NPASS Compound

Natural Product: NPC588756

Natural Product ID	NPC588756
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{S},3~{S},4~{S},5~{R},6~{R})-6-[[(3~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{S},8~{a}~{S},9~{S},12~{a}~{S},14~{a}~{R},14~{b}~{R})-8,9-dihydroxy-8~{a}-(hydroxymethyl)-4,4,6~{a},6~{b},11,11,14~{b}-heptamethyl-1,2,3,4~{a},5,6,7,8,9,10,12,12~{a},14,14~{a}-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{S},3~{S},4~{S},5~{R},6~{R})-6-[[(3~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{S},8~{a}~{S},9~{S},12~{a}~{S},14~{a}~{R},14~{b}~{R})-8,9-dihydroxy-8~{a}-(hydroxymethyl)-4,4,6~{a},6~{b},11,11,14~{b}-heptamethyl-1,2,3,4~{a},5,6,7,8,9,10,12,12~{a},14,14~{a}-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 125131 0 0 0 0 0 0 0 0999 V2000 9.0769 0.5649 2.0369 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7548 1.0531 0.6372 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3328 2.4567 0.5268 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3609 0.1461 -0.3765 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4282 -0.2957 -1.4667 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1026 0.7680 -2.2798 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1537 -0.9380 -0.9162 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4948 -2.4070 -0.6424 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8896 -3.0366 -1.7977 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2004 -0.9374 -2.1004 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7511 -1.7393 -3.1058 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8607 -1.4411 -1.6666 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2263 -0.4804 -0.7368 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7694 0.7262 -1.5500 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1596 -0.0870 0.3529 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6163 0.4128 1.4509 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1865 0.6284 1.7258 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3327 0.0324 0.6760 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9017 -0.2658 1.0684 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7557 -1.2094 2.2084 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2201 1.0409 1.4691 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4481 1.6933 0.2902 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6011 0.8953 -0.2763 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7713 1.1750 0.3821 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7046 1.7922 -0.4483 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0183 3.0653 -0.0620 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8921 3.2173 0.9706 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1514 3.5252 2.2163 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9019 3.6100 2.1870 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8704 3.7120 3.3878 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7685 2.0186 1.2532 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9486 2.4757 1.8462 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1490 1.3206 -0.0265 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9905 0.2623 0.3032 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2296 0.3639 -0.2987 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2801 0.4845 0.6115 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4870 0.0581 0.0554 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.6022 0.5442 0.9840 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8538 0.1513 0.4875 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5175 -1.4461 -0.0401 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.5727 -1.8073 -0.8948 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1932 -1.9255 -0.5756 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3908 -2.4230 0.4634 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4465 -0.7922 -1.2467 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0542 -0.4083 -2.4362 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8763 0.8802 -0.6897 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0885 0.6289 -2.0652 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2518 -0.5881 -0.2338 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6768 -1.1521 -1.6021 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0056 -1.3453 0.7871 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2290 -0.7160 -0.1973 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7661 -2.0509 -0.6516 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2101 -1.8219 -1.0253 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0146 -1.0956 -0.0066 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5255 -2.0959 0.9965 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6431 -0.2225 0.2764 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2616 1.1725 0.4223 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5419 -0.4418 2.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7751 1.2358 2.5697 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1632 0.4820 2.6611 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4528 2.3110 0.5354 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1025 3.0801 1.3994 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0877 2.9349 -0.4452 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8515 -0.7178 0.1375 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1948 0.6899 -0.8803 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9445 -1.0684 -2.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8593 1.4031 -2.3635 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3033 -2.3972 0.1382 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6610 -2.9659 -0.1987 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8652 -3.2241 -1.7317 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2289 0.0872 -2.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5856 -1.3404 -4.0177 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2212 -1.4783 -2.5972 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9994 -2.4587 -1.2619 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8313 1.6695 -0.9753 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3976 0.8981 -2.4509 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7477 0.5546 -1.9998 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3113 0.7023 2.2578 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0665 1.7530 1.8055 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0012 0.2768 2.7582 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1968 0.8570 -0.0918 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7781 -2.2763 1.9592 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2254 -1.0349 2.7432 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5086 -1.0679 3.0104 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5543 0.8422 2.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9177 1.7610 1.9025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 2.6644 0.6392 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3180 1.9485 -0.4703 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7010 1.2393 -1.3294 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2113 1.8990 -1.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5701 4.0821 0.7081 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4359 4.2933 4.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2554 1.3645 1.9615 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3816 1.6587 2.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6343 2.0468 -0.7063 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2209 1.2933 -0.9084 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6860 0.5108 -0.9336 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6055 1.6422 1.0607 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4530 0.0969 1.9831 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8281 0.1435 -0.5039 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7043 -1.8323 0.9960 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2812 -2.5354 -1.5020 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3503 -2.7503 -1.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6240 -2.8965 0.0089 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4447 -1.1952 -1.5170 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7089 -0.9479 -3.1742 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6275 -0.1154 -0.2638 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0756 0.6491 -2.2112 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8196 -2.2397 -1.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6673 -0.6948 -1.8402 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9791 -0.8282 -2.3886 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3362 -0.7447 1.6586 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4415 -2.2560 1.0687 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9501 -1.7147 0.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5963 0.0052 -0.9966 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2248 -2.2953 -1.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5894 -2.8773 0.0235 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6590 -2.8550 -1.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -1.4107 -2.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8380 -2.9924 0.9723 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5141 -2.5007 0.7352 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5839 -1.7364 2.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0337 -0.7823 1.1793 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8524 1.6463 1.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0845 1.8030 -0.4488 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 5 7 1 0 7 8 1 1 8 9 1 0 7 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 2 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 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 31 32 1 0 31 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 37 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 33 46 1 0 46 47 1 0 23 48 1 0 48 49 1 0 48 50 1 0 48 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 1 15 56 1 0 56 57 1 0 57 2 1 0 56 7 1 0 54 13 1 0 54 18 1 0 51 19 1 0 46 25 1 0 44 35 1 0 1 58 1 0 1 59 1 0 1 60 1 0 3 61 1 0 3 62 1 0 3 63 1 0 4 64 1 0 4 65 1 0 5 66 1 6 6 67 1 0 8 68 1 0 8 69 1 0 9 70 1 0 10 71 1 6 11 72 1 0 12 73 1 0 12 74 1 0 14 75 1 0 14 76 1 0 14 77 1 0 16 78 1 0 17 79 1 0 17 80 1 0 18 81 1 6 20 82 1 0 20 83 1 0 20 84 1 0 21 85 1 0 21 86 1 0 22 87 1 0 22 88 1 0 23 89 1 6 25 90 1 6 27 91 1 6 30 92 1 0 31 93 1 1 32 94 1 0 33 95 1 6 35 96 1 6 37 97 1 6 38 98 1 0 38 99 1 0 39100 1 0 40101 1 1 41102 1 0 42103 1 6 43104 1 0 44105 1 6 45106 1 0 46107 1 1 47108 1 0 49109 1 0 49110 1 0 49111 1 0 50112 1 0 50113 1 0 50114 1 0 51115 1 6 52116 1 0 52117 1 0 53118 1 0 53119 1 0 55120 1 0 55121 1 0 55122 1 0 56123 1 1 57124 1 0 57125 1 0 M END

