NPASS Compound

Structure

NPC187826 OpenBabel07101719242D 26 26 0 0 1 0 0 0 0 0999 V2000 2.5981 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4282 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 2.8660 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 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 -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 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 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 -0.0000 -1.0000 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 0.0000 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 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 14 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 10 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 21 1 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 18 2 0 0 0 0 15 3 1 1 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 20 24 2 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.21
Volume:	391.348
LogP:	3.474
LogD:	3.361
LogS:	-3.801
# Rotatable Bonds:	9
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	3.599
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.645
MDCK Permeability:	2.0399718778207898e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.371
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	98.67703247070312%
Volume Distribution (VD):	0.346
Pgp-substrate:	0.851898729801178%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.427
CYP2C19-inhibitor:	0.742
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.954
CYP2D6-substrate:	0.662
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	7.592
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.176
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.59
Skin Sensitization:	0.671
Carcinogencity:	0.058
Eye Corrosion:	0.003
Eye Irritation:	0.743
Respiratory Toxicity:	0.616

Download Data

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

Natural Product: NPC187826

Natural Product ID:	NPC187826
*Common Name:**	Olympicin B
IUPAC Name:	(2S)-1-[2,4-dihydroxy-6-[(2E,5E)-7-hydroxy-3,7-dimethylocta-2,5-dienoxy]phenyl]-2-methylbutan-1-one
Synonyms:	Olympicin B
Standard InCHIKey:	YQCPAHSZPXSDHS-PVKPBJJJSA-N
Standard InCHI:	InChI=1S/C21H30O5/c1-6-15(3)20(24)19-17(23)12-16(22)13-18(19)26-11-9-14(2)8-7-10-21(4,5)25/h7,9-10,12-13,15,22-23,25H,6,8,11H2,1-5H3/b10-7+,14-9+/t15-/m0/s1
SMILES:	CC[C@H](C)C(=O)c1c(cc(cc1OC/C=C(C)/C/C=C/C(C)(C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023359
PubChem CID:	57379192
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO22037	Hypericum olympicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21899267]
NPO22037	Hypericum olympicum	Species	Hypericaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[566970]

