NPASS Compound

Structure

CID217635 OpenBabel06191716012D 37 40 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4128 -0.0296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9128 4.3005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4128 3.4345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 4.3005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 2.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4128 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6915 2.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9128 2.5685 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 -5.4128 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 1.4945 0.0000 C 0 0 1 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 0 0 0 0 0 0 0 0 0 0 -6.9128 0.8364 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 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9128 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4128 5.1665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7405 1.8546 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 -7.4128 -0.0296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 34 1 0 0 0 0 3 4 1 0 0 0 0 3 7 1 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 27 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 19 2 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 15 16 1 0 0 0 0 15 25 2 0 0 0 0 16 11 1 6 0 0 0 16 24 1 0 0 0 0 17 18 2 0 0 0 0 17 35 1 0 0 0 0 18 33 1 0 0 0 0 19 25 1 0 0 0 0 19 34 1 0 0 0 0 20 12 1 6 0 0 0 20 21 1 0 0 0 0 20 36 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 1 0 0 0 22 23 1 0 0 0 0 22 31 1 6 0 0 0 23 26 1 0 0 0 0 23 32 1 1 0 0 0 24 14 1 1 0 0 0 24 37 1 0 0 0 0 25 37 1 0 0 0 0 26 35 1 6 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.21
Volume:	504.9
LogP:	0.231
LogD:	0.379
LogS:	-3.159
# Rotatable Bonds:	10
TPSA:	167.53
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.249
Synthetic Accessibility Score:	4.256
Fsp3:	0.538
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:	-6.113
MDCK Permeability:	4.345479101175442e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.898
Human Intestinal Absorption (HIA):	0.612
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.674

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.209
Plasma Protein Binding (PPB):	54.10316467285156%
Volume Distribution (VD):	0.34
Pgp-substrate:	22.4567813873291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.251
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.532

ADMET: Excretion

Clearance (CL):	3.751
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.36
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.238
AMES Toxicity:	0.141
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.554
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC217635

Natural Product ID:	NPC217635
*Common Name:**	(7S,8R)-Urolignoside
IUPAC Name:	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]oxane-3,4,5-triol
Synonyms:	(7S,8R)-Urolignoside
Standard InCHIKey:	NYAPVWGUAUDHRY-KUCLMONLSA-N
Standard InCHI:	InChI=1S/C26H34O11/c1-33-18-10-14(5-6-17(18)35-26-23(32)22(31)21(30)20(12-29)36-26)24-16(11-28)15-8-13(4-3-7-27)9-19(34-2)25(15)37-24/h5-6,8-10,16,20-24,26-32H,3-4,7,11-12H2,1-2H3/t16-,20+,21+,22-,23+,24+,26+/m0/s1
SMILES:	OCCCc1cc(OC)c2c(c1)[C@H](CO)[C@H](O2)c1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2336751
PubChem CID:	10602086
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)83457-3]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075772]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10757717]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843567]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678669]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[12943781]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951446]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	stems	Thailand	n.a.	PMID[14510595]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	Argentine	n.a.	PMID[14738381]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738381]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043405]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16155971]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125219]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665952]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345641]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18991207]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19824618]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	essential oil	Tibet	n.a.	PMID[20944522]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21667999]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21905650]
NPO32535	dracocephalum ruyschiana	Species	Lamiaceae	Eukaryota	aerial parts	Mongolian	n.a.	PMID[23356964]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24094434]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697288]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27592135]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28541690]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[324959]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33325237]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[9599285]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23706	Breea segeta	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5552	Solanum sisymbriifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13710	Lyophyllum shimeji	Species	Lyophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9903	Engelhardia spicata	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13230	Pedicularis condensata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3391	Jungermannia obovata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8499	Osmerus mordax	Species	Osmeridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7766	Pericopsis schliebenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4935	Dinemasporium strigosum	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2304	Byssovorax cruenta	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1355	Urechis caupo	Species	Urechidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15755	Thymbra spicata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25481	Lonchocarpus oaxacensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7060	Ficus ruficaulis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3830	Euplotes rariseta	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5269	Coleus garckeanus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14034	Salvia coulteri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6310	Ruta bracteosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12680	Perityle vaseyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11881	Adenopeltis colliguaya	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5319	Ulmus thomasii	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15272	Mascarenhasia arborescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8103	Lecanora melanophthalma	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24732	Cereus weberi	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO276	Miscanthus sacchariflorus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15138	Rheum webbianum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13859	Senecio flavus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4267	Ceratocystis clavigera	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14218	Spodoptera littoralis	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15610	Citrus trifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10806	Achillea roseoalba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15015	Meconopsis napaulensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5078	Turraeanthus mannii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4516	Fasciospongia rimosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24370	Crassocephalum crepidioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	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	2
Others	6

