NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.08
Volume:	252.98
LogP:	2.409
LogD:	1.895
LogS:	-2.377
# Rotatable Bonds:	5
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.627
Synthetic Accessibility Score:	2.58
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.666
MDCK Permeability:	1.9849541786243208e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.261
Plasma Protein Binding (PPB):	93.10921478271484%
Volume Distribution (VD):	0.774
Pgp-substrate:	6.154025554656982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.287
CYP2C19-inhibitor:	0.232
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.399
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.397
CYP2D6-substrate:	0.377
CYP3A4-inhibitor:	0.561
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	14.745
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.419
Rat Oral Acute Toxicity:	0.31
Maximum Recommended Daily Dose:	0.615
Skin Sensitization:	0.88
Carcinogencity:	0.697
Eye Corrosion:	0.489
Eye Irritation:	0.968
Respiratory Toxicity:	0.828

Download Data

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

Natural Product: NPC52358

Natural Product ID:	NPC52358
*Common Name:**	Globosumone A
IUPAC Name:	[(E)-2-oxopent-3-enyl] 2,4-dihydroxy-6-methylbenzoate
Synonyms:
Standard InCHIKey:	KIMBFCFJDPSYCZ-ONEGZZNKSA-N
Standard InCHI:	InChI=1S/C13H14O5/c1-3-4-9(14)7-18-13(17)12-8(2)5-10(15)6-11(12)16/h3-6,15-16H,7H2,1-2H3/b4-3+
SMILES:	C/C=C/C(=O)COC(=O)c1c(C)cc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464155
PubChem CID:	11436623
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004701] p-Hydroxybenzoic acid esters [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl esters

*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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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
IC50	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	6500.0	nM	PMID[491694]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	21300.0	nM	PMID[491694]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	8800.0	nM	PMID[491694]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	10600.0	nM	PMID[491694]
NPT27	Others	Unspecified		IC50	=	13000.0	nM	PMID[491694]

☑ 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 NPC52358 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	1531
0.2-0.3	3839
0.3-0.4	8676
0.4-0.5	9733
0.5-0.6	4019
0.6-0.7	6641
0.7-0.8	6497
0.8-0.85	1201
0.85-0.9	178
0.9-0.95	49
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9559	High Similarity	NPC244923
0.9545	High Similarity	NPC153783
0.9481	High Similarity	NPC478200
0.9481	High Similarity	NPC33144
0.9416	High Similarity	NPC478201
0.9416	High Similarity	NPC472035
0.9394	High Similarity	NPC219892
0.9394	High Similarity	NPC189823
0.9338	High Similarity	NPC191835
0.9333	High Similarity	NPC235115
0.9296	High Similarity	NPC84142
0.9275	High Similarity	NPC478217
0.9275	High Similarity	NPC313123
0.927	High Similarity	NPC92655
0.927	High Similarity	NPC268052
0.9265	High Similarity	NPC135837
0.9265	High Similarity	NPC70380
0.9231	High Similarity	NPC164762
0.9225	High Similarity	NPC215711
0.9225	High Similarity	NPC73411
0.9214	High Similarity	NPC210966
0.9214	High Similarity	NPC126882
0.9214	High Similarity	NPC478203
0.9203	High Similarity	NPC158472
0.9197	High Similarity	NPC9121
0.9197	High Similarity	NPC177307
0.9197	High Similarity	NPC94248
0.9197	High Similarity	NPC212693
0.9185	High Similarity	NPC175943
