NPASS Compound

Structure

CID14600 OpenBabel06191715342D 24 25 0 0 1 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 -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 -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 -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 -1.7321 0.0000 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 1.0000 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 -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 -6.0622 2.5000 0.0000 C 0 0 3 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 -6.0622 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 24 1 0 0 0 0 2 8 2 0 0 0 0 2 12 1 0 0 0 0 3 9 2 0 0 0 0 3 12 1 0 0 0 0 4 6 1 0 0 0 0 4 13 2 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 13 16 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 19 2 3 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	329.13
Volume:	336.627
LogP:	1.566
LogD:	1.756
LogS:	-3.606
# Rotatable Bonds:	7
TPSA:	99.02
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.607
Synthetic Accessibility Score:	2.615
Fsp3:	0.167
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:	-4.909
MDCK Permeability:	6.623562512686476e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.16
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	91.30546569824219%
Volume Distribution (VD):	0.516
Pgp-substrate:	6.626734256744385%

ADMET: Metabolism

CYP1A2-inhibitor:	0.527
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.246
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.253
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.268
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	13.547
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.137
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.258
Skin Sensitization:	0.764
Carcinogencity:	0.148
Eye Corrosion:	0.003
Eye Irritation:	0.076
Respiratory Toxicity:	0.09

Download Data

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

Natural Product: NPC14600

Natural Product ID:	NPC14600
*Common Name:**	Trans-N-Feruloyloctopamine
IUPAC Name:	(E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide
Synonyms:	Trans-N-Feruloyloctopamine
Standard InCHIKey:	YMUNILWOTSCYLI-YCRREMRBSA-N
Standard InCHI:	InChI=1S/C18H19NO5/c1-24-17-8-2-12(10-15(17)21)3-9-18(23)19-11-16(22)13-4-6-14(20)7-5-13/h2-10,16,20-22H,11H2,1H3,(H,19,23)/b9-3+
SMILES:	COc1ccc(/C=C/C(=NCC(c2ccc(cc2)O)O)O)cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036084
PubChem CID:	70681748
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]
NPO32523	solanum violaceum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22413887]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO32523	solanum violaceum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23511021]
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]
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[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]
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[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	8
Others	2

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	8.18	ug.mL-1	PMID[572909]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[572909]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	17.53	ug.mL-1	PMID[572909]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	=	16.84	ug.mL-1	PMID[572909]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[572909]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15.31	ug.mL-1	PMID[572909]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	22.58	%	PMID[572909]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	24.05	%	PMID[572909]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24600.0	nM	PMID[572910]
NPT1	Others	Radical scavenging activity		IC50	=	62400.0	nM	PMID[572910]

