NPASS Compound

Structure

CID158963 OpenBabel06191715532D 35 40 0 0 1 0 0 0 0 0999 V2000 -2.0483 4.7732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8152 2.4326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9366 2.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3915 0.4320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4502 1.4923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0654 5.6710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6140 2.6890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6633 2.9060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1633 0.1261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9436 0.8353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9507 -0.2170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9464 3.8034 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0371 1.8104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6140 0.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0991 1.3228 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1357 0.1990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7882 2.2980 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1999 3.5359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7156 2.5993 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7156 1.0215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5226 4.0716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0095 1.8833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7882 1.3228 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0991 2.2980 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6633 0.7148 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9436 2.7856 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6851 -0.6067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5052 4.2203 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0169 0.0941 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4460 3.7582 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3323 5.0280 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 -2.6209 3.3866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2888 1.8104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5588 1.0776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 5 24 1 0 0 0 0 6 31 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 24 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 23 1 0 0 0 0 11 32 1 0 0 0 0 12 1 1 1 0 0 0 12 18 1 0 0 0 0 12 33 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 25 1 0 0 0 0 15 24 1 6 0 0 0 15 25 1 0 0 0 0 16 27 2 0 0 0 0 16 35 1 0 0 0 0 17 19 1 0 0 0 0 17 23 1 1 0 0 0 17 26 1 0 0 0 0 18 26 1 0 0 0 0 18 28 2 0 0 0 0 19 33 1 1 0 0 0 19 34 1 0 0 0 0 20 23 1 0 0 0 0 20 29 2 0 0 0 0 20 34 1 0 0 0 0 21 30 2 0 0 0 0 21 31 1 0 0 0 0 22 35 1 0 0 0 0 23 4 1 6 0 0 0 24 26 1 6 0 0 0 25 11 1 1 0 0 0 25 32 1 0 0 0 0 26 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.19
Volume:	470.207
LogP:	2.317
LogD:	1.692
LogS:	-4.717
# Rotatable Bonds:	2
TPSA:	117.73
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.237
Synthetic Accessibility Score:	6.188
Fsp3:	0.692
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.364
MDCK Permeability:	2.1146626750123687e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.894
Plasma Protein Binding (PPB):	74.35352325439453%
Volume Distribution (VD):	1.481
Pgp-substrate:	25.17304801940918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.739
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.81
CYP3A4-substrate:	0.887

ADMET: Excretion

Clearance (CL):	5.66
Half-life (T1/2):	0.707

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.824
AMES Toxicity:	0.369
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.664
Skin Sensitization:	0.148
Carcinogencity:	0.847
Eye Corrosion:	0.009
Eye Irritation:	0.061
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC158963

Natural Product ID:	NPC158963
*Common Name:**	Berkeleyacetal B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XZKVBCSVEVIEBX-YJCISAIBSA-N
Standard InCHI:	InChI=1S/C26H30O9/c1-12-18(28)26(21(30)31-6)17-19(33-12)34-20(29)23(17,4)10-15-24(26,5)8-7-13-14(25(15)11-32-25)9-16(27)35-22(13,2)3/h7,9,12,15,17,19H,8,10-11H2,1-6H3/t12-,15+,17+,19+,23+,24-,25-,26-/m0/s1
SMILES:	C[C@H]1C(=O)[C@@]2([C@@H]3[C@H](O1)OC(=O)[C@]3(C)C[C@@H]1[C@]2(C)CC=C2C(=CC(=O)OC2(C)C)[C@]21CO2)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252921
PubChem CID:	24179626
