NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.08
Volume:	270.51
LogP:	2.078
LogD:	0.821
LogS:	-3.288
# Rotatable Bonds:	3
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.809
Synthetic Accessibility Score:	3.521
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.487
MDCK Permeability:	4.988148702977924e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.542

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	93.13826751708984%
Volume Distribution (VD):	0.279
Pgp-substrate:	3.6281518936157227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.406
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.212
CYP2C9-substrate:	0.324
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	5.391
Half-life (T1/2):	0.7

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.08
Skin Sensitization:	0.172
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.027
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: NPC14098

Natural Product ID:	NPC14098
*Common Name:**	Alternarienonic Acid
IUPAC Name:	2-hydroxy-6-[(4R)-4-hydroxy-2-methyl-5-oxocyclopenten-1-yl]-4-methoxybenzoic acid
Synonyms:	Alternarienonic Acid
Standard InCHIKey:	KZPGRZQYEBJXQJ-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C14H14O6/c1-6-3-10(16)13(17)11(6)8-4-7(20-2)5-9(15)12(8)14(18)19/h4-5,10,15-16H,3H2,1-2H3,(H,18,19)/t10-/m1/s1
SMILES:	COc1cc(O)c(c(c1)C1=C(C)C[C@H](C1=O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519395
PubChem CID:	24900161
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002344] Methoxybenzoic acids and derivatives [CHEMONTID:0002346] P-methoxybenzoic acids and derivatives

*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
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18494522]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276679]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25265160]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841051]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30794407]

☑ 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
IC50	24
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	23
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	Activity	=	101.2	%	PMID[475861]
NPT1660	Individual Protein	NUAK family SNF1-like kinase 1	Homo sapiens	IC50	=	4.0	ug.mL-1	PMID[475861]
NPT1432	Individual Protein	Serine/threonine-protein kinase Aurora-A	Homo sapiens	IC50	=	4.4	ug.mL-1	PMID[475861]
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[475861]
NPT1434	Individual Protein	Serine/threonine-protein kinase B-raf	Homo sapiens	IC50	=	9.0	ug.mL-1	PMID[475861]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	6.5	ug.mL-1	PMID[475861]
NPT2572	Individual Protein	Ephrin type-B receptor 4	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]
NPT1436	Individual Protein	Focal adhesion kinase 1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]
NPT2571	Individual Protein	Mitogen-activated protein kinase kinase kinase 8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]
NPT1438	Individual Protein	Insulin-like growth factor I receptor	Homo sapiens	IC50	=	3.6	ug.mL-1	PMID[475861]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	=	4.6	ug.mL-1	PMID[475861]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	=	5.1	ug.mL-1	PMID[475861]
NPT2573	Individual Protein	Vascular endothelial growth factor receptor 3	Homo sapiens	IC50	=	3.7	ug.mL-1	PMID[475861]
NPT1650	Individual Protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	IC50	=	6.6	ug.mL-1	PMID[475861]
NPT2574	Individual Protein	Insulin receptor	Homo sapiens	IC50	=	8.1	ug.mL-1	PMID[475861]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	=	9.4	ug.mL-1	PMID[475861]
NPT2575	Individual Protein	Platelet-derived growth factor receptor beta	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]
NPT1598	Individual Protein	Casein kinase II alpha	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]
