NPASS Compound

Structure

CID286347 OpenBabel06191716092D 45 50 0 0 1 0 0 0 0 0999 V2000 4.4990 0.4568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0230 -1.0870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5275 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0373 0.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -0.4902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6981 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5471 2.4510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0943 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9433 1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2452 1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9433 2.4510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7924 2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2452 2.4510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5471 -2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8490 -0.4902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5471 -1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0943 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 0.9804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 0.9804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 3.9216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6414 2.4510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 -2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 6 34 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 33 1 0 0 0 0 13 35 1 0 0 0 0 14 16 1 0 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 15 34 1 0 0 0 0 16 36 1 0 0 0 0 17 36 1 0 0 0 0 18 20 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 34 1 0 0 0 0 20 36 1 6 0 0 0 21 32 1 0 0 0 0 21 33 1 1 0 0 0 22 33 1 1 0 0 0 22 35 1 0 0 0 0 23 32 1 0 0 0 0 23 44 1 1 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 37 1 1 0 0 0 25 27 1 0 0 0 0 25 38 1 6 0 0 0 26 29 1 0 0 0 0 26 39 1 6 0 0 0 27 28 1 1 0 0 0 27 45 1 0 0 0 0 28 40 2 0 0 0 0 28 41 1 0 0 0 0 29 44 1 1 0 0 0 29 45 1 0 0 0 0 30 42 2 0 0 0 0 30 43 1 0 0 0 0 33 5 1 1 0 0 0 34 35 1 1 0 0 0 35 7 1 1 0 0 0 36 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	632.39
Volume:	651.076
LogP:	5.236
LogD:	4.087
LogS:	-3.623
# Rotatable Bonds:	4
TPSA:	153.75
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	5.219
Fsp3:	0.889
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:	-5.918
MDCK Permeability:	7.97697612142656e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.657

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	91.22904205322266%
Volume Distribution (VD):	0.469
Pgp-substrate:	8.068020820617676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.409
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.522
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.271
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.056
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	0.876
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.037
Carcinogencity:	0.099
Eye Corrosion:	0.004
Eye Irritation:	0.025
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC286347

Natural Product ID:	NPC286347
*Common Name:**	Silphioside F
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms:
Standard InCHIKey:	IUCHKMAZAWJNBJ-RCYXVVTDSA-N
Standard InCHI:	InChI=1S/C36H56O9/c1-31(2)14-16-36(30(42)43)17-15-34(6)19(20(36)18-31)8-9-22-33(5)12-11-23(32(3,4)21(33)10-13-35(22,34)7)44-29-26(39)24(37)25(38)27(45-29)28(40)41/h8,20-27,29,37-39H,9-18H2,1-7H3,(H,40,41)(H,42,43)/t20-,21-,22+,23-,24-,25-,26+,27-,29+,33-,34+,35+,36-/m0/s1
SMILES:	O[C@@H]1[C@@H](O)[C@@H](O[C@@H]([C@H]1O)C(=O)O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446866
PubChem CID:	176079
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11430011]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	antarctic	n.a.	PMID[15270575]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387648]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[25442304]
