NPASS Compound

Natural Product: NPC168849

Natural Product ID	NPC168849
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Montanin
IUPAC Name	n.a.
Synonyms	NSC-282158
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL451572
PubChem CID	21575656
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 3D 88 93 0 0 0 0 0 0 0 0999 V2000 8.6401 -2.5167 -0.6712 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1486 -1.6717 0.4861 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4105 -0.4762 -0.0504 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8892 0.4259 1.0246 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9274 -0.2507 1.9509 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7527 -0.7567 1.1833 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0173 0.3423 0.4740 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5061 1.3556 1.4538 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7779 2.4422 0.7077 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6311 1.8688 -0.0525 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6107 1.1741 0.7840 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4820 0.6623 -0.1473 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0215 1.7437 -0.7875 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8747 1.0755 -1.7062 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0591 -0.0947 -2.0717 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0858 -0.0248 -1.2460 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6501 -1.4295 -1.8815 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6624 -1.5496 -0.7557 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5990 -0.3301 0.1073 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2823 -0.1742 0.5090 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0794 0.7627 -0.7957 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5507 2.0275 -0.2430 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5016 2.4461 1.0502 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7352 2.1146 0.5563 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5069 0.9231 0.9295 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8442 -0.3285 1.2546 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3882 -0.3802 1.3738 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1292 -1.5514 2.2381 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2115 -1.8218 2.9450 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2683 -0.8579 2.6080 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2928 -0.5182 3.2477 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4190 -2.9035 3.9456 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2644 -1.3340 0.3717 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4828 0.7249 -0.0828 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6316 3.3656 0.4246 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0048 4.2708 -0.4564 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4826 -2.8749 -0.1454 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6240 0.0476 -3.4894 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6727 0.0808 -3.7597 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6403 0.1497 -4.5850 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4010 -3.5728 -0.4895 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7572 -2.4284 -0.7536 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1588 -2.1881 -1.6109 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0048 -1.2914 1.0933 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5334 -2.2953 1.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5403 -0.8080 -0.6669 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0451 0.1406 -0.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4180 1.3029 0.5121 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7543 0.8118 1.6312 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6350 0.4157 2.7767 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4416 -1.1418 2.3789 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0314 -1.5684 0.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0233 -1.2356 1.8873 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1772 -0.1688 -0.0734 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6253 0.8237 -0.3210 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7838 0.8780 2.1489 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3538 1.7846 2.0480 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5079 2.9146 -0.0014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4602 3.2723 1.3960 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0919 2.7381 -0.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9409 1.1854 -0.8684 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1087 1.9469 1.4252 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9718 0.4010 1.4577 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1705 1.7402 -2.5308 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8008 -2.1612 -1.7247 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0827 -1.7634 -2.8714 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6606 -1.5528 -1.2889 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8587 0.3940 -1.5225 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3951 2.9097 -0.9507 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1482 1.2263 1.8167 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9770 0.4469 2.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2291 -2.1224 2.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9357 -3.8184 3.5059 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8437 -2.6778 4.8683 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4728 -3.0929 4.1301 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1950 -1.1747 0.1160 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1380 0.8959 -0.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5811 3.8473 1.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6414 3.1090 0.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6450 4.8923 -0.8573 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4472 -3.0255 0.2613 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4829 -3.6037 -1.0208 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2831 -3.2589 0.4928 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4278 0.0083 -2.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9941 0.1846 -4.7923 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4139 0.9031 -4.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1168 0.4850 -5.5041 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0499 -0.8664 -4.7861 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 0 9 10 1 0 10 11 1 0 12 11 1 1 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 19 21 1 0 21 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 2 0 29 30 1 0 30 31 2 0 29 32 1 0 26 33 1 6 25 34 1 0 24 35 1 6 35 36 1 0 18 37 1 0 15 38 1 6 38 39 2 0 38 40 1 0 16 12 1 0 27 19 1 0 20 12 1 0 24 22 1 0 30 26 1 0 21 14 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 2 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 5 50 1 0 5 51 1 0 6 52 1 0 6 53 1 0 7 54 1 0 7 55 1 0 8 56 1 0 8 57 1 0 9 58 1 0 9 59 1 0 10 60 1 0 10 61 1 0 11 62 1 0 11 63 1 0 14 64 1 6 17 65 1 0 17 66 1 0 18 67 1 6 21 68 1 6 22 69 1 6 25 70 1 1 27 71 1 1 28 72 1 0 32 73 1 0 32 74 1 0 32 75 1 0 33 76 1 0 34 77 1 0 35 78 1 0 35 79 1 0 36 80 1 0 37 81 1 0 37 82 1 0 37 83 1 0 39 84 1 0 39 85 1 0 40 86 1 0 40 87 1 0 40 88 1 0 M END

