NPASS Compound

Natural Product: NPC188306

Natural Product ID	NPC188306
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VCWMRQDBPZKXKG-DXNLKLAMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

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 45 46 0 0 0 0 0 0 0 0999 V2000 -3.0663 2.1953 0.8344 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3039 0.9848 0.3844 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2082 0.0811 -0.4020 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6033 -1.2670 -0.6808 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9548 -1.7880 0.5882 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9832 -0.7171 1.0698 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7975 0.3461 1.5237 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2209 -0.1992 0.0347 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1341 -0.2546 0.2514 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7596 1.1261 0.3405 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2545 0.9893 0.3210 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7596 0.2923 -0.9144 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6236 -0.2349 -1.7650 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7621 -1.0942 -0.8363 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8342 -1.8268 -1.5346 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9028 0.7497 -2.3904 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5148 -0.8064 -0.5047 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8622 2.2372 0.4356 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4113 1.6195 1.6176 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3586 -3.0145 0.4247 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6557 -2.1214 -1.0389 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3641 -0.1466 0.3760 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5844 2.8542 -0.2842 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3455 2.8774 1.3530 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8939 1.8918 1.4909 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4423 1.2881 -0.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4603 0.6026 -1.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8707 -1.2576 -1.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7758 -1.8871 1.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4075 -1.0972 1.9135 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3141 -0.7263 1.2582 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3545 1.8288 -0.3889 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5324 0.4302 1.2606 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3866 0.9520 -1.5475 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0756 -0.9460 -2.4895 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4851 -1.7979 -0.3474 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8328 -2.7527 -1.2159 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5027 1.5563 -2.4842 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3188 -0.9468 -1.0635 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7978 2.0536 0.7675 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1171 1.3763 2.2838 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6075 -3.6698 1.1510 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5073 -3.0261 -0.6642 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9911 0.6302 0.2955 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1338 2.6154 -1.1184 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 13 16 1 0 12 17 1 0 11 18 1 0 10 19 1 0 5 20 1 0 4 21 1 0 3 22 1 0 1 23 1 0 7 2 1 0 14 9 1 0 1 24 1 0 1 25 1 0 2 26 1 6 3 27 1 6 4 28 1 6 5 29 1 1 6 30 1 1 9 31 1 1 10 32 1 6 11 33 1 1 12 34 1 6 13 35 1 6 14 36 1 1 15 37 1 0 16 38 1 0 17 39 1 0 18 40 1 0 19 41 1 0 20 42 1 0 21 43 1 0 22 44 1 0 23 45 1 0 M END

Standard InCHIKey	VCWMRQDBPZKXKG-DXNLKLAMSA-N
Standard InCHI	InChI=1S/C12H22O11/c13-1-2-3(14)4(15)10(21)12(22-2)23-11-8(19)6(17)5(16)7(18)9(11)20/h2-21H,1H2/t2-,3+,4+,5-,6-,7+,8+,9+,10-,11-,12-/m1/s1
SMILES	C([C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O[C@@H]1[C@H]([C@@H]([C@H]([C@@H]([C@@H]1O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	342.12	Volume:	295.688 ? Van der Waals volume.
Dense:	1.157	LogP:	-2.635 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-2.017 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.336 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	12.0
TPSA:	200.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	9.0	Rings:	2.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.236	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.235	Fsp³:	1.0
MCE-18:	49.583 ? 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:	Rejected
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.2	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.045 ? 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:	0.496	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.845	MDCK Permeability:	-4.809
Pgp-inhibitor:	0.0	Pgp-substrate:	0.963
PAMPA:	1.0 ? 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):	1.0
20% Bioavailability (F20%):	0.983	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.09
Plasma Protein Binding (PPB):	28.545%	Volume Distribution (VD):	-0.532
Fu:	74.503% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.959
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.003
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.006	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:	0.931
HLM stability:	0.0 ? 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):

1.231

Half-life (T1/2):

2.111

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.08
Human Hepatotoxicity (H-HT):	0.259	Drug-induced Liver Injury (DILI):	0.114
AMES Toxicity:	0.832	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	0.96
Carcinogencity:	0.028	Eye Corrosion:	0.0
Eye Irritation:	0.311	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.984
Hematotoxicity:	0.378	Drug-induced Nephrotoxicity:	0.896
Genotoxicity:	0.008	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.14	Hek293 Cytotoxicity:	0.039
BCF:	0.164 ? 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:	1.558 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	2.941 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.185 ? 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 NPC188306 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	35984
0.1-0.2	10577
0.2-0.3	2692
0.3-0.4	493
0.4-0.5	83
0.5-0.6	19
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7	Intermediate Similarity	NPC23134
0.6667	Remote Similarity	NPC42503
0.6667	Remote Similarity	NPC282143
0.6667	Remote Similarity	NPC107914
0.6667	Remote Similarity	NPC242073
0.6667	Remote Similarity	NPC299781
0.6667	Remote Similarity	NPC157193
0.6667	Remote Similarity	NPC608193
0.6061	Remote Similarity	NPC124963
0.5882	Remote Similarity	NPC326533
0.575	Remote Similarity	NPC32148
0.5714	Remote Similarity	NPC317501
0.5714	Remote Similarity	NPC605930
0.5556	Remote Similarity	NPC143326
0.5405	Remote Similarity	NPC31496
0.5385	Remote Similarity	NPC268243
0.5366	Remote Similarity	NPC83248
0.5349	Remote Similarity	NPC604425
0.5263	Remote Similarity	NPC233726
0.525	Remote Similarity	NPC246558
0.525	Remote Similarity	NPC323361
0.525	Remote Similarity	NPC67660
0.525	Remote Similarity	NPC165198
0.525	Remote Similarity	NPC209753
0.525	Remote Similarity	NPC58629
0.5128	Remote Similarity	NPC130683
0.5122	Remote Similarity	NPC290179
0.5122	Remote Similarity	NPC132938

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC188306 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8135
0.1-0.2	860
0.2-0.3	122
0.3-0.4	12
0.4-0.5	6
0.5-0.6	14
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.697	Remote Similarity	NPD905	Phase 4
0.5625	Remote Similarity	NPD8994	Approved
0.5263	Remote Similarity	NPD904	Phase 3
0.525	Remote Similarity	NPD888	Phase 3
0.525	Remote Similarity	NPD889	Approved
0.525	Remote Similarity	NPD890	Clinical (unspecified phase)
0.525	Remote Similarity	NPD891	Phase 3
0.525	Remote Similarity	NPD892	Phase 3
0.525	Remote Similarity	NPD893	Approved
0.525	Remote Similarity	NPD894	Phase 4
0.5227	Remote Similarity	NPD896	Approved
0.5227	Remote Similarity	NPD897	Approved
0.5227	Remote Similarity	NPD898	Phase 4
0.5128	Remote Similarity	NPD887	Approved
0.5128	Remote Similarity	NPD895	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