NPASS Compound

Natural Product: NPC575866

Natural Product ID	NPC575866
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	kaempferol 3-O-[beta-glucosyl-(1â†’2)]-[alpha-rhamnosyl-(1â†’6)]-beta-glucoside-7-O-alpha-rhamnoside
IUPAC Name	3-[(3~{S},4~{S},5~{S},6~{R})-4,5-dihydroxy-3-[(3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[[(3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-methyl-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 113119 0 0 0 0 0 0 0 0999 V2000 -4.1916 6.7991 0.7652 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0169 5.6894 1.3669 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4608 4.4978 0.9955 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0585 3.3699 1.5720 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1550 2.3466 1.3043 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6467 1.6088 0.2360 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7310 0.5728 -0.2593 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4326 -0.4642 0.6048 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2164 -1.0318 0.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2356 -0.1272 0.4199 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0791 -0.0096 0.4818 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8659 -0.2842 1.5551 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3167 -0.7620 2.7981 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1846 -1.4095 3.6925 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7486 -1.8510 4.9294 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5575 -1.6660 5.3181 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0293 -2.1095 6.5739 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 -1.0359 4.4586 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9528 -0.6000 3.2219 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2080 -0.1245 1.4976 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8121 0.2948 0.4336 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1870 0.4614 0.3826 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8908 0.9079 -0.7078 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2560 1.0622 -0.7173 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0775 1.5510 -1.7023 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0062 0.5330 -2.0666 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8007 1.0247 -3.1153 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3228 -0.1196 -3.9104 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8718 1.9265 -2.5413 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0893 3.0260 -3.3540 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3950 2.4281 -1.1769 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7232 1.5399 -0.1530 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9303 2.7295 -1.2294 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5326 3.0468 0.0930 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1574 1.2079 -1.8352 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7676 1.0544 -1.8336 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0408 1.3540 -2.9645 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0956 0.6016 -0.7109 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7340 0.4476 -0.6817 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0657 0.7197 -1.7079 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3636 -1.5752 -1.2372 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1419 -2.7585 -1.0512 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3771 -3.9131 -1.2266 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3943 -4.5986 -0.0048 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3704 -5.9597 -0.0892 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6866 -6.4730 1.1812 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6165 -7.8633 1.1933 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6248 -6.4891 -1.2667 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7079 -7.8715 -1.2754 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1899 -5.9671 -2.5744 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1493 -5.5350 -3.4108 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0597 -4.7707 -2.2585 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3221 -5.1779 -1.8416 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0534 -0.6795 -2.1893 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5079 -1.3950 -3.3024 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2770 -0.0705 -1.5126 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9415 0.8075 -2.3263 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4586 3.5039 2.9793 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2494 2.3223 3.6898 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6026 4.6369 3.5795 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2697 4.4278 3.1832 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0723 5.8907 2.8557 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3663 6.1462 3.2854 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6505 7.2171 -0.1572 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9921 7.6194 1.4741 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1880 6.4000 0.4434 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0341 5.7641 0.9491 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9587 3.2036 0.9203 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5681 1.0901 0.6359 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9281 2.2669 -0.6230 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7394 1.0391 -0.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0929 -1.9872 0.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2065 -1.5691 3.4161 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4312 -2.3566 5.6236 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5243 -2.8640 7.0456 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4513 -0.8646 4.7153 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6782 -0.0825 2.6336 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7661 0.2278 1.2687 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5572 1.8855 -2.6458 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1161 1.6267 -3.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2833 -0.4808 -3.4841 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6302 -0.9902 -3.9290 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4672 0.1434 -4.9876 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7926 1.3631 -2.4385 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2160 3.4701 -3.4870 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9709 3.3582 -0.9946 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9086 1.0508 0.1496 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7593 3.6366 -1.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2497 2.2447 0.5794 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6116 1.5650 -2.7409 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7347 0.6546 -3.6335 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3270 -1.8793 -1.5592 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3256 -3.7192 -1.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4288 -6.3675 -0.0822 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2614 -6.0814 2.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6997 -5.9925 1.2332 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0733 -8.1744 2.0290 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5605 -6.1804 -1.1678 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6384 -8.1684 -1.1218 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8359 -6.7168 -3.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1639 -4.5462 -3.5211 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2526 -4.1729 -3.2004 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4763 -6.0843 -2.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4260 0.1429 -2.5279 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2547 -2.0104 -3.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9235 -0.9178 -1.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9432 0.6688 -2.3015 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5165 3.8479 3.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2530 2.2584 3.8292 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7329 4.7493 4.6512 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8337 5.2495 2.8770 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4341 6.7201 3.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7920 6.8988 2.8043 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 2 0 12 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 23 35 2 0 35 36 1 0 36 37 1 0 36 38 2 0 38 39 1 0 39 40 2 0 9 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 45 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 50 52 1 0 52 53 1 0 41 54 1 0 54 55 1 0 54 56 1 0 56 57 1 0 4 58 1 0 58 59 1 0 58 60 1 0 60 61 1 0 60 62 1 0 62 63 1 0 62 2 1 0 56 7 1 0 39 11 1 0 52 43 1 0 19 13 1 0 38 21 1 0 33 25 1 0 1 64 1 0 1 65 1 0 1 66 1 0 2 67 1 6 4 68 1 0 6 69 1 0 6 70 1 0 7 71 1 6 9 72 1 0 14 73 1 0 15 74 1 0 17 75 1 0 18 76 1 0 19 77 1 0 22 78 1 0 25 79 1 0 27 80 1 6 28 81 1 0 28 82 1 0 28 83 1 0 29 84 1 1 30 85 1 0 31 86 1 1 32 87 1 0 33 88 1 6 34 89 1 0 35 90 1 0 37 91 1 0 41 92 1 6 43 93 1 0 45 94 1 6 46 95 1 0 46 96 1 0 47 97 1 0 48 98 1 1 49 99 1 0 50100 1 6 51101 1 0 52102 1 6 53103 1 0 54104 1 6 55105 1 0 56106 1 1 57107 1 0 58108 1 6 59109 1 0 60110 1 1 61111 1 0 62112 1 6 63113 1 0 M END

