NPASS Compound

Natural Product: NPC521503

Natural Product ID	NPC521503
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{R},3~{S},5~{R})-2-[(2~{R},3~{S},4~{R},5~{R})-4,5-dihydroxy-2-(hydroxymethyl)-6-[(5'~{R},6~{R},7~{S},9~{S},13~{R},16~{S})-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-18-ene-6,2'-tetrahydropyran]-16-yl]oxy-tetrahydropyran-3-yl]oxy-6-methyl-tetrahydropyran-3,4,5-triol
IUPAC Name	(2~{R},3~{S},5~{R})-2-[(2~{R},3~{S},4~{R},5~{R})-4,5-dihydroxy-2-(hydroxymethyl)-6-[(5'~{R},6~{R},7~{S},9~{S},13~{R},16~{S})-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-18-ene-6,2'-tetrahydropyran]-16-yl]oxy-tetrahydropyran-3-yl]oxy-6-methyl-tetrahydropyran-3,4,5-triol
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 113120 0 0 0 0 0 0 0 0999 V2000 11.0660 -1.8218 -0.7574 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2076 -1.0634 0.1863 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0719 -1.7353 0.6158 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1737 -0.8418 1.2464 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6592 -0.0381 0.3215 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3778 -0.0610 -0.0654 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6206 1.2156 0.2136 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6185 1.0319 1.1883 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9030 1.7447 -1.0094 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7452 2.4243 -1.8647 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1091 0.6634 -1.6445 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8728 0.5934 -1.0023 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8391 0.8321 -1.9109 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9187 -0.3625 -1.8754 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4634 -0.5119 -0.4324 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6388 0.5343 -0.1362 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4028 0.9301 1.2973 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3128 1.7070 -0.9702 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2692 2.5272 -1.3654 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6893 2.2371 -0.9472 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8890 0.7964 -1.2701 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2198 0.2313 -1.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3363 0.5806 -1.9926 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4588 -0.2509 -1.3473 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6249 0.4531 -1.2076 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2697 -0.1412 -0.0950 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3237 0.7771 0.3943 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5864 0.1416 0.8500 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8978 -1.1824 0.2435 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.3532 -1.3793 -0.0642 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0293 -1.3544 -0.9890 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7122 -1.3731 -0.5373 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1690 -0.3915 0.9141 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4777 -1.7397 1.5845 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9801 -0.5765 0.0708 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8650 0.4474 0.2519 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4885 1.7695 0.4607 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8529 0.0584 1.2778 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6563 -0.6482 0.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9621 -0.0579 -0.4153 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0753 2.0260 -1.3946 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6921 -0.5888 -1.5611 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1046 -0.4947 -1.4874 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6019 -1.9019 -1.7281 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1267 -2.7935 -0.7830 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8469 -0.2644 2.4403 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2332 -1.2388 3.3642 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1116 0.4740 2.0466 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7737 0.9657 3.1435 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0127 -0.5125 1.3314 C 0 0 1 0 0 0 0 0 0 0 0 0 11.4070 -1.4689 2.2516 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8527 -2.4327 -0.3180 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5972 -1.0656 -1.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4643 -2.4214 -1.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8188 -0.1564 -0.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3653 -1.5078 1.6178 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8792 -0.8573 0.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2845 2.0078 0.6501 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7473 0.1530 1.6477 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1793 2.5179 -0.6124 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5945 2.7253 -1.4552 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9190 0.9129 -2.7311 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2250 0.9990 -2.9378 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4524 -1.3049 -2.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0463 -0.1685 -2.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3362 -0.3688 0.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0359 -1.5283 -0.3308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0327 0.1000 1.8916 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3693 1.7542 1.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2740 1.2972 1.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0416 3.4136 -1.9913 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3118 2.8629 -1.6359 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7541 2.5164 0.1006 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6258 0.6970 -2.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0931 -0.8982 -1.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6206 1.6527 -1.9278 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2002 0.2588 -3.0568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5672 -1.1934 -1.9019 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5181 1.5943 -0.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8975 1.3372 1.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4289 0.8391 0.5654 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6620 0.0806 1.9738 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5861 -1.9683 0.9638 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9384 -0.8651 0.6962 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5678 -2.4716 0.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6094 -1.1102 -1.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2089 -2.3820 -1.4223 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2038 -0.5617 -1.7312 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1222 0.3269 1.7235 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6828 -1.8859 2.3553 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4241 -1.6374 2.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5270 -2.5545 0.8522 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5209 -1.5871 0.1142 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6058 1.7831 0.4160 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1578 2.5913 -0.1629 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2568 2.0793 1.5240 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3653 -0.6278 2.0008 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6446 0.9818 1.8853 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8927 -0.6503 1.6119 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9157 -1.7207 0.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7696 -0.9414 -1.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0806 2.8003 -2.1748 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5718 2.4969 -0.5018 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4057 0.2124 -2.2493 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2825 -2.2901 -2.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7315 -1.9229 -1.7897 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0425 -3.6973 -1.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2295 0.4567 3.0069 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9030 -0.8490 3.9782 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8426 1.3322 1.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5878 1.4236 2.8401 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9005 0.0469 0.9976 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0497 -0.9929 2.8685 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 7 9 1 0 9 10 1 0 9 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 1 16 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 26 25 1 6 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 26 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 1 1 36 38 1 0 38 39 1 0 39 40 1 0 18 41 1 0 11 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 4 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 50 2 1 0 43 6 1 0 41 13 1 0 40 16 1 0 40 21 1 0 36 22 1 0 35 24 1 0 32 26 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 0 4 56 1 1 6 57 1 1 7 58 1 1 8 59 1 0 9 60 1 1 10 61 1 0 11 62 1 0 13 63 1 6 14 64 1 0 14 65 1 0 15 66 1 0 15 67 1 0 17 68 1 0 17 69 1 0 17 70 1 0 19 71 1 0 20 72 1 0 20 73 1 0 21 74 1 0 22 75 1 0 23 76 1 0 23 77 1 0 24 78 1 0 27 79 1 0 27 80 1 0 28 81 1 0 28 82 1 0 29 83 1 1 30 84 1 0 30 85 1 0 30 86 1 0 31 87 1 0 31 88 1 0 33 89 1 1 34 90 1 0 34 91 1 0 34 92 1 0 35 93 1 0 37 94 1 0 37 95 1 0 37 96 1 0 38 97 1 0 38 98 1 0 39 99 1 0 39100 1 0 40101 1 0 41102 1 0 41103 1 0 43104 1 6 44105 1 0 44106 1 0 45107 1 0 46108 1 1 47109 1 0 48110 1 0 49111 1 0 50112 1 6 51113 1 0 M END

