NPASS Compound

Natural Product: NPC554975

Natural Product ID	NPC554975
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},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] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-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 115121 0 0 0 0 0 0 0 0999 V2000 10.1706 -4.5191 0.4336 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2628 -3.2813 0.4323 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4946 -3.3793 -0.7059 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7555 -2.2089 -0.9757 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1166 -1.7521 0.1675 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7523 -1.6397 0.0721 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3148 -0.6132 -0.9822 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9452 -0.6063 -0.9992 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3811 0.5616 -1.5722 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8478 1.3653 -0.5243 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5280 1.3023 -0.1482 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5560 2.1386 -0.5885 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7854 3.2457 -1.5190 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3357 3.8237 -2.1199 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2484 4.9080 -2.9656 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9705 5.4791 -3.2602 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0453 6.5703 -4.1135 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0749 4.9118 -2.6694 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3223 5.4624 -2.9449 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9738 3.8060 -1.8076 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6910 1.9397 -0.1425 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0467 1.0051 0.6876 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3776 0.8715 1.1057 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7826 -0.1085 1.9889 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0570 -0.2934 2.4392 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2104 0.4154 2.1171 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3496 1.3569 3.1904 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1415 2.4237 2.7303 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1249 3.5088 3.7705 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8236 3.9662 3.9911 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5455 1.9131 2.4481 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9964 2.2759 1.1860 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6049 0.4152 2.6866 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6222 0.1999 4.0628 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4685 -0.3333 1.9969 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8278 -0.7758 0.7570 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9365 -2.1138 0.5457 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1956 -2.6182 -0.4878 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8358 -2.7219 -1.6902 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0417 -1.3881 -2.3925 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7270 -1.6019 -3.6075 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0744 -3.5792 -1.6835 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8596 -4.8563 -2.1920 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6518 -3.7346 -0.2971 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.0393 -3.9126 -0.3936 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4391 -2.4048 0.3942 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9977 -2.5282 1.6658 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8041 -0.9724 2.4534 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4803 -0.8624 2.0546 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5066 -1.7279 2.5173 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0944 0.1282 1.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2007 0.2735 0.7518 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0929 -0.5069 1.1687 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3476 1.2451 -2.4555 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7351 0.3568 -3.5021 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5925 1.7046 -1.7222 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5624 3.0230 -1.3374 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8159 0.7587 -0.5787 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1738 1.1237 0.5991 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8065 -1.1800 -1.3612 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7318 -1.8734 -2.1732 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5463 -0.8346 -0.0751 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5765 0.0733 -0.3181 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1873 -2.0945 0.4672 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5320 -1.8556 1.7948 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4018 -4.8291 -0.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6816 -5.3771 0.9072 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1560 -4.2911 0.8938 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6792 -3.3329 1.3731 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0850 -2.4406 -1.8130 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3477 -2.6364 -0.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3624 -1.2994 1.0490 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8031 -0.9059 -1.9121 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5238 0.1792 -2.1531 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3096 3.4007 -1.9114 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1521 5.3324 -3.4176 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9346 6.7883 -4.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3967 6.4765 -2.9807 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8613 3.4275 -1.3590 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1057 1.5487 0.7311 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0095 1.0100 1.1919 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7212 2.7998 1.7926 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7346 4.3708 3.3682 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6163 3.2124 4.7086 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2677 3.8885 3.1846 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2141 2.3867 3.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6454 1.6136 0.5406 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6008 0.0974 2.3081 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5535 1.0123 4.5935 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3457 -1.2730 2.6264 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6689 -2.7046 1.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1193 -3.2688 -2.3788 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6176 -0.6621 -1.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0330 -1.0197 -2.6898 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6976 -1.3961 -3.4584 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8577 -3.1033 -2.3142 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6680 -5.4521 -1.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1917 -4.5372 0.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3573 -4.7435 0.0419 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9790 -1.6056 -0.1145 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8903 -2.0578 1.7186 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0775 -1.7517 3.1423 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3309 -2.5459 3.0676 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8812 2.0933 -2.9736 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1103 -0.3940 -3.5567 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4686 1.5617 -2.4188 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8537 3.6393 -2.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9005 0.7298 -0.3183 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6160 1.8847 1.0080 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4163 -0.2941 -1.8495 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4694 -1.7898 -3.1282 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8144 -0.4181 0.6371 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2242 1.0072 -0.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1371 -2.3068 -0.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7044 -1.6990 2.3108 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 18 20 2 0 12 21 1 0 21 22 1 0 22 23 2 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 28 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 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 24 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 20 13 1 0 51 22 1 0 35 26 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 6 9 74 1 6 14 75 1 0 15 76 1 0 17 77 1 0 19 78 1 0 20 79 1 0 23 80 1 0 26 81 1 6 28 82 1 6 29 83 1 0 29 84 1 0 30 85 1 0 31 86 1 1 32 87 1 0 33 88 1 6 34 89 1 0 35 90 1 1 37 91 1 1 39 92 1 6 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 6 55105 1 0 56106 1 6 57107 1 0 58108 1 1 59109 1 0 60110 1 6 61111 1 0 62112 1 1 63113 1 0 64114 1 6 65115 1 0 M END

