarity	NPD6168	Clinical (unspecified phase)
0.9226	High Similarity	NPD2801	Approved
0.9156	High Similarity	NPD4380	Phase 2
0.9136	High Similarity	NPD7054	Approved
0.908	High Similarity	NPD7472	Approved
0.908	High Similarity	NPD7074	Phase 3
0.9013	High Similarity	NPD1511	Approved
0.8957	High Similarity	NPD3818	Discontinued
0.8909	High Similarity	NPD6797	Phase 2
0.8896	High Similarity	NPD1512	Approved
0.8868	High Similarity	NPD3882	Suspended
0.8855	High Similarity	NPD7251	Discontinued
0.8831	High Similarity	NPD4378	Clinical (unspecified phase)
0.882	High Similarity	NPD5494	Approved
0.8812	High Similarity	NPD4381	Clinical (unspecified phase)
0.8805	High Similarity	NPD3817	Phase 2
0.8802	High Similarity	NPD4338	Clinical (unspecified phase)
0.8802	High Similarity	NPD7808	Phase 3
0.875	High Similarity	NPD4868	Clinical (unspecified phase)
0.8696	High Similarity	NPD7075	Discontinued
0.8675	High Similarity	NPD7804	Clinical (unspecified phase)
0.8625	High Similarity	NPD7096	Clinical (unspecified phase)
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.859	High Similarity	NPD7410	Clinical (unspecified phase)
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8563	High Similarity	NPD5844	Phase 1
0.8562	High Similarity	NPD6801	Discontinued
0.8562	High Similarity	NPD1549	Phase 2
0.8431	Intermediate Similarity	NPD2796	Approved
0.8424	Intermediate Similarity	NPD6959	Discontinued
0.8395	Intermediate Similarity	NPD7819	Suspended
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8373	Intermediate Similarity	NPD6232	Discontinued
0.8366	Intermediate Similarity	NPD1510	Phase 2
0.8353	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8304	Intermediate Similarity	NPD6559	Discontinued
0.8232	Intermediate Similarity	NPD5402	Approved
0.8224	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1613	Approved
0.8176	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD1465	Phase 2
0.8137	Intermediate Similarity	NPD5403	Approved
0.8105	Intermediate Similarity	NPD1240	Approved
0.8095	Intermediate Similarity	NPD1247	Approved
0.8084	Intermediate Similarity	NPD919	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3027	Phase 3
0.8012	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD943	Approved
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3750	Approved
0.7862	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7812	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2800	Approved
0.7811	Intermediate Similarity	NPD3749	Approved
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7791	Intermediate Similarity	NPD2532	Approved
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD4628	Phase 3
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.7758	Intermediate Similarity	NPD1653	Approved
0.774	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3787	Discontinued
0.7709	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7705	Intermediate Similarity	NPD4360	Phase 2
0.7705	Intermediate Similarity	NPD4363	Phase 3
0.7697	Intermediate Similarity	NPD920	Approved
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7685	Pre-registration
0.7674	Intermediate Similarity	NPD7199	Phase 2
0.7661	Intermediate Similarity	NPD6234	Discontinued
0.7657	Intermediate Similarity	NPD7228	Approved
0.7632	Intermediate Similarity	NPD7584	Approved
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7625	Intermediate Similarity	NPD6099	Approved
0.7625	Intermediate Similarity	NPD6100	Approved
0.7622	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6190	Approved
0.7598	Intermediate Similarity	NPD8312	Approved
0.7598	Intermediate Similarity	NPD8313	Approved
0.7595	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5124	Phase 1
0.7595	Intermediate Similarity	NPD447	Suspended
0.7593	Intermediate Similarity	NPD1243	Approved
0.7576	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD37	Approved
0.7562	Intermediate Similarity	NPD7033	Discontinued
0.7562	Intermediate Similarity	NPD3748	Approved
0.7561	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6651	Approved
0.7546	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4965	Approved
0.7544	Intermediate Similarity	NPD4966	Approved
0.7544	Intermediate Similarity	NPD4967	Phase 2
0.7528	Intermediate Similarity	NPD5953	Discontinued
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1933	Approved
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.747	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7453	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD9494	Approved
0.7423	Intermediate Similarity	NPD2424	Discontinued
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7435	Discontinued
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7371	Intermediate Similarity	NPD8151	Discontinued
0.7368	Intermediate Similarity	NPD6844	Discontinued
0.7365	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2344	Approved
0.7342	Intermediate Similarity	NPD4625	Phase 3
0.733	Intermediate Similarity	NPD5710	Approved
0.733	Intermediate Similarity	NPD5711	Approved
0.7326	Intermediate Similarity	NPD8455	Phase 2
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7783	Phase 2
0.7296	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7697	Approved
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD4361	Phase 2
0.7287	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD1610	Phase 2
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
0.7238	Intermediate Similarity	NPD3823	Discontinued
0.7237	Intermediate Similarity	NPD1548	Phase 1
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7231	Intermediate Similarity	NPD7701	Phase 2
0.7231	Intermediate Similarity	NPD7585	Approved
0.7198	Intermediate Similarity	NPD7240	Approved
0.7197	Intermediate Similarity	NPD1203	Approved
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7191	Intermediate Similarity	NPD5242	Approved
0.7188	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD3268	Approved
0.7186	Intermediate Similarity	NPD2309	Approved
0.7184	Intermediate Similarity	NPD5353	Approved
0.7179	Intermediate Similarity	NPD7583	Approved
0.7175	Intermediate Similarity	NPD8127	Discontinued
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7169	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7549	Discontinued
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7874	Approved
0.7152	Intermediate Similarity	NPD2798	Approved
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7121	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7098	Intermediate Similarity	NPD2494	Approved
0.7098	Intermediate Similarity	NPD2493	Approved
0.7089	Intermediate Similarity	NPD2797	Approved
0.707	Intermediate Similarity	NPD4749	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