NPASS Compound

Natural Product: NPC211594

Natural Product ID	NPC211594
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lantanone
IUPAC Name	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-6-methoxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methyl acetate
Synonyms	lantanone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL496041
PubChem CID	10744475
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 63 66 0 0 0 0 0 0 0 0999 V2000 -8.6153 1.8123 -2.7719 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1647 2.0007 -2.5202 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5028 2.8273 -3.1675 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5401 1.2362 -1.5406 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1357 1.4590 -1.3375 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6003 0.5732 -0.2599 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2526 0.8289 1.0808 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7070 -0.2704 2.0047 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2214 -0.0150 2.1220 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6409 -0.1592 0.7070 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3033 0.0013 0.6478 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2121 -0.6775 0.2574 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0317 -0.0353 0.3724 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2271 -0.5907 0.0140 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1792 -1.8849 -0.4977 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3678 -2.4780 -0.8702 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3632 -3.6405 -1.3349 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5391 -1.7510 -0.7129 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5341 -0.4738 -0.2016 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7565 0.3312 -0.0185 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9725 -0.1630 -0.3589 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1292 0.6036 -0.1807 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0184 1.8616 0.3425 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7984 2.3685 0.6884 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6556 1.5965 0.5065 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1623 2.6462 0.5289 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4432 2.1087 0.1623 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3669 0.0482 0.1398 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9693 -2.5264 -0.6150 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2289 -1.9525 -0.2482 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4051 -2.7005 -0.4050 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8049 -3.6434 0.5846 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9741 -3.8214 -1.1332 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2397 0.8330 -0.1041 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5889 -0.8789 2.9787 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3475 -0.2499 3.2330 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6386 0.7622 1.0094 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1622 1.4856 -1.8681 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7703 1.0786 -3.5837 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0441 2.8116 -3.0414 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6710 1.2513 -2.3222 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9475 2.5233 -1.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7777 -0.4973 -0.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8684 1.7799 1.4696 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8376 -1.2218 1.4609 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0731 1.0644 2.4004 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9804 -1.1429 0.3395 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0691 0.9828 0.7751 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4857 -2.2072 -1.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1444 -1.1426 -0.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0927 0.2051 -0.4521 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6992 3.3548 1.0988 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7099 2.0481 0.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4289 1.6815 -0.8444 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1654 2.9596 0.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7169 1.3527 0.9162 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9110 -3.6157 0.6736 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3071 -3.5134 1.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5619 -4.6610 0.1774 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9931 -4.5738 -0.4310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3187 -0.3589 3.8055 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6440 0.6668 3.4870 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9693 1.7022 0.9179 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 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 16 18 1 0 18 19 2 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 23 26 1 0 26 27 1 0 19 28 1 0 15 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 29 33 1 0 10 34 1 0 9 35 1 0 8 36 1 0 7 37 1 0 34 6 1 0 30 12 1 0 28 14 1 0 25 20 1 0 1 38 1 0 1 39 1 0 1 40 1 0 5 41 1 0 5 42 1 0 6 43 1 6 7 44 1 1 8 45 1 6 9 46 1 1 10 47 1 6 13 48 1 0 18 49 1 0 21 50 1 0 22 51 1 0 24 52 1 0 25 53 1 0 27 54 1 0 27 55 1 0 27 56 1 0 32 57 1 0 32 58 1 0 32 59 1 0 33 60 1 0 35 61 1 0 36 62 1 0 37 63 1 0 M END

Standard InCHIKey	FHBWUJAADRENKL-SDPBRJMTSA-N
Standard InCHI	InChI=1S/C25H26O12/c1-11(26)34-10-18-20(28)22(30)23(31)25(37-18)36-17-9-16-19(21(29)24(17)33-3)14(27)8-15(35-16)12-4-6-13(32-2)7-5-12/h4-9,18,20,22-23,25,28-31H,10H2,1-3H3/t18-,20-,22+,23-,25-/m1/s1
SMILES	CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc3c(c(=O)cc(c4ccc(cc4)OC)o3)c(c2OC)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.14	Volume:	488.485 ? Van der Waals volume.
Dense:	1.061	LogP:	1.525 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.901 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.708 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	25.0
TPSA:	174.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.326	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.931	Fsp³:	0.36
MCE-18:	88.941 ? 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:	0
Colloidal aggregators:	0.506	Fluc inhibitor:	0.344 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.905 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.938 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.034	Promiscuous compounds:	0.292

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.912	MDCK Permeability:	-5.18
Pgp-inhibitor:	0.531	Pgp-substrate:	0.128
PAMPA:	0.456 ? 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):	0.838
20% Bioavailability (F20%):	0.542	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.267
Plasma Protein Binding (PPB):	93.973%	Volume Distribution (VD):	-0.292
Fu:	4.833% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.225
BSEP inhibitor:	0.865

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.457 ? 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):

1.986

Half-life (T1/2):

2.356

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.14
Human Hepatotoxicity (H-HT):	0.526	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.941	Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.121	Skin Sensitization:	0.973
Carcinogencity:	0.576	Eye Corrosion:	0.0
Eye Irritation:	0.261	Respiratory Toxicity:	0.029
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.641
Hematotoxicity:	0.379	Drug-induced Nephrotoxicity:	0.584
Genotoxicity:	0.941	RPMI-8226 Immunitoxicity:	0.125
A549 Cytotoxicity:	0.196	Hek293 Cytotoxicity:	0.347
BCF:	0.508 ? 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:	3.242 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.694 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.103 ? 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
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33780581]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36270431]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38257257]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38893531]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39104562]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1859	Lantana camara	Species	Verbenaceae	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