Standard InCHIKey	XPEIWSKZERJYMX-HGEJKOITSA-N
Standard InCHI	InChI=1S/C39H50O26/c1-10-21(45)26(50)30(54)36(58-10)57-9-19-24(48)28(52)32(56)38(63-19)64-34-25(49)20-15(44)5-12(6-16(20)60-33(34)11-2-3-13(42)14(43)4-11)59-39-35(29(53)23(47)18(8-41)62-39)65-37-31(55)27(51)22(46)17(7-40)61-37/h2-6,10,17-19,21-24,26-32,35-48,50-56H,7-9H2,1H3/t10-,17+,18+,19+,21-,22+,23+,24-,26+,27-,28-,29-,30+,31+,32+,35+,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)=C4)OC4=CC(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[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:	-1.696 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.155 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.193 ? 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:	0.075	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.971	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:	1
Colloidal aggregators:	0.642	Fluc inhibitor:	0.288 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.674 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.598 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.343	Promiscuous compounds:	0.618

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.259	MDCK Permeability:	-4.692
Pgp-inhibitor:	0.0	Pgp-substrate:	0.867
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):	0.999
20% Bioavailability (F20%):	0.512	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	60.87%	Volume Distribution (VD):	-0.254
Fu:	32.677% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.016
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:	0.084
HLM stability:	0.002 ? 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):

-0.061

Half-life (T1/2):

