NPASS Compound

Natural Product: NPC80843

Natural Product ID	NPC80843
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-[(O-Beta-D-Glucopyranosy1-(1->2)-Alpha-L-Arabinopyranosyl)Oxy]-16Alpha-Hydroxyolean-12-En-28-Oic Acid
IUPAC Name	(4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-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	CHEMBL540941
PubChem CID	45269267
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 120126 0 0 0 0 0 0 0 0999 V2000 9.5055 3.5796 -1.2129 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1956 3.3488 -0.7847 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3017 2.3779 0.3943 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0287 2.1271 0.8422 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7929 0.8002 1.1563 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4151 0.1151 0.0266 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1301 -0.4053 0.1638 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1962 0.1034 -0.9042 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3824 -0.6550 -2.0951 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6325 -1.2151 -2.1752 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9225 -2.2765 -1.1497 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1532 -1.9296 0.1098 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8463 -2.3758 0.0247 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5465 -3.5467 -1.5592 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9055 -0.1852 -0.5147 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0354 0.8623 -0.5096 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9823 0.7618 -1.5986 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0926 -0.4298 -1.4805 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4783 -0.5963 -0.0597 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1479 0.6630 0.6468 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3027 1.0106 0.7747 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3204 2.5216 1.0874 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0182 0.3495 1.8840 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8912 0.7452 1.9339 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3648 0.7311 1.6160 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8100 -0.6084 0.9925 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9767 -0.6712 -0.2293 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4075 -1.7817 -1.1231 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7639 -1.3494 -1.5635 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6173 -0.8132 -0.7452 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2691 -0.6119 0.6506 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8467 0.6049 1.3315 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0909 -1.7372 1.3181 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2713 -2.1795 0.5672 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9115 -1.3410 -0.4908 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9631 -0.4900 -1.2916 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2267 0.9479 -1.4411 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6275 1.4082 -1.3688 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1127 1.9226 -2.7339 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7374 2.6320 -0.4471 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6253 0.4138 -0.9188 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1591 -0.6465 -0.0011 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5175 -2.3741 -1.4473 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4260 -3.5939 -1.2131 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1729 -1.9733 -2.5818 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3195 -2.4558 1.4918 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5625 -1.6581 2.0204 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1224 -1.8471 0.4832 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9789 0.1607 1.8502 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2235 0.1973 1.0204 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0262 1.1635 -0.1299 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2779 1.5777 -0.5799 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6197 -1.0617 0.5921 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1503 0.8177 3.0720 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4458 3.9314 -2.1504 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7017 4.2607 -0.4174 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5873 2.8552 -1.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8948 2.8163 1.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9636 0.7638 1.8884 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7498 -0.1267 1.1605 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3852 1.1598 -1.1441 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4243 -0.4329 -2.2401 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6712 -1.7312 -3.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0032 -2.2539 -0.8898 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6164 -2.2980 1.0276 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5336 -2.7467 0.8969 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3377 -4.0506 -1.8331 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6353 1.7731 -0.8138 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5713 0.6166 -2.5521 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4871 1.7256 -1.7062 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7289 -0.2537 -2.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6673 -1.3148 -1.8024 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5873 1.4907 0.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2829 2.9575 0.8165 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1407 2.6986 2.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5252 3.0445 0.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4484 -0.6095 1.5826 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4609 0.2563 2.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8943 1.0135 2.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7115 1.8105 2.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5603 0.1244 2.7489 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8719 1.0091 2.5158 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4334 1.4762 0.7620 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2083 0.2915 -0.7929 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4677 -2.7626 -0.5607 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7259 -2.0005 -1.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9724 -1.5257 -2.6379 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3366 1.5403 1.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9445 0.6837 1.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7257 0.3413 2.4388 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4486 -2.6570 1.4683 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3822 -1.4704 2.3554 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0849 -3.2150 0.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0302 -0.8935 -2.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5966 1.6192 -0.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8463 1.2676 -2.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2707 2.2765 -3.3347 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6100 1.0922 -3.2891 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8839 2.7107 -2.6025 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9833 2.6191 0.3494 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6409 3.5769 -1.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7371 2.6807 0.0349 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1727 -0.0586 -1.7841 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4684 0.9504 -0.3746 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9836 -1.4046 0.0850 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0405 -0.2503 1.0361 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1935 -2.5992 -3.3872 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1770 -3.3301 1.9318 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3977 -1.5801 2.7787 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4807 -2.6850 1.6772 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6642 -1.4964 2.6649 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0561 -2.1562 -0.0761 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5880 -2.6874 0.2211 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4031 -1.8404 1.5333 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7021 -0.8882 2.0586 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0422 0.6077 1.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4778 0.6597 -0.9266 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9502 1.5227 0.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3249 -1.7609 1.2419 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7630 1.7215 3.0270 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 11 14 1 0 8 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 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 1 31 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 38 40 1 0 38 41 1 0 41 42 1 0 35 43 1 6 43 44 2 0 43 45 1 0 34 46 1 0 26 47 1 1 19 48 1 1 5 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 51 3 1 0 12 7 1 0 21 16 1 0 31 26 1 0 42 35 1 0 27 19 1 0 36 30 1 0 1 55 1 0 2 56 1 0 2 57 1 0 3 58 1 1 5 59 1 1 7 60 1 1 8 61 1 6 10 62 1 0 10 63 1 0 11 64 1 1 12 65 1 1 13 66 1 0 14 67 1 0 16 68 1 6 17 69 1 0 17 70 1 0 18 71 1 0 18 72 1 0 20 73 1 6 22 74 1 0 22 75 1 0 22 76 1 0 23 77 1 0 23 78 1 0 23 79 1 0 24 80 1 0 24 81 1 0 25 82 1 0 25 83 1 0 27 84 1 6 28 85 1 0 28 86 1 0 29 87 1 0 32 88 1 0 32 89 1 0 32 90 1 0 33 91 1 0 33 92 1 0 34 93 1 6 36 94 1 6 37 95 1 0 37 96 1 0 39 97 1 0 39 98 1 0 39 99 1 0 40100 1 0 40101 1 0 40102 1 0 41103 1 0 41104 1 0 42105 1 0 42106 1 0 45107 1 0 46108 1 0 47109 1 0 47110 1 0 47111 1 0 48112 1 0 48113 1 0 48114 1 0 49115 1 1 50116 1 1 51117 1 6 52118 1 0 53119 1 0 54120 1 0 M END

