NPASS Compound

Natural Product: NPC216663

Natural Product ID	NPC216663
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CMJANKGYCHNBQY-SBJOWSEZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24764026
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

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 60 63 0 0 0 0 0 0 0 0999 V2000 -4.7085 -0.9171 1.5785 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6861 -0.5795 0.7800 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3324 -1.1166 1.1564 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6948 -2.0051 0.1931 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2611 -2.3360 0.2099 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5039 -2.2725 1.4732 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7254 -1.4005 1.5149 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5898 -0.1617 0.6803 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6603 0.7550 0.3110 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9670 0.2906 0.5930 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7975 1.0559 1.3913 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3731 2.1467 1.8489 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1840 0.6508 1.7410 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5123 1.0219 -1.0669 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1306 0.9036 -1.3516 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5251 2.2351 -1.0781 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8954 2.3654 -0.7848 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8216 1.4298 -0.7692 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2773 1.6065 -0.4533 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0096 0.2924 -0.3380 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8966 2.5027 -1.2821 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3196 3.7893 -0.4585 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6751 -0.1759 -0.4348 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5090 -1.5419 -0.9143 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2134 -1.7957 -2.1985 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8572 -2.2649 -1.1054 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3395 0.3601 0.8013 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0272 0.6009 -2.6795 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5209 -1.5426 2.4336 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7284 -0.6033 1.4272 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5935 -1.7611 2.0912 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8185 -0.3068 1.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2627 -3.0200 0.3115 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0347 -1.7526 -0.8338 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1455 -3.3645 -0.1950 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8787 -3.2889 1.8105 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2195 -2.0074 2.2948 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6882 -1.8648 1.3746 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7642 -1.0078 2.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4943 1.7354 0.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2377 0.1403 2.7269 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7813 1.5825 1.8152 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6571 0.0541 0.9348 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0831 2.7162 -0.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7792 2.8778 -1.9754 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5234 0.4285 -1.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3205 2.0581 0.5839 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9221 -0.1969 -1.3351 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0931 0.5752 -0.2768 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7648 2.7442 -0.8736 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5012 4.3701 -0.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7673 4.2729 -1.3229 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0677 3.6602 0.3784 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8341 -2.7350 -2.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5247 -2.1140 -3.0149 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7520 -0.9801 -2.6535 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8686 -3.1173 -0.4076 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7065 -1.6137 -0.9361 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9055 -2.7616 -2.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2403 1.3836 -3.2214 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 2 0 11 13 1 0 9 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 19 21 1 0 17 22 1 0 15 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 23 27 1 1 15 28 1 6 20 2 1 0 24 5 1 0 23 8 1 0 8 27 1 1 1 29 1 0 1 30 1 0 3 31 1 0 3 32 1 0 4 33 1 0 4 34 1 0 5 35 1 6 6 36 1 0 6 37 1 0 7 38 1 0 7 39 1 0 9 40 1 1 13 41 1 0 13 42 1 0 13 43 1 0 16 44 1 0 16 45 1 0 18 46 1 0 19 47 1 1 20 48 1 0 20 49 1 0 21 50 1 0 22 51 1 0 22 52 1 0 22 53 1 0 25 54 1 0 25 55 1 0 25 56 1 0 26 57 1 0 26 58 1 0 26 59 1 0 28 60 1 0 M END

Standard InCHIKey	CMJANKGYCHNBQY-SBJOWSEZSA-N
Standard InCHI	InChI=1S/C22H32O6/c1-13-6-7-16-8-9-20-18(26-15(3)23)27-21(25,12-14(2)11-17(24)10-13)22(20,28-20)19(16,4)5/h11,16-18,24-25H,1,6-10,12H2,2-5H3/b14-11+/t16-,17+,18+,20-,21-,22-/m1/s1
SMILES	C=C1CC[C@@H]2CC[C@@]34[C@@H](OC(=O)C)O[C@](C/C(=C/[C@H](C1)O)/C)([C@]3(C2(C)C)O4)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	392.22	Volume:	399.674 ? Van der Waals volume.
Dense:	0.981	LogP:	2.788 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.712 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.032 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	23.0
TPSA:	88.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.405	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.807	Fsp³:	0.773
MCE-18:	110.0 ? 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:	0.097	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.192	Promiscuous compounds:	0.715

