NPASS Compound

Structure

CID122809 OpenBabel06191715482D 40 44 0 0 1 0 0 0 0 0999 V2000 -5.1486 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0147 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0147 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8807 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6845 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2826 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0646 -2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1486 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8807 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6845 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4166 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2826 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5506 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 3.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5506 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 2.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6456 1.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 1.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6456 4.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8736 -3.1915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7467 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6845 4.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4166 4.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 3.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 -2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -2.1970 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 0.0475 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4166 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 11 2 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 5 14 1 0 0 0 0 6 13 1 0 0 0 0 6 17 2 0 0 0 0 7 15 1 0 0 0 0 7 16 2 0 0 0 0 8 27 1 0 0 0 0 9 26 1 0 0 0 0 9 28 1 0 0 0 0 10 26 1 0 0 0 0 10 36 1 0 0 0 0 11 16 1 0 0 0 0 12 29 1 0 0 0 0 13 37 1 0 0 0 0 14 19 2 0 0 0 0 14 30 1 0 0 0 0 15 19 1 0 0 0 0 15 31 2 0 0 0 0 16 38 1 0 0 0 0 17 19 1 0 0 0 0 17 38 1 0 0 0 0 18 8 1 6 0 0 0 18 20 1 0 0 0 0 18 39 1 0 0 0 0 20 21 1 0 0 0 0 20 32 1 1 0 0 0 21 22 1 0 0 0 0 21 33 1 6 0 0 0 22 24 1 0 0 0 0 22 40 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 6 0 0 0 23 34 1 0 0 0 0 24 37 1 6 0 0 0 24 39 1 0 0 0 0 25 36 1 0 0 0 0 25 40 1 1 0 0 0 26 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	564.15
Volume:	517.441
LogP:	0.769
LogD:	-0.091
LogS:	-4.013
# Rotatable Bonds:	7
TPSA:	228.97
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.164
Synthetic Accessibility Score:	4.627
Fsp3:	0.423
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:	-6.407
MDCK Permeability:	1.210079062730074e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.897
20% Bioavailability (F20%):	0.279
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	86.08834838867188%
Volume Distribution (VD):	0.585
Pgp-substrate:	11.748308181762695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.05
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	1.404
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.431
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.671
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.805
Carcinogencity:	0.384
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC122809

Natural Product ID:	NPC122809
*Common Name:**	Apiin
IUPAC Name:	7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	NTDLXWMIWOECHG-YRCFQSNFSA-N
Standard InCHI:	InChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21+,22-,23+,24-,25+,26-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1OC[C@]([C@H]1O)(O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1535342
PubChem CID:	5280746
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	callus	n.a.	PMID[10552648]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350171]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762792]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO12907	Hypericum carinatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921431]
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	Green Island, Taiwan	2002-MAY	PMID[16180809]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17268112]
NPO6365	Pachychalina alcaloidifera	Species	Niphatidae	Eukaryota	n.a.	Brazilian	n.a.	PMID[17346073]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18214349]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19778086]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	leaves	n.a.	n.a.	PMID[20634065]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24895781]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	flower buds	n.a.	n.a.	PMID[25987378]