Standard InCHIKey	VTXFLUJNMHWAAT-XVGDWFOMSA-N
Standard InCHI	InChI=1S/C42H68O15/c1-37(2)14-20-19-8-9-23-39(5)12-11-26(38(3,4)22(39)10-13-40(23,6)41(19,7)16-25(46)42(20,18-44)24(45)15-37)55-36-31(51)32(30(50)33(57-36)34(52)53)56-35-29(49)28(48)27(47)21(17-43)54-35/h8,20-33,35-36,43-51H,9-18H2,1-7H3,(H,52,53)/t20-,21+,22-,23+,24-,25-,26-,27+,28-,29+,30-,31+,32-,33-,35-,36+,39-,40+,41+,42+/m0/s1
SMILES	CC1(C)C[C@H](O)[C@]2(CO)[C@@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	812.46	Volume:	801.673 ? Van der Waals volume.
Dense:	1.013	LogP:	1.81 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.359 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.039 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	39.0
TPSA:	256.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	10.0	Rings:	7.0
Heavy Atoms:	15.0

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:	6.009	Fsp³:	0.929
MCE-18:	156.222 ? 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:	0.765	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? 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:	0.216	Promiscuous compounds:	0.152

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.14	MDCK Permeability:	-5.115
Pgp-inhibitor:	0.0	Pgp-substrate:	0.275
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):	0.011
20% Bioavailability (F20%):	0.095	30% Bioavailability (F30%):	0.432
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.376
Plasma Protein Binding (PPB):	68.92%	Volume Distribution (VD):	-0.547
Fu:	25.519% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.396	BCRP inhibitor:	0.003
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.004
HLM stability:	0.058 ? 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):

