NPASS Compound

Natural Product: NPC287387

Natural Product ID	NPC287387
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LLUKLZVIROBDGI-SCUASFONSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	156302
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

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 -1.8771 -2.6736 -1.1302 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9388 -1.7637 -0.4295 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5358 -0.6381 -0.0145 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9209 -0.2520 -0.1749 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7756 -0.9967 -0.7398 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1084 1.0672 0.4039 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9505 1.4711 0.8843 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6903 2.7944 1.5749 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8804 0.4817 0.7022 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3117 0.9854 -0.0688 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4771 0.0357 0.2044 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6319 0.9128 -0.0769 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8102 0.7488 -0.6174 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1553 2.2380 0.4327 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9132 3.1958 0.6980 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7604 2.1813 0.5430 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4964 -1.1734 -0.6383 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4556 -2.2184 -0.2962 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7769 -1.7736 -0.5006 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6804 -3.0403 -0.4341 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3205 -3.6105 -1.4201 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2776 -2.2334 -2.0429 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0576 1.5960 0.4177 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 2.7153 2.2782 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5655 3.1344 2.1361 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4426 3.5691 0.8225 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5747 0.1683 1.7321 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0875 1.0662 -1.1280 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5227 -0.1998 1.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2137 -0.1624 -1.0075 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5086 1.6041 -0.7094 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3505 -0.8996 -1.7025 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6816 -3.0988 -0.9263 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6320 -2.5306 0.7515 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6557 -2.7007 -0.8154 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 2 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 14 16 1 0 11 17 1 0 17 18 1 0 17 19 1 0 18 2 1 0 9 3 1 0 16 10 1 0 1 20 1 0 1 21 1 0 1 22 1 0 6 23 1 0 8 24 1 0 8 25 1 0 8 26 1 0 9 27 1 1 10 28 1 6 11 29 1 1 13 30 1 0 13 31 1 0 17 32 1 6 18 33 1 0 18 34 1 0 19 35 1 0 M END

Standard InCHIKey	LLUKLZVIROBDGI-SCUASFONSA-N
Standard InCHI	InChI=1S/C15H16O4/c1-6-4-10(17)13-8(3)15(18)19-14(13)12-7(2)5-9(16)11(6)12/h5,10,12-14,17H,3-4H2,1-2H3/t10-,12-,13+,14+/m0/s1
SMILES	CC1=C2C(=O)C=C(C)[C@@H]2[C@@H]2[C@H](C(=C)C(=O)O2)[C@H](C1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	260.1	Volume:	264.305 ? Van der Waals volume.
Dense:	0.984	LogP:	1.452 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.807 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.99 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	18.0
TPSA:	63.6 ? 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:	0.527	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.41	Fsp³:	0.467
MCE-18:	46.636 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.389	Fluc inhibitor:	0.118 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.44 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.021 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.494	Promiscuous compounds:	0.479

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.839	MDCK Permeability:	-4.565
Pgp-inhibitor:	0.144	Pgp-substrate:	0.84
PAMPA:	0.869 ? 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):	0.207
20% Bioavailability (F20%):	0.272	30% Bioavailability (F30%):	0.571
50% Bioavailability (F50%):	0.912

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085	MRP1:	0.689
Plasma Protein Binding (PPB):	67.028%	Volume Distribution (VD):	-0.043
Fu:	32.03% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.982
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.122
BSEP inhibitor:	0.561

ADMET: Metabolism

CYP1A2-inhibitor:	0.415	CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.28	CYP2C19-substrate:	0.358
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.457
CYP3A4-inhibitor:	0.192	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.969
HLM stability:	0.9 ? 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):

8.086

Half-life (T1/2):