NPO6879	Laetia corymbulosa	Species	Salicaceae	Eukaryota	Bark	n.a.	n.a.	PMID[28290698]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[6893493]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[6893493]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf Wax	n.a.	n.a.	Database[FooDB]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17203	Impatiens siculifer	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12656	Holarrhena febrifuga	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO6879	Laetia corymbulosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17203	Impatiens siculifer	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12656	Holarrhena febrifuga	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13840	Streptomyces incarnatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1763	Rabdosia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8830	Crotalaria orixensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26387	Linum crispum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26501	Palafoxia texana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6365	Pachychalina alcaloidifera	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28772	Polygonum mite	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17743	Solanum aculeatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25071	Aspergillus albus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20602	Trichomanes reniforme	Species	Hymenophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17203	Impatiens siculifer	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25444	Christisonia bicolor	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21533	Smilax bracteata	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12656	Holarrhena febrifuga	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11665	Kloeckera brevis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10235	Castanopsis eyrei	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8710	Licaria brasiliensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22782	Lens culinaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO832	Pseudocinchona pachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2352	Tynanthus panurensis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21477	Euryops rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20180	Rabdosia loxothyrsa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12907	Hypericum carinatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1420	Tenebrio obscurus	Species	Tenebrionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25123	Scutellaria sieberi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26056	Atroxima liberica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19748	Aspergillus phoenicis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20253	Eucalyptus decorticans	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1068	Platytaenia lasiocarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6879	Laetia corymbulosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	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
NPO26721	NPC122809	Other	n.a.	111	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO22782	NPC122809	Raw	n.a.	0.620000005	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO26721	NPC122809	Raw	n.a.	8.370000203	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

☑ 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	2
Potency	7

Activity Type	# Activity
Cell Line	1
Individual Protein	6
Organism	2
PROTEIN COMPLEX	2
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[453358]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	501.2	nM	PMID[453359]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	707.9	nM	PMID[453359]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	145.8	nM	PMID[453359]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[453359]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	22387.2	nM	PMID[453359]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PMID[453359]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	69.17	%	PMID[453360]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	141.47	%	PMID[453360]
NPT22689	PROTEIN COMPLEX	Programmed cell death protein 1/Programmed cell death 1 ligand 1	Homo sapiens	IC50	>	100000.0	nM	PMID[453361]

☑ 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 NPC122809 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	420
0.1-0.2	1627
0.2-0.3	3489
0.3-0.4	8863
0.4-0.5	10046
0.5-0.6	4707
0.6-0.7	5964
0.7-0.8	5697
0.8-0.85	1167
0.85-0.9	558
0.9-0.95	156
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC265480
0.98	High Similarity	NPC149368
0.9799	High Similarity	NPC29763
0.9799	High Similarity	NPC143851
0.9799	High Similarity	NPC83283
0.9799	High Similarity	NPC210003
0.9799	High Similarity	NPC39360
0.9739	High Similarity	NPC150164
0.9737	High Similarity	NPC200708
