NPASS Compound

Natural Product: NPC589540

Natural Product ID	NPC589540
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-[4-hydroxy-3-[(2~{S},3~{S},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-[4-hydroxy-3-[(2~{S},3~{S},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic 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 3D 115121 0 0 0 0 0 0 0 0999 V2000 9.3317 -2.0855 -1.7428 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4443 -1.4839 -0.6247 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1995 -1.4056 -1.1426 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4813 -0.2636 -1.0896 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4519 -0.2955 -0.1253 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1939 -0.2333 -0.7208 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0804 -0.3077 0.3074 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8484 -0.2464 -0.1986 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9861 0.8028 0.0739 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1053 0.3079 1.0684 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9707 -0.5135 0.8962 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2739 -0.1264 0.8297 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7975 1.2070 0.9461 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1451 1.2872 1.3330 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7998 2.4875 1.4621 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1474 3.6701 1.2117 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8170 4.8945 1.3450 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8167 3.6216 0.8260 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2178 4.8242 0.5846 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9523 5.1002 0.1051 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1389 5.7867 1.0125 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7357 7.0023 1.3532 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0041 7.6451 2.5061 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3267 7.9044 2.1977 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6467 7.9201 0.1668 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3293 8.8810 0.4130 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2095 7.1196 -1.0454 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2388 7.9496 -2.1389 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0653 5.8712 -1.2011 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3776 6.1762 -1.5093 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1791 2.3793 0.7044 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1542 -1.1318 0.6483 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9018 -2.3748 0.5351 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9088 -3.3325 0.3433 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6579 -4.6757 0.2166 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5919 -5.6596 0.0260 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9581 -5.4655 -0.0756 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6662 -6.2368 0.8072 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9897 -7.5060 0.4569 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8843 -8.5295 0.6215 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7760 -8.2344 -0.1572 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6133 -7.6670 -0.9164 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7945 -8.3764 -0.9139 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7965 -6.2625 -1.4753 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3850 -6.2913 -2.7376 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4196 -5.6558 -1.5333 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4851 -4.4257 -2.2016 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3023 -5.0604 0.2905 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3085 -4.1384 0.4771 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0400 -4.5116 0.5511 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5949 -2.7963 0.6002 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6073 -1.8751 0.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5839 -2.2018 0.8500 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6233 2.0867 0.3563 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7906 2.8421 -0.8109 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9742 1.9942 1.0343 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0751 2.8188 2.1473 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2612 0.5843 1.4790 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4877 0.5012 2.1117 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2505 1.0252 -1.0418 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0333 1.0671 -2.1978 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2103 0.9153 0.1233 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5325 0.7869 1.3330 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1126 -0.2341 -0.1803 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9219 -0.5182 0.9376 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7061 -2.6467 -2.4760 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7247 -1.2074 -2.2976 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1759 -2.6438 -1.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5322 -2.2635 0.1973 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9168 -0.2084 -2.0813 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1243 0.7860 -1.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1252 -1.0589 -1.4337 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1842 -1.3739 0.7467 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3625 0.8603 -0.8755 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7184 0.3916 1.5469 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8383 2.5500 1.7639 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5212 5.6426 1.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4575 4.1480 -0.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7763 6.8160 1.6980 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4724 8.6039 2.7977 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0456 6.9833 3.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6068 8.7336 2.6390 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6153 8.4365 -0.0183 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0244 9.7637 0.0855 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8315 6.7652 -0.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5865 8.4862 -2.2398 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6387 5.2920 -2.0385 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8524 5.3584 -1.7247 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1621 2.3792 0.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9213 -2.9721 0.2963 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2610 -4.3954 0.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8078 -7.8349 1.1685 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5894 -8.6030 1.7010 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2732 -9.5159 0.3108 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4487 -8.9913 -0.6708 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8787 -8.2018 -1.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8426 -8.9087 -0.0804 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3904 -5.7080 -0.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8630 -5.4383 -2.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6839 -6.2913 -2.0381 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0139 -4.4316 -3.0544 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0946 -6.1120 0.1925 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2554 -5.4721 0.3228 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0105 2.7022 1.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2921 2.3627 -1.4959 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7716 2.2933 0.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2961 3.7483 1.8843 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4770 0.3125 2.2301 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4497 -0.3069 2.6911 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5481 1.8516 -0.9603 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8729 1.5409 -2.0784 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7944 1.8434 0.1399 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5497 -0.1157 1.7056 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8406 0.1390 -0.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7534 -1.4270 1.2667 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 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 16 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 22 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 18 31 2 0 12 32 1 0 32 33 1 0 33 34 2 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 39 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 35 48 2 0 48 49 1 0 49 50 1 0 49 51 2 0 51 52 1 0 52 53 2 0 9 54 1 0 54 55 1 0 54 56 1 0 56 57 1 0 56 58 1 0 58 59 1 0 4 60 1 0 60 61 1 0 60 62 1 0 62 63 1 0 62 64 1 0 64 65 1 0 64 2 1 0 58 7 1 0 52 11 1 0 31 13 1 0 51 33 1 0 29 20 1 0 46 37 1 0 1 66 1 0 1 67 1 0 1 68 1 0 2 69 1 1 4 70 1 6 6 71 1 0 6 72 1 0 7 73 1 1 9 74 1 6 14 75 1 0 15 76 1 0 17 77 1 0 20 78 1 6 22 79 1 1 23 80 1 0 23 81 1 0 24 82 1 0 25 83 1 6 26 84 1 0 27 85 1 1 28 86 1 0 29 87 1 6 30 88 1 0 31 89 1 0 34 90 1 0 37 91 1 1 39 92 1 1 40 93 1 0 40 94 1 0 41 95 1 0 42 96 1 6 43 97 1 0 44 98 1 1 45 99 1 0 46100 1 6 47101 1 0 48102 1 0 50103 1 0 54104 1 1 55105 1 0 56106 1 6 57107 1 0 58108 1 1 59109 1 0 60110 1 1 61111 1 0 62112 1 1 63113 1 0 64114 1 6 65115 1 0 M END

