NPASS Compound

Natural Product: NPC173569

Natural Product ID	NPC173569
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-(P-Coumaroyl)Ursolic Acid
IUPAC Name	(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms	3-(P-Coumaroyl)Ursolic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL463917
PubChem CID	24203733
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 97102 0 0 0 0 0 0 0 0999 V2000 -6.2091 1.4216 -2.9200 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6474 0.2150 -2.0752 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4340 0.7783 -0.9320 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4048 1.3534 0.0325 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7548 0.1059 0.6593 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0369 0.5557 1.8685 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6062 0.1299 2.0047 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8440 0.2709 0.7281 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7895 1.6806 0.2449 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5391 -0.5542 -0.2884 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8404 -1.2001 -1.2157 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3692 -1.1613 -1.3199 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7438 -0.1765 -0.3580 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7363 -0.2274 -0.3502 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3426 -1.5633 -0.6067 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2341 0.6510 -1.5149 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7078 0.7937 -1.5563 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4045 1.0692 -0.2843 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7320 0.6073 0.9674 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3930 -0.6356 1.5441 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9511 1.7163 2.0177 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2502 0.4804 0.8557 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6748 -0.0827 2.1277 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7929 0.3670 2.1080 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4392 -0.3240 0.9557 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6832 -1.7507 1.3732 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6701 0.3871 -0.3363 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8833 1.0188 -0.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9259 2.2671 -0.2509 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1283 0.2220 -0.3749 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2877 0.8260 -0.3569 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5378 0.0944 -0.4112 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7160 0.8327 -0.3874 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9319 0.2153 -0.4349 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0105 -1.1499 -0.5074 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8526 -1.8709 -0.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5990 -1.2737 -0.4836 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2602 -1.7562 -0.5548 O 0 0 0 0 0 1 0 0 0 0 0 0 -5.0306 -0.7116 -0.3299 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5085 -0.6569 -1.7377 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8256 -2.0585 -2.2940 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9453 -0.6970 1.1336 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1856 -1.8579 0.7217 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8213 -0.1534 2.0592 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0497 2.1118 -3.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2745 1.8506 -2.5617 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0138 1.0024 -3.9470 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4049 -0.3007 -2.7391 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0041 -0.0186 -0.4572 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0902 1.5731 -1.3405 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9614 1.8741 0.8289 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6684 1.9831 -0.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0367 1.6830 1.9807 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5341 0.2289 2.8338 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1252 0.8078 2.7602 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5319 -0.8783 2.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5994 2.3232 0.6828 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8437 2.2156 0.5101 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9201 1.7630 -0.8617 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3380 -1.8181 -1.9782 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0569 -0.9023 -2.3452 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9955 -2.1778 -1.0038 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0396 0.8412 -0.7593 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4345 -1.4177 -0.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9396 -1.9256 -1.5891 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2571 -2.3087 0.1669 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8922 0.1597 -2.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7287 1.6487 -1.4610 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9055 1.6592 -2.2633 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1754 -0.0702 -2.1201 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6948 2.1612 -0.2280 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0073 -0.4013 2.4616 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6652 -1.3909 1.8745 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1591 -1.0573 0.8290 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1231 2.4267 2.0345 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8775 2.2819 1.7889 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0553 1.2742 3.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8567 1.5411 0.7879 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6422 -1.2005 2.0680 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2127 0.2962 2.9955 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2640 -0.0380 3.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7805 1.4515 2.0718 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6951 -2.1257 1.0600 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9669 -2.4781 1.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6970 -1.8429 2.4972 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0718 -0.8444 -0.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3086 1.9258 -0.2986 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6491 1.9242 -0.3296 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8146 0.8600 -0.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8569 -2.9549 -0.5875 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7057 -1.8778 -0.5039 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1618 -1.7933 -0.0061 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6441 -0.3167 -2.3892 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4752 -2.8049 -1.5314 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3765 -2.2440 -3.2668 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9387 -2.1711 -2.3008 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3244 -0.7065 2.7458 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 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 18 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 35 38 1 0 10 39 1 0 39 40 1 0 40 41 1 0 5 42 1 1 42 43 2 0 42 44 1 0 40 2 1 0 39 5 1 0 25 8 1 0 37 32 1 0 25 13 1 0 22 14 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 6 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 6 53 1 0 6 54 1 0 7 55 1 0 7 56 1 0 9 57 1 0 9 58 1 0 9 59 1 0 11 60 1 0 12 61 1 0 12 62 1 0 13 63 1 6 15 64 1 0 15 65 1 0 15 66 1 0 16 67 1 0 16 68 1 0 17 69 1 0 17 70 1 0 18 71 1 1 20 72 1 0 20 73 1 0 20 74 1 0 21 75 1 0 21 76 1 0 21 77 1 0 22 78 1 6 23 79 1 0 23 80 1 0 24 81 1 0 24 82 1 0 26 83 1 0 26 84 1 0 26 85 1 0 30 86 1 0 31 87 1 0 33 88 1 0 34 89 1 0 36 90 1 0 37 91 1 0 39 92 1 1 40 93 1 6 41 94 1 0 41 95 1 0 41 96 1 0 44 97 1 0 M CHG 1 38 -1 M END