Standard InCHIKey	CGBWBDPNSXERKW-VQTYLAQXSA-N
Standard InCHI	InChI=1S/C39H50O24/c1-11-21(43)26(48)30(52)36(56-11)55-10-19-24(46)29(51)35(63-38-32(54)28(50)23(45)18(9-40)60-38)39(61-19)62-34-25(47)20-16(42)7-15(58-37-31(53)27(49)22(44)12(2)57-37)8-17(20)59-33(34)13-3-5-14(41)6-4-13/h3-8,11-12,18-19,21-24,26-32,35-46,48-54H,9-10H2,1-2H3/t11-,12-,18-,19-,21-,22-,23-,24-,26+,27+,28+,29+,30+,31+,32-,35+,36?,37?,38?,39?/m1/s1
SMILES	C[C@H]1OC(OC[C@H]2OC(OC3=C(C4=CC=C(O)C=C4)OC4=CC(OC5O[C@H](C)[C@@H](O)[C@H](O)[C@@H]5O)=CC(O)=C4C3=O)[C@@H](OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	902.27	Volume:	813.078 ? Van der Waals volume.
Dense:	1.11	LogP:	-0.635 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.302 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.642 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	42.0
TPSA:	387.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	14.0	Rings:	7.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.086	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.871	Fsp³:	0.615
MCE-18:	181.746 ? 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:	0.615	Fluc inhibitor:	0.219 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.682 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.653 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.346	Promiscuous compounds:	0.334

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.055	MDCK Permeability:	-4.722
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):	0.137
20% Bioavailability (F20%):	0.009	30% Bioavailability (F30%):	0.878
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.003
Plasma Protein Binding (PPB):	70.016%	Volume Distribution (VD):	-0.159
Fu:	25.688% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.008
BSEP inhibitor:	0.002

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:	0.966
HLM stability:	0.001 ? 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):

0.249

Half-life (T1/2):

