NPASS Compound

Natural Product: NPC258469

Natural Product ID	NPC258469
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VEBNYMXKXIIGFX-VOHNXBSUSA-N
IUPAC Name	n.a.
Synonyms	3,5-Dicaffeoylquinic Acid Methyl Ester
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL463337
PubChem CID	NA
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 64 66 0 0 0 0 0 0 0 0999 V2000 0.6137 -6.9518 -0.1778 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4272 -5.6186 0.2714 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2713 -4.5434 -0.5896 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2993 -4.7815 -1.8114 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0838 -3.1982 -0.0103 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0975 -3.2512 1.3819 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1575 -2.5131 -0.4412 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 -1.0718 -0.7643 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2987 -0.4583 -0.5029 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0513 0.1513 -1.4769 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5965 0.1618 -2.6458 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3569 0.7814 -1.1841 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8753 0.8018 -0.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1584 1.4248 0.2701 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6468 1.4013 1.5875 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8536 1.9767 1.8899 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6104 2.5887 0.9086 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1722 2.6361 -0.3967 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9454 2.0443 -0.6719 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9292 3.2494 -1.3832 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8341 3.1632 1.2570 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0063 -0.3163 -0.0066 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2021 -1.1055 0.3828 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2611 -2.3421 -0.5004 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4065 -0.3672 0.3123 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1604 -0.2218 1.4556 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7819 -0.7307 2.5172 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4330 0.5357 1.4646 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8616 1.0856 0.3608 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0966 1.8388 0.3013 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9453 2.0655 1.3544 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1263 2.8064 1.2186 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4877 3.3446 0.0042 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6400 3.1186 -1.0493 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4786 2.3924 -0.9248 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9885 3.6552 -2.2867 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6502 4.0784 -0.1463 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5703 0.2820 1.1369 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2352 -6.9362 -1.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2178 -7.4548 0.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3253 -7.4966 -0.2793 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6866 -4.0003 1.6585 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9512 -2.6889 0.3422 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -3.0541 -1.3470 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8511 -0.9351 -1.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8620 1.2299 -2.0202 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3223 0.3352 0.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0421 0.9147 2.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2131 1.9470 2.9181 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6079 2.0875 -1.7074 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6788 2.8235 -1.8822 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6437 2.8841 0.6968 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3507 0.5345 -0.6436 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0242 -1.4885 1.4195 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2105 -2.8699 -0.4437 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9932 -2.0212 -1.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9773 0.6152 2.3860 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2516 0.9567 -0.5225 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6768 1.6481 2.3229 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7570 2.9505 2.0930 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8094 2.2183 -1.7723 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3811 4.3517 -2.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2456 4.1933 0.6497 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9713 1.1431 0.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 1 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 17 21 1 0 8 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 33 37 1 0 22 38 1 0 24 5 1 0 35 30 1 0 19 14 1 0 1 39 1 0 1 40 1 0 1 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 8 45 1 6 12 46 1 0 13 47 1 0 15 48 1 0 16 49 1 0 19 50 1 0 20 51 1 0 21 52 1 0 22 53 1 6 23 54 1 1 24 55 1 0 24 56 1 0 28 57 1 0 29 58 1 0 31 59 1 0 32 60 1 0 35 61 1 0 36 62 1 0 37 63 1 0 38 64 1 0 M END

Standard InCHIKey	VEBNYMXKXIIGFX-VOHNXBSUSA-N
Standard InCHI	InChI=1S/C26H26O12/c1-36-25(34)26(35)12-20(37-22(31)8-4-14-2-6-16(27)18(29)10-14)24(33)21(13-26)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h2-11,20-21,24,27-30,33,35H,12-13H2,1H3/b8-4+,9-5+/t20-,21-,24-,26+/m1/s1
SMILES	COC(=O)[C@]1(O)C[C@@H](OC(=O)/C=C/c2ccc(c(c2)O)O)[C@H]([C@@H](C1)OC(=O)/C=C/c1ccc(c(c1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	530.14	Volume:	509.064 ? Van der Waals volume.
Dense:	1.041	LogP:	1.718 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.861 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.752 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	23.0
TPSA:	200.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.129	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.86	Fsp³:	0.269
MCE-18:	80.727 ? 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:	0.85	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.064 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.632 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.398	Promiscuous compounds:	0.625

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.361	MDCK Permeability:	-5.251
Pgp-inhibitor:	0.007	Pgp-substrate:	0.026
PAMPA:	0.806 ? 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):	0.053
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:	0.135
Plasma Protein Binding (PPB):	79.312%	Volume Distribution (VD):	0.456
Fu:	25.368% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.008
BSEP inhibitor:	0.19

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:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.101 ? 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):

8.406

Half-life (T1/2):

