NPASS Compound

Structure

NPC209985 OpenBabel07101718242D 26 28 0 0 1 0 0 0 0 0999 V2000 4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 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 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 24 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 17 2 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 11 1 1 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 13 1 6 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.14
Volume:	363.093
LogP:	1.843
LogD:	2.353
LogS:	-3.689
# Rotatable Bonds:	6
TPSA:	88.38
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	3.571
Fsp3:	0.3
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:	-4.753
MDCK Permeability:	8.235002496803645e-06
Pgp-inhibitor:	0.076
Pgp-substrate:	0.745
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.069

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	92.04612731933594%
Volume Distribution (VD):	0.547
Pgp-substrate:	10.810131072998047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.356
CYP1A2-substrate:	0.886
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.41
CYP2C9-inhibitor:	0.285
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.407
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.715

ADMET: Excretion

Clearance (CL):	7.179
Half-life (T1/2):	0.704

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.481
Drug-inuced Liver Injury (DILI):	0.366
AMES Toxicity:	0.379
Rat Oral Acute Toxicity:	0.198
Maximum Recommended Daily Dose:	0.539
Skin Sensitization:	0.925
Carcinogencity:	0.819
Eye Corrosion:	0.003
Eye Irritation:	0.151
Respiratory Toxicity:	0.087

Download Data

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

Natural Product: NPC209985

Natural Product ID:	NPC209985
*Common Name:**	Hierochin A
IUPAC Name:	(2R,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-[(E)-3-methoxyprop-1-enyl]-2,3-dihydro-1-benzofuran-7-ol
Synonyms:	Hierochin A
Standard InCHIKey:	VHVQTNBRDOVOOA-GWKPYITFSA-N
Standard InCHI:	InChI=1S/C20H22O6/c1-24-7-3-4-12-8-14-15(11-21)19(26-20(14)17(23)9-12)13-5-6-16(22)18(10-13)25-2/h3-6,8-10,15,19,21-23H,7,11H2,1-2H3/b4-3+/t15-,19+/m1/s1
SMILES:	COC/C=C/c1cc(O)c2c(c1)[C@@H](CO)[C@@H](O2)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL591727
PubChem CID:	10089764
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12643908]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20189399]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	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	1
Others	6

Activity Type	# Activity
Individual Protein	1
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	<	10.4	%	PMID[473658]
NPT2	Others	Unspecified		Inhibition	=	1.9	%	PMID[473658]
NPT2	Others	Unspecified		Inhibition	=	8.0	%	PMID[473658]
NPT2	Others	Unspecified		Inhibition	=	32.5	%	PMID[473658]
NPT2	Others	Unspecified		Inhibition	=	51.8	%	PMID[473658]
NPT2	Others	Unspecified		IC50	=	25000.0	nM	PMID[473658]
NPT27	Others	Unspecified		Inhibition	<	8.8	%	PMID[473658]

