NPASS Compound

Natural Product: NPC182729

Natural Product ID	NPC182729
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ODHKRSFJWQEWGG-HWGSVKNTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44257291
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 71 75 0 0 0 0 0 0 0 0999 V2000 10.8359 3.1747 0.0782 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6442 1.7796 -0.0634 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3401 1.3067 -0.0529 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2533 2.1441 0.0887 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9576 1.6857 0.1003 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6738 0.3353 -0.0321 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7565 -0.5163 -0.1751 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0444 -0.0354 -0.1839 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3058 -0.1602 -0.0209 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3497 0.4941 -0.7574 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0922 0.0699 -0.7700 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6980 -0.9821 -0.0901 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3816 -1.4142 -0.1121 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9245 -2.5084 0.5828 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8447 -3.2140 1.3480 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1414 -2.7947 1.3744 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5851 -1.7008 0.6763 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9119 -1.2644 0.6978 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7447 -1.8841 1.3763 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0911 -3.4842 2.1354 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4017 -2.9326 0.5524 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4427 -2.3482 -0.1541 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2070 -3.3484 -1.0063 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1930 -2.5294 -1.8338 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1149 -1.8149 -0.8693 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2618 -1.0301 0.0885 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1531 -0.3241 1.1103 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9928 0.5062 0.3916 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8670 1.2152 1.2237 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4935 2.6782 1.0905 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7817 3.0981 -0.3226 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2609 2.9079 -0.5650 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9092 2.0278 0.4802 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1464 0.9346 0.8145 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8653 4.1688 -0.4862 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0389 2.2921 -1.2131 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1741 3.4954 1.9619 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3891 -1.8883 0.7943 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9448 -0.9268 -1.5343 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9155 -3.3361 -2.6934 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3953 -4.0357 -1.8795 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2100 3.6441 -0.7362 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4068 3.5627 1.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8677 3.4854 -0.1065 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4277 3.2204 0.1967 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1014 2.3648 0.2141 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5655 -1.5919 -0.2822 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9063 -0.6983 -0.2961 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6427 1.3790 -1.3394 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7157 -0.8205 -0.7277 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4943 -4.0932 1.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4867 -4.3628 1.8432 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1585 -1.4598 -0.7427 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7877 -4.0018 -0.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -1.7925 -2.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6926 -2.5939 -0.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6569 -0.3199 -0.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7691 -1.0984 1.6112 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5605 0.1832 1.8789 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6393 0.9060 2.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4093 2.7583 1.3433 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5008 4.1763 -0.4562 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4525 2.5433 -1.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8538 1.6332 0.0193 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2548 2.6142 1.3663 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9577 4.4764 0.4550 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6430 1.8055 -1.8055 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6311 3.7582 2.7430 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8806 -1.0971 -1.2942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5271 -4.2317 -2.6794 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4902 -4.1899 -1.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 6 9 1 0 9 10 2 0 10 11 1 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 17 18 1 0 18 19 2 0 16 20 1 0 14 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 26 38 1 0 25 39 1 0 24 40 1 0 23 41 1 0 8 3 1 0 18 9 1 0 38 22 1 0 17 12 1 0 34 29 1 0 1 42 1 0 1 43 1 0 1 44 1 0 4 45 1 0 5 46 1 0 7 47 1 0 8 48 1 0 10 49 1 0 13 50 1 0 15 51 1 0 20 52 1 0 22 53 1 6 23 54 1 1 24 55 1 6 25 56 1 1 26 57 1 6 27 58 1 0 27 59 1 0 29 60 1 1 30 61 1 1 31 62 1 1 32 63 1 6 33 64 1 0 33 65 1 0 35 66 1 0 36 67 1 0 37 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 M END

Standard InCHIKey	ODHKRSFJWQEWGG-HWGSVKNTSA-N
Standard InCHI	InChI=1S/C27H30O14/c1-36-12-4-2-11(3-5-12)14-8-37-17-7-13(6-15(28)19(17)20(14)30)40-27-25(35)23(33)22(32)18(41-27)10-39-26-24(34)21(31)16(29)9-38-26/h2-8,16,18,21-29,31-35H,9-10H2,1H3/t16-,18-,21+,22-,23+,24-,25-,26+,27-/m1/s1
SMILES	COc1ccc(cc1)c1coc2cc(cc(c2c1=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.16	Volume:	534.737 ? Van der Waals volume.
Dense:	1.081	LogP:	0.871 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.401 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.395 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	217.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.176	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.539	Fsp³:	0.444
MCE-18:	112.41 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.611	Fluc inhibitor:	0.306 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.868 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.782 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.057	Promiscuous compounds:	0.316

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.316	MDCK Permeability:	-5.266
Pgp-inhibitor:	0.0	Pgp-substrate:	0.752
PAMPA:	0.994 ? 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):	0.975
20% Bioavailability (F20%):	0.153	30% Bioavailability (F30%):	0.988
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.055
Plasma Protein Binding (PPB):	79.906%	Volume Distribution (VD):	-0.422
Fu:	18.979% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.395
BSEP inhibitor:	0.006

