NPASS Compound

Structure

CID52029 OpenBabel06191715392D 23 24 0 0 0 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 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 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -8.6603 4.0000 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 -0.0000 -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 -4.3301 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 23 1 0 0 0 0 2 6 1 0 0 0 0 2 13 2 0 0 0 0 3 7 2 0 0 0 0 3 13 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 19 2 3 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	228.08
Volume:	241.503
LogP:	3.151
LogD:	3.568
LogS:	-4.529
# Rotatable Bonds:	4
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.757
Synthetic Accessibility Score:	1.984
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.681
MDCK Permeability:	1.233518105436815e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.164
30% Bioavailability (F30%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.21
Plasma Protein Binding (PPB):	96.71855926513672%
Volume Distribution (VD):	0.964
Pgp-substrate:	3.1576857566833496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.554
CYP2C19-inhibitor:	0.954
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.761
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.155
CYP2D6-substrate:	0.7
CYP3A4-inhibitor:	0.204
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	8.205
Half-life (T1/2):	0.501

ADMET: Toxicity

hERG Blockers:	0.274
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.395
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.496
Carcinogencity:	0.748
Eye Corrosion:	0.016
Eye Irritation:	0.974
Respiratory Toxicity:	0.083

Download Data

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

Natural Product: NPC52029

Natural Product ID:	NPC52029
*Common Name:**	Trans-N-Isoferuloyltyramine
IUPAC Name:	(E)-3-(3-hydroxy-4-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
Synonyms:	Trans-N-Isoferuloyltyramine
Standard InCHIKey:	YVJONNCAHSDDLZ-WEVVVXLNSA-N
Standard InCHI:	InChI=1S/C18H19NO4/c1-23-17-8-4-14(12-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+
SMILES:	COc1ccc(cc1O)/C=C/C(=NCCc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337116
PubChem CID:	11289949
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic 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
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31397570]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23429	Lycium barbarum	Species	Solanaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	48800.0	nM	PMID[510041]
NPT1	Others	Radical scavenging activity		IC50	=	67700.0	nM	PMID[510041]