Standard InCHIKey	ZUMDKMTZYHACBK-NTMYTDRJSA-N
Standard InCHI	InChI=1S/C39H62O12/c1-18-8-13-39(46-17-18)19(2)28-26(51-39)15-25-23-7-6-21-14-22(9-11-37(21,4)24(23)10-12-38(25,28)5)48-36-33(45)31(43)34(27(16-40)49-36)50-35-32(44)30(42)29(41)20(3)47-35/h6,18-20,22-36,40-45H,7-17H2,1-5H3/t18-,19+,20?,22+,23?,24?,25?,26?,27-,28?,29+,30?,31-,32+,33-,34-,35-,36?,37+,38+,39-/m1/s1
SMILES	CC1O[C@H](O[C@H]2[C@H](O)[C@@H](O)C(O[C@H]3CC[C@@]4(C)C(=CCC5C6CC7O[C@]8(CC[C@@H](C)CO8)[C@@H](C)C7[C@@]6(C)CCC54)C3)O[C@@H]2CO)[C@@H](O)C(O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	722.42	Volume:	717.494 ? Van der Waals volume.
Dense:	1.007	LogP:	2.714 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.431 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.575 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	42.0
TPSA:	176.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	8.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.229	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.209	Fsp³:	0.949
MCE-18:	198.421 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.742	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.016 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.098	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.256	MDCK Permeability:	-5.012
Pgp-inhibitor:	0.003	Pgp-substrate:	0.883
PAMPA:	0.999 ? 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):	0.0
20% Bioavailability (F20%):	0.048	30% Bioavailability (F30%):	0.528
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.372
Plasma Protein Binding (PPB):	67.748%	Volume Distribution (VD):	-0.254
Fu:	27.071% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.051
BSEP inhibitor:	0.858

