NPASS Compound

Natural Product: NPC56109

Natural Product ID	NPC56109
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ergocristine
IUPAC Name	n.a.
Synonyms	Ergocristine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL446315
PubChem CID	31116
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002679] Ergoline and derivatives [CHEMONTID:0002680] Lysergic acids and derivatives [CHEMONTID:0002030] Ergopeptines [CHEMONTID:0000371] Ergotamines, dihydroergotamines, 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 84 91 0 0 0 0 0 0 0 0999 V2000 -0.1248 -0.6970 -3.6876 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0409 0.2031 -2.4576 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 1.4811 -2.7718 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6003 -0.5350 -1.3067 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0367 -0.7192 -1.7124 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4756 -1.2939 -2.7395 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8085 -0.1051 -0.6892 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1311 0.4969 -0.6156 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0205 0.0480 -1.7068 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3722 0.6266 -1.6783 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4598 -0.0380 -1.1754 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7349 0.5404 -1.1329 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9307 1.8045 -1.6011 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8495 2.5094 -2.1200 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6088 1.9192 -2.1499 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6315 0.3140 0.7500 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7625 -0.1725 1.0610 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7401 0.7324 1.8056 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9577 1.2381 3.1431 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7810 0.6970 3.9213 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8746 -0.0004 2.8970 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3366 0.6672 1.5966 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9071 -0.1875 0.4615 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7995 -1.5423 0.7703 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7187 0.1977 -0.1541 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0735 -1.7556 -1.0785 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1612 -1.9450 -0.4659 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0319 -0.9433 0.1826 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3633 -0.9457 -0.4864 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4279 -0.7274 0.2317 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7583 -0.7262 -0.4205 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9592 -1.4168 -1.5928 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2455 -1.3500 -2.1057 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2714 -0.6237 -1.4664 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0246 0.0604 -0.2832 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7589 -0.0251 0.1906 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5922 0.6798 1.3588 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2699 0.7236 2.0368 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4367 -0.4809 1.6703 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1736 -0.4295 2.3051 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1944 -0.5400 3.7241 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0994 -1.1049 1.6674 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8468 1.2177 1.5916 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7102 0.8358 0.5888 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6021 -3.2814 -0.3913 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9712 -0.4014 -4.3058 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7987 -0.6541 -4.3197 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2685 -1.7494 -3.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0820 0.4783 -2.3141 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7618 1.2576 -3.1422 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2339 2.0771 -3.5435 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8545 2.0136 -1.8091 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0386 1.6303 -0.7339 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1704 -1.0676 -1.5640 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5560 0.1104 -2.7170 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3836 -1.0384 -0.8131 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5618 -0.0256 -0.7250 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9218 2.2247 -1.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0375 3.5134 -2.4853 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7613 2.4588 -2.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9272 0.9358 3.5646 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8291 2.3437 3.1088 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1966 1.4613 4.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1858 -0.0283 4.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8228 0.1833 3.1101 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1778 -1.0690 2.9329 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8215 1.6488 1.5628 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0700 -1.7633 1.3704 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6000 0.0590 -0.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4692 -1.1223 -1.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2095 -1.9737 -2.1029 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4692 -1.8682 -3.0206 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2739 -0.5709 -1.8645 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6803 1.6194 1.6852 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3820 0.7785 3.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9875 -1.3528 2.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1499 -0.5549 4.0964 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7494 -1.4223 4.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6383 0.4137 4.1299 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1982 -2.1888 1.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1534 -0.7049 2.0884 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0835 1.8396 2.4402 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7032 1.0803 0.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2793 -3.9779 -1.0241 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 4 2 1 6 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 8 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 4 26 1 0 26 27 2 3 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 40 42 1 0 37 43 2 0 43 44 1 0 27 45 1 0 25 4 1 0 42 28 1 0 23 7 1 0 39 30 1 0 15 10 1 0 22 18 1 0 36 31 1 0 44 35 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 3 50 1 0 3 51 1 0 3 52 1 0 8 53 1 6 9 54 1 0 9 55 1 0 11 56 1 0 12 57 1 0 13 58 1 0 14 59 1 0 15 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 22 67 1 6 24 68 1 0 28 69 1 1 29 70 1 0 32 71 1 0 33 72 1 0 34 73 1 0 38 74 1 0 38 75 1 0 39 76 1 1 41 77 1 0 41 78 1 0 41 79 1 0 42 80 1 0 42 81 1 0 43 82 1 0 44 83 1 0 45 84 1 0 M END

Standard InCHIKey	HEFIYUQVAZFDEE-MKTPKCENSA-N
Standard InCHI	InChI=1S/C35H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41)/t23-,27-,28+,29+,34-,35+/m1/s1
SMILES	CC(C)[C@@]1(C(=O)N2[C@@H](Cc3ccccc3)C(=O)N3CCC[C@H]3[C@]2(O)O1)N=C([C@@H]1C=C2c3cccc4c3c(C[C@H]2N(C)C1)c[nH]4)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	609.3	Volume:	615.398 ? Van der Waals volume.
Dense:	0.99	LogP:	3.179 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.058 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.231 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	42.0
TPSA:	121.7 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	8.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.301	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.06	Fsp³:	0.457
MCE-18:	161.275 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.667	Fluc inhibitor:	0.018 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.927 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.99 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.942

