NPASS Compound

Natural Product: NPC116857

Natural Product ID	NPC116857
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QVBKGGLCKCDNHS-QAGBWMQISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101682282
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 136143 0 0 0 0 0 0 0 0999 V2000 -6.3005 -4.8139 -0.0849 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5769 -4.1111 -1.2121 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4731 -3.8430 -2.4027 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1635 -2.5264 -2.3156 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2919 -1.4171 -1.8246 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5599 -1.8582 -0.5912 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8574 -3.0169 -0.8278 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5792 -0.9125 -0.1988 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8315 -0.4639 1.0612 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9173 1.0211 1.2429 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4602 1.2420 2.6432 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4159 0.5563 3.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4001 -0.8112 3.3302 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8376 -1.0609 2.0840 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5663 -0.5740 1.9630 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6244 -1.5554 1.6725 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0289 -1.3933 0.3049 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1421 -0.2026 0.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9152 -0.0886 1.2518 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6137 1.1530 2.0153 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8251 -1.3430 2.0846 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9433 -1.2840 3.0693 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2229 -1.5493 2.2703 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4508 -0.3636 1.3826 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8937 0.7628 2.2396 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2424 -0.1186 0.5447 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3832 1.0050 -0.4291 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7744 1.3269 -0.7755 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8291 0.5845 -0.4089 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1564 1.0750 -0.8592 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3036 0.8652 -2.3717 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6921 1.2058 -2.7981 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7680 0.8241 -4.2923 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0063 2.6667 -2.7176 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7084 0.3276 -2.1110 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2264 -0.2974 -0.8423 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3324 0.6255 -0.0837 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8670 -0.0168 1.2232 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8484 -1.0748 1.0322 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5901 -0.6473 0.3902 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1463 -1.6988 -0.6204 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1774 1.7776 0.3930 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3723 1.8507 0.1280 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5860 2.7789 1.1504 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5037 -1.6510 2.6756 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7990 -0.9202 3.9493 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4538 -3.1477 3.0498 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6837 -3.5354 3.5905 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6569 0.6026 2.8786 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5923 1.6195 0.2471 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9410 2.6195 -0.4339 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7700 2.2268 -1.8867 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5019 3.6298 -2.4758 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5017 4.4225 -1.6606 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1023 5.8434 -1.4212 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9514 5.9354 -0.6502 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7600 3.7187 -0.5129 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7336 3.6687 -3.8280 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6240 1.4864 -2.0649 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1347 -0.3312 -1.5433 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3301 -2.6798 -1.5726 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7191 -3.9627 -3.5796 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1698 -5.9335 -0.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9003 -4.5416 0.9143 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3992 -4.6628 -0.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8210 -4.8629 -1.5915 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2337 -4.6453 -2.4397 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5032 -2.2480 -3.3529 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5503 -1.1644 -2.5954 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2654 -1.9851 0.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8128 -0.8998 1.4365 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8880 1.4660 1.2792 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4374 2.3067 2.9513 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4361 1.0151 3.2296 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5659 0.8519 4.5867 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9064 -2.1611 1.9142 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2303 -2.5117 1.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5556 -2.3377 -0.0393 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8784 -1.2325 -0.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8229 0.6995 0.1424 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2808 -0.2416 -0.8606 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4688 1.4601 1.8739 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1813 2.0526 1.7356 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7021 1.0712 3.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0680 -2.1911 1.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0239 -0.3557 3.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8455 -2.1026 3.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0831 -2.5041 1.7771 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0067 -1.6654 3.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4135 1.5807 1.7531 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0956 1.1992 2.8750 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5960 0.3290 3.0067 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1657 -1.0499 -0.1092 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8772 1.9473 -0.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8988 0.7576 -1.4283 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0002 2.2255 -1.3709 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1239 2.2041 -0.7618 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0760 -0.1613 -2.6723 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6071 1.5599 -2.8847 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4077 1.6721 -4.8877 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2512 -0.1156 -4.4829 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8500 0.7037 -4.5333 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8671 3.1098 -3.7325 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0699 2.7822 -2.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4077 3.2249 -1.9679 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6148 0.9522 -1.9124 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0668 -0.4889 -2.8041 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1538 -0.4293 -0.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7622 -1.2977 -1.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7940 -0.5263 1.6240 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6522 0.7858 1.9159 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3339 -1.8614 0.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7362 -1.6019 2.0103 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5778 -2.5205 -0.1936 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1071 -2.1528 -1.0009 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6515 -1.2431 -1.4939 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1130 3.3467 1.8156 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1231 -0.8112 4.5514 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4833 -1.5691 4.5689 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3414 0.0225 3.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1696 -3.7695 2.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2852 -3.2995 3.8501 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8167 -4.4919 3.4005 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3593 1.1998 3.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9177 2.8215 -0.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6607 1.8040 -2.3487 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 3.9836 -2.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4407 4.4506 -2.2883 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9530 6.3123 -0.8524 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0346 6.3928 -2.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0702 6.6852 -0.0130 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1658 4.5067 -4.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8408 2.0901 -2.1774 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5096 -0.0619 -2.4349 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8546 -3.3926 -2.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9961 -4.6327 -3.3592 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 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 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 6 37 42 1 1 42 43 2 0 42 44 1 0 21 45 1 0 45 46 1 1 45 47 1 0 47 48 1 0 11 49 1 0 10 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 53 58 1 0 52 59 1 0 5 60 1 0 4 61 1 0 3 62 1 0 7 2 1 0 14 9 1 0 45 16 1 0 57 51 1 0 26 19 1 0 40 29 1 0 40 24 1 0 37 30 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 6 3 67 1 6 4 68 1 6 5 69 1 6 6 70 1 1 9 71 1 1 10 72 1 1 11 73 1 1 12 74 1 0 12 75 1 0 14 76 1 6 16 77 1 6 17 78 1 0 17 79 1 0 18 80 1 0 18 81 1 0 20 82 1 0 20 83 1 0 20 84 1 0 21 85 1 6 22 86 1 0 22 87 1 0 23 88 1 0 23 89 1 0 25 90 1 0 25 91 1 0 25 92 1 0 26 93 1 6 27 94 1 0 27 95 1 0 28 96 1 0 30 97 1 6 31 98 1 0 31 99 1 0 33100 1 0 33101 1 0 33102 1 0 34103 1 0 34104 1 0 34105 1 0 35106 1 0 35107 1 0 36108 1 0 36109 1 0 38110 1 0 38111 1 0 39112 1 0 39113 1 0 41114 1 0 41115 1 0 41116 1 0 44117 1 0 46118 1 0 46119 1 0 46120 1 0 47121 1 0 47122 1 0 48123 1 0 49124 1 0 51125 1 1 52126 1 6 53127 1 6 54128 1 6 55129 1 0 55130 1 0 56131 1 0 58132 1 0 59133 1 0 60134 1 0 61135 1 0 62136 1 0 M END

