NPASS Compound

Structure

CID256042 OpenBabel06191716062D 21 23 0 0 0 0 0 0 0 0999 V2000 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 8 2 0 0 0 0 4 9 2 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 6 11 2 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.05
Volume:	273.977
LogP:	2.846
LogD:	2.236
LogS:	-3.46
# Rotatable Bonds:	1
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	2.448
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.028
MDCK Permeability:	9.718642104417086e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.819
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	98.69902038574219%
Volume Distribution (VD):	0.465
Pgp-substrate:	4.130649089813232%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.681
CYP2C9-substrate:	0.79
CYP2D6-inhibitor:	0.735
CYP2D6-substrate:	0.239
CYP3A4-inhibitor:	0.522
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	6.115
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.072
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.716
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.112
Skin Sensitization:	0.828
Carcinogencity:	0.064
Eye Corrosion:	0.018
Eye Irritation:	0.938
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC256042

Natural Product ID:	NPC256042
*Common Name:**	Datiscetin
IUPAC Name:	3,5,7-trihydroxy-2-(2-hydroxyphenyl)chromen-4-one
Synonyms:	3,5,7,2'-Tetrahydroxyflavone; Datiscetin
Standard InCHIKey:	WCNLFPKXBGWWDS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6/c16-7-5-10(18)12-11(6-7)21-15(14(20)13(12)19)8-3-1-2-4-9(8)17/h1-6,16-18,20H
SMILES:	Oc1cc(O)c2c(c1)oc(c(c2=O)O)c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503168
PubChem CID:	5281610
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO40537	Koelreuteria henryi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350096]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13167	Scutellaria amoena	Species	Lamiaceae	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
Others	8

Activity Type	# Activity
Individual Protein	6
NON-MOLECULAR	1
Organism	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	23.0	%	PMID[572982]
NPT1380	Individual Protein	Avian myoblastosis virus polyprotein II	Avian myeloblastosis virus	Inhibition	=	28.0	%	PMID[572983]
NPT1443	Individual Protein	Pyruvate dehydrogenase kinase isoform 1	Homo sapiens	Inhibition	=	0.4	%	PMID[572985]
NPT2	Others	Unspecified		Activity	=	28.4	n.a.	PMID[572978]
NPT2	Others	Unspecified		IC50	=	60.0	ug.mL-1	PMID[572979]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	86.5	%	PMID[572980]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	1.68	%	PMID[572982]
NPT35	Others	n.a.		Stability	>	80.0	%	PMID[572984]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	IC50	=	55400.0	nM	PMID[572984]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	TIME	=	6.0	hr	PMID[572984]
NPT2	Others	Unspecified		IC50	=	55400.0	nM	PMID[572986]
NPT2	Others	Unspecified		IC50	=	76900.0	nM	PMID[572987]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	27000.0	nM	PMID[572987]

☑ 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 NPC256042 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	532
0.1-0.2	2249
0.2-0.3	5822
0.3-0.4	11623
0.4-0.5	4956
0.5-0.6	4497
0.6-0.7	5567
0.7-0.8	3956
0.8-0.85	2074
0.85-0.9	986
0.9-0.95	368
0.95-1	67

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC216361
1.0	High Similarity	NPC281917
1.0	High Similarity	NPC187432
1.0	High Similarity	NPC116775
0.9924	High Similarity	NPC299379
0.9846	High Similarity	NPC248872
0.9774	High Similarity	NPC152042
0.9774	High Similarity	NPC143799
0.9774	High Similarity	NPC241838
0.9769	High Similarity	NPC274121