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	38.4	%	PMID[504767]
NPT1	Others	Radical scavenging activity		IC50	>	200.0	ug.mL-1	PMID[504765]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	1.765	log10CFU/ml	PMID[504766]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	1.811	log10CFU/ml	PMID[504766]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	1.858	log10CFU/ml	PMID[504766]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	=	2.043	log10CFU/ml	PMID[504766]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	GI	=	21.0	%	PMID[504766]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	3600.0	nM	PMID[504767]

☑ 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 NPC217635 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	407
0.1-0.2	1436
0.2-0.3	3609
0.3-0.4	9240
0.4-0.5	9318
0.5-0.6	4882
0.6-0.7	8546
0.7-0.8	4147
0.8-0.85	798
0.85-0.9	255
0.9-0.95	43
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC79429
1.0	High Similarity	NPC471667
0.9927	High Similarity	NPC476301
0.9927	High Similarity	NPC43508
0.9784	High Similarity	NPC114505
0.9784	High Similarity	NPC31325
0.9784	High Similarity	NPC224674
0.9784	High Similarity	NPC275284
0.9784	High Similarity	NPC193473
0.9784	High Similarity	NPC213074
0.9784	High Similarity	NPC15956
0.9714	High Similarity	NPC270751
0.9577	High Similarity	NPC98624
0.9565	High Similarity	NPC246947
0.9496	High Similarity	NPC470950
0.9496	High Similarity	NPC185307
0.9444	High Similarity	NPC302610
0.9441	High Similarity	NPC472709
0.9441	High Similarity	NPC472710
0.9429	High Similarity	NPC129417
0.9429	High Similarity	NPC471063
0.9429	High Similarity	NPC283995
0.9429	High Similarity	NPC470235
0.9424	High Similarity	NPC253878
0.9424	High Similarity	NPC476356
0.9362	High Similarity	NPC22150
0.9362	High Similarity	NPC279298
0.9362	High Similarity	NPC38041
0.9357	High Similarity	NPC46092
0.9353	High Similarity	NPC472711
0.9353	High Similarity	NPC471414
0.9348	High Similarity	NPC156376
0.9338	High Similarity	NPC187194
0.9338	High Similarity	NPC476411
0.9296	High Similarity	NPC205796
0.9296	High Similarity	NPC112861
0.9296	High Similarity	NPC276753
0.9231	High Similarity	NPC39657
0.9225	High Similarity	NPC18979
0.922	High Similarity	NPC477898
0.9214	High Similarity	NPC471908
0.9191	High Similarity	NPC230219
0.9189	High Similarity	NPC228357
0.9178	High Similarity	NPC474442
0.9155	High Similarity	NPC84181
0.9149	High Similarity	NPC302506
0.9137	High Similarity	NPC138738
0.9137	High Similarity	NPC470413
0.9124	High Similarity	NPC26394
0.9103	High Similarity	NPC44452
0.9103	High Similarity	NPC55158
0.9103	High Similarity	NPC286235
0.9103	High Similarity	NPC51328
0.9091	High Similarity	NPC475096
0.9078	High Similarity	NPC76871
0.9067	High Similarity	NPC173726
0.9067	High Similarity	NPC241600
0.9067	High Similarity	NPC478269
0.9065	High Similarity	NPC177160
0.9065	High Similarity	NPC199459
0.9065	High Similarity	NPC54743
0.9065	High Similarity	NPC52277
0.9065	High Similarity	NPC263367
0.9065	High Similarity	NPC156502
0.9065	High Similarity	NPC477939
0.9065	High Similarity	NPC29799
0.9065	High Similarity	NPC209985
0.9065	High Similarity	NPC177035
0.9065	High Similarity	NPC10737
0.9058	High Similarity	NPC170779
0.9058	High Similarity	NPC90083
0.9044	High Similarity	NPC472024
0.9044	High Similarity	NPC80600
0.9041	High Similarity	NPC238140
0.9041	High Similarity	NPC158635
0.9041	High Similarity	NPC229882
0.9041	High Similarity	NPC475224
0.9034	High Similarity	NPC130449
0.9034	High Similarity	NPC248132
0.9028	High Similarity	NPC190714
0.9028	High Similarity	NPC99515
0.9021	High Similarity	NPC164183
0.9021	High Similarity	NPC187774
0.9021	High Similarity	NPC472713
0.9021	High Similarity	NPC179521
0.9021	High Similarity	NPC473046
