NPASS Compound

Structure

CID428 OpenBabel06191715322D 24 26 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 5.1962 1.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 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 0.8660 -0.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 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 6.9282 3.0000 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 20 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 20 1 0 0 0 0 8 12 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 8 1 6 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	329.16
Volume:	341.85
LogP:	1.918
LogD:	3.108
LogS:	-1.683
# Rotatable Bonds:	4
TPSA:	62.16
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.903
Synthetic Accessibility Score:	2.806
Fsp3:	0.368
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:	-4.756
MDCK Permeability:	1.5501896996283904e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.764
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.241
30% Bioavailability (F30%):	0.83

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	82.69873809814453%
Volume Distribution (VD):	1.886
Pgp-substrate:	13.068167686462402%

ADMET: Metabolism

CYP1A2-inhibitor:	0.349
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.166
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.722
CYP2D6-inhibitor:	0.431
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	14.589
Half-life (T1/2):	0.865

ADMET: Toxicity

hERG Blockers:	0.591
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.289
AMES Toxicity:	0.268
Rat Oral Acute Toxicity:	0.416
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.82
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.895

Download Data

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

Natural Product: NPC428

Natural Product ID:	NPC428
*Common Name:**	(R)-Reticuline
IUPAC Name:	(1R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
Synonyms:	(R)-Reticuline
Standard InCHIKey:	BHLYRWXGMIUIHG-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m1/s1
SMILES:	CN1CCc2cc(c(cc2[C@H]1Cc1ccc(c(c1)O)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401501
PubChem CID:	440586
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50053a043]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[11045899]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575948]
NPO20958	Smenospongia aurea	Species	Thorectidae	Eukaryota	n.a.	Jamaican	n.a.	PMID[11975483]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO20254	Ipomoea leptophylla	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640518]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO22556	Dendrolobium lanceolatum	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[15217275]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[17340259]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17366734]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	stem	n.a.	PMID[18175990]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[19555186]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19645233]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25612070]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28836430]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277309]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	stem	n.a.	Database[Article]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29868	Dicentra spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17796	Lamprocapnos spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29868	Dicentra spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13346	Lindera strichnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2466	Aloe microstigma	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22556	Dendrolobium lanceolatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18257	Oberna wallichiana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21848	Rosa hybr	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20958	Smenospongia aurea	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6701	Cinnamomum camphora	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17796	Lamprocapnos spectabilis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11791	Magnolia obovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20254	Ipomoea leptophylla	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22817	Actinidia valvata	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7312	Aplidium multiplicatum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17360	Argemone albiflora	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18680	Larix decidua	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10176	Chrozophora prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6328	Corydalis incisa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14326	Pseudocercospora fijiensis	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22495	Cladonia alpestris	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21026	Pericopsis mooniana	Species	Fabaceae	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
Others	2

Activity Type	# Activity
Cell Line	4
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Emax	=	15.9	%	PMID[455664]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[455665]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[455665]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000.0	nM	PMID[455665]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	26830.0	nM	PMID[455665]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	61.4	%	PMID[455666]

