NPASS Compound

Structure

CID115674 OpenBabel06191715472D 42 46 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 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 -6.9282 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 -2.5981 1.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 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 -2.5981 -0.5000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 3.4641 4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 12 1 0 0 0 0 4 10 2 0 0 0 0 4 13 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 11 1 0 0 0 0 6 17 2 0 0 0 0 7 15 1 0 0 0 0 7 16 2 0 0 0 0 8 28 1 0 0 0 0 9 1 1 6 0 0 0 9 20 1 0 0 0 0 9 38 1 0 0 0 0 10 16 1 0 0 0 0 11 39 1 0 0 0 0 12 13 2 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 19 2 0 0 0 0 14 31 1 0 0 0 0 15 19 1 0 0 0 0 15 32 2 0 0 0 0 16 40 1 0 0 0 0 17 19 1 0 0 0 0 17 40 1 0 0 0 0 18 8 1 1 0 0 0 18 21 1 0 0 0 0 18 41 1 0 0 0 0 20 22 1 0 0 0 0 20 33 1 1 0 0 0 21 23 1 0 0 0 0 21 34 1 6 0 0 0 22 24 1 0 0 0 0 22 35 1 6 0 0 0 23 25 1 0 0 0 0 23 36 1 1 0 0 0 24 26 1 0 0 0 0 24 37 1 6 0 0 0 25 27 1 0 0 0 0 25 42 1 6 0 0 0 26 38 1 0 0 0 0 26 42 1 1 0 0 0 27 39 1 1 0 0 0 27 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.16
Volume:	543.527
LogP:	0.66
LogD:	-0.102
LogS:	-3.678
# Rotatable Bonds:	6
TPSA:	249.2
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.149
Synthetic Accessibility Score:	4.705
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.468
MDCK Permeability:	3.059819573536515e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.914
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	87.19339752197266%
Volume Distribution (VD):	0.638
Pgp-substrate:	12.15773868560791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.114
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.576
Half-life (T1/2):	0.691

ADMET: Toxicity

hERG Blockers:	0.253
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.797
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.937
Carcinogencity:	0.143
Eye Corrosion:	0.003
Eye Irritation:	0.297
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC115674

Natural Product ID:	NPC115674
*Common Name:**	Lonicerin
IUPAC Name:	7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-one
Synonyms:	7-Neohesperidosylluteolin; Lonicerin
Standard InCHIKey:	SHPPXMGVUDNKLV-KMFFXDMSSA-N
Standard InCHI:	InChI=1S/C27H30O15/c1-9-20(33)22(35)24(37)26(38-9)42-25-23(36)21(34)18(8-28)41-27(25)39-11-5-14(31)19-15(32)7-16(40-17(19)6-11)10-2-3-12(29)13(30)4-10/h2-7,9,18,20-31,33-37H,8H2,1H3/t9-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1cc(c2c(=O)cc(c3ccc(c(c3)O)O)oc2c1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452979
PubChem CID:	5282152
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jep.2005.01.054]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141124]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11735581]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844965]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17602526]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17996677]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377852]
NPO32732	Pterospermum acerifolium	Species	Malvaceae	Eukaryota	flowers	n.a.	n.a.	PMID[21719287]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[22822669]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214875]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181920]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31418264]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29846	Lonicera dasystyla	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30003	Lonicera confuse	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6237	Cryptocarya aschersoniana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3597	Rheedia acuminata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4706	Streptomyces vinaceusdrappus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4728	Streptomyces tsukubensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6604	Melanothamnus afaqhusainii	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5641	Dendroctonus frontalis	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2832	Hazunta membranacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1899	Aria rostellata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5155	Peritassa compta	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5196	Eupatorium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO978	Panzerina lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO471	Ardisia neriifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO319	Citrus limon	Species	Rutaceae	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
NPO17752	NPC115674	Other	Leaf	12	12	12	mg/100g	Database [DUKE]
NPO319	NPC115674	Beverage (juice)	n.a.	1.850000024	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO17752	NPC115674	Dried Or Powder	n.a.	1170.351852	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

☑ 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	2
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	20.1	%	PMID[497390]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	11900.0	nM	PMID[497391]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2370.0	nM	PMID[497391]