0.9167	High Similarity	NPC91809
0.9155	High Similarity	NPC210320
0.9149	High Similarity	NPC257558
0.9149	High Similarity	NPC472034
0.9143	High Similarity	NPC478202
0.9137	High Similarity	NPC158634
0.913	High Similarity	NPC32360
0.913	High Similarity	NPC105456
0.913	High Similarity	NPC139634
0.9124	High Similarity	NPC71256
0.9118	High Similarity	NPC180905
0.9118	High Similarity	NPC182496
0.9104	High Similarity	NPC198249
0.9097	High Similarity	NPC56204
0.9085	High Similarity	NPC472033
0.9071	High Similarity	NPC474385
0.9065	High Similarity	NPC155205
0.9058	High Similarity	NPC472602
0.9058	High Similarity	NPC472403
0.9051	High Similarity	NPC158481
0.9021	High Similarity	NPC472036
0.9015	High Similarity	NPC95309
0.9007	High Similarity	NPC472006
0.9007	High Similarity	NPC354984
0.9	High Similarity	NPC37530
0.9	High Similarity	NPC90411
0.9	High Similarity	NPC475730
0.9	High Similarity	NPC1704
0.9	High Similarity	NPC67650
0.9	High Similarity	NPC53649
0.9	High Similarity	NPC472603
0.8993	High Similarity	NPC275356
0.8993	High Similarity	NPC247409
0.8993	High Similarity	NPC88269
0.8986	High Similarity	NPC474771
0.8986	High Similarity	NPC474849
0.8986	High Similarity	NPC65837
0.8986	High Similarity	NPC149372
0.8986	High Similarity	NPC194579
0.8986	High Similarity	NPC178467
0.8978	High Similarity	NPC27407
0.8966	High Similarity	NPC472891
0.8963	High Similarity	NPC214702
0.8963	High Similarity	NPC470831
0.8951	High Similarity	NPC202112
0.8951	High Similarity	NPC51513
0.8944	High Similarity	NPC280404
0.8944	High Similarity	NPC151607
0.8944	High Similarity	NPC210425
0.8944	High Similarity	NPC277426
0.8944	High Similarity	NPC42540
0.8944	High Similarity	NPC86373
0.8939	High Similarity	NPC201728
0.8939	High Similarity	NPC262671
0.8929	High Similarity	NPC472601
0.8929	High Similarity	NPC99441
0.8929	High Similarity	NPC472600
0.8921	High Similarity	NPC221104
0.8921	High Similarity	NPC475974
0.8913	High Similarity	NPC50455
0.8913	High Similarity	NPC291454
0.8897	High Similarity	NPC77325
0.8897	High Similarity	NPC4423
0.8889	High Similarity	NPC14098
0.8881	High Similarity	NPC41263
0.8881	High Similarity	NPC83272
0.8873	High Similarity	NPC469542
0.8873	High Similarity	NPC51106
0.8873	High Similarity	NPC159721
0.8865	High Similarity	NPC472604
0.8865	High Similarity	NPC470842
0.8865	High Similarity	NPC472605
0.8859	High Similarity	NPC472889
0.8857	High Similarity	NPC471819
0.8857	High Similarity	NPC474655
0.8851	High Similarity	NPC478221
0.8851	High Similarity	NPC208173
0.8851	High Similarity	NPC472890
0.8851	High Similarity	NPC317585
0.8851	High Similarity	NPC170189
0.8851	High Similarity	NPC99381
0.8849	High Similarity	NPC301915
0.8849	High Similarity	NPC261292
0.8844	High Similarity	NPC115249
0.8844	High Similarity	NPC184284
0.8844	High Similarity	NPC76041
0.8844	High Similarity	NPC478224
0.8841	High Similarity	NPC142027
0.8832	High Similarity	NPC43627
0.8819	High Similarity	NPC107625
0.8803	High Similarity	NPC250755
0.8803	High Similarity	NPC82913
0.8794	High Similarity	NPC156872
0.8794	High Similarity	NPC165172
0.8784	High Similarity	NPC137301
0.8768	High Similarity	NPC474097
0.8767	High Similarity	NPC198927
0.875	High Similarity	NPC247477
0.875	High Similarity	NPC307732
0.875	High Similarity	NPC312789
0.875	High Similarity	NPC42292
0.875	High Similarity	NPC17840
0.875	High Similarity	NPC473692
0.8741	High Similarity	NPC471731
0.8741	High Similarity	NPC472610
0.8733	High Similarity	NPC478225
0.8732	High Similarity	NPC220106
0.8725	High Similarity	NPC69043