☑ 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 NPC14600 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	198
0.1-0.2	1281
0.2-0.3	5851
0.3-0.4	12545
0.4-0.5	4960
0.5-0.6	9007
0.6-0.7	6630
0.7-0.8	1984
0.8-0.85	195
0.85-0.9	22
0.9-0.95	18
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC160607
1.0	High Similarity	NPC41473
1.0	High Similarity	NPC204848
1.0	High Similarity	NPC312770
0.9771	High Similarity	NPC299583
0.9462	High Similarity	NPC214869
0.9457	High Similarity	NPC52029
0.9457	High Similarity	NPC35961
0.9457	High Similarity	NPC195749
0.9385	High Similarity	NPC114102
0.938	High Similarity	NPC155838
0.9302	High Similarity	NPC251571
0.9185	High Similarity	NPC296898
0.9154	High Similarity	NPC186898
0.9154	High Similarity	NPC153990
0.9143	High Similarity	NPC471032
0.9143	High Similarity	NPC470935
0.9077	High Similarity	NPC301713
0.9071	High Similarity	NPC115144
0.9071	High Similarity	NPC277857
0.8929	High Similarity	NPC5462
0.8923	High Similarity	NPC95733
0.8923	High Similarity	NPC62101
0.8741	High Similarity	NPC130595
0.8741	High Similarity	NPC93882
0.8712	High Similarity	NPC29477
0.8705	High Similarity	NPC477837
0.8705	High Similarity	NPC477838
0.8702	High Similarity	NPC211218
0.8702	High Similarity	NPC471693
0.8676	High Similarity	NPC6854
0.8676	High Similarity	NPC313737
0.8676	High Similarity	NPC285078
0.8667	High Similarity	NPC326599
0.8667	High Similarity	NPC329595
0.8615	High Similarity	NPC207613
0.8613	High Similarity	NPC218530
0.8582	High Similarity	NPC100478
0.8582	High Similarity	NPC222039
0.8571	High Similarity	NPC194519
0.8571	High Similarity	NPC148627
0.8562	High Similarity	NPC127402
0.8552	High Similarity	NPC182119
0.855	High Similarity	NPC324571
0.855	High Similarity	NPC54872
0.855	High Similarity	NPC470212
0.855	High Similarity	NPC312675
0.855	High Similarity	NPC473853
0.855	High Similarity	NPC113865
0.855	High Similarity	NPC262156
0.855	High Similarity	NPC184651
0.855	High Similarity	NPC343720
0.8529	High Similarity	NPC308885
0.8529	High Similarity	NPC255550
0.8527	High Similarity	NPC122009
0.8507	High Similarity	NPC191037
0.8507	High Similarity	NPC58607
0.8507	High Similarity	NPC178284
0.8496	Intermediate Similarity	NPC293701
0.8496	Intermediate Similarity	NPC48990
0.8496	Intermediate Similarity	NPC114901
0.8462	Intermediate Similarity	NPC268572
0.845	Intermediate Similarity	NPC283468
0.8444	Intermediate Similarity	NPC118533
0.8444	Intermediate Similarity	NPC118787
0.8444	Intermediate Similarity	NPC183181
0.8444	Intermediate Similarity	NPC319625
0.8444	Intermediate Similarity	NPC147821
0.8444	Intermediate Similarity	NPC165045
0.8444	Intermediate Similarity	NPC41706
0.8444	Intermediate Similarity	NPC163332
0.8444	Intermediate Similarity	NPC111247
0.8444	Intermediate Similarity	NPC292056
0.8429	Intermediate Similarity	NPC254610
0.8392	Intermediate Similarity	NPC63628
0.8392	Intermediate Similarity	NPC178466
0.8389	Intermediate Similarity	NPC107602
0.8385	Intermediate Similarity	NPC470626
0.8385	Intermediate Similarity	NPC255675
0.8382	Intermediate Similarity	NPC245826
0.8382	Intermediate Similarity	NPC206615
0.8382	Intermediate Similarity	NPC474178
0.8382	Intermediate Similarity	NPC98631
0.8382	Intermediate Similarity	NPC186843
0.8382	Intermediate Similarity	NPC470213
0.8382	Intermediate Similarity	NPC252307
0.8378	Intermediate Similarity	NPC275027
0.8358	Intermediate Similarity	NPC94276
0.8358	Intermediate Similarity	NPC109822
0.8356	Intermediate Similarity	NPC153644
0.8346	Intermediate Similarity	NPC85488
0.8346	Intermediate Similarity	NPC71090
0.8333	Intermediate Similarity	NPC284078
0.8321	Intermediate Similarity	NPC320987
0.8321	Intermediate Similarity	NPC475875
0.8321	Intermediate Similarity	NPC5851
0.8321	Intermediate Similarity	NPC181969
0.8321	Intermediate Similarity	NPC476968
0.8321	Intermediate Similarity	NPC311595
0.8321	Intermediate Similarity	NPC170844
0.8321	Intermediate Similarity	NPC24474
0.8321	Intermediate Similarity	NPC43275
