NPASS Compound

Structure

NPC26394 OpenBabel07101718322D 27 29 0 0 1 0 0 0 0 0999 V2000 5.0878 0.0570 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 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 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 -4.4152 -3.3090 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 1 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 3.0878 0.0570 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 0.5878 -0.8090 0.0000 C 0 0 2 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 -4.4152 -4.3090 0.0000 O 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 3.5878 0.9230 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 -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 26 1 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 22 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 19 2 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 23 1 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 12 1 1 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 26 1 0 0 0 0 20 14 1 6 0 0 0 20 27 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	380.389
LogP:	1.899
LogD:	2.295
LogS:	-3.54
# Rotatable Bonds:	7
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.778
Synthetic Accessibility Score:	3.324
Fsp3:	0.333
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:	-4.767
MDCK Permeability:	1.6148733266163617e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.149
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.932
Plasma Protein Binding (PPB):	71.49526977539062%
Volume Distribution (VD):	0.9
Pgp-substrate:	17.9163818359375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.803
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.664
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.796
CYP3A4-inhibitor:	0.584
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	8.287
Half-life (T1/2):	0.619

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.764
AMES Toxicity:	0.432
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.139
Skin Sensitization:	0.851
Carcinogencity:	0.181
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.089

Download Data

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

Natural Product: NPC26394

Natural Product ID:	NPC26394
*Common Name:**	Hierochin B
IUPAC Name:	(E)-3-[(2S,3R)-2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-ol
Synonyms:	Hierochin B
Standard InCHIKey:	IATWXYMZKVGQLC-WXVIEYATSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-24-17-7-6-14(11-18(17)25-2)20-16(12-23)15-9-13(5-4-8-22)10-19(26-3)21(15)27-20/h4-7,9-11,16,20,22-23H,8,12H2,1-3H3/b5-4+/t16-,20+/m0/s1
SMILES:	COc1ccc(cc1OC)[C@@H]1[C@@H](CO)c2cc(/C=C/CO)cc(c2O1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2368657
PubChem CID:	10339234
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	2
Others	9

Activity Type	# Activity
Individual Protein	1
Others	10

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[526606]
NPT2	Others	Unspecified		Inhibition	=	-1.6	%	PMID[526606]
NPT2	Others	Unspecified		Inhibition	=	2.2	%	PMID[526606]
NPT2	Others	Unspecified		Inhibition	=	7.6	%	PMID[526606]
NPT2	Others	Unspecified		Inhibition	=	50.6	%	PMID[526606]
NPT27	Others	Unspecified		Inhibition	=	0.3	%	PMID[526606]
NPT27	Others	Unspecified		Inhibition	=	1.3	%	PMID[526606]
NPT27	Others	Unspecified		Inhibition	=	10.9	%	PMID[526606]
NPT27	Others	Unspecified		Inhibition	=	23.8	%	PMID[526606]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[526606]
NPT2	Others	Unspecified		IC50	=	30000.0	nM	PMID[526606]

