NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	196.07
Volume:	197.575
LogP:	0.571
LogD:	0.759
LogS:	-1.371
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	1.908
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.457
MDCK Permeability:	1.4284068129200023e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.248

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.736
Plasma Protein Binding (PPB):	36.28395080566406%
Volume Distribution (VD):	0.947
Pgp-substrate:	65.17784881591797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.415
CYP1A2-substrate:	0.756
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.633
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.488
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	10.052
Half-life (T1/2):	0.917

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.593
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.238
Carcinogencity:	0.218
Eye Corrosion:	0.104
Eye Irritation:	0.964
Respiratory Toxicity:	0.123

Download Data

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

Natural Product: NPC50763

Natural Product ID:	NPC50763
*Common Name:**	Beta-Hydroxypropiovanillone
IUPAC Name:	3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one
Synonyms:	Beta-Hydroxypropiovanillone; Omega-Hydroxypropioguaiacone
Standard InCHIKey:	NXCPMSUBVRGTSE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O4/c1-14-10-6-7(2-3-9(10)13)8(12)4-5-11/h2-3,6,11,13H,4-5H2,1H3
SMILES:	COc1cc(ccc1O)C(=O)CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485875
PubChem CID:	75142
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11559179]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12643908]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[13465274]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1536925]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[15467233]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180822]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18001808]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[18471021]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[18471021]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	Stems	n.a.	n.a.	PMID[19534471]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19659728]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19813743]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20189399]
NPO10464	Epipedobates anthonyi	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337496]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	trunk	Jeju island, Korea	2005-Dec	PMID[21420296]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21420296]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23479199]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	seed	n.a.	PMID[24225786]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368118]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667820]
NPO21299	Porcelia macrocarpa	Species	n.a.	n.a.	Seeds	n.a.	n.a.	PMID[31046273]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32004936]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3509958]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[8778243]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358636]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14039	Leucaena leucocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4853	Carduus crispus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5933	Drimia fugax	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4853	Carduus crispus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13798	Cheilanthes marantae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3576	Bersama swinnyi	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17814	Berberis turcomanica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14938	Cybister lateralimarginalis	Species	Dytiscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14039	Leucaena leucocephala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6425	Betula davurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19989	Cercosporella acetosella	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27784	Porites lutea	Species	Poritidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19561	Garcinia conrauana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21341	Morus macroura	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25284	Helichrysum davyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22670	Phebalium bilobum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17102	Ocypus olens	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21299	Porcelia macrocarpa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9375	Medium grandiflorum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3277	Salix alba	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2993	0totodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22734	Neopringlea integrifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23441	Schisandra sphaerandra	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5933	Drimia fugax	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8640	Nemuaron humboldtii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22915	Stereocaulon azoreum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22212	Rhizophora mangle	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20218	Lecanora reuteri	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20675	Anaphalis triplinervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10464	Epipedobates anthonyi	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14280	Helichrysum angustifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19030	Delphinium anthriscifolium	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21776	Sesbania grandiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21610	Laurencia rigida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20343	Cephalothecium roseum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22272	Raphanus raphanistrum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20787	Achyranthes aspera	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21361	Anastatica hierochuntica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20057	Urechites suberecta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2408	Millettia laurentii	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	5
MIC	1
Others	2

Activity Type	# Activity
Cell Line	5
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[495756]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000.0	nM	PMID[495756]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	28410.0	nM	PMID[495756]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[495756]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	43800.0	nM	PMID[495757]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	153000.0	nM	PMID[495754]
NPT2	Others	Unspecified		Inhibition	<	15.4	%	PMID[495755]
NPT27	Others	Unspecified		Inhibition	<	8.8	%	PMID[495755]

