NPASS Compound

Structure

CID213552 OpenBabel06191716002D 23 24 0 0 0 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 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 7.7942 3.5000 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 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 1.7321 -0.0000 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 -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 9.5263 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 6 1 0 0 0 0 2 13 2 0 0 0 0 3 7 2 0 0 0 0 3 13 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 23 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 15 19 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 21 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.12
Volume:	325.631
LogP:	3.227
LogD:	3.636
LogS:	-3.528
# Rotatable Bonds:	7
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	2.043
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:	-4.796
MDCK Permeability:	2.0186314941383898e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.779
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	98.34252166748047%
Volume Distribution (VD):	0.437
Pgp-substrate:	1.4386374950408936%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.687
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.891
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.485

ADMET: Excretion

Clearance (CL):	13.811
Half-life (T1/2):	0.931

ADMET: Toxicity

hERG Blockers:	0.394
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.272
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.624
Skin Sensitization:	0.958
Carcinogencity:	0.518
Eye Corrosion:	0.006
Eye Irritation:	0.659
Respiratory Toxicity:	0.246

Download Data

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

Natural Product: NPC213552

Natural Product ID:	NPC213552
*Common Name:**	P-Hydroxyphenethyl Trans-Ferulate
IUPAC Name:	2-(4-hydroxyphenyl)ethyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:	P-Hydroxyphenethyl Trans-Ferulate
Standard InCHIKey:	JMSFLLZUCIXALN-WEVVVXLNSA-N
Standard InCHI:	InChI=1S/C18H18O5/c1-22-17-12-14(4-8-16(17)20)5-9-18(21)23-11-10-13-2-6-15(19)7-3-13/h2-9,12,19-20H,10-11H2,1H3/b9-5+
SMILES:	COc1cc(/C=C/C(=O)OCCc2ccc(cc2)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481245
PubChem CID:	637308
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric 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
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654417]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	tenerife	n.a.	PMID[10924166]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374950]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[12467611]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	aerial parts	Bangdung, Indonesia	2000-Aug	PMID[12608860]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15104497]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309323]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18076141]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19691312]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22165973]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22220686]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24279991]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24784222]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26473275]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28898076]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[31713425]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10994	Sargentodoxa cuneata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31017	Polygonum orientale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10994	Sargentodoxa cuneata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31017	Polygonum orientale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10994	Sargentodoxa cuneata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30125	0topterygium forbesii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10994	Sargentodoxa cuneata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19061	Ceratozamia kuesteriana	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23062	Melibe leonina	Species	Dendronotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18250	Conus tessulatus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1408	Cirsium helenioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11235	Asplenium nidus	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO592	Chroogomphus rutilus	Species	Gomphidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16201	Pteris altissima	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10073	Clusia torresii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14797	Orthosiphon aristatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5890	Astragalus inopinatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14887	Handroanthus guayacan	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21680	Saussurea triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2499	Celmisia petriei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1638	Ulmus laciniata	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17606	Millettia ichthyochtona	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17281	Echinaster echinophorus	Species	Echinasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18716	Parmelia caraccensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10994	Sargentodoxa cuneata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22137	Vernonia serratuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5877	Morus yunnanensis	Species	Moraceae	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
ED50	2
IC50	7
Ki	12
Others	1

