NPASS Compound

Structure

CID222153 OpenBabel06191716012D 54 57 0 0 1 0 0 0 0 0999 V2000 2.7468 10.5579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4151 5.9517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6847 5.2941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0447 -2.3252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0619 -2.3252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4514 -0.4064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7022 -0.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8851 3.6738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7022 0.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8957 11.0493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0446 10.5579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0446 9.5752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1935 9.0838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1935 8.1010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6576 7.6096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6576 6.6269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5087 6.1355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5087 5.1527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3598 4.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3598 3.6786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2109 3.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2109 2.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0620 1.7131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0620 0.7303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3544 3.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9131 0.2390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8511 1.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3634 0.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8511 -1.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3157 4.0558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0507 2.9168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7858 0.1877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4044 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8511 1.4741 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7858 1.7778 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7022 -0.9828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8511 0.4914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5533 0.4914 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4044 -0.9828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9131 -0.7438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6194 4.9905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5533 -1.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8511 0.4914 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 2.0894 2.7125 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7022 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5533 1.4741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8743 -0.9481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1548 3.0162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8844 6.1294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2555 -1.4741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5807 5.1948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 43 1 0 0 0 0 3 43 1 0 0 0 0 4 44 1 0 0 0 0 5 44 1 0 0 0 0 6 45 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 26 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 42 1 0 0 0 0 27 28 1 0 0 0 0 27 36 1 0 0 0 0 28 39 1 0 0 0 0 29 33 1 0 0 0 0 29 37 1 0 0 0 0 30 34 1 0 0 0 0 30 38 1 0 0 0 0 31 43 1 0 0 0 0 32 47 1 0 0 0 0 33 45 1 0 0 0 0 34 46 1 0 0 0 0 35 40 1 0 0 0 0 35 41 1 0 0 0 0 36 37 1 0 0 0 0 36 45 1 6 0 0 0 37 47 1 1 0 0 0 38 44 1 0 0 0 0 38 48 1 1 0 0 0 39 46 1 1 0 0 0 39 48 1 0 0 0 0 40 48 1 1 0 0 0 40 49 1 0 0 0 0 41 44 1 0 0 0 0 41 53 1 1 0 0 0 42 50 2 0 0 0 0 42 53 1 0 0 0 0 43 54 1 0 0 0 0 45 46 1 1 0 0 0 46 7 1 1 0 0 0 47 8 1 6 0 0 0 47 51 1 0 0 0 0 48 9 1 1 0 0 0 52 54 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	758.64
