NPASS Compound

Natural Product: NPC271527

Natural Product ID	NPC271527
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LXPKORXZVZPYLY-IUNQKKBYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	9997459
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

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 46 49 0 0 0 0 0 0 0 0999 V2000 -3.6260 0.7792 0.7329 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3584 1.1256 0.0068 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5975 0.8256 -1.4756 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4537 -0.0600 -1.9279 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4404 0.2002 -0.8982 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1957 0.2465 0.3761 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2741 0.8444 1.4170 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9672 -0.0443 1.4470 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7214 0.0124 0.1133 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0352 -0.6411 0.2543 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7466 -0.1342 1.3135 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0543 1.1886 1.3113 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8066 -0.5874 -0.9263 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8477 -1.9887 -1.2525 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7621 -1.6193 -2.6289 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4384 -0.4668 -2.2672 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2241 0.2790 -2.8885 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9112 1.3834 -0.1282 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5994 -1.3921 1.6339 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6922 -1.8322 1.6579 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1110 -2.8546 2.2450 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7110 -1.0234 0.9155 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3786 -1.8348 0.0200 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0192 1.5213 -1.1533 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4049 1.4983 0.3630 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0152 -0.2252 0.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5596 0.9638 1.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1831 2.2043 0.1893 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5819 0.3474 -1.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5061 1.7923 -2.0066 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0647 0.3182 -2.9189 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7414 -1.0974 -2.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7665 0.6916 2.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0007 1.8778 1.2236 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6211 0.2295 2.2966 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6064 -0.5257 -0.7050 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9507 -1.7400 0.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6411 1.5382 0.4334 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2395 1.8649 1.6198 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8120 1.3184 2.1688 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8075 -2.4823 -1.0380 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0216 -2.6738 -1.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5599 1.4474 -0.8888 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4777 -0.7611 1.7076 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5721 -2.6876 0.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6823 2.1735 -1.1865 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 1 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 9 13 1 0 13 14 1 1 14 15 1 0 15 16 1 0 16 17 2 0 9 18 1 6 8 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 5 24 1 6 6 2 1 0 16 13 1 0 13 5 1 0 22 6 1 0 1 25 1 0 1 26 1 0 1 27 1 0 2 28 1 6 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 7 33 1 0 7 34 1 0 8 35 1 1 10 36 1 0 10 37 1 0 12 38 1 0 12 39 1 0 12 40 1 0 14 41 1 0 14 42 1 0 18 43 1 0 22 44 1 1 23 45 1 0 24 46 1 0 M END

Standard InCHIKey	LXPKORXZVZPYLY-IUNQKKBYSA-N
Standard InCHI	InChI=1S/C16H22O8/c1-8-3-4-16(21)13(8)5-9(24-11(18)10(13)17)15(20,7-22-2)14(16)6-23-12(14)19/h8-10,17,20-21H,3-7H2,1-2H3/t8-,9-,10+,13+,14+,15+,16-/m1/s1
SMILES	C[C@@H]1CC[C@]2([C@]31C[C@H]([C@@](COC)([C@]12COC1=O)O)OC(=O)[C@@H]3O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	342.13	Volume:	316.115 ? Van der Waals volume.
Dense:	1.082	LogP:	-0.025 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.303 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.093 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	20.0
TPSA:	122.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.532	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.692	Fsp³:	0.875
MCE-18:	108.267 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.087	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.357	Promiscuous compounds:	0.415

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.278	MDCK Permeability:	-4.77
Pgp-inhibitor:	0.0	Pgp-substrate:	0.522
PAMPA:	0.99 ? 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):	0.023
20% Bioavailability (F20%):	0.898	30% Bioavailability (F30%):	0.524
50% Bioavailability (F50%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.659	MRP1:	0.975
Plasma Protein Binding (PPB):	46.367%	Volume Distribution (VD):	-0.085
Fu:	60.211% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.402
OATP1B3 inhibitor:	0.424	BCRP inhibitor:	0.004
BSEP inhibitor:	0.05

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.15	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.005
HLM stability:	0.177 ? 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):

2.217

Half-life (T1/2):

3.502

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.085
Human Hepatotoxicity (H-HT):	0.591	Drug-induced Liver Injury (DILI):	0.26
AMES Toxicity:	0.899	Rat Oral Acute Toxicity:	0.374
Maximum Recommended Daily Dose:	0.462	Skin Sensitization:	0.985
Carcinogencity:	0.956	Eye Corrosion:	0.028
Eye Irritation:	0.591	Respiratory Toxicity:	0.16
Drug-induced Neurotoxicity:	0.18	Ototoxicity:	0.394
Hematotoxicity:	0.281	Drug-induced Nephrotoxicity:	0.911
Genotoxicity:	0.927	RPMI-8226 Immunitoxicity:	0.178
A549 Cytotoxicity:	0.068	Hek293 Cytotoxicity:	0.208
BCF:	0.366 ? 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:	3.011 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.405 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.591 ? 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
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)99818-1]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15283458]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[15577257]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38790803]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[8021657]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051910]
NPO16626	Leucetta microrhaphis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18379	Satureja atropatana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14465	Ramalina terebrata	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13368	Monomorium delagoense	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7027	Metapenaeus macleayi	Species	Penaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16137	Mappia foetida	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13730	Magnolia liliiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10551	Acanthopanax ricinifolius	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6519	Calocera viscosa	Species	Dacrymycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13970	Caryopteris mongholica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10773	Dalbergia rubiginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13730	Magnolia liliiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13970	Caryopteris mongholica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10551	Acanthopanax ricinifolius	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18379	Satureja atropatana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7027	Metapenaeus macleayi	Species	Penaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6519	Calocera viscosa	Species	Dacrymycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13368	Monomorium delagoense	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10773	Dalbergia rubiginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16626	Leucetta microrhaphis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16137	Mappia foetida	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14465	Ramalina terebrata	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13730	Magnolia liliiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	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 NPC271527 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	17732
0.1-0.2	29303
0.2-0.3	2819
0.3-0.4	1
0.4-0.5	1
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
0.6182	Remote Similarity	NPC253995
0.5263	Remote Similarity	NPC259654
0.5263	Remote Similarity	NPC298266

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC271527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6170
0.1-0.2	2913
0.2-0.3	67
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