NPASS Compound

Natural Product: NPC109731

Natural Product ID	NPC109731
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SWIROVJVGRGSPO-XRBUSOSMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102437251
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene 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 127132 0 0 0 0 0 0 0 0999 V2000 -4.9071 3.6462 -0.0675 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0885 3.0079 -0.6935 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9415 2.1806 -1.7176 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6328 1.8430 -2.2987 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3452 0.4469 -2.5268 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2734 -0.5527 -1.3739 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9415 -1.8557 -2.1312 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1543 -0.2305 -0.4098 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2120 -1.3244 0.6712 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8126 -1.8936 0.7768 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0302 -0.6285 0.4613 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3105 0.3181 1.5746 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7574 -0.2859 -0.8546 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0544 0.8855 -1.3795 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3861 0.4236 -1.7474 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0503 0.2407 -0.4226 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5533 0.2669 -0.4567 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1559 -0.6174 -1.4777 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9783 1.7028 -0.8050 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4644 1.8723 -0.8116 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2198 0.8333 -0.0125 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4631 0.3901 1.1913 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1189 -0.8343 1.7957 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6517 1.5007 2.2393 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0148 0.0795 0.9625 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5547 -1.2078 1.5670 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0231 -1.1072 1.6706 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4330 -0.9170 0.2757 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5969 -2.2454 -0.4053 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3761 1.5138 0.4437 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5331 0.9786 -0.0519 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2969 1.9571 -0.9370 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4485 1.2444 -1.5573 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1870 0.3198 -0.6487 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2442 -0.4075 0.2561 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9042 -1.3096 1.2450 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8712 -1.9373 1.9780 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4509 0.5631 0.9099 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8041 -0.6599 -1.4561 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3795 2.2255 -1.9744 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5162 2.5122 -1.9174 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4819 1.5158 -2.5017 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4495 -0.5188 -0.8262 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2370 -0.9873 0.0342 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7213 0.0471 1.0678 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3631 -0.6827 2.1966 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6163 -2.1076 1.8901 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9231 -2.4589 0.4789 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3904 -2.7863 0.2673 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8490 -3.6740 1.2488 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4399 -1.5885 -0.4567 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6508 -2.9730 2.4697 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5021 -0.0169 2.6761 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6606 0.7931 1.5654 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4359 3.3358 -0.1931 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2488 4.4340 0.6459 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3101 2.9149 0.4757 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3247 4.1901 -0.8511 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8284 1.7334 -2.1455 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8174 2.4229 -1.7725 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6376 2.3580 -3.3210 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5775 0.2129 -3.3013 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2897 0.0378 -3.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6171 -2.6709 -1.5162 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7779 -2.0314 -2.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0683 -1.5812 -2.7802 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4075 0.7702 -0.0061 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6115 -0.9790 1.6167 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8261 -2.1936 0.3541 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5925 -2.2957 1.7657 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7278 -2.6387 -0.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3148 0.7464 1.6220 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6061 1.1685 1.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1935 -0.2099 2.5744 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5231 -1.1562 -1.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9082 1.6287 -0.5584 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8043 1.2547 -2.3222 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3509 -0.4617 -2.3848 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7741 1.1580 0.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8209 -0.0686 -2.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7438 -1.4545 -1.1021 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3212 -0.9530 -2.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5258 2.3333 0.0018 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5984 2.0301 -1.7767 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6729 2.8992 -0.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8399 1.9124 -1.8742 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6082 0.0177 -0.6420 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2283 -0.7714 1.7880 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8635 -0.8195 2.8965 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8607 -1.7724 1.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7196 1.4643 2.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6680 2.4989 1.7883 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5416 1.3569 2.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4432 0.8807 1.5328 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8984 -1.2514 2.6164 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8778 -2.1196 1.0752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8270 -0.2808 2.3470 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6435 -2.0730 2.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1319 -2.3345 -1.3809 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2255 -3.0164 0.3350 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6788 -2.5362 -0.5060 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2922 0.1050 -0.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7187 2.7193 -0.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1720 0.7139 -2.5045 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9934 0.8205 -0.0673 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5443 -1.0177 -0.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4940 -0.7524 1.9969 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4665 -2.0904 0.7143 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5260 -1.3707 2.6982 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7734 -0.6981 -1.3288 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8720 1.9292 -2.7929 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8943 2.3336 -2.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3708 2.4922 -2.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8406 -1.8001 0.6696 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5263 0.6672 0.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6496 -0.6621 3.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5558 -2.3841 2.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3849 -3.4399 0.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5394 -3.3354 -0.7026 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0341 -1.8997 0.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7246 -4.6155 0.9496 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5944 -3.7576 1.8571 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2663 -0.6460 2.5109 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7359 0.8584 2.5371 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5629 3.0472 0.8680 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6885 4.4116 -0.3174 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2259 2.7814 -0.7661 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 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 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 21 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 35 38 1 0 34 39 1 0 33 40 1 0 32 41 1 0 14 42 1 0 6 43 1 1 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 48 51 1 0 47 52 1 0 46 53 1 0 45 54 1 0 2 55 1 0 13 8 1 0 28 16 1 0 38 31 1 0 51 44 1 0 28 11 1 0 25 17 1 0 1 56 1 0 1 57 1 0 1 58 1 0 3 59 1 0 4 60 1 0 4 61 1 0 5 62 1 0 5 63 1 0 7 64 1 0 7 65 1 0 7 66 1 0 8 67 1 1 9 68 1 0 9 69 1 0 10 70 1 0 10 71 1 0 12 72 1 0 12 73 1 0 12 74 1 0 13 75 1 6 14 76 1 1 15 77 1 0 15 78 1 0 16 79 1 1 18 80 1 0 18 81 1 0 18 82 1 0 19 83 1 0 19 84 1 0 20 85 1 0 20 86 1 0 21 87 1 6 23 88 1 0 23 89 1 0 23 90 1 0 24 91 1 0 24 92 1 0 24 93 1 0 25 94 1 1 26 95 1 0 26 96 1 0 27 97 1 0 27 98 1 0 29 99 1 0 29100 1 0 29101 1 0 31102 1 6 32103 1 1 33104 1 6 34105 1 1 35106 1 6 36107 1 0 36108 1 0 37109 1 0 39110 1 0 40111 1 0 41112 1 0 42113 1 0 44114 1 1 45115 1 6 46116 1 1 47117 1 1 48118 1 6 49119 1 0 49120 1 0 50121 1 0 52122 1 0 53123 1 0 54124 1 0 55125 1 0 55126 1 0 55127 1 0 M END

