NPASS Compound

Structure

CID133065 OpenBabel06191715492D 30 32 0 0 0 0 0 0 0 0999 V2000 3.5491 -7.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -7.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -4.8090 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 -5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -6.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -2.8090 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 -2.0878 0.0570 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 0.0000 -1.6180 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 4.4152 -7.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -4.3090 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 -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 1.8171 -1.8090 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 2.6831 -0.3090 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 0.9511 -0.3090 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 -3.5878 -2.5411 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 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 29 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 15 2 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 16 2 0 0 0 0 9 20 1 0 0 0 0 10 17 2 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 11 19 2 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 13 23 2 0 0 0 0 14 22 2 0 0 0 0 14 24 1 0 0 0 0 17 23 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 25 2 0 0 0 0 21 24 2 0 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 30 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.19
Volume:	435.51
LogP:	6.237
LogD:	4.231
LogS:	-2.852
# Rotatable Bonds:	7
TPSA:	83.06
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.391
Synthetic Accessibility Score:	3.044
Fsp3:	0.28
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.035
MDCK Permeability:	1.570971835462842e-05
Pgp-inhibitor:	0.633
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	96.90784454345703%
Volume Distribution (VD):	1.227
Pgp-substrate:	1.6711578369140625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.481
CYP2C19-inhibitor:	0.959
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.841
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.973
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.763
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	8.377
Half-life (T1/2):	0.608

ADMET: Toxicity

hERG Blockers:	0.261
Human Hepatotoxicity (H-HT):	0.664
Drug-inuced Liver Injury (DILI):	0.182
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.953
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.842
Respiratory Toxicity:	0.666

Download Data

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

Natural Product: NPC133065

Natural Product ID:	NPC133065
*Common Name:**	Mulberrofuran Y
IUPAC Name:	5-[4-[(2E)-3,7-dimethylocta-2,6-dienyl]-6-hydroxy-5-methoxy-1-benzofuran-2-yl]benzene-1,3-diol
Synonyms:	Mulberrofuran Y
Standard InCHIKey:	WLJKBVCQTOXSPP-LZYBPNLTSA-N
Standard InCHI:	InChI=1S/C25H28O5/c1-15(2)6-5-7-16(3)8-9-20-21-13-23(17-10-18(26)12-19(27)11-17)30-24(21)14-22(28)25(20)29-4/h6,8,10-14,26-28H,5,7,9H2,1-4H3/b16-8+
SMILES:	COc1c(O)cc2c(c1C/C=C(/CCC=C(C)C)C)cc(o2)c1cc(O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448850
PubChem CID:	10621441
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
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429996]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
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]
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[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]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9402	Morus mongolica	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[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9402	Morus mongolica	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]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	110000.0	nM	PMID[475230]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	4800.0	nM	PMID[475231]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	=	140000.0	nM	PMID[475230]
NPT27	Others	Unspecified		CC50	=	190000.0	nM	PMID[475230]
NPT27	Others	Unspecified		Ratio	=	1.7	n.a.	PMID[475230]

