NPASS Compound

Natural Product: NPC476613

Natural Product ID	NPC476613
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2S)-2-[8-[(1R,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoyloxy]-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] 8-[(1R,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoate
IUPAC Name	[(2S)-2-[8-[(1R,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoyloxy]-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] 8-[(1R,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoate
Synonyms	Arabidopside B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44583989
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 127129 0 0 0 0 0 0 0 0999 V2000 -12.8765 14.5553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5283 15.2129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1801 15.8704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9366 15.0316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0412 13.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1458 12.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9371 10.5536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2853 9.8960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3272 10.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6230 12.2994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3583 13.4316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4240 9.1440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9110 7.7345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3980 6.3249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8849 4.9154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3719 3.5059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8589 2.0963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3459 0.6868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8328 -0.7228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7970 -1.8718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3556 -0.9832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8426 -2.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3296 -3.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9200 -3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 -2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7981 1.9284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8165 -5.2118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7807 -6.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2579 -6.1004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2677 -7.7705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7546 -9.1800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2416 -10.5895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7286 -11.9991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2156 -13.4086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2975 -14.8181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8105 -16.2277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3235 -17.6372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5323 -19.1226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0095 -19.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7137 -18.0587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1991 -17.8499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6717 -16.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8769 -15.7076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0820 -14.4355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7862 -13.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2853 -13.0588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7844 -13.0064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5340 15.9035 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2847 13.3419 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2247 13.8978 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7878 15.9666 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9625 15.8814 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0755 17.3668 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5884 15.6892 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5448 13.4307 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5136 13.8216 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6467 12.0913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4816 10.9164 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7239 8.4615 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8126 10.7662 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7605 8.4630 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0145 9.6570 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5015 8.2475 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3205 7.2214 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8075 5.8119 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9884 6.8380 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2945 4.4024 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4754 5.4284 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9624 4.0189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7815 2.9928 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2684 1.5833 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4493 2.6093 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7554 0.1737 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1023 1.5256 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7106 -1.4086 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2521 -2.9058 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7391 -4.3153 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4070 -4.6988 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6010 -1.9528 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0865 -1.9801 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7580 0.8169 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 2.7762 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0865 1.9801 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8482 -0.6575 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8321 2.2222 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8626 0.0826 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2899 1.7717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 3.7404 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4176 0.9951 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5706 -2.4621 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6772 -8.2835 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8581 -7.2574 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3451 -8.6670 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1642 -9.6930 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6511 -11.1026 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1679 -10.0765 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6079 -11.3180 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1381 -12.5121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0280 -12.5698 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6251 -13.9216 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1121 -15.3312 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5410 -13.9793 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0540 -15.3888 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5990 -16.7407 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1319 -18.0001 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4533 -20.1646 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6671 -20.7313 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8537 -16.0562 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2363 -15.0737 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4502 -16.1710 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3852 -14.1236 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1523 -11.7516 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2329 -11.5597 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5200 -14.5403 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7320 -11.5073 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8367 -14.5055 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2834 -12.9541 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 7 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 2 0 19 21 1 0 21 22 1 0 22 23 1 0 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 30 32 1 0 32 33 1 0 29 34 1 0 28 35 1 0 27 36 1 0 23 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 50 52 1 0 52 53 1 0 53 54 1 0 54 55 2 0 55 56 1 0 56 57 1 0 10 6 1 0 31 26 1 0 52 47 1 0 1 58 1 0 1 59 1 0 1 60 1 0 2 61 1 0 2 62 1 0 3 63 1 0 4 64 1 0 5 65 1 0 5 66 1 0 6 67 1 1 7 68 1 1 8 69 1 0 9 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 22 85 1 0 22 86 1 0 23 87 1 1 24 88 1 0 24 89 1 0 26 90 1 1 27 91 1 6 28 92 1 1 29 93 1 1 30 94 1 1 32 95 1 0 32 96 1 0 33 97 1 0 34 98 1 0 35 99 1 0 36100 1 0 40101 1 0 40102 1 0 41103 1 0 41104 1 0 42105 1 0 42106 1 0 43107 1 0 43108 1 0 44109 1 0 44110 1 0 45111 1 0 45112 1 0 46113 1 0 46114 1 0 47115 1 6 48116 1 0 49117 1 0 52118 1 6 53119 1 0 53120 1 0 54121 1 0 55122 1 0 56123 1 0 56124 1 0 57125 1 0 57126 1 0 57127 1 0 M END

