NPASS Compound

Structure

CID214869 OpenBabel06191716002D 25 26 0 0 0 0 0 0 0 0999 V2000 -10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -6.9282 0.0000 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 -6.0622 -0.5000 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 -3.4641 0.0000 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 -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 -9.5263 -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 -9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -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 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 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 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 20 2 3 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	343.14
Volume:	353.923
LogP:	2.448
LogD:	2.907
LogS:	-3.287
# Rotatable Bonds:	8
TPSA:	88.02
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	2.089
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.909
MDCK Permeability:	1.2775939467246644e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.773
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.124

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	97.8237075805664%
Volume Distribution (VD):	0.574
Pgp-substrate:	1.4504598379135132%

ADMET: Metabolism

CYP1A2-inhibitor:	0.787
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.559
CYP2C19-substrate:	0.328
CYP2C9-inhibitor:	0.652
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.591
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.373

ADMET: Excretion

Clearance (CL):	11.554
Half-life (T1/2):	0.919

ADMET: Toxicity

hERG Blockers:	0.212
Human Hepatotoxicity (H-HT):	0.507
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.231
Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.845
Skin Sensitization:	0.936
Carcinogencity:	0.414
Eye Corrosion:	0.003
Eye Irritation:	0.06
Respiratory Toxicity:	0.729

Download Data

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

Natural Product: NPC214869

Natural Product ID:	NPC214869
*Common Name:**	N-Trans-Feruloylmethoxytyramine
IUPAC Name:	(E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]prop-2-enamide
Synonyms:	N-Trans-Feruloylmethoxytyramine
Standard InCHIKey:	GRXBVKANHNUZNL-VMPITWQZSA-N
Standard InCHI:	InChI=1S/C19H21NO5/c1-24-17-11-13(3-6-15(17)21)5-8-19(23)20-10-9-14-4-7-16(22)18(12-14)25-2/h3-8,11-12,21-22H,9-10H2,1-2H3,(H,20,23)/b8-5+
SMILES:	COc1cc(CCN=C(/C=C/c2ccc(c(c2)OC)O)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226588
PubChem CID:	5352115
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
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
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]
NPO2324	Phoma herbarum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713403]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[12880323]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387648]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15387664]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17511147]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524603]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20097074]
NPO7472	Litsea hypophaea	Species	Lauraceae	Eukaryota	roots	n.a.	n.a.	PMID[20384293]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21353775]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21500777]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO16241	Eucalyptus perriniana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23980409]
NPO21107	Bassia scoparia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24380276]
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]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO16722	Tolypothrix nodosa	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8792625]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	Suriname rainforest	n.a.	PMID[9428162]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9433811]
NPO16722	Tolypothrix nodosa	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9748382]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
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]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Leaves	n.a.		Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15309	Salsola collina	Species	Chenopodiaceae	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]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13358	Piper brachystachyum	Species	Piperaceae	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]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	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]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO21107	Bassia scoparia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15802	Papaver pseudocanescens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21107	Bassia scoparia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18169	Creosphaeria sassafras	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16587	Actinodaphne longifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15935	Pinus parviflora	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17537	Anthotroche blackii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11646	Morella pensylvanica	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10869	Cota saguramica	Species	Asteraceae	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]
NPO15419	Tunica prolifera	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12914	Sarcophyton flexuosum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19572	Pellacalyx axillaris	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17230	Psidium acutangulum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28392	Macrosiphum liriodendri	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18348	Crotalaria stolzii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8172	Emericellopsis minima	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17354	Micromonospora echinospora	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18424	Selinum libanotis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11081	Baccharis grandicapitulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19371	Costasiella ocellifera	Species	Costasiellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19170	Lasianthaea podocephala	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]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18927	Clinacanthus nutans	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5455	Euploca racemosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17630	Helenium integrifolium	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]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28218	Asplenium adiantum-nigrum	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17389	Papilio xuthus	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4674	Gaillardia powellii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO968	Artemisia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14831	Mastophora hutchinsoni	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7472	Litsea hypophaea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4679	Hedysarum gmelini	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17015	Plantago hookeriana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25370	Botrychium ternatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12870	Curcuma aeruginosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10282	Solenostoma triste	Species	Solenostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28510	Aspergillus pseudodeflectus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16981	Gutierrezia dracunculoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9906	Zephyranthes flava	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19018	Senecio provincialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16722	Tolypothrix nodosa	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16241	Eucalyptus perriniana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15127	Senecio congestus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17114	Streptomyces melanogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16325	Sideritis dasygnaphala	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18262	Aspergillus microcysticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16135	Pestalotiopsis oenotherae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17084	Marsilea quadrifolia	Species	Marsileaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2324	Phoma herbarum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13829	Cryptocarya angulata	Species	Lauraceae	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	4
MIC	1