0.8321	Intermediate Similarity	NPC212015
0.8321	Intermediate Similarity	NPC86030
0.8309	Intermediate Similarity	NPC5428
0.8308	Intermediate Similarity	NPC293619
0.8308	Intermediate Similarity	NPC164386
0.8284	Intermediate Similarity	NPC140359
0.8284	Intermediate Similarity	NPC280704
0.8284	Intermediate Similarity	NPC13020
0.8271	Intermediate Similarity	NPC290451
0.8271	Intermediate Similarity	NPC127389
0.8271	Intermediate Similarity	NPC470804
0.8271	Intermediate Similarity	NPC476343
0.8261	Intermediate Similarity	NPC187998
0.8261	Intermediate Similarity	NPC145305
0.8261	Intermediate Similarity	NPC143483
0.8261	Intermediate Similarity	NPC64201
0.8261	Intermediate Similarity	NPC472338
0.8261	Intermediate Similarity	NPC153739
0.8261	Intermediate Similarity	NPC257582
0.8261	Intermediate Similarity	NPC77040
0.8261	Intermediate Similarity	NPC242807
0.8261	Intermediate Similarity	NPC174495
0.8261	Intermediate Similarity	NPC42300
0.8261	Intermediate Similarity	NPC241522
0.8261	Intermediate Similarity	NPC92164
0.8258	Intermediate Similarity	NPC148615
0.8258	Intermediate Similarity	NPC95614
0.8258	Intermediate Similarity	NPC117780
0.8258	Intermediate Similarity	NPC56214
0.8258	Intermediate Similarity	NPC35071
0.8258	Intermediate Similarity	NPC165133
0.8258	Intermediate Similarity	NPC232316
0.8258	Intermediate Similarity	NPC242885
0.8258	Intermediate Similarity	NPC263835
0.8258	Intermediate Similarity	NPC227217
0.8258	Intermediate Similarity	NPC177475
0.8248	Intermediate Similarity	NPC128208
0.8248	Intermediate Similarity	NPC282703
0.8248	Intermediate Similarity	NPC184733
0.8248	Intermediate Similarity	NPC21867
0.8248	Intermediate Similarity	NPC72529
0.8248	Intermediate Similarity	NPC45774
0.8248	Intermediate Similarity	NPC129570
0.8248	Intermediate Similarity	NPC11258
0.8244	Intermediate Similarity	NPC474214
0.8235	Intermediate Similarity	NPC50380
0.8235	Intermediate Similarity	NPC179250
0.8231	Intermediate Similarity	NPC221049
0.8201	Intermediate Similarity	NPC470096
0.8201	Intermediate Similarity	NPC277804
0.8201	Intermediate Similarity	NPC470095
0.8201	Intermediate Similarity	NPC472597
0.8201	Intermediate Similarity	NPC474017
0.8195	Intermediate Similarity	NPC83279
0.8194	Intermediate Similarity	NPC90984
0.8188	Intermediate Similarity	NPC470706
0.8188	Intermediate Similarity	NPC52475
0.8182	Intermediate Similarity	NPC474320
0.8182	Intermediate Similarity	NPC135961
0.8182	Intermediate Similarity	NPC310338
0.8182	Intermediate Similarity	NPC281298
0.8175	Intermediate Similarity	NPC157740
0.8175	Intermediate Similarity	NPC106511
0.8175	Intermediate Similarity	NPC99798
0.8162	Intermediate Similarity	NPC208950
0.8162	Intermediate Similarity	NPC203133
0.8162	Intermediate Similarity	NPC116907
0.8162	Intermediate Similarity	NPC472093
0.8162	Intermediate Similarity	NPC251855
0.8162	Intermediate Similarity	NPC298757
0.8162	Intermediate Similarity	NPC117214
0.8162	Intermediate Similarity	NPC475169
0.8162	Intermediate Similarity	NPC221077
0.8162	Intermediate Similarity	NPC57490
0.8162	Intermediate Similarity	NPC193544
0.8162	Intermediate Similarity	NPC233410
0.8162	Intermediate Similarity	NPC17943
0.8151	Intermediate Similarity	NPC313414
0.8148	Intermediate Similarity	NPC228922
0.8148	Intermediate Similarity	NPC197757
0.8148	Intermediate Similarity	NPC31344
0.8148	Intermediate Similarity	NPC317769
0.8143	Intermediate Similarity	NPC16208
0.8143	Intermediate Similarity	NPC253105
0.8143	Intermediate Similarity	NPC184447
0.8143	Intermediate Similarity	NPC160991
0.8143	Intermediate Similarity	NPC7903
0.8143	Intermediate Similarity	NPC201587
0.8143	Intermediate Similarity	NPC106739
0.8143	Intermediate Similarity	NPC35932
0.8134	Intermediate Similarity	NPC160380
0.8134	Intermediate Similarity	NPC38996
0.8133	Intermediate Similarity	NPC18614
0.8116	Intermediate Similarity	NPC470084
0.8116	Intermediate Similarity	NPC472968
0.8116	Intermediate Similarity	NPC246974
0.8116	Intermediate Similarity	NPC147247
0.8106	Intermediate Similarity	NPC474040