0.276

Half-life (T1/2):

3.264

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.004
Human Hepatotoxicity (H-HT):	0.519	Drug-induced Liver Injury (DILI):	0.76
AMES Toxicity:	0.799	Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.089	Skin Sensitization:	1.0
Carcinogencity:	0.612	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.082
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.995
Hematotoxicity:	0.574	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.762	RPMI-8226 Immunitoxicity:	0.09
A549 Cytotoxicity:	0.504	Hek293 Cytotoxicity:	0.341
BCF:	0.547 ? 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:	3.279 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.698 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.721 ? 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
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11274-011-0870-8]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11627-014-9655-8]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	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 NPC588756 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	22478
0.1-0.2	22860
0.2-0.3	3203
0.3-0.4	805
0.4-0.5	347
0.5-0.6	136
0.6-0.7	18
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
0.7526	Intermediate Similarity	NPC159309
0.7526	Intermediate Similarity	NPC86222
0.7451	Intermediate Similarity	NPC11242
0.734	Intermediate Similarity	NPC603870
0.7228	Intermediate Similarity	NPC114484
0.69	Remote Similarity	NPC605226
0.6847	Remote Similarity	NPC21691
0.6757	Remote Similarity	NPC4749
0.6667	Remote Similarity	NPC114441
0.6667	Remote Similarity	NPC44716
0.6635	Remote Similarity	NPC302887
0.6635	Remote Similarity	NPC603832
0.6449	Remote Similarity	NPC477193
0.633	Remote Similarity	NPC480936
0.6321	Remote Similarity	NPC64715
0.6296	Remote Similarity	NPC160452
0.6275	Remote Similarity	NPC157868
0.6216	Remote Similarity	NPC609119
0.6146	Remote Similarity	NPC31839
0.6117	Remote Similarity	NPC6377
0.6117	Remote Similarity	NPC208381
0.6105	Remote Similarity	NPC606107
0.6	Remote Similarity	NPC302543
0.5982	Remote Similarity	NPC25998
0.5981	Remote Similarity	NPC475591
0.5981	Remote Similarity	NPC236870
0.5981	Remote Similarity	NPC118440
0.5979	Remote Similarity	NPC224121
0.5963	Remote Similarity	NPC281148
0.596	Remote Similarity	NPC480937
0.5941	Remote Similarity	NPC1046
0.5909	Remote Similarity	NPC477191
0.5905	Remote Similarity	NPC22956
0.5888	Remote Similarity	NPC40775
0.5888	Remote Similarity	NPC251768
0.5862	Remote Similarity	NPC283417
0.5862	Remote Similarity	NPC200049
0.5849	Remote Similarity	NPC192791
0.581	Remote Similarity	NPC473884
0.581	Remote Similarity	NPC472949
0.581	Remote Similarity	NPC603026
0.5804	Remote Similarity	NPC477194
0.5798	Remote Similarity	NPC265841
0.5769	Remote Similarity	NPC475516
0.5763	Remote Similarity	NPC478597
0.5755	Remote Similarity	NPC76497
0.5752	Remote Similarity	NPC477195
0.5741	Remote Similarity	NPC180550
0.5741	Remote Similarity	NPC35405
0.5726	Remote Similarity	NPC602995
0.5714	Remote Similarity	NPC173583
0.5702	Remote Similarity	NPC484059
0.5702	Remote Similarity	NPC484060
0.5702	Remote Similarity	NPC477196
0.5701	Remote Similarity	NPC75417
0.5676	Remote Similarity	NPC236657
0.5667	Remote Similarity	NPC478596
0.5664	Remote Similarity	NPC187290
0.5631	Remote Similarity	NPC270667
0.563	Remote Similarity	NPC329828
0.5625	Remote Similarity	NPC23275
0.5583	Remote Similarity	NPC470518
0.5556	Remote Similarity	NPC284449
0.5556	Remote Similarity	NPC223301
0.5556	Remote Similarity	NPC242840
0.5556	Remote Similarity	NPC171544
