NPASS Compound

Natural Product: NPC82882

Natural Product ID	NPC82882
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SHGCFQDGGXDIFG-OWRRKEEJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101682279
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 116122 0 0 0 0 0 0 0 0999 V2000 -7.7437 2.5122 2.6424 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8116 1.8278 1.2692 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6892 2.6716 0.4071 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3342 0.4307 1.5099 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4714 -0.2694 0.2097 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2459 -0.2523 -0.6763 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6169 -1.6150 -0.5294 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2842 -1.7569 -1.1724 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2895 -0.7449 -0.5745 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1812 -1.1301 0.8757 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9111 0.5602 -0.8208 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2013 1.5271 -1.3692 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7833 1.4583 -1.7891 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1637 0.3616 -0.9799 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6750 0.3108 -1.0388 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0928 0.4288 -2.3991 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2046 1.5444 -0.2492 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2789 1.5475 -0.0899 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8734 0.3038 0.4686 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1788 -0.9738 0.1730 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0295 -1.8111 -0.7557 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1629 -1.7318 1.5245 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5592 -2.9564 1.4503 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2306 -0.8773 -0.2387 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7321 -2.0785 -0.9948 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2374 -2.1335 -0.6757 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9315 -0.8973 -1.2139 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1069 -1.2269 -2.7044 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1852 0.2352 -0.0747 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1674 0.4200 0.8673 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1993 -0.6655 0.7417 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4694 -0.1920 1.4594 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9911 0.7969 2.5298 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4587 2.0053 1.7841 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8448 1.6552 0.5820 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0887 1.2251 3.2801 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2912 0.5110 0.6186 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5853 0.0079 0.5647 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0291 -0.4117 -0.8004 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3842 0.2036 -1.1578 C 0 0 2 0 0 0 0 0 0 0 0 0 11.3853 0.0158 -0.0524 C 0 0 1 0 0 0 0 0 0 0 0 0 10.6948 0.1725 1.2853 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5168 0.9222 1.0631 O 0 0 0 0 0 0 0 0 0 0 0 0 11.9272 -1.2612 -0.1936 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2576 1.5634 -1.4108 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1627 -1.7905 -0.9441 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7835 -1.8311 1.3521 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3341 0.8975 -0.4826 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4156 1.6763 0.7886 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8028 -0.2054 -2.0534 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5749 -1.1213 -2.8539 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5780 0.8696 -2.4355 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3433 3.5418 2.4731 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0573 1.9186 3.2773 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7677 2.5834 3.0234 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2242 2.8679 -0.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8752 3.6891 0.8610 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6875 2.2535 0.2238 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5682 -0.0942 2.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2923 0.4177 2.0257 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8017 -1.3101 0.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3655 0.1935 -0.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6517 -1.9853 0.5265 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2956 -2.3384 -1.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9385 -2.7982 -0.9933 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3931 -1.5099 -2.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3199 -0.7117 1.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1825 -2.2634 0.8862 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0852 -0.9077 1.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6659 2.5266 -1.5633 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7697 1.2782 -2.8778 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3055 2.4435 -1.6333 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4090 0.6345 0.0974 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8602 0.6303 -3.1950 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4964 -0.4268 -2.7478 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5968 1.3193 -2.5132 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4578 2.4871 -0.8059 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6813 1.5453 0.7497 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5004 2.3888 0.6332 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8209 1.8537 -1.0092 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9595 0.4747 1.5805 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4294 -2.3925 -1.4774 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5993 -2.5300 -0.1430 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8168 -1.1998 -1.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1609 -1.8325 1.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6066 -1.0661 2.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1434 -3.6977 1.2030 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8547 -0.8200 0.7076 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5542 -2.0326 -2.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2941 -2.9863 -0.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5912 -3.0478 -1.1531 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2301 -2.1772 0.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6736 -0.4899 -3.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1313 -1.3695 -3.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5736 -2.2547 -2.7140 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7366 0.5253 1.8628 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4301 -0.8381 -0.3401 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9956 -1.0398 1.9427 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2591 0.3394 3.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3470 2.6341 1.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8064 2.6354 2.4106 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5969 0.4447 3.5728 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6226 -0.8755 1.2345 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3365 -0.0669 -1.6029 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7176 -0.3209 -2.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2013 0.7611 -0.1628 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3224 0.6182 2.0553 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3783 -0.8514 1.6015 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1956 -1.3499 -1.1428 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6149 2.0845 -0.6436 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9881 -2.1020 -1.8485 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0891 -2.5938 0.7762 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6897 1.6778 -1.2426 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0304 2.7222 0.5773 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7717 1.3495 1.6151 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2371 0.7126 -3.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 19 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 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 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 31 47 1 0 11 48 1 0 48 49 1 0 6 50 1 6 50 51 2 0 50 52 1 0 49 2 1 0 48 6 1 0 27 9 1 0 35 30 1 0 43 38 1 0 27 14 1 0 24 15 1 0 1 53 1 0 1 54 1 0 1 55 1 0 3 56 1 0 3 57 1 0 3 58 1 0 4 59 1 0 4 60 1 0 5 61 1 0 5 62 1 0 7 63 1 0 7 64 1 0 8 65 1 0 8 66 1 0 10 67 1 0 10 68 1 0 10 69 1 0 12 70 1 0 13 71 1 0 13 72 1 0 14 73 1 1 16 74 1 0 16 75 1 0 16 76 1 0 17 77 1 0 17 78 1 0 18 79 1 0 18 80 1 0 19 81 1 1 21 82 1 0 21 83 1 0 21 84 1 0 22 85 1 0 22 86 1 0 23 87 1 0 24 88 1 1 25 89 1 0 25 90 1 0 26 91 1 0 26 92 1 0 28 93 1 0 28 94 1 0 28 95 1 0 30 96 1 1 31 97 1 6 32 98 1 1 33 99 1 1 34100 1 0 34101 1 0 36102 1 0 38103 1 1 39104 1 6 40105 1 6 41106 1 6 42107 1 0 42108 1 0 44109 1 0 45110 1 0 46111 1 0 47112 1 0 48113 1 6 49114 1 0 49115 1 0 52116 1 0 M END

