NPASS Compound

Natural Product: NPC486060

Natural Product ID	NPC486060
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QSYMCEMXHBPDHG-ZNBKKJCASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10772052
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 115120 0 0 0 0 0 0 0 0999 V2000 0.9882 -0.8813 2.4435 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0619 0.1946 1.9919 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1911 0.2334 2.4106 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5716 -1.1479 2.7029 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7569 -1.5791 1.8988 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2454 -2.5767 2.4330 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5630 -1.2434 0.6885 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9192 -0.8856 1.2645 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7978 -2.5844 0.0300 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6866 -2.8223 -0.9380 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9845 -1.8837 -2.0658 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0351 -0.4370 -1.6805 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3797 -0.3896 -2.2596 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2874 -1.7847 -2.4935 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8930 -0.2377 -0.1534 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0557 1.1934 0.2439 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9529 1.9159 0.9198 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6002 1.9570 0.3114 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5240 1.2587 1.0403 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3488 0.5290 0.1076 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6997 0.7722 -0.0560 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1932 1.6706 0.6507 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5221 0.0057 -1.0229 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6556 -0.6492 -0.2172 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3954 0.3942 0.5220 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3387 0.5261 1.8912 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0339 1.5168 2.5599 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8109 2.4086 1.8680 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8797 2.2918 0.5008 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1867 1.3043 -0.1654 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4961 -1.3052 -1.2010 N 0 0 0 0 0 0 0 0 0 0 0 0 6.5062 -1.9911 -0.7994 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3782 -2.6690 -1.7962 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8884 -2.4752 -3.2004 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5487 -4.1114 -1.4478 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4423 -4.8194 -2.4654 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9940 -4.9867 -1.4433 Cl 0 0 0 0 0 0 0 0 0 0 0 0 8.9859 -1.8726 -1.6817 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.8089 -2.1177 0.5450 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8175 -0.9506 -1.7097 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7948 1.6061 2.4159 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0065 1.6237 3.2300 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8275 2.6479 3.0036 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4129 3.2658 0.9568 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6998 1.9603 -0.7683 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9368 2.5065 -0.7380 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5686 2.2929 0.3244 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5597 3.2818 -1.7877 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8449 3.7413 -1.6077 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5185 4.4861 -2.5342 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9007 4.8063 -3.7156 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6138 4.3571 -3.9172 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9419 3.6020 -2.9694 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9770 0.1819 -2.3912 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8008 0.2163 -3.7292 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6629 -0.3641 -4.4300 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6683 0.8858 -4.4222 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9928 -2.7085 -0.6286 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9529 -1.2564 4.0795 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4599 -2.2438 4.9035 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6523 -3.0836 4.4391 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8380 -2.3737 6.3428 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0181 -0.4200 2.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9099 -1.0960 3.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0277 -1.7523 1.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8316 -1.9244 2.5213 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6276 -0.4278 0.6049 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3546 -1.8466 1.6905 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8663 -0.2601 2.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7691 -3.4220 0.7783 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6881 -2.6437 -0.5451 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8176 -3.8621 -1.3479 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3464 -2.1708 -2.9285 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5095 0.2057 -3.2094 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2674 -0.1948 -1.6678 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7792 -0.4498 -0.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8580 1.1822 1.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2233 3.0381 0.2639 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5202 1.6414 -0.7260 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2473 1.9619 1.5181 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0472 0.7256 -1.6889 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1744 -1.3492 0.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7437 -0.1491 2.4736 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9884 1.6211 3.6345 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3692 3.2024 2.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5039 3.0135 -0.0214 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2569 1.2323 -1.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7133 -2.4800 -3.9245 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0967 -3.2169 -3.4468 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3958 -1.4753 -3.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9701 -4.1857 -0.4164 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2375 -4.1082 -2.7704 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8473 -5.7352 -2.0199 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7870 -5.0970 -3.3249 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0342 -2.1880 1.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8994 -1.0130 -1.2990 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9244 2.0526 2.8141 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2748 0.6214 3.6828 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8214 2.2431 4.1660 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0037 2.1775 3.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3524 3.2773 3.7854 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5309 3.3934 2.2379 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9293 3.4673 1.7498 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3589 3.5060 -0.6900 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5272 4.8387 -2.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4471 5.4044 -4.4545 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1120 4.6051 -4.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9349 3.2418 -3.1096 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3134 0.6922 -3.9013 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5309 0.4173 -5.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8397 1.9674 -4.5585 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7660 -2.2650 -0.2614 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0270 -1.8843 6.9474 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8133 -1.9044 6.5007 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8818 -3.4107 6.6818 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 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 24 31 1 0 31 32 2 3 32 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 35 37 1 0 33 38 1 6 32 39 1 0 23 40 1 0 17 41 1 0 41 42 1 0 41 43 1 0 17 44 1 1 16 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 12 54 1 6 54 55 1 0 55 56 2 0 55 57 1 0 9 58 1 0 4 59 1 0 59 60 1 0 60 61 2 0 60 62 1 0 19 2 1 0 30 25 1 0 53 48 1 0 41 3 1 0 15 7 1 0 14 11 1 0 1 63 1 0 1 64 1 0 1 65 1 0 4 66 1 1 8 67 1 0 8 68 1 0 8 69 1 0 9 70 1 1 10 71 1 0 10 72 1 0 11 73 1 6 13 74 1 0 13 75 1 0 15 76 1 6 16 77 1 1 18 78 1 0 18 79 1 0 19 80 1 1 23 81 1 6 24 82 1 1 26 83 1 0 27 84 1 0 28 85 1 0 29 86 1 0 30 87 1 0 34 88 1 0 34 89 1 0 34 90 1 0 35 91 1 1 36 92 1 0 36 93 1 0 36 94 1 0 39 95 1 0 40 96 1 0 42 97 1 0 42 98 1 0 42 99 1 0 43100 1 0 43101 1 0 43102 1 0 44103 1 0 49104 1 0 50105 1 0 51106 1 0 52107 1 0 53108 1 0 57109 1 0 57110 1 0 57111 1 0 58112 1 0 62113 1 0 62114 1 0 62115 1 0 M END