0.9769	High Similarity	NPC50898
0.9769	High Similarity	NPC78540
0.9769	High Similarity	NPC213216
0.9701	High Similarity	NPC184536
0.9701	High Similarity	NPC146679
0.9701	High Similarity	NPC59951
0.9701	High Similarity	NPC269652
0.9701	High Similarity	NPC281207
0.9701	High Similarity	NPC103342
0.9701	High Similarity	NPC103904
0.9701	High Similarity	NPC230285
0.9695	High Similarity	NPC172262
0.9692	High Similarity	NPC128216
0.963	High Similarity	NPC262094
0.963	High Similarity	NPC136840
0.963	High Similarity	NPC90582
0.9618	High Similarity	NPC57601
0.9615	High Similarity	NPC113006
0.9559	High Similarity	NPC200694
0.9559	High Similarity	NPC473042
0.9552	High Similarity	NPC276905
0.9549	High Similarity	NPC473887
0.9549	High Similarity	NPC231772
0.9549	High Similarity	NPC194281
0.9549	High Similarity	NPC47815
0.9549	High Similarity	NPC234133
0.9549	High Similarity	NPC13408
0.9549	High Similarity	NPC29353
0.9549	High Similarity	NPC124784
0.9549	High Similarity	NPC127447
0.9489	High Similarity	NPC293053
0.9489	High Similarity	NPC24821
0.9489	High Similarity	NPC9117
0.9489	High Similarity	NPC470216
0.9489	High Similarity	NPC212932
0.9489	High Similarity	NPC190637
0.9478	High Similarity	NPC254841
0.9478	High Similarity	NPC250266
0.9478	High Similarity	NPC266597
0.9474	High Similarity	NPC239495
0.9474	High Similarity	NPC9985
0.942	High Similarity	NPC216538
0.942	High Similarity	NPC273538
0.942	High Similarity	NPC326500
0.9407	High Similarity	NPC201395
0.9389	High Similarity	NPC137264
0.9389	High Similarity	NPC5515
0.9389	High Similarity	NPC270369
0.9385	High Similarity	NPC197425
0.9353	High Similarity	NPC153758
0.9353	High Similarity	NPC178343
0.9353	High Similarity	NPC179271
0.9353	High Similarity	NPC306488
0.9353	High Similarity	NPC20791
0.9353	High Similarity	NPC5820
0.9353	High Similarity	NPC124729
0.9348	High Similarity	NPC158874
0.9343	High Similarity	NPC310128
0.9338	High Similarity	NPC301217
0.9338	High Similarity	NPC96565
0.9338	High Similarity	NPC303633
0.9338	High Similarity	NPC216978
0.9338	High Similarity	NPC55018
0.9338	High Similarity	NPC18260
0.9338	High Similarity	NPC220062
0.9338	High Similarity	NPC78913
0.9333	High Similarity	NPC296490
0.9333	High Similarity	NPC275055
0.9333	High Similarity	NPC295261
0.9333	High Similarity	NPC13768
0.9333	High Similarity	NPC79943
0.9333	High Similarity	NPC107586
0.9333	High Similarity	NPC287246
0.9333	High Similarity	NPC12296
0.9333	High Similarity	NPC32441
0.9333	High Similarity	NPC290291
0.9333	High Similarity	NPC243083
0.9333	High Similarity	NPC228661
0.9318	High Similarity	NPC475589
0.9318	High Similarity	NPC31872
0.9318	High Similarity	NPC473584
0.9313	High Similarity	NPC39753
0.9313	High Similarity	NPC115998
0.9286	High Similarity	NPC74881
0.9286	High Similarity	NPC51443
0.9286	High Similarity	NPC14001
0.9286	High Similarity	NPC166757
0.9281	High Similarity	NPC62290
0.9281	High Similarity	NPC4152
0.9281	High Similarity	NPC326506
0.9281	High Similarity	NPC49130
0.9281	High Similarity	NPC279417
0.9281	High Similarity	NPC208176
0.9281	High Similarity	NPC306607
0.9281	High Similarity	NPC142731
0.9275	High Similarity	NPC471520
0.927	High Similarity	NPC270883
0.927	High Similarity	NPC159275
0.927	High Similarity	NPC241100
0.927	High Similarity	NPC261227
0.927	High Similarity	NPC172986
0.9265	High Similarity	NPC99333
0.9265	High Similarity	NPC472460
0.9265	High Similarity	NPC188947
0.9265	High Similarity	NPC147686
0.9265	High Similarity	NPC280284
0.9265	High Similarity	NPC329225
0.9265	High Similarity	NPC118813
0.9259	High Similarity	NPC61546
0.9259	High Similarity	NPC72452
0.9248	High Similarity	NPC25937
0.9248	High Similarity	NPC10971
