NPASS Compound

Natural Product: NPC19404

Natural Product ID	NPC19404
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MKXDAWJZYZIEIP-OAHLLOKOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	156523
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 35 37 0 0 0 0 0 0 0 0999 V2000 3.9772 1.1095 2.2431 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8894 0.2444 1.0452 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7466 -0.0188 0.4339 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5310 -0.8484 -0.7439 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4165 -1.4655 -1.3885 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1097 -0.8518 -1.0631 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3386 -1.4518 -2.0510 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0270 -1.2736 -2.1104 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6320 -0.4644 -1.1419 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1020 -0.2407 -1.1636 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5766 0.3902 0.0996 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9056 -0.2570 0.4696 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8308 1.7635 -0.0479 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7040 0.2666 1.1755 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5252 0.9730 0.8413 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 0.1130 -0.1825 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5210 -0.0591 -0.1135 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4636 0.4396 0.7744 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1220 -0.3578 0.4975 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0921 1.8104 2.2393 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8623 1.7443 2.2742 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8670 0.5241 3.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8458 -2.0658 -2.7750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6518 -1.7271 -2.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6254 -1.1912 -1.4079 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2895 0.4541 -2.0259 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5769 -0.2264 -0.4128 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7565 -1.3001 0.7662 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3963 0.2667 1.3166 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8720 2.1379 0.8622 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8743 1.1165 1.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8219 1.9268 0.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1396 -0.1010 -0.6006 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1072 -1.4570 0.6210 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9883 0.0768 1.0080 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 2 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 6 11 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 2 19 1 0 18 3 1 0 17 6 1 0 16 9 1 0 1 20 1 0 1 21 1 0 1 22 1 0 7 23 1 0 8 24 1 0 10 25 1 0 10 26 1 0 12 27 1 0 12 28 1 0 12 29 1 0 13 30 1 0 15 31 1 0 15 32 1 0 19 33 1 0 19 34 1 0 19 35 1 0 M END

Standard InCHIKey	MKXDAWJZYZIEIP-OAHLLOKOSA-N
Standard InCHI	InChI=1S/C15H16O4/c1-8(2)13-12(16)10-5-4-9-6-15(3,17)18-7-11(9)14(10)19-13/h4-5,17H,6-7H2,1-3H3/t15-/m1/s1
SMILES	CC(=C1C(=O)c2ccc3C[C@](C)(O)OCc3c2O1)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	260.1	Volume:	264.305 ? Van der Waals volume.
Dense:	0.984	LogP:	2.641 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.603 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.234 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	17.0
TPSA:	55.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.727	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.884	Fsp³:	0.4
MCE-18:	62.429 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.045	Fluc inhibitor:	0.363 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.784 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.197 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.305	Promiscuous compounds:	0.358

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.665	MDCK Permeability:	-4.682
Pgp-inhibitor:	0.767	Pgp-substrate:	0.146
PAMPA:	0.402 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.076	30% Bioavailability (F30%):	0.136
50% Bioavailability (F50%):	0.737

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014	MRP1:	0.855
Plasma Protein Binding (PPB):	90.732%	Volume Distribution (VD):	0.378
Fu:	8.133% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.963
OATP1B3 inhibitor:	0.929	BCRP inhibitor:	0.246
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.073	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.709	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.587
HLM stability:	0.008 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

9.437

Half-life (T1/2):

1.342

ADMET: Toxicity

hERG Blockers:	0.083	hERG Blockers (10um):	0.221
Human Hepatotoxicity (H-HT):	0.747	Drug-induced Liver Injury (DILI):	0.457
AMES Toxicity:	0.671	Rat Oral Acute Toxicity:	0.271
Maximum Recommended Daily Dose:	0.846	Skin Sensitization:	0.978
Carcinogencity:	0.839	Eye Corrosion:	0.003
Eye Irritation:	0.844	Respiratory Toxicity:	0.027
Drug-induced Neurotoxicity:	0.229	Ototoxicity:	0.517
Hematotoxicity:	0.401	Drug-induced Nephrotoxicity:	0.61
Genotoxicity:	0.702	RPMI-8226 Immunitoxicity:	0.126
A549 Cytotoxicity:	0.022	Hek293 Cytotoxicity:	0.46
BCF:	0.638 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.23 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.658 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.994 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