Standard InCHIKey	SHGCFQDGGXDIFG-OWRRKEEJSA-N
Standard InCHI	InChI=1S/C40H64O12/c1-35(2)13-15-40(34(47)48)16-14-38(5)21(22(40)17-35)7-8-26-36(3)11-10-27(37(4,20-41)25(36)9-12-39(26,38)6)51-33-30(46)31(24(43)19-50-33)52-32-29(45)28(44)23(42)18-49-32/h7,22-33,41-46H,8-20H2,1-6H3,(H,47,48)/t22-,23+,24-,25+,26+,27-,28-,29+,30+,31-,32-,33-,36-,37-,38+,39+,40-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O)[C@@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	736.44	Volume:	740.71 ? Van der Waals volume.
Dense:	0.994	LogP:	2.252 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.56 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.555 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	39.0
TPSA:	195.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.156	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.759	Fsp³:	0.925
MCE-18:	147.299 ? 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:	0.937	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.178	Promiscuous compounds:	0.091

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.049	MDCK Permeability:	-5.219
Pgp-inhibitor:	0.0	Pgp-substrate:	0.008
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):	0.001
20% Bioavailability (F20%):	0.047	30% Bioavailability (F30%):	0.016
50% Bioavailability (F50%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065	MRP1:	0.614
Plasma Protein Binding (PPB):	80.334%	Volume Distribution (VD):	-0.574
Fu:	12.901% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.508	BCRP inhibitor:	0.005
BSEP inhibitor:	0.184

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:	0.001
CYP3A4-inhibitor:	0.026	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.483 ? 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):

0.264

Half-life (T1/2):

