NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.07
Volume:	267.823
LogP:	2.76
LogD:	2.352
LogS:	-4.432
# Rotatable Bonds:	1
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.863
Synthetic Accessibility Score:	2.803
Fsp3:	0.2
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:	-4.797
MDCK Permeability:	2.1501558876479976e-05
Pgp-inhibitor:	0.48
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	88.98139190673828%
Volume Distribution (VD):	0.692
Pgp-substrate:	10.352956771850586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.92
CYP2C19-inhibitor:	0.484
CYP2C19-substrate:	0.369
CYP2C9-inhibitor:	0.728
CYP2C9-substrate:	0.585
CYP2D6-inhibitor:	0.539
CYP2D6-substrate:	0.266
CYP3A4-inhibitor:	0.621
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	10.354
Half-life (T1/2):	0.588

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.835
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.713
Rat Oral Acute Toxicity:	0.956
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.737
Carcinogencity:	0.874
Eye Corrosion:	0.027
Eye Irritation:	0.5
Respiratory Toxicity:	0.771

Download Data

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

Natural Product: NPC28042

Natural Product ID:	NPC28042
*Common Name:**	Xylariaquinone A
IUPAC Name:	7-hydroxy-8-methoxy-3,6-dimethyldibenzofuran-1,4-dione
Synonyms:
Standard InCHIKey:	PELMMCMFWVEXMP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12O5/c1-6-4-9(16)11-8-5-10(19-3)13(18)7(2)14(8)20-15(11)12(6)17/h4-5,18H,1-3H3
SMILES:	CC1=CC(=O)c2c3cc(c(c(C)c3oc2C1=O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252331
PubChem CID:	23634443
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO33440	Xylaria sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921427]
NPO33440	Xylaria sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17892262]
NPO33440	Xylaria sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18500842]
NPO33440	Xylaria sp.	Species	Xylariaceae	Eukaryota	Isolated from the lichen Leptogium saturninum (Dicks.) Nyl.	Zixi Mountain, Yunnan, China	2006-NOV	PMID[21428374]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	184000.0	nM	PMID[465964]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6680.0	nM	PMID[465964]

