NPASS Compound

Natural Product: NPC138001

Natural Product ID	NPC138001
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VFSRKCNYYCXRGI-OSSYFQCISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10032370
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 128132 0 0 0 0 0 0 0 0999 V2000 11.2809 3.0616 -0.6673 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0986 1.7879 -0.6334 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8613 1.1158 0.6952 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6065 -0.1626 0.8780 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4258 -1.2528 -0.0848 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1042 -1.8748 -0.3145 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0486 -1.0138 -0.8919 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7402 -1.7694 -1.1105 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1542 -2.3336 0.1387 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8340 -1.2939 1.1713 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8315 -0.2731 0.6755 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5260 -0.9270 0.2831 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8576 -1.6626 1.3994 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4895 -0.8244 2.5782 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5373 0.2919 2.2617 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2563 -0.1952 1.7082 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9823 -1.4136 1.5181 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2561 0.6994 1.3575 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0153 0.2839 0.8202 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0492 0.5905 1.8133 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4573 0.4031 1.2164 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5527 1.3860 0.1225 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2954 2.7581 0.7498 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5941 1.0470 -0.9546 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9831 -0.2476 -1.5747 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3902 -0.4926 -1.8745 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4238 0.4379 -1.3263 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0915 1.0778 -2.5775 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9183 1.5538 -0.5213 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8687 2.1474 0.4693 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2653 1.7574 0.2714 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6476 0.6226 -0.2878 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1177 0.3869 -0.4098 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6425 0.0694 0.9631 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0079 -0.5125 1.0128 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0407 0.5862 1.2977 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0882 -1.4358 2.2382 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3886 -1.3550 -0.1654 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1019 -1.8144 -0.8179 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5004 -0.5706 -1.4768 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6361 -0.0002 -2.3415 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4041 -0.9345 -2.4310 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1135 -1.2915 -1.7961 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6106 -0.3312 -0.7403 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2580 -1.1773 0.4550 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1399 0.9331 -0.5209 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6064 -0.0024 -1.4967 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5963 2.2569 -0.6272 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2976 3.4932 0.3615 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7617 3.7936 -1.3272 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2195 2.8709 -0.9071 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8803 1.1454 -1.4929 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1653 2.1000 -0.7373 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3954 1.8482 1.4322 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8388 1.1603 1.0661 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7132 0.1065 0.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3784 -0.5463 1.9173 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1333 -2.1054 0.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8224 -0.9759 -1.1183 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2928 -2.7436 -1.0335 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7451 -2.4205 0.6129 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3714 -0.7337 -1.9397 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8240 -0.0768 -0.4010 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0456 -1.0513 -1.5997 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9522 -2.5561 -1.8586 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8516 -3.0651 0.5901 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2537 -2.9210 -0.1622 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7855 -0.7314 1.3560 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5482 -1.7724 2.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2481 0.2152 -0.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6449 0.4320 1.4931 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8961 -0.1222 -0.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7224 -1.6395 -0.5409 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6309 -2.3989 1.7820 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0603 -2.2952 0.9947 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0061 -1.4761 3.3233 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4094 -0.3722 2.9851 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2929 0.7840 3.2446 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9842 1.0857 1.6432 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0627 -0.8442 0.7530 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9576 1.5639 2.3312 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9975 -0.1797 2.6250 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4629 -0.6629 0.9118 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1545 0.5447 2.0487 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7893 3.5724 0.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7899 2.7580 1.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2547 2.9893 0.9219 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6061 1.8875 -1.7091 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5988 -1.0571 -0.8825 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3124 -0.3746 -2.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4812 -0.6155 -2.9991 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6880 -1.5298 -1.5263 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3838 1.9177 -2.8522 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0258 1.5661 -2.3186 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0781 0.4104 -3.4325 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6834 2.4185 -1.2317 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8270 3.2680 0.4914 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6103 1.8641 1.5328 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0424 2.4638 0.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5574 1.3899 -0.6917 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9500 -0.5630 1.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6761 1.0479 1.5275 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8289 1.4538 0.6606 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0644 0.1876 1.1317 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8813 0.8718 2.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7991 -2.4805 1.9421 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4126 -1.1245 3.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1098 -1.5045 2.6364 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0619 -0.8229 -0.8347 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9322 -2.2947 0.1413 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3492 -2.5627 -1.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4511 -2.2343 -0.0471 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2215 0.7549 -1.8137 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2366 -0.8175 -2.7911 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1620 0.5368 -3.2152 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7678 -1.8710 -2.9562 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3829 -0.1807 -3.2226 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2254 -2.3461 -1.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3760 -1.4316 -2.6394 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4345 -1.8745 0.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1653 -1.8430 0.5973 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1632 -0.6177 1.3861 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.1176 -1.1806 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3750 -1.0495 -1.3479 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5763 0.3745 -2.5226 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0029 3.0461 -1.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0259 2.5638 0.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5288 2.1901 -1.2643 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 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 27 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 38 39 1 0 39 40 1 0 40 41 1 6 40 42 1 0 42 43 1 0 43 44 1 0 44 45 1 1 24 46 1 0 46 47 1 0 46 48 1 0 46 19 1 0 29 22 1 0 44 32 1 0 44 27 1 0 40 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 6 20 81 1 0 20 82 1 0 21 83 1 0 21 84 1 0 23 85 1 0 23 86 1 0 23 87 1 0 24 88 1 0 25 89 1 0 25 90 1 0 26 91 1 0 26 92 1 0 28 93 1 0 28 94 1 0 28 95 1 0 29 96 1 0 30 97 1 0 30 98 1 0 31 99 1 0 33100 1 6 34101 1 0 34102 1 0 36103 1 0 36104 1 0 36105 1 0 37106 1 0 37107 1 0 37108 1 0 38109 1 0 38110 1 0 39111 1 0 39112 1 0 41113 1 0 41114 1 0 41115 1 0 42116 1 0 42117 1 0 43118 1 0 43119 1 0 45120 1 0 45121 1 0 45122 1 0 47123 1 0 47124 1 0 47125 1 0 48126 1 0 48127 1 0 48128 1 0 M END