Activity Type	# Activity
Cell Line	4
CELL-LINE	2
Individual Protein	15
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	47.1	ug ml-1	PMID[488843]
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	IC50	=	47600.0	nM	PMID[488844]
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Inhibition	=	71.0	%	PMID[488844]
NPT1146	Individual Protein	Carbonic anhydrase III	Homo sapiens	Ki	>	50000.0	nM	PMID[488845]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	>	50000.0	nM	PMID[488845]
NPT1062	Individual Protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	44000.0	nM	PMID[488845]
NPT1143	Individual Protein	Carbonic anhydrase VA	Homo sapiens	Ki	=	810.0	nM	PMID[488845]
NPT1144	Individual Protein	Carbonic anhydrase VB	Homo sapiens	Ki	=	670.0	nM	PMID[488845]
NPT1063	Individual Protein	Carbonic anhydrase VI	Homo sapiens	Ki	=	770.0	nM	PMID[488845]
NPT1061	Individual Protein	Carbonic anhydrase XIII	Mus musculus	Ki	=	930.0	nM	PMID[488845]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	=	12900.0	nM	PMID[488846]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	87600.0	nM	PMID[488846]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	IC50	=	95500.0	nM	PMID[488846]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	44300.0	nM	PMID[488846]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	33.7	ug ml-1	PMID[488843]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	>	50000.0	nM	PMID[488845]
NPT955	Individual Protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	620.0	nM	PMID[488845]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	810.0	nM	PMID[488845]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	8470.0	nM	PMID[488845]
NPT954	Individual Protein	Carbonic anhydrase XIV	Homo sapiens	Ki	=	720.0	nM	PMID[488845]
NPT20950	CELL-LINE	Erythrocyte	n.a.	IC50	=	660000.0	nM	PMID[488847]
NPT20950	CELL-LINE	Erythrocyte	n.a.	IC50	=	1010000.0	nM	PMID[488847]