☑ 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 NPC187826 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	327
0.1-0.2	1449
0.2-0.3	3930
0.3-0.4	10119
0.4-0.5	8403
0.5-0.6	3749
0.6-0.7	6053
0.7-0.8	5546
0.8-0.85	1802
0.85-0.9	893
0.9-0.95	410
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC144027
0.9846	High Similarity	NPC236974
0.9699	High Similarity	NPC470399
0.9697	High Similarity	NPC156910
0.9697	High Similarity	NPC470398
0.9697	High Similarity	NPC470397
0.9692	High Similarity	NPC203817
0.9627	High Similarity	NPC23257
0.9556	High Similarity	NPC76445
0.9556	High Similarity	NPC284550
0.9556	High Similarity	NPC129853
0.9556	High Similarity	NPC471587
0.9552	High Similarity	NPC470668
0.9552	High Similarity	NPC124269
0.9552	High Similarity	NPC470669
0.9478	High Similarity	NPC188879
0.942	High Similarity	NPC131579
0.942	High Similarity	NPC131568
0.9412	High Similarity	NPC6407
0.9412	High Similarity	NPC188243
0.9412	High Similarity	NPC110228
0.9407	High Similarity	NPC470671
0.9407	High Similarity	NPC118813
0.9407	High Similarity	NPC474504
0.9407	High Similarity	NPC131130
0.9407	High Similarity	NPC470672
0.9407	High Similarity	NPC474487
0.9403	High Similarity	NPC240147
0.9403	High Similarity	NPC240593
0.9403	High Similarity	NPC121243
0.9403	High Similarity	NPC174999
0.9394	High Similarity	NPC25937
0.9394	High Similarity	NPC10971
0.9385	High Similarity	NPC69235
0.9385	High Similarity	NPC212379
0.9353	High Similarity	NPC285630
0.9353	High Similarity	NPC127059
0.9348	High Similarity	NPC214166
0.9348	High Similarity	NPC478086
0.9348	High Similarity	NPC316816
0.9348	High Similarity	NPC125894
0.9348	High Similarity	NPC107177
0.9348	High Similarity	NPC223812
0.9348	High Similarity	NPC77794
0.9348	High Similarity	NPC85162
0.9348	High Similarity	NPC278249
0.9348	High Similarity	NPC81697
0.9343	High Similarity	NPC282300
0.9338	High Similarity	NPC274784
0.9338	High Similarity	NPC310135
0.9338	High Similarity	NPC140890
0.9338	High Similarity	NPC329203
0.9338	High Similarity	NPC20709
0.9338	High Similarity	NPC265871
0.9338	High Similarity	NPC150648
0.9338	High Similarity	NPC222342
0.9338	High Similarity	NPC139554
0.9338	High Similarity	NPC225153
0.9338	High Similarity	NPC261234
0.9328	High Similarity	NPC60667
0.9328	High Similarity	NPC101752
0.9323	High Similarity	NPC28753
0.9323	High Similarity	NPC294593
0.9323	High Similarity	NPC82225
0.9323	High Similarity	NPC18877
0.9323	High Similarity	NPC223457
0.9323	High Similarity	NPC204960
0.9323	High Similarity	NPC20560
0.9323	High Similarity	NPC159623
0.9323	High Similarity	NPC144051
0.9318	High Similarity	NPC475589
0.9318	High Similarity	NPC31872
0.9318	High Similarity	NPC473584
0.9281	High Similarity	NPC235217
0.9281	High Similarity	NPC311144
0.9281	High Similarity	NPC271288
0.9281	High Similarity	NPC209040
0.9281	High Similarity	NPC473013
0.9281	High Similarity	NPC473014
0.9281	High Similarity	NPC473015
0.9275	High Similarity	NPC167624
0.9275	High Similarity	NPC107572
0.9275	High Similarity	NPC324134
0.9275	High Similarity	NPC223500
0.9275	High Similarity	NPC166934
0.9275	High Similarity	NPC11561
0.9275	High Similarity	NPC227579
0.9275	High Similarity	NPC1089
0.9275	High Similarity	NPC37496
0.9275	High Similarity	NPC328164
0.9275	High Similarity	NPC40833
0.9275	High Similarity	NPC324436
0.9275	High Similarity	NPC76338
0.9275	High Similarity	NPC32739
0.9275	High Similarity	NPC220998
