NPASS Compound

Natural Product: NPC594728

Natural Product ID	NPC594728
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(1~{S},2~{S},3~{R},4~{R},7~{R},9~{S},10~{S},12~{R},15~{S})-4,12-diacetoxy-15-[(2~{R},3~{S})-3-[hexanoyl(methyl)amino]-2-hydroxy-3-phenyl-propanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl] benzoate
IUPAC Name	[(1~{S},2~{S},3~{R},4~{R},7~{R},9~{S},10~{S},12~{R},15~{S})-4,12-diacetoxy-15-[(2~{R},3~{S})-3-[hexanoyl(methyl)amino]-2-hydroxy-3-phenyl-propanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl] benzoate
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 121126 0 0 0 0 0 0 0 0999 V2000 9.7528 -2.6062 -0.9724 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5230 -2.7381 -0.1087 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3624 -3.3107 -0.9016 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1276 -3.4465 -0.0285 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6920 -2.1231 0.5342 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3400 -1.1200 -0.4906 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1804 -1.4945 -1.6720 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1758 0.2493 -0.1790 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4140 0.5993 1.2374 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7890 1.2625 -1.1238 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8036 1.4913 -2.1983 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1337 1.7344 -1.8963 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0897 1.9292 -2.8646 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7420 1.8874 -4.2143 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4242 1.6461 -4.5117 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4716 1.4518 -3.5310 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4041 1.1749 -1.6526 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0325 0.0718 -2.3459 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4786 1.3112 -0.4735 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7763 2.0631 0.4733 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2659 0.6335 -0.3648 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4334 0.7891 0.7741 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8462 1.5582 0.3724 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9663 1.4555 1.3114 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2160 2.7081 1.8759 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3078 1.0128 0.7175 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0560 2.1553 0.3203 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1102 2.7283 0.9342 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5037 2.2062 2.0006 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7912 3.8947 0.4307 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8248 4.4573 1.1075 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5093 5.5556 0.6713 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0992 6.1039 -0.5369 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0450 5.5702 -1.2727 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3985 4.4496 -0.7605 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2408 -0.0695 -0.2916 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0600 0.2939 -1.5429 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4132 0.1529 -1.3693 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4677 0.3919 -2.1801 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8926 0.1582 -1.8092 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2477 0.8375 -3.3184 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4804 1.1429 -2.5688 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8485 0.1731 -3.5125 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5353 -0.7213 -2.5534 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3190 -1.9486 -2.2978 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8916 -2.4386 -0.9444 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7947 -3.4043 -0.4841 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7817 -1.4050 0.1448 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1743 -1.2903 0.7396 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9561 -2.0807 1.1859 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6400 -2.8999 1.7862 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5285 -2.0588 1.7223 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5700 -2.7963 2.9419 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0059 -4.0797 2.9717 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0003 -4.9294 4.1967 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4813 -4.5335 1.9129 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0853 -0.6743 1.9146 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1071 -0.5256 1.3278 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0022 -1.7081 1.2738 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6313 0.5790 2.5442 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6288 1.2699 3.4397 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8334 0.3009 3.3872 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4991 -2.4690 -2.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4463 -3.4833 -0.8365 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3081 -1.6785 -0.6536 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2644 -1.7096 0.2692 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7712 -3.4195 0.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1994 -2.7118 -1.8028 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6502 -4.3391 -1.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3664 -4.1771 0.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3233 -3.8944 -0.6505 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4750 -1.7479 1.2379 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8163 -2.3472 1.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7819 -0.0442 1.8546 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3206 1.6754 1.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4930 0.3334 1.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7958 2.2504 -0.5389 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4300 1.7762 -0.8620 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1451 2.1200 -2.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5274 2.0471 -4.9436 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1556 1.6099 -5.5694 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4592 1.2665 -3.8693 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2661 2.1064 -2.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2877 0.2112 -2.9557 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0035 1.3885 1.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4564 2.6249 0.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0026 1.2899 -0.6755 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3710 2.7157 2.8304 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8552 0.6664 1.6059 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1732 4.0455 2.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3276 6.0096 1.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6031 6.9572 -0.9161 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7441 6.0020 -2.1965 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5785 4.0696 -1.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2155 -0.2869 -0.6560 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4923 1.0851 -1.8751 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2975 -0.4999 -2.6289 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0204 -0.2847 -0.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3840 1.1882 -2.5486 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8729 2.1575 -2.7435 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4437 -0.9491 -2.4362 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0846 -2.7781 -3.0178 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4066 -1.7694 -2.2585 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8819 -2.8909 -1.0625 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6220 -4.2772 -0.9350 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2597 -1.8180 1.7170 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9388 -1.7915 0.0742 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5203 -0.2777 0.9030 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9932 -2.6506 0.9865 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1249 -4.3524 5.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0681 -5.5264 4.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8532 -5.6722 4.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8795 -2.3242 0.3558 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0335 -1.2593 1.1311 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0812 -2.2613 2.2069 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0224 1.4015 4.4996 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4076 2.3151 3.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2782 0.6447 3.6127 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4847 1.1815 3.5405 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4271 -0.5707 3.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4642 0.0752 4.4438 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 6 8 1 0 8 9 1 0 8 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 10 17 1 0 17 18 1 0 17 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 26 36 1 0 36 37 1 0 37 38 1 1 38 39 1 0 39 40 1 0 39 41 2 0 37 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 46 48 1 0 48 49 1 1 48 50 1 0 50 51 2 0 50 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 54 56 2 0 52 57 1 0 57 58 2 0 58 59 1 0 57 60 1 0 60 61 1 0 60 62 1 0 16 11 1 0 58 22 1 0 60 24 1 0 35 30 1 0 48 36 1 0 44 37 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 0 2 67 1 0 3 68 1 0 3 69 1 0 4 70 1 0 4 71 1 0 5 72 1 0 5 73 1 0 9 74 1 0 9 75 1 0 9 76 1 0 10 77 1 1 12 78 1 0 13 79 1 0 14 80 1 0 15 81 1 0 16 82 1 0 17 83 1 6 18 84 1 0 22 85 1 1 23 86 1 0 23 87 1 0 25 88 1 0 26 89 1 1 31 90 1 0 32 91 1 0 33 92 1 0 34 93 1 0 35 94 1 0 36 95 1 6 40 96 1 0 40 97 1 0 40 98 1 0 42 99 1 0 42100 1 0 44101 1 1 45102 1 0 45103 1 0 46104 1 6 47105 1 0 49106 1 0 49107 1 0 49108 1 0 52109 1 6 55110 1 0 55111 1 0 55112 1 0 59113 1 0 59114 1 0 59115 1 0 61116 1 0 61117 1 0 61118 1 0 62119 1 0 62120 1 0 62121 1 0 M END