☑ 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 NPC133065 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	438
0.1-0.2	1745
0.2-0.3	4316
0.3-0.4	10773
0.4-0.5	7354
0.5-0.6	3515
0.6-0.7	5082
0.7-0.8	5510
0.8-0.85	2294
0.85-0.9	1158
0.9-0.95	498
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC39306
0.9806	High Similarity	NPC84515
0.9806	High Similarity	NPC312056
0.9742	High Similarity	NPC188486
0.974	High Similarity	NPC196879
0.9623	High Similarity	NPC247136
0.9613	High Similarity	NPC16935
0.961	High Similarity	NPC45131
0.956	High Similarity	NPC247973
0.9557	High Similarity	NPC36320
0.9557	High Similarity	NPC45449
0.9494	High Similarity	NPC39305
0.9494	High Similarity	NPC263092
0.9494	High Similarity	NPC59295
0.9494	High Similarity	NPC1755
0.9494	High Similarity	NPC1706
0.9434	High Similarity	NPC291110
0.9434	High Similarity	NPC37183
0.943	High Similarity	NPC272722
0.943	High Similarity	NPC238995
0.9423	High Similarity	NPC300727
0.9423	High Similarity	NPC241904
0.9416	High Similarity	NPC125300
0.9383	High Similarity	NPC174700
0.9375	High Similarity	NPC277480
0.9371	High Similarity	NPC475985
0.9363	High Similarity	NPC476242
0.9359	High Similarity	NPC274730
0.9351	High Similarity	NPC58668
0.9351	High Similarity	NPC106372
0.9325	High Similarity	NPC82217
0.9325	High Similarity	NPC310794
0.9325	High Similarity	NPC473834
0.9325	High Similarity	NPC216842
0.9325	High Similarity	NPC476640
0.9317	High Similarity	NPC50394
0.9313	High Similarity	NPC326520
0.9304	High Similarity	NPC228785
0.9304	High Similarity	NPC14353
0.9304	High Similarity	NPC56085
0.929	High Similarity	NPC207624
0.9268	High Similarity	NPC287243
0.9268	High Similarity	NPC227906
0.9264	High Similarity	NPC230619
0.9264	High Similarity	NPC54098
0.9255	High Similarity	NPC170245
0.925	High Similarity	NPC270837
0.9245	High Similarity	NPC278052
0.9245	High Similarity	NPC40491
0.9245	High Similarity	NPC61010
0.9241	High Similarity	NPC100123
0.9241	High Similarity	NPC195832
0.9236	High Similarity	NPC472461
0.9231	High Similarity	NPC89474
0.9226	High Similarity	NPC115324
0.9226	High Similarity	NPC23668
0.9226	High Similarity	NPC193976
0.9212	High Similarity	NPC49667
0.9212	High Similarity	NPC8127
0.9202	High Similarity	NPC476641
0.9202	High Similarity	NPC131866
0.9198	High Similarity	NPC86477
0.9198	High Similarity	NPC470704
0.9187	High Similarity	NPC81679
0.9187	High Similarity	NPC294965
0.9182	High Similarity	NPC200746
0.9182	High Similarity	NPC320359
0.9177	High Similarity	NPC165977
0.9177	High Similarity	NPC36852
0.9177	High Similarity	NPC262286
0.9177	High Similarity	NPC217677
0.9177	High Similarity	NPC469584
0.9172	High Similarity	NPC20830
0.9172	High Similarity	NPC256612
0.9172	High Similarity	NPC208197
0.9172	High Similarity	NPC148938
0.9167	High Similarity	NPC101996
0.9167	High Similarity	NPC142308
0.9157	High Similarity	NPC77179
0.9157	High Similarity	NPC23553
0.9141	High Similarity	NPC211309
0.913	High Similarity	NPC236521
0.913	High Similarity	NPC248638
0.913	High Similarity	NPC7483
0.913	High Similarity	NPC152659
0.913	High Similarity	NPC220313
0.913	High Similarity	NPC236132
0.9125	High Similarity	NPC66288
0.9119	High Similarity	NPC329091
0.9114	High Similarity	NPC138243
0.9114	High Similarity	NPC472916
0.9114	High Similarity	NPC180924
0.9114	High Similarity	NPC142339
0.9108	High Similarity	NPC274327
0.9108	High Similarity	NPC271779
0.9108	High Similarity	NPC167091
