NPASS Compound

Natural Product: NPC248826

Natural Product ID	NPC248826
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SFNFQCXADNWOCI-QSKBEBRPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44257768
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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 72 76 0 0 0 0 0 0 0 0999 V2000 -2.3928 2.4852 -1.0471 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7538 2.4874 -0.9779 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4314 1.4107 -0.4087 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6833 0.3743 0.0667 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2908 0.3953 -0.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5977 1.4638 -0.5815 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1488 1.4581 -0.6533 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5435 2.4953 -1.2032 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9415 2.4690 -1.2620 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6108 3.4052 -1.7606 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5517 1.3477 -0.7375 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8035 0.3287 -0.1937 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4772 -0.7629 0.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8542 -0.8222 0.2713 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6028 0.2070 -0.2775 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9169 1.2796 -0.7740 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6579 2.3108 -1.3234 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0601 0.0612 -0.2803 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7534 0.5921 0.9257 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2516 0.3602 0.7280 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4471 -1.1465 0.5648 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6808 -1.5338 -0.6835 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8543 -3.0261 -0.8741 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2167 -3.3054 -1.1095 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3477 -1.2912 -0.4568 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8038 -1.4414 0.4540 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8746 0.8244 1.8812 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3955 -0.1489 2.0478 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4965 -1.9442 0.7946 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4993 0.4202 -0.1720 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7936 1.4105 -0.3383 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5870 0.4216 0.1947 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4094 0.9601 1.3458 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8261 0.5005 1.3380 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0687 -0.8298 0.7308 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9452 -1.3108 -0.1520 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4605 -2.3037 -1.1536 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4716 -1.7989 -1.9514 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4192 -0.1623 -0.7790 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3936 -1.8298 1.6498 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6654 1.4881 0.7696 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7482 0.6666 2.5373 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8714 3.3457 -1.5006 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3088 3.3193 -1.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1057 -0.5271 0.5356 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6853 -0.4256 0.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0910 3.3765 -1.6169 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9143 -1.5926 0.7532 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8613 3.1777 -0.8701 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4555 0.6220 -1.1726 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6350 1.6685 1.0415 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6429 0.9226 -0.1393 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9842 -1.6108 1.4595 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1059 -0.9636 -1.5276 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2891 -3.3937 -1.7404 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5408 -3.5384 0.0480 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6162 -3.6798 -0.2633 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2071 -0.6626 -0.0342 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0383 1.7992 1.7469 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1324 0.3884 2.8130 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0249 -2.8418 0.7846 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9860 -0.4124 0.5829 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4131 2.0661 1.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1629 0.4442 2.4154 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9720 -0.7442 0.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1601 -1.7806 0.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5955 -2.6948 -1.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8832 -3.1511 -0.5857 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9614 -2.5776 -2.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9977 -1.4739 2.3601 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2057 2.3629 0.7689 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7847 0.6115 2.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 21 26 1 0 20 27 1 0 19 28 1 0 14 29 1 0 12 30 1 0 3 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 6 1 1 0 30 7 1 0 39 32 1 0 16 11 1 0 25 18 1 0 1 43 1 0 2 44 1 0 4 45 1 0 5 46 1 0 8 47 1 0 13 48 1 0 17 49 1 0 18 50 1 6 19 51 1 0 20 52 1 6 21 53 1 1 22 54 1 0 23 55 1 0 23 56 1 0 24 57 1 0 26 58 1 0 27 59 1 0 28 60 1 0 29 61 1 0 32 62 1 1 33 63 1 0 34 64 1 1 35 65 1 6 36 66 1 0 37 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	SFNFQCXADNWOCI-QSKBEBRPSA-N
Standard InCHI	InChI=1S/C27H30O15/c28-7-15-19(32)22(35)24(37)26(41-15)18-12(31)6-14-17(21(18)34)11(30)5-13(40-14)9-1-3-10(4-2-9)39-27-25(38)23(36)20(33)16(8-29)42-27/h1-6,15-16,19-20,22-29,31-38H,7-8H2/t15?,16?,19-,20-,22+,23+,24?,25?,26+,27-/m1/s1
SMILES	c1cc(ccc1c1cc(=O)c2c(cc(c(c2O)[C@H]2C([C@H]([C@@H](C(CO)O2)O)O)O)O)o1)O[C@H]1C([C@H]([C@@H](C(CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	-0.51 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.616 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.2 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	260.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.142	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.68	Fsp³:	0.444
MCE-18:	119.436 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.626	Fluc inhibitor:	0.126 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.951 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.908 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.317	Promiscuous compounds:	0.239

