NPASS Compound

Structure

NPC472455 OpenBabel07101718312D 26 28 0 0 0 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 -0.7934 -0.3912 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 4.3301 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 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 6.0622 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 3.4641 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 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 24 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 20 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 26 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 23 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	360.456
LogP:	4.139
LogD:	3.671
LogS:	-3.822
# Rotatable Bonds:	4
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.815
Synthetic Accessibility Score:	2.765
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.754
MDCK Permeability:	1.6168178262887523e-05
Pgp-inhibitor:	0.641
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	100.64400482177734%
Volume Distribution (VD):	0.424
Pgp-substrate:	1.4836018085479736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.494
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.783
CYP2C9-substrate:	0.839
CYP2D6-inhibitor:	0.736
CYP2D6-substrate:	0.55
CYP3A4-inhibitor:	0.804
CYP3A4-substrate:	0.441

ADMET: Excretion

Clearance (CL):	5.671
Half-life (T1/2):	0.393

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.778
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.633
Maximum Recommended Daily Dose:	0.566
Skin Sensitization:	0.119
Carcinogencity:	0.877
Eye Corrosion:	0.003
Eye Irritation:	0.48
Respiratory Toxicity:	0.84

Download Data

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

Natural Product: NPC472455

Natural Product ID:	NPC472455
*Common Name:**	RNYNDGYJDSVNNS-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RNYNDGYJDSVNNS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-20(2)8-7-12-15(26-20)10-14(22)17(19(12)25-4)18(23)11-5-6-13(21)16(9-11)24-3/h5-10,21-22H,1-4H3
SMILES:	CC1(C=CC2=C(O1)C=C(C(=C2OC)C(=O)C3=CC(=C(C=C3)O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3422282
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO5259	Garcinia buchananii	Species	Clusiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[25625705]
NPO5259	Garcinia buchananii	Species	Clusiaceae	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
EC50	1
Others	4

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.	EC50	<=	53400.0	nM	PMID[566517]
NPT35	Others	n.a.	Activity	=	1.04	mmolequiv/mmol	PMID[566517]
NPT35	Others	n.a.	Activity	=	0.4	mmolequiv/mmol	PMID[566517]
NPT35	Others	n.a.	Activity	=	4.87	mmolequiv/mmol	PMID[566517]
NPT35	Others	n.a.	Activity	=	2.44	mmolequiv/mmol	PMID[566517]