☑ 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 NPC213552 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	273
0.1-0.2	1456
0.2-0.3	4414
0.3-0.4	11022
0.4-0.5	6963
0.5-0.6	4174
0.6-0.7	9336
0.7-0.8	4162
0.8-0.85	621
0.85-0.9	219
0.9-0.95	46
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC120225
0.9916	High Similarity	NPC289459
0.9832	High Similarity	NPC246704
0.9754	High Similarity	NPC83062
0.9667	High Similarity	NPC146886
0.9667	High Similarity	NPC60517
0.9667	High Similarity	NPC20443
0.9512	High Similarity	NPC110313
0.9496	High Similarity	NPC204466
0.9417	High Similarity	NPC70752
0.9412	High Similarity	NPC202474
0.937	High Similarity	NPC135127
0.9355	High Similarity	NPC478215
0.9333	High Similarity	NPC269843
0.9333	High Similarity	NPC470849
0.9333	High Similarity	NPC470848
0.9333	High Similarity	NPC60962
0.9333	High Similarity	NPC224814
0.9333	High Similarity	NPC14007
0.9333	High Similarity	NPC109083
0.9333	High Similarity	NPC189844
0.9328	High Similarity	NPC141791
0.9328	High Similarity	NPC263386
0.9268	High Similarity	NPC87113
0.925	High Similarity	NPC2058
0.9244	High Similarity	NPC277460
0.9244	High Similarity	NPC272471
0.9244	High Similarity	NPC164706
0.9244	High Similarity	NPC137537
0.9244	High Similarity	NPC107588
0.9244	High Similarity	NPC275519
0.9244	High Similarity	NPC70744
0.9225	High Similarity	NPC90431
0.9225	High Similarity	NPC120852
0.9154	High Similarity	NPC126206
0.9127	High Similarity	NPC241354
0.912	High Similarity	NPC151167
0.912	High Similarity	NPC123722
0.912	High Similarity	NPC276466
0.912	High Similarity	NPC5018
0.912	High Similarity	NPC123228
0.9113	High Similarity	NPC280767
0.9106	High Similarity	NPC160900
0.9106	High Similarity	NPC18984
0.9106	High Similarity	NPC229084
0.9106	High Similarity	NPC106659
0.9098	High Similarity	NPC147654
0.9084	High Similarity	NPC284409
0.9083	High Similarity	NPC203124
0.9083	High Similarity	NPC309434
0.9083	High Similarity	NPC470626
0.9077	High Similarity	NPC471664
0.9077	High Similarity	NPC471665
0.904	High Similarity	NPC90128
0.904	High Similarity	NPC84076
0.904	High Similarity	NPC179777
0.904	High Similarity	NPC303680
0.9016	High Similarity	NPC207613
0.9015	High Similarity	NPC110699
0.9015	High Similarity	NPC288452
0.9015	High Similarity	NPC289690
0.9015	High Similarity	NPC106055
0.9008	High Similarity	NPC37858
0.9	High Similarity	NPC293619
0.9	High Similarity	NPC280001
0.8992	High Similarity	NPC475468
0.8976	High Similarity	NPC304622
0.8952	High Similarity	NPC317769
0.8952	High Similarity	NPC31344
0.8943	High Similarity	NPC54872
0.8943	High Similarity	NPC470212
0.8943	High Similarity	NPC324571
0.8943	High Similarity	NPC262156
0.8943	High Similarity	NPC343720
0.8943	High Similarity	NPC312675
0.8943	High Similarity	NPC473853
0.8943	High Similarity	NPC113865
0.8943	High Similarity	NPC184651
0.8939	High Similarity	NPC76032
0.8939	High Similarity	NPC132723
0.8934	High Similarity	NPC242885
0.8934	High Similarity	NPC232316
0.8934	High Similarity	NPC95614
0.8934	High Similarity	NPC117780
0.8934	High Similarity	NPC56214
0.8934	High Similarity	NPC165133
0.8934	High Similarity	NPC227217
0.8923	High Similarity	NPC471110
0.8923	High Similarity	NPC67247
0.8923	High Similarity	NPC476387
0.8923	High Similarity	NPC4982
0.8923	High Similarity	NPC111635
0.8923	High Similarity	NPC176814
0.8923	High Similarity	NPC68779
0.8923	High Similarity	NPC119060