☑ 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 NPC52029 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	190
0.1-0.2	1530
0.2-0.3	8617
0.3-0.4	9932
0.4-0.5	5490
0.5-0.6	9498
0.6-0.7	5565
0.7-0.8	1635
0.8-0.85	185
0.85-0.9	33
0.9-0.95	13
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC35961
1.0	High Similarity	NPC195749
0.9918	High Similarity	NPC155838
0.9839	High Similarity	NPC214869
0.9836	High Similarity	NPC251571
0.9758	High Similarity	NPC114102
0.9675	High Similarity	NPC186898
0.9516	High Similarity	NPC153990
0.9457	High Similarity	NPC14600
0.9457	High Similarity	NPC312770
0.9457	High Similarity	NPC204848
0.9457	High Similarity	NPC41473
0.9457	High Similarity	NPC160607
0.9435	High Similarity	NPC301713
0.9385	High Similarity	NPC299583
0.9385	High Similarity	NPC296898
0.907	High Similarity	NPC130595
0.907	High Similarity	NPC93882
0.903	High Similarity	NPC222039
0.903	High Similarity	NPC100478
0.9016	High Similarity	NPC122009
0.9	High Similarity	NPC6854
0.9	High Similarity	NPC313737
0.9	High Similarity	NPC285078
0.8992	High Similarity	NPC255550
0.8992	High Similarity	NPC308885
0.8971	High Similarity	NPC5462
0.8934	High Similarity	NPC283468
0.8931	High Similarity	NPC218530
0.879	High Similarity	NPC268572
0.8777	High Similarity	NPC471032
0.8777	High Similarity	NPC153644
0.8777	High Similarity	NPC470935
0.871	High Similarity	NPC470626
0.8705	High Similarity	NPC115144
0.8705	High Similarity	NPC277857
0.8651	High Similarity	NPC83279
0.864	High Similarity	NPC43275
0.8629	High Similarity	NPC293619
0.8626	High Similarity	NPC470706
0.8603	High Similarity	NPC477837
0.8603	High Similarity	NPC477838
0.8594	High Similarity	NPC13020
0.8594	High Similarity	NPC140359
0.8592	High Similarity	NPC127402
0.8571	High Similarity	NPC117780
0.8571	High Similarity	NPC227217
0.8571	High Similarity	NPC165133
0.8571	High Similarity	NPC95614
0.8571	High Similarity	NPC56214
0.8571	High Similarity	NPC242885
0.8571	High Similarity	NPC263835
0.8571	High Similarity	NPC232316
0.8538	High Similarity	NPC251466
0.8538	High Similarity	NPC156944
0.8504	High Similarity	NPC207613
0.8492	Intermediate Similarity	NPC281298
0.8492	Intermediate Similarity	NPC310338
0.8473	Intermediate Similarity	NPC99798
0.8473	Intermediate Similarity	NPC157740
0.8473	Intermediate Similarity	NPC291449
0.8473	Intermediate Similarity	NPC41331
0.8462	Intermediate Similarity	NPC71105
0.8462	Intermediate Similarity	NPC170583
0.8462	Intermediate Similarity	NPC152186
0.8462	Intermediate Similarity	NPC182147
0.8462	Intermediate Similarity	NPC52475
0.8462	Intermediate Similarity	NPC207541
0.8462	Intermediate Similarity	NPC246133
0.8456	Intermediate Similarity	NPC254610
0.8438	Intermediate Similarity	NPC113865
0.8438	Intermediate Similarity	NPC324571
0.8438	Intermediate Similarity	NPC470212
0.8438	Intermediate Similarity	NPC160380
0.8438	Intermediate Similarity	NPC54872
0.8438	Intermediate Similarity	NPC312675
0.8438	Intermediate Similarity	NPC473853
0.8438	Intermediate Similarity	NPC38996
0.8438	Intermediate Similarity	NPC262156
0.8438	Intermediate Similarity	NPC184651
0.8438	Intermediate Similarity	NPC343720
0.8414	Intermediate Similarity	NPC107602
0.8409	Intermediate Similarity	NPC147247
0.8409	Intermediate Similarity	NPC246974
0.8403	Intermediate Similarity	NPC18614
0.8403	Intermediate Similarity	NPC275027
0.8387	Intermediate Similarity	NPC142599
0.8385	Intermediate Similarity	NPC62101
0.8385	Intermediate Similarity	NPC95733
0.8385	Intermediate Similarity	NPC300955
0.8372	Intermediate Similarity	NPC471315
0.8372	Intermediate Similarity	NPC471314
0.8372	Intermediate Similarity	NPC85488
0.8359	Intermediate Similarity	NPC14007
0.8359	Intermediate Similarity	NPC189844
0.8359	Intermediate Similarity	NPC109083
0.8359	Intermediate Similarity	NPC284078
0.8359	Intermediate Similarity	NPC224814
0.8359	Intermediate Similarity	NPC269843
0.8359	Intermediate Similarity	NPC60962
0.8333	Intermediate Similarity	NPC191302
0.8333	Intermediate Similarity	NPC86947
