NPASS Compound

Structure

CID137100 OpenBabel06191715492D 34 38 0 0 0 0 0 0 0 0999 V2000 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 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 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.6910 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 -3.0878 -0.0570 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 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 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 -1.5878 0.8090 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 7.0132 -1.1910 0.0000 C 0 0 0 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 -1.5962 3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 4.2633 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 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 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 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.6910 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 -2.5743 3.9360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 5.0064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 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 16 1 0 0 0 0 2 17 1 0 0 0 0 3 7 1 0 0 0 0 3 16 2 0 0 0 0 4 8 2 0 0 0 0 4 16 1 0 0 0 0 5 9 1 0 0 0 0 5 18 2 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 20 2 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 17 2 0 0 0 0 11 24 1 0 0 0 0 12 17 1 0 0 0 0 12 25 2 0 0 0 0 13 19 2 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 14 23 2 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 18 28 1 0 0 0 0 19 26 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 27 2 0 0 0 0 24 33 1 0 0 0 0 25 27 1 0 0 0 0 25 34 1 0 0 0 0 26 27 1 0 0 0 0 26 28 2 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.13
Volume:	465.893
LogP:	5.792
LogD:	3.86
LogS:	-3.707
# Rotatable Bonds:	4
TPSA:	114.29
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.2
Synthetic Accessibility Score:	2.749
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.364
MDCK Permeability:	1.1509504474815913e-05
Pgp-inhibitor:	0.67
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.901
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	100.26396942138672%
Volume Distribution (VD):	0.529
Pgp-substrate:	0.706976592540741%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.871
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.531
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.356
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.683
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	11.249
Half-life (T1/2):	0.838

ADMET: Toxicity

hERG Blockers:	0.269
Human Hepatotoxicity (H-HT):	0.297
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.555
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.842
Skin Sensitization:	0.936
Carcinogencity:	0.083
Eye Corrosion:	0.003
Eye Irritation:	0.86
Respiratory Toxicity:	0.17

Download Data

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

Natural Product: NPC137100

Natural Product ID:	NPC137100
*Common Name:**	5-[4-Hydroxy-2-(4-Hydroxyphenyl)-6-[(E)-2-(4-Hydroxyphenyl)Ethenyl]-1-Benzofuran-3-Yl]Benzene-1,3-Diol
IUPAC Name:	5-[4-hydroxy-2-(4-hydroxyphenyl)-6-[(E)-2-(4-hydroxyphenyl)ethenyl]-1-benzofuran-3-yl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	PKURHFYJMWBEEX-OWOJBTEDSA-N
Standard InCHI:	InChI=1S/C28H20O6/c29-20-7-3-16(4-8-20)1-2-17-11-24(33)27-25(12-17)34-28(18-5-9-21(30)10-6-18)26(27)19-13-22(31)15-23(32)14-19/h1-15,29-33H/b2-1+
SMILES:	Oc1ccc(cc1)/C=C/c1cc(O)c2c(c1)oc(c2c1cc(O)cc(c1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593481
PubChem CID:	636473
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
NPO15254	Macropidia fuliginosa	Species	Haemodoraceae	Eukaryota	n.a.	Australian	n.a.	PMID[26151487]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[30413343]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3783160]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16782	Andrographis viscosula	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10984	Euclea crispa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11360	Tiliacora racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18427	Axinella agnata	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17900	Iotrochota birotulata	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3096	Verbascum laxum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10064	Diospyros canaliculata	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19091	Bacterium from	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16782	Andrographis viscosula	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15254	Macropidia fuliginosa	Species	Haemodoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16548	Chenopodium formosanum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5869	Anthocercis albicans	Species	Solanaceae	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	2

Activity Type	# Activity
Individual Protein	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	8000.0	nM	PMID[485977]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	IZ	=	1.0	mm	PMID[485976]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	2.0	mm	PMID[485976]

