NPASS Compound

Natural Product: NPC288086

Natural Product ID	NPC288086
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S,3R,4E)-2-N-(2'-Hydroxytetracosanoyl)-Heptadecasphinga-4-Ene
IUPAC Name	(2R)-N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]-2-hydroxytetracosanamide
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2268779
PubChem CID	76308629
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000257] Sphingolipids [CHEMONTID:0001418] Ceramides

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 130129 0 0 0 0 0 0 0 0999 V2000 16.4764 -0.1569 1.8594 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5202 -1.2540 0.8243 C 0 0 0 0 0 0 0 0 0 0 0 0 16.9223 -0.7482 -0.5096 C 0 0 0 0 0 0 0 0 0 0 0 0 16.1714 0.3282 -1.1412 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7636 0.1526 -1.4798 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7969 -0.0413 -0.3729 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4103 -0.1340 -1.0168 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3065 -0.3850 -0.0068 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2380 0.6946 0.9704 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3005 0.7173 2.0748 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8397 0.7475 1.9549 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1523 -0.3690 1.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6603 -0.2717 1.3037 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1666 1.0034 0.6615 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6260 1.1132 -0.7547 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2695 0.0891 -1.7089 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9683 -0.1088 -2.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7486 -0.1770 -1.5085 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1929 1.1356 -1.0633 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0156 1.0112 -0.1516 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9027 0.2546 -0.8872 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2356 0.1452 0.0851 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3876 -0.6067 -0.4915 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0046 -0.0357 -1.6875 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2035 0.3712 -1.8276 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2699 0.3827 -0.8661 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1033 -0.8635 -1.0330 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1210 -1.0766 0.0091 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0418 -0.6709 1.2410 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0550 -0.8810 2.2760 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3208 -1.5423 1.8870 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2106 -0.7979 0.9506 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4417 -1.6300 0.6339 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3801 -0.9058 -0.2933 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8693 0.3952 0.2918 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5947 0.2253 1.5788 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8001 -0.6460 1.4795 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7838 0.0094 0.4805 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.9914 -0.8539 0.3797 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.0216 -0.3960 -0.5716 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.6702 0.9139 -0.3467 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.7641 2.0933 -0.4174 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6805 -0.9526 -2.2790 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1305 1.6115 -1.2444 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3498 2.7613 -1.1657 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2143 0.1005 -2.8591 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2632 -0.9768 0.5135 O 0 0 0 0 0 0 0 0 0 0 0 0 17.1997 0.6309 1.6411 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4558 0.2488 1.9946 H 0 0 0 0 0 0 0 0 0 0 0 0 16.7943 -0.6057 2.8375 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6735 -1.9328 0.8120 H 0 0 0 0 0 0 0 0 0 0 0 0 17.4085 -1.9588 1.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 16.9520 -1.6847 -1.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 18.0363 -0.4739 -0.4962 H 0 0 0 0 0 0 0 0 0 0 0 0 16.7562 0.6728 -2.0742 H 0 0 0 0 0 0 0 0 0 0 0 0 16.2384 1.3024 -0.5140 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6494 -0.7061 -2.2293 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4556 1.0509 -2.1103 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9412 -0.9628 0.1578 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8615 0.8208 0.3313 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4637 -0.9720 -1.7491 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2121 0.8464 -1.4893 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6241 -1.3509 0.5017 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4213 -0.5869 -0.6390 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1880 1.6956 0.4211 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2834 0.7758 1.4351 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5234 -0.1516 2.8023 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5647 1.5989 2.7687 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4469 0.7004 3.0279 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4536 1.7602 1.6410 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4444 -1.3129 1.7932 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4016 -0.4484 0.1757 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2733 -1.1722 0.7629 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2917 -0.3220 2.