☑ 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 NPC428 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	261
0.1-0.2	1527
0.2-0.3	7965
0.3-0.4	9974
0.4-0.5	5821
0.5-0.6	11052
0.6-0.7	4483
0.7-0.8	1153
0.8-0.85	259
0.85-0.9	105
0.9-0.95	72
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC24233
1.0	High Similarity	NPC135538
1.0	High Similarity	NPC476571
1.0	High Similarity	NPC246587
1.0	High Similarity	NPC147390
0.9928	High Similarity	NPC321505
0.9928	High Similarity	NPC191376
0.9928	High Similarity	NPC179825
0.9784	High Similarity	NPC185838
0.9718	High Similarity	NPC151895
0.9718	High Similarity	NPC97221
0.9718	High Similarity	NPC88249
0.9718	High Similarity	NPC220858
0.9718	High Similarity	NPC192768
0.9648	High Similarity	NPC477565
0.9648	High Similarity	NPC103379
0.9586	High Similarity	NPC276588
0.9586	High Similarity	NPC2413
0.9586	High Similarity	NPC249797
0.9586	High Similarity	NPC5238
0.9586	High Similarity	NPC39701
0.9586	High Similarity	NPC204828
0.9586	High Similarity	NPC295691
0.9586	High Similarity	NPC207757
0.9586	High Similarity	NPC110416
0.9586	High Similarity	NPC54379
0.9586	High Similarity	NPC278799
0.9586	High Similarity	NPC469817
0.9586	High Similarity	NPC172765
0.9586	High Similarity	NPC127674
0.9586	High Similarity	NPC184026
0.9586	High Similarity	NPC193949
0.9586	High Similarity	NPC189266
0.9514	High Similarity	NPC76213
0.9514	High Similarity	NPC277669
0.9507	High Similarity	NPC476151
0.9496	High Similarity	NPC474915
0.9496	High Similarity	NPC213206
0.9496	High Similarity	NPC328750
0.9496	High Similarity	NPC188163
0.9424	High Similarity	NPC314682
0.9375	High Similarity	NPC60538
0.9375	High Similarity	NPC207824
0.9262	High Similarity	NPC111485
0.9252	High Similarity	NPC2295
0.9252	High Similarity	NPC477564
0.9225	High Similarity	NPC136860
0.9225	High Similarity	NPC128019
0.9225	High Similarity	NPC476567
0.9209	High Similarity	NPC301050
0.9209	High Similarity	NPC131204
0.92	High Similarity	NPC166014
0.92	High Similarity	NPC27410
0.9184	High Similarity	NPC82285
0.9184	High Similarity	NPC133011
0.9145	High Similarity	NPC238530
0.9145	High Similarity	NPC232514
0.9145	High Similarity	NPC276944
0.9128	High Similarity	NPC147091
0.9103	High Similarity	NPC16107
0.9103	High Similarity	NPC210437
0.9103	High Similarity	NPC51957
0.9103	High Similarity	NPC106295
0.9103	High Similarity	NPC476144
0.9085	High Similarity	NPC42549
0.9085	High Similarity	NPC317272
0.9085	High Similarity	NPC256012
0.9085	High Similarity	NPC240841
0.9085	High Similarity	NPC268503
0.9085	High Similarity	NPC250846
0.9085	High Similarity	NPC264850
0.9085	High Similarity	NPC13916
0.9079	High Similarity	NPC324144
0.9054	High Similarity	NPC37272
0.9041	High Similarity	NPC7467
0.9041	High Similarity	NPC475959
0.9028	High Similarity	NPC294249
0.9026	High Similarity	NPC145832
0.9026	High Similarity	NPC474931
0.9026	High Similarity	NPC81218
0.9026	High Similarity	NPC158376
0.9026	High Similarity	NPC306555
0.9026	High Similarity	NPC117188
0.9026	High Similarity	NPC205421
0.9026	High Similarity	NPC12053
0.902	High Similarity	NPC136508
0.902	High Similarity	NPC13504
0.902	High Similarity	NPC24465
0.902	High Similarity	NPC196447
0.902	High Similarity	NPC4138
0.902	High Similarity	NPC284183
0.902	High Similarity	NPC306843
0.902	High Similarity	NPC96603
0.902	High Similarity	NPC253043
0.902	High Similarity	NPC78222
0.902	High Similarity	NPC212794
0.902	High Similarity	NPC121275
0.902	High Similarity	NPC477563
0.9	High Similarity	NPC186063
