NPASS Compound

Natural Product: NPC270667

Natural Product ID	NPC270667
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(4As,6Ar,6As,6Br,8Ar,9R,10S,12Ar,14Bs)-10-[(2R,3R,4S,5R,6R)-3,5-Dihydroxy-6-(Hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-9-(Hydroxymethyl)-2,2,6A,6B,9,12A-Hexamethyl-1,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydropicene-4A-Carboxylic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL445211
PubChem CID	21609763
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 124130 0 0 0 0 0 0 0 0999 V2000 6.5051 1.3677 4.6068 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7132 1.9584 3.5949 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8349 0.8667 3.0566 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9907 1.3145 2.0441 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5650 0.2346 1.2455 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4574 0.6311 0.5542 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3228 -0.1445 0.7996 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4367 0.7222 1.6479 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0128 0.4636 1.5039 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3528 0.6922 0.0222 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7228 -0.5029 -0.6494 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7445 -0.6623 -0.4574 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5175 -0.1686 -1.6896 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9966 -2.1869 -0.4151 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5232 -2.8422 -1.5164 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1383 -0.5287 -2.0991 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6055 -0.9781 -2.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3943 0.0922 -1.3987 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8307 0.6462 -0.1438 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4973 1.9844 0.0971 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9569 1.7074 0.1533 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5498 0.6244 -0.3348 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7826 -0.4605 -1.0105 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5773 -1.7003 -0.2418 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5714 -0.8003 -2.2748 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8745 -1.3907 -1.7616 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6958 -0.2540 -1.2323 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0326 0.5805 -0.1825 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3540 0.2662 1.2311 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7930 -0.1146 1.4711 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9010 -0.6055 2.8988 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7208 1.0717 1.3263 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1678 -1.2465 0.5622 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0420 -0.7799 -0.8475 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9362 0.6264 -2.4407 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5477 1.8220 -2.4688 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5943 0.1498 -3.5654 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7288 1.1406 -2.4620 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7680 2.0058 -0.3373 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6928 -0.0380 0.2965 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9162 -0.3381 1.1386 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6650 -0.3168 2.6099 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1767 -1.5262 3.1104 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9401 0.4819 0.7343 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9776 -0.2496 0.1552 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0745 -0.1037 1.0096 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2150 -0.7052 0.4766 C 0 0 2 0 0 0 0 0 0 0 0 0 11.3130 -0.6014 1.4985 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5486 0.7507 1.7667 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6106 0.1831 -0.7084 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5822 -0.0672 -1.7748 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2205 0.2840 -1.2223 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2403 -0.2591 -2.0613 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8050 0.7314 -2.8946 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8997 -0.0545 -1.1283 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3795 -1.0748 -0.5509 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7959 2.0551 5.2631 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3962 2.4024 2.8702 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0757 2.7072 4.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1901 0.5202 3.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4007 -0.6668 1.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6938 -0.9486 1.5089 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6909 0.5812 2.7416 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6378 1.8024 1.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5625 1.2623 2.0474 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3235 -0.5512 1.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2233 -1.3849 -0.1712 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2077 0.6550 -1.4113 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1447 -0.9617 -2.1414 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8601 0.2158 -2.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4294 -2.6149 0.4681 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0452 -2.4276 -0.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2591 -3.7663 -1.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1578 0.4771 -2.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5602 -1.2222 -2.6951 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6073 -1.9604 -1.6095 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9348 -1.0232 -3.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2178 0.0169 0.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1049 2.3771 1.0565 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2361 2.7342 -0.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5564 2.4717 0.6393 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5602 -1.8751 0.1689 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2656 -1.9129 0.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7201 -2.5817 -0.9424 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8507 0.1072 -2.8483 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0434 -1.5219 -2.9148 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4029 -1.7669 -2.6745 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7382 -2.2263 -1.0848 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4654 1.6254 -0.3424 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2001 1.2096 1.8406 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7425 -0.4766 1.7369 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4259 -1.6107 2.9424 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9506 -0.6040 3.2599 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2776 0.0474 3.5576 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7798 0.7478 1.3814 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5687 1.8112 2.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5120 1.6155 0.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4667 -2.0764 0.7498 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2301 -1.5491 0.7165 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7806 0.0634 -0.9865 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3279 -1.5442 -1.6052 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0639 0.7515 -4.2402 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8404 0.5557 -3.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6623 1.6786 -2.2619 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9449 1.8603 -2.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9298 2.6892 0.5511 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3202 2.0000 -0.5066 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2154 2.5431 -1.1722 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8676 0.8631 -0.3540 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2069 -1.4010 0.8902 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6724 -0.1994 3.1062 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9542 -1.3585 4.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7631 -1.3374 0.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0276 -1.7323 0.1401 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1086 -1.1722 2.4167 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2485 -1.0026 1.0663 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7176 0.8316 2.7497 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5334 1.2276 -0.3200 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5902 -1.1520 -2.0266 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1003 1.3921 -1.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4091 0.1096 -2.9738 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2186 1.5925 -2.6128 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0069 -0.0623 -2.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1616 -1.6083 -0.7927 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 6 12 14 1 0 14 15 1 0 11 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 2 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 30 33 1 0 33 34 1 0 27 35 1 6 35 36 2 0 35 37 1 0 18 38 1 6 10 39 1 6 5 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 51 54 1 0 50 55 1 0 40 56 1 0 42 3 1 0 52 45 1 0 12 7 1 0 23 18 1 0 34 27 1 0 19 10 1 0 28 22 1 0 1 57 1 0 2 58 1 0 2 59 1 0 3 60 1 1 5 61 1 1 7 62 1 1 8 63 1 0 8 64 1 0 9 65 1 0 9 66 1 0 11 67 1 1 13 68 1 0 13 69 1 0 13 70 1 0 14 71 1 0 14 72 1 0 15 73 1 0 16 74 1 0 16 75 1 0 17 76 1 0 17 77 1 0 19 78 1 1 20 79 1 0 20 80 1 0 21 81 1 0 24 82 1 0 24 83 1 0 24 84 1 0 25 85 1 0 25 86 1 0 26 87 1 0 26 88 1 0 28 89 1 6 29 90 1 0 29 91 1 0 31 92 1 0 31 93 1 0 31 94 1 0 32 95 1 0 32 96 1 0 32 97 1 0 33 98 1 0 33 99 1 0 34100 1 0 34101 1 0 37102 1 0 38103 1 0 38104 1 0 38105 1 0 39106 1 0 39107 1 0 39108 1 0 40109 1 6 41110 1 6 42111 1 1 43112 1 0 45113 1 6 47114 1 6 48115 1 0 48116 1 0 49117 1 0 50118 1 1 51119 1 6 52120 1 1 53121 1 0 54122 1 0 55123 1 0 56124 1 0 M END

