NPASS Compound

Natural Product: NPC249104

Natural Product ID	NPC249104
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CAENGMLSMONNBU-IJOAAPTBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10304351
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 73 77 0 0 0 0 0 0 0 0999 V2000 -0.7216 -2.3075 -1.4021 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0680 -0.9343 -0.8899 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9557 -0.9501 0.3139 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2295 -0.4166 1.5208 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2513 -0.7747 1.4702 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8868 -0.2666 0.2379 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0170 -0.0816 -0.8087 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0027 -0.9417 -0.2618 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0712 -0.1754 -0.7075 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9829 0.2192 -2.0418 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0222 -0.1037 -2.7690 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9994 0.9869 -2.5485 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9818 1.4218 -3.8772 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0133 2.1948 -4.3662 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0504 2.5206 -3.5130 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0593 2.0865 -2.2037 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0261 1.3045 -1.6918 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0570 0.9064 -0.4510 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0961 0.1523 0.1065 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2771 -0.2129 1.5072 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2202 0.4933 2.2785 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4528 0.1486 3.5649 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7848 -0.8867 4.1499 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8629 -1.5901 3.4233 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6037 -1.2536 2.0866 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1410 -2.6629 3.9576 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0236 -1.2424 5.4753 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0778 3.2881 -3.9908 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8954 1.0461 -4.6657 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2829 -2.1740 1.4765 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7706 -0.9993 2.6616 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1055 -0.2710 0.0178 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2667 -1.0053 0.1103 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1049 -1.0013 -1.1338 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6634 0.3261 -1.5205 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2437 1.0304 -0.2989 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1815 0.9854 0.7641 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5693 1.7489 1.9839 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7621 1.2927 2.5052 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0380 -0.3738 1.1160 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5985 2.3407 -0.6450 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7805 0.0698 -2.3521 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4513 -1.5967 -2.2118 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5635 -2.9835 -1.1491 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2741 -2.6721 -1.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7399 -2.2400 -2.5324 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4961 -1.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1534 -2.0356 0.5637 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2919 0.6745 1.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7256 -0.4353 2.4073 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2230 0.7993 0.4611 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9817 2.5198 -5.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8759 2.3507 -1.5462 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7434 1.3205 1.7912 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1902 0.7136 4.1403 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8998 -1.8442 1.5304 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1559 -3.5298 3.4126 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0069 -2.2345 5.7375 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0205 4.2973 -4.0380 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2224 1.7693 -4.8953 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3152 -2.5888 2.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0435 -0.9627 3.3626 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1428 -2.0446 0.4304 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9823 -1.6825 -0.9175 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9450 0.9967 -2.0032 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1389 0.4867 0.0635 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2537 1.4031 0.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7704 1.6322 2.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6404 2.8259 1.7143 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1500 1.9080 3.1688 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0827 2.3129 -1.5144 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4441 -0.0008 -3.2824 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5350 -2.6007 -2.1933 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 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 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 23 27 1 0 15 28 1 0 13 29 1 0 5 30 1 0 4 31 1 0 3 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 38 39 1 0 37 40 1 0 36 41 1 0 35 42 1 0 34 43 1 0 7 2 1 0 19 9 2 0 25 20 1 0 40 33 1 0 17 12 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 3 48 1 1 4 49 1 1 5 50 1 1 6 51 1 1 14 52 1 0 16 53 1 0 21 54 1 0 22 55 1 0 25 56 1 0 26 57 1 0 27 58 1 0 28 59 1 0 29 60 1 0 30 61 1 0 31 62 1 0 33 63 1 1 34 64 1 1 35 65 1 6 36 66 1 1 37 67 1 6 38 68 1 0 38 69 1 0 39 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	CAENGMLSMONNBU-IJOAAPTBSA-N
Standard InCHI	InChI=1S/C27H30O16/c1-8-23(42-27-21(37)19(35)17(33)15(7-28)41-27)20(36)22(38)26(39-8)43-25-18(34)16-13(32)5-10(29)6-14(16)40-24(25)9-2-3-11(30)12(31)4-9/h2-6,8,15,17,19-23,26-33,35-38H,7H2,1H3/t8-,15+,17+,19-,20-,21+,22+,23-,26+,27+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O)O)O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	0.823 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.235 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.498 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	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:	0.14	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.776	Fsp³:	0.444
MCE-18:	122.949 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.619	Fluc inhibitor:	0.282 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.849 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.604 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.28	Promiscuous compounds:	0.595

