NPASS Compound

Structure

CID155838 OpenBabel06191715522D 22 23 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 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 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 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 6.9282 -0.0000 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 0.8660 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 1.7321 -0.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 N 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 4.3301 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 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 19 2 3 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	297.14
Volume:	319.047
LogP:	2.878
LogD:	3.3
LogS:	-3.463
# Rotatable Bonds:	7
TPSA:	58.56
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.806
Synthetic Accessibility Score:	1.831
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:	-4.884
MDCK Permeability:	1.9066963432123885e-05
Pgp-inhibitor:	0.171
Pgp-substrate:	0.078
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.163

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.649
Plasma Protein Binding (PPB):	97.2934341430664%
Volume Distribution (VD):	0.668
Pgp-substrate:	1.544065237045288%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.886
CYP2C19-inhibitor:	0.905
CYP2C19-substrate:	0.396
CYP2C9-inhibitor:	0.809
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.777
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.623
CYP3A4-substrate:	0.44

ADMET: Excretion

Clearance (CL):	8.933
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.288
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.59
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.77
Skin Sensitization:	0.924
Carcinogencity:	0.244
Eye Corrosion:	0.004
Eye Irritation:	0.16
Respiratory Toxicity:	0.679

Download Data

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

Natural Product: NPC155838

Natural Product ID:	NPC155838
*Common Name:**	3-(4-Hydroxy-3-Methoxyphenyl)-N-Phenethylacrylamide
IUPAC Name:	(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(2-phenylethyl)prop-2-enamide
Synonyms:
Standard InCHIKey:	QSHSRHRDAVWDHM-CSKARUKUSA-N
Standard InCHI:	InChI=1S/C18H19NO3/c1-22-17-13-15(7-9-16(17)20)8-10-18(21)19-12-11-14-5-3-2-4-6-14/h2-10,13,20H,11-12H2,1H3,(H,19,21)/b10-8+
SMILES:	COc1cc(ccc1O)/C=C/C(=NCCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL206700
PubChem CID:	11162295
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
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	flowers	n.a.	n.a.	PMID[10075775]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479331]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15387664]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524603]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	San Antonio, Texas	2004-JUN	PMID[25685941]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	n.a.	n.a.	PMID[25685941]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26238319]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29924604]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	Suriname rainforest	n.a.	PMID[9428162]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15802	Papaver pseudocanescens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO968	Artemisia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18533	Delisea elegans	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18169	Creosphaeria sassafras	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25370	Botrychium ternatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5455	Euploca racemosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16325	Sideritis dasygnaphala	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19572	Pellacalyx axillaris	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12870	Curcuma aeruginosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19170	Lasianthaea podocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16981	Gutierrezia dracunculoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18424	Selinum libanotis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15127	Senecio congestus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12223	Stellaria media	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18927	Clinacanthus nutans	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11646	Morella pensylvanica	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18262	Aspergillus microcysticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12914	Sarcophyton flexuosum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17354	Micromonospora echinospora	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17230	Psidium acutangulum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17499	Bursera kerberi	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19709	Pseudocyphellaria australiensis	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4679	Hedysarum gmelini	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19371	Costasiella ocellifera	Species	Costasiellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11081	Baccharis grandicapitulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9906	Zephyranthes flava	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17114	Streptomyces melanogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18348	Crotalaria stolzii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16135	Pestalotiopsis oenotherae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17630	Helenium integrifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8172	Emericellopsis minima	Species	n.a.	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	19.0	%	PMID[523512]

