NPASS Compound

Structure

CID230124 OpenBabel06191716022D 30 32 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 -1.7321 0.0000 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 0.0000 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -4.3301 1.5000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 11 1 0 0 0 0 5 13 1 0 0 0 0 6 11 2 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 19 1 0 0 0 0 13 9 1 6 0 0 0 13 14 1 0 0 0 0 14 10 1 1 0 0 0 14 18 1 0 0 0 0 15 20 2 0 0 0 0 15 27 1 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 17 21 2 0 0 0 0 17 29 1 0 0 0 0 18 12 1 6 0 0 0 18 19 1 0 0 0 0 19 22 2 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	417.902
LogP:	1.784
LogD:	1.967
LogS:	-4.03
# Rotatable Bonds:	7
TPSA:	117.84
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	3.716
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.146
MDCK Permeability:	6.286618372541852e-06
Pgp-inhibitor:	0.022
Pgp-substrate:	0.306
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	88.02465057373047%
Volume Distribution (VD):	0.516
Pgp-substrate:	20.790754318237305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.655
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.581
CYP3A4-inhibitor:	0.361
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	11.31
Half-life (T1/2):	0.832

ADMET: Toxicity

hERG Blockers:	0.225
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.683
Skin Sensitization:	0.401
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.08
Respiratory Toxicity:	0.282

Download Data

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

Natural Product: NPC230124

Natural Product ID:	NPC230124
*Common Name:**	(+)-Lyoniresinol
IUPAC Name:	(6R,7R,8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol
Synonyms:	(+)-Lyoniresinol
Standard InCHIKey:	ZDVZKBOFCHOPLM-SUNYJGFJSA-N
Standard InCHI:	InChI=1S/C22H28O8/c1-27-15-7-12(8-16(28-2)20(15)25)18-14(10-24)13(9-23)5-11-6-17(29-3)21(26)22(30-4)19(11)18/h6-8,13-14,18,23-26H,5,9-10H2,1-4H3/t13-,14-,18+/m0/s1
SMILES:	OC[C@@H]1Cc2cc(OC)c(c(c2[C@@H]([C@H]1CO)c1cc(OC)c(c(c1)OC)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455365
PubChem CID:	11711453
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans [CHEMONTID:0003426] 9,9p-dihydroxyaryltetralin lignans

*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
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10757717]
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]
NPO297	Methylobacterium extorquens	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15074037]
NPO21790	Croton insularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104505]
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921425]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	stem	n.a.	PMID[16651764]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19813743]
NPO28146	Liriope spicata	Species	Asparagaceae	Eukaryota	Tuberous root	n.a.	n.a.	PMID[19874043]
NPO28358	Pleuranthodium racemigerum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20297825]
NPO28186	Trididemnum solidum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21341712]
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]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	skin-removed stems	Pingle Town, Sichuang Province, China	2008-AUG	PMID[21469695]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	stem	n.a.	PMID[21469695]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21627109]
NPO28186	Trididemnum solidum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21770369]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21905650]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22690646]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24697288]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26988298]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO28186	Trididemnum solidum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3373220]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[9599285]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13719	Salacia prinoides	Species	Sertulariidae	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]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21919	Polysaccharidum versicolor	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28146	Liriope spicata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23289	Heracleum sphondylium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21919	Polysaccharidum versicolor	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28598	Cotylelobium lanceolatum	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28146	Liriope spicata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14869	Ormosia panamensis	Species	Limoniidae	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]
