NPASS Compound

Natural Product: NPC195165

Natural Product ID	NPC195165
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(R)-2-Hydroxy-N-((2S,3S,4R)-1,3,4-Trihydroxy-14-Methylpentadecan-2-Yl)Docosanamide
IUPAC Name	(2R)-2-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxy-14-methylpentadecan-2-yl]docosanamide
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509564
PubChem CID	10371786
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000331] Fatty amides [CHEMONTID:0001096] N-acyl amines

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 121120 0 0 0 0 0 0 0 0999 V2000 12.4365 2.6701 3.3115 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2551 2.7194 1.8024 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0845 1.6819 1.1184 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9194 1.7420 -0.3552 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4554 1.4857 -0.7461 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3868 1.5523 -2.2248 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1071 1.3542 -2.9199 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4652 0.0539 -2.8874 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0437 -0.5443 -1.5960 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3365 -1.8689 -1.9788 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8135 -2.5908 -0.7783 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7720 -1.8207 -0.0225 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5345 -1.5201 -0.8575 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8751 -2.7743 -1.3147 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6558 -2.6589 -2.1299 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4903 -1.9225 -1.4814 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1536 -2.5996 -0.2167 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0431 -2.1474 0.6227 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.2824 0.2162 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8532 -1.6325 -1.0244 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6630 -0.1801 -1.0261 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3336 0.6247 0.0164 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0652 0.3994 0.9341 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8785 0.0521 1.9347 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0624 -0.8049 1.8502 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2641 -0.4994 1.0792 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3388 0.3253 1.6850 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4899 0.4406 0.6503 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0233 -0.9350 0.2845 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6010 -1.7145 1.3697 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8845 -1.2588 1.9544 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1180 -1.3944 1.2046 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5543 -0.8125 -0.0310 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8395 0.6192 -0.2181 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7715 1.6051 0.0068 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2796 3.0377 -0.2687 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7339 3.0982 -1.7038 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4585 3.2940 0.6435 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0351 -0.3023 -0.2766 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6168 -2.0958 1.3702 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1585 1.2882 2.8204 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7058 2.3292 2.0835 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0086 2.0313 -0.1280 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1368 0.2983 -2.2783 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4578 3.7070 3.7191 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6058 2.1182 3.7748 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4013 2.1854 3.5673 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5561 3.7465 1.4746 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1934 2.5580 1.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1629 1.7712 1.3802 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7788 0.6767 1.5277 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2707 2.7017 -0.7320 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5199 0.9204 -0.7996 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9176 2.4136 -0.3702 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0929 0.6258 -0.2256 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8262 2.5602 -2.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1920 0.8464 -2.6163 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2146 1.6356 -4.0325 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3302 2.1123 -2.5430 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5794 -0.0123 -3.6109 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2224 -0.6993 -3.3229 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4673 0.0674 -0.9202 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9367 -0.9440 -1.0151 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5475 -1.7027 -2.7119 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1230 -2.4964 -2.4384 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6389 -2.7886 -0.0363 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4325 -3.5601 -1.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4147 -2.4862 0.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1905 -0.8702 0.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8703 -0.8982 -0.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7611 -0.8885 -1.7334 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6363 -3.3165 -1.9651 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7793 -3.4533 -0.4370 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9021 -2.2171 -3.1150 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2840 -3.6810 -2.3497 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7830 -0.8331 -1.3206 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7188 -1.8779 -2.2523 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9919 -3.7234 -0.3797 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1324 -2.6323 0.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2653 -1.0711 0.9604 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1520 -2.7179 1.6192 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9736 -1.9112 1.1009 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5490 -3.4243 0.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9656 -1.8959 -1.1830 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4103 -2.1402 -1.8991 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4420 0.0627 -1.0692 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.5750 2.7435 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3917 -1.0767 2.9012 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8013 -1.5610 1.0234 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7912 -0.2555 2.5298 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1005 1.3477 1.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0949 0.9457 -0.2266 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2999 0.9610 1.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2787 -1.5501 -0.2687 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8169 -0.7157 -0.4940 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7538 -2.7901 0.9643 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8284 -1.9169 2.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7892 -0.2047 2.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0122 -1.8489 2.9217 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9610 -1.1717 1.9828 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2777 -2.5506 1.0778 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0039 -1.2488 -0.9533 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6036 -1.3141 -0.2456 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2698 0.8355 -1.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6870 0.8721 0.5145 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8498 1.4299 -0.5692 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5108 1.6369 1.0852 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4540 3.7191 -0.0562 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8108 2.8055 -1.7363 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1439 2.3857 -2.3340 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5946 4.1285 -2.0822 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3532 2.8303 0.1820 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2300 2.9353 1.6476 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6033 4.4090 0.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9781 -1.0922 -0.8251 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7154 -2.0405 0.4011 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1752 1.6779 3.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7431 1.0335 3.7124 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4165 3.2168 2.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5020 2.7286 0.4070 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4065 0.4677 -2.9157 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 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 3 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 26 39 1 0 25 40 1 0 24 41 1 0 41 42 1 0 22 43 1 0 21 44 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 9 63 1 0 10 64 1 0 10 65 1 0 11 66 1 0 11 67 1 0 12 68 1 0 12 69 1 0 13 70 1 0 13 71 1 0 14 72 1 0 14 73 1 0 15 74 1 0 15 75 1 0 16 76 1 0 16 77 1 0 17 78 1 0 17 79 1 0 18 80 1 0 18 81 1 0 19 82 1 0 19 83 1 0 20 84 1 0 20 85 1 0 21 86 1 6 24 87 1 1 25 88 1 1 26 89 1 6 27 90 1 0 27 91 1 0 28 92 1 0 28 93 1 0 29 94 1 0 29 95 1 0 30 96 1 0 30 97 1 0 31 98 1 0 31 99 1 0 32100 1 0 32101 1 0 33102 1 0 33103 1 0 34104 1 0 34105 1 0 35106 1 0 35107 1 0 36108 1 0 37109 1 0 37110 1 0 37111 1 0 38112 1 0 38113 1 0 38114 1 0 39115 1 0 40116 1 0 41117 1 0 41118 1 0 42119 1 0 43120 1 0 44121 1 0 M END