☑ 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 NPC137100 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	503
0.1-0.2	2055
0.2-0.3	4474
0.3-0.4	11589
0.4-0.5	6250
0.5-0.6	4007
0.6-0.7	5706
0.7-0.8	5048
0.8-0.85	2358
0.85-0.9	644
0.9-0.95	59
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9548	High Similarity	NPC169471
0.953	High Similarity	NPC167576
0.9484	High Similarity	NPC159508
0.9477	High Similarity	NPC472877
0.947	High Similarity	NPC72370
0.9427	High Similarity	NPC286230
0.9427	High Similarity	NPC253730
0.9338	High Similarity	NPC193976
0.9338	High Similarity	NPC23668
0.9324	High Similarity	NPC155144
0.9299	High Similarity	NPC474591
0.9295	High Similarity	NPC477239
0.9295	High Similarity	NPC3448
0.9286	High Similarity	NPC212967
0.9286	High Similarity	NPC96342
0.9286	High Similarity	NPC246647
0.9286	High Similarity	NPC164110
0.9281	High Similarity	NPC99199
0.9276	High Similarity	NPC207624
0.9276	High Similarity	NPC142308
0.9272	High Similarity	NPC230713
0.9272	High Similarity	NPC78335
0.9221	High Similarity	NPC180924
0.9216	High Similarity	NPC235333
0.9216	High Similarity	NPC472462
0.9211	High Similarity	NPC170169
0.9211	High Similarity	NPC115324
0.9211	High Similarity	NPC58668
0.9211	High Similarity	NPC106372
0.9205	High Similarity	NPC178202
0.92	High Similarity	NPC17816
0.9193	High Similarity	NPC59491
0.9193	High Similarity	NPC24748
0.9161	High Similarity	NPC268360
0.9156	High Similarity	NPC213936
0.9156	High Similarity	NPC297531
0.9156	High Similarity	NPC148938
0.9136	High Similarity	NPC300657
0.9114	High Similarity	NPC38591
0.9091	High Similarity	NPC213608
0.9091	High Similarity	NPC1477
0.908	High Similarity	NPC101991
0.9079	High Similarity	NPC226644
0.9079	High Similarity	NPC37226
0.9068	High Similarity	NPC476641
0.9067	High Similarity	NPC98926
0.9067	High Similarity	NPC230943
0.9062	High Similarity	NPC470704
0.9038	High Similarity	NPC65504
0.9032	High Similarity	NPC198490
0.9026	High Similarity	NPC5871
0.9013	High Similarity	NPC135325
0.9012	High Similarity	NPC174700
0.9007	High Similarity	NPC210826
0.9	High Similarity	NPC302181
0.8981	High Similarity	NPC177650
0.897	High Similarity	NPC121888
0.8968	High Similarity	NPC183874
0.8961	High Similarity	NPC149085
0.8961	High Similarity	NPC222713
0.8961	High Similarity	NPC138299
0.8961	High Similarity	NPC67322
0.8961	High Similarity	NPC111112
0.8957	High Similarity	NPC65885
0.8957	High Similarity	NPC82217
0.8957	High Similarity	NPC216842
0.8957	High Similarity	NPC476640
0.8954	High Similarity	NPC221868
0.8954	High Similarity	NPC37208
0.8947	High Similarity	NPC130581
0.8947	High Similarity	NPC12148
0.8947	High Similarity	NPC150215
0.8944	High Similarity	NPC50394
0.8933	High Similarity	NPC53192
0.8924	High Similarity	NPC312993
0.8924	High Similarity	NPC186325
0.8916	High Similarity	NPC47883
0.891	High Similarity	NPC226656
0.891	High Similarity	NPC254351
0.891	High Similarity	NPC66508
0.8903	High Similarity	NPC41326
0.8903	High Similarity	NPC67654
0.8902	High Similarity	NPC287243
0.8896	High Similarity	NPC54098
0.8896	High Similarity	NPC13282
0.8896	High Similarity	NPC230619
0.8889	High Similarity	NPC272194
0.8889	High Similarity	NPC53252
0.8882	High Similarity	NPC196114
0.8882	High Similarity	NPC300267
0.8882	High Similarity	NPC51641
0.8874	High Similarity	NPC225884
0.8868	High Similarity	NPC312273
0.8868	High Similarity	NPC301256
0.8868	High Similarity	NPC189552
