NPASS Compound

Natural Product: NPC470950

Natural Product ID	NPC470950
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	4'-O-Lariciresinol-Glucoside
IUPAC Name	(2R,3S,4R,5R,6S)-2-[4-[[(3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL233297
PubChem CID	44429873
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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 71 74 0 0 0 0 0 0 0 0999 V2000 0.6935 0.7955 -1.0266 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7222 1.0706 -0.1663 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7577 -0.0324 -0.2674 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3516 -1.3990 0.0442 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6718 -1.9248 0.7177 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0858 -0.7948 1.4313 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9713 0.2589 0.5245 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2608 0.3756 -0.1658 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4463 0.0370 -1.5153 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6790 0.1950 -2.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7337 0.6844 -1.4125 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5684 1.0311 -0.0555 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3165 0.8652 0.5415 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6142 1.5015 0.5880 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6310 1.9588 1.2136 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9699 0.8359 -2.0443 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2983 -1.7691 0.9738 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0770 -1.3895 0.8463 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 -0.3658 1.5797 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9325 0.0231 1.4799 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8046 -0.6303 0.5919 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2836 -1.6635 -0.1599 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9530 -2.0223 -0.0247 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0697 -2.3585 -1.0630 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4972 -3.3984 -1.8241 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1097 -0.1959 0.5307 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2111 -0.6691 -0.1225 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2923 -0.6812 0.7416 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9914 0.4896 0.8455 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4923 0.7484 2.2591 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4835 0.8427 3.1908 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2152 1.7223 0.4466 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7429 1.5796 -0.9684 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5588 0.1543 -1.3516 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6413 -0.4007 -2.0358 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5037 2.2629 -1.0409 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1502 2.7836 0.4736 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0924 1.5651 -1.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2497 1.9763 -0.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4125 1.3468 0.8203 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9978 -0.0068 -1.3990 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3544 -2.0345 -0.9007 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4090 -2.2117 -0.0146 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4686 -2.7243 1.4172 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7569 1.2002 1.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6669 -0.3651 -2.1283 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8136 -0.0736 -3.1844 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2196 1.1492 1.6089 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5397 1.3005 1.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3961 2.3565 2.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1017 2.8759 0.7283 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0053 1.1308 -3.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6871 -1.5473 2.0265 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3002 -2.9220 1.0073 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0222 0.1972 2.3042 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3435 0.8346 2.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5446 -2.8255 -0.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5821 -3.0516 -2.3560 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2051 -3.8196 -2.5625 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1624 -4.2597 -1.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0936 -1.7551 -0.4552 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9229 0.4996 0.2047 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2236 -0.0606 2.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0986 1.6765 2.2742 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6327 0.5429 2.8312 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4231 1.9958 1.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4160 2.1044 -1.6928 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7028 0.1251 -2.0883 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7778 -1.3310 -1.6826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5358 3.0389 -0.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9228 2.5516 -0.0619 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 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 11 16 1 0 4 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 21 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 7 3 1 0 13 8 1 0 23 18 1 0 34 27 1 0 1 38 1 0 2 39 1 0 2 40 1 0 3 41 1 6 4 42 1 6 5 43 1 0 5 44 1 0 7 45 1 1 9 46 1 0 10 47 1 0 13 48 1 0 15 49 1 0 15 50 1 0 15 51 1 0 16 52 1 0 17 53 1 0 17 54 1 0 19 55 1 0 20 56 1 0 23 57 1 0 25 58 1 0 25 59 1 0 25 60 1 0 27 61 1 6 29 62 1 6 30 63 1 0 30 64 1 0 31 65 1 0 32 66 1 1 33 67 1 6 34 68 1 6 35 69 1 0 36 70 1 0 37 71 1 0 M END

Standard InCHIKey	GAYKAIAESJROGN-JJFAMHGWSA-N
Standard InCHI	InChI=1S/C26H34O11/c1-33-19-9-14(4-5-17(19)29)25-16(10-27)15(12-35-25)7-13-3-6-18(20(8-13)34-2)36-26-24(32)23(31)22(30)21(11-28)37-26/h3-6,8-9,15-16,21-32H,7,10-12H2,1-2H3/t15-,16-,21+,22+,23-,24+,25+,26+/m1/s1
SMILES	OC[C@@H]1[C@@H](CO[C@H]1c1ccc(c(c1)OC)O)Cc1ccc(c(c1)OC)O[C@H]1O[C@@H](CO)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	522.21	Volume:	504.9 ? Van der Waals volume.
Dense:	1.034	LogP:	0.194 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.755 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.199 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	23.0
TPSA:	167.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.265	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.322	Fsp³:	0.538
MCE-18:	89.7 ? 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:	0.554	Fluc inhibitor:	0.242 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.074 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.142 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.087	Promiscuous compounds:	0.111

