NPASS Compound

Natural Product: NPC475391

Natural Product ID	NPC475391
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YIXVDGLDWGKZOK-WZMNZSSYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL504771
PubChem CID	44559776
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

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 82 85 0 0 0 0 0 0 0 0999 V2000 -3.7525 -1.6803 -1.9632 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1525 -3.0737 -1.7630 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4455 -3.8829 -1.0055 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2524 -3.4340 -0.3431 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6091 -4.2542 0.3680 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6934 -2.1748 -0.3821 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5360 -1.7744 0.2668 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8004 -2.3794 0.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5985 -1.6616 -1.0634 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2317 -2.2104 -2.4331 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3631 -0.2086 -0.9985 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9994 0.1698 0.4234 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4186 -0.3277 0.6176 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8274 -1.2062 1.6974 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1501 -1.7609 2.7081 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2359 -1.1586 2.1752 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1278 -0.3655 1.4784 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1367 1.0099 1.4091 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2688 1.6693 2.0430 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1834 1.6578 0.5791 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0835 3.1521 0.5874 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5671 1.2467 1.0424 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0565 1.6395 0.5217 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1539 2.3970 0.4854 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9808 3.8717 0.6028 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7123 4.2696 1.7704 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3581 3.7302 2.9979 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4071 2.9096 3.0486 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0555 4.0801 4.2627 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5789 1.9890 0.3408 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6355 0.7757 -0.5520 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4569 0.6762 -1.4718 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9593 0.3774 -2.8080 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2653 0.5372 -2.8246 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7616 0.9538 -1.5173 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9118 1.3813 -1.2445 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1708 0.3299 -4.0102 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8935 -0.3322 0.1965 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2184 0.0818 -1.7744 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9122 -5.2733 -0.8524 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9357 -1.1271 -1.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7307 -1.5491 -2.3710 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4340 -1.1858 -2.7159 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0723 -3.4239 -2.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4041 -2.2595 0.9575 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7978 -3.4427 -0.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6543 -1.9818 -0.8967 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1405 -2.2391 -3.0682 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9254 -3.2920 -2.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4404 -1.6184 -2.9223 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7374 -0.2549 1.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1431 0.3592 0.1155 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2769 -1.6667 3.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2989 -2.8646 2.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1222 -1.2764 2.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2000 -0.9149 3.2620 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6420 -2.2074 2.1399 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0846 1.2959 -0.4784 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7480 3.5625 1.5653 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0930 3.6156 0.3981 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4379 3.5329 -0.2417 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2507 2.1225 1.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0198 0.4814 0.3675 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5270 0.8442 2.0818 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1249 2.1930 0.6364 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9397 4.1858 0.6688 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5274 4.3419 -0.2576 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5972 5.0275 4.1767 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7359 3.2107 4.4842 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2998 4.1752 5.0889 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1791 2.8271 -0.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9241 1.7348 1.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0224 1.7219 -1.5214 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3711 0.0747 -3.6533 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1669 -0.0123 -3.7152 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7096 -0.4399 -4.6638 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2467 1.2984 -4.5674 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3081 -0.1624 1.0592 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4509 0.5470 -2.6020 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5868 -5.8241 -1.7780 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0218 -5.3512 -0.8388 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4375 -5.8045 -0.0053 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 4 6 1 0 7 6 1 6 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 20 22 1 0 12 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 24 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 34 37 1 0 31 38 1 1 11 39 1 6 3 40 1 0 13 7 1 0 35 31 1 0 14 7 1 0 32 11 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 8 45 1 0 8 46 1 0 9 47 1 1 10 48 1 0 10 49 1 0 10 50 1 0 12 51 1 1 13 52 1 6 15 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 20 58 1 0 21 59 1 0 21 60 1 0 21 61 1 0 22 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 25 66 1 0 25 67 1 0 29 68 1 0 29 69 1 0 29 70 1 0 30 71 1 0 30 72 1 0 32 73 1 6 33 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 38 78 1 0 39 79 1 0 40 80 1 0 40 81 1 0 40 82 1 0 M END

