NPASS Compound

Structure

CID246704 OpenBabel06191716052D 26 27 0 0 0 0 0 0 0 0999 V2000 10.3923 -3.0000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 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 7.7942 -1.5000 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 9.5263 -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 9.5263 -1.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 14 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 26 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 23 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	366.376
LogP:	3.373
LogD:	4.054
LogS:	-3.93
# Rotatable Bonds:	8
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.584
Synthetic Accessibility Score:	2.336
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.803
MDCK Permeability:	1.943522147485055e-05
Pgp-inhibitor:	0.654
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.245
Plasma Protein Binding (PPB):	99.45769500732422%
Volume Distribution (VD):	0.361
Pgp-substrate:	1.7099788188934326%

ADMET: Metabolism

CYP1A2-inhibitor:	0.918
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.745
CYP2C19-substrate:	0.13
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.45
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.777
CYP3A4-substrate:	0.621

ADMET: Excretion

Clearance (CL):	12.299
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.356
Human Hepatotoxicity (H-HT):	0.261
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.351
Rat Oral Acute Toxicity:	0.431
Maximum Recommended Daily Dose:	0.664
Skin Sensitization:	0.966
Carcinogencity:	0.705
Eye Corrosion:	0.004
Eye Irritation:	0.182
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC246704

Natural Product ID:	NPC246704
*Common Name:**	(E)-(E)-3-(4-Hydroxy-3-Methoxyphenyl)Allyl 3-(4-Hydroxy-3-Methoxyphenyl)Acrylate
IUPAC Name:	[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	PGLIMMMHQDNVRS-YZQQHVNFSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-24-18-12-14(5-8-16(18)21)4-3-11-26-20(23)10-7-15-6-9-17(22)19(13-15)25-2/h3-10,12-13,21-22H,11H2,1-2H3/b4-3+,10-7+
SMILES:	COc1cc(/C=C/COC(=O)/C=C/c2ccc(c(c2)OC)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3823769
PubChem CID:	6441913
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	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	4

Activity Type	# Activity
Cell Line	3
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	>	20000.0	nM	PMID[489021]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	22300.0	nM	PMID[489021]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	25600.0	nM	PMID[489021]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	19800.0	nM	PMID[489021]