6.989

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.647	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.967	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.09	Drug-induced Nephrotoxicity:	0.847
Genotoxicity:	0.464	RPMI-8226 Immunitoxicity:	0.198
A549 Cytotoxicity:	0.908	Hek293 Cytotoxicity:	0.164
BCF:	0.327 ? 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:	2.755 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.576 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.583 ? 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
NPO21107	Bassia scoparia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24380276]
NPO21107	Bassia scoparia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15405	Suaeda maritima	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21107	Bassia scoparia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15405	Suaeda maritima	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21107	Bassia scoparia	Species	Chenopodiaceae	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 NPC554975 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	23100
0.1-0.2	22318
0.2-0.3	3567
0.3-0.4	393
0.4-0.5	225
0.5-0.6	110
0.6-0.7	72
0.7-0.8	2
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC480441
0.8182	Intermediate Similarity	NPC25523
0.7778	Intermediate Similarity	NPC14187
0.7629	Intermediate Similarity	NPC32641
0.7629	Intermediate Similarity	NPC256188
0.7629	Intermediate Similarity	NPC35119
0.75	Intermediate Similarity	NPC186816
0.7312	Intermediate Similarity	NPC605784
0.7245	Intermediate Similarity	NPC240306
0.72	Intermediate Similarity	NPC142142
0.7113	Intermediate Similarity	NPC67105
0.7041	Intermediate Similarity	NPC203259
0.7041	Intermediate Similarity	NPC33054
0.7041	Intermediate Similarity	NPC176740
0.7041	Intermediate Similarity	NPC471725
0.7041	Intermediate Similarity	NPC134532
0.7041	Intermediate Similarity	NPC156869
0.7041	Intermediate Similarity	NPC602582
0.697	Remote Similarity	NPC115674
0.6957	Remote Similarity	NPC136042
0.6931	Remote Similarity	NPC122467
0.6869	Remote Similarity	NPC210073
0.6869	Remote Similarity	NPC155877
0.6832	Remote Similarity	NPC470443
0.6827	Remote Similarity	NPC602448
0.6733	Remote Similarity	NPC488073
0.6733	Remote Similarity	NPC126784
0.6733	Remote Similarity	NPC241423
0.6729	Remote Similarity	NPC292019
0.6729	Remote Similarity	NPC202908
0.6702	Remote Similarity	NPC271692
0.6635	Remote Similarity	NPC473073
0.6598	Remote Similarity	NPC116458
0.6598	Remote Similarity	NPC246943
0.6569	Remote Similarity	NPC64425
0.6566	Remote Similarity	NPC8856
0.6526	Remote Similarity	NPC84362
0.6476	Remote Similarity	NPC473071
0.6465	Remote Similarity	NPC254855
0.6465	Remote Similarity	NPC94610
0.6455	Remote Similarity	NPC311850
0.6436	Remote Similarity	NPC173582
0.6436	Remote Similarity	NPC265885
0.6436	Remote Similarity	NPC181465
0.6436	Remote Similarity	NPC215710
0.6436	Remote Similarity	NPC275454
0.6436	Remote Similarity	NPC473438
0.6436	Remote Similarity	NPC227508
0.6436	Remote Similarity	NPC253788
0.64	Remote Similarity	NPC251417
0.6373	Remote Similarity	NPC65003
0.6372	Remote Similarity	NPC298666
0.6372	Remote Similarity	NPC198199
0.6364	Remote Similarity	NPC303694
0.6346	Remote Similarity	NPC12013
0.6346	Remote Similarity	NPC11432
0.6346	Remote Similarity	NPC477613
0.6321	Remote Similarity	NPC89127
0.6293	Remote Similarity	NPC192539
0.6275	Remote Similarity	NPC44931
0.6275	Remote Similarity	NPC39834
0.6275	Remote Similarity	NPC163242
0.6275	Remote Similarity	NPC272068
0.625	Remote Similarity	NPC297987
0.6214	Remote Similarity	NPC65563
0.6214	Remote Similarity	NPC470949
0.6204	Remote Similarity	NPC135358
0.6182	Remote Similarity	NPC189564
0.6154	Remote Similarity	NPC255157
0.6154	Remote Similarity	NPC259896
0.6146	Remote Similarity	NPC289667
0.6146	Remote Similarity	NPC249281
0.614	Remote Similarity	NPC68592
0.6139	Remote Similarity	NPC95866
0.6132	Remote Similarity	NPC473327
0.6117	Remote Similarity	NPC67326
0.6091	Remote Similarity	NPC203145
0.6068	Remote Similarity	NPC120952
0.6068	Remote Similarity	NPC209550
0.6058	Remote Similarity	NPC22062
0.6058	Remote Similarity	NPC473634
0.6058	Remote Similarity	NPC138811
0.604	Remote Similarity	NPC276377
0.602	Remote Similarity	NPC46420
0.6019	Remote Similarity	NPC195257
0.6019	Remote Similarity	NPC476472
0.6019	Remote Similarity	NPC294815
0.6019	Remote Similarity	NPC16194