0.9275	High Similarity	NPC202981
0.9275	High Similarity	NPC265040
0.9275	High Similarity	NPC10937
0.9275	High Similarity	NPC306829
0.9275	High Similarity	NPC194432
0.9275	High Similarity	NPC76372
0.9275	High Similarity	NPC161506
0.9275	High Similarity	NPC148757
0.9275	High Similarity	NPC125855
0.9275	High Similarity	NPC228504
0.9275	High Similarity	NPC296917
0.9275	High Similarity	NPC66515
0.9275	High Similarity	NPC78
0.9275	High Similarity	NPC182852
0.9275	High Similarity	NPC166482
0.9275	High Similarity	NPC177354
0.9275	High Similarity	NPC226636
0.9275	High Similarity	NPC64915
0.927	High Similarity	NPC150522
0.927	High Similarity	NPC159275
0.927	High Similarity	NPC241100
0.927	High Similarity	NPC307990
0.927	High Similarity	NPC477272
0.927	High Similarity	NPC16455
0.9265	High Similarity	NPC99333
0.9265	High Similarity	NPC188947
0.9265	High Similarity	NPC280284
0.9259	High Similarity	NPC473887
0.9259	High Similarity	NPC13408
0.9259	High Similarity	NPC194281
0.9259	High Similarity	NPC231772
0.9259	High Similarity	NPC127447
0.9259	High Similarity	NPC47815
0.9259	High Similarity	NPC29353
0.9259	High Similarity	NPC234133
0.9259	High Similarity	NPC124784
0.9254	High Similarity	NPC164136
0.9254	High Similarity	NPC286336
0.9254	High Similarity	NPC125920
0.9242	High Similarity	NPC5515
0.9242	High Similarity	NPC324482
0.9242	High Similarity	NPC270369
0.9231	High Similarity	NPC128428
0.9231	High Similarity	NPC305518
0.9214	High Similarity	NPC83357
0.9214	High Similarity	NPC246948
0.9214	High Similarity	NPC474161
0.9214	High Similarity	NPC67805
0.9214	High Similarity	NPC88964
0.9214	High Similarity	NPC54577
0.9214	High Similarity	NPC299011
0.9214	High Similarity	NPC301276
0.9214	High Similarity	NPC470647
0.9214	High Similarity	NPC477955
0.9214	High Similarity	NPC475052
0.9214	High Similarity	NPC195621
0.9214	High Similarity	NPC214774
0.9214	High Similarity	NPC476088
0.9214	High Similarity	NPC312973
0.9214	High Similarity	NPC142405
0.9214	High Similarity	NPC111786
0.9214	High Similarity	NPC176229
0.9214	High Similarity	NPC20488
0.9214	High Similarity	NPC267375
0.9209	High Similarity	NPC166138
0.9209	High Similarity	NPC18585
0.9209	High Similarity	NPC169591
0.9209	High Similarity	NPC185276
0.9209	High Similarity	NPC164980
0.9209	High Similarity	NPC149026
0.9209	High Similarity	NPC75049
0.9209	High Similarity	NPC39329
0.9209	High Similarity	NPC175504
0.9209	High Similarity	NPC143896
0.9209	High Similarity	NPC257097
0.9209	High Similarity	NPC106985
0.9209	High Similarity	NPC310130
0.9209	High Similarity	NPC150408
0.9209	High Similarity	NPC221432
0.9209	High Similarity	NPC113770
0.9209	High Similarity	NPC68104
0.9209	High Similarity	NPC91560
0.9203	High Similarity	NPC118840
0.9203	High Similarity	NPC3188
0.9203	High Similarity	NPC279650
0.9203	High Similarity	NPC324386
0.9203	High Similarity	NPC4743
0.9203	High Similarity	NPC96692
0.9203	High Similarity	NPC258630
0.9203	High Similarity	NPC156190
0.9203	High Similarity	NPC64908
0.9203	High Similarity	NPC147688
0.9203	High Similarity	NPC17170
0.9203	High Similarity	NPC110038
0.9203	High Similarity	NPC96408
0.9203	High Similarity	NPC213322
0.9203	High Similarity	NPC103362
0.9203	High Similarity	NPC312391
0.9203	High Similarity	NPC110969
0.9203	High Similarity	NPC205006
0.9203	High Similarity	NPC156590
0.9203	High Similarity	NPC166689
0.9203	High Similarity	NPC248372
0.9197	High Similarity	NPC55018
0.9197	High Similarity	NPC18260

