NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.12
Volume:	249.463
LogP:	3.511
LogD:	2.655
LogS:	-3.418
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	2.927
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.669
MDCK Permeability:	1.6374879123759456e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	98.72085571289062%
Volume Distribution (VD):	0.481
Pgp-substrate:	1.1776043176651%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.3
CYP2C19-substrate:	0.735
CYP2C9-inhibitor:	0.592
CYP2C9-substrate:	0.791
CYP2D6-inhibitor:	0.745
CYP2D6-substrate:	0.685
CYP3A4-inhibitor:	0.635
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	10.655
Half-life (T1/2):	0.379

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.548
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.214
Maximum Recommended Daily Dose:	0.211
Skin Sensitization:	0.722
Carcinogencity:	0.109
Eye Corrosion:	0.006
Eye Irritation:	0.936
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC324482

Natural Product ID:	NPC324482
*Common Name:**	Aspidinol D
IUPAC Name:	1-(2,6-dihydroxy-4-methoxy-3-methylphenyl)-2-methylbutan-1-one
Synonyms:	Aspidinol D
Standard InCHIKey:	HDRPUFIQLCTRLW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H18O4/c1-5-7(2)12(15)11-9(14)6-10(17-4)8(3)13(11)16/h6-7,14,16H,5H2,1-4H3
SMILES:	CCC(C)C(=O)C1=C(C(=C(C=C1O)OC)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641982
PubChem CID:	50908690
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.	root	n.a.	PMID[21043475]
NPO8089	Hypericum chinense	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043475]
NPO3208	Eucalyptus pulverulenta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	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]
NPO3208	Eucalyptus pulverulenta	Species	Myrtaceae	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	=	4.0	ug.mL-1	PMID[475088]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[475088]
NPT1101	Organism	Staphylococcus aureus subsp. aureus RN4220	Staphylococcus aureus subsp. aureus RN4220	MIC	=	8.0	ug.mL-1	PMID[475088]

☑ 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 NPC324482 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	339
0.1-0.2	1629
0.2-0.3	4610
0.3-0.4	11462
0.4-0.5	6706
0.5-0.6	4459
0.6-0.7	6148
0.7-0.8	5010
0.8-0.85	1448
0.85-0.9	644
0.9-0.95	231
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.992	High Similarity	NPC27490
0.9919	High Similarity	NPC84772
0.9839	High Similarity	NPC230818
0.968	High Similarity	NPC212379
0.968	High Similarity	NPC69235
0.9538	High Similarity	NPC156910
0.9535	High Similarity	NPC164136
0.952	High Similarity	NPC128428
0.952	High Similarity	NPC305518
0.9466	High Similarity	NPC153979
0.9462	High Similarity	NPC13575
0.9462	High Similarity	NPC84699
0.9389	High Similarity	NPC98115
0.9389	High Similarity	NPC186838
0.9389	High Similarity	NPC249606
0.9389	High Similarity	NPC150399
0.9389	High Similarity	NPC1486
0.9389	High Similarity	NPC12165
0.9389	High Similarity	NPC477242
0.9389	High Similarity	NPC41461
0.9389	High Similarity	NPC168105
0.9389	High Similarity	NPC25287
0.9389	High Similarity	NPC477243
0.9389	High Similarity	NPC477244
0.9389	High Similarity	NPC174999
0.9389	High Similarity	NPC274109
0.9389	High Similarity	NPC66349
0.9385	High Similarity	NPC125920
0.9385	High Similarity	NPC144027
0.9385	High Similarity	NPC103842
0.9385	High Similarity	NPC236974
0.938	High Similarity	NPC285054
0.9323	High Similarity	NPC477956
0.9318	High Similarity	NPC317119
0.9318	High Similarity	NPC472419
0.9313	High Similarity	NPC156092
0.9313	High Similarity	NPC60667
0.9313	High Similarity	NPC131039
0.9308	High Similarity	NPC28753
0.9308	High Similarity	NPC20560
0.9308	High Similarity	NPC294593
0.9308	High Similarity	NPC82225
0.9308	High Similarity	NPC204960
0.9308	High Similarity	NPC18877
0.9308	High Similarity	NPC93756
0.9308	High Similarity	NPC159623
0.9308	High Similarity	NPC108113
0.9308	High Similarity	NPC144051
0.9291	High Similarity	NPC80694
0.9291	High Similarity	NPC186098
0.9248	High Similarity	NPC251681
0.9248	High Similarity	NPC474487
0.9248	High Similarity	NPC474504
0.9248	High Similarity	NPC243528
0.9248	High Similarity	NPC21350
0.9248	High Similarity	NPC477055
0.9248	High Similarity	NPC470669
0.9248	High Similarity	NPC470668