NPO33325	silphium laciniatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26287548]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[26434122]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33118348]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8321	Allium chinense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14123	Achyranthes fauriei	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8321	Allium chinense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14123	Achyranthes fauriei	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14258	Herba alternantherae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29602	Daiswa yunnanensis	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30617	Kochia scoparia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8321	Allium chinense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8321	Allium chinense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14123	Achyranthes fauriei	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23189	Achyranthes japonica	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26884	Helichrysum davenportii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9554	Parthenium ligulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26109	Pilocarpus spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18292	Guarea trichilioides	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26135	Walsura tubulata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24378	Osmanthus heterophyllus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25583	Beta vulgaris	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8494	Pteris longipes	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26408	Melanophryniscus moreirae	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26678	Calea pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10387	Mandragora vernalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3346	Piper sanctum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3067	Frullania nisquallensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26453	Prunus lusitanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25741	Aster ageratoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11845	Petrorhagia dubia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15071	Lissoclinum perforatum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26430	Aplysina laevis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25849	Streptomyces lomondensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26563	Alectoria japonica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26026	Vitis silvestris	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25793	Gremmeniella abietina	Species	Helotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26289	Lecidella chodati	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13781	Eremostachys moluccelloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6196	Aralia armata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26377	Amelanchier vulgaris	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26903	Plectranthus purpuratus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2344	Carlina acanthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8321	Allium chinense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26186	Stereocaulon leprocauloides	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4520	Allium macrostemon	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26754	Stevia connata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26213	Tephrosia vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26244	Panax papyrifer	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10373	Senna pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO137	Nepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25952	Lastrea thelypteris	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25997	Senecio rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25873	Thaminophyllum multiflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8750	Lychnis githago	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7214	Bufotes viridis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19823	Vicia benghalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26625	Stichopus chloronotus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11459	Parmelia formosana	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26053	Pluchea suaveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10972	Lysimachia patungensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25926	Tephrosia pumila	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26352	Heuchera cylindrica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1620	Dictyopteris prolifera	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27377	Diaporthe helianthi	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26078	Mussaenda parviflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26727	Eremocarpus setiger	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26980	Halocarpus biformis	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26535	Balanus glandula	Species	Balanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO773	Siphonaria maura	Species	Chytriomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	5