Volume:	852.006
LogP:	11.375
LogD:	6.26
LogS:	-5.611
# Rotatable Bonds:	23
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.033
Synthetic Accessibility Score:	5.316
Fsp3:	0.938
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.959
MDCK Permeability:	6.915372978255618e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.3
Plasma Protein Binding (PPB):	96.16968536376953%
Volume Distribution (VD):	1.492
Pgp-substrate:	2.1316473484039307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.259
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.977
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.365
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	4.063
Half-life (T1/2):	0.017

ADMET: Toxicity

hERG Blockers:	0.928
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.959
Carcinogencity:	0.042
Eye Corrosion:	0.939
Eye Irritation:	0.446
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC222153

Natural Product ID:	NPC222153
*Common Name:**	Bruguierin C
IUPAC Name:	[(1R,3S,5S,8R,9S,10R,13R,14R,17S)-17-[(E,2S)-6-hydroperoxy-2-hydroxy-6-methylhept-4-en-2-yl]-1-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] octadecanoate
Synonyms:	bruguierin C
Standard InCHIKey:	PNIOLRUIMUJAKL-MZOLOXAHSA-N
Standard InCHI:	InChI=1S/C48H86O6/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-26-42(50)53-41-35-40(49)48(9)38(44(41,4)5)30-34-46(7)39(48)28-27-36-37(29-33-45(36,46)6)47(8,51)32-25-31-43(2,3)54-52/h25,31,36-41,49,51-52H,10-24,26-30,32-35H2,1-9H3/b31-25+/t36-,37+,38+,39+,40-,41+,45-,46-,47+,48+/m1/s1
SMILES:	CCCCCCCCCCCCCCCCCC(=O)O[C@H]1C[C@@H](O)[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@H]2[C@](C/C=C/C(OO)(C)C)(O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503931
PubChem CID:	11629176
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50063a031]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277746]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO33342	Bruguiera gymnorrhiza	Species	Rhizophoraceae	Eukaryota	stems	Xiamen, China	2002-JUN	PMID[15387677]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	PMID[16254827]
NPO33342	Bruguiera gymnorrhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562850]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18179176]
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19835393]
NPO22097	Plakinastrella clathrata	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21261297]
NPO16812	Ajuga bracteosa	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21539300]
NPO9189	Streptomyces atratus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21868221]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25679537]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25901993]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778454]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	Fruiting Bodies	n.a.	n.a.	PMID[29715021]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158166]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8010	Otostegia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4507	Bruguiera gymnorhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11760	Teucrium orientale	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO9189	Streptomyces atratus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15545	Veltheimia viridifolia	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO84	Isoberlinia angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17304	Sipunculus nudus	Species	Sipunculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13789	Paranephelius uniflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22097	Plakinastrella clathrata	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10770	Ptilota pectinata	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14002	Petalostemon