NPASS Compound

Natural Product: NPC234637

Natural Product ID	NPC234637
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Clusianone
IUPAC Name	n.a.
Synonyms	Clusianone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL459015
PubChem CID	NA
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

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 81 0 0 0 0 0 0 0 0999 V2000 -0.3413 5.2981 0.4748 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8072 4.4799 1.6383 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2300 3.3322 1.9639 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8964 2.8504 1.1620 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6982 1.5076 0.5340 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4786 1.4392 -0.4102 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4239 0.3801 0.0950 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8252 0.5711 -0.3704 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0671 0.5812 -1.7953 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9618 -0.1864 -2.3784 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8512 -1.1629 -1.7071 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1603 -0.1230 -3.8891 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8195 -0.9655 0.0424 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4248 -0.9240 0.9141 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6097 0.4120 1.5539 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6849 0.6420 2.7210 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6933 -1.0795 0.1010 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3337 -2.1498 0.2022 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1671 -0.0164 -0.7723 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9417 1.2368 -0.2917 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8579 2.2272 -0.5756 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9021 -0.1479 -2.0065 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3472 1.0130 -2.4719 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2512 -1.2409 -2.8239 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7434 -2.4956 -2.7355 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1913 -3.5532 -3.5245 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1819 -3.3590 -4.4411 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7261 -2.1117 -4.5718 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2701 -1.0742 -3.7794 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3559 -2.0216 1.9534 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5265 -2.0069 2.8551 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3052 -1.9302 4.1609 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0477 -1.8602 4.7714 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4774 -1.9094 5.0735 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5798 -1.5426 -1.3120 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8627 -1.9122 0.6918 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9571 5.0106 2.4243 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8931 6.2545 0.4051 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5089 4.7052 -0.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7338 5.5592 0.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6243 2.7976 2.8207 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1356 3.5618 0.3551 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8078 2.7739 1.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0641 2.3852 -0.4399 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1463 1.2676 -1.4478 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4845 0.6135 1.2168 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1225 1.5960 0.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4629 -0.1113 0.2278 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4830 1.2521 -2.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8086 -1.3174 -2.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3606 -2.1582 -1.7347 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0825 -0.9179 -0.6505 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2221 -0.0529 -4.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8059 -1.1094 -4.2492 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5734 0.7139 -4.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6544 2.9099 -1.2963 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9263 -2.7485 -2.0805 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7396 -4.5116 -3.3898 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5329 -4.1910 -5.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5103 -1.9757 -5.3024 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7577 -0.1260 -3.9508 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5504 -1.8880 2.5308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4209 -2.9924 1.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5593 -2.0569 2.4844 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6899 -2.7069 4.4491 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5879 -0.9302 4.5213 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0032 -1.8917 5.8787 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6728 -0.8700 5.4417 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3291 -2.5214 5.9798 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3685 -2.3415 4.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5310 -1.6087 -1.9103 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1485 -1.0365 -1.9385 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2608 -2.6246 -1.2526 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6730 -1.9744 -0.0609 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4860 -2.9263 0.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3054 -1.4528 1.5852 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1201 6.0768 2.2080 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8477 4.4270 2.1088 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7722 4.9397 3.5205 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 5 4 1 1 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 3 10 11 1 0 10 12 1 0 7 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 14 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 19 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 14 30 1 1 30 31 1 0 31 32 2 3 32 33 1 0 32 34 1 0 13 35 1 0 13 36 1 0 2 37 1 0 20 5 1 0 29 24 1 0 15 5 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 6 44 1 0 6 45 1 0 7 46 1 1 8 47 1 0 8 48 1 0 9 49 1 0 11 50 1 0 11 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 12 55 1 0 21 56 1 0 25 57 1 0 26 58 1 0 27 59 1 0 28 60 1 0 29 61 1 0 30 62 1 0 30 63 1 0 31 64 1 0 33 65 1 0 33 66 1 0 33 67 1 0 34 68 1 0 34 69 1 0 34 70 1 0 35 71 1 0 35 72 1 0 35 73 1 0 36 74 1 0 36 75 1 0 36 76 1 0 37 77 1 0 37 78 1 0 37 79 1 0 M END

Standard InCHIKey	JXKKYQPCNJMAHZ-BJEYHHSBSA-N
Standard InCHI	InChI=1S/C33H42O4/c1-21(2)14-15-25-20-32(18-16-22(3)4)28(35)26(27(34)24-12-10-9-11-13-24)29(36)33(30(32)37,31(25,7)8)19-17-23(5)6/h9-14,16-17,25,35H,15,18-20H2,1-8H3/t25-,32-,33+/m1/s1
SMILES	CC(=CC[C@@]12C[C@@H](CC=C(C)C)C([C@](C2=O)(C(=O)C(=C1O)C(=O)c1ccccc1)CC=C(C)C)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	502.31	Volume:	562.451 ? Van der Waals volume.
Dense:	0.893	LogP:	6.648 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.984 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.178 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	22.0
TPSA:	71.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.17	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.052	Fsp³:	0.485
MCE-18:	89.714 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.937	Fluc inhibitor:	0.079 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.181 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.488 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.608	Promiscuous compounds:	0.051

