NPASS Compound

Structure

CID122009 OpenBabel06191715472D 22 23 0 0 0 0 0 0 0 0999 V2000 -6.9282 -0.0000 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 -1.7321 -1.0000 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 -7.7942 0.5000 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 -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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 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 -7.7942 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 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 0.8660 0.5000 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 1 5 1 0 0 0 0 1 12 2 0 0 0 0 2 6 2 0 0 0 0 2 12 1 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 13 1 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 18 2 3 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	299.12
Volume:	310.541
LogP:	2.318
LogD:	2.673
LogS:	-2.86
# Rotatable Bonds:	6
TPSA:	89.79
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.503
Synthetic Accessibility Score:	2.061
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.009
MDCK Permeability:	1.2190229426778387e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.499
30% Bioavailability (F30%):	0.219

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	96.58979797363281%
Volume Distribution (VD):	0.566
Pgp-substrate:	2.677647829055786%

ADMET: Metabolism

CYP1A2-inhibitor:	0.713
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.503
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.727
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.67
CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.661
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	16.205
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.119
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.386
Rat Oral Acute Toxicity:	0.56
Maximum Recommended Daily Dose:	0.64
Skin Sensitization:	0.954
Carcinogencity:	0.411
Eye Corrosion:	0.003
Eye Irritation:	0.298
Respiratory Toxicity:	0.187

Download Data

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

Natural Product: NPC122009

Natural Product ID:	NPC122009
*Common Name:**	Trans-N-Caffeoyltyramine
IUPAC Name:	(E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
Synonyms:	Trans-N-Caffeoyltyramine
Standard InCHIKey:	VSHUQLRHTJOKTA-XBXARRHUSA-N
Standard InCHI:	InChI=1S/C17H17NO4/c19-14-5-1-12(2-6-14)9-10-18-17(22)8-4-13-3-7-15(20)16(21)11-13/h1-8,11,19-21H,9-10H2,(H,18,22)/b8-4+
SMILES:	c1cc(ccc1CCN=C(/C=C/c1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL206646
PubChem CID:	9994897
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]
NPO138	Daphniphyllum paxianum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17887722]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[21911291]
NPO1346	Nerine bowdenii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22312717]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO11877	Penicillium herquei	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26848504]
NPO40203	Miliusa cuneata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26928423]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO8752	Xylaria cubensis	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28802670]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31397570]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31675225]
NPO1831	Pseudodistoma arborescens	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8450325]
NPO11877	Penicillium herquei	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8609085]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO4969	Sesbania bispinosa	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8127	Veronica arvensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9153	Sorbaria sorbifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6622	Artemisia klotzchiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9153	Sorbaria sorbifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8127	Veronica arvensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9153	Sorbaria sorbifolia	Species	Rosaceae	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]
NPO6845	Mimusops caffra	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9252	Adina sessilifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1346	Nerine bowdenii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11823	Marine actinobacterium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
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]
NPO138	Daphniphyllum paxianum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4969	Sesbania bispinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21255	Hymenoxys insignis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13472	Cotula cinerea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6622	Artemisia klotzchiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9485	Haplopappus deserticola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11657	Angelica lucida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9144	Atriplex parvifolia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1412	Artemisia juncea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11934	Castanea vesca	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11877	Penicillium herquei	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11473	Viburnum lantana	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19776	Hesperocyparis arizonica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3995	Limonium sinense	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8127	Veronica arvensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1831	Pseudodistoma arborescens	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5735	Solidago serotina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8752	Xylaria cubensis	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11000	Eupatorium laevigatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1697	Bitis gabonica	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9153	Sorbaria sorbifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14564	Oophaga pumilio	Species	Dendrobatidae	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	7
Ki	1
Others	5

Activity Type	# Activity
Cell Line	3
Individual Protein	3
NON-MOLECULAR	1
Organism	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	Activity	=	84.0	%	PMID[496424]
NPT2739	Individual Protein	Tyrosinase	Mus musculus	Activity	=	15.0	%	PMID[496424]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	47800.0	nM	PMID[496427]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	47800.0	nM	PMID[496427]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	100.0	%	PMID[496423]
NPT1	Others	Radical scavenging activity		Activity	=	40.0	%	PMID[496423]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	=	30.0	%	PMID[496424]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	44100.0	nM	PMID[496425]
NPT1	Others	Radical scavenging activity		IC50	=	47600.0	nM	PMID[496425]
NPT2	Others	Unspecified		IC50	=	1860.0	nM	PMID[496426]
NPT2	Others	Unspecified		Ki	=	1770.0	nM	PMID[496426]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	47800.0	nM	PMID[496427]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	23800.0	nM	PMID[496427]

