NPASS Compound

Natural Product: NPC517625

Natural Product ID	NPC517625
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~{S},4~{S},5~{R},6~{S})-4,5-dihydroxy-3-[(2~{R},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6-[[(2~{R},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-hydroxyphenyl)-7-[(2~{S},3~{S},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	3-[(2~{S},3~{S},4~{S},5~{R},6~{S})-4,5-dihydroxy-3-[(2~{R},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6-[[(2~{R},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-hydroxyphenyl)-7-[(2~{S},3~{S},4~{S},5~{R},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 2D 112118 0 0 0 0 0 0 0 0999 V2000 -8.7286 4.1372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9786 2.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7181 1.3609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0586 -0.4512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 -1.7502 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 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 -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 -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 -6.4952 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 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 1.5000 5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 7.0082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 8.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 9.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2709 9.4496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5209 10.7487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1386 8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 8.9366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 7.4594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1491 6.1603 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 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 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 -2.7395 -4.0753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9895 -5.3743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 -6.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3300 -7.1864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0695 -8.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3195 -9.9626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2186 -9.6278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9686 -10.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6281 -9.1148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1281 -9.1148 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 -6.3385 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 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 -5.1595 1.8121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 0.5130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9200 3.2893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8296 3.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0796 5.1013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4786 5.4362 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0277 3.3872 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5307 5.0399 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3882 2.3251 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -0.1163 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6076 -2.5002 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8667 -1.3368 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 -2.7395 -1.1209 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7388 -3.7143 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 5.2500 -3.8971 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 3.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 5.5310 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 7.9724 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9200 11.0835 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4690 9.0345 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9721 10.6872 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2939 10.5467 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2709 12.0477 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 10.4138 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 10.2356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 7.9724 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 6.1603 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 -3.2345 4.0796 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4030 -3.3943 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0878 -6.0159 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3400 -8.1506 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4305 -11.2617 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9795 -9.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5174 -10.8654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1956 -10.7248 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4574 -11.1097 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0667 -10.5492 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8781 -10.4138 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2981 -8.1506 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1274 -6.5214 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0070 -6.2530 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2252 -7.7804 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 -3.9160 2.6509 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8229 -0.9289 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 4.7665 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3340 4.6701 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8525 4.8994 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8296 6.4004 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 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 45 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 41 53 1 0 53 54 1 0 53 55 1 0 55 56 1 0 4 57 1 0 57 58 1 0 57 59 1 0 59 60 1 0 59 61 1 0 61 62 1 0 61 2 1 0 55 7 1 0 39 11 1 0 51 43 1 0 19 13 1 0 38 21 1 0 33 25 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 6 4 67 1 1 6 68 1 0 6 69 1 0 7 70 1 1 9 71 1 6 14 72 1 0 15 73 1 0 17 74 1 0 18 75 1 0 19 76 1 0 22 77 1 0 25 78 1 6 27 79 1 6 28 80 1 0 28 81 1 0 28 82 1 0 29 83 1 6 30 84 1 0 31 85 1 6 32 86 1 0 33 87 1 6 34 88 1 0 35 89 1 0 37 90 1 0 41 91 1 6 43 92 1 1 45 93 1 6 46 94 1 0 46 95 1 0 46 96 1 0 47 97 1 1 48 98 1 0 49 99 1 6 50100 1 0 51101 1 1 52102 1 0 53103 1 6 54104 1 0 55105 1 6 56106 1 0 57107 1 1 58108 1 0 59109 1 6 60110 1 0 61111 1 1 62112 1 0 M END

