NPASS Compound

Structure

CID12013 OpenBabel06191715342D 52 57 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 0.0000 5.0000 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 4.3301 -1.5000 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 -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 0.8660 4.5000 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 1.7321 5.0000 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 2.5981 4.5000 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 2.5981 3.5000 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 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 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 0.8660 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 6.0000 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 3.4641 5.0000 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 3.4641 3.0000 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 0.8660 3.5000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 8 16 2 0 0 0 0 9 46 1 0 0 0 0 10 1 1 1 0 0 0 10 19 1 0 0 0 0 10 47 1 0 0 0 0 11 2 1 1 0 0 0 11 20 1 0 0 0 0 11 48 1 0 0 0 0 12 28 1 0 0 0 0 13 34 1 0 0 0 0 14 35 1 0 0 0 0 15 18 2 0 0 0 0 15 36 1 0 0 0 0 16 18 1 0 0 0 0 16 49 1 0 0 0 0 17 9 1 6 0 0 0 17 21 1 0 0 0 0 17 50 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 37 1 6 0 0 0 20 24 1 0 0 0 0 20 38 1 6 0 0 0 21 25 1 0 0 0 0 21 39 1 6 0 0 0 22 29 1 0 0 0 0 22 40 2 0 0 0 0 23 26 1 0 0 0 0 23 41 1 1 0 0 0 24 27 1 0 0 0 0 24 42 1 1 0 0 0 25 30 1 0 0 0 0 25 43 1 6 0 0 0 26 31 1 0 0 0 0 26 44 1 1 0 0 0 27 32 1 0 0 0 0 27 45 1 1 0 0 0 28 29 2 0 0 0 0 28 49 1 0 0 0 0 29 51 1 0 0 0 0 30 33 1 0 0 0 0 30 52 1 1 0 0 0 31 46 1 6 0 0 0 31 47 1 0 0 0 0 32 48 1 0 0 0 0 32 52 1 6 0 0 0 33 50 1 0 0 0 0 33 51 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	740.22
Volume:	673.908
LogP:	0.057
LogD:	-0.228
LogS:	-3.487
# Rotatable Bonds:	8
TPSA:	308.12
# H-Bond Aceptor:	19
# H-Bond Donor:	11
# Rings:	6
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.113
Synthetic Accessibility Score:	5.308
Fsp3:	0.545
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.462
MDCK Permeability:	4.342898682807572e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.93
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	79.85770416259766%
Volume Distribution (VD):	0.535
Pgp-substrate:	18.39837646484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	0.755
Half-life (T1/2):	0.602

ADMET: Toxicity

hERG Blockers:	0.333
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.79
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.933
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.101
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC12013

Natural Product ID:	NPC12013
*Common Name:**	Mauritianin
IUPAC Name:	3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	WRXVPTMENPZUIZ-MOVIZTNPSA-N
Standard InCHI:	InChI=1S/C33H40O19/c1-10-19(37)23(41)26(44)31(47-10)46-9-17-21(39)25(43)30(52-32-27(45)24(42)20(38)11(2)48-32)33(50-17)51-29-22(40)18-15(36)7-14(35)8-16(18)49-28(29)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-27,30-39,41-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21-,23+,24+,25-,26+,27+,30+,31+,32-,33-/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[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3747539
PubChem CID:	10919701
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]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
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]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10346965]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	root	n.a.	PMID[10617409]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575966]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
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]
NPO7247	Cymbopogon citratus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19924037]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	Sunan County, Gansu Province, China	2006-JUN	PMID[20684529]
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]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	whole plant	Guide County, Qinghai Province, China	2008-AUG	PMID[22775441]