☑ 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 NPC122009 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	205
0.1-0.2	1769
0.2-0.3	10115
0.3-0.4	8396
0.4-0.5	8361
0.5-0.6	9553
0.6-0.7	3586
0.7-0.8	629
0.8-0.85	56
0.85-0.9	18
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC283468
0.9732	High Similarity	NPC268572
0.9224	High Similarity	NPC284078
0.9167	High Similarity	NPC251571
0.9115	High Similarity	NPC142599
0.9091	High Similarity	NPC24101
0.9091	High Similarity	NPC96224
0.9016	High Similarity	NPC195749
0.9016	High Similarity	NPC35961
0.9016	High Similarity	NPC52029
0.8934	High Similarity	NPC155838
0.8871	High Similarity	NPC214869
0.879	High Similarity	NPC114102
0.8699	High Similarity	NPC186898
0.8661	High Similarity	NPC6913
0.8661	High Similarity	NPC142297
0.8629	High Similarity	NPC271808
0.8584	High Similarity	NPC153690
0.8571	High Similarity	NPC231705
0.8548	High Similarity	NPC153990
0.8527	High Similarity	NPC204848
0.8527	High Similarity	NPC312770
0.8527	High Similarity	NPC41473
0.8527	High Similarity	NPC14600
0.8527	High Similarity	NPC160607
0.85	High Similarity	NPC252817
0.8468	Intermediate Similarity	NPC178902
0.8468	Intermediate Similarity	NPC301713
0.8462	Intermediate Similarity	NPC299583
0.8462	Intermediate Similarity	NPC296898
0.8455	Intermediate Similarity	NPC223393
0.8448	Intermediate Similarity	NPC146422
0.8403	Intermediate Similarity	NPC38458
0.8403	Intermediate Similarity	NPC311737
0.84	Intermediate Similarity	NPC477839
0.8393	Intermediate Similarity	NPC471511
0.8348	Intermediate Similarity	NPC254833
0.8348	Intermediate Similarity	NPC228343
0.8348	Intermediate Similarity	NPC258056
0.8319	Intermediate Similarity	NPC82963
0.8276	Intermediate Similarity	NPC174096
0.8276	Intermediate Similarity	NPC120982
0.8276	Intermediate Similarity	NPC226401
0.8276	Intermediate Similarity	NPC474149
0.8276	Intermediate Similarity	NPC147634
0.8276	Intermediate Similarity	NPC79793
0.824	Intermediate Similarity	NPC318965
0.8235	Intermediate Similarity	NPC37302
0.8205	Intermediate Similarity	NPC257430
0.8205	Intermediate Similarity	NPC179002
0.8205	Intermediate Similarity	NPC297657
0.8205	Intermediate Similarity	NPC187583
0.819	Intermediate Similarity	NPC55617
0.819	Intermediate Similarity	NPC62258
0.8182	Intermediate Similarity	NPC85276
0.8158	Intermediate Similarity	NPC239291
0.8142	Intermediate Similarity	NPC196479
0.814	Intermediate Similarity	NPC130595
0.814	Intermediate Similarity	NPC93882
0.8134	Intermediate Similarity	NPC100478
0.8134	Intermediate Similarity	NPC222039
0.8108	Intermediate Similarity	NPC109955
0.8088	Intermediate Similarity	NPC5462
0.8083	Intermediate Similarity	NPC317254
0.8077	Intermediate Similarity	NPC6854
0.8077	Intermediate Similarity	NPC313737