☑ 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 NPC28042 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	456
0.1-0.2	2051
0.2-0.3	5005
0.3-0.4	11361
0.4-0.5	6286
0.5-0.6	4123
0.6-0.7	5162
0.7-0.8	5266
0.8-0.85	1750
0.85-0.9	998
0.9-0.95	237
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9693	High Similarity	NPC289244
0.9394	High Similarity	NPC30550
0.9387	High Similarity	NPC95715
0.9329	High Similarity	NPC202470
0.9321	High Similarity	NPC1755
0.9321	High Similarity	NPC59295
0.9321	High Similarity	NPC39305
0.9321	High Similarity	NPC1706
0.9321	High Similarity	NPC263092
0.9259	High Similarity	NPC238995
0.9226	High Similarity	NPC77179
0.9226	High Similarity	NPC23553
0.9226	High Similarity	NPC221820
0.9176	High Similarity	NPC228209
0.9176	High Similarity	NPC8927
0.9167	High Similarity	NPC8127
0.9167	High Similarity	NPC49667
0.9146	High Similarity	NPC36320
0.9146	High Similarity	NPC45449
0.9107	High Similarity	NPC245975
0.9102	High Similarity	NPC54098
0.9102	High Similarity	NPC230619
0.908	High Similarity	NPC188486
0.9074	High Similarity	NPC16935
0.9074	High Similarity	NPC196879
0.9064	High Similarity	NPC471842
0.9064	High Similarity	NPC246153
0.9053	High Similarity	NPC471841
0.9048	High Similarity	NPC65885
0.9048	High Similarity	NPC82217
0.9048	High Similarity	NPC216842
0.9048	High Similarity	NPC476640
0.9048	High Similarity	NPC277510
0.9036	High Similarity	NPC247973
0.9024	High Similarity	NPC312056
0.9024	High Similarity	NPC84515
0.9024	High Similarity	NPC272722
0.9023	High Similarity	NPC295436
0.9017	High Similarity	NPC240808
0.8994	High Similarity	NPC287243
0.8982	High Similarity	NPC247136
0.897	High Similarity	NPC133065
0.8963	High Similarity	NPC264293
0.8957	High Similarity	NPC195832
0.8953	High Similarity	NPC240508
0.8951	High Similarity	NPC45131
0.8951	High Similarity	NPC472461
0.8947	High Similarity	NPC476273
0.8941	High Similarity	NPC24258
0.8935	High Similarity	NPC233956
0.8935	High Similarity	NPC117450
0.8929	High Similarity	NPC281835
0.8929	High Similarity	NPC476641
0.8922	High Similarity	NPC470704
0.8922	High Similarity	NPC50394
0.8916	High Similarity	NPC37183
0.8916	High Similarity	NPC291110
0.8916	High Similarity	NPC39306
0.8902	High Similarity	NPC246478
0.8882	High Similarity	NPC125300
0.8864	High Similarity	NPC60848
0.8862	High Similarity	NPC277480
0.8848	High Similarity	NPC258331
0.8824	High Similarity	NPC473834
0.8824	High Similarity	NPC261471
0.8824	High Similarity	NPC310794
0.8817	High Similarity	NPC218533
0.8817	High Similarity	NPC78830
0.881	High Similarity	NPC86477
0.881	High Similarity	NPC186392
0.881	High Similarity	NPC241820
0.8795	High Similarity	NPC294965
0.8795	High Similarity	NPC81679
0.8793	High Similarity	NPC71260
0.878	High Similarity	NPC36852
0.878	High Similarity	NPC262286
0.8779	High Similarity	NPC98546
0.8773	High Similarity	NPC234485
0.8765	High Similarity	NPC248593
0.8765	High Similarity	NPC304954
0.8765	High Similarity	NPC28589
0.8765	High Similarity	NPC101996
0.8758	High Similarity	NPC260582
0.8758	High Similarity	NPC103509
0.8743	High Similarity	NPC41301
0.8743	High Similarity	NPC270837
0.8743	High Similarity	NPC470459
0.8721	High Similarity	NPC107244
0.872	High Similarity	NPC43243
0.872	High Similarity	NPC245546
0.872	High Similarity	NPC138243
0.872	High Similarity	NPC266960
0.8713	High Similarity	NPC37606
0.8712	High Similarity	NPC189130
0.8712	High Similarity	NPC271779
