NPASS Compound

Natural Product: NPC171014

Natural Product ID	NPC171014
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Bufalin
IUPAC Name	5-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
Synonyms	Bufalin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL399680
PubChem CID	9547215
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides 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 62 66 0 0 0 0 0 0 0 0999 V2000 -5.5468 0.5094 -2.3835 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3436 0.5893 -1.6868 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5149 1.5755 -0.5492 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1208 1.8227 -0.0058 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4869 0.5662 0.5280 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3850 -0.6216 0.2968 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9424 -0.7168 -1.0771 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7164 -1.9156 0.6424 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3452 -2.0721 0.0682 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5201 -0.8902 0.5545 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1214 0.3368 -0.0867 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2449 1.5204 -0.0635 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0172 1.4142 0.6928 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7371 0.1059 0.5935 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9207 -1.0437 0.1647 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3751 -2.2286 0.7410 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1229 -1.1457 -1.3218 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6068 -0.8694 -1.4503 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8505 0.2141 -0.4608 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1781 0.1861 0.1557 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9331 1.3328 0.2089 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1866 1.3124 0.7802 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6476 0.1163 1.2886 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7929 0.0141 1.8316 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8976 -0.9589 1.2195 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7157 -0.9769 0.6901 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3314 -0.1886 1.9533 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3576 0.7316 2.0298 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3884 -0.0288 -3.1941 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5897 0.9818 -2.4097 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8954 2.5528 -0.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1588 1.1313 0.2303 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2171 2.6188 0.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5374 2.2415 -0.8777 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2366 -0.5022 1.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2719 -1.3108 -1.7629 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8822 -1.3429 -1.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4081 -2.7361 0.3414 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6293 -1.9852 1.7483 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3571 -2.0369 -1.0460 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9332 -3.0300 0.4143 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5803 -0.8869 1.6545 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3242 0.0494 -1.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0040 1.8761 -1.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8347 2.3806 0.3727 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8315 1.7009 1.7707 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7192 2.1993 0.3267 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1818 -3.0182 0.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9451 -2.2127 -1.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5104 -0.4457 -1.9033 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8707 -0.5808 -2.4979 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1202 -1.8343 -1.1720 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7270 1.2032 -0.9977 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5798 2.2794 -0.1882 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8166 2.1999 0.8421 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0892 -1.8642 0.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2636 0.3639 2.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6009 0.2319 2.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3796 -1.2712 2.1830 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3351 0.8663 2.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7824 -0.1323 2.5883 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9371 1.6224 2.3987 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 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 14 27 1 1 5 28 1 1 7 2 1 0 15 10 1 0 26 20 2 0 11 5 1 0 19 14 1 0 1 29 1 0 2 30 1 6 3 31 1 0 3 32 1 0 4 33 1 0 4 34 1 0 6 35 1 1 7 36 1 0 7 37 1 0 8 38 1 0 8 39 1 0 9 40 1 0 9 41 1 0 10 42 1 1 11 43 1 6 12 44 1 0 12 45 1 0 13 46 1 0 13 47 1 0 16 48 1 0 17 49 1 0 17 50 1 0 18 51 1 0 18 52 1 0 19 53 1 6 21 54 1 0 22 55 1 0 26 56 1 0 27 57 1 0 27 58 1 0 27 59 1 0 28 60 1 0 28 61 1 0 28 62 1 0 M END

Standard InCHIKey	QEEBRPGZBVVINN-BMPKRDENSA-N
Standard InCHI	InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1
SMILES	O[C@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2c1ccc(=O)oc1)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	386.25	Volume:	408.129 ? Van der Waals volume.
Dense:	0.946	LogP:	2.428 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.805 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.887 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	70.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.757	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.366	Fsp³:	0.792
MCE-18:	117.512 ? 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:	0.571	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.503 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.098	Promiscuous compounds:	0.422

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.252	MDCK Permeability:	-5.084
Pgp-inhibitor:	0.008	Pgp-substrate:	0.118
PAMPA:	0.521 ? 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):	0.005
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	0.922
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23	MRP1:	0.994
Plasma Protein Binding (PPB):	96.944%	Volume Distribution (VD):	-0.028
Fu:	3.65% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.76
OATP1B3 inhibitor:	0.937	BCRP inhibitor:	0.005
BSEP inhibitor:	0.807