0.8077	Intermediate Similarity	NPC285078
0.8062	Intermediate Similarity	NPC308885
0.8062	Intermediate Similarity	NPC255550
0.8015	Intermediate Similarity	NPC218530
0.8	Intermediate Similarity	NPC120280
0.8	Intermediate Similarity	NPC118202
0.7983	Intermediate Similarity	NPC51698
0.7967	Intermediate Similarity	NPC43275
0.7949	Intermediate Similarity	NPC105727
0.7949	Intermediate Similarity	NPC34864
0.7949	Intermediate Similarity	NPC114392
0.7949	Intermediate Similarity	NPC58427
0.7949	Intermediate Similarity	NPC233835
0.7931	Intermediate Similarity	NPC477814
0.7928	Intermediate Similarity	NPC107522
0.7914	Intermediate Similarity	NPC470935
0.7914	Intermediate Similarity	NPC153644
0.7914	Intermediate Similarity	NPC471032
0.7903	Intermediate Similarity	NPC115627
0.7903	Intermediate Similarity	NPC263835
0.7903	Intermediate Similarity	NPC118522
0.7903	Intermediate Similarity	NPC169207
0.7899	Intermediate Similarity	NPC268032
0.7899	Intermediate Similarity	NPC280382
0.7895	Intermediate Similarity	NPC110764
0.7881	Intermediate Similarity	NPC71266
0.7876	Intermediate Similarity	NPC131587
0.7869	Intermediate Similarity	NPC61062
0.7869	Intermediate Similarity	NPC299252
0.7869	Intermediate Similarity	NPC277394
0.7863	Intermediate Similarity	NPC176527
0.7846	Intermediate Similarity	NPC470706
0.7842	Intermediate Similarity	NPC277857
0.7842	Intermediate Similarity	NPC115144
0.784	Intermediate Similarity	NPC83279
0.7823	Intermediate Similarity	NPC283760
0.7807	Intermediate Similarity	NPC155847
0.7807	Intermediate Similarity	NPC289381
0.7805	Intermediate Similarity	NPC145023
0.7805	Intermediate Similarity	NPC610
0.7805	Intermediate Similarity	NPC175799
0.7805	Intermediate Similarity	NPC200988
0.7786	Intermediate Similarity	NPC473724
0.7786	Intermediate Similarity	NPC45191
0.7778	Intermediate Similarity	NPC474862
0.7769	Intermediate Similarity	NPC471485
0.7768	Intermediate Similarity	NPC274678
0.7761	Intermediate Similarity	NPC126637
0.7759	Intermediate Similarity	NPC52087
0.7759	Intermediate Similarity	NPC120719
0.7759	Intermediate Similarity	NPC12278
0.7746	Intermediate Similarity	NPC127402
0.7742	Intermediate Similarity	NPC86198
0.7742	Intermediate Similarity	NPC470626
0.7742	Intermediate Similarity	NPC144343
0.7734	Intermediate Similarity	NPC95733
0.7734	Intermediate Similarity	NPC62101
0.7721	Intermediate Similarity	NPC477837
0.7721	Intermediate Similarity	NPC477838
0.7721	Intermediate Similarity	NPC323123
0.7719	Intermediate Similarity	NPC125732
0.7717	Intermediate Similarity	NPC471314
0.7717	Intermediate Similarity	NPC471315
0.7704	Intermediate Similarity	NPC254610
0.7699	Intermediate Similarity	NPC82664
0.7699	Intermediate Similarity	NPC292730
0.7699	Intermediate Similarity	NPC132271