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 NPC187826 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	951
0.2-0.3	1680
0.3-0.4	2559
0.4-0.5	1856
0.5-0.6	1152
0.6-0.7	463
0.7-0.8	147
0.8-0.85	30
0.85-0.9	9
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9191	High Similarity	NPD1550	Clinical (unspecified phase)
0.9191	High Similarity	NPD1552	Clinical (unspecified phase)
0.9124	High Similarity	NPD1549	Phase 2
0.903	High Similarity	NPD1240	Approved
0.9007	High Similarity	NPD4378	Clinical (unspecified phase)
0.8905	High Similarity	NPD1510	Phase 2
0.8897	High Similarity	NPD1607	Approved
0.8873	High Similarity	NPD7410	Clinical (unspecified phase)
0.8841	High Similarity	NPD2796	Approved
0.8716	High Similarity	NPD8443	Clinical (unspecified phase)
0.8671	High Similarity	NPD6799	Approved
0.8649	High Similarity	NPD2393	Clinical (unspecified phase)
0.8639	High Similarity	NPD7411	Suspended
0.8582	High Similarity	NPD970	Clinical (unspecified phase)
0.8581	High Similarity	NPD1934	Approved
0.8489	Intermediate Similarity	NPD6651	Approved
0.8477	Intermediate Similarity	NPD7075	Discontinued
0.8467	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD6599	Discontinued
0.8446	Intermediate Similarity	NPD4380	Phase 2
0.8414	Intermediate Similarity	NPD1511	Approved
0.8411	Intermediate Similarity	NPD3882	Suspended
0.84	Intermediate Similarity	NPD7819	Suspended
0.84	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD2801	Approved
0.8392	Intermediate Similarity	NPD2800	Approved
0.8355	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.831	Intermediate Similarity	NPD1551	Phase 2
0.8299	Intermediate Similarity	NPD1512	Approved
0.8264	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD2532	Approved
0.8231	Intermediate Similarity	NPD2533	Approved
0.8231	Intermediate Similarity	NPD2534	Approved
0.8207	Intermediate Similarity	NPD3750	Approved
0.8207	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD7768	Phase 2
0.8153	Intermediate Similarity	NPD6166	Phase 2
0.8153	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD9717	Approved
0.8117	Intermediate Similarity	NPD3749	Approved
0.8105	Intermediate Similarity	NPD3817	Phase 2
0.8077	Intermediate Similarity	NPD6959	Discontinued
0.8056	Intermediate Similarity	NPD6100	Approved
0.8056	Intermediate Similarity	NPD6099	Approved
0.8014	Intermediate Similarity	NPD2654	Approved
0.8014	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2344	Approved
0.7986	Intermediate Similarity	NPD2799	Discontinued
0.7973	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1203	Approved
0.795	Intermediate Similarity	NPD7074	Phase 3
0.7941	Intermediate Similarity	NPD422	Phase 1
0.7937	Intermediate Similarity	NPD3818	Discontinued
0.7931	Intermediate Similarity	NPD2935	Discontinued
0.7929	Intermediate Similarity	NPD6832	Phase 2
0.7929	Intermediate Similarity	NPD4908	Phase 1
0.7914	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD9545	Approved
0.7901	Intermediate Similarity	NPD5953	Discontinued
0.7898	Intermediate Similarity	NPD5494	Approved
0.7888	Intermediate Similarity	NPD7054	Approved
0.7888	Intermediate Similarity	NPD7286	Phase 2
0.7867	Intermediate Similarity	NPD5401	Approved
0.7867	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3748	Approved
0.7862	Intermediate Similarity	NPD7033	Discontinued
0.784	Intermediate Similarity	NPD7472	Approved
0.7838	Intermediate Similarity	NPD4628	Phase 3
0.7838	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD3268	Approved
0.7817	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1610	Phase 2
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7785	Intermediate Similarity	NPD2309	Approved
0.7778	Intermediate Similarity	NPD1548	Phase 1
0.7778	Intermediate Similarity	NPD5124	Phase 1
0.7778	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7473	Discontinued
0.7761	Intermediate Similarity	NPD9493	Approved
0.7744	Intermediate Similarity	NPD7251	Discontinued
0.7714	Intermediate Similarity	NPD2797	Approved
0.7708	Intermediate Similarity	NPD943	Approved
0.7697	Intermediate Similarity	NPD7808	Phase 3
0.7688	Intermediate Similarity	NPD6232	Discontinued
0.7669	Intermediate Similarity	NPD1241	Discontinued
