NPASS Compound

Natural Product: NPC470433

Natural Product ID	NPC470433
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Borassoside E
IUPAC Name	n.a.
Synonyms	Borassoside E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2036081
PubChem CID	60165173
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal 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 133141 0 0 0 0 0 0 0 0999 V2000 -4.9275 -3.8834 3.0753 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2523 -3.6933 1.8522 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3928 -2.2967 1.3953 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6827 -2.0187 0.1929 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3257 -0.6489 0.3092 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4624 -0.3206 -0.7429 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1524 -0.1422 -0.3021 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3658 -1.2988 -0.8856 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0304 -1.2355 -0.3663 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7214 -0.0493 -0.9842 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8786 1.1937 -0.8485 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5178 2.3548 -0.8767 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9739 2.5105 -1.0285 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7616 1.2269 -0.9508 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9439 0.2524 -0.1650 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6829 -0.9701 0.2770 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9857 -0.6374 0.9232 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8466 0.2417 0.0783 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0479 1.4975 -0.2335 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0572 2.2991 -0.9699 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3532 2.0119 -0.2010 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9776 0.8805 0.7739 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2513 0.2314 0.9845 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3059 -1.2012 1.3756 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0767 0.5804 -0.2240 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3524 1.5001 -0.9811 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3711 1.2968 0.1844 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2722 1.4475 -0.9931 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7186 0.0710 -1.4157 C 0 0 1 0 0 0 0 0 0 0 0 0 10.7198 -0.9287 -0.9032 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4313 -0.4845 -1.0073 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8948 -0.0068 -2.9045 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1442 -0.4472 -1.1977 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5800 1.1915 -0.6733 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0534 -0.3699 -2.4052 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5161 0.1996 0.3177 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7496 -0.3076 1.0225 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7717 -1.8361 1.1040 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6825 -2.2329 2.0448 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7840 -2.8773 1.4586 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9316 -2.1126 1.7401 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0253 -2.5057 0.9948 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1644 -1.7498 -0.2978 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9251 -3.9986 0.6429 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3786 -4.7220 1.8631 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9319 -4.2434 2.0431 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1001 -5.1594 1.3805 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3196 -6.0929 1.6013 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2164 -4.4469 0.3941 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8606 0.0282 0.2563 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1887 1.3990 1.0131 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4226 2.5181 0.2383 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1738 3.1736 0.0811 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3450 4.1990 -0.8536 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6255 3.6428 -2.2167 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3617 5.2144 -0.4482 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6523 4.6257 0.0663 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3199 3.4850 0.9892 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4318 2.8243 1.4670 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5108 4.2155 -0.9261 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8265 6.0140 0.5515 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4580 -4.4823 3.6865 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1641 -3.8395 2.1316 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4655 -4.4699 1.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8839 -1.6421 2.1709 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7693 -0.6142 1.2688 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1551 -0.3082 0.7940 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4853 -1.2841 -1.9692 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8294 -2.2253 -0.4622 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6199 -2.1352 -0.6693 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9701 -1.1607 0.7373 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9516 3.2901 -0.7825 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3811 3.2789 -0.3037 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1253 3.0151 -2.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9489 0.9213 -1.9989 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6058 0.7781 0.7682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0458 -1.4593 1.0725 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7702 -1.7585 -0.5154 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4699 -1.6245 1.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7670 -0.2026 1.9391 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8290 2.0386 0.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8485 3.3861 -0.7924 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1444 2.1235 -2.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7113 2.8777 0.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5873 1.4055 1.6691 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7426 0.7856 1.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2602 -1.9320 0.5681 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3213 -1.3800 1.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5998 -1.3614 2.2075 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8984 0.6974 0.9676 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0642 2.2405 0.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1317 2.0627 -0.7160 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7164 1.9831 -1.7896 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6920 -0.1765 -0.9053 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9805 -1.3265 0.0992 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7985 -1.8221 -1.5898 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5777 -0.8389 -3.1592 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9238 -0.2256 -3.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3600 0.9200 -3.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6095 -1.4588 -1.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6987 0.1674 -1.9481 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1667 -0.6762 -1.7017 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1412 1.6255 -1.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8129 1.8661 0.2091 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2460 -0.9054 -2.9462 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9296 -1.0532 -2.4522 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2329 0.5512 -3.0307 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8249 0.5559 -0.7149 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8838 0.1108 2.0280 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0972 -2.2227 0.1094 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6996 -2.9362 0.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9889 -2.4030 1.5582 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3566 -0.6704 -0.1047 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2392 -1.8484 -0.8997 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9962 -2.1318 -0.9114 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3071 -4.1706 -0.2459 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9803 -4.5384 2.7518 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7516 -4.2425 3.1382 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7357 -5.7551 2.0958 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6975 -6.2340 0.8289 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1808 -5.4501 0.4372 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6400 0.2893 0.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8420 2.2738 -0.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3617 4.7375 -0.8919 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9756 4.1186 -2.9506 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4303 2.5540 -2.2326 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6769 3.8062 -2.5427 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5944 5.8224 -1.3561 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1656 5.4374 0.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7078 3.8411 1.8498 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5100 2.9643 2.4406 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4032 4.6594 -0.8632 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5278 6.3731 1.1456 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 2 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 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 18 33 1 6 11 34 1 0 10 35 1 6 5 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 45 48 1 0 44 49 1 0 37 50 1 0 36 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 57 58 1 0 58 59 1 0 57 60 1 0 56 61 1 0 38 3 1 0 46 40 1 0 58 52 1 0 34 7 1 0 15 10 1 0 22 18 1 0 31 25 1 0 19 14 1 0 26 21 1 0 1 62 1 0 2 63 1 0 2 64 1 0 3 65 1 1 5 66 1 1 7 67 1 1 8 68 1 0 8 69 1 0 9 70 1 0 9 71 1 0 12 72 1 0 13 73 1 0 13 74 1 0 14 75 1 6 15 76 1 1 16 77 1 0 16 78 1 0 17 79 1 0 17 80 1 0 19 81 1 1 20 82 1 0 20 83 1 0 21 84 1 1 22 85 1 1 23 86 1 1 24 87 1 0 24 88 1 0 24 89 1 0 27 90 1 0 27 91 1 0 28 92 1 0 28 93 1 0 29 94 1 1 30 95 1 0 30 96 1 0 32 97 1 0 32 98 1 0 32 99 1 0 33100 1 0 33101 1 0 33102 1 0 34103 1 0 34104 1 0 35105 1 0 35106 1 0 35107 1 0 36108 1 6 37109 1 1 38110 1 6 40111 1 6 42112 1 1 43113 1 0 43114 1 0 43115 1 0 44116 1 6 45117 1 1 46118 1 1 47119 1 0 48120 1 0 49121 1 0 50122 1 0 52123 1 6 54124 1 6 55125 1 0 55126 1 0 55127 1 0 56128 1 6 57129 1 1 58130 1 1 59131 1 0 60132 1 0 61133 1 0 M END

