NPASS Compound

Natural Product: NPC72554

Natural Product ID	NPC72554
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Quercetin 3-O-Alpha-L-Rhamnopyranosyl(1->6)-[(4-O-Trans-P-Coumaroyl)-Alpha-L-Rhamnopyranosyl(1->2)]-(3-O-Trans-P-Coumaroyl)-Beta-D-Galactopyranoside
IUPAC Name	[(2S,3R,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-5-hydroxy-4-[(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	CHEMBL461396
PubChem CID	21576262
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 127134 0 0 0 0 0 0 0 0999 V2000 -15.0372 8.4854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.2872 7.1864 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 -14.2872 4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7872 4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0372 5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7872 7.1864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0372 3.2893 0.0000 C 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 -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 -10.5372 0.6912 0.0000 O 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 -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 -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 -5.5586 -1.1209 0.0000 O 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 -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 -6.9681 -3.5623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2286 -5.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5145 -6.0225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6382 -5.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7872 -4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1968 -5.1013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4572 -6.5786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8668 -7.0916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0158 -6.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7554 -4.6502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3458 -4.1372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.4254 -6.6404 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 -2.7395 -6.0037 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 -1.8509 -8.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3509 -8.4450 0.0000 O 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 1.5481 -8.7799 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 -1.8509 -11.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6009 -9.7441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -10.7083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5905 -12.5203 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 -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 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 -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 -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 O 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 1.5000 5.1962 0.0000 O 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 1.5000 -5.1962 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 3.7500 -3.8971 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 5.2500 -3.8971 0.0000 O 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 -16.5372 8.4854 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.5372 5.8874 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.0372 3.2893 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5372 5.8874 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0372 8.4854 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5372 3.2893 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2872 1.9902 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5640 -0.7871 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6052 -3.5830 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 -11.1239 -1.2938 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5156 -1.9022 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 -8.6382 2.9544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9786 1.1424 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 -4.6386 -6.3385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7536 -4.8894 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 -8.8986 -7.0297 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3486 -3.1539 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3082 -7.5427 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1272 -8.5688 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9044 -3.6860 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2674 -2.6392 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.5744 -5.6763 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9681 -6.5167 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 -3.3125 -8.1077 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5481 -10.7083 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5123 -9.9290 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5840 -7.6308 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6972 -7.8157 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6114 -12.5203 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 -3.7500 -8.7799 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -10.1952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 -13.4845 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3191 -13.0334 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 3.8971 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 3.0000 5.1962 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 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 6.0000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 5 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 18 21 1 0 17 22 1 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 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 37 40 1 0 27 41 1 0 26 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 48 53 1 0 24 54 1 0 54 55 1 0 55 56 2 0 56 57 1 0 57 58 1 0 58 59 2 0 59 60 1 0 60 61 2 0 59 62 1 0 62 63 1 0 62 64 2 0 64 65 1 0 65 66 2 0 65 67 1 0 56 68 1 0 68 69 2 0 69 70 1 0 70 71 2 0 71 72 1 0 72 73 2 0 72 74 1 0 71 75 1 0 7 2 1 0 19 13 1 0 28 23 1 0 39 34 1 0 50 44 1 0 60 55 1 0 73 68 1 0 66 58 1 0 1 76 1 0 3 77 1 0 4 78 1 0 6 79 1 0 7 80 1 0 8 81 1 0 9 82 1 0 13 83 1 1 14 84 1 6 15 85 1 0 15 86 1 0 15 87 1 0 17 88 1 1 18 89 1 6 19 90 1 6 20 91 1 0 21 92 1 0 23 93 1 6 24 94 1 1 26 95 1 1 27 96 1 1 28 97 1 1 32 98 1 0 33 99 1 0 35100 1 0 36101 1 0 38102 1 0 39103 1 0 40104 1 0 41105 1 0 42106 1 0 42107 1 0 44108 1 1 46109 1 6 47110 1 0 47111 1 0 47112 1 0 48113 1 1 49114 1 6 50115 1 6 51116 1 0 52117 1 0 53118 1 0 63119 1 0 64120 1 0 66121 1 0 67122 1 0 69123 1 0 70124 1 0 73125 1 0 74126 1 0 75127 1 0 M END

