NPASS Compound

Structure

CID253788 OpenBabel06191716052D 42 46 0 0 1 0 0 0 0 0999 V2000 3.4641 -4.0000 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 -3.4641 0.0000 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 3.4641 -3.0000 0.0000 C 0 0 1 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 0.8660 0.5000 0.0000 C 0 0 2 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 4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 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 4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 -2.5981 -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 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -2.5981 -2.5000 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 38 1 0 0 0 0 9 1 1 6 0 0 0 9 17 1 0 0 0 0 9 39 1 0 0 0 0 10 24 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 16 2 0 0 0 0 13 30 1 0 0 0 0 14 16 1 0 0 0 0 14 40 1 0 0 0 0 15 8 1 1 0 0 0 15 18 1 0 0 0 0 15 41 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 31 1 1 0 0 0 18 21 1 0 0 0 0 18 32 1 1 0 0 0 19 25 1 0 0 0 0 19 33 2 0 0 0 0 20 22 1 0 0 0 0 20 34 1 6 0 0 0 21 23 1 0 0 0 0 21 35 1 1 0 0 0 22 26 1 0 0 0 0 22 36 1 6 0 0 0 23 27 1 0 0 0 0 23 37 1 6 0 0 0 24 25 2 0 0 0 0 24 40 1 0 0 0 0 25 42 1 0 0 0 0 26 38 1 1 0 0 0 26 39 1 0 0 0 0 27 41 1 0 0 0 0 27 42 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.16
Volume:	543.527
LogP:	0.432
LogD:	-0.086
LogS:	-3.618
# 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:	0.159
Synthetic Accessibility Score:	4.68
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.403
MDCK Permeability:	1.992922625504434e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.815
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	86.69530487060547%
Volume Distribution (VD):	0.717
Pgp-substrate:	12.800872802734375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.138
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.202
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	1.241
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.237
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.804
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.92
Carcinogencity:	0.072
Eye Corrosion:	0.003
Eye Irritation:	0.163
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC253788

Natural Product ID:	NPC253788
*Common Name:**	Kaempferol-3-O-Robinobioside
IUPAC Name:	5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	RTATXGUCZHCSNG-KYGWAIEOSA-N
Standard InCHI:	InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18-,20+,21-,22+,23+,26+,27-/m0/s1
SMILES:	Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@@H]([C@@H]([C@H]1O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL79790
PubChem CID:	15944778
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1007/s11418-005-0009-z]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257536]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19177635]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19433363]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	Sunan County, Gansu Province, China	2006-JUN	PMID[20684529]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[22032651]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22032651]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	whole plant	Guide County, Qinghai Province, China	2008-AUG	PMID[22775441]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30219526]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29658	Spinulum annotinum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2670	Maytenus chuchuhuasha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5086	Alternaria macrospora	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1293	Streptomyces matensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2439	Diplopterygium glaucum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29658	Spinulum annotinum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9091	Orthosiphon spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10038.1	