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 NPC14600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	677
0.2-0.3	1144
0.3-0.4	2290
0.4-0.5	2411
0.5-0.6	1499
0.6-0.7	769
0.7-0.8	196
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD2674	Phase 3
0.8714	High Similarity	NPD3060	Approved
0.8529	High Similarity	NPD3145	Approved
0.8529	High Similarity	NPD3144	Approved
0.8414	Intermediate Similarity	NPD4123	Phase 3
0.8321	Intermediate Similarity	NPD3027	Phase 3
0.8264	Intermediate Similarity	NPD6331	Phase 2
0.8212	Intermediate Similarity	NPD2978	Approved
0.8212	Intermediate Similarity	NPD2977	Approved
0.8194	Intermediate Similarity	NPD4237	Approved
0.8194	Intermediate Similarity	NPD4162	Approved
0.8194	Intermediate Similarity	NPD4236	Phase 3
0.8188	Intermediate Similarity	NPD4005	Discontinued
0.8138	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4678	Approved
0.8133	Intermediate Similarity	NPD4675	Approved
0.8112	Intermediate Similarity	NPD2161	Phase 2
0.8108	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD5772	Approved
0.8092	Intermediate Similarity	NPD5773	Approved
0.8082	Intermediate Similarity	NPD5241	Discontinued
0.8052	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1669	Approved
0.8014	Intermediate Similarity	NPD3062	Approved
0.8014	Intermediate Similarity	NPD3059	Approved
0.8014	Intermediate Similarity	NPD3061	Approved
0.8014	Intermediate Similarity	NPD1558	Phase 1
0.8	Intermediate Similarity	NPD7153	Discontinued
0.7986	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD228	Approved
0.7956	Intermediate Similarity	NPD2922	Phase 1
0.7931	Intermediate Similarity	NPD1375	Discontinued
0.7902	Intermediate Similarity	NPD5314	Approved
0.7883	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD52	Approved
0.7867	Intermediate Similarity	NPD7526	Approved
0.7852	Intermediate Similarity	NPD9381	Approved
0.7852	Intermediate Similarity	NPD9384	Approved
0.7823	Intermediate Similarity	NPD5177	Phase 3
0.7817	Intermediate Similarity	NPD839	Approved
0.7817	Intermediate Similarity	NPD840	Approved
0.7808	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4739	Approved
0.7792	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3052	Approved
0.7778	Intermediate Similarity	NPD3054	Approved
0.7763	Intermediate Similarity	NPD3687	Approved
0.7763	Intermediate Similarity	NPD3686	Approved
0.7754	Intermediate Similarity	NPD9622	Approved
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5718	Phase 2
0.7742	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5283	Phase 1
0.7714	Intermediate Similarity	NPD9620	Approved
0.7714	Intermediate Similarity	NPD6584	Phase 3
0.7714	Intermediate Similarity	NPD9619	Approved
0.7714	Intermediate Similarity	NPD9621	Approved
0.7682	Intermediate Similarity	NPD3536	Discontinued
0.7681	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1613	Approved
0.7639	Intermediate Similarity	NPD2238	Phase 2
0.7622	Intermediate Similarity	NPD597	Approved
0.7622	Intermediate Similarity	NPD5110	Phase 2
0.7622	Intermediate Similarity	NPD598	Approved
0.7622	Intermediate Similarity	NPD601	Approved
0.7622	Intermediate Similarity	NPD5109	Approved
0.7622	Intermediate Similarity	NPD5111	Phase 2
0.7616	Intermediate Similarity	NPD4357	Discontinued
0.7603	Intermediate Similarity	NPD6896	Approved
0.7603	Intermediate Similarity	NPD6895	Approved
0.76	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD2667	Approved
0.7591	Intermediate Similarity	NPD2668	Approved
0.7582	Intermediate Similarity	NPD2122	Discontinued
0.7569	Intermediate Similarity	NPD1132	Approved
0.7569	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1136	Approved
0.7569	Intermediate Similarity	NPD1130	Approved
0.7554	Intermediate Similarity	NPD2235	Phase 2
0.7554	Intermediate Similarity	NPD2231	Phase 2
0.7518	Intermediate Similarity	NPD3055	Approved
0.7518	Intermediate Similarity	NPD3053	Approved
0.7517	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3620	Phase 2
0.7516	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3685	Discontinued
0.75	Intermediate Similarity	NPD6582	Phase 2
0.75	Intermediate Similarity	NPD6583	Phase 3
0.75	Intermediate Similarity	NPD6072	Discontinued
0.7484	Intermediate Similarity	NPD4055	Discovery
0.7483	Intermediate Similarity	NPD2219	Phase 1
0.7483	Intermediate Similarity	NPD2677	Approved
0.7469	Intermediate Similarity	NPD4083	Discontinued