purpureum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11408	Podocarpus amarus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17921	Allium monspessulanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16215	Umbilicaria cinereorufescens	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15919	Streptomyces caelestis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16923	Cereus chrysacanthus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17071	Coeloseira pacifica	Species	Champiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17375	Ceramium botryocarpum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28319	Ulva prolifera	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17339	Macaranga sinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4336	Echiochilon pauciflorum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28868	Pardachirus pavoninus	Species	Soleidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17218	Helichrysum nudifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25550	Buchenavia tetraphylla	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16052	Chromodoris obsoleta	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2155	Tephroseris integrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14813	Agaricus silvaticus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15748	Hypoxis nyasica	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16812	Ajuga bracteosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28821	Stichopus horrens	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17844	Agaricus integer	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17602	Arbutus menziesii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13013	Saccharothrix mutabilis	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16695	Fumaria kraliki	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4507	Bruguiera gymnorhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16329	Potebniamyces gallicola	Species	Phacidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7905	Lepista irina	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8010	Otostegia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2550	Trichoderma citrinum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9951	Hyella caespitosa	Species	Hyellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11760	Teucrium orientale	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18073	Justicia trinervia	Species	Acanthaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	15700.0	nM	PMID[520651]

☑ 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 NPC222153 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	194
0.1-0.2	1201
0.2-0.3	4122
0.3-0.4	8778
0.4-0.5	12855
0.5-0.6	5869
0.6-0.7	5503
0.7-0.8	3939
0.8-0.85	210
0.85-0.9	16
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC119036
0.9208	High Similarity	NPC472217
0.9208	High Similarity	NPC472219
0.9208	High Similarity	NPC472218
0.9091	High Similarity	NPC477054
0.9062	High Similarity	NPC279974
0.902	High Similarity	NPC163216
0.899	High Similarity	NPC477051
0.899	High Similarity	NPC477052
0.899	High Similarity	NPC477053
0.8932	High Similarity	NPC472216
0.8932	High Similarity	NPC5475
0.8932	High Similarity	NPC285298
0.8932	High Similarity	NPC284828
0.8932	High Similarity	NPC173905
0.875	High Similarity	NPC257082
0.8738	High Similarity	NPC263729
0.8725	High Similarity	NPC201763
0.8673	High Similarity	NPC84383
0.8667	High Similarity	NPC472215
0.8667	High Similarity	NPC472214
0.8627	High Similarity	NPC36688
0.86	High Similarity	NPC477854
0.8586	High Similarity	NPC471903
0.8558	High Similarity	NPC42847
0.8558	High Similarity	NPC64844
0.8505	High Similarity	NPC470063
0.85	High Similarity	NPC476878
0.85	High Similarity	NPC476879
0.8462	Intermediate Similarity	NPC278628
0.8462	Intermediate Similarity	NPC231530
0.8454	Intermediate Similarity	NPC471896
0.8447	Intermediate Similarity	NPC112009
0.8447	Intermediate Similarity	NPC180204
