NPASS Compound

Structure

NPC474300 OpenBabel07101718252D 31 33 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 2.5981 -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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 0.8660 2.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 0.8660 1.5000 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 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 1.7321 -2.0000 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 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 15 2 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 20 28 2 0 0 0 0 21 12 1 1 0 0 0 21 31 1 0 0 0 0 22 29 2 0 0 0 0 22 31 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.14
Volume:	436.391
LogP:	5.805
LogD:	3.445
LogS:	-3.261
# Rotatable Bonds:	6
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.149
Synthetic Accessibility Score:	3.154
Fsp3:	0.08
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.24
MDCK Permeability:	1.7662790924077854e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.225
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.32
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	101.09317779541016%
Volume Distribution (VD):	0.375
Pgp-substrate:	1.1255440711975098%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.785
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.856
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.796
CYP2D6-substrate:	0.785
CYP3A4-inhibitor:	0.128
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	2.928
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.701
AMES Toxicity:	0.772
Rat Oral Acute Toxicity:	0.324
Maximum Recommended Daily Dose:	0.756
Skin Sensitization:	0.966
Carcinogencity:	0.357
Eye Corrosion:	0.058
Eye Irritation:	0.965
Respiratory Toxicity:	0.46

Download Data

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

Natural Product: NPC474300

Natural Product ID:	NPC474300
*Common Name:**	Cinnamoyl Alkannin
IUPAC Name:	[(1S)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] (E)-3-phenylprop-2-enoate
Synonyms:	Cinnamoyl Alkannin
Standard InCHIKey:	BXLJKAWHYOWTSY-TZTLJZABSA-N
Standard InCHI:	InChI=1S/C25H22O6/c1-15(2)8-12-21(31-22(29)13-9-16-6-4-3-5-7-16)17-14-20(28)23-18(26)10-11-19(27)24(23)25(17)30/h3-11,13-14,21,26-27H,12H2,1-2H3/b13-9+/t21-/m0/s1
SMILES:	O=C(O[C@H](C1=CC(=O)c2c(C1=O)c(O)ccc2O)CC=C(C)C)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464881
PubChem CID:	44567154
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502328]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7775984]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11421	Arnebia euchroma	Species	Boraginaceae	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	5
Others	8

Activity Type	# Activity
Cell Line	3
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT377	Cell Line	OVCAR-3	Homo sapiens	CD50	=	2.4	ug ml-1	PMID[522167]
NPT165	Cell Line	HeLa	Homo sapiens	CD50	=	3.6	ug ml-1	PMID[522167]
NPT65	Cell Line	HepG2	Homo sapiens	CD50	=	3.8	ug ml-1	PMID[522167]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MBC	=	100.0	ug ml-1	PMID[522167]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	25.0	ug.mL-1	PMID[522167]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MBC	=	100.0	ug ml-1	PMID[522167]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	25.0	ug.mL-1	PMID[522167]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MBC	>	100.0	ug ml-1	PMID[522167]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	100.0	ug.mL-1	PMID[522167]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	>	100.0	ug ml-1	PMID[522167]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[522167]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	100.0	ug ml-1	PMID[522167]

