NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.07
Volume:	244.373
LogP:	2.56
LogD:	2.687
LogS:	-4.006
# Rotatable Bonds:	1
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	3.11
Fsp3:	0.214
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:	-4.664
MDCK Permeability:	3.900799492839724e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.529

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	84.91316986083984%
Volume Distribution (VD):	1.105
Pgp-substrate:	15.603280067443848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.906
CYP2C19-inhibitor:	0.786
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.372
CYP2C9-substrate:	0.824
CYP2D6-inhibitor:	0.37
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.131
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	13.388
Half-life (T1/2):	0.302

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.698
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.152
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.482
Skin Sensitization:	0.087
Carcinogencity:	0.751
Eye Corrosion:	0.077
Eye Irritation:	0.596
Respiratory Toxicity:	0.827

Download Data

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

Natural Product: NPC309953

Natural Product ID:	NPC309953
*Common Name:**	Obliquin
IUPAC Name:	(2S)-2-prop-1-en-2-yl-2,3-dihydropyrano[2,3-g][1,4]benzodioxin-7-one
Synonyms:
Standard InCHIKey:	DUECABXXAMFFBH-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C14H12O4/c1-8(2)13-7-16-11-6-10-9(5-12(11)17-13)3-4-14(15)18-10/h3-6,13H,1,7H2,2H3/t13-/m1/s1
SMILES:	CC(=C)[C@H]1COc2c(O1)cc1c(c2)oc(=O)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3039091
PubChem CID:	6708593
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003465] p-Dioxolo[2,3-g]coumarins

*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
NPO1264	Bacillus megaterium	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3025147]
NPO1264	Bacillus megaterium	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4960152]
NPO12285	Cassipourea guianensis	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387055]
NPO18328	Leontopodium alpinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5976	Nicotiana attenuata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO18328	Leontopodium alpinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1153	Crotalaria madurensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9010	Lomatia silaifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18428	Mycosphaerella ligulicola	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5230	Peziza echinospora	Species	Pezizaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1264	Bacillus megaterium	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5976	Nicotiana attenuata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3660	Vernonia angusticeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10873	Cercophora sordarioides	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2738	Chrysolina grossa	Species	Chrysomelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18328	Leontopodium alpinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5747	Streptomyces rugosporus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1153	Crotalaria madurensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12285	Cassipourea guianensis	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8356	Hibiscus abelmoschus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11224	Byrsonima microphylla	Species	Malpighiaceae	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	112.32	%	PMID[522226]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	103.57	%	PMID[522226]