☑ 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 NPC115674 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	437
0.1-0.2	1797
0.2-0.3	4002
0.3-0.4	9556
0.4-0.5	8673
0.5-0.6	4504
0.6-0.7	5402
0.7-0.8	5424
0.8-0.85	1819
0.85-0.9	571
0.9-0.95	415
0.95-1	97

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC210073
0.9873	High Similarity	NPC8856
0.9873	High Similarity	NPC209296
0.9873	High Similarity	NPC195257
0.9872	High Similarity	NPC19709
0.9811	High Similarity	NPC67105
0.9811	High Similarity	NPC150767
0.9811	High Similarity	NPC231194
0.9811	High Similarity	NPC95866
0.9811	High Similarity	NPC51326
0.9811	High Similarity	NPC78734
0.9809	High Similarity	NPC22832
0.9809	High Similarity	NPC311830
0.9808	High Similarity	NPC77660
0.9808	High Similarity	NPC189142
0.9808	High Similarity	NPC473043
0.975	High Similarity	NPC203259
0.975	High Similarity	NPC256760
0.975	High Similarity	NPC471725
0.975	High Similarity	NPC471748
0.975	High Similarity	NPC176740
0.975	High Similarity	NPC33054
0.975	High Similarity	NPC155877
0.975	High Similarity	NPC134532
0.9748	High Similarity	NPC43587
0.9748	High Similarity	NPC227508
0.9748	High Similarity	NPC86008
0.9747	High Similarity	NPC5778
0.9747	High Similarity	NPC236934
0.9745	High Similarity	NPC309025
0.9745	High Similarity	NPC222936
0.9745	High Similarity	NPC270335
0.9745	High Similarity	NPC243930
0.9745	High Similarity	NPC29830
0.9745	High Similarity	NPC168822
0.9745	High Similarity	NPC284960
0.9745	High Similarity	NPC88023
0.9745	High Similarity	NPC191306
0.9689	High Similarity	NPC204693
0.9689	High Similarity	NPC208668
0.9688	High Similarity	NPC105095
0.9688	High Similarity	NPC44328
0.9688	High Similarity	NPC259896
0.9688	High Similarity	NPC156869
0.9688	High Similarity	NPC177731
0.9688	High Similarity	NPC255157
0.9688	High Similarity	NPC218488
0.9688	High Similarity	NPC254855
0.9688	High Similarity	NPC285197
0.9688	High Similarity	NPC136042
0.9688	High Similarity	NPC29958
0.9688	High Similarity	NPC79056
0.9688	High Similarity	NPC67326
0.9686	High Similarity	NPC173637
0.9686	High Similarity	NPC229729
0.9686	High Similarity	NPC127546
0.9686	High Similarity	NPC52550
0.9686	High Similarity	NPC275454
0.9686	High Similarity	NPC84362
0.9686	High Similarity	NPC223424
0.9686	High Similarity	NPC317489
0.9684	High Similarity	NPC277205
0.9684	High Similarity	NPC284277
0.9684	High Similarity	NPC475366
0.9684	High Similarity	NPC475497
0.9682	High Similarity	NPC127782
0.9682	High Similarity	NPC300537
0.963	High Similarity	NPC294815
0.963	High Similarity	NPC198199
0.963	High Similarity	NPC473327
0.963	High Similarity	NPC220173
0.963	High Similarity	NPC19108
0.963	High Similarity	NPC294629
0.963	High Similarity	NPC16194
0.963	High Similarity	NPC476472
0.9627	High Similarity	NPC26230
0.9627	High Similarity	NPC180918
0.9627	High Similarity	NPC259152
0.9627	High Similarity	NPC60735
0.9627	High Similarity	NPC3583
0.9627	High Similarity	NPC301683
0.9625	High Similarity	NPC52382
0.9625	High Similarity	NPC219904
0.9625	High Similarity	NPC229687
0.9625	High Similarity	NPC223747
0.9625	High Similarity	NPC226294
0.9625	High Similarity	NPC120099
0.9625	High Similarity	NPC201292
0.9625	High Similarity	NPC58053
0.9625	High Similarity	NPC270578
0.9625	High Similarity	NPC475942
0.9625	High Similarity	NPC45638
0.9625	High Similarity	NPC293629
0.9625	High Similarity	NPC105283
0.9625	High Similarity	NPC186807
0.9625	High Similarity	NPC93337