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.489	MDCK Permeability:	-5.023
Pgp-inhibitor:	0.0	Pgp-substrate:	0.547
PAMPA:	0.998 ? 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):	0.801
20% Bioavailability (F20%):	0.856	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.12
Plasma Protein Binding (PPB):	84.323%	Volume Distribution (VD):	-0.075
Fu:	14.926% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.714
BSEP inhibitor:	0.001

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:	0.747
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.473
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.602 ? 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):

2.213

Half-life (T1/2):

4.831

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.15
Human Hepatotoxicity (H-HT):	0.537	Drug-induced Liver Injury (DILI):	0.979
AMES Toxicity:	0.937	Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.156	Skin Sensitization:	1.0
Carcinogencity:	0.079	Eye Corrosion:	0.0
Eye Irritation:	0.609	Respiratory Toxicity:	0.038
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.975
Hematotoxicity:	0.109	Drug-induced Nephrotoxicity:	0.245
Genotoxicity:	0.972	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.957	Hek293 Cytotoxicity:	0.695
BCF:	0.425 ? 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:	3.044 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.528 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.661 ? 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
NPO29365	Baileya multiradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29365	Baileya multiradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29365	Baileya multiradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29365	Baileya multiradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18659	Prunus japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29365	Baileya multiradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29249	Prunus humilis	Species	Rosaceae	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 NPC249104 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	21733
0.1-0.2	23807
0.2-0.3	3325
0.3-0.4	520
0.4-0.5	206
0.5-0.6	92
0.6-0.7	73
0.7-0.8	0
0.8-0.85	9
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471748
0.9103	High Similarity	NPC139320
0.8861	High Similarity	NPC29958
0.8193	Intermediate Similarity	NPC605592
0.8182	Intermediate Similarity	NPC145038
0.8182	Intermediate Similarity	NPC56077
0.8182	Intermediate Similarity	NPC281131
0.8182	Intermediate Similarity	NPC253662
0.8182	Intermediate Similarity	NPC179950
0.8182	Intermediate Similarity	NPC88789
0.8182	Intermediate Similarity	NPC491374
0.8046	Intermediate Similarity	NPC471669
0.7792	Intermediate Similarity	NPC67037
0.7792	Intermediate Similarity	NPC255615
0.7558	Intermediate Similarity	NPC156869
0.75	Intermediate Similarity	NPC254855
0.75	Intermediate Similarity	NPC94610
0.7375	Intermediate Similarity	NPC127546
0.7375	Intermediate Similarity	NPC57625
0.7375	Intermediate Similarity	NPC77672
0.7375	Intermediate Similarity	NPC133671
0.7375	Intermediate Similarity	NPC135391
0.7375	Intermediate Similarity	NPC173637
0.7375	Intermediate Similarity	NPC78263
0.7375	Intermediate Similarity	NPC317489