☑ 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 NPC50763 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	318
0.1-0.2	1569
0.2-0.3	4503
0.3-0.4	10601
0.4-0.5	7159
0.5-0.6	3914
0.6-0.7	7428
0.7-0.8	6486
0.8-0.85	545
0.85-0.9	141
0.9-0.95	29
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC16651
0.96	High Similarity	NPC32163
0.9542	High Similarity	NPC325625
0.9462	High Similarity	NPC139519
0.9323	High Similarity	NPC4796
0.9291	High Similarity	NPC203719
0.9291	High Similarity	NPC117237
0.9225	High Similarity	NPC66905
0.9191	High Similarity	NPC46161
0.9191	High Similarity	NPC239608
0.9084	High Similarity	NPC111888
0.9077	High Similarity	NPC298268
0.9048	High Similarity	NPC114298
0.9044	High Similarity	NPC84273
0.904	High Similarity	NPC225245
0.9023	High Similarity	NPC208760
0.9015	High Similarity	NPC283823
0.9015	High Similarity	NPC159418
0.9	High Similarity	NPC261759
0.8992	High Similarity	NPC20287
0.8992	High Similarity	NPC20404
0.8992	High Similarity	NPC293641
0.8992	High Similarity	NPC12022
0.8976	High Similarity	NPC164778
0.8976	High Similarity	NPC4181
0.8976	High Similarity	NPC242372
0.8976	High Similarity	NPC257976
0.8971	High Similarity	NPC50823
0.8955	High Similarity	NPC324929
0.8923	High Similarity	NPC278308
0.8906	High Similarity	NPC312404
0.8906	High Similarity	NPC273686
0.8897	High Similarity	NPC474784
0.888	High Similarity	NPC299406
0.8872	High Similarity	NPC327410
0.8865	High Similarity	NPC474903
0.8849	High Similarity	NPC142165
0.8846	High Similarity	NPC123228
0.8846	High Similarity	NPC5018
0.8846	High Similarity	NPC151167
0.8846	High Similarity	NPC276466
0.8846	High Similarity	NPC123722
0.8841	High Similarity	NPC299154
0.8828	High Similarity	NPC474691
0.8806	High Similarity	NPC237330
0.8806	High Similarity	NPC144662
0.8788	High Similarity	NPC319282
0.8788	High Similarity	NPC65935
0.8788	High Similarity	NPC275724
0.8788	High Similarity	NPC244246
0.8788	High Similarity	NPC311419
0.8788	High Similarity	NPC285776
0.8788	High Similarity	NPC215941
0.8788	High Similarity	NPC137427
0.8788	High Similarity	NPC123196
0.8788	High Similarity	NPC195292
0.8786	High Similarity	NPC160777
0.8786	High Similarity	NPC73416
0.8777	High Similarity	NPC254659
0.8769	High Similarity	NPC84076
0.8769	High Similarity	NPC90128
0.8769	High Similarity	NPC179777
0.8769	High Similarity	NPC303680
0.8741	High Similarity	NPC274613
0.874	High Similarity	NPC158949
0.874	High Similarity	NPC295317
0.8723	High Similarity	NPC226987
0.8723	High Similarity	NPC143903
0.872	High Similarity	NPC150919
0.8714	High Similarity	NPC469683
0.8712	High Similarity	NPC304622
0.8705	High Similarity	NPC229218
0.8705	High Similarity	NPC192597
0.8705	High Similarity	NPC141817
0.8705	High Similarity	NPC169214
0.8705	High Similarity	NPC312256
0.8705	High Similarity	NPC176030
0.8702	High Similarity	NPC281020
0.8696	High Similarity	NPC138438
0.8696	High Similarity	NPC908
0.8686	High Similarity	NPC284409
0.8682	High Similarity	NPC163083
0.8682	High Similarity	NPC244876
0.8672	High Similarity	NPC194416
0.8672	High Similarity	NPC177291
0.8672	High Similarity	NPC201777
0.8671	High Similarity	NPC139293
0.8671	High Similarity	NPC195763
0.8671	High Similarity	NPC69430
0.8671	High Similarity	NPC142876
0.8671	High Similarity	NPC200060
0.8671	High Similarity	NPC333691
0.8671	High Similarity	NPC40290
0.8671	High Similarity	NPC264289
0.8671	High Similarity	NPC264550
0.8667	High Similarity	NPC471110
0.8662	High Similarity	NPC125449
0.8662	High Similarity	NPC188074
0.8652	High Similarity	NPC287495
0.8652	High Similarity	NPC9370
0.8647	High Similarity	NPC172673
0.8647	High Similarity	NPC142985