0.9625	High Similarity	NPC225434
0.9625	High Similarity	NPC469931
0.9625	High Similarity	NPC203050
0.9625	High Similarity	NPC105025
0.9623	High Similarity	NPC88789
0.9623	High Similarity	NPC197285
0.9623	High Similarity	NPC145038
0.9623	High Similarity	NPC281131
0.9623	High Similarity	NPC274618
0.9623	High Similarity	NPC253662
0.9623	High Similarity	NPC21100
0.9623	High Similarity	NPC135599
0.9623	High Similarity	NPC328940
0.9623	High Similarity	NPC113968
0.9623	High Similarity	NPC276222
0.9623	High Similarity	NPC118284
0.9623	High Similarity	NPC277174
0.9623	High Similarity	NPC179950
0.9623	High Similarity	NPC308404
0.9623	High Similarity	NPC73855
0.9623	High Similarity	NPC56077
0.9618	High Similarity	NPC182045
0.9571	High Similarity	NPC169733
0.9571	High Similarity	NPC292019
0.9571	High Similarity	NPC122467
0.9571	High Similarity	NPC14187
0.9571	High Similarity	NPC65563
0.9571	High Similarity	NPC89127
0.9571	High Similarity	NPC202908
0.9571	High Similarity	NPC471669
0.9571	High Similarity	NPC470949
0.9568	High Similarity	NPC25724
0.9568	High Similarity	NPC236191
0.9568	High Similarity	NPC239549
0.9568	High Similarity	NPC472993
0.9568	High Similarity	NPC51774
0.9565	High Similarity	NPC244776
0.9565	High Similarity	NPC206123
0.9565	High Similarity	NPC21190
0.9565	High Similarity	NPC183357
0.9565	High Similarity	NPC22195
0.9565	High Similarity	NPC116864
0.9563	High Similarity	NPC160156
0.9563	High Similarity	NPC226304
0.9563	High Similarity	NPC477502
0.9563	High Similarity	NPC92565
0.9563	High Similarity	NPC58716
0.9563	High Similarity	NPC265530
0.9563	High Similarity	NPC45400
0.9563	High Similarity	NPC146792
0.9563	High Similarity	NPC45618
0.9563	High Similarity	NPC325555
0.956	High Similarity	NPC55786
0.956	High Similarity	NPC240431
0.956	High Similarity	NPC19388
0.956	High Similarity	NPC15358
0.9554	High Similarity	NPC110349
0.9551	High Similarity	NPC129827
0.9551	High Similarity	NPC65003
0.9551	High Similarity	NPC44931
0.9551	High Similarity	NPC473512
0.9512	High Similarity	NPC120952
0.9512	High Similarity	NPC251417
0.9512	High Similarity	NPC89052
0.9512	High Similarity	NPC173837
0.9509	High Similarity	NPC253685
0.9506	High Similarity	NPC307518
0.9506	High Similarity	NPC245452
0.9506	High Similarity	NPC117260
0.9506	High Similarity	NPC67134
0.9506	High Similarity	NPC47140
0.9506	High Similarity	NPC476405
0.9506	High Similarity	NPC254540
0.9506	High Similarity	NPC153755
0.9506	High Similarity	NPC172807
0.9506	High Similarity	NPC235575
0.9506	High Similarity	NPC205076
0.9506	High Similarity	NPC211594
0.9506	High Similarity	NPC190003
0.9506	High Similarity	NPC48773
0.9506	High Similarity	NPC267254
0.9506	High Similarity	NPC175107
0.9506	High Similarity	NPC261254
0.9503	High Similarity	NPC95855
0.9503	High Similarity	NPC170675
0.9503	High Similarity	NPC472381
0.9503	High Similarity	NPC471457
0.9503	High Similarity	NPC472383
0.9503	High Similarity	NPC210042
0.9503	High Similarity	NPC112755
0.95	High Similarity	NPC99957
0.95	High Similarity	NPC181616
0.9497	High Similarity	NPC88043
0.9494	High Similarity	NPC303913
0.949	High Similarity	NPC473634
0.949	High Similarity	NPC22062
0.949	High Similarity	NPC138811
0.9487	High Similarity	NPC261866
0.9455	High Similarity	NPC470443
0.9455	High Similarity	NPC470444
0.9455	High Similarity	NPC110941
0.9455	High Similarity	NPC241423
0.9455	High Similarity	NPC473571
0.9455	High Similarity	NPC192539