Standard InCHIKey	HRPKYCPCIPYAQZ-BXRZXCHISA-N
Standard InCHI	InChI=1S/C39H50O23/c1-11-21(42)26(47)30(51)36(55-11)54-10-19-24(45)29(50)35(62-38-32(53)28(49)23(44)13(3)57-38)39(60-19)61-34-25(46)20-17(41)8-16(58-37-31(52)27(48)22(43)12(2)56-37)9-18(20)59-33(34)14-4-6-15(40)7-5-14/h4-9,11-13,19,21-24,26-32,35-45,47-53H,10H2,1-3H3/t11-,12+,13-,19-,21-,22-,23-,24-,26+,27-,28+,29-,30-,31-,32-,35-,36+,37-,38-,39-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@@H]2O[C@@H](OC3=C(C4=CC=C(O)C=C4)OC4=CC(O[C@@H]5O[C@H](C)[C@H](O)[C@H](O)[C@@H]5O)=CC(O)=C4C3=O)[C@@H](O[C@@H]3O[C@@H](C)[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:	886.27	Volume:	804.288 ? Van der Waals volume.
Dense:	1.102	LogP:	0.636 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.295 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.013 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	42.0
TPSA:	367.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.092	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.853	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:	0.654	Fluc inhibitor:	0.376 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.655 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.375 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.274	Promiscuous compounds:	0.539

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.82	MDCK Permeability:	-4.853
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	0.376
20% Bioavailability (F20%):	0.429	30% Bioavailability (F30%):	0.976
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.011
Plasma Protein Binding (PPB):	78.56%	Volume Distribution (VD):	-0.082
Fu:	19.71% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.971
OATP1B3 inhibitor:	0.931	BCRP inhibitor:	0.001
BSEP inhibitor:	0.003

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:	0.76
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.976
HLM stability:	0.003 ? 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):

0.446

Half-life (T1/2):