☑ 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 NPC474300 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	308
0.1-0.2	1267
0.2-0.3	2875
0.3-0.4	6544
0.4-0.5	11689
0.5-0.6	4695
0.6-0.7	7631
0.7-0.8	7105
0.8-0.85	491
0.85-0.9	63
0.9-0.95	9
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC476473
0.9778	High Similarity	NPC299405
0.9778	High Similarity	NPC111422
0.9778	High Similarity	NPC306835
0.9778	High Similarity	NPC476477
0.9778	High Similarity	NPC471602
0.9778	High Similarity	NPC216312
0.9778	High Similarity	NPC256463
0.9778	High Similarity	NPC29771
0.9706	High Similarity	NPC37992
0.9706	High Similarity	NPC327916
0.9706	High Similarity	NPC241349
0.9706	High Similarity	NPC42262
0.9706	High Similarity	NPC147542
0.9706	High Similarity	NPC32749
0.9706	High Similarity	NPC220496
0.9635	High Similarity	NPC257003
0.9635	High Similarity	NPC471444
0.9489	High Similarity	NPC295339
0.9429	High Similarity	NPC274085
0.9429	High Similarity	NPC89664
0.9416	High Similarity	NPC61590
0.9291	High Similarity	NPC103910
0.922	High Similarity	NPC21873
0.9118	High Similarity	NPC242358
0.9118	High Similarity	NPC110609
0.9118	High Similarity	NPC246693
0.8929	High Similarity	NPC305060
0.8897	High Similarity	NPC147250
0.8873	High Similarity	NPC315578
0.8836	High Similarity	NPC119767
0.8815	High Similarity	NPC306765
0.8811	High Similarity	NPC124365
0.8803	High Similarity	NPC26924
0.8786	High Similarity	NPC281513
0.8786	High Similarity	NPC22222
0.8776	High Similarity	NPC94781
0.8768	High Similarity	NPC205992
0.8759	High Similarity	NPC477409
0.8733	High Similarity	NPC474824
0.8733	High Similarity	NPC182921
0.8733	High Similarity	NPC218870
0.8733	High Similarity	NPC470408
0.8723	High Similarity	NPC141934
0.8723	High Similarity	NPC272268
0.8716	High Similarity	NPC120171
0.8716	High Similarity	NPC44378
0.8716	High Similarity	NPC280753
0.871	High Similarity	NPC474301
0.8676	High Similarity	NPC96915
0.8676	High Similarity	NPC3224
0.8675	High Similarity	NPC66029
0.8671	High Similarity	NPC1268
0.8667	High Similarity	NPC281272
0.8662	High Similarity	NPC245923
0.8658	High Similarity	NPC315520
0.8652	High Similarity	NPC27407
0.8639	High Similarity	NPC300540
0.8618	High Similarity	NPC474861
0.8613	High Similarity	NPC471530
0.8609	High Similarity	NPC474622
0.8609	High Similarity	NPC477691
0.8609	High Similarity	NPC474621
0.8603	High Similarity	NPC103540
0.86	High Similarity	NPC39819
0.8592	High Similarity	NPC474813
0.8582	High Similarity	NPC288089
0.8571	High Similarity	NPC58685
0.8571	High Similarity	NPC474630
0.8571	High Similarity	NPC70622
0.8562	High Similarity	NPC67197
0.8562	High Similarity	NPC29552
0.8551	High Similarity	NPC282923
0.8543	High Similarity	NPC474534
0.8543	High Similarity	NPC474533
0.8543	High Similarity	NPC477690
0.8542	High Similarity	NPC114620
0.8542	High Similarity	NPC103337
0.8533	High Similarity	NPC205766
0.8531	High Similarity	NPC261292
0.8531	High Similarity	NPC301915
0.8523	High Similarity	NPC470479
0.8521	High Similarity	NPC142027
0.8521	High Similarity	NPC161632
0.8521	High Similarity	NPC283088
0.8514	High Similarity	NPC470570
0.8511	High Similarity	NPC115458
0.85	High Similarity	NPC7012
0.8489	Intermediate Similarity	NPC99731
0.8489	Intermediate Similarity	NPC146647
0.8489	Intermediate Similarity	NPC34414
0.8471	Intermediate Similarity	NPC71390
0.8467	Intermediate Similarity	NPC70764
0.8456	Intermediate Similarity	NPC477153
0.8456	Intermediate Similarity	NPC375356
0.8446	Intermediate Similarity	NPC474309
0.8446	Intermediate Similarity	NPC475923
0.8446	Intermediate Similarity	NPC34482
0.8442	Intermediate Similarity	NPC208651
0.8442	Intermediate Similarity	NPC206641
0.844	Intermediate Similarity	NPC477406
0.8435	Intermediate Similarity	NPC66593
0.8431	Intermediate Similarity	NPC174599
0.8431	Intermediate Similarity	NPC82190
0.8431	Intermediate Similarity	NPC3898