0.8725	High Similarity	NPC478230
0.8707	High Similarity	NPC295036
0.8707	High Similarity	NPC470107
0.8699	High Similarity	NPC153417
0.8699	High Similarity	NPC240253
0.8699	High Similarity	NPC471642
0.8699	High Similarity	NPC240622
0.8699	High Similarity	NPC471641
0.869	High Similarity	NPC473023
0.8681	High Similarity	NPC66404
0.8681	High Similarity	NPC475201
0.8681	High Similarity	NPC95123
0.8671	High Similarity	NPC471733
0.8671	High Similarity	NPC96692
0.8671	High Similarity	NPC469579
0.8671	High Similarity	NPC49108
0.8671	High Similarity	NPC105648
0.8658	High Similarity	NPC478231
0.8658	High Similarity	NPC281703
0.8658	High Similarity	NPC125487
0.8652	High Similarity	NPC197666
0.8652	High Similarity	NPC126739
0.8643	High Similarity	NPC242712
0.8639	High Similarity	NPC476684
0.863	High Similarity	NPC476463
0.863	High Similarity	NPC52106
0.863	High Similarity	NPC53362
0.863	High Similarity	NPC259632
0.863	High Similarity	NPC166583
0.8623	High Similarity	NPC478190
0.8623	High Similarity	NPC476389
0.8621	High Similarity	NPC28632
0.8621	High Similarity	NPC134621
0.8613	High Similarity	NPC296158
0.8609	High Similarity	NPC246466
0.8603	High Similarity	NPC179898
0.8603	High Similarity	NPC80694
0.8603	High Similarity	NPC186098
0.8603	High Similarity	NPC293453
0.8592	High Similarity	NPC57380
0.8582	High Similarity	NPC472364
0.8582	High Similarity	NPC472367
0.8582	High Similarity	NPC473391
0.8582	High Similarity	NPC476333
0.8581	High Similarity	NPC469619
0.8581	High Similarity	NPC469670
0.8571	High Similarity	NPC221352
0.8571	High Similarity	NPC278375
0.8571	High Similarity	NPC2569
0.8571	High Similarity	NPC172329
0.8562	High Similarity	NPC317544
0.8562	High Similarity	NPC225173
0.8562	High Similarity	NPC267509
0.8562	High Similarity	NPC163846
0.8562	High Similarity	NPC237208
0.8561	High Similarity	NPC48036
0.8552	High Similarity	NPC257025
0.8552	High Similarity	NPC470216
0.8552	High Similarity	NPC21599
0.8552	High Similarity	NPC193703
0.8542	High Similarity	NPC322112
0.8531	High Similarity	NPC49242
0.8531	High Similarity	NPC230902

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 NPC52358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	949
0.2-0.3	1747
0.3-0.4	2620
0.4-0.5	1885
0.5-0.6	1119
0.6-0.7	388
0.7-0.8	129
0.8-0.85	21
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8993	High Similarity	NPD970	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD230	Phase 1
0.8425	Intermediate Similarity	NPD6799	Approved
0.8411	Intermediate Similarity	NPD7819	Suspended
0.838	Intermediate Similarity	NPD1510	Phase 2
0.838	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD2533	Approved
0.8367	Intermediate Similarity	NPD2532	Approved
0.8367	Intermediate Similarity	NPD2534	Approved
0.8357	Intermediate Similarity	NPD1240	Approved
0.8333	Intermediate Similarity	NPD9545	Approved
0.8247	Intermediate Similarity	NPD7075	Discontinued
0.8239	Intermediate Similarity	NPD1607	Approved
0.8212	Intermediate Similarity	NPD6599	Discontinued
0.8207	Intermediate Similarity	NPD1549	Phase 2
0.8182	Intermediate Similarity	NPD3882	Suspended
0.8182	Intermediate Similarity	NPD9493	Approved
0.817	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD3817	Phase 2
0.8095	Intermediate Similarity	NPD3750	Approved
0.8095	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD1551	Phase 2
0.8067	Intermediate Similarity	NPD1512	Approved
0.7987	Intermediate Similarity	NPD6801	Discontinued
0.7972	Intermediate Similarity	NPD943	Approved
