NPASS Compound

Natural Product: NPC299472

Natural Product ID	NPC299472
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RXAXTTGJEMODPY-IHPAPMAYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10438202
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 69 73 0 0 0 0 0 0 0 0999 V2000 -4.7960 0.2652 -1.1389 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6216 -0.5069 -1.9176 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4399 -1.8631 -2.0079 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4151 -2.4154 -1.2995 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5705 -1.6151 -0.5002 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7343 -0.2677 -0.3991 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9191 0.5630 0.4540 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7071 0.2210 0.9858 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0883 1.1836 1.7935 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0140 0.9802 2.3318 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6698 2.4230 2.0411 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0325 3.3485 2.8402 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6159 4.5688 3.0760 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8298 4.8379 2.5046 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4665 3.9129 1.7062 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8824 2.6646 1.4578 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4435 1.7717 0.7181 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4013 6.0875 2.7608 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1949 3.0504 3.4058 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0746 -0.9659 0.7755 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1010 -1.1745 -0.2498 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2603 -1.4982 0.3653 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5297 -2.9734 0.2059 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4947 -3.4704 -1.1944 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5420 -2.5870 -1.9714 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0634 -3.2762 -3.2261 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5977 -2.3467 -4.0304 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4624 -2.0408 -1.2295 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0266 -4.7841 -1.1982 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4491 -3.6158 0.8647 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1902 -0.6569 -0.0908 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8340 0.1963 0.7049 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3291 -0.0078 0.5795 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1155 1.2666 0.6460 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6700 2.1508 -0.5185 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2662 1.6841 -0.9249 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5600 1.5137 0.2639 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5448 3.4771 -0.1421 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4570 0.9473 0.5530 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7892 -0.8887 1.5628 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2659 -2.6752 -2.7947 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9313 1.3525 -1.0602 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4242 -0.0567 -2.4694 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2304 -3.4879 -1.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7948 -2.1032 0.0635 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0979 5.3027 3.7169 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4210 4.1126 1.2513 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3740 6.2291 2.5125 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2886 3.0348 4.4215 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0017 -0.1717 -0.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1408 -1.3481 1.4595 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4170 -3.2733 0.7879 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4738 -3.4889 -1.7038 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1796 -1.7249 -2.3351 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6474 -4.0948 -3.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9487 -3.6279 -3.7946 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1150 -1.8288 -4.4986 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4445 -5.2949 -0.4413 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0509 -3.0324 1.5517 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5856 0.1979 1.7747 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5985 -0.4961 -0.4029 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8752 1.8370 1.5739 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3915 2.0479 -1.3442 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7920 2.4111 -1.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3907 0.7396 -1.4861 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0736 3.7183 0.6387 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5582 0.3087 -0.1857 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4062 -1.5725 1.2057 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0034 -3.1748 -2.2789 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 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 12 19 1 0 8 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 26 27 1 0 25 28 1 0 24 29 1 0 23 30 1 0 22 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 35 38 1 0 34 39 1 0 33 40 1 0 3 41 1 0 6 1 1 0 17 7 1 0 28 21 1 0 37 32 1 0 16 11 1 0 1 42 1 0 2 43 1 0 4 44 1 0 5 45 1 0 13 46 1 0 15 47 1 0 18 48 1 0 19 49 1 0 21 50 1 6 22 51 1 1 23 52 1 1 24 53 1 6 25 54 1 6 26 55 1 0 26 56 1 0 27 57 1 0 29 58 1 0 30 59 1 0 32 60 1 1 33 61 1 6 34 62 1 1 35 63 1 6 36 64 1 0 36 65 1 0 38 66 1 0 39 67 1 0 40 68 1 0 41 69 1 0 M END

