NPASS Compound

Natural Product: NPC36

Natural Product ID	NPC36
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3S)-3,5,7-Trihydroxy-2-[(2S,3S)-3-(4-Hydroxy-3-Methoxyphenyl)-2-(Hydroxymethyl)-2,3-Dihydro-1,4-Benzodioxin-6-Yl]-2,3-Dihydrochromen-4-One
IUPAC Name	(3S)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL245121
PubChem CID	16211710
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001844] Flavonolignans

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 57 61 0 0 0 0 0 0 0 0999 V2000 7.6829 -0.1692 0.6794 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3969 1.0729 0.0601 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0989 1.3485 -0.3410 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0757 0.4160 -0.1404 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8071 0.7069 -0.5423 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5064 1.9236 -1.1533 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5157 2.8176 -1.3394 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7959 2.5311 -0.9372 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7993 3.4780 -1.1485 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7135 -0.2785 -0.3385 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1159 -1.5501 0.2961 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7037 -2.4464 -0.7898 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1154 -3.6681 -0.2709 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0145 -2.2491 0.8134 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7327 -1.7590 0.7977 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3084 -2.6037 1.0761 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6189 -2.1166 1.0638 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9171 -0.8047 0.7798 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8339 0.0151 0.5041 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4686 -0.4147 0.5036 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5756 0.3546 0.2378 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3005 -0.3452 0.7756 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2277 -1.5469 0.7517 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6499 -1.1001 0.6300 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5821 -1.8191 1.0218 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9348 0.1988 0.0419 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2350 0.6631 -0.0630 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4555 1.8936 -0.6247 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4435 2.6924 -1.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1564 2.2294 -0.9856 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9008 0.9792 -0.4176 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5875 0.5173 -0.3151 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7504 3.9401 -1.6533 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2559 -0.1546 0.4130 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8778 -2.3448 -0.3550 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7311 -0.1587 1.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0194 -0.2958 1.5588 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5745 -0.9595 -0.0745 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3905 -0.5042 0.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4878 2.1223 -1.4601 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2961 3.7718 -1.8151 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5511 4.4430 -1.2671 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3647 -0.5395 -1.3904 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8261 -1.4276 1.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5570 -1.9706 -1.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8607 -2.6144 -1.5051 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9071 -3.6567 0.7109 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1299 -3.6608 1.3095 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3674 -2.8773 1.3033 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0276 1.0459 0.2779 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4808 0.2039 1.7216 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1738 -2.0914 1.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4858 2.2290 -0.6925 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3312 2.8319 -1.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3556 4.5995 -1.1655 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7955 -0.7522 -0.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5011 -2.1460 -1.1046 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 8 9 1 0 5 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 18 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 29 33 1 0 27 34 1 0 23 35 1 0 8 3 1 0 21 10 1 0 32 22 1 0 20 15 1 0 31 26 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 6 40 1 0 7 41 1 0 9 42 1 0 10 43 1 6 11 44 1 1 12 45 1 0 12 46 1 0 13 47 1 0 16 48 1 0 17 49 1 0 19 50 1 0 22 51 1 0 23 52 1 1 28 53 1 0 30 54 1 0 33 55 1 0 34 56 1 0 35 57 1 0 M END

Standard InCHIKey	SEBFKMXJBCUCAI-ILJKEPSESA-N
Standard InCHI	InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25?/m0/s1
SMILES	COc1cc(ccc1O)[C@H]1[C@H](CO)Oc2ccc(cc2O1)C1[C@@H](C(=O)c2c(cc(cc2O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	482.12	Volume:	459.711 ? Van der Waals volume.
Dense:	1.049	LogP:	1.912 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.03 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.011 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	29.0
TPSA:	155.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.374	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.992	Fsp³:	0.24
MCE-18:	97.742 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.731	Fluc inhibitor:	0.333 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.12 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.562 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.36	Promiscuous compounds:	0.362

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.094	MDCK Permeability:	-5.099
Pgp-inhibitor:	0.993	Pgp-substrate:	0.588
PAMPA:	0.273 ? 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%):	0.009	30% Bioavailability (F30%):	0.839
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.959
Plasma Protein Binding (PPB):	94.85%	Volume Distribution (VD):	0.072
Fu:	4.181% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.986
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.99	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.209	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.641
CYP3A4-inhibitor:	0.066	CYP3A4-substrate:	0.983
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.902
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):

6.941

Half-life (T1/2):

