NPASS Compound

Structure

NPC474033 OpenBabel07101719522D 26 29 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 -6.9282 -3.0000 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 -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 -0.0000 -2.0000 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 -2.5981 -1.5000 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 -6.9282 -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 -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 -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 0.8660 -1.5000 0.0000 C 0 0 3 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 -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 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 15 2 0 0 0 0 7 11 1 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 11 19 2 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 22 2 0 0 0 0 15 19 1 0 0 0 0 15 23 1 0 0 0 0 16 10 1 6 0 0 0 16 25 1 0 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	354.536
LogP:	3.14
LogD:	2.793
LogS:	-4.227
# Rotatable Bonds:	1
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.727
Synthetic Accessibility Score:	3.722
Fsp3:	0.35
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:	-4.783
MDCK Permeability:	1.2774215065292083e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.433
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.206

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	93.16498565673828%
Volume Distribution (VD):	0.768
Pgp-substrate:	5.03914737701416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.433
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.549
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.751
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.69
CYP2D6-substrate:	0.34
CYP3A4-inhibitor:	0.481
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	14.306
Half-life (T1/2):	0.553

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.632
Drug-inuced Liver Injury (DILI):	0.647
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.791
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.84
Carcinogencity:	0.723
Eye Corrosion:	0.003
Eye Irritation:	0.132
Respiratory Toxicity:	0.863

Download Data

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

Natural Product: NPC474033

Natural Product ID:	NPC474033
*Common Name:**	(2S)-3',7,8'-Trihydroxy-2',2'-Dimethyl-2,6'-Bichroman-4-One
IUPAC Name:	(2S)-2-(3,8-dihydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-7-hydroxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	VQRCDZLYMBXGNJ-ATNAJCNCSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-20(2)18(24)7-11-5-10(6-15(23)19(11)26-20)16-9-14(22)13-4-3-12(21)8-17(13)25-16/h3-6,8,16,18,21,23-24H,7,9H2,1-2H3/t16-,18?/m0/s1
SMILES:	CC1(C(CC2=C(O1)C(=CC(=C2)C3CC(=O)C4=C(O3)C=C(C=C4)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458814
PubChem CID:	44589232
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[450827]

☑ 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 NPC474033 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	405
0.1-0.2	1617
0.2-0.3	3973
0.3-0.4	9607
0.4-0.5	8587
0.5-0.6	3409
0.6-0.7	4774
0.7-0.8	5374
0.8-0.85	2859
0.85-0.9	1651
0.9-0.95	375
0.95-1	66