Standard InCHIKey	MDBZNSRDVWLBHE-YUYNGSOASA-N
Standard InCHI	InChI=1S/C38H77NO5/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21-25-28-31-36(42)38(44)39-34(32-40)37(43)35(41)30-27-24-22-19-20-23-26-29-33(2)3/h33-37,40-43H,4-32H2,1-3H3,(H,39,44)/t34-,35+,36+,37-/m0/s1
SMILES	CCCCCCCCCCCCCCCCCCCC[C@H](C(=N[C@H]([C@@H]([C@@H](CCCCCCCCCC(C)C)O)O)CO)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	627.58	Volume:	718.115 ? Van der Waals volume.
Dense:	0.874	LogP:	9.211 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.048 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.431 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	34.0	Rigid Bonds:	1.0
TPSA:	113.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	5.0	Rings:	0.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.028	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.017	Fsp³:	0.974
MCE-18:	6.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.702	Fluc inhibitor:	0.062 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.052	Promiscuous compounds:	0.123

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.249	MDCK Permeability:	-4.937
Pgp-inhibitor:	0.0	Pgp-substrate:	0.092
PAMPA:	0.0 ? 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):	0.934
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.957
Plasma Protein Binding (PPB):	101.353%	Volume Distribution (VD):	1.812
Fu:	0.51% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.76
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.912
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.973	CYP2C9-substrate:	0.336
CYP2D6-inhibitor:	0.123	CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.14 ? 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):

3.389

Half-life (T1/2):

3.43

ADMET: Toxicity

hERG Blockers:	0.533	hERG Blockers (10um):	0.712
Human Hepatotoxicity (H-HT):	0.855	Drug-induced Liver Injury (DILI):	0.07
AMES Toxicity:	0.016	Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.137	Skin Sensitization:	1.0
Carcinogencity:	0.159	Eye Corrosion:	0.182
Eye Irritation:	0.983	Respiratory Toxicity:	0.983
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.539
Hematotoxicity:	0.112	Drug-induced Nephrotoxicity:	0.238
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.962	Hek293 Cytotoxicity:	0.105
BCF:	0.586 ? 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:	4.986 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.556 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.319 ? 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
NPO32609	cystodytes cf. dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869204]

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
ED50	1

Activity Type	# Activity
Others	1

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
NPT2	Others	Unspecified	n.a.	ED50	=	100.0	ug ml-1	PubChem BioAssay data set

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 NPC195165 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	15966
0.1-0.2	31998
0.2-0.3	1792
0.3-0.4	93
0.4-0.5	4
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8718	High Similarity	NPC145627
0.7727	Intermediate Similarity	NPC217095
0.7727	Intermediate Similarity	NPC264417
0.5714	Remote Similarity	NPC288086

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC195165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5097
0.1-0.2	3842
0.2-0.3	205
0.3-0.4	6
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