☑ 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 NPC209985 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	407
0.1-0.2	1377
0.2-0.3	3777
0.3-0.4	10098
0.4-0.5	8582
0.5-0.6	3867
0.6-0.7	7559
0.7-0.8	5284
0.8-0.85	936
0.85-0.9	606
0.9-0.95	184
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477939
1.0	High Similarity	NPC156502
1.0	High Similarity	NPC54743
1.0	High Similarity	NPC10737
1.0	High Similarity	NPC177160
1.0	High Similarity	NPC29799
1.0	High Similarity	NPC263367
0.9845	High Similarity	NPC193026
0.9845	High Similarity	NPC49603
0.9845	High Similarity	NPC187616
0.9767	High Similarity	NPC26394
0.9699	High Similarity	NPC87725
0.9699	High Similarity	NPC471414
0.9699	High Similarity	NPC263261
0.969	High Similarity	NPC230219
0.9627	High Similarity	NPC253878
0.9538	High Similarity	NPC18842
0.9535	High Similarity	NPC257582
0.9535	High Similarity	NPC42300
0.9535	High Similarity	NPC187998
0.9535	High Similarity	NPC77040
0.9535	High Similarity	NPC153739
0.9535	High Similarity	NPC242807
0.9535	High Similarity	NPC145305
0.9535	High Similarity	NPC241522
0.9535	High Similarity	NPC174495
0.9535	High Similarity	NPC92164
0.9535	High Similarity	NPC64201
0.9485	High Similarity	NPC474444
0.9485	High Similarity	NPC264706
0.9485	High Similarity	NPC284881
0.9485	High Similarity	NPC93433
0.9481	High Similarity	NPC131971
0.9474	High Similarity	NPC477938
0.9462	High Similarity	NPC277804
0.9457	High Similarity	NPC475875
0.9416	High Similarity	NPC163898
0.9394	High Similarity	NPC16485
0.9394	High Similarity	NPC478085
0.9385	High Similarity	NPC143483
0.938	High Similarity	NPC128208
0.938	High Similarity	NPC21867
0.938	High Similarity	NPC11258
0.938	High Similarity	NPC282703
0.938	High Similarity	NPC45774
0.938	High Similarity	NPC184733
0.938	High Similarity	NPC470084
0.938	High Similarity	NPC129570
0.9348	High Similarity	NPC260397
0.9343	High Similarity	NPC12641
0.9343	High Similarity	NPC280092
0.9343	High Similarity	NPC45257
0.9343	High Similarity	NPC93323
0.9333	High Similarity	NPC254759
0.9333	High Similarity	NPC309124
0.9333	High Similarity	NPC184797
0.9333	High Similarity	NPC160283
0.9313	High Similarity	NPC228346
0.9313	High Similarity	NPC7171
0.9313	High Similarity	NPC27843
0.9313	High Similarity	NPC115207
0.9313	High Similarity	NPC158079
0.9313	High Similarity	NPC40432
0.9313	High Similarity	NPC161557
0.9302	High Similarity	NPC147821
0.9302	High Similarity	NPC183181
0.9302	High Similarity	NPC118787
0.9302	High Similarity	NPC118533
0.9302	High Similarity	NPC111247
0.9302	High Similarity	NPC98745
0.9302	High Similarity	NPC163332
0.9302	High Similarity	NPC41706
0.9302	High Similarity	NPC319625
0.9302	High Similarity	NPC292056
0.9302	High Similarity	NPC165045
0.9281	High Similarity	NPC31325
0.9281	High Similarity	NPC15956
0.9281	High Similarity	NPC193473
0.9281	High Similarity	NPC275284
0.9281	High Similarity	NPC114505
0.9281	High Similarity	NPC213074
0.9281	High Similarity	NPC224674
0.927	High Similarity	NPC47633
0.927	High Similarity	NPC85264
0.927	High Similarity	NPC102044
0.927	High Similarity	NPC477616
0.9265	High Similarity	NPC311530
0.9259	High Similarity	NPC232164
0.9259	High Similarity	NPC236306
0.9259	High Similarity	NPC473739
0.9259	High Similarity	NPC260741
0.9259	High Similarity	NPC292882
0.9259	High Similarity	NPC70682
0.9254	High Similarity	NPC77861
0.9248	High Similarity	NPC287745
0.9242	High Similarity	NPC207400