☑ 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 NPC246704 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	263
0.1-0.2	1430
0.2-0.3	4626
0.3-0.4	11498
0.4-0.5	6479
0.5-0.6	4530
0.6-0.7	9554
0.7-0.8	3542
0.8-0.85	549
0.85-0.9	169
0.9-0.95	47
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9915	High Similarity	NPC289459
0.9832	High Similarity	NPC213552
0.9832	High Similarity	NPC120225
0.9669	High Similarity	NPC110313
0.9658	High Similarity	NPC204466
0.959	High Similarity	NPC83062
0.9576	High Similarity	NPC70752
0.9573	High Similarity	NPC202474
0.95	High Similarity	NPC20443
0.95	High Similarity	NPC146886
0.95	High Similarity	NPC60517
0.9492	High Similarity	NPC14007
0.9492	High Similarity	NPC189844
0.9492	High Similarity	NPC224814
0.9492	High Similarity	NPC269843
0.9492	High Similarity	NPC109083
0.9492	High Similarity	NPC60962
0.9407	High Similarity	NPC2058
0.9402	High Similarity	NPC272471
0.9402	High Similarity	NPC277460
0.9402	High Similarity	NPC70744
0.9402	High Similarity	NPC107588
0.9402	High Similarity	NPC164706
0.9402	High Similarity	NPC137537
0.935	High Similarity	NPC478215
0.9256	High Similarity	NPC160900
0.9256	High Similarity	NPC18984
0.9256	High Similarity	NPC106659
0.9256	High Similarity	NPC229084
0.9237	High Similarity	NPC275519
0.9213	High Similarity	NPC135127
0.9167	High Similarity	NPC470848
0.9167	High Similarity	NPC470849
0.916	High Similarity	NPC37858
0.916	High Similarity	NPC141791
0.916	High Similarity	NPC263386
0.9153	High Similarity	NPC280001
0.9106	High Similarity	NPC87113
0.907	High Similarity	NPC120852
0.907	High Similarity	NPC90431
0.9068	High Similarity	NPC281277
0.9062	High Similarity	NPC111635
0.906	High Similarity	NPC261453
0.906	High Similarity	NPC33749
0.906	High Similarity	NPC328593
0.906	High Similarity	NPC294941
0.904	High Similarity	NPC109275
0.9032	High Similarity	NPC276014
0.9016	High Similarity	NPC286573
0.9	High Similarity	NPC126206
0.8992	High Similarity	NPC39793
0.8983	High Similarity	NPC233669
0.8983	High Similarity	NPC474967
0.8974	High Similarity	NPC95381
0.8968	High Similarity	NPC241354
0.8968	High Similarity	NPC48315
0.896	High Similarity	NPC123722
0.896	High Similarity	NPC151167
0.896	High Similarity	NPC276466
0.896	High Similarity	NPC5018
0.896	High Similarity	NPC123228
0.8952	High Similarity	NPC280767
0.8934	High Similarity	NPC147654
0.8931	High Similarity	NPC284409
0.8923	High Similarity	NPC471665
0.8923	High Similarity	NPC471664
0.8917	High Similarity	NPC470626
0.8917	High Similarity	NPC309434
0.8917	High Similarity	NPC203124
0.8917	High Similarity	NPC124916
0.8906	High Similarity	NPC245120
0.8898	High Similarity	NPC217472
0.888	High Similarity	NPC303680
0.888	High Similarity	NPC90128
0.888	High Similarity	NPC118584
0.888	High Similarity	NPC84076
0.888	High Similarity	NPC179777
0.8864	High Similarity	NPC288452
0.8864	High Similarity	NPC106055
0.8864	High Similarity	NPC110699
0.8864	High Similarity	NPC289690
0.8852	High Similarity	NPC207613
0.8852	High Similarity	NPC471877
0.8852	High Similarity	NPC158949
0.8846	High Similarity	NPC477301
0.8837	High Similarity	NPC475468
0.8833	High Similarity	NPC65791
0.8833	High Similarity	NPC293619
0.8819	High Similarity	NPC304622
0.8803	High Similarity	NPC226250
0.88	High Similarity	NPC300326
0.88	High Similarity	NPC58279
0.88	High Similarity	NPC67951
0.879	High Similarity	NPC317769
0.879	High Similarity	NPC31344