Abies pinsapo var. marocana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21472	Pterolobium hexapetalum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9594	Lysimachia fordiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO376	Suillus tridentinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9867	Ixeris debilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13474	Euphrasia genargentea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9998	Abies excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO593	Wikstroemia viridiflora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9737	Ampelocera edentula	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3838	Chrysosporum ovalisporum	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	5.0	%	PMID[496390]

☑ 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 NPC253788 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	433
0.1-0.2	1737
0.2-0.3	4140
0.3-0.4	9730
0.4-0.5	8694
0.5-0.6	4802
0.6-0.7	5875
0.7-0.8	5231
0.8-0.85	1182
0.85-0.9	390
0.9-0.95	380
0.95-1	103

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC246943
1.0	High Similarity	NPC173582
1.0	High Similarity	NPC163242
1.0	High Similarity	NPC476215
1.0	High Similarity	NPC276377
1.0	High Similarity	NPC249281
1.0	High Similarity	NPC139320
1.0	High Similarity	NPC116458
1.0	High Similarity	NPC181465
1.0	High Similarity	NPC265885
1.0	High Similarity	NPC473438
1.0	High Similarity	NPC215710
0.9935	High Similarity	NPC240306
0.9934	High Similarity	NPC471079
0.9934	High Similarity	NPC304741
0.9934	High Similarity	NPC187379
0.9934	High Similarity	NPC470405
0.9869	High Similarity	NPC64305
0.9869	High Similarity	NPC170052
0.9869	High Similarity	NPC135846
0.9869	High Similarity	NPC297987
0.9868	High Similarity	NPC111929
0.9868	High Similarity	NPC41121
0.9868	High Similarity	NPC320283
0.9868	High Similarity	NPC472459
0.9804	High Similarity	NPC153342
0.9804	High Similarity	NPC136761
0.9803	High Similarity	NPC129827
0.9803	High Similarity	NPC135391
0.9803	High Similarity	NPC182634
0.9803	High Similarity	NPC77672
0.9803	High Similarity	NPC65003
0.9803	High Similarity	NPC473512
0.9803	High Similarity	NPC133671
0.9803	High Similarity	NPC54802
0.9803	High Similarity	NPC108831
0.9803	High Similarity	NPC197304
0.9803	High Similarity	NPC44931
0.9803	High Similarity	NPC78263
0.9744	High Similarity	NPC477613
0.9744	High Similarity	NPC142142
0.9744	High Similarity	NPC476470
0.9744	High Similarity	NPC64425
0.9744	High Similarity	NPC189564
0.9744	High Similarity	NPC221342
0.9744	High Similarity	NPC256188
0.9744	High Similarity	NPC203145
0.9744	High Similarity	NPC186816
0.9744	High Similarity	NPC11432
0.9744	High Similarity	NPC32641
0.9744	High Similarity	NPC12013
0.974	High Similarity	NPC224530
0.974	High Similarity	NPC216496
0.974	High Similarity	NPC470125
0.974	High Similarity	NPC129217
0.974	High Similarity	NPC85707
0.974	High Similarity	NPC159579
0.974	High Similarity	NPC259957
0.974	High Similarity	NPC48093
0.9739	High Similarity	NPC138811
0.9739	High Similarity	NPC473634
0.9739	High Similarity	NPC22062
0.9737	High Similarity	NPC323593
0.9737	High Similarity	NPC203500
0.9737	High Similarity	NPC307938
0.9679	High Similarity	NPC76831
0.9679	High Similarity	NPC135358
0.9679	High Similarity	NPC292929
0.9679	High Similarity	NPC287889
0.9679	High Similarity	NPC289667
0.9677	High Similarity	NPC150164
0.9677	High Similarity	NPC27942
0.9675	High Similarity	NPC473623
0.9671	High Similarity	NPC27408
0.9671	High Similarity	NPC95090
0.962	High Similarity	NPC5319
0.9615	High Similarity	NPC66087
0.9615	High Similarity	NPC278419
0.9615	High Similarity	NPC179198
0.9615	High Similarity	NPC121703
0.9613	High Similarity	NPC282169
0.9613	High Similarity	NPC101636
0.9613	High Similarity	NPC303913
0.961	High Similarity	NPC104677
0.9608	High Similarity	NPC295613
0.9608	High Similarity	NPC473657
0.9608	High Similarity	NPC206378
0.9605	High Similarity	NPC143851
0.9605	High Similarity	NPC83283
0.9605	High Similarity	NPC210003
0.9605	High Similarity	NPC39360