0.9108	High Similarity	NPC47781
0.9108	High Similarity	NPC88645
0.9108	High Similarity	NPC250822
0.9108	High Similarity	NPC69394
0.9108	High Similarity	NPC235333
0.9108	High Similarity	NPC75279
0.9108	High Similarity	NPC280937
0.9108	High Similarity	NPC292214
0.9108	High Similarity	NPC206238
0.9108	High Similarity	NPC160951
0.9108	High Similarity	NPC231018
0.9108	High Similarity	NPC176775
0.9108	High Similarity	NPC255350
0.9108	High Similarity	NPC183878
0.9108	High Similarity	NPC145379
0.9108	High Similarity	NPC22519
0.9108	High Similarity	NPC276409
0.9107	High Similarity	NPC228209
0.9103	High Similarity	NPC202157
0.9103	High Similarity	NPC171010
0.9102	High Similarity	NPC183843
0.9102	High Similarity	NPC476273
0.9097	High Similarity	NPC102003
0.9097	High Similarity	NPC92722
0.9091	High Similarity	NPC17816
0.9091	High Similarity	NPC277510
0.9091	High Similarity	NPC261471
0.9091	High Similarity	NPC30550
0.9091	High Similarity	NPC65885
0.9085	High Similarity	NPC218533
0.9085	High Similarity	NPC78830
0.9074	High Similarity	NPC239752
0.9074	High Similarity	NPC472450
0.9074	High Similarity	NPC473286
0.9074	High Similarity	NPC29411
0.9074	High Similarity	NPC275780
0.9068	High Similarity	NPC25152
0.9062	High Similarity	NPC475886
0.9062	High Similarity	NPC476980
0.9062	High Similarity	NPC139036
0.9062	High Similarity	NPC474287
0.9057	High Similarity	NPC236796
0.9057	High Similarity	NPC474208
0.9057	High Similarity	NPC48208
0.9057	High Similarity	NPC162869
0.9057	High Similarity	NPC181960
0.9057	High Similarity	NPC472911
0.9057	High Similarity	NPC472914
0.9057	High Similarity	NPC99597
0.9057	High Similarity	NPC78225
0.9057	High Similarity	NPC156057
0.9057	High Similarity	NPC475267
0.9057	High Similarity	NPC246647
0.9057	High Similarity	NPC472963
0.9057	High Similarity	NPC96342
0.9057	High Similarity	NPC222814
0.9057	High Similarity	NPC474836
0.9057	High Similarity	NPC210084
0.9057	High Similarity	NPC299520
0.9057	High Similarity	NPC245758
0.9057	High Similarity	NPC96167
0.9057	High Similarity	NPC129684
0.9057	High Similarity	NPC472913
0.9057	High Similarity	NPC472910
0.9057	High Similarity	NPC164110
0.9057	High Similarity	NPC212967
0.9051	High Similarity	NPC92659
0.9051	High Similarity	NPC227325
0.9051	High Similarity	NPC167815
0.9051	High Similarity	NPC201136
0.9051	High Similarity	NPC128863
0.9051	High Similarity	NPC146165
0.9051	High Similarity	NPC213622
0.9051	High Similarity	NPC2476
0.9051	High Similarity	NPC113906
0.9051	High Similarity	NPC99199
0.9051	High Similarity	NPC138360
0.9051	High Similarity	NPC280339
0.9051	High Similarity	NPC213936
0.9051	High Similarity	NPC183597
0.9051	High Similarity	NPC50715
0.9051	High Similarity	NPC196439
0.9051	High Similarity	NPC297531
0.9051	High Similarity	NPC2928
0.9051	High Similarity	NPC163780
0.9051	High Similarity	NPC4455
0.9045	High Similarity	NPC25270
0.9045	High Similarity	NPC222830
0.9045	High Similarity	NPC275836
0.9045	High Similarity	NPC256283
0.9045	High Similarity	NPC71334
0.9045	High Similarity	NPC162313
0.9045	High Similarity	NPC120537
0.9045	High Similarity	NPC57030
0.9045	High Similarity	NPC39732
0.9045	High Similarity	NPC120163
0.9045	High Similarity	NPC188203
0.9045	High Similarity	NPC180234
0.9045	High Similarity	NPC39007
0.9045	High Similarity	NPC131624
0.9045	High Similarity	NPC60972
0.9045	High Similarity	NPC187498
0.9045	High Similarity	NPC156222
0.9045	High Similarity	NPC293183

