NPASS Compound

Natural Product: NPC586434

Natural Product ID	NPC586434
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~{S})-6-[[(3~{S},4~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{a}~{S},12~{a}~{S},14~{a}~{R},14~{b}~{R})-8~{a}-carboxy-4-formyl-4,6~{a},6~{b},11,11,14~{b}-hexamethyl-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~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{S},3~{S},4~{S},5~{R},6~{S})-6-[[(3~{S},4~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{a}~{S},12~{a}~{S},14~{a}~{R},14~{b}~{R})-8~{a}-carboxy-4-formyl-4,6~{a},6~{b},11,11,14~{b}-hexamethyl-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~{R},6~{S})-3,4,5-trihydroxy-6-methyl-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 120126 0 0 0 0 0 0 0 0999 V2000 9.6072 2.4603 2.7536 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0437 2.3473 1.3704 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0387 1.0127 0.9806 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1678 0.8001 -0.1133 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9052 0.6794 0.4148 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3472 -0.5810 0.2227 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0821 -0.5506 -0.5905 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3599 -0.9141 -1.8834 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0429 -1.4339 0.0782 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9264 -1.6094 -0.7327 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7507 -1.1329 -0.1482 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3317 0.0554 -0.9618 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0923 0.4504 -0.7925 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0350 -0.7052 -1.0573 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9376 -1.0617 -2.5029 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4043 -0.2060 -0.6570 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8562 1.0125 -1.3807 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2918 1.2725 -1.2023 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1097 0.4994 -0.4623 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5133 0.9345 -0.4131 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5165 2.2933 0.3034 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8534 2.9716 0.1523 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9166 4.0947 1.1570 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9925 3.5780 -1.2277 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9530 1.9961 0.4601 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3589 0.8021 1.1592 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4815 0.0132 0.1724 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4128 -0.4862 -0.8626 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2863 -0.0996 -2.0412 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4089 -1.3721 -0.5131 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9463 -1.1698 0.9063 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6685 -1.7185 0.3855 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5806 -0.7077 0.2415 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0592 -0.3669 1.6084 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4727 -1.2597 -0.6692 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0911 -1.3740 -2.0471 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0622 -2.5804 -0.1209 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6246 -2.9513 -0.3810 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6883 -1.7853 -0.0987 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7253 -2.2026 0.0096 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1258 -3.3417 -0.9170 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8983 -2.7659 1.3874 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1565 -3.9244 1.6295 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5897 -2.6894 0.3182 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6308 -2.7011 1.2110 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3146 -3.4590 2.4450 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1630 -3.5632 3.3626 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0857 -4.0690 2.6209 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1335 -1.3060 1.5341 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3804 -1.3841 2.1735 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3458 1.9738 -1.0310 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1254 1.6632 -2.3687 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8188 2.3911 -0.9339 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1835 3.2001 -1.9881 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9653 3.0785 0.4123 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6747 4.4252 0.3270 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6456 1.4467 3.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6165 2.9182 2.7353 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9803 3.1409 3.3979 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0267 2.7879 1.3770 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5321 -0.1257 -0.6041 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0959 -1.1818 -0.3318 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7404 0.5206 -0.5954 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1440 -0.2189 -2.5487 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7652 -0.9468 1.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0635 -0.7309 0.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5339 -0.0598 -2.0482 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9472 0.9539 -0.6625 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3262 1.2352 -1.5328 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3366 0.8308 0.2208 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0947 -0.1306 -3.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1114 -1.3577 -2.7098 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5710 -1.8908 -2.8321 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2914 0.0975 0.4289 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3209 1.9116 -0.9494 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6307 1.0433 -2.4546 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6794 2.1674 -1.7258 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7995 1.1942 -1.4762 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7521 2.9676 -0.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2533 2.1902 1.3667 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4336 3.8403 2.1207 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5272 5.0416 0.7248 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9887 4.2777 1.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2024 4.6789 -1.1826 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0881 3.4519 -1.8409 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8633 3.0923 -1.7048 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4681 1.6492 -0.4524 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7365 2.4254 1.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8027 1.0599 2.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2041 0.1390 1.4606 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0898 -1.6394 -1.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8245 -0.9003 1.9798 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6975 -2.0063 0.9020 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8791 -2.3068 -0.5216 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3064 -2.4741 1.1450 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1944 -0.9418 1.9319 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8735 0.7447 1.6300 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8499 -0.5275 2.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9059 -2.4259 -2.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1827 -1.1565 -2.0538 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6445 -0.6897 -2.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2915 -2.7269 0.9547 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6851 -3.3627 -0.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5626 -3.3320 -1.3977 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3628 -3.7372 0.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0324 -1.4143 0.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9308 -3.9618 -0.4165 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6525 -2.9596 -1.8323 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3235 -4.0402 -1.1344 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7844 -2.0894 2.2250 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4732 -3.2337 0.7166 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9320 -4.7432 3.3835 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4210 -0.8371 2.2075 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8673 -2.1194 1.7154 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6806 2.8204 -0.7798 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6698 0.8312 -2.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4045 1.4519 -0.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1853 3.2164 -2.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0049 2.8797 0.7567 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9137 4.7294 -0.5880 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 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 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 6 28 29 2 0 28 30 1 0 27 31 1 0 31 32 1 0 32 33 1 0 33 34 1 1 33 35 1 0 35 36 1 6 35 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 6 40 42 1 0 42 43 2 0 9 44 1 0 44 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 45 49 1 0 49 50 1 0 4 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 53 55 1 0 55 56 1 0 55 2 1 0 49 6 1 0 40 11 1 0 39 14 1 0 35 16 1 0 33 19 1 0 27 20 1 0 1 57 1 0 1 58 1 0 1 59 1 0 2 60 1 1 4 61 1 6 6 62 1 6 7 63 1 6 8 64 1 0 9 65 1 1 11 66 1 1 12 67 1 0 12 68 1 0 13 69 1 0 13 70 1 0 15 71 1 0 15 72 1 0 15 73 1 0 16 74 1 1 17 75 1 0 17 76 1 0 18 77 1 0 20 78 1 6 21 79 1 0 21 80 1 0 23 81 1 0 23 82 1 0 23 83 1 0 24 84 1 0 24 85 1 0 24 86 1 0 25 87 1 0 25 88 1 0 26 89 1 0 26 90 1 0 30 91 1 0 31 92 1 0 31 93 1 0 32 94 1 0 32 95 1 0 34 96 1 0 34 97 1 0 34 98 1 0 36 99 1 0 36100 1 0 36101 1 0 37102 1 0 37103 1 0 38104 1 0 38105 1 0 39106 1 1 41107 1 0 41108 1 0 41109 1 0 42110 1 0 45111 1 6 48112 1 0 49113 1 1 50114 1 0 51115 1 1 52116 1 0 53117 1 1 54118 1 0 55119 1 1 56120 1 0 M END