0.8868	High Similarity	NPC273467
0.8861	High Similarity	NPC226287
0.8861	High Similarity	NPC244750
0.8861	High Similarity	NPC40583
0.8861	High Similarity	NPC51760
0.8861	High Similarity	NPC324736
0.8854	High Similarity	NPC247677
0.8854	High Similarity	NPC309648
0.8854	High Similarity	NPC160015
0.8848	High Similarity	NPC49667
0.8848	High Similarity	NPC8127
0.8846	High Similarity	NPC290830
0.8846	High Similarity	NPC329844
0.8846	High Similarity	NPC71061
0.8846	High Similarity	NPC303485
0.8846	High Similarity	NPC72425
0.8846	High Similarity	NPC194593
0.8841	High Similarity	NPC473834
0.8839	High Similarity	NPC258249
0.8839	High Similarity	NPC156244
0.8831	High Similarity	NPC474052
0.8831	High Similarity	NPC288840
0.8831	High Similarity	NPC291746
0.8831	High Similarity	NPC39929
0.8831	High Similarity	NPC296030
0.8824	High Similarity	NPC77903
0.8824	High Similarity	NPC17101
0.8812	High Similarity	NPC84515
0.8812	High Similarity	NPC473012
0.8812	High Similarity	NPC312056
0.8812	High Similarity	NPC473011
0.881	High Similarity	NPC154527
0.8808	High Similarity	NPC159855
0.8808	High Similarity	NPC169479
0.8808	High Similarity	NPC1534
0.8805	High Similarity	NPC472060
0.8805	High Similarity	NPC115432
0.8805	High Similarity	NPC260296
0.8805	High Similarity	NPC184326
0.8805	High Similarity	NPC470342
0.8805	High Similarity	NPC292863
0.8805	High Similarity	NPC472052
0.8797	High Similarity	NPC296957
0.8797	High Similarity	NPC260902
0.8795	High Similarity	NPC297807
0.8795	High Similarity	NPC475783
0.8792	High Similarity	NPC112757
0.879	High Similarity	NPC215203
0.879	High Similarity	NPC265624
0.879	High Similarity	NPC300668
0.879	High Similarity	NPC150908
0.879	High Similarity	NPC182555
0.879	High Similarity	NPC205026
0.879	High Similarity	NPC159707
0.879	High Similarity	NPC158027
0.879	High Similarity	NPC258474
0.879	High Similarity	NPC134171
0.879	High Similarity	NPC52611
0.879	High Similarity	NPC201227
0.879	High Similarity	NPC248739
0.879	High Similarity	NPC66441
0.879	High Similarity	NPC100049
0.879	High Similarity	NPC14606
0.879	High Similarity	NPC186227
0.879	High Similarity	NPC121649
0.8782	High Similarity	NPC40356
0.8782	High Similarity	NPC154683
0.8782	High Similarity	NPC125300
0.8782	High Similarity	NPC253872
0.878	High Similarity	NPC248593
0.878	High Similarity	NPC28589
0.8766	High Similarity	NPC106328
0.8766	High Similarity	NPC37135
0.8766	High Similarity	NPC35150
0.8766	High Similarity	NPC186397
0.8765	High Similarity	NPC277480
0.8758	High Similarity	NPC299011
0.8758	High Similarity	NPC473009
0.8758	High Similarity	NPC130176
0.8758	High Similarity	NPC99454
0.8758	High Similarity	NPC469758
0.8758	High Similarity	NPC155640
0.8757	High Similarity	NPC226725
0.875	High Similarity	NPC231758
0.875	High Similarity	NPC18380
0.875	High Similarity	NPC45124
0.875	High Similarity	NPC30655
0.875	High Similarity	NPC74854
0.875	High Similarity	NPC304387
0.875	High Similarity	NPC137232
0.875	High Similarity	NPC188486
0.8742	High Similarity	NPC476349
0.8742	High Similarity	NPC190487
0.8742	High Similarity	NPC18699
0.8742	High Similarity	NPC154304
0.8742	High Similarity	NPC55443
0.8742	High Similarity	NPC14871
0.8742	High Similarity	NPC195167
0.8742	High Similarity	NPC476350
0.8734	High Similarity	NPC45131
0.8734	High Similarity	NPC13879
0.8734	High Similarity	NPC56049
0.8734	High Similarity	NPC472461
0.8734	High Similarity	NPC69531
0.8734	High Similarity	NPC61112