0.8712	High Similarity	NPC167091
0.8712	High Similarity	NPC292214
0.8712	High Similarity	NPC88645
0.8712	High Similarity	NPC206238
0.8712	High Similarity	NPC127172
0.8706	High Similarity	NPC131866
0.8704	High Similarity	NPC171010
0.869	High Similarity	NPC470457
0.869	High Similarity	NPC38914
0.869	High Similarity	NPC29411
0.869	High Similarity	NPC326520
0.8688	High Similarity	NPC61871
0.8688	High Similarity	NPC55557
0.8688	High Similarity	NPC30647
0.8688	High Similarity	NPC251188
0.8686	High Similarity	NPC476170
0.8678	High Similarity	NPC47883
0.8678	High Similarity	NPC475996
0.8675	High Similarity	NPC14353
0.8675	High Similarity	NPC476980
0.8675	High Similarity	NPC56085
0.8675	High Similarity	NPC84571
0.8675	High Similarity	NPC228785
0.8671	High Similarity	NPC297807
0.8671	High Similarity	NPC246877
0.8667	High Similarity	NPC305663
0.8667	High Similarity	NPC176665
0.8667	High Similarity	NPC163524
0.8667	High Similarity	NPC78225
0.8667	High Similarity	NPC7973
0.8667	High Similarity	NPC203891
0.8667	High Similarity	NPC101830
0.8667	High Similarity	NPC287979
0.8667	High Similarity	NPC472438
0.8667	High Similarity	NPC78302
0.8667	High Similarity	NPC29841
0.8667	High Similarity	NPC110070
0.8667	High Similarity	NPC235215
0.8663	High Similarity	NPC227906
0.8659	High Similarity	NPC44079
0.8659	High Similarity	NPC201451
0.8659	High Similarity	NPC26227
0.8659	High Similarity	NPC113906
0.8659	High Similarity	NPC472048
0.8659	High Similarity	NPC268008
0.8655	High Similarity	NPC174700
0.8655	High Similarity	NPC307286
0.865	High Similarity	NPC199100
0.865	High Similarity	NPC120537
0.865	High Similarity	NPC161277
0.865	High Similarity	NPC39007
0.865	High Similarity	NPC180234
0.8647	High Similarity	NPC165979
0.8647	High Similarity	NPC152477
0.8647	High Similarity	NPC163130
0.8647	High Similarity	NPC211309
0.8642	High Similarity	NPC179183
0.8639	High Similarity	NPC62444
0.8639	High Similarity	NPC170245
0.8639	High Similarity	NPC470462
0.8634	High Similarity	NPC287395
0.8634	High Similarity	NPC183655
0.8634	High Similarity	NPC19545
0.8631	High Similarity	NPC476822
0.8631	High Similarity	NPC473313
0.8631	High Similarity	NPC472278
0.8631	High Similarity	NPC15819
0.8631	High Similarity	NPC18100
0.8631	High Similarity	NPC179464
0.8631	High Similarity	NPC329669
0.8631	High Similarity	NPC472582
0.8631	High Similarity	NPC236132
0.8623	High Similarity	NPC278052
0.8623	High Similarity	NPC66288
0.8623	High Similarity	NPC269117
0.8623	High Similarity	NPC308992
0.8623	High Similarity	NPC40491
0.8623	High Similarity	NPC61010
0.8623	High Similarity	NPC311740
0.8621	High Similarity	NPC183843
0.8614	High Similarity	NPC105242
0.8614	High Similarity	NPC104876
0.8614	High Similarity	NPC100123
0.8614	High Similarity	NPC55738
0.8614	High Similarity	NPC261004
0.8614	High Similarity	NPC18772
0.8614	High Similarity	NPC130894
0.8614	High Similarity	NPC152166
0.8614	High Similarity	NPC143828
0.8614	High Similarity	NPC477410
0.8614	High Similarity	NPC300943
0.8614	High Similarity	NPC176300
0.8614	High Similarity	NPC253634
0.8614	High Similarity	NPC9609
0.8614	High Similarity	NPC25495
0.8614	High Similarity	NPC22472
0.8614	High Similarity	NPC115798
0.8614	High Similarity	NPC245891
0.8614	High Similarity	NPC18607
0.8614	High Similarity	NPC204854
0.8614	High Similarity	NPC250076
0.8614	High Similarity	NPC19687
0.8614	High Similarity	NPC191459
0.8614	High Similarity	NPC7846
0.8614	High Similarity	NPC4481

