NPASS Compound

Natural Product: NPC95243

Natural Product ID	NPC95243
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	21Beta,25-Dimethylmelianodiol
IUPAC Name	(5R,9R,10R,13S,14S,17S)-17-[(2S,3S,5R)-5-[(1S)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms	21Beta,25-Dimethylmelianodiol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL452105
PubChem CID	21668674
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 89 93 0 0 0 0 0 0 0 0999 V2000 -6.8403 2.1528 0.4565 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4407 0.7664 -0.0658 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1556 0.6045 -1.3918 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9752 0.6826 -0.2936 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6078 0.3110 -1.7099 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1990 -0.1528 -1.8179 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3404 -0.2228 -0.8195 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7785 0.1872 0.5444 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8953 -0.4191 1.5707 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4821 -0.0122 1.3281 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1014 0.2647 -0.0812 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4478 1.6523 -0.5415 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2643 -0.1582 -0.4788 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1385 -0.5054 -1.9718 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3379 -0.4061 -2.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9436 -0.6861 -0.9518 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7101 -2.1187 -0.6201 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3652 0.7995 -0.3495 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6587 0.0993 -0.8481 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6832 1.0444 -0.3078 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8849 0.4343 0.3204 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7791 -0.3778 -0.5908 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4156 0.4816 -1.6588 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0916 -1.5709 -1.1813 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8152 -0.8185 0.2282 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7843 -1.5745 -0.3894 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7259 1.4590 0.8433 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0620 1.8229 0.6771 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8575 1.1532 1.0123 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2380 0.1080 1.8103 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7834 0.3500 3.1014 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2385 -0.2223 0.6779 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4678 -1.6645 0.3599 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7340 0.0223 2.0919 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1662 -0.4018 2.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9020 -0.2264 0.9107 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8773 -0.9254 0.7181 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8049 2.4472 0.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0852 2.8927 0.1213 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8364 2.1321 1.5723 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7279 1.2748 -2.1517 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2373 -0.4495 -1.7089 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2108 0.9636 -1.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5349 1.7101 -0.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6876 1.2102 -2.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2434 -0.4644 -2.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8564 -0.4567 -2.8003 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7706 1.2863 0.6903 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0438 -1.5167 1.6693 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2265 -0.0113 2.5726 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1726 -0.8009 1.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3005 0.9401 1.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6554 2.3532 0.2841 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3424 2.1136 -1.1660 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3634 1.6787 -1.2027 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5426 -1.1072 0.0260 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5677 -1.4818 -2.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6460 0.2520 -2.6018 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6178 -1.1811 -3.0444 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5825 0.5661 -2.7209 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0008 -2.6045 -1.3553 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1720 -2.2479 0.3651 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6204 -2.7570 -0.6728 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3170 1.7130 -0.9508 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5739 0.1240 -1.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7049 -0.8948 -0.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9332 1.7610 -1.1319 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5949 -0.1906 1.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7899 -0.2085 -2.4512 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2377 1.0946 -1.2525 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6992 1.1711 -2.1347 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8327 -2.2314 -1.7318 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6607 -2.2370 -0.4189 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3763 -1.3063 -2.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5679 -1.8046 0.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3270 -1.0452 -1.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4153 -2.5874 -0.7092 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3957 1.7000 1.7332 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2877 1.8883 1.5714 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6837 0.4494 3.1664 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1895 1.3428 3.4411 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0650 -0.4582 3.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3148 -2.1036 0.9272 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5921 -2.3114 0.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6707 -1.8090 -0.7160 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5728 1.0752 2.3868 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1503 -0.6547 2.7654 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2982 -1.4352 2.5844 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6530 0.2844 2.9400 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 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 1 0 14 15 1 0 15 16 1 0 16 17 1 1 13 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 21 27 1 0 20 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 8 32 1 0 32 33 1 6 32 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 2 1 0 32 4 1 0 16 7 1 0 29 18 1 0 16 11 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 3 43 1 0 4 44 1 1 5 45 1 0 5 46 1 0 6 47 1 0 8 48 1 6 9 49 1 0 9 50 1 0 10 51 1 0 10 52 1 0 12 53 1 0 12 54 1 0 12 55 1 0 13 56 1 1 14 57 1 0 14 58 1 0 15 59 1 0 15 60 1 0 17 61 1 0 17 62 1 0 17 63 1 0 18 64 1 6 19 65 1 0 19 66 1 0 20 67 1 6 21 68 1 1 23 69 1 0 23 70 1 0 23 71 1 0 24 72 1 0 24 73 1 0 24 74 1 0 26 75 1 0 26 76 1 0 26 77 1 0 27 78 1 0 29 79 1 1 31 80 1 0 31 81 1 0 31 82 1 0 33 83 1 0 33 84 1 0 33 85 1 0 34 86 1 0 34 87 1 0 35 88 1 0 35 89 1 0 M END