0.8923	High Similarity	NPC300776
0.8923	High Similarity	NPC249791
0.8923	High Similarity	NPC237594
0.8923	High Similarity	NPC5310
0.8917	High Similarity	NPC281277
0.8908	High Similarity	NPC328593
0.8908	High Similarity	NPC33749
0.8908	High Similarity	NPC261453
0.8908	High Similarity	NPC294941
0.8898	High Similarity	NPC109275
0.8889	High Similarity	NPC276014
0.8881	High Similarity	NPC140502
0.8881	High Similarity	NPC67467
0.8871	High Similarity	NPC286573
0.8871	High Similarity	NPC85488
0.8852	High Similarity	NPC310338
0.8852	High Similarity	NPC281298
0.8843	High Similarity	NPC175799
0.8843	High Similarity	NPC200988
0.8843	High Similarity	NPC86947
0.8843	High Similarity	NPC610
0.8843	High Similarity	NPC145023
0.8843	High Similarity	NPC39793
0.8833	High Similarity	NPC233669
0.8833	High Similarity	NPC474967
0.8828	High Similarity	NPC48315
0.8824	High Similarity	NPC95381
0.881	High Similarity	NPC194519
0.881	High Similarity	NPC257589
0.881	High Similarity	NPC53305
0.88	High Similarity	NPC280704
0.88	High Similarity	NPC164778
0.88	High Similarity	NPC242372
0.88	High Similarity	NPC471693
0.88	High Similarity	NPC4181
0.88	High Similarity	NPC257976
0.879	High Similarity	NPC127389
0.879	High Similarity	NPC38996
0.879	High Similarity	NPC177291
0.879	High Similarity	NPC290451
0.879	High Similarity	NPC160380
0.879	High Similarity	NPC194416
0.8788	High Similarity	NPC471988
0.8779	High Similarity	NPC473054
0.877	High Similarity	NPC124916
0.877	High Similarity	NPC86198
0.8769	High Similarity	NPC245120
0.875	High Similarity	NPC226661
0.875	High Similarity	NPC217472
0.874	High Similarity	NPC191037
0.874	High Similarity	NPC127937
0.874	High Similarity	NPC58607
0.874	High Similarity	NPC118584
0.874	High Similarity	NPC178284
0.874	High Similarity	NPC92207
0.873	High Similarity	NPC114901
0.873	High Similarity	NPC273686
0.873	High Similarity	NPC293701
0.873	High Similarity	NPC312404
0.873	High Similarity	NPC48990
0.8722	High Similarity	NPC281780
0.872	High Similarity	NPC114298
0.8712	High Similarity	NPC477301
0.8712	High Similarity	NPC214729
0.8712	High Similarity	NPC113295
0.871	High Similarity	NPC158949
0.871	High Similarity	NPC471877
0.8702	High Similarity	NPC36490
0.8699	High Similarity	NPC470215
0.8699	High Similarity	NPC70084
0.8699	High Similarity	NPC24474
0.8699	High Similarity	NPC311595
0.8699	High Similarity	NPC470214
0.8699	High Similarity	NPC109371
0.8689	High Similarity	NPC65791
0.8689	High Similarity	NPC164386
0.8686	High Similarity	NPC473909
0.8686	High Similarity	NPC143120
0.8686	High Similarity	NPC258671
0.8686	High Similarity	NPC274960
0.8686	High Similarity	NPC34587
0.8686	High Similarity	NPC252292
0.8686	High Similarity	NPC53884
0.8686	High Similarity	NPC100998
0.8686	High Similarity	NPC476382
0.8686	High Similarity	NPC163898
0.8686	High Similarity	NPC34927
0.8678	High Similarity	NPC296526
0.8676	High Similarity	NPC478239
0.8672	High Similarity	NPC147821
0.8672	High Similarity	NPC118787
0.8672	High Similarity	NPC163332
0.8672	High Similarity	NPC319625
0.8672	High Similarity	NPC41706
0.8672	High Similarity	NPC111247
0.8672	High Similarity	NPC183181
0.8672	High Similarity	NPC292056
0.8661	High Similarity	NPC58279
0.8661	High Similarity	NPC300326
0.8661	High Similarity	NPC67951
0.8661	High Similarity	NPC148627
0.8655	High Similarity	NPC226250
0.8655	High Similarity	NPC8547
0.8655	High Similarity	NPC173746
0.8655	High Similarity	NPC257124