0.9605	High Similarity	NPC29763
0.956	High Similarity	NPC209550
0.956	High Similarity	NPC95866
0.956	High Similarity	NPC138990
0.956	High Similarity	NPC277532
0.956	High Similarity	NPC175429
0.9554	High Similarity	NPC129264
0.9554	High Similarity	NPC85751
0.9554	High Similarity	NPC19240
0.9554	High Similarity	NPC139060
0.9554	High Similarity	NPC72016
0.9554	High Similarity	NPC205824
0.9551	High Similarity	NPC298171
0.9551	High Similarity	NPC131745
0.9551	High Similarity	NPC244875
0.9551	High Similarity	NPC259834
0.9551	High Similarity	NPC475382
0.9551	High Similarity	NPC44947
0.9548	High Similarity	NPC142860
0.9548	High Similarity	NPC97285
0.9548	High Similarity	NPC246469
0.9548	High Similarity	NPC271270
0.9545	High Similarity	NPC60966
0.9545	High Similarity	NPC288084
0.9545	High Similarity	NPC6985
0.9542	High Similarity	NPC26195
0.9542	High Similarity	NPC39351
0.9542	High Similarity	NPC72649
0.9542	High Similarity	NPC97052
0.9542	High Similarity	NPC169248
0.95	High Similarity	NPC474522
0.95	High Similarity	NPC33054
0.95	High Similarity	NPC176740
0.95	High Similarity	NPC203259
0.95	High Similarity	NPC471748
0.95	High Similarity	NPC134532
0.95	High Similarity	NPC471725
0.95	High Similarity	NPC155877
0.949	High Similarity	NPC124155
0.949	High Similarity	NPC183672
0.949	High Similarity	NPC311850
0.949	High Similarity	NPC80068
0.949	High Similarity	NPC257566
0.949	High Similarity	NPC473644
0.9487	High Similarity	NPC47923
0.9484	High Similarity	NPC73511
0.9481	High Similarity	NPC170475
0.9477	High Similarity	NPC106625
0.9437	High Similarity	NPC164704
0.9437	High Similarity	NPC254855
0.9437	High Similarity	NPC470712
0.9437	High Similarity	NPC136042
0.9437	High Similarity	NPC29958
0.9437	High Similarity	NPC259896
0.9437	High Similarity	NPC156869
0.9437	High Similarity	NPC67326
0.9437	High Similarity	NPC255157
0.9437	High Similarity	NPC67105
0.9434	High Similarity	NPC173637
0.9434	High Similarity	NPC127546
0.9434	High Similarity	NPC52550
0.9434	High Similarity	NPC317489
0.9434	High Similarity	NPC84362
0.9434	High Similarity	NPC223424
0.9427	High Similarity	NPC190450
0.9419	High Similarity	NPC122809
0.9419	High Similarity	NPC258035
0.9419	High Similarity	NPC156457
0.9419	High Similarity	NPC161749
0.9419	High Similarity	NPC197896
0.9419	High Similarity	NPC313163
0.9416	High Similarity	NPC99233
0.9412	High Similarity	NPC88484
0.9412	High Similarity	NPC259182
0.9412	High Similarity	NPC259767
0.9412	High Similarity	NPC121001
0.9408	High Similarity	NPC191154
0.9383	High Similarity	NPC473327
0.9383	High Similarity	NPC294629
0.9383	High Similarity	NPC16194
0.9383	High Similarity	NPC220173
0.9383	High Similarity	NPC476472
0.9383	High Similarity	NPC294815
0.9383	High Similarity	NPC19108
0.9379	High Similarity	NPC221288
0.9379	High Similarity	NPC26230
0.9379	High Similarity	NPC470716
0.9379	High Similarity	NPC470714
0.9379	High Similarity	NPC470715
0.9379	High Similarity	NPC217822
0.9379	High Similarity	NPC101399
0.9379	High Similarity	NPC60735
0.9379	High Similarity	NPC11847
0.9375	High Similarity	NPC227508
0.9375	High Similarity	NPC225434
0.9375	High Similarity	NPC52382
0.9375	High Similarity	NPC120099
0.9375	High Similarity	NPC219904
0.9375	High Similarity	NPC223747
0.9375	High Similarity	NPC203050
0.9375	High Similarity	NPC270578
0.9371	High Similarity	NPC308404
0.9371	High Similarity	NPC276222
0.9371	High Similarity	NPC262222
0.9371	High Similarity	NPC179950
0.9371	High Similarity	NPC145038
0.9371	High Similarity	NPC115674
0.9371	High Similarity	NPC68592
0.9371	High Similarity	NPC113968

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 NPC253788 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	917
0.2-0.3	1877
0.3-0.4	2787
0.4-0.5	1909
0.5-0.6	896
0.6-0.7	244
0.7-0.8	110
0.8-0.85	18
0.85-0.9	3
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.962	High Similarity	NPD7804	Clinical (unspecified phase)
0.95	High Similarity	NPD6797	Phase 2
0.9441	High Similarity	NPD7251	Discontinued
0.9419	High Similarity	NPD4381	Clinical (unspecified phase)