☑ 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 NPC309953 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	451
0.1-0.2	2001
0.2-0.3	5518
0.3-0.4	11313
0.4-0.5	5966
0.5-0.6	4094
0.6-0.7	5801
0.7-0.8	5393
0.8-0.85	1683
0.85-0.9	397
0.9-0.95	74
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC137669
0.9685	High Similarity	NPC244799
0.9685	High Similarity	NPC240722
0.9612	High Similarity	NPC241341
0.9612	High Similarity	NPC36437
0.9612	High Similarity	NPC233018
0.9606	High Similarity	NPC123127
0.9606	High Similarity	NPC27239
0.9398	High Similarity	NPC270256
0.9394	High Similarity	NPC167517
0.9385	High Similarity	NPC319969
0.938	High Similarity	NPC19242
0.9323	High Similarity	NPC20796
0.9318	High Similarity	NPC234865
0.9259	High Similarity	NPC300611
0.9254	High Similarity	NPC13067
0.9254	High Similarity	NPC164148
0.9254	High Similarity	NPC43500
0.9248	High Similarity	NPC286843
0.9179	High Similarity	NPC52086
0.9179	High Similarity	NPC95162
0.9179	High Similarity	NPC76336
0.9179	High Similarity	NPC148835
0.9179	High Similarity	NPC139548
0.9179	High Similarity	NPC20511
0.9173	High Similarity	NPC240915
0.9137	High Similarity	NPC15577
0.9124	High Similarity	NPC138212
0.9104	High Similarity	NPC82271
0.9104	High Similarity	NPC126682
0.9098	High Similarity	NPC474600
0.9098	High Similarity	NPC7163
0.9091	High Similarity	NPC123954
0.9071	High Similarity	NPC96294
0.903	High Similarity	NPC311430
0.903	High Similarity	NPC224941
0.903	High Similarity	NPC73071
0.9023	High Similarity	NPC472522
0.9007	High Similarity	NPC176903
0.9007	High Similarity	NPC30688
0.8955	High Similarity	NPC92830
0.8955	High Similarity	NPC147030
0.8944	High Similarity	NPC294522
0.8944	High Similarity	NPC120426
0.8944	High Similarity	NPC114740
0.8944	High Similarity	NPC21184
0.8944	High Similarity	NPC205727
0.8939	High Similarity	NPC476399
0.8931	High Similarity	NPC474616
0.8929	High Similarity	NPC205361
0.8923	High Similarity	NPC127604
0.8881	High Similarity	NPC471910
0.8881	High Similarity	NPC207002
0.8881	High Similarity	NPC26673
0.8881	High Similarity	NPC296624
0.8881	High Similarity	NPC318400
0.8881	High Similarity	NPC167111
0.8881	High Similarity	NPC133956
0.8881	High Similarity	NPC213197
0.8873	High Similarity	NPC206264
0.8873	High Similarity	NPC313334
0.8873	High Similarity	NPC212670
0.8865	High Similarity	NPC476347
0.8857	High Similarity	NPC476450
0.8855	High Similarity	NPC474670
0.8855	High Similarity	NPC194841
0.8849	High Similarity	NPC34245
0.8849	High Similarity	NPC91492
0.8849	High Similarity	NPC236419
0.8849	High Similarity	NPC7439
0.8849	High Similarity	NPC110067
0.8849	High Similarity	NPC256555
0.8819	High Similarity	NPC163598
0.8819	High Similarity	NPC120774
0.8819	High Similarity	NPC264875
0.8815	High Similarity	NPC267412
0.8815	High Similarity	NPC287182
0.8815	High Similarity	NPC260265
0.8815	High Similarity	NPC47163
0.8815	High Similarity	NPC84894
0.8815	High Similarity	NPC319859
0.8815	High Similarity	NPC100986
0.8815	High Similarity	NPC195343
0.8815	High Similarity	NPC164269
0.8815	High Similarity	NPC127888
0.8815	High Similarity	NPC166672
0.8815	High Similarity	NPC18804
0.8815	High Similarity	NPC198381
0.8815	High Similarity	NPC74655
0.8806	High Similarity	NPC137949
0.8803	High Similarity	NPC476348
0.8803	High Similarity	NPC187398
0.8788	High Similarity	NPC474623
0.8788	High Similarity	NPC474651
0.8788	High Similarity	NPC210674
0.876	High Similarity	NPC194626
0.876	High Similarity	NPC288238
0.875	High Similarity	NPC471625
0.875	High Similarity	NPC281241
