NPASS Compound

Natural Product: NPC83838

Natural Product ID	NPC83838
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OQGXDKRHMBRZCS-PWFXJFPMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1761950
PubChem CID	54585297
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans

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 52 54 0 0 0 0 0 0 0 0999 V2000 0.4845 -3.3201 -1.3561 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7070 -2.4381 -0.1852 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1820 -2.1027 0.7129 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6574 -2.5873 0.6272 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2904 -1.1896 0.5377 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6464 -0.9997 0.0402 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7746 -1.4080 0.9439 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7430 0.2528 -0.6621 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4086 0.8729 -1.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8265 1.7518 -0.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3577 1.9568 -0.0309 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5216 1.4450 -0.8367 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9706 1.6593 -0.8184 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6107 0.7714 0.2511 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7076 1.3496 0.6126 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7357 0.9138 1.6296 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8006 2.6396 -0.1416 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4512 2.8917 -0.4957 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8697 -0.4286 0.6383 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9986 -1.6040 -0.3120 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1360 2.8982 1.0597 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9512 -1.0589 -1.3182 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4326 -3.8701 -1.6278 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1712 -2.7837 -2.2552 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2431 -4.1416 -1.1059 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0204 -1.5071 1.5984 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9598 -3.0288 1.5732 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8205 -3.1458 -0.2814 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5141 -0.5779 0.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2699 -0.8320 1.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7529 -1.1120 0.5490 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6038 -1.0883 1.9943 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7658 -2.5368 0.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6657 0.8204 -0.7047 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7536 0.2011 -1.5707 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7413 1.5944 -1.9027 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2496 2.8037 -0.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1739 1.4850 1.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1627 0.7679 -1.6366 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4693 1.3408 -1.7546 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5675 -0.1450 1.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7669 1.6100 2.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7297 0.9259 1.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1701 3.4546 0.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4191 2.4713 -1.0169 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0596 -0.7785 1.6508 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7852 -0.1363 0.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9753 -1.2094 -1.3375 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8816 -2.2154 -0.1580 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5179 2.8902 1.9335 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1745 3.9401 0.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1313 2.5373 1.3986 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 1 0 5 6 1 0 6 7 1 1 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 15 17 1 0 17 18 1 0 14 19 1 0 19 20 1 0 11 21 1 0 8 22 1 0 20 2 1 0 22 6 1 0 18 13 1 0 1 23 1 0 1 24 1 0 1 25 1 0 3 26 1 0 4 27 1 0 4 28 1 0 5 29 1 0 5 30 1 0 7 31 1 0 7 32 1 0 7 33 1 0 8 34 1 1 9 35 1 0 9 36 1 0 10 37 1 0 10 38 1 0 12 39 1 0 13 40 1 6 16 41 1 0 16 42 1 0 16 43 1 0 17 44 1 0 17 45 1 0 19 46 1 0 19 47 1 0 20 48 1 0 20 49 1 0 21 50 1 0 21 51 1 0 21 52 1 0 M END

Standard InCHIKey	OQGXDKRHMBRZCS-PWFXJFPMSA-N
Standard InCHI	InChI=1S/C20H30O2/c1-14-6-5-11-20(4)19(22-20)10-8-15(2)12-18-17(9-7-14)16(3)13-21-18/h6,12,18-19H,5,7-11,13H2,1-4H3/b14-6+,15-12+/t18-,19-,20+/m1/s1
SMILES	C/C/1=CCC[C@@]2(C)[C@@H](CC/C(=C/[C@@H]3C(=C(C)CO3)CC1)/C)O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	302.22	Volume:	338.478 ? Van der Waals volume.
Dense:	0.893	LogP:	3.386 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.31 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.009 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	20.0
TPSA:	21.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.458	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.891	Fsp³:	0.7
MCE-18:	46.588 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.472	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.097 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.877	Promiscuous compounds:	0.198

