NPASS Compound

Natural Product: NPC537050

Natural Product ID	NPC537050
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~{S},10~{S},12~{R},15~{R})-15-[(2~{R},3~{S})-3-acetamido-2-hydroxy-3-phenyl-propanoyl]oxy-4,12-diacetoxy-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~{S},10~{S},12~{R},15~{R})-15-[(2~{R},3~{S})-3-acetamido-2-hydroxy-3-phenyl-propanoyl]oxy-4,12-diacetoxy-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 106111 0 0 0 0 0 0 0 0999 V2000 3.7648 -3.4493 -1.4007 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5231 -2.6121 -0.4468 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6354 -2.9898 0.7387 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1334 -1.3850 -0.8292 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8835 -0.5288 0.0542 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2464 -0.2570 -0.3792 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2782 -0.3639 0.5630 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5977 -0.1221 0.2534 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9375 0.2442 -1.0436 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9211 0.3491 -1.9703 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6032 0.1078 -1.6625 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0876 0.7269 0.4009 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7876 1.3726 -0.7825 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9137 0.4169 1.2248 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9368 -0.0779 2.3737 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6589 0.6516 0.7861 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4574 0.4272 1.4262 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6014 -0.6855 0.8218 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7512 -0.1651 0.6361 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2764 0.9158 -0.2315 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7510 -0.5758 -0.3298 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4947 -1.7080 0.1570 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3901 -2.9772 -0.3554 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5858 -3.1337 -1.3372 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1107 -4.1313 0.1335 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9589 -5.3666 -0.4364 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6277 -6.4686 0.0363 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4720 -6.3157 1.1131 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6572 -5.1023 1.7167 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9625 -4.0055 1.2115 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7034 0.4445 -0.8637 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2544 -0.2497 -2.0788 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0827 -1.3601 -1.7724 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2730 -1.2607 -1.0869 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1233 -2.4564 -0.7887 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6968 -0.1702 -0.6864 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3723 -0.5816 -3.2047 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8835 0.4398 -4.0418 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9109 0.5682 -3.1196 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2806 1.9410 -2.7535 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8764 2.4085 -1.4244 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7000 3.8130 -1.5859 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4583 1.8808 -0.9666 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6169 2.4273 -2.0816 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2381 2.7313 0.2227 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0783 3.5873 0.4599 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2035 2.9318 1.3867 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5465 4.0694 1.0412 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7367 5.2934 1.6818 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0161 6.5220 1.2955 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5688 5.3576 2.6427 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6150 1.6969 1.7369 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6733 1.6898 1.7468 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3385 2.9427 2.0678 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2495 0.3356 1.9652 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6460 -0.2941 3.1958 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7003 0.4012 2.2166 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3180 -3.5950 -2.3710 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8012 -2.9710 -1.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5780 -4.4606 -1.0014 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0169 -1.1043 -1.8286 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9289 -1.0939 1.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0613 -0.6492 1.5968 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3958 -0.2079 0.9901 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9822 0.4298 -1.2651 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1894 0.6331 -2.9745 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8464 0.2028 -2.4189 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7494 1.3903 1.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8320 2.3426 -0.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7933 0.0314 2.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1420 -0.9236 -0.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7242 -1.6474 1.3372 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1595 0.4712 -1.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1796 -1.0139 -1.1939 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2785 -5.4648 -1.2958 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4902 -7.4178 -0.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0059 -7.1798 1.4947 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3355 -5.0131 2.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1284 -3.0607 1.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5796 0.3685 -0.1669 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4035 -2.4561 0.2960 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0687 -2.3780 -1.3537 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6339 -3.4035 -1.0841 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6310 -1.5491 -3.7403 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2899 -0.5810 -3.1210 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7981 0.0344 -3.5948 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4084 2.0695 -2.7895 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9596 2.6156 -3.6051 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6014 2.2875 -0.6302 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4389 4.1536 -2.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1369 3.0548 -2.8349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0068 1.7418 -2.6519 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8552 3.1663 -1.6694 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8609 3.1922 2.2856 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7995 6.2625 0.5835 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3582 7.0059 2.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7529 7.2264 0.8296 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3622 2.5990 2.4559 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6507 3.5910 1.2391 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9676 3.4614 2.9729 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0751 0.4825 3.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4367 -0.5692 3.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1251 -1.2234 3.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2024 -0.5405 2.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 1.3240 1.9568 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8514 0.4655 3.3528 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 5 12 1 0 12 13 1 0 12 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 21 31 1 0 31 32 1 0 32 33 1 1 33 34 1 0 34 35 1 0 34 36 2 0 32 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 43 44 1 6 43 45 1 0 45 46 2 0 45 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 49 51 2 0 47 52 1 0 52 53 2 0 53 54 1 0 52 55 1 0 55 56 1 0 55 57 1 0 11 6 1 0 53 17 1 0 55 19 1 0 30 25 1 0 43 31 1 0 39 32 1 0 1 58 1 0 1 59 1 0 1 60 1 0 4 61 1 0 5 62 1 1 7 63 1 0 8 64 1 0 9 65 1 0 10 66 1 0 11 67 1 0 12 68 1 1 13 69 1 0 17 70 1 1 18 71 1 0 18 72 1 0 20 73 1 0 21 74 1 6 26 75 1 0 27 76 1 0 28 77 1 0 29 78 1 0 30 79 1 0 31 80 1 1 35 81 1 0 35 82 1 0 35 83 1 0 37 84 1 0 37 85 1 0 39 86 1 6 40 87 1 0 40 88 1 0 41 89 1 1 42 90 1 0 44 91 1 0 44 92 1 0 44 93 1 0 47 94 1 1 50 95 1 0 50 96 1 0 50 97 1 0 54 98 1 0 54 99 1 0 54100 1 0 56101 1 0 56102 1 0 56103 1 0 57104 1 0 57105 1 0 57106 1 0 M END