Standard InCHIKey	OLFGQBKWRYLUAQ-YDFLGPKDSA-N
Standard InCHI	InChI=1S/C42H64O14/c1-20-26(44)27(45)28(46)34(53-20)55-31-29(47)32(33(49)50)56-35(30(31)48)54-25-11-12-38(4)23(39(25,5)19-43)10-13-41(7)24(38)9-8-21-22-18-37(2,3)14-16-42(22,36(51)52)17-15-40(21,41)6/h8,19-20,22-32,34-35,44-48H,9-18H2,1-7H3,(H,49,50)(H,51,52)/t20-,22-,23+,24+,25-,26-,27-,28+,29-,30+,31-,32-,34-,35-,38-,39-,40+,41+,42-/m0/s1
SMILES	C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O[C@H]3CC[C@]4(C)[C@H]5CC=C6[C@@H]7CC(C)(C)CC[C@]7(C(=O)O)CC[C@@]6(C)[C@]5(C)CC[C@H]4[C@]3(C)C=O)O[C@H](C(=O)O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	792.43	Volume:	787.61 ? Van der Waals volume.
Dense:	1.006	LogP:	1.888 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.232 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.866 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	41.0
TPSA:	229.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.112	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.933	Fsp³:	0.881
MCE-18:	154.532 ? 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:	0.91	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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.206	Promiscuous compounds:	0.042

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.966	MDCK Permeability:	-5.204
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
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):	0.004
20% Bioavailability (F20%):	0.179	30% Bioavailability (F30%):	0.062
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.791
Plasma Protein Binding (PPB):	78.103%	Volume Distribution (VD):	-0.541
Fu:	16.364% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.001
BSEP inhibitor:	0.282

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.695
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.494

Half-life (T1/2):

4.613

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.037
Human Hepatotoxicity (H-HT):	0.609	Drug-induced Liver Injury (DILI):	0.847
AMES Toxicity:	0.065	Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.074	Skin Sensitization:	0.881
Carcinogencity:	0.114	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.136
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.984
Hematotoxicity:	0.22	Drug-induced Nephrotoxicity:	0.931
Genotoxicity:	0.633	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.005	Hek293 Cytotoxicity:	0.049
BCF:	0.41 ? 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:	3.616 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.436 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.437 ? 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
NPO1209	Swartzia madagascariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1209	Swartzia madagascariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1209	Swartzia madagascariensis	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