0.9021	High Similarity	NPC472712
0.9021	High Similarity	NPC118385
0.9014	High Similarity	NPC60249
0.9007	High Similarity	NPC106944
0.8993	High Similarity	NPC101624
0.8993	High Similarity	NPC184938
0.8993	High Similarity	NPC79957
0.8986	High Similarity	NPC25821
0.8978	High Similarity	NPC9912
0.8973	High Similarity	NPC55715
0.8973	High Similarity	NPC35877
0.8973	High Similarity	NPC95392
0.8971	High Similarity	NPC26653
0.8971	High Similarity	NPC270849
0.8966	High Similarity	NPC227902
0.8958	High Similarity	NPC272619
0.8958	High Similarity	NPC180953
0.8958	High Similarity	NPC286245
0.8958	High Similarity	NPC181615
0.8958	High Similarity	NPC469586
0.8951	High Similarity	NPC278961
0.8951	High Similarity	NPC113680
0.8947	High Similarity	NPC478267
0.8944	High Similarity	NPC108674
0.8921	High Similarity	NPC187616
0.8921	High Similarity	NPC16485
0.8921	High Similarity	NPC193026
0.8921	High Similarity	NPC49603
0.8913	High Similarity	NPC18842
0.8912	High Similarity	NPC183380
0.8904	High Similarity	NPC71726
0.8904	High Similarity	NPC175976
0.8897	High Similarity	NPC93610
0.8897	High Similarity	NPC125755
0.8897	High Similarity	NPC241846
0.8897	High Similarity	NPC260397
0.8897	High Similarity	NPC302378
0.8889	High Similarity	NPC25292
0.8889	High Similarity	NPC471065
0.8889	High Similarity	NPC253015
0.8889	High Similarity	NPC473045
0.8881	High Similarity	NPC131971
0.8881	High Similarity	NPC472714
0.8881	High Similarity	NPC5262
0.8881	High Similarity	NPC469559
0.8881	High Similarity	NPC475084
0.8881	High Similarity	NPC189115
0.8873	High Similarity	NPC226547
0.8865	High Similarity	NPC477938
0.8865	High Similarity	NPC304152
0.8859	High Similarity	NPC61604
0.8859	High Similarity	NPC299706
0.8859	High Similarity	NPC245615
0.8859	High Similarity	NPC115466
0.8857	High Similarity	NPC236522
0.8857	High Similarity	NPC93783
0.8844	High Similarity	NPC240521
0.8836	High Similarity	NPC99183
0.8832	High Similarity	NPC166040
0.8832	High Similarity	NPC248355
0.8828	High Similarity	NPC277867
0.8828	High Similarity	NPC307466
0.8828	High Similarity	NPC161700
0.8824	High Similarity	NPC98745
0.8819	High Similarity	NPC81638
0.8819	High Similarity	NPC473044
0.8811	High Similarity	NPC469661
0.8811	High Similarity	NPC263261
0.8811	High Similarity	NPC87725
0.8803	High Similarity	NPC292487
0.88	High Similarity	NPC159922
0.8794	High Similarity	NPC77861
0.8794	High Similarity	NPC25695
0.8794	High Similarity	NPC172818
0.8792	High Similarity	NPC21902
0.8792	High Similarity	NPC59692
0.8786	High Similarity	NPC47181
0.8786	High Similarity	NPC478085
0.8786	High Similarity	NPC35731
0.8786	High Similarity	NPC470881
0.8784	High Similarity	NPC185955
0.8784	High Similarity	NPC214326
0.8784	High Similarity	NPC9933
0.8784	High Similarity	NPC218041
0.8784	High Similarity	NPC182368
0.8784	High Similarity	NPC469706
0.8784	High Similarity	NPC469707
0.8784	High Similarity	NPC225815
0.8784	High Similarity	NPC260781
0.8784	High Similarity	NPC145979
0.8777	High Similarity	NPC219671
0.8777	High Similarity	NPC7744
0.8777	High Similarity	NPC104077
0.8777	High Similarity	NPC471505
0.8777	High Similarity	NPC147616
0.8777	High Similarity	NPC106739
0.8777	High Similarity	NPC259742
0.8776	High Similarity	NPC474795
0.8776	High Similarity	NPC301961
0.8776	High Similarity	NPC166584
0.8776	High Similarity	NPC159697
0.8776	High Similarity	NPC226153
0.8776	High Similarity	NPC130959
0.8776	High Similarity	NPC474940
0.8776	High Similarity	NPC304048
0.8776	High Similarity	NPC303013
0.8767	High Similarity	NPC162193
0.8759	High Similarity	NPC76176
0.8759	High Similarity	NPC138227
0.8759	High Similarity	NPC133251
0.8759	High Similarity	NPC45257
0.8759	High Similarity	NPC469313
0.8759	High Similarity	NPC280092
0.8759	High Similarity	NPC12641