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12416	Quercus mongolica	Species	Fagaceae	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]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28146	Liriope spicata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16758	Satureja cuneifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15510	Kummerowia striata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2353	Bituminaria bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13548	Chrozophora obliqua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16428	Millettia conraui	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16678	Flindersia brayleyana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15272	Mascarenhasia arborescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8499	Osmerus mordax	Species	Osmeridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21790	Croton insularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24732	Cereus weberi	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO297	Methylobacterium extorquens	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28286	Mitragyna hirsuta	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15138	Rheum webbianum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28548	Thalictrum strictum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5078	Turraeanthus mannii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28076	Celtis durandii	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4267	Ceratocystis clavigera	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12680	Perityle vaseyi	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]
NPO14034	Salvia coulteri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14787	Argyrochosma fendleri	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15393	Eucalyptus flocktoniae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24176	Streptomyces fradiae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14555	Porella swartziana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29418	Rugosa rugosa	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16847	Consolida ajacis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9780	Merremia umbellata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28376	Syncarpia laurifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26017	Dalbergia stipulacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28598	Cotylelobium lanceolatum	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5777	Pimelobacter simplex	Species	0cardioidaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28186	Trididemnum solidum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19192	Sinocalamus affinis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13859	Senecio flavus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28395	Tradescantia pallida	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4935	Dinemasporium strigosum	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15858	Phoebe formosana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14218	Spodoptera littoralis	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15755	Thymbra spicata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5552	Solanum sisymbriifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28358	Pleuranthodium racemigerum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5728	Gerbera piloselloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27993	Bacillus badius	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5269	Coleus garckeanus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15015	Meconopsis napaulensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16175	Trichia floriformis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28146	Liriope spicata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4001	Berberis koreana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13710	Lyophyllum shimeji	Species	Lyophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7484	Salacia chinensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13230	Pedicularis condensata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28706	Sideritis caesarea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3391	Jungermannia obovata	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11881	Adenopeltis colliguaya	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9420	Aspergillus arenarius	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16516	Centaurea seridis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14869	Ormosia panamensis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23289	Heracleum sphondylium	Species	Apiaceae	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	6
Others	2