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 NPC133065 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	959
0.2-0.3	1818
0.3-0.4	2703
0.4-0.5	1772
0.5-0.6	953
0.6-0.7	392
0.7-0.8	129
0.8-0.85	21
0.85-0.9	17
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9108	High Similarity	NPD2801	Approved
0.8994	High Similarity	NPD3882	Suspended
0.8805	High Similarity	NPD1934	Approved
0.8634	High Similarity	NPD2393	Clinical (unspecified phase)
0.8623	High Similarity	NPD3818	Discontinued
0.8598	High Similarity	NPD5494	Approved
0.8554	High Similarity	NPD3926	Phase 2
0.8535	High Similarity	NPD1511	Approved
0.8503	High Similarity	NPD6168	Clinical (unspecified phase)
0.8503	High Similarity	NPD6166	Phase 2
0.8503	High Similarity	NPD6167	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6232	Discontinued
0.8452	Intermediate Similarity	NPD7473	Discontinued
0.8434	Intermediate Similarity	NPD1247	Approved
0.8428	Intermediate Similarity	NPD1512	Approved
0.8415	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD1465	Phase 2
0.8364	Intermediate Similarity	NPD3749	Approved
0.8353	Intermediate Similarity	NPD5844	Phase 1
0.8242	Intermediate Similarity	NPD3817	Phase 2
0.8198	Intermediate Similarity	NPD7074	Phase 3
0.8161	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD2344	Approved
0.814	Intermediate Similarity	NPD7054	Approved
0.8137	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6959	Discontinued
0.8103	Intermediate Similarity	NPD6559	Discontinued
0.8095	Intermediate Similarity	NPD919	Approved
0.8092	Intermediate Similarity	NPD7472	Approved
0.8072	Intermediate Similarity	NPD7819	Suspended
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD1549	Phase 2
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6799	Approved
0.795	Intermediate Similarity	NPD2309	Approved
0.7943	Intermediate Similarity	NPD6797	Phase 2
0.7943	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD2800	Approved
0.7929	Intermediate Similarity	NPD7075	Discontinued
0.7929	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1510	Phase 2
0.7898	Intermediate Similarity	NPD7251	Discontinued
0.7898	Intermediate Similarity	NPD1607	Approved
0.7892	Intermediate Similarity	NPD6599	Discontinued
0.7889	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2796	Approved
0.7857	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7808	Phase 3
0.7826	Intermediate Similarity	NPD1243	Approved
0.7818	Intermediate Similarity	NPD920	Approved
0.7818	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD5402	Approved
0.7799	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.7778	Intermediate Similarity	NPD3750	Approved
0.775	Intermediate Similarity	NPD2935	Discontinued
0.7738	Intermediate Similarity	NPD7411	Suspended
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7701	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6801	Discontinued
0.7661	Intermediate Similarity	NPD7768	Phase 2
0.7657	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD447	Suspended
0.7588	Intermediate Similarity	NPD37	Approved
0.7578	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3751	Discontinued
0.7564	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4967	Phase 2
0.7558	Intermediate Similarity	NPD4965	Approved
0.7558	Intermediate Similarity	NPD4966	Approved
0.753	Intermediate Similarity	NPD7390	Discontinued
0.753	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3226	Approved
0.7513	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7472	Intermediate Similarity	NPD7228	Approved
0.7469	Intermediate Similarity	NPD3748	Approved
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7455	Intermediate Similarity	NPD4628	Phase 3
0.7443	Intermediate Similarity	NPD5710	Approved
0.7443	Intermediate Similarity	NPD5711	Approved
0.7443	Intermediate Similarity	NPD3787	Discontinued
0.7438	Intermediate Similarity	NPD1613	Approved
0.7438	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6099	Approved
0.7423	Intermediate Similarity	NPD6100	Approved