Standard InCHIKey	VNONINPVFQTJOC-VJNDXYECSA-N
Standard InCHI	InChI=1S/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(52)34(50)32(48)22(4)56-41)37(53)38(29(17-46)58-42)59-40-35(51)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3/t19-,20+,21-,22-,24-,25+,26-,27-,28-,29+,30-,31-,32-,33+,34+,35+,36+,37-,38+,39+,40-,41-,42+,43-,44-,45-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@H]4C[C@H]4[C@@H]3[C@@H](C)[C@@]3(O4)CC[C@@H](CO3)C)C)C2)C)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	868.48	Volume:	847.875 ? Van der Waals volume.
Dense:	1.024	LogP:	1.871 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.618 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.263 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	48.0
TPSA:	235.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	9.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.168	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.675	Fsp³:	0.956
MCE-18:	229.091 ? 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:	0.777	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.237	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.21	MDCK Permeability:	-5.015
Pgp-inhibitor:	0.0	Pgp-substrate:	0.988
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):	0.001
20% Bioavailability (F20%):	0.234	30% Bioavailability (F30%):	0.753
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.124
Plasma Protein Binding (PPB):	74.028%	Volume Distribution (VD):	-0.323
Fu:	19.314% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.065
BSEP inhibitor:	0.074

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:	0.001
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.702
HLM stability:	0.362 ? 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):

0.234

Half-life (T1/2):