NPT1702	Individual Protein	Serine/threonine-protein kinase PLK4	Homo sapiens	IC50	=	2.5	ug.mL-1	PMID[475861]
NPT2576	Individual Protein	Tyrosine-protein kinase TIE-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]
NPT728	Individual Protein	Serine/threonine-protein kinase AKT	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]
NPT1560	Protein Complex	Cyclin-dependent kinase 4/cyclin D1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475861]

☑ 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 NPC14098 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	1490
0.2-0.3	3679
0.3-0.4	8345
0.4-0.5	10284
0.5-0.6	3905
0.6-0.7	6249
0.7-0.8	6620
0.8-0.85	1502
0.85-0.9	238
0.9-0.95	54
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9247	High Similarity	NPC153417
0.9184	High Similarity	NPC4423
0.9184	High Similarity	NPC77325
0.9178	High Similarity	NPC472036
0.9178	High Similarity	NPC210320
0.9172	High Similarity	NPC472034
0.9167	High Similarity	NPC472006
0.9167	High Similarity	NPC469542
0.9167	High Similarity	NPC51106
0.9161	High Similarity	NPC67650
0.9161	High Similarity	NPC1704
0.9149	High Similarity	NPC135837
0.9143	High Similarity	NPC182496
0.9143	High Similarity	NPC180905
0.9139	High Similarity	NPC473395
0.9116	High Similarity	NPC471642
0.9116	High Similarity	NPC73411
0.9116	High Similarity	NPC240253
0.9116	High Similarity	NPC471641
0.9116	High Similarity	NPC215711
0.9116	High Similarity	NPC240622
0.911	High Similarity	NPC472033
0.9097	High Similarity	NPC474385
0.9054	High Similarity	NPC198927
0.9041	High Similarity	NPC473692
0.9028	High Similarity	NPC475730
0.9028	High Similarity	NPC90411
0.9028	High Similarity	NPC244923
0.9028	High Similarity	NPC313123
0.9028	High Similarity	NPC478217
0.9021	High Similarity	NPC92655
0.9021	High Similarity	NPC268052
0.898	High Similarity	NPC107625
0.8973	High Similarity	NPC210425
0.8973	High Similarity	NPC86373
0.8973	High Similarity	NPC280404
0.8973	High Similarity	NPC277426
0.8966	High Similarity	NPC469579
0.8958	High Similarity	NPC165172
0.8951	High Similarity	NPC475974
0.8951	High Similarity	NPC94248
0.8951	High Similarity	NPC212693
0.8951	High Similarity	NPC191835
0.8912	High Similarity	NPC312789
0.8904	High Similarity	NPC478202
0.8897	High Similarity	NPC472035
0.8897	High Similarity	NPC478201
0.8889	High Similarity	NPC52358
0.8889	High Similarity	NPC474655
0.8889	High Similarity	NPC105456
0.8889	High Similarity	NPC32360
0.8889	High Similarity	NPC139634
0.8882	High Similarity	NPC99381
0.8881	High Similarity	NPC65837
0.8881	High Similarity	NPC474771
0.8881	High Similarity	NPC474849
0.8881	High Similarity	NPC70380
0.8881	High Similarity	NPC178467
0.8881	High Similarity	NPC149372
0.8865	High Similarity	NPC153783
0.8857	High Similarity	NPC219892
0.8857	High Similarity	NPC189823
0.8836	High Similarity	NPC250755
0.8819	High Similarity	NPC478200
0.8819	High Similarity	NPC33144
0.8811	High Similarity	NPC235115
0.8808	High Similarity	NPC200773
0.8808	High Similarity	NPC240768
0.88	High Similarity	NPC270160
0.88	High Similarity	NPC237440
0.8784	High Similarity	NPC257558
0.8776	High Similarity	NPC354984
0.8776	High Similarity	NPC471643
0.8776	High Similarity	NPC471639
0.8767	High Similarity	NPC158634
0.8759	High Similarity	NPC57380
0.8742	High Similarity	NPC469670
0.8742	High Similarity	NPC60413
0.8742	High Similarity	NPC179178
0.8742	High Similarity	NPC469619
0.8716	High Similarity	NPC210966
0.8716	High Similarity	NPC478203
0.8716	High Similarity	NPC126882
0.8707	High Similarity	NPC471644
0.8707	High Similarity	NPC471640
0.8699	High Similarity	NPC158472
0.8699	High Similarity	NPC99441
0.869	High Similarity	NPC472602
0.869	High Similarity	NPC9121
0.869	High Similarity	NPC472403
0.869	High Similarity	NPC177307
0.8684	High Similarity	NPC70016
0.8684	High Similarity	NPC215921
0.8681	High Similarity	NPC158481
0.8681	High Similarity	NPC84699
0.8675	High Similarity	NPC6923
0.8675	High Similarity	NPC476684
0.8671	High Similarity	NPC175943