0.8643	High Similarity	NPC287722
0.8643	High Similarity	NPC46880
0.8643	High Similarity	NPC469615
0.8633	High Similarity	NPC110419
0.8615	High Similarity	NPC30216
0.8613	High Similarity	NPC110899
0.8613	High Similarity	NPC125417
0.8613	High Similarity	NPC112068
0.8613	High Similarity	NPC25305
0.8613	High Similarity	NPC95679
0.8603	High Similarity	NPC204592
0.8601	High Similarity	NPC139364
0.8601	High Similarity	NPC203747
0.8601	High Similarity	NPC254702
0.8601	High Similarity	NPC80710
0.8601	High Similarity	NPC194653
0.8601	High Similarity	NPC287395
0.8601	High Similarity	NPC183655
0.8593	High Similarity	NPC307006
0.8593	High Similarity	NPC129889
0.8582	High Similarity	NPC207732
0.8582	High Similarity	NPC469480
0.8571	High Similarity	NPC226855
0.8571	High Similarity	NPC301178
0.8571	High Similarity	NPC11314
0.8571	High Similarity	NPC284556
0.8562	High Similarity	NPC25127
0.8561	High Similarity	NPC158654
0.8561	High Similarity	NPC286683
0.8561	High Similarity	NPC326065
0.8552	High Similarity	NPC118427
0.8552	High Similarity	NPC31363
0.855	High Similarity	NPC53305
0.855	High Similarity	NPC257589
0.855	High Similarity	NPC280767
0.8542	High Similarity	NPC237441
0.8542	High Similarity	NPC205054
0.8542	High Similarity	NPC102003
0.8542	High Similarity	NPC92722
0.8531	High Similarity	NPC472969
0.8521	High Similarity	NPC30890
0.8519	High Similarity	NPC239302
0.8511	High Similarity	NPC473090
0.8511	High Similarity	NPC471417
0.8511	High Similarity	NPC50954
0.8511	High Similarity	NPC119663
0.8493	Intermediate Similarity	NPC291802
0.8493	Intermediate Similarity	NPC269451
0.8493	Intermediate Similarity	NPC100971
0.8493	Intermediate Similarity	NPC121522
0.8493	Intermediate Similarity	NPC35763
0.8493	Intermediate Similarity	NPC257648
0.8493	Intermediate Similarity	NPC100263
0.8493	Intermediate Similarity	NPC164912
0.8493	Intermediate Similarity	NPC181209
0.8493	Intermediate Similarity	NPC245382
0.8493	Intermediate Similarity	NPC477231
0.8493	Intermediate Similarity	NPC209487
0.8493	Intermediate Similarity	NPC131266
0.8493	Intermediate Similarity	NPC216769
0.8489	Intermediate Similarity	NPC322021
0.8485	Intermediate Similarity	NPC276014
0.8485	Intermediate Similarity	NPC92207
0.8485	Intermediate Similarity	NPC127937
0.8485	Intermediate Similarity	NPC154275
0.8483	Intermediate Similarity	NPC472279
0.8483	Intermediate Similarity	NPC29231
0.8472	Intermediate Similarity	NPC476394
0.8472	Intermediate Similarity	NPC15329
0.8472	Intermediate Similarity	NPC98809
0.8472	Intermediate Similarity	NPC131451
0.8467	Intermediate Similarity	NPC470990
0.8462	Intermediate Similarity	NPC165389
0.8462	Intermediate Similarity	NPC286573
0.8462	Intermediate Similarity	NPC12377
0.8456	Intermediate Similarity	NPC475468
0.8451	Intermediate Similarity	NPC242893
0.8451	Intermediate Similarity	NPC38065
0.8451	Intermediate Similarity	NPC327052
0.8451	Intermediate Similarity	NPC275278
0.8435	Intermediate Similarity	NPC287504
0.8435	Intermediate Similarity	NPC124714
0.8429	Intermediate Similarity	NPC28398
0.8425	Intermediate Similarity	NPC39793
0.8425	Intermediate Similarity	NPC256406
0.8425	Intermediate Similarity	NPC302783
0.8425	Intermediate Similarity	NPC45291
0.8425	Intermediate Similarity	NPC151425
0.8425	Intermediate Similarity	NPC144283
0.8425	Intermediate Similarity	NPC19980
0.8425	Intermediate Similarity	NPC473201
0.8409	Intermediate Similarity	NPC473626
0.8406	Intermediate Similarity	NPC90431
0.8403	Intermediate Similarity	NPC168803
0.8403	Intermediate Similarity	NPC119660
0.8403	Intermediate Similarity	NPC55557
0.8403	Intermediate Similarity	NPC61871
0.8403	Intermediate Similarity	NPC30647

