NPASS Compound

Natural Product: NPC598381

Natural Product ID	NPC598381
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(-)-epiafzelechin-(4beta-8)-(-)-epicatechin
IUPAC Name	(2~{R},3~{R},4~{R})-4-[(2~{R},3~{R})-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]-2-(4-hydroxyphenyl)chromane-3,5,7-triol
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 67 72 0 0 0 0 0 0 0 0999 V2000 -7.2586 3.0509 3.0172 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2757 2.3275 2.3740 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0643 2.0142 2.9751 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0856 1.3008 2.3529 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2847 0.8623 1.0733 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2959 0.0946 0.3266 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3072 0.5951 -1.0299 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5451 -0.0934 -1.9866 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9235 -0.2928 -3.2823 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1133 -0.9755 -4.1322 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5029 -1.1810 -5.4677 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8963 -1.4686 -3.6692 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5321 -1.2591 -2.3655 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7069 -1.7796 -1.9560 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3446 -0.5711 -1.5052 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8834 -0.3567 -0.1015 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0619 -1.4972 0.3835 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6007 -2.7430 0.5415 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9392 -3.0232 0.2483 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1592 -3.8226 1.0086 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4774 -3.6466 1.3205 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2713 -4.7155 1.7944 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0374 -2.3976 1.1670 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2783 -1.3282 0.7025 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8434 -0.0859 0.5515 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1398 0.1650 1.0389 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7207 1.3776 0.4083 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0185 2.5706 0.3552 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5839 3.6708 -0.2499 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8413 3.6083 -0.8072 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3891 4.7410 -1.4144 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5410 2.4370 -0.7602 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8040 2.3671 -1.3175 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9663 1.3309 -0.1488 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0182 -1.0145 0.7608 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0438 -1.2344 -0.6112 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4633 -2.2181 1.5100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9142 0.1001 0.8532 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5999 1.4403 1.2160 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4936 1.1613 0.4399 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4842 1.8873 1.0808 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2547 4.0362 3.1671 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9160 2.3668 3.9893 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1628 1.0680 2.8416 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6723 -0.9686 0.3304 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8655 0.0964 -3.6177 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1065 -1.9589 -5.9478 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2750 -2.0074 -4.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1946 -2.4797 -2.4665 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1638 0.5399 -0.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4707 -3.4769 0.9769 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2710 -4.8020 1.1311 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6404 -5.3065 1.0368 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0623 0.3423 2.1595 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0412 2.6074 0.7926 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0472 4.6246 -0.3037 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4032 4.7960 -1.4822 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6172 2.4746 -0.7407 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6011 0.4460 -0.1688 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0621 -0.8599 1.1358 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7693 -2.1591 -0.8487 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6220 -2.0173 2.5881 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0365 -3.1054 1.1981 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8658 -0.5471 1.7608 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8766 1.9667 0.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6872 0.8339 -0.5653 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4057 2.0920 0.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 10 12 2 0 12 13 1 0 13 14 1 0 13 15 2 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 18 20 1 0 20 21 2 0 21 22 1 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 2 0 26 35 1 0 35 36 1 0 35 37 1 0 16 38 1 0 38 39 1 0 5 40 1 0 40 41 2 0 41 2 1 0 38 6 1 0 15 8 1 0 24 17 1 0 34 27 1 0 37 23 1 0 1 42 1 0 3 43 1 0 4 44 1 0 6 45 1 6 9 46 1 0 11 47 1 0 12 48 1 0 14 49 1 0 16 50 1 6 19 51 1 0 20 52 1 0 22 53 1 0 26 54 1 1 28 55 1 0 29 56 1 0 31 57 1 0 33 58 1 0 34 59 1 0 35 60 1 1 36 61 1 0 37 62 1 0 37 63 1 0 38 64 1 1 39 65 1 0 40 66 1 0 41 67 1 0 M END

Standard InCHIKey	KUODBSWFMJMVJV-NFJBMHMQSA-N
Standard InCHI	InChI=1S/C30H26O11/c31-14-4-1-12(2-5-14)29-27(39)26(24-20(36)8-15(32)9-23(24)40-29)25-21(37)11-18(34)16-10-22(38)28(41-30(16)25)13-3-6-17(33)19(35)7-13/h1-9,11,22,26-29,31-39H,10H2/t22-,26-,27-,28-,29-/m1/s1
SMILES	OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3[C@H](C3=C(O)C=C(O)C4=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@H](O)C4)[C@H]2O)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	562.15	Volume:	541.152 ? Van der Waals volume.
Dense:	1.039	LogP:	1.152 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.55 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.225 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	34.0
TPSA:	200.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.166	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.423	Fsp³:	0.2
MCE-18:	123.333 ? 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:	0.874	Fluc inhibitor:	0.265 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.167 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.417 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.532	Promiscuous compounds:	0.176

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.957	MDCK Permeability:	-4.865
Pgp-inhibitor:	0.0	Pgp-substrate:	0.566
PAMPA:	0.073 ? 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%):	0.969	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.956
Plasma Protein Binding (PPB):	92.854%	Volume Distribution (VD):	0.257
Fu:	10.591% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.066
BSEP inhibitor:	0.015

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.728	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

5.535

Half-life (T1/2):