0.9242	High Similarity	NPC181049
0.9231	High Similarity	NPC472968
0.9225	High Similarity	NPC58607
0.9225	High Similarity	NPC206882
0.9225	High Similarity	NPC191037
0.9225	High Similarity	NPC178284
0.9214	High Similarity	NPC473408
0.9203	High Similarity	NPC63879
0.9197	High Similarity	NPC107161
0.9179	High Similarity	NPC256262
0.9173	High Similarity	NPC158331
0.9173	High Similarity	NPC475840
0.916	High Similarity	NPC86030
0.916	High Similarity	NPC5851
0.9154	High Similarity	NPC21563
0.9154	High Similarity	NPC5428
0.9147	High Similarity	NPC81641
0.9147	High Similarity	NPC148627
0.9147	High Similarity	NPC194519
0.9143	High Similarity	NPC21776
0.9143	High Similarity	NPC101376
0.9143	High Similarity	NPC16269
0.9137	High Similarity	NPC43508
0.9137	High Similarity	NPC181615
0.9137	High Similarity	NPC476301
0.9124	High Similarity	NPC247291
0.9124	High Similarity	NPC471389
0.9124	High Similarity	NPC35216
0.9111	High Similarity	NPC16435
0.9111	High Similarity	NPC470802
0.9111	High Similarity	NPC306441
0.9111	High Similarity	NPC270456
0.9111	High Similarity	NPC472334
0.9111	High Similarity	NPC162659
0.9111	High Similarity	NPC265433
0.9111	High Similarity	NPC472336
0.9111	High Similarity	NPC248727
0.9104	High Similarity	NPC471942
0.9104	High Similarity	NPC326095
0.9104	High Similarity	NPC67247
0.9104	High Similarity	NPC244983
0.9098	High Similarity	NPC175067
0.9098	High Similarity	NPC4940
0.9098	High Similarity	NPC204215
0.9085	High Similarity	NPC98624
0.9084	High Similarity	NPC72529
0.9084	High Similarity	NPC474178
0.9084	High Similarity	NPC252307
0.9084	High Similarity	NPC245826
0.9078	High Similarity	NPC236166
0.9071	High Similarity	NPC324492
0.9071	High Similarity	NPC317053
0.907	High Similarity	NPC48990
0.907	High Similarity	NPC109822
0.907	High Similarity	NPC114901
0.907	High Similarity	NPC293701
0.907	High Similarity	NPC94276
0.9065	High Similarity	NPC471667
0.9065	High Similarity	NPC217635
0.9065	High Similarity	NPC79429
0.9065	High Similarity	NPC473108
0.9058	High Similarity	NPC476356
0.9058	High Similarity	NPC41782
0.9058	High Similarity	NPC59841
0.9058	High Similarity	NPC475891
0.9058	High Similarity	NPC2613
0.9058	High Similarity	NPC204347
0.9051	High Similarity	NPC55793
0.9051	High Similarity	NPC27495
0.9051	High Similarity	NPC259519
0.9037	High Similarity	NPC112939
0.9037	High Similarity	NPC112246
0.9037	High Similarity	NPC94750
0.9037	High Similarity	NPC121812
0.9037	High Similarity	NPC47398
0.9037	High Similarity	NPC234333
0.9037	High Similarity	NPC99572
0.9037	High Similarity	NPC61946
0.9037	High Similarity	NPC472337
0.9037	High Similarity	NPC473413
0.9037	High Similarity	NPC470356
0.9037	High Similarity	NPC126409
0.9037	High Similarity	NPC474206
0.9037	High Similarity	NPC101624
0.9037	High Similarity	NPC260898
0.9037	High Similarity	NPC134968
0.9037	High Similarity	NPC93783
0.9037	High Similarity	NPC184938
0.903	High Similarity	NPC170185
0.9023	High Similarity	NPC474017
0.9023	High Similarity	NPC472597
0.9007	High Similarity	NPC328567
0.9007	High Similarity	NPC327412
0.9007	High Similarity	NPC320970
0.9007	High Similarity	NPC320671
0.9	High Similarity	NPC469557
0.9	High Similarity	NPC180953
0.8993	High Similarity	NPC185307
0.8993	High Similarity	NPC470950
0.8993	High Similarity	NPC474104
0.8992	High Similarity	NPC471693
0.8992	High Similarity	NPC473451
0.8992	High Similarity	NPC317769
0.8992	High Similarity	NPC280704