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.598	MDCK Permeability:	-4.615
Pgp-inhibitor:	0.989	Pgp-substrate:	0.157
PAMPA:	0.002 ? 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):	0.006
20% Bioavailability (F20%):	0.404	30% Bioavailability (F30%):	0.837
50% Bioavailability (F50%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093	MRP1:	0.967
Plasma Protein Binding (PPB):	95.248%	Volume Distribution (VD):	0.337
Fu:	5.68% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.943	BCRP inhibitor:	0.064
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.947	CYP1A2-substrate:	0.986
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.907	CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.88	CYP2D6-substrate:	0.267
CYP3A4-inhibitor:	0.897	CYP3A4-substrate:	0.982
CYP2B6-substrate:	0.018	CYP2C8-inhibitor:	0.989
HLM stability:	0.669 ? 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):

13.306

Half-life (T1/2):

1.278

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.212
Human Hepatotoxicity (H-HT):	0.718	Drug-induced Liver Injury (DILI):	0.74
AMES Toxicity:	0.445	Rat Oral Acute Toxicity:	0.4
Maximum Recommended Daily Dose:	0.607	Skin Sensitization:	0.982
Carcinogencity:	0.344	Eye Corrosion:	0.011
Eye Irritation:	0.855	Respiratory Toxicity:	0.178
Drug-induced Neurotoxicity:	0.764	Ototoxicity:	0.273
Hematotoxicity:	0.344	Drug-induced Nephrotoxicity:	0.485
Genotoxicity:	0.716	RPMI-8226 Immunitoxicity:	0.163
A549 Cytotoxicity:	0.146	Hek293 Cytotoxicity:	0.272
BCF:	3.005 ? 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:	4.657 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.37 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.463 ? 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
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10556916]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757709]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[11141104]
NPO15773	Ecteinascidia thurstoni	Species	Perophoridae	Eukaryota	n.a.	Thai	n.a.	PMID[12088444]
NPO10443	Sloanea zuliaensis	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640532]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872152]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067165]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125220]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17685627]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19406895]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19917748]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20932054]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[22014827]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23078294]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23513740]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25043228]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25960261]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31994397]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32603106]
NPO14107	Teucrium montanum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33530639]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	Antarctic	n.a.	PMID[8882433]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15674	Acanthosyris spinescens	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26988	Acinos thymoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11762	Agrimonia eupatoria	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14434	Alluaudia humbertii	Species	Didiereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13264	Alstonia lanceolifera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14909	Artemisia caerulescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12217	Buccinum undatum	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6809	Cailliea cinerea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13417	Campanula medium	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15428	Cheilanthes tenuifolia	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5127	Cladocroce incurvata	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1655	Corydendrium parasiticum	Species	Oceaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13036	Culicinomyces clavisporus	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25278	Cystofilobasidium infirmominiatum	Species	Cystofilobasidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12451	Dermocybe cinnabarina	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15037	Echinops spinosissimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15773	Ecteinascidia thurstoni	Species	Perophoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20404.1	Eruca vesicaria subsp. sativa	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15879	Euphorbia nivulia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO639	Formica polyctena	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9314	Gouania ulmifolia	Species	Gobiesocidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5719	Hedyotis lawsoniae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16740	Helipterum venustum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16774	Hermidium alipes	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10877	Humboldtia laurifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16301	Ilex macropoda	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11365	Lecidea lithophila	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16453	Lycium cestroides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2584	Monostroma fuscum	Species	Monostromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16617	Paepalanthus hilairei	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13577	Pieris formosa	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO73	Pseudanabaena persicina	Species	Pseudanabaenaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16534	Pterocaulon alopecuroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14591	Rhabdodendron amazonicum	Species	Rhabdodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13733	Saccharopolyspora erythraea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13931	Selaginella uncinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10443	Sloanea zuliaensis	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7023	Tetracera rosiflora	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14107	Teucrium montanum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12764	Tillandsia fragrans	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15983	Udotea cyathiformis	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16206	Umbilicaria indica	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26508	Uvariopsis tripetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29	Laburnum alpinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2783	Lobophytum sarcophytoides	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5562	Armillaria novae-zelandiae	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6518	Aspilia laevissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO943	Carex nigra	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1860	Ceratium reticulatum	Species	Ceratiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4638	Cynoglossum gansuense	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13417	Campanula medium	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13931	Selaginella uncinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20404.1	Eruca vesicaria subsp. sativa	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20404.1	Eruca vesicaria subsp. sativa	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13931	Selaginella uncinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13577	Pieris formosa	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13417	Campanula medium	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26508	Uvariopsis tripetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15983	Udotea cyathiformis	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12764	Tillandsia fragrans	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15879	Euphorbia nivulia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO73	Pseudanabaena persicina	Species	Pseudanabaenaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16774	Hermidium alipes	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25715	Senna siamea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15674	Acanthosyris spinescens	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9314	Gouania ulmifolia	Species	Gobiesocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15773	Ecteinascidia thurstoni	Species	Perophoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13036	Culicinomyces clavisporus	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16453	Lycium cestroides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6809	Cailliea cinerea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9909	Sarcophyton crassocaule	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13931	Selaginella uncinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16617	Paepalanthus hilairei	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12217	Buccinum undatum	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16301	Ilex macropoda	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16740	Helipterum venustum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1655	Corydendrium parasiticum	Species	Oceaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13264	Alstonia lanceolifera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7023	Tetracera rosiflora	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16206	Umbilicaria indica	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14107	Teucrium montanum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14909	Artemisia caerulescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11762	Agrimonia eupatoria	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5719	Hedyotis lawsoniae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12451	Dermocybe cinnabarina	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29	Laburnum alpinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14434	Alluaudia humbertii	Species	Didiereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14591	Rhabdodendron amazonicum	Species	Rhabdodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2584	Monostroma fuscum	Species	Monostromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25278	Cystofilobasidium infirmominiatum	Species	Cystofilobasidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5127	Cladocroce incurvata	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20404.1	Eruca vesicaria subsp. sativa	Subspecies	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15037	Echinops spinosissimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26988	Acinos thymoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10443	Sloanea zuliaensis	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16534	Pterocaulon alopecuroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15428	Cheilanthes tenuifolia	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13733	Saccharopolyspora erythraea	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13417	Campanula medium	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5562	Armillaria novae-zelandiae	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11365	Lecidea lithophila	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13577	Pieris formosa	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10877	Humboldtia laurifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6518	Aspilia laevissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO639	Formica polyctena	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2783	Lobophytum sarcophytoides	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4638	Cynoglossum gansuense	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1860	Ceratium reticulatum	Species	Ceratiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO943	Carex nigra	Species	Cyperaceae	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
EC50	1
IC50	1

Activity Type	# Activity
Individual protein	1
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3973	Individual protein	Endothelial PAS domain-containing protein 1	Homo sapiens	EC50	=	183300.0	nM	PMID[21353547]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	291200.0	nM	PMID[21353547]

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 NPC83838 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	30957
0.1-0.2	18249
0.2-0.3	527
0.3-0.4	91
0.4-0.5	16
0.5-0.6	7
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC143810
1.0	High Similarity	NPC605986
1.0	High Similarity	NPC609177
0.7	Intermediate Similarity	NPC276290
0.6545	Remote Similarity	NPC606888
0.6481	Remote Similarity	NPC607496
0.6316	Remote Similarity	NPC485432
0.6182	Remote Similarity	NPC608635
0.6111	Remote Similarity	NPC603424
0.5893	Remote Similarity	NPC600730
0.5741	Remote Similarity	NPC605688
0.5741	Remote Similarity	NPC609651
0.5517	Remote Similarity	NPC129630
0.5283	Remote Similarity	NPC127824
0.5273	Remote Similarity	NPC485573
0.5085	Remote Similarity	NPC246621

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC83838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7931
0.1-0.2	1206
0.2-0.3	11
0.3-0.4	1
0.4-0.5	1
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