Standard InCHIKey	ZOXDAGKKDOEJBW-YVZDRRNJSA-N
Standard InCHI	InChI=1S/C39H54O5/c1-24-16-21-39(34(42)43)23-22-37(6)28(33(39)25(24)2)13-14-30-36(5)19-18-31(35(3,4)29(36)17-20-38(30,37)7)44-32(41)15-10-26-8-11-27(40)12-9-26/h8-13,15,24-25,29-31,33,40H,14,16-23H2,1-7H3,(H,42,43)/p-1/b15-10+/t24-,25+,29+,30-,31+,33+,36+,37-,38-,39+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)/C=C/c3ccc(cc3)[O-])[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.4	Volume:	657.257 ? Van der Waals volume.
Dense:	0.917	LogP:	6.529 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.662 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.048 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	35.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.204	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.88	Fsp³:	0.692
MCE-18:	158.667 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.992	Fluc inhibitor:	0.989 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.293 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.214	Promiscuous compounds:	0.066

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.536	MDCK Permeability:	-5.096
Pgp-inhibitor:	0.939	Pgp-substrate:	0.0
PAMPA:	0.988 ? 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%):	0.874	30% Bioavailability (F30%):	0.687
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.572
Plasma Protein Binding (PPB):	98.528%	Volume Distribution (VD):	-0.394
Fu:	1.1% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.979	BCRP inhibitor:	0.007
BSEP inhibitor:	0.999

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:	0.0
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.994
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.941
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):

2.355

Half-life (T1/2):

1.151

ADMET: Toxicity

hERG Blockers:	0.064	hERG Blockers (10um):	0.095
Human Hepatotoxicity (H-HT):	0.76	Drug-induced Liver Injury (DILI):	0.894
AMES Toxicity:	0.407	Rat Oral Acute Toxicity:	0.262
Maximum Recommended Daily Dose:	0.781	Skin Sensitization:	0.99
Carcinogencity:	0.901	Eye Corrosion:	0.005
Eye Irritation:	0.485	Respiratory Toxicity:	0.825
Drug-induced Neurotoxicity:	0.168	Ototoxicity:	0.461
Hematotoxicity:	0.383	Drug-induced Nephrotoxicity:	0.964
Genotoxicity:	0.958	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.224	Hek293 Cytotoxicity:	0.569
BCF:	0.997 ? 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:	4.527 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.576 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.268 ? 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
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/np50070a005]
NPO27072	Monochaetum vulcanicum	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165161]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	leaves	Botanical Garden of Innsbruck, Austria	n.a.	PMID[20100662]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21923134]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37656744]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27072	Monochaetum vulcanicum	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27072	Monochaetum vulcanicum	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25618	Eriobotrya japonica	Species	Rosaceae	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
MIC	1

