NPASS Compound

Natural Product: NPC176244

Natural Product ID	NPC176244
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UZFVFMDEGBUPFO-ZZZQZPNGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44207161
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid O-glycosides

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 73 77 0 0 0 0 0 0 0 0999 V2000 6.8909 -1.6147 0.7592 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2066 -1.7622 1.1817 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5392 -2.7644 2.0916 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5405 -3.6028 2.5613 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2502 -3.4285 2.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8924 -2.4443 1.2219 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5117 -2.2588 0.7512 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7344 -3.3269 0.3519 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4999 -3.2044 -0.0757 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9532 -1.9982 -0.1347 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6394 -1.8244 -0.5851 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0054 -0.6147 -0.6750 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7208 0.5329 -0.2890 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0179 0.3816 0.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6315 -0.8620 0.2370 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9288 -1.0078 0.6844 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5792 -0.0065 1.0307 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7861 1.4728 0.5545 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1124 1.7465 -0.3744 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7807 2.3721 0.4961 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0017 3.3042 1.4075 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8983 4.2463 2.1810 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0470 4.7403 1.3740 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7299 3.5013 0.7646 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9986 3.9913 0.0680 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6516 2.9837 -0.6036 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8381 2.9631 -0.1387 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9244 5.4306 2.2080 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1399 5.2656 2.7453 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6121 2.4971 2.3953 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2897 -0.4945 -1.1250 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0514 -1.5593 -1.5888 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0971 -2.0130 -0.5817 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3716 -1.2406 -0.6390 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8705 -1.0688 -2.0429 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8879 -1.7054 -3.0047 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3196 -1.3214 -4.4002 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5887 -1.8500 -4.7062 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6430 -1.1532 -2.7831 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1384 -1.6577 -2.1934 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1767 0.0047 -0.0516 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2965 -3.3803 -0.7679 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8620 -2.8859 2.4945 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6767 -0.8319 0.0568 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0031 -1.1158 0.8244 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8371 -4.3677 3.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4675 -4.0790 2.4841 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2178 -4.3147 0.4126 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1483 -2.7641 -0.8605 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2164 2.0915 -0.1245 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1768 1.5773 1.1864 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7870 3.8506 0.8954 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3406 3.6405 3.0282 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7342 5.3565 0.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9807 2.8306 1.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6916 4.8464 -0.5572 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6719 4.3408 0.8966 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3167 2.8472 -1.5298 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8695 6.4219 2.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0764 5.0962 3.6960 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2919 1.5676 2.3415 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4379 -2.4299 -1.8093 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6733 -1.8828 0.4314 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1029 -1.7777 0.0082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9844 -0.0042 -2.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9082 -2.8018 -2.9532 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6250 -1.7149 -5.1756 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3971 -0.2415 -4.5361 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6294 -2.1126 -5.6379 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1473 -2.4154 -1.5571 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4042 0.4238 -0.5197 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3779 -3.7689 -0.9256 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5740 -2.6514 1.7881 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 6 7 1 0 7 8 2 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 15 16 1 0 16 17 2 0 14 18 1 0 13 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 22 29 1 0 21 30 1 0 12 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 3 43 1 0 6 1 1 0 16 7 1 0 27 20 1 0 39 32 1 0 15 10 1 0 1 44 1 0 2 45 1 0 4 46 1 0 5 47 1 0 8 48 1 0 11 49 1 0 18 50 1 0 20 51 1 1 21 52 1 6 22 53 1 1 23 54 1 6 24 55 1 1 25 56 1 0 25 57 1 0 26 58 1 0 28 59 1 0 29 60 1 0 30 61 1 0 32 62 1 6 33 63 1 1 34 64 1 1 35 65 1 6 36 66 1 6 37 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	UZFVFMDEGBUPFO-ZZZQZPNGSA-N
Standard InCHI	InChI=1S/C27H30O16/c28-6-14-18(32)21(35)23(37)26(41-14)40-13-5-12-16(17(31)11(8-39-12)9-1-3-10(30)4-2-9)20(34)25(13)43-27-24(38)22(36)19(33)15(7-29)42-27/h1-5,8,14-15,18-19,21-24,26-30,32-38H,6-7H2/t14-,15-,18-,19-,21+,22+,23-,24-,26-,27+/m1/s1
SMILES	c1cc(ccc1c1coc2cc(c(c(c2c1=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	-0.562 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.538 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.317 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.13	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.744	Fsp³:	0.444
MCE-18:	119.436 ? 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:	0.596	Fluc inhibitor:	0.273 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.739 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.532 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.275	Promiscuous compounds:	0.513

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.71	MDCK Permeability:	-4.93
Pgp-inhibitor:	0.0	Pgp-substrate:	0.186
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):	0.965
20% Bioavailability (F20%):	0.214	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.01
Plasma Protein Binding (PPB):	80.208%	Volume Distribution (VD):	-0.145
Fu:	20.122% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.025
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.129
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):