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 NPC50763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	976
0.2-0.3	1688
0.3-0.4	2621
0.4-0.5	1806
0.5-0.6	1099
0.6-0.7	547
0.7-0.8	113
0.8-0.85	10
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9291	High Similarity	NPD9494	Approved
0.8397	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD3882	Suspended
0.8243	Intermediate Similarity	NPD1934	Approved
0.824	Intermediate Similarity	NPD228	Approved
0.8188	Intermediate Similarity	NPD447	Suspended
0.8188	Intermediate Similarity	NPD230	Phase 1
0.8188	Intermediate Similarity	NPD2801	Approved
0.8069	Intermediate Similarity	NPD1511	Approved
0.7986	Intermediate Similarity	NPD943	Approved
0.7959	Intermediate Similarity	NPD1512	Approved
0.7947	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD1510	Phase 2
0.7863	Intermediate Similarity	NPD5536	Phase 2
0.7857	Intermediate Similarity	NPD1240	Approved
0.7848	Intermediate Similarity	NPD3818	Discontinued
0.7834	Intermediate Similarity	NPD6166	Phase 2
0.7834	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD9545	Approved
0.78	Intermediate Similarity	NPD824	Approved
0.7762	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1607	Approved
0.774	Intermediate Similarity	NPD4628	Phase 3
0.7708	Intermediate Similarity	NPD2935	Discontinued
0.7692	Intermediate Similarity	NPD1241	Discontinued
0.7688	Intermediate Similarity	NPD7054	Approved
0.7662	Intermediate Similarity	NPD3817	Phase 2
0.7655	Intermediate Similarity	NPD2344	Approved
0.7647	Intermediate Similarity	NPD9269	Phase 2
0.764	Intermediate Similarity	NPD7472	Approved
0.764	Intermediate Similarity	NPD7074	Phase 3
0.7632	Intermediate Similarity	NPD4380	Phase 2
0.7613	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1549	Phase 2
0.7603	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD9493	Approved
0.7518	Intermediate Similarity	NPD3972	Approved
0.7518	Intermediate Similarity	NPD3027	Phase 3
0.7518	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6797	Phase 2
0.7484	Intermediate Similarity	NPD6232	Discontinued
0.7467	Intermediate Similarity	NPD6799	Approved
0.7453	Intermediate Similarity	NPD7473	Discontinued
0.745	Intermediate Similarity	NPD2309	Approved
0.745	Intermediate Similarity	NPD6190	Approved
0.7439	Intermediate Similarity	NPD7251	Discontinued
0.7434	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2799	Discontinued
0.7394	Intermediate Similarity	NPD7808	Phase 3
0.7388	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1465	Phase 2
0.7358	Intermediate Similarity	NPD5494	Approved
0.7357	Intermediate Similarity	NPD1203	Approved
0.7355	Intermediate Similarity	NPD6385	Approved
0.7355	Intermediate Similarity	NPD6386	Approved
0.7353	Intermediate Similarity	NPD9268	Approved
0.7353	Intermediate Similarity	NPD1357	Approved
0.7343	Intermediate Similarity	NPD411	Approved
0.7342	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7075	Discontinued
0.7338	Intermediate Similarity	NPD3455	Phase 2
0.7333	Intermediate Similarity	NPD7685	Pre-registration
0.7319	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1247	Approved
0.731	Intermediate Similarity	NPD1933	Approved
0.7305	Intermediate Similarity	NPD5647	Approved
0.7305	Intermediate Similarity	NPD2798	Approved
0.7303	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD919	Approved
0.7293	Intermediate Similarity	NPD5283	Phase 1
0.7286	Intermediate Similarity	NPD1876	Approved
0.7273	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8166	Discontinued
0.7261	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1358	Approved
0.723	Intermediate Similarity	NPD2796	Approved
0.7226	Intermediate Similarity	NPD7458	Discontinued
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD2354	Approved
0.7197	Intermediate Similarity	NPD6801	Discontinued
0.719	Intermediate Similarity	NPD2533	Approved
0.719	Intermediate Similarity	NPD2532	Approved
0.719	Intermediate Similarity	NPD2534	Approved
0.7181	Intermediate Similarity	NPD2346	Discontinued
0.7179	Intermediate Similarity	NPD6599	Discontinued
0.7176	Intermediate Similarity	NPD2684	Approved
0.7163	Intermediate Similarity	NPD1283	Approved
