NPASS Compound

Natural Product: NPC514511

Natural Product ID	NPC514511
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~{S},7~{R},9~{R},10~{S},12~{R},15~{R})-4,12-diacetoxy-15-[(2~{R},3~{S})-2-acetoxy-3-[[(~{E})-2-methylbut-2-enoyl]amino]-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~{S},7~{R},9~{R},10~{S},12~{R},15~{R})-4,12-diacetoxy-15-[(2~{R},3~{S})-2-acetoxy-3-[[(~{E})-2-methylbut-2-enoyl]amino]-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 118123 0 0 0 0 0 0 0 0999 V2000 6.8833 -3.9549 0.1163 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9187 -2.9393 0.6730 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9999 -1.6926 0.2384 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0266 -1.3573 -0.7669 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0642 -0.7160 0.7791 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2067 -1.0327 1.6212 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0840 0.6559 0.3697 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1271 1.6228 0.9321 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8697 2.6682 1.6820 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4513 3.1981 2.8899 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1806 4.1540 3.5552 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3595 4.6287 3.0529 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8033 4.1191 1.8484 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0600 3.1593 1.1916 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4394 2.2896 -0.2363 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4328 2.9445 -0.9920 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4409 4.3467 -1.1022 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4866 5.0437 -1.8934 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5145 4.9303 -0.4906 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6452 1.3351 -1.0290 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8750 1.1278 -2.2382 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6296 0.6547 -0.4333 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7760 -0.2665 -0.9513 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6486 0.2654 -0.9547 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4335 0.0715 0.2857 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3646 1.3289 0.9591 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9134 -0.1877 0.0879 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2995 1.1133 -0.4705 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8446 2.1221 0.2485 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0409 1.9875 1.4588 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1883 3.3504 -0.4280 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9671 3.5647 -1.7659 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3103 4.7571 -2.4166 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8984 5.7496 -1.6532 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1341 5.5692 -0.3116 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7829 4.3766 0.3041 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4294 -1.2401 -0.7298 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9014 -0.9547 -1.0836 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4989 0.0406 -0.3760 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7321 0.5636 -0.3671 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1706 1.6648 0.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5803 0.1162 -1.1460 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9167 -1.9896 -1.2289 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3226 -1.3166 -2.4260 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9609 -1.1190 -2.5606 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2806 -2.3982 -2.9642 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5248 -3.2002 -2.0547 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2457 -3.4566 -2.6377 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3089 -2.6725 -0.5947 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2904 -3.3617 0.3679 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0535 -3.3579 -0.2545 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2198 -4.5448 -0.4921 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6345 -3.3215 0.2540 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5304 -3.9804 1.4965 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1906 -5.1252 1.7309 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2194 -5.7265 3.0902 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8172 -5.6381 0.7582 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2507 -1.9096 0.4619 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7357 -1.6204 -0.3634 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7098 -2.6820 -0.6642 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8012 -0.8423 1.3043 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7034 -1.3674 2.3504 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3253 -0.1444 2.0750 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6316 -4.1391 -0.9463 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9173 -3.6104 0.2030 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7980 -4.9146 0.6742 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1845 -3.2481 1.4113 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6679 -0.6564 -1.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8509 -0.8302 -0.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4531 -2.2469 -1.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8033 0.9203 -0.3367 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4306 1.0639 1.5920 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5019 2.8119 3.2874 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8107 4.5334 4.4870 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9826 5.3811 3.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7385 4.4620 1.4066 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4400 2.7754 0.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7712 3.0614 0.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5977 6.1091 -1.5524 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3307 4.9728 -2.9869 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4634 4.5702 -1.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0582 -0.4185 -2.0363 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1206 -0.1473 -1.8689 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4931 1.3583 -1.2204 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8843 2.0044 0.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3370 -0.1522 1.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5040 2.7949 -2.3763 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1279 4.9076 -3.4716 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1969 6.7137 -2.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5932 6.3666 0.2390 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9811 4.2629 1.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9035 -1.0487 -1.7646 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0128 2.6140 -0.0135 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6962 1.6249 1.5350 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2934 1.5776 0.6336 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8101 -3.0060 -1.5075 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8318 -1.9562 -0.5435 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6402 -0.2286 -3.1022 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0718 -3.0502 -3.4599 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6697 -2.1194 -3.8838 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8891 -4.2294 -1.8920 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0787 -2.8135 -3.3829 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6569 -4.3307 -0.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7335 -3.7270 1.3060 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0147 -2.7013 0.8285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0294 -3.8844 -0.4497 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9894 -5.2250 3.7005 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7638 -5.5587 3.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4051 -6.8119 2.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5095 -3.2643 -1.5817 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6355 -2.0995 -0.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0592 -3.2717 0.1867 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1677 -2.2435 2.8197 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7624 -0.6645 3.2488 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6714 -1.7470 2.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3274 0.9444 1.9309 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1838 -0.2428 3.1973 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3034 -0.6469 1.9288 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 8 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 2 0 15 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 27 37 1 0 37 38 1 0 38 39 1 6 39 40 1 0 40 41 1 0 40 42 2 0 38 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 47 49 1 0 49 50 1 1 49 51 1 0 51 52 2 0 51 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 55 57 2 0 53 58 1 0 58 59 2 0 59 60 1 0 58 61 1 0 61 62 1 0 61 63 1 0 14 9 1 0 59 23 1 0 61 25 1 0 36 31 1 0 49 37 1 0 45 38 1 0 1 64 1 0 1 65 1 0 1 66 1 0 2 67 1 0 4 68 1 0 4 69 1 0 4 70 1 0 7 71 1 0 8 72 1 1 10 73 1 0 11 74 1 0 12 75 1 0 13 76 1 0 14 77 1 0 15 78 1 1 18 79 1 0 18 80 1 0 18 81 1 0 23 82 1 6 24 83 1 0 24 84 1 0 26 85 1 0 27 86 1 1 32 87 1 0 33 88 1 0 34 89 1 0 35 90 1 0 36 91 1 0 37 92 1 6 41 93 1 0 41 94 1 0 41 95 1 0 43 96 1 0 43 97 1 0 45 98 1 6 46 99 1 0 46100 1 0 47101 1 1 48102 1 0 50103 1 0 50104 1 0 50105 1 0 53106 1 6 56107 1 0 56108 1 0 56109 1 0 60110 1 0 60111 1 0 60112 1 0 62113 1 0 62114 1 0 62115 1 0 63116 1 0 63117 1 0 63118 1 0 M END