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.634	MDCK Permeability:	-5.132
Pgp-inhibitor:	1.0	Pgp-substrate:	1.0
PAMPA:	0.003 ? 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):	0.142
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.636
Plasma Protein Binding (PPB):	96.549%	Volume Distribution (VD):	0.967
Fu:	1.474% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.962	BCRP inhibitor:	0.211
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.971	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.992	CYP2C19-substrate:	0.015
CYP2C9-inhibitor:	0.708	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.362
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.009
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.601 ? 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):

12.307

Half-life (T1/2):

2.054

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.078
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.905	Rat Oral Acute Toxicity:	0.73
Maximum Recommended Daily Dose:	0.869	Skin Sensitization:	1.0
Carcinogencity:	0.949	Eye Corrosion:	0.0
Eye Irritation:	0.017	Respiratory Toxicity:	0.43
Drug-induced Neurotoxicity:	0.752	Ototoxicity:	0.75
Hematotoxicity:	0.49	Drug-induced Nephrotoxicity:	0.348
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.078
A549 Cytotoxicity:	0.043	Hek293 Cytotoxicity:	0.721
BCF:	1.236 ? 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:	4.091 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.453 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.024 ? 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
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17841110]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20778930]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24009	Claviceps purpurea	Species	Clavicipitaceae	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
Activity	1
Potency	25
Ki	4

Activity Type	# Activity
Individual protein	24
Protein-protein interaction	2
Organism	2
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT211	Individual protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT3	Individual protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	8912.5	nM	PubChem BioAssay data set
NPT151	Individual protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT1456	Individual protein	P-glycoprotein 1	Mus musculus	Ki	=	15300.0	nM	PMID[12235267]
NPT1455	Individual protein	P-glycoprotein 3	Mus musculus	Ki	=	39400.0	nM	PMID[12235267]
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	2310.9	nM	PubChem BioAssay data set
NPT105	Individual protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT55	Individual protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	3154.8	nM	PubChem BioAssay data set
NPT533	Protein-protein interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT612	Individual protein	Canalicular multispecific organic anion transporter 1	Homo sapiens	Activity	=	60.0	%	PMID[18457386]
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT54	Individual protein	Nonstructural protein 1	Influenza A virus	Potency	=	2511.9	nM	PubChem BioAssay data set
NPT61	Individual protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT46	Individual protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	=	50118.7	nM	PubChem BioAssay data set
NPT93	Individual protein	Survival motor neuron protein	Homo sapiens	Potency	=	1122.0	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT53	Individual protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	56234.1	nM	PubChem BioAssay data set
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	8912.5	nM	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	13330.0	nM	PMID[11961113]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	42800.0	nM	PMID[11961113]
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	1122.0	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2332.3	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2936.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	29092.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	20596.2	nM	PubChem BioAssay data set

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 NPC56109 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	21195
0.1-0.2	27352
0.2-0.3	1279
0.3-0.4	22
0.4-0.5	4
0.5-0.6	3
0.6-0.7	1
0.7-0.8	2
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8969	High Similarity	NPC191382
0.8454	Intermediate Similarity	NPC155444
0.6036	Remote Similarity	NPC603739
0.5657	Remote Similarity	NPC68354
0.534	Remote Similarity	NPC611966
0.5146	Remote Similarity	NPC604662

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC56109 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2850
0.1-0.2	6001
0.2-0.3	266
0.3-0.4	10
0.4-0.5	3
0.5-0.6	8
0.6-0.7	8
0.7-0.8	2
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8969	High Similarity	NPD7781	Phase 4
0.8365	Intermediate Similarity	NPD7780	Approved
0.7358	Intermediate Similarity	NPD7952	Approved
0.7358	Intermediate Similarity	NPD7953	Pre-clinical
0.6789	Remote Similarity	NPD7717	Phase 4
0.6577	Remote Similarity	NPD7790	Approved
0.6577	Remote Similarity	NPD7791	Phase 4
0.6555	Remote Similarity	NPD7951	Phase 4
0.6491	Remote Similarity	NPD7716	Approved
0.6293	Remote Similarity	NPD7789	Approved
0.629	Remote Similarity	NPD7950	Approved
0.6126	Remote Similarity	NPD7731	Pre-clinical
0.5965	Remote Similarity	NPD7824	Approved
0.5913	Remote Similarity	NPD7271	Approved
0.5862	Remote Similarity	NPD7730	Approved
0.57	Remote Similarity	NPD4079	Phase 4
0.5657	Remote Similarity	NPD3506	Phase 4
0.5377	Remote Similarity	NPD4076	Approved
0.5333	Remote Similarity	NPD3505	Approved
0.5051	Remote Similarity	NPD4075	Phase 2

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