NPASS Compound

Natural Product: NPC52912

Natural Product ID	NPC52912
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DBXFAPJCZABTDR-CFKFQIECSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	45358115
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

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 113118 0 0 0 0 0 0 0 0999 V2000 9.5108 0.1532 0.0838 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1239 0.3159 0.6100 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6590 -0.5583 1.4448 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5503 -1.6951 1.8375 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3249 -0.5232 2.0454 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4957 0.3202 1.8426 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0520 1.4800 1.2375 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7642 1.4124 -0.1963 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0887 2.4582 -1.0391 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8516 2.3800 -2.3879 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2803 1.2253 -2.8719 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9520 0.1762 -2.0428 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1955 0.2724 -0.7009 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8772 2.0178 2.0616 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7943 1.0635 2.2669 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6555 0.4152 3.3222 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8773 0.8534 1.2895 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8017 0.0395 1.2484 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4864 0.8871 1.4133 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4310 0.3230 0.4531 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8953 0.3301 0.5711 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6634 -0.8335 0.1437 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2753 -2.1542 -0.3326 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3258 -3.2796 0.7244 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4592 -2.5141 -1.2943 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7433 -1.9140 -1.1819 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0837 -0.8869 -0.1358 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9631 -0.8218 0.8603 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6753 -2.0982 1.2084 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8626 -1.3337 0.9441 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2141 0.0516 1.8928 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7034 0.0719 3.1666 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9099 -0.8354 3.4787 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0198 1.0866 4.2032 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4962 -3.8920 -1.4763 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0860 -2.4762 -1.1075 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3127 -3.3670 -1.9034 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5802 -2.1839 -1.3915 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1951 -0.9759 -0.7714 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7112 -1.0056 0.1778 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5991 -2.1787 0.1409 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8146 0.4045 -0.8915 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7063 0.4904 -2.0955 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2904 1.3661 -1.1510 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1795 -3.2605 -1.5815 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6717 -3.8371 -2.6766 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3528 -3.2441 -3.7258 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5113 -5.0422 -2.7744 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3335 1.5262 -0.1428 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7234 2.6733 0.4682 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6983 2.7339 1.7227 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1812 3.8707 -0.2493 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2741 3.8385 -1.6117 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6972 4.9685 -2.2831 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0330 6.1372 -1.6312 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9230 6.1185 -0.2580 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5060 5.0152 0.4434 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3672 -1.0189 1.0556 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3925 2.2754 3.3807 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9717 -1.5728 2.9460 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2423 0.3544 0.9126 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6713 -0.8462 -0.3620 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7288 0.9033 -0.7023 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5502 1.1460 0.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0708 -2.3720 2.5499 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4077 -1.2188 2.3852 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9577 -2.2159 0.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8757 2.2731 1.3885 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5367 3.3352 -0.5822 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1245 3.2218 -2.9925 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0991 1.1786 -3.9449 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5020 -0.7302 -2.4288 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9562 -0.5261 -0.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5935 3.0089 1.6748 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8036 -0.5586 2.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8911 0.7897 2.4680 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2722 1.9610 1.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0734 0.6477 1.6166 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0632 -0.3855 -0.9037 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5193 -2.9202 1.7303 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8402 -4.1819 0.3822 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2729 -3.7241 0.8516 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0176 -2.1858 -2.3064 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0325 -1.3779 -2.1530 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5787 -2.6659 -1.1618 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4776 0.0859 -0.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7552 -2.3480 2.3037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7765 -2.9416 0.6208 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1053 1.2760 4.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3798 2.0206 3.7731 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7611 0.6588 4.9326 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9948 -4.0920 -2.2977 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7215 -1.8529 -2.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1297 -3.1092 0.5082 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1919 -2.2763 -0.7680 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3646 -2.0090 0.9300 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9918 0.5586 -2.9965 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2023 1.4493 -2.1566 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2524 -0.3977 -2.3784 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1863 1.9031 -2.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3759 2.2423 -0.5047 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2723 0.8454 -1.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3054 -4.8480 -3.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9138 -5.3680 -1.7925 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8943 -5.8868 -3.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0236 2.9241 -2.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7623 4.9181 -3.3667 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3695 7.0284 -2.1857 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1789 7.0205 0.2888 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4269 5.0312 1.5453 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6428 -0.9494 1.9737 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5905 1.3976 3.7478 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1435 -1.4409 3.5118 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 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 7 14 1 0 14 15 1 0 15 16 2 0 15 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 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 1 31 32 1 0 32 33 2 0 32 34 1 0 25 35 1 0 23 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 39 40 2 0 40 41 1 0 39 42 1 0 42 43 1 0 42 44 1 0 38 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 21 49 1 0 49 50 1 0 50 51 2 0 50 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 20 58 1 1 14 59 1 0 5 60 1 0 13 8 1 0 40 18 1 0 57 52 1 0 42 20 1 0 28 22 1 0 30 27 1 0 1 61 1 0 1 62 1 0 1 63 1 0 2 64 1 0 4 65 1 0 4 66 1 0 4 67 1 0 7 68 1 0 9 69 1 0 10 70 1 0 11 71 1 0 12 72 1 0 13 73 1 0 14 74 1 0 18 75 1 1 19 76 1 0 19 77 1 0 21 78 1 1 22 79 1 6 24 80 1 0 24 81 1 0 24 82 1 0 25 83 1 6 26 84 1 0 26 85 1 0 27 86 1 6 29 87 1 0 29 88 1 0 34 89 1 0 34 90 1 0 34 91 1 0 35 92 1 0 38 93 1 6 41 94 1 0 41 95 1 0 41 96 1 0 43 97 1 0 43 98 1 0 43 99 1 0 44100 1 0 44101 1 0 44102 1 0 48103 1 0 48104 1 0 48105 1 0 53106 1 0 54107 1 0 55108 1 0 56109 1 0 57110 1 0 58111 1 0 59112 1 0 60113 1 0 M END

