NPASS Compound

Natural Product: NPC231787

Natural Product ID	NPC231787
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-Alpha-L-Rhamnopyranosyl(1->6)-[(4-O-Trans-P-Coumaroyl)-Alpha-L-Rhamnopyranosyl(1-> 2)]-(4-O-Trans-P-Coumaroyl)-Beta-D-Galactopyranoside
IUPAC Name	[(2S,3R,4S,5R,6S)-6-[(2S,3R,4S,5R,6R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4-hydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL449412
PubChem CID	21576261
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 2D 126133 0 0 0 0 0 0 0 0999 V2000 1.5905 -12.5203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8509 -11.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3509 -11.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -9.7441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3509 -8.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8509 -8.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5905 -6.9678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -6.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8886 -5.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2981 -4.5264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -3.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4095 -2.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -4.0753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -1.1209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 -1.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2286 -0.1567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6382 0.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7872 -0.6078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5268 -2.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0268 -2.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1172 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5372 0.6912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0372 0.6912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7872 -0.6078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7872 1.9902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2872 1.9902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0372 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2872 4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0372 5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5372 5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.2872 4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5372 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.2872 7.1864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8882 1.6554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7286 -0.1567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 -3.5623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -6.0037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 -6.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1172 -5.5525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2286 -7.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6382 -8.5069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8986 -9.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7496 -10.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0100 -12.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4196 -12.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5686 -11.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3082 -10.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6800 -14.4158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6009 -9.7441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6114 -6.9678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5481 -8.7799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0586 -11.5562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0677 -12.7808 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7944 -12.4786 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3300 -13.9975 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2605 -11.5562 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3926 -11.8392 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6571 -10.5610 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0586 -7.9320 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3125 -8.1077 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7753 -4.8546 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8366 -7.0266 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6386 -6.3385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7981 -4.5264 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6007 -1.9703 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6595 -0.7860 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -1.1209 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -7.7942 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5548 -3.0758 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 1.3205 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7872 1.3205 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2488 -0.9452 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7872 -3.5623 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0268 -3.5850 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2096 -0.5962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5268 -2.0850 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0372 3.2893 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0372 0.6912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7872 4.5883 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2872 7.1864 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.7872 4.5883 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.2872 1.9902 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.7872 7.1864 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6382 2.9544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6866 -1.2356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3164 -2.9048 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0796 -8.9581 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7872 -7.5427 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3400 -10.4353 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8610 -13.3897 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9782 -12.4874 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4572 -9.5330 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0896 -14.9288 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 -6.1290 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9577 -9.2929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3166 -10.7392 0.0000 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 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 22 34 1 0 20 35 1 0 12 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 40 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 52 55 1 0 39 56 1 0 38 57 1 0 11 58 1 0 10 59 1 0 59 60 1 0 60 61 2 0 60 62 1 0 62 63 2 0 63 64 1 0 64 65 2 0 65 66 1 0 66 67 2 0 67 68 1 0 68 69 2 0 67 70 1 0 6 71 1 0 5 72 1 0 4 73 1 0 3 74 1 0 71 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 43 37 1 0 54 49 1 0 69 64 1 0 24 19 1 0 1 75 1 0 1 76 1 0 1 77 1 0 2 78 1 6 3 79 1 1 4 80 1 6 5 81 1 6 6 82 1 1 8 83 1 0 8 84 1 0 9 85 1 6 10 86 1 6 11 87 1 6 12 88 1 1 13 89 1 6 21 90 1 0 23 91 1 0 28 92 1 0 29 93 1 0 31 94 1 0 32 95 1 0 33 96 1 0 34 97 1 0 35 98 1 0 37 99 1 6 38100 1 1 39101 1 1 40102 1 6 41103 1 1 42104 1 0 42105 1 0 42106 1 0 47107 1 0 48108 1 0 50109 1 0 51110 1 0 53111 1 0 54112 1 0 55113 1 0 56114 1 0 57115 1 0 58116 1 0 62117 1 0 63118 1 0 65119 1 0 66120 1 0 68121 1 0 69122 1 0 70123 1 0 72124 1 0 73125 1 0 74126 1 0 M END