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001818] Furopyrans

*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]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277746]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO10881	Gyrophyllum sibogae	Species	Pennatulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270580]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	PMID[16254827]
NPO3909	Leucas aspera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872130]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18179176]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19835393]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
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]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO40990	Penicillium sp. MA-37	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23148724]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
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]
NPO40981	Penicillium chrysogenum MT-12	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28960979]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	Fruiting Bodies	n.a.	n.a.	PMID[29715021]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158166]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
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]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8010	Otostegia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3909	Leucas aspera	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]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	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]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11760	Teucrium orientale	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15056	Helianthus pumilus	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]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15056	Helianthus pumilus	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]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3909	Leucas aspera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28319	Ulva prolifera	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17218	Helichrysum nudifolium	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]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3221	Schkuhria anthemoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28821	Stichopus horrens	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28868	Pardachirus pavoninus	Species	Soleidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16052	Chromodoris obsoleta	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13013	Saccharothrix mutabilis	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25550	Buchenavia tetraphylla	Species	Combretaceae	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]
NPO7905	Lepista irina	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17844	Agaricus integer	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17828	Talaromyces ruber	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17602	Arbutus menziesii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17339	Macaranga sinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11760	Teucrium orientale	Species	Lamiaceae	Eukaryota	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]
NPO4336	Echiochilon pauciflorum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO84	Isoberlinia angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8010	Otostegia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16329	Potebniamyces gallicola	Species	Phacidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18073	Justicia trinervia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9306	Globularia nudicaulis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2550	Trichoderma citrinum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2155	Tephroseris integrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11408	Podocarpus amarus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9189	Streptomyces atratus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO263	Clibadium microcephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16215	Umbilicaria cinereorufescens	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22097	Plakinastrella clathrata	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15438	Stemona parviflora	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17304	