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 NPC213552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	903
0.2-0.3	1595
0.3-0.4	2619
0.4-0.5	1823
0.5-0.6	1073
0.6-0.7	729
0.7-0.8	159
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9106	High Similarity	NPD4379	Clinical (unspecified phase)
0.8655	High Similarity	NPD228	Approved
0.8537	High Similarity	NPD5536	Phase 2
0.8397	Intermediate Similarity	NPD3027	Phase 3
0.8361	Intermediate Similarity	NPD5283	Phase 1
0.8346	Intermediate Similarity	NPD4060	Phase 1
0.8319	Intermediate Similarity	NPD1358	Approved
0.8248	Intermediate Similarity	NPD7266	Discontinued
0.8106	Intermediate Similarity	NPD9494	Approved
0.8083	Intermediate Similarity	NPD3134	Approved
0.8033	Intermediate Similarity	NPD3022	Approved
0.8033	Intermediate Similarity	NPD3021	Approved
0.8028	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD7095	Approved
0.7984	Intermediate Similarity	NPD3496	Discontinued
0.7907	Intermediate Similarity	NPD4626	Approved
0.784	Intermediate Similarity	NPD5535	Approved
0.7829	Intermediate Similarity	NPD1357	Approved
0.7829	Intermediate Similarity	NPD5691	Approved
0.7817	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD8166	Discontinued
0.7817	Intermediate Similarity	NPD4628	Phase 3
0.7817	Intermediate Similarity	NPD4110	Phase 3
0.781	Intermediate Similarity	NPD3620	Phase 2
0.781	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1613	Approved
0.7808	Intermediate Similarity	NPD1653	Approved
0.7805	Intermediate Similarity	NPD2684	Approved
0.7794	Intermediate Similarity	NPD6798	Discontinued
0.7786	Intermediate Similarity	NPD2935	Discontinued
0.7778	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD6190	Approved
0.7755	Intermediate Similarity	NPD3455	Phase 2
0.7754	Intermediate Similarity	NPD6355	Discontinued
0.7754	Intermediate Similarity	NPD4340	Discontinued
0.7737	Intermediate Similarity	NPD4062	Phase 3
0.7737	Intermediate Similarity	NPD6233	Phase 2
0.771	Intermediate Similarity	NPD3847	Discontinued
0.7704	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7843	Approved
0.7682	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3882	Suspended
0.7681	Intermediate Similarity	NPD1558	Phase 1
0.7656	Intermediate Similarity	NPD7157	Approved
0.7652	Intermediate Similarity	NPD3705	Approved
0.7626	Intermediate Similarity	NPD447	Suspended
0.7626	Intermediate Similarity	NPD230	Phase 1
0.7615	Intermediate Similarity	NPD1894	Discontinued
0.7609	Intermediate Similarity	NPD2674	Phase 3
0.76	Intermediate Similarity	NPD1934	Approved
0.7557	Intermediate Similarity	NPD5585	Approved
0.755	Intermediate Similarity	NPD2801	Approved
0.7537	Intermediate Similarity	NPD2982	Phase 2
0.7537	Intermediate Similarity	NPD2983	Phase 2
0.7537	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD422	Phase 1
0.7519	Intermediate Similarity	NPD1535	Discovery
0.7518	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD3060	Approved
0.75	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD6584	Phase 3
0.7481	Intermediate Similarity	NPD1283	Approved
0.7468	Intermediate Similarity	NPD6234	Discontinued
0.7463	Intermediate Similarity	NPD2981	Phase 2
0.7463	Intermediate Similarity	NPD1481	Phase 2
0.7447	Intermediate Similarity	NPD6653	Approved
0.7445	Intermediate Similarity	NPD3018	Phase 2
0.7434	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4140	Approved
0.7426	Intermediate Similarity	NPD2797	Approved
0.7417	Intermediate Similarity	NPD6385	Approved
0.7417	Intermediate Similarity	NPD6386	Approved
0.7415	Intermediate Similarity	NPD4357	Discontinued
0.7413	Intermediate Similarity	NPD6032	Approved
0.741	Intermediate Similarity	NPD3145	Approved
0.741	Intermediate Similarity	NPD3144	Approved
0.741	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD2933	Approved
0.7395	Intermediate Similarity	NPD9296	Approved
0.7395	Intermediate Similarity	NPD2934	Approved
0.7385	Intermediate Similarity	NPD6671	Approved
0.7383	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4162	Approved
0.7379	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1933	Approved
0.7368	Intermediate Similarity	NPD1778	Approved
0.7368	Intermediate Similarity	NPD5846	Approved
0.7368	Intermediate Similarity	NPD6516	Phase 2
0.7364	Intermediate Similarity	NPD1241	Discontinued
0.7361	Intermediate Similarity	NPD5762	Approved
0.7361	Intermediate Similarity	NPD5763	Approved
0.7357	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9545	Approved