☑ 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 NPC472455 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	415
0.1-0.2	1697
0.2-0.3	4331
0.3-0.4	10608
0.4-0.5	7240
0.5-0.6	3328
0.6-0.7	4808
0.7-0.8	5333
0.8-0.85	2584
0.85-0.9	1638
0.9-0.95	669
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC472280
0.9932	High Similarity	NPC234255
0.9867	High Similarity	NPC204879
0.9801	High Similarity	NPC476980
0.98	High Similarity	NPC218313
0.98	High Similarity	NPC474681
0.9799	High Similarity	NPC168247
0.9799	High Similarity	NPC256925
0.9799	High Similarity	NPC152951
0.9799	High Similarity	NPC57674
0.9799	High Similarity	NPC230149
0.9799	High Similarity	NPC117992
0.9797	High Similarity	NPC237994
0.9735	High Similarity	NPC74178
0.9735	High Similarity	NPC184755
0.9733	High Similarity	NPC5322
0.9733	High Similarity	NPC133970
0.9733	High Similarity	NPC6633
0.9732	High Similarity	NPC273462
0.9732	High Similarity	NPC33051
0.9732	High Similarity	NPC227337
0.9732	High Similarity	NPC49402
0.9732	High Similarity	NPC70433
0.973	High Similarity	NPC154345
0.9673	High Similarity	NPC83922
0.9673	High Similarity	NPC472448
0.9669	High Similarity	NPC52889
0.9669	High Similarity	NPC476981
0.9667	High Similarity	NPC200246
0.9664	High Similarity	NPC39732
0.9664	High Similarity	NPC471982
0.9664	High Similarity	NPC60972
0.9608	High Similarity	NPC258331
0.9608	High Similarity	NPC29876
0.9608	High Similarity	NPC234644
0.9608	High Similarity	NPC259456
0.9608	High Similarity	NPC57715
0.9608	High Similarity	NPC167678
0.9603	High Similarity	NPC471985
0.9603	High Similarity	NPC282307
0.9603	High Similarity	NPC170026
0.9603	High Similarity	NPC470600
0.9597	High Similarity	NPC256406
0.9545	High Similarity	NPC474162
0.9545	High Similarity	NPC474150
0.9545	High Similarity	NPC261470
0.9542	High Similarity	NPC119209
0.9542	High Similarity	NPC204290
0.9542	High Similarity	NPC328102
0.9542	High Similarity	NPC188433
0.9542	High Similarity	NPC118256
0.9542	High Similarity	NPC471973
0.9542	High Similarity	NPC192686
0.9539	High Similarity	NPC136674
0.9539	High Similarity	NPC219867
0.9539	High Similarity	NPC27337
0.9539	High Similarity	NPC78225
0.9539	High Similarity	NPC291508
0.9539	High Similarity	NPC161960
0.9539	High Similarity	NPC304008
0.9539	High Similarity	NPC36852
0.9539	High Similarity	NPC262286
0.9539	High Similarity	NPC187745
0.9539	High Similarity	NPC180011
0.9536	High Similarity	NPC20830
0.9536	High Similarity	NPC256612
0.9533	High Similarity	NPC477231
0.9533	High Similarity	NPC257648
0.953	High Similarity	NPC472279
0.953	High Similarity	NPC29231
0.953	High Similarity	NPC3825
0.953	High Similarity	NPC88804
0.9484	High Similarity	NPC124038
0.9481	High Similarity	NPC134783
0.9481	High Similarity	NPC474038
0.9474	High Similarity	NPC278778
0.9474	High Similarity	NPC138243
0.9474	High Similarity	NPC195796
0.9474	High Similarity	NPC191146
0.9474	High Similarity	NPC265511
0.9474	High Similarity	NPC291878
0.9474	High Similarity	NPC35038
0.9474	High Similarity	NPC68093
0.9474	High Similarity	NPC115853
0.947	High Similarity	NPC170492
0.947	High Similarity	NPC47781
0.947	High Similarity	NPC183878
0.947	High Similarity	NPC160951
0.947	High Similarity	NPC22519
0.947	High Similarity	NPC231018
0.947	High Similarity	NPC255350
0.947	High Similarity	NPC145379
0.947	High Similarity	NPC69394
0.947	High Similarity	NPC176775
0.947	High Similarity	NPC274327
0.9467	High Similarity	NPC31363