1.999

ADMET: Toxicity

hERG Blockers:	0.084	hERG Blockers (10um):	0.379
Human Hepatotoxicity (H-HT):	0.774	Drug-induced Liver Injury (DILI):	0.682
AMES Toxicity:	0.778	Rat Oral Acute Toxicity:	0.401
Maximum Recommended Daily Dose:	0.294	Skin Sensitization:	0.946
Carcinogencity:	0.266	Eye Corrosion:	0.0
Eye Irritation:	0.893	Respiratory Toxicity:	0.583
Drug-induced Neurotoxicity:	0.204	Ototoxicity:	0.743
Hematotoxicity:	0.157	Drug-induced Nephrotoxicity:	0.648
Genotoxicity:	0.976	RPMI-8226 Immunitoxicity:	0.227
A549 Cytotoxicity:	0.531	Hek293 Cytotoxicity:	0.677
BCF:	0.854 ? 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:	3.543 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.8 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.001 ? 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
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/10496475.2013.791908]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16394559]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24456525]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24597776]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5645	Silybum marianum	Species	Asteraceae	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
Potency	11
IC50	3
IC25	3
pIC25	2

Activity Type	# Activity
Individual protein	8
Others	5
Organism	2
Non-molecular	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3	Individual protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	44668.4	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	6513.1	nM	PubChem BioAssay data set
NPT11	Individual protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	25118.9	nM	PubChem BioAssay data set
NPT9	Individual protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	56234.1	nM	PubChem BioAssay data set
NPT7	Individual protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT4	Individual protein	Large T antigen	Simian virus 40	IC50	n.a.	57450.0	nM	PubChem BioAssay data set
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	25118.9	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	13115.4	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC25	=	7.7	uM	PMID[17166721]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC25	=	140.0	uM	PMID[17166721]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	pIC25	=	-2.15	n.a.	PMID[17166721]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	128824955.17	nM	PMID[17166721]
NPT1	Others	Radical scavenging activity	n.a.	IC25	=	61.4	uM	PMID[17166721]
NPT1	Others	Radical scavenging activity	n.a.	pIC25	=	-1.79	n.a.	PMID[17166721]
NPT2	Others	Unspecified	n.a.	IC50	=	31430.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	8912.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	31622.8	nM	PubChem BioAssay data set

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 NPC36 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	24274
0.1-0.2	21330
0.2-0.3	3537
0.3-0.4	593
0.4-0.5	83
0.5-0.6	24
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC36916
1.0	High Similarity	NPC7154
1.0	High Similarity	NPC125039
1.0	High Similarity	NPC7688
0.9545	High Similarity	NPC138688
0.9545	High Similarity	NPC72787
0.9545	High Similarity	NPC217795
0.9545	High Similarity	NPC58223
0.7656	Intermediate Similarity	NPC326037
0.7656	Intermediate Similarity	NPC13858
0.6154	Remote Similarity	NPC606364
0.6087	Remote Similarity	NPC320825
0.6049	Remote Similarity	NPC279209
0.6049	Remote Similarity	NPC102277
0.6049	Remote Similarity	NPC479117
0.5882	Remote Similarity	NPC44721
0.5882	Remote Similarity	NPC211466
0.5882	Remote Similarity	NPC605332
0.5857	Remote Similarity	NPC52530
0.5821	Remote Similarity	NPC62290
0.5821	Remote Similarity	NPC142731
0.5821	Remote Similarity	NPC326506
0.5797	Remote Similarity	NPC36835
0.5797	Remote Similarity	NPC246162
0.5797	Remote Similarity	NPC9743
0.5797	Remote Similarity	NPC260491
0.5797	Remote Similarity	NPC61506
0.5797	Remote Similarity	NPC240476
0.5753	Remote Similarity	NPC5851
0.5571	Remote Similarity	NPC250922
0.5529	Remote Similarity	NPC158188
0.5467	Remote Similarity	NPC86030
0.5362	Remote Similarity	NPC4152
0.5342	Remote Similarity	NPC236637
0.5286	Remote Similarity	NPC19721
0.5217	Remote Similarity	NPC21835
0.5205	Remote Similarity	NPC16435
0.5143	Remote Similarity	NPC279417
0.5143	Remote Similarity	NPC49130

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC36 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5398
0.1-0.2	3668
0.2-0.3	75
0.3-0.4	4
0.4-0.5	2
0.5-0.6	0
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	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6166	Phase 2
1.0	High Similarity	NPD6167	Clinical (unspecified phase)
1.0	High Similarity	NPD6168	Clinical (unspecified phase)

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