2.07

ADMET: Toxicity

hERG Blockers:	0.118	hERG Blockers (10um):	0.521
Human Hepatotoxicity (H-HT):	0.529	Drug-induced Liver Injury (DILI):	0.38
AMES Toxicity:	0.43	Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.875	Skin Sensitization:	1.0
Carcinogencity:	0.139	Eye Corrosion:	0.0
Eye Irritation:	0.368	Respiratory Toxicity:	0.161
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.929
Hematotoxicity:	0.006	Drug-induced Nephrotoxicity:	0.145
Genotoxicity:	0.881	RPMI-8226 Immunitoxicity:	0.011
A549 Cytotoxicity:	0.952	Hek293 Cytotoxicity:	0.366
BCF:	0.614 ? 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:	3.631 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.993 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.738 ? 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
NPO10374	Dichrocephala bicolor	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/np980153o]
NPO10374	Dichrocephala bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096846]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	tenerife	n.a.	PMID[10924166]
NPO30518.1	Solidago virgaaurea var. gigantea	Varieties	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15022716]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730248]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	Leaves	Khon Kaen, Thailand	2002-APR	PMID[15921434]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309323]
NPO29981	Suaeda glauca	Species	Chenopodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18481014]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	ground entire plants	Hainan Province, China	2004-APR	PMID[19061389]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061389]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21338052]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21469692]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21469692]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22220686]
NPO33307	pimpinella brachycarpa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23462643]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24279991]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24784222]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31017778]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36441179]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19061	Ceratozamia kuesteriana	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17606	Millettia ichthyochtona	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18250	Conus tessulatus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17281	Echinaster echinophorus	Species	Echinasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33307	pimpinella brachycarpa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18716	Parmelia caraccensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16201	Pteris altissima	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10374	Dichrocephala bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10374	Dichrocephala bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16201	Pteris altissima	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17281	Echinaster echinophorus	Species	Echinasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17606	Millettia ichthyochtona	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18250	Conus tessulatus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19061	Ceratozamia kuesteriana	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18716	Parmelia caraccensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	6
Inhibition	11
Activity	1
FC	1

Activity Type	# Activity
Individual protein	1
Cell line	7
Organism	8
Protein family	2
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	42700.0	nM	PMID[29525218]
NPT664	Protein family	Histone deacetylase	Homo sapiens	IC50	=	4990.0	nM	PMID[26996372]
NPT664	Protein family	Histone deacetylase	Homo sapiens	IC50	=	7590.0	nM	PMID[26996372]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	26.0	%	PMID[21469692]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	85.0	%	PMID[21469692]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	90.0	%	PMID[21469692]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	42870.0	nM	PMID[23462643]
NPT34	Cell line	BV-2	Mus musculus	Activity	=	91.1	%	PMID[23462643]
NPT34	Cell line	BV-2	Mus musculus	IC50	=	9040.0	nM	PMID[23462643]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	22.27	%	PMID[25497988]
NPT2	Others	Unspecified	n.a.	IC50	=	5800.0	nM	PMID[15921434]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	45.0	%	PMID[21469692]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	>	50.0	%	PMID[21469692]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	60.0	%	PMID[21469692]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	39.0	%	PMID[21469692]
NPT32	Organism	Mus musculus	Mus musculus	FC	=	2.0	n.a.	PMID[21469692]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	49.0	%	PMID[21469692]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	29.0	%	PMID[21469692]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	41.0	%	PMID[21469692]

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 NPC258469 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	9588
0.1-0.2	35529
0.2-0.3	4114
0.3-0.4	466
0.4-0.5	103
0.5-0.6	35
0.6-0.7	13
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	NPC43158
1.0	High Similarity	NPC610147
0.8214	Intermediate Similarity	NPC163883
0.7963	Intermediate Similarity	NPC295492
0.7963	Intermediate Similarity	NPC303683
0.7963	Intermediate Similarity	NPC274891
0.7222	Intermediate Similarity	NPC26241
0.7097	Intermediate Similarity	NPC146277
0.6897	Remote Similarity	NPC277315
0.6897	Remote Similarity	NPC472016
0.6897	Remote Similarity	NPC192831
0.6863	Remote Similarity	NPC224208
0.6863	Remote Similarity	NPC41661
0.6667	Remote Similarity	NPC205751
0.6552	Remote Similarity	NPC233350
0.6552	Remote Similarity	NPC70680
0.6379	Remote Similarity	NPC13818
0.6226	Remote Similarity	NPC474275
0.617	Remote Similarity	NPC226250
0.6061	Remote Similarity	NPC322660
0.6	Remote Similarity	NPC474875
0.597	Remote Similarity	NPC306343
0.5968	Remote Similarity	NPC471027
0.5926	Remote Similarity	NPC147192
0.5893	Remote Similarity	NPC168799
0.5882	Remote Similarity	NPC93498
0.5862	Remote Similarity	NPC182217
0.5849	Remote Similarity	NPC233669
0.5821	Remote Similarity	NPC270993
0.5741	Remote Similarity	NPC281277
0.5692	Remote Similarity	NPC483141
0.5636	Remote Similarity	NPC309434
0.5517	Remote Similarity	NPC470849
0.5517	Remote Similarity	NPC488563
0.5469	Remote Similarity	NPC37250
0.5469	Remote Similarity	NPC142703
0.5469	Remote Similarity	NPC152942
0.5469	Remote Similarity	NPC9991
0.5469	Remote Similarity	NPC302857
0.5469	Remote Similarity	NPC600892
0.5345	Remote Similarity	NPC106406
0.5323	Remote Similarity	NPC219428
0.5254	Remote Similarity	NPC474895
0.5224	Remote Similarity	NPC284948
0.5224	Remote Similarity	NPC303090
0.5224	Remote Similarity	NPC301382
0.5224	Remote Similarity	NPC37331
0.5192	Remote Similarity	NPC95381
0.5185	Remote Similarity	NPC217472
0.5135	Remote Similarity	NPC19380
0.5085	Remote Similarity	NPC605000
0.5082	Remote Similarity	NPC470848
0.5082	Remote Similarity	NPC155209
0.5077	Remote Similarity	NPC319628
0.507	Remote Similarity	NPC156875
0.5065	Remote Similarity	NPC44730

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC258469 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3815
0.1-0.2	5185
0.2-0.3	146
0.3-0.4	3
0.4-0.5	0
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5224	Remote 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