NPASS Compound

Natural Product: NPC535948

Natural Product ID	NPC535948
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(2~{S},3~{R},4~{S},5~{R},6~{S})-4,5-dihydroxy-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6-[[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	3-[(2~{S},3~{R},4~{S},5~{R},6~{S})-4,5-dihydroxy-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6-[[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-[(2~{S},3~{S},4~{R},5~{R},6~{S})-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 2D 116122 0 0 0 0 0 0 0 0999 V2000 -6.0000 -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 -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 -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 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 O 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 4.6386 -6.3385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3886 -7.6375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6386 -8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0481 -9.4496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3086 -10.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 -12.2259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1595 -11.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4095 -13.1900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -11.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -11.3780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4895 -9.9008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -8.6017 0.0000 O 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 6.7981 -4.5264 0.0000 O 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 6.3086 -1.7502 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 3.6595 -0.7860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4095 0.5130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5586 -0.4512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 0.0619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4681 0.0619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2286 1.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9786 2.8381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0796 2.5033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3296 3.8023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6700 1.9902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 1.9902 0.0000 O 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 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 5.1962 0.0000 O 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 -2.7395 6.6734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 7.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6386 8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2981 7.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7981 7.1245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5586 5.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 4.3483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 4.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 3.3841 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 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 -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 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2990 -3.3481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7010 -1.8481 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 2.7395 -1.1209 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 -6.0037 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2578 -6.9246 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0194 -5.7524 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3806 -8.1197 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7181 -10.4138 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 -13.5249 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3576 -11.4759 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8607 -13.1286 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1825 -12.9881 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9207 -13.3729 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3114 -12.8124 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -12.6770 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0800 -10.4138 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2395 -8.6017 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7367 -5.9609 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5481 -5.8255 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9681 -3.5623 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7640 -2.1132 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7578 -1.4276 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.0261 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4067 -1.3726 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9681 0.0619 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6510 1.5507 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6510 -1.4269 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6902 1.2017 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4786 2.8381 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2286 3.4675 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0796 5.1013 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5915 3.4882 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7566 3.4322 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5861 3.9788 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 -2.7395 3.7189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 8.6017 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3886 10.2356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3396 9.6866 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0194 8.3505 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7367 8.5590 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5481 8.4236 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9681 6.1603 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8086 4.3483 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5586 3.7189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 2.0850 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 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 -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 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 2 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 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 11 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 7 40 1 0 40 41 2 0 40 42 1 0 42 43 2 0 43 44 1 0 43 45 1 0 45 46 2 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 50 52 1 0 52 53 1 0 52 54 1 0 54 55 1 0 54 56 1 0 56 57 1 0 46 58 1 0 58 59 2 0 59 60 1 0 5 61 2 0 61 62 1 0 62 63 2 0 63 64 1 0 63 3 1 0 60 6 1 0 28 9 1 0 38 30 1 0 59 42 1 0 22 14 1 0 56 48 1 0 1 65 1 0 1 66 1 0 1 67 1 0 4 68 1 0 9 69 1 6 11 70 1 1 12 71 1 0 12 72 1 0 14 73 1 1 16 74 1 6 17 75 1 0 17 76 1 0 17 77 1 0 18 78 1 1 19 79 1 0 20 80 1 6 21 81 1 0 22 82 1 1 23 83 1 0 24 84 1 6 25 85 1 0 26 86 1 6 27 87 1 0 28 88 1 1 30 89 1 6 32 90 1 1 33 91 1 0 33 92 1 0 33 93 1 0 34 94 1 6 35 95 1 0 36 96 1 1 37 97 1 0 38 98 1 6 39 99 1 0 44100 1 0 45101 1 0 48102 1 6 50103 1 1 51104 1 0 51105 1 0 51106 1 0 52107 1 6 53108 1 0 54109 1 1 55110 1 0 56111 1 6 57112 1 0 58113 1 0 61114 1 0 62115 1 0 64116 1 0 M END

Standard InCHIKey	RFGSFRBMLXKAEM-RYMPBZBPSA-N
Standard InCHI	InChI=1S/C40H52O24/c1-11-22(43)27(48)31(52)37(57-11)56-10-20-25(46)30(51)36(64-39-33(54)29(50)24(45)13(3)59-39)40(62-20)63-35-26(47)21-17(42)8-15(60-38-32(53)28(49)23(44)12(2)58-38)9-19(21)61-34(35)14-5-6-16(41)18(7-14)55-4/h5-9,11-13,20,22-25,27-33,36-46,48-54H,10H2,1-4H3/t11-,12-,13-,20-,22-,23-,24-,25-,27+,28+,29+,30-,31-,32-,33-,36+,37+,38-,39-,40-/m0/s1
SMILES	COC1=CC(C2=C(O[C@@H]3O[C@@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]4O)[C@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]3O)C(=O)C3=C(O)C=C(O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]4O)C=C3O2)=CC=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	916.28	Volume:	830.374 ? Van der Waals volume.
Dense:	1.103	LogP:	-1.283 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.206 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.305 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	42.0
TPSA:	376.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.087	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.924	Fsp³:	0.625
MCE-18:	184.385 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.66	Fluc inhibitor:	0.428 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.666 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.416 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.202	Promiscuous compounds:	0.516