Activity Type	# Activity
Cell Line	3
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[553469]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[553469]
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[553469]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	1000000.0	nM	PMID[553471]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	1.6	ug.mL-1	PMID[553470]

☑ 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 NPC214869 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	194
0.1-0.2	1473
0.2-0.3	7989
0.3-0.4	10484
0.4-0.5	5341
0.5-0.6	9552
0.6-0.7	5723
0.7-0.8	1675
0.8-0.85	208
0.85-0.9	33
0.9-0.95	15
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC35961
0.9839	High Similarity	NPC52029
0.9839	High Similarity	NPC195749
0.976	High Similarity	NPC114102
0.9758	High Similarity	NPC155838
0.9677	High Similarity	NPC153990
0.9677	High Similarity	NPC251571
0.9597	High Similarity	NPC301713
0.952	High Similarity	NPC186898
0.9462	High Similarity	NPC41473
0.9462	High Similarity	NPC204848
0.9462	High Similarity	NPC14600
0.9462	High Similarity	NPC312770
0.9462	High Similarity	NPC160607
0.9389	High Similarity	NPC299583
0.9242	High Similarity	NPC296898
0.9225	High Similarity	NPC93882
0.9225	High Similarity	NPC130595
0.9154	High Similarity	NPC313737
0.9154	High Similarity	NPC6854
0.9154	High Similarity	NPC285078
0.9084	High Similarity	NPC218530
0.9	High Similarity	NPC255550
0.9	High Similarity	NPC308885
0.8978	High Similarity	NPC5462
0.8897	High Similarity	NPC222039
0.8897	High Similarity	NPC100478
0.8871	High Similarity	NPC122009
0.8849	High Similarity	NPC277857
0.8849	High Similarity	NPC115144
0.88	High Similarity	NPC268572
0.879	High Similarity	NPC283468
0.8786	High Similarity	NPC470935
0.8786	High Similarity	NPC471032
0.875	High Similarity	NPC140359
0.875	High Similarity	NPC13020
0.872	High Similarity	NPC470626
0.8652	High Similarity	NPC153644
0.8651	High Similarity	NPC43275
0.864	High Similarity	NPC293619
0.8613	High Similarity	NPC477838
0.8613	High Similarity	NPC477837
0.8601	High Similarity	NPC127402
0.8583	High Similarity	NPC165133
0.8583	High Similarity	NPC232316
0.8583	High Similarity	NPC95614
0.8583	High Similarity	NPC117780
0.8583	High Similarity	NPC242885
0.8583	High Similarity	NPC56214
0.8583	High Similarity	NPC227217
0.8548	High Similarity	NPC142599
0.8542	High Similarity	NPC275027
0.8516	High Similarity	NPC207613
0.8516	High Similarity	NPC83279
0.8504	High Similarity	NPC310338
0.8504	High Similarity	NPC281298
0.8496	Intermediate Similarity	NPC470706
0.8485	Intermediate Similarity	NPC157740
0.8485	Intermediate Similarity	NPC99798
0.8472	Intermediate Similarity	NPC52475
0.8467	Intermediate Similarity	NPC254610
0.845	Intermediate Similarity	NPC473853
0.845	Intermediate Similarity	NPC113865
