NPASS Compound

Structure

CID76128 OpenBabel06191715412D 32 35 0 0 1 0 0 0 0 0999 V2000 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 30 1 0 0 0 0 3 8 2 0 0 0 0 3 10 1 0 0 0 0 4 8 1 0 0 0 0 4 12 2 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 13 2 0 0 0 0 7 23 1 0 0 0 0 9 30 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 31 1 0 0 0 0 14 7 1 6 0 0 0 14 18 1 0 0 0 0 14 32 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 17 25 2 0 0 0 0 18 20 1 0 0 0 0 18 26 1 1 0 0 0 19 27 2 0 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 31 1 6 0 0 0 22 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.12
Volume:	421.653
LogP:	1.945
LogD:	1.507
LogS:	-4.747
# Rotatable Bonds:	4
TPSA:	162.98
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	3.854
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.024
MDCK Permeability:	1.631777013244573e-05
Pgp-inhibitor:	0.699
Pgp-substrate:	0.815
Human Intestinal Absorption (HIA):	0.82
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	85.9957046508789%
Volume Distribution (VD):	0.673
Pgp-substrate:	4.407368183135986%

ADMET: Metabolism

CYP1A2-inhibitor:	0.329
CYP1A2-substrate:	0.176
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.122
CYP2D6-inhibitor:	0.131
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.184
CYP3A4-substrate:	0.093

ADMET: Excretion

Clearance (CL):	7.284
Half-life (T1/2):	0.241

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.895
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.08
Carcinogencity:	0.365
Eye Corrosion:	0.003
Eye Irritation:	0.506
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC76128