Standard InCHIKey	DBXFAPJCZABTDR-CFKFQIECSA-N
Standard InCHI	InChI=1S/C45H53NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(H,46,52)/b23-9+/t29-,30-,31+,33?,34?,35+,36-,38-,43+,44-,45+/m0/s1
SMILES	C/C=C(C)/C(=NC(c1ccccc1)C(C(=O)O[C@H]1C[C@]2([C@H]([C@H]3[C@@](C)([C@H](C[C@@H]4[C@]3(CO4)OC(=O)C)O)C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)OC(=O)c1ccccc1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	831.35	Volume:	832.687 ? Van der Waals volume.
Dense:	0.998	LogP:	2.893 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.071 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.06 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	39.0
TPSA:	224.78 ? 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:	0.087	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.282	Fsp³:	0.511
MCE-18:	165.735 ? 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:	0.839	Fluc inhibitor:	0.01 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.089 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.306 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.004	Promiscuous compounds:	0.005

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.64	MDCK Permeability:	-5.089
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):	0.009
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):	92.254%	Volume Distribution (VD):	0.03
Fu:	6.999% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.0
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.939	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.781 ? 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):

2.696

Half-life (T1/2):

2.96

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.032
Human Hepatotoxicity (H-HT):	0.932	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.992	Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.945	Skin Sensitization:	1.0
Carcinogencity:	0.912	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.067
Drug-induced Neurotoxicity:	0.98	Ototoxicity:	0.936
Hematotoxicity:	0.843	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.356
A549 Cytotoxicity:	0.839	Hek293 Cytotoxicity:	0.838
BCF:	0.443 ? 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:	3.286 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.073 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.131 ? 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
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[12502326]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220355]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23265441]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
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]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18950	Cephalotaxus fortunei	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 NPC52912 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	9354
0.1-0.2	37661
0.2-0.3	2679
0.3-0.4	95
0.4-0.5	11
0.5-0.6	12
0.6-0.7	13
0.7-0.8	4
0.8-0.85	6
0.85-0.9	11
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC33372
1.0	High Similarity	NPC67246
0.8947	High Similarity	NPC324251
0.8947	High Similarity	NPC206211
0.8854	High Similarity	NPC487360
0.8854	High Similarity	NPC479182
0.8854	High Similarity	NPC479180
0.8854	High Similarity	NPC471629
0.8854	High Similarity	NPC306001
0.8687	High Similarity	NPC487361
0.8673	High Similarity	NPC275170
0.8586	High Similarity	NPC486061
0.8586	High Similarity	NPC486060
0.8454	Intermediate Similarity	NPC471623
0.8454	Intermediate Similarity	NPC453583
0.8454	Intermediate Similarity	NPC208553
0.8454	Intermediate Similarity	NPC181964
0.8454	Intermediate Similarity	NPC307628
0.8283	Intermediate Similarity	NPC478329
0.7476	Intermediate Similarity	NPC471754
0.7476	Intermediate Similarity	NPC479183
0.7476	Intermediate Similarity	NPC479181
0.7379	Intermediate Similarity	NPC453588
0.7364	Intermediate Similarity	NPC472391
0.7245	Intermediate Similarity	NPC603140
0.7212	Intermediate Similarity	NPC473400
0.7115	Intermediate Similarity	NPC321072
0.7115	Intermediate Similarity	NPC215892
0.7115	Intermediate Similarity	NPC242662
0.7115	Intermediate Similarity	NPC102167
0.7115	Intermediate Similarity	NPC488127
0.7019	Intermediate Similarity	NPC36607
0.6887	Remote Similarity	NPC191193
0.6887	Remote Similarity	NPC603171
0.6792	Remote Similarity	NPC327699
0.6724	Remote Similarity	NPC479184
0.6552	Remote Similarity	NPC479185
0.6495	Remote Similarity	NPC155329
0.6495	Remote Similarity	NPC114357
0.6486	Remote Similarity	NPC471606
0.6466	Remote Similarity	NPC479173
0.6389	Remote Similarity	NPC473300
0.6293	Remote Similarity	NPC116862
0.6126	Remote Similarity	NPC317882
0.6036	Remote Similarity	NPC478328
0.595	Remote Similarity	NPC472375
0.59	Remote Similarity	NPC605573
0.5893	Remote Similarity	NPC473490
0.5785	Remote Similarity	NPC479186
0.5577	Remote Similarity	NPC259144
0.5537	Remote Similarity	NPC289383
0.5429	Remote Similarity	NPC219419
0.534	Remote Similarity	NPC197037
0.534	Remote Similarity	NPC229545
0.534	Remote Similarity	NPC248265
0.534	Remote Similarity	NPC134685
0.5048	Remote Similarity	NPC91730

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC52912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3022
0.1-0.2	5927
0.2-0.3	188
0.3-0.4	0
0.4-0.5	4
0.5-0.6	1
0.6-0.7	3
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8454	Intermediate Similarity	NPD8485	Phase 4
0.7596	Intermediate Similarity	NPD8486	Phase 1
0.7282	Intermediate Similarity	NPD8424	Phase 3
0.7115	Intermediate Similarity	NPD8360	Approved
0.7115	Intermediate Similarity	NPD8361	Phase 4
0.6729	Remote Similarity	NPD8435	Phase 4
0.6525	Remote Similarity	NPD8462	Phase 2
0.6514	Remote Similarity	NPD8368	Phase 2
0.5126	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