NPO27632	Idesia polycarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23628332]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO14608	Ralstonia solanacearum	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25033087]
NPO11296	Arthrinium arundinis	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25626143]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark	Urubamba, Cusco, Peru	n.a.	PMID[25927586]
NPO40038	Astragalus monspessulanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26558405]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30219526]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO28686	Syzygium claviflorum	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8176401]
NPO29196	Cryptocarya kurzii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377019]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7247	Cymbopogon citratus	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7247	Cymbopogon citratus	Species	Poaceae	Eukaryota	Leaf Wax	n.a.	n.a.	Database[FooDB]
NPO7247	Cymbopogon citratus	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7247	Cymbopogon citratus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22524	Ranunculus sceleratus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28802	Pratia nummularia	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7247	Cymbopogon citratus	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7247	Cymbopogon citratus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22524	Ranunculus sceleratus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28802	Pratia nummularia	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22409	Cyanostegia microphylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	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]
NPO29062	Hibiscus syriacus	Species	Malvaceae	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]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29062	Hibiscus syriacus	Species	Malvaceae	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]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22524	Ranunculus sceleratus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9737	Ampelocera edentula	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22593	Graphis rikuzensis	Species	Aclididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5216	Bacillus pumilus	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2217	Valeriana wolgensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1118	Elymus repens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29274	Euphorbia sororia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11296	Arthrinium arundinis	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2439	Diplopterygium glaucum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22006	Maytenus aquifolium	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29196	Cryptocarya kurzii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29076	Iris versicolor	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1293	Streptomyces matensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28818	Datura quercifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22806	Euphorbia leuconeura	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5086	Alternaria macrospora	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29184	Friesodielsia enghiana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28879	Dorstenia cayapia	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6909	Zaluzania augusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22409	Cyanostegia microphylla	Species	Lamiaceae	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]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9091	Orthosiphon spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29447	Cladosporium cladosporioides	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14608	Ralstonia solanacearum	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7798	Elaeocarpus sylvestris	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29121	Trichogonia prancii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20702	Discodermia dissoluta	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28802	Pratia nummularia	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9876	Isocoma pluriflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13457	