NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	296.24
Volume:	338.345
LogP:	5.17
LogD:	2.969
LogS:	-3.836
# Rotatable Bonds:	15
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	2.297
Fsp3:	0.778
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.905
MDCK Permeability:	2.399987351964228e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.723
30% Bioavailability (F30%):	0.554

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.422
Plasma Protein Binding (PPB):	97.63240814208984%
Volume Distribution (VD):	0.419
Pgp-substrate:	1.4740358591079712%

ADMET: Metabolism

CYP1A2-inhibitor:	0.104
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.324
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	3.134
Half-life (T1/2):	0.85

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.528
Carcinogencity:	0.159
Eye Corrosion:	0.957
Eye Irritation:	0.94
Respiratory Toxicity:	0.367

Download Data

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

Natural Product: NPC27490

Natural Product ID:	NPC27490
*Common Name:**	Aspidinol C
IUPAC Name:	1-(2,6-dihydroxy-4-methoxy-3-methylphenyl)-3-methylbutan-1-one
Synonyms:	Aspidinol C
Standard InCHIKey:	LFTHKHYHTUZOJP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H18O4/c1-7(2)5-9(14)12-10(15)6-11(17-4)8(3)13(12)16/h6-7,15-16H,5H2,1-4H3
SMILES:	COc1cc(O)c(c(c1C)O)C(=O)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641981
PubChem CID:	50899947
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
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19606850]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043475]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[21043475]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074257]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8089	Hypericum chinense	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	=	2.0	ug.mL-1	PMID[535962]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[535962]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[535962]
NPT1101	Organism	Staphylococcus aureus subsp. aureus RN4220	Staphylococcus aureus subsp. aureus RN4220	MIC	=	16.0	ug.mL-1	PMID[535962]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[535962]