ADMET: Metabolism

CYP1A2-inhibitor:	0.099	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.085	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.715	CYP3A4-substrate:	0.903
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.979
HLM stability:	0.72 ? 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):

13.803

Half-life (T1/2):

1.689

ADMET: Toxicity

hERG Blockers:	0.1	hERG Blockers (10um):	0.211
Human Hepatotoxicity (H-HT):	0.586	Drug-induced Liver Injury (DILI):	0.127
AMES Toxicity:	0.598	Rat Oral Acute Toxicity:	0.67
Maximum Recommended Daily Dose:	0.982	Skin Sensitization:	0.934
Carcinogencity:	0.957	Eye Corrosion:	0.001
Eye Irritation:	0.287	Respiratory Toxicity:	0.839
Drug-induced Neurotoxicity:	0.575	Ototoxicity:	0.197
Hematotoxicity:	0.467	Drug-induced Nephrotoxicity:	0.967
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.367
A549 Cytotoxicity:	0.702	Hek293 Cytotoxicity:	0.939
BCF:	1.109 ? 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:	3.337 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.61 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.192 ? 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]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575946]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141860]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15635246]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730237]
NPO8520	Mucor spinosus	Species	Mucoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844967]
NPO40825	Cunninghamella blakesleana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15844967]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17504571]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21185919]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	twigs and leaves	Yunnan Province, China	2008-OCT	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21954912]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22708620]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	venom	n.a.	n.a.	PMID[24050254]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28256122]
NPO40527	Helleborus thibetanus Franch	Strain	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30245398]
NPO40826	Cyanobacterial Blooms	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[30369239]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO2917	Artemisia oranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40825	Cunninghamella blakesleana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1504	Alicyclobacillus cycloheptanicus	Species	Alicyclobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26231	Vicia villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12250	Strychnos fendleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11515	Streptomyces plumbeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6011	Pleurotus citrinopileatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6887	Lytanthus salicinus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5177	Lecanora conizaeoides	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7543	Haplopappus venetus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12735	Halimeda macroloba	Species	Halimedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4797	Gavia immer	Species	Gaviidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21463	Aruncus dioicus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12952	Cabucala madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9398	Cortinarius rubellus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19205	Buxus sempervirens	Species	Buxaceae	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]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO641	Astragalus globiceps	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12735	Halimeda macroloba	Species	Halimedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6011	Pleurotus citrinopileatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11515	Streptomyces plumbeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2917	Artemisia oranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12250	Strychnos fendleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1504	Alicyclobacillus cycloheptanicus	Species	Alicyclobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4797	Gavia immer	Species	Gaviidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5177	Lecanora conizaeoides	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6887	Lytanthus salicinus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9117	Hammada elegans	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9398	Cortinarius rubellus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21463	Aruncus dioicus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26231	Vicia villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7543	Haplopappus venetus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12952	Cabucala madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8520	Mucor spinosus	Species	Mucoraceae	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
Inhibition	4
FC	1
Ki	2
IC50	32
TDI	4
Ratio IC50	4
Kinact	2
IC50 ratio	4
Activity	45
EC50	11

