NPASS Compound

Natural Product: NPC303090

Natural Product ID	NPC303090
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1R,3R,4S,5R)-1,3-Bis[3-(3,4-Dihydroxyphenyl)Prop-2-Enoyloxy]-4,5-Dihydroxycyclohexane-1-Carboxylic Acid
IUPAC Name	(1R,3R,4S,5R)-1,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2356300
PubChem CID	122685
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002512] Quinic acids and derivatives

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 61 63 0 0 0 0 0 0 0 0999 V2000 -7.8616 0.2580 0.3311 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1156 0.8012 0.1676 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3646 2.0295 -0.3954 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2626 2.7450 -0.8163 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9956 2.2162 -0.6604 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7619 0.9805 -0.0930 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4057 0.4891 0.0366 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0553 -0.6682 0.5533 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6689 -1.0985 0.6517 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3549 -2.2216 1.1541 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5844 -0.3604 0.2256 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2420 -0.7794 0.3212 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4586 0.0747 1.2840 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0064 -0.3760 1.2055 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0647 -1.8098 0.7338 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6157 -1.9435 -0.7037 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5638 -0.9955 -0.9821 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0507 0.1130 -1.5987 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2461 -3.2716 -0.8948 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5910 -0.3062 2.5586 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0645 -1.0099 3.4867 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6741 0.4605 2.9314 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7124 0.4381 0.3199 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1011 0.2718 0.1024 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6352 -0.6245 0.7539 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7925 1.1097 -0.8200 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0010 1.1608 -1.2224 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2079 0.4407 -0.9772 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3447 -0.8025 -0.4471 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5886 -1.3935 -0.1519 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7413 -0.7078 -0.4021 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6530 0.5478 -0.9385 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4364 1.1037 -1.2165 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8367 1.2284 -1.1870 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9729 -1.2673 -0.1205 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4515 3.9889 -1.3913 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6520 2.5453 -0.5434 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6924 -0.7065 0.7747 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9746 0.2311 0.5013 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1259 2.8024 -1.0037 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6026 1.1480 -0.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8146 -1.3291 0.9200 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2971 -1.8017 0.8030 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8387 -0.1531 2.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5723 1.1487 1.1370 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4825 -2.4864 1.4288 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0898 -2.1729 0.8029 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4713 -1.7331 -1.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2511 -1.5873 -1.6282 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5648 0.4746 -2.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7534 -3.7183 -1.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9587 0.5289 3.9126 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1327 1.9225 -1.3172 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1981 1.9931 -2.0244 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5202 -1.4430 -0.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6564 -2.3857 0.2718 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4163 2.0993 -1.6366 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6802 1.0276 -0.6293 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5321 -1.0194 0.6880 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6869 4.7803 -0.7957 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9075 3.2726 0.1205 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 3 8 9 1 0 9 10 2 0 9 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 1 0 17 18 1 0 16 19 1 0 14 20 1 0 20 21 2 0 20 22 1 0 14 23 1 6 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 3 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 31 35 1 0 4 36 1 0 3 37 1 0 6 1 1 0 17 12 1 0 33 28 1 0 1 38 1 0 2 39 1 0 5 40 1 0 7 41 1 0 8 42 1 0 12 43 1 1 13 44 1 0 13 45 1 0 15 46 1 0 15 47 1 0 16 48 1 6 17 49 1 6 18 50 1 0 19 51 1 0 22 52 1 0 26 53 1 0 27 54 1 0 29 55 1 0 30 56 1 0 33 57 1 0 34 58 1 0 35 59 1 0 36 60 1 0 37 61 1 0 M END

Standard InCHIKey	YDDUMTOHNYZQPO-GCBRTHAASA-N
Standard InCHI	InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/t19-,20-,23+,25-/m1/s1
SMILES	c1cc(c(cc1C=CC(=O)O[C@@H]1C[C@](C[C@H]([C@@H]1O)O)(C(=O)O)OC(=O)C=Cc1ccc(c(c1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.13	Volume:	491.768 ? Van der Waals volume.
Dense:	1.05	LogP:	1.467 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.6 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.4 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	23.0
TPSA:	211.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.156	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.164	Fsp³:	0.24
MCE-18:	81.29 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.829	Fluc inhibitor:	0.999 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.22 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.637 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.453	Promiscuous compounds:	0.318

