NPASS Compound

Natural Product: NPC220214

Natural Product ID	NPC220214
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VGOZKGCKBLEHMS-OBJIMVFSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102000761
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 84 87 0 0 0 0 0 0 0 0999 V2000 -2.6504 -3.1276 2.4016 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6382 -3.2979 1.3266 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1998 -3.9890 0.0829 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8388 -3.1444 -1.1388 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3079 -1.6845 -0.9173 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8581 -1.1838 0.3518 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9221 -2.1866 0.9595 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9675 -0.0794 0.3952 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2115 0.7310 1.4972 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0659 0.9939 2.2152 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6956 2.2952 1.6790 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1931 2.1798 1.8336 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7009 1.0952 1.0982 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9947 0.6600 1.0198 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8822 1.2410 1.6518 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3590 -0.5101 0.1834 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5979 -0.8992 0.1443 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0791 -2.0208 -0.6325 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2245 -2.7365 -1.4279 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6998 -3.8065 -2.1704 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0275 -4.1458 -2.1045 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9241 -3.4612 -1.3226 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4092 -2.4004 -0.5984 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2474 -3.8227 -1.2742 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2729 -3.2351 -0.5254 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4586 -5.2269 -2.8679 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2696 2.5089 0.3847 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0350 2.9654 0.3922 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9209 2.0273 1.1240 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3261 2.6193 2.3457 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5047 3.2374 -0.8859 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9493 4.4414 -1.2094 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1502 5.0151 -0.5241 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4354 4.3399 -0.8198 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5743 4.6276 -0.0855 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8150 4.0491 -0.2880 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9258 3.1217 -1.2945 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8142 2.8021 -2.0571 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6077 3.4015 -1.8158 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0029 1.8521 -3.0663 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1441 2.5166 -1.5336 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0414 5.1384 0.8358 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1889 1.2075 3.5547 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6662 -1.7095 -1.2111 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4132 -3.6873 -2.2437 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6170 -5.2389 -0.1036 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6963 -3.4059 2.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4388 -3.8114 3.2873 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6154 -2.1048 2.8723 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8623 -4.0124 1.7455 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2764 -4.1197 0.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7292 -3.0698 -1.2458 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8422 -1.1530 -1.8203 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5134 -1.0805 1.2012 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9688 0.2044 2.1314 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7941 0.1570 2.1402 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3381 3.1074 2.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4052 2.1543 2.9151 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6465 3.1044 1.4130 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6005 -1.0203 -0.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3678 -0.3498 0.7372 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1883 -2.5007 -1.4964 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0429 -4.3897 -2.8122 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0824 -1.8143 0.0474 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1315 -3.4533 0.5690 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2358 -3.7213 -0.8558 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3160 -2.1624 -0.7417 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3982 -5.5710 -2.7453 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0907 3.9590 0.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8401 1.7108 0.5824 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1167 2.1117 2.6976 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1505 5.2563 -1.2080 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2185 4.4120 -2.3161 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2045 6.1012 -0.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4793 5.3744 0.7088 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6191 4.3658 0.3553 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7638 3.1255 -2.4422 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7662 2.0787 -3.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8486 2.8648 -2.1237 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5146 5.9163 1.0635 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1504 1.2183 3.7405 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0562 -2.5763 -0.9906 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5197 -4.6917 -2.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6404 -5.6869 0.8057 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 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 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 11 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 38 40 1 0 37 41 1 0 33 42 1 0 10 43 1 0 5 44 1 0 4 45 1 0 3 46 1 0 7 2 1 0 29 9 1 0 39 34 1 0 23 18 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 1 3 51 1 1 4 52 1 6 5 53 1 6 6 54 1 1 9 55 1 1 10 56 1 1 11 57 1 1 12 58 1 0 12 59 1 0 16 60 1 0 17 61 1 0 19 62 1 0 20 63 1 0 23 64 1 0 25 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 28 69 1 1 29 70 1 6 30 71 1 0 32 72 1 0 32 73 1 0 33 74 1 6 35 75 1 0 36 76 1 0 39 77 1 0 40 78 1 0 41 79 1 0 42 80 1 0 43 81 1 0 44 82 1 0 45 83 1 0 46 84 1 0 M END