☑ 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 NPC155838 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	191
0.1-0.2	1675
0.2-0.3	9299
0.3-0.4	9155
0.4-0.5	5602
0.5-0.6	9703
0.6-0.7	5340
0.7-0.8	1517
0.8-0.85	160
0.85-0.9	33
0.9-0.95	14
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC195749
0.9918	High Similarity	NPC35961
0.9918	High Similarity	NPC52029
0.9758	High Similarity	NPC214869
0.9754	High Similarity	NPC251571
0.9677	High Similarity	NPC114102
0.9593	High Similarity	NPC186898
0.9593	High Similarity	NPC153990
0.9512	High Similarity	NPC301713
0.938	High Similarity	NPC312770
0.938	High Similarity	NPC14600
0.938	High Similarity	NPC204848
0.938	High Similarity	NPC160607
0.938	High Similarity	NPC41473
0.9308	High Similarity	NPC296898
0.9308	High Similarity	NPC299583
0.9141	High Similarity	NPC130595
0.9141	High Similarity	NPC93882
0.907	High Similarity	NPC6854
0.907	High Similarity	NPC313737
0.907	High Similarity	NPC285078
0.9062	High Similarity	NPC255550
0.9062	High Similarity	NPC308885
0.9008	High Similarity	NPC283468
0.9	High Similarity	NPC218530
0.8955	High Similarity	NPC222039
0.8955	High Similarity	NPC100478
0.8934	High Similarity	NPC122009
0.8897	High Similarity	NPC5462
0.871	High Similarity	NPC43275
0.871	High Similarity	NPC268572
0.8705	High Similarity	NPC471032
0.8705	High Similarity	NPC470935
0.8705	High Similarity	NPC153644
0.8692	High Similarity	NPC470706
0.8661	High Similarity	NPC13020
0.8661	High Similarity	NPC140359
0.864	High Similarity	NPC263835
0.8633	High Similarity	NPC277857
0.8633	High Similarity	NPC115144
0.8629	High Similarity	NPC470626
0.8605	High Similarity	NPC251466
0.8605	High Similarity	NPC156944
0.8571	High Similarity	NPC83279
0.856	High Similarity	NPC310338
0.856	High Similarity	NPC281298
0.8548	High Similarity	NPC293619
0.8538	High Similarity	NPC99798
0.8538	High Similarity	NPC157740
0.8538	High Similarity	NPC41331
0.8538	High Similarity	NPC291449
0.8529	High Similarity	NPC477837
0.8529	High Similarity	NPC477838
0.8527	High Similarity	NPC246133
0.8527	High Similarity	NPC71105
0.8527	High Similarity	NPC182147
0.8527	High Similarity	NPC152186
0.8527	High Similarity	NPC170583
0.8527	High Similarity	NPC207541
0.8521	High Similarity	NPC127402
0.8519	High Similarity	NPC254610
0.8492	Intermediate Similarity	NPC117780
0.8492	Intermediate Similarity	NPC232316
0.8492	Intermediate Similarity	NPC227217
0.8492	Intermediate Similarity	NPC165133
0.8492	Intermediate Similarity	NPC95614
0.8492	Intermediate Similarity	NPC242885
0.8492	Intermediate Similarity	NPC56214
0.8473	Intermediate Similarity	NPC246974
0.8473	Intermediate Similarity	NPC147247
0.8455	Intermediate Similarity	NPC142599
0.845	Intermediate Similarity	NPC62101
0.845	Intermediate Similarity	NPC300955
0.845	Intermediate Similarity	NPC95733
0.8438	Intermediate Similarity	NPC471314
0.8438	Intermediate Similarity	NPC471315
0.8425	Intermediate Similarity	NPC207613
0.84	Intermediate Similarity	NPC86947
0.8397	Intermediate Similarity	NPC191302
0.8392	Intermediate Similarity	NPC52475
0.8387	Intermediate Similarity	NPC303370
0.8382	Intermediate Similarity	NPC193528
0.8372	Intermediate Similarity	NPC211218
0.8361	Intermediate Similarity	NPC8547
0.8361	Intermediate Similarity	NPC156840
0.8361	Intermediate Similarity	NPC173746
0.8361	Intermediate Similarity	NPC257124
0.8361	Intermediate Similarity	NPC166837
0.8359	Intermediate Similarity	NPC160380
0.8359	Intermediate Similarity	NPC324571
0.8359	Intermediate Similarity	NPC54872
0.8359	Intermediate Similarity	NPC38996
0.8359	Intermediate Similarity	NPC184651
0.8359	Intermediate Similarity	NPC343720
0.8359	Intermediate Similarity	NPC113865
0.8359	Intermediate Similarity	NPC473853
0.8359	Intermediate Similarity	NPC262156
0.8359	Intermediate Similarity	NPC312675
0.8359	Intermediate Similarity	NPC470212
0.8347	Intermediate Similarity	NPC233731
0.8347	Intermediate Similarity	NPC7097
0.8347	Intermediate Similarity	NPC246358
0.8347	Intermediate Similarity	NPC36108