0.8321	Intermediate Similarity	NPC193528
0.832	Intermediate Similarity	NPC303370
0.8308	Intermediate Similarity	NPC471693
0.8308	Intermediate Similarity	NPC211218
0.8308	Intermediate Similarity	NPC280704
0.8308	Intermediate Similarity	NPC317769
0.8308	Intermediate Similarity	NPC31344
0.8293	Intermediate Similarity	NPC8547
0.8293	Intermediate Similarity	NPC166837
0.8293	Intermediate Similarity	NPC257124
0.8293	Intermediate Similarity	NPC156840
0.8293	Intermediate Similarity	NPC173746
0.8279	Intermediate Similarity	NPC246358
0.8279	Intermediate Similarity	NPC233731
0.8279	Intermediate Similarity	NPC36108
0.8279	Intermediate Similarity	NPC7097
0.8271	Intermediate Similarity	NPC469977
0.8235	Intermediate Similarity	NPC473463
0.8231	Intermediate Similarity	NPC71579
0.8231	Intermediate Similarity	NPC473411
0.8231	Intermediate Similarity	NPC262253
0.8203	Intermediate Similarity	NPC24474
0.8203	Intermediate Similarity	NPC311595
0.8197	Intermediate Similarity	NPC96224
0.8197	Intermediate Similarity	NPC24101
0.8195	Intermediate Similarity	NPC172403
0.8194	Intermediate Similarity	NPC182119
0.8189	Intermediate Similarity	NPC164386
0.8182	Intermediate Similarity	NPC233410
0.8182	Intermediate Similarity	NPC116907
0.8182	Intermediate Similarity	NPC257589
0.8182	Intermediate Similarity	NPC9067
0.8182	Intermediate Similarity	NPC194519
0.8182	Intermediate Similarity	NPC298757
0.8182	Intermediate Similarity	NPC203133
0.8182	Intermediate Similarity	NPC251855
0.8182	Intermediate Similarity	NPC472093
0.8182	Intermediate Similarity	NPC57490
0.8182	Intermediate Similarity	NPC117214
0.8182	Intermediate Similarity	NPC266705
0.8182	Intermediate Similarity	NPC29477
0.8182	Intermediate Similarity	NPC29008
0.8182	Intermediate Similarity	NPC53305
0.8182	Intermediate Similarity	NPC228771
0.8182	Intermediate Similarity	NPC221077
0.8182	Intermediate Similarity	NPC193544
0.8182	Intermediate Similarity	NPC475169
0.8182	Intermediate Similarity	NPC17943
0.8182	Intermediate Similarity	NPC208950
0.8182	Intermediate Similarity	NPC148627
0.8175	Intermediate Similarity	NPC37302
0.8168	Intermediate Similarity	NPC229084
0.8168	Intermediate Similarity	NPC228922
0.8168	Intermediate Similarity	NPC197757
0.8168	Intermediate Similarity	NPC106659
0.8168	Intermediate Similarity	NPC160900
0.8168	Intermediate Similarity	NPC18984
0.8154	Intermediate Similarity	NPC290451
0.8154	Intermediate Similarity	NPC127389
0.8148	Intermediate Similarity	NPC326599
0.8148	Intermediate Similarity	NPC329595
0.8145	Intermediate Similarity	NPC78918
0.8145	Intermediate Similarity	NPC139617
0.814	Intermediate Similarity	NPC474565
0.814	Intermediate Similarity	NPC289330
0.814	Intermediate Similarity	NPC61516
0.814	Intermediate Similarity	NPC10932
0.814	Intermediate Similarity	NPC232084
0.814	Intermediate Similarity	NPC53596
0.814	Intermediate Similarity	NPC471308
0.814	Intermediate Similarity	NPC160120
0.814	Intermediate Similarity	NPC17388
0.814	Intermediate Similarity	NPC247364
0.8138	Intermediate Similarity	NPC478189
0.8129	Intermediate Similarity	NPC231572
0.8125	Intermediate Similarity	NPC474214
0.8125	Intermediate Similarity	NPC428
0.8125	Intermediate Similarity	NPC474040
0.8125	Intermediate Similarity	NPC24233
0.8125	Intermediate Similarity	NPC135538
0.8125	Intermediate Similarity	NPC476571
0.8125	Intermediate Similarity	NPC147390
0.8125	Intermediate Similarity	NPC246587
0.8121	Intermediate Similarity	NPC329837
0.812	Intermediate Similarity	NPC127937
0.812	Intermediate Similarity	NPC214406
0.812	Intermediate Similarity	NPC303680
0.812	Intermediate Similarity	NPC120225
0.812	Intermediate Similarity	NPC28730
0.812	Intermediate Similarity	NPC274356
0.812	Intermediate Similarity	NPC44748
0.812	Intermediate Similarity	NPC17837
0.812	Intermediate Similarity	NPC103823
0.812	Intermediate Similarity	NPC92207
0.812	Intermediate Similarity	NPC213552
0.812	Intermediate Similarity	NPC84076
0.812	Intermediate Similarity	NPC191037
0.812	Intermediate Similarity	NPC223136

