NPASS Compound

Natural Product: NPC222307

Natural Product ID	NPC222307
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Fischerosides A
IUPAC Name	n.a.
Synonyms	Fischerosides A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1813581
PubChem CID	53360347
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene 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 79 83 0 0 0 0 0 0 0 0999 V2000 8.4035 -1.5403 -0.1307 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0969 -1.6478 -0.6026 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3559 -0.3112 -0.4467 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0907 -0.4980 -0.9286 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2466 0.5755 -0.7971 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9965 0.0868 -0.4248 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0095 0.3967 -1.3498 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7308 -0.1864 -0.8233 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2754 0.6439 -0.5805 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6405 0.3501 -0.0624 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5090 1.4591 -0.6681 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9101 1.4678 -0.1865 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0391 2.5036 0.3421 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4348 2.4550 1.7218 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2113 3.9062 -0.2023 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8514 1.8628 -1.1724 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1932 1.9687 -0.9761 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6805 1.7096 0.1511 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1001 2.3886 -2.0794 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1491 0.1265 0.4554 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6614 -0.9799 -0.4956 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1635 -0.9985 -0.5785 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5120 -2.1768 -0.0211 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1086 -2.0016 0.4999 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7785 -1.6848 -0.6382 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0287 -1.0018 1.4521 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1017 -3.2768 1.1864 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1526 -3.9441 1.2497 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2319 -3.5661 1.7769 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1431 -2.9214 1.0650 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4575 -4.4417 2.9663 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8481 -0.9406 -1.9644 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3111 -0.7126 -1.8616 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6925 1.5665 0.2596 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1138 0.7183 1.4670 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4074 0.0256 1.0228 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4228 0.9909 1.2030 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1741 -0.2975 1.6238 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7736 2.3386 -0.1850 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4705 -1.8523 0.8190 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0984 -1.9699 -1.6682 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5706 -2.4089 0.0107 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9622 0.4144 -1.0628 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2240 1.1224 -1.7639 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8419 1.4967 -1.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1958 -0.0828 -2.3300 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0341 1.7006 -0.8046 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7377 0.4283 1.0221 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2626 1.8546 -1.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3272 2.4798 1.7132 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7842 1.5956 2.3257 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7681 3.3638 2.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9084 4.4266 0.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2439 4.4693 -0.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5909 3.9280 -1.2299 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7463 3.2313 -1.6970 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5408 2.7904 -2.9412 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7800 1.5914 -2.4045 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2387 -0.0374 0.5310 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6950 0.0034 1.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1315 -1.8978 -0.1347 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3902 -2.9447 -0.8516 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8249 -1.9224 -0.3726 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5080 -2.1992 -1.5895 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4031 -1.2278 2.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1816 -2.9699 1.2922 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7954 -3.8254 3.8392 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5462 -4.9753 3.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2409 -5.2068 2.6940 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8327 -0.0332 -2.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8641 0.1282 -2.3837 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0651 -1.6353 -2.4649 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3918 -0.7089 -1.7406 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8842 2.2563 0.4958 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2527 1.3249 2.3635 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6471 -0.8279 1.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9011 1.1643 0.3604 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3073 0.0495 1.9880 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6674 2.4933 -1.1487 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 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 12 16 1 6 16 17 1 0 17 18 2 0 17 19 1 0 12 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 1 24 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 29 31 1 0 22 32 1 6 21 33 1 0 5 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 35 38 1 0 34 39 1 0 36 3 1 0 25 8 1 0 22 10 1 0 30 23 1 0 13 11 1 0 1 40 1 0 2 41 1 0 2 42 1 0 3 43 1 6 5 44 1 6 7 45 1 0 7 46 1 0 9 47 1 0 10 48 1 1 11 49 1 6 14 50 1 0 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 15 55 1 0 19 56 1 0 19 57 1 0 19 58 1 0 20 59 1 0 20 60 1 0 21 61 1 1 23 62 1 6 25 63 1 0 25 64 1 0 26 65 1 0 30 66 1 0 31 67 1 0 31 68 1 0 31 69 1 0 32 70 1 0 33 71 1 0 33 72 1 0 33 73 1 0 34 74 1 1 35 75 1 1 36 76 1 1 37 77 1 0 38 78 1 0 39 79 1 0 M END