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6041 1.9063 1.1938 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1022 1.0754 0.8610 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7524 1.2404 -0.7320 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2656 2.1569 -1.0849 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5766 -0.9644 -1.3004 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0658 0.1315 -2.5895 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8048 0.6470 -3.1821 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0634 -1.0726 -2.9587 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9938 -0.7734 -2.0913 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8585 -0.7923 -0.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8972 1.8725 -0.7307 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7131 1.6292 -2.0235 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6327 2.0094 0.1106 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2749 0.4710 0.7874 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2261 -0.7453 -1.2167 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6164 0.8498 -1.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0603 -0.3700 1.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4932 1.1781 0.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9338 -1.6061 -0.8298 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8764 0.5639 0.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4086 -1.7546 -0.9638 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9947 -1.6624 -0.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1441 -0.1254 1.5326 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5864 -1.5520 3.0703 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2318 0.0709 2.8558 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1398 -2.5674 1.4452 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8662 -1.7856 2.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5304 0.1329 1.5280 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7950 -0.4103 0.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9129 -1.9943 1.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0983 -2.5435 0.0851 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7695 -0.6256 -1.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2238 -1.5473 -0.5285 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0139 1.1225 0.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5255 0.8809 -0.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9477 -0.1384 2.4075 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9567 1.2284 1.9374 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3091 -0.8068 2.4478 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5086 -1.6178 1.0352 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3420 0.1047 -0.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9409 1.0106 0.8997 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.4466 -0.9817 1.4107 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.6895 -1.9093 0.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -17.8477 -1.1665 -0.5752 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.6215 -0.4575 -1.6345 H 0 0 0 0 0 0 0 0 0 0 0 0 -18.1883 0.8795 0.6696 H 0 0 0 0 0 0 0 0 0 0 0 0 -18.4948 1.0590 -1.0958 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.8690 1.8808 -1.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.5880 2.5526 0.5744 H 0 0 0 0 0 0 0 0 0 0 0 0 -17.2757 2.9409 -0.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0839 -1.1089 -3.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4736 1.5172 -2.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9740 1.7155 -0.5644 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4969 2.5953 -1.6264 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6843 0.1286 -3.7489 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7792 -0.9484 1.3681 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 1 0 23 24 1 0 24 25 2 3 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 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 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 27 43 1 0 26 44 1 0 44 45 1 0 24 46 1 0 23 47 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 0 2 52 1 0 3 53 1 0 3 54 1 0 4 55 1 0 4 56 1 0 5 57 1 0 5 58 1 0 6 59 1 0 6 60 1 0 7 61 1 0 7 62 1 0 8 63 1 0 8 64 1 0 9 65 1 0 9 66 1 0 10 67 1 0 10 68 1 0 11 69 1 0 11 70 1 0 12 71 1 0 12 72 1 0 13 73 1 0 13 74 1 0 14 75 1 0 14 76 1 0 15 77 1 0 15 78 1 0 16 79 1 0 16 80 1 0 17 81 1 0 17 82 1 0 18 83 1 0 18 84 1 0 19 85 1 0 19 86 1 0 20 87 1 0 20 88 1 0 21 89 1 0 21 90 1 0 22 91 1 0 22 92 1 0 23 93 1 6 26 94 1 1 27 95 1 6 28 96 1 0 29 97 1 0 30 98 1 0 30 99 1 0 31100 1 0 31101 1 0 32102 1 0 32103 1 0 33104 1 0 33105 1 0 34106 1 0 34107 1 0 35108 1 0 35109 1 0 36110 1 0 36111 1 0 37112 1 0 37113 1 0 38114 1 0 38115 1 0 39116 1 0 39117 1 0 40118 1 0 40119 1 0 41120 1 0 41121 1 0 42122 1 0 42123 1 0 42124 1 0 43125 1 0 44126 1 0 44127 1 0 45128 1 0 46129 1 0 47130 1 0 M END