0.845	Intermediate Similarity	NPC324571
0.845	Intermediate Similarity	NPC262156
0.845	Intermediate Similarity	NPC184651
0.845	Intermediate Similarity	NPC160380
0.845	Intermediate Similarity	NPC343720
0.845	Intermediate Similarity	NPC38996
0.845	Intermediate Similarity	NPC54872
0.845	Intermediate Similarity	NPC470212
0.845	Intermediate Similarity	NPC312675
0.8438	Intermediate Similarity	NPC263835
0.8425	Intermediate Similarity	NPC107602
0.8421	Intermediate Similarity	NPC147247
0.8421	Intermediate Similarity	NPC246974
0.8414	Intermediate Similarity	NPC18614
0.8409	Intermediate Similarity	NPC156944
0.8409	Intermediate Similarity	NPC251466
0.8397	Intermediate Similarity	NPC62101
0.8397	Intermediate Similarity	NPC95733
0.8385	Intermediate Similarity	NPC471314
0.8385	Intermediate Similarity	NPC471315
0.8385	Intermediate Similarity	NPC85488
0.8372	Intermediate Similarity	NPC284078
0.8346	Intermediate Similarity	NPC41331
0.8346	Intermediate Similarity	NPC191302
0.8346	Intermediate Similarity	NPC291449
0.8346	Intermediate Similarity	NPC86947
0.8333	Intermediate Similarity	NPC170583
0.8333	Intermediate Similarity	NPC246133
0.8333	Intermediate Similarity	NPC207541
0.8333	Intermediate Similarity	NPC182119
0.8333	Intermediate Similarity	NPC71105
0.8333	Intermediate Similarity	NPC152186
0.8333	Intermediate Similarity	NPC193528
0.8333	Intermediate Similarity	NPC182147
0.8321	Intermediate Similarity	NPC280704
0.8321	Intermediate Similarity	NPC471693
0.8321	Intermediate Similarity	NPC317769
0.8321	Intermediate Similarity	NPC31344
0.8321	Intermediate Similarity	NPC211218
0.8306	Intermediate Similarity	NPC173746
0.8306	Intermediate Similarity	NPC8547
0.8306	Intermediate Similarity	NPC156840
0.8306	Intermediate Similarity	NPC257124
0.8296	Intermediate Similarity	NPC329595
0.8296	Intermediate Similarity	NPC326599
0.8276	Intermediate Similarity	NPC478189
0.8264	Intermediate Similarity	NPC24233
0.8264	Intermediate Similarity	NPC147390
0.8264	Intermediate Similarity	NPC476571
0.8264	Intermediate Similarity	NPC246587
0.8264	Intermediate Similarity	NPC135538
0.8264	Intermediate Similarity	NPC428
0.8258	Intermediate Similarity	NPC300955
0.8255	Intermediate Similarity	NPC329837
0.8231	Intermediate Similarity	NPC269843
0.8231	Intermediate Similarity	NPC14007
0.8231	Intermediate Similarity	NPC60962
0.8231	Intermediate Similarity	NPC224814
0.8231	Intermediate Similarity	NPC189844
0.8231	Intermediate Similarity	NPC109083
0.8217	Intermediate Similarity	NPC24474
0.8217	Intermediate Similarity	NPC311595
0.8209	Intermediate Similarity	NPC172403
0.8203	Intermediate Similarity	NPC120075
0.8203	Intermediate Similarity	NPC164386
0.8195	Intermediate Similarity	NPC221077
0.8195	Intermediate Similarity	NPC193544
0.8195	Intermediate Similarity	NPC475169
0.8195	Intermediate Similarity	NPC208950