Standard InCHIKey	SNFRINMTRPQQLE-KPYDUSLXSA-N
Standard InCHI	InChI=1S/C32H48O8/c1-6-7-8-9-10-11-12-13-14-15-30-38-25-23-26-29(18-33,37-26)27(35)31(36)22(16-20(4)24(31)34)32(23,40-30)21(5)17-28(25,39-30)19(2)3/h16,21-23,25-27,33,35-36H,2,6-15,17-18H2,1,3-5H3/t21-,22-,23-,25-,26+,27-,28-,29+,30-,31-,32+/m1/s1
SMILES	CCCCCCCCCCC[C@@]12O[C@H]3[C@@](O1)(C[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)C(=C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	560.33	Volume:	573.102 ? Van der Waals volume.
Dense:	0.978	LogP:	5.013 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.114 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.596 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	26.0
TPSA:	117.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.186	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.423	Fsp³:	0.844
MCE-18:	101.085 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.427	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.145	Promiscuous compounds:	0.215

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.031	MDCK Permeability:	-4.634
Pgp-inhibitor:	0.0	Pgp-substrate:	0.008
PAMPA:	0.043 ? 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):	0.044
20% Bioavailability (F20%):	0.866	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.843	MRP1:	0.999
Plasma Protein Binding (PPB):	97.327%	Volume Distribution (VD):	0.739
Fu:	3.465% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.028
BSEP inhibitor:	0.876

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.831
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.026
CYP2C9-inhibitor:	0.956	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.812	CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	0.999
HLM stability:	0.098 ? 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):

5.703

Half-life (T1/2):

0.81

ADMET: Toxicity

hERG Blockers:	0.189	hERG Blockers (10um):	0.805
Human Hepatotoxicity (H-HT):	0.181	Drug-induced Liver Injury (DILI):	0.747
AMES Toxicity:	0.85	Rat Oral Acute Toxicity:	0.661
Maximum Recommended Daily Dose:	0.163	Skin Sensitization:	1.0
Carcinogencity:	0.508	Eye Corrosion:	0.076
Eye Irritation:	0.889	Respiratory Toxicity:	0.32
Drug-induced Neurotoxicity:	0.198	Ototoxicity:	0.729
Hematotoxicity:	0.37	Drug-induced Nephrotoxicity:	0.185
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.212
A549 Cytotoxicity:	0.884	Hek293 Cytotoxicity:	0.893
BCF:	2.287 ? 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:	5.462 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.442 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.322 ? 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
NPO32485	cunuria spruceana	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[541688]

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
ED50	1

Activity Type	# Activity
Cell line	1

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
NPT168	Cell line	P388	Mus musculus	ED50	=	0.06	ug ml-1	PMID[26123643]

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 NPC168849 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	15833
0.1-0.2	32472
0.2-0.3	1438
0.3-0.4	30
0.4-0.5	38
0.5-0.6	29
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475273
1.0	High Similarity	NPC217901
1.0	High Similarity	NPC611341
0.726	Intermediate Similarity	NPC162495
0.6974	Remote Similarity	NPC474508
0.6974	Remote Similarity	NPC473485
0.6974	Remote Similarity	NPC171411
0.6974	Remote Similarity	NPC485701
0.6842	Remote Similarity	NPC251564
0.6842	Remote Similarity	NPC477189
0.6486	Remote Similarity	NPC608985
0.6463	Remote Similarity	NPC605479
0.64	Remote Similarity	NPC605473
0.64	Remote Similarity	NPC610597
0.6316	Remote Similarity	NPC142882
0.6316	Remote Similarity	NPC608716
0.6316	Remote Similarity	NPC609033
0.6136	Remote Similarity	NPC486154
0.5663	Remote Similarity	NPC180902
0.5581	Remote Similarity	NPC475139
0.5529	Remote Similarity	NPC182266
0.5529	Remote Similarity	NPC475154
0.5529	Remote Similarity	NPC485700
0.5476	Remote Similarity	NPC485693
0.5432	Remote Similarity	NPC329008
0.5432	Remote Similarity	NPC317635
0.5432	Remote Similarity	NPC146310
0.5432	Remote Similarity	NPC485696
0.5412	Remote Similarity	NPC223356
0.5412	Remote Similarity	NPC298697
0.5412	Remote Similarity	NPC475500
0.5412	Remote Similarity	NPC100017
0.5412	Remote Similarity	NPC481742
0.5357	Remote Similarity	NPC475314
0.5357	Remote Similarity	NPC102997
0.5349	Remote Similarity	NPC75831
0.5349	Remote Similarity	NPC471137
0.5287	Remote Similarity	NPC471136
0.5287	Remote Similarity	NPC116727
0.5287	Remote Similarity	NPC39509
0.5227	Remote Similarity	NPC481744
0.5227	Remote Similarity	NPC481743
0.5176	Remote Similarity	NPC324104
0.5176	Remote Similarity	NPC473548
0.5119	Remote Similarity	NPC475606
0.5111	Remote Similarity	NPC475548
0.5111	Remote Similarity	NPC485698

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC168849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6253
0.1-0.2	2869
0.2-0.3	27
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