Standard InCHIKey	WAYLDHLWVYQNSQ-CFBMXOPXSA-N
Standard InCHI	InChI=1S/C42H83NO4/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-37-41(46)42(47)43-39(38-44)40(45)36-34-32-30-28-26-24-16-14-12-10-8-6-4-2/h34,36,39-41,44-46H,3-33,35,37-38H2,1-2H3,(H,43,47)/b36-34+/t39-,40+,41+/m0/s1
SMILES	CCCCCCCCCCCCCCCCCCCCCC[C@H](C(=N[C@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)CO)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	665.63	Volume:	775.873 ? Van der Waals volume.
Dense:	0.858	LogP:	11.271 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.539 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-9.771 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	38.0	Rigid Bonds:	2.0
TPSA:	93.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	0.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.023	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.901	Fsp³:	0.929
MCE-18:	4.0 ? 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:	0.903	Fluc inhibitor:	0.165 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.121	Promiscuous compounds:	0.372

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.186	MDCK Permeability:	-4.916
Pgp-inhibitor:	0.0	Pgp-substrate:	0.026
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):	0.993
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.44
Plasma Protein Binding (PPB):	103.324%	Volume Distribution (VD):	2.416
Fu:	0.195% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.966
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.978
BSEP inhibitor:	0.9

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.942	CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.998	CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.063 ? 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):

3.461

Half-life (T1/2):

5.395

ADMET: Toxicity

hERG Blockers:	0.256	hERG Blockers (10um):	0.703
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	0.892
AMES Toxicity:	0.007	Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.136	Skin Sensitization:	1.0
Carcinogencity:	0.053	Eye Corrosion:	0.0
Eye Irritation:	0.854	Respiratory Toxicity:	0.999
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.797
Hematotoxicity:	0.055	Drug-induced Nephrotoxicity:	0.362
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.022
A549 Cytotoxicity:	0.997	Hek293 Cytotoxicity:	0.211
BCF:	-0.159 ? 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:	5.626 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.125 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.955 ? 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
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	whole plants	Wenshan, Yunnan Province, China	2012-Nov	PMID[25798528]
NPO27626	Limonia acidissima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27626	Limonia acidissima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3216	Comactinia meridionalis	Species	Comatulidae	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
Activity	1
mortality	1

Activity Type	# Activity
Organism	2

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
NPT785	Organism	Pieris brassicae	Pieris brassicae	Activity	=	0.0	%	PMID[14611152]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT785	Organism	Pieris brassicae	Pieris brassicae	mortality	=	0.0	%	PMID[14611152]

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 NPC288086 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	23212
0.1-0.2	24753
0.2-0.3	1627
0.3-0.4	199
0.4-0.5	33
0.5-0.6	25
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.775	Intermediate Similarity	NPC489235
0.7111	Intermediate Similarity	NPC217095
0.7111	Intermediate Similarity	NPC264417
0.7045	Intermediate Similarity	NPC99959
0.7045	Intermediate Similarity	NPC291196
0.7045	Intermediate Similarity	NPC489236
0.7045	Intermediate Similarity	NPC489237
0.6739	Remote Similarity	NPC103712
0.6364	Remote Similarity	NPC145627
0.5714	Remote Similarity	NPC195165
0.5574	Remote Similarity	NPC263545
0.5574	Remote Similarity	NPC473950
0.5574	Remote Similarity	NPC111567
0.5574	Remote Similarity	NPC186840
0.5574	Remote Similarity	NPC144916
0.5574	Remote Similarity	NPC486421
0.5574	Remote Similarity	NPC309898
0.5574	Remote Similarity	NPC273493
0.5574	Remote Similarity	NPC475125
0.5574	Remote Similarity	NPC486419
0.5574	Remote Similarity	NPC15851
0.5574	Remote Similarity	NPC115448
0.5574	Remote Similarity	NPC20819
0.5574	Remote Similarity	NPC486418
0.5574	Remote Similarity	NPC473604
0.5574	Remote Similarity	NPC486420
0.5574	Remote Similarity	NPC479188
0.5574	Remote Similarity	NPC81468
0.5397	Remote Similarity	NPC156782
0.5397	Remote Similarity	NPC54961
0.5312	Remote Similarity	NPC158445
0.5312	Remote Similarity	NPC157353
0.5312	Remote Similarity	NPC282088
0.5116	Remote Similarity	NPC270041

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC288086 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6240
0.1-0.2	2760
0.2-0.3	142
0.3-0.4	7
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