Standard InCHIKey	LJTMOSWWGSCCPR-NZDCSBJXSA-N
Standard InCHI	InChI=1S/C47H59NO14/c1-9-10-13-22-34(52)48(8)36(29-18-14-11-15-19-29)37(53)43(56)60-31-24-47(57)41(61-42(55)30-20-16-12-17-21-30)39-45(7,32(51)23-33-46(39,25-58-33)62-28(4)50)40(54)38(59-27(3)49)35(26(31)2)44(47,5)6/h11-12,14-21,31-33,36-39,41,51,53,57H,9-10,13,22-25H2,1-8H3/t31-,32-,33+,36-,37+,38+,39-,41-,45+,46+,47+/m0/s1
SMILES	CCCCCC(=O)N(C)[C@@H](C1=CC=CC=C1)[C@@H](O)C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)C3=CC=CC=C3)[C@@H]3[C@@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=O)C(=C1C)C2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	861.39	Volume:	869.915 ? Van der Waals volume.
Dense:	0.99	LogP:	3.521 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.567 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.041 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	18.0	Rigid Bonds:	38.0
TPSA:	212.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.111	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.094	Fsp³:	0.574
MCE-18:	164.216 ? 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:	0.954	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.038 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.103 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.003	Promiscuous compounds:	0.136

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.626	MDCK Permeability:	-5.1
Pgp-inhibitor:	1.0	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):	0.007
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	92.724%	Volume Distribution (VD):	0.013
Fu:	6.175% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.944	BCRP inhibitor:	0.0
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.71
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.953	CYP3A4-substrate:	0.515
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.995 ? 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):

