NPASS Compound

Natural Product: NPC471426

Natural Product ID	NPC471426
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DCQSTROBYCAYEV-NEDZPZAFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2442980
PubChem CID	46930488
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 184194 0 0 0 0 0 0 0 0999 V2000 -3.7750 -0.7738 -5.9113 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4968 -1.9286 -6.0974 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4256 -2.2188 -4.9725 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8920 -2.4247 -3.7421 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6225 -1.3579 -2.9379 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5107 -0.6722 -3.3855 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6009 -0.3828 -2.3806 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3537 -1.2683 -2.5575 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2250 -0.5170 -2.2813 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4213 0.0083 -0.9180 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1911 1.2343 -1.1685 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1112 1.0318 -2.3654 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4128 1.2752 -3.5623 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8203 1.8757 -0.1422 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2920 3.0111 0.3309 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4438 3.0623 1.6913 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0310 4.1652 2.3489 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1205 4.4745 3.4320 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2778 4.8523 2.7380 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4756 5.2403 3.2536 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5714 5.2504 4.5278 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6516 5.6504 2.4795 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8850 5.4389 1.6111 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4399 5.4856 0.2400 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1159 4.2199 -0.1714 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0867 4.1026 -1.5893 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3956 6.5079 0.1477 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4953 5.7632 1.6058 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8539 0.0931 -0.3876 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2185 -0.9279 0.4410 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2219 -1.7355 -0.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5308 -1.1057 -0.5730 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1023 -0.2847 0.5586 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3149 -0.6233 1.7561 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8267 -0.4329 1.7089 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3078 -1.3862 2.8157 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3499 0.9356 2.0945 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8673 -0.0917 3.0496 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1931 -0.8048 3.2479 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1312 -0.5582 2.1035 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5350 -0.7295 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-5.8263 -0.3774 -2.8794 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9598 -1.1548 -3.4566 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6138 -1.2355 -4.9819 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6794 -1.6924 -5.7008 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2395 -0.7417 -3.2775 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1139 -1.8344 -3.1458 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2077 -1.6446 -3.9349 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9532 -0.5712 -3.5233 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.0138 -0.2078 -4.5625 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6113 -0.7768 -2.1912 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6307 -1.2883 -1.1913 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5041 -2.0879 -1.7220 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9054 -3.4538 -1.6436 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3759 -2.1004 -0.2946 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1075 0.4460 -1.7270 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0992 -0.0244 -1.5943 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0731 1.2901 -1.2374 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9947 1.4382 -0.3572 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2614 2.1277 0.7904 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3352 1.5218 1.6375 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5399 1.1650 0.7902 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3455 1.7732 -0.5786 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3577 3.1694 -0.5277 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6117 -0.2211 0.6028 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7322 2.2959 2.6873 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1540 -0.6796 -6.6794 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8471 -2.8028 -6.3325 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0898 -1.7739 -7.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9326 -3.2042 -5.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5384 -1.6825 -1.8875 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0455 -0.6578 -1.4290 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3363 -1.7432 -3.5293 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3912 -2.0529 -1.7764 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9194 -0.8624 -0.4609 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4063 1.9912 -1.5117 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9814 1.6851 -2.3460 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4893 1.5444 -3.4332 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2837 3.2774 -0.0588 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0782 3.9533 2.9014 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7288 5.2701 4.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3337 3.5486 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-6.5573 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5357 -2.7774 -3.4349 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3065 0.3334 -3.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8705 -0.7126 -5.5189 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9998 -0.5556 -4.1518 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0849 0.8797 -4.6511 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5034 -1.4462 -2.2639 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2770 -0.4447 -0.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5987 -1.9723 -1.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1135 -4.0255 -1.5049 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8334 -2.8998 -0.0858 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4830 0.8803 -1.0876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8671 1.9370 -2.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3112 2.0535 1.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3619 3.2422 0.6579 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9547 0.5559 2.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4991 1.5307 1.1964 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2442 1.4938 -1.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1817 3.4419 -0.0380 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7055 -0.6120 0.6803 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7213 2.3884 2.6766 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 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 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 1 0 14 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 2 0 20 22 1 0 17 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 10 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 35 36 1 0 35 37 1 0 34 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 6 45 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 52 54 1 0 52 55 1 0 55 56 1 0 49 57 1 1 57 58 1 0 48 59 1 0 40 60 1 6 33 61 1 6 5 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 63 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 0 69 71 1 0 71 72 1 0 72 73 1 0 73 74 1 0 72 75 1 0 71 76 1 0 62 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 82 85 1 0 81 86 1 0 64 3 1 0 73 67 1 0 83 78 1 0 12 7 1 0 25 15 1 0 35 30 1 0 45 40 1 0 56 49 1 0 41 33 1 0 44 58 1 1 50 44 1 0 1 87 1 0 2 88 1 0 2 89 1 0 3 90 1 6 5 91 1 1 7 92 1 1 8 93 1 0 8 94 1 0 10 95 1 1 11 96 1 6 12 97 1 1 13 98 1 0 15 99 1 1 17100 1 1 18101 1 0 18102 1 0 22103 1 0 22104 1 0 22105 1 0 23106 1 1 24107 1 6 25108 1 1 26109 1 0 27110 1 0 28111 1 0 30112 1 1 31113 1 0 31114 1 0 32115 1 0 32116 1 0 34117 1 1 36118 1 0 36119 1 0 36120 1 0 37121 1 0 37122 1 0 37123 1 0 38124 1 0 38125 1 0 39126 1 0 39127 1 0 41128 1 6 42129 1 0 42130 1 0 43131 1 0 43132 1 0 46133 1 0 46134 1 0 46135 1 0 47136 1 0 47137 1 0 48138 1 1 50139 1 6 51140 1 0 51141 1 0 53142 1 0 53143 1 0 53144 1 0 54145 1 0 54146 1 0 54147 1 0 55148 1 0 55149 1 0 56150 1 0 56151 1 0 57152 1 0 57153 1 0 59154 1 0 60155 1 0 60156 1 0 60157 1 0 61158 1 0 61159 1 0 61160 1 0 62161 1 6 63162 1 1 64163 1 6 65164 1 0 67165 1 6 69166 1 1 70167 1 0 70168 1 0 70169 1 0 71170 1 6 72171 1 1 73172 1 1 74173 1 0 75174 1 0 76175 1 0 78176 1 6 80177 1 0 80178 1 0 81179 1 1 82180 1 1 83181 1 6 84182 1 0 85183 1 0 86184 1 0 M END

