NPASS Compound

Structure

CID45131 OpenBabel06191715382D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.7321 -1.0000 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 4.7709 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7709 0.3660 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2709 -0.5000 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 4.2709 -0.5000 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 5.7709 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7709 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2709 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2709 1.2321 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 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 9 2 0 0 0 0 3 11 1 0 0 0 0 4 9 1 0 0 0 0 4 12 2 0 0 0 0 5 10 1 0 0 0 0 5 13 2 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 21 1 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	3.393
LogD:	3.006
LogS:	-3.731
# Rotatable Bonds:	3
TPSA:	72.06
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.77
Synthetic Accessibility Score:	2.255
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.869
MDCK Permeability:	1.5623763829353265e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.674
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	95.8896484375%
Volume Distribution (VD):	0.89
Pgp-substrate:	5.483146667480469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.617
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.77
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	10.45
Half-life (T1/2):	0.85

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.67
AMES Toxicity:	0.121
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.918
Carcinogencity:	0.033
Eye Corrosion:	0.008
Eye Irritation:	0.734
Respiratory Toxicity:	0.589

Download Data

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

Natural Product: NPC45131

Natural Product ID:	NPC45131
*Common Name:**	5-(5,6-Dimethoxybenzofuran-2-Yl)Benzene-1,3-Diol
IUPAC Name:	5-(5,6-dimethoxy-1-benzofuran-2-yl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	MQRQKQBOYQLFAI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-19-15-6-10-5-13(21-14(10)8-16(15)20-2)9-3-11(17)7-12(18)4-9/h3-8,17-18H,1-2H3
SMILES:	COc1cc2cc(c3cc(cc(c3)O)O)oc2cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397393
PubChem CID:	5319889
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
NPO28803	Artocarpus chama	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15165133]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO27320	Morus notabilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21737271]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27089	Nectandra glabrescens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28584	Euphorbia indica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28803	Artocarpus chama	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27368	Sinularia mayi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27589	Artemisia lehmanniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27280	Stachys spectabilis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27147	Habenaria repens	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27320	Morus notabilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27071	Spirastrella coccinea	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29149	Zexmenia phyllocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27478	Geodia japonica	Species	Geodiidae	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
MIC	10

Activity Type	# Activity
Organism	4
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[468680]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	100.0	ug.mL-1	PMID[468680]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[468680]
NPT610	Others	Molecular identity unknown		MIC	=	50.0	ug.mL-1	PMID[468680]
NPT610	Others	Molecular identity unknown		MIC	=	200.0	ug.mL-1	PMID[468680]
NPT610	Others	Molecular identity unknown		MIC	=	1000.0	ug.mL-1	PMID[468680]
NPT2955	Organism	Rosellinia necatrix	Rosellinia necatrix	MIC	=	50.0	ug.mL-1	PMID[468680]
NPT610	Others	Molecular identity unknown		MIC	=	100.0	ug.mL-1	PMID[468680]