Others	21

Activity Type	# Activity
Cell Line	22
NON-MOLECULAR	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	6000.0	nM	PMID[528916]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11330.0	nM	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	87.5	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	11.6	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.2	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.7	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	52.0	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	46.0	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	1.3	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.8	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	14.0	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	54.9	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	45.9	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	24.3	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	29.7	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	35.1	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	17.0	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	47.1	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	50.4	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	99.9	%	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio	=	6.14	n.a.	PMID[528917]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio	=	0.821	n.a.	PMID[528917]
NPT3469	Organism	Biomphalaria glabrata	Biomphalaria glabrata	Activity	=	2.0	ppm	PMID[528915]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11880.0	nM	PMID[528917]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18000.0	nM	PMID[528917]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13340.0	nM	PMID[528917]

☑ 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 NPC286347 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	282
0.1-0.2	1947
0.2-0.3	5383
0.3-0.4	10205
0.4-0.5	11150
0.5-0.6	6944
0.6-0.7	3888
0.7-0.8	1900
0.8-0.85	420
0.85-0.9	120
0.9-0.95	336
0.95-1	122

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC114441
0.9908	High Similarity	NPC35405
0.9908	High Similarity	NPC39211
0.9908	High Similarity	NPC469945
0.9908	High Similarity	NPC11551
0.9908	High Similarity	NPC475171
0.9908	High Similarity	NPC208381
0.9908	High Similarity	NPC157868
0.9908	High Similarity	NPC473884
0.9908	High Similarity	NPC472949
0.9908	High Similarity	NPC180550
0.9908	High Similarity	NPC214484
0.9908	High Similarity	NPC309780
0.9908	High Similarity	NPC6377
0.9907	High Similarity	NPC224121
0.9818	High Similarity	NPC294112
0.973	High Similarity	NPC62725
0.973	High Similarity	NPC75417
0.973	High Similarity	NPC171544
0.973	High Similarity	NPC301449
0.973	High Similarity	NPC64715
0.973	High Similarity	NPC22956
0.973	High Similarity	NPC222580
0.973	High Similarity	NPC31193
0.973	High Similarity	NPC159309
0.973	High Similarity	NPC11242
0.973	High Similarity	NPC86222
0.973	High Similarity	NPC297263
0.973	High Similarity	NPC223301
0.973	High Similarity	NPC31838
0.973	High Similarity	NPC114484
0.973	High Similarity	NPC104372
0.973	High Similarity	NPC242840
0.9643	High Similarity	NPC475591
0.9643	High Similarity	NPC471965
0.9643	High Similarity	NPC236870
0.9643	High Similarity	NPC4749
0.9643	High Similarity	NPC249848
0.9643	High Similarity	NPC80986
0.9643	High Similarity	NPC40775
0.9643	High Similarity	NPC187290
0.9643	High Similarity	NPC235438
0.9643	High Similarity	NPC21691
0.9643	High Similarity	NPC213952
0.9643	High Similarity	NPC10607
0.9643	High Similarity	NPC162574
0.9643	High Similarity	NPC107966
0.964	High Similarity	NPC118440
0.964	High Similarity	NPC236657
0.9558	High Similarity	NPC200049
0.9558	High Similarity	NPC30735
0.9558	High Similarity	NPC202666
0.9558	High Similarity	NPC257211
0.9558	High Similarity	NPC262199
0.9558	High Similarity	NPC258617
0.9558	High Similarity	NPC2370
0.9558	High Similarity	NPC44716
0.9558	High Similarity	NPC471961
