NPASS Compound

Natural Product: NPC59754

Natural Product ID	NPC59754
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NSEWTSAADLNHNH-IETZNNBHSA-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:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 66 72 0 0 0 0 0 0 0 0999 V2000 -4.0153 1.3760 0.5933 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9708 2.0475 1.3476 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1440 1.4115 1.7023 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3559 0.1152 1.3040 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3841 -0.5317 0.5509 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2085 0.0870 0.1882 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2184 -0.6745 -0.6191 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2406 -0.2441 -2.0732 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3640 -1.2490 -2.8312 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9682 -1.0885 -2.3036 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0940 -1.3009 -3.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3630 -1.1448 -2.6422 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5424 -0.7907 -1.3231 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4488 -0.5845 -0.4850 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7563 -0.2121 0.9182 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3480 -1.3780 1.6103 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5478 -2.3874 2.0969 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0588 -3.5054 2.7713 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4191 -3.6163 2.9655 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2022 -2.5967 2.4718 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7100 -1.4892 1.8048 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5897 -0.4936 1.3343 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0614 0.3092 0.2617 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0550 1.3434 -0.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2631 0.9569 -0.6867 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2058 1.9018 -1.0372 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9960 3.2508 -0.8386 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8099 3.6487 -0.2746 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8607 2.6842 0.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5398 5.0051 -0.0482 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9588 4.1676 -1.2005 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7965 0.9178 0.7779 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2432 1.7466 -0.2228 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8152 -0.6236 -0.7823 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9364 -4.7188 3.6320 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -2.3852 1.9619 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8308 -0.7332 -0.9778 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9104 -0.5230 -0.1445 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1089 -1.6630 -4.5037 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5417 -0.3005 -2.5670 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5470 -0.5092 1.6724 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1257 2.0491 2.4568 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1063 1.8983 0.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8429 3.0623 1.6789 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6002 -1.5494 0.2638 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4595 -1.7568 -0.5859 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7981 0.7581 -2.1960 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3595 -1.0510 -3.9135 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7322 -2.2650 -2.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2360 -1.2983 -3.2665 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1488 0.1713 1.4263 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3915 -4.2762 3.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2801 -2.6528 2.6080 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4196 -0.1103 -0.8396 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1509 1.5927 -1.4859 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9586 3.0791 0.5192 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6256 5.3209 -0.3458 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6787 5.0272 -1.6666 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9337 1.4140 1.7331 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5007 2.2586 0.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4914 -5.4103 3.1291 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2684 -3.0988 1.3596 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1421 -2.6790 -4.6655 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0277 0.4573 -2.1373 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4486 -0.0306 1.5965 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5757 2.8644 2.0188 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 1 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 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 6 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 23 32 1 0 32 33 1 0 23 34 1 0 19 35 1 0 17 36 1 0 14 37 2 0 37 38 1 0 11 39 1 0 8 40 1 0 4 41 1 0 3 42 1 0 6 1 1 0 38 7 1 0 37 10 1 0 34 13 1 0 32 15 1 0 21 16 1 0 29 24 1 0 1 43 1 0 2 44 1 0 5 45 1 0 7 46 1 6 8 47 1 1 9 48 1 0 9 49 1 0 12 50 1 0 15 51 1 1 18 52 1 0 20 53 1 0 25 54 1 0 26 55 1 0 29 56 1 0 30 57 1 0 31 58 1 0 32 59 1 1 33 60 1 0 35 61 1 0 36 62 1 0 39 63 1 0 40 64 1 0 41 65 1 0 42 66 1 0 M END

Standard InCHIKey	NSEWTSAADLNHNH-IETZNNBHSA-N
Standard InCHI	InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27+,29+,30+/m1/s1
SMILES	c1cc(c(cc1[C@H]1[C@@H](Cc2c(cc3c([C@H]4c5c(cc(cc5O[C@](c5ccc(c(c5)O)O)([C@H]4O)O3)O)O)c2O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.13	Volume:	541.386 ? Van der Waals volume.
Dense:	1.064	LogP:	1.533 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.726 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.776 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	37.0
TPSA:	209.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.158	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.361	Fsp³:	0.2
MCE-18:	143.333 ? 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:	1
Colloidal aggregators:	0.92	Fluc inhibitor:	0.057 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.667 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.591 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.513	Promiscuous compounds:	0.15

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.154	MDCK Permeability:	-4.879
Pgp-inhibitor:	0.0	Pgp-substrate:	0.224
PAMPA:	0.119 ? 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):	0.0
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.951
Plasma Protein Binding (PPB):	92.493%	Volume Distribution (VD):	0.276
Fu:	11.5% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.987
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.009
BSEP inhibitor:	0.006

ADMET: Metabolism

CYP1A2-inhibitor:	0.987	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:	0.064	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.326
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):

9.255

Half-life (T1/2):