6.853

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.068
Human Hepatotoxicity (H-HT):	0.373	Drug-induced Liver Injury (DILI):	0.965
AMES Toxicity:	0.944	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	0.998
Carcinogencity:	0.01	Eye Corrosion:	0.0
Eye Irritation:	0.006	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.996
Hematotoxicity:	0.078	Drug-induced Nephrotoxicity:	0.804
Genotoxicity:	0.779	RPMI-8226 Immunitoxicity:	0.259
A549 Cytotoxicity:	0.493	Hek293 Cytotoxicity:	0.492
BCF:	0.325 ? 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:	2.696 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.507 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.491 ? 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
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24024688]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38194794]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38195615]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38681233]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38731845]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39553766]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39723058]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798960]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	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 NPC575866 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	23645
0.1-0.2	21674
0.2-0.3	3639
0.3-0.4	427
0.4-0.5	247
0.5-0.6	118
0.6-0.7	60
0.7-0.8	0
0.8-0.85	2
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9778	High Similarity	NPC25523
0.8936	High Similarity	NPC480441
0.8681	High Similarity	NPC142142
0.8571	High Similarity	NPC32641
0.8571	High Similarity	NPC256188
0.8571	High Similarity	NPC35119
0.8043	Intermediate Similarity	NPC186816
0.8021	Intermediate Similarity	NPC602448
0.7957	Intermediate Similarity	NPC240306
0.75	Intermediate Similarity	NPC12013
0.75	Intermediate Similarity	NPC11432
0.75	Intermediate Similarity	NPC477613
0.7473	Intermediate Similarity	NPC116458
0.7473	Intermediate Similarity	NPC246943
0.74	Intermediate Similarity	NPC14187
0.7216	Intermediate Similarity	NPC64425
0.7103	Intermediate Similarity	NPC298666
0.7064	Intermediate Similarity	NPC209550
0.703	Intermediate Similarity	NPC292929
0.703	Intermediate Similarity	NPC221342
0.703	Intermediate Similarity	NPC476470
0.7	Intermediate Similarity	NPC249281
0.6923	Remote Similarity	NPC297987
0.69	Remote Similarity	NPC122467
0.6848	Remote Similarity	NPC46420
0.6847	Remote Similarity	NPC192539
0.6842	Remote Similarity	NPC276377
0.6737	Remote Similarity	NPC605784
0.6735	Remote Similarity	NPC163242
0.6735	Remote Similarity	NPC272068
0.6667	Remote Similarity	NPC150164
0.6574	Remote Similarity	NPC311850
0.6566	Remote Similarity	NPC173582
0.6566	Remote Similarity	NPC44931
0.6566	Remote Similarity	NPC265885
0.6566	Remote Similarity	NPC181465
0.6566	Remote Similarity	NPC215710
0.6566	Remote Similarity	NPC473438
0.6566	Remote Similarity	NPC253788
0.6531	Remote Similarity	NPC251417
0.6509	Remote Similarity	NPC89052
0.65	Remote Similarity	NPC65003
0.6486	Remote Similarity	NPC198199
0.6396	Remote Similarity	NPC68592
0.6355	Remote Similarity	NPC203145
0.633	Remote Similarity	NPC303694
0.633	Remote Similarity	NPC164704
0.6327	Remote Similarity	NPC170052
0.6327	Remote Similarity	NPC476215
0.6327	Remote Similarity	NPC135846
0.6316	Remote Similarity	NPC120952
0.6296	Remote Similarity	NPC189564
0.6286	Remote Similarity	NPC89127
0.6277	Remote Similarity	NPC289667
0.6275	Remote Similarity	NPC470444
0.625	Remote Similarity	NPC72016
0.6238	Remote Similarity	NPC67105
0.6211	Remote Similarity	NPC136042
0.62	Remote Similarity	NPC473682
0.6195	Remote Similarity	NPC480445
0.6176	Remote Similarity	NPC65563
0.6176	Remote Similarity	NPC210073
0.6176	Remote Similarity	NPC470949
0.6176	Remote Similarity	NPC155877
0.6146	Remote Similarity	NPC271692
0.6121	Remote Similarity	NPC175429
0.6117	Remote Similarity	NPC115674
0.6117	Remote Similarity	NPC473571
0.6117	Remote Similarity	NPC110941
0.6078	Remote Similarity	NPC470405
0.6055	Remote Similarity	NPC11468
0.6036	Remote Similarity	NPC470715
0.6019	Remote Similarity	NPC203259
0.6019	Remote Similarity	NPC33054
0.6019	Remote Similarity	NPC304741
0.6019	Remote Similarity	NPC176740
0.6019	Remote Similarity	NPC471725
0.6019	Remote Similarity	NPC134532
0.6019	Remote Similarity	NPC156869
0.6019	Remote Similarity	NPC602582
0.6	Remote Similarity	NPC473554
0.6	Remote Similarity	NPC470717
0.5981	Remote Similarity	NPC76831
