NPASS Compound

Natural Product: NPC275740

Natural Product ID	NPC275740
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Tirucalla-8,24-Diene-3Beta-Ol-7-One
IUPAC Name	(3S,5R,10S,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-17-[(2S)-6-methylhept-5-en-2-yl]-1,2,3,5,6,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-7-one
Synonyms	epi-kansenone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL513851
PubChem CID	21629616
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 80 83 0 0 0 0 0 0 0 0999 V2000 8.1206 -0.2975 0.5622 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8551 -1.0286 0.3226 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6902 -0.4088 0.3519 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4255 -1.1148 0.1172 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6210 -0.7187 -1.0494 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1054 0.6314 -1.2210 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2318 1.6439 -1.2800 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0372 1.1944 -0.4194 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1479 1.3389 1.0448 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7277 1.7809 1.4515 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0738 1.7391 0.1836 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0471 3.0567 -0.5518 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4573 1.3148 0.3334 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0486 0.7872 -0.7523 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3756 0.6249 -2.0399 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1189 0.5469 -1.9451 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6570 0.6287 -0.5709 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4193 -0.6304 0.2023 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4712 0.3906 -0.5255 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2431 1.6851 -0.2252 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1480 -0.2374 -1.6745 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1931 -1.7312 -1.6578 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6477 -2.3158 -0.3528 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5941 -1.4169 0.8242 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3059 -2.3070 2.0488 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9168 -0.7671 1.1335 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4514 -0.4811 0.7206 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2135 0.3693 1.9481 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2156 1.4225 1.5831 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9761 2.4249 2.2991 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9605 -2.8271 -0.4483 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9066 -2.4934 0.0435 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6588 -0.6395 1.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8866 0.7786 0.7336 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7990 -0.3227 -0.3293 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7122 0.6474 0.5720 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7222 -2.2070 -0.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8969 -1.1798 1.0868 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8502 -1.5324 -1.2430 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3206 -0.9191 -1.9359 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6849 0.6590 -2.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1762 1.2398 -1.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9295 2.4086 -2.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2910 2.2517 -0.3543 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9221 2.2673 -0.8007 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3543 0.4712 1.6496 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8822 2.1276 1.3223 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7947 2.8572 1.7541 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2968 1.1508 2.2297 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0760 2.9932 -1.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7093 3.7648 -0.1515 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0418 3.5645 -0.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6589 1.4591 -2.7114 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7356 -0.3096 -2.5143 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4712 -0.4398 -2.3709 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6132 1.2986 -2.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1313 -1.3543 -0.4683 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3454 -1.0849 0.6052 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2561 -0.4966 1.0738 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5425 2.5403 -0.1561 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7953 1.6277 0.7177 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9350 1.9507 -1.0606 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6854 0.0958 -2.6217 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2232 0.1075 -1.7750 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2163 -2.1466 -1.9963 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9325 -2.0494 -2.4320 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0065 -3.2016 -0.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1530 -1.7014 2.9481 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5358 -3.0492 1.8382 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2702 -2.8648 2.2099 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6369 -1.6177 1.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3622 -0.2068 0.2946 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8757 -0.2031 2.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5267 -1.1230 0.6145 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1120 0.7559 2.4231 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6916 -0.2890 2.6995 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5688 -2.1907 -0.8714 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9527 -2.8605 0.0167 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3458 -3.0878 0.7979 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4769 -2.7443 -0.9552 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 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 14 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 24 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 23 31 1 0 2 32 1 0 17 8 1 0 27 19 1 0 17 11 1 0 29 13 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 6 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 6 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 18 57 1 0 18 58 1 0 18 59 1 0 20 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 23 67 1 1 25 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 26 72 1 0 26 73 1 0 27 74 1 6 28 75 1 0 28 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 32 80 1 0 M END

Standard InCHIKey	TVMGQCAMNPECHD-VGYIVZNUSA-N
Standard InCHI	InChI=1S/C30H48O2/c1-19(2)10-9-11-20(3)21-12-17-30(8)26-22(13-16-29(21,30)7)28(6)15-14-25(32)27(4,5)24(28)18-23(26)31/h10,20-21,24-25,32H,9,11-18H2,1-8H3/t20-,21-,24-,25-,28+,29-,30+/m0/s1
SMILES	CC(=CCC[C@H](C)[C@@H]1CC[C@]2(C)C3=C(CC[C@@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.37	Volume:	502.881 ? Van der Waals volume.
Dense:	0.876	LogP:	5.931 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.49 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.65 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	22.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.456	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.683	Fsp³:	0.833
MCE-18:	80.291 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.812	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.058 ? 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:	0.562	Promiscuous compounds:	0.362