0.9558	High Similarity	NPC302543
0.9558	High Similarity	NPC235405
0.9558	High Similarity	NPC471964
0.9558	High Similarity	NPC281148
0.9558	High Similarity	NPC14617
0.9558	High Similarity	NPC283417
0.9554	High Similarity	NPC302887
0.9554	High Similarity	NPC187618
0.955	High Similarity	NPC192791
0.9474	High Similarity	NPC33068
0.9474	High Similarity	NPC471963
0.9474	High Similarity	NPC470477
0.9474	High Similarity	NPC471962
0.9474	High Similarity	NPC247315
0.9474	High Similarity	NPC160452
0.9469	High Similarity	NPC275343
0.9469	High Similarity	NPC131469
0.9469	High Similarity	NPC313110
0.9444	High Similarity	NPC31839
0.9391	High Similarity	NPC469947
0.9391	High Similarity	NPC285091
0.9391	High Similarity	NPC470218
0.9391	High Similarity	NPC475368
0.9391	High Similarity	NPC284449
0.9391	High Similarity	NPC181066
0.9386	High Similarity	NPC478066
0.9364	High Similarity	NPC475633
0.9358	High Similarity	NPC48249
0.9358	High Similarity	NPC80843
0.9358	High Similarity	NPC1046
0.9352	High Similarity	NPC242611
0.9304	High Similarity	NPC23275
0.9286	High Similarity	NPC109588
0.9279	High Similarity	NPC37134
0.9279	High Similarity	NPC291903
0.9273	High Similarity	NPC238935
0.9273	High Similarity	NPC475208
0.9266	High Similarity	NPC191763
0.9259	High Similarity	NPC167383
0.9259	High Similarity	NPC306746
0.9259	High Similarity	NPC204407
0.9259	High Similarity	NPC237503
0.9259	High Similarity	NPC57362
0.9231	High Similarity	NPC470475
0.9196	High Similarity	NPC300419
0.9196	High Similarity	NPC475119
0.9196	High Similarity	NPC473824
0.9189	High Similarity	NPC164389
0.9189	High Similarity	NPC475486
0.9182	High Similarity	NPC128925
0.9182	High Similarity	NPC256798
0.9182	High Similarity	NPC116794
0.9182	High Similarity	NPC100383
0.9182	High Similarity	NPC46388
0.9182	High Similarity	NPC37739
0.9174	High Similarity	NPC164194
0.9174	High Similarity	NPC68419
0.9174	High Similarity	NPC476883
0.9174	High Similarity	NPC476885
0.9174	High Similarity	NPC102914
0.9174	High Similarity	NPC199457
0.9174	High Similarity	NPC476884
0.9174	High Similarity	NPC127056
0.9174	High Similarity	NPC476887
0.9174	High Similarity	NPC136877
0.9174	High Similarity	NPC56713
0.9174	High Similarity	NPC270667
0.9174	High Similarity	NPC108709
0.9174	High Similarity	NPC476886
0.9174	High Similarity	NPC110139
0.9174	High Similarity	NPC59804
0.9174	High Similarity	NPC475296
0.9174	High Similarity	NPC476881
0.9174	High Similarity	NPC174679
0.9174	High Similarity	NPC274507
0.9174	High Similarity	NPC29069
0.9174	High Similarity	NPC474589
0.9174	High Similarity	NPC7870
0.9174	High Similarity	NPC279554
0.9174	High Similarity	NPC476882
0.9174	High Similarity	NPC75747
0.9174	High Similarity	NPC90856
0.9174	High Similarity	NPC476880
0.9167	High Similarity	NPC177246
0.9167	High Similarity	NPC476123
0.9167	High Similarity	NPC284807
0.9167	High Similarity	NPC28198
0.9153	High Similarity	NPC477196
0.9115	High Similarity	NPC232237
0.9115	High Similarity	NPC105800
0.9107	High Similarity	NPC305267
0.9107	High Similarity	NPC288205
0.9107	High Similarity	NPC51465
0.9107	High Similarity	NPC26626
0.9107	High Similarity	NPC75287
0.9107	High Similarity	NPC476992
0.9099	High Similarity	NPC189884
0.9099	High Similarity	NPC271138
0.9099	High Similarity	NPC204458
0.9099	High Similarity	NPC47063
0.9099	High Similarity	NPC138334
0.9099	High Similarity	NPC269315
0.9091	High Similarity	NPC179434
0.9091	High Similarity	NPC235841
0.9091	High Similarity	NPC108748
0.9091	High Similarity	NPC297208
0.9091	High Similarity	NPC164419
0.9091	High Similarity	NPC30397
0.9091	High Similarity	NPC211798
0.9091	High Similarity	NPC473481
0.9083	High Similarity	NPC127853
0.9083	High Similarity	NPC137917
0.9076	High Similarity	NPC477197
0.9074	High Similarity	NPC283849
0.9074	High Similarity	NPC473538
0.9068	High Similarity	NPC477192
0.9068	High Similarity	NPC477078
0.9068	High Similarity	NPC477191
0.9068	High Similarity	NPC475281
0.9068	High Similarity	NPC477075
0.9068	High Similarity	NPC329923
0.9068	High Similarity	NPC470476
0.9068	High Similarity	NPC477194
0.9068	High Similarity	NPC477193
0.9035	High Similarity	NPC25663
0.9035	High Similarity	NPC51564
0.9035	High Similarity	NPC207738
0.9035	High Similarity	NPC135849
0.9027	High Similarity	NPC470876
0.9027	High Similarity	NPC8524
0.9027	High Similarity	NPC323359
0.9027	High Similarity	NPC286457
0.9027	High Similarity	NPC123522
0.9027	High Similarity	NPC33012