Activity Type	# Activity
Cell Line	6
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	69140.0	nM	PMID[512029]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[512029]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000.0	nM	PMID[512029]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	7140.0	nM	PMID[512029]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[512029]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	79.4	%	PMID[512030]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	100000.0	nM	PMID[512028]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	Inhibition	=	10.0	%	PMID[512028]

☑ 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 NPC230124 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	438
0.1-0.2	1546
0.2-0.3	4171
0.3-0.4	10809
0.4-0.5	7797
0.5-0.6	3781
0.6-0.7	7117
0.7-0.8	5356
0.8-0.85	957
0.85-0.9	557
0.9-0.95	149
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC114171
1.0	High Similarity	NPC6300
0.9848	High Similarity	NPC184613
0.9621	High Similarity	NPC313081
0.9549	High Similarity	NPC143139
0.9549	High Similarity	NPC202846
0.9545	High Similarity	NPC209199
0.9545	High Similarity	NPC125649
0.9542	High Similarity	NPC14224
0.9542	High Similarity	NPC161958
0.9493	High Similarity	NPC112251
0.9474	High Similarity	NPC69029
0.9474	High Similarity	NPC158142
0.9474	High Similarity	NPC294884
0.9474	High Similarity	NPC108198
0.9474	High Similarity	NPC10314
0.9474	High Similarity	NPC200557
0.9407	High Similarity	NPC212942
0.9407	High Similarity	NPC29868
0.9407	High Similarity	NPC79622
0.9398	High Similarity	NPC311256
0.9398	High Similarity	NPC160697
0.9338	High Similarity	NPC308768
0.9338	High Similarity	NPC12668
0.9333	High Similarity	NPC242715
0.9333	High Similarity	NPC86605
0.9333	High Similarity	NPC22902
0.9333	High Similarity	NPC301765
0.9333	High Similarity	NPC56329
0.9333	High Similarity	NPC3072
0.9333	High Similarity	NPC46277
0.9333	High Similarity	NPC156948
0.9328	High Similarity	NPC241241
0.9265	High Similarity	NPC243759
0.9265	High Similarity	NPC243996
0.9265	High Similarity	NPC132804
0.9265	High Similarity	NPC275061
0.9265	High Similarity	NPC218131
0.9265	High Similarity	NPC105847
0.9265	High Similarity	NPC220344
0.9259	High Similarity	NPC205442
0.9259	High Similarity	NPC30632
0.9259	High Similarity	NPC133025
0.9254	High Similarity	NPC289258
0.9254	High Similarity	NPC555
0.9254	High Similarity	NPC56764
0.9254	High Similarity	NPC206737
0.9254	High Similarity	NPC188378
0.9254	High Similarity	NPC7515
0.9254	High Similarity	NPC276026
0.9254	High Similarity	NPC469659
0.9242	High Similarity	NPC126836
0.9225	High Similarity	NPC182368
0.9225	High Similarity	NPC469707
0.9225	High Similarity	NPC185955
0.9225	High Similarity	NPC9933
0.9225	High Similarity	NPC214326
0.9225	High Similarity	NPC469706
0.9225	High Similarity	NPC260781
0.9225	High Similarity	NPC225815
0.9225	High Similarity	NPC218041
0.9225	High Similarity	NPC145979
0.9203	High Similarity	NPC191231
0.9203	High Similarity	NPC175838
0.9191	High Similarity	NPC200935
0.9191	High Similarity	NPC151656
0.9191	High Similarity	NPC230919
0.9191	High Similarity	NPC266453
0.9191	High Similarity	NPC266006
0.9185	High Similarity	NPC180602
0.9185	High Similarity	NPC214853
0.9185	High Similarity	NPC240279
0.9185	High Similarity	NPC256262
0.9185	High Similarity	NPC55239
0.9173	High Similarity	NPC474017
0.9137	High Similarity	NPC469630
0.9124	High Similarity	NPC260741
0.9124	High Similarity	NPC70682
0.9124	High Similarity	NPC471183
0.9118	High Similarity	NPC265433
0.9118	High Similarity	NPC162659
0.9118	High Similarity	NPC270456
0.9118	High Similarity	NPC248727
0.9111	High Similarity	NPC326095
0.9111	High Similarity	NPC244983
0.9104	High Similarity	NPC6451