0.922	High Similarity	NPC296869
0.922	High Similarity	NPC244407
0.9214	High Similarity	NPC229190
0.9214	High Similarity	NPC220418
0.9214	High Similarity	NPC169749
0.9214	High Similarity	NPC470458
0.9214	High Similarity	NPC148011
0.9214	High Similarity	NPC1940
0.9209	High Similarity	NPC279121
0.9203	High Similarity	NPC118840
0.9203	High Similarity	NPC110969
0.9203	High Similarity	NPC147688
0.9203	High Similarity	NPC64908
0.9203	High Similarity	NPC282300
0.9203	High Similarity	NPC156590
0.9203	High Similarity	NPC14871
0.9203	High Similarity	NPC205006
0.9197	High Similarity	NPC329203
0.9197	High Similarity	NPC150648
0.9197	High Similarity	NPC261234
0.9197	High Similarity	NPC53181
0.9197	High Similarity	NPC217186
0.9197	High Similarity	NPC225153
0.9197	High Similarity	NPC20709
0.9197	High Similarity	NPC316480
0.9197	High Similarity	NPC274784
0.9197	High Similarity	NPC310135
0.9197	High Similarity	NPC265871
0.9197	High Similarity	NPC222342
0.9191	High Similarity	NPC84585
0.9191	High Similarity	NPC188879
0.9191	High Similarity	NPC160972
0.9191	High Similarity	NPC476480
0.9185	High Similarity	NPC234560
0.9185	High Similarity	NPC39426
0.9179	High Similarity	NPC223457
0.9179	High Similarity	NPC93756
0.9179	High Similarity	NPC108113
0.9173	High Similarity	NPC278556
0.9173	High Similarity	NPC65060
0.9155	High Similarity	NPC195351
0.9155	High Similarity	NPC270465
0.9155	High Similarity	NPC269420
0.9155	High Similarity	NPC470461
0.9155	High Similarity	NPC159103
0.9155	High Similarity	NPC87125
0.9149	High Similarity	NPC211466
0.9149	High Similarity	NPC40086
0.9149	High Similarity	NPC3779
0.9149	High Similarity	NPC472918
0.9149	High Similarity	NPC476182
0.9149	High Similarity	NPC44721
0.9149	High Similarity	NPC259632
0.9149	High Similarity	NPC122828
0.9149	High Similarity	NPC176869
0.9143	High Similarity	NPC71210
0.9143	High Similarity	NPC70136
0.9137	High Similarity	NPC62840
0.9137	High Similarity	NPC214236
0.9137	High Similarity	NPC59739
0.9137	High Similarity	NPC11561
0.9137	High Similarity	NPC226636
0.9137	High Similarity	NPC159855
0.9137	High Similarity	NPC169479
0.9137	High Similarity	NPC217083
0.9137	High Similarity	NPC175013
0.9137	High Similarity	NPC299080
0.9137	High Similarity	NPC293852
0.9137	High Similarity	NPC78803
0.913	High Similarity	NPC235239
0.913	High Similarity	NPC129853
0.913	High Similarity	NPC110228
0.913	High Similarity	NPC69769
0.913	High Similarity	NPC6407
0.913	High Similarity	NPC475680
0.913	High Similarity	NPC188243
0.913	High Similarity	NPC150522
0.913	High Similarity	NPC76445

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 NPC256042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	483
0.1-0.2	1027
0.2-0.3	1819
0.3-0.4	2749
0.4-0.5	1693
0.5-0.6	947
0.6-0.7	287
0.7-0.8	95
0.8-0.85	30
0.85-0.9	14
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.942	High Similarity	NPD4378	Clinical (unspecified phase)
0.9353	High Similarity	NPD1512	Approved
0.9333	High Similarity	NPD1552	Clinical (unspecified phase)
0.9333	High Similarity	NPD1550	Clinical (unspecified phase)
0.9265	High Similarity	NPD1549	Phase 2
0.9209	High Similarity	NPD1511	Approved
0.9185	High Similarity	NPD1510	Phase 2
0.903	High Similarity	NPD1240	Approved
0.8897	High Similarity	NPD1607	Approved
0.8873	High Similarity	NPD7410	Clinical (unspecified phase)
0.8705	High Similarity	NPD2796	Approved
0.8671	High Similarity	NPD6799	Approved
0.8649	High Similarity	NPD2801	Approved
0.8592	High Similarity	NPD3750	Approved
0.8581	High Similarity	NPD1934	Approved
0.8571	High Similarity	NPD4380	Phase 2
0.8523	High Similarity	NPD2393	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD7075	Discontinued