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474034
0.9935	High Similarity	NPC472632
0.9869	High Similarity	NPC174953
0.9805	High Similarity	NPC474038
0.9805	High Similarity	NPC134783
0.9805	High Similarity	NPC471210
0.9804	High Similarity	NPC473990
0.9742	High Similarity	NPC476247
0.974	High Similarity	NPC475784
0.974	High Similarity	NPC118256
0.974	High Similarity	NPC192686
0.974	High Similarity	NPC119209
0.9739	High Similarity	NPC472598
0.9739	High Similarity	NPC474055
0.9739	High Similarity	NPC291508
0.9739	High Similarity	NPC471209
0.9739	High Similarity	NPC27337
0.9682	High Similarity	NPC471213
0.9679	High Similarity	NPC472625
0.9679	High Similarity	NPC124038
0.9677	High Similarity	NPC471212
0.9677	High Similarity	NPC472634
0.9677	High Similarity	NPC471211
0.9677	High Similarity	NPC26326
0.9673	High Similarity	NPC278778
0.9673	High Similarity	NPC35038
0.9673	High Similarity	NPC195796
0.9673	High Similarity	NPC291878
0.9618	High Similarity	NPC293319
0.9618	High Similarity	NPC62261
0.9615	High Similarity	NPC472635
0.9613	High Similarity	NPC287328
0.9613	High Similarity	NPC472630
0.9613	High Similarity	NPC282009
0.9613	High Similarity	NPC472631
0.9613	High Similarity	NPC472624
0.961	High Similarity	NPC52889
0.961	High Similarity	NPC284820
0.961	High Similarity	NPC473272
0.9608	High Similarity	NPC470327
0.9608	High Similarity	NPC321779
0.9608	High Similarity	NPC477503
0.9608	High Similarity	NPC45849
0.9608	High Similarity	NPC200761
0.9554	High Similarity	NPC186686
0.9551	High Similarity	NPC471499
0.9551	High Similarity	NPC142252
0.9548	High Similarity	NPC74178
0.9548	High Similarity	NPC22192
0.9548	High Similarity	NPC53545
0.9548	High Similarity	NPC117418
0.9548	High Similarity	NPC204879
0.9548	High Similarity	NPC184755
0.9545	High Similarity	NPC470328
0.9545	High Similarity	NPC209614
0.9545	High Similarity	NPC470600
0.9545	High Similarity	NPC472626
0.9542	High Similarity	NPC192083
0.9542	High Similarity	NPC18727
0.9542	High Similarity	NPC213896
0.9542	High Similarity	NPC74924
0.9497	High Similarity	NPC477154
0.9497	High Similarity	NPC474024
0.9497	High Similarity	NPC6588
0.9497	High Similarity	NPC117854
0.9494	High Similarity	NPC300053
0.9494	High Similarity	NPC108433
0.949	High Similarity	NPC474162
0.949	High Similarity	NPC220912
0.949	High Similarity	NPC474150
0.949	High Similarity	NPC472448
0.949	High Similarity	NPC83922
0.949	High Similarity	NPC472964
0.9487	High Similarity	NPC36217
0.9487	High Similarity	NPC470326
0.9487	High Similarity	NPC471976
0.9487	High Similarity	NPC328102
0.9487	High Similarity	NPC472902
0.9484	High Similarity	NPC474681
0.9484	High Similarity	NPC223787
0.9484	High Similarity	NPC218313
0.9484	High Similarity	NPC78071
0.9484	High Similarity	NPC67876
0.9484	High Similarity	NPC52530
0.9481	High Similarity	NPC256925
0.9481	High Similarity	NPC57674
0.9481	High Similarity	NPC168247
0.9481	High Similarity	NPC152951
0.9481	High Similarity	NPC234255
0.9481	High Similarity	NPC117992
0.9481	High Similarity	NPC230149
0.9481	High Similarity	NPC226025
0.9481	High Similarity	NPC477958
0.9477	High Similarity	NPC475790
0.9477	High Similarity	NPC106976
0.9477	High Similarity	NPC219582
0.9477	High Similarity	NPC302950
0.9477	High Similarity	NPC236637
0.9437	High Similarity	NPC288813
0.9434	High Similarity	NPC43319