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.59	MDCK Permeability:	-5.118
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.944	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.059
Plasma Protein Binding (PPB):	74.307%	Volume Distribution (VD):	-0.11
Fu:	23.334% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.089
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:	0.258
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.965
HLM stability:	0.005 ? 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):

0.458

Half-life (T1/2):

4.482

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.04
Human Hepatotoxicity (H-HT):	0.634	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.995	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.392	Drug-induced Nephrotoxicity:	0.99
Genotoxicity:	0.806	RPMI-8226 Immunitoxicity:	0.762
A549 Cytotoxicity:	0.962	Hek293 Cytotoxicity:	0.428
BCF:	0.416 ? 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:	3.114 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.712 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.872 ? 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
NPO50639	Chrysothamnus nauseosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23888	Chrysothamnus viscidiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24555	Coleogyne ramosissima	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24555	Coleogyne ramosissima	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23888	Chrysothamnus viscidiflorus	Species	Asteraceae	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 NPC535948 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	22752
0.1-0.2	23581
0.2-0.3	2697
0.3-0.4	410
0.4-0.5	244
0.5-0.6	111
0.6-0.7	38
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8191	Intermediate Similarity	NPC142142
0.7959	Intermediate Similarity	NPC89052
0.79	Intermediate Similarity	NPC480441
0.79	Intermediate Similarity	NPC25523
0.7282	Intermediate Similarity	NPC173837
0.7216	Intermediate Similarity	NPC186816
0.703	Intermediate Similarity	NPC476472
0.703	Intermediate Similarity	NPC294815
0.703	Intermediate Similarity	NPC16194
0.7	Intermediate Similarity	NPC32641
0.7	Intermediate Similarity	NPC256188
0.6937	Remote Similarity	NPC192539
0.6847	Remote Similarity	NPC209550
0.6832	Remote Similarity	NPC35119
0.68	Remote Similarity	NPC240306
0.6733	Remote Similarity	NPC12013
0.6733	Remote Similarity	NPC11432
0.6733	Remote Similarity	NPC477613
0.6667	Remote Similarity	NPC122467
0.6538	Remote Similarity	NPC220173
0.6509	Remote Similarity	NPC14187
0.6458	Remote Similarity	NPC611303
0.6421	Remote Similarity	NPC46420
0.6421	Remote Similarity	NPC271692
0.6415	Remote Similarity	NPC602448
0.6381	Remote Similarity	NPC195257
0.6346	Remote Similarity	NPC209296
0.6321	Remote Similarity	NPC221342
0.6321	Remote Similarity	NPC476470
0.6296	Remote Similarity	NPC11468
0.6283	Remote Similarity	NPC198199
0.625	Remote Similarity	NPC470443
0.6239	Remote Similarity	NPC473072
0.6211	Remote Similarity	NPC249281
0.6176	Remote Similarity	NPC67105
0.6162	Remote Similarity	NPC223747
0.6126	Remote Similarity	NPC473644
0.6121	Remote Similarity	NPC120952
0.6117	Remote Similarity	NPC22062
0.6117	Remote Similarity	NPC473634
0.6117	Remote Similarity	NPC210073
0.6117	Remote Similarity	NPC138811
0.61	Remote Similarity	NPC276377
0.6075	Remote Similarity	NPC89127
0.6071	Remote Similarity	NPC311850
0.6038	Remote Similarity	NPC473327
0.6019	Remote Similarity	NPC44931
0.6	Remote Similarity	NPC126784
0.6	Remote Similarity	NPC241423
0.5982	Remote Similarity	NPC303694
0.598	Remote Similarity	NPC251417
0.5979	Remote Similarity	NPC158674
0.595	Remote Similarity	NPC473554
0.5932	Remote Similarity	NPC175429
0.5913	Remote Similarity	NPC68592
0.5905	Remote Similarity	NPC473571
0.5905	Remote Similarity	NPC110941
0.5888	Remote Similarity	NPC606657
0.5865	Remote Similarity	NPC173582
0.5865	Remote Similarity	NPC265885
0.5865	Remote Similarity	NPC181465