Standard InCHIKey	OMIUWTZERGHBER-YYSIKCHTSA-N
Standard InCHI	InChI=1S/C39H50O26/c1-10-21(44)26(49)30(53)36(58-10)57-9-19-24(47)29(52)33(56)39(64-19)65-35-25(48)20-14(43)5-12(59-37-31(54)27(50)22(45)17(7-40)62-37)6-16(20)60-34(35)11-2-3-13(42)15(4-11)61-38-32(55)28(51)23(46)18(8-41)63-38/h2-6,10,17-19,21-24,26-33,36-47,49-56H,7-9H2,1H3/t10-,17+,18-,19-,21-,22+,23+,24+,26-,27-,28-,29-,30+,31+,32-,33+,36+,37+,38+,39-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@@H]2O[C@@H](OC3=C(C4=CC=C(O)C(O[C@@H]5O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]5O)=C4)OC4=CC(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)=CC(O)=C4C3=O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	934.26	Volume:	830.659 ? Van der Waals volume.
Dense:	1.125	LogP:	-1.301 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.244 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.342 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	42.0
TPSA:	427.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	16.0	Rings:	7.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.08	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.962	Fsp³:	0.615
MCE-18:	185.381 ? 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:	0
Colloidal aggregators:	0.645	Fluc inhibitor:	0.327 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.683 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.615 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.258	Promiscuous compounds:	0.609

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.379	MDCK Permeability:	-4.683
Pgp-inhibitor:	0.0	Pgp-substrate:	0.997
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):	1.0
20% Bioavailability (F20%):	0.966	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.011
Plasma Protein Binding (PPB):	66.573%	Volume Distribution (VD):	-0.188
Fu:	27.876% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.987
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.008
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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.069
HLM stability:	0.0 ? 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):

-0.175

Half-life (T1/2):