0.8431	Intermediate Similarity	NPC192219
0.8429	Intermediate Similarity	NPC31539
0.8429	Intermediate Similarity	NPC55949
0.8429	Intermediate Similarity	NPC475741
0.8429	Intermediate Similarity	NPC199253
0.8429	Intermediate Similarity	NPC136588
0.8425	Intermediate Similarity	NPC283292
0.8425	Intermediate Similarity	NPC187843
0.8425	Intermediate Similarity	NPC130485
0.8421	Intermediate Similarity	NPC478220
0.8417	Intermediate Similarity	NPC48248
0.8414	Intermediate Similarity	NPC477408
0.8406	Intermediate Similarity	NPC1991
0.8406	Intermediate Similarity	NPC231774
0.84	Intermediate Similarity	NPC2569
0.84	Intermediate Similarity	NPC172329
0.8394	Intermediate Similarity	NPC234890
0.8394	Intermediate Similarity	NPC74507
0.8389	Intermediate Similarity	NPC211565
0.8389	Intermediate Similarity	NPC60389
0.8389	Intermediate Similarity	NPC285122
0.8387	Intermediate Similarity	NPC477692
0.8382	Intermediate Similarity	NPC300274
0.838	Intermediate Similarity	NPC43627
0.838	Intermediate Similarity	NPC314048
0.838	Intermediate Similarity	NPC472591
0.8378	Intermediate Similarity	NPC21599
0.8378	Intermediate Similarity	NPC477913
0.8378	Intermediate Similarity	NPC29932
0.8378	Intermediate Similarity	NPC193703
0.8378	Intermediate Similarity	NPC42540
0.8378	Intermediate Similarity	NPC48762
0.8378	Intermediate Similarity	NPC151607
0.8377	Intermediate Similarity	NPC283480
0.8377	Intermediate Similarity	NPC478027
0.8377	Intermediate Similarity	NPC313299
0.8377	Intermediate Similarity	NPC148323
0.8377	Intermediate Similarity	NPC472050
0.8369	Intermediate Similarity	NPC470831
0.8369	Intermediate Similarity	NPC244699
0.8369	Intermediate Similarity	NPC85342
0.8369	Intermediate Similarity	NPC214702
0.8366	Intermediate Similarity	NPC135522
0.8357	Intermediate Similarity	NPC278928
0.8356	Intermediate Similarity	NPC168471
0.8356	Intermediate Similarity	NPC156872
0.8356	Intermediate Similarity	NPC225243
0.8356	Intermediate Similarity	NPC183345
0.8356	Intermediate Similarity	NPC155205
0.8355	Intermediate Similarity	NPC205918
0.8354	Intermediate Similarity	NPC178281
0.8345	Intermediate Similarity	NPC33144
0.8345	Intermediate Similarity	NPC126739
0.8345	Intermediate Similarity	NPC191835
0.8345	Intermediate Similarity	NPC173980
0.8345	Intermediate Similarity	NPC197666
0.8345	Intermediate Similarity	NPC478200
0.8345	Intermediate Similarity	NPC221104
0.8344	Intermediate Similarity	NPC478219
0.8333	Intermediate Similarity	NPC472308
0.8333	Intermediate Similarity	NPC291454
0.8333	Intermediate Similarity	NPC155211
0.8333	Intermediate Similarity	NPC284495
0.8323	Intermediate Similarity	NPC44199
0.8323	Intermediate Similarity	NPC263483
0.8322	Intermediate Similarity	NPC170055
0.8322	Intermediate Similarity	NPC1249
0.8322	Intermediate Similarity	NPC474097
0.8312	Intermediate Similarity	NPC3449
0.8311	Intermediate Similarity	NPC143898
0.8311	Intermediate Similarity	NPC469885
0.8311	Intermediate Similarity	NPC471731
0.8311	Intermediate Similarity	NPC478202
0.8311	Intermediate Similarity	NPC159721
0.831	Intermediate Similarity	NPC309430
0.8301	Intermediate Similarity	NPC474843
0.8301	Intermediate Similarity	NPC115249
0.8301	Intermediate Similarity	NPC175978
0.8299	Intermediate Similarity	NPC53649
0.8299	Intermediate Similarity	NPC470842
0.8299	Intermediate Similarity	NPC472603
0.8299	Intermediate Similarity	NPC478217
0.8299	Intermediate Similarity	NPC149533
0.8299	Intermediate Similarity	NPC313123
0.8299	Intermediate Similarity	NPC472035
0.8299	Intermediate Similarity	NPC478201
0.8296	Intermediate Similarity	NPC285829
0.8296	Intermediate Similarity	NPC206778
0.8289	Intermediate Similarity	NPC294646
0.8289	Intermediate Similarity	NPC470107
0.8289	Intermediate Similarity	NPC295036
0.8289	Intermediate Similarity	NPC470568
0.8286	Intermediate Similarity	NPC237225
0.8286	Intermediate Similarity	NPC165257
0.828	Intermediate Similarity	NPC24761