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.4	MDCK Permeability:	-5.429
Pgp-inhibitor:	0.001	Pgp-substrate:	0.719
PAMPA:	0.862 ? 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):	0.33
20% Bioavailability (F20%):	0.548	30% Bioavailability (F30%):	0.968
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08	MRP1:	0.119
Plasma Protein Binding (PPB):	76.907%	Volume Distribution (VD):	-0.101
Fu:	22.525% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.116
BSEP inhibitor:	0.027

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.437	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.025	CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.05	CYP3A4-substrate:	0.977
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.604
HLM stability:	0.009 ? 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):

2.534

Half-life (T1/2):

2.596

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.134
Human Hepatotoxicity (H-HT):	0.893	Drug-induced Liver Injury (DILI):	0.91
AMES Toxicity:	0.891	Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.013	Skin Sensitization:	0.998
Carcinogencity:	0.105	Eye Corrosion:	0.0
Eye Irritation:	0.631	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.045	Ototoxicity:	0.931
Hematotoxicity:	0.277	Drug-induced Nephrotoxicity:	0.909
Genotoxicity:	0.566	RPMI-8226 Immunitoxicity:	0.246
A549 Cytotoxicity:	0.364	Hek293 Cytotoxicity:	0.16
BCF:	0.692 ? 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:	3.306 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.028 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.077 ? 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
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17287127]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6536	Marrubium velutinum	Species	Lamiaceae	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
Inhibition	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	Inhibition	=	12.27	%	PMID[23398362]

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 NPC470950 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	14087
0.1-0.2	30478
0.2-0.3	4114
0.3-0.4	911
0.4-0.5	200
0.5-0.6	28
0.6-0.7	26
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8919	High Similarity	NPC185307
0.8649	High Similarity	NPC39657
0.8472	Intermediate Similarity	NPC471063
0.7368	Intermediate Similarity	NPC38041
0.7368	Intermediate Similarity	NPC22150
0.7195	Intermediate Similarity	NPC129417
0.7195	Intermediate Similarity	NPC283995
0.7089	Intermediate Similarity	NPC605526
0.6829	Remote Similarity	NPC299706
0.6829	Remote Similarity	NPC115466
0.6829	Remote Similarity	NPC61604
0.6667	Remote Similarity	NPC478055
0.6471	Remote Similarity	NPC46092
0.6471	Remote Similarity	NPC163635
0.64	Remote Similarity	NPC64201
0.6395	Remote Similarity	NPC112861
0.6395	Remote Similarity	NPC470235
0.6389	Remote Similarity	NPC187998
0.6389	Remote Similarity	NPC257582
0.6389	Remote Similarity	NPC241522
0.6375	Remote Similarity	NPC51328
0.6375	Remote Similarity	NPC286235
0.6375	Remote Similarity	NPC55158
0.6296	Remote Similarity	NPC18979
0.6296	Remote Similarity	NPC279298
0.6235	Remote Similarity	NPC245615
0.6207	Remote Similarity	NPC486548
0.6184	Remote Similarity	NPC276753
0.6184	Remote Similarity	NPC205796
0.6162	Remote Similarity	NPC475224
0.6104	Remote Similarity	NPC246947
0.6049	Remote Similarity	NPC158635
0.6049	Remote Similarity	NPC229882
0.6	Remote Similarity	NPC282833
0.5844	Remote Similarity	NPC42300
0.5843	Remote Similarity	NPC486549
0.5843	Remote Similarity	NPC476356
0.5789	Remote Similarity	NPC486558
0.5778	Remote Similarity	NPC486546
0.5769	Remote Similarity	NPC278961
0.5769	Remote Similarity	NPC113680
0.5753	Remote Similarity	NPC206882
0.56	Remote Similarity	NPC472024
0.56	Remote Similarity	NPC270849
0.5581	Remote Similarity	NPC472711
0.5526	Remote Similarity	NPC26653
0.5526	Remote Similarity	NPC80600
0.5506	Remote Similarity	NPC486545
0.5301	Remote Similarity	NPC216129
0.5301	Remote Similarity	NPC130449
0.5301	Remote Similarity	NPC248132
0.5263	Remote Similarity	NPC11411
0.5176	Remote Similarity	NPC606627
0.5172	Remote Similarity	NPC227902
0.5165	Remote Similarity	NPC186316
0.5161	Remote Similarity	NPC486547
0.5132	Remote Similarity	NPC9912
0.5125	Remote Similarity	NPC302378
0.5114	Remote Similarity	NPC84181
0.5111	Remote Similarity	NPC469586
0.5111	Remote Similarity	NPC44452
0.5063	Remote Similarity	NPC248355

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470950 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3863
0.1-0.2	5110
0.2-0.3	163
0.3-0.4	14
0.4-0.5	0
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

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