Acacia pachyphloia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7247	Cymbopogon citratus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13474	Euphrasia genargentea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19626	Lavandula dentata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO593	Wikstroemia viridiflora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28686	Syzygium claviflorum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9594	Lysimachia fordiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9867	Ixeris debilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21472	Pterolobium hexapetalum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29507	Erythroxylum argentinum	Species	Erythroxylaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27632	Idesia polycarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21358	Pyrus ussuriensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28893	Diphasia klaineana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16652	Centipeda cunninghami	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3838	Chrysosporum ovalisporum	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29433	Nephroma arcticum	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6807	Ranunculus asiaticus	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]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2670	Maytenus chuchuhuasha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20567	Montipora mollis	Species	Acroporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29167	Bombus consobrinus	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9998	Abies excelsa	Species	Pinaceae	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
NPT984	Cell Line	Hepatocyte		Activity	=	168.0	%	PMID[491957]

☑ 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 NPC12013 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	446
0.1-0.2	1698
0.2-0.3	3984
0.3-0.4	9458
0.4-0.5	8779
0.5-0.6	5447
0.6-0.7	5906
0.7-0.8	5277
0.8-0.85	909
0.85-0.9	432
0.9-0.95	299
0.95-1	62

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC186816
1.0	High Similarity	NPC477613
1.0	High Similarity	NPC11432
1.0	High Similarity	NPC32641
1.0	High Similarity	NPC256188
1.0	High Similarity	NPC221342
1.0	High Similarity	NPC203145
1.0	High Similarity	NPC142142
1.0	High Similarity	NPC476470
1.0	High Similarity	NPC189564
0.9936	High Similarity	NPC292929
0.9936	High Similarity	NPC135358
0.9936	High Similarity	NPC287889
0.9936	High Similarity	NPC76831
0.9936	High Similarity	NPC289667
0.9808	High Similarity	NPC244875
0.9808	High Similarity	NPC475382
0.9808	High Similarity	NPC240306
0.9747	High Similarity	NPC64425
0.9745	High Similarity	NPC473644
0.9745	High Similarity	NPC311850
0.9744	High Similarity	NPC265885
0.9744	High Similarity	NPC116458
0.9744	High Similarity	NPC170052
0.9744	High Similarity	NPC163242
0.9744	High Similarity	NPC246943
0.9744	High Similarity	NPC476215
0.9744	High Similarity	NPC215710
0.9744	High Similarity	NPC139320
0.9744	High Similarity	NPC473438
0.9744	High Similarity	NPC253788
0.9744	High Similarity	NPC173582
0.9744	High Similarity	NPC64305
0.9744	High Similarity	NPC276377
0.9744	High Similarity	NPC135846
0.9744	High Similarity	NPC249281
0.9744	High Similarity	NPC297987
0.9744	High Similarity	NPC181465
0.9688	High Similarity	NPC209550
0.9688	High Similarity	NPC175429
0.9688	High Similarity	NPC277532
0.9688	High Similarity	NPC138990
0.9679	High Similarity	NPC304741
0.9679	High Similarity	NPC136761
0.9679	High Similarity	NPC471079
0.9679	High Similarity	NPC187379
0.9679	High Similarity	NPC470405
0.9627	High Similarity	NPC470715
0.9627	High Similarity	NPC470714
0.9627	High Similarity	NPC474522
0.9627	High Similarity	NPC470716
0.9625	High Similarity	NPC5319
0.9623	High Similarity	NPC262222
0.9623	High Similarity	NPC68592
0.9623	High Similarity	NPC298666
0.9615	High Similarity	NPC41121
0.9615	High Similarity	NPC138811
0.9615	High Similarity	NPC473634
0.9615	High Similarity	NPC320283
0.9615	High Similarity	NPC22062
0.9615	High Similarity	NPC472459
0.9615	High Similarity	NPC111929
0.9571	High Similarity	NPC292019
0.9571	High Similarity	NPC202908
0.9571	High Similarity	NPC122467
0.9571	High Similarity	NPC231787
0.9571	High Similarity	NPC48984
0.9571	High Similarity	NPC14187