Natural Product ID:	NPC76128
*Common Name:**	Physcion-1-O-D-Glucoside
IUPAC Name:	1-hydroxy-6-methoxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	POMKXWCJRHNLRP-DQMLXFRHSA-N
Standard InCHI:	InChI=1S/C22H22O10/c1-8-3-10-15(12(24)4-8)19(27)16-11(17(10)25)5-9(30-2)6-13(16)31-22-21(29)20(28)18(26)14(7-23)32-22/h3-6,14,18,20-24,26,28-29H,7H2,1-2H3/t14-,18-,20+,21-,22-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(OC)cc3c2C(=O)c2c(C3=O)cc(cc2O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518860
PubChem CID:	168938
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/jo00051a050]
NPO2508	Selaginella delicatula	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843573]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978210]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087602]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11454355]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932124]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15730265]
NPO8819	Nepeta parnassica	Species	Lamiaceae	Eukaryota	aerial parts	Mt. Parnassos, Greece	n.a.	PMID[18393463]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19012276]
NPO397	Thymelaea hirsuta	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19284745]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO19996	Caulerpa peltata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25593390]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	Flowers	Johor, Malaysia		PMID[26399961]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	Flowers	Kelantan, Malaysia		PMID[26399961]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	Flowers	Pahang, Malaysia		PMID[26399961]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	Aerial Parts	n.a.	n.a.	PMID[28581290]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29517220]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3417561]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2228	Photinia serratifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3980	Frangula purshiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27140	Amanita phalloides	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19050	Garcinia polyantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13754	Tanacetum coccineum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26899	Cheilanthes argentea	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19037	Senecio praecox	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13716	Aconitum tasiromontanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2508	Selaginella delicatula	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12108	Aizopsis selskiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26972	Baccharis potosina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9448	Dictyopteris australis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19671	Dipsacus azureus	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17822	Fridericia triplinervia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3214	Lavandula vera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18287	Penicillium bilaiae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24629	Achromobacter denitrificans	Species	Alcaligenaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1501	Senecio subdentatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27564	Stevia berlandieri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17856	Anaphalis lactea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3980	Frangula purshiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22675	Helichrysum chionosphaerum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4367	Actinobacillus equuli	Species	Pasteurellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27454	Turbo cornutus	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13246	Pinalia stricta	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14217	Adansonia grandidieri	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21112	Chaetomium carinthiacum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27790	Delia arenicola	Species	Anthomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20560	Polyporus betulinus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15422	Carduus tenuiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9105	Polygonum hypoleucum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10359	Chaiturus marrubiastrum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13754	Tanacetum coccineum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19512	Gleichenia quadripartita	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26393.1	Petunia integrifolia subsp. inflata	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15472	Oryctes monoceros	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18144	Metrodorea nigra	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8819	Nepeta parnassica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22526	Justicia secunda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10239	Magnolia figo	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16572	Rhododendron dahuricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11749	Eria mollis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19818	Jacquemontia paniculata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4071	Cytisus uniflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO624	Isaria fumosorosea	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6079	Adalia bipunctata	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4997	Xerochrysum viscosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10216	Leptocereus quadricostatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19050	Garcinia polyantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19395	Nepeta granatensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8576	Cissus rheifolia	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19996	Caulerpa peltata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13403	Gadus morhua callarias	Species	Gadidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO986	Rattus rattus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20625	Delphinium virgatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20223	Rosa pomifera	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20422	Albizia myriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14412	Aphyllocladus denticulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20844	Sphaerella rosigena	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14932.1	Dalbergia lanceolaria subsp. paniculata	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27873	Ravenia spectabilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21376	Lupinus corymbosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20753	Grangea maderaspatana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO397	Thymelaea hirsuta	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7573	Psidium araca	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27164	Aspergillus alliaceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27737	Penicillium shearii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26899	Cheilanthes argentea	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8605	Xalocoa ocellata	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21564	Senecio behnii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4132	Cranfillia fluviatilis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18867	Stephanitis takeyai	Species	Tingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16142	Verbascum thapsiforme	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27140	Amanita phalloides	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10688	Flacourtia jangomas	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2228	Photinia serratifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20353	Degenia velebitica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16590	Cytophaga hutchinsoni	Species	Cytophagaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4345	Caulocystis cephalornithos	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24407	Bipolaris heveae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8386	Enceliopsis argophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17568	Balanophora laxiflora	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4437	Hymenoxys lemmoni	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14248	Mandragora autumnalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13421	Sphaerella laricina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2631	Aster sedifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2198	Rivularia firma	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14800	Oophaga granulifera	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19913	Rhynchophorus ferrugineus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19232	Anchusa azurea	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12252	Psychotria stachyoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13523	Neobalanocarpus heimii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14104	Dendriopoterium menendezii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13454	Amphorogyne spicata	Species	Amphorogynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4158	Hymenoxys lemmonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9752	Miliusa velutina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20947	Tagetes filifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	<	50.0	%	PMID[512035]