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 NPC474300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	852
0.2-0.3	1433
0.3-0.4	2412
0.4-0.5	2253
0.5-0.6	1257
0.6-0.7	510
0.7-0.8	161
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8603	High Similarity	NPD1470	Approved
0.8467	Intermediate Similarity	NPD3226	Approved
0.8345	Intermediate Similarity	NPD2346	Discontinued
0.8309	Intermediate Similarity	NPD1201	Approved
0.8276	Intermediate Similarity	NPD2935	Discontinued
0.8042	Intermediate Similarity	NPD3764	Approved
0.8027	Intermediate Similarity	NPD5406	Approved
0.8027	Intermediate Similarity	NPD5408	Approved
0.8027	Intermediate Similarity	NPD5405	Approved
0.8027	Intermediate Similarity	NPD5404	Approved
0.8013	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD2313	Discontinued
0.7917	Intermediate Similarity	NPD8150	Discontinued
0.7888	Intermediate Similarity	NPD6232	Discontinued
0.7853	Intermediate Similarity	NPD7473	Discontinued
0.7848	Intermediate Similarity	NPD5402	Approved
0.7843	Intermediate Similarity	NPD2533	Approved
0.7843	Intermediate Similarity	NPD2532	Approved
0.7843	Intermediate Similarity	NPD2534	Approved
0.7838	Intermediate Similarity	NPD2799	Discontinued
0.7836	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3750	Approved
0.7748	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD8312	Approved
0.7738	Intermediate Similarity	NPD8313	Approved
0.7697	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1551	Phase 2
0.7651	Intermediate Similarity	NPD5844	Phase 1
0.7643	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7075	Discontinued
0.7639	Intermediate Similarity	NPD2798	Approved
0.7613	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD9493	Approved
0.7607	Intermediate Similarity	NPD6959	Discontinued
0.76	Intermediate Similarity	NPD1510	Phase 2
0.7597	Intermediate Similarity	NPD3300	Phase 2
0.7595	Intermediate Similarity	NPD4380	Phase 2
0.7582	Intermediate Similarity	NPD4628	Phase 3
0.7582	Intermediate Similarity	NPD8166	Discontinued
0.7578	Intermediate Similarity	NPD7768	Phase 2
0.7566	Intermediate Similarity	NPD1549	Phase 2
0.7562	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2801	Approved
0.7548	Intermediate Similarity	NPD7390	Discontinued
0.7547	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD1934	Approved
0.7483	Intermediate Similarity	NPD3748	Approved
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7003	Approved
0.7467	Intermediate Similarity	NPD1607	Approved
0.7452	Intermediate Similarity	NPD6273	Approved
0.745	Intermediate Similarity	NPD1240	Approved
0.7448	Intermediate Similarity	NPD1164	Approved
0.7448	Intermediate Similarity	NPD1203	Approved
0.7443	Intermediate Similarity	NPD6534	Approved
0.7443	Intermediate Similarity	NPD6535	Approved
0.7439	Intermediate Similarity	NPD5494	Approved
0.7434	Intermediate Similarity	NPD2796	Approved
0.7432	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3749	Approved
0.7419	Intermediate Similarity	NPD6190	Approved
0.7415	Intermediate Similarity	NPD6832	Phase 2
0.7413	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6559	Discontinued
0.7407	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5403	Approved
0.7403	Intermediate Similarity	NPD7435	Discontinued
0.74	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8434	Phase 2
0.7391	Intermediate Similarity	NPD6801	Discontinued
0.7391	Intermediate Similarity	NPD6844	Discontinued
0.7386	Intermediate Similarity	NPD2344	Approved
0.7386	Intermediate Similarity	NPD6212	Phase 3
0.7386	Intermediate Similarity	NPD6213	Phase 3
0.7386	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6663	Approved
0.7375	Intermediate Similarity	NPD6599	Discontinued
0.7365	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5736	Approved
0.7333	Intermediate Similarity	NPD6782	Approved
0.7333	Intermediate Similarity	NPD6781	Approved
0.7333	Intermediate Similarity	NPD6778	Approved
0.7333	Intermediate Similarity	NPD943	Approved
0.7333	Intermediate Similarity	NPD6777	Approved
0.7333	Intermediate Similarity	NPD6780	Approved
0.7333	Intermediate Similarity	NPD6776	Approved
0.7333	Intermediate Similarity	NPD6779	Approved