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]
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]
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]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37687143]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158166]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15919	Streptomyces caelestis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9189	Streptomyces atratus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17844	Agaricus integer	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14813	Agaricus silvaticus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16812	Ajuga bracteosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17921	Allium monspessulanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17602	Arbutus menziesii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4507	Bruguiera gymnorhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25550	Buchenavia tetraphylla	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17375	Ceramium botryocarpum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16923	Cereus chrysacanthus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16052	Chromodoris obsoleta	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16566	Cinnamosma madagascariensis	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17071	Coeloseira pacifica	Species	Champiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4336	Echiochilon pauciflorum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16695	Fumaria kraliki	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17218	Helichrysum nudifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9951	Hyella caespitosa	Species	Hyellaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15748	Hypoxis nyasica	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO84	Isoberlinia angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18073	Justicia trinervia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7905	Lepista irina	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17339	Macaranga sinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8010	Otostegia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13789	Paranephelius uniflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28868	Pardachirus pavoninus	Species	Soleidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14002	Petalostemon purpureum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22097	Plakinastrella clathrata	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11408	Podocarpus amarus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16329	Potebniamyces gallicola	Species	Phacidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10770	Ptilota pectinata	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13013	Saccharothrix mutabilis	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17304	Sipunculus nudus	Species	Sipunculidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28821	Stichopus horrens	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2155	Tephroseris integrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11760	Teucrium orientale	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2550	Trichoderma citrinum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28319	Ulva prolifera	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16215	Umbilicaria cinereorufescens	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15545	Veltheimia viridifolia	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
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]
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]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16456	Mirabilis jalapa	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4507	Bruguiera gymnorhiza	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO15004	Artemisia taurica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21437	Rhododendron aureum	Species	Ericaceae	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]
NPO5119	Pseudomonas chlororaphis	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14813	Agaricus silvaticus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28821	Stichopus horrens	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13013	Saccharothrix mutabilis	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7905	Lepista irina	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11760	Teucrium orientale	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO84	Isoberlinia angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14575	Periploca forrestii	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11408	Podocarpus amarus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16215	Umbilicaria cinereorufescens	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15919	Streptomyces caelestis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17071	Coeloseira pacifica	Species	Champiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17375	Ceramium botryocarpum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17218	Helichrysum nudifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16052	Chromodoris obsoleta	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16812	Ajuga bracteosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17602	Arbutus menziesii	Species	Ericaceae	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]
NPO2550	Trichoderma citrinum	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9189	Streptomyces atratus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17304	Sipunculus nudus	Species	Sipunculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10770	Ptilota pectinata	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	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]
NPO28319	Ulva prolifera	Species	Ulvaceae	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]
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]
NPO17844	Agaricus integer	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16695	Fumaria kraliki	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8010	Otostegia fruticosa	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]
NPO15004	Artemisia taurica	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]
NPO17921	Allium monspessulanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21437	Rhododendron aureum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17999	Sonneratia alba	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17339	Macaranga sinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4336	Echiochilon pauciflorum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15599	Daldinia concentrica	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2155	Tephroseris integrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9951	Hyella caespitosa	Species	Hyellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15545	Veltheimia viridifolia	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13789	Paranephelius uniflorus	Species	Asteraceae	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	Organism Name	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

Molecular-level activity

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

In vitro activity

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

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC19404 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	18215
0.1-0.2	31092
0.2-0.3	546
0.3-0.4	1
0.4-0.5	2
0.5-0.6	3
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.566	Remote Similarity	NPC469385
0.5179	Remote Similarity	NPC217914
0.5172	Remote Similarity	NPC175617

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC19404 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3432
0.1-0.2	5692
0.2-0.3	26
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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