Standard InCHIKey	RXAXTTGJEMODPY-IHPAPMAYSA-N
Standard InCHI	InChI=1S/C26H28O15/c27-7-15-18(33)20(35)24(41-25-21(36)17(32)13(31)8-37-25)26(39-15)40-23-19(34)16-12(30)5-11(29)6-14(16)38-22(23)9-1-3-10(28)4-2-9/h1-6,13,15,17-18,20-21,24-33,35-36H,7-8H2/t13-,15-,17+,18+,20+,21-,24-,25+,26+/m1/s1
SMILES	c1cc(ccc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	580.14	Volume:	526.232 ? Van der Waals volume.
Dense:	1.102	LogP:	0.837 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.157 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.139 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.156	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.627	Fsp³:	0.423
MCE-18:	116.838 ? 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:	0.625	Fluc inhibitor:	0.278 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.68 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.576 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.198	Promiscuous compounds:	0.607

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.57	MDCK Permeability:	-5.046
Pgp-inhibitor:	0.0	Pgp-substrate:	0.808
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):	0.195
20% Bioavailability (F20%):	0.524	30% Bioavailability (F30%):	0.99
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.429
Plasma Protein Binding (PPB):	83.463%	Volume Distribution (VD):	-0.097
Fu:	14.31% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.953
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.201
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.037	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.553
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.009
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.959 ? 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):

1.69

Half-life (T1/2):