Standard InCHIKey	SWIROVJVGRGSPO-XRBUSOSMSA-N
Standard InCHI	InChI=1S/C42H72O13/c1-21(2)10-9-14-42(8,55-37-35(51)33(49)31(47)25(20-44)53-37)22-11-16-41(7)29(22)23(45)18-27-39(5)15-13-28(38(3,4)26(39)12-17-40(27,41)6)54-36-34(50)32(48)30(46)24(19-43)52-36/h10,22-37,43-51H,9,11-20H2,1-8H3/t22-,23+,24+,25+,26-,27+,28+,29-,30+,31+,32-,33-,34+,35+,36-,37-,39-,40+,41+,42-/m0/s1
SMILES	CC(=CCC[C@@](C)([C@H]1CC[C@]2(C)[C@@H]1[C@@H](C[C@@H]1[C@@]3(C)CC[C@H](C(C)(C)[C@@H]3CC[C@@]21C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	784.5	Volume:	795.286 ? Van der Waals volume.
Dense:	0.986	LogP:	3.12 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.469 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.819 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	33.0
TPSA:	218.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.115	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.883	Fsp³:	0.952
MCE-18:	132.927 ? 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:	0.888	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.253	Promiscuous compounds:	0.205

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.228	MDCK Permeability:	-5.071
Pgp-inhibitor:	0.0	Pgp-substrate:	0.077
PAMPA:	0.995 ? 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):	0.063
20% Bioavailability (F20%):	0.021	30% Bioavailability (F30%):	0.802
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219	MRP1:	0.055
Plasma Protein Binding (PPB):	72.457%	Volume Distribution (VD):	-0.458
Fu:	20.69% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.106	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.181	CYP3A4-substrate:	0.054
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.722
HLM stability:	0.034 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.036

Half-life (T1/2):

