NPASS Compound

Natural Product: NPC475509

Natural Product ID	NPC475509
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hopenyl Palmitate
IUPAC Name	[(3S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bS)-5a,5b,8,8,11a,13b-hexamethyl-3-prop-1-en-2-yl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-9-yl] hexadecanoate
Synonyms	Hopenyl Palmitate
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL507015
PubChem CID	44575981
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001823] Hopanoids

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 128132 0 0 0 0 0 0 0 0999 V2000 15.3460 -0.9999 -0.8353 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8716 -0.7567 -1.1276 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3324 0.1832 -0.0976 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8157 0.4657 -0.3371 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6467 1.1112 -1.6437 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3640 1.6161 -2.0749 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1651 0.8780 -2.2976 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2633 0.2144 -1.3486 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7016 -0.8710 -0.4887 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6631 -1.5874 0.2697 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8628 -0.9825 1.3034 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9076 0.1311 1.0942 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2254 0.4600 2.4473 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2908 1.5784 2.2535 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1935 1.3575 1.2968 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2720 0.2575 1.5410 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6093 -0.7207 2.2677 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0040 0.1415 1.0592 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1011 -0.9211 1.2776 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8528 -0.5845 2.4223 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1357 0.0119 2.0716 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5096 0.0699 0.5939 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0384 -1.1960 0.0238 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5598 -1.4673 0.0774 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4374 -2.9966 0.0634 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1605 -1.1204 -1.2176 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6125 -1.4955 -1.3421 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1238 -1.6677 -1.1000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6917 -0.3031 -0.6785 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0259 0.0734 0.5772 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6037 1.2991 1.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0157 0.8493 1.6524 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7128 0.6337 0.3350 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1938 -0.5212 -0.4222 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3577 -1.8565 0.2359 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9034 -0.6730 -1.7522 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4317 -0.5532 -1.5799 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6536 0.7749 -1.0320 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2048 0.8074 0.4041 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8994 -0.1398 1.3202 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5590 2.2045 0.8162 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5900 2.6712 -0.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9252 1.4668 -1.0298 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.1676 0.7941 -0.7561 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8946 1.0725 0.2766 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6366 -0.2674 -1.6940 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5400 0.5913 -1.8397 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9784 1.3507 0.0929 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8518 -1.3485 -1.7781 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8364 -0.0620 -0.5121 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4613 -1.8212 -0.0912 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3735 -1.7580 -1.0614 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8272 -0.4063 -2.1651 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3940 -0.3007 0.8889 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8401 1.1611 -0.1139 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4586 0.9703 0.5399 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3994 -0.5972 -0.3411 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4540 1.9295 -1.7102 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0040 0.3249 -2.4275 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1137 2.5587 -1.3840 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6187 2.2410 -3.0527 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3379 0.0716 -3.1477 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4761 1.5800 -2.9458 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3025 -0.0496 -1.9341 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8740 1.0755 -0.6769 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3246 -0.3695 0.3594 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3652 -1.5975 -1.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9309 -1.9867 -0.5420 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0893 -2.6170 0.6272 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5527 -0.6086 2.1610 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2441 -1.8100 1.8286 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0588 -0.1021 0.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3858 1.0295 0.7230 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0565 0.8224 3.1267 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7478 -0.4158 2.8788 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8478 2.5043 1.8681 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8452 1.9655 3.2057 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5615 2.3087 1.3204 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5348 1.3385 0.2210 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7399 -1.6852 1.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3223 0.0714 3.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0604 -1.4982 3.0437 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1603 1.0488 2.5059 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9729 -0.5751 2.5649 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4979 -1.9859 0.6845 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1849 -3.3849 0.7759 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5695 -3.4039 -0.9569 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5774 -3.2556 0.4267 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1216 -1.6923 -1.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4320 -1.6138 -2.0379 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2602 -0.0889 -1.4605 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2637 -2.4594 -1.7087 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4065 -0.7247 -2.0826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6464 -2.0894 -1.9522 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1665 -2.2989 -0.1627 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2650 -0.7666 1.3132 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8039 2.1163 0.4948 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1118 1.6117 2.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8956 -0.1418 2.1365 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4973 1.5965 2.2825 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4266 1.5493 -0.2853 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4079 -2.1024 0.4795 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7613 -2.0672 1.1072 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1074 -2.6320 -0.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6865 0.1404 -2.4725 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7499 -1.6798 -2.1925 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8426 -1.4236 -1.0729 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8193 -0.6144 -2.6392 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9102 1.4741 -1.5597 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4630 -0.9293 0.7935 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2017 -0.5564 2.1061 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6659 0.3799 1.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0223 2.1863 1.8396 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6571 2.8662 0.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4424 3.2043 0.2343 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0435 3.4439 -0.8088 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0540 1.9182 -2.0857 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6032 1.8432 1.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8635 0.6325 0.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7628 -0.3178 -1.7264 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3348 -0.0285 -2.7495 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2671 -1.2585 -1.4133 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5488 1.0357 -1.9846 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2499 1.4300 -1.9283 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6887 -0.0334 -2.7732 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8212 2.0942 0.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2606 1.8569 0.8075 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4891 1.3931 -0.8659 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 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 24 25 1 0 24 26 1 0 23 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 1 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 1 39 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 29 47 1 6 22 48 1 6 24 19 1 0 34 29 1 0 43 38 1 0 30 22 1 0 39 33 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 0 2 53 1 0 3 54 1 0 3 55 1 0 4 56 1 0 4 57 1 0 5 58 1 0 5 59 1 0 6 60 1 0 6 61 1 0 7 62 1 0 7 63 1 0 8 64 1 0 8 65 1 0 9 66 1 0 9 67 1 0 10 68 1 0 10 69 1 0 11 70 1 0 11 71 1 0 12 72 1 0 12 73 1 0 13 74 1 0 13 75 1 0 14 76 1 0 14 77 1 0 15 78 1 0 15 79 1 0 19 80 1 1 20 81 1 0 20 82 1 0 21 83 1 0 21 84 1 0 23 85 1 1 25 86 1 0 25 87 1 0 25 88 1 0 26 89 1 0 26 90 1 0 26 91 1 0 27 92 1 0 27 93 1 0 28 94 1 0 28 95 1 0 30 96 1 1 31 97 1 0 31 98 1 0 32 99 1 0 32100 1 0 33101 1 0 35102 1 0 35103 1 0 35104 1 0 36105 1 0 36106 1 0 37107 1 0 37108 1 0 38109 1 6 40110 1 0 40111 1 0 40112 1 0 41113 1 0 41114 1 0 42115 1 0 42116 1 0 43117 1 6 45118 1 0 45119 1 0 46120 1 0 46121 1 0 46122 1 0 47123 1 0 47124 1 0 47125 1 0 48126 1 0 48127 1 0 48128 1 0 M END