Sipunculus nudus	Species	Sipunculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9951	Hyella caespitosa	Species	Hyellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10881	Gyrophyllum sibogae	Species	Pennatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17921	Allium monspessulanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10770	Ptilota pectinata	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15545	Veltheimia viridifolia	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15919	Streptomyces caelestis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13789	Paranephelius uniflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17071	Coeloseira pacifica	Species	Champiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17375	Ceramium botryocarpum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16923	Cereus chrysacanthus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14002	Petalostemon purpureum	Species	Fabaceae	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
LD50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	50.0	%	PMID[471007]
NPT140	Organism	Artemia	Artemia	LD50	=	160.0	uM	PMID[471006]

☑ 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 NPC158963 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	297
0.1-0.2	1735
0.2-0.3	5445
0.3-0.4	9074
0.4-0.5	12777
0.5-0.6	8235
0.6-0.7	4587
0.7-0.8	529
0.8-0.85	8
0.85-0.9	4
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8016	Intermediate Similarity	NPC476851
0.8016	Intermediate Similarity	NPC476854
0.7966	Intermediate Similarity	NPC222834
0.7953	Intermediate Similarity	NPC476855
0.7953	Intermediate Similarity	NPC476863
0.7953	Intermediate Similarity	NPC476852
0.7953	Intermediate Similarity	NPC476862
0.7937	Intermediate Similarity	NPC476859
0.7838	Intermediate Similarity	NPC112654
0.7826	Intermediate Similarity	NPC325769
0.7719	Intermediate Similarity	NPC473384
0.7712	Intermediate Similarity	NPC23497
0.7705	Intermediate Similarity	NPC243298
0.768	Intermediate Similarity	NPC287236
0.7661	Intermediate Similarity	NPC147635
0.7661	Intermediate Similarity	NPC163693
0.7623	Intermediate Similarity	NPC477509
0.7603	Intermediate Similarity	NPC159333
0.7586	Intermediate Similarity	NPC25666
0.7586	Intermediate Similarity	NPC271059
0.7563	Intermediate Similarity	NPC112457
0.7561	Intermediate Similarity	NPC13713
0.7561	Intermediate Similarity	NPC23046
0.7544	Intermediate Similarity	NPC264378
0.7542	Intermediate Similarity	NPC180744
0.754	Intermediate Similarity	NPC470419
0.7522	Intermediate Similarity	NPC311166
0.7522	Intermediate Similarity	NPC476275
0.7521	Intermediate Similarity	NPC265391
0.75	Intermediate Similarity	NPC222307
0.748	Intermediate Similarity	NPC270478
0.7478	Intermediate Similarity	NPC476933
0.7477	Intermediate Similarity	NPC20713
0.7463	Intermediate Similarity	NPC596
0.746	Intermediate Similarity	NPC204731
0.7458	Intermediate Similarity	NPC476761
0.7458	Intermediate Similarity	NPC476762
0.7458	Intermediate Similarity	NPC476760
0.7458	Intermediate Similarity	NPC469607
0.7444	Intermediate Similarity	NPC262813
0.7442	Intermediate Similarity	NPC298841
0.7442	Intermediate Similarity	NPC42399
0.744	Intermediate Similarity	NPC268958
0.744	Intermediate Similarity	NPC245320
0.7436	Intermediate Similarity	NPC471364
0.7436	Intermediate Similarity	NPC471365
0.7436	Intermediate Similarity	NPC132395
0.7434	Intermediate Similarity	NPC473369
0.7422	Intermediate Similarity	NPC24651
0.7422	Intermediate Similarity	NPC470922
0.7419	Intermediate Similarity	NPC53396
0.7419	Intermediate Similarity	NPC98249
0.7417	Intermediate Similarity	NPC469370
0.7402	Intermediate Similarity	NPC312833
0.7395	Intermediate Similarity	NPC133422
0.7388	Intermediate Similarity	NPC471089
0.7388	Intermediate Similarity	NPC141215
0.7388	Intermediate Similarity	NPC251998
0.7388	Intermediate Similarity	NPC243014
0.7388	Intermediate Similarity	NPC190065
0.7387	Intermediate Similarity	NPC469595
0.7387	Intermediate Similarity	NPC212679
0.7387	Intermediate Similarity	NPC329857
0.7387	Intermediate Similarity	NPC220454
0.7387	Intermediate Similarity	NPC469718
0.7385	Intermediate Similarity	NPC473620
0.7385	Intermediate Similarity	NPC270109
0.7381	Intermediate Similarity	NPC473145
0.7381	Intermediate Similarity	NPC31641
0.7381	Intermediate Similarity	NPC476815
0.7373	Intermediate Similarity	NPC476764
0.7373	Intermediate Similarity	NPC476763
0.7373	Intermediate Similarity	NPC474898