0.9565	High Similarity	NPC164704
0.9565	High Similarity	NPC470712
0.9557	High Similarity	NPC298171
0.9554	High Similarity	NPC271270
0.9554	High Similarity	NPC153342
0.9554	High Similarity	NPC473623
0.9554	High Similarity	NPC142860
0.9554	High Similarity	NPC97285
0.9554	High Similarity	NPC246469
0.9551	High Similarity	NPC108831
0.9551	High Similarity	NPC129827
0.9551	High Similarity	NPC65003
0.9551	High Similarity	NPC78263
0.9551	High Similarity	NPC133671
0.9551	High Similarity	NPC135391
0.9551	High Similarity	NPC197304
0.9551	High Similarity	NPC77672
0.9551	High Similarity	NPC54802
0.9551	High Similarity	NPC182634
0.9551	High Similarity	NPC44931
0.9551	High Similarity	NPC473512
0.9512	High Similarity	NPC251417
0.9512	High Similarity	NPC89052
0.9494	High Similarity	NPC224530
0.9494	High Similarity	NPC48093
0.9494	High Similarity	NPC216496
0.9494	High Similarity	NPC159579
0.9494	High Similarity	NPC101636
0.9494	High Similarity	NPC259957
0.9494	High Similarity	NPC129217
0.9494	High Similarity	NPC470125
0.9494	High Similarity	NPC85707
0.9487	High Similarity	NPC307938
0.9487	High Similarity	NPC295613
0.9487	High Similarity	NPC323593
0.9487	High Similarity	NPC203500
0.9487	High Similarity	NPC473657
0.9455	High Similarity	NPC192539
0.9451	High Similarity	NPC219043
0.9434	High Similarity	NPC150164
0.9434	High Similarity	NPC190450
0.9434	High Similarity	NPC27942
0.9423	High Similarity	NPC27408
0.9423	High Similarity	NPC95090
0.939	High Similarity	NPC16194
0.939	High Similarity	NPC220173
0.939	High Similarity	NPC294815
0.939	High Similarity	NPC19108
0.939	High Similarity	NPC476472
0.939	High Similarity	NPC473327
0.9387	High Similarity	NPC217822
0.9387	High Similarity	NPC155877
0.9387	High Similarity	NPC203259
0.9387	High Similarity	NPC471725
0.9387	High Similarity	NPC471748
0.9387	High Similarity	NPC11847
0.9387	High Similarity	NPC101399
0.9387	High Similarity	NPC221288
0.9387	High Similarity	NPC176740
0.9387	High Similarity	NPC134532
0.9387	High Similarity	NPC33054
0.9375	High Similarity	NPC124155
0.9375	High Similarity	NPC66087
0.9375	High Similarity	NPC121703
0.9375	High Similarity	NPC179198
0.9375	High Similarity	NPC257566
0.9375	High Similarity	NPC278419
0.9371	High Similarity	NPC303913
0.9371	High Similarity	NPC282169
0.9371	High Similarity	NPC473516
0.9367	High Similarity	NPC104677
0.9363	High Similarity	NPC206378
0.9359	High Similarity	NPC83283
0.9359	High Similarity	NPC143851
0.9359	High Similarity	NPC210003
0.9359	High Similarity	NPC39360
0.9359	High Similarity	NPC29763
0.9333	High Similarity	NPC471669
0.9333	High Similarity	NPC89127
0.9333	High Similarity	NPC473862
0.9325	High Similarity	NPC218161
0.9325	High Similarity	NPC469344
0.9325	High Similarity	NPC136042
0.9325	High Similarity	NPC280642
0.9325	High Similarity	NPC67326
0.9325	High Similarity	NPC92815
0.9325	High Similarity	NPC67105
0.9325	High Similarity	NPC156869
0.9325	High Similarity	NPC29958
0.9325	High Similarity	NPC259896
0.9325	High Similarity	NPC96605
0.9325	High Similarity	NPC188815
0.9325	High Similarity	NPC254855
0.9325	High Similarity	NPC95866
0.9325	High Similarity	NPC255157
0.9317	High Similarity	NPC85751
0.9317	High Similarity	NPC129264
0.9317	High Similarity	NPC72016
0.9317	High Similarity	NPC19240
0.9317	High Similarity	NPC205824
0.9317	High Similarity	NPC139060
0.9313	High Similarity	NPC44947
0.9313	High Similarity	NPC259834
0.9313	High Similarity	NPC131745
0.9308	High Similarity	NPC321478
0.9304	High Similarity	NPC288084
0.9304	High Similarity	NPC6985
0.9304	High Similarity	NPC60966
0.9299	High Similarity	NPC169248
0.9299	High Similarity	NPC97052
0.9299	High Similarity	NPC26195
0.9299	High Similarity	NPC39351
0.9299	High Similarity	NPC72649
0.9286	High Similarity	NPC249560
0.9286	High Similarity	NPC223860
0.9286	High Similarity	NPC275977
0.9277	High Similarity	NPC173837
0.9273	High Similarity	NPC198199
0.9268	High Similarity	NPC288152
0.9268	High Similarity	NPC9002
0.9268	High Similarity	NPC180918
0.9268	High Similarity	NPC60735
0.9268	High Similarity	NPC137871
0.9268	High Similarity	NPC26230
0.9268	High Similarity	NPC257011
0.9264	High Similarity	NPC227508
0.9259	High Similarity	NPC70441
0.9255	High Similarity	NPC80068
0.9255	High Similarity	NPC183672
0.925	High Similarity	NPC47923
0.9245	High Similarity	NPC73511
0.9241	High Similarity	NPC170475