Standard InCHIKey	JMDGBSYRPFFZBO-WHDWRCRCSA-N
Standard InCHI	InChI=1S/C28H40O11/c1-12-6-18-26(35,23(12)34)9-15(11-37-24-21(33)20(32)19(31)17(10-29)38-24)7-16-22-25(4,5)27(22,39-14(3)30)8-13(2)28(16,18)36/h6-7,13,16-22,24,29,31-33,35-36H,8-11H2,1-5H3/t13-,16+,17-,18-,19-,20+,21-,22-,24-,26-,27+,28-/m1/s1
SMILES	OC[C@H]1O[C@@H](OCC2=C[C@H]3[C@H]4[C@@](C4(C)C)(OC(=O)C)C[C@H]([C@@]3([C@H]3[C@@](C2)(O)C(=O)C(=C3)C)O)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.26	Volume:	536.208 ? Van der Waals volume.
Dense:	1.03	LogP:	-0.002 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.568 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.816 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	26.0
TPSA:	183.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.188	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.434	Fsp³:	0.786
MCE-18:	104.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.571	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.028 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.126	Promiscuous compounds:	0.378

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.695	MDCK Permeability:	-5.093
Pgp-inhibitor:	0.003	Pgp-substrate:	0.841
PAMPA:	0.987 ? 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):	0.225
20% Bioavailability (F20%):	0.267	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.799
Plasma Protein Binding (PPB):	52.012%	Volume Distribution (VD):	-0.416
Fu:	45.678% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	0.082

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.88
HLM stability:	0.223 ? 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):

1.672

Half-life (T1/2):

2.241

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.045
Human Hepatotoxicity (H-HT):	0.768	Drug-induced Liver Injury (DILI):	0.541
AMES Toxicity:	0.819	Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.082	Skin Sensitization:	0.999
Carcinogencity:	0.226	Eye Corrosion:	0.0
Eye Irritation:	0.047	Respiratory Toxicity:	0.059
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.938
Hematotoxicity:	0.733	Drug-induced Nephrotoxicity:	0.742
Genotoxicity:	0.899	RPMI-8226 Immunitoxicity:	0.094
A549 Cytotoxicity:	0.32	Hek293 Cytotoxicity:	0.197
BCF:	0.455 ? 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:	3.14 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.803 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.003 ? 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
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[16792421]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	whole plants	Panshi, Jilin Province, China	2009-JUN	PMID[21534540]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25453801]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26702644]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28383891]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16205	Euphorbia fischeriana	Species	Euphorbiaceae	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
EC50	1
CC50	1

Activity Type	# Activity
Cell line	1
Organism	1

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
NPT1452	Cell line	C8166	Homo sapiens	CC50	>	360.0	nM	PMID[21534540]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	170.0	nM	PMID[21534540]

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 NPC222307 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	16212
0.1-0.2	28373
0.2-0.3	4882
0.3-0.4	323
0.4-0.5	32
0.5-0.6	22
0.6-0.7	9
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
0.7403	Intermediate Similarity	NPC270109
0.7	Intermediate Similarity	NPC96739
0.6966	Remote Similarity	NPC102367
0.6703	Remote Similarity	NPC478682
0.6486	Remote Similarity	NPC174471
0.6413	Remote Similarity	NPC478683
0.6316	Remote Similarity	NPC474871
0.6316	Remote Similarity	NPC260786
0.6282	Remote Similarity	NPC170212
0.625	Remote Similarity	NPC153036
0.6027	Remote Similarity	NPC91189
0.5976	Remote Similarity	NPC183540
0.5904	Remote Similarity	NPC479000
0.5875	Remote Similarity	NPC17138
0.5875	Remote Similarity	NPC101825
0.5875	Remote Similarity	NPC215643
0.5875	Remote Similarity	NPC265499
0.5802	Remote Similarity	NPC221511
0.5698	Remote Similarity	NPC159692
0.5658	Remote Similarity	NPC158523
0.5595	Remote Similarity	NPC151216
0.5595	Remote Similarity	NPC89227
0.5581	Remote Similarity	NPC602538
0.5513	Remote Similarity	NPC71889
0.5513	Remote Similarity	NPC475937
0.5309	Remote Similarity	NPC485736
0.5309	Remote Similarity	NPC277477
0.5309	Remote Similarity	NPC479003
0.5309	Remote Similarity	NPC485735
0.5181	Remote Similarity	NPC482454
0.5176	Remote Similarity	NPC475391
0.5122	Remote Similarity	NPC485733
0.5057	Remote Similarity	NPC474937

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC222307 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6442
0.1-0.2	2630
0.2-0.3	74
0.3-0.4	4
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