2.916

ADMET: Toxicity

hERG Blockers:	0.057	hERG Blockers (10um):	0.305
Human Hepatotoxicity (H-HT):	0.377	Drug-induced Liver Injury (DILI):	0.851
AMES Toxicity:	0.857	Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.023	Skin Sensitization:	1.0
Carcinogencity:	0.035	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.996
Hematotoxicity:	0.107	Drug-induced Nephrotoxicity:	0.685
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.35
A549 Cytotoxicity:	0.756	Hek293 Cytotoxicity:	0.608
BCF:	2.199 ? 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:	3.735 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.902 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.38 ? 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
NPO32523	solanum violaceum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22413887]
NPO32523	solanum violaceum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23511021]

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	8

Activity Type	# Activity
Cell line	5
Non-molecular	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
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	1.83	ug.mL-1	PMID[16919944]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	2.61	ug.mL-1	Open TG-GATES in vivo data: Hematology
NPT81	Cell line	A549	Homo sapiens	IC50	=	2.34	ug.mL-1	DrugMatrix in vitro pharmacology data
NPT1031	Cell line	Ca9-22	Homo sapiens	IC50	=	2.33	ug.mL-1	DOI[10.6019/CHEMBL1201861]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	2.75	ug.mL-1	PMID[21652215]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2.03	ug.mL-1	PMID[22413887]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	0.62	ug.mL-1	PMID[22413887]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	111.05	ug.mL-1	PMID[22413887]