0.8431	Intermediate Similarity	NPC289670
0.8431	Intermediate Similarity	NPC115899
0.84	Intermediate Similarity	NPC477853
0.84	Intermediate Similarity	NPC54248
0.84	Intermediate Similarity	NPC276103
0.84	Intermediate Similarity	NPC327788
0.8384	Intermediate Similarity	NPC474922
0.8381	Intermediate Similarity	NPC59530
0.8367	Intermediate Similarity	NPC26888
0.8365	Intermediate Similarity	NPC29705
0.8351	Intermediate Similarity	NPC475921
0.8351	Intermediate Similarity	NPC474704
0.835	Intermediate Similarity	NPC22388
0.835	Intermediate Similarity	NPC475558
0.835	Intermediate Similarity	NPC32577
0.835	Intermediate Similarity	NPC155332
0.835	Intermediate Similarity	NPC473788
0.835	Intermediate Similarity	NPC114540
0.835	Intermediate Similarity	NPC476081
0.8333	Intermediate Similarity	NPC266955
0.8333	Intermediate Similarity	NPC251680
0.8333	Intermediate Similarity	NPC167974
0.8333	Intermediate Similarity	NPC94906
0.8317	Intermediate Similarity	NPC253586
0.8317	Intermediate Similarity	NPC108078
0.8304	Intermediate Similarity	NPC41123
0.8304	Intermediate Similarity	NPC145074
0.8304	Intermediate Similarity	NPC114939
0.8302	Intermediate Similarity	NPC94529
0.83	Intermediate Similarity	NPC474727
0.8286	Intermediate Similarity	NPC472655
0.8273	Intermediate Similarity	NPC72772
0.8273	Intermediate Similarity	NPC469794
0.8269	Intermediate Similarity	NPC189588
0.8269	Intermediate Similarity	NPC97487
0.8269	Intermediate Similarity	NPC120321
0.8269	Intermediate Similarity	NPC249187
0.8269	Intermediate Similarity	NPC10232
0.8269	Intermediate Similarity	NPC478057
0.8269	Intermediate Similarity	NPC196471
0.8269	Intermediate Similarity	NPC247957
0.8269	Intermediate Similarity	NPC187302
0.8265	Intermediate Similarity	NPC148414
0.8265	Intermediate Similarity	NPC175628
0.8265	Intermediate Similarity	NPC111585
0.8252	Intermediate Similarity	NPC75941
0.8252	Intermediate Similarity	NPC235142
0.8252	Intermediate Similarity	NPC476897
0.8247	Intermediate Similarity	NPC193360
0.8235	Intermediate Similarity	NPC191565
0.8235	Intermediate Similarity	NPC472028
0.8235	Intermediate Similarity	NPC300179
0.8235	Intermediate Similarity	NPC102426
0.8224	Intermediate Similarity	NPC218853
0.8218	Intermediate Similarity	NPC253115
0.8218	Intermediate Similarity	NPC120708
0.8218	Intermediate Similarity	NPC304899
0.8208	Intermediate Similarity	NPC473173
0.8208	Intermediate Similarity	NPC255387
0.8208	Intermediate Similarity	NPC131665
0.8208	Intermediate Similarity	NPC469318
0.8208	Intermediate Similarity	NPC473284
0.82	Intermediate Similarity	NPC209662
0.82	Intermediate Similarity	NPC159365
0.819	Intermediate Similarity	NPC473543
0.819	Intermediate Similarity	NPC471293
0.8182	Intermediate Similarity	NPC234335
0.8173	Intermediate Similarity	NPC271980
0.8173	Intermediate Similarity	NPC475344
0.8173	Intermediate Similarity	NPC476471
0.8173	Intermediate Similarity	NPC124544
0.8173	Intermediate Similarity	NPC193934
0.8165	Intermediate Similarity	NPC280782
0.8163	Intermediate Similarity	NPC474889
0.8163	Intermediate Similarity	NPC128496
0.8155	Intermediate Similarity	NPC201406
0.8155	Intermediate Similarity	NPC180733
0.8155	Intermediate Similarity	NPC471041
0.8155	Intermediate Similarity	NPC108371
0.8155	Intermediate Similarity	NPC37047
0.8155	Intermediate Similarity	NPC41971
0.8148	Intermediate Similarity	NPC197428
0.8148	Intermediate Similarity	NPC475134
0.8148	Intermediate Similarity	NPC101450
0.8148	Intermediate Similarity	NPC475563
0.8144	Intermediate Similarity	NPC142361
0.8144	Intermediate Similarity	NPC128644
0.8144	Intermediate Similarity	NPC474684
0.8137	Intermediate Similarity	NPC291634
0.8137	Intermediate Similarity	NPC57416
0.8137	Intermediate Similarity	NPC320306
0.8131	Intermediate Similarity	NPC258323
0.8119	Intermediate Similarity	NPC37787
0.8119	Intermediate Similarity	NPC473415
0.8119	Intermediate Similarity	NPC180557
0.8119	Intermediate Similarity	NPC469329
0.8119	Intermediate Similarity	NPC30677
0.8119	Intermediate Similarity	NPC266899