Standard InCHIKey	VHDYGKCMNQFOEX-HIIJJAAKSA-N
Standard InCHI	InChI=1S/C51H52O23/c1-22-37(59)39(61)41(63)49(67-22)66-21-33-46(72-35(58)18-8-25-5-13-28(53)14-6-25)43(65)48(74-50-42(64)40(62)44(23(2)68-50)71-34(57)17-7-24-3-11-27(52)12-4-24)51(70-33)73-47-38(60)36-31(56)19-30(55)20-32(36)69-45(47)26-9-15-29(54)16-10-26/h3-20,22-23,33,37,39-44,46,48-56,59,61-65H,21H2,1-2H3/b17-7+,18-8+/t22-,23-,33+,37-,39+,40-,41+,42+,43-,44-,46-,48+,49+,50-,51-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(cc2)O)O)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)OC(=O)/C=C/c2ccc(cc2)O)O)O)O)OC(=O)/C=C/c2ccc(cc2)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1032.29	Volume:	976.919 ? Van der Waals volume.
Dense:	1.057	LogP:	2.132 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.055 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.874 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	52.0
TPSA:	360.72 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.055	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.985	Fsp³:	0.353
MCE-18:	185.478 ? 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:	0.937	Fluc inhibitor:	0.846 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.617 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.36	Promiscuous compounds:	0.555

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.456	MDCK Permeability:	-5.12
Pgp-inhibitor:	0.0	Pgp-substrate:	0.57
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):	0.005
20% Bioavailability (F20%):	0.889	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):	84.976%	Volume Distribution (VD):	0.017
Fu:	11.008% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.053
BSEP inhibitor:	0.983

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.379
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.972
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.631 ? 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):

0.884

Half-life (T1/2):

5.67

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.358
Human Hepatotoxicity (H-HT):	0.41	Drug-induced Liver Injury (DILI):	0.925
AMES Toxicity:	0.636	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.556	Skin Sensitization:	1.0
Carcinogencity:	0.013	Eye Corrosion:	0.0
Eye Irritation:	0.2	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.909
Hematotoxicity:	0.004	Drug-induced Nephrotoxicity:	0.219
Genotoxicity:	0.971	RPMI-8226 Immunitoxicity:	0.134
A549 Cytotoxicity:	0.746	Hek293 Cytotoxicity:	0.991
BCF:	0.856 ? 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:	3.968 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.243 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.84 ? 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
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043423]
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
FC	1

Activity Type	# Activity
Others	1

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
NPT2	Others	Unspecified	n.a.	FC	=	5.0	n.a.	PMID[20192239]