Standard InCHIKey	VFSRKCNYYCXRGI-OSSYFQCISA-N
Standard InCHI	InChI=1S/C46H80O2/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-40(47)48-39-27-28-44(7)37(42(39,4)5)26-29-46(9)38(44)25-24-35-36-34-41(2,3)30-31-43(36,6)32-33-45(35,46)8/h24,36-39H,10-23,25-34H2,1-9H3/t36-,37?,38?,39-,43+,44-,45+,46+/m0/s1
SMILES	CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(CC[C@]3(C)C2CC=C2[C@@H]4CC(C)(C)CC[C@]4(C)CC[C@@]32C)C1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	664.62	Volume:	773.697 ? Van der Waals volume.
Dense:	0.859	LogP:	12.336 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	6.224 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-11.636 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	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:	0.099	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.716	Fsp³:	0.935
MCE-18:	95.528 ? 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:	0.971	Fluc inhibitor:	0.014 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.752	Promiscuous compounds:	0.237

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.093	MDCK Permeability:	-4.764
Pgp-inhibitor:	0.967	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%):	0.961	30% Bioavailability (F30%):	0.974
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164	MRP1:	0.996
Plasma Protein Binding (PPB):	101.728%	Volume Distribution (VD):	1.927
Fu:	0.311% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.16
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.181	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.989
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.914	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.995	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.986	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

5.979

Half-life (T1/2):

0.677

ADMET: Toxicity

hERG Blockers:	0.603	hERG Blockers (10um):	0.868
Human Hepatotoxicity (H-HT):	0.681	Drug-induced Liver Injury (DILI):	0.088
AMES Toxicity:	0.012	Rat Oral Acute Toxicity:	0.347
Maximum Recommended Daily Dose:	0.791	Skin Sensitization:	0.983
Carcinogencity:	0.712	Eye Corrosion:	0.049
Eye Irritation:	0.392	Respiratory Toxicity:	0.877
Drug-induced Neurotoxicity:	0.022	Ototoxicity:	0.457
Hematotoxicity:	0.089	Drug-induced Nephrotoxicity:	0.296
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.915	Hek293 Cytotoxicity:	0.751
BCF:	0.798 ? 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:	5.755 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.531 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.375 ? 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
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27772	Flos inulae	Species	Lycaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27772	Flos inulae	Species	Lycaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	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

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 NPC138001 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	23218
0.1-0.2	22493
0.2-0.3	3208
0.3-0.4	761
0.4-0.5	139
0.5-0.6	19
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC10005
1.0	High Similarity	NPC91525
0.8421	Intermediate Similarity	NPC195334
0.7742	Intermediate Similarity	NPC329943
0.746	Intermediate Similarity	NPC9892
0.7377	Intermediate Similarity	NPC224145
0.7353	Intermediate Similarity	NPC86368
0.7164	Intermediate Similarity	NPC488525
0.7031	Intermediate Similarity	NPC162107
0.7031	Intermediate Similarity	NPC46912
0.6923	Remote Similarity	NPC191965
0.6866	Remote Similarity	NPC488523
0.6818	Remote Similarity	NPC286786
0.6667	Remote Similarity	NPC488524
0.6406	Remote Similarity	NPC290495
0.6389	Remote Similarity	NPC488522
0.6164	Remote Similarity	NPC485586
0.6029	Remote Similarity	NPC137306
0.597	Remote Similarity	NPC480944
0.5938	Remote Similarity	NPC142754
0.589	Remote Similarity	NPC488520
0.5781	Remote Similarity	NPC290598
0.5781	Remote Similarity	NPC30590
0.5775	Remote Similarity	NPC23621
0.5479	Remote Similarity	NPC120840
0.5441	Remote Similarity	NPC235341
0.5352	Remote Similarity	NPC127855
0.5294	Remote Similarity	NPC196753
0.5224	Remote Similarity	NPC474488
0.5211	Remote Similarity	NPC246708
0.52	Remote Similarity	NPC485589
0.5181	Remote Similarity	NPC477877
0.5143	Remote Similarity	NPC470588
0.5075	Remote Similarity	NPC601696
0.507	Remote Similarity	NPC267517
0.507	Remote Similarity	NPC611062
0.5065	Remote Similarity	NPC488521

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC138001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7289
0.1-0.2	1786
0.2-0.3	63
0.3-0.4	9
0.4-0.5	3
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