NPASS Compound

Structure

NPC470398 OpenBabel07101718312D 27 27 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 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 3 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 3 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 -0.0000 -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 -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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 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 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 13 2 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 26 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 19 2 0 0 0 0 13 18 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 21 24 2 0 0 0 0 25 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.2
Volume:	400.138
LogP:	3.631
LogD:	3.556
LogS:	-3.658
# Rotatable Bonds:	11
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.22
Synthetic Accessibility Score:	3.872
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.684
MDCK Permeability:	1.526523192296736e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.065
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.83
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	98.32836151123047%
Volume Distribution (VD):	0.472
Pgp-substrate:	0.8849101066589355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.885
CYP1A2-substrate:	0.761
CYP2C19-inhibitor:	0.27
CYP2C19-substrate:	0.133
CYP2C9-inhibitor:	0.59
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.63
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	9.506
Half-life (T1/2):	0.48

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.451
Drug-inuced Liver Injury (DILI):	0.128
AMES Toxicity:	0.252
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.814
Skin Sensitization:	0.687
Carcinogencity:	0.258
Eye Corrosion:	0.003
Eye Irritation:	0.682
Respiratory Toxicity:	0.807

Download Data

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

Natural Product: NPC470398

Natural Product ID:	NPC470398
*Common Name:**	Olympicin D
IUPAC Name:	1-[2-[(2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienoxy]-4,6-dihydroxyphenyl]-2-methylbutan-1-one
Synonyms:	Olympicin D
Standard InCHIKey:	BMEORAQEILRDFC-NTEUORMPSA-N
Standard InCHI:	InChI=1S/C21H30O6/c1-6-15(5)21(24)20-17(23)11-16(22)12-19(20)26-10-9-14(4)7-8-18(27-25)13(2)3/h9,11-12,15,18,22-23,25H,2,6-8,10H2,1,3-5H3/b14-9+
SMILES:	CCC(C(=O)c1c(OC/C=C(/CCC(C(=C)C)OO)C)cc(cc1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023361
PubChem CID:	57379194
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[514600]