Standard InCHIKey	YIXVDGLDWGKZOK-WZMNZSSYSA-N
Standard InCHI	InChI=1S/C31H42O9/c1-9-17(4)27(35)40-30-12-19(6)31(37)22(24(30)28(30,8)15-39-26(34)16(2)3)11-21(14-38-20(7)32)13-29(36)23(31)10-18(5)25(29)33/h9-11,16,19,22-24,36-37H,12-15H2,1-8H3/b17-9-/t19-,22+,23-,24-,28-,29-,30+,31-/m1/s1
SMILES	C/C=C(C(=O)O[C@@]12C[C@@H](C)[C@]3([C@H]([C@@H]1[C@@]2(C)COC(=O)C(C)C)C=C(COC(=O)C)C[C@]1([C@H]3C=C(C1=O)C)O)O)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	558.28	Volume:	571.163 ? Van der Waals volume.
Dense:	0.977	LogP:	2.219 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.422 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.872 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	23.0
TPSA:	136.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.209	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.369	Fsp³:	0.677
MCE-18:	85.846 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.268	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.277	Promiscuous compounds:	0.366

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.112	MDCK Permeability:	-4.772
Pgp-inhibitor:	0.325	Pgp-substrate:	0.49
PAMPA:	0.887 ? 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):	0.097
20% Bioavailability (F20%):	0.947	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034	MRP1:	0.989
Plasma Protein Binding (PPB):	79.184%	Volume Distribution (VD):	0.038
Fu:	26.047% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.019
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.609	CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	0.012	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.73
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.98
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.995 ? 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):

5.694

Half-life (T1/2):

0.679

ADMET: Toxicity

hERG Blockers:	0.078	hERG Blockers (10um):	0.255
Human Hepatotoxicity (H-HT):	0.529	Drug-induced Liver Injury (DILI):	0.452
AMES Toxicity:	0.541	Rat Oral Acute Toxicity:	0.348
Maximum Recommended Daily Dose:	0.539	Skin Sensitization:	0.927
Carcinogencity:	0.735	Eye Corrosion:	0.013
Eye Irritation:	0.149	Respiratory Toxicity:	0.367
Drug-induced Neurotoxicity:	0.253	Ototoxicity:	0.486
Hematotoxicity:	0.691	Drug-induced Nephrotoxicity:	0.746
Genotoxicity:	0.873	RPMI-8226 Immunitoxicity:	0.122
A549 Cytotoxicity:	0.068	Hek293 Cytotoxicity:	0.141
BCF:	0.526 ? 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:	3.535 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.61 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.932 ? 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
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25960	Euphorbia triangularis	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
Activity	2

Activity Type	# Activity
Organism	2

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
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.91	nmol	PubChem BioAssay data set
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.1	/nmol	PMID[19877653]

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 NPC475391 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	19011
0.1-0.2	29116
0.2-0.3	1620
0.3-0.4	54
0.4-0.5	28
0.5-0.6	18
0.6-0.7	5
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC474937
0.8088	Intermediate Similarity	NPC474872
0.803	Intermediate Similarity	NPC474871
0.7714	Intermediate Similarity	NPC482317
0.7206	Intermediate Similarity	NPC174471
0.7015	Intermediate Similarity	NPC96739
0.6761	Remote Similarity	NPC260786
0.6364	Remote Similarity	NPC151216
0.6364	Remote Similarity	NPC89227
0.6111	Remote Similarity	NPC71889
0.6053	Remote Similarity	NPC170212
0.5844	Remote Similarity	NPC17138
0.5844	Remote Similarity	NPC101825
0.5844	Remote Similarity	NPC215643
0.5844	Remote Similarity	NPC265499
0.5769	Remote Similarity	NPC221511
0.5732	Remote Similarity	NPC602538
0.5679	Remote Similarity	NPC479000
0.5663	Remote Similarity	NPC153651
0.5405	Remote Similarity	NPC158523
0.5366	Remote Similarity	NPC183540
0.5342	Remote Similarity	NPC153036
0.5342	Remote Similarity	NPC91189
0.5227	Remote Similarity	NPC180640
0.5176	Remote Similarity	NPC222307
0.5169	Remote Similarity	NPC185876
0.5169	Remote Similarity	NPC19336
0.5116	Remote Similarity	NPC159692
0.5065	Remote Similarity	NPC475937

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6870
0.1-0.2	2269
0.2-0.3	11
0.3-0.4	0
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