Standard InCHIKey	CTTLCTYXPWGOMY-JYTHRGSDSA-N
Standard InCHI	InChI=1S/C41H66O13/c1-36(2)14-15-41(35(49)50)21(16-36)20-8-9-25-38(5)12-11-27(37(3,4)24(38)10-13-39(25,6)40(20,7)17-26(41)44)53-34-32(28(45)22(43)19-51-34)54-33-31(48)30(47)29(46)23(18-42)52-33/h8,21-34,42-48H,9-19H2,1-7H3,(H,49,50)/t21-,22-,23+,24-,25+,26+,27-,28-,29+,30-,31+,32+,33-,34-,38-,39+,40+,41+/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC[C@@H]([C@@H]2O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@H]([C@@]2([C@H]3CC(C)(C)CC2)C(=O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	766.45	Volume:	766.797 ? Van der Waals volume.
Dense:	1.0	LogP:	2.152 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.697 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.082 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	39.0
TPSA:	215.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.144	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.808	Fsp³:	0.927
MCE-18:	151.772 ? 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:	0.844	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? 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:	0.182	Promiscuous compounds:	0.128

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.964	MDCK Permeability:	-5.111
Pgp-inhibitor:	0.0	Pgp-substrate:	0.006
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):	0.097
20% Bioavailability (F20%):	0.295	30% Bioavailability (F30%):	0.835
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085	MRP1:	0.401
Plasma Protein Binding (PPB):	75.267%	Volume Distribution (VD):	-0.555
Fu:	18.227% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.004
BSEP inhibitor:	0.014

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.057
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):

0.33

Half-life (T1/2):

2.091

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.005
Human Hepatotoxicity (H-HT):	0.804	Drug-induced Liver Injury (DILI):	0.934
AMES Toxicity:	0.868	Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.013	Skin Sensitization:	1.0
Carcinogencity:	0.688	Eye Corrosion:	0.0
Eye Irritation:	0.032	Respiratory Toxicity:	0.08
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.988
Hematotoxicity:	0.836	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.667	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.703	Hek293 Cytotoxicity:	0.251
BCF:	1.033 ? 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:	3.59 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.177 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.278 ? 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
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	Eukaryota	underground parts	n.a.	n.a.	PMID[19449879]
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25841	Caulophyllum thalictroides	Species	Berberidaceae	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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	11.8	ug.mL-1	PMID[8864235]