Standard InCHIKey	NSOXFPIGIUWTDU-SCYPOZLLSA-N
Standard InCHI	InChI=1S/C51H52O24/c1-21-37(60)40(63)42(65)49(68-21)67-20-33-38(61)46(73-35(59)16-8-24-5-12-27(53)13-6-24)48(75-50-43(66)41(64)44(22(2)69-50)72-34(58)15-7-23-3-10-26(52)11-4-23)51(71-33)74-47-39(62)36-31(57)18-28(54)19-32(36)70-45(47)25-9-14-29(55)30(56)17-25/h3-19,21-22,33,37-38,40-44,46,48-57,60-61,63-66H,20H2,1-2H3/b15-7+,16-8+/t21-,22-,33+,37-,38-,40+,41-,42+,43+,44-,46-,48+,49+,50-,51-/m0/s1
SMILES	Oc1ccc(cc1)/C=C/C(=O)O[C@H]1[C@H](C)O[C@H]([C@@H]([C@@H]1O)O)O[C@H]1[C@@H](O[C@@H]([C@@H]([C@@H]1OC(=O)/C=C/c1ccc(cc1)O)O)CO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1048.28	Volume:	985.709 ? Van der Waals volume.
Dense:	1.063	LogP:	1.708 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.536 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.847 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	52.0
TPSA:	380.95 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	12.0	Rings:	8.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.042	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.063	Fsp³:	0.353
MCE-18:	188.913 ? 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:	0.909	Fluc inhibitor:	0.674 ? 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:	0.667 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.358	Promiscuous compounds:	0.598

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.524	MDCK Permeability:	-5.162
Pgp-inhibitor:	0.0	Pgp-substrate:	0.105
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):	0.046
20% Bioavailability (F20%):	0.996	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):	85.065%	Volume Distribution (VD):	0.012
Fu:	12.263% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.026
BSEP inhibitor:	0.883

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.989
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.346 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.292

Half-life (T1/2):

5.538

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.469
Human Hepatotoxicity (H-HT):	0.311	Drug-induced Liver Injury (DILI):	0.899
AMES Toxicity:	0.697	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.495	Skin Sensitization:	1.0
Carcinogencity:	0.009	Eye Corrosion:	0.0
Eye Irritation:	0.169	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.969
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.128
Genotoxicity:	0.946	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.914	Hek293 Cytotoxicity:	0.98
BCF:	0.675 ? 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:	3.802 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.173 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.753 ? 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	=	10.0	n.a.	PMID[17850214]