0.875	High Similarity	NPC472424
0.875	High Similarity	NPC163200
0.875	High Similarity	NPC472521
0.875	High Similarity	NPC471909
0.875	High Similarity	NPC86892
0.8741	High Similarity	NPC277021
0.874	High Similarity	NPC281356
0.874	High Similarity	NPC298796
0.8732	High Similarity	NPC52740
0.8732	High Similarity	NPC231149
0.8732	High Similarity	NPC41844
0.8731	High Similarity	NPC73738
0.8714	High Similarity	NPC230157
0.8712	High Similarity	NPC474821
0.8705	High Similarity	NPC472520
0.8705	High Similarity	NPC279851
0.8686	High Similarity	NPC78746
0.8686	High Similarity	NPC149320
0.8686	High Similarity	NPC160727
0.8686	High Similarity	NPC128529
0.8686	High Similarity	NPC177281
0.8686	High Similarity	NPC188380
0.8686	High Similarity	NPC476455
0.8686	High Similarity	NPC283019
0.8686	High Similarity	NPC224543
0.8686	High Similarity	NPC471630
0.8686	High Similarity	NPC55615
0.8672	High Similarity	NPC222175
0.8671	High Similarity	NPC93924
0.8671	High Similarity	NPC139839
0.8667	High Similarity	NPC5423
0.8661	High Similarity	NPC152306
0.8661	High Similarity	NPC265547
0.8657	High Similarity	NPC79184
0.8657	High Similarity	NPC307042
0.8657	High Similarity	NPC474617
0.8652	High Similarity	NPC471763
0.8647	High Similarity	NPC31707
0.8647	High Similarity	NPC199204
0.8636	High Similarity	NPC474632
0.8623	High Similarity	NPC38874
0.8623	High Similarity	NPC153818
0.8623	High Similarity	NPC294456
0.8623	High Similarity	NPC474530
0.8623	High Similarity	NPC212124
0.8623	High Similarity	NPC225106
0.8623	High Similarity	NPC232246
0.8623	High Similarity	NPC281014
0.8623	High Similarity	NPC474540
0.8623	High Similarity	NPC474521
0.8623	High Similarity	NPC184861
0.8605	High Similarity	NPC267064
0.8605	High Similarity	NPC235190
0.8605	High Similarity	NPC180006
0.8582	High Similarity	NPC168710
0.8581	High Similarity	NPC284810
0.8562	High Similarity	NPC476352
0.8562	High Similarity	NPC215060
0.8561	High Similarity	NPC27352
0.8561	High Similarity	NPC211110
0.8561	High Similarity	NPC279573
0.855	High Similarity	NPC108545
0.8542	High Similarity	NPC48366
0.854	High Similarity	NPC307412
0.854	High Similarity	NPC474478
0.854	High Similarity	NPC55149
0.8538	High Similarity	NPC310373
0.8531	High Similarity	NPC475872
0.8529	High Similarity	NPC245120
0.8529	High Similarity	NPC14248
0.8521	High Similarity	NPC185127
0.8519	High Similarity	NPC80170
0.8516	High Similarity	NPC96705
0.8511	High Similarity	NPC469564
0.8507	High Similarity	NPC474636
0.8504	High Similarity	NPC128633
0.85	High Similarity	NPC312881
0.8496	Intermediate Similarity	NPC234109
0.8496	Intermediate Similarity	NPC101894
0.8496	Intermediate Similarity	NPC471826
0.8496	Intermediate Similarity	NPC188327
0.8489	Intermediate Similarity	NPC474886
0.8485	Intermediate Similarity	NPC111347
0.8478	Intermediate Similarity	NPC33986
0.8478	Intermediate Similarity	NPC469675
0.8472	Intermediate Similarity	NPC178129
0.8467	Intermediate Similarity	NPC222036
0.8467	Intermediate Similarity	NPC7526
0.8456	Intermediate Similarity	NPC29734
0.845	Intermediate Similarity	NPC308217
0.8446	Intermediate Similarity	NPC186507
0.844	Intermediate Similarity	NPC195357
0.844	Intermediate Similarity	NPC287286
0.844	Intermediate Similarity	NPC152771
0.8438	Intermediate Similarity	NPC52464
0.8438	Intermediate Similarity	NPC304208
0.8435	Intermediate Similarity	NPC470264
0.8433	Intermediate Similarity	NPC258567
0.8433	Intermediate Similarity	NPC224774
0.8433	Intermediate Similarity	NPC121740
0.8417	Intermediate Similarity	NPC103409