0.9733	High Similarity	NPC95090
0.9733	High Similarity	NPC27408
0.9669	High Similarity	NPC203500
0.9669	High Similarity	NPC307938
0.9669	High Similarity	NPC323593
0.9613	High Similarity	NPC72016
0.9605	High Similarity	NPC54802
0.9605	High Similarity	NPC135391
0.9605	High Similarity	NPC156457
0.9605	High Similarity	NPC197304
0.9605	High Similarity	NPC78263
0.9605	High Similarity	NPC44931
0.9605	High Similarity	NPC313163
0.9605	High Similarity	NPC473512
0.9605	High Similarity	NPC108831
0.9605	High Similarity	NPC129827
0.9605	High Similarity	NPC133671
0.9605	High Similarity	NPC197896
0.9605	High Similarity	NPC65003
0.9605	High Similarity	NPC60966
0.9605	High Similarity	NPC161749
0.9605	High Similarity	NPC288084
0.9605	High Similarity	NPC182634
0.9605	High Similarity	NPC77672
0.9605	High Similarity	NPC258035
0.9603	High Similarity	NPC97052
0.9603	High Similarity	NPC72649
0.9603	High Similarity	NPC169248
0.9603	High Similarity	NPC26195
0.9603	High Similarity	NPC39351
0.96	High Similarity	NPC259767
0.96	High Similarity	NPC88484
0.96	High Similarity	NPC259182
0.96	High Similarity	NPC121001
0.9542	High Similarity	NPC22062
0.9542	High Similarity	NPC138811
0.9542	High Similarity	NPC473634
0.9542	High Similarity	NPC41121
0.9542	High Similarity	NPC472459
0.9542	High Similarity	NPC111929
0.9542	High Similarity	NPC320283
0.9542	High Similarity	NPC73511
0.9539	High Similarity	NPC206378
0.9539	High Similarity	NPC261866
0.9539	High Similarity	NPC170475
0.9536	High Similarity	NPC106625
0.9481	High Similarity	NPC187379
0.9481	High Similarity	NPC136761
0.9481	High Similarity	NPC304741
0.9481	High Similarity	NPC473623
0.9481	High Similarity	NPC471079
0.9481	High Similarity	NPC470405
0.9474	High Similarity	NPC99233
0.9467	High Similarity	NPC191154
0.9423	High Similarity	NPC121703
0.9423	High Similarity	NPC183672
0.9419	High Similarity	NPC470125
0.9419	High Similarity	NPC473438
0.9419	High Similarity	NPC276377
0.9419	High Similarity	NPC270675
0.9419	High Similarity	NPC135846
0.9419	High Similarity	NPC477628
0.9419	High Similarity	NPC215710
0.9419	High Similarity	NPC224530
0.9419	High Similarity	NPC216496
0.9419	High Similarity	NPC210961
0.9419	High Similarity	NPC159579
0.9419	High Similarity	NPC64305
0.9419	High Similarity	NPC249281
0.9419	High Similarity	NPC181465
0.9419	High Similarity	NPC47923
0.9419	High Similarity	NPC170052
0.9419	High Similarity	NPC246943
0.9419	High Similarity	NPC303913
0.9419	High Similarity	NPC472994
0.9419	High Similarity	NPC173582
0.9419	High Similarity	NPC139320
0.9419	High Similarity	NPC282169
0.9419	High Similarity	NPC476215
0.9419	High Similarity	NPC477629
0.9419	High Similarity	NPC116458
0.9419	High Similarity	NPC101636
0.9419	High Similarity	NPC265885
0.9419	High Similarity	NPC253788
0.9419	High Similarity	NPC297987
0.9419	High Similarity	NPC85707
0.9419	High Similarity	NPC259957
0.9419	High Similarity	NPC195685
0.9419	High Similarity	NPC48093
0.9419	High Similarity	NPC163242
0.9419	High Similarity	NPC129217
0.9416	High Similarity	NPC470607
0.9416	High Similarity	NPC308265
0.9412	High Similarity	NPC295613
0.9412	High Similarity	NPC45165
0.9412	High Similarity	NPC473657
0.9412	High Similarity	NPC127406
0.9404	High Similarity	NPC23253
0.9404	High Similarity	NPC134819
0.9359	High Similarity	NPC77660
0.9359	High Similarity	NPC475382
0.9359	High Similarity	NPC189142
0.9359	High Similarity	NPC27942
0.9359	High Similarity	NPC240306
0.9359	High Similarity	NPC44947
0.9359	High Similarity	NPC298171
0.9359	High Similarity	NPC131745
0.9355	High Similarity	NPC472320
0.9355	High Similarity	NPC97285
0.9355	High Similarity	NPC271479
0.9355	High Similarity	NPC153342
0.9355	High Similarity	NPC142860
0.9355	High Similarity	NPC246469
0.9355	High Similarity	NPC271270
0.9351	High Similarity	NPC6985
0.9351	High Similarity	NPC43638
0.9351	High Similarity	NPC470606
0.9351	High Similarity	NPC23817
0.9333	High Similarity	NPC199335
0.9313	High Similarity	NPC235575
0.9313	High Similarity	NPC245452
0.9299	High Similarity	NPC473644
0.9299	High Similarity	NPC309025
0.9299	High Similarity	NPC257566
0.9299	High Similarity	NPC124155
0.9299	High Similarity	NPC311850
0.9299	High Similarity	NPC88023
0.9299	High Similarity	NPC270335
0.9299	High Similarity	NPC179198
0.9299	High Similarity	NPC243930
0.9299	High Similarity	NPC66087
0.9299	High Similarity	NPC191306
0.9299	High Similarity	NPC19709
0.9299	High Similarity	NPC168822
0.9299	High Similarity	NPC80068
0.9299	High Similarity	NPC278419
0.929	High Similarity	NPC104677
0.929	High Similarity	NPC43761
0.9286	High Similarity	NPC17521
0.9281	High Similarity	NPC211158
0.9281	High Similarity	NPC87304
0.9281	High Similarity	NPC78021
0.9281	High Similarity	NPC268950
0.9281	High Similarity	NPC108706
0.9267	High Similarity	NPC23084
0.9241	High Similarity	NPC139060
0.9241	High Similarity	NPC289667