0.9091	High Similarity	NPC28765
0.9091	High Similarity	NPC307050
0.9091	High Similarity	NPC24425
0.9091	High Similarity	NPC277458
0.9084	High Similarity	NPC76451
0.9078	High Similarity	NPC260397
0.9071	High Similarity	NPC473108
0.9065	High Similarity	NPC183709
0.9065	High Similarity	NPC472088
0.9065	High Similarity	NPC472087
0.9065	High Similarity	NPC470917
0.9058	High Similarity	NPC34431
0.9058	High Similarity	NPC472092
0.9058	High Similarity	NPC73505
0.9058	High Similarity	NPC472091
0.9058	High Similarity	NPC472090
0.9058	High Similarity	NPC259519
0.9058	High Similarity	NPC266197
0.9058	High Similarity	NPC165026
0.9058	High Similarity	NPC291101
0.9058	High Similarity	NPC295719
0.9051	High Similarity	NPC6262
0.9051	High Similarity	NPC73535
0.9051	High Similarity	NPC90615
0.9051	High Similarity	NPC272157
0.9051	High Similarity	NPC25111
0.9051	High Similarity	NPC201145
0.9044	High Similarity	NPC47398
0.9044	High Similarity	NPC234333
0.9044	High Similarity	NPC260898
0.9037	High Similarity	NPC32778
0.903	High Similarity	NPC232275
0.903	High Similarity	NPC474356
0.903	High Similarity	NPC45715
0.903	High Similarity	NPC15543
0.903	High Similarity	NPC12275
0.9023	High Similarity	NPC476968
0.9023	High Similarity	NPC212015
0.9023	High Similarity	NPC170844
0.9015	High Similarity	NPC159968
0.9015	High Similarity	NPC324112
0.9015	High Similarity	NPC236791
0.9015	High Similarity	NPC252131
0.9015	High Similarity	NPC127587
0.9015	High Similarity	NPC74817
0.9015	High Similarity	NPC82679
0.9015	High Similarity	NPC169474
0.9015	High Similarity	NPC293054
0.9015	High Similarity	NPC246620
0.9015	High Similarity	NPC282000
0.9015	High Similarity	NPC124452
0.9015	High Similarity	NPC471986
0.9014	High Similarity	NPC262297
0.9014	High Similarity	NPC474397
0.8993	High Similarity	NPC178054
0.8993	High Similarity	NPC311530
0.8993	High Similarity	NPC35216
0.8993	High Similarity	NPC87725
0.8993	High Similarity	NPC265075
0.8993	High Similarity	NPC263261
0.8993	High Similarity	NPC472089
0.8993	High Similarity	NPC471389
0.8986	High Similarity	NPC245207
0.8986	High Similarity	NPC319647
0.8986	High Similarity	NPC127218
0.8986	High Similarity	NPC32630
0.8986	High Similarity	NPC22517
0.8986	High Similarity	NPC25966
0.8978	High Similarity	NPC234952
0.8978	High Similarity	NPC300846
0.8978	High Similarity	NPC306441
0.8978	High Similarity	NPC16435
0.8978	High Similarity	NPC470802
0.8978	High Similarity	NPC476639
0.8978	High Similarity	NPC68292
0.8978	High Similarity	NPC114155
0.8971	High Similarity	NPC317380
0.8971	High Similarity	NPC471942
0.8971	High Similarity	NPC287745
0.8966	High Similarity	NPC21902
0.8963	High Similarity	NPC127624
0.8963	High Similarity	NPC204215
0.8963	High Similarity	NPC201587
0.8963	High Similarity	NPC253105
0.8963	High Similarity	NPC175067
0.8963	High Similarity	NPC228843
0.8955	High Similarity	NPC299221
0.8955	High Similarity	NPC234488
0.8955	High Similarity	NPC192687
0.8955	High Similarity	NPC311680
0.8955	High Similarity	NPC51840
0.8955	High Similarity	NPC224157
0.8947	High Similarity	NPC470213
0.8947	High Similarity	NPC98631
0.8947	High Similarity	NPC206615
0.8947	High Similarity	NPC186843
0.8947	High Similarity	NPC472968
0.8947	High Similarity	NPC154866
0.8944	High Similarity	NPC317053
0.8944	High Similarity	NPC126291
0.8944	High Similarity	NPC233980
0.8944	High Similarity	NPC474054
0.8944	High Similarity	NPC324492
0.8939	High Similarity	NPC18924
0.8939	High Similarity	NPC44748
0.8939	High Similarity	NPC223136
0.8939	High Similarity	NPC28730
0.8939	High Similarity	NPC214406
0.8939	High Similarity	NPC78974
0.8939	High Similarity	NPC103823
0.8936	High Similarity	NPC469795
0.8936	High Similarity	NPC87883
0.8936	High Similarity	NPC50250
0.8929	High Similarity	NPC475891

