NPASS Compound

Natural Product: NPC473548

Natural Product ID	NPC473548
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VJELPTFOTXKQJX-GDLUAPLLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL445255
PubChem CID	44559852
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 82 87 0 0 0 0 0 0 0 0999 V2000 -1.9844 14.0128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5510 13.5706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8823 13.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3157 12.6864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6495 11.2240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5499 10.2037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8837 8.7413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7841 7.7211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1179 6.2587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0183 5.2384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1974 3.7491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1636 3.1186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1839 4.2182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4534 5.5283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0836 5.4184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5729 5.2393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4941 6.7977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6463 3.8844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0884 2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0682 1.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5989 2.5992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6058 1.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6058 -1.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0682 -1.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7190 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2054 -0.2013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4732 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1523 -2.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9510 -3.8745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8247 -2.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0812 -0.2218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2566 -3.0367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4120 -1.9894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2569 -3.2287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4232 3.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7210 5.3825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0559 6.0668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3159 5.2530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1306 7.5650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4265 12.5794 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5422 15.4461 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4177 14.4549 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1089 15.0040 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9931 12.1373 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3245 14.5618 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4402 11.6951 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4153 13.7066 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0828 10.7818 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1166 10.6458 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3171 8.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6492 8.1632 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5513 5.8165 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8225 4.5793 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7363 6.1861 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7411 4.2983 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7912 7.5509 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0131 6.5594 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9045 8.1770 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1346 4.0709 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9941 1.2553 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2370 2.2988 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5567 1.8771 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5558 -2.7564 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2460 -1.4044 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2420 0.8828 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1739 -3.6795 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4755 -0.9766 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1761 -2.9789 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5831 -0.1470 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4116 -4.2760 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7151 -2.9791 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6513 -1.1444 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7528 -3.1166 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4458 4.6352 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1075 1.8005 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7580 3.8197 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6288 7.4902 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6528 7.8218 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2054 9.0631 0.0000 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 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 10 9 1 6 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 6 15 16 2 0 15 17 1 0 13 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 27 34 1 1 26 35 1 0 25 36 1 1 36 37 1 0 19 38 1 0 18 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 14 10 1 0 28 20 1 0 21 10 1 0 25 23 1 0 31 27 1 0 22 12 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 5 51 1 0 6 52 1 0 7 53 1 0 8 54 1 0 9 55 1 0 12 56 1 1 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 17 61 1 0 18 62 1 6 19 63 1 1 22 64 1 1 23 65 1 1 26 66 1 6 28 67 1 6 29 68 1 0 33 69 1 0 33 70 1 0 33 71 1 0 34 72 1 0 35 73 1 0 36 74 1 0 36 75 1 0 37 76 1 0 38 77 1 0 38 78 1 0 38 79 1 0 42 80 1 0 42 81 1 0 42 82 1 0 M END

Standard InCHIKey	VJELPTFOTXKQJX-GDLUAPLLSA-N
Standard InCHI	InChI=1S/C32H40O10/c1-7-8-9-10-11-12-13-14-29-40-26-22-25-28(16-33,39-25)27(36)30(37)21(15-18(4)23(30)35)32(22,42-29)19(5)24(38-20(6)34)31(26,41-29)17(2)3/h9-15,19,21-22,24-27,33,36-37H,2,7-8,16H2,1,3-6H3/b10-9-,12-11+,14-13+/t19-,21-,22+,24-,25+,26-,27-,28+,29-,30-,31-,32+/m1/s1
SMILES	CCC/C=CC=CC=C[C@@]12O[C@H]3[C@@](O1)(C(=C)C)[C@@H]([C@H]([C@@]1(O2)[C@H]3[C@@H]2O[C@@]2([C@H]([C@]2([C@H]1C=C(C2=O)C)O)O)CO)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	584.26	Volume:	580.136 ? Van der Waals volume.
Dense:	1.007	LogP:	3.232 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.334 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.939 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	144.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.168	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.993	Fsp³:	0.625
MCE-18:	108.308 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.62	Fluc inhibitor:	0.118 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.011 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.312	Promiscuous compounds:	0.277

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.254	MDCK Permeability:	-4.889
Pgp-inhibitor:	0.019	Pgp-substrate:	0.006
PAMPA:	0.112 ? 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):	0.005
20% Bioavailability (F20%):	0.146	30% Bioavailability (F30%):	0.95
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129	MRP1:	0.939
Plasma Protein Binding (PPB):	72.047%	Volume Distribution (VD):	-0.12
Fu:	26.105% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.029
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.016	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.02	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.092	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.088	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.413
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.786
HLM stability:	0.402 ? 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):