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 NPC217635 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	809
0.2-0.3	1701
0.3-0.4	2780
0.4-0.5	1805
0.5-0.6	998
0.6-0.7	608
0.7-0.8	110
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8944	High Similarity	NPD6674	Discontinued
0.8252	Intermediate Similarity	NPD1613	Approved
0.8252	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5058	Phase 3
0.8129	Intermediate Similarity	NPD37	Approved
0.8116	Intermediate Similarity	NPD3705	Approved
0.8116	Intermediate Similarity	NPD1091	Approved
0.8113	Intermediate Similarity	NPD7199	Phase 2
0.8089	Intermediate Similarity	NPD4966	Approved
0.8089	Intermediate Similarity	NPD4965	Approved
0.8089	Intermediate Similarity	NPD4967	Phase 2
0.8086	Intermediate Similarity	NPD7228	Approved
0.8077	Intermediate Similarity	NPD8455	Phase 2
0.8054	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD3027	Phase 3
0.8041	Intermediate Similarity	NPD7266	Discontinued
0.8028	Intermediate Similarity	NPD2861	Phase 2
0.7987	Intermediate Similarity	NPD6234	Discontinued
0.7987	Intermediate Similarity	NPD1653	Approved
0.7972	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7240	Approved
0.7879	Intermediate Similarity	NPD7074	Phase 3
0.7866	Intermediate Similarity	NPD3818	Discontinued
0.7862	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7054	Approved
0.7817	Intermediate Similarity	NPD8651	Approved
0.7785	Intermediate Similarity	NPD5588	Approved
0.7771	Intermediate Similarity	NPD7472	Approved
0.777	Intermediate Similarity	NPD1357	Approved
0.7755	Intermediate Similarity	NPD4060	Phase 1
0.7724	Intermediate Similarity	NPD4908	Phase 1
0.7721	Intermediate Similarity	NPD5283	Phase 1
0.7718	Intermediate Similarity	NPD4536	Approved
0.7718	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4538	Approved
0.7714	Intermediate Similarity	NPD5126	Approved
0.7714	Intermediate Similarity	NPD5125	Phase 3
0.7682	Intermediate Similarity	NPD5762	Approved
0.7682	Intermediate Similarity	NPD5763	Approved
0.7679	Intermediate Similarity	NPD6559	Discontinued
0.7633	Intermediate Similarity	NPD7808	Phase 3
0.7613	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7157	Approved
0.7606	Intermediate Similarity	NPD1610	Phase 2
0.76	Intermediate Similarity	NPD7097	Phase 1
0.7584	Intermediate Similarity	NPD6355	Discontinued
0.7584	Intermediate Similarity	NPD5735	Approved
0.7574	Intermediate Similarity	NPD7251	Discontinued
0.755	Intermediate Similarity	NPD5960	Phase 3
0.755	Intermediate Similarity	NPD4108	Discontinued
0.7532	Intermediate Similarity	NPD6331	Phase 2
0.7518	Intermediate Similarity	NPD7843	Approved
0.7517	Intermediate Similarity	NPD3620	Phase 2
0.7517	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5494	Approved
0.7485	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7685	Pre-registration
0.7455	Intermediate Similarity	NPD8127	Discontinued
0.7453	Intermediate Similarity	NPD1934	Approved
0.7451	Intermediate Similarity	NPD1375	Discontinued
0.7432	Intermediate Similarity	NPD4625	Phase 3
0.7427	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3018	Phase 2
0.741	Intermediate Similarity	NPD3051	Approved
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7365	Intermediate Similarity	NPD2969	Approved
0.7365	Intermediate Similarity	NPD2970	Approved
0.7353	Intermediate Similarity	NPD2684	Approved
0.7321	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6166	Phase 2
0.7321	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7095	Approved
0.7308	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4110	Phase 3
0.7301	Intermediate Similarity	NPD2978	Approved
0.7301	Intermediate Similarity	NPD2977	Approved
0.729	Intermediate Similarity	NPD2424	Discontinued
0.7285	Intermediate Similarity	NPD4140	Approved
0.7279	Intermediate Similarity	NPD290	Approved
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7261	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2677	Approved
0.726	Intermediate Similarity	NPD5327	Phase 3
0.726	Intermediate Similarity	NPD4749	Approved