0.7368	Intermediate Similarity	NPC473548
0.7368	Intermediate Similarity	NPC242486
0.7368	Intermediate Similarity	NPC15215
0.7368	Intermediate Similarity	NPC223356
0.7368	Intermediate Similarity	NPC100017
0.7368	Intermediate Similarity	NPC475500
0.7368	Intermediate Similarity	NPC475154
0.7368	Intermediate Similarity	NPC471137
0.7368	Intermediate Similarity	NPC182266
0.7368	Intermediate Similarity	NPC471234
0.7368	Intermediate Similarity	NPC471136
0.7364	Intermediate Similarity	NPC477745
0.736	Intermediate Similarity	NPC284707
0.736	Intermediate Similarity	NPC470420
0.7355	Intermediate Similarity	NPC253906
0.7355	Intermediate Similarity	NPC281624
0.7355	Intermediate Similarity	NPC478209
0.7355	Intermediate Similarity	NPC235014
0.735	Intermediate Similarity	NPC469606
0.735	Intermediate Similarity	NPC273005
0.735	Intermediate Similarity	NPC31058
0.7348	Intermediate Similarity	NPC6274
0.7348	Intermediate Similarity	NPC33378
0.7348	Intermediate Similarity	NPC254146
0.7345	Intermediate Similarity	NPC88507
0.7344	Intermediate Similarity	NPC472077
0.7344	Intermediate Similarity	NPC18945
0.7344	Intermediate Similarity	NPC105926
0.7344	Intermediate Similarity	NPC265557
0.7344	Intermediate Similarity	NPC67251
0.7344	Intermediate Similarity	NPC472078
0.7344	Intermediate Similarity	NPC91693
0.7333	Intermediate Similarity	NPC295885
0.7333	Intermediate Similarity	NPC140045
0.7333	Intermediate Similarity	NPC322903
0.7323	Intermediate Similarity	NPC473228
0.7323	Intermediate Similarity	NPC102822
0.7323	Intermediate Similarity	NPC470779
0.7323	Intermediate Similarity	NPC470418
0.7323	Intermediate Similarity	NPC470829
0.7323	Intermediate Similarity	NPC477046
0.7321	Intermediate Similarity	NPC65513
0.7317	Intermediate Similarity	NPC326264
0.7317	Intermediate Similarity	NPC474271
0.7317	Intermediate Similarity	NPC33360
0.7317	Intermediate Similarity	NPC157441
0.7311	Intermediate Similarity	NPC478208
0.7308	Intermediate Similarity	NPC470780
0.7308	Intermediate Similarity	NPC11732
0.7308	Intermediate Similarity	NPC476008
0.7302	Intermediate Similarity	NPC475520
0.7302	Intermediate Similarity	NPC319570
0.7295	Intermediate Similarity	NPC470246
0.7295	Intermediate Similarity	NPC469656
0.7295	Intermediate Similarity	NPC469655
0.7295	Intermediate Similarity	NPC304180
0.7295	Intermediate Similarity	NPC474846
0.7295	Intermediate Similarity	NPC179798
0.7293	Intermediate Similarity	NPC478151
0.7293	Intermediate Similarity	NPC168879
0.7288	Intermediate Similarity	NPC474166
0.7288	Intermediate Similarity	NPC320154
0.7288	Intermediate Similarity	NPC19239
0.7287	Intermediate Similarity	NPC32868
0.7287	Intermediate Similarity	NPC318135
0.7287	Intermediate Similarity	NPC241456
0.7287	Intermediate Similarity	NPC476729
0.7281	Intermediate Similarity	NPC474947
0.7281	Intermediate Similarity	NPC31021
0.728	Intermediate Similarity	NPC469684
0.728	Intermediate Similarity	NPC58662
0.728	Intermediate Similarity	NPC478204
0.7273	Intermediate Similarity	NPC475377
0.7273	Intermediate Similarity	NPC173435
0.7273	Intermediate Similarity	NPC301639
0.7273	Intermediate Similarity	NPC478065
0.7273	Intermediate Similarity	NPC476074
0.7273	Intermediate Similarity	NPC262796
0.7273	Intermediate Similarity	NPC474242
0.7273	Intermediate Similarity	NPC45346
0.7273	Intermediate Similarity	NPC251564
0.7273	Intermediate Similarity	NPC172374
0.7273	Intermediate Similarity	NPC264566
0.7273	Intermediate Similarity	NPC329993
0.7273	Intermediate Similarity	NPC475167
0.7273	Intermediate Similarity	NPC478064
0.7273	Intermediate Similarity	NPC213634
0.7273	Intermediate Similarity	NPC475606
0.7273	Intermediate Similarity	NPC134914
0.7273	Intermediate Similarity	NPC475314
0.7273	Intermediate Similarity	NPC250018
0.7273	Intermediate Similarity	NPC477189
0.7265	Intermediate Similarity	NPC323441
0.7265	Intermediate Similarity	NPC474912
0.7265	Intermediate Similarity	NPC474899
0.7259	Intermediate Similarity	NPC68282
0.7258	Intermediate Similarity	NPC299849
0.7257	Intermediate Similarity	NPC471571
0.725	Intermediate Similarity	NPC475510
0.725	Intermediate Similarity	NPC475587
0.7244	Intermediate Similarity	NPC109607
0.7244	Intermediate Similarity	NPC107338
0.7241	Intermediate Similarity	NPC54843
0.7236	Intermediate Similarity	NPC317687
0.7236	Intermediate Similarity	NPC12046
0.7236	Intermediate Similarity	NPC194951
0.7227	Intermediate Similarity	NPC471143
0.7227	Intermediate Similarity	NPC477510
0.7227	Intermediate Similarity	NPC476001