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 NPC115674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	935
0.2-0.3	1887
0.3-0.4	2761
0.4-0.5	1833
0.5-0.6	909
0.6-0.7	281
0.7-0.8	116
0.8-0.85	21
0.85-0.9	7
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9873	High Similarity	NPD7054	Approved
0.9811	High Similarity	NPD7472	Approved
0.975	High Similarity	NPD6797	Phase 2
0.9689	High Similarity	NPD7251	Discontinued
0.9688	High Similarity	NPD7074	Phase 3
0.9509	High Similarity	NPD7808	Phase 3
0.9321	High Similarity	NPD3818	Discontinued
0.9304	High Similarity	NPD4381	Clinical (unspecified phase)
0.9273	High Similarity	NPD4338	Clinical (unspecified phase)
0.9198	High Similarity	NPD6168	Clinical (unspecified phase)
0.9198	High Similarity	NPD6167	Clinical (unspecified phase)
0.9198	High Similarity	NPD6166	Phase 2
0.9146	High Similarity	NPD7804	Clinical (unspecified phase)
0.9051	High Similarity	NPD1934	Approved
0.8994	High Similarity	NPD2393	Clinical (unspecified phase)
0.8875	High Similarity	NPD2801	Approved
0.8782	High Similarity	NPD1511	Approved
0.8704	High Similarity	NPD3817	Phase 2
0.8688	High Similarity	NPD4380	Phase 2
0.8671	High Similarity	NPD1512	Approved
0.865	High Similarity	NPD4868	Clinical (unspecified phase)
0.8538	High Similarity	NPD6559	Discontinued
0.8537	High Similarity	NPD3882	Suspended
0.848	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7075	Discontinued
0.828	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD5494	Approved
0.8261	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5402	Approved
0.8242	Intermediate Similarity	NPD6801	Discontinued
0.8228	Intermediate Similarity	NPD1549	Phase 2
0.8225	Intermediate Similarity	NPD6959	Discontinued
0.8221	Intermediate Similarity	NPD1653	Approved
0.8193	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD5403	Approved
0.8144	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD2796	Approved
0.8092	Intermediate Similarity	NPD7228	Approved
0.8086	Intermediate Similarity	NPD6799	Approved
0.8084	Intermediate Similarity	NPD1465	Phase 2
0.8084	Intermediate Similarity	NPD7819	Suspended
0.8072	Intermediate Similarity	NPD7411	Suspended
0.8046	Intermediate Similarity	NPD5844	Phase 1
0.8038	Intermediate Similarity	NPD1510	Phase 2
0.8037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5401	Approved
0.8023	Intermediate Similarity	NPD8312	Approved
0.8023	Intermediate Similarity	NPD8313	Approved
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7685	Pre-registration
0.7989	Intermediate Similarity	NPD3751	Discontinued
0.7965	Intermediate Similarity	NPD6232	Discontinued
0.7965	Intermediate Similarity	NPD3787	Discontinued
0.7939	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7266	Discontinued
0.7931	Intermediate Similarity	NPD7473	Discontinued
0.7907	Intermediate Similarity	NPD7199	Phase 2
0.7898	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1613	Approved
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6599	Discontinued
0.7791	Intermediate Similarity	NPD6234	Discontinued
0.7791	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1240	Approved
0.7778	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD8455	Phase 2
0.776	Intermediate Similarity	NPD8151	Discontinued
0.7749	Intermediate Similarity	NPD7584	Approved
0.7714	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD6776	Approved
0.7713	Intermediate Similarity	NPD6779	Approved
0.7713	Intermediate Similarity	NPD6780	Approved
0.7713	Intermediate Similarity	NPD6781	Approved
0.7713	Intermediate Similarity	NPD6777	Approved
0.7713	Intermediate Similarity	NPD6782	Approved
0.7713	Intermediate Similarity	NPD6778	Approved
0.7706	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD1607	Approved
0.7683	Intermediate Similarity	NPD3750	Approved
0.7674	Intermediate Similarity	NPD4967	Phase 2
0.7674	Intermediate Similarity	NPD4966	Approved
0.7674	Intermediate Similarity	NPD4965	Approved
0.7673	Intermediate Similarity	NPD943	Approved
0.7651	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD230	Phase 1
0.7625	Intermediate Similarity	NPD1933	Approved
0.7611	Intermediate Similarity	NPD7240	Approved
0.7595	Intermediate Similarity	NPD3027	Phase 3
0.7592	Intermediate Similarity	NPD7435	Discontinued