0.8667	High Similarity	NPC8817
0.8658	High Similarity	NPC134621
0.8645	High Similarity	NPC246466
0.8643	High Similarity	NPC41263
0.8643	High Similarity	NPC293453
0.8639	High Similarity	NPC472604
0.8639	High Similarity	NPC53649
0.8639	High Similarity	NPC37530
0.8639	High Similarity	NPC16455
0.8639	High Similarity	NPC220106
0.8639	High Similarity	NPC472605
0.8639	High Similarity	NPC307990
0.8639	High Similarity	NPC472603
0.8636	High Similarity	NPC79998
0.863	High Similarity	NPC247409
0.863	High Similarity	NPC88269
0.863	High Similarity	NPC275356
0.8627	High Similarity	NPC167903
0.8621	High Similarity	NPC71256
0.8621	High Similarity	NPC194579
0.8618	High Similarity	NPC56204
0.8618	High Similarity	NPC96501
0.8618	High Similarity	NPC119929
0.8609	High Similarity	NPC172329
0.8609	High Similarity	NPC2569
0.86	High Similarity	NPC237208
0.86	High Similarity	NPC225173
0.86	High Similarity	NPC163846
0.86	High Similarity	NPC138978
0.86	High Similarity	NPC267509
0.86	High Similarity	NPC470357
0.8599	High Similarity	NPC117985
0.8591	High Similarity	NPC66404
0.8591	High Similarity	NPC95123
0.8582	High Similarity	NPC212379
0.8582	High Similarity	NPC69235
0.8581	High Similarity	NPC182255
0.8581	High Similarity	NPC94076
0.8581	High Similarity	NPC96692
0.8581	High Similarity	NPC297985
0.8581	High Similarity	NPC105648
0.8581	High Similarity	NPC82913
0.8581	High Similarity	NPC49108
0.8571	High Similarity	NPC192189
0.8571	High Similarity	NPC305518
0.8571	High Similarity	NPC472601
0.8571	High Similarity	NPC128428
0.8571	High Similarity	NPC472600
0.8571	High Similarity	NPC155205
0.8571	High Similarity	NPC37206
0.8571	High Similarity	NPC281477
0.8552	High Similarity	NPC50455
0.8552	High Similarity	NPC242712
0.8543	High Similarity	NPC53362
0.8543	High Similarity	NPC125801
0.8543	High Similarity	NPC166583
0.8535	High Similarity	NPC243701
0.8533	High Similarity	NPC32470
0.8533	High Similarity	NPC316535
0.8533	High Similarity	NPC75694
0.8533	High Similarity	NPC28632
0.8533	High Similarity	NPC83272
0.8533	High Similarity	NPC29577
0.8526	High Similarity	NPC190020
0.8526	High Similarity	NPC84935
0.8526	High Similarity	NPC77679
0.8523	High Similarity	NPC471731
0.8523	High Similarity	NPC310340
0.8523	High Similarity	NPC159721
0.8523	High Similarity	NPC84266
0.8521	High Similarity	NPC42292
0.8521	High Similarity	NPC307732
0.8516	High Similarity	NPC38898
0.8516	High Similarity	NPC16082
0.8516	High Similarity	NPC82592
0.8516	High Similarity	NPC199926
0.8514	High Similarity	NPC275734
0.8506	High Similarity	NPC478224
0.8506	High Similarity	NPC271681
0.8506	High Similarity	NPC273483
0.8497	Intermediate Similarity	NPC472891
0.8497	Intermediate Similarity	NPC470107
0.8497	Intermediate Similarity	NPC475460
0.8493	Intermediate Similarity	NPC193792
0.8493	Intermediate Similarity	NPC121243
0.8493	Intermediate Similarity	NPC222633
0.8493	Intermediate Similarity	NPC240147
0.8493	Intermediate Similarity	NPC470397
0.8483	Intermediate Similarity	NPC27407
0.8483	Intermediate Similarity	NPC142027
0.8483	Intermediate Similarity	NPC164136
0.8477	Intermediate Similarity	NPC473023
0.8477	Intermediate Similarity	NPC260946
0.8472	Intermediate Similarity	NPC48036
0.8471	Intermediate Similarity	NPC470339
0.8467	Intermediate Similarity	NPC470932
0.8467	Intermediate Similarity	NPC184702
0.8467	Intermediate Similarity	NPC42540
0.8467	Intermediate Similarity	NPC19896
0.8467	Intermediate Similarity	NPC245482
0.8467	Intermediate Similarity	NPC301751
0.8467	Intermediate Similarity	NPC151607

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 NPC14098 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	988
0.2-0.3	1834
0.3-0.4	2526
0.4-0.5	1898
0.5-0.6	1062
0.6-0.7	404
0.7-0.8	135
0.8-0.85	18
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD970	Clinical (unspecified phase)
0.8533	High Similarity	NPD2532	Approved
0.8533	High Similarity	NPD2534	Approved
0.8533	High Similarity	NPD2533	Approved
0.8299	Intermediate Similarity	NPD1510	Phase 2
