NPASS Compound

Natural Product: NPC483878

Natural Product ID	NPC483878
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UCMCNBKFGRBCRY-JHAMKKRDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44361722
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 -3.9834 2.9905 1.1725 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7373 1.5494 1.4452 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9669 1.0917 2.6181 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2726 0.6658 0.5074 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0353 -0.7321 0.7774 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9020 -1.6035 -0.0191 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3231 -2.2775 -1.2034 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7198 -1.6656 -2.5324 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8302 -2.4338 -1.1794 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5129 -3.6961 -0.4346 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1136 -3.9685 -1.0102 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7754 -2.9624 -0.3832 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3884 -1.5597 -0.6961 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0958 -1.2703 -0.6059 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2750 -0.0080 -1.4321 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5656 -0.9607 0.7643 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9799 0.2667 1.2374 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2347 0.3641 2.3885 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0662 -0.6912 3.0486 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3571 1.5922 2.8756 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1008 1.5945 4.0279 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6756 2.7758 4.5114 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4978 3.9598 3.8277 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7462 3.9628 2.6613 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1825 2.7732 2.1980 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1624 -0.6374 0.0333 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0427 0.2701 -0.5637 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0962 0.2011 -1.8162 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8430 1.2253 0.1842 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6418 2.0316 -0.4943 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4975 3.0329 0.0989 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2747 3.8246 -0.7145 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1268 4.8040 -0.2026 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1742 4.9642 1.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 4.1929 2.0026 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5802 3.2314 1.4448 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4541 -3.6773 -2.4651 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2206 -4.8808 -2.9859 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7664 -3.4988 -3.3109 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3174 -2.6139 -2.4709 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8534 -3.5956 -1.2236 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5568 3.6202 1.9909 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0676 3.1988 1.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4610 3.2810 0.2541 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3246 -0.8209 1.8722 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4436 -2.3251 0.6650 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7542 -0.9660 -0.4122 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3294 -0.7444 -2.4181 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3542 -2.3521 -3.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8164 -1.4828 -3.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5243 -3.6261 0.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2142 -4.4837 -0.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1984 -5.0006 -0.8554 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8397 -3.0787 -0.6229 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6789 -3.0869 0.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6439 -1.3945 -1.7797 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3164 0.2621 -1.5943 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7473 0.8194 -0.9240 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7982 -0.1153 -2.4307 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2899 -1.7113 1.5241 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2406 0.6703 4.5642 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2674 2.7992 5.4149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9257 4.8867 4.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6107 4.8835 2.1344 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3977 2.8109 1.2841 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8244 1.3135 1.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6670 1.9451 -1.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2410 3.7022 -1.7825 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7060 5.3886 -0.8931 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8380 5.7255 1.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4785 4.3482 3.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0022 2.6491 2.1494 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4076 -5.6348 -2.2234 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2114 -4.5913 -3.4020 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6735 -5.3735 -3.8208 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6675 -2.7127 -4.0801 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6903 -3.3593 -2.6758 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9811 -4.4471 -3.8852 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6957 -3.6283 -0.7060 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 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 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 13 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 11 37 1 0 37 38 1 0 37 39 1 0 37 40 1 0 7 41 1 6 16 5 1 0 25 20 1 0 36 31 1 0 14 9 1 0 40 9 1 0 1 42 1 0 1 43 1 0 1 44 1 0 5 45 1 1 6 46 1 0 6 47 1 0 8 48 1 0 8 49 1 0 8 50 1 0 10 51 1 0 10 52 1 0 11 53 1 0 12 54 1 0 12 55 1 0 13 56 1 6 15 57 1 0 15 58 1 0 15 59 1 0 16 60 1 1 21 61 1 0 22 62 1 0 23 63 1 0 24 64 1 0 25 65 1 0 29 66 1 0 30 67 1 0 32 68 1 0 33 69 1 0 34 70 1 0 35 71 1 0 36 72 1 0 38 73 1 0 38 74 1 0 38 75 1 0 39 76 1 0 39 77 1 0 39 78 1 0 41 79 1 0 M END

Standard InCHIKey	UCMCNBKFGRBCRY-JHAMKKRDSA-N
Standard InCHI	InChI=1S/C33H38O8/c1-21(34)38-25-20-31(4,37)33-19-24(30(2,3)41-33)18-26(39-27(35)17-16-22-12-8-6-9-13-22)32(33,5)28(25)40-29(36)23-14-10-7-11-15-23/h6-17,24-26,28,37H,18-20H2,1-5H3/b17-16+/t24?,25-,26-,28-,31-,32+,33?/m0/s1
SMILES	CC(=O)O[C@H]1C[C@@](C)(C23CC(C[C@@H]([C@]2(C)[C@H]1OC(=O)c1ccccc1)OC(=O)/C=C/c1ccccc1)C(C)(C)O3)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	562.26	Volume:	580.499 ? Van der Waals volume.
Dense:	0.969	LogP:	4.433 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.723 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.767 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	108.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.301	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.681	Fsp³:	0.485
MCE-18:	160.163 ? 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:	0.815	Fluc inhibitor:	0.853 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.559 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.173	Promiscuous compounds:	0.178