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.621	MDCK Permeability:	-4.799
Pgp-inhibitor:	0.986	Pgp-substrate:	0.077
PAMPA:	0.526 ? 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):	0.001
20% Bioavailability (F20%):	0.602	30% Bioavailability (F30%):	0.142
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.797	MRP1:	0.993
Plasma Protein Binding (PPB):	96.122%	Volume Distribution (VD):	0.113
Fu:	3.864% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.482
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.823	CYP1A2-substrate:	0.308
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.899	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.937
HLM stability:	0.314 ? 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):

10.121

Half-life (T1/2):

0.294

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.208
Human Hepatotoxicity (H-HT):	0.657	Drug-induced Liver Injury (DILI):	0.148
AMES Toxicity:	0.455	Rat Oral Acute Toxicity:	0.26
Maximum Recommended Daily Dose:	0.474	Skin Sensitization:	0.992
Carcinogencity:	0.848	Eye Corrosion:	0.22
Eye Irritation:	0.919	Respiratory Toxicity:	0.854
Drug-induced Neurotoxicity:	0.103	Ototoxicity:	0.531
Hematotoxicity:	0.619	Drug-induced Nephrotoxicity:	0.798
Genotoxicity:	0.229	RPMI-8226 Immunitoxicity:	0.081
A549 Cytotoxicity:	0.478	Hek293 Cytotoxicity:	0.309
BCF:	2.341 ? 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:	4.808 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.026 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.692 ? 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
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	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
Activity	1

Activity Type	# Activity
Organism	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
NPT693	Organism	Xenopus laevis	Xenopus laevis	Activity	>	50.0	%	PMID[12762796]

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 NPC275740 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	17156
0.1-0.2	25627
0.2-0.3	6373
0.3-0.4	562
0.4-0.5	91
0.5-0.6	22
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC86319
0.8772	High Similarity	NPC69454
0.7797	Intermediate Similarity	NPC259286
0.7797	Intermediate Similarity	NPC83216
0.7797	Intermediate Similarity	NPC484085
0.7759	Intermediate Similarity	NPC110021
0.7759	Intermediate Similarity	NPC482426
0.7742	Intermediate Similarity	NPC601194
0.7627	Intermediate Similarity	NPC482424
0.7377	Intermediate Similarity	NPC183283
0.7167	Intermediate Similarity	NPC482423
0.7069	Intermediate Similarity	NPC46160
0.7069	Intermediate Similarity	NPC202642
0.6964	Remote Similarity	NPC482425
0.6667	Remote Similarity	NPC482518
0.6462	Remote Similarity	NPC191684
0.6308	Remote Similarity	NPC41539
0.6308	Remote Similarity	NPC472940
0.625	Remote Similarity	NPC249954
0.6119	Remote Similarity	NPC482597
0.6094	Remote Similarity	NPC90965
0.6094	Remote Similarity	NPC94755
0.6056	Remote Similarity	NPC489808
0.6056	Remote Similarity	NPC489800
0.6	Remote Similarity	NPC482515
0.6	Remote Similarity	NPC482517
0.5873	Remote Similarity	NPC205455
0.5781	Remote Similarity	NPC214570
0.5758	Remote Similarity	NPC99909
0.5692	Remote Similarity	NPC131470
0.5672	Remote Similarity	NPC475772
0.5429	Remote Similarity	NPC8571
0.5397	Remote Similarity	NPC73428
0.5385	Remote Similarity	NPC231477
0.5385	Remote Similarity	NPC123724
0.5362	Remote Similarity	NPC484084
0.5352	Remote Similarity	NPC318332
0.5352	Remote Similarity	NPC484971
0.5352	Remote Similarity	NPC484970
0.5312	Remote Similarity	NPC118508
0.5312	Remote Similarity	NPC484086
0.5231	Remote Similarity	NPC275910
0.5231	Remote Similarity	NPC318136
0.5224	Remote Similarity	NPC471724
0.5217	Remote Similarity	NPC471722
0.5217	Remote Similarity	NPC605915
0.5147	Remote Similarity	NPC202389
0.5075	Remote Similarity	NPC482427

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC275740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6860
0.1-0.2	2104
0.2-0.3	183
0.3-0.4	3
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