NPASS Compound

Natural Product: NPC471385

Natural Product ID	NPC471385
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3 Beta-O-{Beta-D-Xylopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-[Beta-D-Glucopyranosyl-(1->4)Beta-D-Glucopyranosyl-(1->4)]-Alpha-L-Arabinopyranosyl}Hederagenin
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxyoxan-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	CHEMBL2430037
PubChem CID	72190161
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 178187 0 0 0 0 0 0 0 0999 V2000 6.7971 4.5307 -0.9924 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2914 4.5812 -0.9369 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7775 5.5844 -1.9274 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2719 5.6104 -2.0321 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6463 4.2538 -1.7843 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3651 3.4688 -0.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7107 3.3550 -1.2278 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8505 2.2338 -0.4843 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5984 2.0968 0.8481 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7837 1.3633 1.5406 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2861 -0.0631 1.8811 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2479 0.1518 2.9213 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6088 1.4242 2.7775 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3733 1.5344 1.3560 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1390 2.0409 1.1000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8770 1.1014 0.9928 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8670 1.4835 2.0702 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3001 1.2611 1.7199 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4905 0.0274 0.8339 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7863 0.3444 -0.4624 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4499 0.9826 -0.3681 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4921 0.1101 -1.1931 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3885 2.3179 -1.0782 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0325 3.3582 -0.4973 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8785 -0.8476 -1.3553 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0676 -1.7188 -1.1677 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2839 -1.0913 -0.5748 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9619 -0.0457 0.4672 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9276 0.0270 1.5815 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2674 -0.3804 1.0749 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5080 -1.3967 0.2515 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2503 -2.1429 -0.1471 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5266 -3.1212 -1.2667 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8664 -3.8014 -1.1177 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9314 -2.7335 -1.2922 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8484 -1.7623 -0.1892 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7898 -0.6446 -0.4454 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1798 -1.1089 -0.7948 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3981 -2.5643 -0.8254 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2673 -3.4681 -1.1047 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1106 -0.5229 0.2704 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6394 -0.4704 -2.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8977 -2.3048 -2.6655 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7091 -1.1844 -3.1593 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1191 -3.3270 -3.6379 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8758 -3.0005 1.0181 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9951 -0.3269 -1.7117 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9425 -1.1118 1.5994 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3581 -0.8545 2.2759 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8016 -1.6972 1.2399 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4189 -3.1285 1.4042 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3959 -3.8905 2.1955 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7923 -3.5997 1.6646 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0458 -2.1114 1.6658 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1002 -1.4443 0.8931 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3704 -1.8636 0.9947 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6642 -0.4908 0.9374 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6637 -4.2720 2.4732 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4971 -5.1740 1.8592 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9161 -5.0528 2.2846 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5430 -6.4392 2.3656 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1005 -7.2666 1.1600 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5820 -7.3007 1.1176 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0674 -6.5005 2.1537 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0880 -8.7156 1.1736 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4001 -9.3804 2.3474 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5448 -8.5651 1.3652 O 0 0 0 0 0 0 0 0 0 0 0 0 11.9329 -6.2740 2.2338 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9701 -4.5577 3.6133 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1497 -5.2597 2.0829 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3904 -3.6900 0.1096 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1476 1.9791 2.7182 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3332 4.5434 -1.3345 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6817 6.5111 -1.1879 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0779 7.6052 -1.8116 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6148 7.7172 -1.5640 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0599 8.9078 -2.3108 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9700 10.0860 -2.1868 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9611 9.8118 -1.0584 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7314 8.7149 -1.3220 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2097 11.1933 -1.7975 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2457 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-0.7766 2.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6493 -1.7218 2.1634 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3028 -1.7423 0.9472 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1743 -1.3660 0.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3744 -3.1935 1.7876 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3596 -3.6100 3.2893 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8222 -3.9175 0.6044 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0886 -1.7109 2.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2059 -2.4438 1.3820 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2352 -2.1579 -0.0787 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8144 -0.0125 0.9715 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4017 -5.0426 0.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5378 -4.3878 1.6368 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3526 -6.9449 3.3089 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5565 -6.8824 0.2293 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2702 -6.8422 0.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5661 -9.3253 0.3493 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9828 -8.7456 1.0467 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6079 -9.8127 2.7651 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8772 -9.0000 0.5557 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3719 -6.3866 3.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2728 -5.2185 4.2586 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1727 -5.4436 2.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7776 -3.1654 -0.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1432 2.9702 2.6634 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2034 4.2298 -0.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2690 7.5744 -2.9257 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0447 6.8389 -1.9798 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0116 8.6533 -3.4086 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5075 10.3678 -3.1146 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5879 10.7442 -0.9563 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3744 9.7852 -0.1206 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7574 11.9349 -1.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3477 10.0966 -1.5659 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6326 8.2882 -0.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2119 5.5804 -3.3170 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 20 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 2 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 38 42 1 0 35 43 1 0 43 44 2 0 43 45 1 0 32 46 1 0 27 47 1 0 19 48 1 0 11 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 54 56 1 0 56 57 1 0 53 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 63 65 1 0 65 66 1 0 62 67 1 0 61 68 1 0 60 69 1 0 52 70 1 0 51 71 1 0 10 72 1 0 5 73 1 0 4 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 78 81 1 0 77 82 1 0 76 83 1 0 3 84 1 0 7 2 1 0 80 75 1 0 14 9 1 0 21 16 1 0 28 19 1 0 32 27 1 0 36 31 1 0 40 35 1 0 55 50 1 0 64 59 1 0 1 85 1 0 1 86 1 0 1 87 1 0 2 88 1 0 3 89 1 0 4 90 1 0 5 91 1 0 6 92 1 0 9 93 1 0 10 94 1 0 11 95 1 0 12 96 1 0 12 97 1 0 14 98 1 0 16 99 1 0 17100 1 0 17101 1 0 18102 1 0 18103 1 0 20104 1 0 22105 1 0 22106 1 0 22107 1 0 23108 1 0 23109 1 0 24110 1 0 25111 1 0 25112 1 0 26113 1 0 26114 1 0 28115 1 0 29116 1 0 29117 1 0 30118 1 0 33119 1 0 33120 1 0 34121 1 0 34122 1 0 36123 1 0 37124 1 0 37125 1 0 39126 1 0 39127 1 0 40128 1 0 40129 1 0 41130 1 0 41131 1 0 41132 1 0 42133 1 0 42134 1 0 42135 1 0 45136 1 0 46137 1 0 46138 1 0 46139 1 0 47140 1 0 47141 1 0 47142 1 0 48143 1 0 48144 1 0 48145 1 0 50146 1 0 51147 1 0 52148 1 0 53149 1 0 54150 1 0 56151 1 0 56152 1 0 57153 1 0 59154 1 0 60155 1 0 61156 1 0 62157 1 0 63158 1 0 65159 1 0 65160 1 0 66161 1 0 67162 1 0 68163 1 0 69164 1 0 70165 1 0 71166 1 0 72167 1 0 73168 1 0 75169 1 0 76170 1 0 77171 1 0 78172 1 0 79173 1 0 79174 1 0 81175 1 0 82176 1 0 83177 1 0 84178 1 0 M END

