NPASS Compound

Natural Product: NPC5441

Natural Product ID	NPC5441
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FAGOJCSZVVRBFD-KAKDVIIHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001691] Steroid esters

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 57 60 0 0 0 0 0 0 0 0999 V2000 -1.4934 4.6829 -0.1779 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7067 3.5009 0.2851 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1986 3.7257 1.1361 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9342 2.2400 -0.1707 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1960 1.1324 0.2640 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7295 0.5574 -0.8012 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7008 -0.3065 0.0191 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4022 0.4987 1.0595 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9374 -1.4637 0.5097 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9076 -2.3811 -0.7219 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2882 -2.2293 -1.3262 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7663 -0.9062 -0.8956 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0441 -0.8506 -0.3379 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1031 -0.1204 -0.7850 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9181 0.5793 -1.8067 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4421 -0.0939 -0.1582 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4140 -1.2406 1.0970 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2587 -2.4655 0.8136 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6292 -2.2215 1.4212 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2667 -1.0557 0.7795 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5403 -0.9687 0.4838 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0062 0.2825 -0.1631 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1851 0.6436 0.1346 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1318 1.0425 -1.0933 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7507 0.3545 -1.0208 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4544 0.1337 0.4115 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0637 0.0695 0.9072 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1407 4.9608 -1.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3587 5.5510 0.4748 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5877 4.4194 -0.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5420 1.5682 1.0085 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1326 -0.0590 -1.4629 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2487 1.3772 -1.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9132 0.4802 2.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4483 0.1176 1.2496 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5756 1.5537 0.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6209 -2.0338 1.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8017 -3.4342 -0.3906 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1841 -2.0843 -1.4734 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9268 -3.0885 -1.0514 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2016 -2.2977 -2.4526 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7937 -0.2310 -1.7798 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5415 -1.0621 0.4093 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5456 0.7297 0.5561 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2053 -0.0971 -0.9523 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2302 -1.3927 2.2224 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2973 -2.7400 -0.2433 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8120 -3.3166 1.3556 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2486 -3.1173 1.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4440 -1.9369 2.4859 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2199 -1.7912 0.7099 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5494 0.9480 -2.1075 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0553 2.1062 -0.8215 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0295 0.8514 -1.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9827 -0.6176 -1.5592 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9859 0.9820 0.9669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1461 0.5147 1.9714 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 9 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 5 1 0 12 7 1 0 27 17 1 0 26 20 1 0 1 28 1 0 1 29 1 0 1 30 1 0 5 31 1 1 6 32 1 0 6 33 1 0 8 34 1 0 8 35 1 0 8 36 1 0 9 37 1 1 10 38 1 0 10 39 1 0 11 40 1 0 11 41 1 0 12 42 1 6 16 43 1 0 16 44 1 0 16 45 1 0 17 46 1 1 18 47 1 0 18 48 1 0 19 49 1 0 19 50 1 0 21 51 1 0 24 52 1 0 24 53 1 0 25 54 1 0 25 55 1 0 26 56 1 1 27 57 1 1 M END

Standard InCHIKey	FAGOJCSZVVRBFD-KAKDVIIHSA-N
Standard InCHI	InChI=1S/C22H30O5/c1-12(23)26-19-11-22(3)18(8-9-20(22)27-13(2)24)17-6-4-14-10-15(25)5-7-16(14)21(17)19/h10,16-21H,4-9,11H2,1-3H3/t16-,17-,18+,19+,20-,21-,22-/m0/s1
SMILES	CC(=O)O[C@@H]1C[C@@]2(C)[C@H](CC[C@@H]2OC(=O)C)[C@@H]2CCC3=CC(=O)CC[C@@H]3[C@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	374.21	Volume:	388.248 ? Van der Waals volume.
Dense:	0.964	LogP:	2.182 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.419 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.626 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	23.0
TPSA:	69.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.691	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.405	Fsp³:	0.773
MCE-18:	67.949 ? 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:	0.414	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.372	Promiscuous compounds:	0.882

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.56	MDCK Permeability:	-4.675
Pgp-inhibitor:	0.112	Pgp-substrate:	0.367
PAMPA:	0.013 ? 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):	0.0
20% Bioavailability (F20%):	0.928	30% Bioavailability (F30%):	0.457
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.209	MRP1:	0.999
Plasma Protein Binding (PPB):	75.385%	Volume Distribution (VD):	-0.214
Fu:	17.476% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.019
OATP1B3 inhibitor:	0.001	BCRP inhibitor:	0.007
BSEP inhibitor:	0.921

ADMET: Metabolism

CYP1A2-inhibitor:	0.262	CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.208	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.276
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.816	CYP3A4-substrate:	0.541
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.987
HLM stability:	0.895 ? 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):

6.883

Half-life (T1/2):