Standard InCHIKey	QVBKGGLCKCDNHS-QAGBWMQISA-N
Standard InCHI	InChI=1S/C46H74O16/c1-22-30(50)32(52)34(54)37(58-22)62-36-35(61-38-33(53)31(51)26(19-47)59-38)25(49)20-57-39(36)60-29-11-12-42(4)27(43(29,5)21-48)10-13-45(7)28(42)9-8-23-24-18-41(2,3)14-16-46(24,40(55)56)17-15-44(23,45)6/h8,22,24-39,47-54H,9-21H2,1-7H3,(H,55,56)/t22-,24-,25-,26-,27+,28+,29-,30-,31-,32+,33+,34+,35-,36+,37-,38-,39+,42-,43-,44+,45+,46-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](CO[C@@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O)[C@]1(C)CO)O)O[C@H]1[C@@H]([C@H]([C@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	882.5	Volume:	871.091 ? Van der Waals volume.
Dense:	1.013	LogP:	1.62 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.103 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.887 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	44.0
TPSA:	254.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	8.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.119	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.195	Fsp³:	0.935
MCE-18:	168.607 ? 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:	0.914	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.199	Promiscuous compounds:	0.136

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.642	MDCK Permeability:	-5.089
Pgp-inhibitor:	0.0	Pgp-substrate:	0.027
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):	0.033
20% Bioavailability (F20%):	0.282	30% Bioavailability (F30%):	0.603
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.514
Plasma Protein Binding (PPB):	79.724%	Volume Distribution (VD):	-0.489
Fu:	12.894% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.0
BSEP inhibitor:	0.022

