NPASS Compound

Structure

NPC249194 OpenBabel06302216202D 22 25 0 0 1 0 0 0 0 0999 V2000 2.7256 -2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1504 -1.3132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9086 -0.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9086 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1503 0.4379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3921 0.0001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3921 0.8496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3921 -0.8755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6339 -1.3133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8756 -0.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8756 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1173 0.4378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1173 1.3134 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8755 1.7512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6338 1.3134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6338 0.4378 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3205 0.5551 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9615 0.5551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4801 0.1783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5751 -2.0489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4247 -2.0489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 8 1 0 0 0 0 2 3 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 16 1 0 0 0 0 6 7 1 1 0 0 0 6 8 1 0 0 0 0 8 9 1 1 0 0 0 9 10 1 0 0 0 0 11 10 1 1 0 0 0 11 18 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 13 12 1 1 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 16 15 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 6 0 0 0 19 20 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	665.47
Volume:	740.589
LogP:	8.266
LogD:	5.031
LogS:	-2.957
# Rotatable Bonds:	28
TPSA:	105.09
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.053
Synthetic Accessibility Score:	3.667
Fsp3:	0.61
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.942
MDCK Permeability:	2.2043366698198952e-05
Pgp-inhibitor:	0.957
Pgp-substrate:	0.142
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	100.29891204833984%
Volume Distribution (VD):	1.274
Pgp-substrate:	0.4423738121986389%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.549
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.746
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.668
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	4.998
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.787
Human Hepatotoxicity (H-HT):	0.462
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.955
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.103

Download Data

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

Natural Product: NPC249194

Natural Product ID:	NPC249194
*Common Name:**	BQTHAHCFODJOGN-DUBPVYKHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BQTHAHCFODJOGN-DUBPVYKHSA-N
Standard InCHI:	InChI=1S/C20H34O2/c1-18(13-22)7-3-8-19(2)16(18)6-9-20-10-14(4-5-17(19)20)15(11-20)12-21/h14-17,21-22H,3-13H2,1-2H3/t14-,15-,16-,17+,18+,19-,20+/m1/s1
SMILES:	C[C@]1(CCC[C@]2(C)[C@@H]1CC[C@]13C[C@@H](CC[C@@H]23)[C@H](C1)CO)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	102594837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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]
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	flowers	n.a.	n.a.	PMID[10075775]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479331]
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]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15387664]
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]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18179176]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524603]
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]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
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]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25679537]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	San Antonio, Texas	2004-JUN	PMID[25685941]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	n.a.	n.a.	PMID[25685941]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25901993]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26238319]
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]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29924604]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158166]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	Suriname rainforest	n.a.	PMID[9428162]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
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]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	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[TCMID]
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]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	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]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11760	Teucrium orientale	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4507	Bruguiera gymnorhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18424	Selinum libanotis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO968	Artemisia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9906	Zephyranthes flava	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14002	Petalostemon purpureum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16923	Cereus chrysacanthus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11408	Podocarpus amarus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4336	Echiochilon pauciflorum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25370	Botrychium ternatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17114	Streptomyces melanogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17218	Helichrysum nudifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16215	Umbilicaria cinereorufescens	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18927	Clinacanthus nutans	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10770	Ptilota pectinata	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16135	Pestalotiopsis oenotherae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16052	Chromodoris obsoleta	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28319	Ulva prolifera	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5455	Euploca racemosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17921	Allium monspessulanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16812	Ajuga bracteosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17354	Micromonospora echinospora	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11081	Baccharis grandicapitulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16325	Sideritis dasygnaphala	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]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17602	Arbutus menziesii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15919	Streptomyces caelestis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2155	Tephroseris integrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19709	Pseudocyphellaria australiensis	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15802	Papaver pseudocanescens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19170	Lasianthaea podocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28868	Pardachirus pavoninus	Species	Soleidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9951	Hyella caespitosa	Species	Hyellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14813	Agaricus silvaticus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17230	Psidium acutangulum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25550	Buchenavia tetraphylla	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12870	Curcuma aeruginosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15545	Veltheimia viridifolia	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28821	Stichopus horrens	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18169	Creosphaeria sassafras	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15748	Hypoxis nyasica	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13789	Paranephelius uniflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12223	Stellaria media	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4507	Bruguiera gymnorhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17844	Agaricus integer	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16981	Gutierrezia dracunculoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13013	Saccharothrix mutabilis	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19371	Costasiella ocellifera	Species	Costasiellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16329	Potebniamyces gallicola	Species	Phacidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16695	Fumaria kraliki	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17071	Coeloseira pacifica	Species	Champiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7905	Lepista irina	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2550	Trichoderma citrinum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8010	Otostegia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17375	Ceramium botryocarpum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11760	Teucrium orientale	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4679	Hedysarum gmelini	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15127	Senecio congestus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11646	Morella pensylvanica	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18348	Crotalaria stolzii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9189	Streptomyces atratus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18073	Justicia trinervia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12914	Sarcophyton flexuosum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8172	Emericellopsis minima	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19572	Pellacalyx axillaris	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17304	Sipunculus nudus	Species	Sipunculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18533	Delisea elegans	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17339	Macaranga sinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17630	Helenium integrifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22097	Plakinastrella clathrata	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17499	Bursera kerberi	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18262	Aspergillus microcysticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO84	Isoberlinia angolensis	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC249194 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	305
0.1-0.2	5794
0.2-0.3	18422
0.3-0.4	7398
0.4-0.5	5124
0.5-0.6	3827
0.6-0.7	1324
0.7-0.8	386
0.8-0.85	80
0.85-0.9	27
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID

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 NPC249194 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	4506
0.2-0.3	3161
0.3-0.4	647
0.4-0.5	229
0.5-0.6	184
0.6-0.7	57
0.7-0.8	22
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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