0.8477	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD3817	Phase 2
0.8456	Intermediate Similarity	NPD6801	Discontinued
0.8451	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD1551	Phase 2
0.8411	Intermediate Similarity	NPD3882	Suspended
0.84	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD7411	Suspended
0.837	Intermediate Similarity	NPD1203	Approved
0.8367	Intermediate Similarity	NPD5403	Approved
0.8356	Intermediate Similarity	NPD5401	Approved
0.8344	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD6599	Discontinued
0.8269	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD6166	Phase 2
0.8264	Intermediate Similarity	NPD2800	Approved
0.8239	Intermediate Similarity	NPD3748	Approved
0.8235	Intermediate Similarity	NPD3749	Approved
0.8228	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1548	Phase 1
0.8158	Intermediate Similarity	NPD7819	Suspended
0.8138	Intermediate Similarity	NPD1243	Approved
0.8125	Intermediate Similarity	NPD6797	Phase 2
0.8105	Intermediate Similarity	NPD5402	Approved
0.8075	Intermediate Similarity	NPD7251	Discontinued
0.8074	Intermediate Similarity	NPD422	Phase 1
0.8071	Intermediate Similarity	NPD2313	Discontinued
0.805	Intermediate Similarity	NPD3818	Discontinued
0.8025	Intermediate Similarity	NPD7808	Phase 3
0.8025	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD9717	Approved
0.8014	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD2344	Approved
0.7987	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6959	Discontinued
0.7959	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD943	Approved
0.795	Intermediate Similarity	NPD7472	Approved
0.7941	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD7768	Phase 2
0.7925	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD3225	Approved
0.7847	Intermediate Similarity	NPD6651	Approved
0.784	Intermediate Similarity	NPD7074	Phase 3
0.7821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD3268	Approved
0.781	Intermediate Similarity	NPD1610	Phase 2
0.7808	Intermediate Similarity	NPD2935	Discontinued
0.7785	Intermediate Similarity	NPD2309	Approved
0.774	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD2799	Discontinued
0.7736	Intermediate Similarity	NPD1247	Approved
0.7722	Intermediate Similarity	NPD919	Approved
0.7714	Intermediate Similarity	NPD2797	Approved
0.7697	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.7692	Intermediate Similarity	NPD1296	Phase 2
0.7688	Intermediate Similarity	NPD6232	Discontinued
0.7687	Intermediate Similarity	NPD6100	Approved
0.7687	Intermediate Similarity	NPD6099	Approved
0.7676	Intermediate Similarity	NPD6832	Phase 2
0.7676	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD5494	Approved
0.7669	Intermediate Similarity	NPD7286	Phase 2
0.7662	Intermediate Similarity	NPD3226	Approved
0.766	Intermediate Similarity	NPD2798	Approved
0.7654	Intermediate Similarity	NPD7473	Discontinued
0.7632	Intermediate Similarity	NPD2533	Approved
0.7632	Intermediate Similarity	NPD2534	Approved
0.7632	Intermediate Similarity	NPD2532	Approved
0.7626	Intermediate Similarity	NPD1481	Phase 2
0.7619	Intermediate Similarity	NPD7033	Discontinued
0.7619	Intermediate Similarity	NPD4308	Phase 3
0.7606	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD3266	Approved
0.7589	Intermediate Similarity	NPD3267	Approved
0.7576	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5953	Discontinued
0.7554	Intermediate Similarity	NPD1535	Discovery
0.7552	Intermediate Similarity	NPD4908	Phase 1
0.7534	Intermediate Similarity	NPD447	Suspended
0.7533	Intermediate Similarity	NPD2654	Approved
0.7532	Intermediate Similarity	NPD4288	Approved
0.7531	Intermediate Similarity	NPD3926	Phase 2