0.6	Remote Similarity	NPC473571
0.6	Remote Similarity	NPC110941
0.5981	Remote Similarity	NPC209296
0.5963	Remote Similarity	NPC292929
0.5963	Remote Similarity	NPC221342
0.5963	Remote Similarity	NPC476470
0.5946	Remote Similarity	NPC89052
0.5946	Remote Similarity	NPC11468
0.5926	Remote Similarity	NPC486577
0.5918	Remote Similarity	NPC277205
0.5918	Remote Similarity	NPC158674
0.5918	Remote Similarity	NPC37919
0.5905	Remote Similarity	NPC150164
0.59	Remote Similarity	NPC611303
0.5882	Remote Similarity	NPC170052
0.5882	Remote Similarity	NPC135846
0.5872	Remote Similarity	NPC76831
0.5872	Remote Similarity	NPC220173
0.5849	Remote Similarity	NPC470444
0.5847	Remote Similarity	NPC480444
0.5825	Remote Similarity	NPC116864
0.5825	Remote Similarity	NPC244776
0.5818	Remote Similarity	NPC470445
0.5816	Remote Similarity	NPC238376
0.5806	Remote Similarity	NPC223860
0.5794	Remote Similarity	NPC488074
0.5789	Remote Similarity	NPC164704
0.5758	Remote Similarity	NPC145038
0.5758	Remote Similarity	NPC56077
0.5758	Remote Similarity	NPC281131
0.5758	Remote Similarity	NPC253662
0.5758	Remote Similarity	NPC179950
0.5758	Remote Similarity	NPC88789
0.5758	Remote Similarity	NPC491374
0.5755	Remote Similarity	NPC605592
0.5741	Remote Similarity	NPC65711
0.5739	Remote Similarity	NPC277532
0.5714	Remote Similarity	NPC480466
0.5714	Remote Similarity	NPC470720
0.5702	Remote Similarity	NPC219043
0.5702	Remote Similarity	NPC262222
0.569	Remote Similarity	NPC488083
0.566	Remote Similarity	NPC471748
0.5657	Remote Similarity	NPC127546
0.5657	Remote Similarity	NPC57625
0.5657	Remote Similarity	NPC173637
0.5657	Remote Similarity	NPC317489
0.5657	Remote Similarity	NPC223424
0.5657	Remote Similarity	NPC600591
0.5652	Remote Similarity	NPC473644
0.5652	Remote Similarity	NPC470715
0.563	Remote Similarity	NPC162394
0.563	Remote Similarity	NPC488740
0.5625	Remote Similarity	NPC470446
0.5619	Remote Similarity	NPC473682
0.561	Remote Similarity	NPC21359
0.561	Remote Similarity	NPC460984
0.5607	Remote Similarity	NPC479405
0.5607	Remote Similarity	NPC304741
0.5607	Remote Similarity	NPC303913
0.56	Remote Similarity	NPC189142
0.56	Remote Similarity	NPC77660
0.5596	Remote Similarity	NPC483414
0.5588	Remote Similarity	NPC488071
0.5577	Remote Similarity	NPC476215
0.5574	Remote Similarity	NPC480442
0.5566	Remote Similarity	NPC471079
0.5566	Remote Similarity	NPC29958
0.5565	Remote Similarity	NPC487499
0.5556	Remote Similarity	NPC479404
0.5545	Remote Similarity	NPC27640
0.5545	Remote Similarity	NPC72016
0.5526	Remote Similarity	NPC121703
0.55	Remote Similarity	NPC470719
0.55	Remote Similarity	NPC19709
0.55	Remote Similarity	NPC488736
0.55	Remote Similarity	NPC488733
0.55	Remote Similarity	NPC470717
0.5492	Remote Similarity	NPC175429
0.549	Remote Similarity	NPC42773
0.549	Remote Similarity	NPC45522
0.549	Remote Similarity	NPC599850
0.5487	Remote Similarity	NPC253685
0.5478	Remote Similarity	NPC473072
0.5469	Remote Similarity	NPC249560
0.5462	Remote Similarity	NPC295625
0.5455	Remote Similarity	NPC479403
0.5446	Remote Similarity	NPC475382
0.5446	Remote Similarity	NPC471669
0.5439	Remote Similarity	NPC244875
0.5431	Remote Similarity	NPC48984
0.5431	Remote Similarity	NPC173837
0.5424	Remote Similarity	NPC255799
0.5417	Remote Similarity	NPC480445
0.541	Remote Similarity	NPC138990
0.541	Remote Similarity	NPC488737
0.5405	Remote Similarity	NPC606657
0.5398	Remote Similarity	NPC287889
0.5392	Remote Similarity	NPC305811
0.5391	Remote Similarity	NPC487502
0.5391	Remote Similarity	NPC25724
0.537	Remote Similarity	NPC470405
0.5345	Remote Similarity	NPC488075
0.534	Remote Similarity	NPC59534
0.5315	Remote Similarity	NPC480471
0.5315	Remote Similarity	NPC488076
0.5294	Remote Similarity	NPC323593
0.5294	Remote Similarity	NPC203500
0.5285	Remote Similarity	NPC241781
0.5278	Remote Similarity	NPC187379
0.5276	Remote Similarity	NPC473554
0.5268	Remote Similarity	NPC229409

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC554975 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5949
0.1-0.2	3139
0.2-0.3	53
0.3-0.4	3
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
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
0.7835	Intermediate Similarity	NPD7251	Phase 2
0.7041	Intermediate Similarity	NPD6797	Phase 2
0.6698	Remote Similarity	NPD7808	Phase 3
0.5981	Remote Similarity	NPD7054	Phase 4

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