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 NPC28042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	1047
0.2-0.3	2046
0.3-0.4	2753
0.4-0.5	1575
0.5-0.6	888
0.6-0.7	288
0.7-0.8	108
0.8-0.85	20
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8963	High Similarity	NPD1247	Approved
0.872	High Similarity	NPD3882	Suspended
0.8485	Intermediate Similarity	NPD2801	Approved
0.8393	Intermediate Similarity	NPD919	Approved
0.8313	Intermediate Similarity	NPD1934	Approved
0.8304	Intermediate Similarity	NPD3926	Phase 2
0.8282	Intermediate Similarity	NPD1512	Approved
0.8263	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5494	Approved
0.816	Intermediate Similarity	NPD1511	Approved
0.8057	Intermediate Similarity	NPD3818	Discontinued
0.8046	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD6166	Phase 2
0.8035	Intermediate Similarity	NPD6232	Discontinued
0.8025	Intermediate Similarity	NPD2800	Approved
0.8	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD3817	Phase 2
0.7933	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7075	Discontinued
0.7836	Intermediate Similarity	NPD1465	Phase 2
0.7836	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD5844	Phase 1
0.7805	Intermediate Similarity	NPD1243	Approved
0.7798	Intermediate Similarity	NPD920	Approved
0.7791	Intermediate Similarity	NPD2344	Approved
0.7791	Intermediate Similarity	NPD1471	Phase 3
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7765	Intermediate Similarity	NPD6599	Discontinued
0.7746	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6799	Approved
0.7722	Intermediate Similarity	NPD6797	Phase 2
0.768	Intermediate Similarity	NPD7251	Discontinued
0.7679	Intermediate Similarity	NPD2533	Approved
0.7679	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD2534	Approved
0.7679	Intermediate Similarity	NPD2532	Approved
0.7674	Intermediate Similarity	NPD6801	Discontinued
0.7667	Intermediate Similarity	NPD7074	Phase 3
0.7661	Intermediate Similarity	NPD4380	Phase 2
0.7654	Intermediate Similarity	NPD1607	Approved
0.764	Intermediate Similarity	NPD943	Approved
0.764	Intermediate Similarity	NPD1240	Approved
0.7637	Intermediate Similarity	NPD7808	Phase 3
0.7636	Intermediate Similarity	NPD1549	Phase 2
0.7611	Intermediate Similarity	NPD7054	Approved
0.7605	Intermediate Similarity	NPD2309	Approved
0.76	Intermediate Similarity	NPD3749	Approved
0.7586	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5402	Approved
0.7576	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6959	Discontinued
0.7569	Intermediate Similarity	NPD7472	Approved
0.7568	Intermediate Similarity	NPD8434	Phase 2
0.7561	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1510	Phase 2
0.756	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7819	Suspended
0.7527	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD3226	Approved
0.7487	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD230	Phase 1
0.7471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD3751	Discontinued
0.7455	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2403	Approved
0.7444	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2935	Discontinued
0.7407	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD447	Suspended
0.7326	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2796	Approved
0.7263	Intermediate Similarity	NPD6234	Discontinued
0.7263	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7768	Phase 2
0.7235	Intermediate Similarity	NPD3750	Approved
0.7231	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6651	Approved
0.7222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1551	Phase 2
0.7198	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5403	Approved
0.7184	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2163	Approved
0.7174	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7117	Intermediate Similarity	NPD9494	Approved
0.7108	Intermediate Similarity	NPD1613	Approved
0.7108	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2296	Approved
0.7079	Intermediate Similarity	NPD37	Approved
0.7067	Intermediate Similarity	NPD7907	Approved
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.7059	Intermediate Similarity	NPD5953	Discontinued
0.7059	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6778	Approved
0.7056	Intermediate Similarity	NPD4965	Approved
0.7056	Intermediate Similarity	NPD6781	Approved
0.7056	Intermediate Similarity	NPD6779	Approved
0.7056	Intermediate Similarity	NPD6777	Approved
0.7056	Intermediate Similarity	NPD6780	Approved
0.7056	Intermediate Similarity	NPD4967	Phase 2
0.7056	Intermediate Similarity	NPD6782	Approved
0.7056	Intermediate Similarity	NPD4966	Approved
0.7056	Intermediate Similarity	NPD6776	Approved
0.7049	Intermediate Similarity	NPD3787	Discontinued
0.7041	Intermediate Similarity	NPD2799	Discontinued
0.7035	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7435	Discontinued
0.7035	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4628	Phase 3
0.7011	Intermediate Similarity	NPD7390	Discontinued
0.6995	Remote Similarity	NPD7199	Phase 2
0.6994	Remote Similarity	NPD6190	Approved
0.6989	Remote Similarity	NPD7228	Approved
0.6984	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4665	Approved
0.6971	Remote Similarity	NPD4111	Phase 1
0.6952	Remote Similarity	NPD7286	Phase 2
0.6949	Remote Similarity	NPD1653	Approved
0.6941	Remote Similarity	NPD3748	Approved
0.6928	Remote Similarity	NPD3027	Phase 3
0.6927	Remote Similarity	NPD8150	Discontinued
0.6914	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD9269	Phase 2
0.6901	Remote Similarity	NPD6100	Approved
0.6901	Remote Similarity	NPD6099	Approved
0.6886	Remote Similarity	NPD2313	Discontinued
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7698	Approved
0.6866	Remote Similarity	NPD7697	Approved
0.6866	Remote Similarity	NPD7696	Phase 3
0.6865	Remote Similarity	NPD6808	Phase 2
0.6863	Remote Similarity	NPD8151	Discontinued
0.6832	Remote Similarity	NPD7870	Phase 2
0.6832	Remote Similarity	NPD7871	Phase 2
0.6829	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7874	Approved
0.6825	Remote Similarity	NPD1729	Discontinued
0.6818	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7701	Phase 2
0.6802	Remote Similarity	NPD6535	Approved
0.6802	Remote Similarity	NPD6534	Approved
0.6796	Remote Similarity	NPD6279	Approved
0.6796	Remote Similarity	NPD6280	Approved
0.6788	Remote Similarity	NPD1470	Approved
0.6788	Remote Similarity	NPD1203	Approved
0.6786	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7229	Phase 3
0.6771	Remote Similarity	NPD8312	Approved
0.6771	Remote Similarity	NPD8313	Approved
0.6769	Remote Similarity	NPD4287	Approved
0.6765	Remote Similarity	NPD1933	Approved
0.6738	Remote Similarity	NPD5242	Approved
0.6733	Remote Similarity	NPD3057	Approved
0.6715	Remote Similarity	NPD7801	Approved
0.6707	Remote Similarity	NPD9717	Approved
0.6706	Remote Similarity	NPD4060	Phase 1
0.6702	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7700	Phase 2
0.67	Remote Similarity	NPD7699	Phase 2
0.6686	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2654	Approved
0.6686	Remote Similarity	NPD411	Approved
0.6683	Remote Similarity	NPD2494	Approved
0.6683	Remote Similarity	NPD2493	Approved
0.6682	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9268	Approved
0.6667	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD5760	Phase 2
0.665	Remote Similarity	NPD3533	Approved
0.665	Remote Similarity	NPD2972	Approved
0.665	Remote Similarity	NPD2491	Approved
0.6635	Remote Similarity	NPD7783	Phase 2
0.6635	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5353	Approved
0.6627	Remote Similarity	NPD4625	Phase 3
0.6615	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2354	Approved
0.6606	Remote Similarity	NPD1608	Approved
0.6601	Remote Similarity	NPD3450	Approved
0.6601	Remote Similarity	NPD3452	Approved
0.66	Remote Similarity	NPD4361	Phase 2
0.66	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4907	Clinical (unspecified phase)

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