☑ 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 NPC470398 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	330
0.1-0.2	1422
0.2-0.3	4018
0.3-0.4	9961
0.4-0.5	8681
0.5-0.6	3861
0.6-0.7	6073
0.7-0.8	5542
0.8-0.85	1661
0.85-0.9	847
0.9-0.95	294
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC470397
0.9846	High Similarity	NPC144027
0.9846	High Similarity	NPC236974
0.9699	High Similarity	NPC470399
0.9697	High Similarity	NPC156910
0.9697	High Similarity	NPC187826
0.9692	High Similarity	NPC203817
0.9481	High Similarity	NPC140890
0.9481	High Similarity	NPC139554
0.9412	High Similarity	NPC6407
0.9412	High Similarity	NPC188243
0.9412	High Similarity	NPC129853
0.9412	High Similarity	NPC76445
0.9412	High Similarity	NPC284550
0.9412	High Similarity	NPC110228
0.9407	High Similarity	NPC124269
0.9403	High Similarity	NPC240147
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
0.9348	High Similarity	NPC81697
0.9348	High Similarity	NPC125894
0.9348	High Similarity	NPC223812
0.9348	High Similarity	NPC77794
0.9348	High Similarity	NPC107177
0.9348	High Similarity	NPC85162
0.9348	High Similarity	NPC278249
0.9343	High Similarity	NPC166689
0.9343	High Similarity	NPC96408
0.9343	High Similarity	NPC17170
0.9343	High Similarity	NPC156190
0.9343	High Similarity	NPC258630
0.9343	High Similarity	NPC279650
0.9338	High Similarity	NPC274784
0.9338	High Similarity	NPC329203
0.9338	High Similarity	NPC20709
0.9338	High Similarity	NPC265871
0.9338	High Similarity	NPC310135
0.9338	High Similarity	NPC150648
0.9338	High Similarity	NPC23257
0.9338	High Similarity	NPC222342
0.9338	High Similarity	NPC225153
0.9333	High Similarity	NPC188879
0.9328	High Similarity	NPC60667
0.9323	High Similarity	NPC223457
0.9318	High Similarity	NPC475589
0.9318	High Similarity	NPC31872
0.9318	High Similarity	NPC473584
0.9281	High Similarity	NPC473013
0.9281	High Similarity	NPC235217
0.9281	High Similarity	NPC473014
0.9281	High Similarity	NPC473015
0.9281	High Similarity	NPC131579
0.9281	High Similarity	NPC131568
0.9275	High Similarity	NPC107572
0.9275	High Similarity	NPC64915
0.9275	High Similarity	NPC324134
0.9275	High Similarity	NPC223500
0.9275	High Similarity	NPC166934
0.9275	High Similarity	NPC167624
0.9275	High Similarity	NPC227579
0.9275	High Similarity	NPC1089
0.9275	High Similarity	NPC37496
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	NPC265040
0.9275	High Similarity	NPC328164
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	NPC296917
0.9275	High Similarity	NPC10937
0.9275	High Similarity	NPC66515
0.9275	High Similarity	NPC228504
0.9275	High Similarity	NPC78
0.9275	High Similarity	NPC182852
0.9275	High Similarity	NPC166482
0.9275	High Similarity	NPC177354
0.927	High Similarity	NPC471587
0.927	High Similarity	NPC307990
0.927	High Similarity	NPC16455
0.9265	High Similarity	NPC474487
0.9265	High Similarity	NPC470672
0.9265	High Similarity	NPC470669
0.9265	High Similarity	NPC470668
0.9265	High Similarity	NPC474504
0.9265	High Similarity	NPC131130
0.9265	High Similarity	NPC470671
0.9265	High Similarity	NPC118813
0.9259	High Similarity	NPC240593
0.9254	High Similarity	NPC125920
0.9242	High Similarity	NPC270369
0.9242	High Similarity	NPC324482
0.9242	High Similarity	NPC5515
0.9231	High Similarity	NPC128428
0.9231	High Similarity	NPC305518
0.9214	High Similarity	NPC285630
0.9214	High Similarity	NPC476088
0.9214	High Similarity	NPC127059
0.9214	High Similarity	NPC474161
0.9209	High Similarity	NPC75049
0.9209	High Similarity	NPC169591
0.9209	High Similarity	NPC185276
0.9209	High Similarity	NPC164980
0.9209	High Similarity	NPC175504
0.9209	High Similarity	NPC149026
0.9209	High Similarity	NPC39329
0.9209	High Similarity	NPC143896
0.9209	High Similarity	NPC257097
0.9209	High Similarity	NPC310130
0.9209	High Similarity	NPC150408
0.9209	High Similarity	NPC316816
0.9209	High Similarity	NPC221432
0.9209	High Similarity	NPC68104
0.9209	High Similarity	NPC91560
0.9209	High Similarity	NPC478086
0.9209	High Similarity	NPC214166
0.9203	High Similarity	NPC213322
0.9203	High Similarity	NPC312391
0.9203	High Similarity	NPC324386
0.9203	High Similarity	NPC4743
0.9203	High Similarity	NPC110038
0.9203	High Similarity	NPC171870
0.9203	High Similarity	NPC282300
0.9203	High Similarity	NPC248372
0.9197	High Similarity	NPC37206
0.9197	High Similarity	NPC261234
0.9191	High Similarity	NPC13768
0.9191	High Similarity	NPC295261
0.9191	High Similarity	NPC107586
0.9191	High Similarity	NPC296490
0.9191	High Similarity	NPC79943
0.9191	High Similarity	NPC243083
0.9191	High Similarity	NPC32441
0.9191	High Similarity	NPC287246
0.9191	High Similarity	NPC12296
0.9185	High Similarity	NPC84699
0.9179	High Similarity	NPC144051
0.9179	High Similarity	NPC28753
0.9179	High Similarity	NPC93756
0.9179	High Similarity	NPC20560
0.9179	High Similarity	NPC18877
0.9179	High Similarity	NPC159623
0.9179	High Similarity	NPC294593
0.9179	High Similarity	NPC108113
0.9179	High Similarity	NPC82225
0.9179	High Similarity	NPC204960
0.9173	High Similarity	NPC27490
0.9167	High Similarity	NPC84772
0.9149	High Similarity	NPC473133
0.9149	High Similarity	NPC47388
0.9149	High Similarity	NPC470670
0.9143	High Similarity	NPC236766
0.9143	High Similarity	NPC197252
0.9143	High Similarity	NPC311144
0.9143	High Similarity	NPC209040
0.9143	High Similarity	NPC224714
0.9143	High Similarity	NPC470890
0.9143	High Similarity	NPC271288
0.9143	High Similarity	NPC319752
0.9137	High Similarity	NPC202981
0.9137	High Similarity	NPC73028
0.9137	High Similarity	NPC325346
0.913	High Similarity	NPC241100
0.913	High Similarity	NPC477272
0.913	High Similarity	NPC159275
0.9124	High Similarity	NPC280284
0.9124	High Similarity	NPC147686
0.9124	High Similarity	NPC329225
0.9124	High Similarity	NPC99333
0.9124	High Similarity	NPC472460
0.9124	High Similarity	NPC188947
0.9118	High Similarity	NPC47815
0.9118	High Similarity	NPC13408
0.9118	High Similarity	NPC29353
0.9118	High Similarity	NPC231772
0.9118	High Similarity	NPC124784
0.9118	High Similarity	NPC473887
0.9118	High Similarity	NPC127447
0.9118	High Similarity	NPC194281
0.9118	High Similarity	NPC234133
0.9111	High Similarity	NPC164136
0.9111	High Similarity	NPC286336
0.9091	High Similarity	NPC473894
0.9091	High Similarity	NPC230818
0.9078	High Similarity	NPC470647
0.9078	High Similarity	NPC24136
0.9078	High Similarity	NPC246948
0.9078	High Similarity	NPC470134
0.9078	High Similarity	NPC142405
0.9078	High Similarity	NPC176229