Standard InCHIKey	DCQSTROBYCAYEV-NEDZPZAFSA-N
Standard InCHI	InChI=1S/C60H98O26/c1-25-36(65)41(70)44(73)50(79-25)84-46-39(68)28(20-61)80-53(48(46)86-49-43(72)37(66)27(63)21-76-49)82-30-23-77-52(47(40(30)69)85-51-45(74)42(71)38(67)29(81-51)22-75-26(2)62)83-35-12-13-56(7)31(55(35,5)6)10-14-57(8)32(56)11-15-60-33-18-54(3,4)16-17-59(33,24-78-60)34(64)19-58(57,60)9/h25,27-53,61,63-74H,10-24H2,1-9H3/t25-,27+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39+,40-,41+,42-,43+,44+,45+,46-,47+,48+,49-,50-,51-,52-,53-,56-,57+,58-,59+,60-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CO[C@H]([C@@H]([C@H]2O)O[C@@H]2O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]2O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC[C@]34[C@@]2(C)C[C@H]([C@@]2([C@H]4CC(C)(C)CC2)CO3)O)C)C)[C@@H]([C@H]([C@@H]1O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1234.63	Volume:	1178.104 ? Van der Waals volume.
Dense:	1.048	LogP:	0.042 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.854 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.995 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	60.0
TPSA:	390.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	13.0	Rings:	11.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.073	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.238	Fsp³:	0.983
MCE-18:	315.958 ? 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:	0.915	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.282	Promiscuous compounds:	0.194