☑ 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 NPC45131 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	448
0.1-0.2	1976
0.2-0.3	4891
0.3-0.4	11382
0.4-0.5	6101
0.5-0.6	3794
0.6-0.7	5107
0.7-0.8	5270
0.8-0.85	2151
0.85-0.9	1068
0.9-0.95	491
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC196879
0.9737	High Similarity	NPC188486
0.9735	High Similarity	NPC16935
0.9673	High Similarity	NPC312056
0.9673	High Similarity	NPC84515
0.961	High Similarity	NPC133065
0.9548	High Similarity	NPC36320
0.9548	High Similarity	NPC39306
0.9533	High Similarity	NPC125300
0.9484	High Similarity	NPC1755
0.9484	High Similarity	NPC1706
0.9484	High Similarity	NPC39305
0.9484	High Similarity	NPC263092
0.9484	High Similarity	NPC59295
0.9459	High Similarity	NPC17816
0.9427	High Similarity	NPC247973
0.9423	High Similarity	NPC45449
0.9419	High Similarity	NPC238995
0.9419	High Similarity	NPC272722
0.94	High Similarity	NPC179183
0.9367	High Similarity	NPC211309
0.9359	High Similarity	NPC110257
0.9346	High Similarity	NPC472461
0.9342	High Similarity	NPC280937
0.9338	High Similarity	NPC149614
0.9338	High Similarity	NPC117579
0.9308	High Similarity	NPC476641
0.9299	High Similarity	NPC291110
0.9299	High Similarity	NPC37183
0.9276	High Similarity	NPC101996
0.9272	High Similarity	NPC306821
0.925	High Similarity	NPC174700
0.925	High Similarity	NPC54098
0.925	High Similarity	NPC230619
0.9245	High Similarity	NPC247136
0.9241	High Similarity	NPC277480
0.9226	High Similarity	NPC195832
0.9216	High Similarity	NPC472915
0.9216	High Similarity	NPC167091
0.9216	High Similarity	NPC88645
0.9216	High Similarity	NPC292214
0.9216	High Similarity	NPC271779
0.9216	High Similarity	NPC206238
0.9211	High Similarity	NPC170169
0.9211	High Similarity	NPC58668
0.9211	High Similarity	NPC106372
0.9211	High Similarity	NPC208043
0.9211	High Similarity	NPC308451
0.9211	High Similarity	NPC226973
0.9211	High Similarity	NPC171010
0.9211	High Similarity	NPC115324
0.9205	High Similarity	NPC178202
0.9205	High Similarity	NPC328119
0.92	High Similarity	NPC119660
0.92	High Similarity	NPC93034
0.9195	High Similarity	NPC155144
0.9195	High Similarity	NPC98926
0.9193	High Similarity	NPC473834
0.9193	High Similarity	NPC65885
0.9193	High Similarity	NPC216842
0.9193	High Similarity	NPC476640
0.9193	High Similarity	NPC82217
0.9193	High Similarity	NPC310794
0.9182	High Similarity	NPC470704
0.9182	High Similarity	NPC86477
0.9182	High Similarity	NPC50394
0.9172	High Similarity	NPC81679
0.9161	High Similarity	NPC181960
0.9161	High Similarity	NPC476981
0.9161	High Similarity	NPC99597
0.9161	High Similarity	NPC210084
0.9161	High Similarity	NPC262286
0.9161	High Similarity	NPC36852
0.9156	High Similarity	NPC37392
0.9156	High Similarity	NPC20830
0.9156	High Similarity	NPC2928
0.9156	High Similarity	NPC256612
0.9156	High Similarity	NPC208197
0.9156	High Similarity	NPC472909
0.915	High Similarity	NPC222830
0.915	High Similarity	NPC25270
0.915	High Similarity	NPC100887
0.915	High Similarity	NPC239128
0.915	High Similarity	NPC198826
0.915	High Similarity	NPC301123
0.915	High Similarity	NPC187498
0.915	High Similarity	NPC162313
0.915	High Similarity	NPC120163
0.915	High Similarity	NPC71334
0.915	High Similarity	NPC199100
0.915	High Similarity	NPC212678
0.915	High Similarity	NPC275722
0.915	High Similarity	NPC57030
0.915	High Similarity	NPC39007
0.915	High Similarity	NPC180234
0.915	High Similarity	NPC188203