Activity Type	# Activity
Activity	3

Activity Type	# Activity
Organism	3

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
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	Activity	=	90.0	%	DOI[10.1007/s00044-010-9338-x]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	Activity	=	95.0	%	PMID[3210015]

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 NPC211594 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	13038
0.1-0.2	32436
0.2-0.3	3254
0.3-0.4	781
0.4-0.5	248
0.5-0.6	70
0.6-0.7	21
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8395	Intermediate Similarity	NPC204693
0.8228	Intermediate Similarity	NPC172807
0.7901	Intermediate Similarity	NPC254540
0.7882	Intermediate Similarity	NPC483707
0.7692	Intermediate Similarity	NPC186807
0.7215	Intermediate Similarity	NPC58053
0.6854	Remote Similarity	NPC46202
0.6818	Remote Similarity	NPC22062
0.6818	Remote Similarity	NPC473634
0.6818	Remote Similarity	NPC138811
0.663	Remote Similarity	NPC488089
0.6627	Remote Similarity	NPC105025
0.6522	Remote Similarity	NPC473623
0.6471	Remote Similarity	NPC609451
0.6444	Remote Similarity	NPC233994
0.6353	Remote Similarity	NPC201292
0.6237	Remote Similarity	NPC211532
0.6237	Remote Similarity	NPC488364
0.6235	Remote Similarity	NPC181712
0.6207	Remote Similarity	NPC605067
0.6164	Remote Similarity	NPC145379
0.6136	Remote Similarity	NPC602805
0.6122	Remote Similarity	NPC11468
0.6118	Remote Similarity	NPC93337
0.6118	Remote Similarity	NPC95090
0.6118	Remote Similarity	NPC27408
0.6	Remote Similarity	NPC209296
0.5957	Remote Similarity	NPC64051
0.5876	Remote Similarity	NPC477629
0.587	Remote Similarity	NPC295613
0.587	Remote Similarity	NPC473657
0.5862	Remote Similarity	NPC45638
0.5833	Remote Similarity	NPC229409
0.5825	Remote Similarity	NPC488087
0.5806	Remote Similarity	NPC44931
0.5778	Remote Similarity	NPC607707
0.5773	Remote Similarity	NPC270675
0.5773	Remote Similarity	NPC195685
0.5714	Remote Similarity	NPC488086
0.5686	Remote Similarity	NPC472993
0.5657	Remote Similarity	NPC101636
0.5657	Remote Similarity	NPC298171
0.5612	Remote Similarity	NPC479766
0.5604	Remote Similarity	NPC99957
0.56	Remote Similarity	NPC472994
0.5579	Remote Similarity	NPC210073
0.5566	Remote Similarity	NPC68592
0.5556	Remote Similarity	NPC479765
0.5495	Remote Similarity	NPC243930
0.5484	Remote Similarity	NPC477848
0.5464	Remote Similarity	NPC475366
0.5455	Remote Similarity	NPC143851
0.5444	Remote Similarity	NPC27942
0.5417	Remote Similarity	NPC473512
0.5417	Remote Similarity	NPC129827
0.5376	Remote Similarity	NPC190003
0.5341	Remote Similarity	NPC331652
0.5327	Remote Similarity	NPC488088
0.5326	Remote Similarity	NPC22832
0.5326	Remote Similarity	NPC21666
0.5326	Remote Similarity	NPC80188
0.5306	Remote Similarity	NPC284277
0.5306	Remote Similarity	NPC475497
0.5275	Remote Similarity	NPC117260
0.5269	Remote Similarity	NPC220169
0.5253	Remote Similarity	NPC65711
0.5234	Remote Similarity	NPC488083
0.5208	Remote Similarity	NPC609888
0.5195	Remote Similarity	NPC239128
0.519	Remote Similarity	NPC69394
0.5189	Remote Similarity	NPC473644
0.5169	Remote Similarity	NPC473043
0.5161	Remote Similarity	NPC608742
0.5158	Remote Similarity	NPC116864
0.5158	Remote Similarity	NPC244776
0.5155	Remote Similarity	NPC15358
0.5152	Remote Similarity	NPC153755
0.5146	Remote Similarity	NPC135358
0.514	Remote Similarity	NPC311850
0.514	Remote Similarity	NPC277532
0.5135	Remote Similarity	NPC488079
0.5135	Remote Similarity	NPC488078
0.5128	Remote Similarity	NPC120163
0.5125	Remote Similarity	NPC160951
0.5111	Remote Similarity	NPC39360
0.5111	Remote Similarity	NPC19709
0.5111	Remote Similarity	NPC29763
0.5111	Remote Similarity	NPC210003
0.5106	Remote Similarity	NPC88023
0.5106	Remote Similarity	NPC309025
0.51	Remote Similarity	NPC483414
0.51	Remote Similarity	NPC483415
0.5098	Remote Similarity	NPC475382
0.5054	Remote Similarity	NPC488071
0.5052	Remote Similarity	NPC187379
0.505	Remote Similarity	NPC483416
0.505	Remote Similarity	NPC124155

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC211594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4090
0.1-0.2	4932
0.2-0.3	114
0.3-0.4	6
0.4-0.5	6
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
0.6	Remote Similarity	NPD7054	Phase 4
0.5192	Remote Similarity	NPD7472	Pre-clinical

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