0.5979	Remote Similarity	NPC84362
0.5946	Remote Similarity	NPC173837
0.5932	Remote Similarity	NPC262222
0.5929	Remote Similarity	NPC488083
0.5897	Remote Similarity	NPC138990
0.5893	Remote Similarity	NPC473644
0.5872	Remote Similarity	NPC135358
0.5865	Remote Similarity	NPC22062
0.5865	Remote Similarity	NPC479405
0.5865	Remote Similarity	NPC473634
0.5865	Remote Similarity	NPC303913
0.5865	Remote Similarity	NPC138811
0.5859	Remote Similarity	NPC611303
0.5849	Remote Similarity	NPC470443
0.5847	Remote Similarity	NPC480443
0.5833	Remote Similarity	NPC473071
0.5833	Remote Similarity	NPC220173
0.5812	Remote Similarity	NPC480444
0.5812	Remote Similarity	NPC470720
0.581	Remote Similarity	NPC479404
0.5804	Remote Similarity	NPC292019
0.5804	Remote Similarity	NPC202908
0.5794	Remote Similarity	NPC209296
0.5784	Remote Similarity	NPC254855
0.5784	Remote Similarity	NPC94610
0.5784	Remote Similarity	NPC95866
0.5773	Remote Similarity	NPC108831
0.5773	Remote Similarity	NPC182634
0.5769	Remote Similarity	NPC275454
0.5769	Remote Similarity	NPC227508
0.5766	Remote Similarity	NPC121703
0.5728	Remote Similarity	NPC8856
0.5726	Remote Similarity	NPC162394
0.5714	Remote Similarity	NPC158674
0.5714	Remote Similarity	NPC323593
0.5714	Remote Similarity	NPC203500
0.5702	Remote Similarity	NPC277532
0.569	Remote Similarity	NPC488739
0.5688	Remote Similarity	NPC195257
0.5688	Remote Similarity	NPC476472
0.5688	Remote Similarity	NPC294815
0.5688	Remote Similarity	NPC473073
0.5688	Remote Similarity	NPC16194
0.5673	Remote Similarity	NPC471079
0.567	Remote Similarity	NPC111929
0.567	Remote Similarity	NPC320283
0.567	Remote Similarity	NPC331652
0.567	Remote Similarity	NPC41121
0.5664	Remote Similarity	NPC219043
0.5648	Remote Similarity	NPC473327
0.5619	Remote Similarity	NPC39834
0.5612	Remote Similarity	NPC39360
0.5612	Remote Similarity	NPC77672
0.5612	Remote Similarity	NPC133671
0.5612	Remote Similarity	NPC135391
0.5612	Remote Similarity	NPC29763
0.5612	Remote Similarity	NPC78263
0.5612	Remote Similarity	NPC210003
0.5612	Remote Similarity	NPC250069
0.5607	Remote Similarity	NPC488073
0.5607	Remote Similarity	NPC126784
0.5607	Remote Similarity	NPC241423
0.5556	Remote Similarity	NPC488734
0.5556	Remote Similarity	NPC249560
0.5556	Remote Similarity	NPC295625
0.5556	Remote Similarity	NPC488735
0.5556	Remote Similarity	NPC479403
0.5556	Remote Similarity	NPC488732
0.5556	Remote Similarity	NPC488738
0.5528	Remote Similarity	NPC487499
0.5524	Remote Similarity	NPC139320
0.552	Remote Similarity	NPC223860
0.5514	Remote Similarity	NPC255157
0.5514	Remote Similarity	NPC259896
0.55	Remote Similarity	NPC24043
0.5495	Remote Similarity	NPC101636
0.5476	Remote Similarity	NPC487502
0.5462	Remote Similarity	NPC470719
0.5455	Remote Similarity	NPC238376
0.5439	Remote Similarity	NPC473072
0.541	Remote Similarity	NPC480442
0.5405	Remote Similarity	NPC475382
0.54	Remote Similarity	NPC277205
0.54	Remote Similarity	NPC37919
0.5391	Remote Similarity	NPC48984
0.5385	Remote Similarity	NPC470716
0.5372	Remote Similarity	NPC488737
0.5366	Remote Similarity	NPC25946
0.5364	Remote Similarity	NPC606657
0.534	Remote Similarity	NPC224530
0.5333	Remote Similarity	NPC488740
0.53	Remote Similarity	NPC19709
0.5294	Remote Similarity	NPC488086
0.5268	Remote Similarity	NPC470447
0.5254	Remote Similarity	NPC488087
0.5254	Remote Similarity	NPC255799
0.5248	Remote Similarity	NPC64305
0.5248	Remote Similarity	NPC189142
0.5248	Remote Similarity	NPC77660
0.5243	Remote Similarity	NPC285197
0.5234	Remote Similarity	NPC480466
0.5229	Remote Similarity	NPC122809
0.5221	Remote Similarity	NPC287889
0.5207	Remote Similarity	NPC488736
0.5207	Remote Similarity	NPC488733
0.5196	Remote Similarity	NPC488080
0.5196	Remote Similarity	NPC169977
0.5191	Remote Similarity	NPC487500
0.5185	Remote Similarity	NPC67326
0.5152	Remote Similarity	NPC487501
0.5149	Remote Similarity	NPC127546
0.5149	Remote Similarity	NPC57625
0.5149	Remote Similarity	NPC173637
0.5149	Remote Similarity	NPC317489
0.5149	Remote Similarity	NPC223424
0.5149	Remote Similarity	NPC600591
0.5146	Remote Similarity	NPC216496

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC575866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5985
0.1-0.2	3101
0.2-0.3	54
0.3-0.4	3
0.4-0.5	3
0.5-0.6	1
0.6-0.7	3
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
0.6765	Remote Similarity	NPD7251	Phase 2
0.6355	Remote Similarity	NPD7808	Phase 3
0.6019	Remote Similarity	NPD6797	Phase 2
0.5794	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