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 NPC209985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	835
0.2-0.3	1806
0.3-0.4	2644
0.4-0.5	1680
0.5-0.6	946
0.6-0.7	688
0.7-0.8	207
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8872	High Similarity	NPD3027	Phase 3
0.8815	High Similarity	NPD1613	Approved
0.8815	High Similarity	NPD1612	Clinical (unspecified phase)
0.8519	High Similarity	NPD1529	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD2861	Phase 2
0.8273	Intermediate Similarity	NPD4060	Phase 1
0.8261	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6674	Discontinued
0.8143	Intermediate Similarity	NPD3620	Phase 2
0.8143	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD5283	Phase 1
0.8116	Intermediate Similarity	NPD4908	Phase 1
0.8	Intermediate Similarity	NPD1610	Phase 2
0.7984	Intermediate Similarity	NPD228	Approved
0.7974	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD8651	Approved
0.7917	Intermediate Similarity	NPD5588	Approved
0.7908	Intermediate Similarity	NPD1934	Approved
0.7885	Intermediate Similarity	NPD6234	Discontinued
0.7883	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD3705	Approved
0.7847	Intermediate Similarity	NPD4538	Approved
0.7847	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD4536	Approved
0.7829	Intermediate Similarity	NPD3021	Approved
0.7829	Intermediate Similarity	NPD3022	Approved
0.7808	Intermediate Similarity	NPD5762	Approved
0.7808	Intermediate Similarity	NPD5763	Approved
0.7801	Intermediate Similarity	NPD4625	Phase 3
0.7792	Intermediate Similarity	NPD37	Approved
0.7785	Intermediate Similarity	NPD5058	Phase 3
0.777	Intermediate Similarity	NPD6331	Phase 2
0.7762	Intermediate Similarity	NPD1558	Phase 1
0.7756	Intermediate Similarity	NPD3882	Suspended
0.7756	Intermediate Similarity	NPD4965	Approved
0.7756	Intermediate Similarity	NPD4966	Approved
0.7756	Intermediate Similarity	NPD4967	Phase 2
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD2684	Approved
0.7746	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7157	Approved
0.7737	Intermediate Similarity	NPD1091	Approved
0.7708	Intermediate Similarity	NPD5735	Approved
0.7708	Intermediate Similarity	NPD6355	Discontinued
0.7704	Intermediate Similarity	NPD1548	Phase 1
0.7698	Intermediate Similarity	NPD6696	Suspended
0.7674	Intermediate Similarity	NPD290	Approved
0.7673	Intermediate Similarity	NPD7199	Phase 2
0.7671	Intermediate Similarity	NPD5960	Phase 3
0.766	Intermediate Similarity	NPD3018	Phase 2
0.7654	Intermediate Similarity	NPD7228	Approved
0.7654	Intermediate Similarity	NPD3818	Discontinued
0.7652	Intermediate Similarity	NPD7843	Approved
0.7647	Intermediate Similarity	NPD1653	Approved
0.7647	Intermediate Similarity	NPD1357	Approved
0.764	Intermediate Similarity	NPD2489	Approved
0.764	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD27	Approved
0.764	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6166	Phase 2
0.7628	Intermediate Similarity	NPD2801	Approved
0.7626	Intermediate Similarity	NPD4749	Approved
0.7612	Intermediate Similarity	NPD6671	Approved
0.761	Intermediate Similarity	NPD5494	Approved
0.76	Intermediate Similarity	NPD2677	Approved
0.7584	Intermediate Similarity	NPD4236	Phase 3
0.7584	Intermediate Similarity	NPD4237	Approved
0.758	Intermediate Similarity	NPD2560	Approved
0.758	Intermediate Similarity	NPD2563	Approved
0.7578	Intermediate Similarity	NPD2970	Approved
0.7578	Intermediate Similarity	NPD2969	Approved
0.7568	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6002	Phase 3
0.7568	Intermediate Similarity	NPD6005	Phase 3
0.7568	Intermediate Similarity	NPD6004	Phase 3
0.7568	Intermediate Similarity	NPD7266	Discontinued
0.7568	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4110	Phase 3
0.7532	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2424	Discontinued
0.7516	Intermediate Similarity	NPD3051	Approved
0.7516	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD2982	Phase 2
0.75	Intermediate Similarity	NPD5844	Phase 1
0.7485	Intermediate Similarity	NPD7310	Approved
0.7485	Intermediate Similarity	NPD7313	Approved
0.7485	Intermediate Similarity	NPD7311	Approved
0.7485	Intermediate Similarity	NPD7312	Approved
0.7469	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3060	Approved
0.7467	Intermediate Similarity	NPD5177	Phase 3
0.7465	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4663	Approved