☑ 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 NPC76128 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	412
0.1-0.2	1639
0.2-0.3	3452
0.3-0.4	8102
0.4-0.5	9598
0.5-0.6	4720
0.6-0.7	5087
0.7-0.8	5723
0.8-0.85	3014
0.85-0.9	850
0.9-0.95	77
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC271385
1.0	High Similarity	NPC111536
1.0	High Similarity	NPC5029
1.0	High Similarity	NPC30432
0.9877	High Similarity	NPC68381
0.9816	High Similarity	NPC46958
0.9816	High Similarity	NPC475246
0.9816	High Similarity	NPC475233
0.9755	High Similarity	NPC3718
0.9752	High Similarity	NPC222455
0.9697	High Similarity	NPC114257
0.9697	High Similarity	NPC277710
0.9697	High Similarity	NPC299149
0.9697	High Similarity	NPC212290
0.9697	High Similarity	NPC153578
0.9693	High Similarity	NPC98776
0.9691	High Similarity	NPC298778
0.9639	High Similarity	NPC477860
0.9639	High Similarity	NPC475161
0.9634	High Similarity	NPC146803
0.963	High Similarity	NPC259905
0.9627	High Similarity	NPC178851
0.9573	High Similarity	NPC472054
0.9515	High Similarity	NPC474345
0.9467	High Similarity	NPC87583
0.9455	High Similarity	NPC213052
0.9455	High Similarity	NPC85368
0.9455	High Similarity	NPC199357
0.9441	High Similarity	NPC278329
0.9441	High Similarity	NPC146837
0.9441	High Similarity	NPC212099
0.9441	High Similarity	NPC101116
0.9412	High Similarity	NPC105591
0.9405	High Similarity	NPC315221
0.9398	High Similarity	NPC470454
0.9398	High Similarity	NPC199533
0.9349	High Similarity	NPC313452
0.9325	High Similarity	NPC178281
0.9321	High Similarity	NPC216752
0.9281	High Similarity	NPC63105
0.9273	High Similarity	NPC473202
0.9235	High Similarity	NPC473717
0.9235	High Similarity	NPC475662
0.9235	High Similarity	NPC293227
0.9235	High Similarity	NPC473631
0.9231	High Similarity	NPC245059
0.9231	High Similarity	NPC84494
0.9222	High Similarity	NPC203751
0.9207	High Similarity	NPC478022
0.9207	High Similarity	NPC478020
0.9198	High Similarity	NPC472320
0.9193	High Similarity	NPC23817
0.9176	High Similarity	NPC470448
0.9176	High Similarity	NPC164047
0.9176	High Similarity	NPC470453
0.9176	High Similarity	NPC470452
0.9136	High Similarity	NPC73511
0.913	High Similarity	NPC261866
0.9128	High Similarity	NPC473686
0.9128	High Similarity	NPC475220
0.9128	High Similarity	NPC221140
0.9128	High Similarity	NPC229817
0.9128	High Similarity	NPC475352
0.9112	High Similarity	NPC289876
0.9112	High Similarity	NPC102053
0.9096	High Similarity	NPC63470
0.9096	High Similarity	NPC477502
0.9096	High Similarity	NPC249977
0.9091	High Similarity	NPC7752
0.9085	High Similarity	NPC131745
0.9085	High Similarity	NPC44947
0.9085	High Similarity	NPC259834
0.908	High Similarity	NPC271479
0.908	High Similarity	NPC314672
0.908	High Similarity	NPC470810
0.9074	High Similarity	NPC313163
0.9074	High Similarity	NPC161749
0.9074	High Similarity	NPC197896
0.9074	High Similarity	NPC258035
0.9074	High Similarity	NPC156457
0.9068	High Similarity	NPC470603
0.9068	High Similarity	NPC470604
0.9068	High Similarity	NPC470605
0.9068	High Similarity	NPC99233
0.9064	High Similarity	NPC208069
0.9062	High Similarity	NPC40356
0.9062	High Similarity	NPC154683
0.9042	High Similarity	NPC229687
0.903	High Similarity	NPC66087
0.903	High Similarity	NPC257566
0.903	High Similarity	NPC183672
0.903	High Similarity	NPC179198
0.903	High Similarity	NPC124155
0.903	High Similarity	NPC278419
0.9024	High Similarity	NPC303913
0.9024	High Similarity	NPC47923