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 NPC470398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	957
0.2-0.3	1764
0.3-0.4	2583
0.4-0.5	1827
0.5-0.6	1124
0.6-0.7	432
0.7-0.8	129
0.8-0.85	29
0.85-0.9	7
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9191	High Similarity	NPD1552	Clinical (unspecified phase)
0.9191	High Similarity	NPD1550	Clinical (unspecified phase)
0.9124	High Similarity	NPD1549	Phase 2
0.8889	High Similarity	NPD1240	Approved
0.8873	High Similarity	NPD4378	Clinical (unspecified phase)
0.8841	High Similarity	NPD2796	Approved
0.8768	High Similarity	NPD1510	Phase 2
0.8759	High Similarity	NPD1607	Approved
0.8716	High Similarity	NPD8443	Clinical (unspecified phase)
0.8649	High Similarity	NPD2393	Clinical (unspecified phase)
0.8611	High Similarity	NPD7410	Clinical (unspecified phase)
0.8582	High Similarity	NPD970	Clinical (unspecified phase)
0.8581	High Similarity	NPD1934	Approved
0.8542	High Similarity	NPD6799	Approved
0.8514	High Similarity	NPD7411	Suspended
0.8489	Intermediate Similarity	NPD6651	Approved
0.8477	Intermediate Similarity	NPD7075	Discontinued
0.8446	Intermediate Similarity	NPD4380	Phase 2
0.84	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2800	Approved
0.8355	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD6599	Discontinued
0.8289	Intermediate Similarity	NPD3882	Suspended
0.8288	Intermediate Similarity	NPD1511	Approved
0.8278	Intermediate Similarity	NPD7819	Suspended
0.8278	Intermediate Similarity	NPD2801	Approved
0.8231	Intermediate Similarity	NPD2532	Approved
0.8231	Intermediate Similarity	NPD2533	Approved
0.8231	Intermediate Similarity	NPD2534	Approved
0.8194	Intermediate Similarity	NPD6959	Discontinued
0.8182	Intermediate Similarity	NPD1551	Phase 2
0.8176	Intermediate Similarity	NPD1512	Approved
0.8153	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6166	Phase 2
0.8138	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD3750	Approved
0.8082	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD7768	Phase 2
0.8038	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD9717	Approved
0.8014	Intermediate Similarity	NPD2654	Approved
0.8014	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3817	Phase 2
0.795	Intermediate Similarity	NPD7074	Phase 3
0.7937	Intermediate Similarity	NPD3818	Discontinued
0.7935	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6099	Approved
0.7931	Intermediate Similarity	NPD6100	Approved
0.7898	Intermediate Similarity	NPD5494	Approved
0.7888	Intermediate Similarity	NPD7054	Approved
0.7885	Intermediate Similarity	NPD3749	Approved
0.7881	Intermediate Similarity	NPD920	Approved
0.7877	Intermediate Similarity	NPD2344	Approved
0.7867	Intermediate Similarity	NPD5401	Approved
0.7862	Intermediate Similarity	NPD2799	Discontinued
0.7852	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1203	Approved
0.784	Intermediate Similarity	NPD7472	Approved
0.7838	Intermediate Similarity	NPD4628	Phase 3
0.781	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD422	Phase 1
0.7808	Intermediate Similarity	NPD2935	Discontinued
0.7805	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD6832	Phase 2
0.7801	Intermediate Similarity	NPD4908	Phase 1
0.7791	Intermediate Similarity	NPD5953	Discontinued
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.7778	Intermediate Similarity	NPD9545	Approved
0.7748	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7251	Discontinued
0.774	Intermediate Similarity	NPD3748	Approved
0.774	Intermediate Similarity	NPD7033	Discontinued
0.7718	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7808	Phase 3
0.7692	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3268	Approved
0.7681	Intermediate Similarity	NPD1610	Phase 2
0.7667	Intermediate Similarity	NPD2309	Approved
0.7655	Intermediate Similarity	NPD230	Phase 1
0.7655	Intermediate Similarity	NPD5124	Phase 1
0.7655	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7473	Discontinued
0.7647	Intermediate Similarity	NPD1548	Phase 1
0.7643	Intermediate Similarity	NPD5402	Approved