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.71	MDCK Permeability:	-4.681
Pgp-inhibitor:	0.036	Pgp-substrate:	0.09
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):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.175

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.347	MRP1:	0.79
Plasma Protein Binding (PPB):	88.804%	Volume Distribution (VD):	0.213
Fu:	11.218% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.894
OATP1B3 inhibitor:	0.03	BCRP inhibitor:	0.003
BSEP inhibitor:	0.018

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.99	CYP2C19-substrate:	0.028
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.314	CYP3A4-substrate:	0.107
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.932
HLM stability:	1.0 ? 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):

4.491

Half-life (T1/2):

0.937

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.189
Human Hepatotoxicity (H-HT):	0.789	Drug-induced Liver Injury (DILI):	0.58
AMES Toxicity:	0.396	Rat Oral Acute Toxicity:	0.869
Maximum Recommended Daily Dose:	0.169	Skin Sensitization:	0.93
Carcinogencity:	0.501	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.907
Drug-induced Neurotoxicity:	0.404	Ototoxicity:	0.803
Hematotoxicity:	0.684	Drug-induced Nephrotoxicity:	0.991
Genotoxicity:	0.993	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.4	Hek293 Cytotoxicity:	0.222
BCF:	1.964 ? 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:	5.301 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.208 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.106 ? 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
NPO33514	garcinia assigu	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608850]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	seeds and rinds	n.a.	n.a.	PMID[21028890]

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	8
IC50	1
MIC	2

Activity Type	# Activity
Cell line	4
Others	5
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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[12608850]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[12608850]
NPT1	Others	Radical scavenging activity	n.a.	IC50	>	100000.0	nM	PMID[12608850]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[32791400]
NPT2	Others	Unspecified	n.a.	Activity	=	17.4	%	PMID[12608850]
NPT2	Others	Unspecified	n.a.	Activity	=	53.7	%	PMID[12608850]
NPT2	Others	Unspecified	n.a.	Activity	=	87.7	%	PMID[12608850]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[12608850]

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 NPC234637 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	7624
0.1-0.2	40138
0.2-0.3	1923
0.3-0.4	76
0.4-0.5	43
0.5-0.6	20
0.6-0.7	30
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259400
1.0	High Similarity	NPC130591
0.8929	High Similarity	NPC611064
0.7705	Intermediate Similarity	NPC149773
0.6818	Remote Similarity	NPC600618
0.6812	Remote Similarity	NPC165191
0.6812	Remote Similarity	NPC30846
0.6812	Remote Similarity	NPC177501
0.6774	Remote Similarity	NPC471481
0.6774	Remote Similarity	NPC610194
0.6667	Remote Similarity	NPC114333
0.6667	Remote Similarity	NPC28592
0.6667	Remote Similarity	NPC51531
0.662	Remote Similarity	NPC603871
0.6618	Remote Similarity	NPC46242
0.6618	Remote Similarity	NPC479147
0.6618	Remote Similarity	NPC91887
0.6618	Remote Similarity	NPC93556
0.6571	Remote Similarity	NPC473479
0.6571	Remote Similarity	NPC50615
0.6571	Remote Similarity	NPC141650
0.6522	Remote Similarity	NPC297797
0.6522	Remote Similarity	NPC198803
0.6338	Remote Similarity	NPC469857
0.6338	Remote Similarity	NPC245760
0.6301	Remote Similarity	NPC237441
0.6232	Remote Similarity	NPC289358
0.6232	Remote Similarity	NPC4289
0.6232	Remote Similarity	NPC42384
0.6212	Remote Similarity	NPC218855
0.6164	Remote Similarity	NPC471971
0.6164	Remote Similarity	NPC471972
0.6164	Remote Similarity	NPC469855
0.614	Remote Similarity	NPC602123
0.5932	Remote Similarity	NPC600619
0.5867	Remote Similarity	NPC25736
0.5733	Remote Similarity	NPC5014
0.5658	Remote Similarity	NPC469856
0.56	Remote Similarity	NPC23667
0.56	Remote Similarity	NPC157284
0.56	Remote Similarity	NPC294330
0.5584	Remote Similarity	NPC471970
0.5526	Remote Similarity	NPC469854
0.541	Remote Similarity	NPC605738
0.5405	Remote Similarity	NPC48949
0.5263	Remote Similarity	NPC479148
0.525	Remote Similarity	NPC482618
0.5205	Remote Similarity	NPC483069
0.5205	Remote Similarity	NPC268930
0.5195	Remote Similarity	NPC482621
0.5195	Remote Similarity	NPC479151
0.5185	Remote Similarity	NPC482617
0.5185	Remote Similarity	NPC482616
0.5139	Remote Similarity	NPC608846

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC234637 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2580
0.1-0.2	6405
0.2-0.3	164
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