7.073

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.743	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.99	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.003	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.434	Drug-induced Nephrotoxicity:	0.991
Genotoxicity:	0.399	RPMI-8226 Immunitoxicity:	0.502
A549 Cytotoxicity:	0.896	Hek293 Cytotoxicity:	0.197
BCF:	0.289 ? 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:	2.658 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.525 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.475 ? 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
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	DOI[10.1016/j.foodchem.2007.08.004]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/j.phytochem.2007.01.008]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17328933]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917288]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15336	Prunus avium	Species	Rosaceae	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 NPC589540 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	23684
0.1-0.2	22232
0.2-0.3	2947
0.3-0.4	509
0.4-0.5	265
0.5-0.6	124
0.6-0.7	66
0.7-0.8	2
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
0.7826	Intermediate Similarity	NPC186816
0.7426	Intermediate Similarity	NPC480441
0.7426	Intermediate Similarity	NPC25523
0.7245	Intermediate Similarity	NPC476472
0.7245	Intermediate Similarity	NPC294815
0.7245	Intermediate Similarity	NPC16194
0.7065	Intermediate Similarity	NPC116458
0.7065	Intermediate Similarity	NPC246943
0.7065	Intermediate Similarity	NPC605784
0.7021	Intermediate Similarity	NPC251417
0.6972	Remote Similarity	NPC192539
0.6703	Remote Similarity	NPC297987
0.6703	Remote Similarity	NPC136042
0.6701	Remote Similarity	NPC67105
0.6699	Remote Similarity	NPC14187
0.6633	Remote Similarity	NPC210073
0.66	Remote Similarity	NPC470443
0.6531	Remote Similarity	NPC173582
0.6531	Remote Similarity	NPC44931
0.6531	Remote Similarity	NPC265885
0.6531	Remote Similarity	NPC181465
0.6531	Remote Similarity	NPC215710
0.6531	Remote Similarity	NPC473438
0.6531	Remote Similarity	NPC253788
0.6465	Remote Similarity	NPC203259
0.6465	Remote Similarity	NPC33054
0.6465	Remote Similarity	NPC176740
0.6465	Remote Similarity	NPC471725
0.6465	Remote Similarity	NPC134532
0.6465	Remote Similarity	NPC156869
0.6465	Remote Similarity	NPC602582
0.6421	Remote Similarity	NPC601144
0.6413	Remote Similarity	NPC289667
0.6413	Remote Similarity	NPC249281
0.6373	Remote Similarity	NPC32641
0.6373	Remote Similarity	NPC256188
0.6373	Remote Similarity	NPC209296
0.6373	Remote Similarity	NPC35119
0.6337	Remote Similarity	NPC488073
0.6337	Remote Similarity	NPC126784
0.6337	Remote Similarity	NPC241423
0.6311	Remote Similarity	NPC142142
0.6289	Remote Similarity	NPC276377
0.6289	Remote Similarity	NPC601586
0.6277	Remote Similarity	NPC46420
0.6277	Remote Similarity	NPC84362
0.6277	Remote Similarity	NPC271692
0.625	Remote Similarity	NPC473073
0.6239	Remote Similarity	NPC277532
0.6238	Remote Similarity	NPC473571
0.6238	Remote Similarity	NPC110941
0.6214	Remote Similarity	NPC473327
0.62	Remote Similarity	NPC275454
0.62	Remote Similarity	NPC227508
0.6146	Remote Similarity	NPC611303
0.6139	Remote Similarity	NPC22062
0.6139	Remote Similarity	NPC65563
0.6139	Remote Similarity	NPC473634
0.6139	Remote Similarity	NPC470949
0.6139	Remote Similarity	NPC138811
0.6139	Remote Similarity	NPC150164
0.6122	Remote Similarity	NPC203050
0.6122	Remote Similarity	NPC488072
0.6122	Remote Similarity	NPC225434
0.6111	Remote Similarity	NPC189564
0.6055	Remote Similarity	NPC219043
0.6055	Remote Similarity	NPC292019
0.6055	Remote Similarity	NPC202908
0.604	Remote Similarity	NPC39834
0.602	Remote Similarity	NPC311830
0.6019	Remote Similarity	NPC89052
0.6019	Remote Similarity	NPC121703
0.6019	Remote Similarity	NPC240306
0.6019	Remote Similarity	NPC64425
0.6019	Remote Similarity	NPC203145
0.6019	Remote Similarity	NPC153755
0.5918	Remote Similarity	NPC101026
0.5918	Remote Similarity	NPC488077
0.5909	Remote Similarity	NPC173837
0.5859	Remote Similarity	NPC223747
0.5833	Remote Similarity	NPC158674
0.5833	Remote Similarity	NPC602448
0.5776	Remote Similarity	NPC488079
0.5755	Remote Similarity	NPC72016
0.5688	Remote Similarity	NPC135358
0.5673	Remote Similarity	NPC479405
0.5673	Remote Similarity	NPC303913
0.567	Remote Similarity	NPC277205