0.9241	High Similarity	NPC292929
0.9241	High Similarity	NPC287889
0.9241	High Similarity	NPC205824
0.9241	High Similarity	NPC277205
0.9241	High Similarity	NPC85751
0.9241	High Similarity	NPC22832
0.9241	High Similarity	NPC311830
0.9241	High Similarity	NPC19240
0.9241	High Similarity	NPC76831
0.9241	High Similarity	NPC129264
0.9241	High Similarity	NPC135358
0.9236	High Similarity	NPC93215
0.9236	High Similarity	NPC259834
0.9236	High Similarity	NPC472876
0.9236	High Similarity	NPC190450
0.9236	High Similarity	NPC473043
0.9221	High Similarity	NPC470605
0.9221	High Similarity	NPC470604
0.9221	High Similarity	NPC470603
0.9211	High Similarity	NPC106025
0.9211	High Similarity	NPC477240
0.9211	High Similarity	NPC213723
0.9211	High Similarity	NPC214454
0.9193	High Similarity	NPC261254
0.9182	High Similarity	NPC298666
0.9182	High Similarity	NPC186816
0.9182	High Similarity	NPC203145
0.9182	High Similarity	NPC256188
0.9182	High Similarity	NPC210073
0.9182	High Similarity	NPC253662
0.9182	High Similarity	NPC308404
0.9182	High Similarity	NPC262222
0.9182	High Similarity	NPC32641
0.9182	High Similarity	NPC8856
0.9182	High Similarity	NPC179950
0.9182	High Similarity	NPC274618
0.9182	High Similarity	NPC118284
0.9182	High Similarity	NPC145038
0.9182	High Similarity	NPC89809
0.9182	High Similarity	NPC254306
0.9182	High Similarity	NPC64425
0.9182	High Similarity	NPC276222
0.9182	High Similarity	NPC11432
0.9182	High Similarity	NPC221342

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 NPC122809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	844
0.2-0.3	1725
0.3-0.4	2733
0.4-0.5	2093
0.5-0.6	987
0.6-0.7	263
0.7-0.8	123
0.8-0.85	14
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD4381	Clinical (unspecified phase)
0.9125	High Similarity	NPD3818	Discontinued
0.9068	High Similarity	NPD7054	Approved
0.9068	High Similarity	NPD7804	Clinical (unspecified phase)
0.9012	High Similarity	NPD7472	Approved
0.8961	High Similarity	NPD4380	Phase 2
0.8957	High Similarity	NPD6797	Phase 2
0.8902	High Similarity	NPD7251	Discontinued
0.8896	High Similarity	NPD7074	Phase 3
0.8848	High Similarity	NPD4338	Clinical (unspecified phase)
0.8848	High Similarity	NPD7808	Phase 3
0.8675	High Similarity	NPD6559	Discontinued
0.8667	High Similarity	NPD1550	Clinical (unspecified phase)
0.8667	High Similarity	NPD1552	Clinical (unspecified phase)
0.8609	High Similarity	NPD1549	Phase 2
0.8526	High Similarity	NPD5403	Approved
0.8509	High Similarity	NPD7075	Discontinued
0.8491	Intermediate Similarity	NPD6801	Discontinued
0.8491	Intermediate Similarity	NPD1934	Approved
0.8438	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6166	Phase 2
0.8424	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD5401	Approved
0.8397	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD1511	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7411	Suspended
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8272	Intermediate Similarity	NPD5402	Approved
0.8272	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD3817	Phase 2
0.8235	Intermediate Similarity	NPD2796	Approved
0.8228	Intermediate Similarity	NPD1512	Approved
0.8221	Intermediate Similarity	NPD3882	Suspended
0.8221	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD3749	Approved
0.8026	Intermediate Similarity	NPD1240	Approved
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.7988	Intermediate Similarity	NPD7819	Suspended
0.7964	Intermediate Similarity	NPD5494	Approved
0.7946	Intermediate Similarity	NPD7584	Approved
0.7922	Intermediate Similarity	NPD1607	Approved
0.7921	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6959	Discontinued
0.7911	Intermediate Similarity	NPD3750	Approved
0.7911	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3751	Discontinued
0.7882	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3787	Discontinued
0.7861	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD8312	Approved
0.7829	Intermediate Similarity	NPD8313	Approved
0.7791	Intermediate Similarity	NPD1653	Approved
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7771	Intermediate Similarity	NPD8455	Phase 2
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7685	Pre-registration
0.7707	Intermediate Similarity	NPD7033	Discontinued
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.7679	Intermediate Similarity	NPD7768	Phase 2
0.7673	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1091	Approved
0.7644	Intermediate Similarity	NPD5844	Phase 1
0.7625	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2800	Approved
0.7622	Intermediate Similarity	NPD6780	Approved
0.7622	Intermediate Similarity	NPD6777	Approved
0.7622	Intermediate Similarity	NPD6782	Approved
0.7622	Intermediate Similarity	NPD920	Approved
0.7622	Intermediate Similarity	NPD6776	Approved
0.7622	Intermediate Similarity	NPD6781	Approved