0.7152	Intermediate Similarity	NPD7819	Suspended
0.7152	Intermediate Similarity	NPD5844	Phase 1
0.7152	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD1608	Approved
0.7123	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3620	Phase 2
0.7123	Intermediate Similarity	NPD3142	Approved
0.7123	Intermediate Similarity	NPD1613	Approved
0.7123	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3140	Approved
0.7117	Intermediate Similarity	NPD3926	Phase 2
0.7114	Intermediate Similarity	NPD1551	Phase 2
0.7113	Intermediate Similarity	NPD1470	Approved
0.7107	Intermediate Similarity	NPD5978	Approved
0.7107	Intermediate Similarity	NPD5977	Approved
0.7107	Intermediate Similarity	NPD5402	Approved
0.7101	Intermediate Similarity	NPD1651	Approved
0.709	Intermediate Similarity	NPD7843	Approved
0.7083	Intermediate Similarity	NPD6832	Phase 2
0.7078	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1471	Phase 3
0.7063	Intermediate Similarity	NPD1019	Discontinued
0.7059	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7157	Approved
0.7055	Intermediate Similarity	NPD2674	Phase 3
0.7047	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD9296	Approved
0.7025	Intermediate Similarity	NPD7411	Suspended
0.7021	Intermediate Similarity	NPD1481	Phase 2
0.7007	Intermediate Similarity	NPD826	Approved
0.7007	Intermediate Similarity	NPD825	Approved
0.7006	Intermediate Similarity	NPD2649	Approved
0.7006	Intermediate Similarity	NPD2651	Approved
0.7006	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5353	Approved
0.6993	Remote Similarity	NPD3887	Approved
0.6992	Remote Similarity	NPD3021	Approved
0.6992	Remote Similarity	NPD3022	Approved
0.6988	Remote Similarity	NPD2163	Approved
0.6987	Remote Similarity	NPD5403	Approved
0.6986	Remote Similarity	NPD6798	Discontinued
0.6986	Remote Similarity	NPD3764	Approved
0.6981	Remote Similarity	NPD6844	Discontinued
0.6978	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2800	Approved
0.697	Remote Similarity	NPD290	Approved
0.6968	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4661	Approved
0.6968	Remote Similarity	NPD4662	Approved
0.6968	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5401	Approved
0.6968	Remote Similarity	NPD3146	Approved
0.6966	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7028	Phase 2
0.6959	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD555	Phase 2
0.6954	Remote Similarity	NPD2353	Approved
0.6954	Remote Similarity	NPD7266	Discontinued
0.6954	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1201	Approved
0.695	Remote Similarity	NPD1281	Approved
0.695	Remote Similarity	NPD1535	Discovery
0.6946	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD257	Approved
0.6944	Remote Similarity	NPD258	Approved
0.6943	Remote Similarity	NPD1653	Approved
0.6939	Remote Similarity	NPD6233	Phase 2
0.6939	Remote Similarity	NPD259	Phase 1
0.6939	Remote Similarity	NPD4062	Phase 3
0.6929	Remote Similarity	NPD4626	Approved
0.6929	Remote Similarity	NPD17	Approved
0.6929	Remote Similarity	NPD1778	Approved
0.6928	Remote Similarity	NPD3750	Approved
0.6923	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD6559	Discontinued
0.6918	Remote Similarity	NPD958	Approved
0.6918	Remote Similarity	NPD6873	Phase 2
0.6917	Remote Similarity	NPD74	Approved
0.6917	Remote Similarity	NPD9266	Approved
0.6913	Remote Similarity	NPD6651	Approved
0.6913	Remote Similarity	NPD6653	Approved
0.6909	Remote Similarity	NPD5242	Approved
0.6908	Remote Similarity	NPD2424	Discontinued
0.6906	Remote Similarity	NPD1894	Discontinued
0.6903	Remote Similarity	NPD4357	Discontinued
0.6897	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3134	Approved
0.6894	Remote Similarity	NPD2296	Approved
0.6892	Remote Similarity	NPD4060	Phase 1
0.6892	Remote Similarity	NPD1558	Phase 1
0.689	Remote Similarity	NPD2821	Approved
0.6887	Remote Similarity	NPD9570	Approved
0.6886	Remote Similarity	NPD3751	Discontinued
0.6879	Remote Similarity	NPD920	Approved
0.6879	Remote Similarity	NPD3496	Discontinued
0.6875	Remote Similarity	NPD37	Approved
0.6871	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3145	Approved
0.6871	Remote Similarity	NPD6234	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