NPASS Compound

Natural Product: NPC191998

Natural Product ID	NPC191998
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CUPUFOPSEXRTQZ-DPWNYAQNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101630650
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 132140 0 0 0 0 0 0 0 0999 V2000 12.9035 0.8404 1.8404 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4242 0.3779 0.4962 C 0 0 2 0 0 0 0 0 0 0 0 0 11.7005 1.4638 -0.2755 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6261 0.7599 -1.1106 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5469 0.3093 -0.1506 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5739 -0.6695 -0.7776 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9763 -2.1113 -0.5562 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3405 -0.4023 0.0379 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5504 1.0318 0.5363 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4412 1.8306 -0.1740 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3731 0.8216 -0.1408 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0779 1.1029 -0.7827 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6264 2.4788 -0.4152 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2176 2.6071 -0.9480 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8802 3.4408 -1.7372 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2984 1.5716 -0.3728 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1260 1.8558 -0.6959 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9909 0.9656 0.1756 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1708 -0.0327 0.9498 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8644 -0.7412 0.1547 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7331 0.1746 -0.6742 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4679 -0.1858 -2.1326 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1524 -0.0031 -0.2986 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7528 -1.3044 -0.8390 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1307 -1.5626 -0.3287 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0575 -0.4277 -0.7007 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2457 -0.3490 -2.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9626 0.3961 -0.6013 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2213 0.8166 -0.1840 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9083 1.6641 -1.2097 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3937 1.6418 -1.1491 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7853 0.1626 -1.0541 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2641 -0.2775 0.2568 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7647 -1.6948 0.5470 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3403 -2.1602 1.7914 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8022 -1.4679 2.8663 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5307 -2.2949 3.9043 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0261 -1.3046 4.9546 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9057 -0.4281 5.4564 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1927 0.2153 4.3069 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7077 -0.7952 3.4698 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0338 -1.1355 6.2792 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5570 -1.9779 6.0638 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6591 -2.8365 3.2944 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8813 -0.2520 0.2869 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0701 -0.0599 -1.3942 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2915 -0.7188 -2.5774 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1087 -1.9534 -2.2891 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4637 -1.8526 -2.9923 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9948 -0.4765 -2.6029 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1534 0.5321 -3.3302 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1755 1.8087 -2.4960 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4567 2.3014 -2.3115 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8865 0.1249 -3.4647 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3531 -0.3480 -2.8315 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2954 -2.7953 -2.4031 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4160 -3.0888 -2.6043 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9587 2.2730 -2.2343 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4532 2.9883 -1.1981 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7956 1.4348 0.1721 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1595 -0.2512 0.9635 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4203 -0.7540 0.7057 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8825 0.3505 2.0600 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2028 0.4878 2.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0424 1.9420 1.8751 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2589 0.0269 -0.1466 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1725 2.0767 0.4830 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3504 2.0787 -0.8992 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2056 1.5531 -1.7783 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0505 -0.0709 -1.6922 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4976 -0.4579 -1.8378 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6657 -2.4779 -1.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3563 -2.2517 0.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0376 -2.7288 -0.5939 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2625 -1.0916 0.9081 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3250 1.0833 1.6029 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7460 2.1500 -1.1720 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1726 2.7240 0.4368 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1627 0.5571 0.9329 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0767 1.0501 -1.8899 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6353 2.5596 0.6894 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 3.2088 -0.9425 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4115 1.7034 0.7445 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3434 1.6742 -1.7819 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3045 2.9406 -0.5022 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4600 1.6255 0.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8852 -0.7880 1.3442 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2438 0.4715 1.8430 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3402 -1.5160 -0.4601 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4926 -1.3254 0.8716 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7525 -1.2594 -2.2617 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9684 0.4767 -2.8400 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3536 -0.1802 -2.2590 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2260 -0.0709 0.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0976 -2.1717 -0.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7668 -1.3231 -1.9409 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0972 -1.6664 0.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4898 -2.4980 -0.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7628 -1.2916 -2.4930 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8356 0.5555 -2.4354 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3236 -0.2981 -2.7605 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0645 1.5039 0.6752 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6098 1.2558 -2.2182 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7143 2.1935 -0.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1350 -0.3064 -1.8580 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5819 0.3522 1.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8749 -1.7256 0.5318 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3936 -2.3982 -0.2162 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4930 -0.6366 2.5779 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9013 -3.0455 4.3843 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8126 -0.6378 4.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3689 0.3677 6.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9386 0.8234 3.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3477 0.8248 4.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9646 -0.7328 7.1615 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2137 -1.4148 6.5375 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9766 -2.2008 2.6082 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3195 -1.0364 -3.0404 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3624 -1.9941 -1.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3997 -1.8893 -4.0746 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7587 -0.3468 -1.5069 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6776 0.7145 -4.3080 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5686 2.5839 -3.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6642 1.6211 -1.5352 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9044 1.8717 -1.5501 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8038 -0.3078 -1.9564 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8929 -3.6840 -2.3052 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5090 -3.2643 -3.5735 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7511 1.8021 -3.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7411 3.3687 -2.0848 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4855 -1.3848 -0.1962 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7112 -1.3849 1.5809 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 2 0 14 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 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 18 28 1 0 28 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 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 33 45 1 0 32 46 1 0 46 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 51 54 1 0 50 55 1 0 49 56 1 0 48 57 1 0 31 58 1 0 30 59 1 0 9 60 1 0 5 61 1 1 61 62 1 0 62 2 1 0 60 5 1 0 26 8 1 0 45 29 1 0 54 47 1 0 26 11 1 0 41 36 1 0 23 12 1 0 21 16 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 6 3 67 1 0 3 68 1 0 4 69 1 0 4 70 1 0 6 71 1 6 7 72 1 0 7 73 1 0 7 74 1 0 8 75 1 1 9 76 1 1 10 77 1 0 10 78 1 0 11 79 1 1 12 80 1 6 13 81 1 0 13 82 1 0 16 83 1 1 17 84 1 0 17 85 1 0 18 86 1 1 19 87 1 0 19 88 1 0 20 89 1 0 20 90 1 0 22 91 1 0 22 92 1 0 22 93 1 0 23 94 1 1 24 95 1 0 24 96 1 0 25 97 1 0 25 98 1 0 27 99 1 0 27100 1 0 27101 1 0 29102 1 1 30103 1 6 31104 1 1 32105 1 6 33106 1 1 34107 1 0 34108 1 0 36109 1 6 37110 1 1 38111 1 6 39112 1 1 40113 1 0 40114 1 0 42115 1 0 43116 1 0 44117 1 0 47118 1 6 48119 1 1 49120 1 6 50121 1 1 51122 1 6 52123 1 0 52124 1 0 53125 1 0 55126 1 0 56127 1 0 57128 1 0 58129 1 0 59130 1 0 62131 1 0 62132 1 0 M END