0.8195	Intermediate Similarity	NPC29477
0.8195	Intermediate Similarity	NPC17943
0.8195	Intermediate Similarity	NPC148627
0.8195	Intermediate Similarity	NPC233410
0.8195	Intermediate Similarity	NPC116907
0.8195	Intermediate Similarity	NPC29008
0.8195	Intermediate Similarity	NPC9067
0.8195	Intermediate Similarity	NPC257589
0.8195	Intermediate Similarity	NPC298757
0.8195	Intermediate Similarity	NPC203133
0.8195	Intermediate Similarity	NPC472093
0.8195	Intermediate Similarity	NPC251855
0.8195	Intermediate Similarity	NPC57490
0.8195	Intermediate Similarity	NPC117214
0.8195	Intermediate Similarity	NPC194519
0.8195	Intermediate Similarity	NPC266705
0.8195	Intermediate Similarity	NPC228771
0.8195	Intermediate Similarity	NPC53305
0.8194	Intermediate Similarity	NPC179825
0.8194	Intermediate Similarity	NPC191376
0.8194	Intermediate Similarity	NPC321505
0.8189	Intermediate Similarity	NPC303370
0.8182	Intermediate Similarity	NPC197757
0.8182	Intermediate Similarity	NPC228922
0.8168	Intermediate Similarity	NPC290451
0.8168	Intermediate Similarity	NPC127389
0.816	Intermediate Similarity	NPC166837
0.8154	Intermediate Similarity	NPC289330
0.8154	Intermediate Similarity	NPC160120
0.8154	Intermediate Similarity	NPC17388
0.8154	Intermediate Similarity	NPC471308
0.8154	Intermediate Similarity	NPC53596
0.8148	Intermediate Similarity	NPC469977
0.8145	Intermediate Similarity	NPC233731
0.8145	Intermediate Similarity	NPC7097
0.8145	Intermediate Similarity	NPC36108
0.8145	Intermediate Similarity	NPC246358
0.8143	Intermediate Similarity	NPC231572
0.814	Intermediate Similarity	NPC474040
0.814	Intermediate Similarity	NPC474214
0.8134	Intermediate Similarity	NPC120225
0.8134	Intermediate Similarity	NPC90128
0.8134	Intermediate Similarity	NPC213552
0.8134	Intermediate Similarity	NPC304630
0.8134	Intermediate Similarity	NPC58607
0.8134	Intermediate Similarity	NPC191037
0.8134	Intermediate Similarity	NPC92207
0.8134	Intermediate Similarity	NPC78974
0.8134	Intermediate Similarity	NPC274356
0.8134	Intermediate Similarity	NPC223136
0.8134	Intermediate Similarity	NPC17837
0.8134	Intermediate Similarity	NPC178284
0.8134	Intermediate Similarity	NPC303680
0.8134	Intermediate Similarity	NPC103823
0.8134	Intermediate Similarity	NPC28730
0.8134	Intermediate Similarity	NPC44748
0.8134	Intermediate Similarity	NPC18924
0.8134	Intermediate Similarity	NPC214406
0.8134	Intermediate Similarity	NPC84076
0.8134	Intermediate Similarity	NPC127937
0.8129	Intermediate Similarity	NPC301050
0.8129	Intermediate Similarity	NPC131204
0.812	Intermediate Similarity	NPC114901
0.812	Intermediate Similarity	NPC293701
0.812	Intermediate Similarity	NPC48990
0.8116	Intermediate Similarity	NPC473463
0.8106	Intermediate Similarity	NPC262253
0.8106	Intermediate Similarity	NPC71579