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.509	MDCK Permeability:	-5.039
Pgp-inhibitor:	0.0	Pgp-substrate:	0.013
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):	0.635
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.902
Plasma Protein Binding (PPB):	75.724%	Volume Distribution (VD):	0.059
Fu:	23.049% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.989
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

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:	0.0	CYP3A4-substrate:	0.768
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

5.112

Half-life (T1/2):

3.179

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.217
Human Hepatotoxicity (H-HT):	0.356	Drug-induced Liver Injury (DILI):	0.353
AMES Toxicity:	0.711	Rat Oral Acute Toxicity:	0.12
Maximum Recommended Daily Dose:	0.797	Skin Sensitization:	1.0
Carcinogencity:	0.118	Eye Corrosion:	0.001
Eye Irritation:	0.439	Respiratory Toxicity:	0.089
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.851
Hematotoxicity:	0.007	Drug-induced Nephrotoxicity:	0.659
Genotoxicity:	0.719	RPMI-8226 Immunitoxicity:	0.021
A549 Cytotoxicity:	0.886	Hek293 Cytotoxicity:	0.22
BCF:	0.621 ? 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:	3.355 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.616 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.327 ? 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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jep.2005.01.054]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643020]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17996677]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26081757]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214875]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[27169184]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27276091]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181920]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31418264]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38754641]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4014	Erigeron breviscapus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17782	Inula britannica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4014	Erigeron breviscapus	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
Potency	7
AC50	3

Activity Type	# Activity
Individual protein	2
Others	8

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	668.2	nM	PubChem BioAssay data set
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	26601.1	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Potency	n.a.	13332.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10590.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	26832.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	3548.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	28183.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	19952.6	nM	PubChem BioAssay data set

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 NPC303090 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	9416
0.1-0.2	37291
0.2-0.3	2706
0.3-0.4	332
0.4-0.5	68
0.5-0.6	22
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC284948
1.0	High Similarity	NPC301382
1.0	High Similarity	NPC37331
0.9333	High Similarity	NPC220664
0.85	High Similarity	NPC283560
0.85	High Similarity	NPC24295
0.7826	Intermediate Similarity	NPC471076
0.7826	Intermediate Similarity	NPC192568
0.7143	Intermediate Similarity	NPC319628
0.6552	Remote Similarity	NPC224208
0.6552	Remote Similarity	NPC41661
0.6515	Remote Similarity	NPC37250
0.6515	Remote Similarity	NPC142703
0.6515	Remote Similarity	NPC152942
0.6515	Remote Similarity	NPC9991
0.6515	Remote Similarity	NPC302857
0.6515	Remote Similarity	NPC600892
0.6324	Remote Similarity	NPC477334
0.6154	Remote Similarity	NPC13818
0.5797	Remote Similarity	NPC471027
0.5672	Remote Similarity	NPC219428
0.5625	Remote Similarity	NPC488563
0.5507	Remote Similarity	NPC295492
0.5507	Remote Similarity	NPC303683
0.5507	Remote Similarity	NPC274891
0.5417	Remote Similarity	NPC278068
0.5357	Remote Similarity	NPC473275
0.5278	Remote Similarity	NPC205751
0.5278	Remote Similarity	NPC206095
0.5278	Remote Similarity	NPC35702
0.5278	Remote Similarity	NPC224389
0.5238	Remote Similarity	NPC474275
0.5224	Remote Similarity	NPC258469
0.5224	Remote Similarity	NPC43158
0.5224	Remote Similarity	NPC610147
0.5195	Remote Similarity	NPC156875
0.5161	Remote Similarity	NPC217052
0.5161	Remote Similarity	NPC329344
0.5161	Remote Similarity	NPC237506
0.5161	Remote Similarity	NPC32626
0.5139	Remote Similarity	NPC477333

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC303090 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3018
0.1-0.2	5997
0.2-0.3	131
0.3-0.4	3
0.4-0.5	0
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	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6190	Approved

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