☑ 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 NPC26394 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	386
0.1-0.2	1354
0.2-0.3	3620
0.3-0.4	9743
0.4-0.5	9030
0.5-0.6	3835
0.6-0.7	8231
0.7-0.8	4954
0.8-0.85	947
0.85-0.9	502
0.9-0.95	78
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC230219
0.9767	High Similarity	NPC54743
0.9767	High Similarity	NPC10737
0.9767	High Similarity	NPC209985
0.9767	High Similarity	NPC263367
0.9767	High Similarity	NPC156502
0.9767	High Similarity	NPC477939
0.9767	High Similarity	NPC29799
0.9767	High Similarity	NPC177160
0.9692	High Similarity	NPC477938
0.9612	High Similarity	NPC193026
0.9612	High Similarity	NPC187616
0.9612	High Similarity	NPC49603
0.9609	High Similarity	NPC18842
0.9524	High Similarity	NPC98745
0.9474	High Similarity	NPC87725
0.9474	High Similarity	NPC263261
0.9474	High Similarity	NPC471414
0.9462	High Similarity	NPC16485
0.9449	High Similarity	NPC470084
0.9444	High Similarity	NPC206882
0.9403	High Similarity	NPC253878
0.9302	High Similarity	NPC153739
0.9302	High Similarity	NPC257582
0.9302	High Similarity	NPC42300
0.9302	High Similarity	NPC145305
0.9302	High Similarity	NPC187998
0.9302	High Similarity	NPC64201
0.9302	High Similarity	NPC241522
0.9302	High Similarity	NPC242807
0.9302	High Similarity	NPC92164
0.9302	High Similarity	NPC77040
0.9302	High Similarity	NPC174495
0.9265	High Similarity	NPC474444
0.9265	High Similarity	NPC264706
0.9265	High Similarity	NPC93433
0.9265	High Similarity	NPC284881
0.9259	High Similarity	NPC131971
0.9231	High Similarity	NPC277804
0.9225	High Similarity	NPC475875
0.9213	High Similarity	NPC81641
0.9197	High Similarity	NPC163898
0.9197	High Similarity	NPC181615
0.9197	High Similarity	NPC43508
0.9197	High Similarity	NPC476301
0.9167	High Similarity	NPC478085
0.9154	High Similarity	NPC143483
0.9147	High Similarity	NPC21867
0.9147	High Similarity	NPC45774
0.9147	High Similarity	NPC11258
0.9147	High Similarity	NPC184733
0.9147	High Similarity	NPC128208
0.9147	High Similarity	NPC129570
0.9147	High Similarity	NPC282703
0.9134	High Similarity	NPC109822
0.9134	High Similarity	NPC94276
0.913	High Similarity	NPC260397
0.9124	High Similarity	NPC79429
0.9124	High Similarity	NPC12641
0.9124	High Similarity	NPC217635
0.9124	High Similarity	NPC45257
0.9124	High Similarity	NPC280092
0.9124	High Similarity	NPC471667
0.9124	High Similarity	NPC93323
0.9111	High Similarity	NPC184797
0.9111	High Similarity	NPC27495
0.9111	High Similarity	NPC309124
0.9111	High Similarity	NPC254759
0.9111	High Similarity	NPC160283
0.9098	High Similarity	NPC93783
0.9084	High Similarity	NPC40432
0.9084	High Similarity	NPC158079
0.9084	High Similarity	NPC161557
0.9084	High Similarity	NPC115207
0.9084	High Similarity	NPC228346
0.9084	High Similarity	NPC7171
0.9084	High Similarity	NPC27843
0.907	High Similarity	NPC118787
0.907	High Similarity	NPC118533
0.907	High Similarity	NPC41706
0.907	High Similarity	NPC183181
0.907	High Similarity	NPC111247
0.907	High Similarity	NPC163332
0.907	High Similarity	NPC147821
0.907	High Similarity	NPC165045
0.907	High Similarity	NPC292056
0.907	High Similarity	NPC319625
0.9065	High Similarity	NPC114505
0.9065	High Similarity	NPC193473
0.9065	High Similarity	NPC15956
0.9065	High Similarity	NPC224674
0.9065	High Similarity	NPC31325
0.9065	High Similarity	NPC275284
0.9065	High Similarity	NPC213074
0.9058	High Similarity	NPC180953
0.9058	High Similarity	NPC469557