0.753	Intermediate Similarity	NPD6559	Discontinued
0.7518	Intermediate Similarity	NPD9545	Approved
0.7517	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD9493	Approved
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7466	Intermediate Similarity	NPD1613	Approved
0.7466	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7390	Discontinued
0.7448	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD411	Approved
0.7429	Intermediate Similarity	NPD1201	Approved
0.7415	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1933	Approved
0.7415	Intermediate Similarity	NPD230	Phase 1
0.7413	Intermediate Similarity	NPD1019	Discontinued
0.7407	Intermediate Similarity	NPD1241	Discontinued
0.74	Intermediate Similarity	NPD1471	Phase 3
0.7394	Intermediate Similarity	NPD3751	Discontinued
0.7371	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4360	Phase 2
0.7356	Intermediate Similarity	NPD4363	Phase 3
0.7349	Intermediate Similarity	NPD5844	Phase 1
0.7347	Intermediate Similarity	NPD4307	Phase 2
0.7343	Intermediate Similarity	NPD1470	Approved
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7329	Intermediate Similarity	NPD3764	Approved
0.732	Intermediate Similarity	NPD2354	Approved
0.731	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD17	Approved
0.7279	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3787	Discontinued
0.7254	Intermediate Similarity	NPD3972	Approved
0.7233	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4287	Approved
0.7222	Intermediate Similarity	NPD1164	Approved
0.7216	Intermediate Similarity	NPD4361	Phase 2
0.7216	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2296	Approved
0.7202	Intermediate Similarity	NPD1729	Discontinued
0.7197	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1652	Phase 2
0.7181	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5124	Phase 1
0.7179	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2353	Approved
0.7169	Intermediate Similarity	NPD2403	Approved
0.7164	Intermediate Similarity	NPD9266	Approved
0.7164	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.709	Intermediate Similarity	NPD9263	Approved
0.709	Intermediate Similarity	NPD9267	Approved
0.709	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD9264	Approved
0.7083	Intermediate Similarity	NPD4749	Approved
0.7081	Intermediate Similarity	NPD6844	Discontinued
0.7067	Intermediate Similarity	NPD4340	Discontinued
0.7067	Intermediate Similarity	NPD6355	Discontinued
0.7051	Intermediate Similarity	NPD7440	Discontinued
0.7048	Intermediate Similarity	NPD5710	Approved
0.7048	Intermediate Similarity	NPD5711	Approved
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5049	Phase 3
0.7018	Intermediate Similarity	NPD6104	Discontinued
0.7015	Intermediate Similarity	NPD968	Approved
0.7014	Intermediate Similarity	NPD9269	Phase 2
0.7007	Intermediate Similarity	NPD2861	Phase 2
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5404	Approved
0.6993	Remote Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD5408	Approved
0.6993	Remote Similarity	NPD5405	Approved
0.6987	Remote Similarity	NPD3887	Approved
0.6987	Remote Similarity	NPD6190	Approved
0.6982	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9268	Approved
0.6957	Remote Similarity	NPD6585	Discontinued
0.6948	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7229	Phase 3
0.6937	Remote Similarity	NPD1653	Approved
0.6933	Remote Similarity	NPD4062	Phase 3
0.6919	Remote Similarity	NPD7584	Approved
0.6918	Remote Similarity	NPD1876	Approved
0.6914	Remote Similarity	NPD5889	Approved
0.6914	Remote Similarity	NPD5890	Approved
0.6914	Remote Similarity	NPD8434	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