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 NPC214869 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	748
0.2-0.3	1134
0.3-0.4	2133
0.4-0.5	2471
0.5-0.6	1551
0.6-0.7	765
0.7-0.8	186
0.8-0.85	11
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9225	High Similarity	NPD2674	Phase 3
0.9	High Similarity	NPD3145	Approved
0.9	High Similarity	NPD3144	Approved
0.8429	Intermediate Similarity	NPD6331	Phase 2
0.8357	Intermediate Similarity	NPD3060	Approved
0.8322	Intermediate Similarity	NPD4123	Phase 3
0.8321	Intermediate Similarity	NPD1669	Approved
0.8306	Intermediate Similarity	NPD228	Approved
0.8298	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD2161	Phase 2
0.8258	Intermediate Similarity	NPD2922	Phase 1
0.8162	Intermediate Similarity	NPD5718	Phase 2
0.8156	Intermediate Similarity	NPD7153	Discontinued
0.8099	Intermediate Similarity	NPD4162	Approved
0.8045	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD1558	Phase 1
0.8041	Intermediate Similarity	NPD4675	Approved
0.8041	Intermediate Similarity	NPD4678	Approved
0.8031	Intermediate Similarity	NPD5283	Phase 1
0.8	Intermediate Similarity	NPD6895	Approved
0.8	Intermediate Similarity	NPD6896	Approved
0.7986	Intermediate Similarity	NPD5241	Discontinued
0.7973	Intermediate Similarity	NPD4005	Discontinued
0.797	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD3027	Phase 3
0.7945	Intermediate Similarity	NPD4739	Approved
0.7926	Intermediate Similarity	NPD3053	Approved
0.7926	Intermediate Similarity	NPD3055	Approved
0.7899	Intermediate Similarity	NPD5111	Phase 2
0.7899	Intermediate Similarity	NPD5109	Approved
0.7899	Intermediate Similarity	NPD5110	Phase 2
0.7891	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2977	Approved
0.7881	Intermediate Similarity	NPD2978	Approved
0.7879	Intermediate Similarity	NPD2668	Approved
0.7879	Intermediate Similarity	NPD2667	Approved
0.7852	Intermediate Similarity	NPD5311	Approved
0.7852	Intermediate Similarity	NPD5310	Approved
0.7832	Intermediate Similarity	NPD1375	Discontinued
0.7815	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD9377	Approved
0.7812	Intermediate Similarity	NPD9379	Approved
0.7778	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD7526	Approved
0.777	Intermediate Similarity	NPD52	Approved
0.7763	Intermediate Similarity	NPD5773	Approved
0.7763	Intermediate Similarity	NPD5772	Approved
0.7737	Intermediate Similarity	NPD6584	Phase 3
0.7727	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD5177	Phase 3
0.7724	Intermediate Similarity	NPD4237	Approved
0.7724	Intermediate Similarity	NPD4236	Phase 3
0.7717	Intermediate Similarity	NPD3021	Approved
0.7717	Intermediate Similarity	NPD3022	Approved
0.7714	Intermediate Similarity	NPD840	Approved
0.7714	Intermediate Similarity	NPD839	Approved
0.7707	Intermediate Similarity	NPD4083	Discontinued
0.7704	Intermediate Similarity	NPD2233	Approved
0.7704	Intermediate Similarity	NPD2232	Approved
0.7704	Intermediate Similarity	NPD2230	Approved
0.7698	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD3059	Approved
0.766	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD3062	Approved
0.766	Intermediate Similarity	NPD3061	Approved
0.7635	Intermediate Similarity	NPD4357	Discontinued
0.7613	Intermediate Similarity	NPD4055	Discovery
0.7589	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1024	Discontinued
0.7569	Intermediate Similarity	NPD4108	Discontinued
0.7568	Intermediate Similarity	NPD7124	Phase 2
0.7552	Intermediate Similarity	NPD5314	Approved
0.7552	Intermediate Similarity	NPD2653	Approved
0.7519	Intermediate Similarity	NPD5536	Phase 2
0.7518	Intermediate Similarity	NPD6583	Phase 3
0.7518	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6582	Phase 2
0.7516	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2219	Phase 1
0.7483	Intermediate Similarity	NPD2122	Discontinued
0.7481	Intermediate Similarity	NPD9381	Approved
0.7481	Intermediate Similarity	NPD9384	Approved
0.7467	Intermediate Similarity	NPD4584	Approved
0.7465	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD7477	Discontinued
0.7464	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2235	Phase 2
0.7445	Intermediate Similarity	NPD2231	Phase 2
0.7434	Intermediate Similarity	NPD3686	Approved
0.7434	Intermediate Similarity	NPD3687	Approved