5.979

Half-life (T1/2):

1.252

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.181
Human Hepatotoxicity (H-HT):	0.565	Drug-induced Liver Injury (DILI):	0.108
AMES Toxicity:	0.967	Rat Oral Acute Toxicity:	0.408
Maximum Recommended Daily Dose:	0.724	Skin Sensitization:	1.0
Carcinogencity:	0.307	Eye Corrosion:	0.009
Eye Irritation:	0.486	Respiratory Toxicity:	0.731
Drug-induced Neurotoxicity:	0.084	Ototoxicity:	0.829
Hematotoxicity:	0.471	Drug-induced Nephrotoxicity:	0.38
Genotoxicity:	0.036	RPMI-8226 Immunitoxicity:	0.237
A549 Cytotoxicity:	0.655	Hek293 Cytotoxicity:	0.779
BCF:	0.593 ? 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:	3.487 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.323 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.557 ? 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
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000015]
NPO33116	synaptolepis retusa	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]
NPO33116	synaptolepis retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	6
Survival	1

Activity Type	# Activity
Organism	7

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	=	1.1	nmol	PMID[17822299]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.91	/nmol	PMID[1593279]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.0	%	PMID[21044847]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.0	n.a.	PMID[21044847]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	100.0	%	PMID[23398362]

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 NPC473548 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	18505
0.1-0.2	29775
0.2-0.3	1485
0.3-0.4	22
0.4-0.5	16
0.5-0.6	12
0.6-0.7	7
0.7-0.8	0
0.8-0.85	6
0.85-0.9	2
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC324104
0.9167	High Similarity	NPC223356
0.9167	High Similarity	NPC298697
0.9167	High Similarity	NPC475500
0.9167	High Similarity	NPC100017
0.9167	High Similarity	NPC481742
0.9041	High Similarity	NPC182266
0.9041	High Similarity	NPC475154
0.9041	High Similarity	NPC485700
0.8533	High Similarity	NPC75831
0.8533	High Similarity	NPC471137
0.8421	Intermediate Similarity	NPC471136
0.8421	Intermediate Similarity	NPC116727
0.8421	Intermediate Similarity	NPC39509
0.8312	Intermediate Similarity	NPC481744
0.8312	Intermediate Similarity	NPC481743
0.8267	Intermediate Similarity	NPC180902
0.7765	Intermediate Similarity	NPC130886
0.7619	Intermediate Similarity	NPC164150
0.7619	Intermediate Similarity	NPC481754
0.7586	Intermediate Similarity	NPC481774
0.7403	Intermediate Similarity	NPC475606
0.7191	Intermediate Similarity	NPC101786
0.7089	Intermediate Similarity	NPC251564
0.7089	Intermediate Similarity	NPC477189
0.7045	Intermediate Similarity	NPC92598
0.7045	Intermediate Similarity	NPC43304
0.7045	Intermediate Similarity	NPC481753
0.7045	Intermediate Similarity	NPC477188
0.7045	Intermediate Similarity	NPC477190
0.7033	Intermediate Similarity	NPC481773
0.7	Intermediate Similarity	NPC474508
0.7	Intermediate Similarity	NPC473485
0.7	Intermediate Similarity	NPC171411
0.7	Intermediate Similarity	NPC485701
0.6947	Remote Similarity	NPC191992
0.679	Remote Similarity	NPC475314
0.679	Remote Similarity	NPC102997
0.6707	Remote Similarity	NPC485693
0.6593	Remote Similarity	NPC486153
0.6465	Remote Similarity	NPC69240
0.622	Remote Similarity	NPC162495
0.5851	Remote Similarity	NPC68282
0.573	Remote Similarity	NPC473838
0.5579	Remote Similarity	NPC156682
0.5579	Remote Similarity	NPC49297
0.5361	Remote Similarity	NPC486154
0.5361	Remote Similarity	NPC481745
0.5269	Remote Similarity	NPC605479
0.5176	Remote Similarity	NPC475273
0.5176	Remote Similarity	NPC168849
0.5176	Remote Similarity	NPC217901
0.5176	Remote Similarity	NPC611341
0.5169	Remote Similarity	NPC181924

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473548 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6869
0.1-0.2	2271
0.2-0.3	10
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