0.8968	High Similarity	NPC83198
0.8968	High Similarity	NPC204908
0.8947	High Similarity	NPC205167
0.8919	High Similarity	NPC274026
0.8903	High Similarity	NPC210140
0.8889	High Similarity	NPC60186
0.8846	High Similarity	NPC66573
0.8839	High Similarity	NPC476573
0.8839	High Similarity	NPC81247
0.8839	High Similarity	NPC35627
0.8831	High Similarity	NPC1229
0.8824	High Similarity	NPC249274
0.8816	High Similarity	NPC475326
0.88	High Similarity	NPC26601
0.8797	High Similarity	NPC152680
0.8797	High Similarity	NPC232386
0.8797	High Similarity	NPC190783
0.879	High Similarity	NPC109925
0.8777	High Similarity	NPC160193
0.8774	High Similarity	NPC134858
0.875	High Similarity	NPC323123
0.8734	High Similarity	NPC239775
0.8734	High Similarity	NPC475215
0.8734	High Similarity	NPC108434
0.8733	High Similarity	NPC81733
0.8733	High Similarity	NPC326316
0.8733	High Similarity	NPC476568
0.871	High Similarity	NPC233650
0.8707	High Similarity	NPC130926
0.8684	High Similarity	NPC216459
0.8684	High Similarity	NPC41178
0.8684	High Similarity	NPC138487
0.8681	High Similarity	NPC170170
0.8681	High Similarity	NPC219233
0.8681	High Similarity	NPC211468
0.8679	High Similarity	NPC477020
0.8679	High Similarity	NPC192135
0.8679	High Similarity	NPC66341
0.8675	High Similarity	NPC210148
0.8675	High Similarity	NPC233029
0.8671	High Similarity	NPC26240
0.8671	High Similarity	NPC69712
0.8671	High Similarity	NPC477562
0.8671	High Similarity	NPC168753
0.8671	High Similarity	NPC118274
0.8662	High Similarity	NPC298979
0.8636	High Similarity	NPC59028
0.8636	High Similarity	NPC92191
0.8634	High Similarity	NPC320223
0.8634	High Similarity	NPC114364
0.8633	High Similarity	NPC172403
0.8627	High Similarity	NPC25084
0.8627	High Similarity	NPC146288
0.8627	High Similarity	NPC247639
0.8625	High Similarity	NPC199465
0.8625	High Similarity	NPC128560
0.8625	High Similarity	NPC229166
0.8611	High Similarity	NPC253429
0.8611	High Similarity	NPC193528
0.8608	High Similarity	NPC470324
0.86	High Similarity	NPC92541
0.86	High Similarity	NPC219162
0.8581	High Similarity	NPC226428
0.858	High Similarity	NPC32154
0.8571	High Similarity	NPC476572
0.8562	High Similarity	NPC325871
0.8562	High Similarity	NPC99659
0.8562	High Similarity	NPC80129
0.8562	High Similarity	NPC187022
0.8544	High Similarity	NPC150879
0.8535	High Similarity	NPC255607
0.8535	High Similarity	NPC3375
0.8533	High Similarity	NPC130941
0.8528	High Similarity	NPC286119
0.8506	High Similarity	NPC234392
0.8506	High Similarity	NPC31311
0.8487	Intermediate Similarity	NPC476579
0.8481	Intermediate Similarity	NPC124657
0.8476	Intermediate Similarity	NPC328155
0.8476	Intermediate Similarity	NPC8836
0.8476	Intermediate Similarity	NPC7715
0.8476	Intermediate Similarity	NPC285931
0.8476	Intermediate Similarity	NPC271013
0.8476	Intermediate Similarity	NPC182052
0.8476	Intermediate Similarity	NPC251735
0.8476	Intermediate Similarity	NPC239824
0.8476	Intermediate Similarity	NPC54654
0.8476	Intermediate Similarity	NPC290582
0.8476	Intermediate Similarity	NPC217748
0.8476	Intermediate Similarity	NPC104196
0.8476	Intermediate Similarity	NPC279228
0.8476	Intermediate Similarity	NPC222661
0.8476	Intermediate Similarity	NPC258657
0.8476	Intermediate Similarity	NPC223690
0.8476	Intermediate Similarity	NPC49075
0.8476	Intermediate Similarity	NPC229373
0.8476	Intermediate Similarity	NPC90998
0.8476	Intermediate Similarity	NPC311973
0.8476	Intermediate Similarity	NPC290005
0.8476	Intermediate Similarity	NPC181796
0.8476	Intermediate Similarity	NPC30779