1.847

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.241
Human Hepatotoxicity (H-HT):	0.778	Drug-induced Liver Injury (DILI):	0.949
AMES Toxicity:	0.853	Rat Oral Acute Toxicity:	0.508
Maximum Recommended Daily Dose:	0.395	Skin Sensitization:	0.999
Carcinogencity:	0.748	Eye Corrosion:	0.141
Eye Irritation:	0.903	Respiratory Toxicity:	0.343
Drug-induced Neurotoxicity:	0.542	Ototoxicity:	0.417
Hematotoxicity:	0.911	Drug-induced Nephrotoxicity:	0.905
Genotoxicity:	0.976	RPMI-8226 Immunitoxicity:	0.245
A549 Cytotoxicity:	0.414	Hek293 Cytotoxicity:	0.299
BCF:	1.0 ? 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:	3.585 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.412 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.745 ? 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
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/JMPR.9000078]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[12130858]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	roots	Rat Buri Province, Thailand	1988-DEC	PMID[14987064]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[16204992]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16724853]
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16724853]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO16660	Phomopsis archeri	Species	Valsaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21341709]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25590529]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26099993]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28156114]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29400471]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30726671]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO13180	Jasminum officinale	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39524716]
NPO2733	Sarcomelicope argyrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5634	Wallago attu	Species	Siluridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11020	Streptomyces purpeofuscus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11831	Achillea collina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18962	Actinobacillus pleuropneumoniae	Species	Pasteurellaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13422	Amoora yunnanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9428	Annona rensoniana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17945	Arachniodes dimorphophylla	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10436	Aristolochia maxima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17100	Artemisia vachanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13856	Bergenia purpurascens	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11559	Betula mandshurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17355	Bischofia trifoliata	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17706	Caragana tibetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14408	Chrysolina fastuosa	Species	Chrysomelidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17327	Cotoneaster orbicularis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16374	Crataegus sinaica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18709	Discaria crenata	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11420	Dolichospermum affine	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17870	Euphorbia ferganensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16510	Ganoderma australe	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13180	Jasminum officinale	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21802	Julocroton camporum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17175	Lasiocephalus ovatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15667	Ligularia platyglossa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17739	Macrotyloma axillare	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16620	Malus asiatica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12559	Mikania obtusata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11925	Mola mola	Species	Molidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17244	Montrouziera sphaeroidea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9523	Nephroma antarcticum	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18027	Oreosolen wattii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12733	Pentapora fascialis	Species	Bitectiporidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1148	Phalium undulatum	Species	Cassidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16660	Phomopsis archeri	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14698	Phyllospongia madagascarensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17637	Pimpinella saxifraga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15079	Polygala myrtifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16253	Rapanea myricoides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15814	Rhodiola krylovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2733	Sarcomelicope argyrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2589	Solanum bahamense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26487	Tinospora smilacina	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17029	Tridacna gigas	Species	Tridacnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22469	Tropaeolum speciosum	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15964	Tropiometra afra	Species	Tropiometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6939	Vatica diospyroides	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17706	Caragana tibetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10436	Aristolochia maxima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13180	Jasminum officinale	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16620	Malus asiatica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13856	Bergenia purpurascens	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17637	Pimpinella saxifraga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17244	Montrouziera sphaeroidea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13856	Bergenia purpurascens	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17706	Caragana tibetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17637	Pimpinella saxifraga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13180	Jasminum officinale	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10436	Aristolochia maxima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13180	Jasminum officinale	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11925	Mola mola	Species	Molidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22469	Tropaeolum speciosum	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16374	Crataegus sinaica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11559	Betula mandshurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2589	Solanum bahamense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15667	Ligularia platyglossa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2733	Sarcomelicope argyrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16510	Ganoderma australe	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11420	Dolichospermum affine	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17327	Cotoneaster orbicularis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12733	Pentapora fascialis	Species	Bitectiporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18027	Oreosolen wattii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17706	Caragana tibetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16253	Rapanea myricoides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15079	Polygala myrtifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9523	Nephroma antarcticum	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15814	Rhodiola krylovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16620	Malus asiatica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15964	Tropiometra afra	Species	Tropiometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16660	Phomopsis archeri	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17739	Macrotyloma axillare	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10436	Aristolochia maxima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18709	Discaria crenata	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13856	Bergenia purpurascens	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13422	Amoora yunnanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13180	Jasminum officinale	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21802	Julocroton camporum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17029	Tridacna gigas	Species	Tridacnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1148	Phalium undulatum	Species	Cassidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17244	Montrouziera sphaeroidea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6939	Vatica diospyroides	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11020	Streptomyces purpeofuscus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17355	Bischofia trifoliata	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5634	Wallago attu	Species	Siluridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14408	Chrysolina fastuosa	Species	Chrysomelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11831	Achillea collina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17175	Lasiocephalus ovatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12559	Mikania obtusata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18962	Actinobacillus pleuropneumoniae	Species	Pasteurellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17945	Arachniodes dimorphophylla	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17100	Artemisia vachanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14698	Phyllospongia madagascarensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26487	Tinospora smilacina	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9428	Annona rensoniana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17870	Euphorbia ferganensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17637	Pimpinella saxifraga	Species	Apiaceae	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

Activity Type	# Activity
Inhibition	4
IC50	2

Activity Type	# Activity
Unchecked	6

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
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	n.a.	n.a.	%	PMID[36351173]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	15100.0	nM	PMID[36351173]

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 NPC287387 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	15931
0.1-0.2	29117
0.2-0.3	4570
0.3-0.4	205
0.4-0.5	23
0.5-0.6	7
0.6-0.7	2
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
0.7826	Intermediate Similarity	NPC129419
0.6327	Remote Similarity	NPC165287
0.6122	Remote Similarity	NPC302426
0.5882	Remote Similarity	NPC605675
0.5769	Remote Similarity	NPC115786
0.566	Remote Similarity	NPC608666
0.5556	Remote Similarity	NPC603713
0.5455	Remote Similarity	NPC609013
0.5455	Remote Similarity	NPC610156
0.5185	Remote Similarity	NPC268298

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC287387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6200
0.1-0.2	2880
0.2-0.3	68
0.3-0.4	2
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