0.915	High Similarity	NPC156222
0.915	High Similarity	NPC301323
0.915	High Similarity	NPC120537
0.915	High Similarity	NPC83508
0.915	High Similarity	NPC293183
0.915	High Similarity	NPC161277
0.915	High Similarity	NPC207624
0.915	High Similarity	NPC256283
0.915	High Similarity	NPC275836
0.915	High Similarity	NPC131624
0.915	High Similarity	NPC241498
0.9145	High Similarity	NPC156953
0.9145	High Similarity	NPC230713
0.9145	High Similarity	NPC167576
0.9145	High Similarity	NPC78335
0.9145	High Similarity	NPC239363
0.9139	High Similarity	NPC287395
0.9139	High Similarity	NPC183655
0.9136	High Similarity	NPC290304
0.9136	High Similarity	NPC287243
0.9136	High Similarity	NPC236327
0.9128	High Similarity	NPC302181
0.9103	High Similarity	NPC154304
0.9103	High Similarity	NPC190487
0.9097	High Similarity	NPC255106
0.9097	High Similarity	NPC138243
0.9097	High Similarity	NPC472916
0.9097	High Similarity	NPC235165
0.9091	High Similarity	NPC231018
0.9091	High Similarity	NPC47781
0.9091	High Similarity	NPC276409
0.9091	High Similarity	NPC255350
0.9091	High Similarity	NPC145379
0.9091	High Similarity	NPC22519
0.9091	High Similarity	NPC176775
0.9091	High Similarity	NPC69394
0.9091	High Similarity	NPC75279
0.9091	High Similarity	NPC274327
0.9091	High Similarity	NPC183878
0.9091	High Similarity	NPC160951
0.9091	High Similarity	NPC86485
0.9091	High Similarity	NPC183874
0.9091	High Similarity	NPC250822
0.9085	High Similarity	NPC251110
0.9085	High Similarity	NPC262623
0.9085	High Similarity	NPC193976
0.9085	High Similarity	NPC19980
0.9085	High Similarity	NPC45291
0.9085	High Similarity	NPC23668
0.908	High Similarity	NPC49667
0.908	High Similarity	NPC8127
0.9079	High Similarity	NPC92722
0.9079	High Similarity	NPC102003
0.9079	High Similarity	NPC226644
0.9079	High Similarity	NPC37226
0.9073	High Similarity	NPC62536
0.9073	High Similarity	NPC33265
0.9073	High Similarity	NPC46941
0.9073	High Similarity	NPC61871
0.9073	High Similarity	NPC55557
0.9073	High Similarity	NPC12200
0.9073	High Similarity	NPC30647
0.9068	High Similarity	NPC131866
0.9067	High Similarity	NPC472917
0.9067	High Similarity	NPC230943
0.906	High Similarity	NPC53192
0.9057	High Similarity	NPC29411
0.9051	High Similarity	NPC469575
0.9045	High Similarity	NPC304839
0.9045	High Similarity	NPC220582
0.9045	High Similarity	NPC188967
0.9045	High Similarity	NPC476980
0.9038	High Similarity	NPC162869
0.9038	High Similarity	NPC48208
0.9038	High Similarity	NPC472911
0.9038	High Similarity	NPC167595
0.9038	High Similarity	NPC165977
0.9038	High Similarity	NPC245758
0.9038	High Similarity	NPC78225
0.9038	High Similarity	NPC217677
0.9038	High Similarity	NPC96167
0.9038	High Similarity	NPC222814
0.9038	High Similarity	NPC474836
0.9038	High Similarity	NPC475267
0.9038	High Similarity	NPC472913
0.9038	High Similarity	NPC472910
0.9038	High Similarity	NPC474208
0.9038	High Similarity	NPC469584
0.9038	High Similarity	NPC472914
0.9038	High Similarity	NPC300727
0.9038	High Similarity	NPC156057
0.9038	High Similarity	NPC241904
0.9032	High Similarity	NPC196439
0.9032	High Similarity	NPC4455
0.9032	High Similarity	NPC213622
0.9032	High Similarity	NPC2476
0.9032	High Similarity	NPC26227
0.9032	High Similarity	NPC189960
0.9032	High Similarity	NPC31018
0.9032	High Similarity	NPC201136
0.9032	High Similarity	NPC44079
0.9032	High Similarity	NPC128863
0.9032	High Similarity	NPC32557
0.9032	High Similarity	NPC201451