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 NPC428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	735
0.2-0.3	1038
0.3-0.4	1707
0.4-0.5	2640
0.5-0.6	1843
0.6-0.7	723
0.7-0.8	245
0.8-0.85	35
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9496	High Similarity	NPD4664	Clinical (unspecified phase)
0.9103	High Similarity	NPD4584	Approved
0.8961	High Similarity	NPD4010	Discontinued
0.8733	High Similarity	NPD4017	Approved
0.8639	High Similarity	NPD5241	Discontinued
0.8618	High Similarity	NPD4773	Phase 2
0.8618	High Similarity	NPD4772	Phase 2
0.8608	High Similarity	NPD2898	Approved
0.859	High Similarity	NPD7201	Clinical (unspecified phase)
0.8562	High Similarity	NPD7298	Approved
0.8477	Intermediate Similarity	NPD3639	Approved
0.8477	Intermediate Similarity	NPD6031	Approved
0.8477	Intermediate Similarity	NPD3641	Approved
0.8477	Intermediate Similarity	NPD6030	Approved
0.8477	Intermediate Similarity	NPD3640	Phase 3
0.8476	Intermediate Similarity	NPD8054	Approved
0.8476	Intermediate Similarity	NPD8053	Approved
0.8467	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD2421	Approved
0.84	Intermediate Similarity	NPD2420	Approved
0.8387	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7831	Phase 2
0.8344	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7833	Phase 2
0.8333	Intermediate Similarity	NPD3845	Phase 1
0.8322	Intermediate Similarity	NPD5718	Phase 2
0.8264	Intermediate Similarity	NPD2674	Phase 3
0.8261	Intermediate Similarity	NPD27	Approved
0.8261	Intermediate Similarity	NPD2489	Approved
0.8252	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6297	Approved
0.8108	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD2970	Approved
0.8086	Intermediate Similarity	NPD2969	Approved
0.8069	Intermediate Similarity	NPD3144	Approved
0.8069	Intermediate Similarity	NPD3145	Approved
0.8056	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD8099	Discontinued
0.8049	Intermediate Similarity	NPD8251	Approved
0.8049	Intermediate Similarity	NPD8252	Approved
0.8041	Intermediate Similarity	NPD6896	Approved
0.8041	Intermediate Similarity	NPD6895	Approved
0.8025	Intermediate Similarity	NPD6071	Discontinued
0.8025	Intermediate Similarity	NPD3051	Approved
0.8013	Intermediate Similarity	NPD5177	Phase 3
0.8013	Intermediate Similarity	NPD3060	Approved
0.8	Intermediate Similarity	NPD8156	Discontinued
0.7988	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2563	Approved
0.7987	Intermediate Similarity	NPD2560	Approved
0.7963	Intermediate Similarity	NPD7802	Discontinued
0.7963	Intermediate Similarity	NPD6107	Approved
0.7937	Intermediate Similarity	NPD6788	Approved
0.7929	Intermediate Similarity	NPD6853	Approved
0.7929	Intermediate Similarity	NPD6851	Approved
0.7925	Intermediate Similarity	NPD2978	Approved
0.7925	Intermediate Similarity	NPD2977	Approved
0.7922	Intermediate Similarity	NPD3124	Discontinued
0.7895	Intermediate Similarity	NPD7906	Approved
0.787	Intermediate Similarity	NPD7312	Approved
0.787	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7313	Approved
0.787	Intermediate Similarity	NPD7310	Approved
0.787	Intermediate Similarity	NPD7311	Approved
0.7867	Intermediate Similarity	NPD1753	Discontinued
0.7847	Intermediate Similarity	NPD3053	Approved
0.7847	Intermediate Similarity	NPD3055	Approved
0.7824	Intermediate Similarity	NPD7309	Approved
0.7805	Intermediate Similarity	NPD4166	Phase 2
0.7792	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4162	Approved
0.7765	Intermediate Similarity	NPD4577	Approved
0.7765	Intermediate Similarity	NPD4578	Approved
0.7764	Intermediate Similarity	NPD5977	Approved
0.7764	Intermediate Similarity	NPD5978	Approved
0.7742	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4663	Approved
0.7718	Intermediate Similarity	NPD3109	Approved
0.7718	Intermediate Similarity	NPD3110	Approved
0.7716	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7110	Phase 1
0.7688	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5312	Approved
0.7679	Intermediate Similarity	NPD5313	Approved
0.7676	Intermediate Similarity	NPD2667	Approved
0.7676	Intermediate Similarity	NPD2668	Approved
0.7673	Intermediate Similarity	NPD824	Approved
0.7673	Intermediate Similarity	NPD4005	Discontinued
0.7669	Intermediate Similarity	NPD4055	Discovery
0.7662	Intermediate Similarity	NPD4237	Approved
0.7662	Intermediate Similarity	NPD4236	Phase 3
0.7651	Intermediate Similarity	NPD4474	Approved