1.795

Half-life (T1/2):

5.231

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.024
Human Hepatotoxicity (H-HT):	0.84	Drug-induced Liver Injury (DILI):	0.987
AMES Toxicity:	0.961	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	1.0
Carcinogencity:	0.092	Eye Corrosion:	0.0
Eye Irritation:	0.006	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.995
Hematotoxicity:	0.227	Drug-induced Nephrotoxicity:	0.828
Genotoxicity:	0.944	RPMI-8226 Immunitoxicity:	0.084
A549 Cytotoxicity:	0.381	Hek293 Cytotoxicity:	0.317
BCF:	0.308 ? 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:	2.744 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.445 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.394 ? 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
NPO25932	Delphinium barbeyi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf00025a020]
NPO9446	Asterias rathbuni	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473430]
NPO13715	Bertya dimerostigma	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6243	Fomes fastuosus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5081	Amorphinopsis foetida	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25932	Delphinium barbeyi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9446	Asterias rathbuni	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25932	Delphinium barbeyi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8707.2	Pueraria montana var. thomsonii	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25932	Delphinium barbeyi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8707.2	Pueraria montana var. thomsonii	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13715	Bertya dimerostigma	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8707.2	Pueraria montana var. thomsonii	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25932	Delphinium barbeyi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5479	Astragalus wiedemannianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9446	Asterias rathbuni	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6243	Fomes fastuosus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5081	Amorphinopsis foetida	Species	Halichondriidae	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 NPC176244 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	21279
0.1-0.2	24684
0.2-0.3	2670
0.3-0.4	955
0.4-0.5	203
0.5-0.6	40
0.6-0.7	15
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9275	High Similarity	NPC205076
0.7792	Intermediate Similarity	NPC48773
0.7703	Intermediate Similarity	NPC197896
0.7703	Intermediate Similarity	NPC313163
0.7467	Intermediate Similarity	NPC105511
0.7436	Intermediate Similarity	NPC307518
0.7403	Intermediate Similarity	NPC224462
0.7237	Intermediate Similarity	NPC161749
0.6835	Remote Similarity	NPC100720
0.6512	Remote Similarity	NPC479405
0.65	Remote Similarity	NPC73511
0.6456	Remote Similarity	NPC348541
0.6437	Remote Similarity	NPC479404
0.6375	Remote Similarity	NPC156457
0.6341	Remote Similarity	NPC481043
0.6341	Remote Similarity	NPC80140
0.6296	Remote Similarity	NPC105025
0.625	Remote Similarity	NPC259070
0.6173	Remote Similarity	NPC93337
0.6173	Remote Similarity	NPC258035
0.6143	Remote Similarity	NPC216769
0.6125	Remote Similarity	NPC135345
0.6049	Remote Similarity	NPC211014
0.5976	Remote Similarity	NPC234739
0.5926	Remote Similarity	NPC45165
0.5811	Remote Similarity	NPC285973
0.5747	Remote Similarity	NPC479407
0.5714	Remote Similarity	NPC186807
0.5714	Remote Similarity	NPC24043
0.5698	Remote Similarity	NPC229729
0.5647	Remote Similarity	NPC138540
0.5647	Remote Similarity	NPC201292
0.5632	Remote Similarity	NPC479406
0.5604	Remote Similarity	NPC303913
0.5581	Remote Similarity	NPC609451
0.5542	Remote Similarity	NPC160515
0.5529	Remote Similarity	NPC45638
0.5517	Remote Similarity	NPC601607
0.5476	Remote Similarity	NPC58053
0.5465	Remote Similarity	NPC117260
0.5455	Remote Similarity	NPC602805
0.5426	Remote Similarity	NPC479403
0.5412	Remote Similarity	NPC146792
0.5402	Remote Similarity	NPC488071
0.5368	Remote Similarity	NPC257714
0.5341	Remote Similarity	NPC21666
0.5294	Remote Similarity	NPC39360
0.5294	Remote Similarity	NPC29763
0.5294	Remote Similarity	NPC210003
0.5233	Remote Similarity	NPC603782
0.5227	Remote Similarity	NPC479402
0.5227	Remote Similarity	NPC479401
0.5222	Remote Similarity	NPC488072
0.5172	Remote Similarity	NPC84265
0.5172	Remote Similarity	NPC603655
0.5169	Remote Similarity	NPC605067
0.5169	Remote Similarity	NPC610187
0.5116	Remote Similarity	NPC83283
0.5111	Remote Similarity	NPC607201
0.5057	Remote Similarity	NPC297987
0.5057	Remote Similarity	NPC323593
0.5057	Remote Similarity	NPC203500
0.5057	Remote Similarity	NPC259152

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC176244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5398
0.1-0.2	3675
0.2-0.3	60
0.3-0.4	12
0.4-0.5	3
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.7237	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.5542	Remote Similarity	NPD3818	Discontinued

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