Standard InCHIKey	GSOMSXJOAJCAIV-YFNOCVKUSA-N
Standard InCHI	InChI=1S/C58H94O26/c1-24-34(63)45(83-47-40(69)35(64)27(62)21-75-47)43(72)50(77-24)84-46-37(66)30(80-48-42(71)39(68)44(29(20-60)79-48)82-49-41(70)38(67)36(65)28(19-59)78-49)22-76-51(46)81-33-11-12-54(4)31(55(33,5)23-61)10-13-57(7)32(54)9-8-25-26-18-53(2,3)14-16-58(26,52(73)74)17-15-56(25,57)6/h8,24,26-51,59-72H,9-23H2,1-7H3,(H,73,74)/t24-,26-,27+,28+,29+,30-,31+,32+,33-,34-,35-,36+,37-,38-,39+,40+,41+,42+,43+,44+,45+,46+,47-,48-,49-,50-,51-,54-,55-,56+,57+,58-/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)OC8C(C(C(C(O8)CO)OC9C(C(C(C(O9)CO)O)O)O)O)O)O)O)OC1C(C(C(CO1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1206.6	Volume:	1149.432 ? Van der Waals volume.
Dense:	1.05	LogP:	-0.851 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.152 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.688 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	57.0
TPSA:	412.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	15.0	Rings:	10.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.064	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.222	Fsp³:	0.948
MCE-18:	215.327 ? 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:	0.008	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.374 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.422	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.584	MDCK Permeability:	-4.855
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
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):	1.0
20% Bioavailability (F20%):	0.357	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	40.471%	Volume Distribution (VD):	-0.444
Fu:	30.885% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.006	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.973	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