0.9434	High Similarity	NPC119589
0.9427	High Similarity	NPC173137
0.9427	High Similarity	NPC228383
0.9427	High Similarity	NPC158188
0.9427	High Similarity	NPC289771
0.9427	High Similarity	NPC29876
0.9427	High Similarity	NPC167678
0.9427	High Similarity	NPC3629
0.9423	High Similarity	NPC250214
0.9423	High Similarity	NPC187792
0.9423	High Similarity	NPC95936
0.9419	High Similarity	NPC282307
0.9419	High Similarity	NPC208152
0.9419	High Similarity	NPC133970
0.9419	High Similarity	NPC326037
0.9419	High Similarity	NPC6633
0.9419	High Similarity	NPC320825
0.9419	High Similarity	NPC13858
0.9419	High Similarity	NPC170026
0.9419	High Similarity	NPC5322
0.9419	High Similarity	NPC472455
0.9419	High Similarity	NPC78492
0.9419	High Similarity	NPC471985
0.9416	High Similarity	NPC227337
0.9416	High Similarity	NPC223701
0.9416	High Similarity	NPC7989
0.9416	High Similarity	NPC273462
0.9416	High Similarity	NPC298692
0.9416	High Similarity	NPC49402
0.9416	High Similarity	NPC70433
0.9416	High Similarity	NPC33051
0.9416	High Similarity	NPC472583
0.9412	High Similarity	NPC472422
0.9412	High Similarity	NPC471676
0.9412	High Similarity	NPC472420
0.9412	High Similarity	NPC474021
0.9412	High Similarity	NPC244577
0.9412	High Similarity	NPC474023
0.9412	High Similarity	NPC263384
0.9379	High Similarity	NPC103307
0.9375	High Similarity	NPC477502
0.9375	High Similarity	NPC14662
0.9375	High Similarity	NPC218226
0.9371	High Similarity	NPC72787
0.9371	High Similarity	NPC58223
0.9371	High Similarity	NPC7688
0.9371	High Similarity	NPC224280
0.9371	High Similarity	NPC7154
0.9371	High Similarity	NPC50960
0.9371	High Similarity	NPC36916
0.9371	High Similarity	NPC36
0.9371	High Similarity	NPC234052
0.9371	High Similarity	NPC472277
0.9371	High Similarity	NPC125039
0.9367	High Similarity	NPC201800
0.9367	High Similarity	NPC261470
0.9363	High Similarity	NPC321399
0.9363	High Similarity	NPC204290
0.9363	High Similarity	NPC470183
0.9363	High Similarity	NPC476980
0.9363	High Similarity	NPC474960
0.9359	High Similarity	NPC210084
0.9359	High Similarity	NPC471479
0.9359	High Similarity	NPC475267
0.9359	High Similarity	NPC48208
0.9359	High Similarity	NPC474208
0.9359	High Similarity	NPC262286
0.9359	High Similarity	NPC471515
0.9359	High Similarity	NPC299520
0.9359	High Similarity	NPC36852
0.9359	High Similarity	NPC474836
0.9359	High Similarity	NPC99597
0.9359	High Similarity	NPC129684
0.9359	High Similarity	NPC162869
0.9359	High Similarity	NPC156057
0.9359	High Similarity	NPC78225
0.9355	High Similarity	NPC200246
0.9355	High Similarity	NPC472280
0.9351	High Similarity	NPC324233
0.9351	High Similarity	NPC40033
0.9351	High Similarity	NPC471982
0.9351	High Similarity	NPC237994
0.9351	High Similarity	NPC472912
0.9351	High Similarity	NPC477231
0.9351	High Similarity	NPC323626
0.9351	High Similarity	NPC257648
0.9346	High Similarity	NPC338131
0.9321	High Similarity	NPC121333
0.9321	High Similarity	NPC256760
0.9317	High Similarity	NPC152477
0.9317	High Similarity	NPC229687
0.9317	High Similarity	NPC475212
0.9313	High Similarity	NPC236934
0.9313	High Similarity	NPC5778
0.9313	High Similarity	NPC120593
0.9313	High Similarity	NPC173292
0.9313	High Similarity	NPC13481
0.9313	High Similarity	NPC477517
0.9313	High Similarity	NPC235610
0.9313	High Similarity	NPC207575