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 NPC80843 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	22007
0.1-0.2	22920
0.2-0.3	3349
0.3-0.4	916
0.4-0.5	434
0.5-0.6	132
0.6-0.7	45
0.7-0.8	0
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC475486
0.8571	High Similarity	NPC288205
0.8571	High Similarity	NPC51465
0.8462	Intermediate Similarity	NPC127056
0.8372	Intermediate Similarity	NPC31839
0.8144	Intermediate Similarity	NPC488515
0.7766	Intermediate Similarity	NPC59804
0.7667	Intermediate Similarity	NPC242611
0.7624	Intermediate Similarity	NPC324875
0.7624	Intermediate Similarity	NPC292677
0.7604	Intermediate Similarity	NPC488516
0.7579	Intermediate Similarity	NPC56713
0.75	Intermediate Similarity	NPC475119
0.7282	Intermediate Similarity	NPC291903
0.7263	Intermediate Similarity	NPC164194
0.7103	Intermediate Similarity	NPC473824
0.7071	Intermediate Similarity	NPC488561
0.7064	Intermediate Similarity	NPC219180
0.7064	Intermediate Similarity	NPC251263
0.7041	Intermediate Similarity	NPC174679
0.7041	Intermediate Similarity	NPC279554
0.7019	Intermediate Similarity	NPC276093
0.699	Remote Similarity	NPC257468
0.697	Remote Similarity	NPC480424
0.6957	Remote Similarity	NPC606107
0.6952	Remote Similarity	NPC75318
0.6907	Remote Similarity	NPC76999
0.69	Remote Similarity	NPC472949
0.6869	Remote Similarity	NPC25605
0.6796	Remote Similarity	NPC104400
0.6796	Remote Similarity	NPC10320
0.6762	Remote Similarity	NPC79718
0.6729	Remote Similarity	NPC488564
0.6699	Remote Similarity	NPC114304
0.6667	Remote Similarity	NPC481082
0.6667	Remote Similarity	NPC164419
0.6667	Remote Similarity	NPC22956
0.6634	Remote Similarity	NPC109079
0.6607	Remote Similarity	NPC166422
0.6542	Remote Similarity	NPC37134
0.6518	Remote Similarity	NPC133818
0.6455	Remote Similarity	NPC480939
0.6415	Remote Similarity	NPC139044
0.6339	Remote Similarity	NPC200788
0.6316	Remote Similarity	NPC204407
0.6306	Remote Similarity	NPC62725
0.6296	Remote Similarity	NPC119794
0.6286	Remote Similarity	NPC469945
0.6286	Remote Similarity	NPC112352
0.6275	Remote Similarity	NPC12288
0.6261	Remote Similarity	NPC283417
0.6261	Remote Similarity	NPC200049
0.625	Remote Similarity	NPC283849
0.6218	Remote Similarity	NPC161717
0.6207	Remote Similarity	NPC54636
0.6196	Remote Similarity	NPC601365
0.6182	Remote Similarity	NPC323359
0.6168	Remote Similarity	NPC164389
0.6168	Remote Similarity	NPC180550
0.6168	Remote Similarity	NPC35405
0.6161	Remote Similarity	NPC280941
0.6161	Remote Similarity	NPC235772
0.6117	Remote Similarity	NPC136877
0.6111	Remote Similarity	NPC63159
0.6087	Remote Similarity	NPC323341
0.6036	Remote Similarity	NPC23275
0.6	Remote Similarity	NPC302887
0.5983	Remote Similarity	NPC475140
0.5982	Remote Similarity	NPC160452
0.5966	Remote Similarity	NPC21691
0.5948	Remote Similarity	NPC243680
0.5946	Remote Similarity	NPC145899
0.5922	Remote Similarity	NPC270667
0.5917	Remote Similarity	NPC265841
0.5917	Remote Similarity	NPC488308
0.5882	Remote Similarity	NPC4749
0.5872	Remote Similarity	NPC44716
0.5872	Remote Similarity	NPC480475
0.5868	Remote Similarity	NPC312650
0.5862	Remote Similarity	NPC151543
0.5856	Remote Similarity	NPC64715
0.5841	Remote Similarity	NPC488209
0.5818	Remote Similarity	NPC471383
0.5812	Remote Similarity	NPC471384
0.5789	Remote Similarity	NPC104137
0.5789	Remote Similarity	NPC26626
0.578	Remote Similarity	NPC160415
0.578	Remote Similarity	NPC117714
0.5766	Remote Similarity	NPC73829
0.576	Remote Similarity	NPC488309
0.5758	Remote Similarity	NPC28198
0.5758	Remote Similarity	NPC476123
0.5752	Remote Similarity	NPC301449
0.5752	Remote Similarity	NPC601290
0.5738	Remote Similarity	NPC271610
0.5728	Remote Similarity	NPC191410
0.5727	Remote Similarity	NPC251768
0.5714	Remote Similarity	NPC228784
