NPASS Compound

Natural Product: NPC288944

Natural Product ID	NPC288944
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NJIBYWMHTBDPCP-UNLHVXOPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11051372
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

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 129134 0 0 0 0 0 0 0 0999 V2000 3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 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 0.4895 -2.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2291 -4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1805 -4.7665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3781 -5.2176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1176 -6.6949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8572 -8.1721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3572 -8.1721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1072 -9.4711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3572 -10.7701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8572 -10.7701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1176 -12.2474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0314 -13.2115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1805 -14.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3296 -15.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7391 -14.6269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8882 -15.5910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6277 -17.0683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2181 -17.5813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0691 -16.6171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9577 -19.0585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7768 -18.0324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1072 -9.4711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7667 -11.2832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2562 -8.5069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6658 -9.0200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9263 -7.5427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3358 -7.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4849 -7.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2244 -9.4711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7244 -9.4711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8148 -9.9841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2349 -6.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5858 -5.7307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4263 -7.5427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0967 -6.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6872 -6.1818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0770 -4.8115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4619 -7.1460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8714 -6.6330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0205 -7.5972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4300 -7.0841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5791 -8.0483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3186 -9.5255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9091 -10.0385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7600 -9.0744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6486 -11.5158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4677 -10.4897 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 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 2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 2.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3086 5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 7.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8086 8.3287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 4.7665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2181 5.2176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7286 2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0796 1.4772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0490 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5521 -2.2018 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0420 1.0790 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 1.9667 -3.0367 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0068 -2.8810 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6140 -6.5901 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3787 -6.7996 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6346 -8.0154 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6007 -7.3332 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1301 -10.5682 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0967 -12.2474 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6044 -11.1075 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9328 -14.3606 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1285 -12.1886 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1447 -13.0267 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2163 -15.3248 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9996 -13.1497 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2977 -15.0780 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6595 -17.1301 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5481 -19.5715 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5163 -19.5097 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0272 -12.7604 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0797 -10.4007 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6658 -6.0655 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4849 -6.0655 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9464 -8.3313 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4849 -10.9483 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7244 -10.9711 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9072 -7.9823 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2244 -9.4711 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7349 -6.6949 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3358 -4.4316 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6763 -6.2437 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5666 -8.6423 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -5.1350 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8686 -5.6497 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9887 -7.5353 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3505 -9.5874 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7977 -12.4799 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8772 -9.9767 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3114 2.7335 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9312 3.4721 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 4.2535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1567 6.6521 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 6.6949 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4394 6.4437 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7596 7.7797 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 9.6278 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 6.5167 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2286 2.4414 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 0.1782 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0490 -3.1471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3692 -4.4832 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6528 -5.0950 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 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 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 21 25 1 0 14 26 1 0 13 27 1 0 12 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 33 35 1 0 32 36 1 0 31 37 1 0 30 38 1 0 11 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 48 50 1 0 47 51 1 0 4 52 1 0 52 53 2 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 61 64 1 0 60 65 1 0 59 66 1 0 58 67 1 0 52 68 1 0 68 69 2 0 68 70 1 0 70 71 1 0 55 3 1 0 64 57 1 0 26 10 1 0 35 29 1 0 49 44 1 0 23 18 1 0 1 72 1 0 1 73 1 0 1 74 1 0 2 75 1 0 4 76 1 1 5 77 1 0 5 78 1 0 9 79 1 0 9 80 1 0 10 81 1 1 11 82 1 6 12 83 1 1 13 84 1 6 14 85 1 1 16 86 1 0 16 87 1 0 17 88 1 0 17 89 1 0 19 90 1 0 20 91 1 0 23 92 1 0 24 93 1 0 25 94 1 0 27 95 1 0 29 96 1 6 30 97 1 1 31 98 1 1 32 99 1 6 33100 1 1 34101 1 0 34102 1 0 34103 1 0 36104 1 0 37105 1 0 38106 1 0 42107 1 0 43108 1 0 45109 1 0 46110 1 0 49111 1 0 50112 1 0 51113 1 0 53114 1 0 55115 1 6 57116 1 1 58117 1 6 59118 1 1 60119 1 6 61120 1 1 62121 1 0 62122 1 0 63123 1 0 65124 1 0 66125 1 0 67126 1 0 71127 1 0 71128 1 0 71129 1 0 M END

Standard InCHIKey	NJIBYWMHTBDPCP-UNLHVXOPSA-N
Standard InCHI	InChI=1S/C46H58O25/c1-4-22-23(24(42(61)62-3)17-65-43(22)71-46-38(59)36(57)34(55)29(16-47)67-46)15-32(53)64-18-30-40(69-31(52)10-7-20-5-8-25(48)27(50)13-20)41(70-45-37(58)35(56)33(54)19(2)66-45)39(60)44(68-30)63-12-11-21-6-9-26(49)28(51)14-21/h4-10,13-14,17,19,23,29-30,33-41,43-51,54-60H,11-12,15-16,18H2,1-3H3/b10-7+,22-4+/t19-,23-,29+,30+,33-,34+,35+,36-,37+,38+,39+,40+,41+,43-,44+,45-,46-/m0/s1
SMILES	C/C=C/1[C@H](CC(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](OCCc3ccc(c(c3)O)O)O2)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)OC(=O)/C=C/c2ccc(c(c2)O)O)C(=CO[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1010.33	Volume:	940.951 ? Van der Waals volume.
Dense:	1.074	LogP:	0.247 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.855 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.306 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	20.0	Rigid Bonds:	41.0
TPSA:	386.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.026	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.229	Fsp³:	0.543
MCE-18:	160.028 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.773	Fluc inhibitor:	0.659 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.295 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.637 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.219	Promiscuous compounds:	0.29

