NPASS Compound

Natural Product: NPC137462

Natural Product ID	NPC137462
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Telocinobufagin
IUPAC Name	5-[(3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
Synonyms	telocinobufagin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL463273
PubChem CID	259991
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 63 67 0 0 0 0 0 0 0 0999 V2000 6.3994 -0.3198 -0.2205 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0669 -0.7846 -0.1207 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5442 -0.2994 1.1979 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0769 -0.1745 1.2903 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4095 0.4500 0.0836 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8104 -0.3399 -1.1284 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3191 -0.2368 -1.2748 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3002 0.1232 -2.3119 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4372 -1.7806 -0.8796 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0422 -1.9832 -0.4170 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2634 -0.7123 -0.4237 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9238 0.4118 0.3306 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2193 1.6864 -0.0608 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0272 1.4711 -0.8512 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9025 0.3540 -0.3849 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1679 -0.8873 0.0083 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6584 -1.9945 -0.7268 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3738 -1.1705 1.4389 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1963 -0.0275 1.9884 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7381 0.7257 0.8204 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1924 0.4769 0.5999 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1082 1.5264 0.4897 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4391 1.2291 0.2884 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8783 -0.0612 0.1950 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0772 -0.3912 0.0123 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9874 -1.0155 0.3037 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7054 -0.7947 0.4962 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8708 0.0333 -1.5062 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9264 1.8873 0.0325 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5391 0.4762 0.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1349 -1.8829 -0.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8637 -1.0704 1.9623 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1072 0.6263 1.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8439 0.5196 2.1520 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6231 -1.1424 1.5798 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5744 -0.8491 -2.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6117 0.8011 -1.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1237 1.0698 -2.3760 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6801 -2.3689 -1.8036 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1218 -2.1934 -0.0961 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5404 -2.6709 -1.1581 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9601 -2.5377 0.5575 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1765 -0.3809 -1.4857 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7072 0.2817 1.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9256 2.2754 -0.6825 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0211 2.3287 0.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6324 2.4140 -0.7808 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7769 1.3673 -1.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8071 -2.7754 -0.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4617 -1.2678 2.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9555 -2.1182 1.6299 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5902 0.6704 2.5993 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0232 -0.3962 2.6495 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6224 1.8437 0.9190 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7617 2.5388 0.5633 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1951 2.0228 0.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0530 -1.6344 0.5728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1194 -1.0531 -1.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3993 0.3378 -2.4627 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8033 0.6602 -1.4154 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9825 1.9138 0.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9442 2.3006 -0.9736 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3463 2.4916 0.7651 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 6 6 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 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 15 28 1 6 5 29 1 6 7 2 1 0 16 11 1 0 27 21 2 0 12 5 1 0 20 15 1 0 1 30 1 0 2 31 1 1 3 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 7 36 1 0 7 37 1 0 8 38 1 0 9 39 1 0 9 40 1 0 10 41 1 0 10 42 1 0 11 43 1 6 12 44 1 1 13 45 1 0 13 46 1 0 14 47 1 0 14 48 1 0 17 49 1 0 18 50 1 0 18 51 1 0 19 52 1 0 19 53 1 0 20 54 1 1 22 55 1 0 23 56 1 0 27 57 1 0 28 58 1 0 28 59 1 0 28 60 1 0 29 61 1 0 29 62 1 0 29 63 1 0 M END

Standard InCHIKey	PBSOJKPTQWWJJD-ZBDZJSKLSA-N
Standard InCHI	InChI=1S/C24H34O5/c1-21-9-5-16(25)13-23(21,27)11-7-19-18(21)6-10-22(2)17(8-12-24(19,22)28)15-3-4-20(26)29-14-15/h3-4,14,16-19,25,27-28H,5-13H2,1-2H3/t16-,17+,18-,19+,21+,22+,23-,24-/m0/s1
SMILES	O[C@H]1CC[C@]2([C@](C1)(O)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:	402.24	Volume:	416.92 ? Van der Waals volume.
Dense:	0.965	LogP:	1.509 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.976 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.627 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	90.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.67	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.561	Fsp³:	0.792
MCE-18:	125.093 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.472	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.487 ? 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:	0.086	Promiscuous compounds:	0.492

