NPASS Compound

Natural Product: NPC137383

Natural Product ID	NPC137383
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LQIRTDPVBLPFPL-FWDPRUGSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21575437
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

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 122128 0 0 0 0 0 0 0 0999 V2000 5.7429 -1.7444 -1.7071 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0592 -1.5717 -0.6304 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7778 -0.3127 0.0401 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2262 -0.1957 0.2156 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5790 -0.0534 -1.1129 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0941 0.0589 -1.1134 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4810 -1.0995 -0.5101 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6468 -2.3040 -1.2292 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6925 -3.4257 -0.1903 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4119 -3.2029 0.7850 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8918 -4.0781 1.7508 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5468 -5.3547 2.1301 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2155 -5.9992 3.1541 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2463 -5.3514 3.8067 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5864 -4.0724 3.4211 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9131 -3.4195 2.3873 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0433 -2.2062 1.8328 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1571 -2.0332 0.8624 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8837 -0.8644 -0.0547 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8620 -0.8052 -1.1570 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2932 -0.5579 -0.8770 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7774 0.6921 -0.2871 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9815 1.2723 0.8267 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6470 2.5199 1.0215 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2786 1.7574 -1.2476 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0473 1.3333 -2.5785 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4764 0.0403 -2.9173 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1202 -0.9289 -2.0874 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5353 -2.2848 -2.3773 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2490 -2.5134 -3.4390 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2604 -3.4130 -1.6439 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7229 -4.7087 -2.0335 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6750 1.8427 -1.1062 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1359 3.1068 -0.7700 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1149 3.5171 -1.8514 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2029 2.4641 -1.8823 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9203 2.5492 -0.5563 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0906 3.2332 0.5048 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6091 2.6637 1.8375 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9439 3.3004 2.8524 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7545 2.9737 0.4707 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0848 3.2978 -0.7155 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5634 1.2137 -1.9140 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6841 4.7642 -1.5960 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0397 0.9614 1.1335 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8130 2.0435 0.9085 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7091 2.0706 -0.1085 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3824 0.9024 -0.5520 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7324 0.9890 -0.1729 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6299 1.1634 -1.1768 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3388 2.4955 -1.2006 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5713 2.5210 -0.3462 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3709 1.2529 -0.4948 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4535 0.0647 -0.4341 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9299 -0.2003 0.9434 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2458 -1.4267 0.9717 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5038 0.1303 -1.4292 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0150 1.3076 -1.7417 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3030 2.6983 1.0120 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7833 2.7698 -2.5135 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0717 0.9532 2.2076 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9512 1.9592 2.9354 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2509 -0.1200 2.4850 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3002 -0.1040 3.5440 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8796 -2.7894 -2.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2320 -1.0208 -2.3422 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6333 -2.4797 -0.1428 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1977 -0.3978 1.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9341 -1.1050 0.7835 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9925 0.9003 -1.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9843 -0.8497 -1.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7307 0.2748 -2.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8236 0.9375 -0.4745 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5925 -2.3314 -1.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1409 -2.6038 -1.9329 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6260 -4.4299 -0.6564 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6373 -3.2957 0.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2768 -5.8344 1.5868 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9223 -6.9871 3.4248 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7934 -5.8282 4.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3861 -3.5642 3.9261 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7684 -1.5479 2.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8283 0.0959 0.4802 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8463 -1.7793 -1.7506 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5351 -0.0639 -1.9660 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6287 -1.3899 -0.1278 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7618 0.3880 0.2645 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6437 0.5898 1.6390 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9155 3.3261 0.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0420 2.7508 1.9275 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9004 2.7607 -1.0650 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0581 -0.1322 -3.8072 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0428 -5.2596 -1.1364 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9115 -5.2801 -2.5493 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5640 -4.6491 -2.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3092 3.8455 -0.6752 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5889 3.5731 -2.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8956 2.5924 -2.7413 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2252 1.5230 -0.2082 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3407 4.3268 0.5792 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3858 1.5854 1.8243 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7201 2.8416 1.9223 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3744 4.2019 2.9813 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8709 2.6838 -0.6994 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7005 0.6968 -1.0679 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6228 4.8353 -1.8572 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6469 2.8669 1.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2502 0.8926 -1.6616 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9801 1.1909 -2.1316 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6683 3.3387 -0.9581 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1770 3.4157 -0.6724 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1819 1.2010 0.2702 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1287 -0.8282 -0.6596 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3614 0.6116 1.4018 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8020 -0.3710 1.6526 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8673 -2.1725 0.7897 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8774 1.7956 -1.6128 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0253 2.3417 1.5782 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2140 2.2943 -3.1485 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1996 -1.1133 4.0031 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7009 0.5765 4.3181 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6663 0.3174 3.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 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 2 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 25 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 38 41 1 0 37 42 1 0 36 43 1 0 35 44 1 0 4 45 1 0 45 46 2 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 53 58 1 0 52 59 1 0 51 60 1 0 45 61 1 0 61 62 2 0 61 63 1 0 63 64 1 0 48 3 1 0 57 50 1 0 19 7 1 0 28 21 1 0 41 34 1 0 18 10 2 0 16 11 1 0 1 65 1 0 1 66 1 0 2 67 1 0 3 68 1 1 4 69 1 1 5 70 1 0 5 71 1 0 6 72 1 0 6 73 1 0 8 74 1 0 8 75 1 0 9 76 1 0 9 77 1 0 12 78 1 0 13 79 1 0 14 80 1 0 15 81 1 0 17 82 1 0 19 83 1 1 20 84 1 0 20 85 1 0 21 86 1 1 22 87 1 1 23 88 1 0 24 89 1 0 24 90 1 0 25 91 1 1 27 92 1 0 32 93 1 0 32 94 1 0 32 95 1 0 34 96 1 1 35 97 1 6 36 98 1 6 37 99 1 1 38100 1 1 39101 1 0 39102 1 0 40103 1 0 42104 1 0 43105 1 0 44106 1 0 46107 1 0 48108 1 6 50109 1 6 51110 1 1 52111 1 6 53112 1 1 54113 1 6 55114 1 0 55115 1 0 56116 1 0 58117 1 0 59118 1 0 60119 1 0 64120 1 0 64121 1 0 64122 1 0 M END