Standard InCHIKey	NANZRVGWMMGVIQ-UJNNUTRWSA-N
Standard InCHI	InChI=1S/C42H49NO14/c1-21-27(55-38(51)32(48)31(43-22(2)44)25-14-10-8-11-15-25)19-42(52)36(56-37(50)26-16-12-9-13-17-26)34-40(7,28(47)18-29-41(34,20-53-29)57-24(4)46)35(49)33(54-23(3)45)30(21)39(42,5)6/h8-17,27-29,31-34,36,47-48,52H,18-20H2,1-7H3,(H,43,44)/t27-,28+,29-,31+,32-,33-,34+,36+,40-,41+,42-/m1/s1
SMILES	CC(=O)N[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:	791.32	Volume:	783.435 ? Van der Waals volume.
Dense:	1.01	LogP:	2.171 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.568 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.198 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	38.0
TPSA:	221.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.163	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.899	Fsp³:	0.524
MCE-18:	163.5 ? 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:	0.802	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.036 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.194 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.09

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.922	MDCK Permeability:	-5.221
Pgp-inhibitor:	0.689	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):	0.002
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):	88.224%	Volume Distribution (VD):	0.065
Fu:	12.198% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.0
BSEP inhibitor:	0.679

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:	0.044	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.991
HLM stability:	0.048 ? 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):

4.134

Half-life (T1/2):

2.693

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.064
Human Hepatotoxicity (H-HT):	0.932	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.731
Maximum Recommended Daily Dose:	0.994	Skin Sensitization:	1.0
Carcinogencity:	0.74	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.027
Drug-induced Neurotoxicity:	0.999	Ototoxicity:	0.891
Hematotoxicity:	0.963	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.695
A549 Cytotoxicity:	0.967	Hek293 Cytotoxicity:	0.882
BCF:	0.472 ? 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:	3.281 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.953 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.051 ? 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 NPC537050 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	11749
0.1-0.2	35985
0.2-0.3	1961
0.3-0.4	90
0.4-0.5	18
0.5-0.6	23
0.6-0.7	9
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC473400
0.8617	High Similarity	NPC603171
0.8081	Intermediate Similarity	NPC471606
0.7653	Intermediate Similarity	NPC473300
0.7553	Intermediate Similarity	NPC603140
0.7525	Intermediate Similarity	NPC487360
0.75	Intermediate Similarity	NPC317882
0.7426	Intermediate Similarity	NPC33372
0.7426	Intermediate Similarity	NPC67246
0.7426	Intermediate Similarity	NPC324251
0.7426	Intermediate Similarity	NPC206211
0.7379	Intermediate Similarity	NPC275170
0.7353	Intermediate Similarity	NPC479182
0.7353	Intermediate Similarity	NPC479180
0.7353	Intermediate Similarity	NPC471629
0.7353	Intermediate Similarity	NPC306001
0.7327	Intermediate Similarity	NPC471623
0.7327	Intermediate Similarity	NPC208553
0.7327	Intermediate Similarity	NPC181964
0.7327	Intermediate Similarity	NPC307628
0.7238	Intermediate Similarity	NPC487361
0.7143	Intermediate Similarity	NPC486061
0.7143	Intermediate Similarity	NPC486060
0.7129	Intermediate Similarity	NPC36607
0.6596	Remote Similarity	NPC155329
0.6596	Remote Similarity	NPC114357
0.6204	Remote Similarity	NPC453583
0.6146	Remote Similarity	NPC605573
0.6091	Remote Similarity	NPC478329
0.6055	Remote Similarity	NPC453588
0.6	Remote Similarity	NPC471754
0.6	Remote Similarity	NPC479183
0.6	Remote Similarity	NPC479181
0.5963	Remote Similarity	NPC321072
0.5963	Remote Similarity	NPC215892
0.5963	Remote Similarity	NPC242662
0.5963	Remote Similarity	NPC102167
0.5963	Remote Similarity	NPC473490
0.5963	Remote Similarity	NPC488127
0.5948	Remote Similarity	NPC472392
0.5909	Remote Similarity	NPC191193
0.5818	Remote Similarity	NPC327699
0.5644	Remote Similarity	NPC259144
0.5644	Remote Similarity	NPC219419
0.5574	Remote Similarity	NPC479184
0.5455	Remote Similarity	NPC472391
0.5417	Remote Similarity	NPC116862
0.541	Remote Similarity	NPC479185
0.54	Remote Similarity	NPC197037
0.54	Remote Similarity	NPC229545
0.54	Remote Similarity	NPC248265
0.54	Remote Similarity	NPC134685
0.5248	Remote Similarity	NPC91730
0.5217	Remote Similarity	NPC473558
0.5196	Remote Similarity	NPC217918
0.513	Remote Similarity	NPC478328

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC537050 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3350
0.1-0.2	5671
0.2-0.3	116
0.3-0.4	0
0.4-0.5	4
0.5-0.6	4
0.6-0.7	4
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
0.7327	Intermediate Similarity	NPD8485	Phase 4
0.6604	Remote Similarity	NPD8368	Phase 2
0.6574	Remote Similarity	NPD8486	Phase 1
0.6111	Remote Similarity	NPD8424	Phase 3
0.605	Remote Similarity	NPD8462	Phase 2
0.5963	Remote Similarity	NPD8360	Approved
0.5963	Remote Similarity	NPD8361	Phase 4
0.5766	Remote Similarity	NPD8435	Phase 4
0.5043	Remote Similarity	NPD8407	Phase 2

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