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.229	MDCK Permeability:	-5.498
Pgp-inhibitor:	0.0	Pgp-substrate:	0.12
PAMPA:	1.0 ? 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):	0.842
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.075
Plasma Protein Binding (PPB):	69.383%	Volume Distribution (VD):	-0.328
Fu:	27.264% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.017
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.146 ? 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):

0.971

Half-life (T1/2):

4.261

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.392
Human Hepatotoxicity (H-HT):	0.691	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.966	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.077	Skin Sensitization:	1.0
Carcinogencity:	0.007	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.053	Drug-induced Nephrotoxicity:	0.77
Genotoxicity:	0.996	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.992	Hek293 Cytotoxicity:	0.501
BCF:	0.492 ? 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:	3.448 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.356 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.632 ? 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
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/P19890001079]
NPO12062	Pseudoxandra cuspidata	Species	Annonaceae	Eukaryota	Bark	n.a.	n.a.	PMID[19299148]
NPO12298	Epilobium parviflorum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37111814]
NPO15096	Penicillium sclerotiorum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13239	Eudistoma toealensis	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10656	Rzedowskia tolantonguensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11272	Plectranthus parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8614	Cinchona succirubra	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8614	Cinchona succirubra	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15096	Penicillium sclerotiorum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6240	Paliurus spina-christi	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10146	Bassia parkii	Species	Abylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13363	Rumex aquaticus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11606	Anemoclema glaucifolium	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14760	Eulophia ochreata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14219	Aconitum racemulosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12062	Pseudoxandra cuspidata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1197	Panax trifoliatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12298	Epilobium parviflorum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10656	Rzedowskia tolantonguensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15910	Calea morii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2891	Montanelia tominii	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15423	Senecio ilicifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13239	Eudistoma toealensis	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1552	Euonymus japonicus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16173	Parmelia norcrambidiocarpa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14343	Scapharca broughtonii	Species	Arcidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9574	Trametes albida	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3128	Solanum dasyphyllum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11272	Plectranthus parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8614	Cinchona succirubra	Species	Rubiaceae	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 NPC288944 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	13186
0.1-0.2	32228
0.2-0.3	3970
0.3-0.4	353
0.4-0.5	58
0.5-0.6	37
0.6-0.7	23
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
0.7143	Intermediate Similarity	NPC298257
0.7143	Intermediate Similarity	NPC175214
0.6923	Remote Similarity	NPC611289
0.681	Remote Similarity	NPC488390
0.6759	Remote Similarity	NPC198577
0.6757	Remote Similarity	NPC106818
0.6699	Remote Similarity	NPC296643
0.6699	Remote Similarity	NPC299576
0.6667	Remote Similarity	NPC76406
0.6667	Remote Similarity	NPC488389
0.6574	Remote Similarity	NPC23677
0.6522	Remote Similarity	NPC87403
0.6514	Remote Similarity	NPC205864
0.6514	Remote Similarity	NPC247032
0.6321	Remote Similarity	NPC472350
0.6321	Remote Similarity	NPC197316
0.6321	Remote Similarity	NPC89105
0.6283	Remote Similarity	NPC300894
0.6283	Remote Similarity	NPC23845
0.6102	Remote Similarity	NPC64195
0.6071	Remote Similarity	NPC65262
0.6071	Remote Similarity	NPC84429
0.6071	Remote Similarity	NPC101686
0.6034	Remote Similarity	NPC476384
0.6017	Remote Similarity	NPC470933
0.5982	Remote Similarity	NPC269141
0.5981	Remote Similarity	NPC169398
0.5826	Remote Similarity	NPC100998
0.5798	Remote Similarity	NPC476380
0.5789	Remote Similarity	NPC252292
0.5785	Remote Similarity	NPC488386
0.5739	Remote Similarity	NPC119537
0.5702	Remote Similarity	NPC469364
0.5702	Remote Similarity	NPC488387
0.5702	Remote Similarity	NPC609284
0.5669	Remote Similarity	NPC257970
0.5667	Remote Similarity	NPC476381
0.5664	Remote Similarity	NPC488383
0.5603	Remote Similarity	NPC112
0.56	Remote Similarity	NPC476386
0.5593	Remote Similarity	NPC259347
0.5545	Remote Similarity	NPC46137
0.5455	Remote Similarity	NPC196063
0.5455	Remote Similarity	NPC81515
0.5455	Remote Similarity	NPC604195
0.5446	Remote Similarity	NPC600692
0.5357	Remote Similarity	NPC64141
0.5357	Remote Similarity	NPC205195
0.5323	Remote Similarity	NPC470934
0.5317	Remote Similarity	NPC229505
0.531	Remote Similarity	NPC483705
0.5299	Remote Similarity	NPC34587
0.5294	Remote Similarity	NPC34927
0.5259	Remote Similarity	NPC263829
0.525	Remote Similarity	NPC96795
0.525	Remote Similarity	NPC264632
0.5246	Remote Similarity	NPC476375
0.5221	Remote Similarity	NPC483706
0.5191	Remote Similarity	NPC470927
0.513	Remote Similarity	NPC68092
0.5124	Remote Similarity	NPC610636
0.504	Remote Similarity	NPC476378

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC288944 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5402
0.1-0.2	3687
0.2-0.3	60
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
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
0.6321	Remote Similarity	NPD7266	Phase 2

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