6.213

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.104
Human Hepatotoxicity (H-HT):	0.413	Drug-induced Liver Injury (DILI):	0.968
AMES Toxicity:	0.979	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.009	Skin Sensitization:	1.0
Carcinogencity:	0.003	Eye Corrosion:	0.0
Eye Irritation:	0.016	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.601	Drug-induced Nephrotoxicity:	0.958
Genotoxicity:	0.732	RPMI-8226 Immunitoxicity:	0.496
A549 Cytotoxicity:	0.899	Hek293 Cytotoxicity:	0.601
BCF:	0.408 ? 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:	3.053 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.694 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.739 ? 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
NPO63989	Astragalus shikokianus	Genus	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC517625 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	22891
0.1-0.2	23294
0.2-0.3	2855
0.3-0.4	357
0.4-0.5	231
0.5-0.6	121
0.6-0.7	60
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9222	High Similarity	NPC25523
0.9186	High Similarity	NPC142142
0.8506	High Similarity	NPC186816
0.8404	Intermediate Similarity	NPC480441
0.8222	Intermediate Similarity	NPC32641
0.8222	Intermediate Similarity	NPC256188
0.8022	Intermediate Similarity	NPC35119
0.7912	Intermediate Similarity	NPC12013
0.7912	Intermediate Similarity	NPC11432
0.7912	Intermediate Similarity	NPC477613
0.7609	Intermediate Similarity	NPC240306
0.75	Intermediate Similarity	NPC602448
0.7412	Intermediate Similarity	NPC249281
0.7396	Intermediate Similarity	NPC221342
0.7396	Intermediate Similarity	NPC476470
0.7263	Intermediate Similarity	NPC122467
0.7241	Intermediate Similarity	NPC46420
0.7238	Intermediate Similarity	NPC209550
0.7222	Intermediate Similarity	NPC276377
0.6923	Remote Similarity	NPC116458
0.6923	Remote Similarity	NPC246943
0.6915	Remote Similarity	NPC173582
0.6915	Remote Similarity	NPC44931
0.6915	Remote Similarity	NPC265885
0.6915	Remote Similarity	NPC181465
0.6915	Remote Similarity	NPC215710
0.6915	Remote Similarity	NPC473438
0.6915	Remote Similarity	NPC253788
0.69	Remote Similarity	NPC14187
0.6842	Remote Similarity	NPC150164
0.6832	Remote Similarity	NPC89052
0.6701	Remote Similarity	NPC64425
0.6667	Remote Similarity	NPC476215
0.6636	Remote Similarity	NPC298666
0.66	Remote Similarity	NPC89127
0.6566	Remote Similarity	NPC72016
0.6562	Remote Similarity	NPC67105
0.6535	Remote Similarity	NPC292929
0.6495	Remote Similarity	NPC65563
0.6495	Remote Similarity	NPC210073
0.6495	Remote Similarity	NPC470949
0.6484	Remote Similarity	NPC271692
0.6476	Remote Similarity	NPC303694
0.6429	Remote Similarity	NPC473571
0.6429	Remote Similarity	NPC110941
0.6396	Remote Similarity	NPC192539
0.6392	Remote Similarity	NPC163242
0.6392	Remote Similarity	NPC272068
0.6374	Remote Similarity	NPC297987
0.6346	Remote Similarity	NPC11468
0.633	Remote Similarity	NPC480445
0.6327	Remote Similarity	NPC203259
0.6327	Remote Similarity	NPC33054
0.6327	Remote Similarity	NPC176740
0.6327	Remote Similarity	NPC471725
0.6327	Remote Similarity	NPC134532
0.6327	Remote Similarity	NPC602582
0.6261	Remote Similarity	NPC473554
0.6226	Remote Similarity	NPC173837
0.6211	Remote Similarity	NPC605784
0.617	Remote Similarity	NPC611303
0.6168	Remote Similarity	NPC473644
0.6162	Remote Similarity	NPC22062
0.6162	Remote Similarity	NPC65003
0.6162	Remote Similarity	NPC473634
0.6162	Remote Similarity	NPC303913
0.6162	Remote Similarity	NPC138811
0.6139	Remote Similarity	NPC470443
0.6111	Remote Similarity	NPC311850
0.6106	Remote Similarity	NPC480443
0.6106	Remote Similarity	NPC175429
0.6087	Remote Similarity	NPC108831
0.6087	Remote Similarity	NPC182634
0.6082	Remote Similarity	NPC95866
0.6078	Remote Similarity	NPC209296
0.6061	Remote Similarity	NPC227508
0.6036	Remote Similarity	NPC198199
0.6022	Remote Similarity	NPC158674
0.602	Remote Similarity	NPC251417
0.5982	Remote Similarity	NPC162394
0.5978	Remote Similarity	NPC111929
0.5978	Remote Similarity	NPC320283
0.5978	Remote Similarity	NPC331652
0.5978	Remote Similarity	NPC41121
0.5962	Remote Similarity	NPC476472
0.5962	Remote Similarity	NPC294815
0.5962	Remote Similarity	NPC473073
0.5962	Remote Similarity	NPC16194
0.596	Remote Similarity	NPC471079
0.5946	Remote Similarity	NPC68592