0.7699	Intermediate Similarity	NPC216520
0.768	Intermediate Similarity	NPC470215
0.768	Intermediate Similarity	NPC70084
0.768	Intermediate Similarity	NPC470214
0.768	Intermediate Similarity	NPC141791
0.768	Intermediate Similarity	NPC217174
0.768	Intermediate Similarity	NPC109371
0.768	Intermediate Similarity	NPC263386
0.7679	Intermediate Similarity	NPC151715
0.7679	Intermediate Similarity	NPC76938
0.7672	Intermediate Similarity	NPC68055
0.7672	Intermediate Similarity	NPC477802
0.7672	Intermediate Similarity	NPC477801
0.7661	Intermediate Similarity	NPC277588
0.7661	Intermediate Similarity	NPC86947
0.7661	Intermediate Similarity	NPC293619
0.7661	Intermediate Similarity	NPC278652
0.7656	Intermediate Similarity	NPC140359
0.7656	Intermediate Similarity	NPC13020
0.7656	Intermediate Similarity	NPC211218
0.7647	Intermediate Similarity	NPC170170
0.7647	Intermediate Similarity	NPC219233
0.7647	Intermediate Similarity	NPC211468
0.7642	Intermediate Similarity	NPC303370
0.7634	Intermediate Similarity	NPC325651
0.7632	Intermediate Similarity	NPC107619
0.7627	Intermediate Similarity	NPC1786
0.7627	Intermediate Similarity	NPC1075
0.7627	Intermediate Similarity	NPC294902
0.7622	Intermediate Similarity	NPC52475
0.7619	Intermediate Similarity	NPC232316
0.7619	Intermediate Similarity	NPC227217
0.7619	Intermediate Similarity	NPC475245
0.7619	Intermediate Similarity	NPC117780
0.7619	Intermediate Similarity	NPC165133
0.7619	Intermediate Similarity	NPC242885
0.7619	Intermediate Similarity	NPC95614
0.7619	Intermediate Similarity	NPC56214
0.7619	Intermediate Similarity	NPC265454
0.7619	Intermediate Similarity	NPC34634
0.7615	Intermediate Similarity	NPC156944
0.7615	Intermediate Similarity	NPC251466
0.7615	Intermediate Similarity	NPC323775
0.7615	Intermediate Similarity	NPC236347
0.7611	Intermediate Similarity	NPC32714
0.7611	Intermediate Similarity	NPC26244
0.7607	Intermediate Similarity	NPC79672
0.7603	Intermediate Similarity	NPC166837
0.7603	Intermediate Similarity	NPC163674
0.7594	Intermediate Similarity	NPC244866
0.7586	Intermediate Similarity	NPC107602
0.7576	Intermediate Similarity	NPC474091
0.7574	Intermediate Similarity	NPC471283
0.7569	Intermediate Similarity	NPC275027
0.7569	Intermediate Similarity	NPC18614
0.7559	Intermediate Similarity	NPC24125
0.7559	Intermediate Similarity	NPC207613
0.7559	Intermediate Similarity	NPC470848
0.7559	Intermediate Similarity	NPC470849
0.7559	Intermediate Similarity	NPC98305
0.7557	Intermediate Similarity	NPC145888
0.7557	Intermediate Similarity	NPC291449
0.7557	Intermediate Similarity	NPC41331
0.7557	Intermediate Similarity	NPC161593
0.7557	Intermediate Similarity	NPC157740
0.7557	Intermediate Similarity	NPC99798
0.7557	Intermediate Similarity	NPC16031

