NPASS Compound

Natural Product: NPC87095

Natural Product ID	NPC87095
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ilekudinol B
IUPAC Name	(1S,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-1,2,6a,6b,12a-pentamethyl-9-methylidene-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms	ilekudinol B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL523827
PubChem CID	10647480
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 77 81 0 0 0 0 0 0 0 0999 V2000 -5.3209 2.3789 0.3744 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7946 1.1210 -0.3305 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3463 -0.0556 0.4405 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2317 -0.9999 0.7969 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3561 -1.2729 -0.4331 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4275 -2.3776 -0.0711 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2436 -1.9947 0.7244 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5930 -0.7034 0.3455 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5514 0.2536 1.5185 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2200 -0.0393 -0.8222 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4986 0.5539 -1.7681 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9777 0.6271 -1.7794 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4964 0.2496 -0.4122 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9723 0.3371 -0.2673 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7533 -0.7152 -0.9850 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4377 1.7009 -0.6659 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9516 1.8441 -0.4976 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3991 1.4912 0.8762 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6506 0.4049 1.5281 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2622 -0.3603 2.4154 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2260 0.1320 1.2291 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7873 -1.2197 1.6845 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5241 -1.7294 1.1484 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8791 -1.0355 0.0277 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7909 -1.9532 -1.1991 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7593 1.1809 0.8481 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2102 3.2203 -0.6965 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7062 -0.0349 -0.9389 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2865 1.1771 -0.1977 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8202 2.4542 -0.8227 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3084 -1.8293 -1.4631 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4381 -1.2097 -2.5486 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0247 -2.9779 -1.2453 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2823 2.1313 0.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6216 2.7017 1.1821 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5415 3.1856 -0.3207 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1430 1.1704 -1.3661 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1172 -0.5222 -0.1747 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8313 0.2463 1.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6528 -0.6812 1.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7187 -1.9917 1.0296 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0238 -3.1180 0.5419 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1960 -2.9438 -1.0126 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5657 -1.9213 1.8047 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5338 -2.8688 0.7222 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3702 0.1946 2.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7021 1.3047 1.2278 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3874 -0.0065 2.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0275 1.0184 -2.5918 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2190 1.7235 -1.9140 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4597 0.1111 -2.6058 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0812 1.0496 0.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5798 -1.7361 -0.5764 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6948 -0.6618 -2.0842 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8404 -0.5118 -0.7459 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9864 2.4726 -0.0094 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2379 1.8858 -1.7393 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5037 1.3306 -1.3113 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3143 2.4052 1.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3020 -0.1644 2.6379 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8024 -1.1735 2.9423 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6375 0.9045 1.7883 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7760 -1.1874 2.8127 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6443 -1.9218 1.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6676 -2.8198 0.8743 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7763 -1.8012 1.9968 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1608 -1.8869 -1.7149 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8874 -3.0053 -0.8207 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5928 -1.7998 -1.9115 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9214 0.3633 0.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4334 3.4022 -1.6434 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9818 0.1208 -2.0039 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0793 1.1172 0.8885 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7749 2.7161 -0.5665 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4700 3.2877 -0.4860 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9559 2.3647 -1.9199 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8712 -3.1025 -1.8175 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 1 1 8 10 1 0 10 11 2 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 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 18 26 1 0 17 27 1 0 10 28 1 0 28 29 1 0 29 30 1 0 5 31 1 6 31 32 2 0 31 33 1 0 29 2 1 0 28 5 1 0 24 8 1 0 24 13 1 0 21 14 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 6 42 1 0 6 43 1 0 7 44 1 0 7 45 1 0 9 46 1 0 9 47 1 0 9 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 1 15 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 6 18 59 1 1 20 60 1 0 20 61 1 0 21 62 1 1 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 25 67 1 0 25 68 1 0 25 69 1 0 26 70 1 0 27 71 1 0 28 72 1 6 29 73 1 1 30 74 1 0 30 75 1 0 30 76 1 0 33 77 1 0 M END

Standard InCHIKey	RDOIACMZJPLQIZ-FNVOJQHCSA-N
Standard InCHI	InChI=1S/C29H44O4/c1-16-9-12-29(25(32)33)14-13-27(5)20(23(29)17(16)2)7-8-22-26(4)15-21(30)24(31)18(3)19(26)10-11-28(22,27)6/h7,16-17,19,21-24,30-31H,3,8-15H2,1-2,4-6H3,(H,32,33)/t16-,17+,19+,21-,22-,23+,24-,26+,27-,28-,29+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(=C)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.32	Volume:	494.609 ? Van der Waals volume.
Dense:	0.923	LogP:	3.259 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.952 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.054 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	28.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.45	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.109	Fsp³:	0.828
MCE-18:	100.528 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.846	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.091 ? 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:	0.339	Promiscuous compounds:	0.067

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.458	MDCK Permeability:	-4.864
Pgp-inhibitor:	0.0	Pgp-substrate:	0.009
PAMPA:	0.997 ? 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):	0.002
20% Bioavailability (F20%):	0.784	30% Bioavailability (F30%):	0.524
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.629	MRP1:	0.581
Plasma Protein Binding (PPB):	86.808%	Volume Distribution (VD):	-0.281
Fu:	12.771% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.976	BCRP inhibitor:	0.285
BSEP inhibitor:	0.731

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.962
HLM stability:	0.061 ? 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):

3.561

Half-life (T1/2):

