NPASS Compound

Natural Product: NPC8979

Natural Product ID	NPC8979
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Phytosphingosine
IUPAC Name	(2S,3S,4R)-2-aminooctadecane-1,3,4-triol
Synonyms	Phytosphingosine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL236036
PubChem CID	122121
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004707] Organic nitrogen compounds [CHEMONTID:0000278] Organonitrogen compounds [CHEMONTID:0002449] Amines [CHEMONTID:0002460] Alkanolamines [CHEMONTID:0001852] 1,3-aminoalcohols

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 61 60 0 0 0 0 0 0 0 0999 V2000 -7.8274 0.1959 0.9795 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3265 0.1373 0.7518 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9086 -1.2750 0.9971 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4258 -1.4639 0.8149 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0533 -1.1032 -0.5905 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5912 -1.3133 -0.8130 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7647 -0.4816 0.1045 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0027 0.9947 -0.0256 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7265 1.5378 -1.3834 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3155 1.3131 -1.8039 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6726 1.9744 -0.8729 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0550 1.6527 -1.4599 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0983 2.2708 -0.6083 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1150 1.8070 0.7916 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3875 0.3586 0.9993 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7219 -0.0491 0.4486 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2185 -1.3847 0.9457 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6219 -1.6506 0.4132 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0457 -2.8624 0.9445 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3842 -2.4554 0.5206 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6398 0.9170 0.9266 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3966 -0.4641 0.5395 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2226 1.2123 0.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2915 -0.3461 0.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0830 -0.3991 1.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1588 0.3938 -0.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7776 0.8322 1.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4336 -1.9759 0.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1620 -1.5402 2.0539 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1985 -2.5144 1.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8560 -0.7663 1.5016 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2670 -0.0285 -0.8100 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6708 -1.6603 -1.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3908 -2.3956 -0.6414 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2932 -1.1475 -1.8794 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6727 -0.7235 -0.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9137 -0.7667 1.1642 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0754 1.2042 0.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3554 1.5223 0.7128 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 1.2163 -2.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8895 2.6546 -1.3103 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0455 0.2182 -1.7994 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1292 1.6370 -2.8529 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5275 3.0530 -0.7654 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5542 1.4989 0.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0992 0.5858 -1.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1181 2.1808 -2.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8861 3.3869 -0.5927 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1175 2.2323 -1.0964 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8465 2.4376 1.3643 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1222 2.0679 1.2461 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4553 0.2402 2.1524 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7303 0.0002 -0.6430 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3474 -1.3697 2.0682 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2606 -0.8264 0.8465 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6730 -1.6003 -0.6794 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4708 -3.4476 0.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6763 -2.8667 -0.4103 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2905 -3.2234 1.2323 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0356 1.4358 0.1847 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7291 -1.0682 -0.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 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 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 16 21 1 0 15 22 1 0 1 23 1 0 1 24 1 0 1 25 1 0 2 26 1 0 2 27 1 0 3 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 0 5 33 1 0 6 34 1 0 6 35 1 0 7 36 1 0 7 37 1 0 8 38 1 0 8 39 1 0 9 40 1 0 9 41 1 0 10 42 1 0 10 43 1 0 11 44 1 0 11 45 1 0 12 46 1 0 12 47 1 0 13 48 1 0 13 49 1 0 14 50 1 0 14 51 1 0 15 52 1 1 16 53 1 6 17 54 1 1 18 55 1 0 18 56 1 0 19 57 1 0 20 58 1 0 20 59 1 0 21 60 1 0 22 61 1 0 M END

Standard InCHIKey	AERBNCYCJBRYDG-KSZLIROESA-N
Standard InCHI	InChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1
SMILES	CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)N)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	317.29	Volume:	357.252 ? Van der Waals volume.
Dense:	0.888	LogP:	4.319 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.284 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.698 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	0.0
TPSA:	86.71 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	5.0	Rings:	0.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.329	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.197	Fsp³:	1.0
MCE-18:	3.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.614	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.222	Promiscuous compounds:	0.051

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.12	MDCK Permeability:	-4.818
Pgp-inhibitor:	0.0	Pgp-substrate:	0.149
PAMPA:	0.116 ? 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):	0.178
20% Bioavailability (F20%):	0.528	30% Bioavailability (F30%):	0.936
50% Bioavailability (F50%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.338
Plasma Protein Binding (PPB):	97.649%	Volume Distribution (VD):	0.723
Fu:	3.126% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.81
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.388
BSEP inhibitor:	0.03