0.7451	Intermediate Similarity	NPD3985	Discontinued
0.7451	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5311	Approved
0.7447	Intermediate Similarity	NPD5310	Approved
0.7434	Intermediate Similarity	NPD7124	Phase 2
0.7432	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4108	Discontinued
0.7432	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2233	Approved
0.7429	Intermediate Similarity	NPD2232	Approved
0.7429	Intermediate Similarity	NPD2562	Approved
0.7429	Intermediate Similarity	NPD2230	Approved
0.7429	Intermediate Similarity	NPD2561	Approved
0.7424	Intermediate Similarity	NPD3021	Approved
0.7424	Intermediate Similarity	NPD3022	Approved
0.7423	Intermediate Similarity	NPD27	Approved
0.7423	Intermediate Similarity	NPD2489	Approved
0.7415	Intermediate Similarity	NPD823	Approved
0.7415	Intermediate Similarity	NPD817	Approved
0.7405	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4666	Phase 3
0.7391	Intermediate Similarity	NPD1357	Approved
0.7388	Intermediate Similarity	NPD9377	Approved
0.7388	Intermediate Similarity	NPD9379	Approved
0.7379	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4659	Approved
0.7375	Intermediate Similarity	NPD5604	Discontinued
0.7372	Intermediate Similarity	NPD3455	Phase 2
0.7361	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2563	Approved
0.7358	Intermediate Similarity	NPD2560	Approved
0.7338	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1423	Approved
0.7329	Intermediate Similarity	NPD3531	Approved
0.7329	Intermediate Similarity	NPD3532	Approved
0.7329	Intermediate Similarity	NPD5709	Phase 3
0.7329	Intermediate Similarity	NPD3530	Approved
0.7329	Intermediate Similarity	NPD7477	Discontinued
0.732	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3179	Approved
0.731	Intermediate Similarity	NPD3180	Approved
0.731	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1024	Discontinued
0.7297	Intermediate Similarity	NPD2568	Approved
0.7297	Intermediate Similarity	NPD2157	Approved
0.7293	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4993	Discontinued
0.7292	Intermediate Similarity	NPD1712	Approved
0.7284	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1774	Approved
0.7273	Intermediate Similarity	NPD4103	Phase 2
0.7273	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD821	Approved
0.7256	Intermediate Similarity	NPD2969	Approved
0.7256	Intermediate Similarity	NPD2970	Approved
0.7254	Intermediate Similarity	NPD2982	Phase 2
0.7254	Intermediate Similarity	NPD2983	Phase 2
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7246	Intermediate Similarity	NPD856	Approved
0.7246	Intermediate Similarity	NPD16	Approved
0.7241	Intermediate Similarity	NPD600	Approved
0.7241	Intermediate Similarity	NPD596	Approved
0.7239	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD558	Phase 2
0.7219	Intermediate Similarity	NPD3656	Approved
0.7218	Intermediate Similarity	NPD2684	Approved
0.7211	Intermediate Similarity	NPD6405	Approved
0.7211	Intermediate Similarity	NPD6407	Approved
0.7209	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2154	Approved
0.72	Intermediate Similarity	NPD2156	Approved
0.72	Intermediate Similarity	NPD2155	Approved
0.7197	Intermediate Similarity	NPD4210	Discontinued
0.7195	Intermediate Similarity	NPD3051	Approved
0.7183	Intermediate Similarity	NPD2981	Phase 2
0.7181	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2653	Approved
0.7174	Intermediate Similarity	NPD3596	Phase 2
0.7172	Intermediate Similarity	NPD3018	Phase 2
0.7171	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5090	Approved
0.717	Intermediate Similarity	NPD5089	Approved
0.717	Intermediate Similarity	NPD6386	Approved
0.717	Intermediate Similarity	NPD6385	Approved
0.7161	Intermediate Similarity	NPD7213	Phase 3
0.7161	Intermediate Similarity	NPD7212	Phase 2
0.716	Intermediate Similarity	NPD7039	Approved
0.716	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7833	Phase 2
0.716	Intermediate Similarity	NPD7831	Phase 2
0.716	Intermediate Similarity	NPD7038	Approved
0.7153	Intermediate Similarity	NPD1819	Approved
0.7153	Intermediate Similarity	NPD1820	Approved
0.7153	Intermediate Similarity	NPD1817	Approved
0.7153	Intermediate Similarity	NPD1818	Approved
0.7152	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3111	Phase 1
0.7152	Intermediate Similarity	NPD6032	Approved
0.7143	Intermediate Similarity	NPD3559	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