0.9027	High Similarity	NPC85154
0.9027	High Similarity	NPC69811
0.9027	High Similarity	NPC220160
0.9027	High Similarity	NPC475514
0.9027	High Similarity	NPC475209
0.9027	High Similarity	NPC104137
0.9027	High Similarity	NPC309223
0.9027	High Similarity	NPC102505

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 NPC286347 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	2249
0.2-0.3	3838
0.3-0.4	1775
0.4-0.5	587
0.5-0.6	260
0.6-0.7	131
0.7-0.8	41
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9558	High Similarity	NPD8328	Phase 3
0.9545	High Similarity	NPD8295	Clinical (unspecified phase)
0.8571	High Similarity	NPD8132	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7736	Approved
0.8065	Intermediate Similarity	NPD8293	Discontinued
0.7937	Intermediate Similarity	NPD7319	Approved
0.7886	Intermediate Similarity	NPD6370	Approved
0.784	Intermediate Similarity	NPD7507	Approved
0.7815	Intermediate Similarity	NPD8133	Approved
0.7805	Intermediate Similarity	NPD8517	Approved
0.7805	Intermediate Similarity	NPD8513	Phase 3
0.7805	Intermediate Similarity	NPD8516	Approved
0.7805	Intermediate Similarity	NPD8515	Approved
0.776	Intermediate Similarity	NPD7492	Approved
0.7759	Intermediate Similarity	NPD6412	Phase 2
0.7724	Intermediate Similarity	NPD6059	Approved
0.7724	Intermediate Similarity	NPD6319	Approved
0.7724	Intermediate Similarity	NPD6054	Approved
0.7698	Intermediate Similarity	NPD6616	Approved
0.7692	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6686	Approved
0.7679	Intermediate Similarity	NPD7902	Approved
0.7638	Intermediate Similarity	NPD7078	Approved
0.7583	Intermediate Similarity	NPD8297	Approved
0.7583	Intermediate Similarity	NPD6882	Approved
0.7568	Intermediate Similarity	NPD7748	Approved
0.752	Intermediate Similarity	NPD6016	Approved
0.752	Intermediate Similarity	NPD6015	Approved
0.748	Intermediate Similarity	NPD6009	Approved
0.7479	Intermediate Similarity	NPD6373	Approved
0.7479	Intermediate Similarity	NPD6372	Approved
0.746	Intermediate Similarity	NPD5988	Approved
0.744	Intermediate Similarity	NPD8294	Approved
0.744	Intermediate Similarity	NPD8377	Approved
0.7411	Intermediate Similarity	NPD7900	Approved
0.7411	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7515	Phase 2
0.7381	Intermediate Similarity	NPD8379	Approved
0.7381	Intermediate Similarity	NPD8335	Approved
0.7381	Intermediate Similarity	NPD8296	Approved
0.7381	Intermediate Similarity	NPD8378	Approved
0.7381	Intermediate Similarity	NPD8033	Approved
0.7381	Intermediate Similarity	NPD8380	Approved
0.7373	Intermediate Similarity	NPD6402	Approved
0.7373	Intermediate Similarity	NPD6675	Approved
0.7373	Intermediate Similarity	NPD7128	Approved
0.7373	Intermediate Similarity	NPD5739	Approved
0.7355	Intermediate Similarity	NPD6649	Approved
0.7355	Intermediate Similarity	NPD6650	Approved
0.728	Intermediate Similarity	NPD7328	Approved
0.728	Intermediate Similarity	NPD7327	Approved
0.725	Intermediate Similarity	NPD7320	Approved
0.725	Intermediate Similarity	NPD6899	Approved
0.725	Intermediate Similarity	NPD6881	Approved
0.7236	Intermediate Similarity	NPD4632	Approved
0.7222	Intermediate Similarity	NPD7516	Approved
0.7213	Intermediate Similarity	NPD8130	Phase 1
0.7176	Intermediate Similarity	NPD6033	Approved
0.7167	Intermediate Similarity	NPD5701	Approved
0.7167	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6883	Approved
0.7131	Intermediate Similarity	NPD7290	Approved
0.7131	Intermediate Similarity	NPD7102	Approved
0.7109	Intermediate Similarity	NPD6921	Approved
0.7109	Intermediate Similarity	NPD7503	Approved
0.708	Intermediate Similarity	NPD8034	Phase 2
0.708	Intermediate Similarity	NPD8035	Phase 2
0.708	Intermediate Similarity	NPD6411	Approved
0.7073	Intermediate Similarity	NPD6869	Approved
0.7073	Intermediate Similarity	NPD6847	Approved
0.7073	Intermediate Similarity	NPD6617	Approved
0.7073	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6013	Approved
0.7049	Intermediate Similarity	NPD6014	Approved
0.7049	Intermediate Similarity	NPD6012	Approved
0.7	Intermediate Similarity	NPD7604	Phase 2
0.6992	Remote Similarity	NPD4634	Approved
0.6977	Remote Similarity	NPD5983	Phase 2
0.697	Remote Similarity	NPD8074	Phase 3
0.6967	Remote Similarity	NPD6011	Approved
0.6935	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7115	Discovery
0.6903	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6101	Approved
0.6894	Remote Similarity	NPD6336	Discontinued
