NPASS Compound

Natural Product: NPC237408

Natural Product ID	NPC237408
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DUJXEXZHKSKPIY-HNNXBMFYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44207164
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

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 54 57 0 0 0 0 0 0 0 0999 V2000 -4.1248 4.1521 0.5495 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3262 2.8119 0.2335 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3035 1.8691 0.1688 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0131 2.2566 0.4254 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9822 1.2965 0.3569 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3853 1.7841 0.5879 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3811 0.7649 1.0146 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0916 -0.6122 0.5431 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1294 -1.5322 0.5882 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4846 -1.1222 1.0162 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8128 0.2277 0.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7239 1.1733 0.6689 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0935 2.5373 0.5734 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2779 3.4503 0.7842 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3905 2.9490 0.2382 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7298 4.3237 0.1507 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8658 -2.8228 0.2132 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6275 -3.2205 -0.2010 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4401 -2.2960 -0.2575 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1961 -1.0109 0.1171 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2652 -0.0088 0.0396 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5694 -0.4019 -0.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5680 0.5575 -0.1480 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8636 0.1706 -0.4061 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2502 -1.1318 -0.7373 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6577 -2.7922 -0.7060 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7931 -2.8579 -2.1540 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3283 -4.5164 -0.5858 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3694 -5.4796 -0.5454 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3639 4.3213 1.3510 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0383 4.6593 0.9212 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7609 4.6971 -0.3454 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7495 3.2830 0.6816 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2954 2.5619 1.3982 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7247 2.2440 -0.3804 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3271 0.7413 2.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2691 -1.8277 0.6822 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5032 -1.0502 2.1166 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7431 0.5818 0.8861 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9766 0.1897 -0.6749 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3282 4.6057 1.0234 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8505 4.9603 -0.0294 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3968 4.4541 -0.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6698 -3.5295 0.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9044 -1.3760 -0.4192 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6753 -1.4635 -1.6084 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3391 -1.0997 -0.9854 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0583 -1.7668 0.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1786 -3.6582 -2.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8719 -2.9324 -2.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4156 -1.8884 -2.5314 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2313 -5.1800 -1.1850 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9384 -6.4234 -0.9590 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7634 -5.6227 0.4730 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 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 9 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 19 26 1 0 26 27 1 0 18 28 1 0 28 29 1 0 23 3 1 0 21 5 2 0 12 7 1 0 20 8 1 0 1 30 1 0 1 31 1 0 1 32 1 0 4 33 1 0 6 34 1 0 6 35 1 0 7 36 1 1 10 37 1 0 10 38 1 0 11 39 1 0 11 40 1 0 16 41 1 0 16 42 1 0 16 43 1 0 17 44 1 0 22 45 1 0 25 46 1 0 25 47 1 0 25 48 1 0 27 49 1 0 27 50 1 0 27 51 1 0 29 52 1 0 29 53 1 0 29 54 1 0 M END

Standard InCHIKey	DUJXEXZHKSKPIY-HNNXBMFYSA-N
Standard InCHI	InChI=1S/C22H25NO6/c1-25-16-10-13-8-15-19-12(6-7-23(15)22(24)29-5)9-18(27-3)21(28-4)20(19)14(13)11-17(16)26-2/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1
SMILES	COc1cc2C[C@H]3c4c(CCN3C(=O)OC)cc(c(c4-c2cc1OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	399.17	Volume:	400.125 ? Van der Waals volume.
Dense:	0.998	LogP:	2.553 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.818 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.683 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	21.0
TPSA:	66.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.783	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.018	Fsp³:	0.409
MCE-18:	78.194 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.119	Fluc inhibitor:	0.354 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.679 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.564 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.003	Promiscuous compounds:	0.419