1.868

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.759	Drug-induced Liver Injury (DILI):	0.828
AMES Toxicity:	0.685	Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.032	Skin Sensitization:	1.0
Carcinogencity:	0.489	Eye Corrosion:	0.0
Eye Irritation:	0.021	Respiratory Toxicity:	0.104
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.979
Hematotoxicity:	0.729	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	0.122	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.247	Hek293 Cytotoxicity:	0.148
BCF:	0.864 ? 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:	3.616 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.263 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.31 ? 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
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19649	Akebia quinata	Species	Lardizabalaceae	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 NPC82882 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	20545
0.1-0.2	24976
0.2-0.3	3140
0.3-0.4	768
0.4-0.5	308
0.5-0.6	69
0.6-0.7	35
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8875	High Similarity	NPC28198
0.8875	High Similarity	NPC476123
0.7976	Intermediate Similarity	NPC283849
0.7701	Intermediate Similarity	NPC100383
0.7634	Intermediate Similarity	NPC6377
0.7634	Intermediate Similarity	NPC208381
0.7283	Intermediate Similarity	NPC270667
0.7241	Intermediate Similarity	NPC204407
0.7079	Intermediate Similarity	NPC177246
0.7	Intermediate Similarity	NPC481082
0.7	Intermediate Similarity	NPC164419
0.6981	Remote Similarity	NPC323341
0.6957	Remote Similarity	NPC284807
0.6947	Remote Similarity	NPC136877
0.6907	Remote Similarity	NPC488561
0.6875	Remote Similarity	NPC174679
0.6875	Remote Similarity	NPC279554
0.6875	Remote Similarity	NPC59804
0.6863	Remote Similarity	NPC276093
0.6634	Remote Similarity	NPC104400
0.6634	Remote Similarity	NPC10320
0.66	Remote Similarity	NPC469945
0.6593	Remote Similarity	NPC606107
0.6559	Remote Similarity	NPC242611
0.6491	Remote Similarity	NPC471385
0.6455	Remote Similarity	NPC166422
0.6442	Remote Similarity	NPC79718
0.6392	Remote Similarity	NPC127853
0.6364	Remote Similarity	NPC133818
0.6321	Remote Similarity	NPC324875
0.6321	Remote Similarity	NPC292677
0.6311	Remote Similarity	NPC180550
0.6311	Remote Similarity	NPC35405
0.63	Remote Similarity	NPC114441
0.63	Remote Similarity	NPC127056
0.6277	Remote Similarity	NPC286347
0.6263	Remote Similarity	NPC12288
0.625	Remote Similarity	NPC473538
0.62	Remote Similarity	NPC56713
0.619	Remote Similarity	NPC73829
0.6095	Remote Similarity	NPC139044
0.6095	Remote Similarity	NPC471383
0.6082	Remote Similarity	NPC294112
0.6018	Remote Similarity	NPC219180
0.6	Remote Similarity	NPC280941
0.6	Remote Similarity	NPC235772
0.5963	Remote Similarity	NPC488209
0.5905	Remote Similarity	NPC114304
0.59	Remote Similarity	NPC164194
0.5877	Remote Similarity	NPC251263
0.5769	Remote Similarity	NPC472949
0.5769	Remote Similarity	NPC488516
0.5729	Remote Similarity	NPC57362
0.5728	Remote Similarity	NPC25605
0.5714	Remote Similarity	NPC22956
0.5698	Remote Similarity	NPC480946
0.5698	Remote Similarity	NPC130577
0.5698	Remote Similarity	NPC142415
0.5698	Remote Similarity	NPC102683
0.5688	Remote Similarity	NPC119794
0.5682	Remote Similarity	NPC120840
0.5673	Remote Similarity	NPC109079
0.5667	Remote Similarity	NPC161717
0.5632	Remote Similarity	NPC270768
0.5632	Remote Similarity	NPC59263
0.5632	Remote Similarity	NPC210106
0.5596	Remote Similarity	NPC257468
0.5545	Remote Similarity	NPC488515
0.5508	Remote Similarity	NPC54636
0.5455	Remote Similarity	NPC31839
0.5446	Remote Similarity	NPC323359
0.5446	Remote Similarity	NPC477191
0.5437	Remote Similarity	NPC22676
0.5435	Remote Similarity	NPC96580
0.5398	Remote Similarity	NPC488564
0.5398	Remote Similarity	NPC477192
0.5393	Remote Similarity	NPC158141
0.5393	Remote Similarity	NPC110308
0.5392	Remote Similarity	NPC191410
0.5391	Remote Similarity	NPC476992
0.5385	Remote Similarity	NPC471384
0.5377	Remote Similarity	NPC173583
0.5377	Remote Similarity	NPC480424
0.5351	Remote Similarity	NPC475486
0.534	Remote Similarity	NPC475472
0.534	Remote Similarity	NPC475611
0.5333	Remote Similarity	NPC298554
0.5304	Remote Similarity	NPC62725
0.5283	Remote Similarity	NPC475516
0.5281	Remote Similarity	NPC275809
0.5278	Remote Similarity	NPC80843
0.5259	Remote Similarity	NPC288205
0.5259	Remote Similarity	NPC51465
0.5222	Remote Similarity	NPC231063
0.5222	Remote Similarity	NPC282395
0.5196	Remote Similarity	NPC256798
0.5185	Remote Similarity	NPC295371
0.5175	Remote Similarity	NPC75318
0.5165	Remote Similarity	NPC200752
0.5147	Remote Similarity	NPC264270
0.5135	Remote Similarity	NPC473383
0.5111	Remote Similarity	NPC182797
0.5111	Remote Similarity	NPC282616
0.5111	Remote Similarity	NPC84319
0.5111	Remote Similarity	NPC52021
0.5111	Remote Similarity	NPC52169
0.5111	Remote Similarity	NPC488562
0.5111	Remote Similarity	NPC599947
0.5057	Remote Similarity	NPC604575
0.5055	Remote Similarity	NPC481360
0.5053	Remote Similarity	NPC474727
0.5048	Remote Similarity	NPC189884
0.5048	Remote Similarity	NPC138334
0.5048	Remote Similarity	NPC480938
0.5043	Remote Similarity	NPC11242

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC82882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6391
0.1-0.2	2705
0.2-0.3	45
0.3-0.4	8
0.4-0.5	0
0.5-0.6	1
0.6-0.7	0
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
0.5283	Remote Similarity	NPD8295	Clinical (unspecified phase)

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