0.8276	Intermediate Similarity	NPD1240	Approved
0.8217	Intermediate Similarity	NPD7819	Suspended
0.8188	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1607	Approved
0.8133	Intermediate Similarity	NPD1549	Phase 2
0.8063	Intermediate Similarity	NPD7075	Discontinued
0.8052	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6799	Approved
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7937	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1934	Approved
0.7925	Intermediate Similarity	NPD6801	Discontinued
0.7911	Intermediate Similarity	NPD6599	Discontinued
0.7908	Intermediate Similarity	NPD3750	Approved
0.7888	Intermediate Similarity	NPD3882	Suspended
0.7885	Intermediate Similarity	NPD1512	Approved
0.7875	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6232	Discontinued
0.784	Intermediate Similarity	NPD3749	Approved
0.7831	Intermediate Similarity	NPD7473	Discontinued
0.7826	Intermediate Similarity	NPD3817	Phase 2
0.7805	Intermediate Similarity	NPD6959	Discontinued
0.7799	Intermediate Similarity	NPD4380	Phase 2
0.7771	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6166	Phase 2
0.7763	Intermediate Similarity	NPD2796	Approved
0.7763	Intermediate Similarity	NPD2935	Discontinued
0.7763	Intermediate Similarity	NPD1551	Phase 2
0.7758	Intermediate Similarity	NPD5710	Approved
0.7758	Intermediate Similarity	NPD5711	Approved
0.7756	Intermediate Similarity	NPD1511	Approved
0.7733	Intermediate Similarity	NPD230	Phase 1
0.7727	Intermediate Similarity	NPD2800	Approved
0.7727	Intermediate Similarity	NPD1243	Approved
0.7697	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD919	Approved
0.7625	Intermediate Similarity	NPD3226	Approved
0.7622	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD5403	Approved
0.761	Intermediate Similarity	NPD920	Approved
0.7607	Intermediate Similarity	NPD5402	Approved
0.7595	Intermediate Similarity	NPD5401	Approved
0.7582	Intermediate Similarity	NPD3748	Approved
0.758	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3818	Discontinued
0.7566	Intermediate Similarity	NPD6651	Approved
0.7561	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7768	Phase 2
0.7558	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2801	Approved
0.7544	Intermediate Similarity	NPD6797	Phase 2
0.7533	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5844	Phase 1
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7251	Discontinued
0.7485	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7484	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9545	Approved
0.7466	Intermediate Similarity	NPD9717	Approved
0.7465	Intermediate Similarity	NPD9493	Approved
0.7457	Intermediate Similarity	NPD7808	Phase 3
0.7452	Intermediate Similarity	NPD4628	Phase 3
0.7442	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7434	Intermediate Similarity	NPD943	Approved
0.7427	Intermediate Similarity	NPD7054	Approved
0.7416	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6559	Discontinued
0.7389	Intermediate Similarity	NPD2654	Approved
0.7384	Intermediate Similarity	NPD7472	Approved
0.7378	Intermediate Similarity	NPD37	Approved
0.7342	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5494	Approved
0.7315	Intermediate Similarity	NPD1203	Approved
0.7312	Intermediate Similarity	NPD7390	Discontinued
0.7308	Intermediate Similarity	NPD6100	Approved
0.7308	Intermediate Similarity	NPD6099	Approved
0.7303	Intermediate Similarity	NPD411	Approved
0.7284	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD422	Phase 1
0.7273	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1471	Phase 3
0.7261	Intermediate Similarity	NPD2344	Approved
0.7261	Intermediate Similarity	NPD2346	Discontinued
0.7246	Intermediate Similarity	NPD4967	Phase 2
0.7246	Intermediate Similarity	NPD4966	Approved
0.7246	Intermediate Similarity	NPD4965	Approved
0.7244	Intermediate Similarity	NPD7033	Discontinued
0.7244	Intermediate Similarity	NPD2799	Discontinued