0.9018	High Similarity	NPC308265
0.9012	High Similarity	NPC208152
0.9012	High Similarity	NPC78492
0.9012	High Similarity	NPC170475
0.9012	High Similarity	NPC206378
0.9012	High Similarity	NPC45165
0.9006	High Similarity	NPC106625
0.9006	High Similarity	NPC268950
0.9006	High Similarity	NPC211158
0.9006	High Similarity	NPC108706
0.9006	High Similarity	NPC78021
0.9006	High Similarity	NPC87304
0.9006	High Similarity	NPC58538
0.9	High Similarity	NPC470569
0.8988	High Similarity	NPC241874
0.8988	High Similarity	NPC44558
0.8988	High Similarity	NPC105511
0.8988	High Similarity	NPC478021
0.8988	High Similarity	NPC76047
0.8988	High Similarity	NPC78734
0.8988	High Similarity	NPC150767
0.8988	High Similarity	NPC224462
0.8982	High Similarity	NPC229729
0.8982	High Similarity	NPC45400
0.8982	High Similarity	NPC474024
0.8977	High Similarity	NPC314459
0.8977	High Similarity	NPC470199
0.8976	High Similarity	NPC165720
0.897	High Similarity	NPC190450
0.897	High Similarity	NPC473043
0.897	High Similarity	NPC127782
0.897	High Similarity	NPC300537
0.8963	High Similarity	NPC328093
0.8963	High Similarity	NPC470358
0.8957	High Similarity	NPC177742
0.8957	High Similarity	NPC6985
0.8957	High Similarity	NPC470606
0.8957	High Similarity	NPC43638
0.8953	High Similarity	NPC85316
0.8953	High Similarity	NPC197357
0.8951	High Similarity	NPC95090
0.8951	High Similarity	NPC169248
0.8951	High Similarity	NPC27408
0.8951	High Similarity	NPC72649
0.8951	High Similarity	NPC97052
0.8951	High Similarity	NPC39351
0.8951	High Similarity	NPC26195
0.8944	High Similarity	NPC259767
0.8944	High Similarity	NPC259182
0.8944	High Similarity	NPC88484
0.8944	High Similarity	NPC121001
0.8941	High Similarity	NPC108202
0.8941	High Similarity	NPC470667
0.8941	High Similarity	NPC186800
0.8938	High Similarity	NPC147735
0.8938	High Similarity	NPC202595
0.8938	High Similarity	NPC470568
0.8935	High Similarity	NPC260263
0.8935	High Similarity	NPC48773
0.8935	High Similarity	NPC205076
0.8935	High Similarity	NPC256760
0.8935	High Similarity	NPC294501
0.8935	High Similarity	NPC307518
0.8929	High Similarity	NPC470206
0.8929	High Similarity	NPC470207
0.8929	High Similarity	NPC246274
0.8929	High Similarity	NPC472383
0.8929	High Similarity	NPC472381
0.8929	High Similarity	NPC191653
0.8929	High Similarity	NPC183036
0.8922	High Similarity	NPC236934
0.8922	High Similarity	NPC5778
0.8922	High Similarity	NPC70441
0.8922	High Similarity	NPC178173
0.892	High Similarity	NPC264302
0.8916	High Similarity	NPC284960
0.8916	High Similarity	NPC168822
0.8916	High Similarity	NPC243930
0.8916	High Similarity	NPC29830
0.8916	High Similarity	NPC19709
0.8916	High Similarity	NPC309025
0.8916	High Similarity	NPC88023
0.8916	High Similarity	NPC222936
0.8916	High Similarity	NPC88043
0.8914	High Similarity	NPC205721
0.8908	High Similarity	NPC241847
0.8902	High Similarity	NPC43761
0.8902	High Similarity	NPC324736
0.8902	High Similarity	NPC470607
0.8902	High Similarity	NPC85121
0.8896	High Similarity	NPC127406
0.8889	High Similarity	NPC83283
0.8889	High Similarity	NPC143851
0.8889	High Similarity	NPC312630
0.8889	High Similarity	NPC469405
0.8889	High Similarity	NPC324220
0.8889	High Similarity	NPC29763
0.8889	High Similarity	NPC39360
0.8889	High Similarity	NPC210003
0.8882	High Similarity	NPC172033
0.8882	High Similarity	NPC175230
0.8882	High Similarity	NPC168789
0.8882	High Similarity	NPC25724
0.8882	High Similarity	NPC154986