☑ 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 NPC27490 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	347
0.1-0.2	1631
0.2-0.3	4422
0.3-0.4	11109
0.4-0.5	7169
0.5-0.6	4210
0.6-0.7	6164
0.7-0.8	5092
0.8-0.85	1608
0.85-0.9	745
0.9-0.95	191
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.992	High Similarity	NPC324482
0.984	High Similarity	NPC84772
0.976	High Similarity	NPC230818
0.9603	High Similarity	NPC212379
0.9603	High Similarity	NPC69235
0.9538	High Similarity	NPC84699
0.9466	High Similarity	NPC156910
0.9462	High Similarity	NPC164136
0.9457	High Similarity	NPC285054
0.9444	High Similarity	NPC305518
0.9444	High Similarity	NPC128428
0.9398	High Similarity	NPC477956
0.9394	High Similarity	NPC153979
0.9389	High Similarity	NPC13575
0.9323	High Similarity	NPC474504
0.9323	High Similarity	NPC131130
0.9323	High Similarity	NPC474487
0.9323	High Similarity	NPC21350
0.9323	High Similarity	NPC470671
0.9323	High Similarity	NPC470672
0.9318	High Similarity	NPC477244
0.9318	High Similarity	NPC25287
0.9318	High Similarity	NPC274109
0.9318	High Similarity	NPC174999
0.9318	High Similarity	NPC477243
0.9318	High Similarity	NPC168105
0.9318	High Similarity	NPC186838
0.9318	High Similarity	NPC66349
0.9318	High Similarity	NPC98115
0.9318	High Similarity	NPC249606
0.9318	High Similarity	NPC150399
0.9318	High Similarity	NPC477242
0.9318	High Similarity	NPC1486
0.9318	High Similarity	NPC12165
0.9318	High Similarity	NPC41461
0.9313	High Similarity	NPC236974
0.9313	High Similarity	NPC103842
0.9313	High Similarity	NPC125920
0.9313	High Similarity	NPC144027
0.9248	High Similarity	NPC472419
0.9248	High Similarity	NPC317119
0.9242	High Similarity	NPC131039
0.9242	High Similarity	NPC156092
0.9242	High Similarity	NPC60667
0.9237	High Similarity	NPC82225
0.9237	High Similarity	NPC144051
0.9237	High Similarity	NPC18877
0.9237	High Similarity	NPC28753
0.9237	High Similarity	NPC294593
0.9237	High Similarity	NPC204960
0.9237	High Similarity	NPC159623
0.9237	High Similarity	NPC93756
0.9237	High Similarity	NPC108113
0.9237	High Similarity	NPC20560
0.9219	High Similarity	NPC80694
0.9219	High Similarity	NPC186098
0.9191	High Similarity	NPC297600
0.9185	High Similarity	NPC215311
0.9185	High Similarity	NPC204985
0.9185	High Similarity	NPC253822
0.9185	High Similarity	NPC219917
0.9185	High Similarity	NPC213659
0.9185	High Similarity	NPC265178
0.9185	High Similarity	NPC477272
0.9185	High Similarity	NPC326109
0.9185	High Similarity	NPC144118
0.9185	High Similarity	NPC80962
0.9185	High Similarity	NPC48624
0.9185	High Similarity	NPC259166
0.9185	High Similarity	NPC11056
0.9185	High Similarity	NPC172250
0.9179	High Similarity	NPC243528
0.9179	High Similarity	NPC470668
0.9179	High Similarity	NPC477056
0.9179	High Similarity	NPC470669
0.9179	High Similarity	NPC477055
0.9179	High Similarity	NPC251681
0.9173	High Similarity	NPC24394
0.9173	High Similarity	NPC470397
0.9173	High Similarity	NPC470398
0.9173	High Similarity	NPC213603
0.9173	High Similarity	NPC187826
0.9173	High Similarity	NPC222633
0.9167	High Similarity	NPC286336
0.916	High Similarity	NPC203817
0.916	High Similarity	NPC103105
0.916	High Similarity	NPC25937
0.916	High Similarity	NPC15834
0.916	High Similarity	NPC215875
0.9154	High Similarity	NPC250057
0.9118	High Similarity	NPC40118
0.9118	High Similarity	NPC52789
0.9118	High Similarity	NPC282300
0.9118	High Similarity	NPC268204
0.9118	High Similarity	NPC469404