0.567	Remote Similarity	NPC37919
0.5657	Remote Similarity	NPC285197
0.5648	Remote Similarity	NPC195257
0.5648	Remote Similarity	NPC220173
0.5631	Remote Similarity	NPC471079
0.5619	Remote Similarity	NPC479404
0.5607	Remote Similarity	NPC606657
0.5603	Remote Similarity	NPC198199
0.5593	Remote Similarity	NPC209550
0.5577	Remote Similarity	NPC67326
0.5556	Remote Similarity	NPC486577
0.5545	Remote Similarity	NPC206123
0.5514	Remote Similarity	NPC65711
0.5514	Remote Similarity	NPC479403
0.551	Remote Similarity	NPC323593
0.551	Remote Similarity	NPC203500
0.551	Remote Similarity	NPC189142
0.551	Remote Similarity	NPC77660
0.5508	Remote Similarity	NPC470720
0.5481	Remote Similarity	NPC480466
0.547	Remote Similarity	NPC298666
0.5462	Remote Similarity	NPC120952
0.5462	Remote Similarity	NPC138990
0.5455	Remote Similarity	NPC101636
0.5446	Remote Similarity	NPC486578
0.5439	Remote Similarity	NPC164704
0.5424	Remote Similarity	NPC470719
0.5424	Remote Similarity	NPC470717
0.5421	Remote Similarity	NPC488074
0.5417	Remote Similarity	NPC175429
0.5408	Remote Similarity	NPC39360
0.5408	Remote Similarity	NPC77672
0.5408	Remote Similarity	NPC133671
0.5408	Remote Similarity	NPC135391
0.5408	Remote Similarity	NPC29763
0.5408	Remote Similarity	NPC78263
0.5408	Remote Similarity	NPC210003
0.5408	Remote Similarity	NPC250069
0.5408	Remote Similarity	NPC238376
0.5398	Remote Similarity	NPC473072
0.5391	Remote Similarity	NPC311850
0.5385	Remote Similarity	NPC295625
0.5378	Remote Similarity	NPC488078
0.537	Remote Similarity	NPC12013
0.537	Remote Similarity	NPC11432
0.537	Remote Similarity	NPC477613
0.5354	Remote Similarity	NPC145038
0.5354	Remote Similarity	NPC56077
0.5354	Remote Similarity	NPC281131
0.5354	Remote Similarity	NPC253662
0.5354	Remote Similarity	NPC179950
0.5354	Remote Similarity	NPC88789
0.5354	Remote Similarity	NPC491374
0.5347	Remote Similarity	NPC60735
0.5347	Remote Similarity	NPC26230
0.5347	Remote Similarity	NPC488071
0.5345	Remote Similarity	NPC470716
0.5321	Remote Similarity	NPC122467
0.5304	Remote Similarity	NPC217520
0.5304	Remote Similarity	NPC470715
0.53	Remote Similarity	NPC24043
0.5294	Remote Similarity	NPC22832
0.5294	Remote Similarity	NPC197285
0.5288	Remote Similarity	NPC116864
0.5288	Remote Similarity	NPC244776
0.5268	Remote Similarity	NPC470446
0.5254	Remote Similarity	NPC68592
0.5253	Remote Similarity	NPC108831
0.5253	Remote Similarity	NPC19709
0.5253	Remote Similarity	NPC182634
0.5248	Remote Similarity	NPC42773
0.5248	Remote Similarity	NPC45522
0.5248	Remote Similarity	NPC325555
0.5248	Remote Similarity	NPC226304
0.5225	Remote Similarity	NPC89127
0.5214	Remote Similarity	NPC139571
0.52	Remote Similarity	NPC64305
0.5196	Remote Similarity	NPC307938
0.5192	Remote Similarity	NPC469931
0.5189	Remote Similarity	NPC187379
0.5189	Remote Similarity	NPC609888
0.5185	Remote Similarity	NPC204693
0.5185	Remote Similarity	NPC115674
0.5182	Remote Similarity	NPC473623
0.5182	Remote Similarity	NPC229409
0.5179	Remote Similarity	NPC292929
0.5179	Remote Similarity	NPC470449
0.5179	Remote Similarity	NPC221342
0.5179	Remote Similarity	NPC470445
0.5179	Remote Similarity	NPC476470
0.5152	Remote Similarity	NPC111929
0.5152	Remote Similarity	NPC320283
0.5152	Remote Similarity	NPC331652
0.5152	Remote Similarity	NPC41121
0.5149	Remote Similarity	NPC27640
0.5149	Remote Similarity	NPC488080
0.5149	Remote Similarity	NPC169977
0.5146	Remote Similarity	NPC120099
0.5146	Remote Similarity	NPC601710
0.5138	Remote Similarity	NPC64051
0.5135	Remote Similarity	NPC488089
0.5118	Remote Similarity	NPC223860
0.51	Remote Similarity	NPC127546
0.51	Remote Similarity	NPC261866
0.51	Remote Similarity	NPC57625
0.51	Remote Similarity	NPC173637
0.51	Remote Similarity	NPC317489
0.51	Remote Similarity	NPC223424
0.51	Remote Similarity	NPC600591
0.5098	Remote Similarity	NPC472459
0.5098	Remote Similarity	NPC59534
0.5098	Remote Similarity	NPC599850

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC589540 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5960
0.1-0.2	3138
0.2-0.3	40
0.3-0.4	6
0.4-0.5	1
0.5-0.6	1
0.6-0.7	2
0.7-0.8	2
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
0.7423	Intermediate Similarity	NPD7251	Phase 2
0.7129	Intermediate Similarity	NPD7808	Phase 3
0.6465	Remote Similarity	NPD6797	Phase 2
0.6373	Remote Similarity	NPD7054	Phase 4
0.5175	Remote Similarity	NPD7472	Pre-clinical

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