NPASS Compound

Natural Product: NPC325191

Natural Product ID	NPC325191
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AZRLZPIFEZUZLW-KQYNXXCUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24892762
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0001506] Purine nucleotides [CHEMONTID:0001544] Purine ribonucleotides [CHEMONTID:0000026] Purine ribonucleoside bisphosphates [CHEMONTID:0002209] Purine ribonucleoside 3',5'-bisphosphates

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 48 0 0 0 0 0 0 0 0999 V2000 -4.6568 -2.3947 1.0709 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7422 -1.8273 0.5189 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6986 -0.8179 -0.3655 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4349 -0.3611 -0.7046 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3283 -0.9515 -0.1315 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4235 -1.9676 0.7565 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2485 -0.2931 -0.6568 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6615 0.6569 -1.5117 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0056 0.6070 -1.5340 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8712 -0.5861 -0.3310 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3521 0.2706 0.8061 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3961 1.3108 0.0012 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8837 0.5396 -1.1613 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0073 -0.4950 -1.3806 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2734 0.0162 -0.8628 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3011 -0.7950 0.2721 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8879 -1.3054 0.4999 P 0 0 0 0 0 0 0 0 0 0 0 0 4.4130 -0.6252 1.7482 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8587 -0.9188 -0.8421 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9435 -2.9753 0.7282 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6089 -3.6221 0.3150 Se 0 0 0 0 0 6 0 0 0 0 0 0 5.5757 -4.5119 -1.0752 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1848 -4.6233 1.5045 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8217 -2.2528 0.1026 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2817 2.4513 -0.2365 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2637 3.8726 0.3752 P 0 0 0 0 0 0 0 0 0 0 0 0 1.1915 4.6382 -0.5372 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1987 3.5137 1.7519 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9573 4.9162 0.9118 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3937 0.8149 1.5412 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8488 -0.2264 -0.9413 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8040 -3.2170 1.7856 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9978 1.3204 -2.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8199 -1.6487 0.0499 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3407 -0.2942 1.4293 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2770 1.5779 0.6268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9420 1.1071 -2.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6838 -0.5598 -1.7249 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9900 0.8327 -0.6780 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3636 -0.0742 -0.6834 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2720 -2.3204 -0.7951 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5953 4.3027 2.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5770 5.1704 0.1658 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5623 1.7249 1.1629 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0996 -0.2776 -1.9519 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4940 0.2979 -0.3166 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 2 0 7 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 17 20 1 0 20 21 1 0 21 22 2 0 21 23 2 0 21 24 1 0 12 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 26 29 1 0 11 30 1 0 3 31 1 0 6 1 1 0 9 4 1 0 14 10 1 0 1 32 1 0 8 33 1 0 10 34 1 0 11 35 1 0 12 36 1 0 13 37 1 0 15 38 1 0 15 39 1 0 19 40 1 0 24 41 1 0 28 42 1 0 29 43 1 0 30 44 1 0 31 45 1 0 31 46 1 0 M END

Standard InCHIKey	AZRLZPIFEZUZLW-KQYNXXCUSA-N
Standard InCHI	InChI=1S/C10H15N5O13P2Se/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/t4-,6-,7-,10-/m1/s1
SMILES	C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O[Se](=O)(=O)O)OP(=O)(O)O)O)N

Calculated Properties

Physi-Chem Properties

Molecular Weight:	554.93	Volume:	28731260.307 ? Van der Waals volume.
Dense:	0.0	LogP:	-3.357 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.526 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.765 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	19.0
TPSA:	275.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	7.0	Rings:	3.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.146	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.858	Fsp³:	0.5
MCE-18:	91.867 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.003	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.073 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.327	Promiscuous compounds:	0.053

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.761	MDCK Permeability:	-5.252
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.999 ? 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):	0.105
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.094
50% Bioavailability (F50%):	0.275

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.48
Plasma Protein Binding (PPB):	22.768%	Volume Distribution (VD):	-0.901
Fu:	59.161% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.004
BSEP inhibitor:	0.098

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.823	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.042 ? 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):

1.558

Half-life (T1/2):

1.733

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.015
Human Hepatotoxicity (H-HT):	0.191	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.088	Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.998	Skin Sensitization:	0.976
Carcinogencity:	0.836	Eye Corrosion:	0.0
Eye Irritation:	0.347	Respiratory Toxicity:	0.993
Drug-induced Neurotoxicity:	0.514	Ototoxicity:	0.266
Hematotoxicity:	0.061	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.135
A549 Cytotoxicity:	0.001	Hek293 Cytotoxicity:	0.537
BCF:	0.075 ? 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:	2.374 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.533 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.483 ? 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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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 NPC325191 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	37207
0.1-0.2	12476
0.2-0.3	74
0.3-0.4	39
0.4-0.5	31
0.5-0.6	17
0.6-0.7	10
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	NPC164952
0.7971	Intermediate Similarity	NPC302778
0.7971	Intermediate Similarity	NPC329404
0.7971	Intermediate Similarity	NPC212551
0.7	Intermediate Similarity	NPC85689
0.6383	Remote Similarity	NPC189261
0.6364	Remote Similarity	NPC130586
0.6203	Remote Similarity	NPC174802
0.6133	Remote Similarity	NPC185991
0.6133	Remote Similarity	NPC321814
0.6125	Remote Similarity	NPC481375
0.6125	Remote Similarity	NPC606410
0.6026	Remote Similarity	NPC324198
0.6026	Remote Similarity	NPC326529
0.6026	Remote Similarity	NPC319100
0.5823	Remote Similarity	NPC224076
0.5732	Remote Similarity	NPC161224
0.5663	Remote Similarity	NPC323091
0.5658	Remote Similarity	NPC211025
0.5641	Remote Similarity	NPC121222
0.5393	Remote Similarity	NPC326082
0.5352	Remote Similarity	NPC317821
0.5294	Remote Similarity	NPC316618
0.5263	Remote Similarity	NPC136349
0.5263	Remote Similarity	NPC219313
0.5233	Remote Similarity	NPC607463
0.5205	Remote Similarity	NPC156461
0.5205	Remote Similarity	NPC107374
0.5205	Remote Similarity	NPC600382
0.5205	Remote Similarity	NPC612067
0.5135	Remote Similarity	NPC229974
0.5128	Remote Similarity	NPC601970

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC325191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6518
0.1-0.2	2508
0.2-0.3	59
0.3-0.4	44
0.4-0.5	13
0.5-0.6	5
0.6-0.7	2
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
0.6203	Remote Similarity	NPD339	Phase 2
0.6133	Remote Similarity	NPD283	Phase 4
0.5823	Remote Similarity	NPD169	Phase 2
0.5357	Remote Similarity	NPD6417	Clinical (unspecified phase)
0.5263	Remote Similarity	NPD548	Clinical (unspecified phase)
0.5205	Remote Similarity	NPD249	Phase 4
0.5205	Remote Similarity	NPD250	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