Activity Type	# Activity
Individual protein	18
Cell line	63
Single protein	2
Protein complex group	1
Unchecked	4
Others	19
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	1130.0	nM	PMID[35094507]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	11310.0	nM	PMID[35094507]
NPT240	Individual protein	Cytochrome P450 2A6	Homo sapiens	TDI	n.a.	n.a.	n.a.	PMID[35094507]
NPT212	Individual protein	Cytochrome P450 2C9	Homo sapiens	TDI	n.a.	n.a.	n.a.	PMID[35094507]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	20900.0	nM	PMID[35094507]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	IC50	=	1900.0	nM	PMID[31945667]
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	TDI	n.a.	n.a.	n.a.	PMID[35094507]
NPT241	Individual protein	Cytochrome P450 2E1	Homo sapiens	TDI	n.a.	n.a.	n.a.	PMID[35094507]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Ratio IC50	=	25.13	n.a.	PMID[35094507]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	450.0	nM	PMID[35094507]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Inhibition	=	50.0	%	PMID[35094507]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Kinact	=	0.14	/min	PMID[35094507]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Kinact	=	0.097	/min	PMID[35094507]
NPT24845	Single protein	Cytochrome P450 3A7	Homo sapiens	IC50	>	100000.0	nM	PMID[35094507]
NPT4023	Individual protein	Cytochrome P450 3A5	Homo sapiens	IC50	=	2760.0	nM	PMID[35094507]
NPT4023	Individual protein	Cytochrome P450 3A5	Homo sapiens	Ratio IC50	=	1.18	n.a.	PMID[35094507]
NPT30132	Protein complex group	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	22.0	nM	PMID[31945667]
NPT24845	Single protein	Cytochrome P450 3A7	Homo sapiens	Ratio IC50	>	1.5	n.a.	PMID[35094507]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	-0.26	%	PMID[23062825]
NPT4775	Individual protein	H(+)/Cl(-) exchange transporter 3	Homo sapiens	FC	=	17.0	n.a.	PMID[23799775]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	17.22	%	PMID[23062825]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	640.0	nM	PMID[17911017]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	730.0	nM	PMID[17911017]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	990.0	nM	PMID[17911017]
NPT91	Cell line	KB	Homo sapiens	IC50	=	0.67	ug.mL-1	PMID[11575946]
NPT116	Cell line	HL-60	Homo sapiens	IC50	<	0.01	ug.mL-1	PMID[11575946]
NPT1366	Cell line	MH60	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[11575946]
NPT1366	Cell line	MH60	Mus musculus	IC50	=	31900.0	nM	PMID[15620253]
NPT1366	Cell line	MH60	Mus musculus	IC50	>	64800.0	nM	PMID[15620253]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	7.0	nM	PMID[15844967]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	45.0	nM	PMID[15844967]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	28.0	nM	PMID[15844967]
NPT1317	Cell line	CCRF S-180	Mus musculus	IC50	>	50000.0	nM	PMID[23799775]
NPT1357	Cell line	H22	Mus musculus	IC50	>	50000.0	nM	PMID[23799775]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	345.0	nM	PMID[23799775]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	589.0	nM	PMID[23799775]
NPT81	Cell line	A549	Homo sapiens	IC50	=	600.0	nM	PMID[24050254]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	600.0	nM	PMID[24050254]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	594.2	nM	PMID[30245398]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	279.9	nM	PMID[30245398]
NPT165	Cell line	HeLa	Homo sapiens	Activity	=	53.3	%	PMID[30245398]
NPT165	Cell line	HeLa	Homo sapiens	Activity	=	30.9	%	PMID[30245398]
NPT165	Cell line	HeLa	Homo sapiens	Activity	=	13.9	%	PMID[30245398]
NPT165	Cell line	HeLa	Homo sapiens	Activity	=	1.86	%	PMID[30245398]
NPT146	Cell line	SK-OV-3	Homo sapiens	EC50	=	10.0	nM	PMID[30369239]
NPT393	Cell line	HCT-116	Homo sapiens	EC50	=	11.0	nM	PMID[30369239]
NPT65	Cell line	HepG2	Homo sapiens	EC50	=	35.0	nM	PMID[30369239]
NPT2844	Cell line	MES-SA	Homo sapiens	EC50	=	28.0	nM	PMID[30369239]
NPT401	Cell line	786-0	Homo sapiens	EC50	=	7.5	nM	PMID[30369239]
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	42.0	nM	PMID[30369239]
NPT1081	Cell line	BXPC-3	Homo sapiens	EC50	=	11.0	nM	PMID[30369239]
NPT1535	Cell line	U-87 MG	Homo sapiens	EC50	=	14.0	nM	PMID[30369239]
NPT2341	Cell line	NCI-H1975	Homo sapiens	EC50	=	13.0	nM	PMID[30369239]
NPT737	Cell line	HUVEC	Homo sapiens	EC50	=	12.0	nM	PMID[30369239]
NPT1317	Cell line	CCRF S-180	Mus musculus	EC50	>	20000.0	nM	PMID[30369239]
NPT22964	Cell line	CNE2Z	Homo sapiens	Activity	=	35.2	%	PMID[23799775]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	11420.0	nM	PMID[35094507]
NPT28438	Unchecked	Unchecked	n.a.	Ratio IC50	=	15.46	n.a.	PMID[35094507]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	=	53.0	%	PMID[35094507]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	740.0	nM	PMID[35094507]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	40.9	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	31.7	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	21.5	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	42.7	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	33.9	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	23.1	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	43.9	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	36.9	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	26.5	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	59.1	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	50.5	%	PMID[23799775]
NPT610	Others	Molecular identity unknown	n.a.	Activity	=	39.1	%	PMID[23799775]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	460.0	nM	PMID[23799775]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	279.0	nM	PMID[23799775]
NPT897	Others	Monoclonal antibody (mAb)	n.a.	IC50 ratio	=	6700.0	n.a.	PMID[12109909]
NPT897	Others	Monoclonal antibody (mAb)	n.a.	IC50 ratio	=	550.0	n.a.	PMID[12109909]
NPT897	Others	Monoclonal antibody (mAb)	n.a.	IC50 ratio	=	260.0	n.a.	PMID[12109909]
NPT897	Others	Monoclonal antibody (mAb)	n.a.	IC50 ratio	=	250.0	n.a.	PMID[12109909]
NPT2	Others	Unspecified	n.a.	IC50	=	0.00028	ug.mL-1	PMID[12459012]
NPT2	Others	Unspecified	n.a.	IC50	=	11.0	nM	PMID[24050254]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-3.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-2.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-4.4	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	12.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	17.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	32.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	62.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	42.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-0.6	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-2.7	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	11.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	8.9	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	4.3	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-2.9	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-10.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	3.1	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	10.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	34.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	35.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-22.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	7.6	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-32.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	21.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-62.0	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	-84.3	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	1.8	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	2.8	%	PMID[30369239]
NPT24974	Cell line	Cardiac muscle cell	n.a.	Activity	=	8.5	%	PMID[30369239]