Standard InCHIKey	SYJOSMLJXIQXFJ-IVVROMSISA-N
Standard InCHI	InChI=1S/C45H70O12/c1-3-5-13-21-35-32(25-27-37(35)47)19-15-9-7-11-17-23-40(49)54-30-34(31-55-45-44(53)43(52)42(51)39(29-46)57-45)56-41(50)24-18-12-8-10-16-20-33-26-28-38(48)36(33)22-14-6-4-2/h5-6,13-14,25-28,32-36,39,42-46,51-53H,3-4,7-12,15-24,29-31H2,1-2H3/b13-5-,14-6-/t32-,33-,34-,35-,36-,39-,42+,43+,44-,45-/m1/s1
SMILES	CC/C=C\C[C@@H]1[C@@H](C=CC1=O)CCCCCCCC(=O)OC[C@H](CO[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)OC(=O)CCCCCCC[C@@H]3C=CC(=O)[C@@H]3C/C=C\CC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	802.49	Volume:	845.597 ? Van der Waals volume.
Dense:	0.949	LogP:	5.884 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.59 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.686 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	31.0	Rigid Bonds:	22.0
TPSA:	186.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.038	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.427	Fsp³:	0.733
MCE-18:	51.308 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.998	Fluc inhibitor:	0.014 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.008 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.546	Promiscuous compounds:	0.634

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.289	MDCK Permeability:	-5.141
Pgp-inhibitor:	0.208	Pgp-substrate:	0.002
PAMPA:	0.035 ? 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):	0.045
20% Bioavailability (F20%):	0.973	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.943
Plasma Protein Binding (PPB):	97.002%	Volume Distribution (VD):	-0.49
Fu:	2.813% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.006
OATP1B3 inhibitor:	0.9	BCRP inhibitor:	0.007
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.176
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.062	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.904 ? 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):

2.617

Half-life (T1/2):

1.042

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.077
Human Hepatotoxicity (H-HT):	0.616	Drug-induced Liver Injury (DILI):	0.21
AMES Toxicity:	0.994	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.118	Eye Corrosion:	0.034
Eye Irritation:	0.379	Respiratory Toxicity:	0.454
Drug-induced Neurotoxicity:	0.378	Ototoxicity:	0.831
Hematotoxicity:	0.091	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.305
A549 Cytotoxicity:	0.947	Hek293 Cytotoxicity:	0.242
BCF:	1.043 ? 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:	5.36 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.883 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.131 ? 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
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	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
Inhibition	1

Activity Type	# Activity
Organism	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
NPT3130	Organism	Lepidium sativum	Lepidium sativum	Inhibition	=	30	%	PMID[15844959]

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 NPC476613 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	16747
0.1-0.2	27352
0.2-0.3	5175
0.3-0.4	549
0.4-0.5	17
0.5-0.6	5
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476612
0.9265	High Similarity	NPC476611
0.6857	Remote Similarity	NPC236649
0.6769	Remote Similarity	NPC488690
0.6667	Remote Similarity	NPC488689
0.6438	Remote Similarity	NPC110813
0.64	Remote Similarity	NPC38295
0.6389	Remote Similarity	NPC21693
0.6234	Remote Similarity	NPC470313
0.6234	Remote Similarity	NPC473500
0.6234	Remote Similarity	NPC611497
0.6216	Remote Similarity	NPC156089
0.6216	Remote Similarity	NPC133377
0.5342	Remote Similarity	NPC83839
0.5132	Remote Similarity	NPC488693
0.5125	Remote Similarity	NPC488694
0.5116	Remote Similarity	NPC22558
0.5065	Remote Similarity	NPC331437

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6197
0.1-0.2	2803
0.2-0.3	136
0.3-0.4	14
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