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 NPC586434 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	21027
0.1-0.2	25036
0.2-0.3	2773
0.3-0.4	709
0.4-0.5	221
0.5-0.6	67
0.6-0.7	20
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8778	High Similarity	NPC114441
0.7802	Intermediate Similarity	NPC294112
0.7347	Intermediate Similarity	NPC6377
0.7347	Intermediate Similarity	NPC208381
0.7021	Intermediate Similarity	NPC100383
0.6737	Remote Similarity	NPC286347
0.6729	Remote Similarity	NPC323359
0.6667	Remote Similarity	NPC270667
0.6596	Remote Similarity	NPC204407
0.6526	Remote Similarity	NPC606107
0.6373	Remote Similarity	NPC12288
0.6311	Remote Similarity	NPC174679
0.6311	Remote Similarity	NPC25605
0.6311	Remote Similarity	NPC279554
0.6311	Remote Similarity	NPC56713
0.6286	Remote Similarity	NPC22956
0.6262	Remote Similarity	NPC180550
0.6262	Remote Similarity	NPC35405
0.619	Remote Similarity	NPC472949
0.6182	Remote Similarity	NPC114484
0.6036	Remote Similarity	NPC276093
0.602	Remote Similarity	NPC283849
0.602	Remote Similarity	NPC28198
0.602	Remote Similarity	NPC476123
0.6019	Remote Similarity	NPC114304
0.5982	Remote Similarity	NPC324875
0.5982	Remote Similarity	NPC292677
0.5909	Remote Similarity	NPC139044
0.5909	Remote Similarity	NPC471383
0.5905	Remote Similarity	NPC136877
0.5865	Remote Similarity	NPC164194
0.5856	Remote Similarity	NPC481082
0.5856	Remote Similarity	NPC164419
0.5856	Remote Similarity	NPC257468
0.5818	Remote Similarity	NPC159309
0.5818	Remote Similarity	NPC86222
0.5728	Remote Similarity	NPC284807
0.5701	Remote Similarity	NPC59804
0.5648	Remote Similarity	NPC127056
0.5648	Remote Similarity	NPC109079
0.563	Remote Similarity	NPC323341
0.563	Remote Similarity	NPC133818
0.5619	Remote Similarity	NPC480938
0.5583	Remote Similarity	NPC166422
0.5583	Remote Similarity	NPC219180
0.5583	Remote Similarity	NPC251263
0.5556	Remote Similarity	NPC477195
0.5536	Remote Similarity	NPC104400
0.5536	Remote Similarity	NPC10320
0.552	Remote Similarity	NPC161717
0.5495	Remote Similarity	NPC242840
0.5492	Remote Similarity	NPC54636
0.5484	Remote Similarity	NPC298554
0.5437	Remote Similarity	NPC31839
0.536	Remote Similarity	NPC478596
0.5357	Remote Similarity	NPC469945
0.5326	Remote Similarity	NPC480946
0.5326	Remote Similarity	NPC130577
0.5326	Remote Similarity	NPC142415
0.5326	Remote Similarity	NPC102683
0.5323	Remote Similarity	NPC478597
0.5321	Remote Similarity	NPC603870
0.5319	Remote Similarity	NPC120840
0.5315	Remote Similarity	NPC488561
0.5294	Remote Similarity	NPC480936
0.5289	Remote Similarity	NPC478600
0.5289	Remote Similarity	NPC478599
0.5283	Remote Similarity	NPC473538
0.528	Remote Similarity	NPC21691
0.5276	Remote Similarity	NPC471385
0.5259	Remote Similarity	NPC79718
0.5254	Remote Similarity	NPC488209
0.525	Remote Similarity	NPC476992
0.5243	Remote Similarity	NPC57362
0.5185	Remote Similarity	NPC475472
0.5167	Remote Similarity	NPC11242
0.5167	Remote Similarity	NPC62725
0.5159	Remote Similarity	NPC478598
0.5128	Remote Similarity	NPC119794
0.5126	Remote Similarity	NPC488564
0.5106	Remote Similarity	NPC270768
0.5106	Remote Similarity	NPC59263
0.5106	Remote Similarity	NPC210106
0.5106	Remote Similarity	NPC275809
0.5093	Remote Similarity	NPC191410
0.5083	Remote Similarity	NPC475486
0.5053	Remote Similarity	NPC158141
0.5046	Remote Similarity	NPC475611
0.5043	Remote Similarity	NPC31193
0.5043	Remote Similarity	NPC73829
0.5041	Remote Similarity	NPC480939
0.5036	Remote Similarity	NPC475368

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC586434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6583
0.1-0.2	2513
0.2-0.3	50
0.3-0.4	3
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
0.5135	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