Standard InCHIKey	QSYMCEMXHBPDHG-ZNBKKJCASA-N
Standard InCHI	InChI=1S/C45H53Cl2NO14/c1-22-28(60-39(55)33(52)32(26-15-11-9-12-16-26)48-40(56)43(8,47)23(2)46)20-45(57)37(61-38(54)27-17-13-10-14-18-27)35-42(7,29(51)19-30-44(35,21-58-30)62-25(4)50)36(53)34(59-24(3)49)31(22)41(45,5)6/h9-18,23,28-30,32-35,37,51-52,57H,19-21H2,1-8H3,(H,48,56)/t23-,28-,29-,30+,32-,33+,34+,35-,37-,42+,43-,44-,45+/m0/s1
SMILES	CC1=C2[C@H](C(=O)[C@]3(C)[C@H](C[C@@H]4[C@@](CO4)([C@H]3[C@@H]([C@](C[C@@H]1OC(=O)[C@@H]([C@H](c1ccccc1)N=C([C@](C)([C@H](C)Cl)Cl)O)O)(C2(C)C)O)OC(=O)c1ccccc1)OC(=O)C)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	901.28	Volume:	865.745 ? Van der Waals volume.
Dense:	1.041	LogP:	3.624 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.324 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.86 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	38.0
TPSA:	224.78 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.059	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.505	Fsp³:	0.556
MCE-18:	175.314 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.922	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.033 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.29 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.042	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.897	MDCK Permeability:	-5.351
Pgp-inhibitor:	0.045	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):	0.0
20% Bioavailability (F20%):	0.93	30% Bioavailability (F30%):	0.888
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	94.332%	Volume Distribution (VD):	0.186
Fu:	3.551% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.981	BCRP inhibitor:	0.0
BSEP inhibitor:	0.587

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.966 ? 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):