Standard InCHIKey	LQIRTDPVBLPFPL-FWDPRUGSSA-N
Standard InCHI	InChI=1S/C44H58N2O18/c1-5-20-22(26(39(55)57-3)18-59-41(20)63-43-37(53)35(51)33(49)30(16-47)61-43)11-13-46-14-12-24-23-9-7-8-10-28(23)45-32(24)29(46)15-25-21(6-2)42(60-19-27(25)40(56)58-4)64-44-38(54)36(52)34(50)31(17-48)62-44/h5-10,18-22,25,29-31,33-38,41-45,47-54H,1-2,11-17H2,3-4H3/t20-,21-,22+,25+,29+,30-,31-,33-,34-,35+,36+,37-,38-,41+,42+,43+,44+/m1/s1
SMILES	C=C[C@@H]1[C@H](CCN2CCc3c4ccccc4[nH]c3[C@@H]2C[C@H]2[C@@H](C=C)[C@@H](OC=C2C(=O)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)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:	902.37	Volume:	863.538 ? Van der Waals volume.
Dense:	1.045	LogP:	0.851 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.336 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.714 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	43.0
TPSA:	288.85 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.078	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.195	Fsp³:	0.591
MCE-18:	166.514 ? 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:	0.681	Fluc inhibitor:	0.01 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.418 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.046 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.017	Promiscuous compounds:	0.203

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.959	MDCK Permeability:	-5.26
Pgp-inhibitor:	0.0	Pgp-substrate:	0.978
PAMPA:	0.655 ? 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):	0.003
20% Bioavailability (F20%):	0.221	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017	MRP1:	0.971
Plasma Protein Binding (PPB):	75.159%	Volume Distribution (VD):	-0.483
Fu:	24.092% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.134
BSEP inhibitor:	0.004

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:	0.016
CYP3A4-inhibitor:	0.035	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.009 ? 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):

1.231

Half-life (T1/2):

3.282

ADMET: Toxicity

hERG Blockers:	0.087	hERG Blockers (10um):	0.046
Human Hepatotoxicity (H-HT):	0.854	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.994	Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.054	Skin Sensitization:	1.0
Carcinogencity:	0.232	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.054	Ototoxicity:	1.0
Hematotoxicity:	0.646	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.938	RPMI-8226 Immunitoxicity:	0.263
A549 Cytotoxicity:	0.959	Hek293 Cytotoxicity:	0.702
BCF:	0.553 ? 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:	3.355 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.101 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.169 ? 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
NPO22818	Acritopappus confertus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22475.1	Brachylaena discolor var. rotundata	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22818	Acritopappus confertus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21220	Pulicaria uliginosa	Species	Asteraceae	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 NPC137383 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	16569
0.1-0.2	30896
0.2-0.3	2070
0.3-0.4	225
0.4-0.5	60
0.5-0.6	25
0.6-0.7	10
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC486444
0.8	Intermediate Similarity	NPC649
0.7404	Intermediate Similarity	NPC199607
0.7404	Intermediate Similarity	NPC54591
0.6542	Remote Similarity	NPC52254
0.6542	Remote Similarity	NPC611036
0.6364	Remote Similarity	NPC486448
0.633	Remote Similarity	NPC474905
0.6296	Remote Similarity	NPC82070
0.6296	Remote Similarity	NPC40703
0.6182	Remote Similarity	NPC599983
0.6161	Remote Similarity	NPC201287
0.6161	Remote Similarity	NPC475271
0.6161	Remote Similarity	NPC601145
0.596	Remote Similarity	NPC273374
0.5702	Remote Similarity	NPC603178
0.5631	Remote Similarity	NPC312870
0.5631	Remote Similarity	NPC199851
0.5631	Remote Similarity	NPC294909
0.5631	Remote Similarity	NPC254240
0.5631	Remote Similarity	NPC128265
0.5631	Remote Similarity	NPC604675
0.5508	Remote Similarity	NPC485121
0.5508	Remote Similarity	NPC485120
0.549	Remote Similarity	NPC486449
0.549	Remote Similarity	NPC63199
0.549	Remote Similarity	NPC111602
0.549	Remote Similarity	NPC102338
0.549	Remote Similarity	NPC196251
0.534	Remote Similarity	NPC486443
0.534	Remote Similarity	NPC486446
0.531	Remote Similarity	NPC180804
0.531	Remote Similarity	NPC227138
0.531	Remote Similarity	NPC174788
0.5288	Remote Similarity	NPC107782
0.5288	Remote Similarity	NPC486454
0.5254	Remote Similarity	NPC84073
0.5143	Remote Similarity	NPC175474
0.5143	Remote Similarity	NPC99921

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC137383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4143
0.1-0.2	4910
0.2-0.3	88
0.3-0.4	5
0.4-0.5	2
0.5-0.6	2
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
0.5631	Remote Similarity	NPD4500	Approved
0.5631	Remote Similarity	NPD4501	Approved

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