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.018
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.944
HLM stability:	0.219 ? 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):

1.887

Half-life (T1/2):

2.822

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.127
Human Hepatotoxicity (H-HT):	0.655	Drug-induced Liver Injury (DILI):	0.488
AMES Toxicity:	0.797	Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.467	Skin Sensitization:	0.979
Carcinogencity:	0.483	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.009
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.992
Hematotoxicity:	0.029	Drug-induced Nephrotoxicity:	0.454
Genotoxicity:	0.008	RPMI-8226 Immunitoxicity:	0.128
A549 Cytotoxicity:	0.692	Hek293 Cytotoxicity:	0.765
BCF:	2.02 ? 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:	4.145 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.593 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.839 ? 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
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[11141122]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	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 NPC521503 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	22951
0.1-0.2	23279
0.2-0.3	2884
0.3-0.4	484
0.4-0.5	111
0.5-0.6	79
0.6-0.7	34
0.7-0.8	1
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470432
1.0	High Similarity	NPC230507
0.8587	High Similarity	NPC6806
0.837	Intermediate Similarity	NPC470433
0.837	Intermediate Similarity	NPC46190
0.837	Intermediate Similarity	NPC171073
0.828	Intermediate Similarity	NPC477809
0.8235	Intermediate Similarity	NPC181845
0.8229	Intermediate Similarity	NPC269297
0.8229	Intermediate Similarity	NPC222202
0.8105	Intermediate Similarity	NPC480555
0.8105	Intermediate Similarity	NPC150372
0.8043	Intermediate Similarity	NPC14704
0.7979	Intermediate Similarity	NPC602423
0.7849	Intermediate Similarity	NPC113044
0.7849	Intermediate Similarity	NPC283829
0.7849	Intermediate Similarity	NPC161676
0.7812	Intermediate Similarity	NPC300557
0.7778	Intermediate Similarity	NPC475333
0.7778	Intermediate Similarity	NPC224098
0.7778	Intermediate Similarity	NPC208383
0.7708	Intermediate Similarity	NPC248746
0.7647	Intermediate Similarity	NPC477811
0.7624	Intermediate Similarity	NPC480554
0.7476	Intermediate Similarity	NPC480553
0.7383	Intermediate Similarity	NPC224314
0.7327	Intermediate Similarity	NPC475550
0.7273	Intermediate Similarity	NPC42171
0.7255	Intermediate Similarity	NPC32361
0.7184	Intermediate Similarity	NPC194207
0.7184	Intermediate Similarity	NPC22779
0.7143	Intermediate Similarity	NPC325828
0.713	Intermediate Similarity	NPC480556
0.6923	Remote Similarity	NPC309278
0.6852	Remote Similarity	NPC232054
0.6765	Remote Similarity	NPC249553
0.6737	Remote Similarity	NPC250393
0.6735	Remote Similarity	NPC15249
0.6735	Remote Similarity	NPC25455
0.6606	Remote Similarity	NPC31896
0.6465	Remote Similarity	NPC107962
0.6452	Remote Similarity	NPC486114
0.6429	Remote Similarity	NPC19400
0.6404	Remote Similarity	NPC477808
0.6383	Remote Similarity	NPC485594
0.6337	Remote Similarity	NPC141433
0.6296	Remote Similarity	NPC13193
0.6275	Remote Similarity	NPC305423
0.6263	Remote Similarity	NPC306131
0.6263	Remote Similarity	NPC200802
0.625	Remote Similarity	NPC100451
0.6238	Remote Similarity	NPC485595
0.6238	Remote Similarity	NPC6295
0.6207	Remote Similarity	NPC210569
0.6174	Remote Similarity	NPC477807
0.6132	Remote Similarity	NPC124677
0.6132	Remote Similarity	NPC182900
0.61	Remote Similarity	NPC107188
