NPASS Compound

Structure

CID193026 OpenBabel06191715582D 24 26 0 0 1 0 0 0 0 0999 V2000 -5.2812 -1.8090 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 4.5878 -2.5411 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 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 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 -2.6831 -0.3090 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 -0.0000 -1.6180 0.0000 C 0 0 3 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 3.5878 -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 -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 3 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 4.5878 -0.8090 0.0000 O 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 -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 5 1 0 0 0 0 2 12 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 16 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 18 2 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.15
Volume:	345.512
LogP:	3.525
LogD:	3.597
LogS:	-4.084
# Rotatable Bonds:	4
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.886
Synthetic Accessibility Score:	3.28
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.828
MDCK Permeability:	1.314573637500871e-05
Pgp-inhibitor:	0.95
Pgp-substrate:	0.947
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.072

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	98.4262924194336%
Volume Distribution (VD):	1.368
Pgp-substrate:	1.8284850120544434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.573
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.853
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.83
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.471
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.72
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	4.489
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.629
AMES Toxicity:	0.272
Rat Oral Acute Toxicity:	0.148
Maximum Recommended Daily Dose:	0.823
Skin Sensitization:	0.455
Carcinogencity:	0.084
Eye Corrosion:	0.003
Eye Irritation:	0.287
Respiratory Toxicity:	0.495

Download Data

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

Natural Product: NPC193026

Natural Product ID:	NPC193026
*Common Name:**	Dehrodiisoeugenol
IUPAC Name:	2-methoxy-4-[7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
Synonyms:
Standard InCHIKey:	ITDOFWOJEDZPCF-AATRIKPKSA-N
Standard InCHI:	InChI=1S/C20H22O4/c1-5-6-13-9-15-12(2)19(24-20(15)18(10-13)23-4)14-7-8-16(21)17(11-14)22-3/h5-12,19,21H,1-4H3/b6-5+
SMILES:	C/C=C/c1cc2C(C)C(c3ccc(c(c3)OC)O)Oc2c(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2442730
PubChem CID:	5379033
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
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Inhibition	=	28.0	%	PMID[498570]