0.9118	High Similarity	NPC470089
0.9118	High Similarity	NPC26051
0.9118	High Similarity	NPC232021
0.9118	High Similarity	NPC126534
0.9118	High Similarity	NPC171870
0.9118	High Similarity	NPC321980
0.9118	High Similarity	NPC55832
0.9118	High Similarity	NPC470087
0.9111	High Similarity	NPC472366
0.9111	High Similarity	NPC37206
0.9111	High Similarity	NPC470211
0.9111	High Similarity	NPC295384
0.9111	High Similarity	NPC23257
0.9111	High Similarity	NPC139554
0.9111	High Similarity	NPC283429
0.9104	High Similarity	NPC255801
0.9104	High Similarity	NPC322301
0.9091	High Similarity	NPC263670
0.9091	High Similarity	NPC472365
0.9091	High Similarity	NPC312318
0.9091	High Similarity	NPC139813
0.9091	High Similarity	NPC16197
0.9091	High Similarity	NPC188646
0.9091	High Similarity	NPC56031
0.9091	High Similarity	NPC242294
0.9091	High Similarity	NPC175098
0.9091	High Similarity	NPC337373
0.9091	High Similarity	NPC192304
0.9091	High Similarity	NPC27643
0.9084	High Similarity	NPC186097
0.9084	High Similarity	NPC31872
0.9084	High Similarity	NPC475009
0.9084	High Similarity	NPC473584
0.9084	High Similarity	NPC475589
0.9084	High Similarity	NPC313618
0.9084	High Similarity	NPC475008
0.9077	High Similarity	NPC186628
0.907	High Similarity	NPC293453
0.9058	High Similarity	NPC271288
0.9058	High Similarity	NPC328623
0.9051	High Similarity	NPC84266
0.9044	High Similarity	NPC159275
0.9044	High Similarity	NPC16455
0.9044	High Similarity	NPC471587
0.9044	High Similarity	NPC241100
0.9044	High Similarity	NPC307990
0.9044	High Similarity	NPC101366
0.9037	High Similarity	NPC470399
0.9037	High Similarity	NPC472368
0.9037	High Similarity	NPC471620
0.903	High Similarity	NPC472364
0.903	High Similarity	NPC473391
0.9015	High Similarity	NPC87231
0.9015	High Similarity	NPC129132
0.9015	High Similarity	NPC205468
0.9015	High Similarity	NPC257756
0.9015	High Similarity	NPC10971
0.9015	High Similarity	NPC212631
0.9008	High Similarity	NPC5515
0.9008	High Similarity	NPC279566
0.9008	High Similarity	NPC270369
0.8993	High Similarity	NPC25844
0.8993	High Similarity	NPC477955
0.8986	High Similarity	NPC278249
0.8986	High Similarity	NPC476178
0.8986	High Similarity	NPC475705
0.8986	High Similarity	NPC125894
0.8986	High Similarity	NPC81697
0.8986	High Similarity	NPC85162
0.8986	High Similarity	NPC166138
0.8986	High Similarity	NPC18585
0.8986	High Similarity	NPC245482
0.8986	High Similarity	NPC107177
0.8986	High Similarity	NPC301751
0.8986	High Similarity	NPC51887
0.8986	High Similarity	NPC117836
0.8986	High Similarity	NPC77794
0.8986	High Similarity	NPC106985
0.8986	High Similarity	NPC223812
0.8984	High Similarity	NPC65041
0.8984	High Similarity	NPC475733
0.8978	High Similarity	NPC166689
0.8978	High Similarity	NPC279650
0.8978	High Similarity	NPC110969
0.8978	High Similarity	NPC94076
0.8978	High Similarity	NPC17170
0.8978	High Similarity	NPC26238
0.8978	High Similarity	NPC156190
0.8978	High Similarity	NPC96408
0.8978	High Similarity	NPC182255
0.8978	High Similarity	NPC258630
0.8976	High Similarity	NPC65761
0.8976	High Similarity	NPC472029
0.8971	High Similarity	NPC109232
0.8971	High Similarity	NPC471697
0.8971	High Similarity	NPC220062
0.8971	High Similarity	NPC137009
0.8971	High Similarity	NPC165172
0.8971	High Similarity	NPC303633
0.8971	High Similarity	NPC473076
0.8971	High Similarity	NPC96565
0.8971	High Similarity	NPC216978
0.8971	High Similarity	NPC78913
0.8971	High Similarity	NPC55018
0.8971	High Similarity	NPC301217