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:	0.575	CYP3A4-substrate:	0.107
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.049
HLM stability:	0.0 ? 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):

0.102

Half-life (T1/2):

3.1

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.025
Human Hepatotoxicity (H-HT):	0.688	Drug-induced Liver Injury (DILI):	0.921
AMES Toxicity:	0.557	Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	0.999
Carcinogencity:	0.214	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.037
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.996
Hematotoxicity:	0.483	Drug-induced Nephrotoxicity:	0.985
Genotoxicity:	0.411	RPMI-8226 Immunitoxicity:	0.15
A549 Cytotoxicity:	0.305	Hek293 Cytotoxicity:	0.242
BCF:	0.948 ? 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:	3.466 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.974 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.019 ? 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
NPO11357	Nephelium lappaceum	Species	Sapindaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[16180821]
NPO5258	Fagara zanthoxyloides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22472691]
NPO21322	Plinia cauliflora	Species	Myrtaceae	Eukaryota	leaves	n.a.	n.a.	PMID[32706260]
NPO11357	Nephelium lappaceum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO358	Uncaria guianensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4307	Canarium album	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6469	Clematis angustifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5258	Fagara zanthoxyloides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3619	Ilex hainanensis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4676	Melicope sarcococca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5868	Morus rubra	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21322	Plinia cauliflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10396	Pteris australis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1933	Sideritis nutans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO816	Stenomesson miniatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12378	Streptomyces blastmyceticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3084	Xylopia brasiliensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11357	Nephelium lappaceum	Species	Sapindaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4307	Canarium album	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO358	Uncaria guianensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO358	Uncaria guianensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4307	Canarium album	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4307	Canarium album	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4307	Canarium album	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5868	Morus rubra	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO816	Stenomesson miniatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21322	Plinia cauliflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO358	Uncaria guianensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1933	Sideritis nutans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10396	Pteris australis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4307	Canarium album	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3084	Xylopia brasiliensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11357	Nephelium lappaceum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12378	Streptomyces blastmyceticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5258	Fagara zanthoxyloides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4676	Melicope sarcococca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3619	Ilex hainanensis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6469	Clematis angustifolia	Species	Ranunculaceae	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 NPC116857 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	22094
0.1-0.2	23374
0.2-0.3	2987
0.3-0.4	907
0.4-0.5	374
0.5-0.6	72
0.6-0.7	34
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	Natural Product ID
0.7895	Intermediate Similarity	NPC174679
0.7895	Intermediate Similarity	NPC279554
0.7604	Intermediate Similarity	NPC12288