Activity Type	# Activity
Individual protein	1
Organism	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT59	Individual protein	DNA polymerase beta	Homo sapiens	IC50	>	50000.0	nM	PMID[15165161]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	6.25	ug.mL-1	PMID[29202408]

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 NPC173569 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	13708
0.1-0.2	32618
0.2-0.3	2878
0.3-0.4	465
0.4-0.5	118
0.5-0.6	52
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8861	High Similarity	NPC485587
0.7468	Intermediate Similarity	NPC485588
0.7403	Intermediate Similarity	NPC485589
0.7037	Intermediate Similarity	NPC485586
0.6957	Remote Similarity	NPC172311
0.6882	Remote Similarity	NPC304110
0.6882	Remote Similarity	NPC27518
0.6882	Remote Similarity	NPC611516
0.6824	Remote Similarity	NPC485585
0.6782	Remote Similarity	NPC485882
0.6566	Remote Similarity	NPC118033
0.6458	Remote Similarity	NPC178093
0.6421	Remote Similarity	NPC479744
0.6392	Remote Similarity	NPC610795
0.6344	Remote Similarity	NPC477874
0.6327	Remote Similarity	NPC479745
0.6211	Remote Similarity	NPC477873
0.5977	Remote Similarity	NPC230151
0.5918	Remote Similarity	NPC482052
0.5876	Remote Similarity	NPC22676
0.58	Remote Similarity	NPC479747
0.58	Remote Similarity	NPC479746
0.5765	Remote Similarity	NPC113989
0.566	Remote Similarity	NPC53520
0.5647	Remote Similarity	NPC120840
0.5625	Remote Similarity	NPC182249
0.5612	Remote Similarity	NPC171007
0.5612	Remote Similarity	NPC190849
0.5556	Remote Similarity	NPC488215
0.5545	Remote Similarity	NPC25491
0.5542	Remote Similarity	NPC274050
0.5542	Remote Similarity	NPC162632
0.549	Remote Similarity	NPC479739
0.5465	Remote Similarity	NPC173089
0.5464	Remote Similarity	NPC473591
0.5446	Remote Similarity	NPC605663
0.5437	Remote Similarity	NPC482051
0.5437	Remote Similarity	NPC324798
0.5437	Remote Similarity	NPC479742
0.5412	Remote Similarity	NPC51700
0.5412	Remote Similarity	NPC88716
0.5412	Remote Similarity	NPC68160
0.5327	Remote Similarity	NPC481234
0.5327	Remote Similarity	NPC479431
0.5312	Remote Similarity	NPC177246
0.5306	Remote Similarity	NPC248287
0.5306	Remote Similarity	NPC234548
0.5294	Remote Similarity	NPC488214
0.5294	Remote Similarity	NPC54627
0.5294	Remote Similarity	NPC249817
0.5234	Remote Similarity	NPC601567
0.5234	Remote Similarity	NPC606631
0.5208	Remote Similarity	NPC57362
0.52	Remote Similarity	NPC8102
0.52	Remote Similarity	NPC66894
0.5192	Remote Similarity	NPC475482
0.5172	Remote Similarity	NPC61543
0.5172	Remote Similarity	NPC293048
0.5172	Remote Similarity	NPC225585
0.5169	Remote Similarity	NPC477290
0.5114	Remote Similarity	NPC477288
0.5096	Remote Similarity	NPC205392
0.5096	Remote Similarity	NPC105942
0.5093	Remote Similarity	NPC310729
0.5093	Remote Similarity	NPC150310
0.5091	Remote Similarity	NPC481235
0.5047	Remote Similarity	NPC479740
0.5047	Remote Similarity	NPC479741
0.5042	Remote Similarity	NPC488211

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC173569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3967
0.1-0.2	5132
0.2-0.3	42
0.3-0.4	6
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