0.9463	High Similarity	NPC38545
0.9463	High Similarity	NPC200060
0.9463	High Similarity	NPC48479
0.9463	High Similarity	NPC52005
0.9463	High Similarity	NPC142876
0.9463	High Similarity	NPC171916
0.9463	High Similarity	NPC183950
0.9463	High Similarity	NPC40290
0.9463	High Similarity	NPC223579
0.9463	High Similarity	NPC69430
0.9463	High Similarity	NPC177298
0.9463	High Similarity	NPC139293
0.9463	High Similarity	NPC264289
0.9463	High Similarity	NPC137062
0.9463	High Similarity	NPC195763
0.9463	High Similarity	NPC264550
0.9463	High Similarity	NPC333691
0.9463	High Similarity	NPC287101
0.9459	High Similarity	NPC168803
0.9423	High Similarity	NPC300053
0.9423	High Similarity	NPC303174
0.9423	High Similarity	NPC108433
0.9423	High Similarity	NPC239752
0.9423	High Similarity	NPC50960
0.9423	High Similarity	NPC472450
0.9423	High Similarity	NPC275780
0.9419	High Similarity	NPC81679
0.9419	High Similarity	NPC474033
0.9419	High Similarity	NPC474034
0.9416	High Similarity	NPC474960
0.9416	High Similarity	NPC28241
0.9416	High Similarity	NPC475784
0.9416	High Similarity	NPC246478
0.9416	High Similarity	NPC472624
0.9412	High Similarity	NPC129684
0.9412	High Similarity	NPC472963
0.9412	High Similarity	NPC474055
0.9412	High Similarity	NPC473272
0.9412	High Similarity	NPC299520
0.9412	High Similarity	NPC67876
0.9412	High Similarity	NPC472598
0.9412	High Similarity	NPC284820
0.9412	High Similarity	NPC78071
0.9408	High Similarity	NPC134287
0.9408	High Similarity	NPC45849
0.9408	High Similarity	NPC200761
0.9408	High Similarity	NPC130589
0.9408	High Similarity	NPC4455
0.9408	High Similarity	NPC146165
0.9408	High Similarity	NPC113906
0.9408	High Similarity	NPC470327
0.9408	High Similarity	NPC92659
0.9408	High Similarity	NPC213622
0.9408	High Similarity	NPC183597
0.9408	High Similarity	NPC133392
0.9408	High Similarity	NPC2476
0.9408	High Similarity	NPC477503
0.9408	High Similarity	NPC128863
0.9408	High Similarity	NPC138360
0.9408	High Similarity	NPC280339
0.9408	High Similarity	NPC208197
0.9408	High Similarity	NPC227325
0.9408	High Similarity	NPC196439
0.9408	High Similarity	NPC163780
0.9408	High Similarity	NPC167815
0.9408	High Similarity	NPC50715
0.9408	High Similarity	NPC201136
0.9408	High Similarity	NPC39184
0.9404	High Similarity	NPC188203
0.9404	High Similarity	NPC37684
0.9404	High Similarity	NPC131624
0.9404	High Similarity	NPC241498
0.9404	High Similarity	NPC256283
0.9404	High Similarity	NPC100887
0.9404	High Similarity	NPC71334
0.9404	High Similarity	NPC120163
0.9404	High Similarity	NPC83508
0.9404	High Similarity	NPC198826
0.9404	High Similarity	NPC63187
0.9404	High Similarity	NPC301323
0.9404	High Similarity	NPC275836
0.9404	High Similarity	NPC275722
0.9404	High Similarity	NPC212678
0.9404	High Similarity	NPC162313
0.9404	High Similarity	NPC187498
0.9404	High Similarity	NPC25270
0.9404	High Similarity	NPC293183
0.9404	High Similarity	NPC472912
0.9404	High Similarity	NPC156222
0.9404	High Similarity	NPC55205
0.9404	High Similarity	NPC222830
0.9404	High Similarity	NPC239128
0.9404	High Similarity	NPC157784
0.9404	High Similarity	NPC57030
0.9396	High Similarity	NPC196277
0.9396	High Similarity	NPC203747
0.9396	High Similarity	NPC203077
0.9396	High Similarity	NPC195202
0.9396	High Similarity	NPC120464
0.9396	High Similarity	NPC238279
0.9396	High Similarity	NPC272721
0.9396	High Similarity	NPC166036
0.9396	High Similarity	NPC139364
0.9396	High Similarity	NPC194653