Standard InCHIKey	HABFHSNAEWDJCC-CBFBYORPSA-N
Standard InCHI	InChI=1S/C46H80O2/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-41(47)48-40-29-31-44(7)37(42(40,4)5)28-33-46(9)39(44)25-24-38-43(6)30-26-35(34(2)3)36(43)27-32-45(38,46)8/h35-40H,2,10-33H2,1,3-9H3/t35-,36+,37+,38?,39-,40+,43+,44+,45-,46-/m1/s1
SMILES	CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CCC2[C@@]1(C)CC[C@@H]1[C@]2(C)CC[C@@H]1C(=C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	664.62	Volume:	773.697 ? Van der Waals volume.
Dense:	0.859	LogP:	13.496 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	6.862 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-14.433 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	27.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.093	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.801	Fsp³:	0.935
MCE-18:	93.933 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.853	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.742	Promiscuous compounds:	0.163

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.088	MDCK Permeability:	-4.689
Pgp-inhibitor:	0.972	Pgp-substrate:	0.0
PAMPA:	0.0 ? 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):	0.0
20% Bioavailability (F20%):	0.808	30% Bioavailability (F30%):	0.91
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035	MRP1:	0.987
Plasma Protein Binding (PPB):	100.978%	Volume Distribution (VD):	1.696
Fu:	0.479% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.96
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.945	CYP2C19-substrate:	0.983
CYP2C9-inhibitor:	0.356	CYP2C9-substrate:	0.432
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.729 ? 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):

6.616

Half-life (T1/2):

0.733

ADMET: Toxicity

hERG Blockers:	0.621	hERG Blockers (10um):	0.729
Human Hepatotoxicity (H-HT):	0.586	Drug-induced Liver Injury (DILI):	0.361
AMES Toxicity:	0.073	Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.832	Skin Sensitization:	0.998
Carcinogencity:	0.912	Eye Corrosion:	0.671
Eye Irritation:	0.939	Respiratory Toxicity:	0.987
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.425
Hematotoxicity:	0.429	Drug-induced Nephrotoxicity:	0.812
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.04
A549 Cytotoxicity:	0.893	Hek293 Cytotoxicity:	0.616
BCF:	0.973 ? 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:	6.179 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.345 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	8.036 ? 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
NPO12713	Brachylaena ramiflora	Species	Asteraceae	Eukaryota	twigs	Madagascar rainforest	n.a.	PMID[12193040]
NPO12713	Brachylaena ramiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell line	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
NPT179	Cell line	A2780	Homo sapiens	IC50	=	11.6	ug.mL-1	PMID[17190444]

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 NPC475509 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	23830
0.1-0.2	21608
0.2-0.3	4119
0.3-0.4	239
0.4-0.5	43
0.5-0.6	12
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	Natural Product ID
0.7069	Intermediate Similarity	NPC611062
0.5833	Remote Similarity	NPC305835
0.5821	Remote Similarity	NPC475416
0.5652	Remote Similarity	NPC479062
0.5556	Remote Similarity	NPC98270
0.5469	Remote Similarity	NPC5280
0.5385	Remote Similarity	NPC304194
0.5352	Remote Similarity	NPC239362
0.5283	Remote Similarity	NPC127944
0.5224	Remote Similarity	NPC4309
0.5161	Remote Similarity	NPC488509
0.5075	Remote Similarity	NPC168231
0.5072	Remote Similarity	NPC160506

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475509 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7190
0.1-0.2	1846
0.2-0.3	102
0.3-0.4	11
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
0.5072	Remote Similarity	NPD8035	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