0.8345	Intermediate Similarity	NPC107602
0.8333	Intermediate Similarity	NPC18614
0.8333	Intermediate Similarity	NPC275027
0.8333	Intermediate Similarity	NPC469977
0.8295	Intermediate Similarity	NPC85488
0.8281	Intermediate Similarity	NPC224814
0.8281	Intermediate Similarity	NPC189844
0.8281	Intermediate Similarity	NPC284078
0.8281	Intermediate Similarity	NPC109083
0.8281	Intermediate Similarity	NPC60962
0.8281	Intermediate Similarity	NPC269843
0.8281	Intermediate Similarity	NPC14007
0.8264	Intermediate Similarity	NPC96224
0.8264	Intermediate Similarity	NPC24101
0.8258	Intermediate Similarity	NPC172403
0.8254	Intermediate Similarity	NPC164386
0.8244	Intermediate Similarity	NPC29477
0.8231	Intermediate Similarity	NPC317769
0.8231	Intermediate Similarity	NPC471693
0.8231	Intermediate Similarity	NPC31344
0.8231	Intermediate Similarity	NPC280704
0.8217	Intermediate Similarity	NPC290451
0.8217	Intermediate Similarity	NPC127389
0.8211	Intermediate Similarity	NPC139617
0.8211	Intermediate Similarity	NPC78918
0.8209	Intermediate Similarity	NPC326599
0.8209	Intermediate Similarity	NPC329595
0.8203	Intermediate Similarity	NPC289330
0.8203	Intermediate Similarity	NPC17388
0.8203	Intermediate Similarity	NPC53596
0.8203	Intermediate Similarity	NPC160120
0.8203	Intermediate Similarity	NPC471308
0.8188	Intermediate Similarity	NPC231572
0.8162	Intermediate Similarity	NPC473463
0.8154	Intermediate Similarity	NPC473411
0.8154	Intermediate Similarity	NPC41562
0.8154	Intermediate Similarity	NPC71579
0.8154	Intermediate Similarity	NPC262253
0.8125	Intermediate Similarity	NPC24474
0.8125	Intermediate Similarity	NPC311595
0.8125	Intermediate Similarity	NPC182119
0.8125	Intermediate Similarity	NPC256369
0.8112	Intermediate Similarity	NPC191376
0.8112	Intermediate Similarity	NPC179825
0.8112	Intermediate Similarity	NPC321505
0.811	Intermediate Similarity	NPC120075
0.8106	Intermediate Similarity	NPC193544
0.8106	Intermediate Similarity	NPC116907
0.8106	Intermediate Similarity	NPC148627
0.8106	Intermediate Similarity	NPC203133
0.8106	Intermediate Similarity	NPC251855
0.8106	Intermediate Similarity	NPC472093
0.8106	Intermediate Similarity	NPC228771
0.8106	Intermediate Similarity	NPC57490
0.8106	Intermediate Similarity	NPC266705
0.8106	Intermediate Similarity	NPC9067
0.8106	Intermediate Similarity	NPC194519
0.8106	Intermediate Similarity	NPC257589
0.8106	Intermediate Similarity	NPC53305
0.8106	Intermediate Similarity	NPC298757
0.8106	Intermediate Similarity	NPC221077
0.8106	Intermediate Similarity	NPC117214
0.8106	Intermediate Similarity	NPC234400
0.8106	Intermediate Similarity	NPC475169
0.8106	Intermediate Similarity	NPC29008
0.8106	Intermediate Similarity	NPC60885
0.8106	Intermediate Similarity	NPC233410
0.8106	Intermediate Similarity	NPC17943
0.8106	Intermediate Similarity	NPC208950
0.8095	Intermediate Similarity	NPC37302
0.8092	Intermediate Similarity	NPC229084
0.8092	Intermediate Similarity	NPC160900
0.8092	Intermediate Similarity	NPC18984
0.8092	Intermediate Similarity	NPC228922
0.8092	Intermediate Similarity	NPC106659
0.8092	Intermediate Similarity	NPC197757
0.8069	Intermediate Similarity	NPC478189
0.8065	Intermediate Similarity	NPC195873
0.8062	Intermediate Similarity	NPC10932
0.8062	Intermediate Similarity	NPC474565
0.8062	Intermediate Similarity	NPC247364
0.8062	Intermediate Similarity	NPC232084
0.8062	Intermediate Similarity	NPC61516
0.8056	Intermediate Similarity	NPC476571
0.8056	Intermediate Similarity	NPC24233
0.8056	Intermediate Similarity	NPC147390
0.8056	Intermediate Similarity	NPC246587
0.8056	Intermediate Similarity	NPC428
0.8056	Intermediate Similarity	NPC135538
0.8054	Intermediate Similarity	NPC329837
0.8047	Intermediate Similarity	NPC474040
0.8047	Intermediate Similarity	NPC474214
0.8045	Intermediate Similarity	NPC103823
0.8045	Intermediate Similarity	NPC84076
0.8045	Intermediate Similarity	NPC28730
0.8045	Intermediate Similarity	NPC303680
0.8045	Intermediate Similarity	NPC17837