Standard InCHIKey	CUPUFOPSEXRTQZ-DPWNYAQNSA-N
Standard InCHI	InChI=1S/C44H70O18/c1-18-5-10-44(57-15-18)19(2)30-27(62-44)13-23-21-12-25(46)24-11-20(6-8-42(24,3)22(21)7-9-43(23,30)4)58-40-37(54)34(51)38(61-41-36(53)33(50)32(49)28(14-45)59-41)29(60-40)17-56-39-35(52)31(48)26(47)16-55-39/h18-24,26-41,45,47-54H,5-17H2,1-4H3/t18-,19+,20+,21-,22+,23+,24-,26+,27+,28-,29-,30+,31+,32-,33+,34-,35-,36-,37-,38-,39+,40-,41+,42-,43+,44-/m1/s1
SMILES	C[C@@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC(=O)[C@H]6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]4[C@@H]([C@H]([C@H](CO4)O)O)O)O3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	886.46	Volume:	848.159 ? Van der Waals volume.
Dense:	1.045	LogP:	1.15 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.907 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.724 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	49.0
TPSA:	272.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	9.0	Rings:	9.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.133	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.752	Fsp³:	0.977
MCE-18:	231.034 ? 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:	0.662	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.214	Promiscuous compounds:	0.084

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.213	MDCK Permeability:	-5.08
Pgp-inhibitor:	0.001	Pgp-substrate:	0.565
PAMPA:	0.996 ? 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):	0.035
20% Bioavailability (F20%):	0.04	30% Bioavailability (F30%):	0.963
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.019
Plasma Protein Binding (PPB):	49.36%	Volume Distribution (VD):	-0.454
Fu:	43.358% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.225
BSEP inhibitor:	0.016

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:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.71
HLM stability:	0.079 ? 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):

0.4

Half-life (T1/2):