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 NPC72554 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	16262
0.1-0.2	29513
0.2-0.3	3315
0.3-0.4	450
0.4-0.5	170
0.5-0.6	101
0.6-0.7	33
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9633	High Similarity	NPC97817
0.8261	Intermediate Similarity	NPC30011
0.8246	Intermediate Similarity	NPC275977
0.7857	Intermediate Similarity	NPC162394
0.7778	Intermediate Similarity	NPC231787
0.7719	Intermediate Similarity	NPC241781
0.7544	Intermediate Similarity	NPC156785
0.746	Intermediate Similarity	NPC33083
0.7097	Intermediate Similarity	NPC249560
0.688	Remote Similarity	NPC487502
0.6667	Remote Similarity	NPC474522
0.6607	Remote Similarity	NPC101399
0.6607	Remote Similarity	NPC217822
0.6607	Remote Similarity	NPC11847
0.6607	Remote Similarity	NPC198938
0.6549	Remote Similarity	NPC89127
0.6518	Remote Similarity	NPC122467
0.6518	Remote Similarity	NPC104883
0.6518	Remote Similarity	NPC488679
0.646	Remote Similarity	NPC221288
0.646	Remote Similarity	NPC194836
0.646	Remote Similarity	NPC91493
0.646	Remote Similarity	NPC605081
0.6364	Remote Similarity	NPC487501
0.6293	Remote Similarity	NPC223426
0.625	Remote Similarity	NPC473554
0.6239	Remote Similarity	NPC483765
0.6165	Remote Similarity	NPC487500
0.6161	Remote Similarity	NPC203259
0.6161	Remote Similarity	NPC33054
0.6161	Remote Similarity	NPC176740
0.6161	Remote Similarity	NPC471725
0.6161	Remote Similarity	NPC134532
0.6161	Remote Similarity	NPC602582
0.6154	Remote Similarity	NPC483767
0.6154	Remote Similarity	NPC483769
0.6154	Remote Similarity	NPC483768
0.6154	Remote Similarity	NPC483766
0.614	Remote Similarity	NPC12013
0.614	Remote Similarity	NPC11432
0.614	Remote Similarity	NPC477613
0.6017	Remote Similarity	NPC218161
0.5902	Remote Similarity	NPC303694
0.5882	Remote Similarity	NPC602448
0.5847	Remote Similarity	NPC85751
0.5847	Remote Similarity	NPC19240
0.5846	Remote Similarity	NPC21359
0.5846	Remote Similarity	NPC460984
0.5833	Remote Similarity	NPC96605
0.5833	Remote Similarity	NPC280642
0.5833	Remote Similarity	NPC81042
0.582	Remote Similarity	NPC173837
0.5804	Remote Similarity	NPC95866
0.5798	Remote Similarity	NPC221342
0.5798	Remote Similarity	NPC476470
0.5789	Remote Similarity	NPC173582
0.5789	Remote Similarity	NPC265885
0.5789	Remote Similarity	NPC181465
0.5789	Remote Similarity	NPC215710
0.5789	Remote Similarity	NPC473438
0.5789	Remote Similarity	NPC253788
0.5785	Remote Similarity	NPC89052
0.5785	Remote Similarity	NPC203145
0.5755	Remote Similarity	NPC482521
0.5714	Remote Similarity	NPC471669
0.5702	Remote Similarity	NPC478277
0.5702	Remote Similarity	NPC478276
0.5702	Remote Similarity	NPC478275
0.5702	Remote Similarity	NPC92815
0.5682	Remote Similarity	NPC487499
0.5672	Remote Similarity	NPC223860
0.5645	Remote Similarity	NPC470712
0.563	Remote Similarity	NPC205824
0.5625	Remote Similarity	NPC488740
0.5625	Remote Similarity	NPC488736
0.5625	Remote Similarity	NPC488733
0.5603	Remote Similarity	NPC155877
0.5603	Remote Similarity	NPC605592
0.5591	Remote Similarity	NPC474093
0.5591	Remote Similarity	NPC104910
0.5581	Remote Similarity	NPC480444
0.5574	Remote Similarity	NPC214621
0.5574	Remote Similarity	NPC34267
0.5565	Remote Similarity	NPC292019
0.5565	Remote Similarity	NPC202908
0.5556	Remote Similarity	NPC470718
0.5546	Remote Similarity	NPC473327
0.5538	Remote Similarity	NPC488737
0.553	Remote Similarity	NPC25946
0.552	Remote Similarity	NPC217520
0.5517	Remote Similarity	NPC39834
0.5492	Remote Similarity	NPC470446
0.547	Remote Similarity	NPC156869
0.5455	Remote Similarity	NPC476472
0.5455	Remote Similarity	NPC294815
0.5455	Remote Similarity	NPC16194
0.544	Remote Similarity	NPC477895
0.5439	Remote Similarity	NPC476215
0.5423	Remote Similarity	NPC482520
0.5423	Remote Similarity	NPC482519
0.5385	Remote Similarity	NPC471748
0.5385	Remote Similarity	NPC67326
0.5364	Remote Similarity	NPC127546
0.5364	Remote Similarity	NPC57625
0.5364	Remote Similarity	NPC173637
0.5364	Remote Similarity	NPC317489
0.5364	Remote Similarity	NPC223424
0.5364	Remote Similarity	NPC600591
0.531	Remote Similarity	NPC48093
0.5308	Remote Similarity	NPC480445
0.5259	Remote Similarity	NPC116864
0.5259	Remote Similarity	NPC244776
0.5254	Remote Similarity	NPC163242
0.5254	Remote Similarity	NPC272068
0.525	Remote Similarity	NPC470125
0.525	Remote Similarity	NPC126784
0.525	Remote Similarity	NPC241423
0.5238	Remote Similarity	NPC189564
0.5231	Remote Similarity	NPC488734
0.5231	Remote Similarity	NPC488735
0.5231	Remote Similarity	NPC488739
0.5231	Remote Similarity	NPC488732
0.5231	Remote Similarity	NPC488738
0.5194	Remote Similarity	NPC139571
0.5191	Remote Similarity	NPC470713
0.5175	Remote Similarity	NPC159579
0.5161	Remote Similarity	NPC292929
0.5161	Remote Similarity	NPC470449
0.5149	Remote Similarity	NPC192539
0.513	Remote Similarity	NPC259957
0.5128	Remote Similarity	NPC254855
0.5128	Remote Similarity	NPC94610
0.5122	Remote Similarity	NPC142142
0.5043	Remote Similarity	NPC175107
0.5042	Remote Similarity	NPC471079
0.5042	Remote Similarity	NPC29958
0.5042	Remote Similarity	NPC139320
0.5041	Remote Similarity	NPC255157
0.5041	Remote Similarity	NPC35167
0.5041	Remote Similarity	NPC259896
0.504	Remote Similarity	NPC260504
0.504	Remote Similarity	NPC89809
0.5039	Remote Similarity	NPC480441

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC72554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4931
0.1-0.2	4166
0.2-0.3	44
0.3-0.4	6
0.4-0.5	2
0.5-0.6	0
0.6-0.7	1
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
0.6161	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