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 NPC171014 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	15926
0.1-0.2	32925
0.2-0.3	887
0.3-0.4	50
0.4-0.5	29
0.5-0.6	25
0.6-0.7	9
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8088	Intermediate Similarity	NPC73050
0.8088	Intermediate Similarity	NPC605625
0.803	Intermediate Similarity	NPC481624
0.803	Intermediate Similarity	NPC481626
0.7794	Intermediate Similarity	NPC295843
0.7647	Intermediate Similarity	NPC275060
0.7647	Intermediate Similarity	NPC304276
0.6901	Remote Similarity	NPC137462
0.6761	Remote Similarity	NPC481625
0.6757	Remote Similarity	NPC146786
0.6711	Remote Similarity	NPC75389
0.6622	Remote Similarity	NPC184555
0.6301	Remote Similarity	NPC606351
0.6216	Remote Similarity	NPC481623
0.6081	Remote Similarity	NPC603706
0.6	Remote Similarity	NPC189863
0.5976	Remote Similarity	NPC183603
0.5696	Remote Similarity	NPC185287
0.5696	Remote Similarity	NPC43063
0.5696	Remote Similarity	NPC79298
0.557	Remote Similarity	NPC12795
0.5556	Remote Similarity	NPC488753
0.5542	Remote Similarity	NPC154815
0.5542	Remote Similarity	NPC247760
0.5542	Remote Similarity	NPC55602
0.55	Remote Similarity	NPC171126
0.5484	Remote Similarity	NPC16270
0.5422	Remote Similarity	NPC609315
0.5412	Remote Similarity	NPC233041
0.5385	Remote Similarity	NPC606297
0.5294	Remote Similarity	NPC241977
0.525	Remote Similarity	NPC604982
0.525	Remote Similarity	NPC608996
0.5244	Remote Similarity	NPC610731
0.5233	Remote Similarity	NPC488752
0.5222	Remote Similarity	NPC62172
0.5176	Remote Similarity	NPC221414
0.5165	Remote Similarity	NPC611669
0.5109	Remote Similarity	NPC289700
0.5059	Remote Similarity	NPC157380
0.5056	Remote Similarity	NPC47870

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC171014 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3974
0.1-0.2	5106
0.2-0.3	58
0.3-0.4	9
0.4-0.5	2
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
0.5165	Remote Similarity	NPD7503	Phase 4

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