0.7636	Intermediate Similarity	NPD6559	Discontinued
0.763	Intermediate Similarity	NPD9493	Approved
0.759	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2797	Approved
0.7586	Intermediate Similarity	NPD943	Approved
0.7578	Intermediate Similarity	NPD6232	Discontinued
0.7537	Intermediate Similarity	NPD1241	Discontinued
0.7535	Intermediate Similarity	NPD1019	Discontinued
0.7535	Intermediate Similarity	NPD2798	Approved
0.7515	Intermediate Similarity	NPD1729	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD5711	Approved
0.7469	Intermediate Similarity	NPD5710	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	NPD1296	Phase 2
0.7448	Intermediate Similarity	NPD411	Approved
0.7448	Intermediate Similarity	NPD2313	Discontinued
0.7447	Intermediate Similarity	NPD4749	Approved
0.7425	Intermediate Similarity	NPD6104	Discontinued
0.7423	Intermediate Similarity	NPD3926	Phase 2
0.7415	Intermediate Similarity	NPD447	Suspended
0.7407	Intermediate Similarity	NPD1247	Approved
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2403	Approved
0.7376	Intermediate Similarity	NPD3972	Approved
0.7376	Intermediate Similarity	NPD1608	Approved
0.7343	Intermediate Similarity	NPD3267	Approved
0.7343	Intermediate Similarity	NPD3266	Approved
0.7338	Intermediate Similarity	NPD7390	Discontinued
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7329	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3226	Approved
0.7314	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4361	Phase 2
0.7297	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD6004	Phase 3
0.7285	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
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	NPD3225	Approved
0.7273	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1465	Phase 2
0.723	Intermediate Similarity	NPD1613	Approved
0.723	Intermediate Similarity	NPD3142	Approved
0.723	Intermediate Similarity	NPD3140	Approved
0.723	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1652	Phase 2
0.7181	Intermediate Similarity	NPD1933	Approved
0.7179	Intermediate Similarity	NPD4662	Approved
0.7179	Intermediate Similarity	NPD4661	Approved
0.7172	Intermediate Similarity	NPD5647	Approved
0.7171	Intermediate Similarity	NPD2346	Discontinued
0.7163	Intermediate Similarity	NPD1778	Approved
0.7163	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7124	Intermediate Similarity	NPD2424	Discontinued
0.7123	Intermediate Similarity	NPD2861	Phase 2
0.7123	Intermediate Similarity	NPD9494	Approved
0.7123	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7458	Discontinued
0.7099	Intermediate Similarity	NPD846	Approved
0.7099	Intermediate Similarity	NPD4288	Approved
0.7099	Intermediate Similarity	NPD940	Approved
0.7099	Intermediate Similarity	NPD2296	Approved
0.7097	Intermediate Similarity	NPD3887	Approved
0.7091	Intermediate Similarity	NPD7199	Phase 2
0.7075	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7229	Phase 3
0.7047	Intermediate Similarity	NPD6233	Phase 2
0.7037	Intermediate Similarity	NPD9266	Approved
0.7037	Intermediate Similarity	NPD5760	Phase 2
0.7037	Intermediate Similarity	NPD74	Approved
0.7037	Intermediate Similarity	NPD2684	Approved
0.7037	Intermediate Similarity	NPD5761	Phase 2
0.7034	Intermediate Similarity	NPD1876	Approved
0.7027	Intermediate Similarity	NPD4625	Phase 3
0.7021	Intermediate Similarity	NPD1894	Discontinued
0.7014	Intermediate Similarity	NPD1481	Phase 2
0.7006	Intermediate Similarity	NPD7212	Phase 2
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7213	Phase 3
0.7	Intermediate Similarity	NPD4307	Phase 2
0.6994	Remote Similarity	NPD5353	Approved
0.6993	Remote Similarity	NPD3496	Discontinued
0.6987	Remote Similarity	NPD2354	Approved
0.6982	Remote Similarity	NPD3751	Discontinued
0.6982	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3764	Approved
0.6975	Remote Similarity	NPD37	Approved
0.6975	Remote Similarity	NPD7577	Discontinued
0.6975	Remote Similarity	NPD6279	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