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.893	MDCK Permeability:	-4.723
Pgp-inhibitor:	0.993	Pgp-substrate:	0.065
PAMPA:	0.259 ? 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):	0.092
20% Bioavailability (F20%):	0.764	30% Bioavailability (F30%):	0.939
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.557
Plasma Protein Binding (PPB):	73.963%	Volume Distribution (VD):	-0.168
Fu:	20.642% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.059
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.451	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.105	CYP3A4-substrate:	0.388
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.978
HLM stability:	0.896 ? 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):

9.746

Half-life (T1/2):

1.662

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.229
Human Hepatotoxicity (H-HT):	0.503	Drug-induced Liver Injury (DILI):	0.327
AMES Toxicity:	0.528	Rat Oral Acute Toxicity:	0.368
Maximum Recommended Daily Dose:	0.924	Skin Sensitization:	0.965
Carcinogencity:	0.121	Eye Corrosion:	0.004
Eye Irritation:	0.612	Respiratory Toxicity:	0.722
Drug-induced Neurotoxicity:	0.236	Ototoxicity:	0.728
Hematotoxicity:	0.439	Drug-induced Nephrotoxicity:	0.729
Genotoxicity:	0.443	RPMI-8226 Immunitoxicity:	0.256
A549 Cytotoxicity:	0.062	Hek293 Cytotoxicity:	0.19
BCF:	0.505 ? 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:	3.352 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.188 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.271 ? 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
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398538]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933873]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18484775]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061391]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21513294]
NPO20428	Debregeasia salicifolia	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25684	Fagus dombeyi	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25516	Dahlia sherffii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28702	Cyclolepis genistoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25452	Crucigenia apiculata	Species	Scenedesmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24435	Beschorneria bracteata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25606	Aster patagonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25485	Agathosma lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5278	Acacia cyperophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5543	Persicaria tomentosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25205	Thymus borgiae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25427	Solanum vespertilio	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23999	Rhipidothuria racowitzai	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19210	Quercus lusitanica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25655	Pseudocyphellaria granulata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25631	Picris kamtschatica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24482	Phyllanthus oxyphyllus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25314	Usnea ceratina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24616	Ottonia vahlii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11177	Noctiluca scintillans	Species	Noctilucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23333	Michelia excelsa	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25061	Lactarius glyciosmus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2404	Heterophragma quadriloculare	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3706	Hedypnois rhagadioloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6639	Flagelloscypha pilatii	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11177	Noctiluca scintillans	Species	Noctilucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3706	Hedypnois rhagadioloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19210	Quercus lusitanica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25485	Agathosma lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28702	Cyclolepis genistoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25452	Crucigenia apiculata	Species	Scenedesmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25516	Dahlia sherffii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25427	Solanum vespertilio	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2404	Heterophragma quadriloculare	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25655	Pseudocyphellaria granulata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25631	Picris kamtschatica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25684	Fagus dombeyi	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24616	Ottonia vahlii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5543	Persicaria tomentosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25205	Thymus borgiae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24435	Beschorneria bracteata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25606	Aster patagonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25314	Usnea ceratina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23999	Rhipidothuria racowitzai	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6639	Flagelloscypha pilatii	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24482	Phyllanthus oxyphyllus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23333	Michelia excelsa	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20428	Debregeasia salicifolia	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25061	Lactarius glyciosmus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5278	Acacia cyperophylla	Species	Fabaceae	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 NPC216663 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	17829
0.1-0.2	30162
0.2-0.3	1855
0.3-0.4	11
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC216663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7065
0.1-0.2	2042
0.2-0.3	43
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