0.9248	High Similarity	NPC470671
0.9248	High Similarity	NPC131130
0.9248	High Similarity	NPC470672
0.9248	High Similarity	NPC477056
0.9242	High Similarity	NPC470398
0.9242	High Similarity	NPC222633
0.9242	High Similarity	NPC187826
0.9242	High Similarity	NPC470397
0.9237	High Similarity	NPC286336
0.9231	High Similarity	NPC15834
0.9231	High Similarity	NPC203817
0.9231	High Similarity	NPC103105
0.9231	High Similarity	NPC25937
0.9231	High Similarity	NPC215875
0.9225	High Similarity	NPC250057
0.9185	High Similarity	NPC282300
0.9179	High Similarity	NPC470211
0.9179	High Similarity	NPC472366
0.9179	High Similarity	NPC23257
0.9179	High Similarity	NPC139554
0.916	High Similarity	NPC188646
0.916	High Similarity	NPC56031
0.916	High Similarity	NPC472365
0.916	High Similarity	NPC312318
0.916	High Similarity	NPC263670
0.916	High Similarity	NPC242294
0.916	High Similarity	NPC27643
0.916	High Similarity	NPC175098
0.916	High Similarity	NPC139813
0.916	High Similarity	NPC16197
0.916	High Similarity	NPC337373
0.916	High Similarity	NPC192304
0.9154	High Similarity	NPC475009
0.9154	High Similarity	NPC473584
0.9154	High Similarity	NPC475589
0.9154	High Similarity	NPC313618
0.9154	High Similarity	NPC475008
0.9154	High Similarity	NPC186097
0.9154	High Similarity	NPC31872
0.9147	High Similarity	NPC186628
0.9141	High Similarity	NPC293453
0.9118	High Similarity	NPC297600
0.9111	High Similarity	NPC48624
0.9111	High Similarity	NPC219917
0.9111	High Similarity	NPC471587
0.9111	High Similarity	NPC477272
0.9111	High Similarity	NPC11056
0.9111	High Similarity	NPC204985
0.9111	High Similarity	NPC16455
0.9111	High Similarity	NPC241100
0.9111	High Similarity	NPC213659
0.9111	High Similarity	NPC144118
0.9111	High Similarity	NPC259166
0.9111	High Similarity	NPC307990
0.9111	High Similarity	NPC159275
0.9111	High Similarity	NPC80962
0.9111	High Similarity	NPC172250
0.9111	High Similarity	NPC253822
0.9111	High Similarity	NPC265178
0.9111	High Similarity	NPC215311
0.9111	High Similarity	NPC326109
0.9104	High Similarity	NPC471620
0.9104	High Similarity	NPC470399
0.9104	High Similarity	NPC472368
0.9098	High Similarity	NPC213603
0.9098	High Similarity	NPC24394
0.9084	High Similarity	NPC257756
0.9084	High Similarity	NPC212631
0.9084	High Similarity	NPC10971
0.9084	High Similarity	NPC129132
0.9084	High Similarity	NPC205468
0.9084	High Similarity	NPC87231
0.9077	High Similarity	NPC270369
0.9077	High Similarity	NPC5515
0.9077	High Similarity	NPC279566
0.9055	High Similarity	NPC65041
0.9051	High Similarity	NPC223812
0.9051	High Similarity	NPC125894
0.9051	High Similarity	NPC77794
0.9051	High Similarity	NPC278249
0.9051	High Similarity	NPC85162
0.9051	High Similarity	NPC107177
0.9051	High Similarity	NPC81697
0.9048	High Similarity	NPC65761
0.9048	High Similarity	NPC472029
0.9044	High Similarity	NPC17170
0.9044	High Similarity	NPC470087
0.9044	High Similarity	NPC26238
0.9044	High Similarity	NPC96408
0.9044	High Similarity	NPC156190
0.9044	High Similarity	NPC40118
0.9044	High Similarity	NPC166689
0.9044	High Similarity	NPC268204
0.9044	High Similarity	NPC55832
0.9044	High Similarity	NPC110969
0.9044	High Similarity	NPC469404
0.9044	High Similarity	NPC126534
0.9044	High Similarity	NPC279650
0.9044	High Similarity	NPC171870
0.9044	High Similarity	NPC470089
0.9044	High Similarity	NPC232021
0.9044	High Similarity	NPC258630
0.9044	High Similarity	NPC52789
0.9044	High Similarity	NPC321980
0.9044	High Similarity	NPC26051
0.904	High Similarity	NPC215392
0.9037	High Similarity	NPC78913
0.9037	High Similarity	NPC220062
0.9037	High Similarity	NPC473076
0.9037	High Similarity	NPC18260
0.9037	High Similarity	NPC283429
0.9037	High Similarity	NPC37206
0.9037	High Similarity	NPC301217
0.9037	High Similarity	NPC303633
0.9037	High Similarity	NPC53181
0.9037	High Similarity	NPC471697
0.9037	High Similarity	NPC217186
0.9037	High Similarity	NPC96565
0.9037	High Similarity	NPC295384
0.9037	High Similarity	NPC216978
0.9037	High Similarity	NPC55018
0.903	High Similarity	NPC322301
0.903	High Similarity	NPC255801
0.9023	High Similarity	NPC151113
0.9023	High Similarity	NPC101752
0.9015	High Similarity	NPC223457
0.9008	High Similarity	NPC164236
0.9008	High Similarity	NPC128348
0.9008	High Similarity	NPC112192
0.9008	High Similarity	NPC308037
0.9008	High Similarity	NPC189106