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 NPC52029 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	752
0.2-0.3	1138
0.3-0.4	2162
0.4-0.5	2522
0.5-0.6	1516
0.6-0.7	745
0.7-0.8	160
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.907	High Similarity	NPD2674	Phase 3
0.8992	High Similarity	NPD3145	Approved
0.8992	High Similarity	NPD3144	Approved
0.8308	Intermediate Similarity	NPD1669	Approved
0.8293	Intermediate Similarity	NPD228	Approved
0.8286	Intermediate Similarity	NPD6331	Phase 2
0.8244	Intermediate Similarity	NPD2922	Phase 1
0.8214	Intermediate Similarity	NPD3060	Approved
0.8182	Intermediate Similarity	NPD4123	Phase 3
0.8168	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2161	Phase 2
0.8092	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD1558	Phase 1
0.8016	Intermediate Similarity	NPD5283	Phase 1
0.8015	Intermediate Similarity	NPD5718	Phase 2
0.8014	Intermediate Similarity	NPD7153	Discontinued
0.7958	Intermediate Similarity	NPD4162	Approved
0.7941	Intermediate Similarity	NPD3027	Phase 3
0.7905	Intermediate Similarity	NPD4675	Approved
0.7905	Intermediate Similarity	NPD4678	Approved
0.7883	Intermediate Similarity	NPD5110	Phase 2
0.7883	Intermediate Similarity	NPD5111	Phase 2
0.7883	Intermediate Similarity	NPD5109	Approved
0.7877	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD2668	Approved
0.7863	Intermediate Similarity	NPD2667	Approved
0.7857	Intermediate Similarity	NPD6896	Approved
0.7857	Intermediate Similarity	NPD6895	Approved
0.7847	Intermediate Similarity	NPD5241	Discontinued
0.7838	Intermediate Similarity	NPD4005	Discontinued
0.7808	Intermediate Similarity	NPD4739	Approved
0.78	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3055	Approved
0.7778	Intermediate Similarity	NPD3053	Approved
0.7748	Intermediate Similarity	NPD2977	Approved
0.7748	Intermediate Similarity	NPD2978	Approved
0.774	Intermediate Similarity	NPD4357	Discontinued
0.7721	Intermediate Similarity	NPD6584	Phase 3
0.7708	Intermediate Similarity	NPD4236	Phase 3
0.7708	Intermediate Similarity	NPD5177	Phase 3
0.7708	Intermediate Similarity	NPD4237	Approved
0.7704	Intermediate Similarity	NPD5311	Approved
0.7704	Intermediate Similarity	NPD5310	Approved
0.7698	Intermediate Similarity	NPD3022	Approved
0.7698	Intermediate Similarity	NPD3021	Approved
0.7692	Intermediate Similarity	NPD1375	Discontinued
0.7687	Intermediate Similarity	NPD2230	Approved
0.7687	Intermediate Similarity	NPD2232	Approved
0.7687	Intermediate Similarity	NPD2233	Approved
0.7656	Intermediate Similarity	NPD9377	Approved
0.7656	Intermediate Similarity	NPD9379	Approved
0.7643	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD52	Approved
0.7635	Intermediate Similarity	NPD7526	Approved
0.7635	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5536	Phase 2
0.7632	Intermediate Similarity	NPD5772	Approved
0.7632	Intermediate Similarity	NPD5773	Approved
0.7597	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4083	Discontinued
0.7571	Intermediate Similarity	NPD839	Approved
0.7571	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD840	Approved
0.7554	Intermediate Similarity	NPD1024	Discontinued
0.7554	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4108	Discontinued
0.7518	Intermediate Similarity	NPD3062	Approved
0.7518	Intermediate Similarity	NPD3059	Approved
0.7518	Intermediate Similarity	NPD3061	Approved
0.75	Intermediate Similarity	NPD6582	Phase 2
0.75	Intermediate Similarity	NPD6583	Phase 3
0.7484	Intermediate Similarity	NPD4055	Discovery
0.7483	Intermediate Similarity	NPD2219	Phase 1
0.7467	Intermediate Similarity	NPD2122	Discontinued
0.745	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3656	Approved
0.7448	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7477	Discontinued
0.7432	Intermediate Similarity	NPD7124	Phase 2
0.7426	Intermediate Similarity	NPD2235	Phase 2
0.7426	Intermediate Similarity	NPD2231	Phase 2
0.7413	Intermediate Similarity	NPD2157	Approved
0.7413	Intermediate Similarity	NPD5314	Approved
0.7413	Intermediate Similarity	NPD2653	Approved
0.741	Intermediate Similarity	NPD1712	Approved
0.741	Intermediate Similarity	NPD4993	Discontinued
0.7403	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3620	Phase 2