0.7343	Intermediate Similarity	NPD2799	Discontinued
0.7338	Intermediate Similarity	NPD5163	Phase 2
0.7333	Intermediate Similarity	NPD3687	Approved
0.7333	Intermediate Similarity	NPD2859	Approved
0.7333	Intermediate Similarity	NPD1608	Approved
0.7333	Intermediate Similarity	NPD3686	Approved
0.7333	Intermediate Similarity	NPD2860	Approved
0.7324	Intermediate Similarity	NPD2653	Approved
0.732	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2861	Phase 2
0.731	Intermediate Similarity	NPD4534	Discontinued
0.7305	Intermediate Similarity	NPD825	Approved
0.7305	Intermediate Similarity	NPD2979	Phase 3
0.7305	Intermediate Similarity	NPD826	Approved
0.7302	Intermediate Similarity	NPD290	Approved
0.7299	Intermediate Similarity	NPD1203	Approved
0.7297	Intermediate Similarity	NPD6799	Approved
0.7297	Intermediate Similarity	NPD1511	Approved
0.7295	Intermediate Similarity	NPD3020	Approved
0.7292	Intermediate Similarity	NPD2438	Suspended
0.7286	Intermediate Similarity	NPD5111	Phase 2
0.7286	Intermediate Similarity	NPD5110	Phase 2
0.7286	Intermediate Similarity	NPD5109	Approved
0.7286	Intermediate Similarity	NPD3268	Approved
0.7285	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3111	Phase 1
0.7284	Intermediate Similarity	NPD7685	Pre-registration
0.728	Intermediate Similarity	NPD9697	Approved
0.7279	Intermediate Similarity	NPD4359	Approved
0.7279	Intermediate Similarity	NPD6583	Phase 3
0.7279	Intermediate Similarity	NPD6582	Phase 2
0.7273	Intermediate Similarity	NPD7097	Phase 1
0.7266	Intermediate Similarity	NPD6832	Phase 2
0.7266	Intermediate Similarity	NPD4908	Phase 1
0.7261	Intermediate Similarity	NPD8127	Discontinued
0.726	Intermediate Similarity	NPD4236	Phase 3
0.726	Intermediate Similarity	NPD4237	Approved
0.7259	Intermediate Similarity	NPD1281	Approved
0.7255	Intermediate Similarity	NPD37	Approved
0.725	Intermediate Similarity	NPD3818	Discontinued
0.7248	Intermediate Similarity	NPD3536	Discontinued
0.7233	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6166	Phase 2
0.7233	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4965	Approved
0.7226	Intermediate Similarity	NPD2922	Phase 1
0.7226	Intermediate Similarity	NPD3225	Approved
0.7226	Intermediate Similarity	NPD4967	Phase 2
0.7226	Intermediate Similarity	NPD4966	Approved
0.7218	Intermediate Similarity	NPD1548	Phase 1
0.7215	Intermediate Similarity	NPD6232	Discontinued
0.7212	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6331	Phase 2
0.7208	Intermediate Similarity	NPD2977	Approved
0.7208	Intermediate Similarity	NPD2978	Approved
0.7208	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1465	Phase 2
0.7205	Intermediate Similarity	NPD7054	Approved
0.7205	Intermediate Similarity	NPD5844	Phase 1
0.72	Intermediate Similarity	NPD1512	Approved
0.72	Intermediate Similarity	NPD6273	Approved
0.7192	Intermediate Similarity	NPD5958	Discontinued
0.719	Intermediate Similarity	NPD6873	Phase 2
0.7188	Intermediate Similarity	NPD5451	Approved
0.7179	Intermediate Similarity	NPD7075	Discontinued
0.7177	Intermediate Similarity	NPD291	Approved
0.7174	Intermediate Similarity	NPD987	Approved
0.7171	Intermediate Similarity	NPD7458	Discontinued
0.7164	Intermediate Similarity	NPD1651	Approved
0.7163	Intermediate Similarity	NPD5718	Phase 2
0.7163	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3764	Approved
0.7162	Intermediate Similarity	NPD5241	Discontinued
0.7162	Intermediate Similarity	NPD2354	Approved
0.716	Intermediate Similarity	NPD7472	Approved
0.716	Intermediate Similarity	NPD7074	Phase 3
0.7154	Intermediate Similarity	NPD821	Approved
0.7152	Intermediate Similarity	NPD2821	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2614	Approved
0.7134	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD555	Phase 2
0.7133	Intermediate Similarity	NPD4123	Phase 3
0.7132	Intermediate Similarity	NPD1610	Phase 2
0.7132	Intermediate Similarity	NPD1611	Approved
0.7124	Intermediate Similarity	NPD7028	Phase 2
0.7122	Intermediate Similarity	NPD5647	Approved
0.7121	Intermediate Similarity	NPD4198	Discontinued
0.7117	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7440	Discontinued
0.7111	Intermediate Similarity	NPD17	Approved
0.7103	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4308	Phase 3
0.7097	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3750	Approved
0.7095	Intermediate Similarity	NPD7003	Approved
0.7086	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2492	Phase 1

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