0.5537	Remote Similarity	NPC488308
0.552	Remote Similarity	NPC484063
0.552	Remote Similarity	NPC484064
0.551	Remote Similarity	NPC204407
0.5505	Remote Similarity	NPC114304
0.55	Remote Similarity	NPC286347
0.5492	Remote Similarity	NPC271610
0.5492	Remote Similarity	NPC312650
0.5487	Remote Similarity	NPC301449
0.5487	Remote Similarity	NPC601290
0.5481	Remote Similarity	NPC164194
0.5455	Remote Similarity	NPC164389
0.5431	Remote Similarity	NPC472267
0.5431	Remote Similarity	NPC115656
0.5417	Remote Similarity	NPC47995
0.5398	Remote Similarity	NPC114692
0.5398	Remote Similarity	NPC104372
0.5391	Remote Similarity	NPC475486
0.5385	Remote Similarity	NPC214484
0.5377	Remote Similarity	NPC203354
0.5364	Remote Similarity	NPC117714
0.5364	Remote Similarity	NPC30289
0.5351	Remote Similarity	NPC324875
0.5351	Remote Similarity	NPC292677
0.5328	Remote Similarity	NPC484061
0.5328	Remote Similarity	NPC484062
0.5327	Remote Similarity	NPC235405
0.5321	Remote Similarity	NPC80843
0.5321	Remote Similarity	NPC475171
0.5315	Remote Similarity	NPC11551
0.5315	Remote Similarity	NPC2370
0.531	Remote Similarity	NPC95437
0.5304	Remote Similarity	NPC477192
0.53	Remote Similarity	NPC57362
0.5285	Remote Similarity	NPC476774
0.5283	Remote Similarity	NPC48499
0.5278	Remote Similarity	NPC249848
0.5278	Remote Similarity	NPC127056
0.5278	Remote Similarity	NPC109079
0.5278	Remote Similarity	NPC107966
0.5276	Remote Similarity	NPC488309
0.5268	Remote Similarity	NPC258885
0.5259	Remote Similarity	NPC469947
0.5259	Remote Similarity	NPC480948
0.5246	Remote Similarity	NPC85154
0.5238	Remote Similarity	NPC473481
0.5229	Remote Similarity	NPC39211
0.5225	Remote Similarity	NPC30735
0.5221	Remote Similarity	NPC131469
0.5217	Remote Similarity	NPC218954
0.5214	Remote Similarity	NPC480939
0.5214	Remote Similarity	NPC605294
0.521	Remote Similarity	NPC151543
0.52	Remote Similarity	NPC476779
0.5185	Remote Similarity	NPC25605
0.5182	Remote Similarity	NPC263756
0.5182	Remote Similarity	NPC213674
0.5172	Remote Similarity	NPC187618
0.5169	Remote Similarity	NPC107536
0.5169	Remote Similarity	NPC280029
0.5169	Remote Similarity	NPC9470
0.5143	Remote Similarity	NPC480943
0.5138	Remote Similarity	NPC58448
0.5133	Remote Similarity	NPC235438
0.5128	Remote Similarity	NPC329976
0.5128	Remote Similarity	NPC104137
0.5128	Remote Similarity	NPC26626
0.5126	Remote Similarity	NPC252657
0.5126	Remote Similarity	NPC88311
0.5122	Remote Similarity	NPC82380
0.5122	Remote Similarity	NPC244296
0.512	Remote Similarity	NPC475514
0.5094	Remote Similarity	NPC90856
0.5094	Remote Similarity	NPC480938
0.5088	Remote Similarity	NPC31193
0.5088	Remote Similarity	NPC123796
0.5086	Remote Similarity	NPC606145
0.5083	Remote Similarity	NPC123522
0.5083	Remote Similarity	NPC478600
0.5083	Remote Similarity	NPC478599
0.5082	Remote Similarity	NPC470218
0.5082	Remote Similarity	NPC475140
0.5057	Remote Similarity	NPC311078
0.5047	Remote Similarity	NPC211798
0.5046	Remote Similarity	NPC309780
0.5046	Remote Similarity	NPC108748
0.5043	Remote Similarity	NPC120116
0.5043	Remote Similarity	NPC471435
0.5043	Remote Similarity	NPC471434
0.5041	Remote Similarity	NPC277212
0.5041	Remote Similarity	NPC30279
0.5041	Remote Similarity	NPC473918
0.504	Remote Similarity	NPC476780

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC588756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6864
0.1-0.2	2211
0.2-0.3	70
0.3-0.4	4
0.4-0.5	0
0.5-0.6	1
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
0.5185	Remote Similarity	NPD8295	Clinical (unspecified phase)

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