NPASS Compound

Natural Product: NPC526064

Natural Product ID	NPC526064
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~{R},5~{R},6~{S})-6-[[(2~{R},3~{S},4~{R},5~{R},6~{S})-3,4-dihydroxy-6-methyl-5-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-6-[[(2~{R},3~{S},4~{R},5~{R},6~{S})-3,4-dihydroxy-6-methyl-5-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2~{S},3~{R},4~{S},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 3D 112118 0 0 0 0 0 0 0 0999 V2000 -8.9821 -2.9407 0.2885 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6481 -2.9833 -1.0796 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6528 -2.9652 -2.0406 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3308 -1.6307 -2.3420 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0639 -1.5664 -2.9135 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8841 -1.2103 -2.3103 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7244 -1.1498 -3.0890 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5064 -0.8004 -2.5388 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3449 -0.7308 -3.2801 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4153 -0.5006 -1.1846 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2214 -0.1494 -0.6073 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1724 -0.0883 -1.2931 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1926 0.1420 0.7665 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9608 0.5033 1.2991 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5218 1.8656 1.2078 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4100 1.8177 0.1321 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3992 2.7587 0.2434 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0104 3.1551 -1.0578 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6184 2.1602 -1.7738 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6572 1.5340 -1.1634 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8501 1.8421 -1.8332 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9470 1.5612 -1.0109 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7993 2.5465 0.1528 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9270 0.1750 -0.4254 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7382 -0.6686 -1.1631 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8981 -1.0525 -0.5193 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9544 -0.6548 -1.3345 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1777 -0.7265 -0.6845 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2624 -0.5274 -1.7128 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3145 -2.0129 0.0964 C 0 0 2 0 0 0 0 0 0 0 0 0 11.5964 -2.5046 -0.1328 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3363 -3.0543 -0.4022 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7109 -3.5438 -1.6563 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9157 -2.5504 -0.4141 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3220 -2.9932 0.7760 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6135 -0.3704 -0.0436 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5611 -1.7569 0.0373 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5183 0.0362 -1.0068 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6326 -0.6215 -2.2284 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8195 3.9994 0.9182 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6909 5.0517 0.6594 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7644 3.6587 2.4080 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0840 4.6198 3.1170 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1011 2.2899 2.4850 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9970 1.3413 2.9802 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3256 0.0692 1.4972 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4762 0.3251 2.9211 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7539 0.5402 3.4579 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9420 0.7131 4.7963 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8934 0.6858 5.6954 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1023 0.8639 7.0575 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6475 0.4737 5.1545 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4203 0.2936 3.7959 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4392 -0.2766 0.8552 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5227 -0.5511 -0.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7517 -0.9068 -0.9777 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4205 -1.1244 -3.2593 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1705 0.1733 -3.7048 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7356 -1.2444 -2.5374 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.6153 -2.0575 -3.2528 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5385 -1.7633 -1.1525 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.7838 -2.1304 -0.6383 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6184 -1.9017 0.5157 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7244 -3.1406 1.1131 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1571 -3.6542 0.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2845 -3.8857 -1.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3146 -1.1216 -1.3606 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7709 -1.3785 -4.1415 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3254 -0.6932 -4.2911 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3365 2.5424 0.9300 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2222 2.4201 0.9367 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1932 3.5644 -1.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6676 4.0359 -0.8777 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8049 1.9603 -0.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8593 1.7787 -1.5743 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2028 3.4329 -0.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4382 2.0805 1.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8257 2.9341 0.3723 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4940 0.2964 0.5590 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9905 -0.6467 0.5074 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2311 0.1091 0.0324 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8330 -0.0314 -2.6328 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0250 0.1958 -1.3540 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7775 -1.4627 -1.9759 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2194 -1.8308 1.1819 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6270 -3.1904 -0.8577 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4051 -3.9165 0.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7274 -2.7614 -2.2921 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3150 -3.0323 -1.2227 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1455 -3.9518 0.6951 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2442 -0.0063 0.9636 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8907 -2.0997 0.6646 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5329 -0.1730 -0.5764 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9602 -1.5295 -2.0708 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1940 4.1826 0.5282 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1694 5.8815 0.6644 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7992 3.5874 2.7554 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7772 4.8729 2.6973 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7119 2.4107 3.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8391 0.4868 2.5340 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6015 0.5646 2.7552 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9569 0.8800 5.1662 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6901 0.1874 7.7124 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7733 0.4419 5.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 0.1090 3.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6059 -0.9362 -0.3285 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4742 -1.8156 -4.1521 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3488 0.2374 -4.6615 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1367 -0.1993 -2.4523 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3049 -2.3612 -2.5902 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1582 -0.9505 -0.4653 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2283 -1.4245 -0.1445 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 2 0 7 8 1 0 8 9 1 0 8 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 24 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 17 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 13 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 50 52 1 0 52 53 2 0 46 54 1 0 54 55 1 0 55 56 2 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 56 6 1 0 55 10 1 0 44 15 1 0 53 47 1 0 38 20 1 0 34 26 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 1 4 67 1 1 7 68 1 0 9 69 1 0 15 70 1 6 17 71 1 1 18 72 1 0 18 73 1 0 20 74 1 1 22 75 1 6 23 76 1 0 23 77 1 0 23 78 1 0 24 79 1 1 26 80 1 1 28 81 1 1 29 82 1 0 29 83 1 0 29 84 1 0 30 85 1 1 31 86 1 0 32 87 1 1 33 88 1 0 34 89 1 6 35 90 1 0 36 91 1 1 37 92 1 0 38 93 1 1 39 94 1 0 40 95 1 6 41 96 1 0 42 97 1 1 43 98 1 0 44 99 1 1 45100 1 0 48101 1 0 49102 1 0 51103 1 0 52104 1 0 53105 1 0 56106 1 0 57107 1 6 58108 1 0 59109 1 1 60110 1 0 61111 1 1 62112 1 0 M END