☑ 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 NPC193026 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	402
0.1-0.2	1445
0.2-0.3	3819
0.3-0.4	11010
0.4-0.5	7654
0.5-0.6	3866
0.6-0.7	7890
0.7-0.8	4980
0.8-0.85	894
0.85-0.9	576
0.9-0.95	142
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC187616
1.0	High Similarity	NPC49603
0.9845	High Similarity	NPC177160
0.9845	High Similarity	NPC29799
0.9845	High Similarity	NPC54743
0.9845	High Similarity	NPC156502
0.9845	High Similarity	NPC209985
0.9845	High Similarity	NPC10737
0.9845	High Similarity	NPC263367
0.9845	High Similarity	NPC477939
0.9612	High Similarity	NPC26394
0.9549	High Similarity	NPC471414
0.9549	High Similarity	NPC87725
0.9549	High Similarity	NPC263261
0.9535	High Similarity	NPC230219
0.9528	High Similarity	NPC45774
0.9528	High Similarity	NPC129570
0.9528	High Similarity	NPC21867
0.9528	High Similarity	NPC282703
0.9528	High Similarity	NPC184733
0.9528	High Similarity	NPC128208
0.9528	High Similarity	NPC11258
0.9478	High Similarity	NPC253878
0.9478	High Similarity	NPC131971
0.9449	High Similarity	NPC98745
0.9385	High Similarity	NPC18842
0.938	High Similarity	NPC241522
0.938	High Similarity	NPC174495
0.938	High Similarity	NPC257582
0.938	High Similarity	NPC153739
0.938	High Similarity	NPC187998
0.938	High Similarity	NPC242807
0.938	High Similarity	NPC145305
0.938	High Similarity	NPC143483
0.938	High Similarity	NPC42300
0.938	High Similarity	NPC77040
0.938	High Similarity	NPC92164
0.938	High Similarity	NPC64201
0.9338	High Similarity	NPC474444
0.9338	High Similarity	NPC93433
0.9338	High Similarity	NPC45257
0.9338	High Similarity	NPC284881
0.9338	High Similarity	NPC93323
0.9338	High Similarity	NPC12641
0.9338	High Similarity	NPC280092
0.9338	High Similarity	NPC264706
0.9328	High Similarity	NPC254759
0.9328	High Similarity	NPC184797
0.9328	High Similarity	NPC160283
0.9328	High Similarity	NPC309124
0.9323	High Similarity	NPC477938
0.9308	High Similarity	NPC40432
0.9308	High Similarity	NPC277804
0.9308	High Similarity	NPC228346
0.9308	High Similarity	NPC161557
0.9308	High Similarity	NPC7171
0.9308	High Similarity	NPC27843
0.9308	High Similarity	NPC115207
0.9308	High Similarity	NPC158079
0.9302	High Similarity	NPC475875
0.9297	High Similarity	NPC21563
0.927	High Similarity	NPC163898
0.9265	High Similarity	NPC47633
0.9265	High Similarity	NPC85264
0.9265	High Similarity	NPC102044
0.9254	High Similarity	NPC292882
0.9254	High Similarity	NPC260741
0.9254	High Similarity	NPC236306
0.9254	High Similarity	NPC70682
0.9254	High Similarity	NPC473739
0.9254	High Similarity	NPC232164
0.9248	High Similarity	NPC77861
0.9242	High Similarity	NPC16485
0.9242	High Similarity	NPC478085
0.9242	High Similarity	NPC471942
0.9237	High Similarity	NPC207400
0.9237	High Similarity	NPC181049
0.9225	High Similarity	NPC472968
0.9225	High Similarity	NPC470084
0.9219	High Similarity	NPC178284
0.9219	High Similarity	NPC58607
0.9219	High Similarity	NPC191037
0.9203	High Similarity	NPC260397
0.9197	High Similarity	NPC63879
0.9191	High Similarity	NPC107161
0.9167	High Similarity	NPC158331
0.9167	High Similarity	NPC170185
0.9147	High Similarity	NPC147821
0.9147	High Similarity	NPC319625
0.9147	High Similarity	NPC118787
0.9147	High Similarity	NPC118533
0.9147	High Similarity	NPC163332
0.9147	High Similarity	NPC183181
0.9147	High Similarity	NPC292056
0.9147	High Similarity	NPC41706
0.9147	High Similarity	NPC165045