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 NPC76128 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	929
0.2-0.3	1797
0.3-0.4	2637
0.4-0.5	1873
0.5-0.6	977
0.6-0.7	366
0.7-0.8	131
0.8-0.85	55
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9074	High Similarity	NPD4381	Clinical (unspecified phase)
0.8882	High Similarity	NPD6559	Discontinued
0.8857	High Similarity	NPD7879	Clinical (unspecified phase)
0.8817	High Similarity	NPD7804	Clinical (unspecified phase)
0.8795	High Similarity	NPD6959	Discontinued
0.8765	High Similarity	NPD7074	Phase 3
0.8757	High Similarity	NPD3818	Discontinued
0.8706	High Similarity	NPD7054	Approved
0.8704	High Similarity	NPD4380	Phase 2
0.8671	High Similarity	NPD8312	Approved
0.8671	High Similarity	NPD8313	Approved
0.8655	High Similarity	NPD7472	Approved
0.8605	High Similarity	NPD6797	Phase 2
0.8555	High Similarity	NPD7251	Discontinued
0.8545	High Similarity	NPD2393	Clinical (unspecified phase)
0.8545	High Similarity	NPD7819	Suspended
0.8521	High Similarity	NPD6232	Discontinued
0.8516	High Similarity	NPD6776	Approved
0.8516	High Similarity	NPD6779	Approved
0.8516	High Similarity	NPD6782	Approved
0.8516	High Similarity	NPD6778	Approved
0.8516	High Similarity	NPD6780	Approved
0.8516	High Similarity	NPD6777	Approved
0.8516	High Similarity	NPD6781	Approved
0.8506	High Similarity	NPD4338	Clinical (unspecified phase)
0.8506	High Similarity	NPD7808	Phase 3
0.8503	High Similarity	NPD7075	Discontinued
0.8488	Intermediate Similarity	NPD5844	Phase 1
0.848	Intermediate Similarity	NPD7473	Discontinued
0.8449	Intermediate Similarity	NPD8151	Discontinued
0.8443	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6166	Phase 2
0.8421	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD7435	Discontinued
0.8373	Intermediate Similarity	NPD1934	Approved
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7411	Suspended
0.828	Intermediate Similarity	NPD7698	Approved
0.828	Intermediate Similarity	NPD7696	Phase 3
0.828	Intermediate Similarity	NPD7697	Approved
0.8263	Intermediate Similarity	NPD6801	Discontinued
0.8242	Intermediate Similarity	NPD6534	Approved
0.8242	Intermediate Similarity	NPD6535	Approved
0.8235	Intermediate Similarity	NPD7871	Phase 2
0.8235	Intermediate Similarity	NPD7870	Phase 2
0.8218	Intermediate Similarity	NPD3751	Discontinued
0.8201	Intermediate Similarity	NPD7701	Phase 2
0.8193	Intermediate Similarity	NPD3226	Approved
0.8187	Intermediate Similarity	NPD5494	Approved
0.8171	Intermediate Similarity	NPD2534	Approved
0.8171	Intermediate Similarity	NPD2533	Approved
0.8171	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD2532	Approved
0.8171	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD1549	Phase 2
0.8128	Intermediate Similarity	NPD6823	Phase 2
0.8122	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD7874	Approved
0.8114	Intermediate Similarity	NPD7228	Approved
0.8108	Intermediate Similarity	NPD7700	Phase 2
0.8108	Intermediate Similarity	NPD7699	Phase 2
0.8107	Intermediate Similarity	NPD2801	Approved
0.8103	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD7801	Approved
0.8073	Intermediate Similarity	NPD7783	Phase 2
0.8073	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD5402	Approved
0.8047	Intermediate Similarity	NPD37	Approved
0.8036	Intermediate Similarity	NPD6599	Discontinued
0.8023	Intermediate Similarity	NPD6234	Discontinued
0.8012	Intermediate Similarity	NPD4965	Approved
0.8012	Intermediate Similarity	NPD4967	Phase 2
0.8012	Intermediate Similarity	NPD4966	Approved
0.8012	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD1465	Phase 2
0.7989	Intermediate Similarity	NPD6213	Phase 3
0.7989	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6212	Phase 3
0.7989	Intermediate Similarity	NPD3787	Discontinued
0.7965	Intermediate Similarity	NPD3749	Approved
0.7953	Intermediate Similarity	NPD3817	Phase 2
0.7947	Intermediate Similarity	NPD8320	Phase 1
0.7947	Intermediate Similarity	NPD8319	Approved
0.7907	Intermediate Similarity	NPD7768	Phase 2
0.7901	Intermediate Similarity	NPD2796	Approved
0.7892	Intermediate Similarity	NPD6799	Approved