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 NPC27490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	1028
0.2-0.3	1748
0.3-0.4	2746
0.4-0.5	1726
0.5-0.6	1088
0.6-0.7	345
0.7-0.8	122
0.8-0.85	20
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9084	High Similarity	NPD1240	Approved
0.8955	High Similarity	NPD1510	Phase 2
0.8947	High Similarity	NPD1607	Approved
0.8947	High Similarity	NPD6651	Approved
0.8921	High Similarity	NPD4378	Clinical (unspecified phase)
0.8759	High Similarity	NPD970	Clinical (unspecified phase)
0.8686	High Similarity	NPD1552	Clinical (unspecified phase)
0.8686	High Similarity	NPD1550	Clinical (unspecified phase)
0.8623	High Similarity	NPD1549	Phase 2
0.8561	High Similarity	NPD2800	Approved
0.8521	High Similarity	NPD7410	Clinical (unspecified phase)
0.8503	High Similarity	NPD8443	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD4380	Phase 2
0.8435	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2534	Approved
0.8392	Intermediate Similarity	NPD2532	Approved
0.8392	Intermediate Similarity	NPD2533	Approved
0.8345	Intermediate Similarity	NPD2796	Approved
0.8299	Intermediate Similarity	NPD7411	Suspended
0.8267	Intermediate Similarity	NPD7075	Discontinued
0.8214	Intermediate Similarity	NPD2935	Discontinued
0.8194	Intermediate Similarity	NPD1511	Approved
0.8188	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD7819	Suspended
0.8169	Intermediate Similarity	NPD1243	Approved
0.8121	Intermediate Similarity	NPD6801	Discontinued
0.8121	Intermediate Similarity	NPD1934	Approved
0.8112	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6959	Discontinued
0.8082	Intermediate Similarity	NPD1512	Approved
0.8069	Intermediate Similarity	NPD6799	Approved
0.8067	Intermediate Similarity	NPD2801	Approved
0.8042	Intermediate Similarity	NPD2654	Approved
0.8027	Intermediate Similarity	NPD920	Approved
0.8014	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7473	Discontinued
0.7961	Intermediate Similarity	NPD7768	Phase 2
0.7961	Intermediate Similarity	NPD3882	Suspended
0.7958	Intermediate Similarity	NPD1551	Phase 2
0.7949	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6232	Discontinued
0.7917	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD2799	Discontinued
0.7877	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD6599	Discontinued
0.7862	Intermediate Similarity	NPD3750	Approved
0.7857	Intermediate Similarity	NPD943	Approved
0.7842	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD9493	Approved
0.7778	Intermediate Similarity	NPD9717	Approved
0.777	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6166	Phase 2
0.7716	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6100	Approved
0.7708	Intermediate Similarity	NPD6099	Approved
0.7703	Intermediate Similarity	NPD7390	Discontinued
0.7702	Intermediate Similarity	NPD5953	Discontinued
0.7692	Intermediate Similarity	NPD5494	Approved
0.7688	Intermediate Similarity	NPD7286	Phase 2
0.7681	Intermediate Similarity	NPD2798	Approved
0.7677	Intermediate Similarity	NPD3749	Approved
0.7676	Intermediate Similarity	NPD230	Phase 1
0.7669	Intermediate Similarity	NPD9545	Approved
0.7662	Intermediate Similarity	NPD3817	Phase 2
0.7655	Intermediate Similarity	NPD2344	Approved
0.7619	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1203	Approved
0.7595	Intermediate Similarity	NPD5710	Approved
0.7595	Intermediate Similarity	NPD5711	Approved
0.7589	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD422	Phase 1
0.7531	Intermediate Similarity	NPD7074	Phase 3
0.7531	Intermediate Similarity	NPD1729	Discontinued
0.7517	Intermediate Similarity	NPD3748	Approved
0.7517	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD919	Approved
0.7516	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7054	Approved
0.7465	Intermediate Similarity	NPD2313	Discontinued
0.745	Intermediate Similarity	NPD2309	Approved
0.7447	Intermediate Similarity	NPD4908	Phase 1
0.7445	Intermediate Similarity	NPD1610	Phase 2
0.7439	Intermediate Similarity	NPD6559	Discontinued
0.7434	Intermediate Similarity	NPD5403	Approved
0.7423	Intermediate Similarity	NPD7472	Approved
0.7421	Intermediate Similarity	NPD1247	Approved
0.7391	Intermediate Similarity	NPD3972	Approved