0.7933	Intermediate Similarity	NPD1511	Approved
0.7922	Intermediate Similarity	NPD7411	Suspended
0.7898	Intermediate Similarity	NPD3749	Approved
0.7871	Intermediate Similarity	NPD1934	Approved
0.7848	Intermediate Similarity	NPD919	Approved
0.7823	Intermediate Similarity	NPD2935	Discontinued
0.7823	Intermediate Similarity	NPD2796	Approved
0.7821	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD5403	Approved
0.7771	Intermediate Similarity	NPD5402	Approved
0.777	Intermediate Similarity	NPD9717	Approved
0.7763	Intermediate Similarity	NPD5401	Approved
0.7755	Intermediate Similarity	NPD3748	Approved
0.7742	Intermediate Similarity	NPD4380	Phase 2
0.7722	Intermediate Similarity	NPD7768	Phase 2
0.7716	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3764	Approved
0.7707	Intermediate Similarity	NPD2801	Approved
0.7667	Intermediate Similarity	NPD1243	Approved
0.7662	Intermediate Similarity	NPD920	Approved
0.7658	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD9269	Phase 2
0.764	Intermediate Similarity	NPD6959	Discontinued
0.7632	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD9268	Approved
0.7607	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6166	Phase 2
0.7606	Intermediate Similarity	NPD1203	Approved
0.7606	Intermediate Similarity	NPD1470	Approved
0.7605	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5710	Approved
0.7593	Intermediate Similarity	NPD5711	Approved
0.759	Intermediate Similarity	NPD6797	Phase 2
0.7586	Intermediate Similarity	NPD411	Approved
0.7584	Intermediate Similarity	NPD5408	Approved
0.7584	Intermediate Similarity	NPD5404	Approved
0.7584	Intermediate Similarity	NPD5406	Approved
0.7584	Intermediate Similarity	NPD5405	Approved
0.7582	Intermediate Similarity	NPD7390	Discontinued
0.7576	Intermediate Similarity	NPD9266	Approved
0.7576	Intermediate Similarity	NPD74	Approved
0.7571	Intermediate Similarity	NPD1201	Approved
0.7564	Intermediate Similarity	NPD3226	Approved
0.7562	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD447	Suspended
0.755	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2800	Approved
0.7545	Intermediate Similarity	NPD7251	Discontinued
0.7532	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD9267	Approved
0.75	Intermediate Similarity	NPD9263	Approved
0.75	Intermediate Similarity	NPD9264	Approved
0.75	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1465	Phase 2
0.7483	Intermediate Similarity	NPD1164	Approved
0.747	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5844	Phase 1
0.7457	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6190	Approved
0.7447	Intermediate Similarity	NPD422	Phase 1
0.7423	Intermediate Similarity	NPD1247	Approved
0.7417	Intermediate Similarity	NPD2346	Discontinued
0.741	Intermediate Similarity	NPD3818	Discontinued
0.74	Intermediate Similarity	NPD2799	Discontinued
0.7386	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4628	Phase 3
0.7383	Intermediate Similarity	NPD6651	Approved
0.7381	Intermediate Similarity	NPD5953	Discontinued
0.7365	Intermediate Similarity	NPD7054	Approved
0.7329	Intermediate Similarity	NPD6832	Phase 2
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.7321	Intermediate Similarity	NPD7472	Approved
0.7321	Intermediate Similarity	NPD7074	Phase 3
0.7315	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1019	Discontinued
0.7305	Intermediate Similarity	NPD3751	Discontinued
0.7303	Intermediate Similarity	NPD2344	Approved
0.7278	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1608	Approved