0.7375	Intermediate Similarity	NPC250069
0.7375	Intermediate Similarity	NPC223424
0.7375	Intermediate Similarity	NPC600591
0.716	Intermediate Similarity	NPC19388
0.716	Intermediate Similarity	NPC240431
0.716	Intermediate Similarity	NPC55786
0.7159	Intermediate Similarity	NPC155877
0.7024	Intermediate Similarity	NPC159579
0.7024	Intermediate Similarity	NPC175107
0.7	Intermediate Similarity	NPC288084
0.6979	Remote Similarity	NPC292019
0.6979	Remote Similarity	NPC202908
0.6867	Remote Similarity	NPC64305
0.6824	Remote Similarity	NPC182121
0.6824	Remote Similarity	NPC60735
0.6824	Remote Similarity	NPC26230
0.679	Remote Similarity	NPC34531
0.6782	Remote Similarity	NPC203050
0.6782	Remote Similarity	NPC170052
0.6782	Remote Similarity	NPC225434
0.6782	Remote Similarity	NPC135846
0.6778	Remote Similarity	NPC203259
0.6778	Remote Similarity	NPC33054
0.6778	Remote Similarity	NPC176740
0.6778	Remote Similarity	NPC471725
0.6778	Remote Similarity	NPC134532
0.6778	Remote Similarity	NPC602582
0.6744	Remote Similarity	NPC120099
0.6706	Remote Similarity	NPC472459
0.6706	Remote Similarity	NPC599850
0.6705	Remote Similarity	NPC116864
0.6705	Remote Similarity	NPC244776
0.6705	Remote Similarity	NPC95866
0.6667	Remote Similarity	NPC67326
0.6627	Remote Similarity	NPC111929
0.6627	Remote Similarity	NPC320283
0.6627	Remote Similarity	NPC41121
0.6522	Remote Similarity	NPC255157
0.6522	Remote Similarity	NPC259896
0.6512	Remote Similarity	NPC42773
0.6512	Remote Similarity	NPC45522
0.6512	Remote Similarity	NPC325555
0.6512	Remote Similarity	NPC226304
0.6484	Remote Similarity	NPC470405
0.6484	Remote Similarity	NPC163242
0.6484	Remote Similarity	NPC272068
0.6471	Remote Similarity	NPC136042
0.6429	Remote Similarity	NPC135599
0.6429	Remote Similarity	NPC73855
0.6429	Remote Similarity	NPC113968
0.6429	Remote Similarity	NPC328940
0.6429	Remote Similarity	NPC277174
0.6429	Remote Similarity	NPC606877
0.6386	Remote Similarity	NPC276222
0.6386	Remote Similarity	NPC274618
0.6386	Remote Similarity	NPC118284
0.6386	Remote Similarity	NPC608147
0.6364	Remote Similarity	NPC189564
0.6364	Remote Similarity	NPC609478
0.6292	Remote Similarity	NPC209023
0.6292	Remote Similarity	NPC605784
0.6263	Remote Similarity	NPC203145
0.6207	Remote Similarity	NPC52550
0.6146	Remote Similarity	NPC122467
0.6146	Remote Similarity	NPC104883
0.6146	Remote Similarity	NPC488679
0.6129	Remote Similarity	NPC173582
0.6129	Remote Similarity	NPC265885
0.6129	Remote Similarity	NPC181465
0.6129	Remote Similarity	NPC215710
0.6129	Remote Similarity	NPC473438
0.6129	Remote Similarity	NPC253788
0.6111	Remote Similarity	NPC223747
0.6105	Remote Similarity	NPC488073
0.6067	Remote Similarity	NPC219904
0.6067	Remote Similarity	NPC488071
0.6061	Remote Similarity	NPC602448
0.6044	Remote Similarity	NPC476215
0.6038	Remote Similarity	NPC156785
0.6023	Remote Similarity	NPC84362
0.6022	Remote Similarity	NPC471079
0.602	Remote Similarity	NPC135831
0.602	Remote Similarity	NPC220173
0.5979	Remote Similarity	NPC37668
0.5957	Remote Similarity	NPC39834
0.5938	Remote Similarity	NPC154741
0.5909	Remote Similarity	NPC8573
0.5909	Remote Similarity	NPC297987
0.5909	Remote Similarity	NPC265530
0.5895	Remote Similarity	NPC304741
0.5889	Remote Similarity	NPC235260
0.5889	Remote Similarity	NPC155763