0.8788	High Similarity	NPC132723
0.8788	High Similarity	NPC76032
0.878	High Similarity	NPC470212
0.878	High Similarity	NPC324571
0.878	High Similarity	NPC54872
0.878	High Similarity	NPC473853
0.878	High Similarity	NPC113865
0.878	High Similarity	NPC312675
0.878	High Similarity	NPC262156
0.878	High Similarity	NPC184651
0.878	High Similarity	NPC343720
0.8779	High Similarity	NPC157554
0.877	High Similarity	NPC95614
0.877	High Similarity	NPC56214
0.877	High Similarity	NPC242885
0.877	High Similarity	NPC227217
0.877	High Similarity	NPC117780
0.877	High Similarity	NPC165133
0.877	High Similarity	NPC232316
0.8769	High Similarity	NPC4982
0.8769	High Similarity	NPC68779
0.8769	High Similarity	NPC67247
0.8769	High Similarity	NPC249791
0.8769	High Similarity	NPC237594
0.8769	High Similarity	NPC471110
0.8769	High Similarity	NPC5310
0.8769	High Similarity	NPC476387
0.8769	High Similarity	NPC300776
0.8769	High Similarity	NPC176814
0.8769	High Similarity	NPC119060
0.876	High Similarity	NPC5423
0.8731	High Similarity	NPC157816
0.8731	High Similarity	NPC67467
0.8731	High Similarity	NPC140502
0.8729	High Similarity	NPC131530
0.872	High Similarity	NPC74478
0.871	High Similarity	NPC85488
0.8692	High Similarity	NPC36490
0.8689	High Similarity	NPC310338
0.8689	High Similarity	NPC281298
0.8678	High Similarity	NPC610
0.8678	High Similarity	NPC86947
0.8678	High Similarity	NPC175799
0.8678	High Similarity	NPC185738
0.8678	High Similarity	NPC145023
0.8678	High Similarity	NPC200988
0.8667	High Similarity	NPC478239
0.8651	High Similarity	NPC53305
0.8651	High Similarity	NPC197832
0.8651	High Similarity	NPC194519
0.8651	High Similarity	NPC257589
0.8651	High Similarity	NPC27352
0.8647	High Similarity	NPC226005
0.8647	High Similarity	NPC100389
0.8644	High Similarity	NPC78918
0.8644	High Similarity	NPC139617
0.864	High Similarity	NPC471693
0.864	High Similarity	NPC4181
0.864	High Similarity	NPC164778
0.864	High Similarity	NPC306100
0.864	High Similarity	NPC280704
0.864	High Similarity	NPC285345
0.864	High Similarity	NPC212541
0.864	High Similarity	NPC242372
0.864	High Similarity	NPC257976
0.8636	High Similarity	NPC471988
0.8632	High Similarity	NPC36108
0.8632	High Similarity	NPC246358
0.8632	High Similarity	NPC7097
0.8632	High Similarity	NPC233731
0.8629	High Similarity	NPC177291
0.8629	High Similarity	NPC127389
0.8629	High Similarity	NPC114845
0.8629	High Similarity	NPC290451
0.8629	High Similarity	NPC160380
0.8629	High Similarity	NPC38996
0.8629	High Similarity	NPC194416
0.8626	High Similarity	NPC473054
0.8607	High Similarity	NPC212743
0.8607	High Similarity	NPC86198
0.8605	High Similarity	NPC66905
0.8603	High Similarity	NPC110063
0.8594	High Similarity	NPC226661
0.8583	High Similarity	NPC58607
0.8583	High Similarity	NPC191037
0.8583	High Similarity	NPC178284
0.8583	High Similarity	NPC92207
0.8583	High Similarity	NPC127937
0.8571	High Similarity	NPC48990
0.8571	High Similarity	NPC114901
0.8571	High Similarity	NPC281780
0.8571	High Similarity	NPC293701
0.8571	High Similarity	NPC273686
0.8571	High Similarity	NPC312404
0.8561	High Similarity	NPC214729
0.8561	High Similarity	NPC113295
0.856	High Similarity	NPC288238
0.856	High Similarity	NPC114298
0.856	High Similarity	NPC262253
0.856	High Similarity	NPC473411
0.856	High Similarity	NPC71579
0.8548	High Similarity	NPC307253
0.854	High Similarity	NPC143120
0.854	High Similarity	NPC53884
0.854	High Similarity	NPC473909