3.252

Half-life (T1/2):

2.411

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.117
Human Hepatotoxicity (H-HT):	0.871	Drug-induced Liver Injury (DILI):	0.952
AMES Toxicity:	0.905	Rat Oral Acute Toxicity:	0.491
Maximum Recommended Daily Dose:	0.901	Skin Sensitization:	1.0
Carcinogencity:	0.46	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.02
Drug-induced Neurotoxicity:	0.959	Ototoxicity:	0.808
Hematotoxicity:	0.837	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.372
A549 Cytotoxicity:	0.936	Hek293 Cytotoxicity:	0.525
BCF:	0.505 ? 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:	3.488 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.279 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.389 ? 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
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23265441]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561894]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7908950]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO52496	Taxus media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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 NPC594728 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	11409
0.1-0.2	36312
0.2-0.3	1971
0.3-0.4	96
0.4-0.5	18
0.5-0.6	28
0.6-0.7	13
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC36607
0.766	Intermediate Similarity	NPC603140
0.7115	Intermediate Similarity	NPC471629
0.7115	Intermediate Similarity	NPC306001
0.7087	Intermediate Similarity	NPC471623
0.7087	Intermediate Similarity	NPC208553
0.7087	Intermediate Similarity	NPC181964
0.7087	Intermediate Similarity	NPC307628
0.7019	Intermediate Similarity	NPC33372
0.7019	Intermediate Similarity	NPC67246
0.7019	Intermediate Similarity	NPC324251
0.7019	Intermediate Similarity	NPC206211
0.6952	Remote Similarity	NPC487360
0.6952	Remote Similarity	NPC479182
0.6952	Remote Similarity	NPC479180
0.6923	Remote Similarity	NPC473400
0.6923	Remote Similarity	NPC603171
0.6822	Remote Similarity	NPC275170
0.6759	Remote Similarity	NPC486061
0.6759	Remote Similarity	NPC486060
0.6697	Remote Similarity	NPC487361
0.6526	Remote Similarity	NPC155329
0.6526	Remote Similarity	NPC114357
0.6514	Remote Similarity	NPC471606
0.6082	Remote Similarity	NPC605573
0.5856	Remote Similarity	NPC453583
0.5856	Remote Similarity	NPC317882
0.5856	Remote Similarity	NPC453588
0.5804	Remote Similarity	NPC471754
0.5766	Remote Similarity	NPC321072
0.5766	Remote Similarity	NPC215892
0.5766	Remote Similarity	NPC242662
0.5766	Remote Similarity	NPC102167
0.5766	Remote Similarity	NPC488127
0.5752	Remote Similarity	NPC478329
0.5743	Remote Similarity	NPC259144
0.5743	Remote Similarity	NPC219419
0.5714	Remote Similarity	NPC191193
0.5676	Remote Similarity	NPC473300
0.5664	Remote Similarity	NPC479183
0.5664	Remote Similarity	NPC479181
0.5625	Remote Similarity	NPC327699
0.5403	Remote Similarity	NPC479184
0.5351	Remote Similarity	NPC473490
0.5347	Remote Similarity	NPC197037
0.5347	Remote Similarity	NPC229545
0.5347	Remote Similarity	NPC248265
0.5347	Remote Similarity	NPC134685
0.5246	Remote Similarity	NPC116862
0.5196	Remote Similarity	NPC91730
0.5161	Remote Similarity	NPC472391
0.5146	Remote Similarity	NPC217918
0.512	Remote Similarity	NPC479185

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC594728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3542
0.1-0.2	5478
0.2-0.3	117
0.3-0.4	0
0.4-0.5	5
0.5-0.6	4
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
0.7087	Intermediate Similarity	NPD8485	Phase 4
0.6389	Remote Similarity	NPD8368	Phase 2
0.6364	Remote Similarity	NPD8486	Phase 1
0.6	Remote Similarity	NPD8462	Phase 2
0.5909	Remote Similarity	NPD8424	Phase 3
0.5766	Remote Similarity	NPD8360	Approved
0.5766	Remote Similarity	NPD8361	Phase 4
0.5439	Remote Similarity	NPD8435	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