0.9008	High Similarity	NPC66384
0.9008	High Similarity	NPC309717
0.9008	High Similarity	NPC64359
0.9008	High Similarity	NPC262359
0.9	High Similarity	NPC307732
0.9	High Similarity	NPC42292
0.9	High Similarity	NPC185497
0.8986	High Similarity	NPC473013
0.8986	High Similarity	NPC235217
0.8986	High Similarity	NPC131579
0.8986	High Similarity	NPC473014

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 NPC324482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	1030
0.2-0.3	1751
0.3-0.4	2761
0.4-0.5	1712
0.5-0.6	1105
0.6-0.7	335
0.7-0.8	115
0.8-0.85	20
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9154	High Similarity	NPD1240	Approved
0.9015	High Similarity	NPD1607	Approved
0.9015	High Similarity	NPD6651	Approved
0.8881	High Similarity	NPD1510	Phase 2
0.8849	High Similarity	NPD4378	Clinical (unspecified phase)
0.875	High Similarity	NPD1550	Clinical (unspecified phase)
0.875	High Similarity	NPD1552	Clinical (unspecified phase)
0.8686	High Similarity	NPD1549	Phase 2
0.8686	High Similarity	NPD970	Clinical (unspecified phase)
0.8582	High Similarity	NPD7410	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD2800	Approved
0.8435	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD4380	Phase 2
0.8367	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD7411	Suspended
0.8322	Intermediate Similarity	NPD2533	Approved
0.8322	Intermediate Similarity	NPD2534	Approved
0.8322	Intermediate Similarity	NPD2532	Approved
0.8273	Intermediate Similarity	NPD2796	Approved
0.82	Intermediate Similarity	NPD7075	Discontinued
0.8176	Intermediate Similarity	NPD6801	Discontinued
0.8143	Intermediate Similarity	NPD2935	Discontinued
0.8125	Intermediate Similarity	NPD6799	Approved
0.8125	Intermediate Similarity	NPD1511	Approved
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD2654	Approved
0.8099	Intermediate Similarity	NPD1243	Approved
0.8054	Intermediate Similarity	NPD1934	Approved
0.8042	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD6959	Discontinued
0.8014	Intermediate Similarity	NPD1512	Approved
0.8	Intermediate Similarity	NPD2801	Approved
0.7972	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD920	Approved
0.7949	Intermediate Similarity	NPD7473	Discontinued
0.7943	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6599	Discontinued
0.7899	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7768	Phase 2
0.7895	Intermediate Similarity	NPD3882	Suspended
0.7887	Intermediate Similarity	NPD1551	Phase 2
0.7885	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6232	Discontinued
0.7846	Intermediate Similarity	NPD9493	Approved
0.7843	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD9717	Approved
0.7817	Intermediate Similarity	NPD2799	Discontinued
0.7808	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD3750	Approved
0.7786	Intermediate Similarity	NPD943	Approved
0.7736	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7286	Phase 2
0.7727	Intermediate Similarity	NPD9545	Approved
0.7703	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1203	Approved
0.7658	Intermediate Similarity	NPD6166	Phase 2
0.7658	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5953	Discontinued
0.7639	Intermediate Similarity	NPD6099	Approved
0.7639	Intermediate Similarity	NPD6100	Approved
0.7635	Intermediate Similarity	NPD7390	Discontinued
0.763	Intermediate Similarity	NPD422	Phase 1
0.7628	Intermediate Similarity	NPD5494	Approved
0.7613	Intermediate Similarity	NPD3749	Approved
0.7609	Intermediate Similarity	NPD2798	Approved
0.7606	Intermediate Similarity	NPD230	Phase 1
0.7597	Intermediate Similarity	NPD3817	Phase 2
0.7586	Intermediate Similarity	NPD2344	Approved
0.7578	Intermediate Similarity	NPD1729	Discontinued
0.7551	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5710	Approved
0.7532	Intermediate Similarity	NPD5711	Approved
0.7518	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5403	Approved
0.7469	Intermediate Similarity	NPD7074	Phase 3
0.7453	Intermediate Similarity	NPD3818	Discontinued
0.7452	Intermediate Similarity	NPD919	Approved
0.7448	Intermediate Similarity	NPD3748	Approved
0.7448	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD3972	Approved
0.7436	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD3268	Approved
0.7394	Intermediate Similarity	NPD2313	Discontinued
0.7383	Intermediate Similarity	NPD2309	Approved