3.853

ADMET: Toxicity

hERG Blockers:	0.086	hERG Blockers (10um):	0.774
Human Hepatotoxicity (H-HT):	0.967	Drug-induced Liver Injury (DILI):	0.944
AMES Toxicity:	0.631	Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.889	Skin Sensitization:	1.0
Carcinogencity:	0.038	Eye Corrosion:	0.0
Eye Irritation:	0.546	Respiratory Toxicity:	0.88
Drug-induced Neurotoxicity:	0.042	Ototoxicity:	0.987
Hematotoxicity:	0.038	Drug-induced Nephrotoxicity:	0.736
Genotoxicity:	0.978	RPMI-8226 Immunitoxicity:	0.177
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.984
BCF:	1.305 ? 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:	3.843 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.233 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.599 ? 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
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	2007; 2008	DOI[10.1007/s11746-010-1589-7]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90246-6]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	cotyledon	n.a.	PMID[11283027]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[12670184]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[21348467]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22537213]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Peanut Skins	n.a.	n.a.	PMID[28231711]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[36431807]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oil	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.		Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oils	n.a.		Database[Phenol-Explorer]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seeds	n.a.		Database[Phenol-Explorer]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3806	Garcinia morella	Species	Clusiaceae	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 NPC59754 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	26840
0.1-0.2	20753
0.2-0.3	1988
0.3-0.4	154
0.4-0.5	48
0.5-0.6	33
0.6-0.7	17
0.7-0.8	0
0.8-0.85	7
0.85-0.9	1
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC272552
1.0	High Similarity	NPC226108
1.0	High Similarity	NPC322899
0.9394	High Similarity	NPC478616
0.9394	High Similarity	NPC478339
0.9231	High Similarity	NPC46283
0.9231	High Similarity	NPC469944
0.9231	High Similarity	NPC134911
0.9091	High Similarity	NPC44192
0.8571	High Similarity	NPC471404
0.8493	Intermediate Similarity	NPC78074
0.8378	Intermediate Similarity	NPC478337
0.8378	Intermediate Similarity	NPC478338
0.8333	Intermediate Similarity	NPC155564
0.8333	Intermediate Similarity	NPC147743
0.8333	Intermediate Similarity	NPC4809
0.8333	Intermediate Similarity	NPC73517
0.7867	Intermediate Similarity	NPC86630
0.7848	Intermediate Similarity	NPC478617
0.7763	Intermediate Similarity	NPC478340
0.7595	Intermediate Similarity	NPC159526
0.7308	Intermediate Similarity	NPC106601
0.7308	Intermediate Similarity	NPC151474
0.7215	Intermediate Similarity	NPC212614
0.7215	Intermediate Similarity	NPC205613
0.6747	Remote Similarity	NPC484331
0.6667	Remote Similarity	NPC12326
0.6494	Remote Similarity	NPC20050
0.6479	Remote Similarity	NPC58190
0.6479	Remote Similarity	NPC108811
0.6479	Remote Similarity	NPC170103
0.6479	Remote Similarity	NPC236202
0.6479	Remote Similarity	NPC262911
0.6479	Remote Similarity	NPC202742
0.6389	Remote Similarity	NPC246202
0.6389	Remote Similarity	NPC224161
0.6389	Remote Similarity	NPC46335
0.6389	Remote Similarity	NPC279406
0.6389	Remote Similarity	NPC486519
0.6322	Remote Similarity	NPC185231
0.6207	Remote Similarity	NPC484330
0.6203	Remote Similarity	NPC306267
0.5974	Remote Similarity	NPC226809
0.5946	Remote Similarity	NPC294558
0.5946	Remote Similarity	NPC18185
0.5946	Remote Similarity	NPC263940
0.5823	Remote Similarity	NPC278548
0.5758	Remote Similarity	NPC261619
0.5758	Remote Similarity	NPC61477
0.5758	Remote Similarity	NPC78770
0.5758	Remote Similarity	NPC219876
0.5758	Remote Similarity	NPC126029
0.5758	Remote Similarity	NPC15658
0.5733	Remote Similarity	NPC20757
0.5733	Remote Similarity	NPC227516
0.5625	Remote Similarity	NPC302549
0.5584	Remote Similarity	NPC313116
0.5584	Remote Similarity	NPC603340
0.5542	Remote Similarity	NPC135021
0.5443	Remote Similarity	NPC70409
0.5443	Remote Similarity	NPC204770
0.5443	Remote Similarity	NPC600551
0.5443	Remote Similarity	NPC601980
0.5443	Remote Similarity	NPC602065
0.5443	Remote Similarity	NPC611024
0.5352	Remote Similarity	NPC178054
0.5333	Remote Similarity	NPC96576
0.5309	Remote Similarity	NPC600630
0.5309	Remote Similarity	NPC607896
0.5309	Remote Similarity	NPC611369
0.5256	Remote Similarity	NPC184245
0.5256	Remote Similarity	NPC187801
0.5256	Remote Similarity	NPC610920
0.5195	Remote Similarity	NPC277331
0.5195	Remote Similarity	NPC100482

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC59754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5666
0.1-0.2	3448
0.2-0.3	30
0.3-0.4	4
0.4-0.5	0
0.5-0.6	2
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
0.5758	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD1613	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