0.7383	Intermediate Similarity	NPD4628	Phase 3
0.7378	Intermediate Similarity	NPD6797	Phase 2
0.7357	Intermediate Similarity	NPD1164	Approved
0.7343	Intermediate Similarity	NPD411	Approved
0.7343	Intermediate Similarity	NPD3268	Approved
0.7338	Intermediate Similarity	NPD7458	Discontinued
0.7338	Intermediate Similarity	NPD3226	Approved
0.7333	Intermediate Similarity	NPD7251	Discontinued
0.7324	Intermediate Similarity	NPD6832	Phase 2
0.732	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1201	Approved
0.731	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5124	Phase 1
0.731	Intermediate Similarity	NPD447	Suspended
0.7303	Intermediate Similarity	NPD5401	Approved
0.7289	Intermediate Similarity	NPD7808	Phase 3
0.7284	Intermediate Similarity	NPD2403	Approved
0.7279	Intermediate Similarity	NPD1548	Phase 1
0.7267	Intermediate Similarity	NPD4360	Phase 2
0.7267	Intermediate Similarity	NPD4363	Phase 3
0.7267	Intermediate Similarity	NPD7003	Approved
0.7266	Intermediate Similarity	NPD1608	Approved
0.7261	Intermediate Similarity	NPD1465	Phase 2
0.7256	Intermediate Similarity	NPD5844	Phase 1
0.7254	Intermediate Similarity	NPD9494	Approved
0.7244	Intermediate Similarity	NPD846	Approved
0.7244	Intermediate Similarity	NPD940	Approved
0.7234	Intermediate Similarity	NPD1470	Approved
0.7234	Intermediate Similarity	NPD2797	Approved
0.7225	Intermediate Similarity	NPD4361	Phase 2
0.7225	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3926	Phase 2
0.7222	Intermediate Similarity	NPD1296	Phase 2
0.7215	Intermediate Similarity	NPD5402	Approved
0.7214	Intermediate Similarity	NPD4749	Approved
0.7186	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1019	Discontinued
0.7181	Intermediate Similarity	NPD2346	Discontinued
0.7176	Intermediate Similarity	NPD74	Approved
0.7176	Intermediate Similarity	NPD9266	Approved
0.7174	Intermediate Similarity	NPD4626	Approved
0.7164	Intermediate Similarity	NPD1241	Discontinued
0.7163	Intermediate Similarity	NPD1876	Approved
0.7163	Intermediate Similarity	NPD1283	Approved
0.7162	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7134	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6104	Discontinued
0.7114	Intermediate Similarity	NPD5404	Approved
0.7114	Intermediate Similarity	NPD5406	Approved
0.7114	Intermediate Similarity	NPD5405	Approved
0.7114	Intermediate Similarity	NPD5408	Approved
0.7103	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD9268	Approved
0.7101	Intermediate Similarity	NPD1651	Approved
0.7099	Intermediate Similarity	NPD9267	Approved
0.7099	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD9263	Approved
0.7099	Intermediate Similarity	NPD9264	Approved
0.7067	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6002	Phase 3
0.7067	Intermediate Similarity	NPD6005	Phase 3
0.7067	Intermediate Similarity	NPD6004	Phase 3
0.7066	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD17	Approved
0.7047	Intermediate Similarity	NPD4308	Phase 3
0.7034	Intermediate Similarity	NPD4625	Phase 3
0.7034	Intermediate Similarity	NPD3027	Phase 3
0.7014	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3267	Approved
0.6993	Remote Similarity	NPD3266	Approved
0.6989	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3764	Approved
0.6986	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD37	Approved
0.6972	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1471	Phase 3
0.6951	Remote Similarity	NPD7229	Phase 3
0.695	Remote Similarity	NPD1281	Approved
0.6929	Remote Similarity	NPD1778	Approved
0.6923	Remote Similarity	NPD3225	Approved
0.6908	Remote Similarity	NPD2424	Discontinued
0.6899	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4288	Approved
0.6894	Remote Similarity	NPD2296	Approved
0.6892	Remote Similarity	NPD1613	Approved
0.6892	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6234	Discontinued
0.6866	Remote Similarity	NPD4750	Phase 3
0.6861	Remote Similarity	NPD9281	Approved
0.6859	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5691	Approved
0.6853	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4967	Phase 2
0.6852	Remote Similarity	NPD4965	Approved
0.6852	Remote Similarity	NPD4966	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