0.7892	Intermediate Similarity	NPD7390	Discontinued
0.7892	Intermediate Similarity	NPD1511	Approved
0.7857	Intermediate Similarity	NPD5403	Approved
0.7853	Intermediate Similarity	NPD2346	Discontinued
0.784	Intermediate Similarity	NPD1510	Phase 2
0.7829	Intermediate Similarity	NPD7199	Phase 2
0.7826	Intermediate Similarity	NPD1607	Approved
0.7818	Intermediate Similarity	NPD4628	Phase 3
0.7818	Intermediate Similarity	NPD3750	Approved
0.7814	Intermediate Similarity	NPD8150	Discontinued
0.7805	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1512	Approved
0.7791	Intermediate Similarity	NPD8455	Phase 2
0.7772	Intermediate Similarity	NPD7584	Approved
0.7765	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7458	Discontinued
0.776	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD5401	Approved
0.7735	Intermediate Similarity	NPD7240	Approved
0.7711	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1240	Approved
0.7684	Intermediate Similarity	NPD5710	Approved
0.7684	Intermediate Similarity	NPD5711	Approved
0.7651	Intermediate Similarity	NPD6674	Discontinued
0.7651	Intermediate Similarity	NPD2800	Approved
0.7651	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5953	Discontinued
0.7576	Intermediate Similarity	NPD1551	Phase 2
0.7576	Intermediate Similarity	NPD2935	Discontinued
0.7576	Intermediate Similarity	NPD6099	Approved
0.7576	Intermediate Similarity	NPD6100	Approved
0.7541	Intermediate Similarity	NPD7685	Pre-registration
0.7529	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8434	Phase 2
0.7524	Intermediate Similarity	NPD8059	Phase 3
0.7524	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3926	Phase 2
0.7442	Intermediate Similarity	NPD920	Approved
0.7427	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2799	Discontinued
0.7377	Intermediate Similarity	NPD7286	Phase 2
0.7374	Intermediate Similarity	NPD7585	Approved
0.7365	Intermediate Similarity	NPD5408	Approved
0.7365	Intermediate Similarity	NPD5404	Approved
0.7365	Intermediate Similarity	NPD5405	Approved
0.7365	Intermediate Similarity	NPD5406	Approved
0.7362	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1243	Approved
0.7333	Intermediate Similarity	NPD1247	Approved
0.7326	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7583	Approved
0.7321	Intermediate Similarity	NPD2344	Approved
0.732	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8285	Discontinued
0.7318	Intermediate Similarity	NPD919	Approved
0.7312	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4625	Phase 3
0.7293	Intermediate Similarity	NPD7229	Phase 3
0.7292	Intermediate Similarity	NPD4360	Phase 2
0.7292	Intermediate Similarity	NPD4363	Phase 3
0.7289	Intermediate Similarity	NPD6651	Approved
0.7283	Intermediate Similarity	NPD6273	Approved
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1470	Approved
0.7256	Intermediate Similarity	NPD2313	Discontinued
0.7256	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7930	Approved
0.7239	Intermediate Similarity	NPD4908	Phase 1
0.7235	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD230	Phase 1
0.7228	Intermediate Similarity	NPD7177	Discontinued
0.7219	Intermediate Similarity	NPD7266	Discontinued
0.7209	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7003	Approved
0.7172	Intermediate Similarity	NPD7680	Approved
0.7151	Intermediate Similarity	NPD2309	Approved
0.7151	Intermediate Similarity	NPD6190	Approved
0.7126	Intermediate Similarity	NPD1933	Approved
0.7117	Intermediate Similarity	NPD2798	Approved
0.7115	Intermediate Similarity	NPD8366	Approved
0.7101	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5760	Phase 2
0.7095	Intermediate Similarity	NPD5761	Phase 2
0.7083	Intermediate Similarity	NPD4287	Approved
0.7079	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4060	Phase 1
0.7053	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8127	Discontinued
0.7048	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7097	Phase 1
0.7039	Intermediate Similarity	NPD6844	Discontinued
0.7033	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6832	Phase 2

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