0.7222	Intermediate Similarity	NPC473720
0.7222	Intermediate Similarity	NPC108581
0.7222	Intermediate Similarity	NPC478205
0.7222	Intermediate Similarity	NPC478206
0.7222	Intermediate Similarity	NPC21326
0.7222	Intermediate Similarity	NPC13710
0.7222	Intermediate Similarity	NPC113448
0.7222	Intermediate Similarity	NPC297179
0.7222	Intermediate Similarity	NPC17772
0.7218	Intermediate Similarity	NPC475139
0.7218	Intermediate Similarity	NPC478152
0.7218	Intermediate Similarity	NPC180902
0.7218	Intermediate Similarity	NPC473485
0.7218	Intermediate Similarity	NPC478150
0.7218	Intermediate Similarity	NPC231240
0.7218	Intermediate Similarity	NPC474508
0.7218	Intermediate Similarity	NPC478154
0.7218	Intermediate Similarity	NPC478153

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 NPC158963 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	1823
0.2-0.3	3951
0.3-0.4	2043
0.4-0.5	679
0.5-0.6	243
0.6-0.7	152
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7049	Intermediate Similarity	NPD6686	Approved
0.7025	Intermediate Similarity	NPD6008	Approved
0.6947	Remote Similarity	NPD8328	Phase 3
0.6923	Remote Similarity	NPD8513	Phase 3
0.6815	Remote Similarity	NPD7319	Approved
0.6794	Remote Similarity	NPD8515	Approved
0.6794	Remote Similarity	NPD8517	Approved
0.6794	Remote Similarity	NPD8516	Approved
0.6791	Remote Similarity	NPD8293	Discontinued
0.6744	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6370	Approved
0.6741	Remote Similarity	NPD7736	Approved
0.6716	Remote Similarity	NPD7507	Approved
0.6715	Remote Similarity	NPD7260	Phase 2
0.6694	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6845	Suspended
0.6642	Remote Similarity	NPD7492	Approved
0.6593	Remote Similarity	NPD6616	Approved
0.6591	Remote Similarity	NPD6054	Approved
0.6591	Remote Similarity	NPD6059	Approved
0.6581	Remote Similarity	NPD5693	Phase 1
0.6562	Remote Similarity	NPD6882	Approved
0.6544	Remote Similarity	NPD7078	Approved
0.6541	Remote Similarity	NPD6016	Approved
0.6541	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5696	Approved
0.6508	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5692	Phase 3
0.6493	Remote Similarity	NPD5988	Approved
0.6491	Remote Similarity	NPD1694	Approved
0.6489	Remote Similarity	NPD6009	Approved
0.6489	Remote Similarity	NPD7115	Discovery
0.6484	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5282	Discontinued
0.6466	Remote Similarity	NPD6319	Approved
0.6466	Remote Similarity	NPD6672	Approved
0.6466	Remote Similarity	NPD5737	Approved
0.6457	Remote Similarity	NPD6372	Approved
0.6457	Remote Similarity	NPD6373	Approved
0.6441	Remote Similarity	NPD6050	Approved
0.6441	Remote Similarity	NPD5694	Approved
0.6434	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD6412	Phase 2
0.6429	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7503	Approved
0.6417	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6371	Approved
0.6372	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6649	Approved
0.6357	Remote Similarity	NPD6650	Approved
0.6349	Remote Similarity	NPD7128	Approved
0.6349	Remote Similarity	NPD6675	Approved
0.6349	Remote Similarity	NPD5739	Approved
0.6349	Remote Similarity	NPD6402	Approved
0.6328	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5959	Approved
0.6304	Remote Similarity	NPD8074	Phase 3
0.6299	Remote Similarity	NPD5697	Approved
0.6299	Remote Similarity	NPD5701	Approved
0.6281	Remote Similarity	NPD5695	Phase 3
0.6281	Remote Similarity	NPD5654	Approved
0.6271	Remote Similarity	NPD6080	Approved
0.6271	Remote Similarity	NPD1695	Approved
0.6271	Remote Similarity	NPD6904	Approved
0.6271	Remote Similarity	NPD6673	Approved
0.626	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7638	Approved
0.6259	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD6899	Approved
0.6218	Remote Similarity	NPD6698	Approved
0.6218	Remote Similarity	NPD46	Approved
0.6218	Remote Similarity	NPD5207	Approved
0.621	Remote Similarity	NPD7640	Approved
0.621	Remote Similarity	NPD7639	Approved
0.6207	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7830	Approved
0.6204	Remote Similarity	NPD7642	Approved
0.6204	Remote Similarity	NPD7829	Approved
0.6202	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6013	Approved
0.6202	Remote Similarity	NPD6012	Approved
0.6202	Remote Similarity	NPD6014	Approved
0.6194	Remote Similarity	NPD7328	Approved
0.6194	Remote Similarity	NPD7327	Approved
0.6183	Remote Similarity	NPD8297	Approved
0.6179	Remote Similarity	NPD6084	Phase 2