0.5946	Remote Similarity	NPC488739
0.5941	Remote Similarity	NPC470444
0.5929	Remote Similarity	NPC480444
0.5922	Remote Similarity	NPC473327
0.59	Remote Similarity	NPC39834
0.5888	Remote Similarity	NPC121703
0.5888	Remote Similarity	NPC203145
0.5882	Remote Similarity	NPC126784
0.5882	Remote Similarity	NPC241423
0.5877	Remote Similarity	NPC120952
0.5872	Remote Similarity	NPC164704
0.5842	Remote Similarity	NPC155877
0.5833	Remote Similarity	NPC189564
0.5816	Remote Similarity	NPC170052
0.5816	Remote Similarity	NPC135846
0.5804	Remote Similarity	NPC488734
0.5804	Remote Similarity	NPC488735
0.5804	Remote Similarity	NPC488732
0.5804	Remote Similarity	NPC488738
0.5784	Remote Similarity	NPC115674
0.5763	Remote Similarity	NPC487499
0.5755	Remote Similarity	NPC101636
0.5745	Remote Similarity	NPC289667
0.5745	Remote Similarity	NPC238376
0.5739	Remote Similarity	NPC138990
0.5702	Remote Similarity	NPC487502
0.57	Remote Similarity	NPC473682
0.5686	Remote Similarity	NPC304741
0.5684	Remote Similarity	NPC136042
0.5641	Remote Similarity	NPC480442
0.5619	Remote Similarity	NPC606657
0.5603	Remote Similarity	NPC488737
0.5588	Remote Similarity	NPC470405
0.5586	Remote Similarity	NPC470715
0.5579	Remote Similarity	NPC19709
0.5565	Remote Similarity	NPC488740
0.5565	Remote Similarity	NPC470717
0.5534	Remote Similarity	NPC156869
0.5526	Remote Similarity	NPC488086
0.5514	Remote Similarity	NPC470447
0.5514	Remote Similarity	NPC76831
0.5514	Remote Similarity	NPC473071
0.5514	Remote Similarity	NPC220173
0.5508	Remote Similarity	NPC262222
0.5487	Remote Similarity	NPC488087
0.5487	Remote Similarity	NPC488083
0.5464	Remote Similarity	NPC84362
0.5437	Remote Similarity	NPC67326
0.5431	Remote Similarity	NPC488736
0.5431	Remote Similarity	NPC488733
0.5417	Remote Similarity	NPC127546
0.5417	Remote Similarity	NPC57625
0.5417	Remote Similarity	NPC173637
0.5417	Remote Similarity	NPC317489
0.5417	Remote Similarity	NPC223424
0.5417	Remote Similarity	NPC600591
0.5413	Remote Similarity	NPC135358
0.5408	Remote Similarity	NPC216496
0.5397	Remote Similarity	NPC487500
0.5385	Remote Similarity	NPC479405
0.5385	Remote Similarity	NPC470720
0.5377	Remote Similarity	NPC483414
0.537	Remote Similarity	NPC195257
0.5357	Remote Similarity	NPC292019
0.5357	Remote Similarity	NPC202908
0.5354	Remote Similarity	NPC487501
0.534	Remote Similarity	NPC187379
0.5333	Remote Similarity	NPC479404
0.5328	Remote Similarity	NPC231787
0.5321	Remote Similarity	NPC298171
0.5321	Remote Similarity	NPC470449
0.5306	Remote Similarity	NPC27640
0.5294	Remote Similarity	NPC254855
0.5294	Remote Similarity	NPC94610
0.5288	Remote Similarity	NPC275454
0.5278	Remote Similarity	NPC486577
0.5263	Remote Similarity	NPC277532
0.5258	Remote Similarity	NPC348541
0.5243	Remote Similarity	NPC8856
0.5234	Remote Similarity	NPC65711
0.5221	Remote Similarity	NPC219043
0.5204	Remote Similarity	NPC323593
0.5204	Remote Similarity	NPC203500
0.5189	Remote Similarity	NPC204693
0.5189	Remote Similarity	NPC255157
0.5189	Remote Similarity	NPC259896
0.5185	Remote Similarity	NPC482026
0.5185	Remote Similarity	NPC473623
0.5169	Remote Similarity	NPC474522
0.5159	Remote Similarity	NPC249560
0.5155	Remote Similarity	NPC473043
0.5146	Remote Similarity	NPC116864
0.5146	Remote Similarity	NPC244776
0.514	Remote Similarity	NPC488073
0.514	Remote Similarity	NPC488074
0.514	Remote Similarity	NPC64051
0.5138	Remote Similarity	NPC488089
0.5133	Remote Similarity	NPC473072
0.5128	Remote Similarity	NPC295625
0.512	Remote Similarity	NPC223860
0.5102	Remote Similarity	NPC39360
0.5102	Remote Similarity	NPC77672
0.5102	Remote Similarity	NPC133671
0.5102	Remote Similarity	NPC135391
0.5102	Remote Similarity	NPC29763
0.5102	Remote Similarity	NPC78263
0.5102	Remote Similarity	NPC210003
0.5102	Remote Similarity	NPC250069
0.51	Remote Similarity	NPC59534
0.51	Remote Similarity	NPC27942

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC517625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5778
0.1-0.2	3326
0.2-0.3	38
0.3-0.4	2
0.4-0.5	2
0.5-0.6	0
0.6-0.7	4
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
0.6939	Remote Similarity	NPD7251	Phase 2
0.6505	Remote Similarity	NPD7808	Phase 3
0.6327	Remote Similarity	NPD6797	Phase 2
0.6078	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