ADMET: Metabolism

CYP1A2-inhibitor:	0.039	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:	0.049
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
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):

1.515

Half-life (T1/2):

3.702

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.097
Human Hepatotoxicity (H-HT):	0.512	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.917	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.032	Skin Sensitization:	0.949
Carcinogencity:	0.084	Eye Corrosion:	0.0
Eye Irritation:	0.082	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.971
Hematotoxicity:	0.169	Drug-induced Nephrotoxicity:	0.913
Genotoxicity:	0.442	RPMI-8226 Immunitoxicity:	0.19
A549 Cytotoxicity:	0.194	Hek293 Cytotoxicity:	0.214
BCF:	0.374 ? 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:	3.137 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.632 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.791 ? 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
NPO24639	Streptomyces filamentosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17284073]
NPO546	Candida albicans	Species	Debaryomycetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23902158]
NPO4061	Trollius europaeus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12152	Nicotiana raimondii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO546	Candida albicans	Species	Debaryomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12152	Nicotiana raimondii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9830	Arum maximum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11127	Inulanthera calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24639	Streptomyces filamentosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15875	Scolopia chinensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7011	Chamomilla recutita	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4061	Trollius europaeus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26656	Heliotropium hirsutissimum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO546	Candida albicans	Species	Debaryomycetaceae	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 NPC182729 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	19197
0.1-0.2	26693
0.2-0.3	3054
0.3-0.4	629
0.4-0.5	217
0.5-0.6	48
0.6-0.7	12
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
0.7586	Intermediate Similarity	NPC479405
0.7586	Intermediate Similarity	NPC303913
0.75	Intermediate Similarity	NPC479404
0.7065	Intermediate Similarity	NPC51326
0.7024	Intermediate Similarity	NPC73511
0.6867	Remote Similarity	NPC160515
0.6774	Remote Similarity	NPC479403
0.6737	Remote Similarity	NPC231194
0.6395	Remote Similarity	NPC348541
0.6322	Remote Similarity	NPC197896
0.6322	Remote Similarity	NPC313163
0.6304	Remote Similarity	NPC487212
0.6277	Remote Similarity	NPC475155
0.6105	Remote Similarity	NPC22062
0.6105	Remote Similarity	NPC473634
0.6105	Remote Similarity	NPC138811
0.6	Remote Similarity	NPC235575
0.5974	Remote Similarity	NPC116632
0.5955	Remote Similarity	NPC234739
0.5895	Remote Similarity	NPC295613
0.5895	Remote Similarity	NPC473657
0.58	Remote Similarity	NPC488089
0.5778	Remote Similarity	NPC487213
0.57	Remote Similarity	NPC473623
0.57	Remote Similarity	NPC257714
0.5604	Remote Similarity	NPC156457
0.5591	Remote Similarity	NPC80140
0.5567	Remote Similarity	NPC51774
0.5545	Remote Similarity	NPC209296
0.551	Remote Similarity	NPC301683
0.5464	Remote Similarity	NPC156977
0.5455	Remote Similarity	NPC473512
0.5455	Remote Similarity	NPC129827
0.5429	Remote Similarity	NPC475261
0.5385	Remote Similarity	NPC45165
0.5354	Remote Similarity	NPC44931
0.5347	Remote Similarity	NPC46202
0.5347	Remote Similarity	NPC284277
0.5347	Remote Similarity	NPC475497
0.5312	Remote Similarity	NPC293004
0.5309	Remote Similarity	NPC303644
0.5287	Remote Similarity	NPC249824
0.5287	Remote Similarity	NPC133400
0.5253	Remote Similarity	NPC236191
0.5248	Remote Similarity	NPC186816
0.5217	Remote Similarity	NPC135345
0.5208	Remote Similarity	NPC610187
0.52	Remote Similarity	NPC67105
0.5189	Remote Similarity	NPC135358
0.5158	Remote Similarity	NPC205076
0.5149	Remote Similarity	NPC210073
0.5146	Remote Similarity	NPC65711
0.5116	Remote Similarity	NPC298845
0.51	Remote Similarity	NPC471079
0.5098	Remote Similarity	NPC204693
0.5055	Remote Similarity	NPC25547
0.5053	Remote Similarity	NPC229687
0.5053	Remote Similarity	NPC181712
0.5051	Remote Similarity	NPC52353
0.505	Remote Similarity	NPC15358
0.505	Remote Similarity	NPC67326
0.505	Remote Similarity	NPC275454
0.505	Remote Similarity	NPC227508
0.5049	Remote Similarity	NPC488074
0.5044	Remote Similarity	NPC473895

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC182729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4681
0.1-0.2	4404
0.2-0.3	51
0.3-0.4	7
0.4-0.5	6
0.5-0.6	1
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5545	Remote Similarity	NPD7054	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