3.118

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.079
Human Hepatotoxicity (H-HT):	0.57	Drug-induced Liver Injury (DILI):	0.796
AMES Toxicity:	0.901	Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.097	Skin Sensitization:	1.0
Carcinogencity:	0.161	Eye Corrosion:	0.0
Eye Irritation:	0.892	Respiratory Toxicity:	0.02
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.868
Hematotoxicity:	0.128	Drug-induced Nephrotoxicity:	0.339
Genotoxicity:	0.864	RPMI-8226 Immunitoxicity:	0.11
A549 Cytotoxicity:	0.784	Hek293 Cytotoxicity:	0.827
BCF:	0.371 ? 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:	2.877 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.346 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.516 ? 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
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22779710]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[22779710]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31625742]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13645	Armoracia rusticana	Species	Brassicaceae	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 NPC299472 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	22334
0.1-0.2	23406
0.2-0.3	3249
0.3-0.4	473
0.4-0.5	167
0.5-0.6	108
0.6-0.7	66
0.7-0.8	0
0.8-0.85	5
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304741
0.9125	High Similarity	NPC255157
0.9125	High Similarity	NPC259896
0.8706	High Similarity	NPC292929
0.8608	High Similarity	NPC170052
0.8608	High Similarity	NPC135846
0.8372	Intermediate Similarity	NPC76831
0.8193	Intermediate Similarity	NPC470405
0.8193	Intermediate Similarity	NPC163242
0.8193	Intermediate Similarity	NPC272068
0.8022	Intermediate Similarity	NPC219043
0.7865	Intermediate Similarity	NPC221342
0.7865	Intermediate Similarity	NPC476470
0.7831	Intermediate Similarity	NPC254855
0.7831	Intermediate Similarity	NPC94610
0.7683	Intermediate Similarity	NPC224530
0.7634	Intermediate Similarity	NPC48984
0.7582	Intermediate Similarity	NPC602448
0.7471	Intermediate Similarity	NPC155877
0.7294	Intermediate Similarity	NPC476215
0.7222	Intermediate Similarity	NPC12013
0.7222	Intermediate Similarity	NPC11432
0.7222	Intermediate Similarity	NPC477613
0.7045	Intermediate Similarity	NPC471079
0.7	Intermediate Similarity	NPC54802
0.7	Intermediate Similarity	NPC197304
0.6989	Remote Similarity	NPC220173
0.6893	Remote Similarity	NPC192539
0.6867	Remote Similarity	NPC77672
0.6867	Remote Similarity	NPC133671
0.6867	Remote Similarity	NPC135391
0.6867	Remote Similarity	NPC78263
0.6867	Remote Similarity	NPC250069
0.6804	Remote Similarity	NPC488075
0.6739	Remote Similarity	NPC61904
0.6707	Remote Similarity	NPC288084
0.663	Remote Similarity	NPC470444
0.6629	Remote Similarity	NPC95866
0.6628	Remote Similarity	NPC216496
0.6604	Remote Similarity	NPC25946
0.6596	Remote Similarity	NPC122467
0.6559	Remote Similarity	NPC240306
0.6556	Remote Similarity	NPC473682
0.6484	Remote Similarity	NPC139320
0.6421	Remote Similarity	NPC32641
0.6421	Remote Similarity	NPC256188
0.6421	Remote Similarity	NPC35119
0.6413	Remote Similarity	NPC67326
0.6344	Remote Similarity	NPC156869
0.6337	Remote Similarity	NPC303694
0.631	Remote Similarity	NPC276222
0.631	Remote Similarity	NPC274618
0.631	Remote Similarity	NPC118284
0.631	Remote Similarity	NPC608147
0.6237	Remote Similarity	NPC173582
0.6237	Remote Similarity	NPC265885
0.6237	Remote Similarity	NPC181465
0.6237	Remote Similarity	NPC215710
0.6237	Remote Similarity	NPC473438
0.6237	Remote Similarity	NPC253788
0.6211	Remote Similarity	NPC253521
0.6211	Remote Similarity	NPC113836
0.6207	Remote Similarity	NPC145038
0.6207	Remote Similarity	NPC56077
0.6207	Remote Similarity	NPC281131
0.6207	Remote Similarity	NPC64305
0.6207	Remote Similarity	NPC253662
0.6207	Remote Similarity	NPC179950
0.6207	Remote Similarity	NPC88789
0.6207	Remote Similarity	NPC491374
0.62	Remote Similarity	NPC89052
0.62	Remote Similarity	NPC203145
0.619	Remote Similarity	NPC480445
0.6176	Remote Similarity	NPC470712
0.6163	Remote Similarity	NPC111929
0.6163	Remote Similarity	NPC320283
0.6163	Remote Similarity	NPC41121
0.6122	Remote Similarity	NPC89127
0.6111	Remote Similarity	NPC259957
0.6095	Remote Similarity	NPC488734
0.6095	Remote Similarity	NPC488735
0.6095	Remote Similarity	NPC488739
0.6095	Remote Similarity	NPC488732
0.6095	Remote Similarity	NPC488738