2.893

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.043
Human Hepatotoxicity (H-HT):	0.733	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.986	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.018	Skin Sensitization:	1.0
Carcinogencity:	0.093	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.997
Hematotoxicity:	0.26	Drug-induced Nephrotoxicity:	0.924
Genotoxicity:	0.27	RPMI-8226 Immunitoxicity:	0.39
A549 Cytotoxicity:	0.979	Hek293 Cytotoxicity:	0.93
BCF:	1.139 ? 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:	3.386 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.793 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.029 ? 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
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444689]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785389]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	PMID[33016699]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964794]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23658	Paeonia hybr	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22917	Flustra foliacea	Species	Flustridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24936	Mentha asiatica	Species	Lamiaceae	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 NPC191998 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	23739
0.1-0.2	22748
0.2-0.3	2840
0.3-0.4	347
0.4-0.5	99
0.5-0.6	74
0.6-0.7	10
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
0.75	Intermediate Similarity	NPC107188
0.6887	Remote Similarity	NPC128572
0.6827	Remote Similarity	NPC202898
0.66	Remote Similarity	NPC250393
0.6465	Remote Similarity	NPC325828
0.6465	Remote Similarity	NPC177834
0.6364	Remote Similarity	NPC97700
0.6364	Remote Similarity	NPC30856
0.6321	Remote Similarity	NPC160426
0.6262	Remote Similarity	NPC475351
0.625	Remote Similarity	NPC264101
0.5983	Remote Similarity	NPC132080
0.5941	Remote Similarity	NPC485594
0.5888	Remote Similarity	NPC107962
0.5888	Remote Similarity	NPC215408
0.5882	Remote Similarity	NPC181845
0.5849	Remote Similarity	NPC211354
0.5847	Remote Similarity	NPC233433
0.5776	Remote Similarity	NPC475625
0.5776	Remote Similarity	NPC116756
0.5769	Remote Similarity	NPC234352
0.5763	Remote Similarity	NPC476112
0.5763	Remote Similarity	NPC307534
0.5755	Remote Similarity	NPC206003
0.5755	Remote Similarity	NPC473610
0.5739	Remote Similarity	NPC475319
0.5726	Remote Similarity	NPC232037
0.5714	Remote Similarity	NPC475643
0.5673	Remote Similarity	NPC297348
0.5673	Remote Similarity	NPC249204
0.5673	Remote Similarity	NPC48339
0.5673	Remote Similarity	NPC141769
0.5673	Remote Similarity	NPC477547
0.5641	Remote Similarity	NPC473518
0.5625	Remote Similarity	NPC473601
0.5614	Remote Similarity	NPC51172
0.5614	Remote Similarity	NPC49032
0.5603	Remote Similarity	NPC115165
0.5545	Remote Similarity	NPC470432
0.5545	Remote Similarity	NPC230507
0.5545	Remote Similarity	NPC6295
0.5537	Remote Similarity	NPC31896
0.5526	Remote Similarity	NPC477809
0.552	Remote Similarity	NPC220836
0.5517	Remote Similarity	NPC184617
0.5472	Remote Similarity	NPC80191
0.5447	Remote Similarity	NPC470866
0.5421	Remote Similarity	NPC477451
0.5391	Remote Similarity	NPC92890
0.5378	Remote Similarity	NPC475333
0.5378	Remote Similarity	NPC224098
0.5378	Remote Similarity	NPC208383
0.5345	Remote Similarity	NPC471464
0.5345	Remote Similarity	NPC6806
0.5328	Remote Similarity	NPC477811
0.5294	Remote Similarity	NPC277715
0.528	Remote Similarity	NPC94086
0.528	Remote Similarity	NPC473817
0.5273	Remote Similarity	NPC19400
0.5268	Remote Similarity	NPC485595
0.5234	Remote Similarity	NPC210569
0.5214	Remote Similarity	NPC300557
0.5182	Remote Similarity	NPC121453
0.5169	Remote Similarity	NPC480555
0.5169	Remote Similarity	NPC150372
0.5164	Remote Similarity	NPC108072
0.5145	Remote Similarity	NPC481189
0.5143	Remote Similarity	NPC24960
0.5133	Remote Similarity	NPC125324
0.5122	Remote Similarity	NPC83137
0.512	Remote Similarity	NPC232054
0.5118	Remote Similarity	NPC480556
0.5115	Remote Similarity	NPC305771
0.5115	Remote Similarity	NPC94072
0.5115	Remote Similarity	NPC169816
0.5082	Remote Similarity	NPC232611
0.5049	Remote Similarity	NPC88962
0.5046	Remote Similarity	NPC294686
0.5043	Remote Similarity	NPC113044
0.5043	Remote Similarity	NPC283829
0.5043	Remote Similarity	NPC14704
0.5043	Remote Similarity	NPC161676
0.5043	Remote Similarity	NPC602423
0.5042	Remote Similarity	NPC151134
0.5041	Remote Similarity	NPC470864

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC191998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7247
0.1-0.2	1820
0.2-0.3	74
0.3-0.4	6
0.4-0.5	1
0.5-0.6	0
0.6-0.7	2
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
0.6465	Remote Similarity	NPD8171	Phase 2
0.6132	Remote Similarity	NPD8170	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