0.7423	Intermediate Similarity	NPD1551	Phase 2
0.7419	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4287	Approved
0.7399	Intermediate Similarity	NPD2296	Approved
0.7396	Intermediate Similarity	NPD5403	Approved
0.7394	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1471	Phase 3
0.7378	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD2799	Discontinued
0.7345	Intermediate Similarity	NPD7229	Phase 3
0.7342	Intermediate Similarity	NPD9494	Approved
0.7312	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5401	Approved
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2403	Approved
0.7253	Intermediate Similarity	NPD5953	Discontinued
0.7251	Intermediate Similarity	NPD1653	Approved
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6651	Approved
0.7238	Intermediate Similarity	NPD7286	Phase 2
0.7228	Intermediate Similarity	NPD8313	Approved
0.7228	Intermediate Similarity	NPD8312	Approved
0.7213	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8151	Discontinued
0.7207	Intermediate Similarity	NPD5242	Approved
0.7205	Intermediate Similarity	NPD3764	Approved
0.7202	Intermediate Similarity	NPD6190	Approved
0.7184	Intermediate Similarity	NPD6280	Approved
0.7184	Intermediate Similarity	NPD6279	Approved
0.7178	Intermediate Similarity	NPD1933	Approved
0.715	Intermediate Similarity	NPD6778	Approved
0.715	Intermediate Similarity	NPD6776	Approved
0.715	Intermediate Similarity	NPD6782	Approved
0.715	Intermediate Similarity	NPD6777	Approved
0.715	Intermediate Similarity	NPD6781	Approved
0.715	Intermediate Similarity	NPD6779	Approved
0.715	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD9269	Phase 2
0.712	Intermediate Similarity	NPD7685	Pre-registration
0.7107	Intermediate Similarity	NPD1203	Approved
0.7099	Intermediate Similarity	NPD2313	Discontinued
0.7088	Intermediate Similarity	NPD2163	Approved
0.7088	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2654	Approved
0.7081	Intermediate Similarity	NPD4908	Phase 1
0.7076	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7907	Approved
0.7072	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4111	Phase 1
0.7059	Intermediate Similarity	NPD4665	Approved
0.7056	Intermediate Similarity	NPD6808	Phase 2
0.705	Intermediate Similarity	NPD7783	Phase 2
0.705	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5761	Phase 2
0.7045	Intermediate Similarity	NPD5760	Phase 2
0.7041	Intermediate Similarity	NPD7435	Discontinued
0.7037	Intermediate Similarity	NPD4625	Phase 3
0.7035	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7240	Approved
0.7021	Intermediate Similarity	NPD8150	Discontinued
0.7018	Intermediate Similarity	NPD4357	Discontinued
0.7011	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7006	Intermediate Similarity	NPD5353	Approved
0.7005	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7871	Phase 2
0.7005	Intermediate Similarity	NPD7870	Phase 2
0.7	Intermediate Similarity	NPD1470	Approved
0.6994	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6832	Phase 2
0.697	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2798	Approved
0.6954	Remote Similarity	NPD7696	Phase 3
0.6954	Remote Similarity	NPD7698	Approved
0.6954	Remote Similarity	NPD7697	Approved
0.6932	Remote Similarity	NPD6386	Approved
0.6932	Remote Similarity	NPD6385	Approved
0.6919	Remote Similarity	NPD1729	Discontinued
0.6918	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD9717	Approved
0.6914	Remote Similarity	NPD2861	Phase 2
0.691	Remote Similarity	NPD4288	Approved
0.6909	Remote Similarity	NPD4060	Phase 1
0.6907	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6823	Phase 2
0.69	Remote Similarity	NPD7701	Phase 2
0.6898	Remote Similarity	NPD7549	Discontinued
0.6893	Remote Similarity	NPD6844	Discontinued
0.6891	Remote Similarity	NPD6534	Approved
0.6891	Remote Similarity	NPD6535	Approved
0.689	Remote Similarity	NPD3268	Approved
0.689	Remote Similarity	NPD1699	Clinical (unspecified phase)

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