Standard InCHIKey	XDOWLZLNKGBUOB-PTTHGKMSSA-N
Standard InCHI	InChI=1S/C42H68O14/c1-37(2)13-15-42(36(51)52)16-14-40(5)21(22(42)17-37)7-8-26-38(3)11-10-27(39(4,20-45)25(38)9-12-41(26,40)6)55-35-32(50)33(29(47)24(19-44)54-35)56-34-31(49)30(48)28(46)23(18-43)53-34/h7,22-35,43-50H,8-20H2,1-6H3,(H,51,52)/t22-,23+,24+,25+,26+,27-,28+,29+,30-,31+,32+,33-,34-,35-,38-,39-,40+,41+,42-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	796.46	Volume:	792.883 ? Van der Waals volume.
Dense:	1.005	LogP:	1.225 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.972 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.542 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	39.0
TPSA:	236.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.126	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.833	Fsp³:	0.929
MCE-18:	150.741 ? 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:	0.911	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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.206	Promiscuous compounds:	0.125

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.305	MDCK Permeability:	-5.167
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
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):	0.003
20% Bioavailability (F20%):	0.006	30% Bioavailability (F30%):	0.039
50% Bioavailability (F50%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023	MRP1:	0.18
Plasma Protein Binding (PPB):	78.117%	Volume Distribution (VD):	-0.596
Fu:	14.362% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.924	BCRP inhibitor:	0.002
BSEP inhibitor:	0.041