0.7431	Intermediate Similarity	NPD2157	Approved
0.7429	Intermediate Similarity	NPD1712	Approved
0.7421	Intermediate Similarity	NPD4010	Discontinued
0.7419	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3620	Phase 2
0.7413	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2238	Phase 2
0.7405	Intermediate Similarity	NPD821	Approved
0.7391	Intermediate Similarity	NPD9622	Approved
0.7389	Intermediate Similarity	NPD5604	Discontinued
0.7389	Intermediate Similarity	NPD7833	Phase 2
0.7389	Intermediate Similarity	NPD7831	Phase 2
0.7389	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3455	Phase 2
0.7383	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6030	Approved
0.7368	Intermediate Similarity	NPD6031	Approved
0.7368	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD709	Approved
0.7358	Intermediate Similarity	NPD2821	Approved
0.7357	Intermediate Similarity	NPD9619	Approved
0.7357	Intermediate Similarity	NPD9620	Approved
0.7357	Intermediate Similarity	NPD7905	Discontinued
0.7357	Intermediate Similarity	NPD9621	Approved
0.7351	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD2228	Approved
0.7348	Intermediate Similarity	NPD2234	Approved
0.7348	Intermediate Similarity	NPD2229	Approved
0.7347	Intermediate Similarity	NPD3656	Approved
0.7333	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3054	Approved
0.731	Intermediate Similarity	NPD3052	Approved
0.7305	Intermediate Similarity	NPD4993	Discontinued
0.7305	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2808	Discontinued
0.7297	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1613	Approved
0.7292	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5090	Approved
0.729	Intermediate Similarity	NPD6072	Discontinued
0.729	Intermediate Similarity	NPD5089	Approved
0.7284	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4093	Discontinued
0.7279	Intermediate Similarity	NPD1357	Approved
0.7273	Intermediate Similarity	NPD601	Approved
0.7273	Intermediate Similarity	NPD597	Approved
0.7273	Intermediate Similarity	NPD824	Approved
0.7273	Intermediate Similarity	NPD598	Approved
0.7267	Intermediate Similarity	NPD3692	Discontinued
0.7266	Intermediate Similarity	NPD3685	Discontinued
0.7266	Intermediate Similarity	NPD2982	Phase 2
0.7266	Intermediate Similarity	NPD2983	Phase 2
0.7266	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3536	Discontinued
0.7237	Intermediate Similarity	NPD3985	Discontinued
0.7234	Intermediate Similarity	NPD7451	Discontinued
0.7231	Intermediate Similarity	NPD2684	Approved
0.7226	Intermediate Similarity	NPD3296	Phase 1
0.7222	Intermediate Similarity	NPD27	Approved
0.7222	Intermediate Similarity	NPD3530	Approved
0.7222	Intermediate Similarity	NPD2489	Approved
0.7222	Intermediate Similarity	NPD1136	Approved
0.7222	Intermediate Similarity	NPD1130	Approved
0.7222	Intermediate Similarity	NPD3532	Approved
0.7222	Intermediate Similarity	NPD3531	Approved
0.7222	Intermediate Similarity	NPD1132	Approved
0.7222	Intermediate Similarity	NPD259	Phase 1
0.7208	Intermediate Similarity	NPD2883	Discontinued
0.7205	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2981	Phase 2
0.7192	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3596	Phase 2
0.7183	Intermediate Similarity	NPD3018	Phase 2
0.7179	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7110	Phase 1
0.7176	Intermediate Similarity	NPD1792	Phase 2
0.7174	Intermediate Similarity	NPD3847	Discontinued
0.7172	Intermediate Similarity	NPD4060	Phase 1
0.7161	Intermediate Similarity	NPD4017	Approved
0.7161	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3111	Phase 1
0.7153	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1039	Discontinued
0.7152	Intermediate Similarity	NPD2560	Approved
0.7152	Intermediate Similarity	NPD2563	Approved
0.7143	Intermediate Similarity	NPD6111	Discontinued
0.7143	Intermediate Similarity	NPD7843	Approved
0.7134	Intermediate Similarity	NPD5720	Discontinued
0.7133	Intermediate Similarity	NPD2458	Approved
0.7133	Intermediate Similarity	NPD2460	Phase 3
0.7133	Intermediate Similarity	NPD2459	Approved
0.7133	Intermediate Similarity	NPD596	Approved
0.7133	Intermediate Similarity	NPD600	Approved
0.7124	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD555	Phase 2

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