1.583

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.077
Human Hepatotoxicity (H-HT):	0.701	Drug-induced Liver Injury (DILI):	0.627
AMES Toxicity:	0.225	Rat Oral Acute Toxicity:	0.229
Maximum Recommended Daily Dose:	0.458	Skin Sensitization:	0.636
Carcinogencity:	0.723	Eye Corrosion:	0.0
Eye Irritation:	0.272	Respiratory Toxicity:	0.798
Drug-induced Neurotoxicity:	0.042	Ototoxicity:	0.839
Hematotoxicity:	0.467	Drug-induced Nephrotoxicity:	0.787
Genotoxicity:	0.417	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.144	Hek293 Cytotoxicity:	0.221
BCF:	1.588 ? 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:	4.004 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.417 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.875 ? 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
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425145]
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479318]
NPO4734	Syzygium nervosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27797185]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4734	Syzygium nervosum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	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
IC50	4
Activity	2

Activity Type	# Activity
Individual protein	1
Cell line	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3065	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 1	Rattus norvegicus	IC50	=	44000.0	nM	PMID[10425145]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[27797185]
NPT465	Cell line	NCI-N87	Homo sapiens	IC50	=	9100.0	nM	PMID[27797185]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[27797185]
NPT20950	Cell line	Erythrocyte	n.a.	Activity	=	0.123	mg/ml	PMID[28094185]
NPT20950	Cell line	Erythrocyte	n.a.	Activity	=	0.586	mg/ml	PMID[28094185]

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 NPC87095 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	22507
0.1-0.2	23005
0.2-0.3	3559
0.3-0.4	523
0.4-0.5	167
0.5-0.6	59
0.6-0.7	13
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
0.7424	Intermediate Similarity	NPC71074
0.7424	Intermediate Similarity	NPC605937
0.7313	Intermediate Similarity	NPC32407
0.7313	Intermediate Similarity	NPC263548
0.7313	Intermediate Similarity	NPC606320
0.7121	Intermediate Similarity	NPC477289
0.7015	Intermediate Similarity	NPC51700
0.7015	Intermediate Similarity	NPC88716
0.7015	Intermediate Similarity	NPC68160
0.6812	Remote Similarity	NPC305464
0.6812	Remote Similarity	NPC19376
0.6812	Remote Similarity	NPC25848
0.6667	Remote Similarity	NPC61543
0.6667	Remote Similarity	NPC293048
0.6667	Remote Similarity	NPC225585
0.6571	Remote Similarity	NPC173089
0.6486	Remote Similarity	NPC230151
0.6338	Remote Similarity	NPC477288
0.6232	Remote Similarity	NPC274050
0.6232	Remote Similarity	NPC162632
0.6197	Remote Similarity	NPC37221
0.6027	Remote Similarity	NPC485589
0.5946	Remote Similarity	NPC25299
0.5946	Remote Similarity	NPC481322
0.5915	Remote Similarity	NPC274330
0.5867	Remote Similarity	NPC20235
0.5867	Remote Similarity	NPC299996
0.5753	Remote Similarity	NPC300351
0.5733	Remote Similarity	NPC477290
0.5732	Remote Similarity	NPC57362
0.5714	Remote Similarity	NPC485586
0.5714	Remote Similarity	NPC485588
0.5676	Remote Similarity	NPC40092
0.5663	Remote Similarity	NPC177246
0.5616	Remote Similarity	NPC84319
0.5616	Remote Similarity	NPC52021
0.5616	Remote Similarity	NPC599947
0.5541	Remote Similarity	NPC106112
0.5541	Remote Similarity	NPC261935
0.5541	Remote Similarity	NPC231063
0.5541	Remote Similarity	NPC282395
0.5541	Remote Similarity	NPC88116
0.5541	Remote Similarity	NPC481360
0.5541	Remote Similarity	NPC110308
0.5495	Remote Similarity	NPC479747
0.5495	Remote Similarity	NPC479746
0.5467	Remote Similarity	NPC259733
0.5467	Remote Similarity	NPC158371
0.5467	Remote Similarity	NPC207922
0.5467	Remote Similarity	NPC293564
0.5455	Remote Similarity	NPC117663
0.5405	Remote Similarity	NPC195019
0.5395	Remote Similarity	NPC35239
0.5395	Remote Similarity	NPC247139
0.5385	Remote Similarity	NPC479743
0.5366	Remote Similarity	NPC485585
0.5333	Remote Similarity	NPC173744
0.5333	Remote Similarity	NPC204961
0.5333	Remote Similarity	NPC472149
0.5333	Remote Similarity	NPC73004
0.5333	Remote Similarity	NPC111214
0.5333	Remote Similarity	NPC609452
0.5325	Remote Similarity	NPC127689
0.527	Remote Similarity	NPC480946
0.527	Remote Similarity	NPC130577
0.527	Remote Similarity	NPC142415
0.527	Remote Similarity	NPC102683
0.5263	Remote Similarity	NPC202728
0.5263	Remote Similarity	NPC158059
0.5217	Remote Similarity	NPC304110
0.5217	Remote Similarity	NPC27518
0.5217	Remote Similarity	NPC611516
0.52	Remote Similarity	NPC479079
0.5195	Remote Similarity	NPC610635
0.5176	Remote Similarity	NPC485882
0.5161	Remote Similarity	NPC178093
0.5109	Remote Similarity	NPC479744
0.5067	Remote Similarity	NPC187722
0.5065	Remote Similarity	NPC136697
0.5063	Remote Similarity	NPC157113
0.5053	Remote Similarity	NPC479745

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC87095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6500
0.1-0.2	2589
0.2-0.3	57
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