0.5714	Remote Similarity	NPC324341
0.5714	Remote Similarity	NPC601810
0.5702	Remote Similarity	NPC187618
0.5702	Remote Similarity	NPC480473
0.5702	Remote Similarity	NPC480474
0.5691	Remote Similarity	NPC471385
0.5688	Remote Similarity	NPC192791
0.5652	Remote Similarity	NPC481078
0.5641	Remote Similarity	NPC475287
0.5636	Remote Similarity	NPC30289
0.5631	Remote Similarity	NPC475633
0.562	Remote Similarity	NPC488211
0.5619	Remote Similarity	NPC1046
0.5607	Remote Similarity	NPC475296
0.5596	Remote Similarity	NPC263756
0.5596	Remote Similarity	NPC469946
0.5593	Remote Similarity	NPC79643
0.5575	Remote Similarity	NPC484832
0.5546	Remote Similarity	NPC284449
0.5536	Remote Similarity	NPC475591
0.5536	Remote Similarity	NPC236870
0.5524	Remote Similarity	NPC475472
0.5517	Remote Similarity	NPC469947
0.5517	Remote Similarity	NPC480948
0.5517	Remote Similarity	NPC187290
0.5505	Remote Similarity	NPC6377
0.5505	Remote Similarity	NPC208381
0.55	Remote Similarity	NPC135904
0.5495	Remote Similarity	NPC605226
0.5492	Remote Similarity	NPC71391
0.549	Remote Similarity	NPC286347
0.5487	Remote Similarity	NPC275668
0.5487	Remote Similarity	NPC475504
0.5463	Remote Similarity	NPC474589
0.5462	Remote Similarity	NPC120667
0.5462	Remote Similarity	NPC278272
0.5455	Remote Similarity	NPC213674
0.5446	Remote Similarity	NPC488526
0.5439	Remote Similarity	NPC471435
0.5439	Remote Similarity	NPC471434
0.5437	Remote Similarity	NPC100383
0.5424	Remote Similarity	NPC476992
0.5413	Remote Similarity	NPC114441
0.5385	Remote Similarity	NPC207738
0.5378	Remote Similarity	NPC313110
0.5377	Remote Similarity	NPC473481
0.5372	Remote Similarity	NPC123199
0.5368	Remote Similarity	NPC222047
0.5366	Remote Similarity	NPC85154
0.5366	Remote Similarity	NPC192765
0.5351	Remote Similarity	NPC222580
0.5351	Remote Similarity	NPC123796
0.5351	Remote Similarity	NPC297263
0.5345	Remote Similarity	NPC218954
0.5323	Remote Similarity	NPC178264
0.5321	Remote Similarity	NPC251309
0.5319	Remote Similarity	NPC201657
0.5317	Remote Similarity	NPC476779
0.531	Remote Similarity	NPC473383
0.531	Remote Similarity	NPC2370
0.5294	Remote Similarity	NPC57362
0.5294	Remote Similarity	NPC185466
0.528	Remote Similarity	NPC286457
0.528	Remote Similarity	NPC476774
0.528	Remote Similarity	NPC476780
0.5276	Remote Similarity	NPC110700
0.5271	Remote Similarity	NPC220160
0.5271	Remote Similarity	NPC488212
0.5267	Remote Similarity	NPC489209
0.5254	Remote Similarity	NPC31838
0.525	Remote Similarity	NPC60557
0.525	Remote Similarity	NPC67857
0.525	Remote Similarity	NPC610204
0.5242	Remote Similarity	NPC181066
0.5238	Remote Similarity	NPC41061
0.5238	Remote Similarity	NPC227551
0.5234	Remote Similarity	NPC302543
0.5234	Remote Similarity	NPC480938
0.5225	Remote Similarity	NPC470512
0.5221	Remote Similarity	NPC480947
0.5214	Remote Similarity	NPC481079
0.5214	Remote Similarity	NPC606145
0.521	Remote Similarity	NPC11242
0.5203	Remote Similarity	NPC470218
0.5203	Remote Similarity	NPC602995
0.52	Remote Similarity	NPC57484
0.5197	Remote Similarity	NPC484059
0.5197	Remote Similarity	NPC484060
0.5189	Remote Similarity	NPC284807
0.5182	Remote Similarity	NPC108748
0.5175	Remote Similarity	NPC232237
0.5175	Remote Similarity	NPC46665
0.5167	Remote Similarity	NPC25998
0.5156	Remote Similarity	NPC305981
0.5156	Remote Similarity	NPC111466
0.5156	Remote Similarity	NPC476777
0.5154	Remote Similarity	NPC484063
0.5154	Remote Similarity	NPC484064
0.5138	Remote Similarity	NPC48499
0.5124	Remote Similarity	NPC609119
0.5122	Remote Similarity	NPC603137

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC80843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6576
0.1-0.2	2500
0.2-0.3	63
0.3-0.4	9
0.4-0.5	2
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