0.6068	Remote Similarity	NPC15918
0.605	Remote Similarity	NPC305771
0.605	Remote Similarity	NPC94072
0.605	Remote Similarity	NPC169816
0.6023	Remote Similarity	NPC235126
0.6023	Remote Similarity	NPC242419
0.6019	Remote Similarity	NPC97700
0.6019	Remote Similarity	NPC184617
0.6019	Remote Similarity	NPC30856
0.596	Remote Similarity	NPC477451
0.5909	Remote Similarity	NPC247037
0.5872	Remote Similarity	NPC73243
0.5872	Remote Similarity	NPC244086
0.5872	Remote Similarity	NPC84956
0.5865	Remote Similarity	NPC70204
0.5849	Remote Similarity	NPC42482
0.5841	Remote Similarity	NPC23808
0.5841	Remote Similarity	NPC87998
0.578	Remote Similarity	NPC475182
0.5769	Remote Similarity	NPC94272
0.5745	Remote Similarity	NPC144790
0.5745	Remote Similarity	NPC149400
0.5741	Remote Similarity	NPC122819
0.5727	Remote Similarity	NPC294129
0.5714	Remote Similarity	NPC195297
0.5702	Remote Similarity	NPC83137
0.5701	Remote Similarity	NPC40440
0.57	Remote Similarity	NPC234352
0.5686	Remote Similarity	NPC206003
0.5686	Remote Similarity	NPC473610
0.5664	Remote Similarity	NPC232037
0.5656	Remote Similarity	NPC263359
0.5652	Remote Similarity	NPC132080
0.5614	Remote Similarity	NPC249265
0.5603	Remote Similarity	NPC308140
0.56	Remote Similarity	NPC297348
0.56	Remote Similarity	NPC249204
0.56	Remote Similarity	NPC48339
0.56	Remote Similarity	NPC141769
0.56	Remote Similarity	NPC477547
0.5596	Remote Similarity	NPC92890
0.5586	Remote Similarity	NPC102016
0.5586	Remote Similarity	NPC95051
0.5575	Remote Similarity	NPC475625
0.5556	Remote Similarity	NPC98696
0.5543	Remote Similarity	NPC486119
0.5534	Remote Similarity	NPC121453
0.5446	Remote Similarity	NPC177834
0.5439	Remote Similarity	NPC116756
0.5437	Remote Similarity	NPC222731
0.5431	Remote Similarity	NPC476112
0.5431	Remote Similarity	NPC307534
0.5413	Remote Similarity	NPC161738
0.5408	Remote Similarity	NPC481420
0.5408	Remote Similarity	NPC473774
0.5408	Remote Similarity	NPC481419
0.5408	Remote Similarity	NPC481417
0.5408	Remote Similarity	NPC481421
0.5405	Remote Similarity	NPC471464
0.5403	Remote Similarity	NPC244431
0.5398	Remote Similarity	NPC115165
0.537	Remote Similarity	NPC160426
0.5361	Remote Similarity	NPC277715
0.5357	Remote Similarity	NPC150057
0.5357	Remote Similarity	NPC147753
0.5345	Remote Similarity	NPC218571
0.5345	Remote Similarity	NPC487615
0.5345	Remote Similarity	NPC470864
0.5339	Remote Similarity	NPC287885
0.5333	Remote Similarity	NPC211354
0.5321	Remote Similarity	NPC475351
0.5254	Remote Similarity	NPC233433
0.5248	Remote Similarity	NPC165439
0.5243	Remote Similarity	NPC131693
0.5243	Remote Similarity	NPC475436
0.5172	Remote Similarity	NPC473518
0.5161	Remote Similarity	NPC79900
0.5138	Remote Similarity	NPC475670
0.5124	Remote Similarity	NPC470866
0.5106	Remote Similarity	NPC177818
0.5096	Remote Similarity	NPC294686
0.5093	Remote Similarity	NPC295980
0.5089	Remote Similarity	NPC265275
0.5088	Remote Similarity	NPC128572
0.505	Remote Similarity	NPC24960
0.5046	Remote Similarity	NPC125324
0.5045	Remote Similarity	NPC112274
0.5043	Remote Similarity	NPC475247

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC521503 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7423
0.1-0.2	1624
0.2-0.3	90
0.3-0.4	7
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
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
0.7143	Intermediate Similarity	NPD8171	Phase 2
0.64	Remote Similarity	NPD8170	Phase 2
0.5741	Remote Similarity	NPD8449	Approved
0.5357	Remote Similarity	NPD8450	Suspended

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