0.9051	High Similarity	NPC47633
0.9051	High Similarity	NPC477616
0.9051	High Similarity	NPC85264
0.9051	High Similarity	NPC102044
0.9048	High Similarity	NPC312713
0.9048	High Similarity	NPC57268
0.9048	High Similarity	NPC172676
0.9048	High Similarity	NPC65933
0.9048	High Similarity	NPC216929
0.9048	High Similarity	NPC126935
0.9044	High Similarity	NPC311530
0.9037	High Similarity	NPC260741
0.9037	High Similarity	NPC292882
0.9037	High Similarity	NPC236306
0.9037	High Similarity	NPC473739
0.9037	High Similarity	NPC471388
0.9037	High Similarity	NPC70682
0.9037	High Similarity	NPC232164
0.903	High Similarity	NPC77861
0.903	High Similarity	NPC78047
0.9023	High Similarity	NPC90083
0.9023	High Similarity	NPC287745
0.9023	High Similarity	NPC170779
0.9015	High Similarity	NPC181049
0.9015	High Similarity	NPC207400
0.9	High Similarity	NPC472968
0.9	High Similarity	NPC473408
0.8992	High Similarity	NPC191037
0.8992	High Similarity	NPC58607
0.8992	High Similarity	NPC178284
0.8986	High Similarity	NPC63879
0.8984	High Similarity	NPC18449
0.8984	High Similarity	NPC114901
0.8984	High Similarity	NPC293701
0.8984	High Similarity	NPC34902
0.8984	High Similarity	NPC121783
0.8984	High Similarity	NPC48990
0.8978	High Similarity	NPC107161
0.8976	High Similarity	NPC150026
0.8976	High Similarity	NPC71090
0.8955	High Similarity	NPC61946
0.8955	High Similarity	NPC256262
0.8947	High Similarity	NPC158331
0.8947	High Similarity	NPC263064
0.8947	High Similarity	NPC475840
0.8931	High Similarity	NPC210623
0.8931	High Similarity	NPC273295
0.8931	High Similarity	NPC86030
0.8931	High Similarity	NPC3439
0.8931	High Similarity	NPC226788
0.8931	High Similarity	NPC190629
0.8931	High Similarity	NPC218856
0.8931	High Similarity	NPC5851
0.8931	High Similarity	NPC202582
0.8931	High Similarity	NPC470258
0.8931	High Similarity	NPC285339
0.8931	High Similarity	NPC222004
0.8929	High Similarity	NPC16269
0.8929	High Similarity	NPC21776
0.8929	High Similarity	NPC101376
0.8923	High Similarity	NPC242032
0.8923	High Similarity	NPC5428
0.8923	High Similarity	NPC21563
0.8921	High Similarity	NPC221318
0.8915	High Similarity	NPC194519
0.8915	High Similarity	NPC148627
0.8905	High Similarity	NPC35216
0.8905	High Similarity	NPC471389
0.8905	High Similarity	NPC247291
0.8897	High Similarity	NPC260842
0.8889	High Similarity	NPC306441
0.8889	High Similarity	NPC472336
0.8889	High Similarity	NPC248727
0.8889	High Similarity	NPC270456
0.8889	High Similarity	NPC173660
0.8889	High Similarity	NPC16435
0.8889	High Similarity	NPC162659
0.8889	High Similarity	NPC265433
0.8889	High Similarity	NPC470802
0.8889	High Similarity	NPC472334
0.8881	High Similarity	NPC326095
0.8881	High Similarity	NPC471942
0.8881	High Similarity	NPC474478
0.8881	High Similarity	NPC67247
0.8881	High Similarity	NPC244983
0.8873	High Similarity	NPC98624
0.8872	High Similarity	NPC204215
0.8872	High Similarity	NPC259742
0.8872	High Similarity	NPC104077
0.8872	High Similarity	NPC175067
0.8872	High Similarity	NPC219671
0.8872	High Similarity	NPC4940
0.8872	High Similarity	NPC147616
0.8865	High Similarity	NPC270751
0.8865	High Similarity	NPC236166
0.8857	High Similarity	NPC324492
0.8857	High Similarity	NPC317053
0.8855	High Similarity	NPC474178
0.8855	High Similarity	NPC72529
0.8855	High Similarity	NPC252307
0.8855	High Similarity	NPC245826
0.8849	High Similarity	NPC473108
0.8846	High Similarity	NPC112571
0.8846	High Similarity	NPC285725