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.109	MDCK Permeability:	-4.711
Pgp-inhibitor:	0.994	Pgp-substrate:	0.008
PAMPA:	0.454 ? 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):	0.0
20% Bioavailability (F20%):	0.188	30% Bioavailability (F30%):	0.663
50% Bioavailability (F50%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177	MRP1:	0.945
Plasma Protein Binding (PPB):	92.024%	Volume Distribution (VD):	-0.179
Fu:	10.244% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.015
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.993
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.43 ? 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):

6.23

Half-life (T1/2):

0.689

ADMET: Toxicity

hERG Blockers:	0.195	hERG Blockers (10um):	0.618
Human Hepatotoxicity (H-HT):	0.378	Drug-induced Liver Injury (DILI):	0.534
AMES Toxicity:	0.351	Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.719	Skin Sensitization:	0.984
Carcinogencity:	0.329	Eye Corrosion:	0.0
Eye Irritation:	0.199	Respiratory Toxicity:	0.119
Drug-induced Neurotoxicity:	0.674	Ototoxicity:	0.315
Hematotoxicity:	0.033	Drug-induced Nephrotoxicity:	0.397
Genotoxicity:	0.23	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.339	Hek293 Cytotoxicity:	0.607
BCF:	0.921 ? 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:	3.884 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.476 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.036 ? 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
NPO3859	Maytenus magellanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11741484]
NPO10966	Maytenus chubutensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11741484]
NPO10966	Maytenus chubutensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3859	Maytenus magellanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10966	Maytenus chubutensis	Species	Celastraceae	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
Inhibition	6

Activity Type	# Activity
Others	6

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
NPT2	Others	Unspecified	n.a.	Inhibition	=	7.5	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	94.3	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	7.3	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	92.8	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	0.0	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	88.2	%	PMID[11741484]

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 NPC483878 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	10125
0.1-0.2	35781
0.2-0.3	3217
0.3-0.4	580
0.4-0.5	104
0.5-0.6	38
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8077	Intermediate Similarity	NPC86800
0.7826	Intermediate Similarity	NPC483879
0.7763	Intermediate Similarity	NPC25768
0.7439	Intermediate Similarity	NPC483873
0.7	Intermediate Similarity	NPC469349
0.6711	Remote Similarity	NPC473889
0.6667	Remote Similarity	NPC214550
0.6341	Remote Similarity	NPC472571
0.631	Remote Similarity	NPC483874
0.6222	Remote Similarity	NPC483891
0.6118	Remote Similarity	NPC184817
0.6	Remote Similarity	NPC174982
0.6	Remote Similarity	NPC483865
0.5974	Remote Similarity	NPC37641
0.5952	Remote Similarity	NPC483867
0.593	Remote Similarity	NPC188865
0.5882	Remote Similarity	NPC473109
0.5783	Remote Similarity	NPC473085
0.5769	Remote Similarity	NPC114927
0.5747	Remote Similarity	NPC171525
0.5698	Remote Similarity	NPC483866
0.5647	Remote Similarity	NPC488912
0.5647	Remote Similarity	NPC488910
0.5632	Remote Similarity	NPC483861
0.5595	Remote Similarity	NPC607428
0.5517	Remote Similarity	NPC70403
0.5517	Remote Similarity	NPC177940
0.5455	Remote Similarity	NPC125106
0.5455	Remote Similarity	NPC472573
0.5455	Remote Similarity	NPC481066
0.5443	Remote Similarity	NPC84129
0.5412	Remote Similarity	NPC473112
0.5402	Remote Similarity	NPC470159
0.5402	Remote Similarity	NPC488919
0.5361	Remote Similarity	NPC483880
0.5361	Remote Similarity	NPC156941
0.5349	Remote Similarity	NPC609221
0.5341	Remote Similarity	NPC605086
0.5294	Remote Similarity	NPC473082
0.5287	Remote Similarity	NPC29704
0.5287	Remote Similarity	NPC470157
0.5244	Remote Similarity	NPC475933
0.5172	Remote Similarity	NPC481050
0.5122	Remote Similarity	NPC70973
0.5122	Remote Similarity	NPC281717
0.5116	Remote Similarity	NPC210591
0.506	Remote Similarity	NPC472576
0.5059	Remote Similarity	NPC473110
0.5056	Remote Similarity	NPC603877
0.5055	Remote Similarity	NPC488916
0.5054	Remote Similarity	NPC473214

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483878 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3981
0.1-0.2	5031
0.2-0.3	137
0.3-0.4	1
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