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 NPC137100 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	456
0.1-0.2	993
0.2-0.3	1596
0.3-0.4	2729
0.4-0.5	1860
0.5-0.6	1027
0.6-0.7	320
0.7-0.8	118
0.8-0.85	38
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9038	High Similarity	NPD3749	Approved
0.875	High Similarity	NPD6959	Discontinued
0.8571	High Similarity	NPD7410	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD2344	Approved
0.8452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1549	Phase 2
0.8387	Intermediate Similarity	NPD1511	Approved
0.8385	Intermediate Similarity	NPD7768	Phase 2
0.8364	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8333	Intermediate Similarity	NPD1607	Approved
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD6559	Discontinued
0.828	Intermediate Similarity	NPD1512	Approved
0.8272	Intermediate Similarity	NPD3882	Suspended
0.8269	Intermediate Similarity	NPD7390	Discontinued
0.8261	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD2801	Approved
0.8258	Intermediate Similarity	NPD2309	Approved
0.825	Intermediate Similarity	NPD7411	Suspended
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.82	Intermediate Similarity	NPD1240	Approved
0.8199	Intermediate Similarity	NPD1934	Approved
0.8194	Intermediate Similarity	NPD3750	Approved
0.8187	Intermediate Similarity	NPD4380	Phase 2
0.817	Intermediate Similarity	NPD2796	Approved
0.816	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD3818	Discontinued
0.8148	Intermediate Similarity	NPD7819	Suspended
0.8144	Intermediate Similarity	NPD6166	Phase 2
0.8144	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2800	Approved
0.8121	Intermediate Similarity	NPD5494	Approved
0.811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD2533	Approved
0.8101	Intermediate Similarity	NPD2532	Approved
0.8101	Intermediate Similarity	NPD2534	Approved
0.8084	Intermediate Similarity	NPD3926	Phase 2
0.8013	Intermediate Similarity	NPD1243	Approved
0.8012	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7955	Intermediate Similarity	NPD4287	Approved
0.7935	Intermediate Similarity	NPD5404	Approved
0.7935	Intermediate Similarity	NPD5406	Approved
0.7935	Intermediate Similarity	NPD5405	Approved
0.7935	Intermediate Similarity	NPD1551	Phase 2
0.7935	Intermediate Similarity	NPD5408	Approved
0.7907	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7075	Discontinued
0.7875	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD3748	Approved
0.7862	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6099	Approved
0.7821	Intermediate Similarity	NPD6100	Approved
0.7818	Intermediate Similarity	NPD1465	Phase 2
0.7818	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6799	Approved
0.7785	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.7771	Intermediate Similarity	NPD5402	Approved
0.7771	Intermediate Similarity	NPD3817	Phase 2
0.7751	Intermediate Similarity	NPD1247	Approved
0.7746	Intermediate Similarity	NPD7074	Phase 3
0.7727	Intermediate Similarity	NPD943	Approved
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7688	Intermediate Similarity	NPD7054	Approved
0.767	Intermediate Similarity	NPD8313	Approved
0.767	Intermediate Similarity	NPD8312	Approved
0.7665	Intermediate Similarity	NPD2296	Approved
0.7651	Intermediate Similarity	NPD6801	Discontinued
0.7644	Intermediate Similarity	NPD7472	Approved
0.7643	Intermediate Similarity	NPD2799	Discontinued
0.7633	Intermediate Similarity	NPD919	Approved
0.7625	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6797	Phase 2
0.7597	Intermediate Similarity	NPD3764	Approved
0.7597	Intermediate Similarity	NPD2313	Discontinued
0.7586	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4908	Phase 1
0.7576	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5403	Approved
0.7557	Intermediate Similarity	NPD7251	Discontinued
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1471	Phase 3
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD7808	Phase 3
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD7229	Phase 3