0.9147	High Similarity	NPC111247
0.9141	High Similarity	NPC148627
0.9141	High Similarity	NPC194519
0.9137	High Similarity	NPC213074
0.9137	High Similarity	NPC275284
0.9137	High Similarity	NPC224674
0.9137	High Similarity	NPC193473
0.9137	High Similarity	NPC21776
0.9137	High Similarity	NPC114505
0.9137	High Similarity	NPC15956
0.9137	High Similarity	NPC16269
0.9137	High Similarity	NPC31325
0.9134	High Similarity	NPC317769
0.9134	High Similarity	NPC31344
0.9124	High Similarity	NPC477616
0.9118	High Similarity	NPC35216
0.9118	High Similarity	NPC247291
0.9118	High Similarity	NPC311530
0.9104	High Similarity	NPC265433
0.9104	High Similarity	NPC248727
0.9104	High Similarity	NPC162659
0.9104	High Similarity	NPC270456
0.9098	High Similarity	NPC67247
0.9098	High Similarity	NPC287745
0.9091	High Similarity	NPC4940
0.9091	High Similarity	NPC175067
0.9091	High Similarity	NPC204215
0.9091	High Similarity	NPC471505
0.9071	High Similarity	NPC473408
0.9071	High Similarity	NPC236166
0.907	High Similarity	NPC206882
0.9062	High Similarity	NPC109822
0.9062	High Similarity	NPC94276
0.9058	High Similarity	NPC473108
0.9055	High Similarity	NPC150026
0.9051	High Similarity	NPC41782
0.9051	High Similarity	NPC59841
0.9051	High Similarity	NPC475891
0.9051	High Similarity	NPC2613
0.9051	High Similarity	NPC204347
0.9044	High Similarity	NPC27495
0.9044	High Similarity	NPC259519
0.903	High Similarity	NPC473413
0.903	High Similarity	NPC112939
0.903	High Similarity	NPC256262
0.903	High Similarity	NPC93783
0.903	High Similarity	NPC112246
0.903	High Similarity	NPC474206
0.903	High Similarity	NPC142547
0.903	High Similarity	NPC126409
0.903	High Similarity	NPC470356
0.903	High Similarity	NPC134968
0.903	High Similarity	NPC99572
0.903	High Similarity	NPC135777
0.903	High Similarity	NPC121812
0.903	High Similarity	NPC94750
0.9023	High Similarity	NPC475840
0.9008	High Similarity	NPC86030
0.9008	High Similarity	NPC5851
0.9	High Similarity	NPC5428
0.9	High Similarity	NPC101376
0.8993	High Similarity	NPC469557
0.8993	High Similarity	NPC180953
0.8993	High Similarity	NPC476301
0.8993	High Similarity	NPC43508
0.8993	High Similarity	NPC181615
0.8992	High Similarity	NPC81641
0.8986	High Similarity	NPC474104
0.8984	High Similarity	NPC471693
0.8978	High Similarity	NPC470372
0.8978	High Similarity	NPC471389
0.8976	High Similarity	NPC172676
0.8976	High Similarity	NPC57268
0.8976	High Similarity	NPC65933
0.8976	High Similarity	NPC216929
0.8976	High Similarity	NPC126935
0.8976	High Similarity	NPC312713
0.8971	High Similarity	NPC25966
0.8971	High Similarity	NPC245207
0.8971	High Similarity	NPC319647
0.8971	High Similarity	NPC32630
0.8971	High Similarity	NPC127218
0.8963	High Similarity	NPC16435
0.8963	High Similarity	NPC472334
0.8963	High Similarity	NPC474639
0.8963	High Similarity	NPC470802
0.8963	High Similarity	NPC471988
0.8963	High Similarity	NPC230734
0.8963	High Similarity	NPC472336
0.8963	High Similarity	NPC227503
0.8963	High Similarity	NPC306441
0.8955	High Similarity	NPC90083
0.8955	High Similarity	NPC317380
0.8955	High Similarity	NPC244983
0.8955	High Similarity	NPC326095
0.8955	High Similarity	NPC170779
0.8947	High Similarity	NPC106739
0.8944	High Similarity	NPC98624
0.8931	High Similarity	NPC72529
0.8931	High Similarity	NPC474178
0.8931	High Similarity	NPC252307
0.8931	High Similarity	NPC245826
0.8929	High Similarity	NPC324492
0.8929	High Similarity	NPC317053