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 NPC155838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	795
0.2-0.3	1116
0.3-0.4	2154
0.4-0.5	2517
0.5-0.6	1518
0.6-0.7	721
0.7-0.8	171
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9141	High Similarity	NPD2674	Phase 3
0.9062	High Similarity	NPD3144	Approved
0.9062	High Similarity	NPD3145	Approved
0.8372	Intermediate Similarity	NPD1669	Approved
0.8361	Intermediate Similarity	NPD228	Approved
0.8345	Intermediate Similarity	NPD6331	Phase 2
0.8195	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2161	Phase 2
0.8168	Intermediate Similarity	NPD2922	Phase 1
0.8154	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD3060	Approved
0.8112	Intermediate Similarity	NPD4123	Phase 3
0.8092	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD1558	Phase 1
0.8085	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD5718	Phase 2
0.8071	Intermediate Similarity	NPD7153	Discontinued
0.7955	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD5283	Phase 1
0.7931	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD2668	Approved
0.7923	Intermediate Similarity	NPD2667	Approved
0.7902	Intermediate Similarity	NPD5241	Discontinued
0.7887	Intermediate Similarity	NPD4162	Approved
0.7868	Intermediate Similarity	NPD3027	Phase 3
0.7838	Intermediate Similarity	NPD4675	Approved
0.7838	Intermediate Similarity	NPD4678	Approved
0.7836	Intermediate Similarity	NPD3053	Approved
0.7836	Intermediate Similarity	NPD3055	Approved
0.781	Intermediate Similarity	NPD5109	Approved
0.781	Intermediate Similarity	NPD5111	Phase 2
0.781	Intermediate Similarity	NPD5110	Phase 2
0.7786	Intermediate Similarity	NPD6895	Approved
0.7786	Intermediate Similarity	NPD6896	Approved
0.7778	Intermediate Similarity	NPD6584	Phase 3
0.777	Intermediate Similarity	NPD4005	Discontinued
0.7762	Intermediate Similarity	NPD5177	Phase 3
0.7761	Intermediate Similarity	NPD5311	Approved
0.7761	Intermediate Similarity	NPD5310	Approved
0.7744	Intermediate Similarity	NPD2230	Approved
0.7744	Intermediate Similarity	NPD2232	Approved
0.7744	Intermediate Similarity	NPD2233	Approved
0.774	Intermediate Similarity	NPD4739	Approved
0.7733	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD9379	Approved
0.7717	Intermediate Similarity	NPD9377	Approved
0.7698	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2977	Approved
0.7682	Intermediate Similarity	NPD2978	Approved
0.7671	Intermediate Similarity	NPD4357	Discontinued
0.7639	Intermediate Similarity	NPD4236	Phase 3
0.7639	Intermediate Similarity	NPD4237	Approved
0.7622	Intermediate Similarity	NPD1375	Discontinued
0.7619	Intermediate Similarity	NPD3022	Approved
0.7619	Intermediate Similarity	NPD3021	Approved
0.7609	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1024	Discontinued
0.7606	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7526	Approved
0.7568	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD52	Approved
0.7566	Intermediate Similarity	NPD5773	Approved
0.7566	Intermediate Similarity	NPD5772	Approved
0.7557	Intermediate Similarity	NPD5536	Phase 2
0.7556	Intermediate Similarity	NPD6582	Phase 2
0.7556	Intermediate Similarity	NPD6583	Phase 3
0.7532	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2122	Discontinued
0.7516	Intermediate Similarity	NPD4083	Discontinued
0.75	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD840	Approved
0.75	Intermediate Similarity	NPD7477	Discontinued
0.75	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD839	Approved
0.7483	Intermediate Similarity	NPD4108	Discontinued
0.7481	Intermediate Similarity	NPD2231	Phase 2
0.7481	Intermediate Similarity	NPD2235	Phase 2
0.7465	Intermediate Similarity	NPD2157	Approved
0.7464	Intermediate Similarity	NPD4993	Discontinued
0.7464	Intermediate Similarity	NPD1712	Approved
0.7448	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3620	Phase 2
0.7447	Intermediate Similarity	NPD3061	Approved
0.7447	Intermediate Similarity	NPD3062	Approved
0.7447	Intermediate Similarity	NPD3059	Approved
0.7444	Intermediate Similarity	NPD1357	Approved
0.7442	Intermediate Similarity	NPD821	Approved
0.7436	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5604	Discontinued
0.7419	Intermediate Similarity	NPD4055	Discovery
0.7415	Intermediate Similarity	NPD2219	Phase 1
0.7405	Intermediate Similarity	NPD709	Approved