0.7241	Intermediate Similarity	NPD5953	Discontinued
0.723	Intermediate Similarity	NPD1608	Approved
0.7193	Intermediate Similarity	NPD3926	Phase 2
0.7193	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3764	Approved
0.719	Intermediate Similarity	NPD3268	Approved
0.719	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7168	Intermediate Similarity	NPD3751	Discontinued
0.7162	Intermediate Similarity	NPD1201	Approved
0.716	Intermediate Similarity	NPD6234	Discontinued
0.7159	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4626	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1283	Approved
0.7126	Intermediate Similarity	NPD7286	Phase 2
0.7117	Intermediate Similarity	NPD6273	Approved
0.7114	Intermediate Similarity	NPD9269	Phase 2
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7091	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5405	Approved
0.7089	Intermediate Similarity	NPD5404	Approved
0.7089	Intermediate Similarity	NPD5408	Approved
0.7089	Intermediate Similarity	NPD5406	Approved
0.7086	Intermediate Similarity	NPD1470	Approved
0.7081	Intermediate Similarity	NPD2309	Approved
0.7075	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD6832	Phase 2
0.7052	Intermediate Similarity	NPD2403	Approved
0.7051	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6355	Discontinued
0.7044	Intermediate Similarity	NPD6002	Phase 3
0.7044	Intermediate Similarity	NPD6004	Phase 3
0.7044	Intermediate Similarity	NPD6005	Phase 3
0.7044	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1019	Discontinued
0.7039	Intermediate Similarity	NPD2798	Approved
0.7035	Intermediate Similarity	NPD7229	Phase 3
0.7035	Intermediate Similarity	NPD3787	Discontinued
0.7027	Intermediate Similarity	NPD17	Approved
0.7021	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD8150	Discontinued
0.6994	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9494	Approved
0.6987	Remote Similarity	NPD4060	Phase 1
0.6986	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4288	Approved
0.6974	Remote Similarity	NPD1164	Approved
0.6974	Remote Similarity	NPD3266	Approved
0.6974	Remote Similarity	NPD3267	Approved
0.6973	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7228	Approved
0.6968	Remote Similarity	NPD2313	Discontinued
0.6968	Remote Similarity	NPD1296	Phase 2
0.6959	Remote Similarity	NPD5691	Approved
0.6952	Remote Similarity	NPD6782	Approved
0.6952	Remote Similarity	NPD6780	Approved
0.6952	Remote Similarity	NPD6777	Approved
0.6952	Remote Similarity	NPD6781	Approved
0.6952	Remote Similarity	NPD6778	Approved
0.6952	Remote Similarity	NPD6779	Approved
0.6952	Remote Similarity	NPD6776	Approved
0.6943	Remote Similarity	NPD5124	Phase 1
0.6943	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5763	Approved
0.6937	Remote Similarity	NPD5762	Approved
0.6933	Remote Similarity	NPD1610	Phase 2
0.6933	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1281	Approved
0.6928	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8312	Approved
0.6927	Remote Similarity	NPD8313	Approved
0.6927	Remote Similarity	NPD8151	Discontinued
0.6923	Remote Similarity	NPD4287	Approved
0.6923	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7003	Approved
0.6913	Remote Similarity	NPD1778	Approved
0.691	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1876	Approved
0.6903	Remote Similarity	NPD3027	Phase 3
0.6901	Remote Similarity	NPD9266	Approved
0.6901	Remote Similarity	NPD74	Approved
0.6886	Remote Similarity	NPD7458	Discontinued
0.6879	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1613	Approved
0.6875	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6190	Approved
0.6863	Remote Similarity	NPD2797	Approved
0.6862	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6798	Discontinued
0.6842	Remote Similarity	NPD7697	Approved
0.6842	Remote Similarity	NPD7698	Approved
0.6842	Remote Similarity	NPD7696	Phase 3
0.6839	Remote Similarity	NPD6808	Phase 2

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