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 NPC470433 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	23994
0.1-0.2	22482
0.2-0.3	2630
0.3-0.4	498
0.4-0.5	115
0.5-0.6	66
0.6-0.7	30
0.7-0.8	0
0.8-0.85	10
0.85-0.9	4
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC46190
1.0	High Similarity	NPC171073
0.9667	High Similarity	NPC480555
0.9667	High Similarity	NPC150372
0.9355	High Similarity	NPC269297
0.9355	High Similarity	NPC222202
0.9255	High Similarity	NPC475333
0.9255	High Similarity	NPC224098
0.9255	High Similarity	NPC208383
0.9231	High Similarity	NPC248746
0.9062	High Similarity	NPC480554
0.8878	High Similarity	NPC480553
0.8723	High Similarity	NPC42171
0.8571	High Similarity	NPC194207
0.8571	High Similarity	NPC22779
0.8447	Intermediate Similarity	NPC480556
0.8387	Intermediate Similarity	NPC113044
0.8387	Intermediate Similarity	NPC283829
0.8387	Intermediate Similarity	NPC161676
0.837	Intermediate Similarity	NPC470432
0.837	Intermediate Similarity	NPC230507
0.8365	Intermediate Similarity	NPC224314
0.8155	Intermediate Similarity	NPC232054
0.8125	Intermediate Similarity	NPC602423
0.81	Intermediate Similarity	NPC32361
0.7959	Intermediate Similarity	NPC300557
0.7849	Intermediate Similarity	NPC19400
0.7677	Intermediate Similarity	NPC477809
0.7629	Intermediate Similarity	NPC14704
0.7604	Intermediate Similarity	NPC485595
0.7604	Intermediate Similarity	NPC6295
0.7582	Intermediate Similarity	NPC181845
0.7573	Intermediate Similarity	NPC13193
0.7426	Intermediate Similarity	NPC124677
0.7297	Intermediate Similarity	NPC477808
0.7255	Intermediate Similarity	NPC6806
0.7115	Intermediate Similarity	NPC73243
0.7115	Intermediate Similarity	NPC244086
0.7115	Intermediate Similarity	NPC84956
0.7075	Intermediate Similarity	NPC309278
0.7071	Intermediate Similarity	NPC94272
0.7019	Intermediate Similarity	NPC475182
0.6981	Remote Similarity	NPC247037
0.6832	Remote Similarity	NPC141433
0.6832	Remote Similarity	NPC195297
0.6827	Remote Similarity	NPC122819
0.6822	Remote Similarity	NPC475550
0.6818	Remote Similarity	NPC477811
0.6789	Remote Similarity	NPC249265
0.6765	Remote Similarity	NPC305423
0.6727	Remote Similarity	NPC23808
0.6727	Remote Similarity	NPC87998
0.6604	Remote Similarity	NPC471464
0.66	Remote Similarity	NPC306131
0.66	Remote Similarity	NPC200802
0.6562	Remote Similarity	NPC165439
0.6465	Remote Similarity	NPC477451
0.646	Remote Similarity	NPC308140
0.6316	Remote Similarity	NPC287885
0.6286	Remote Similarity	NPC160426
0.6168	Remote Similarity	NPC40440
0.6111	Remote Similarity	NPC265275
0.61	Remote Similarity	NPC297348
0.61	Remote Similarity	NPC249204
0.61	Remote Similarity	NPC48339
0.61	Remote Similarity	NPC141769
0.61	Remote Similarity	NPC477547
0.6071	Remote Similarity	NPC486386
0.6038	Remote Similarity	NPC70204
0.6034	Remote Similarity	NPC31896
0.6019	Remote Similarity	NPC98696
0.6	Remote Similarity	NPC107962
0.5965	Remote Similarity	NPC254255
0.5946	Remote Similarity	NPC128572
0.5941	Remote Similarity	NPC325828
0.5914	Remote Similarity	NPC100451
0.59	Remote Similarity	NPC485594
0.5893	Remote Similarity	NPC102016
0.5893	Remote Similarity	NPC95051
0.5865	Remote Similarity	NPC206003
0.5865	Remote Similarity	NPC473610
0.581	Remote Similarity	NPC211354
0.5769	Remote Similarity	NPC222731
0.5766	Remote Similarity	NPC469348
0.5714	Remote Similarity	NPC249553
0.5699	Remote Similarity	NPC235126
0.5699	Remote Similarity	NPC242419
0.5691	Remote Similarity	NPC210569
0.5676	Remote Similarity	NPC475643
0.5648	Remote Similarity	NPC15249
0.5648	Remote Similarity	NPC25455
0.5641	Remote Similarity	NPC218571
0.5641	Remote Similarity	NPC487615
0.5619	Remote Similarity	NPC250393
0.5614	Remote Similarity	NPC294129
0.5586	Remote Similarity	NPC42482
0.5528	Remote Similarity	NPC477807
0.5495	Remote Similarity	NPC475351
0.5455	Remote Similarity	NPC144790
0.5455	Remote Similarity	NPC149400
0.544	Remote Similarity	NPC15918
0.5439	Remote Similarity	NPC274200
0.5439	Remote Similarity	NPC182900
0.5433	Remote Similarity	NPC305771
0.5433	Remote Similarity	NPC94072
0.5433	Remote Similarity	NPC169816
0.5429	Remote Similarity	NPC294686
0.5429	Remote Similarity	NPC234352
0.5391	Remote Similarity	NPC150057
0.5391	Remote Similarity	NPC147753
0.537	Remote Similarity	NPC107188
0.5345	Remote Similarity	NPC97700
0.5345	Remote Similarity	NPC184617
0.5345	Remote Similarity	NPC30856
0.534	Remote Similarity	NPC486114
0.5339	Remote Similarity	NPC475625
0.5315	Remote Similarity	NPC475670
0.531	Remote Similarity	NPC486388
0.5258	Remote Similarity	NPC486119
0.5225	Remote Similarity	NPC125324
0.5225	Remote Similarity	NPC306991
0.5221	Remote Similarity	NPC112274
0.5217	Remote Similarity	NPC92890
0.5207	Remote Similarity	NPC83137
0.5194	Remote Similarity	NPC263359
0.5146	Remote Similarity	NPC481420
0.5146	Remote Similarity	NPC473774
0.5146	Remote Similarity	NPC481419
0.5146	Remote Similarity	NPC481417
0.5146	Remote Similarity	NPC481421
0.514	Remote Similarity	NPC131693
0.514	Remote Similarity	NPC475436
0.5133	Remote Similarity	NPC470748
0.5098	Remote Similarity	NPC277715
0.5047	Remote Similarity	NPC177834
0.5043	Remote Similarity	NPC197231
0.5041	Remote Similarity	NPC232037
0.5041	Remote Similarity	NPC132080

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470433 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7622
0.1-0.2	1452
0.2-0.3	64
0.3-0.4	6
0.4-0.5	2
0.5-0.6	3
0.6-0.7	1
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
0.6827	Remote Similarity	NPD8449	Approved
0.5941	Remote Similarity	NPD8171	Phase 2
0.5391	Remote Similarity	NPD8450	Suspended
0.5364	Remote Similarity	NPD8170	Phase 2

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