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.139	MDCK Permeability:	-4.929
Pgp-inhibitor:	0.002	Pgp-substrate:	0.694
PAMPA:	0.861 ? 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):	0.002
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	0.941
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.146	MRP1:	0.998
Plasma Protein Binding (PPB):	96.629%	Volume Distribution (VD):	0.347
Fu:	2.591% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.43
OATP1B3 inhibitor:	0.618	BCRP inhibitor:	0.002
BSEP inhibitor:	0.861

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.022	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.364	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.413
HLM stability:	0.022 ? 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):

10.739

Half-life (T1/2):

2.66

ADMET: Toxicity

hERG Blockers:	0.062	hERG Blockers (10um):	0.168
Human Hepatotoxicity (H-HT):	0.511	Drug-induced Liver Injury (DILI):	0.028
AMES Toxicity:	0.577	Rat Oral Acute Toxicity:	0.73
Maximum Recommended Daily Dose:	0.986	Skin Sensitization:	0.94
Carcinogencity:	0.96	Eye Corrosion:	0.0
Eye Irritation:	0.134	Respiratory Toxicity:	0.833
Drug-induced Neurotoxicity:	0.453	Ototoxicity:	0.182
Hematotoxicity:	0.469	Drug-induced Nephrotoxicity:	0.99
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.401
A549 Cytotoxicity:	0.651	Hek293 Cytotoxicity:	0.943
BCF:	0.566 ? 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:	3.076 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.366 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.745 ? 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]
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	n.a.	twig	n.a.	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	twigs and leaves	Yunnan Province, China	2008-OCT	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]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO25922	Hedyotis verticillata	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7938277]
NPO2917	Artemisia oranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	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]
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]
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]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12952	Cabucala madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21463	Aruncus dioicus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11981	Bufo gargarizans	Species	Bufonidae	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]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	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]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	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]
NPO5721	Psorothamnus spinosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4797	Gavia immer	Species	Gaviidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5177	Lecanora conizaeoides	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12250	Strychnos fendleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2917	Artemisia oranensis	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]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6011	Pleurotus citrinopileatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	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]
NPO12735	Halimeda macroloba	Species	Halimedaceae	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]
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]
NPO2208	Doronicum hungaricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25922	Hedyotis verticillata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9576	Bufo bufo	Species	Bufonidae	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	47
Kd	2
IC50	12
Activity	23