0.5865	Remote Similarity	NPC215710
0.5865	Remote Similarity	NPC473438
0.5865	Remote Similarity	NPC253788
0.5862	Remote Similarity	NPC298666
0.5849	Remote Similarity	NPC153755
0.5842	Remote Similarity	NPC116458
0.5842	Remote Similarity	NPC246943
0.5842	Remote Similarity	NPC605784
0.581	Remote Similarity	NPC203259
0.581	Remote Similarity	NPC33054
0.581	Remote Similarity	NPC176740
0.581	Remote Similarity	NPC471725
0.581	Remote Similarity	NPC134532
0.581	Remote Similarity	NPC150164
0.581	Remote Similarity	NPC602582
0.5752	Remote Similarity	NPC219043
0.5726	Remote Similarity	NPC480445
0.5714	Remote Similarity	NPC227508
0.5701	Remote Similarity	NPC64425
0.5636	Remote Similarity	NPC473073
0.5631	Remote Similarity	NPC476215
0.563	Remote Similarity	NPC480444
0.5596	Remote Similarity	NPC72016
0.5586	Remote Similarity	NPC292929
0.5581	Remote Similarity	NPC487501
0.5577	Remote Similarity	NPC95866
0.5575	Remote Similarity	NPC121703
0.5546	Remote Similarity	NPC162394
0.5514	Remote Similarity	NPC65563
0.5514	Remote Similarity	NPC470949
0.5508	Remote Similarity	NPC488086
0.5504	Remote Similarity	NPC487500
0.5492	Remote Similarity	NPC262222
0.547	Remote Similarity	NPC488087
0.547	Remote Similarity	NPC488083
0.5463	Remote Similarity	NPC115674
0.5463	Remote Similarity	NPC470444
0.5455	Remote Similarity	NPC138990
0.5446	Remote Similarity	NPC84362
0.5421	Remote Similarity	NPC39834
0.5421	Remote Similarity	NPC163242
0.5421	Remote Similarity	NPC272068
0.5417	Remote Similarity	NPC470719
0.5417	Remote Similarity	NPC470717
0.54	Remote Similarity	NPC238376
0.5398	Remote Similarity	NPC135358
0.5385	Remote Similarity	NPC311830
0.5385	Remote Similarity	NPC78326
0.5378	Remote Similarity	NPC295625
0.537	Remote Similarity	NPC65003
0.537	Remote Similarity	NPC155877
0.537	Remote Similarity	NPC303913
0.5366	Remote Similarity	NPC480442
0.5364	Remote Similarity	NPC483414
0.536	Remote Similarity	NPC487499
0.5347	Remote Similarity	NPC297987
0.5347	Remote Similarity	NPC136042
0.5333	Remote Similarity	NPC203050
0.5333	Remote Similarity	NPC488072
0.5333	Remote Similarity	NPC225434
0.5312	Remote Similarity	NPC487502
0.5294	Remote Similarity	NPC27640
0.5285	Remote Similarity	NPC480443
0.5273	Remote Similarity	NPC488073
0.5268	Remote Similarity	NPC486577
0.5254	Remote Similarity	NPC277532
0.5248	Remote Similarity	NPC289667
0.5248	Remote Similarity	NPC108831
0.5248	Remote Similarity	NPC19709
0.5248	Remote Similarity	NPC182634
0.5246	Remote Similarity	NPC470720
0.5243	Remote Similarity	NPC59534
0.5221	Remote Similarity	NPC473071
0.5192	Remote Similarity	NPC219904
0.5189	Remote Similarity	NPC601586
0.5182	Remote Similarity	NPC204693
0.5179	Remote Similarity	NPC482026
0.5179	Remote Similarity	NPC473623
0.5175	Remote Similarity	NPC470445
0.5169	Remote Similarity	NPC217520
0.5169	Remote Similarity	NPC164704
0.5149	Remote Similarity	NPC331652
0.5146	Remote Similarity	NPC305811
0.5143	Remote Similarity	NPC101026
0.5143	Remote Similarity	NPC488077
0.5135	Remote Similarity	NPC488074
0.5133	Remote Similarity	NPC488089
0.5124	Remote Similarity	NPC488739
0.5093	Remote Similarity	NPC473682
0.5091	Remote Similarity	NPC156869
0.5088	Remote Similarity	NPC470447
0.5088	Remote Similarity	NPC475382
0.5085	Remote Similarity	NPC48984
0.5083	Remote Similarity	NPC139571
0.5046	Remote Similarity	NPC471079
0.5043	Remote Similarity	NPC101636
0.5043	Remote Similarity	NPC203145
0.5042	Remote Similarity	NPC470715
0.5041	Remote Similarity	NPC488740

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC535948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5846
0.1-0.2	3261
0.2-0.3	35
0.3-0.4	2
0.4-0.5	1
0.5-0.6	2
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
0.6538	Remote Similarity	NPD7251	Phase 2
0.6449	Remote Similarity	NPD7808	Phase 3
0.6346	Remote Similarity	NPD7054	Phase 4
0.581	Remote Similarity	NPD6797	Phase 2
0.5043	Remote Similarity	NPD7472	Pre-clinical

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data