0.687	Remote Similarity	NPD6399	Phase 3
0.6864	Remote Similarity	NPD7638	Approved
0.6807	Remote Similarity	NPD7640	Approved
0.6807	Remote Similarity	NPD7639	Approved
0.6783	Remote Similarity	NPD7983	Approved
0.678	Remote Similarity	NPD6083	Phase 2
0.678	Remote Similarity	NPD4755	Approved
0.678	Remote Similarity	NPD6084	Phase 2
0.6774	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7645	Phase 2
0.6742	Remote Similarity	NPD6067	Discontinued
0.6724	Remote Similarity	NPD5778	Approved
0.6724	Remote Similarity	NPD5779	Approved
0.6723	Remote Similarity	NPD4225	Approved
0.672	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6274	Approved
0.6696	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4697	Phase 3
0.6692	Remote Similarity	NPD7100	Approved
0.6692	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6615	Remote Similarity	NPD6335	Approved
0.6609	Remote Similarity	NPD5328	Approved
0.6591	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6908	Approved
0.6591	Remote Similarity	NPD6909	Approved
0.6589	Remote Similarity	NPD6868	Approved
0.6583	Remote Similarity	NPD5696	Approved
0.6579	Remote Similarity	NPD3573	Approved
0.6557	Remote Similarity	NPD5226	Approved
0.6557	Remote Similarity	NPD4633	Approved
0.6557	Remote Similarity	NPD5224	Approved
0.6557	Remote Similarity	NPD5211	Phase 2
0.6557	Remote Similarity	NPD5225	Approved
0.6555	Remote Similarity	NPD5222	Approved
0.6555	Remote Similarity	NPD5221	Approved
0.6555	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD8080	Discontinued
0.6538	Remote Similarity	NPD6317	Approved
0.6532	Remote Similarity	NPD4768	Approved
0.6532	Remote Similarity	NPD4767	Approved
0.6522	Remote Similarity	NPD5737	Approved
0.6522	Remote Similarity	NPD6672	Approved
0.6504	Remote Similarity	NPD5175	Approved
0.6504	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD5173	Approved
0.6496	Remote Similarity	NPD6079	Approved
0.6491	Remote Similarity	NPD3618	Phase 1
0.6489	Remote Similarity	NPD6313	Approved
0.6489	Remote Similarity	NPD6314	Approved
0.648	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5223	Approved
0.6471	Remote Similarity	NPD5695	Phase 3
0.6466	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5141	Approved
0.6449	Remote Similarity	NPD5956	Approved
0.6444	Remote Similarity	NPD8299	Approved
0.6444	Remote Similarity	NPD8342	Approved
0.6444	Remote Similarity	NPD8341	Approved
0.6444	Remote Similarity	NPD8340	Approved
0.6441	Remote Similarity	NPD8171	Discontinued
0.6429	Remote Similarity	NPD4729	Approved
0.6429	Remote Similarity	NPD4730	Approved
0.6417	Remote Similarity	NPD7839	Suspended
0.6412	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6698	Approved
0.641	Remote Similarity	NPD46	Approved
0.6408	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD8451	Approved
0.6383	Remote Similarity	NPD8415	Approved
0.6379	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD4754	Approved
0.6358	Remote Similarity	NPD7799	Discontinued
0.635	Remote Similarity	NPD8448	Approved
0.6349	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD8391	Approved
0.6331	Remote Similarity	NPD8392	Approved
0.6331	Remote Similarity	NPD8390	Approved
0.6328	Remote Similarity	NPD5250	Approved
0.6328	Remote Similarity	NPD5247	Approved
0.6328	Remote Similarity	NPD5251	Approved
0.6328	Remote Similarity	NPD5248	Approved
0.6328	Remote Similarity	NPD5249	Phase 3
0.6316	Remote Similarity	NPD4786	Approved
0.6304	Remote Similarity	NPD8336	Approved
0.6304	Remote Similarity	NPD8337	Approved
0.6299	Remote Similarity	NPD5128	Approved
0.629	Remote Similarity	NPD7632	Discontinued
0.6286	Remote Similarity	NPD7260	Phase 2
0.6283	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD7829	Approved
0.625	Remote Similarity	NPD6333	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD7830	Approved
0.625	Remote Similarity	NPD6334	Approved
0.6241	Remote Similarity	NPD7641	Discontinued
0.6241	Remote Similarity	NPD8338	Approved
0.6228	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD3669	Approved
0.6222	Remote Similarity	NPD8444	Approved
0.6212	Remote Similarity	NPD6940	Discontinued
0.6207	Remote Similarity	NPD5330	Approved
0.6207	Remote Similarity	NPD6409	Approved
0.6207	Remote Similarity	NPD6684	Approved
0.6207	Remote Similarity	NPD7521	Approved
0.6207	Remote Similarity	NPD7146	Approved
0.6207	Remote Similarity	NPD6098	Approved
0.6207	Remote Similarity	NPD7334	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data