Standard InCHIKey	YQYRKKVPBWOSFA-QCBMGQFLSA-N
Standard InCHI	InChI=1S/C47H55NO15/c1-10-24(2)41(54)48-35(29-17-13-11-14-18-29)37(60-27(5)50)43(56)61-31-22-47(57)40(62-42(55)30-19-15-12-16-20-30)38-45(9,32(52)21-33-46(38,23-58-33)63-28(6)51)39(53)36(59-26(4)49)34(25(31)3)44(47,7)8/h10-20,31-33,35-38,40,52,57H,21-23H2,1-9H3,(H,48,54)/b24-10+/t31-,32-,33-,35+,36-,37-,38+,40+,45-,46+,47-/m1/s1
SMILES	C/C=C(C)C(=O)N[C@@H](C1=CC=CC=C1)[C@@H](OC(C)=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:	873.36	Volume:	873.432 ? Van der Waals volume.
Dense:	1.0	LogP:	2.892 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.917 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.181 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	40.0
TPSA:	227.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.126	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.196	Fsp³:	0.511
MCE-18:	168.31 ? 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:	0.896	Fluc inhibitor:	0.017 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.21 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.198 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.29

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.404	MDCK Permeability:	-4.955
Pgp-inhibitor:	0.999	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):	0.003
20% Bioavailability (F20%):	0.997	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):	89.734%	Volume Distribution (VD):	-0.086
Fu:	8.936% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.977	BCRP inhibitor:	0.0
BSEP inhibitor:	0.966

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.661	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.927 ? 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):