-0.879

Half-life (T1/2):

4.313

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.035
Human Hepatotoxicity (H-HT):	0.293	Drug-induced Liver Injury (DILI):	0.197
AMES Toxicity:	0.219	Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.051	Skin Sensitization:	0.015
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.139	Ototoxicity:	1.0
Hematotoxicity:	0.004	Drug-induced Nephrotoxicity:	0.016
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.006	Hek293 Cytotoxicity:	0.582
BCF:	0.13 ? 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:	3.891 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.173 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.018 ? 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
NPO32682	anemone taipaiensis	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23992864]
NPO32682	anemone taipaiensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
IC50	5

Activity Type	# Activity
Cell line	4
Non-molecular	1

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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	19560.0	nM	PMID[18676884]
NPT81	Cell line	A549	Homo sapiens	IC50	=	27310.0	nM	PMID[23190013]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	21560.0	nM	PMID[19795841]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	18390.0	nM	PMID[16441059]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	29290.0	nM	PMID[23992864]

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 NPC471385 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	25209
0.1-0.2	20811
0.2-0.3	2490
0.3-0.4	793
0.4-0.5	402
0.5-0.6	90
0.6-0.7	41
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC323341
0.8839	High Similarity	NPC54636
0.8739	High Similarity	NPC133818
0.8661	High Similarity	NPC166422
0.8174	Intermediate Similarity	NPC251263
0.8018	Intermediate Similarity	NPC276093
0.7909	Intermediate Similarity	NPC139044
0.7851	Intermediate Similarity	NPC161717
0.7712	Intermediate Similarity	NPC219180
0.7479	Intermediate Similarity	NPC471384
0.7478	Intermediate Similarity	NPC324875
0.7478	Intermediate Similarity	NPC292677
0.7414	Intermediate Similarity	NPC488564
0.7368	Intermediate Similarity	NPC257468
0.7281	Intermediate Similarity	NPC471383
0.7217	Intermediate Similarity	NPC481082
0.7217	Intermediate Similarity	NPC164419
0.7179	Intermediate Similarity	NPC323359
0.7117	Intermediate Similarity	NPC59804
0.6875	Remote Similarity	NPC65105
0.6875	Remote Similarity	NPC136877
0.6847	Remote Similarity	NPC270667
0.6814	Remote Similarity	NPC174679
0.6814	Remote Similarity	NPC279554
0.6742	Remote Similarity	NPC250247
0.6609	Remote Similarity	NPC127056
0.6583	Remote Similarity	NPC79718
0.6579	Remote Similarity	NPC12288
0.6565	Remote Similarity	NPC136768
0.6565	Remote Similarity	NPC202828
0.6565	Remote Similarity	NPC119592
0.6557	Remote Similarity	NPC488209
0.6552	Remote Similarity	NPC488561
0.6532	Remote Similarity	NPC476992
0.6525	Remote Similarity	NPC114304
0.6515	Remote Similarity	NPC298034
0.6515	Remote Similarity	NPC71065
0.6504	Remote Similarity	NPC475486
0.6471	Remote Similarity	NPC104400
0.6471	Remote Similarity	NPC10320
0.6422	Remote Similarity	NPC28198
0.6422	Remote Similarity	NPC476123
0.6364	Remote Similarity	NPC43550
0.633	Remote Similarity	NPC204407
0.6239	Remote Similarity	NPC56713
0.6165	Remote Similarity	NPC41061
0.6165	Remote Similarity	NPC227551
0.6121	Remote Similarity	NPC164194
0.6119	Remote Similarity	NPC293330
0.6102	Remote Similarity	NPC25605
0.6094	Remote Similarity	NPC475287
0.6074	Remote Similarity	NPC236638