0.7592	Intermediate Similarity	NPD7696	Phase 3
0.7592	Intermediate Similarity	NPD7698	Approved
0.7592	Intermediate Similarity	NPD7697	Approved
0.759	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7783	Phase 2
0.7586	Intermediate Similarity	NPD919	Approved
0.758	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4628	Phase 3
0.7572	Intermediate Similarity	NPD7768	Phase 2
0.7547	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1551	Phase 2
0.753	Intermediate Similarity	NPD6190	Approved
0.7529	Intermediate Similarity	NPD3749	Approved
0.7526	Intermediate Similarity	NPD7701	Phase 2
0.7514	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD1247	Approved
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7448	Intermediate Similarity	NPD6823	Phase 2
0.7447	Intermediate Similarity	NPD6534	Approved
0.7447	Intermediate Similarity	NPD6535	Approved
0.7439	Intermediate Similarity	NPD2935	Discontinued
0.7421	Intermediate Similarity	NPD7699	Phase 2
0.7421	Intermediate Similarity	NPD7700	Phase 2
0.741	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD447	Suspended
0.7396	Intermediate Similarity	NPD2533	Approved
0.7396	Intermediate Similarity	NPD2532	Approved
0.7396	Intermediate Similarity	NPD2534	Approved
0.7378	Intermediate Similarity	NPD3748	Approved
0.7368	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7874	Approved
0.7347	Intermediate Similarity	NPD7585	Approved
0.7326	Intermediate Similarity	NPD7458	Discontinued
0.7323	Intermediate Similarity	NPD7801	Approved
0.731	Intermediate Similarity	NPD920	Approved
0.7308	Intermediate Similarity	NPD1091	Approved
0.7305	Intermediate Similarity	NPD2800	Approved
0.7296	Intermediate Similarity	NPD7583	Approved
0.7294	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8320	Phase 1
0.7282	Intermediate Similarity	NPD8319	Approved
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7268	Intermediate Similarity	NPD5953	Discontinued
0.7263	Intermediate Similarity	NPD4360	Phase 2
0.7263	Intermediate Similarity	NPD4363	Phase 3
0.7254	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7390	Discontinued
0.7231	Intermediate Similarity	NPD7680	Approved
0.7229	Intermediate Similarity	NPD6099	Approved
0.7229	Intermediate Similarity	NPD6100	Approved
0.7225	Intermediate Similarity	NPD3226	Approved
0.7219	Intermediate Similarity	NPD8150	Discontinued
0.7211	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6212	Phase 3
0.7211	Intermediate Similarity	NPD6213	Phase 3
0.7205	Intermediate Similarity	NPD6832	Phase 2
0.7205	Intermediate Similarity	NPD4908	Phase 1
0.7202	Intermediate Similarity	NPD6674	Discontinued
0.7202	Intermediate Similarity	NPD1243	Approved
0.7202	Intermediate Similarity	NPD1652	Phase 2
0.72	Intermediate Similarity	NPD6844	Discontinued
0.7193	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2798	Approved
0.7176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7286	Phase 2
0.7152	Intermediate Similarity	NPD6651	Approved
0.7143	Intermediate Similarity	NPD9494	Approved
0.7128	Intermediate Similarity	NPD8434	Phase 2
0.7125	Intermediate Similarity	NPD1203	Approved
0.7117	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.7107	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5124	Phase 1
0.7091	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2346	Discontinued
0.7083	Intermediate Similarity	NPD2344	Approved
0.7066	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1548	Phase 1
0.7029	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5353	Approved
0.7019	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD3268	Approved
0.7012	Intermediate Similarity	NPD6798	Discontinued
0.7005	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD422	Phase 1
0.6981	Remote Similarity	NPD1610	Phase 2
0.6978	Remote Similarity	NPD5710	Approved
0.6978	Remote Similarity	NPD5711	Approved
0.697	Remote Similarity	NPD6233	Phase 2
0.6964	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7930	Approved
0.6957	Remote Similarity	NPD3225	Approved
0.6949	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5242	Approved
0.6937	Remote Similarity	NPD9717	Approved
0.6937	Remote Similarity	NPD9269	Phase 2
0.6923	Remote Similarity	NPD8127	Discontinued

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