0.5862	Remote Similarity	NPC476771
0.5859	Remote Similarity	NPC76831
0.5859	Remote Similarity	NPC89127
0.5851	Remote Similarity	NPC480466
0.5843	Remote Similarity	NPC305811
0.5843	Remote Similarity	NPC488080
0.5843	Remote Similarity	NPC169977
0.5825	Remote Similarity	NPC219043
0.5824	Remote Similarity	NPC85707
0.5824	Remote Similarity	NPC224530
0.58	Remote Similarity	NPC292929
0.5773	Remote Similarity	NPC253521
0.5773	Remote Similarity	NPC113836
0.5761	Remote Similarity	NPC116458
0.5761	Remote Similarity	NPC246943
0.5743	Remote Similarity	NPC223426
0.5714	Remote Similarity	NPC75574
0.5714	Remote Similarity	NPC483415
0.57	Remote Similarity	NPC476472
0.57	Remote Similarity	NPC294815
0.57	Remote Similarity	NPC16194
0.5698	Remote Similarity	NPC54802
0.5698	Remote Similarity	NPC197304
0.5686	Remote Similarity	NPC14187
0.5686	Remote Similarity	NPC81042
0.5684	Remote Similarity	NPC476773
0.5667	Remote Similarity	NPC271692
0.5657	Remote Similarity	NPC473327
0.5652	Remote Similarity	NPC259957
0.5652	Remote Similarity	NPC189913
0.5619	Remote Similarity	NPC303694
0.5612	Remote Similarity	NPC153755
0.5588	Remote Similarity	NPC470446
0.5556	Remote Similarity	NPC12013
0.5556	Remote Similarity	NPC245452
0.5556	Remote Similarity	NPC11432
0.5556	Remote Similarity	NPC477613
0.5556	Remote Similarity	NPC609879
0.5545	Remote Similarity	NPC480444
0.5524	Remote Similarity	NPC48984
0.5513	Remote Similarity	NPC286342
0.551	Remote Similarity	NPC129264
0.55	Remote Similarity	NPC270448
0.55	Remote Similarity	NPC35119
0.5495	Remote Similarity	NPC24043
0.5495	Remote Similarity	NPC27640
0.5484	Remote Similarity	NPC101026
0.5484	Remote Similarity	NPC488077
0.5484	Remote Similarity	NPC197285
0.5484	Remote Similarity	NPC484158
0.5484	Remote Similarity	NPC601710
0.5472	Remote Similarity	NPC480441
0.5455	Remote Similarity	NPC470125
0.5455	Remote Similarity	NPC296018
0.5455	Remote Similarity	NPC126784
0.5455	Remote Similarity	NPC241423
0.5455	Remote Similarity	NPC474522
0.5455	Remote Similarity	NPC488736
0.5455	Remote Similarity	NPC488733
0.5455	Remote Similarity	NPC488074
0.5446	Remote Similarity	NPC192539
0.5444	Remote Similarity	NPC289667
0.5444	Remote Similarity	NPC143851
0.5444	Remote Similarity	NPC476772
0.5439	Remote Similarity	NPC21359
0.5439	Remote Similarity	NPC460984
0.5435	Remote Similarity	NPC21100
0.5424	Remote Similarity	NPC249560
0.5385	Remote Similarity	NPC282987
0.5385	Remote Similarity	NPC30011
0.5385	Remote Similarity	NPC72554
0.5376	Remote Similarity	NPC191306
0.5376	Remote Similarity	NPC129217
0.537	Remote Similarity	NPC470718
0.5361	Remote Similarity	NPC609888
0.5357	Remote Similarity	NPC488737
0.5357	Remote Similarity	NPC241781
0.5354	Remote Similarity	NPC35167
0.5347	Remote Similarity	NPC32641
0.5347	Remote Similarity	NPC256188
0.5327	Remote Similarity	NPC470712
0.5323	Remote Similarity	NPC33083
0.5315	Remote Similarity	NPC488740

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC249104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5871
0.1-0.2	3193
0.2-0.3	75
0.3-0.4	5
0.4-0.5	4
0.5-0.6	1
0.6-0.7	1
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
0.6778	Remote Similarity	NPD6797	Phase 2
0.5243	Remote Similarity	NPD7251	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