0.6074	Remote Similarity	NPC294453
0.6074	Remote Similarity	NPC305981
0.6066	Remote Similarity	NPC180550
0.6066	Remote Similarity	NPC35405
0.6061	Remote Similarity	NPC481080
0.6029	Remote Similarity	NPC261506
0.6029	Remote Similarity	NPC4328
0.6	Remote Similarity	NPC472949
0.597	Remote Similarity	NPC110633
0.5968	Remote Similarity	NPC475504
0.5942	Remote Similarity	NPC220160
0.5917	Remote Similarity	NPC109079
0.5902	Remote Similarity	NPC469945
0.5891	Remote Similarity	NPC288205
0.5891	Remote Similarity	NPC51465
0.5862	Remote Similarity	NPC284807
0.5841	Remote Similarity	NPC283849
0.5841	Remote Similarity	NPC606107
0.582	Remote Similarity	NPC22956
0.5814	Remote Similarity	NPC280941
0.5814	Remote Similarity	NPC235772
0.5794	Remote Similarity	NPC119794
0.5789	Remote Similarity	NPC191827
0.5782	Remote Similarity	NPC40085
0.5738	Remote Similarity	NPC6377
0.5738	Remote Similarity	NPC208381
0.5725	Remote Similarity	NPC76972
0.5725	Remote Similarity	NPC469782
0.5725	Remote Similarity	NPC204414
0.5714	Remote Similarity	NPC123199
0.5691	Remote Similarity	NPC80843
0.569	Remote Similarity	NPC100383
0.5672	Remote Similarity	NPC475140
0.5669	Remote Similarity	NPC488515
0.5659	Remote Similarity	NPC241909
0.5615	Remote Similarity	NPC481078
0.56	Remote Similarity	NPC264270
0.5591	Remote Similarity	NPC73829
0.5573	Remote Similarity	NPC62725
0.5564	Remote Similarity	NPC79643
0.5556	Remote Similarity	NPC473383
0.5512	Remote Similarity	NPC91838
0.55	Remote Similarity	NPC481081
0.5489	Remote Similarity	NPC473824
0.5481	Remote Similarity	NPC135904
0.5403	Remote Similarity	NPC114441
0.5397	Remote Similarity	NPC240734
0.536	Remote Similarity	NPC488516
0.5357	Remote Similarity	NPC258617
0.5354	Remote Similarity	NPC309714
0.5333	Remote Similarity	NPC151543
0.5328	Remote Similarity	NPC100639
0.5303	Remote Similarity	NPC187618
0.5299	Remote Similarity	NPC475119
0.529	Remote Similarity	NPC488560
0.5286	Remote Similarity	NPC473452
0.528	Remote Similarity	NPC480424
0.5278	Remote Similarity	NPC488212
0.5259	Remote Similarity	NPC60557
0.5259	Remote Similarity	NPC67857
0.5259	Remote Similarity	NPC610204
0.5254	Remote Similarity	NPC177246
0.5227	Remote Similarity	NPC291903
0.5217	Remote Similarity	NPC475160
0.5217	Remote Similarity	NPC473714
0.5214	Remote Similarity	NPC476068
0.5214	Remote Similarity	NPC57484
0.5212	Remote Similarity	NPC469777
0.521	Remote Similarity	NPC469772
0.5207	Remote Similarity	NPC473538
0.5203	Remote Similarity	NPC127853
0.5191	Remote Similarity	NPC484832
0.5188	Remote Similarity	NPC295823
0.5188	Remote Similarity	NPC174720
0.5188	Remote Similarity	NPC475467
0.5188	Remote Similarity	NPC469775
0.5185	Remote Similarity	NPC469774
0.5169	Remote Similarity	NPC57362
0.5154	Remote Similarity	NPC257964
0.5152	Remote Similarity	NPC37134
0.5149	Remote Similarity	NPC609281
0.5148	Remote Similarity	NPC469773
0.5145	Remote Similarity	NPC155410
0.5139	Remote Similarity	NPC302543
0.5135	Remote Similarity	NPC488210
0.5118	Remote Similarity	NPC295371
0.5115	Remote Similarity	NPC275668
0.5113	Remote Similarity	NPC606145
0.5111	Remote Similarity	NPC75287
0.5109	Remote Similarity	NPC192600
0.5091	Remote Similarity	NPC100925
0.5078	Remote Similarity	NPC473734
0.5069	Remote Similarity	NPC111466
0.5041	Remote Similarity	NPC242611
0.5038	Remote Similarity	NPC258885
0.5036	Remote Similarity	NPC313110
0.5035	Remote Similarity	NPC470876
0.5035	Remote Similarity	NPC475514

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7237
0.1-0.2	1854
0.2-0.3	52
0.3-0.4	6
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