0.9383	High Similarity	NPD7808	Phase 3
0.9255	High Similarity	NPD7054	Approved
0.9198	High Similarity	NPD7472	Approved
0.908	High Similarity	NPD7074	Phase 3
0.903	High Similarity	NPD4338	Clinical (unspecified phase)
0.8834	High Similarity	NPD6166	Phase 2
0.8834	High Similarity	NPD6168	Clinical (unspecified phase)
0.8834	High Similarity	NPD6167	Clinical (unspecified phase)
0.8812	High Similarity	NPD7075	Discontinued
0.8797	High Similarity	NPD6801	Discontinued
0.879	High Similarity	NPD4380	Phase 2
0.8727	High Similarity	NPD3818	Discontinued
0.8718	High Similarity	NPD5403	Approved
0.8645	High Similarity	NPD6799	Approved
0.8625	High Similarity	NPD7096	Clinical (unspecified phase)
0.859	High Similarity	NPD5401	Approved
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.8571	High Similarity	NPD3817	Phase 2
0.8497	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD5402	Approved
0.8447	Intermediate Similarity	NPD1934	Approved
0.8442	Intermediate Similarity	NPD1549	Phase 2
0.8412	Intermediate Similarity	NPD6559	Discontinued
0.8395	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6599	Discontinued
0.8302	Intermediate Similarity	NPD1512	Approved
0.8293	Intermediate Similarity	NPD3882	Suspended
0.8282	Intermediate Similarity	NPD2801	Approved
0.8272	Intermediate Similarity	NPD7411	Suspended
0.8239	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2796	Approved
0.8192	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1511	Approved
0.814	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8095	Intermediate Similarity	NPD6959	Discontinued
0.8072	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3751	Discontinued
0.8047	Intermediate Similarity	NPD3787	Discontinued
0.7987	Intermediate Similarity	NPD1240	Approved
0.7953	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7819	Suspended
0.7898	Intermediate Similarity	NPD8312	Approved
0.7898	Intermediate Similarity	NPD8313	Approved
0.7885	Intermediate Similarity	NPD1607	Approved
0.7875	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD8455	Phase 2
0.7824	Intermediate Similarity	NPD5494	Approved
0.7819	Intermediate Similarity	NPD7584	Approved
0.7814	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6777	Approved
0.7784	Intermediate Similarity	NPD6780	Approved
0.7784	Intermediate Similarity	NPD6779	Approved
0.7784	Intermediate Similarity	NPD6782	Approved
0.7784	Intermediate Similarity	NPD6781	Approved
0.7784	Intermediate Similarity	NPD6776	Approved
0.7784	Intermediate Similarity	NPD6778	Approved
0.7764	Intermediate Similarity	NPD3750	Approved
0.7754	Intermediate Similarity	NPD7435	Discontinued
0.7742	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7698	Approved
0.766	Intermediate Similarity	NPD7696	Phase 3
0.766	Intermediate Similarity	NPD7697	Approved
0.7654	Intermediate Similarity	NPD4628	Phase 3
0.7651	Intermediate Similarity	NPD1653	Approved
0.7647	Intermediate Similarity	NPD7768	Phase 2
0.764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7614	Intermediate Similarity	NPD5844	Phase 1
0.7602	Intermediate Similarity	NPD3749	Approved
0.7593	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD7701	Phase 2
0.7586	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7228	Approved
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7543	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6232	Discontinued
0.7529	Intermediate Similarity	NPD1465	Phase 2
0.7526	Intermediate Similarity	NPD7870	Phase 2
0.7526	Intermediate Similarity	NPD7871	Phase 2
0.7516	Intermediate Similarity	NPD6798	Discontinued
0.7514	Intermediate Similarity	NPD6535	Approved
0.7514	Intermediate Similarity	NPD6534	Approved
0.7513	Intermediate Similarity	NPD7874	Approved
0.7513	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD7473	Discontinued
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1933	Approved
0.7474	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7783	Phase 2
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7468	Intermediate Similarity	NPD6233	Phase 2
0.7457	Intermediate Similarity	NPD919	Approved