0.701

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.18
Human Hepatotoxicity (H-HT):	0.526	Drug-induced Liver Injury (DILI):	0.611
AMES Toxicity:	0.694	Rat Oral Acute Toxicity:	0.528
Maximum Recommended Daily Dose:	0.506	Skin Sensitization:	0.96
Carcinogencity:	0.753	Eye Corrosion:	0.02
Eye Irritation:	0.319	Respiratory Toxicity:	0.243
Drug-induced Neurotoxicity:	0.453	Ototoxicity:	0.288
Hematotoxicity:	0.844	Drug-induced Nephrotoxicity:	0.389
Genotoxicity:	0.99	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.547	Hek293 Cytotoxicity:	0.474
BCF:	0.609 ? 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:	3.246 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.508 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.132 ? 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
NPO12029	Sicana odorifera	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11312792]
NPO15997	Aglaia cordata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754603]
NPO11261	Euclea natalensis	Species	Ebenaceae	Eukaryota	root bark	n.a.	n.a.	PMID[15568795]
NPO25076	Salicornia herbacea	Species	Chenopodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16276965]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[17405024]
NPO22561	Dickeya chrysanthemi	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18803373]
NPO25076	Salicornia herbacea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22652051]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[27908762]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO6038	Acanthamoeba culbertsoni	Species	Acanthamoebidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15302	Acronychia acidula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15997	Aglaia cordata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15092	Alternaria infectoria	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1159	Artemisia laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23600	Bridelia moonii	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15723	Bupleurum aureum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11598	Callitris macleayana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10093	Castanopsis hystrix	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22561	Dickeya chrysanthemi	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15410	Erlangea cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11261	Euclea natalensis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7859	Euonymus atropurpurea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1836	Eupatorium recurvans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13232	Gaillardia tontalensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15903	Goupia tomentosa	Species	Goupiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8604	Helichrysum zeyheri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9145	Herbertus aduncus	Species	Herbertaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13481	Laurencia claviformis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5208	Ligusticum lucidum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13749	Luvunga scandens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4299	Michelia longifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27213	Nephrolepis biserrata	Species	Lomariopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10595	Othonna cylindrica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12805	Othonna intermedia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14624	Pertusaria pseudocorallina	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14334	Picea jezoensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14873	Pityrodia ternifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7047	Psiadia arabica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2740	Pteris plumbea	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15398	Rhizopus stolonifer	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12291	Rhodococcus ruber	Species	Nocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25076	Salicornia herbacea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14467	Senecio taiwanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13895	Sessibugula translucens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12029	Sicana odorifera	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26219	Sorbus coronata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15813	Spiraea formosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12505	Stigmodera macularia	Species	Buprestidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9204	Streptomyces argillaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14893	Streptomyces eurocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15628	Strychnos panamensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9541	Suaeda salsa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16742.1	Syringa pubescens subsp. patula	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14061	Tetraploa aristata	Species	Tetraplosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13356	Thalictrum fauriei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13028	Trichoscypha acuminata	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14205	Uraria picta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14746	Uroblaniulus canadensis	Species	Parajulidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14334	Picea jezoensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13749	Luvunga scandens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15723	Bupleurum aureum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14334	Picea jezoensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13749	Luvunga scandens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15723	Bupleurum aureum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12505	Stigmodera macularia	Species	Buprestidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15813	Spiraea formosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7859	Euonymus atropurpurea	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10595	Othonna cylindrica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7047	Psiadia arabica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6038	Acanthamoeba culbertsoni	Species	Acanthamoebidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13232	Gaillardia tontalensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15092	Alternaria infectoria	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15398	Rhizopus stolonifer	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12291	Rhodococcus ruber	Species	Nocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14205	Uraria picta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11598	Callitris macleayana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8604	Helichrysum zeyheri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5208	Ligusticum lucidum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13028	Trichoscypha acuminata	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15723	Bupleurum aureum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1836	Eupatorium recurvans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14893	Streptomyces eurocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22561	Dickeya chrysanthemi	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13481	Laurencia claviformis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16742.1	Syringa pubescens subsp. patula	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15997	Aglaia cordata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12805	Othonna intermedia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9145	Herbertus aduncus	Species	Herbertaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14061	Tetraploa aristata	Species	Tetraplosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11796	Morus australis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10093	Castanopsis hystrix	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14873	Pityrodia ternifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9204	Streptomyces argillaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14624	Pertusaria pseudocorallina	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1159	Artemisia laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27213	Nephrolepis biserrata	Species	Lomariopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13749	Luvunga scandens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15302	Acronychia acidula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11261	Euclea natalensis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15903	Goupia tomentosa	Species	Goupiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13356	Thalictrum fauriei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2740	Pteris plumbea	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13895	Sessibugula translucens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14746	Uroblaniulus canadensis	Species	Parajulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14467	Senecio taiwanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12029	Sicana odorifera	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15628	Strychnos panamensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26219	Sorbus coronata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15410	Erlangea cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4299	Michelia longifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23600	Bridelia moonii	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9541	Suaeda salsa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14334	Picea jezoensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25076	Salicornia herbacea	Species	Chenopodiaceae	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 NPC5441 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	18886
0.1-0.2	27788
0.2-0.3	3105
0.3-0.4	75
0.4-0.5	3
0.5-0.6	2
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
0.5833	Remote Similarity	NPC323765
0.5781	Remote Similarity	NPC195640

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC5441 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6398
0.1-0.2	2535
0.2-0.3	171
0.3-0.4	32
0.4-0.5	10
0.5-0.6	4
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
0.5781	Remote Similarity	NPD7146	Phase 4
0.5278	Remote Similarity	NPD6858	Phase 4
0.5238	Remote Similarity	NPD5330	Phase 4
0.5077	Remote Similarity	NPD6409	Approved

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