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 NPC193026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	866
0.2-0.3	1735
0.3-0.4	2644
0.4-0.5	1719
0.5-0.6	930
0.6-0.7	703
0.7-0.8	212
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
0.8722	High Similarity	NPD3027	Phase 3
0.8667	High Similarity	NPD1613	Approved
0.8667	High Similarity	NPD1612	Clinical (unspecified phase)
0.8571	High Similarity	NPD2861	Phase 2
0.8507	High Similarity	NPD1529	Clinical (unspecified phase)
0.8433	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD4060	Phase 1
0.8268	Intermediate Similarity	NPD5283	Phase 1
0.8248	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3620	Phase 2
0.8129	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD228	Approved
0.8102	Intermediate Similarity	NPD4908	Phase 1
0.8056	Intermediate Similarity	NPD6674	Discontinued
0.8056	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD3705	Approved
0.7985	Intermediate Similarity	NPD1610	Phase 2
0.7961	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3021	Approved
0.7953	Intermediate Similarity	NPD3022	Approved
0.7941	Intermediate Similarity	NPD8651	Approved
0.7895	Intermediate Similarity	NPD1934	Approved
0.7877	Intermediate Similarity	NPD6331	Phase 2
0.7872	Intermediate Similarity	NPD1558	Phase 1
0.7871	Intermediate Similarity	NPD6234	Discontinued
0.7868	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6355	Discontinued
0.781	Intermediate Similarity	NPD6696	Suspended
0.7793	Intermediate Similarity	NPD5762	Approved
0.7793	Intermediate Similarity	NPD5763	Approved
0.7786	Intermediate Similarity	NPD4625	Phase 3
0.7778	Intermediate Similarity	NPD5588	Approved
0.7742	Intermediate Similarity	NPD3882	Suspended
0.7734	Intermediate Similarity	NPD2684	Approved
0.7727	Intermediate Similarity	NPD6671	Approved
0.7727	Intermediate Similarity	NPD7157	Approved
0.7708	Intermediate Similarity	NPD4538	Approved
0.7708	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4536	Approved
0.7692	Intermediate Similarity	NPD5735	Approved
0.7687	Intermediate Similarity	NPD1548	Phase 1
0.7671	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD37	Approved
0.7651	Intermediate Similarity	NPD5058	Phase 3
0.7643	Intermediate Similarity	NPD3018	Phase 2
0.7635	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4110	Phase 3
0.7634	Intermediate Similarity	NPD7843	Approved
0.763	Intermediate Similarity	NPD1357	Approved
0.7628	Intermediate Similarity	NPD4966	Approved
0.7628	Intermediate Similarity	NPD4967	Phase 2
0.7628	Intermediate Similarity	NPD4965	Approved
0.7625	Intermediate Similarity	NPD2489	Approved
0.7625	Intermediate Similarity	NPD27	Approved
0.7616	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2801	Approved
0.7609	Intermediate Similarity	NPD4749	Approved
0.7606	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5494	Approved
0.7591	Intermediate Similarity	NPD1091	Approved
0.7584	Intermediate Similarity	NPD2677	Approved
0.7568	Intermediate Similarity	NPD4236	Phase 3
0.7568	Intermediate Similarity	NPD4237	Approved
0.7562	Intermediate Similarity	NPD2969	Approved
0.7562	Intermediate Similarity	NPD2970	Approved
0.7551	Intermediate Similarity	NPD1375	Discontinued
0.7547	Intermediate Similarity	NPD7199	Phase 2
0.7534	Intermediate Similarity	NPD5960	Phase 3
0.7534	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3818	Discontinued
0.7531	Intermediate Similarity	NPD7228	Approved
0.7519	Intermediate Similarity	NPD290	Approved
0.7516	Intermediate Similarity	NPD6166	Phase 2
0.7516	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1653	Approved
0.7516	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3051	Approved
0.7483	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2161	Phase 2
0.7483	Intermediate Similarity	NPD6798	Discontinued
0.7482	Intermediate Similarity	NPD2983	Phase 2
0.7482	Intermediate Similarity	NPD5327	Phase 3
0.7482	Intermediate Similarity	NPD2982	Phase 2
0.747	Intermediate Similarity	NPD7312	Approved
0.747	Intermediate Similarity	NPD7310	Approved
0.747	Intermediate Similarity	NPD7313	Approved
0.747	Intermediate Similarity	NPD7311	Approved
0.7453	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2563	Approved
0.7452	Intermediate Similarity	NPD2560	Approved
0.745	Intermediate Similarity	NPD3060	Approved
0.7447	Intermediate Similarity	NPD6584	Phase 3
0.7442	Intermediate Similarity	NPD968	Approved
0.7434	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4123	Phase 3