2.875

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.025
Human Hepatotoxicity (H-HT):	0.599	Drug-induced Liver Injury (DILI):	0.683
AMES Toxicity:	0.933	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.139	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.997
Hematotoxicity:	0.732	Drug-induced Nephrotoxicity:	0.967
Genotoxicity:	0.097	RPMI-8226 Immunitoxicity:	0.146
A549 Cytotoxicity:	0.853	Hek293 Cytotoxicity:	0.335
BCF:	1.791 ? 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:	3.762 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.139 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.421 ? 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
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 17560738]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2015.01.015]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2008-1074888]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10553679]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720520]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12055308]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15070765]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15730262]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	PMID[16462067]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	roots	Gabon	1987	PMID[18327911]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19276083]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20448045]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20509707]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20550123]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20843794]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22194604]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22530813]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22966846]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964677]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24516143]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25028392]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26466957]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26774486]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26938998]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26996316]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27242221]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27807341]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37770099]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8917504]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[97292]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27959	Codonocarpus australis	Species	Gyrostemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28704	Agaricus hortensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28481	Cerbera dilatata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16669	Diospyros verrucosa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28656	Lactobacillus casei	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28161	Stephania sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28691	Streptomyces odorifer	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27867	Turbo argyrostoma	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28481	Cerbera dilatata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20395	Athanasia crithmifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28053	Quercus serrata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29353	Benzoin praecox	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28374	Pleogyne cunninghami	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28073	Crateva nurvala	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28200	Unonopsis glaucopetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16669	Diospyros verrucosa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28704	Agaricus hortensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28131	Polygala amara	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27943	Cardamine pinnata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29115	Rhinella arenarum	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27959	Codonocarpus australis	Species	Gyrostemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28633	Bystropogon origanifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6331	Jacobaea subalpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28656	Lactobacillus casei	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28303	Pleogyne cunninghamii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27990	Schizonepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28670	Mortierella elongata	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25704	Tetraneuris acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28269	Rubus rosa	Species	Rosaceae	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 NPC109731 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	20342
0.1-0.2	24221
0.2-0.3	4099
0.3-0.4	1021
0.4-0.5	110
0.5-0.6	28
0.6-0.7	19
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC31907
0.88	High Similarity	NPC69737
0.8667	High Similarity	NPC208477
0.8243	Intermediate Similarity	NPC157659
0.7917	Intermediate Similarity	NPC66654
0.7831	Intermediate Similarity	NPC208650
0.7647	Intermediate Similarity	NPC220427
0.7407	Intermediate Similarity	NPC181467
0.7386	Intermediate Similarity	NPC14946
0.7386	Intermediate Similarity	NPC63368
0.7229	Intermediate Similarity	NPC269627
0.7191	Intermediate Similarity	NPC159005
0.7143	Intermediate Similarity	NPC135369
0.7105	Intermediate Similarity	NPC234287
0.7105	Intermediate Similarity	NPC88000
0.7105	Intermediate Similarity	NPC4831
0.7105	Intermediate Similarity	NPC472023
0.6875	Remote Similarity	NPC114874
0.6842	Remote Similarity	NPC280825
0.6842	Remote Similarity	NPC473198
0.6842	Remote Similarity	NPC241381
0.6835	Remote Similarity	NPC160734
0.6701	Remote Similarity	NPC488292
0.6701	Remote Similarity	NPC146868
0.6465	Remote Similarity	NPC488294
0.6383	Remote Similarity	NPC246124
0.6304	Remote Similarity	NPC65167
0.625	Remote Similarity	NPC180183
0.625	Remote Similarity	NPC488291
0.6235	Remote Similarity	NPC312553
0.6235	Remote Similarity	NPC8039
0.6235	Remote Similarity	NPC120123
0.618	Remote Similarity	NPC127801
0.618	Remote Similarity	NPC152584
0.6145	Remote Similarity	NPC309425
0.6	Remote Similarity	NPC159036
0.5914	Remote Similarity	NPC208594
0.5872	Remote Similarity	NPC488293
0.5778	Remote Similarity	NPC213190
0.5684	Remote Similarity	NPC476360
0.5684	Remote Similarity	NPC476361
0.5618	Remote Similarity	NPC472987
0.5595	Remote Similarity	NPC473200
0.5568	Remote Similarity	NPC472897
0.5568	Remote Similarity	NPC472896
0.5567	Remote Similarity	NPC160816
0.5521	Remote Similarity	NPC472988
0.5521	Remote Similarity	NPC38217
0.5484	Remote Similarity	NPC472715
0.5422	Remote Similarity	NPC607273
0.5393	Remote Similarity	NPC274833
0.5349	Remote Similarity	NPC43912
0.5341	Remote Similarity	NPC8431
0.5319	Remote Similarity	NPC194842
0.5312	Remote Similarity	NPC234160
0.5275	Remote Similarity	NPC16573
0.5275	Remote Similarity	NPC165033
0.5275	Remote Similarity	NPC273879
0.5269	Remote Similarity	NPC131479
0.5213	Remote Similarity	NPC472719
0.5196	Remote Similarity	NPC472718
0.5146	Remote Similarity	NPC6931
0.5114	Remote Similarity	NPC470312
0.5057	Remote Similarity	NPC131466

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC109731 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7459
0.1-0.2	1615
0.2-0.3	69
0.3-0.4	7
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