0.8113	Intermediate Similarity	NPC119855
0.8113	Intermediate Similarity	NPC477877
0.8113	Intermediate Similarity	NPC220217
0.8113	Intermediate Similarity	NPC196528
0.8113	Intermediate Similarity	NPC257353
0.81	Intermediate Similarity	NPC86368
0.81	Intermediate Similarity	NPC473690
0.81	Intermediate Similarity	NPC470224
0.81	Intermediate Similarity	NPC471902
0.81	Intermediate Similarity	NPC287118
0.8095	Intermediate Similarity	NPC72151
0.8095	Intermediate Similarity	NPC312900
0.8095	Intermediate Similarity	NPC474124
0.8095	Intermediate Similarity	NPC473523
0.8095	Intermediate Similarity	NPC95899
0.8081	Intermediate Similarity	NPC469400
0.8081	Intermediate Similarity	NPC10274
0.8081	Intermediate Similarity	NPC232202
0.8077	Intermediate Similarity	NPC268829
0.8077	Intermediate Similarity	NPC222875
0.8077	Intermediate Similarity	NPC295110
0.8077	Intermediate Similarity	NPC247701
0.8077	Intermediate Similarity	NPC475617
0.8077	Intermediate Similarity	NPC471412
0.8077	Intermediate Similarity	NPC253886
0.8077	Intermediate Similarity	NPC25177
0.8077	Intermediate Similarity	NPC121218
0.8073	Intermediate Similarity	NPC475480
0.8073	Intermediate Similarity	NPC475668
0.8073	Intermediate Similarity	NPC473921
0.8061	Intermediate Similarity	NPC4309
0.8061	Intermediate Similarity	NPC242864
0.8058	Intermediate Similarity	NPC470068
0.8058	Intermediate Similarity	NPC218107
0.8058	Intermediate Similarity	NPC470066
0.8058	Intermediate Similarity	NPC58942
0.8058	Intermediate Similarity	NPC78427
0.8058	Intermediate Similarity	NPC38471
0.8058	Intermediate Similarity	NPC234617
0.8058	Intermediate Similarity	NPC260149
0.8058	Intermediate Similarity	NPC20479
0.8058	Intermediate Similarity	NPC38296
0.8058	Intermediate Similarity	NPC114274
0.8058	Intermediate Similarity	NPC28864
0.8058	Intermediate Similarity	NPC16911
0.8058	Intermediate Similarity	NPC98837
0.8058	Intermediate Similarity	NPC162459
0.8058	Intermediate Similarity	NPC470067
0.8058	Intermediate Similarity	NPC124703
0.8056	Intermediate Similarity	NPC475065
0.8056	Intermediate Similarity	NPC10064
0.8056	Intermediate Similarity	NPC170221
0.8041	Intermediate Similarity	NPC474970
0.8041	Intermediate Similarity	NPC264127
0.8041	Intermediate Similarity	NPC325594
0.8041	Intermediate Similarity	NPC73038
0.8041	Intermediate Similarity	NPC155011
0.8039	Intermediate Similarity	NPC160056
0.8039	Intermediate Similarity	NPC7124
0.8039	Intermediate Similarity	NPC235053
0.8039	Intermediate Similarity	NPC327179
0.8039	Intermediate Similarity	NPC173272
0.8039	Intermediate Similarity	NPC471777
0.8037	Intermediate Similarity	NPC475294
0.8037	Intermediate Similarity	NPC187435
0.8037	Intermediate Similarity	NPC475781
0.8037	Intermediate Similarity	NPC67321
0.8036	Intermediate Similarity	NPC476959

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 NPC222153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1419
0.2-0.3	3794
0.3-0.4	2457
0.4-0.5	748
0.5-0.6	235
0.6-0.7	212
0.7-0.8	121
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8416	Intermediate Similarity	NPD7638	Approved
0.8333	Intermediate Similarity	NPD7640	Approved
0.8333	Intermediate Similarity	NPD7639	Approved
0.7921	Intermediate Similarity	NPD6399	Phase 3
0.7822	Intermediate Similarity	NPD8034	Phase 2
0.7822	Intermediate Similarity	NPD8035	Phase 2
0.7822	Intermediate Similarity	NPD7637	Suspended
0.7798	Intermediate Similarity	NPD6881	Approved
0.7798	Intermediate Similarity	NPD6899	Approved
0.7778	Intermediate Similarity	NPD6675	Approved
0.7778	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD7128	Approved
0.7778	Intermediate Similarity	NPD5739	Approved
0.7755	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD8130	Phase 1
0.7719	Intermediate Similarity	NPD7115	Discovery
0.7706	Intermediate Similarity	NPD5697	Approved
0.7679	Intermediate Similarity	NPD8297	Approved
0.767	Intermediate Similarity	NPD7748	Approved
0.7664	Intermediate Similarity	NPD7632	Discontinued