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.021	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.143	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.441 ? 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):

0.291

Half-life (T1/2):

2.757

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.803	Drug-induced Liver Injury (DILI):	0.935
AMES Toxicity:	0.872	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.548	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.009
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.998
Hematotoxicity:	0.766	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	0.278	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.351	Hek293 Cytotoxicity:	0.131
BCF:	0.735 ? 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:	3.425 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.854 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.949 ? 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
NPO29483	Swartzia schomburgkii	Species	Fabaceae	Eukaryota	n.a.	suriname rainforest	n.a.	PMID[11087583]
NPO29483	Swartzia schomburgkii	Species	Fabaceae	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

Activity Type	# Activity
IC12	3
IC50	1

Activity Type	# Activity
Cell line	1
Organism	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
NPT726	Cell line	M109	Mus musculus	IC50	=	15.5	ug.mL-1	PMID[17461599]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	400.0	ug ml-1	PMID[19188377]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	600.0	ug ml-1	PMID[19188377]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	1000.0	ug ml-1	PMID[17461599]

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 NPC270667 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	21577
0.1-0.2	23337
0.2-0.3	3465
0.3-0.4	943
0.4-0.5	386
0.5-0.6	85
0.6-0.7	36
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8861	High Similarity	NPC204407
0.8072	Intermediate Similarity	NPC606107
0.8043	Intermediate Similarity	NPC114304
0.8	Intermediate Similarity	NPC276093
0.7978	Intermediate Similarity	NPC136877
0.7957	Intermediate Similarity	NPC180550
0.7957	Intermediate Similarity	NPC35405
0.7692	Intermediate Similarity	NPC59804
0.7582	Intermediate Similarity	NPC12288
0.7379	Intermediate Similarity	NPC323341
0.7379	Intermediate Similarity	NPC133818
0.7374	Intermediate Similarity	NPC324875
0.7374	Intermediate Similarity	NPC292677
0.7363	Intermediate Similarity	NPC164194
0.732	Intermediate Similarity	NPC139044
0.7241	Intermediate Similarity	NPC28198
0.7241	Intermediate Similarity	NPC476123
0.7234	Intermediate Similarity	NPC109079
0.7053	Intermediate Similarity	NPC127056
0.7045	Intermediate Similarity	NPC57362
0.6979	Remote Similarity	NPC472949
0.6947	Remote Similarity	NPC174679
0.6947	Remote Similarity	NPC25605
0.6947	Remote Similarity	NPC279554
0.6875	Remote Similarity	NPC114441
0.6848	Remote Similarity	NPC284807
0.6847	Remote Similarity	NPC471385
0.6822	Remote Similarity	NPC166422
0.6822	Remote Similarity	NPC219180
0.6822	Remote Similarity	NPC251263
0.6735	Remote Similarity	NPC22956
0.6733	Remote Similarity	NPC257468
0.6703	Remote Similarity	NPC31839
0.6697	Remote Similarity	NPC54636
0.6667	Remote Similarity	NPC79718
0.6634	Remote Similarity	NPC471383
0.6604	Remote Similarity	NPC476992
0.6538	Remote Similarity	NPC323359
0.6484	Remote Similarity	NPC283849
0.6476	Remote Similarity	NPC488564
0.6465	Remote Similarity	NPC488561
0.6408	Remote Similarity	NPC481082
0.6408	Remote Similarity	NPC164419
0.6346	Remote Similarity	NPC119794
0.6344	Remote Similarity	NPC286347