0.7388	Intermediate Similarity	NPD9381	Approved
0.7388	Intermediate Similarity	NPD9384	Approved
0.7385	Intermediate Similarity	NPD2234	Approved
0.7385	Intermediate Similarity	NPD2229	Approved
0.7385	Intermediate Similarity	NPD2228	Approved
0.7379	Intermediate Similarity	NPD3656	Approved
0.7376	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7124	Phase 2
0.7343	Intermediate Similarity	NPD3052	Approved
0.7343	Intermediate Similarity	NPD2653	Approved
0.7343	Intermediate Similarity	NPD5314	Approved
0.7343	Intermediate Similarity	NPD3054	Approved
0.7338	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2808	Discontinued
0.7324	Intermediate Similarity	NPD2238	Phase 2
0.7313	Intermediate Similarity	NPD4093	Discontinued
0.7308	Intermediate Similarity	NPD7833	Phase 2
0.7308	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7831	Phase 2
0.7303	Intermediate Similarity	NPD824	Approved
0.7299	Intermediate Similarity	NPD2983	Phase 2
0.7299	Intermediate Similarity	NPD9622	Approved
0.7299	Intermediate Similarity	NPD2982	Phase 2
0.7297	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2821	Approved
0.7273	Intermediate Similarity	NPD9296	Approved
0.7267	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4584	Approved
0.7266	Intermediate Similarity	NPD9621	Approved
0.7266	Intermediate Similarity	NPD7905	Discontinued
0.7266	Intermediate Similarity	NPD2684	Approved
0.7266	Intermediate Similarity	NPD9620	Approved
0.7266	Intermediate Similarity	NPD9619	Approved
0.7254	Intermediate Similarity	NPD3532	Approved
0.7254	Intermediate Similarity	NPD3530	Approved
0.7254	Intermediate Similarity	NPD3531	Approved
0.7248	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3686	Approved
0.7237	Intermediate Similarity	NPD2883	Discontinued
0.7237	Intermediate Similarity	NPD3687	Approved
0.7233	Intermediate Similarity	NPD4010	Discontinued
0.7233	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2981	Phase 2
0.7222	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2492	Phase 1
0.7218	Intermediate Similarity	NPD3596	Phase 2
0.7214	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD9494	Approved
0.7211	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1792	Phase 2
0.7208	Intermediate Similarity	NPD6072	Discontinued
0.7206	Intermediate Similarity	NPD3421	Phase 3
0.7205	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1613	Approved
0.719	Intermediate Similarity	NPD3455	Phase 2
0.7183	Intermediate Similarity	NPD1039	Discontinued
0.7183	Intermediate Similarity	NPD597	Approved
0.7183	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD601	Approved
0.7183	Intermediate Similarity	NPD598	Approved
0.7181	Intermediate Similarity	NPD3692	Discontinued
0.7174	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3685	Discontinued
0.7172	Intermediate Similarity	NPD6111	Discontinued
0.7171	Intermediate Similarity	NPD6030	Approved
0.7171	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6031	Approved
0.7161	Intermediate Similarity	NPD5720	Discontinued
0.7154	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3536	Discontinued
0.7152	Intermediate Similarity	NPD3985	Discontinued
0.7143	Intermediate Similarity	NPD27	Approved
0.7143	Intermediate Similarity	NPD2489	Approved
0.7143	Intermediate Similarity	NPD7451	Discontinued
0.7133	Intermediate Similarity	NPD1423	Approved
0.7133	Intermediate Similarity	NPD1136	Approved
0.7133	Intermediate Similarity	NPD1130	Approved
0.7133	Intermediate Similarity	NPD1132	Approved
0.7132	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD2933	Approved
0.7131	Intermediate Similarity	NPD2934	Approved
0.7122	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2486	Discontinued
0.7111	Intermediate Similarity	NPD6581	Approved
0.7111	Intermediate Similarity	NPD6580	Approved
0.7109	Intermediate Similarity	NPD1444	Approved
0.7109	Intermediate Similarity	NPD1445	Approved
0.7103	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4097	Suspended
0.7097	Intermediate Similarity	NPD5089	Approved
0.7097	Intermediate Similarity	NPD5090	Approved
0.7095	Intermediate Similarity	NPD7037	Approved
0.7092	Intermediate Similarity	NPD3018	Phase 2
0.7083	Intermediate Similarity	NPD4060	Phase 1
0.708	Intermediate Similarity	NPD3847	Discontinued
0.7078	Intermediate Similarity	NPD3111	Phase 1
0.7078	Intermediate Similarity	NPD4017	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