0.7453	Intermediate Similarity	NPD3748	Approved
0.7453	Intermediate Similarity	NPD7033	Discontinued
0.7435	Intermediate Similarity	NPD8319	Approved
0.7435	Intermediate Similarity	NPD8320	Phase 1
0.7409	Intermediate Similarity	NPD7585	Approved
0.7396	Intermediate Similarity	NPD7458	Discontinued
0.7389	Intermediate Similarity	NPD6832	Phase 2
0.7385	Intermediate Similarity	NPD7801	Approved
0.7381	Intermediate Similarity	NPD920	Approved
0.7378	Intermediate Similarity	NPD1652	Phase 2
0.7378	Intermediate Similarity	NPD2800	Approved
0.7371	Intermediate Similarity	NPD1247	Approved
0.7362	Intermediate Similarity	NPD7266	Discontinued
0.7358	Intermediate Similarity	NPD7583	Approved
0.7348	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5953	Discontinued
0.733	Intermediate Similarity	NPD6823	Phase 2
0.7329	Intermediate Similarity	NPD6651	Approved
0.7326	Intermediate Similarity	NPD4363	Phase 3
0.7326	Intermediate Similarity	NPD4360	Phase 2
0.7322	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7286	Phase 2
0.7312	Intermediate Similarity	NPD1613	Approved
0.7312	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1203	Approved
0.7301	Intermediate Similarity	NPD2935	Discontinued
0.7297	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6190	Approved
0.7288	Intermediate Similarity	NPD3926	Phase 2
0.7278	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1243	Approved
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5124	Phase 1
0.7267	Intermediate Similarity	NPD37	Approved
0.7262	Intermediate Similarity	NPD2534	Approved
0.7262	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2532	Approved
0.7262	Intermediate Similarity	NPD2533	Approved
0.7261	Intermediate Similarity	NPD2798	Approved
0.7257	Intermediate Similarity	NPD6234	Discontinued
0.7246	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4965	Approved
0.7241	Intermediate Similarity	NPD4966	Approved
0.7241	Intermediate Similarity	NPD4967	Phase 2
0.7237	Intermediate Similarity	NPD1548	Phase 1
0.7202	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7240	Approved
0.7189	Intermediate Similarity	NPD8150	Discontinued
0.7189	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2313	Discontinued
0.7188	Intermediate Similarity	NPD3268	Approved
0.7161	Intermediate Similarity	NPD422	Phase 1
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4062	Phase 3
0.7134	Intermediate Similarity	NPD3225	Approved
0.7134	Intermediate Similarity	NPD2799	Discontinued
0.7115	Intermediate Similarity	NPD9717	Approved
0.711	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7390	Discontinued
0.7099	Intermediate Similarity	NPD943	Approved
0.7093	Intermediate Similarity	NPD3226	Approved
0.7091	Intermediate Similarity	NPD6100	Approved
0.7091	Intermediate Similarity	NPD6099	Approved
0.709	Intermediate Similarity	NPD6213	Phase 3
0.709	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6212	Phase 3
0.7089	Intermediate Similarity	NPD2797	Approved
0.7083	Intermediate Similarity	NPD3887	Approved
0.7083	Intermediate Similarity	NPD2354	Approved
0.7073	Intermediate Similarity	NPD7097	Phase 1
0.7069	Intermediate Similarity	NPD6844	Discontinued
0.7063	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4340	Discontinued
0.7055	Intermediate Similarity	NPD230	Phase 1
0.7051	Intermediate Similarity	NPD1610	Phase 2
0.7019	Intermediate Similarity	NPD3027	Phase 3
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2309	Approved
0.6964	Remote Similarity	NPD2654	Approved
0.6961	Remote Similarity	NPD2403	Approved
0.6959	Remote Similarity	NPD4661	Approved
0.6959	Remote Similarity	NPD4662	Approved
0.6954	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD447	Suspended
0.6951	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2346	Discontinued
0.6928	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4308	Phase 3
0.6927	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4361	Phase 2
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5049	Phase 3

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