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.538	MDCK Permeability:	-4.578
Pgp-inhibitor:	0.869	Pgp-substrate:	0.864
PAMPA:	0.009 ? 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):	0.467
20% Bioavailability (F20%):	0.827	30% Bioavailability (F30%):	0.593
50% Bioavailability (F50%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053	MRP1:	0.842
Plasma Protein Binding (PPB):	91.162%	Volume Distribution (VD):	0.435
Fu:	6.202% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.974
OATP1B3 inhibitor:	0.985	BCRP inhibitor:	0.928
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.99	CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.127
CYP2C9-inhibitor:	0.178	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.96	CYP2D6-substrate:	0.331
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.75
CYP2B6-substrate:	0.036	CYP2C8-inhibitor:	0.936
HLM stability:	0.57 ? 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):

9.477

Half-life (T1/2):

1.458

ADMET: Toxicity

hERG Blockers:	0.265	hERG Blockers (10um):	0.558
Human Hepatotoxicity (H-HT):	0.843	Drug-induced Liver Injury (DILI):	0.847
AMES Toxicity:	0.427	Rat Oral Acute Toxicity:	0.697
Maximum Recommended Daily Dose:	0.92	Skin Sensitization:	0.735
Carcinogencity:	0.787	Eye Corrosion:	0.0
Eye Irritation:	0.094	Respiratory Toxicity:	0.938
Drug-induced Neurotoxicity:	0.908	Ototoxicity:	0.793
Hematotoxicity:	0.525	Drug-induced Nephrotoxicity:	0.817
Genotoxicity:	0.83	RPMI-8226 Immunitoxicity:	0.134
A549 Cytotoxicity:	0.436	Hek293 Cytotoxicity:	0.277
BCF:	1.444 ? 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:	3.888 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.526 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.647 ? 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
NPO27883	Bursera simaruba	Species	Burseraceae	Eukaryota	Resin	n.a.	n.a.	PMID[1294696]
NPO28935	Ericameria laricifolia	Species	Asteraceae	Eukaryota	n.a.	Sonoran Desert	n.a.	PMID[15043404]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18991207]
NPO27883	Bursera simaruba	Species	Burseraceae	Eukaryota	n.a.	bark	n.a.	PMID[19329133]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	essential oil	Tibet	n.a.	PMID[20944522]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28541690]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36552598]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37746728]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39013008]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39395223]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[9170290]
NPO28959	Cissus quadrangularis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29411	Streptomyces nigrescens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27883	Bursera simaruba	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29377	Callistemon speciosus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16079	Cephalaria leucantha	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1079	Vachellia karroo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27562	Coleus wulfenioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18780	Diplacus aurantiacus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28935	Ericameria laricifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26851	Eupatorium rebaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29307	Loranthus longiflorus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28549	Mentha incana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29144	Ormosia fordiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO862	Podocarpus elatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26549	Polanisia trachysperma	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29218	Ramalina farinacea	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27256	Solanum boerhaavii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26851	Eupatorium rebaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1079	Vachellia karroo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26851	Eupatorium rebaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18780	Diplacus aurantiacus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29411	Streptomyces nigrescens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26851	Eupatorium rebaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26549	Polanisia trachysperma	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28959	Cissus quadrangularis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29377	Callistemon speciosus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29218	Ramalina farinacea	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29144	Ormosia fordiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28935	Ericameria laricifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27903	Delphinium denudatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27883	Bursera simaruba	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO862	Podocarpus elatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29307	Loranthus longiflorus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27724	Polygala senega	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16079	Cephalaria leucantha	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1079	Vachellia karroo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18780	Diplacus aurantiacus	Species	Phrymaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28549	Mentha incana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27256	Solanum boerhaavii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27562	Coleus wulfenioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC237408 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	22273
0.1-0.2	26128
0.2-0.3	1411
0.3-0.4	38
0.4-0.5	6
0.5-0.6	2
0.6-0.7	1
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	Natural Product ID
0.6567	Remote Similarity	NPC116284
0.5224	Remote Similarity	NPC611314
0.5068	Remote Similarity	NPC82763

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC237408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4758
0.1-0.2	4284
0.2-0.3	108
0.3-0.4	0
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	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