0.6091	Remote Similarity	NPC21359
0.6091	Remote Similarity	NPC460984
0.6067	Remote Similarity	NPC472459
0.6047	Remote Similarity	NPC67037
0.6047	Remote Similarity	NPC255615
0.6044	Remote Similarity	NPC136761
0.6042	Remote Similarity	NPC64425
0.6019	Remote Similarity	NPC25523
0.598	Remote Similarity	NPC189564
0.5979	Remote Similarity	NPC480471
0.5979	Remote Similarity	NPC488076
0.5957	Remote Similarity	NPC29958
0.5905	Remote Similarity	NPC470718
0.5895	Remote Similarity	NPC471748
0.5872	Remote Similarity	NPC488737
0.5859	Remote Similarity	NPC142142
0.5824	Remote Similarity	NPC159579
0.5824	Remote Similarity	NPC60735
0.5824	Remote Similarity	NPC26230
0.5824	Remote Similarity	NPC48093
0.5806	Remote Similarity	NPC203050
0.5806	Remote Similarity	NPC225434
0.578	Remote Similarity	NPC480444
0.5769	Remote Similarity	NPC173837
0.5761	Remote Similarity	NPC120099
0.5741	Remote Similarity	NPC470713
0.573	Remote Similarity	NPC19388
0.573	Remote Similarity	NPC240431
0.573	Remote Similarity	NPC104677
0.573	Remote Similarity	NPC55786
0.5702	Remote Similarity	NPC473554
0.57	Remote Similarity	NPC603079
0.5688	Remote Similarity	NPC488740
0.5688	Remote Similarity	NPC488736
0.5688	Remote Similarity	NPC488733
0.5686	Remote Similarity	NPC218161
0.567	Remote Similarity	NPC203259
0.567	Remote Similarity	NPC33054
0.567	Remote Similarity	NPC176740
0.567	Remote Similarity	NPC471725
0.567	Remote Similarity	NPC134532
0.567	Remote Similarity	NPC602582
0.5657	Remote Similarity	NPC297503
0.5591	Remote Similarity	NPC609478
0.5568	Remote Similarity	NPC34531
0.5556	Remote Similarity	NPC127546
0.5556	Remote Similarity	NPC57625
0.5556	Remote Similarity	NPC173637
0.5556	Remote Similarity	NPC317489
0.5556	Remote Similarity	NPC223424
0.5556	Remote Similarity	NPC600591
0.5545	Remote Similarity	NPC162394
0.5543	Remote Similarity	NPC325555
0.5543	Remote Similarity	NPC226304
0.551	Remote Similarity	NPC605592
0.5495	Remote Similarity	NPC297987
0.549	Remote Similarity	NPC473071
0.5484	Remote Similarity	NPC175107
0.5484	Remote Similarity	NPC129217
0.5481	Remote Similarity	NPC14187
0.5478	Remote Similarity	NPC487499
0.5474	Remote Similarity	NPC276377
0.5472	Remote Similarity	NPC292019
0.5472	Remote Similarity	NPC202908
0.5455	Remote Similarity	NPC129264
0.5455	Remote Similarity	NPC144097
0.5435	Remote Similarity	NPC488080
0.5435	Remote Similarity	NPC169977
0.5431	Remote Similarity	NPC275977
0.5431	Remote Similarity	NPC231787
0.5426	Remote Similarity	NPC85707
0.5424	Remote Similarity	NPC487502
0.5421	Remote Similarity	NPC480441
0.5421	Remote Similarity	NPC164704
0.5417	Remote Similarity	NPC116864
0.5417	Remote Similarity	NPC244776
0.5403	Remote Similarity	NPC33083
0.54	Remote Similarity	NPC470125
0.5392	Remote Similarity	NPC221288
0.5392	Remote Similarity	NPC194836
0.5392	Remote Similarity	NPC91493
0.5392	Remote Similarity	NPC605081
0.5378	Remote Similarity	NPC249560
0.5354	Remote Similarity	NPC65003
0.534	Remote Similarity	NPC476472
0.534	Remote Similarity	NPC294815
0.534	Remote Similarity	NPC85751
0.534	Remote Similarity	NPC16194
0.534	Remote Similarity	NPC19240
0.5326	Remote Similarity	NPC8573
0.5316	Remote Similarity	NPC103342
0.53	Remote Similarity	NPC122809
0.53	Remote Similarity	NPC35167
0.5294	Remote Similarity	NPC270448
0.5294	Remote Similarity	NPC473327
0.5253	Remote Similarity	NPC39834
0.5248	Remote Similarity	NPC296018
0.5248	Remote Similarity	NPC488074
0.5243	Remote Similarity	NPC205824
0.5243	Remote Similarity	NPC97119
0.5208	Remote Similarity	NPC223747
0.5208	Remote Similarity	NPC116458
0.5208	Remote Similarity	NPC246943
0.5204	Remote Similarity	NPC8856
0.5192	Remote Similarity	NPC471669
0.5189	Remote Similarity	NPC214621
0.5189	Remote Similarity	NPC34267
0.5175	Remote Similarity	NPC209550
0.5158	Remote Similarity	NPC219904
0.5146	Remote Similarity	NPC104883
0.5146	Remote Similarity	NPC488679
0.5138	Remote Similarity	NPC470715
0.5133	Remote Similarity	NPC474522
0.5133	Remote Similarity	NPC470717
0.5122	Remote Similarity	NPC487500
0.5109	Remote Similarity	NPC135599

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC299472 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5808
0.1-0.2	3281
0.2-0.3	48
0.3-0.4	10
0.4-0.5	2
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
0.567	Remote Similarity	NPD6797	Phase 2

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