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.37	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.85	CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.991	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.952
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.986
HLM stability:	0.0 ? 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):

4.581

Half-life (T1/2):

0.975

ADMET: Toxicity

hERG Blockers:	0.233	hERG Blockers (10um):	0.404
Human Hepatotoxicity (H-HT):	0.666	Drug-induced Liver Injury (DILI):	0.011
AMES Toxicity:	0.086	Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.063	Skin Sensitization:	0.989
Carcinogencity:	0.176	Eye Corrosion:	0.87
Eye Irritation:	0.971	Respiratory Toxicity:	0.879
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.76
Hematotoxicity:	0.14	Drug-induced Nephrotoxicity:	0.359
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.189	Hek293 Cytotoxicity:	0.034
BCF:	1.581 ? 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:	4.667 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.652 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.575 ? 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
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0003-9861(62)90112-1]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11035032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12902239]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[13835567]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14389294]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1449509]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14607989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15375647]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15744050]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16850348]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17439666]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22031445]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2405251]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24305546]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24678285]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24733517]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24831709]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24981409]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2687322]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3289762]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4266242]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4616942]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5764336]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6306574]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[767332]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7929110]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8017107]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8798704]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8852895]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8971708]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748245]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20338	Mus musculus	Species	Muridae	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
Kcat/Km	3
Potency	3
Inhibition	8
IC50	6
Ratio IC50	3
MFC	3
Ki	1

Activity Type	# Activity
Individual protein	7
Cell line	7
Single protein	4
Organism	8
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT198	Individual protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	29934.9	nM	PubChem BioAssay data set
NPT27302	Single protein	Endoglycoceramidase II	Rhodococcus sp	Kcat/Km	=	3.1	/s/M	PMID[19525967]
NPT27302	Single protein	Endoglycoceramidase II	Rhodococcus sp	Kcat/Km	=	2.1	/s/M	PMID[19525967]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	7.46	%	PMID[23062825]
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-6.311	%	DOI[10.6019/CHEMBL4495564]
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	4.33	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	0.56	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	24.41	%	PMID[23062825]
NPT53	Individual protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	31622.8	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell line	Jurkat	Homo sapiens	IC50	=	3750.0	nM	PMID[17400555]
NPT15	Cell line	Jurkat	Homo sapiens	IC50	=	6570.0	nM	PMID[17400555]
NPT15	Cell line	Jurkat	Homo sapiens	IC50	=	5290.0	nM	PMID[17400555]
NPT15	Cell line	Jurkat	Homo sapiens	IC50	=	4120.0	nM	PMID[17400555]
NPT15	Cell line	Jurkat	Homo sapiens	Ratio IC50	=	1.8	n.a.	PMID[17400555]
NPT15	Cell line	Jurkat	Homo sapiens	Ratio IC50	=	1.4	n.a.	PMID[17400555]
NPT15	Cell line	Jurkat	Homo sapiens	Ratio IC50	=	1.1	n.a.	PMID[17400555]
NPT554	Organism	Candida glabrata	Candida glabrata	MFC	=	1.0	ug ml-1	PMID[18524581]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	48.01	%	DOI[10.21203/rs.3.rs-23951/v1]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.13	%	DOI[10.6019/CHEMBL4495565]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	DOI[10.6019/CHEMBL4651402]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	DOI[10.6019/CHEMBL4651402]
NPT20	Organism	Candida albicans	Candida albicans	MFC	=	1.0	ug ml-1	PMID[18524581]
NPT2	Others	Unspecified	n.a.	Ki	=	850000.0	nM	PMID[19525967]

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 NPC8979 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	34068
0.1-0.2	14772
0.2-0.3	880
0.3-0.4	115
0.4-0.5	16
0.5-0.6	6
0.6-0.7	1
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
0.6667	Remote Similarity	NPC123814
0.5556	Remote Similarity	NPC478319
0.5556	Remote Similarity	NPC121062
0.5556	Remote Similarity	NPC29222
0.5556	Remote Similarity	NPC96966
0.5556	Remote Similarity	NPC602997
0.5152	Remote Similarity	NPC47333

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC8979 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7543
0.1-0.2	1536
0.2-0.3	63
0.3-0.4	5
0.4-0.5	1
0.5-0.6	1
0.6-0.7	1
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
0.6667	Remote Similarity	NPD3215	Phase 2
0.5556	Remote Similarity	NPD3214	Discontinued

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