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 NPC122009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	756
0.2-0.3	1088
0.3-0.4	2150
0.4-0.5	2856
0.5-0.6	1561
0.6-0.7	484
0.7-0.8	96
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8908	High Similarity	NPD2337	Clinical (unspecified phase)
0.8455	Intermediate Similarity	NPD5310	Approved
0.8455	Intermediate Similarity	NPD5311	Approved
0.8448	Intermediate Similarity	NPD9379	Approved
0.8448	Intermediate Similarity	NPD9377	Approved
0.8387	Intermediate Similarity	NPD3055	Approved
0.8387	Intermediate Similarity	NPD3053	Approved
0.8348	Intermediate Similarity	NPD3021	Approved
0.8348	Intermediate Similarity	NPD3022	Approved
0.814	Intermediate Similarity	NPD2674	Phase 3
0.8077	Intermediate Similarity	NPD3059	Approved
0.8077	Intermediate Similarity	NPD3062	Approved
0.8077	Intermediate Similarity	NPD3061	Approved
0.8062	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD3144	Approved
0.8062	Intermediate Similarity	NPD3145	Approved
0.7966	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD5314	Approved
0.7917	Intermediate Similarity	NPD2228	Approved
0.7917	Intermediate Similarity	NPD2229	Approved
0.7917	Intermediate Similarity	NPD2234	Approved
0.7903	Intermediate Similarity	NPD9381	Approved
0.7903	Intermediate Similarity	NPD9384	Approved
0.7874	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD4093	Discontinued
0.7752	Intermediate Similarity	NPD7451	Discontinued
0.7731	Intermediate Similarity	NPD1792	Phase 2
0.7679	Intermediate Similarity	NPD2933	Approved
0.7679	Intermediate Similarity	NPD2934	Approved
0.7656	Intermediate Similarity	NPD9622	Approved
0.7656	Intermediate Similarity	NPD1669	Approved
0.7627	Intermediate Similarity	NPD1445	Approved
0.7627	Intermediate Similarity	NPD1444	Approved
0.7615	Intermediate Similarity	NPD9621	Approved
0.7615	Intermediate Similarity	NPD9620	Approved
0.7615	Intermediate Similarity	NPD9619	Approved
0.7611	Intermediate Similarity	NPD2859	Approved
0.7611	Intermediate Similarity	NPD2860	Approved
0.7565	Intermediate Similarity	NPD3020	Approved
0.7559	Intermediate Similarity	NPD3421	Phase 3
0.7557	Intermediate Similarity	NPD9569	Approved
0.7519	Intermediate Similarity	NPD598	Approved
0.7519	Intermediate Similarity	NPD597	Approved
0.7519	Intermediate Similarity	NPD601	Approved
0.7518	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1132	Approved
0.7463	Intermediate Similarity	NPD1136	Approved
0.7463	Intermediate Similarity	NPD1130	Approved
0.746	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD9610	Approved
0.7458	Intermediate Similarity	NPD9608	Approved
0.7429	Intermediate Similarity	NPD6331	Phase 2
0.7426	Intermediate Similarity	NPD823	Approved
0.7426	Intermediate Similarity	NPD817	Approved
0.7407	Intermediate Similarity	NPD6346	Approved
0.7385	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3060	Approved
0.735	Intermediate Similarity	NPD1242	Phase 1
0.7348	Intermediate Similarity	NPD258	Approved
0.7348	Intermediate Similarity	NPD257	Approved
0.7344	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1751	Approved
0.7343	Intermediate Similarity	NPD4123	Phase 3
0.7333	Intermediate Similarity	NPD259	Phase 1
0.7328	Intermediate Similarity	NPD2922	Phase 1
0.7324	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3845	Phase 1
0.7323	Intermediate Similarity	NPD5304	Approved
0.7323	Intermediate Similarity	NPD1759	Phase 1
0.7323	Intermediate Similarity	NPD5303	Approved
0.7317	Intermediate Similarity	NPD228	Approved
0.7313	Intermediate Similarity	NPD9537	Phase 1
0.7313	Intermediate Similarity	NPD9536	Phase 1
0.7308	Intermediate Similarity	NPD2562	Approved
0.7308	Intermediate Similarity	NPD2561	Approved
0.7305	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1983	Approved
0.7287	Intermediate Similarity	NPD1980	Approved
0.7287	Intermediate Similarity	NPD1981	Approved
0.728	Intermediate Similarity	NPD1791	Approved
0.728	Intermediate Similarity	NPD1793	Approved
0.7279	Intermediate Similarity	NPD1558	Phase 1
0.7273	Intermediate Similarity	NPD2420	Approved
0.7273	Intermediate Similarity	NPD2421	Approved
0.7266	Intermediate Similarity	NPD2161	Phase 2
0.7252	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD4659	Approved
0.7244	Intermediate Similarity	NPD1758	Phase 1
0.7239	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD555	Phase 2
0.7209	Intermediate Similarity	NPD2668	Approved
0.7209	Intermediate Similarity	NPD2667	Approved
0.7194	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3136	Phase 2