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 NPC231787 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	15653
0.1-0.2	30081
0.2-0.3	3380
0.3-0.4	432
0.4-0.5	167
0.5-0.6	92
0.6-0.7	35
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9439	High Similarity	NPC30011
0.7778	Intermediate Similarity	NPC72554
0.7522	Intermediate Similarity	NPC156785
0.7522	Intermediate Similarity	NPC474522
0.7521	Intermediate Similarity	NPC97817
0.7217	Intermediate Similarity	NPC162394
0.7196	Intermediate Similarity	NPC221288
0.7196	Intermediate Similarity	NPC194836
0.7196	Intermediate Similarity	NPC91493
0.7196	Intermediate Similarity	NPC605081
0.6944	Remote Similarity	NPC104883
0.6944	Remote Similarity	NPC488679
0.6807	Remote Similarity	NPC241781
0.6748	Remote Similarity	NPC275977
0.6696	Remote Similarity	NPC483767
0.6696	Remote Similarity	NPC483769
0.6696	Remote Similarity	NPC483768
0.6696	Remote Similarity	NPC483766
0.6577	Remote Similarity	NPC101399
0.6577	Remote Similarity	NPC217822
0.6577	Remote Similarity	NPC11847
0.6577	Remote Similarity	NPC198938
0.6545	Remote Similarity	NPC12013
0.6545	Remote Similarity	NPC11432
0.6545	Remote Similarity	NPC477613
0.6535	Remote Similarity	NPC249560
0.6491	Remote Similarity	NPC483765
0.648	Remote Similarity	NPC473554
0.6457	Remote Similarity	NPC487502
0.6404	Remote Similarity	NPC218161
0.6262	Remote Similarity	NPC476215
0.6261	Remote Similarity	NPC602448
0.6174	Remote Similarity	NPC221342
0.6174	Remote Similarity	NPC476470
0.6148	Remote Similarity	NPC33083
0.6087	Remote Similarity	NPC85751
0.6087	Remote Similarity	NPC19240
0.6068	Remote Similarity	NPC478277
0.6068	Remote Similarity	NPC478276
0.6068	Remote Similarity	NPC478275
0.6068	Remote Similarity	NPC92815
0.6053	Remote Similarity	NPC122467
0.6036	Remote Similarity	NPC163242
0.6036	Remote Similarity	NPC272068
0.6	Remote Similarity	NPC470712
0.5984	Remote Similarity	NPC25946
0.5948	Remote Similarity	NPC89127
0.5932	Remote Similarity	NPC96605
0.5932	Remote Similarity	NPC280642
0.5893	Remote Similarity	NPC173582
0.5893	Remote Similarity	NPC265885
0.5893	Remote Similarity	NPC181465
0.5893	Remote Similarity	NPC215710
0.5893	Remote Similarity	NPC473438
0.5893	Remote Similarity	NPC253788
0.5882	Remote Similarity	NPC89052
0.5862	Remote Similarity	NPC205824
0.5852	Remote Similarity	NPC487501
0.5806	Remote Similarity	NPC488734
0.5806	Remote Similarity	NPC488735
0.5806	Remote Similarity	NPC488739
0.5806	Remote Similarity	NPC488732
0.5806	Remote Similarity	NPC488738
0.5785	Remote Similarity	NPC173837
0.578	Remote Similarity	NPC259957
0.5772	Remote Similarity	NPC470718
0.5766	Remote Similarity	NPC95866
0.576	Remote Similarity	NPC480445
0.575	Remote Similarity	NPC203145
0.5714	Remote Similarity	NPC223426
0.5667	Remote Similarity	NPC214621
0.5667	Remote Similarity	NPC34267
0.5662	Remote Similarity	NPC487500
0.5625	Remote Similarity	NPC488737
0.5596	Remote Similarity	NPC216496
0.5573	Remote Similarity	NPC21359
0.5573	Remote Similarity	NPC460984
0.5565	Remote Similarity	NPC155877
0.5556	Remote Similarity	NPC474093
0.5556	Remote Similarity	NPC104910
0.5545	Remote Similarity	NPC159579
0.5536	Remote Similarity	NPC170052
0.5536	Remote Similarity	NPC135846
0.5528	Remote Similarity	NPC477895
0.55	Remote Similarity	NPC292929
0.5484	Remote Similarity	NPC217520
0.5484	Remote Similarity	NPC303694
0.5478	Remote Similarity	NPC470405
0.547	Remote Similarity	NPC470125
0.5469	Remote Similarity	NPC488740
0.5469	Remote Similarity	NPC488736
0.5469	Remote Similarity	NPC488733
0.5462	Remote Similarity	NPC142142
0.5431	Remote Similarity	NPC203259
0.5431	Remote Similarity	NPC33054
0.5431	Remote Similarity	NPC304741
0.5431	Remote Similarity	NPC176740
0.5431	Remote Similarity	NPC471725
0.5431	Remote Similarity	NPC134532
0.5431	Remote Similarity	NPC602582
0.5426	Remote Similarity	NPC480444
0.5417	Remote Similarity	NPC220173
0.5407	Remote Similarity	NPC223860
0.5391	Remote Similarity	NPC470713
0.5391	Remote Similarity	NPC139320
0.539	Remote Similarity	NPC482521
0.5378	Remote Similarity	NPC473327
0.537	Remote Similarity	NPC111929
0.537	Remote Similarity	NPC320283
0.537	Remote Similarity	NPC41121
0.536	Remote Similarity	NPC164704
0.5323	Remote Similarity	NPC189564
0.5299	Remote Similarity	NPC487499
0.5289	Remote Similarity	NPC476472
0.5289	Remote Similarity	NPC294815
0.5289	Remote Similarity	NPC16194
0.5285	Remote Similarity	NPC81042
0.5268	Remote Similarity	NPC48093
0.5246	Remote Similarity	NPC470449
0.5227	Remote Similarity	NPC192539
0.5227	Remote Similarity	NPC175429
0.5221	Remote Similarity	NPC224530
0.5169	Remote Similarity	NPC605592
0.5164	Remote Similarity	NPC471669
0.5128	Remote Similarity	NPC471079
0.5126	Remote Similarity	NPC129264
0.5126	Remote Similarity	NPC470444
0.5122	Remote Similarity	NPC36138
0.5118	Remote Similarity	NPC470715
0.5118	Remote Similarity	NPC25523
0.5086	Remote Similarity	NPC254855
0.5086	Remote Similarity	NPC94610
0.5085	Remote Similarity	NPC39834
0.5083	Remote Similarity	NPC240306
0.5069	Remote Similarity	NPC482520
0.5069	Remote Similarity	NPC482519
0.5039	Remote Similarity	NPC139571

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC231787 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4801
0.1-0.2	4286
0.2-0.3	56
0.3-0.4	4
0.4-0.5	2
0.5-0.6	1
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
0.5431	Remote Similarity	NPD6797	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data