0.7651	Intermediate Similarity	NPD4475	Approved
0.7643	Intermediate Similarity	NPD4123	Phase 3
0.7639	Intermediate Similarity	NPD2230	Approved
0.7639	Intermediate Similarity	NPD2232	Approved
0.7639	Intermediate Similarity	NPD2233	Approved
0.7628	Intermediate Similarity	NPD7124	Phase 2
0.7627	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3636	Approved
0.7619	Intermediate Similarity	NPD3637	Approved
0.7619	Intermediate Similarity	NPD3635	Approved
0.7613	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4093	Discontinued
0.7605	Intermediate Similarity	NPD4481	Phase 3
0.76	Intermediate Similarity	NPD2488	Approved
0.76	Intermediate Similarity	NPD2490	Approved
0.7595	Intermediate Similarity	NPD6090	Discontinued
0.7564	Intermediate Similarity	NPD3692	Discontinued
0.7558	Intermediate Similarity	NPD7280	Phase 3
0.7558	Intermediate Similarity	NPD7281	Phase 3
0.7547	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6688	Approved
0.7545	Intermediate Similarity	NPD6687	Approved
0.7534	Intermediate Similarity	NPD5311	Approved
0.7534	Intermediate Similarity	NPD5310	Approved
0.7532	Intermediate Similarity	NPD1424	Approved
0.7532	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5156	Approved
0.7517	Intermediate Similarity	NPD5155	Approved
0.75	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6331	Phase 2
0.75	Intermediate Similarity	NPD823	Approved
0.75	Intermediate Similarity	NPD817	Approved
0.7485	Intermediate Similarity	NPD5772	Approved
0.7485	Intermediate Similarity	NPD5773	Approved
0.7484	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2238	Phase 2
0.7466	Intermediate Similarity	NPD1669	Approved
0.7455	Intermediate Similarity	NPD5604	Discontinued
0.745	Intermediate Similarity	NPD3595	Approved
0.745	Intermediate Similarity	NPD2605	Approved
0.745	Intermediate Similarity	NPD2606	Approved
0.745	Intermediate Similarity	NPD3594	Approved
0.744	Intermediate Similarity	NPD4083	Discontinued
0.7432	Intermediate Similarity	NPD6584	Phase 3
0.7432	Intermediate Similarity	NPD7905	Discontinued
0.7429	Intermediate Similarity	NPD5283	Phase 1
0.7423	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3656	Approved
0.7417	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD228	Approved
0.7407	Intermediate Similarity	NPD4678	Approved
0.7407	Intermediate Similarity	NPD6875	Approved
0.7407	Intermediate Similarity	NPD4675	Approved
0.7407	Intermediate Similarity	NPD6876	Approved
0.7401	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6748	Discontinued
0.7386	Intermediate Similarity	NPD7291	Discontinued
0.7372	Intermediate Similarity	NPD7037	Approved
0.7372	Intermediate Similarity	NPD7153	Discontinued
0.7368	Intermediate Similarity	NPD3059	Approved
0.7368	Intermediate Similarity	NPD3062	Approved
0.7368	Intermediate Similarity	NPD3061	Approved
0.7365	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4103	Phase 2
0.7365	Intermediate Similarity	NPD5677	Discontinued
0.7365	Intermediate Similarity	NPD4098	Discontinued
0.7356	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2161	Phase 2
0.7347	Intermediate Similarity	NPD4659	Approved
0.7342	Intermediate Similarity	NPD5160	Discontinued
0.7329	Intermediate Similarity	NPD2122	Discontinued
0.7326	Intermediate Similarity	NPD3920	Phase 2
0.7326	Intermediate Similarity	NPD7479	Phase 2
0.7325	Intermediate Similarity	NPD44	Approved
0.7325	Intermediate Similarity	NPD6364	Approved
0.7322	Intermediate Similarity	NPD2493	Approved
0.7322	Intermediate Similarity	NPD2494	Approved
0.7322	Intermediate Similarity	NPD3452	Approved
0.7322	Intermediate Similarity	NPD3450	Approved
0.7317	Intermediate Similarity	NPD5720	Discontinued
0.7314	Intermediate Similarity	NPD6618	Phase 2
0.731	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1132	Approved
0.7303	Intermediate Similarity	NPD1136	Approved
0.7303	Intermediate Similarity	NPD1130	Approved
0.7292	Intermediate Similarity	NPD5304	Approved
0.7292	Intermediate Similarity	NPD5303	Approved
0.7285	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5314	Approved
0.7267	Intermediate Similarity	NPD4873	Discontinued
0.7263	Intermediate Similarity	NPD3922	Approved
0.7263	Intermediate Similarity	NPD3921	Approved
0.7263	Intermediate Similarity	NPD3923	Approved
0.7263	Intermediate Similarity	NPD3924	Approved
0.7262	Intermediate Similarity	NPD4666	Phase 3
0.7255	Intermediate Similarity	NPD3620	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