0.63	Remote Similarity	NPC6377
0.63	Remote Similarity	NPC208381
0.6277	Remote Similarity	NPC100383
0.6263	Remote Similarity	NPC56713
0.6262	Remote Similarity	NPC475486
0.6204	Remote Similarity	NPC62725
0.6146	Remote Similarity	NPC294112
0.6082	Remote Similarity	NPC191410
0.6058	Remote Similarity	NPC104400
0.6058	Remote Similarity	NPC10320
0.602	Remote Similarity	NPC475472
0.5983	Remote Similarity	NPC161717
0.5979	Remote Similarity	NPC475633
0.5979	Remote Similarity	NPC473538
0.5922	Remote Similarity	NPC80843
0.5905	Remote Similarity	NPC473383
0.5849	Remote Similarity	NPC258885
0.5798	Remote Similarity	NPC111466
0.5765	Remote Similarity	NPC480946
0.5765	Remote Similarity	NPC130577
0.5765	Remote Similarity	NPC142415
0.5765	Remote Similarity	NPC102683
0.5729	Remote Similarity	NPC177246
0.5728	Remote Similarity	NPC150400
0.5714	Remote Similarity	NPC469945
0.5702	Remote Similarity	NPC471384
0.5698	Remote Similarity	NPC270768
0.5698	Remote Similarity	NPC59263
0.5698	Remote Similarity	NPC210106
0.5648	Remote Similarity	NPC475504
0.5586	Remote Similarity	NPC488209
0.5568	Remote Similarity	NPC120840
0.5524	Remote Similarity	NPC473884
0.5524	Remote Similarity	NPC488516
0.5517	Remote Similarity	NPC275809
0.5505	Remote Similarity	NPC73829
0.549	Remote Similarity	NPC211798
0.5463	Remote Similarity	NPC159309
0.5463	Remote Similarity	NPC86222
0.5455	Remote Similarity	NPC158141
0.5455	Remote Similarity	NPC242611
0.5455	Remote Similarity	NPC110308
0.5421	Remote Similarity	NPC223301
0.5421	Remote Similarity	NPC171544
0.5413	Remote Similarity	NPC118440
0.5393	Remote Similarity	NPC298554
0.5392	Remote Similarity	NPC473481
0.5351	Remote Similarity	NPC480939
0.534	Remote Similarity	NPC22676
0.5326	Remote Similarity	NPC96580
0.5304	Remote Similarity	NPC288205
0.5304	Remote Similarity	NPC51465
0.5288	Remote Similarity	NPC473127
0.5288	Remote Similarity	NPC110656
0.5281	Remote Similarity	NPC231063
0.5281	Remote Similarity	NPC282395
0.5273	Remote Similarity	NPC91838
0.5268	Remote Similarity	NPC114692
0.5268	Remote Similarity	NPC114484
0.5243	Remote Similarity	NPC162354
0.5238	Remote Similarity	NPC603870
0.5225	Remote Similarity	NPC609763
0.5217	Remote Similarity	NPC280941
0.5217	Remote Similarity	NPC235772
0.5196	Remote Similarity	NPC209894
0.5192	Remote Similarity	NPC127853
0.5189	Remote Similarity	NPC108748
0.5189	Remote Similarity	NPC475516
0.5185	Remote Similarity	NPC475171
0.5179	Remote Similarity	NPC95437
0.5179	Remote Similarity	NPC488515
0.5169	Remote Similarity	NPC182797
0.5169	Remote Similarity	NPC282616
0.5169	Remote Similarity	NPC84319
0.5169	Remote Similarity	NPC52021
0.5169	Remote Similarity	NPC52169
0.5169	Remote Similarity	NPC488562
0.5169	Remote Similarity	NPC599947
0.5149	Remote Similarity	NPC40085
0.514	Remote Similarity	NPC480424
0.5133	Remote Similarity	NPC236657
0.5133	Remote Similarity	NPC104372
0.5116	Remote Similarity	NPC604575
0.5111	Remote Similarity	NPC481360
0.5096	Remote Similarity	NPC51947
0.5096	Remote Similarity	NPC475611
0.5096	Remote Similarity	NPC480938
0.5093	Remote Similarity	NPC295371
0.5089	Remote Similarity	NPC131469
0.5056	Remote Similarity	NPC198664
0.5054	Remote Similarity	NPC296164
0.505	Remote Similarity	NPC224121
0.5048	Remote Similarity	NPC76999
0.5045	Remote Similarity	NPC40775
0.5045	Remote Similarity	NPC11551
0.5043	Remote Similarity	NPC187618

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC270667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6701
0.1-0.2	2369
0.2-0.3	67
0.3-0.4	12
0.4-0.5	1
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