3.941

ADMET: Toxicity

hERG Blockers:	0.15	hERG Blockers (10um):	0.827
Human Hepatotoxicity (H-HT):	0.874	Drug-induced Liver Injury (DILI):	0.321
AMES Toxicity:	0.475	Rat Oral Acute Toxicity:	0.635
Maximum Recommended Daily Dose:	0.987	Skin Sensitization:	0.998
Carcinogencity:	0.009	Eye Corrosion:	0.0
Eye Irritation:	0.888	Respiratory Toxicity:	0.877
Drug-induced Neurotoxicity:	0.065	Ototoxicity:	0.936
Hematotoxicity:	0.045	Drug-induced Nephrotoxicity:	0.176
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.99
BCF:	1.186 ? 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:	3.728 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.647 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.147 ? 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
NPO3160	Cassia fistula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38590868]
NPO3160	Cassia fistula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3160	Cassia fistula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3160	Cassia fistula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3160	Cassia fistula	Species	Fabaceae	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 NPC598381 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	22345
0.1-0.2	23854
0.2-0.3	3221
0.3-0.4	277
0.4-0.5	68
0.5-0.6	16
0.6-0.7	36
0.7-0.8	0
0.8-0.85	10
0.85-0.9	0
0.9-0.95	11
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9483	High Similarity	NPC58190
0.9483	High Similarity	NPC108811
0.9483	High Similarity	NPC170103
0.9483	High Similarity	NPC236202
0.9483	High Similarity	NPC262911
0.9483	High Similarity	NPC202742
0.9322	High Similarity	NPC246202
0.9322	High Similarity	NPC224161
0.9322	High Similarity	NPC46335
0.9322	High Similarity	NPC279406
0.9322	High Similarity	NPC486519
0.8438	Intermediate Similarity	NPC70409
0.8438	Intermediate Similarity	NPC204770
0.8438	Intermediate Similarity	NPC600551
0.8438	Intermediate Similarity	NPC601980
0.8438	Intermediate Similarity	NPC602065
0.8438	Intermediate Similarity	NPC611024
0.8333	Intermediate Similarity	NPC278548
0.8125	Intermediate Similarity	NPC313116
0.8125	Intermediate Similarity	NPC603340
0.803	Intermediate Similarity	NPC211561
0.7903	Intermediate Similarity	NPC96576
0.7761	Intermediate Similarity	NPC226809
0.7656	Intermediate Similarity	NPC601999
0.7647	Intermediate Similarity	NPC600630
0.7647	Intermediate Similarity	NPC607896
0.7647	Intermediate Similarity	NPC611369
0.75	Intermediate Similarity	NPC601997
0.75	Intermediate Similarity	NPC609211
0.75	Intermediate Similarity	NPC610665
0.7333	Intermediate Similarity	NPC86630
0.7297	Intermediate Similarity	NPC147743
0.7297	Intermediate Similarity	NPC4809
0.7297	Intermediate Similarity	NPC73517
0.7273	Intermediate Similarity	NPC294558
0.7273	Intermediate Similarity	NPC18185
0.7273	Intermediate Similarity	NPC263940
0.7237	Intermediate Similarity	NPC106601
0.7237	Intermediate Similarity	NPC151474
0.7143	Intermediate Similarity	NPC212614
0.7143	Intermediate Similarity	NPC205613
0.6935	Remote Similarity	NPC178054
0.6875	Remote Similarity	NPC159526
0.6757	Remote Similarity	NPC306267
0.6667	Remote Similarity	NPC261619
0.6667	Remote Similarity	NPC61477
0.6667	Remote Similarity	NPC78770
0.6667	Remote Similarity	NPC219876
0.6667	Remote Similarity	NPC126029
0.6667	Remote Similarity	NPC15658
0.6618	Remote Similarity	NPC277331
0.6618	Remote Similarity	NPC100482
0.6575	Remote Similarity	NPC46283
0.6575	Remote Similarity	NPC469944
0.6575	Remote Similarity	NPC302549
0.6429	Remote Similarity	NPC184245
0.6429	Remote Similarity	NPC187801
0.6429	Remote Similarity	NPC610920
0.64	Remote Similarity	NPC20050
0.6375	Remote Similarity	NPC78074
0.6351	Remote Similarity	NPC134911
0.6333	Remote Similarity	NPC207179
0.6333	Remote Similarity	NPC167571
0.6333	Remote Similarity	NPC278552
0.6234	Remote Similarity	NPC135021
0.6216	Remote Similarity	NPC272552
0.6216	Remote Similarity	NPC226108
0.6216	Remote Similarity	NPC322899
0.6203	Remote Similarity	NPC9309
0.6173	Remote Similarity	NPC478340
0.6154	Remote Similarity	NPC471404
0.6104	Remote Similarity	NPC478616
0.6104	Remote Similarity	NPC478339
0.6098	Remote Similarity	NPC478337
0.6098	Remote Similarity	NPC478338
0.6053	Remote Similarity	NPC44192
0.6027	Remote Similarity	NPC155564
0.593	Remote Similarity	NPC478617
0.5915	Remote Similarity	NPC82917
0.5714	Remote Similarity	NPC65333
0.5541	Remote Similarity	NPC165483
0.5529	Remote Similarity	NPC479793
0.5467	Remote Similarity	NPC28440
0.5402	Remote Similarity	NPC479794
0.5397	Remote Similarity	NPC601844
0.5312	Remote Similarity	NPC268266
0.5312	Remote Similarity	NPC42760
0.5312	Remote Similarity	NPC220825
0.5312	Remote Similarity	NPC268342
0.5217	Remote Similarity	NPC171932
0.52	Remote Similarity	NPC20757
0.52	Remote Similarity	NPC227516
0.5165	Remote Similarity	NPC185231

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC598381 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4566
0.1-0.2	4506
0.2-0.3	68
0.3-0.4	8
0.4-0.5	0
0.5-0.6	0
0.6-0.7	2
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
0.6667	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6667	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