0.7658	Intermediate Similarity	NPD6883	Approved
0.7658	Intermediate Similarity	NPD7290	Approved
0.7658	Intermediate Similarity	NPD7102	Approved
0.7653	Intermediate Similarity	NPD4786	Approved
0.7636	Intermediate Similarity	NPD7320	Approved
0.7619	Intermediate Similarity	NPD6083	Phase 2
0.7619	Intermediate Similarity	NPD6084	Phase 2
0.7589	Intermediate Similarity	NPD6617	Approved
0.7589	Intermediate Similarity	NPD6847	Approved
0.7589	Intermediate Similarity	NPD6650	Approved
0.7589	Intermediate Similarity	NPD6869	Approved
0.7589	Intermediate Similarity	NPD6649	Approved
0.7579	Intermediate Similarity	NPD6115	Approved
0.7579	Intermediate Similarity	NPD6697	Approved
0.7579	Intermediate Similarity	NPD6118	Approved
0.7579	Intermediate Similarity	NPD6114	Approved
0.7568	Intermediate Similarity	NPD6372	Approved
0.7568	Intermediate Similarity	NPD6013	Approved
0.7568	Intermediate Similarity	NPD6373	Approved
0.7568	Intermediate Similarity	NPD6012	Approved
0.7568	Intermediate Similarity	NPD6014	Approved
0.7545	Intermediate Similarity	NPD5701	Approved
0.7522	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD7507	Approved
0.7477	Intermediate Similarity	NPD6011	Approved
0.7476	Intermediate Similarity	NPD7515	Phase 2
0.7476	Intermediate Similarity	NPD6079	Approved
0.7459	Intermediate Similarity	NPD7319	Approved
0.7456	Intermediate Similarity	NPD4632	Approved
0.7455	Intermediate Similarity	NPD6008	Approved
0.7453	Intermediate Similarity	NPD7902	Approved
0.7451	Intermediate Similarity	NPD5328	Approved
0.7449	Intermediate Similarity	NPD3667	Approved
0.7423	Intermediate Similarity	NPD7525	Registered
0.7411	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7736	Approved
0.7374	Intermediate Similarity	NPD6695	Phase 3
0.7373	Intermediate Similarity	NPD6319	Approved
0.7368	Intermediate Similarity	NPD6117	Approved
0.735	Intermediate Similarity	NPD7328	Approved
0.735	Intermediate Similarity	NPD7327	Approved
0.7339	Intermediate Similarity	NPD5211	Phase 2
0.7327	Intermediate Similarity	NPD3618	Phase 1
0.7321	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5286	Approved
0.7315	Intermediate Similarity	NPD4696	Approved
0.7315	Intermediate Similarity	NPD5285	Approved
0.7311	Intermediate Similarity	NPD8379	Approved
0.7311	Intermediate Similarity	NPD8033	Approved
0.7311	Intermediate Similarity	NPD8296	Approved
0.7311	Intermediate Similarity	NPD8380	Approved
0.7311	Intermediate Similarity	NPD8335	Approved
0.7311	Intermediate Similarity	NPD8378	Approved
0.7304	Intermediate Similarity	NPD8133	Approved
0.73	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6116	Phase 1
0.729	Intermediate Similarity	NPD4755	Approved
0.7288	Intermediate Similarity	NPD7516	Approved
0.7281	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7492	Approved
0.7265	Intermediate Similarity	NPD6009	Approved
0.7264	Intermediate Similarity	NPD5695	Phase 3
0.7255	Intermediate Similarity	NPD7750	Discontinued
0.7238	Intermediate Similarity	NPD5778	Approved
0.7238	Intermediate Similarity	NPD5779	Approved
0.7238	Intermediate Similarity	NPD4202	Approved
0.7227	Intermediate Similarity	NPD8377	Approved
0.7227	Intermediate Similarity	NPD8294	Approved
0.7227	Intermediate Similarity	NPD6054	Approved
0.7222	Intermediate Similarity	NPD5696	Approved
0.7217	Intermediate Similarity	NPD6053	Discontinued
0.7216	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6616	Approved
0.7207	Intermediate Similarity	NPD5141	Approved
0.7196	Intermediate Similarity	NPD5221	Approved
0.7196	Intermediate Similarity	NPD5222	Approved
0.7196	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7604	Phase 2
0.7184	Intermediate Similarity	NPD5737	Approved
0.7184	Intermediate Similarity	NPD6672	Approved
0.7184	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5226	Approved
0.7182	Intermediate Similarity	NPD4633	Approved
0.7182	Intermediate Similarity	NPD5225	Approved
0.7182	Intermediate Similarity	NPD5224	Approved
0.717	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7900	Approved