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 NPC230124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	898
0.2-0.3	1871
0.3-0.4	2809
0.4-0.5	1598
0.5-0.6	864
0.6-0.7	602
0.7-0.8	128
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9023	High Similarity	NPD3027	Phase 3
0.8686	High Similarity	NPD1612	Clinical (unspecified phase)
0.8686	High Similarity	NPD1613	Approved
0.8593	High Similarity	NPD1530	Clinical (unspecified phase)
0.8529	High Similarity	NPD1529	Clinical (unspecified phase)
0.8523	High Similarity	NPD37	Approved
0.8487	Intermediate Similarity	NPD6234	Discontinued
0.8417	Intermediate Similarity	NPD3620	Phase 2
0.8417	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD4967	Phase 2
0.8355	Intermediate Similarity	NPD4966	Approved
0.8355	Intermediate Similarity	NPD4965	Approved
0.8273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4908	Phase 1
0.8228	Intermediate Similarity	NPD7228	Approved
0.8116	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD6674	Discontinued
0.8071	Intermediate Similarity	NPD4625	Phase 3
0.8058	Intermediate Similarity	NPD3018	Phase 2
0.8015	Intermediate Similarity	NPD1610	Phase 2
0.8014	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7937	Intermediate Similarity	NPD7473	Discontinued
0.7911	Intermediate Similarity	NPD7199	Phase 2
0.7899	Intermediate Similarity	NPD2983	Phase 2
0.7899	Intermediate Similarity	NPD2982	Phase 2
0.7899	Intermediate Similarity	NPD4749	Approved
0.7879	Intermediate Similarity	NPD5283	Phase 1
0.7838	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD2981	Phase 2
0.7806	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD4060	Phase 1
0.7771	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD6166	Phase 2
0.7764	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD5844	Phase 1
0.7727	Intermediate Similarity	NPD228	Approved
0.7727	Intermediate Similarity	NPD4005	Discontinued
0.7721	Intermediate Similarity	NPD1548	Phase 1
0.7702	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7240	Approved
0.7676	Intermediate Similarity	NPD2861	Phase 2
0.7662	Intermediate Similarity	NPD1653	Approved
0.7643	Intermediate Similarity	NPD2801	Approved
0.7626	Intermediate Similarity	NPD3705	Approved
0.7576	Intermediate Similarity	NPD3021	Approved
0.7576	Intermediate Similarity	NPD3022	Approved
0.7535	Intermediate Similarity	NPD3094	Phase 2
0.7532	Intermediate Similarity	NPD1465	Phase 2
0.7518	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5735	Approved
0.7483	Intermediate Similarity	NPD3657	Discovery
0.747	Intermediate Similarity	NPD7074	Phase 3
0.7467	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3540	Phase 1
0.7456	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3818	Discontinued
0.7452	Intermediate Similarity	NPD4380	Phase 2
0.7444	Intermediate Similarity	NPD4750	Phase 3
0.7438	Intermediate Similarity	NPD3882	Suspended
0.7432	Intermediate Similarity	NPD4097	Suspended
0.741	Intermediate Similarity	NPD7054	Approved
0.7403	Intermediate Similarity	NPD1511	Approved
0.74	Intermediate Similarity	NPD3539	Phase 1
0.74	Intermediate Similarity	NPD6099	Approved
0.74	Intermediate Similarity	NPD6100	Approved
0.7386	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD3092	Approved
0.7375	Intermediate Similarity	NPD3817	Phase 2
0.7368	Intermediate Similarity	NPD5177	Phase 3
0.7365	Intermediate Similarity	NPD7472	Approved
0.7362	Intermediate Similarity	NPD6959	Discontinued
0.7355	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7266	Discontinued
0.7351	Intermediate Similarity	NPD5763	Approved
0.7351	Intermediate Similarity	NPD5762	Approved
0.7345	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD8651	Approved
0.7321	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3892	Phase 2
0.731	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1512	Approved
0.7297	Intermediate Similarity	NPD2238	Phase 2
0.7284	Intermediate Similarity	NPD4055	Discovery
0.7267	Intermediate Similarity	NPD4663	Approved
0.7251	Intermediate Similarity	NPD8054	Approved
0.7251	Intermediate Similarity	NPD8053	Approved
0.7246	Intermediate Similarity	NPD7157	Approved
0.7244	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4624	Approved
0.7234	Intermediate Similarity	NPD4626	Approved
0.7229	Intermediate Similarity	NPD27	Approved
0.7229	Intermediate Similarity	NPD2489	Approved
0.7226	Intermediate Similarity	NPD7124	Phase 2