0.7622	Intermediate Similarity	NPD6779	Approved
0.7622	Intermediate Similarity	NPD6778	Approved
0.7607	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3748	Approved
0.7593	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7228	Approved
0.7571	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1465	Phase 2
0.7558	Intermediate Similarity	NPD6232	Discontinued
0.7554	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7473	Discontinued
0.7526	Intermediate Similarity	NPD7585	Approved
0.7516	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD1243	Approved
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7474	Intermediate Similarity	NPD7583	Approved
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.7452	Intermediate Similarity	NPD1613	Approved
0.7452	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1203	Approved
0.7444	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7417	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7783	Phase 2
0.7409	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7696	Phase 3
0.7407	Intermediate Similarity	NPD1652	Phase 2
0.7407	Intermediate Similarity	NPD7697	Approved
0.7407	Intermediate Similarity	NPD7698	Approved
0.7405	Intermediate Similarity	NPD5124	Phase 1
0.7405	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8151	Discontinued
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2344	Approved
0.7384	Intermediate Similarity	NPD919	Approved
0.7383	Intermediate Similarity	NPD1548	Phase 1
0.7368	Intermediate Similarity	NPD7871	Phase 2
0.7368	Intermediate Similarity	NPD7870	Phase 2
0.736	Intermediate Similarity	NPD5953	Discontinued
0.7358	Intermediate Similarity	NPD6651	Approved
0.7354	Intermediate Similarity	NPD6823	Phase 2
0.7351	Intermediate Similarity	NPD6535	Approved
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.7351	Intermediate Similarity	NPD6534	Approved
0.7345	Intermediate Similarity	NPD7286	Phase 2
0.7344	Intermediate Similarity	NPD7701	Phase 2
0.7329	Intermediate Similarity	NPD2935	Discontinued
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7321	Intermediate Similarity	NPD7458	Discontinued
0.7314	Intermediate Similarity	NPD3926	Phase 2
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7308	Intermediate Similarity	NPD4908	Phase 1
0.7299	Intermediate Similarity	NPD1247	Approved
0.729	Intermediate Similarity	NPD2798	Approved
0.7284	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD3225	Approved
0.7273	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7874	Approved
0.7234	Intermediate Similarity	NPD7700	Phase 2
0.7234	Intermediate Similarity	NPD7699	Phase 2
0.7233	Intermediate Similarity	NPD943	Approved
0.7231	Intermediate Similarity	NPD7801	Approved
0.7228	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7240	Approved
0.7222	Intermediate Similarity	NPD6100	Approved
0.7222	Intermediate Similarity	NPD6099	Approved
0.7215	Intermediate Similarity	NPD6798	Discontinued
0.7215	Intermediate Similarity	NPD3268	Approved
0.7215	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2309	Approved
0.7212	Intermediate Similarity	NPD6190	Approved
0.7197	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2654	Approved
0.719	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD1610	Phase 2
0.717	Intermediate Similarity	NPD6233	Phase 2
0.716	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD9717	Approved
0.7135	Intermediate Similarity	NPD4287	Approved
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7134	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4361	Phase 2
0.7121	Intermediate Similarity	NPD7930	Approved
0.7118	Intermediate Similarity	NPD3226	Approved
0.7115	Intermediate Similarity	NPD2797	Approved
0.7099	Intermediate Similarity	NPD7097	Phase 1
0.7098	Intermediate Similarity	NPD8319	Approved
0.7098	Intermediate Similarity	NPD8320	Phase 1
0.7093	Intermediate Similarity	NPD6844	Discontinued
0.7081	Intermediate Similarity	NPD6355	Discontinued
0.7081	Intermediate Similarity	NPD230	Phase 1
0.7066	Intermediate Similarity	NPD5058	Phase 3
0.7062	Intermediate Similarity	NPD5710	Approved
0.7062	Intermediate Similarity	NPD5711	Approved
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7048	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3027	Phase 3
0.7027	Intermediate Similarity	NPD8150	Discontinued
0.7024	Intermediate Similarity	NPD7390	Discontinued
0.7021	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6212	Phase 3
0.7021	Intermediate Similarity	NPD6213	Phase 3
0.7018	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD3764	Approved
0.6983	Remote Similarity	NPD2403	Approved
0.6982	Remote Similarity	NPD4662	Approved
0.6982	Remote Similarity	NPD4661	Approved
0.6975	Remote Similarity	NPD447	Suspended
0.6975	Remote Similarity	NPD1899	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