0.7325	Intermediate Similarity	NPD6799	Approved
0.7318	Intermediate Similarity	NPD7699	Phase 2
0.7318	Intermediate Similarity	NPD7700	Phase 2
0.7317	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3817	Phase 2
0.7285	Intermediate Similarity	NPD447	Suspended
0.7285	Intermediate Similarity	NPD230	Phase 1
0.7279	Intermediate Similarity	NPD2182	Approved
0.7278	Intermediate Similarity	NPD3818	Discontinued
0.7278	Intermediate Similarity	NPD7177	Discontinued
0.7278	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5401	Approved
0.7273	Intermediate Similarity	NPD2932	Approved
0.7267	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1283	Approved
0.7256	Intermediate Similarity	NPD3882	Suspended
0.7255	Intermediate Similarity	NPD4308	Phase 3
0.7255	Intermediate Similarity	NPD7033	Discontinued
0.7248	Intermediate Similarity	NPD7008	Discontinued
0.7246	Intermediate Similarity	NPD5711	Approved
0.7246	Intermediate Similarity	NPD5710	Approved
0.7241	Intermediate Similarity	NPD9717	Approved
0.7241	Intermediate Similarity	NPD1608	Approved
0.7219	Intermediate Similarity	NPD2979	Phase 3
0.7215	Intermediate Similarity	NPD1511	Approved
0.7214	Intermediate Similarity	NPD5951	Approved
0.7213	Intermediate Similarity	NPD7698	Approved
0.7213	Intermediate Similarity	NPD7696	Phase 3
0.7213	Intermediate Similarity	NPD7697	Approved
0.7211	Intermediate Similarity	NPD2797	Approved
0.7205	Intermediate Similarity	NPD7458	Discontinued
0.72	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD3268	Approved
0.7197	Intermediate Similarity	NPD2309	Approved
0.7178	Intermediate Similarity	NPD37	Approved
0.7176	Intermediate Similarity	NPD3751	Discontinued
0.7174	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7871	Phase 2
0.7174	Intermediate Similarity	NPD7870	Phase 2
0.7174	Intermediate Similarity	NPD8319	Approved
0.7174	Intermediate Similarity	NPD8320	Phase 1
0.7169	Intermediate Similarity	NPD6234	Discontinued
0.7166	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7874	Approved
0.7162	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1471	Phase 3
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6166	Phase 2
0.7158	Intermediate Similarity	NPD6823	Phase 2
0.7153	Intermediate Similarity	NPD3019	Approved
0.7153	Intermediate Similarity	NPD74	Approved
0.7153	Intermediate Similarity	NPD4626	Approved
0.7153	Intermediate Similarity	NPD9266	Approved
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD4966	Approved
0.7151	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1512	Approved
0.7114	Intermediate Similarity	NPD2861	Phase 2
0.7105	Intermediate Similarity	NPD4060	Phase 1
0.7103	Intermediate Similarity	NPD3496	Discontinued
0.7093	Intermediate Similarity	NPD7074	Phase 3
0.7083	Intermediate Similarity	NPD5691	Approved
0.7081	Intermediate Similarity	NPD920	Approved
0.708	Intermediate Similarity	NPD9263	Approved
0.708	Intermediate Similarity	NPD9264	Approved
0.708	Intermediate Similarity	NPD9267	Approved
0.7076	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7635	Approved
0.707	Intermediate Similarity	NPD2800	Approved
0.7059	Intermediate Similarity	NPD7701	Phase 2
0.7055	Intermediate Similarity	NPD1611	Approved
0.7055	Intermediate Similarity	NPD1281	Approved
0.7051	Intermediate Similarity	NPD7266	Discontinued
0.7044	Intermediate Similarity	NPD7236	Approved
0.7043	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7286	Phase 2
0.7035	Intermediate Similarity	NPD7054	Approved
0.7034	Intermediate Similarity	NPD17	Approved
0.7034	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1465	Phase 2
0.7027	Intermediate Similarity	NPD1876	Approved
0.7	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7472	Approved
0.6993	Remote Similarity	NPD4307	Phase 2
0.6987	Remote Similarity	NPD4477	Approved
0.6987	Remote Similarity	NPD2438	Suspended
0.6987	Remote Similarity	NPD6099	Approved
0.6987	Remote Similarity	NPD6100	Approved
0.6987	Remote Similarity	NPD4476	Approved
0.6985	Remote Similarity	NPD164	Approved
0.6974	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6798	Discontinued

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