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 NPC26394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	842
0.2-0.3	1713
0.3-0.4	2632
0.4-0.5	1720
0.5-0.6	988
0.6-0.7	694
0.7-0.8	236
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8647	High Similarity	NPD3027	Phase 3
0.8593	High Similarity	NPD1613	Approved
0.8593	High Similarity	NPD1612	Clinical (unspecified phase)
0.8496	Intermediate Similarity	NPD2861	Phase 2
0.8333	Intermediate Similarity	NPD5283	Phase 1
0.8309	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6674	Discontinued
0.8222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD4060	Phase 1
0.8162	Intermediate Similarity	NPD4908	Phase 1
0.8045	Intermediate Similarity	NPD3705	Approved
0.8045	Intermediate Similarity	NPD1610	Phase 2
0.8	Intermediate Similarity	NPD8651	Approved
0.7958	Intermediate Similarity	NPD5588	Approved
0.7947	Intermediate Similarity	NPD37	Approved
0.7931	Intermediate Similarity	NPD6331	Phase 2
0.7929	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3620	Phase 2
0.7926	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD4967	Phase 2
0.7908	Intermediate Similarity	NPD4965	Approved
0.7908	Intermediate Similarity	NPD4966	Approved
0.7887	Intermediate Similarity	NPD4538	Approved
0.7887	Intermediate Similarity	NPD4536	Approved
0.7887	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD5763	Approved
0.7847	Intermediate Similarity	NPD5762	Approved
0.7842	Intermediate Similarity	NPD4625	Phase 3
0.7826	Intermediate Similarity	NPD3018	Phase 2
0.7823	Intermediate Similarity	NPD5058	Phase 3
0.782	Intermediate Similarity	NPD1357	Approved
0.7795	Intermediate Similarity	NPD2684	Approved
0.7786	Intermediate Similarity	NPD7157	Approved
0.7786	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1091	Approved
0.7778	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5494	Approved
0.7752	Intermediate Similarity	NPD228	Approved
0.7746	Intermediate Similarity	NPD6355	Discontinued
0.7746	Intermediate Similarity	NPD5735	Approved
0.7744	Intermediate Similarity	NPD1548	Phase 1
0.774	Intermediate Similarity	NPD4236	Phase 3
0.774	Intermediate Similarity	NPD4237	Approved
0.7737	Intermediate Similarity	NPD6696	Suspended
0.7727	Intermediate Similarity	NPD2563	Approved
0.7727	Intermediate Similarity	NPD2560	Approved
0.7724	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6004	Phase 3
0.7724	Intermediate Similarity	NPD6005	Phase 3
0.7724	Intermediate Similarity	NPD6002	Phase 3
0.7724	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD290	Approved
0.7712	Intermediate Similarity	NPD1934	Approved
0.7708	Intermediate Similarity	NPD5960	Phase 3
0.7707	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD7843	Approved
0.7692	Intermediate Similarity	NPD6234	Discontinued
0.7687	Intermediate Similarity	NPD4110	Phase 3
0.7687	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD4749	Approved
0.7664	Intermediate Similarity	NPD2983	Phase 2
0.7664	Intermediate Similarity	NPD2982	Phase 2
0.7652	Intermediate Similarity	NPD6671	Approved
0.764	Intermediate Similarity	NPD5844	Phase 1
0.7635	Intermediate Similarity	NPD2677	Approved
0.7626	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5177	Phase 3
0.761	Intermediate Similarity	NPD2969	Approved
0.761	Intermediate Similarity	NPD2970	Approved
0.7603	Intermediate Similarity	NPD1375	Discontinued
0.7597	Intermediate Similarity	NPD3022	Approved
0.7597	Intermediate Similarity	NPD3021	Approved
0.7591	Intermediate Similarity	NPD2981	Phase 2
0.7586	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3882	Suspended
0.7552	Intermediate Similarity	NPD1558	Phase 1
0.7552	Intermediate Similarity	NPD4140	Approved
0.7552	Intermediate Similarity	NPD2238	Phase 2
0.7551	Intermediate Similarity	NPD2424	Discontinued
0.7547	Intermediate Similarity	NPD3051	Approved
0.7536	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD5327	Phase 3
0.7534	Intermediate Similarity	NPD2161	Phase 2
0.7533	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3060	Approved
0.75	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5124	Phase 1
0.7484	Intermediate Similarity	NPD8127	Discontinued
0.7483	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4123	Phase 3
0.7469	Intermediate Similarity	NPD7228	Approved
0.7469	Intermediate Similarity	NPD3818	Discontinued
0.7467	Intermediate Similarity	NPD6666	Approved
0.7467	Intermediate Similarity	NPD6667	Approved