0.7389	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1357	Approved
0.7385	Intermediate Similarity	NPD821	Approved
0.7376	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5604	Discontinued
0.7372	Intermediate Similarity	NPD2982	Phase 2
0.7372	Intermediate Similarity	NPD2983	Phase 2
0.7365	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD709	Approved
0.7342	Intermediate Similarity	NPD2821	Approved
0.7333	Intermediate Similarity	NPD9384	Approved
0.7333	Intermediate Similarity	NPD4584	Approved
0.7333	Intermediate Similarity	NPD9381	Approved
0.7328	Intermediate Similarity	NPD2228	Approved
0.7328	Intermediate Similarity	NPD2229	Approved
0.7328	Intermediate Similarity	NPD2234	Approved
0.7324	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3686	Approved
0.7303	Intermediate Similarity	NPD3687	Approved
0.7299	Intermediate Similarity	NPD2981	Phase 2
0.7296	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4010	Discontinued
0.7292	Intermediate Similarity	NPD3054	Approved
0.7292	Intermediate Similarity	NPD3052	Approved
0.729	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2808	Discontinued
0.7279	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6072	Discontinued
0.7273	Intermediate Similarity	NPD2238	Phase 2
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD7833	Phase 2
0.7261	Intermediate Similarity	NPD7831	Phase 2
0.7261	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4093	Discontinued
0.7255	Intermediate Similarity	NPD824	Approved
0.7255	Intermediate Similarity	NPD3455	Phase 2
0.7248	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD9622	Approved
0.7246	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3685	Discontinued
0.7237	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6031	Approved
0.7237	Intermediate Similarity	NPD6030	Approved
0.7231	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3985	Discontinued
0.7219	Intermediate Similarity	NPD3536	Discontinued
0.7214	Intermediate Similarity	NPD7905	Discontinued
0.7214	Intermediate Similarity	NPD9620	Approved
0.7214	Intermediate Similarity	NPD9621	Approved
0.7214	Intermediate Similarity	NPD9619	Approved
0.7214	Intermediate Similarity	NPD7451	Discontinued
0.7213	Intermediate Similarity	NPD9296	Approved
0.7209	Intermediate Similarity	NPD2684	Approved
0.7203	Intermediate Similarity	NPD3532	Approved
0.7203	Intermediate Similarity	NPD3530	Approved
0.7203	Intermediate Similarity	NPD3531	Approved
0.72	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2883	Discontinued
0.7172	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2492	Phase 1
0.7164	Intermediate Similarity	NPD3596	Phase 2
0.7163	Intermediate Similarity	NPD3018	Phase 2
0.7163	Intermediate Similarity	NPD9494	Approved
0.7162	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5090	Approved
0.7161	Intermediate Similarity	NPD5089	Approved
0.716	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1792	Phase 2
0.7153	Intermediate Similarity	NPD4060	Phase 1
0.7153	Intermediate Similarity	NPD3847	Discontinued
0.7153	Intermediate Similarity	NPD3421	Phase 3
0.7143	Intermediate Similarity	NPD3111	Phase 1
0.7133	Intermediate Similarity	NPD601	Approved
0.7133	Intermediate Similarity	NPD3692	Discontinued
0.7133	Intermediate Similarity	NPD598	Approved
0.7133	Intermediate Similarity	NPD597	Approved
0.7133	Intermediate Similarity	NPD1039	Discontinued
0.7133	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6111	Discontinued
0.7121	Intermediate Similarity	NPD7843	Approved
0.7115	Intermediate Similarity	NPD5720	Discontinued
0.7099	Intermediate Similarity	NPD27	Approved
0.7099	Intermediate Similarity	NPD2489	Approved
0.7097	Intermediate Similarity	NPD3296	Phase 1
0.709	Intermediate Similarity	NPD7157	Approved
0.7083	Intermediate Similarity	NPD1132	Approved
0.7083	Intermediate Similarity	NPD1136	Approved
0.7083	Intermediate Similarity	NPD1423	Approved
0.7083	Intermediate Similarity	NPD259	Phase 1
0.7083	Intermediate Similarity	NPD1130	Approved
0.708	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2933	Approved
0.7073	Intermediate Similarity	NPD2934	Approved
0.7071	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD6580	Approved
0.7059	Intermediate Similarity	NPD3647	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