0.7168	Intermediate Similarity	NPD6686	Approved
0.7167	Intermediate Similarity	NPD5983	Phase 2
0.7158	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7146	Approved
0.7157	Intermediate Similarity	NPD7521	Approved
0.7157	Intermediate Similarity	NPD7334	Approved
0.7157	Intermediate Similarity	NPD6409	Approved
0.7157	Intermediate Similarity	NPD6684	Approved
0.7157	Intermediate Similarity	NPD5330	Approved
0.7156	Intermediate Similarity	NPD4700	Approved
0.7154	Intermediate Similarity	NPD7078	Approved
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD7100	Approved
0.7143	Intermediate Similarity	NPD7101	Approved
0.713	Intermediate Similarity	NPD5173	Approved
0.7117	Intermediate Similarity	NPD5174	Approved
0.7117	Intermediate Similarity	NPD5175	Approved
0.7115	Intermediate Similarity	NPD4753	Phase 2
0.7107	Intermediate Similarity	NPD6370	Approved
0.7103	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5223	Approved
0.7087	Intermediate Similarity	NPD7524	Approved
0.7083	Intermediate Similarity	NPD6059	Approved
0.708	Intermediate Similarity	NPD6412	Phase 2
0.7073	Intermediate Similarity	NPD6336	Discontinued
0.7071	Intermediate Similarity	NPD7514	Phase 3
0.7071	Intermediate Similarity	NPD6930	Phase 2
0.7071	Intermediate Similarity	NPD6931	Approved
0.7064	Intermediate Similarity	NPD4225	Approved
0.7059	Intermediate Similarity	NPD6335	Approved
0.7043	Intermediate Similarity	NPD4634	Approved
0.7037	Intermediate Similarity	NPD4697	Phase 3
0.7034	Intermediate Similarity	NPD6868	Approved
0.7034	Intermediate Similarity	NPD6274	Approved
0.703	Intermediate Similarity	NPD5362	Discontinued
0.7025	Intermediate Similarity	NPD6016	Approved
0.7025	Intermediate Similarity	NPD6015	Approved
0.7019	Intermediate Similarity	NPD6903	Approved
0.699	Remote Similarity	NPD6098	Approved
0.6975	Remote Similarity	NPD6317	Approved
0.697	Remote Similarity	NPD6929	Approved
0.6967	Remote Similarity	NPD5988	Approved
0.6961	Remote Similarity	NPD3665	Phase 1
0.6961	Remote Similarity	NPD3666	Approved
0.6961	Remote Similarity	NPD3668	Phase 3
0.6961	Remote Similarity	NPD3133	Approved
0.6957	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6051	Approved
0.6952	Remote Similarity	NPD6101	Approved
0.6952	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6673	Approved
0.6952	Remote Similarity	NPD6904	Approved
0.6952	Remote Similarity	NPD6080	Approved
0.6944	Remote Similarity	NPD5210	Approved
0.6944	Remote Similarity	NPD4629	Approved
0.6939	Remote Similarity	NPD6932	Approved
0.693	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4251	Approved
0.6923	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4250	Approved
0.6917	Remote Similarity	NPD6313	Approved
0.6917	Remote Similarity	NPD6314	Approved
0.6907	Remote Similarity	NPD7339	Approved
0.6907	Remote Similarity	NPD6942	Approved
0.69	Remote Similarity	NPD4819	Approved
0.69	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7332	Phase 2
0.69	Remote Similarity	NPD4821	Approved
0.69	Remote Similarity	NPD4820	Approved
0.69	Remote Similarity	NPD4822	Approved
0.6885	Remote Similarity	NPD7503	Approved
0.6885	Remote Similarity	NPD6908	Approved
0.6885	Remote Similarity	NPD6909	Approved
0.687	Remote Similarity	NPD4730	Approved
0.687	Remote Similarity	NPD4729	Approved
0.6869	Remote Similarity	NPD7145	Approved
0.6863	Remote Similarity	NPD7154	Phase 3
0.6863	Remote Similarity	NPD4788	Approved
0.6842	Remote Similarity	NPD4768	Approved
0.6842	Remote Similarity	NPD4767	Approved
0.6833	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6902	Approved
0.6832	Remote Similarity	NPD5369	Approved
0.6827	Remote Similarity	NPD4249	Approved
0.6822	Remote Similarity	NPD7087	Discontinued
0.6822	Remote Similarity	NPD5281	Approved
0.6822	Remote Similarity	NPD5284	Approved
0.6822	Remote Similarity	NPD5693	Phase 1
0.6814	Remote Similarity	NPD4754	Approved
0.68	Remote Similarity	NPD7645	Phase 2
0.6786	Remote Similarity	NPD5344	Discontinued

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