0.7466	Intermediate Similarity	NPD7033	Discontinued
0.7464	Intermediate Similarity	NPD2235	Phase 2
0.7464	Intermediate Similarity	NPD2231	Phase 2
0.7453	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6166	Phase 2
0.7453	Intermediate Similarity	NPD27	Approved
0.7453	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2489	Approved
0.7451	Intermediate Similarity	NPD1653	Approved
0.745	Intermediate Similarity	NPD4628	Phase 3
0.745	Intermediate Similarity	NPD3892	Phase 2
0.7448	Intermediate Similarity	NPD6653	Approved
0.7448	Intermediate Similarity	NPD2157	Approved
0.7438	Intermediate Similarity	NPD6071	Discontinued
0.7436	Intermediate Similarity	NPD5773	Approved
0.7436	Intermediate Similarity	NPD5772	Approved
0.7436	Intermediate Similarity	NPD2801	Approved
0.7434	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7526	Approved
0.7434	Intermediate Similarity	NPD52	Approved
0.7413	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6798	Discontinued
0.7407	Intermediate Similarity	NPD5536	Phase 2
0.7405	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5976	Discontinued
0.7383	Intermediate Similarity	NPD4162	Approved
0.7379	Intermediate Similarity	NPD3657	Discovery
0.7376	Intermediate Similarity	NPD3690	Phase 2
0.7376	Intermediate Similarity	NPD3691	Phase 2
0.7376	Intermediate Similarity	NPD6584	Phase 3
0.7372	Intermediate Similarity	NPD6516	Phase 2
0.7372	Intermediate Similarity	NPD5846	Approved
0.7372	Intermediate Similarity	NPD5125	Phase 3
0.7372	Intermediate Similarity	NPD4626	Approved
0.7372	Intermediate Similarity	NPD5126	Approved
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.7365	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD968	Approved
0.7361	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4678	Approved
0.7355	Intermediate Similarity	NPD4675	Approved
0.7343	Intermediate Similarity	NPD7095	Approved
0.7342	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3687	Approved
0.7338	Intermediate Similarity	NPD1608	Approved
0.7338	Intermediate Similarity	NPD3686	Approved
0.7333	Intermediate Similarity	NPD4535	Phase 3
0.7329	Intermediate Similarity	NPD6353	Approved
0.7329	Intermediate Similarity	NPD4097	Suspended
0.7325	Intermediate Similarity	NPD8455	Phase 2
0.7323	Intermediate Similarity	NPD291	Approved
0.7319	Intermediate Similarity	NPD3496	Discontinued
0.7308	Intermediate Similarity	NPD6072	Discontinued
0.7305	Intermediate Similarity	NPD7310	Approved
0.7305	Intermediate Similarity	NPD7312	Approved
0.7305	Intermediate Similarity	NPD7311	Approved
0.7305	Intermediate Similarity	NPD7313	Approved
0.7305	Intermediate Similarity	NPD3094	Phase 2
0.7303	Intermediate Similarity	NPD1774	Approved
0.7299	Intermediate Similarity	NPD5691	Approved
0.7297	Intermediate Similarity	NPD6032	Approved
0.7292	Intermediate Similarity	NPD5111	Phase 2
0.7292	Intermediate Similarity	NPD5110	Phase 2
0.7292	Intermediate Similarity	NPD5109	Approved
0.7279	Intermediate Similarity	NPD7097	Phase 1
0.7278	Intermediate Similarity	NPD3817	Phase 2
0.7278	Intermediate Similarity	NPD4663	Approved
0.7273	Intermediate Similarity	NPD7074	Phase 3
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1611	Approved
0.7262	Intermediate Similarity	NPD7309	Approved
0.7255	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5709	Phase 3
0.7248	Intermediate Similarity	NPD3540	Phase 1
0.7244	Intermediate Similarity	NPD4380	Phase 2
0.7241	Intermediate Similarity	NPD6233	Phase 2
0.7226	Intermediate Similarity	NPD4210	Discontinued
0.7226	Intermediate Similarity	NPD1182	Approved
0.7222	Intermediate Similarity	NPD6232	Discontinued
0.7222	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2977	Approved
0.7215	Intermediate Similarity	NPD5929	Approved
0.7215	Intermediate Similarity	NPD2978	Approved
0.7214	Intermediate Similarity	NPD1840	Phase 2
0.7214	Intermediate Similarity	NPD2230	Approved
0.7214	Intermediate Similarity	NPD2232	Approved
0.7214	Intermediate Similarity	NPD2233	Approved
0.7212	Intermediate Similarity	NPD7054	Approved
0.7208	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7340	Approved
0.7205	Intermediate Similarity	NPD4666	Phase 3
0.7203	Intermediate Similarity	NPD1712	Approved
0.7202	Intermediate Similarity	NPD4577	Approved
0.7202	Intermediate Similarity	NPD4578	Approved
0.72	Intermediate Similarity	NPD7037	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