0.7185	Intermediate Similarity	NPD5156	Approved
0.7185	Intermediate Similarity	NPD5155	Approved
0.7174	Intermediate Similarity	NPD2568	Approved
0.7164	Intermediate Similarity	NPD3637	Approved
0.7164	Intermediate Similarity	NPD3635	Approved
0.7164	Intermediate Similarity	NPD3636	Approved
0.7163	Intermediate Similarity	NPD7153	Discontinued
0.7153	Intermediate Similarity	NPD826	Approved
0.7153	Intermediate Similarity	NPD825	Approved
0.7143	Intermediate Similarity	NPD9618	Approved
0.7143	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4103	Phase 2
0.7143	Intermediate Similarity	NPD7450	Phase 2
0.7143	Intermediate Similarity	NPD9614	Approved
0.7132	Intermediate Similarity	NPD5718	Phase 2
0.7113	Intermediate Similarity	NPD4162	Approved
0.7111	Intermediate Similarity	NPD2606	Approved
0.7111	Intermediate Similarity	NPD2605	Approved
0.7111	Intermediate Similarity	NPD3594	Approved
0.7111	Intermediate Similarity	NPD3595	Approved
0.7109	Intermediate Similarity	NPD9616	Approved
0.7109	Intermediate Similarity	NPD9613	Approved
0.7109	Intermediate Similarity	NPD16	Approved
0.7109	Intermediate Similarity	NPD9615	Approved
0.7109	Intermediate Similarity	NPD856	Approved
0.7095	Intermediate Similarity	NPD4678	Approved
0.7095	Intermediate Similarity	NPD4675	Approved
0.709	Intermediate Similarity	NPD2195	Approved
0.709	Intermediate Similarity	NPD6584	Phase 3
0.709	Intermediate Similarity	NPD2194	Approved
0.708	Intermediate Similarity	NPD6405	Approved
0.708	Intermediate Similarity	NPD6407	Approved
0.708	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1969	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1972	Approved
0.7075	Intermediate Similarity	NPD1973	Approved
0.7069	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5283	Phase 1
0.7059	Intermediate Similarity	NPD3027	Phase 3
0.7059	Intermediate Similarity	NPD2372	Approved
0.7055	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD316	Approved
0.7045	Intermediate Similarity	NPD2232	Approved
0.7045	Intermediate Similarity	NPD2233	Approved
0.7045	Intermediate Similarity	NPD2230	Approved
0.7027	Intermediate Similarity	NPD4005	Discontinued
0.7027	Intermediate Similarity	NPD111	Approved
0.7027	Intermediate Similarity	NPD3455	Phase 2
0.7021	Intermediate Similarity	NPD9570	Approved
0.7014	Intermediate Similarity	NPD5241	Discontinued
0.7014	Intermediate Similarity	NPD302	Approved
0.7009	Intermediate Similarity	NPD844	Approved
0.7007	Intermediate Similarity	NPD5110	Phase 2
0.7007	Intermediate Similarity	NPD5111	Phase 2
0.7007	Intermediate Similarity	NPD5109	Approved
0.7	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3553	Approved
0.7	Intermediate Similarity	NPD3554	Approved
0.7	Intermediate Similarity	NPD3555	Approved
0.7	Intermediate Similarity	NPD6895	Approved
0.7	Intermediate Similarity	NPD6896	Approved
0.7	Intermediate Similarity	NPD3552	Approved
0.6986	Remote Similarity	NPD4739	Approved
0.6986	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD274	Approved
0.6978	Remote Similarity	NPD275	Approved
0.6977	Remote Similarity	NPD318	Approved
0.6977	Remote Similarity	NPD317	Approved
0.6972	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD839	Approved
0.6957	Remote Similarity	NPD840	Approved
0.6954	Remote Similarity	NPD2978	Approved
0.6954	Remote Similarity	NPD2977	Approved
0.695	Remote Similarity	NPD4108	Discontinued
0.6947	Remote Similarity	NPD2286	Discontinued
0.6934	Remote Similarity	NPD1024	Discontinued
0.6918	Remote Similarity	NPD4357	Discontinued
0.6917	Remote Similarity	NPD3028	Approved
0.6917	Remote Similarity	NPD2235	Phase 2
0.6917	Remote Similarity	NPD2231	Phase 2
0.6906	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD9568	Approved
0.6891	Remote Similarity	NPD9273	Approved
0.6875	Remote Similarity	NPD5177	Phase 3
0.6875	Remote Similarity	NPD4237	Approved
0.6875	Remote Similarity	NPD4236	Phase 3
0.6871	Remote Similarity	NPD3645	Discontinued
0.6866	Remote Similarity	NPD6583	Phase 3
0.6866	Remote Similarity	NPD1755	Approved
0.6866	Remote Similarity	NPD6582	Phase 2
0.6861	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1375	Discontinued
0.6842	Remote Similarity	NPD5773	Approved
0.6842	Remote Similarity	NPD5772	Approved
0.6835	Remote Similarity	NPD7477	Discontinued
0.6828	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3400	Discontinued
0.6824	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7526	Approved
0.6824	Remote Similarity	NPD52	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data