0.7262	Intermediate Similarity	NPD7286	Phase 2
0.7256	Intermediate Similarity	NPD5494	Approved
0.7246	Intermediate Similarity	NPD9281	Approved
0.7237	Intermediate Similarity	NPD6100	Approved
0.7237	Intermediate Similarity	NPD6099	Approved
0.7235	Intermediate Similarity	NPD6559	Discontinued
0.7229	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3926	Phase 2
0.7215	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2654	Approved
0.7197	Intermediate Similarity	NPD9261	Approved
0.719	Intermediate Similarity	NPD1471	Phase 3
0.7181	Intermediate Similarity	NPD520	Approved
0.7143	Intermediate Similarity	NPD9494	Approved
0.7133	Intermediate Similarity	NPD4060	Phase 1
0.7117	Intermediate Similarity	NPD4288	Approved
0.7115	Intermediate Similarity	NPD2309	Approved
0.7114	Intermediate Similarity	NPD2313	Discontinued
0.7075	Intermediate Similarity	NPD2798	Approved
0.7066	Intermediate Similarity	NPD3787	Discontinued
0.7063	Intermediate Similarity	NPD1778	Approved
0.7063	Intermediate Similarity	NPD4626	Approved
0.7063	Intermediate Similarity	NPD17	Approved
0.7055	Intermediate Similarity	NPD1283	Approved
0.7049	Intermediate Similarity	NPD7435	Discontinued
0.7019	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8320	Phase 1
0.7011	Intermediate Similarity	NPD8319	Approved
0.7006	Intermediate Similarity	NPD7199	Phase 2
0.7	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3268	Approved
0.7	Intermediate Similarity	NPD1296	Phase 2
0.6994	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5691	Approved
0.6983	Remote Similarity	NPD6535	Approved
0.6983	Remote Similarity	NPD6534	Approved
0.6981	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6355	Discontinued
0.6966	Remote Similarity	NPD1610	Phase 2
0.6966	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7229	Phase 3
0.6949	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4287	Approved
0.6948	Remote Similarity	NPD7033	Discontinued
0.6948	Remote Similarity	NPD4308	Phase 3
0.6943	Remote Similarity	NPD8166	Discontinued
0.6943	Remote Similarity	NPD7003	Approved
0.6934	Remote Similarity	NPD2182	Approved
0.6929	Remote Similarity	NPD1241	Discontinued
0.6923	Remote Similarity	NPD1548	Phase 1
0.6918	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7458	Discontinued
0.6899	Remote Similarity	NPD2354	Approved
0.6892	Remote Similarity	NPD2797	Approved
0.689	Remote Similarity	NPD37	Approved
0.6889	Remote Similarity	NPD164	Approved
0.6887	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6798	Discontinued
0.6886	Remote Similarity	NPD6234	Discontinued
0.6885	Remote Similarity	NPD6778	Approved
0.6885	Remote Similarity	NPD6780	Approved
0.6885	Remote Similarity	NPD6776	Approved
0.6885	Remote Similarity	NPD6781	Approved
0.6885	Remote Similarity	NPD6777	Approved
0.6885	Remote Similarity	NPD6779	Approved
0.6885	Remote Similarity	NPD6782	Approved
0.6882	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7699	Phase 2
0.6868	Remote Similarity	NPD7700	Phase 2
0.6867	Remote Similarity	NPD4965	Approved
0.6867	Remote Similarity	NPD4966	Approved
0.6867	Remote Similarity	NPD4908	Phase 1
0.6867	Remote Similarity	NPD4967	Phase 2
0.6866	Remote Similarity	NPD940	Approved
0.6866	Remote Similarity	NPD846	Approved
0.6863	Remote Similarity	NPD1933	Approved
0.6857	Remote Similarity	NPD8312	Approved
0.6857	Remote Similarity	NPD8313	Approved
0.6855	Remote Similarity	NPD3300	Phase 2
0.6855	Remote Similarity	NPD7236	Approved
0.6849	Remote Similarity	NPD1281	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