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.576	MDCK Permeability:	-5.001
Pgp-inhibitor:	0.0	Pgp-substrate:	0.982
PAMPA:	1.0 ? 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):	0.998
20% Bioavailability (F20%):	0.956	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.839
Plasma Protein Binding (PPB):	84.132%	Volume Distribution (VD):	0.063
Fu:	13.691% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.054
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.002
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.088	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.012
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.959
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):

2.099

Half-life (T1/2):

4.605

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.088
Human Hepatotoxicity (H-HT):	0.635	Drug-induced Liver Injury (DILI):	0.903
AMES Toxicity:	0.801	Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.054	Skin Sensitization:	0.901
Carcinogencity:	0.085	Eye Corrosion:	0.0
Eye Irritation:	0.023	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.979
Hematotoxicity:	0.075	Drug-induced Nephrotoxicity:	0.285
Genotoxicity:	0.794	RPMI-8226 Immunitoxicity:	0.158
A549 Cytotoxicity:	0.239	Hek293 Cytotoxicity:	0.342
BCF:	0.322 ? 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:	2.726 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.646 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.442 ? 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
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30164	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30164	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	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 NPC248826 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	20434
0.1-0.2	25610
0.2-0.3	2646
0.3-0.4	880
0.4-0.5	219
0.5-0.6	49
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC603300
0.7215	Intermediate Similarity	NPC328740
0.7215	Intermediate Similarity	NPC289774
0.6914	Remote Similarity	NPC53545
0.6829	Remote Similarity	NPC143851
0.6744	Remote Similarity	NPC111249
0.6742	Remote Similarity	NPC47923
0.6596	Remote Similarity	NPC256760
0.6517	Remote Similarity	NPC472607
0.6484	Remote Similarity	NPC218488
0.6484	Remote Similarity	NPC607513
0.6429	Remote Similarity	NPC58053
0.6279	Remote Similarity	NPC186807
0.6279	Remote Similarity	NPC602537
0.6163	Remote Similarity	NPC95090
0.6163	Remote Similarity	NPC27408
0.5778	Remote Similarity	NPC191306
0.5698	Remote Similarity	NPC289771
0.5698	Remote Similarity	NPC268193
0.5682	Remote Similarity	NPC39360
0.5682	Remote Similarity	NPC29763
0.5682	Remote Similarity	NPC210003
0.5652	Remote Similarity	NPC88023
0.5652	Remote Similarity	NPC309025
0.5604	Remote Similarity	NPC609451
0.5556	Remote Similarity	NPC124155
0.5556	Remote Similarity	NPC10807
0.5556	Remote Similarity	NPC161881
0.5556	Remote Similarity	NPC105025
0.5556	Remote Similarity	NPC10097
0.5543	Remote Similarity	NPC22832
0.5543	Remote Similarity	NPC243930
0.5543	Remote Similarity	NPC605067
0.5542	Remote Similarity	NPC139966
0.5506	Remote Similarity	NPC45618
0.5484	Remote Similarity	NPC607707
0.5444	Remote Similarity	NPC93337
0.5444	Remote Similarity	NPC64305
0.5444	Remote Similarity	NPC146792
0.5444	Remote Similarity	NPC259152
0.5444	Remote Similarity	NPC189142
0.5444	Remote Similarity	NPC77660
0.5393	Remote Similarity	NPC112701
0.5376	Remote Similarity	NPC601710
0.5361	Remote Similarity	NPC78734
0.5361	Remote Similarity	NPC604854
0.5333	Remote Similarity	NPC261866
0.5333	Remote Similarity	NPC83283
0.5326	Remote Similarity	NPC201292
0.5275	Remote Similarity	NPC168822
0.5253	Remote Similarity	NPC257566
0.5248	Remote Similarity	NPC150767
0.5217	Remote Similarity	NPC58716
0.5217	Remote Similarity	NPC45638
0.5217	Remote Similarity	NPC610763
0.5213	Remote Similarity	NPC601144
0.5165	Remote Similarity	NPC289667
0.5161	Remote Similarity	NPC472459
0.5158	Remote Similarity	NPC311830
0.5158	Remote Similarity	NPC602805
0.5054	Remote Similarity	NPC181712
0.5053	Remote Similarity	NPC148710
0.5052	Remote Similarity	NPC294629
0.5052	Remote Similarity	NPC131407
0.5052	Remote Similarity	NPC190393

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC248826 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4759
0.1-0.2	4295
0.2-0.3	77
0.3-0.4	16
0.4-0.5	3
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