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 NPC309953 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	1016
0.2-0.3	1999
0.3-0.4	2674
0.4-0.5	1675
0.5-0.6	906
0.6-0.7	332
0.7-0.8	101
0.8-0.85	29
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8873	High Similarity	NPD1653	Approved
0.8182	Intermediate Similarity	NPD1652	Phase 2
0.8129	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1613	Approved
0.812	Intermediate Similarity	NPD422	Phase 1
0.7973	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5844	Phase 1
0.7908	Intermediate Similarity	NPD3817	Phase 2
0.7899	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5494	Approved
0.7817	Intermediate Similarity	NPD5124	Phase 1
0.7817	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1934	Approved
0.7756	Intermediate Similarity	NPD919	Approved
0.7742	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7549	Discontinued
0.7727	Intermediate Similarity	NPD2801	Approved
0.7692	Intermediate Similarity	NPD447	Suspended
0.766	Intermediate Similarity	NPD3027	Phase 3
0.7656	Intermediate Similarity	NPD1358	Approved
0.7647	Intermediate Similarity	NPD3496	Discontinued
0.7643	Intermediate Similarity	NPD3018	Phase 2
0.7638	Intermediate Similarity	NPD9697	Approved
0.7606	Intermediate Similarity	NPD1296	Phase 2
0.7569	Intermediate Similarity	NPD1933	Approved
0.7564	Intermediate Similarity	NPD5402	Approved
0.7556	Intermediate Similarity	NPD1548	Phase 1
0.7547	Intermediate Similarity	NPD1247	Approved
0.7536	Intermediate Similarity	NPD2981	Phase 2
0.7534	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2796	Approved
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1511	Approved
0.7482	Intermediate Similarity	NPD2982	Phase 2
0.7482	Intermediate Similarity	NPD2983	Phase 2
0.7481	Intermediate Similarity	NPD5536	Phase 2
0.7464	Intermediate Similarity	NPD1610	Phase 2
0.7452	Intermediate Similarity	NPD5353	Approved
0.7451	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD230	Phase 1
0.7389	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1512	Approved
0.7378	Intermediate Similarity	NPD7054	Approved
0.7375	Intermediate Similarity	NPD5677	Discontinued
0.7368	Intermediate Similarity	NPD6799	Approved
0.7343	Intermediate Similarity	NPD4908	Phase 1
0.7338	Intermediate Similarity	NPD1611	Approved
0.7338	Intermediate Similarity	NPD1091	Approved
0.7338	Intermediate Similarity	NPD3705	Approved
0.7338	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD7472	Approved
0.7329	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5401	Approved
0.7317	Intermediate Similarity	NPD3818	Discontinued
0.7315	Intermediate Similarity	NPD7266	Discontinued
0.7308	Intermediate Similarity	NPD3134	Approved
0.7305	Intermediate Similarity	NPD3225	Approved
0.7301	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6166	Phase 2
0.7301	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3882	Suspended
0.7285	Intermediate Similarity	NPD3750	Approved
0.7285	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7819	Suspended
0.7273	Intermediate Similarity	NPD2861	Phase 2
0.7267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1549	Phase 2
0.725	Intermediate Similarity	NPD7075	Discontinued
0.7248	Intermediate Similarity	NPD1551	Phase 2
0.7246	Intermediate Similarity	NPD5691	Approved
0.7241	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5535	Approved
0.7229	Intermediate Similarity	NPD7074	Phase 3
0.7226	Intermediate Similarity	NPD5403	Approved
0.7222	Intermediate Similarity	NPD7199	Phase 2
0.7219	Intermediate Similarity	NPD1243	Approved
0.7215	Intermediate Similarity	NPD6801	Discontinued
0.7215	Intermediate Similarity	NPD37	Approved
0.7208	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1019	Discontinued
0.7202	Intermediate Similarity	NPD7808	Phase 3
0.72	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1778	Approved
0.7192	Intermediate Similarity	NPD6233	Phase 2
0.719	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4966	Approved
0.7188	Intermediate Similarity	NPD4967	Phase 2
0.7188	Intermediate Similarity	NPD4965	Approved