0.7432	Intermediate Similarity	NPD6002	Phase 3
0.7432	Intermediate Similarity	NPD6004	Phase 3
0.7432	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6005	Phase 3
0.7432	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7266	Discontinued
0.7425	Intermediate Similarity	NPD7309	Approved
0.7413	Intermediate Similarity	NPD7095	Approved
0.741	Intermediate Similarity	NPD2981	Phase 2
0.74	Intermediate Similarity	NPD4628	Phase 3
0.7397	Intermediate Similarity	NPD2157	Approved
0.7389	Intermediate Similarity	NPD2978	Approved
0.7389	Intermediate Similarity	NPD2977	Approved
0.7383	Intermediate Similarity	NPD2424	Discontinued
0.7379	Intermediate Similarity	NPD4140	Approved
0.7378	Intermediate Similarity	NPD5844	Phase 1
0.7368	Intermediate Similarity	NPD1511	Approved
0.7365	Intermediate Similarity	NPD4578	Approved
0.7365	Intermediate Similarity	NPD4577	Approved
0.7353	Intermediate Similarity	NPD5536	Phase 2
0.7343	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5976	Discontinued
0.7337	Intermediate Similarity	NPD4663	Approved
0.7333	Intermediate Similarity	NPD5177	Phase 3
0.7333	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD4162	Approved
0.7329	Intermediate Similarity	NPD3657	Discovery
0.7329	Intermediate Similarity	NPD8127	Discontinued
0.7324	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5846	Approved
0.7319	Intermediate Similarity	NPD6516	Phase 2
0.7319	Intermediate Similarity	NPD4626	Approved
0.731	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6667	Approved
0.7303	Intermediate Similarity	NPD6666	Approved
0.7294	Intermediate Similarity	NPD7906	Approved
0.7286	Intermediate Similarity	NPD1608	Approved
0.7286	Intermediate Similarity	NPD2235	Phase 2
0.7286	Intermediate Similarity	NPD2231	Phase 2
0.7279	Intermediate Similarity	NPD7340	Approved
0.7279	Intermediate Similarity	NPD6353	Approved
0.7279	Intermediate Similarity	NPD6653	Approved
0.7278	Intermediate Similarity	NPD5773	Approved
0.7278	Intermediate Similarity	NPD5929	Approved
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5772	Approved
0.7273	Intermediate Similarity	NPD1512	Approved
0.7273	Intermediate Similarity	NPD7054	Approved
0.7267	Intermediate Similarity	NPD4666	Phase 3
0.7267	Intermediate Similarity	NPD7037	Approved
0.7266	Intermediate Similarity	NPD3496	Discontinued
0.7261	Intermediate Similarity	NPD6072	Discontinued
0.726	Intermediate Similarity	NPD2238	Phase 2
0.726	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1774	Approved
0.7254	Intermediate Similarity	NPD3094	Phase 2
0.7248	Intermediate Similarity	NPD6032	Approved
0.7246	Intermediate Similarity	NPD5691	Approved
0.7244	Intermediate Similarity	NPD3020	Approved
0.7244	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5111	Phase 2
0.7241	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5109	Approved
0.7241	Intermediate Similarity	NPD5110	Phase 2
0.7237	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6582	Phase 2
0.7234	Intermediate Similarity	NPD6583	Phase 3
0.7233	Intermediate Similarity	NPD3817	Phase 2
0.7233	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7097	Phase 1
0.7229	Intermediate Similarity	NPD7472	Approved
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3092	Approved
0.7214	Intermediate Similarity	NPD1611	Approved
0.7211	Intermediate Similarity	NPD5124	Phase 1
0.7211	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5709	Phase 3
0.7197	Intermediate Similarity	NPD4380	Phase 2
0.7197	Intermediate Similarity	NPD4675	Approved
0.7197	Intermediate Similarity	NPD4678	Approved
0.7194	Intermediate Similarity	NPD5125	Phase 3
0.7194	Intermediate Similarity	NPD5126	Approved
0.7192	Intermediate Similarity	NPD6233	Phase 2
0.7192	Intermediate Similarity	NPD2674	Phase 3
0.7185	Intermediate Similarity	NPD1398	Phase 1
0.7181	Intermediate Similarity	NPD7033	Discontinued
0.7179	Intermediate Similarity	NPD4210	Discontinued
0.7179	Intermediate Similarity	NPD3687	Approved
0.7179	Intermediate Similarity	NPD3686	Approved
0.7178	Intermediate Similarity	NPD6071	Discontinued
0.7178	Intermediate Similarity	NPD6232	Discontinued
0.7174	Intermediate Similarity	NPD1182	Approved
0.7171	Intermediate Similarity	NPD3892	Phase 2
0.7171	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4535	Phase 3
0.717	Intermediate Similarity	NPD8455	Phase 2
0.7163	Intermediate Similarity	NPD2233	Approved
0.7163	Intermediate Similarity	NPD1840	Phase 2
0.7163	Intermediate Similarity	NPD2232	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