Standard InCHIKey	MFMPPIGSYYTBKG-HOJXTWBASA-N
Standard InCHI	InChI=1S/C39H50O23/c1-11-21(42)25(46)29(50)37(55-11)58-16-8-17(41)20-18(9-16)59-34(14-4-6-15(40)7-5-14)35(24(20)45)62-39-31(52)27(48)23(44)19(60-39)10-54-36-32(53)28(49)33(13(3)57-36)61-38-30(51)26(47)22(43)12(2)56-38/h4-9,11-13,19,21-23,25-33,36-44,46-53H,10H2,1-3H3/t11-,12+,13-,19-,21-,22-,23-,25-,26-,27+,28+,29+,30+,31-,32-,33-,36+,37-,38-,39-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@@H]4O[C@@H](CO[C@@H]5O[C@@H](C)[C@H](O[C@@H]6O[C@H](C)[C@H](O)[C@H](O)[C@H]6O)[C@H](O)[C@@H]5O)[C@H](O)[C@@H](O)[C@@H]4O)=C(C4=CC=C(O)C=C4)OC3=C2)[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:	0.72 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.211 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.148 ? 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:	0.644	Fluc inhibitor:	0.351 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.645 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.383 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.253	Promiscuous compounds:	0.531

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.874	MDCK Permeability:	-4.871
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):	0.987
20% Bioavailability (F20%):	0.893	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.189
Plasma Protein Binding (PPB):	76.209%	Volume Distribution (VD):	-0.03
Fu:	20.42% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.978
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.097
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:	0.989
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.938
HLM stability:	0.066 ? 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):

0.508

Half-life (T1/2):