0.6179	Remote Similarity	NPD6083	Phase 2
0.6176	Remote Similarity	NPD8444	Approved
0.6176	Remote Similarity	NPD8033	Approved
0.6167	Remote Similarity	NPD6411	Approved
0.6154	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD7521	Approved
0.6154	Remote Similarity	NPD7334	Approved
0.6154	Remote Similarity	NPD6409	Approved
0.6154	Remote Similarity	NPD6684	Approved
0.6154	Remote Similarity	NPD5330	Approved
0.6154	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD7146	Approved
0.6154	Remote Similarity	NPD6883	Approved
0.6148	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7516	Approved
0.6143	Remote Similarity	NPD8336	Approved
0.6143	Remote Similarity	NPD8337	Approved
0.6136	Remote Similarity	NPD8133	Approved
0.6136	Remote Similarity	NPD4632	Approved
0.6129	Remote Similarity	NPD4225	Approved
0.6116	Remote Similarity	NPD5779	Approved
0.6116	Remote Similarity	NPD5778	Approved
0.6116	Remote Similarity	NPD6399	Phase 3
0.6107	Remote Similarity	NPD6617	Approved
0.6107	Remote Similarity	NPD6869	Approved
0.6107	Remote Similarity	NPD6847	Approved
0.6107	Remote Similarity	NPD8130	Phase 1
0.6107	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD8377	Approved
0.6103	Remote Similarity	NPD8294	Approved
0.6102	Remote Similarity	NPD3573	Approved
0.6087	Remote Similarity	NPD7604	Phase 2
0.6087	Remote Similarity	NPD5209	Approved
0.6066	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7900	Approved
0.6058	Remote Similarity	NPD8296	Approved
0.6058	Remote Similarity	NPD6921	Approved
0.6058	Remote Similarity	NPD5983	Phase 2
0.6058	Remote Similarity	NPD8378	Approved
0.6058	Remote Similarity	NPD8380	Approved
0.6058	Remote Similarity	NPD8335	Approved
0.6058	Remote Similarity	NPD8379	Approved
0.6056	Remote Similarity	NPD6914	Discontinued
0.605	Remote Similarity	NPD6903	Approved
0.605	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5281	Approved
0.6033	Remote Similarity	NPD5284	Approved
0.6017	Remote Similarity	NPD6098	Approved
0.6014	Remote Similarity	NPD8080	Discontinued
0.6	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5968	Remote Similarity	NPD7839	Suspended
0.5957	Remote Similarity	NPD8448	Approved
0.5944	Remote Similarity	NPD8390	Approved
0.5944	Remote Similarity	NPD8392	Approved
0.5944	Remote Similarity	NPD8391	Approved
0.5944	Remote Similarity	NPD5956	Approved
0.5935	Remote Similarity	NPD6001	Approved
0.5928	Remote Similarity	NPD7799	Discontinued
0.5926	Remote Similarity	NPD6274	Approved
0.5923	Remote Similarity	NPD6614	Approved
0.592	Remote Similarity	NPD7902	Approved
0.592	Remote Similarity	NPD4755	Approved
0.5909	Remote Similarity	NPD4634	Approved
0.5902	Remote Similarity	NPD7983	Approved
0.589	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD4629	Approved
0.5887	Remote Similarity	NPD6336	Discontinued
0.5887	Remote Similarity	NPD5210	Approved
0.5882	Remote Similarity	NPD5279	Phase 3
0.5882	Remote Similarity	NPD6317	Approved
0.5862	Remote Similarity	NPD1780	Approved
0.5862	Remote Similarity	NPD1779	Approved
0.5859	Remote Similarity	NPD7632	Discontinued
0.5859	Remote Similarity	NPD5211	Phase 2
0.584	Remote Similarity	NPD4697	Phase 3
0.5839	Remote Similarity	NPD6335	Approved
0.5839	Remote Similarity	NPD6314	Approved
0.5839	Remote Similarity	NPD6313	Approved
0.5827	Remote Similarity	NPD4696	Approved
0.5827	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD5286	Approved
0.5827	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD6648	Approved
0.5827	Remote Similarity	NPD4700	Approved
0.5827	Remote Similarity	NPD5285	Approved
0.582	Remote Similarity	NPD5785	Approved
0.582	Remote Similarity	NPD7838	Discovery
0.5816	Remote Similarity	NPD8340	Approved
0.5816	Remote Similarity	NPD8299	Approved
0.5816	Remote Similarity	NPD8342	Approved
0.5816	Remote Similarity	NPD8341	Approved
0.5806	Remote Similarity	NPD7748	Approved
0.5797	Remote Similarity	NPD7101	Approved
0.5797	Remote Similarity	NPD7100	Approved
0.5785	Remote Similarity	NPD5208	Approved
0.5781	Remote Similarity	NPD5223	Approved
0.5772	Remote Similarity	NPD7637	Suspended
0.5769	Remote Similarity	NPD5141	Approved
0.5753	Remote Similarity	NPD8338	Approved
0.575	Remote Similarity	NPD5280	Approved
0.575	Remote Similarity	NPD4694	Approved
0.575	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD6067	Discontinued
0.5738	Remote Similarity	NPD6051	Approved
0.5738	Remote Similarity	NPD4753	Phase 2
0.5736	Remote Similarity	NPD4633	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