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.355	MDCK Permeability:	-5.148
Pgp-inhibitor:	0.0	Pgp-substrate:	0.977
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):	0.087
20% Bioavailability (F20%):	0.071	30% Bioavailability (F30%):	0.98
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.004
Plasma Protein Binding (PPB):	63.022%	Volume Distribution (VD):	-0.359
Fu:	23.17% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.004
BSEP inhibitor:	0.0

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:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.497
HLM stability:	0.059 ? 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):

-0.709

Half-life (T1/2):

3.869

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.358	Drug-induced Liver Injury (DILI):	0.754
AMES Toxicity:	0.972	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.006	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.374	Drug-induced Nephrotoxicity:	0.956
Genotoxicity:	0.014	RPMI-8226 Immunitoxicity:	0.342
A549 Cytotoxicity:	0.824	Hek293 Cytotoxicity:	0.401
BCF:	1.319 ? 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:	3.846 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.603 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.729 ? 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
NPO32586	ardisia gigantifolia stapf.	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24095094]
NPO32586	ardisia gigantifolia stapf.	Species	Primulaceae	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
IC50	3

Activity Type	# Activity
Cell line	3

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
NPT180	Cell line	HCT-8	Homo sapiens	IC50	=	9280.0	nM	PubChem BioAssay data set
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	8400.0	nM	DOI[10.6019/CHEMBL1201861]
NPT81	Cell line	A549	Homo sapiens	IC50	=	8060.0	nM	DailyMed

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 NPC471426 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	27895
0.1-0.2	19078
0.2-0.3	1971
0.3-0.4	645
0.4-0.5	217
0.5-0.6	7
0.6-0.7	18
0.7-0.8	0
0.8-0.85	6
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC471431
0.9174	High Similarity	NPC471425
0.8772	High Similarity	NPC471427
0.8596	High Similarity	NPC231566
0.8509	High Similarity	NPC471429
0.8421	Intermediate Similarity	NPC189575
0.8378	Intermediate Similarity	NPC209798
0.8246	Intermediate Similarity	NPC262567
0.8205	Intermediate Similarity	NPC106701
0.8158	Intermediate Similarity	NPC205129
0.8136	Intermediate Similarity	NPC471424
0.7768	Intermediate Similarity	NPC77717
0.7724	Intermediate Similarity	NPC471428
0.7679	Intermediate Similarity	NPC253611
0.7679	Intermediate Similarity	NPC488782
0.7561	Intermediate Similarity	NPC471626
0.7431	Intermediate Similarity	NPC18724
0.7265	Intermediate Similarity	NPC138219
0.7265	Intermediate Similarity	NPC475234
0.7203	Intermediate Similarity	NPC473688
0.712	Intermediate Similarity	NPC471430
0.7094	Intermediate Similarity	NPC471373
0.7094	Intermediate Similarity	NPC40716
0.704	Intermediate Similarity	NPC22709
0.7009	Intermediate Similarity	NPC267238
0.6957	Remote Similarity	NPC171741
0.6917	Remote Similarity	NPC471375
0.687	Remote Similarity	NPC323231
0.6842	Remote Similarity	NPC158051
0.6754	Remote Similarity	NPC224003
0.6721	Remote Similarity	NPC51579
0.6694	Remote Similarity	NPC475630
0.6667	Remote Similarity	NPC148593
0.65	Remote Similarity	NPC158367
0.6457	Remote Similarity	NPC66513
0.6423	Remote Similarity	NPC273189
0.6417	Remote Similarity	NPC119628
0.6371	Remote Similarity	NPC471374
0.6349	Remote Similarity	NPC126753
0.6341	Remote Similarity	NPC184805
0.6311	Remote Similarity	NPC470623
0.6048	Remote Similarity	NPC207693
0.6	Remote Similarity	NPC157571
0.5522	Remote Similarity	NPC470622
0.5267	Remote Similarity	NPC87393
0.5154	Remote Similarity	NPC267637
0.5078	Remote Similarity	NPC157474
0.5074	Remote Similarity	NPC607904
0.5068	Remote Similarity	NPC250247
0.5039	Remote Similarity	NPC30289

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471426 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7856
0.1-0.2	1261
0.2-0.3	31
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
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
		NPD

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