0.7186	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6797	Phase 2
0.7185	Intermediate Similarity	NPD5283	Phase 1
0.7143	Intermediate Similarity	NPD5297	Approved
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD3539	Phase 1
0.7133	Intermediate Similarity	NPD3267	Approved
0.7124	Intermediate Similarity	NPD6190	Approved
0.7121	Intermediate Similarity	NPD290	Approved
0.7117	Intermediate Similarity	NPD8127	Discontinued
0.7113	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4749	Approved
0.7103	Intermediate Similarity	NPD6832	Phase 2
0.7102	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6234	Discontinued
0.7095	Intermediate Similarity	NPD4340	Discontinued
0.7089	Intermediate Similarity	NPD4380	Phase 2
0.7089	Intermediate Similarity	NPD6599	Discontinued
0.7086	Intermediate Similarity	NPD3540	Phase 1
0.7073	Intermediate Similarity	NPD6232	Discontinued
0.707	Intermediate Similarity	NPD3686	Approved
0.707	Intermediate Similarity	NPD3687	Approved
0.7067	Intermediate Similarity	NPD1510	Phase 2
0.7059	Intermediate Similarity	NPD1241	Discontinued
0.7044	Intermediate Similarity	NPD7411	Suspended
0.7042	Intermediate Similarity	NPD9717	Approved
0.7037	Intermediate Similarity	NPD228	Approved
0.7032	Intermediate Similarity	NPD4357	Discontinued
0.7032	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5242	Approved
0.7027	Intermediate Similarity	NPD4307	Phase 2
0.7027	Intermediate Similarity	NPD4060	Phase 1
0.702	Intermediate Similarity	NPD2935	Discontinued
0.7014	Intermediate Similarity	NPD2797	Approved
0.7013	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6798	Discontinued
0.7007	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5585	Approved
0.6993	Remote Similarity	NPD6674	Discontinued
0.6987	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6671	Approved
0.695	Remote Similarity	NPD17	Approved
0.695	Remote Similarity	NPD4626	Approved
0.6948	Remote Similarity	NPD4110	Phase 3
0.6948	Remote Similarity	NPD4628	Phase 3
0.6948	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7473	Discontinued
0.6941	Remote Similarity	NPD6559	Discontinued
0.6939	Remote Similarity	NPD4625	Phase 3
0.6937	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6386	Approved
0.6937	Remote Similarity	NPD6385	Approved
0.6933	Remote Similarity	NPD2653	Approved
0.6928	Remote Similarity	NPD3926	Phase 2
0.6928	Remote Similarity	NPD2424	Discontinued
0.6918	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2237	Approved
0.6905	Remote Similarity	NPD3751	Discontinued
0.6905	Remote Similarity	NPD7228	Approved
0.6897	Remote Similarity	NPD1203	Approved
0.6892	Remote Similarity	NPD411	Approved
0.6892	Remote Similarity	NPD3268	Approved
0.6887	Remote Similarity	NPD7097	Phase 1
0.6886	Remote Similarity	NPD4481	Phase 3
0.6883	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1357	Approved
0.6879	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3146	Approved
0.6875	Remote Similarity	NPD4675	Approved
0.6875	Remote Similarity	NPD4678	Approved
0.6871	Remote Similarity	NPD7768	Phase 2
0.6867	Remote Similarity	NPD6355	Discontinued
0.6863	Remote Similarity	NPD5763	Approved
0.6863	Remote Similarity	NPD1375	Discontinued
0.6863	Remote Similarity	NPD5762	Approved
0.6857	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4308	Phase 3
0.6842	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7033	Discontinued
0.6842	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5090	Approved
0.6832	Remote Similarity	NPD5089	Approved
0.6828	Remote Similarity	NPD8651	Approved
0.6824	Remote Similarity	NPD7095	Approved
0.6815	Remote Similarity	NPD2684	Approved
0.6815	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1774	Approved
0.6806	Remote Similarity	NPD1608	Approved
0.6803	Remote Similarity	NPD9494	Approved
0.68	Remote Similarity	NPD4140	Approved
0.68	Remote Similarity	NPD6841	Approved
0.68	Remote Similarity	NPD1240	Approved
0.68	Remote Similarity	NPD6843	Phase 3
0.68	Remote Similarity	NPD6842	Approved
0.6797	Remote Similarity	NPD6032	Approved
0.6795	Remote Similarity	NPD2219	Phase 1
0.6791	Remote Similarity	NPD968	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