0.7526	Intermediate Similarity	NPC59804
0.7363	Intermediate Similarity	NPC204407
0.7353	Intermediate Similarity	NPC139044
0.7172	Intermediate Similarity	NPC56713
0.7143	Intermediate Similarity	NPC276093
0.71	Intermediate Similarity	NPC109079
0.7091	Intermediate Similarity	NPC133818
0.7071	Intermediate Similarity	NPC136877
0.7019	Intermediate Similarity	NPC471383
0.7	Intermediate Similarity	NPC25605
0.6961	Remote Similarity	NPC22956
0.6931	Remote Similarity	NPC127056
0.6887	Remote Similarity	NPC79718
0.6792	Remote Similarity	NPC257468
0.6737	Remote Similarity	NPC28198
0.6737	Remote Similarity	NPC476123
0.6737	Remote Similarity	NPC606107
0.67	Remote Similarity	NPC270667
0.6606	Remote Similarity	NPC323359
0.6606	Remote Similarity	NPC324875
0.6606	Remote Similarity	NPC292677
0.6579	Remote Similarity	NPC251263
0.6577	Remote Similarity	NPC62725
0.6535	Remote Similarity	NPC164194
0.64	Remote Similarity	NPC284807
0.6396	Remote Similarity	NPC488564
0.6348	Remote Similarity	NPC323341
0.6333	Remote Similarity	NPC471385
0.6333	Remote Similarity	NPC161717
0.6293	Remote Similarity	NPC219180
0.625	Remote Similarity	NPC488209
0.6238	Remote Similarity	NPC473538
0.6226	Remote Similarity	NPC472949
0.6226	Remote Similarity	NPC488561
0.6204	Remote Similarity	NPC114304
0.6186	Remote Similarity	NPC54636
0.6147	Remote Similarity	NPC46665
0.6132	Remote Similarity	NPC114441
0.6102	Remote Similarity	NPC100639
0.6061	Remote Similarity	NPC283849
0.6036	Remote Similarity	NPC481082
0.6036	Remote Similarity	NPC164419
0.6	Remote Similarity	NPC104400
0.6	Remote Similarity	NPC10320
0.5982	Remote Similarity	NPC119794
0.59	Remote Similarity	NPC57362
0.5882	Remote Similarity	NPC166422
0.5882	Remote Similarity	NPC100383
0.5872	Remote Similarity	NPC263756
0.5872	Remote Similarity	NPC161674
0.5872	Remote Similarity	NPC80843
0.5856	Remote Similarity	NPC180550
0.5856	Remote Similarity	NPC35405
0.5714	Remote Similarity	NPC191410
0.5676	Remote Similarity	NPC469945
0.5664	Remote Similarity	NPC68175
0.5641	Remote Similarity	NPC475486
0.5631	Remote Similarity	NPC286347
0.5631	Remote Similarity	NPC31839
0.562	Remote Similarity	NPC155410
0.5556	Remote Similarity	NPC187618
0.5487	Remote Similarity	NPC117714
0.5478	Remote Similarity	NPC73829
0.5472	Remote Similarity	NPC294112
0.5462	Remote Similarity	NPC280941
0.5462	Remote Similarity	NPC235772
0.5439	Remote Similarity	NPC473383
0.5385	Remote Similarity	NPC177246
0.5378	Remote Similarity	NPC36831
0.5372	Remote Similarity	NPC313110
0.537	Remote Similarity	NPC475472
0.537	Remote Similarity	NPC475611
0.5357	Remote Similarity	NPC6377
0.5357	Remote Similarity	NPC208381
0.5339	Remote Similarity	NPC218954
0.5333	Remote Similarity	NPC480939
0.5319	Remote Similarity	NPC270768
0.5319	Remote Similarity	NPC59263
0.5319	Remote Similarity	NPC210106
0.5289	Remote Similarity	NPC288205
0.5289	Remote Similarity	NPC51465
0.5289	Remote Similarity	NPC476992
0.5246	Remote Similarity	NPC76972
0.5246	Remote Similarity	NPC469782
0.5246	Remote Similarity	NPC204414
0.5238	Remote Similarity	NPC488211
0.5214	Remote Similarity	NPC131469
0.5213	Remote Similarity	NPC480946
0.5213	Remote Similarity	NPC130577
0.5213	Remote Similarity	NPC142415
0.5213	Remote Similarity	NPC102683
0.5208	Remote Similarity	NPC120840
0.5185	Remote Similarity	NPC475633
0.5169	Remote Similarity	NPC95437
0.5169	Remote Similarity	NPC488515
0.5159	Remote Similarity	NPC47995
0.514	Remote Similarity	NPC242611
0.5128	Remote Similarity	NPC475591
0.5128	Remote Similarity	NPC236870
0.5126	Remote Similarity	NPC114692
0.5126	Remote Similarity	NPC236657
0.5122	Remote Similarity	NPC268184
0.5104	Remote Similarity	NPC231063
0.5104	Remote Similarity	NPC282395
0.5104	Remote Similarity	NPC110308
0.5088	Remote Similarity	NPC488516
0.5086	Remote Similarity	NPC605226
0.5085	Remote Similarity	NPC475504
0.5045	Remote Similarity	NPC22676
0.5045	Remote Similarity	NPC127853
0.5044	Remote Similarity	NPC475296
0.5044	Remote Similarity	NPC108748
0.5043	Remote Similarity	NPC44716
0.5043	Remote Similarity	NPC213674
0.5041	Remote Similarity	NPC120116
0.5038	Remote Similarity	NPC481081

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC116857 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6659
0.1-0.2	2424
0.2-0.3	59
0.3-0.4	8
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