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 NPC474033 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	921
0.2-0.3	1784
0.3-0.4	2611
0.4-0.5	1814
0.5-0.6	988
0.6-0.7	471
0.7-0.8	143
0.8-0.85	33
0.85-0.9	16
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9542	High Similarity	NPD2393	Clinical (unspecified phase)
0.9477	High Similarity	NPD1934	Approved
0.9371	High Similarity	NPD6168	Clinical (unspecified phase)
0.9371	High Similarity	NPD6166	Phase 2
0.9371	High Similarity	NPD6167	Clinical (unspecified phase)
0.9141	High Similarity	NPD7074	Phase 3
0.9097	High Similarity	NPD4380	Phase 2
0.908	High Similarity	NPD7054	Approved
0.9045	High Similarity	NPD2801	Approved
0.9024	High Similarity	NPD7472	Approved
0.9	High Similarity	NPD5494	Approved
0.8931	High Similarity	NPD3882	Suspended
0.8902	High Similarity	NPD3818	Discontinued
0.8855	High Similarity	NPD6797	Phase 2
0.8831	High Similarity	NPD1511	Approved
0.8812	High Similarity	NPD4868	Clinical (unspecified phase)
0.8802	High Similarity	NPD7251	Discontinued
0.8758	High Similarity	NPD4381	Clinical (unspecified phase)
0.8758	High Similarity	NPD7075	Discontinued
0.875	High Similarity	NPD7808	Phase 3
0.8718	High Similarity	NPD1512	Approved
0.8688	High Similarity	NPD7096	Clinical (unspecified phase)
0.8654	High Similarity	NPD4378	Clinical (unspecified phase)
0.8639	High Similarity	NPD4338	Clinical (unspecified phase)
0.8634	High Similarity	NPD3817	Phase 2
0.8627	High Similarity	NPD1549	Phase 2
0.8623	High Similarity	NPD7804	Clinical (unspecified phase)
0.8623	High Similarity	NPD5844	Phase 1
0.8562	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1552	Clinical (unspecified phase)
0.8535	High Similarity	NPD7410	Clinical (unspecified phase)
0.8521	High Similarity	NPD7993	Clinical (unspecified phase)
0.8519	High Similarity	NPD8443	Clinical (unspecified phase)
0.8509	High Similarity	NPD6801	Discontinued
0.8485	Intermediate Similarity	NPD6959	Discontinued
0.8457	Intermediate Similarity	NPD7819	Suspended
0.8447	Intermediate Similarity	NPD7411	Suspended
0.8377	Intermediate Similarity	NPD2796	Approved
0.8363	Intermediate Similarity	NPD6559	Discontinued
0.8344	Intermediate Similarity	NPD1465	Phase 2
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8312	Intermediate Similarity	NPD1510	Phase 2
0.8284	Intermediate Similarity	NPD7473	Discontinued
0.8239	Intermediate Similarity	NPD6799	Approved
0.8182	Intermediate Similarity	NPD5402	Approved
0.817	Intermediate Similarity	NPD1240	Approved
0.817	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1613	Approved
0.8118	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD5403	Approved
0.8065	Intermediate Similarity	NPD1607	Approved
0.8052	Intermediate Similarity	NPD943	Approved
0.8049	Intermediate Similarity	NPD6599	Discontinued
0.8047	Intermediate Similarity	NPD1247	Approved
0.8036	Intermediate Similarity	NPD919	Approved
0.8024	Intermediate Similarity	NPD7768	Phase 2
0.7974	Intermediate Similarity	NPD3027	Phase 3
0.7963	Intermediate Similarity	NPD5401	Approved
0.7911	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3749	Approved
0.7849	Intermediate Similarity	NPD3926	Phase 2
0.7845	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3750	Approved
0.7826	Intermediate Similarity	NPD4628	Phase 3
0.7816	Intermediate Similarity	NPD3751	Discontinued
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2800	Approved
0.7758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD8313	Approved
0.7753	Intermediate Similarity	NPD8312	Approved
0.7744	Intermediate Similarity	NPD2533	Approved
0.7744	Intermediate Similarity	NPD2532	Approved
0.7744	Intermediate Similarity	NPD2534	Approved
0.7742	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7228	Approved
0.7711	Intermediate Similarity	NPD1653	Approved
0.7702	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1551	Phase 2
0.7688	Intermediate Similarity	NPD3787	Discontinued
0.7669	Intermediate Similarity	NPD6190	Approved
0.7658	Intermediate Similarity	NPD447	Suspended
0.7651	Intermediate Similarity	NPD920	Approved
0.764	Intermediate Similarity	NPD7685	Pre-registration
0.763	Intermediate Similarity	NPD7199	Phase 2