Standard InCHIKey	VGOZKGCKBLEHMS-OBJIMVFSSA-N
Standard InCHI	InChI=1S/C30H38O16/c1-13-23(36)25(38)26(39)30(44-13)46-28-24(37)21(12-42-22(35)8-4-14-3-6-17(32)20(9-14)41-2)45-29(27(28)40)43-11-19(34)15-5-7-16(31)18(33)10-15/h3-10,13,19,21,23-34,36-40H,11-12H2,1-2H3/b8-4+/t13-,19-,21+,23-,24+,25+,26+,27+,28-,29+,30-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)O[C@H]([C@@H]1O)OC[C@@H](c1ccc(c(c1)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.22	Volume:	612.762 ? Van der Waals volume.
Dense:	1.068	LogP:	-0.171 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.74 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.587 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	26.0
TPSA:	254.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	4.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.078	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.827	Fsp³:	0.5
MCE-18:	103.333 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.685	Fluc inhibitor:	0.665 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.138 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.53 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.171	Promiscuous compounds:	0.305

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.441	MDCK Permeability:	-5.36
Pgp-inhibitor:	0.0	Pgp-substrate:	0.459
PAMPA:	0.989 ? 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):	0.651
20% Bioavailability (F20%):	0.994	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.004
Plasma Protein Binding (PPB):	69.711%	Volume Distribution (VD):	-0.382
Fu:	28.192% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.051
BSEP inhibitor:	0.003

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:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.976
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.161 ? 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):

1.364

Half-life (T1/2):

3.526

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.448
Human Hepatotoxicity (H-HT):	0.278	Drug-induced Liver Injury (DILI):	0.452
AMES Toxicity:	0.812	Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.077	Skin Sensitization:	0.999
Carcinogencity:	0.028	Eye Corrosion:	0.0
Eye Irritation:	0.404	Respiratory Toxicity:	0.014
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.913
Hematotoxicity:	0.027	Drug-induced Nephrotoxicity:	0.608
Genotoxicity:	0.262	RPMI-8226 Immunitoxicity:	0.143
A549 Cytotoxicity:	0.815	Hek293 Cytotoxicity:	0.27
BCF:	0.49 ? 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:	3.116 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.93 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.048 ? 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
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4203	Phlomoides rotata	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

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 NPC220214 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	15492
0.1-0.2	29123
0.2-0.3	4405
0.3-0.4	657
0.4-0.5	143
0.5-0.6	31
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	Natural Product ID
0.7363	Intermediate Similarity	NPC600370
0.6374	Remote Similarity	NPC64141
0.6214	Remote Similarity	NPC476398
0.5978	Remote Similarity	NPC235294
0.5833	Remote Similarity	NPC188393
0.5684	Remote Similarity	NPC205195
0.5684	Remote Similarity	NPC476868
0.5591	Remote Similarity	NPC291296
0.5567	Remote Similarity	NPC262182
0.5567	Remote Similarity	NPC476865
0.5532	Remote Similarity	NPC471405
0.551	Remote Similarity	NPC83743
0.5446	Remote Similarity	NPC173343
0.5437	Remote Similarity	NPC100998
0.5417	Remote Similarity	NPC226005
0.54	Remote Similarity	NPC300262
0.5333	Remote Similarity	NPC259347
0.5294	Remote Similarity	NPC125823
0.5294	Remote Similarity	NPC7145
0.5294	Remote Similarity	NPC143480
0.5288	Remote Similarity	NPC201148
0.5258	Remote Similarity	NPC476869
0.5243	Remote Similarity	NPC3460
0.5233	Remote Similarity	NPC157554
0.5229	Remote Similarity	NPC470933
0.5217	Remote Similarity	NPC157898
0.5146	Remote Similarity	NPC287615
0.5146	Remote Similarity	NPC34587
0.5143	Remote Similarity	NPC34927
0.5094	Remote Similarity	NPC232992
0.5052	Remote Similarity	NPC476867
0.5051	Remote Similarity	NPC488082
0.505	Remote Similarity	NPC265648
0.5048	Remote Similarity	NPC476397

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC220214 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4771
0.1-0.2	4270
0.2-0.3	103
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	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