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 NPC472455 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	987
0.2-0.3	1713
0.3-0.4	2632
0.4-0.5	1762
0.5-0.6	1005
0.6-0.7	477
0.7-0.8	145
0.8-0.85	33
0.85-0.9	18
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD2801	Approved
0.9342	High Similarity	NPD2393	Clinical (unspecified phase)
0.9276	High Similarity	NPD1934	Approved
0.9221	High Similarity	NPD3882	Suspended
0.9128	High Similarity	NPD1511	Approved
0.9007	High Similarity	NPD1512	Approved
0.8944	High Similarity	NPD3818	Discontinued
0.894	High Similarity	NPD4378	Clinical (unspecified phase)
0.882	High Similarity	NPD6168	Clinical (unspecified phase)
0.882	High Similarity	NPD6167	Clinical (unspecified phase)
0.882	High Similarity	NPD6166	Phase 2
0.8816	High Similarity	NPD7410	Clinical (unspecified phase)
0.879	High Similarity	NPD3817	Phase 2
0.8774	High Similarity	NPD4380	Phase 2
0.8688	High Similarity	NPD5494	Approved
0.8679	High Similarity	NPD7075	Discontinued
0.8659	High Similarity	NPD7054	Approved
0.8616	High Similarity	NPD4868	Clinical (unspecified phase)
0.8608	High Similarity	NPD7096	Clinical (unspecified phase)
0.8606	High Similarity	NPD7472	Approved
0.8606	High Similarity	NPD7074	Phase 3
0.8591	High Similarity	NPD1510	Phase 2
0.858	High Similarity	NPD6232	Discontinued
0.8544	High Similarity	NPD6801	Discontinued
0.8543	High Similarity	NPD1549	Phase 2
0.8537	High Similarity	NPD7473	Discontinued
0.8533	High Similarity	NPD2796	Approved
0.8491	Intermediate Similarity	NPD7819	Suspended
0.8477	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1240	Approved
0.8446	Intermediate Similarity	NPD943	Approved
0.8443	Intermediate Similarity	NPD6797	Phase 2
0.8393	Intermediate Similarity	NPD7251	Discontinued
0.8387	Intermediate Similarity	NPD6799	Approved
0.8365	Intermediate Similarity	NPD7411	Suspended
0.8343	Intermediate Similarity	NPD7808	Phase 3
0.8333	Intermediate Similarity	NPD1607	Approved
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD1247	Approved
0.8282	Intermediate Similarity	NPD919	Approved
0.8261	Intermediate Similarity	NPD1465	Phase 2
0.8214	Intermediate Similarity	NPD5844	Phase 1
0.8214	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3926	Phase 2
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8118	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5402	Approved
0.8077	Intermediate Similarity	NPD3750	Approved
0.8072	Intermediate Similarity	NPD6959	Discontinued
0.807	Intermediate Similarity	NPD6559	Discontinued
0.8065	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2935	Discontinued
0.8049	Intermediate Similarity	NPD7768	Phase 2
0.8036	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2800	Approved
0.8013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3749	Approved
0.7933	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD447	Suspended
0.7908	Intermediate Similarity	NPD230	Phase 1
0.7898	Intermediate Similarity	NPD1243	Approved
0.7888	Intermediate Similarity	NPD920	Approved
0.7875	Intermediate Similarity	NPD2532	Approved
0.7875	Intermediate Similarity	NPD2534	Approved
0.7875	Intermediate Similarity	NPD2533	Approved
0.7875	Intermediate Similarity	NPD5401	Approved
0.7871	Intermediate Similarity	NPD2799	Discontinued
0.7871	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD2313	Discontinued
0.7821	Intermediate Similarity	NPD1551	Phase 2
0.7803	Intermediate Similarity	NPD5953	Discontinued
0.7791	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD2344	Approved
0.7764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3027	Phase 3
0.7756	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD3748	Approved
0.7753	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD9494	Approved
0.7742	Intermediate Similarity	NPD6651	Approved
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7736	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6099	Approved
0.7707	Intermediate Similarity	NPD6100	Approved
0.7702	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7286	Phase 2
0.7677	Intermediate Similarity	NPD1933	Approved
0.7658	Intermediate Similarity	NPD2346	Discontinued
0.7647	Intermediate Similarity	NPD7199	Phase 2
0.7633	Intermediate Similarity	NPD6234	Discontinued
0.7625	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2309	Approved
0.7578	Intermediate Similarity	NPD6190	Approved
0.7569	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7515	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7451	Intermediate Similarity	NPD2798	Approved
0.744	Intermediate Similarity	NPD37	Approved
0.7421	Intermediate Similarity	NPD4308	Phase 3
0.7421	Intermediate Similarity	NPD7033	Discontinued
0.7419	Intermediate Similarity	NPD4625	Phase 3
0.7412	Intermediate Similarity	NPD4965	Approved
0.7412	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD4966	Approved
0.7399	Intermediate Similarity	NPD3787	Discontinued
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7372	Intermediate Similarity	NPD3268	Approved
0.7356	Intermediate Similarity	NPD5242	Approved
0.7355	Intermediate Similarity	NPD6832	Phase 2
0.7355	Intermediate Similarity	NPD4908	Phase 1
0.7351	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7228	Approved
0.733	Intermediate Similarity	NPD7584	Approved
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7303	Intermediate Similarity	NPD9717	Approved
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7297	Intermediate Similarity	NPD4363	Phase 3
0.7297	Intermediate Similarity	NPD4360	Phase 2
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD2797	Approved
0.7262	Intermediate Similarity	NPD7458	Discontinued
0.7258	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4361	Phase 2
0.7253	Intermediate Similarity	NPD8150	Discontinued
0.7248	Intermediate Similarity	NPD5536	Phase 2
0.7237	Intermediate Similarity	NPD1610	Phase 2
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7233	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5124	Phase 1
0.7233	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2403	Approved
0.72	Intermediate Similarity	NPD7229	Phase 3
0.719	Intermediate Similarity	NPD1608	Approved
0.7186	Intermediate Similarity	NPD5049	Phase 3
0.7179	Intermediate Similarity	NPD3018	Phase 2
0.7178	Intermediate Similarity	NPD2424	Discontinued
0.7176	Intermediate Similarity	NPD6386	Approved
0.7176	Intermediate Similarity	NPD6385	Approved
0.7176	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7435	Discontinued
0.717	Intermediate Similarity	NPD4307	Phase 2
0.717	Intermediate Similarity	NPD4060	Phase 1
0.7165	Intermediate Similarity	NPD8151	Discontinued
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.7152	Intermediate Similarity	NPD411	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7151	Intermediate Similarity	NPD5353	Approved
0.7151	Intermediate Similarity	NPD4288	Approved
0.7151	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD4749	Approved
0.7135	Intermediate Similarity	NPD6844	Discontinued
0.7134	Intermediate Similarity	NPD2654	Approved
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1201	Approved
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7097	Intermediate Similarity	NPD3225	Approved
0.7083	Intermediate Similarity	NPD7697	Approved
0.7083	Intermediate Similarity	NPD7696	Phase 3
0.7083	Intermediate Similarity	NPD7698	Approved
0.7081	Intermediate Similarity	NPD4287	Approved
0.7078	Intermediate Similarity	NPD3972	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