6.499

Half-life (T1/2):

1.973

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.038
Human Hepatotoxicity (H-HT):	0.935	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.996	Rat Oral Acute Toxicity:	0.824
Maximum Recommended Daily Dose:	0.99	Skin Sensitization:	1.0
Carcinogencity:	0.826	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.024
Drug-induced Neurotoxicity:	0.998	Ototoxicity:	0.836
Hematotoxicity:	0.861	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.723
A549 Cytotoxicity:	0.925	Hek293 Cytotoxicity:	0.787
BCF:	0.489 ? 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:	3.387 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.09 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.282 ? 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
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-9452(00)00306-X]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np990201k]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	Needles	n.a.	n.a.	PMID[11325226]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13290	Taxus canadensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13290	Taxus canadensis	Species	Taxaceae	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 NPC514511 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	10981
0.1-0.2	36887
0.2-0.3	1836
0.3-0.4	87
0.4-0.5	16
0.5-0.6	24
0.6-0.7	22
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	Natural Product ID
0.7476	Intermediate Similarity	NPC473400
0.7143	Intermediate Similarity	NPC603171
0.7075	Intermediate Similarity	NPC33372
0.7075	Intermediate Similarity	NPC67246
0.6952	Remote Similarity	NPC473300
0.6832	Remote Similarity	NPC603140
0.6727	Remote Similarity	NPC471606
0.6606	Remote Similarity	NPC324251
0.6606	Remote Similarity	NPC206211
0.6545	Remote Similarity	NPC487360
0.6545	Remote Similarity	NPC479182
0.6545	Remote Similarity	NPC479180
0.6545	Remote Similarity	NPC471629
0.6545	Remote Similarity	NPC306001
0.6514	Remote Similarity	NPC471623
0.6514	Remote Similarity	NPC208553
0.6514	Remote Similarity	NPC181964
0.6514	Remote Similarity	NPC307628
0.6481	Remote Similarity	NPC36607
0.646	Remote Similarity	NPC487361
0.6429	Remote Similarity	NPC275170
0.6372	Remote Similarity	NPC486061
0.6372	Remote Similarity	NPC486060
0.6263	Remote Similarity	NPC155329
0.6263	Remote Similarity	NPC114357
0.6216	Remote Similarity	NPC317882
0.5929	Remote Similarity	NPC473558
0.5929	Remote Similarity	NPC453583
0.5842	Remote Similarity	NPC605573
0.5826	Remote Similarity	NPC478329
0.5702	Remote Similarity	NPC473490
0.5652	Remote Similarity	NPC453588
0.547	Remote Similarity	NPC471754
0.547	Remote Similarity	NPC479183
0.547	Remote Similarity	NPC479181
0.5447	Remote Similarity	NPC472392
0.5437	Remote Similarity	NPC248265
0.5431	Remote Similarity	NPC321072
0.5431	Remote Similarity	NPC215892
0.5431	Remote Similarity	NPC242662
0.5431	Remote Similarity	NPC102167
0.5431	Remote Similarity	NPC488127
0.5377	Remote Similarity	NPC259144
0.5377	Remote Similarity	NPC219419
0.5288	Remote Similarity	NPC197037
0.5288	Remote Similarity	NPC229545
0.5288	Remote Similarity	NPC134685
0.5254	Remote Similarity	NPC191193
0.5238	Remote Similarity	NPC472391
0.5169	Remote Similarity	NPC327699

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC514511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3676
0.1-0.2	5407
0.2-0.3	54
0.3-0.4	1
0.4-0.5	4
0.5-0.6	7
0.6-0.7	1
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
0.6514	Remote Similarity	NPD8485	Phase 4
0.5877	Remote Similarity	NPD8368	Phase 2
0.5862	Remote Similarity	NPD8486	Phase 1
0.5565	Remote Similarity	NPD8424	Phase 3
0.5556	Remote Similarity	NPD8462	Phase 2
0.5431	Remote Similarity	NPD8360	Approved
0.5431	Remote Similarity	NPD8361	Phase 4
0.5126	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