Standard InCHIKey	LEHCWPXGSDLCRO-GFYVDCOPSA-N
Standard InCHI	InChI=1S/C32H52O5/c1-28(2)24-11-10-22-21(30(24,5)15-14-25(28)33)13-17-31(6)20(12-16-32(22,31)7)19-18-23(37-27(19)35-8)26(34)29(3,4)36-9/h10,19-21,23-24,26-27,34H,11-18H2,1-9H3/t19-,20-,21-,23+,24-,26-,27-,30+,31-,32+/m0/s1
SMILES	CC1(C)[C@@H]2CC=C3[C@H](CC[C@@]4(C)[C@@H](CC[C@]34C)[C@@H]3C[C@H]([C@@H](C(C)(C)OC)O)O[C@@H]3OC)[C@@]2(C)CCC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.38	Volume:	557.924 ? Van der Waals volume.
Dense:	0.926	LogP:	4.004 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.682 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.936 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	26.0
TPSA:	64.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.433	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.224	Fsp³:	0.906
MCE-18:	101.016 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.865	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.239	Promiscuous compounds:	0.285

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.931	MDCK Permeability:	-4.91
Pgp-inhibitor:	0.921	Pgp-substrate:	0.008
PAMPA:	0.285 ? 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%):	0.005	30% Bioavailability (F30%):	0.006
50% Bioavailability (F50%):	0.554

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.179	MRP1:	0.733
Plasma Protein Binding (PPB):	90.882%	Volume Distribution (VD):	0.543
Fu:	8.654% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.57
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.939	CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.984 ? 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):

11.697

Half-life (T1/2):

0.487

ADMET: Toxicity

hERG Blockers:	0.106	hERG Blockers (10um):	0.364
Human Hepatotoxicity (H-HT):	0.687	Drug-induced Liver Injury (DILI):	0.57
AMES Toxicity:	0.497	Rat Oral Acute Toxicity:	0.71
Maximum Recommended Daily Dose:	0.742	Skin Sensitization:	0.753
Carcinogencity:	0.717	Eye Corrosion:	0.004
Eye Irritation:	0.396	Respiratory Toxicity:	0.592
Drug-induced Neurotoxicity:	0.502	Ototoxicity:	0.717
Hematotoxicity:	0.557	Drug-induced Nephrotoxicity:	0.772
Genotoxicity:	0.945	RPMI-8226 Immunitoxicity:	0.143
A549 Cytotoxicity:	0.36	Hek293 Cytotoxicity:	0.476
BCF:	2.039 ? 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:	4.17 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.443 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.954 ? 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
NPO8325	Raulinoa echinata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11704964]
NPO8325	Raulinoa echinata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975501]
NPO8325	Raulinoa echinata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8325	Raulinoa echinata	Species	Rutaceae	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	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
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	114.5	ug.mL-1	PMID[17958396]

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
-	Artemia salina	LD50	>	100.0	ug ml-1	PMID[22652254]

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 NPC95243 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	17918
0.1-0.2	26290
0.2-0.3	5220
0.3-0.4	326
0.4-0.5	54
0.5-0.6	23
0.6-0.7	19
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC63023
0.8529	High Similarity	NPC121566
0.8529	High Similarity	NPC100955
0.7534	Intermediate Similarity	NPC189282
0.7534	Intermediate Similarity	NPC237402
0.6486	Remote Similarity	NPC5358
0.6486	Remote Similarity	NPC216260
0.641	Remote Similarity	NPC484792
0.6301	Remote Similarity	NPC486521
0.6301	Remote Similarity	NPC262870
0.6203	Remote Similarity	NPC85593
0.6203	Remote Similarity	NPC31430
0.6133	Remote Similarity	NPC324598
0.6111	Remote Similarity	NPC470052
0.6111	Remote Similarity	NPC260992
0.6027	Remote Similarity	NPC470047
0.6027	Remote Similarity	NPC470046
0.6	Remote Similarity	NPC484789
0.6	Remote Similarity	NPC484801
0.6	Remote Similarity	NPC67831
0.6	Remote Similarity	NPC484786
0.6	Remote Similarity	NPC174051
0.6	Remote Similarity	NPC484787
0.6	Remote Similarity	NPC484788
0.5921	Remote Similarity	NPC605437
0.589	Remote Similarity	NPC90652
0.589	Remote Similarity	NPC155255
0.589	Remote Similarity	NPC470417
0.5833	Remote Similarity	NPC101450
0.5769	Remote Similarity	NPC273669
0.5769	Remote Similarity	NPC484802
0.5769	Remote Similarity	NPC118647
0.5714	Remote Similarity	NPC479667
0.5658	Remote Similarity	NPC471224
0.5616	Remote Similarity	NPC470223
0.5584	Remote Similarity	NPC470050
0.5584	Remote Similarity	NPC470051
0.5556	Remote Similarity	NPC470078
0.5309	Remote Similarity	NPC73506
0.525	Remote Similarity	NPC484791
0.525	Remote Similarity	NPC484790
0.519	Remote Similarity	NPC472239
0.519	Remote Similarity	NPC484798
0.5132	Remote Similarity	NPC82902
0.5132	Remote Similarity	NPC474218
0.5125	Remote Similarity	NPC154101
0.5062	Remote Similarity	NPC107243

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC95243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6992
0.1-0.2	1973
0.2-0.3	184
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