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 NPC246704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	867
0.2-0.3	1644
0.3-0.4	2682
0.4-0.5	1826
0.5-0.6	1064
0.6-0.7	707
0.7-0.8	123
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9256	High Similarity	NPD4379	Clinical (unspecified phase)
0.8678	High Similarity	NPD5536	Phase 2
0.8487	Intermediate Similarity	NPD228	Approved
0.8462	Intermediate Similarity	NPD1358	Approved
0.8244	Intermediate Similarity	NPD3027	Phase 3
0.8231	Intermediate Similarity	NPD9494	Approved
0.822	Intermediate Similarity	NPD3134	Approved
0.8197	Intermediate Similarity	NPD5283	Phase 1
0.8195	Intermediate Similarity	NPD4060	Phase 1
0.8102	Intermediate Similarity	NPD7266	Discontinued
0.7953	Intermediate Similarity	NPD1357	Approved
0.7887	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD3022	Approved
0.7869	Intermediate Similarity	NPD3021	Approved
0.7836	Intermediate Similarity	NPD7095	Approved
0.7829	Intermediate Similarity	NPD3496	Discontinued
0.7793	Intermediate Similarity	NPD1653	Approved
0.7752	Intermediate Similarity	NPD4626	Approved
0.7746	Intermediate Similarity	NPD6190	Approved
0.768	Intermediate Similarity	NPD5535	Approved
0.7676	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD4628	Phase 3
0.7676	Intermediate Similarity	NPD4110	Phase 3
0.7676	Intermediate Similarity	NPD8166	Discontinued
0.7674	Intermediate Similarity	NPD5691	Approved
0.7664	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD3620	Phase 2
0.7664	Intermediate Similarity	NPD1613	Approved
0.7664	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD2982	Phase 2
0.7652	Intermediate Similarity	NPD2983	Phase 2
0.7647	Intermediate Similarity	NPD6798	Discontinued
0.7643	Intermediate Similarity	NPD2935	Discontinued
0.7642	Intermediate Similarity	NPD2684	Approved
0.763	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3455	Phase 2
0.7609	Intermediate Similarity	NPD230	Phase 1
0.7609	Intermediate Similarity	NPD4340	Discontinued
0.7609	Intermediate Similarity	NPD447	Suspended
0.7609	Intermediate Similarity	NPD6355	Discontinued
0.7591	Intermediate Similarity	NPD6233	Phase 2
0.7591	Intermediate Similarity	NPD4062	Phase 3
0.7576	Intermediate Similarity	NPD2981	Phase 2
0.7557	Intermediate Similarity	NPD3847	Discontinued
0.7556	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3882	Suspended
0.754	Intermediate Similarity	NPD7843	Approved
0.7538	Intermediate Similarity	NPD5585	Approved
0.7536	Intermediate Similarity	NPD1558	Phase 1
0.7521	Intermediate Similarity	NPD9296	Approved
0.7518	Intermediate Similarity	NPD3145	Approved
0.7518	Intermediate Similarity	NPD3144	Approved
0.7517	Intermediate Similarity	NPD4357	Discontinued
0.75	Intermediate Similarity	NPD7157	Approved
0.75	Intermediate Similarity	NPD3705	Approved
0.748	Intermediate Similarity	NPD968	Approved
0.7467	Intermediate Similarity	NPD1934	Approved
0.7464	Intermediate Similarity	NPD2674	Phase 3
0.7462	Intermediate Similarity	NPD1894	Discontinued
0.7426	Intermediate Similarity	NPD3018	Phase 2
0.7417	Intermediate Similarity	NPD2801	Approved
0.7388	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3817	Phase 2
0.7368	Intermediate Similarity	NPD1535	Discovery
0.7368	Intermediate Similarity	NPD422	Phase 1
0.7361	Intermediate Similarity	NPD3060	Approved
0.7357	Intermediate Similarity	NPD1933	Approved
0.7353	Intermediate Similarity	NPD6584	Phase 3
0.7348	Intermediate Similarity	NPD1778	Approved
0.7338	Intermediate Similarity	NPD6234	Discontinued
0.7333	Intermediate Similarity	NPD1283	Approved
0.7328	Intermediate Similarity	NPD9545	Approved
0.7313	Intermediate Similarity	NPD1481	Phase 2
0.7305	Intermediate Similarity	NPD6653	Approved
0.7303	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD291	Approved
0.7286	Intermediate Similarity	NPD4140	Approved
0.7285	Intermediate Similarity	NPD6386	Approved
0.7285	Intermediate Similarity	NPD6385	Approved
0.728	Intermediate Similarity	NPD290	Approved
0.7279	Intermediate Similarity	NPD1203	Approved
0.7279	Intermediate Similarity	NPD2797	Approved
0.7273	Intermediate Similarity	NPD6032	Approved
0.7267	Intermediate Similarity	NPD3111	Phase 1
0.7267	Intermediate Similarity	NPD7685	Pre-registration
0.7266	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4359	Approved
0.7258	Intermediate Similarity	NPD9697	Approved
0.7248	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4162	Approved
0.7231	Intermediate Similarity	NPD6671	Approved
0.7227	Intermediate Similarity	NPD2933	Approved
0.7227	Intermediate Similarity	NPD2934	Approved
0.7222	Intermediate Similarity	NPD5762	Approved