0.7225	Intermediate Similarity	NPD7906	Approved
0.7222	Intermediate Similarity	NPD6696	Suspended
0.7219	Intermediate Similarity	NPD6797	Phase 2
0.7214	Intermediate Similarity	NPD3091	Approved
0.7212	Intermediate Similarity	NPD3051	Approved
0.7208	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7819	Suspended
0.7197	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5494	Approved
0.7193	Intermediate Similarity	NPD4577	Approved
0.7193	Intermediate Similarity	NPD4578	Approved
0.719	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7680	Approved
0.7181	Intermediate Similarity	NPD1558	Phase 1
0.7181	Intermediate Similarity	NPD4140	Approved
0.7179	Intermediate Similarity	NPD7041	Phase 2
0.7179	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7251	Discontinued
0.7169	Intermediate Similarity	NPD2970	Approved
0.7169	Intermediate Similarity	NPD2969	Approved
0.7162	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5109	Approved
0.7162	Intermediate Similarity	NPD5110	Phase 2
0.7162	Intermediate Similarity	NPD5111	Phase 2
0.7161	Intermediate Similarity	NPD5241	Discontinued
0.7161	Intermediate Similarity	NPD6190	Approved
0.7161	Intermediate Similarity	NPD2677	Approved
0.716	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7843	Approved
0.7153	Intermediate Similarity	NPD5327	Phase 3
0.7152	Intermediate Similarity	NPD4536	Approved
0.7152	Intermediate Similarity	NPD6111	Discontinued
0.7152	Intermediate Similarity	NPD4538	Approved
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8127	Discontinued
0.7152	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3060	Approved
0.7135	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7808	Phase 3
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7134	Intermediate Similarity	NPD2533	Approved
0.7134	Intermediate Similarity	NPD2534	Approved
0.7134	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7447	Phase 1
0.7134	Intermediate Similarity	NPD2532	Approved
0.7133	Intermediate Similarity	NPD1091	Approved
0.7133	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5124	Phase 1
0.7125	Intermediate Similarity	NPD4678	Approved
0.7125	Intermediate Similarity	NPD4675	Approved
0.7111	Intermediate Similarity	NPD2684	Approved
0.7108	Intermediate Similarity	NPD7229	Phase 3
0.7105	Intermediate Similarity	NPD1510	Phase 2
0.7097	Intermediate Similarity	NPD3750	Approved
0.7093	Intermediate Similarity	NPD7311	Approved
0.7093	Intermediate Similarity	NPD7310	Approved
0.7093	Intermediate Similarity	NPD7313	Approved
0.7093	Intermediate Similarity	NPD7312	Approved
0.7086	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5090	Approved
0.7081	Intermediate Similarity	NPD5089	Approved
0.7076	Intermediate Similarity	NPD6559	Discontinued
0.7073	Intermediate Similarity	NPD7075	Discontinued
0.7073	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4357	Discontinued
0.707	Intermediate Similarity	NPD7212	Phase 2
0.707	Intermediate Similarity	NPD7213	Phase 3
0.707	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7309	Approved
0.7051	Intermediate Similarity	NPD2219	Phase 1
0.7045	Intermediate Similarity	NPD940	Approved
0.7045	Intermediate Similarity	NPD846	Approved
0.7042	Intermediate Similarity	NPD1357	Approved
0.7042	Intermediate Similarity	NPD5691	Approved
0.7032	Intermediate Similarity	NPD1652	Phase 2
0.7029	Intermediate Similarity	NPD7635	Approved
0.7025	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5536	Phase 2
0.702	Intermediate Similarity	NPD230	Phase 1
0.7014	Intermediate Similarity	NPD422	Phase 1
0.7007	Intermediate Similarity	NPD6584	Phase 3
0.7006	Intermediate Similarity	NPD3787	Discontinued
0.7	Intermediate Similarity	NPD6671	Approved
0.6993	Remote Similarity	NPD5960	Phase 3
0.6993	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5588	Approved
0.6993	Remote Similarity	NPD5126	Approved
0.6993	Remote Similarity	NPD6516	Phase 2
0.6993	Remote Similarity	NPD5125	Phase 3
0.6993	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3095	Discontinued
0.6993	Remote Similarity	NPD5846	Approved
0.6987	Remote Similarity	NPD6331	Phase 2
0.6987	Remote Similarity	NPD8166	Discontinued
0.6986	Remote Similarity	NPD1283	Approved
0.698	Remote Similarity	NPD7095	Approved
0.6974	Remote Similarity	NPD1607	Approved
0.6974	Remote Similarity	NPD6353	Approved
0.697	Remote Similarity	NPD7832	Clinical (unspecified phase)

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