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5401	Approved
0.7438	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3751	Discontinued
0.7429	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7177	Discontinued
0.7419	Intermediate Similarity	NPD4625	Phase 3
0.7407	Intermediate Similarity	NPD7003	Approved
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7399	Intermediate Similarity	NPD3787	Discontinued
0.7396	Intermediate Similarity	NPD5760	Phase 2
0.7396	Intermediate Similarity	NPD5761	Phase 2
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7351	Intermediate Similarity	NPD1201	Approved
0.7338	Intermediate Similarity	NPD2798	Approved
0.7337	Intermediate Similarity	NPD6280	Approved
0.7337	Intermediate Similarity	NPD6279	Approved
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4308	Phase 3
0.7296	Intermediate Similarity	NPD6651	Approved
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7458	Discontinued
0.7261	Intermediate Similarity	NPD3268	Approved
0.7261	Intermediate Similarity	NPD411	Approved
0.7255	Intermediate Similarity	NPD4749	Approved
0.7254	Intermediate Similarity	NPD8151	Discontinued
0.7253	Intermediate Similarity	NPD8434	Phase 2
0.7251	Intermediate Similarity	NPD4288	Approved
0.7244	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7199	Phase 2
0.7237	Intermediate Similarity	NPD1610	Phase 2
0.7237	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD447	Suspended
0.72	Intermediate Similarity	NPD6808	Phase 2
0.7196	Intermediate Similarity	NPD6778	Approved
0.7196	Intermediate Similarity	NPD6779	Approved
0.7196	Intermediate Similarity	NPD6776	Approved
0.7196	Intermediate Similarity	NPD6777	Approved
0.7196	Intermediate Similarity	NPD6782	Approved
0.7196	Intermediate Similarity	NPD6780	Approved
0.7196	Intermediate Similarity	NPD6781	Approved
0.719	Intermediate Similarity	NPD3972	Approved
0.719	Intermediate Similarity	NPD9717	Approved
0.719	Intermediate Similarity	NPD1608	Approved
0.7186	Intermediate Similarity	NPD6273	Approved
0.7179	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2797	Approved
0.7159	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD37	Approved
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7134	Intermediate Similarity	NPD2654	Approved
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7126	Intermediate Similarity	NPD6234	Discontinued
0.7125	Intermediate Similarity	NPD230	Phase 1
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4360	Phase 2
0.7112	Intermediate Similarity	NPD4363	Phase 3
0.711	Intermediate Similarity	NPD4966	Approved
0.711	Intermediate Similarity	NPD4967	Phase 2
0.711	Intermediate Similarity	NPD4965	Approved
0.7104	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7033	Discontinued
0.7097	Intermediate Similarity	NPD3225	Approved
0.7093	Intermediate Similarity	NPD8455	Phase 2
0.7086	Intermediate Similarity	NPD1548	Phase 1
0.7083	Intermediate Similarity	NPD7697	Approved
0.7083	Intermediate Similarity	NPD7435	Discontinued
0.7083	Intermediate Similarity	NPD7696	Phase 3
0.7083	Intermediate Similarity	NPD7698	Approved
0.7074	Intermediate Similarity	NPD4361	Phase 2
0.7074	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2861	Phase 2
0.7069	Intermediate Similarity	NPD6971	Discontinued
0.7063	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4307	Phase 2
0.7063	Intermediate Similarity	NPD1613	Approved
0.7056	Intermediate Similarity	NPD1729	Discontinued
0.7052	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6844	Discontinued
0.7022	Intermediate Similarity	NPD2403	Approved
0.7016	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD422	Phase 1
0.7005	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7783	Phase 2
0.6993	Remote Similarity	NPD17	Approved
0.6989	Remote Similarity	NPD6746	Phase 2
0.6973	Remote Similarity	NPD8150	Discontinued
0.6944	Remote Similarity	NPD7228	Approved
0.6943	Remote Similarity	NPD3267	Approved
0.6943	Remote Similarity	NPD3266	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