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 NPC12013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	934
0.2-0.3	1929
0.3-0.4	2805
0.4-0.5	1891
0.5-0.6	833
0.6-0.7	242
0.7-0.8	101
0.8-0.85	16
0.85-0.9	3
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9625	High Similarity	NPD7804	Clinical (unspecified phase)
0.9509	High Similarity	NPD7808	Phase 3
0.9448	High Similarity	NPD7251	Discontinued
0.9387	High Similarity	NPD6797	Phase 2
0.9207	High Similarity	NPD7472	Approved
0.9182	High Similarity	NPD4381	Clinical (unspecified phase)
0.9146	High Similarity	NPD7054	Approved
0.9091	High Similarity	NPD7074	Phase 3
0.8817	High Similarity	NPD4338	Clinical (unspecified phase)
0.8712	High Similarity	NPD7075	Discontinued
0.8623	High Similarity	NPD6168	Clinical (unspecified phase)
0.8623	High Similarity	NPD6167	Clinical (unspecified phase)
0.8623	High Similarity	NPD6166	Phase 2
0.858	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD4380	Phase 2
0.8528	High Similarity	NPD7096	Clinical (unspecified phase)
0.8521	High Similarity	NPD3818	Discontinued
0.85	High Similarity	NPD5403	Approved
0.8428	Intermediate Similarity	NPD6799	Approved
0.8375	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD5401	Approved
0.8364	Intermediate Similarity	NPD3817	Phase 2
0.828	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5402	Approved
0.8242	Intermediate Similarity	NPD1934	Approved
0.8228	Intermediate Similarity	NPD1549	Phase 2
0.8218	Intermediate Similarity	NPD6559	Discontinued
0.8212	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6599	Discontinued
0.8098	Intermediate Similarity	NPD1512	Approved
0.8095	Intermediate Similarity	NPD3882	Suspended
0.8084	Intermediate Similarity	NPD2801	Approved
0.8072	Intermediate Similarity	NPD7411	Suspended
0.8037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD8313	Approved
0.8023	Intermediate Similarity	NPD8312	Approved
0.7987	Intermediate Similarity	NPD2796	Approved
0.7976	Intermediate Similarity	NPD7819	Suspended
0.7976	Intermediate Similarity	NPD8455	Phase 2
0.7975	Intermediate Similarity	NPD1511	Approved
0.7925	Intermediate Similarity	NPD1510	Phase 2
0.7907	Intermediate Similarity	NPD6959	Discontinued
0.7886	Intermediate Similarity	NPD3751	Discontinued
0.7882	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD3787	Discontinued
0.7838	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1240	Approved
0.7749	Intermediate Similarity	NPD7584	Approved
0.7688	Intermediate Similarity	NPD1607	Approved
0.7684	Intermediate Similarity	NPD7435	Discontinued
0.7684	Intermediate Similarity	NPD7697	Approved
0.7684	Intermediate Similarity	NPD7696	Phase 3
0.7684	Intermediate Similarity	NPD7698	Approved
0.7683	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7768	Phase 2
0.7668	Intermediate Similarity	NPD8151	Discontinued
0.7658	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5494	Approved
0.7619	Intermediate Similarity	NPD6776	Approved
0.7619	Intermediate Similarity	NPD6777	Approved
0.7619	Intermediate Similarity	NPD6781	Approved
0.7619	Intermediate Similarity	NPD6779	Approved
0.7619	Intermediate Similarity	NPD6780	Approved
0.7619	Intermediate Similarity	NPD6782	Approved
0.7619	Intermediate Similarity	NPD6778	Approved
0.7617	Intermediate Similarity	NPD7701	Phase 2
0.759	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7783	Phase 2
0.7576	Intermediate Similarity	NPD3750	Approved
0.7571	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7871	Phase 2
0.7552	Intermediate Similarity	NPD8320	Phase 1
0.7552	Intermediate Similarity	NPD7870	Phase 2
0.7552	Intermediate Similarity	NPD8319	Approved
0.7538	Intermediate Similarity	NPD7874	Approved
0.7538	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.7513	Intermediate Similarity	NPD7699	Phase 2
0.7513	Intermediate Similarity	NPD7700	Phase 2
0.7486	Intermediate Similarity	NPD7228	Approved
0.7471	Intermediate Similarity	NPD1653	Approved
0.747	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5844	Phase 1
0.7439	Intermediate Similarity	NPD1551	Phase 2
0.743	Intermediate Similarity	NPD7473	Discontinued
0.7429	Intermediate Similarity	NPD3749	Approved
0.7416	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7801	Approved
0.741	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6232	Discontinued