0.7378	Intermediate Similarity	NPD6559	Discontinued
0.7376	Intermediate Similarity	NPD6832	Phase 2
0.7376	Intermediate Similarity	NPD4908	Phase 1
0.7372	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1610	Phase 2
0.7362	Intermediate Similarity	NPD7472	Approved
0.7361	Intermediate Similarity	NPD5124	Phase 1
0.7361	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1247	Approved
0.7351	Intermediate Similarity	NPD5401	Approved
0.7333	Intermediate Similarity	NPD1548	Phase 1
0.7317	Intermediate Similarity	NPD6797	Phase 2
0.7315	Intermediate Similarity	NPD4628	Phase 3
0.7302	Intermediate Similarity	NPD940	Approved
0.7302	Intermediate Similarity	NPD846	Approved
0.7286	Intermediate Similarity	NPD2797	Approved
0.7286	Intermediate Similarity	NPD1164	Approved
0.7273	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD1296	Phase 2
0.7273	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD7251	Discontinued
0.7255	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1201	Approved
0.7241	Intermediate Similarity	NPD447	Suspended
0.7234	Intermediate Similarity	NPD1019	Discontinued
0.7231	Intermediate Similarity	NPD9266	Approved
0.7231	Intermediate Similarity	NPD74	Approved
0.7229	Intermediate Similarity	NPD7808	Phase 3
0.7222	Intermediate Similarity	NPD2403	Approved
0.7218	Intermediate Similarity	NPD1241	Discontinued
0.7211	Intermediate Similarity	NPD7033	Discontinued
0.7209	Intermediate Similarity	NPD4363	Phase 3
0.7209	Intermediate Similarity	NPD4360	Phase 2
0.72	Intermediate Similarity	NPD7003	Approved
0.7197	Intermediate Similarity	NPD1465	Phase 2
0.7195	Intermediate Similarity	NPD5844	Phase 1
0.7194	Intermediate Similarity	NPD1608	Approved
0.7183	Intermediate Similarity	NPD9494	Approved
0.7179	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6104	Discontinued
0.7168	Intermediate Similarity	NPD4361	Phase 2
0.7168	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1470	Approved
0.716	Intermediate Similarity	NPD3926	Phase 2
0.7154	Intermediate Similarity	NPD9263	Approved
0.7154	Intermediate Similarity	NPD9264	Approved
0.7154	Intermediate Similarity	NPD9267	Approved
0.7154	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7126	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2346	Discontinued
0.7113	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4626	Approved
0.7092	Intermediate Similarity	NPD1283	Approved
0.7092	Intermediate Similarity	NPD1876	Approved
0.7071	Intermediate Similarity	NPD9269	Phase 2
0.7047	Intermediate Similarity	NPD5406	Approved
0.7047	Intermediate Similarity	NPD5404	Approved
0.7047	Intermediate Similarity	NPD5408	Approved
0.7047	Intermediate Similarity	NPD5405	Approved
0.7042	Intermediate Similarity	NPD3267	Approved
0.7042	Intermediate Similarity	NPD3266	Approved
0.7034	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD9268	Approved
0.7029	Intermediate Similarity	NPD1651	Approved
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6002	Phase 3
0.7	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD6005	Phase 3
0.698	Remote Similarity	NPD4308	Phase 3
0.6978	Remote Similarity	NPD17	Approved
0.6972	Remote Similarity	NPD3225	Approved
0.6966	Remote Similarity	NPD3027	Phase 3
0.6966	Remote Similarity	NPD4625	Phase 3
0.6948	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD37	Approved
0.6918	Remote Similarity	NPD3764	Approved
0.6912	Remote Similarity	NPD9281	Approved
0.6903	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1933	Approved
0.6892	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7229	Phase 3
0.6887	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1471	Phase 3
0.6879	Remote Similarity	NPD1281	Approved
0.6857	Remote Similarity	NPD1778	Approved
0.6846	Remote Similarity	NPD9261	Approved
0.6842	Remote Similarity	NPD2424	Discontinued
0.6835	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4288	Approved
0.6832	Remote Similarity	NPD2296	Approved
0.6831	Remote Similarity	NPD1481	Phase 2
0.6824	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1613	Approved
0.6824	Remote Similarity	NPD3140	Approved
0.6824	Remote Similarity	NPD3142	Approved
0.6816	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6234	Discontinued
0.6809	Remote Similarity	NPD3847	Discontinued

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