NPASS Compound

Natural Product: NPC275932

Natural Product ID	NPC275932
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GZCGUPFRVQAUEE-KCDKBNATSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	3037556
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0001540] Monosaccharides [CHEMONTID:0001498] Hexoses

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 24 23 0 0 0 0 0 0 0 0999 V2000 -2.1268 1.0558 0.3818 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2629 1.1697 0.7909 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8127 0.1746 -0.7516 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9577 -0.9560 -0.2423 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1923 -0.5510 0.6128 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4508 -0.1440 -0.0886 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4425 1.1960 -0.7418 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7887 1.4435 -1.1267 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3831 0.0220 0.9934 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5767 -1.7532 1.3082 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6790 -1.9016 -1.2054 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0384 -0.4146 -1.1739 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3711 1.6413 0.9034 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3776 0.7557 -1.5720 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7124 -1.5145 0.4509 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0656 0.1610 1.4029 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8396 -0.9148 -0.7625 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8574 1.2701 -1.6784 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1352 1.9654 -0.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3851 1.1007 -0.3871 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8960 0.6492 1.6146 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4433 -1.5673 1.7775 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1017 -2.4393 -0.8942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0881 -0.4488 -2.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 1 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 6 9 1 0 5 10 1 0 4 11 1 0 3 12 1 0 1 13 1 0 3 14 1 6 4 15 1 1 5 16 1 1 6 17 1 6 7 18 1 0 7 19 1 0 8 20 1 0 9 21 1 0 10 22 1 0 11 23 1 0 12 24 1 0 M END

Standard InCHIKey	GZCGUPFRVQAUEE-KCDKBNATSA-N
Standard InCHI	InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6-/m0/s1
SMILES	C(=O)[C@@H]([C@H]([C@H]([C@@H](CO)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	180.06	Volume:	162.437 ? Van der Waals volume.
Dense:	1.108	LogP:	-1.974 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-1.253 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	0.141 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	1.0
TPSA:	118.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	5.0	Rings:	0.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.282	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.905	Fsp³:	0.833
MCE-18:	4.0 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.049	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.032 ? 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:	0.586	Promiscuous compounds:	0.072

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.697	MDCK Permeability:	-4.301
Pgp-inhibitor:	0.0	Pgp-substrate:	0.435
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):	0.17
20% Bioavailability (F20%):	0.194	30% Bioavailability (F30%):	0.454
50% Bioavailability (F50%):	0.818

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055	MRP1:	0.015
Plasma Protein Binding (PPB):	26.633%	Volume Distribution (VD):	-0.474
Fu:	79.64% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.967
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.045
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.03
CYP2C9-inhibitor:	0.986	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.891
HLM stability:	0.023 ? 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):

2.383

Half-life (T1/2):

2.147

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.075
Human Hepatotoxicity (H-HT):	0.286	Drug-induced Liver Injury (DILI):	0.016
AMES Toxicity:	0.863	Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	0.957
Carcinogencity:	0.342	Eye Corrosion:	0.006
Eye Irritation:	0.71	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.019	Ototoxicity:	0.92
Hematotoxicity:	0.217	Drug-induced Nephrotoxicity:	0.5
Genotoxicity:	0.253	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.039	Hek293 Cytotoxicity:	0.043
BCF:	0.139 ? 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:	1.997 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.486 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.908 ? 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
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[18952419]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	root	n.a.	PMID[22233034]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23316950]
NPO25543	Vitex leptobotrys	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24404757]
NPO4633	Calypogeia integristipula	Species	Calypogeiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37959695]
NPO28881	Virola sebifera	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39065009]
NPO3729	Cetraria islandica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561895]
NPO7201	Rhodopila globiformis	Species	Acetobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25424	Putterlickia verrucosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4633	Calypogeia integristipula	Species	Calypogeiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3729	Cetraria islandica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2777	Cirsium brevistylum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5786	Desmodium oxyphyllum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6513	Vernonia condensata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28881	Virola sebifera	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16888	Sophora davidii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11117	Xerula melanotricha	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5413	Adonis mongolica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15057	Isodon gesneroides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25543	Vitex leptobotrys	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12519	Asarum caulescens	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21924	Althaea officinalis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15779	Larix laricina	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14022	Salvia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23265	Dianthus caryophyllus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11742	Eupatorium altissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO581	Conyza bonariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12519	Asarum caulescens	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5413	Adonis mongolica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11742	Eupatorium altissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12519	Asarum caulescens	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23265	Dianthus caryophyllus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15057	Isodon gesneroides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11742	Eupatorium altissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5413	Adonis mongolica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25424	Putterlickia verrucosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO581	Conyza bonariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14022	Salvia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21924	Althaea officinalis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11742	Eupatorium altissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16888	Sophora davidii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11742	Eupatorium altissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2777	Cirsium brevistylum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7201	Rhodopila globiformis	Species	Acetobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17117	Diaporthe amygdali	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27	Gentiana dahurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4633	Calypogeia integristipula	Species	Calypogeiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11895	Nama johnstonii	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5413	Adonis mongolica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13085	Islaya minor	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15779	Larix laricina	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3729	Cetraria islandica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15057	Isodon gesneroides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11478	Aniba duckei	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5786	Desmodium oxyphyllum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21924	Althaea officinalis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6513	Vernonia condensata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25424	Putterlickia verrucosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11117	Xerula melanotricha	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23265	Dianthus caryophyllus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25543	Vitex leptobotrys	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28881	Virola sebifera	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12034	Dictamnus gymnostylis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO581	Conyza bonariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14022	Salvia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12519	Asarum caulescens	Species	Aristolochiaceae	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 NPC275932 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	38081
0.1-0.2	11560
0.2-0.3	187
0.3-0.4	15
0.4-0.5	1
0.5-0.6	6
0.6-0.7	0
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC606151
0.8333	Intermediate Similarity	NPC270088
0.8333	Intermediate Similarity	NPC200137
0.5882	Remote Similarity	NPC293908
0.5882	Remote Similarity	NPC66052
0.5882	Remote Similarity	NPC192065
0.5882	Remote Similarity	NPC86412
0.5556	Remote Similarity	NPC261351
0.5556	Remote Similarity	NPC31981

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC275932 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8096
0.1-0.2	967
0.2-0.3	60
0.3-0.4	16
0.4-0.5	5
0.5-0.6	3
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	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD9001	Phase 2
1.0	High Similarity	NPD9002	Approved
0.5882	Remote Similarity	NPD9051	Approved
0.5882	Remote Similarity	NPD9052	Phase 4
0.5882	Remote Similarity	NPD9053	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