0.7356	Intermediate Similarity	NPD1465	Phase 2
0.7354	Intermediate Similarity	NPD6535	Approved
0.7354	Intermediate Similarity	NPD6534	Approved
0.7351	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7585	Approved
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7326	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7458	Discontinued
0.7312	Intermediate Similarity	NPD6832	Phase 2
0.7312	Intermediate Similarity	NPD8434	Phase 2
0.731	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1091	Approved
0.7303	Intermediate Similarity	NPD7199	Phase 2
0.7301	Intermediate Similarity	NPD1933	Approved
0.7296	Intermediate Similarity	NPD7583	Approved
0.7289	Intermediate Similarity	NPD7266	Discontinued
0.7288	Intermediate Similarity	NPD919	Approved
0.7284	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD3748	Approved
0.7268	Intermediate Similarity	NPD6823	Phase 2
0.7256	Intermediate Similarity	NPD6651	Approved
0.7253	Intermediate Similarity	NPD7286	Phase 2
0.7228	Intermediate Similarity	NPD7240	Approved
0.7219	Intermediate Similarity	NPD8150	Discontinued
0.7209	Intermediate Similarity	NPD920	Approved
0.7207	Intermediate Similarity	NPD1247	Approved
0.7202	Intermediate Similarity	NPD2800	Approved
0.7202	Intermediate Similarity	NPD1652	Phase 2
0.7195	Intermediate Similarity	NPD6355	Discontinued
0.7189	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5953	Discontinued
0.7173	Intermediate Similarity	NPD4363	Phase 3
0.7173	Intermediate Similarity	NPD4360	Phase 2
0.7171	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1613	Approved
0.7134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD3926	Phase 2
0.7126	Intermediate Similarity	NPD2935	Discontinued
0.7125	Intermediate Similarity	NPD1203	Approved
0.7118	Intermediate Similarity	NPD6190	Approved
0.7102	Intermediate Similarity	NPD37	Approved
0.7101	Intermediate Similarity	NPD1243	Approved
0.7099	Intermediate Similarity	NPD4908	Phase 1
0.7095	Intermediate Similarity	NPD6234	Discontinued
0.7093	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2533	Approved
0.7093	Intermediate Similarity	NPD2532	Approved
0.7093	Intermediate Similarity	NPD2534	Approved
0.7091	Intermediate Similarity	NPD5124	Phase 1
0.7091	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2798	Approved
0.7079	Intermediate Similarity	NPD4967	Phase 2
0.7079	Intermediate Similarity	NPD4966	Approved
0.7079	Intermediate Similarity	NPD4965	Approved
0.7076	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1548	Phase 1
0.7045	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6100	Approved
0.7024	Intermediate Similarity	NPD6099	Approved
0.7012	Intermediate Similarity	NPD3268	Approved
0.7012	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2313	Discontinued
0.7006	Intermediate Similarity	NPD7097	Phase 1
0.7006	Intermediate Similarity	NPD6844	Discontinued
0.6994	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2344	Approved
0.6981	Remote Similarity	NPD422	Phase 1
0.697	Remote Similarity	NPD4062	Phase 3
0.6964	Remote Similarity	NPD2799	Discontinued
0.6957	Remote Similarity	NPD3225	Approved
0.6943	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6212	Phase 3
0.6943	Remote Similarity	NPD6213	Phase 3
0.6937	Remote Similarity	NPD9717	Approved
0.6936	Remote Similarity	NPD7390	Discontinued
0.6932	Remote Similarity	NPD3226	Approved
0.6928	Remote Similarity	NPD943	Approved
0.6919	Remote Similarity	NPD3887	Approved
0.6919	Remote Similarity	NPD2354	Approved
0.6914	Remote Similarity	NPD2797	Approved
0.689	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD230	Phase 1
0.6886	Remote Similarity	NPD4340	Discontinued
0.6878	Remote Similarity	NPD7930	Approved
0.6875	Remote Similarity	NPD1610	Phase 2
0.686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3027	Phase 3
0.6829	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2309	Approved
0.6818	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD2403	Approved
0.6802	Remote Similarity	NPD2654	Approved
0.68	Remote Similarity	NPD7680	Approved
0.68	Remote Similarity	NPD4662	Approved
0.68	Remote Similarity	NPD4661	Approved
0.6786	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD447	Suspended
0.6786	Remote Similarity	NPD4361	Phase 2
0.6786	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2346	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