1.834

Half-life (T1/2):

2.935

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.011
Human Hepatotoxicity (H-HT):	0.999	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.982	Skin Sensitization:	1.0
Carcinogencity:	0.41	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.274
Drug-induced Neurotoxicity:	0.997	Ototoxicity:	0.89
Hematotoxicity:	0.963	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.766
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.935
BCF:	0.566 ? 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:	3.562 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.133 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.385 ? 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
NPO41064	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461653]
NPO41064	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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

Activity Type	# Activity
GI50	1
TGI	1

Activity Type	# Activity
Non-molecular	2

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	210.0	nM	PMID[9461653]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	TGI	=	6300.0	nM	PMID[9461653]

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 NPC486060 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	11787
0.1-0.2	36109
0.2-0.3	1856
0.3-0.4	41
0.4-0.5	10
0.5-0.6	11
0.6-0.7	19
0.7-0.8	1
0.8-0.85	6
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC486061
0.8586	High Similarity	NPC33372
0.8586	High Similarity	NPC67246
0.8586	High Similarity	NPC324251
0.8586	High Similarity	NPC206211
0.85	High Similarity	NPC487360
0.85	High Similarity	NPC479182
0.85	High Similarity	NPC479180
0.85	High Similarity	NPC471629
0.85	High Similarity	NPC306001
0.8333	Intermediate Similarity	NPC275170
0.8173	Intermediate Similarity	NPC487361
0.8119	Intermediate Similarity	NPC471623
0.8119	Intermediate Similarity	NPC208553
0.8119	Intermediate Similarity	NPC181964
0.8119	Intermediate Similarity	NPC307628
0.7264	Intermediate Similarity	NPC453583
0.713	Intermediate Similarity	NPC478329
0.7037	Intermediate Similarity	NPC471754
0.7037	Intermediate Similarity	NPC479183
0.7037	Intermediate Similarity	NPC479181
0.6961	Remote Similarity	NPC603140
0.6944	Remote Similarity	NPC473400
0.6789	Remote Similarity	NPC453588
0.6759	Remote Similarity	NPC36607
0.6697	Remote Similarity	NPC321072
0.6697	Remote Similarity	NPC215892
0.6697	Remote Similarity	NPC242662
0.6697	Remote Similarity	NPC102167
0.6697	Remote Similarity	NPC488127
0.6636	Remote Similarity	NPC191193
0.6636	Remote Similarity	NPC603171
0.6545	Remote Similarity	NPC327699
0.65	Remote Similarity	NPC479184
0.6387	Remote Similarity	NPC472391
0.6333	Remote Similarity	NPC479185
0.6261	Remote Similarity	NPC471606
0.6238	Remote Similarity	NPC155329
0.6238	Remote Similarity	NPC114357
0.6083	Remote Similarity	NPC116862
0.5776	Remote Similarity	NPC317882
0.5739	Remote Similarity	NPC473300
0.569	Remote Similarity	NPC473490
0.569	Remote Similarity	NPC478328
0.5673	Remote Similarity	NPC605573
0.5635	Remote Similarity	NPC472375
0.56	Remote Similarity	NPC479173
0.5476	Remote Similarity	NPC479186
0.537	Remote Similarity	NPC259144
0.5238	Remote Similarity	NPC289383
0.5229	Remote Similarity	NPC219419

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3187
0.1-0.2	5812
0.2-0.3	138
0.3-0.4	0
0.4-0.5	5
0.5-0.6	0
0.6-0.7	6
0.7-0.8	1
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
0.8119	Intermediate Similarity	NPD8485	Phase 4
0.7315	Intermediate Similarity	NPD8486	Phase 1
0.6852	Remote Similarity	NPD8424	Phase 3
0.6697	Remote Similarity	NPD8360	Approved
0.6697	Remote Similarity	NPD8361	Phase 4
0.6486	Remote Similarity	NPD8435	Phase 4
0.6311	Remote Similarity	NPD8462	Phase 2
0.6283	Remote Similarity	NPD8368	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