0.766	Intermediate Similarity	NPD1019	Discontinued
0.766	Intermediate Similarity	NPD2798	Approved
0.7655	Intermediate Similarity	NPD230	Phase 1
0.7643	Intermediate Similarity	NPD5402	Approved
0.7636	Intermediate Similarity	NPD6559	Discontinued
0.7622	Intermediate Similarity	NPD1729	Discontinued
0.761	Intermediate Similarity	NPD919	Approved
0.759	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4749	Approved
0.7569	Intermediate Similarity	NPD2313	Discontinued
0.7569	Intermediate Similarity	NPD1296	Phase 2
0.7569	Intermediate Similarity	NPD411	Approved
0.7534	Intermediate Similarity	NPD447	Suspended
0.7531	Intermediate Similarity	NPD3926	Phase 2
0.753	Intermediate Similarity	NPD6104	Discontinued
0.7516	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7485	Intermediate Similarity	NPD2403	Approved
0.7469	Intermediate Similarity	NPD5711	Approved
0.7469	Intermediate Similarity	NPD5710	Approved
0.7465	Intermediate Similarity	NPD3267	Approved
0.7465	Intermediate Similarity	NPD3266	Approved
0.7457	Intermediate Similarity	NPD4360	Phase 2
0.7457	Intermediate Similarity	NPD4363	Phase 3
0.7455	Intermediate Similarity	NPD5844	Phase 1
0.7452	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3226	Approved
0.7415	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4361	Phase 2
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3225	Approved
0.7383	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3140	Approved
0.7347	Intermediate Similarity	NPD3142	Approved
0.7338	Intermediate Similarity	NPD7390	Discontinued
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7308	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6355	Discontinued
0.7297	Intermediate Similarity	NPD1933	Approved
0.7286	Intermediate Similarity	NPD17	Approved
0.7286	Intermediate Similarity	NPD1778	Approved
0.7285	Intermediate Similarity	NPD2346	Discontinued
0.7285	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6004	Phase 3
0.7285	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6002	Phase 3
0.7285	Intermediate Similarity	NPD6005	Phase 3
0.7273	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4625	Phase 3
0.725	Intermediate Similarity	NPD1465	Phase 2
0.7241	Intermediate Similarity	NPD9494	Approved
0.7237	Intermediate Similarity	NPD2424	Discontinued
0.7231	Intermediate Similarity	NPD940	Approved
0.7231	Intermediate Similarity	NPD846	Approved
0.723	Intermediate Similarity	NPD1613	Approved
0.723	Intermediate Similarity	NPD4307	Phase 2
0.723	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7458	Discontinued
0.7214	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3764	Approved
0.7208	Intermediate Similarity	NPD2354	Approved
0.7208	Intermediate Similarity	NPD3887	Approved
0.7205	Intermediate Similarity	NPD4288	Approved
0.7205	Intermediate Similarity	NPD2296	Approved
0.7195	Intermediate Similarity	NPD7199	Phase 2
0.7192	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1652	Phase 2
0.7188	Intermediate Similarity	NPD7577	Discontinued
0.7179	Intermediate Similarity	NPD4662	Approved
0.7179	Intermediate Similarity	NPD4661	Approved
0.7172	Intermediate Similarity	NPD5647	Approved
0.7171	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9266	Approved
0.7164	Intermediate Similarity	NPD2684	Approved
0.7164	Intermediate Similarity	NPD74	Approved
0.7153	Intermediate Similarity	NPD1876	Approved
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.7143	Intermediate Similarity	NPD5761	Phase 2
0.7133	Intermediate Similarity	NPD1481	Phase 2
0.7126	Intermediate Similarity	NPD4287	Approved
0.7123	Intermediate Similarity	NPD2861	Phase 2
0.7123	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3496	Discontinued
0.7108	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD9264	Approved
0.709	Intermediate Similarity	NPD9263	Approved
0.709	Intermediate Similarity	NPD9267	Approved
0.709	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3751	Discontinued
0.7081	Intermediate Similarity	NPD6280	Approved
0.7081	Intermediate Similarity	NPD6279	Approved
0.708	Intermediate Similarity	NPD7843	Approved
0.7066	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1535	Discovery

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