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 NPC45131 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	1001
0.2-0.3	1865
0.3-0.4	2675
0.4-0.5	1725
0.5-0.6	959
0.6-0.7	350
0.7-0.8	121
0.8-0.85	28
0.85-0.9	12
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD2801	Approved
0.8974	High Similarity	NPD3882	Suspended
0.8903	High Similarity	NPD1934	Approved
0.875	High Similarity	NPD1247	Approved
0.8688	High Similarity	NPD5494	Approved
0.8642	High Similarity	NPD3926	Phase 2
0.8627	High Similarity	NPD1511	Approved
0.8608	High Similarity	NPD2393	Clinical (unspecified phase)
0.8598	High Similarity	NPD3818	Discontinued
0.8516	High Similarity	NPD1512	Approved
0.8476	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD6166	Phase 2
0.8476	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD919	Approved
0.8385	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD2344	Approved
0.8354	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8322	Intermediate Similarity	NPD1240	Approved
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8301	Intermediate Similarity	NPD1549	Phase 2
0.8235	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1510	Phase 2
0.8214	Intermediate Similarity	NPD5844	Phase 1
0.8212	Intermediate Similarity	NPD1607	Approved
0.8176	Intermediate Similarity	NPD6559	Discontinued
0.8166	Intermediate Similarity	NPD7074	Phase 3
0.8148	Intermediate Similarity	NPD1465	Phase 2
0.8141	Intermediate Similarity	NPD2309	Approved
0.8129	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2800	Approved
0.8129	Intermediate Similarity	NPD1243	Approved
0.8113	Intermediate Similarity	NPD920	Approved
0.8107	Intermediate Similarity	NPD7054	Approved
0.8101	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD943	Approved
0.8075	Intermediate Similarity	NPD4380	Phase 2
0.8059	Intermediate Similarity	NPD7472	Approved
0.8052	Intermediate Similarity	NPD2796	Approved
0.8038	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD2935	Discontinued
0.7927	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7819	Suspended
0.7919	Intermediate Similarity	NPD7808	Phase 3
0.7914	Intermediate Similarity	NPD7411	Suspended
0.7908	Intermediate Similarity	NPD447	Suspended
0.7907	Intermediate Similarity	NPD6797	Phase 2
0.7907	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5402	Approved
0.7879	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2534	Approved
0.7875	Intermediate Similarity	NPD2533	Approved
0.7875	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7251	Discontinued
0.7853	Intermediate Similarity	NPD6599	Discontinued
0.7792	Intermediate Similarity	NPD230	Phase 1
0.7758	Intermediate Similarity	NPD6801	Discontinued
0.7736	Intermediate Similarity	NPD3750	Approved
0.7725	Intermediate Similarity	NPD7768	Phase 2
0.7719	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7702	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2296	Approved
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.7532	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3226	Approved
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5403	Approved
0.7452	Intermediate Similarity	NPD1933	Approved
0.744	Intermediate Similarity	NPD37	Approved
0.7439	Intermediate Similarity	NPD5401	Approved
0.7438	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3751	Discontinued
0.7427	Intermediate Similarity	NPD6234	Discontinued
0.7421	Intermediate Similarity	NPD3748	Approved
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7419	Intermediate Similarity	NPD3027	Phase 3
0.7412	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD4965	Approved
0.7412	Intermediate Similarity	NPD4966	Approved
0.7407	Intermediate Similarity	NPD4628	Phase 3
0.7405	Intermediate Similarity	NPD6651	Approved
0.7403	Intermediate Similarity	NPD9494	Approved
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7386	Intermediate Similarity	NPD1203	Approved
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.738	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7390	Discontinued
0.7375	Intermediate Similarity	NPD6100	Approved
0.7375	Intermediate Similarity	NPD6099	Approved
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7363	Intermediate Similarity	NPD4287	Approved
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD1471	Phase 3
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD2403	Approved
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5242	Approved
0.7255	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2654	Approved
0.7235	Intermediate Similarity	NPD6280	Approved
0.7235	Intermediate Similarity	NPD6279	Approved
0.7233	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1653	Approved
0.72	Intermediate Similarity	NPD3787	Discontinued
0.72	Intermediate Similarity	NPD7229	Phase 3
0.7195	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9269	Phase 2
0.719	Intermediate Similarity	NPD9717	Approved
0.7189	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4357	Discontinued
0.7152	Intermediate Similarity	NPD9268	Approved
0.7152	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.7151	Intermediate Similarity	NPD5353	Approved
0.7135	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD2163	Approved
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7134	Intermediate Similarity	NPD4908	Phase 1
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6808	Phase 2
0.7078	Intermediate Similarity	NPD1608	Approved
0.7076	Intermediate Similarity	NPD6386	Approved
0.7076	Intermediate Similarity	NPD6385	Approved
0.7072	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD1729	Discontinued
0.7044	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD411	Approved
0.7035	Intermediate Similarity	NPD6844	Discontinued
0.7024	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5536	Phase 2
0.7017	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1610	Phase 2
0.7013	Intermediate Similarity	NPD422	Phase 1
0.7006	Intermediate Similarity	NPD2798	Approved
0.6995	Remote Similarity	NPD8313	Approved
0.6995	Remote Similarity	NPD8312	Approved
0.6994	Remote Similarity	NPD5761	Phase 2
0.6994	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7033	Discontinued
0.6994	Remote Similarity	NPD5760	Phase 2
0.6994	Remote Similarity	NPD4308	Phase 3
0.699	Remote Similarity	NPD8151	Discontinued
0.6982	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7685	Pre-registration
0.6974	Remote Similarity	NPD1548	Phase 1
0.6962	Remote Similarity	NPD2861	Phase 2
0.6962	Remote Similarity	NPD3018	Phase 2
0.6947	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1470	Approved
0.694	Remote Similarity	NPD7549	Discontinued
0.6937	Remote Similarity	NPD3268	Approved
0.6927	Remote Similarity	NPD6777	Approved
0.6927	Remote Similarity	NPD6779	Approved
0.6927	Remote Similarity	NPD6776	Approved
0.6927	Remote Similarity	NPD6781	Approved
0.6927	Remote Similarity	NPD6778	Approved
0.6927	Remote Similarity	NPD6782	Approved
0.6927	Remote Similarity	NPD6780	Approved
0.6914	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4361	Phase 2
0.6895	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6233	Phase 2
0.6883	Remote Similarity	NPD17	Approved
0.6875	Remote Similarity	NPD6971	Discontinued
0.6875	Remote Similarity	NPD4625	Phase 3
0.6872	Remote Similarity	NPD7871	Phase 2
0.6872	Remote Similarity	NPD7870	Phase 2
0.6863	Remote Similarity	NPD9545	Approved
0.686	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1481	Phase 2
0.6859	Remote Similarity	NPD3972	Approved
0.6857	Remote Similarity	NPD4288	Approved
0.6848	Remote Similarity	NPD5406	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