4.844

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.031
Human Hepatotoxicity (H-HT):	0.634	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	1.0
Carcinogencity:	0.008	Eye Corrosion:	0.0
Eye Irritation:	0.01	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.997
Hematotoxicity:	0.434	Drug-induced Nephrotoxicity:	0.902
Genotoxicity:	0.902	RPMI-8226 Immunitoxicity:	0.553
A549 Cytotoxicity:	0.997	Hek293 Cytotoxicity:	0.92
BCF:	0.475 ? 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:	3.15 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.711 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.837 ? 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
NPO22530	Vigna luteola	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22530	Vigna luteola	Species	Fabaceae	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 NPC526064 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	23481
0.1-0.2	22884
0.2-0.3	2689
0.3-0.4	368
0.4-0.5	237
0.5-0.6	127
0.6-0.7	56
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8953	High Similarity	NPC186816
0.7442	Intermediate Similarity	NPC249281
0.7327	Intermediate Similarity	NPC25523
0.7312	Intermediate Similarity	NPC173582
0.7312	Intermediate Similarity	NPC265885
0.7312	Intermediate Similarity	NPC181465
0.7312	Intermediate Similarity	NPC215710
0.7312	Intermediate Similarity	NPC473438
0.7312	Intermediate Similarity	NPC253788
0.7273	Intermediate Similarity	NPC46420
0.7253	Intermediate Similarity	NPC276377
0.7216	Intermediate Similarity	NPC142142
0.7128	Intermediate Similarity	NPC44931
0.6957	Remote Similarity	NPC116458
0.6957	Remote Similarity	NPC246943
0.6875	Remote Similarity	NPC65563
0.6875	Remote Similarity	NPC470949
0.6875	Remote Similarity	NPC150164
0.6804	Remote Similarity	NPC473571
0.6804	Remote Similarity	NPC110941
0.6771	Remote Similarity	NPC67105
0.6768	Remote Similarity	NPC32641
0.6768	Remote Similarity	NPC256188
0.6701	Remote Similarity	NPC203259
0.6701	Remote Similarity	NPC33054
0.6701	Remote Similarity	NPC210073
0.6701	Remote Similarity	NPC176740
0.6701	Remote Similarity	NPC471725
0.6701	Remote Similarity	NPC134532
0.6701	Remote Similarity	NPC602582
0.6667	Remote Similarity	NPC480441
0.66	Remote Similarity	NPC72016
0.66	Remote Similarity	NPC35119
0.6569	Remote Similarity	NPC470449
0.6522	Remote Similarity	NPC271692
0.65	Remote Similarity	NPC470443
0.6413	Remote Similarity	NPC297987
0.6364	Remote Similarity	NPC303913
0.6327	Remote Similarity	NPC471079
0.6311	Remote Similarity	NPC476472
0.6311	Remote Similarity	NPC294815
0.6311	Remote Similarity	NPC473073
0.6311	Remote Similarity	NPC16194
0.6263	Remote Similarity	NPC39834
0.6263	Remote Similarity	NPC227508
0.625	Remote Similarity	NPC605784
0.6238	Remote Similarity	NPC126784
0.6238	Remote Similarity	NPC240306
0.6238	Remote Similarity	NPC241423
0.6226	Remote Similarity	NPC121703
0.62	Remote Similarity	NPC22062
0.62	Remote Similarity	NPC473634
0.62	Remote Similarity	NPC138811
0.6176	Remote Similarity	NPC12013
0.6176	Remote Similarity	NPC11432
0.6176	Remote Similarity	NPC477613
0.6168	Remote Similarity	NPC189564
0.6117	Remote Similarity	NPC209296
0.6117	Remote Similarity	NPC473327
0.6075	Remote Similarity	NPC203145
0.6064	Remote Similarity	NPC158674
0.6058	Remote Similarity	NPC488089
0.6042	Remote Similarity	NPC611303
0.6038	Remote Similarity	NPC470446
0.6022	Remote Similarity	NPC111929
0.6022	Remote Similarity	NPC320283
0.6022	Remote Similarity	NPC41121
0.6	Remote Similarity	NPC471669
0.6	Remote Similarity	NPC139320
0.5981	Remote Similarity	NPC14187
0.5957	Remote Similarity	NPC108831
0.5957	Remote Similarity	NPC182634
0.5943	Remote Similarity	NPC101636
0.5913	Remote Similarity	NPC209550
0.5888	Remote Similarity	NPC602448
0.5882	Remote Similarity	NPC156869
0.5851	Remote Similarity	NPC331652
0.5794	Remote Similarity	NPC221342
0.5794	Remote Similarity	NPC476470
0.5784	Remote Similarity	NPC67326
0.5769	Remote Similarity	NPC64425
0.5743	Remote Similarity	NPC251417
0.5729	Remote Similarity	NPC136042
0.5676	Remote Similarity	NPC292019
0.5676	Remote Similarity	NPC202908
0.566	Remote Similarity	NPC122467
0.5648	Remote Similarity	NPC298171
0.5641	Remote Similarity	NPC138990