Activity Type	# Activity
Individual protein	31
Cell line	41
Unchecked	6
Others	2
Organism	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT38	Individual protein	Signal transducer and activator of transcription 3	Homo sapiens	Inhibition	n.a.	n.a.	%	PMID[35200033]
NPT38	Individual protein	Signal transducer and activator of transcription 3	Homo sapiens	Kd	=	0.00598	1/s	PMID[35200033]
NPT38	Individual protein	Signal transducer and activator of transcription 3	Homo sapiens	Kd	=	50300.0	nM	PMID[35200033]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell line	KB	Homo sapiens	IC50	=	1.3	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]
NPT81	Cell line	A549	Homo sapiens	IC50	=	3000.0	nM	PMID[24050254]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	2400.0	nM	PMID[24050254]
NPT916	Cell line	SK-MEL	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[33882233]
NPT916	Cell line	SK-MEL	Homo sapiens	IC50	=	50.0	nM	PMID[33882233]
NPT81	Cell line	A549	Homo sapiens	Inhibition	n.a.	n.a.	%	PMID[35200033]
NPT2410	Cell line	NCI-H1299	Homo sapiens	Inhibition	n.a.	n.a.	%	PMID[35200033]
NPT2410	Cell line	NCI-H1299	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35200033]
NPT81	Cell line	A549	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35200033]
NPT2410	Cell line	NCI-H1299	Homo sapiens	Activity	=	38.41	%	PMID[35200033]
NPT2410	Cell line	NCI-H1299	Homo sapiens	IC50	=	106.6	nM	PMID[35200033]
NPT2410	Cell line	NCI-H1299	Homo sapiens	Activity	=	16.98	%	PMID[35200033]
NPT2410	Cell line	NCI-H1299	Homo sapiens	Activity	=	25.06	%	PMID[35200033]
NPT81	Cell line	A549	Homo sapiens	IC50	=	124.4	nM	PMID[35200033]
NPT29074	Cell line	PC-9	Homo sapiens	Inhibition	n.a.	n.a.	%	PMID[35200033]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	n.a.	n.a.	%	PMID[35200033]
NPT29074	Cell line	PC-9	Homo sapiens	Activity	=	6.66	%	PMID[35200033]
NPT28438	Unchecked	Unchecked	n.a.	Activity	n.a.	n.a.	n.a.	PMID[35200033]
NPT29074	Cell line	PC-9	Homo sapiens	Activity	=	22.7	%	PMID[35200033]
NPT29074	Cell line	PC-9	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35200033]
NPT29074	Cell line	PC-9	Homo sapiens	IC50	=	618.5	nM	PMID[35200033]
NPT29074	Cell line	PC-9	Homo sapiens	Activity	=	11.37	%	PMID[35200033]
NPT617	Organism	Danio rerio	Danio rerio	Activity	n.a.	n.a.	n.a.	PMID[33882233]
NPT2	Others	Unspecified	n.a.	IC50	=	0.000345	ug.mL-1	PMID[12459012]
NPT2	Others	Unspecified	n.a.	IC50	=	0.0026	ug.mL-1	PMID[12459012]

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 NPC137462 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	18993
0.1-0.2	30332
0.2-0.3	449
0.3-0.4	20
0.4-0.5	27
0.5-0.6	21
0.6-0.7	13
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8358	Intermediate Similarity	NPC184555
0.791	Intermediate Similarity	NPC481623
0.791	Intermediate Similarity	NPC606297
0.6901	Remote Similarity	NPC171014
0.6849	Remote Similarity	NPC12795
0.6842	Remote Similarity	NPC44537
0.6761	Remote Similarity	NPC603706
0.6761	Remote Similarity	NPC606351
0.6753	Remote Similarity	NPC247760
0.6622	Remote Similarity	NPC73050
0.6622	Remote Similarity	NPC605625
0.6438	Remote Similarity	NPC304276
0.6154	Remote Similarity	NPC488753
0.6125	Remote Similarity	NPC154815
0.6125	Remote Similarity	NPC55602
0.6	Remote Similarity	NPC609315
0.5976	Remote Similarity	NPC233041
0.5949	Remote Similarity	NPC112936
0.5747	Remote Similarity	NPC62172
0.5714	Remote Similarity	NPC295843
0.5658	Remote Similarity	NPC481624
0.5658	Remote Similarity	NPC481626
0.5618	Remote Similarity	NPC289700
0.5443	Remote Similarity	NPC604982
0.5443	Remote Similarity	NPC608996
0.5412	Remote Similarity	NPC183603
0.5385	Remote Similarity	NPC275060
0.5333	Remote Similarity	NPC611669
0.5294	Remote Similarity	NPC213761
0.5287	Remote Similarity	NPC257610
0.5256	Remote Similarity	NPC481625
0.5244	Remote Similarity	NPC610731
0.5233	Remote Similarity	NPC488752
0.5227	Remote Similarity	NPC47870
0.5155	Remote Similarity	NPC603497
0.5114	Remote Similarity	NPC485878
0.5106	Remote Similarity	NPC155529

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC137462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4338
0.1-0.2	4765
0.2-0.3	44
0.3-0.4	2
0.4-0.5	0
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5333	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