0.726	Intermediate Similarity	NPD2983	Phase 2
0.726	Intermediate Similarity	NPD2982	Phase 2
0.726	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3817	Phase 2
0.725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5177	Phase 3
0.7244	Intermediate Similarity	NPD4236	Phase 3
0.7244	Intermediate Similarity	NPD4237	Approved
0.7238	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5124	Phase 1
0.7237	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6671	Approved
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6004	Phase 3
0.7226	Intermediate Similarity	NPD6002	Phase 3
0.7226	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6005	Phase 3
0.7226	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2489	Approved
0.7219	Intermediate Similarity	NPD27	Approved
0.7216	Intermediate Similarity	NPD6841	Approved
0.7216	Intermediate Similarity	NPD6842	Approved
0.7216	Intermediate Similarity	NPD6843	Phase 3
0.7211	Intermediate Similarity	NPD6696	Suspended
0.7203	Intermediate Similarity	NPD1548	Phase 1
0.7202	Intermediate Similarity	NPD3787	Discontinued
0.7202	Intermediate Similarity	NPD6071	Discontinued
0.7197	Intermediate Similarity	NPD4535	Phase 3
0.7195	Intermediate Similarity	NPD7819	Suspended
0.7195	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD228	Approved
0.7192	Intermediate Similarity	NPD2981	Phase 2
0.719	Intermediate Similarity	NPD6653	Approved
0.7188	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7313	Approved
0.7184	Intermediate Similarity	NPD7312	Approved
0.7184	Intermediate Similarity	NPD7311	Approved
0.7184	Intermediate Similarity	NPD7310	Approved
0.7174	Intermediate Similarity	NPD7680	Approved
0.7169	Intermediate Similarity	NPD7075	Discontinued
0.716	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2563	Approved
0.7152	Intermediate Similarity	NPD2560	Approved
0.7143	Intermediate Similarity	NPD7309	Approved
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7119	Intermediate Similarity	NPD7906	Approved
0.7117	Intermediate Similarity	NPD4380	Phase 2
0.7117	Intermediate Similarity	NPD7028	Phase 2
0.7115	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3882	Suspended
0.7107	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6667	Approved
0.7107	Intermediate Similarity	NPD6666	Approved
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7103	Intermediate Similarity	NPD6516	Phase 2
0.7103	Intermediate Similarity	NPD5846	Approved
0.7101	Intermediate Similarity	NPD7229	Phase 3
0.7097	Intermediate Similarity	NPD7033	Discontinued
0.7091	Intermediate Similarity	NPD5772	Approved
0.7091	Intermediate Similarity	NPD2801	Approved
0.7091	Intermediate Similarity	NPD5773	Approved
0.7089	Intermediate Similarity	NPD4628	Phase 3
0.7081	Intermediate Similarity	NPD52	Approved
0.7081	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7526	Approved
0.7079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6353	Approved
0.7076	Intermediate Similarity	NPD7473	Discontinued
0.7073	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1774	Approved
0.7062	Intermediate Similarity	NPD4663	Approved
0.7059	Intermediate Similarity	NPD1558	Phase 1
0.7051	Intermediate Similarity	NPD2161	Phase 2
0.705	Intermediate Similarity	NPD3021	Approved
0.705	Intermediate Similarity	NPD3022	Approved
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7119	Phase 2
0.703	Intermediate Similarity	NPD3382	Approved
0.703	Intermediate Similarity	NPD3384	Approved
0.703	Intermediate Similarity	NPD3383	Approved
0.7027	Intermediate Similarity	NPD3685	Discontinued
0.7027	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4162	Approved
0.7022	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4481	Phase 3
0.7013	Intermediate Similarity	NPD3657	Discovery
0.7	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6387	Discontinued
0.6989	Remote Similarity	NPD4578	Approved
0.6989	Remote Similarity	NPD4577	Approved
0.6988	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3892	Phase 2
0.6981	Remote Similarity	NPD7466	Approved

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