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.7598	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD7584	Approved
0.7584	Intermediate Similarity	NPD5953	Discontinued
0.7581	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6100	Approved
0.7578	Intermediate Similarity	NPD6099	Approved
0.7571	Intermediate Similarity	NPD7286	Phase 2
0.7568	Intermediate Similarity	NPD4360	Phase 2
0.7568	Intermediate Similarity	NPD4363	Phase 3
0.756	Intermediate Similarity	NPD3226	Approved
0.7553	Intermediate Similarity	NPD6777	Approved
0.7553	Intermediate Similarity	NPD6780	Approved
0.7553	Intermediate Similarity	NPD6778	Approved
0.7553	Intermediate Similarity	NPD6779	Approved
0.7553	Intermediate Similarity	NPD6776	Approved
0.7553	Intermediate Similarity	NPD6781	Approved
0.7553	Intermediate Similarity	NPD6782	Approved
0.7547	Intermediate Similarity	NPD1933	Approved
0.7546	Intermediate Similarity	NPD1243	Approved
0.7531	Intermediate Similarity	NPD2346	Discontinued
0.753	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD37	Approved
0.7527	Intermediate Similarity	NPD8150	Discontinued
0.7516	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4966	Approved
0.747	Intermediate Similarity	NPD7390	Discontinued
0.747	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7468	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4908	Phase 1
0.7451	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5124	Phase 1
0.7438	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7435	Discontinued
0.7435	Intermediate Similarity	NPD7698	Approved
0.7435	Intermediate Similarity	NPD7696	Phase 3
0.7435	Intermediate Similarity	NPD7697	Approved
0.7432	Intermediate Similarity	NPD8434	Phase 2
0.7425	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2344	Approved
0.7423	Intermediate Similarity	NPD7266	Discontinued
0.7407	Intermediate Similarity	NPD7033	Discontinued
0.7384	Intermediate Similarity	NPD8455	Phase 2
0.7378	Intermediate Similarity	NPD2424	Discontinued
0.7371	Intermediate Similarity	NPD7701	Phase 2
0.7347	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7783	Phase 2
0.7326	Intermediate Similarity	NPD6844	Discontinued
0.7321	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7871	Phase 2
0.7306	Intermediate Similarity	NPD7870	Phase 2
0.7296	Intermediate Similarity	NPD4625	Phase 3
0.7293	Intermediate Similarity	NPD3823	Discontinued
0.7292	Intermediate Similarity	NPD6823	Phase 2
0.7288	Intermediate Similarity	NPD5710	Approved
0.7288	Intermediate Similarity	NPD5711	Approved
0.7287	Intermediate Similarity	NPD6534	Approved
0.7287	Intermediate Similarity	NPD6535	Approved
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7699	Phase 2
0.7263	Intermediate Similarity	NPD7700	Phase 2
0.7261	Intermediate Similarity	NPD1203	Approved
0.7253	Intermediate Similarity	NPD7240	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.7247	Intermediate Similarity	NPD5242	Approved
0.7246	Intermediate Similarity	NPD2309	Approved
0.7241	Intermediate Similarity	NPD5353	Approved
0.7233	Intermediate Similarity	NPD6832	Phase 2
0.7232	Intermediate Similarity	NPD8127	Discontinued
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7222	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7874	Approved
0.7208	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7585	Approved
0.7172	Intermediate Similarity	NPD7801	Approved
0.7158	Intermediate Similarity	NPD4361	Phase 2
0.7158	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7583	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8319	Approved
0.7128	Intermediate Similarity	NPD8320	Phase 1
0.7126	Intermediate Similarity	NPD6674	Discontinued
0.7126	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1652	Phase 2
0.712	Intermediate Similarity	NPD7549	Discontinued
0.7118	Intermediate Similarity	NPD4661	Approved
0.7118	Intermediate Similarity	NPD4662	Approved
0.7107	Intermediate Similarity	NPD2798	Approved
0.7095	Intermediate Similarity	NPD7229	Phase 3
0.7094	Intermediate Similarity	NPD4111	Phase 1
0.7094	Intermediate Similarity	NPD4665	Approved
0.7091	Intermediate Similarity	NPD4308	Phase 3
0.7086	Intermediate Similarity	NPD5761	Phase 2
0.7086	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