0.7222	Intermediate Similarity	NPD5763	Approved
0.7218	Intermediate Similarity	NPD5846	Approved
0.7218	Intermediate Similarity	NPD6516	Phase 2
0.7214	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1241	Discontinued
0.7206	Intermediate Similarity	NPD2922	Phase 1
0.7206	Intermediate Similarity	NPD3225	Approved
0.7203	Intermediate Similarity	NPD2799	Discontinued
0.72	Intermediate Similarity	NPD3687	Approved
0.72	Intermediate Similarity	NPD3686	Approved
0.7194	Intermediate Similarity	NPD5163	Phase 2
0.719	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1608	Approved
0.7183	Intermediate Similarity	NPD2492	Phase 1
0.7183	Intermediate Similarity	NPD2653	Approved
0.7174	Intermediate Similarity	NPD2861	Phase 2
0.7172	Intermediate Similarity	NPD4534	Discontinued
0.7167	Intermediate Similarity	NPD2860	Approved
0.7167	Intermediate Similarity	NPD2859	Approved
0.7163	Intermediate Similarity	NPD825	Approved
0.7163	Intermediate Similarity	NPD826	Approved
0.7163	Intermediate Similarity	NPD2979	Phase 3
0.7162	Intermediate Similarity	NPD1511	Approved
0.7162	Intermediate Similarity	NPD6799	Approved
0.7153	Intermediate Similarity	NPD2438	Suspended
0.7152	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5110	Phase 2
0.7143	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD5111	Phase 2
0.7143	Intermediate Similarity	NPD5109	Approved
0.7134	Intermediate Similarity	NPD8127	Discontinued
0.7134	Intermediate Similarity	NPD2821	Approved
0.7133	Intermediate Similarity	NPD7097	Phase 1
0.7132	Intermediate Similarity	NPD6582	Phase 2
0.7132	Intermediate Similarity	NPD6583	Phase 3
0.7131	Intermediate Similarity	NPD3020	Approved
0.7125	Intermediate Similarity	NPD3818	Discontinued
0.7124	Intermediate Similarity	NPD37	Approved
0.7123	Intermediate Similarity	NPD4237	Approved
0.7123	Intermediate Similarity	NPD4236	Phase 3
0.7122	Intermediate Similarity	NPD6832	Phase 2
0.7122	Intermediate Similarity	NPD4908	Phase 1
0.7114	Intermediate Similarity	NPD3536	Discontinued
0.7114	Intermediate Similarity	NPD4123	Phase 3
0.7113	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1281	Approved
0.7107	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6166	Phase 2
0.7101	Intermediate Similarity	NPD5647	Approved
0.7097	Intermediate Similarity	NPD4966	Approved
0.7097	Intermediate Similarity	NPD4965	Approved
0.7097	Intermediate Similarity	NPD4967	Phase 2
0.7091	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6232	Discontinued
0.7081	Intermediate Similarity	NPD5844	Phase 1
0.7081	Intermediate Similarity	NPD7054	Approved
0.7078	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2977	Approved
0.7078	Intermediate Similarity	NPD1465	Phase 2
0.7078	Intermediate Similarity	NPD2978	Approved
0.7075	Intermediate Similarity	NPD6331	Phase 2
0.7068	Intermediate Similarity	NPD1548	Phase 1
0.7067	Intermediate Similarity	NPD6273	Approved
0.7067	Intermediate Similarity	NPD1512	Approved
0.7059	Intermediate Similarity	NPD9717	Approved
0.7059	Intermediate Similarity	NPD6873	Phase 2
0.7055	Intermediate Similarity	NPD5958	Discontinued
0.7051	Intermediate Similarity	NPD7075	Discontinued
0.7039	Intermediate Similarity	NPD824	Approved
0.7039	Intermediate Similarity	NPD7458	Discontinued
0.7037	Intermediate Similarity	NPD7074	Phase 3
0.7037	Intermediate Similarity	NPD7472	Approved
0.7034	Intermediate Similarity	NPD1551	Phase 2
0.7031	Intermediate Similarity	NPD5451	Approved
0.7029	Intermediate Similarity	NPD987	Approved
0.7027	Intermediate Similarity	NPD2354	Approved
0.7027	Intermediate Similarity	NPD5241	Discontinued
0.7025	Intermediate Similarity	NPD7199	Phase 2
0.7021	Intermediate Similarity	NPD3764	Approved
0.7021	Intermediate Similarity	NPD5718	Phase 2
0.7021	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7228	Approved
0.7015	Intermediate Similarity	NPD1651	Approved
0.7013	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1652	Phase 2
0.7	Intermediate Similarity	NPD821	Approved
0.7	Intermediate Similarity	NPD2614	Approved
0.6994	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7028	Phase 2
0.6993	Remote Similarity	NPD555	Phase 2
0.6986	Remote Similarity	NPD3656	Approved
0.6985	Remote Similarity	NPD1610	Phase 2
0.6985	Remote Similarity	NPD1611	Approved
0.6985	Remote Similarity	NPD1091	Approved
0.698	Remote Similarity	NPD7440	Discontinued
0.697	Remote Similarity	NPD4198	Discontinued
0.6968	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4308	Phase 3
0.6966	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8397	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