0.7455	Intermediate Similarity	NPD7074	Phase 3
0.745	Intermediate Similarity	NPD1375	Discontinued
0.744	Intermediate Similarity	NPD7309	Approved
0.7432	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2981	Phase 2
0.7417	Intermediate Similarity	NPD4628	Phase 3
0.7415	Intermediate Similarity	NPD6653	Approved
0.7405	Intermediate Similarity	NPD2977	Approved
0.7405	Intermediate Similarity	NPD2978	Approved
0.7397	Intermediate Similarity	NPD4140	Approved
0.7397	Intermediate Similarity	NPD2238	Phase 2
0.7394	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD3094	Phase 2
0.7386	Intermediate Similarity	NPD1511	Approved
0.7386	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2161	Phase 2
0.7381	Intermediate Similarity	NPD4577	Approved
0.7381	Intermediate Similarity	NPD4578	Approved
0.7379	Intermediate Similarity	NPD6798	Discontinued
0.7376	Intermediate Similarity	NPD5327	Phase 3
0.7358	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4162	Approved
0.7349	Intermediate Similarity	NPD7472	Approved
0.7347	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5124	Phase 1
0.7346	Intermediate Similarity	NPD8127	Discontinued
0.7343	Intermediate Similarity	NPD6584	Phase 3
0.7338	Intermediate Similarity	NPD5125	Phase 3
0.7338	Intermediate Similarity	NPD4123	Phase 3
0.7338	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5126	Approved
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6516	Phase 2
0.7338	Intermediate Similarity	NPD5846	Approved
0.7328	Intermediate Similarity	NPD968	Approved
0.7325	Intermediate Similarity	NPD4380	Phase 2
0.732	Intermediate Similarity	NPD6666	Approved
0.732	Intermediate Similarity	NPD6667	Approved
0.7315	Intermediate Similarity	NPD7033	Discontinued
0.731	Intermediate Similarity	NPD7906	Approved
0.731	Intermediate Similarity	NPD7095	Approved
0.7305	Intermediate Similarity	NPD2231	Phase 2
0.7305	Intermediate Similarity	NPD2235	Phase 2
0.7303	Intermediate Similarity	NPD4535	Phase 3
0.7303	Intermediate Similarity	NPD3892	Phase 2
0.7301	Intermediate Similarity	NPD6071	Discontinued
0.7297	Intermediate Similarity	NPD2157	Approved
0.7296	Intermediate Similarity	NPD5773	Approved
0.7296	Intermediate Similarity	NPD5772	Approved
0.7296	Intermediate Similarity	NPD8455	Phase 2
0.7294	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD52	Approved
0.729	Intermediate Similarity	NPD1512	Approved
0.729	Intermediate Similarity	NPD7526	Approved
0.7287	Intermediate Similarity	NPD291	Approved
0.7284	Intermediate Similarity	NPD4666	Phase 3
0.7278	Intermediate Similarity	NPD6072	Discontinued
0.7273	Intermediate Similarity	NPD1774	Approved
0.7267	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6559	Discontinued
0.7261	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3817	Phase 2
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7244	Intermediate Similarity	NPD5976	Discontinued
0.7241	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3092	Approved
0.723	Intermediate Similarity	NPD3657	Discovery
0.7226	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5709	Phase 3
0.7222	Intermediate Similarity	NPD3691	Phase 2
0.7222	Intermediate Similarity	NPD3690	Phase 2
0.7215	Intermediate Similarity	NPD4678	Approved
0.7215	Intermediate Similarity	NPD4675	Approved
0.7214	Intermediate Similarity	NPD4626	Approved
0.7211	Intermediate Similarity	NPD6233	Phase 2
0.7211	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6797	Phase 2
0.7197	Intermediate Similarity	NPD3686	Approved
0.7197	Intermediate Similarity	NPD3687	Approved
0.7195	Intermediate Similarity	NPD6232	Discontinued
0.7188	Intermediate Similarity	NPD5929	Approved
0.7183	Intermediate Similarity	NPD1608	Approved
0.7181	Intermediate Similarity	NPD4097	Suspended
0.7181	Intermediate Similarity	NPD6353	Approved
0.7174	Intermediate Similarity	NPD7340	Approved
0.7171	Intermediate Similarity	NPD7037	Approved
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7163	Intermediate Similarity	NPD3496	Discontinued
0.7162	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7041	Phase 2
0.716	Intermediate Similarity	NPD7075	Discontinued
0.716	Intermediate Similarity	NPD7240	Approved
0.716	Intermediate Similarity	NPD7251	Discontinued
0.7152	Intermediate Similarity	NPD6032	Approved
0.7152	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD5691	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