0.5625	Remote Similarity	NPC289667
0.5625	Remote Similarity	NPC238376
0.5607	Remote Similarity	NPC486577
0.5593	Remote Similarity	NPC175429
0.5577	Remote Similarity	NPC479405
0.5577	Remote Similarity	NPC605592
0.5556	Remote Similarity	NPC470447
0.5524	Remote Similarity	NPC479404
0.5514	Remote Similarity	NPC606657
0.549	Remote Similarity	NPC116864
0.549	Remote Similarity	NPC244776
0.5481	Remote Similarity	NPC471748
0.5481	Remote Similarity	NPC275454
0.5472	Remote Similarity	NPC488073
0.5472	Remote Similarity	NPC488074
0.5472	Remote Similarity	NPC64051
0.547	Remote Similarity	NPC474522
0.5464	Remote Similarity	NPC127546
0.5464	Remote Similarity	NPC57625
0.5464	Remote Similarity	NPC19709
0.5464	Remote Similarity	NPC173637
0.5464	Remote Similarity	NPC317489
0.5464	Remote Similarity	NPC223424
0.5464	Remote Similarity	NPC600591
0.5439	Remote Similarity	NPC277532
0.5421	Remote Similarity	NPC65711
0.5421	Remote Similarity	NPC483415
0.5413	Remote Similarity	NPC89127
0.5405	Remote Similarity	NPC470455
0.54	Remote Similarity	NPC159579
0.5392	Remote Similarity	NPC476215
0.5385	Remote Similarity	NPC298666
0.5385	Remote Similarity	NPC187379
0.5377	Remote Similarity	NPC129264
0.5366	Remote Similarity	NPC483159
0.5366	Remote Similarity	NPC231787
0.5366	Remote Similarity	NPC483160
0.5357	Remote Similarity	NPC89052
0.5354	Remote Similarity	NPC84362
0.5354	Remote Similarity	NPC27640
0.5327	Remote Similarity	NPC470125
0.528	Remote Similarity	NPC72554
0.5278	Remote Similarity	NPC479403
0.5273	Remote Similarity	NPC85751
0.5273	Remote Similarity	NPC19240
0.5259	Remote Similarity	NPC488087
0.5243	Remote Similarity	NPC66087
0.5234	Remote Similarity	NPC204693
0.5229	Remote Similarity	NPC473623
0.5229	Remote Similarity	NPC270448
0.5221	Remote Similarity	NPC11468
0.521	Remote Similarity	NPC156785
0.5189	Remote Similarity	NPC163242
0.5189	Remote Similarity	NPC272068
0.5185	Remote Similarity	NPC153755
0.5182	Remote Similarity	NPC270675
0.5182	Remote Similarity	NPC195685
0.5179	Remote Similarity	NPC135358
0.5159	Remote Similarity	NPC223860
0.5152	Remote Similarity	NPC77672
0.5152	Remote Similarity	NPC133671
0.5152	Remote Similarity	NPC135391
0.5152	Remote Similarity	NPC78263
0.5152	Remote Similarity	NPC250069
0.5152	Remote Similarity	NPC348541
0.5149	Remote Similarity	NPC59534
0.5146	Remote Similarity	NPC223747
0.514	Remote Similarity	NPC473512
0.514	Remote Similarity	NPC65003
0.514	Remote Similarity	NPC129827
0.5135	Remote Similarity	NPC80068
0.5133	Remote Similarity	NPC214621
0.5133	Remote Similarity	NPC34267
0.513	Remote Similarity	NPC173837
0.5128	Remote Similarity	NPC488083
0.5126	Remote Similarity	NPC480445
0.5124	Remote Similarity	NPC241781
0.512	Remote Similarity	NPC473554
0.5116	Remote Similarity	NPC97817
0.51	Remote Similarity	NPC323593
0.51	Remote Similarity	NPC203500
0.5091	Remote Similarity	NPC229409
0.5089	Remote Similarity	NPC292929
0.5089	Remote Similarity	NPC470445
0.5086	Remote Similarity	NPC303694
0.5086	Remote Similarity	NPC164704
0.5082	Remote Similarity	NPC192539
0.5051	Remote Similarity	NPC473043
0.5051	Remote Similarity	NPC135599
0.5051	Remote Similarity	NPC73855
0.5051	Remote Similarity	NPC113968
0.5051	Remote Similarity	NPC328940
0.5051	Remote Similarity	NPC277174
0.5051	Remote Similarity	NPC606877
0.505	Remote Similarity	NPC305811
0.505	Remote Similarity	NPC24043
0.5048	Remote Similarity	NPC265115
0.5044	Remote Similarity	NPC470450
0.5044	Remote Similarity	NPC472994
0.5043	Remote Similarity	NPC470451
0.5042	Remote Similarity	NPC488734
0.5042	Remote Similarity	NPC488735
0.5042	Remote Similarity	NPC488739
0.5042	Remote Similarity	NPC488732
0.5042	Remote Similarity	NPC488738
0.5039	Remote Similarity	NPC30011
0.5038	Remote Similarity	NPC482520
0.5038	Remote Similarity	NPC482519

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC526064 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5932
0.1-0.2	3167
0.2-0.3	43
0.3-0.4	2
0.4-0.5	2
0.5-0.6	0
0.6-0.7	3
0.7-0.8	1
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
0.732	Intermediate Similarity	NPD7251	Phase 2
0.6701	Remote Similarity	NPD6797	Phase 2
0.6699	Remote Similarity	NPD7808	Phase 3
0.6117	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