NPASS Compound

Natural Product: NPC173272

Natural Product ID	NPC173272
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	15R-Hydroxytrametenolic Acid
IUPAC Name	(2R)-2-[(3S,5R,10S,13R,14R,15S,17R)-3,15-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms	15R-Hydroxytrametenolic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL482587
PubChem CID	44575773
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 82 85 0 0 0 0 0 0 0 0999 V2000 9.1334 0.1977 -0.3917 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6125 0.1622 -0.1817 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9094 -0.0309 -1.2416 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4691 -0.1223 -1.4048 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6084 -0.1421 -0.1923 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1590 -0.2020 -0.7136 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1809 -0.2272 0.4058 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2632 0.9855 1.2983 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8534 1.5371 1.3431 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0540 0.2871 1.2059 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7493 -0.4079 0.0241 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3687 0.1939 -1.2802 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2720 -1.8263 0.0929 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2040 -1.8823 0.0511 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9163 -0.5920 0.2461 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3434 0.4729 0.7975 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0101 1.7841 1.0139 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2120 1.8623 0.0753 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0230 0.6268 0.3570 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3424 -0.5684 -0.2188 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3562 -0.6366 -1.7087 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1048 -1.7639 0.3242 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4680 -1.7387 -0.3037 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2345 -0.4825 -0.0951 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4608 0.7730 -0.0140 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0954 1.6139 1.1114 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6208 1.6242 -1.2777 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1434 -0.3694 -1.1610 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1478 -0.5402 2.4416 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6507 2.0641 2.6149 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1093 -1.4062 -1.5731 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7946 -1.3622 -2.7984 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4135 -2.6836 -1.0705 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1634 0.3834 1.2037 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3907 1.2632 -0.4321 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3702 -0.3399 -1.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5487 -0.3343 0.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5300 -0.1471 -2.1936 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1626 0.8291 -1.9687 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1715 -0.9375 -2.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8087 -1.1045 0.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7724 0.7629 0.3958 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0869 0.6852 -1.3737 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4474 -1.1305 1.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5898 0.7064 2.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9986 1.7297 0.9460 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6790 2.2735 0.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1239 0.8905 -1.7203 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1379 -0.6374 -1.9982 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5611 0.8016 -1.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6712 -2.3655 0.9909 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7114 -2.3779 -0.7773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5957 -2.6392 0.7675 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5142 -2.2631 -0.9664 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3622 1.8474 2.0652 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3218 2.6419 0.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7652 1.7284 -0.9529 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7650 2.7989 0.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9940 0.4879 1.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1864 -1.7187 -1.9881 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3370 -0.3932 -2.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5701 -0.0639 -2.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1565 -1.7707 1.4150 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5799 -2.6654 -0.0378 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0303 -2.6109 0.1265 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3451 -1.9860 -1.3821 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8892 -0.6447 0.8123 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6117 1.3645 2.0885 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1753 1.4404 1.1275 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9118 2.6967 0.9328 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2308 1.0700 -2.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1914 2.5559 -1.0977 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6479 1.9376 -1.6951 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8651 0.2804 -0.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0948 0.1207 3.3495 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0813 -1.1141 2.5486 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7539 -1.2113 2.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3757 1.8786 3.2429 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8457 -3.3342 -1.7332 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0974 0.3477 1.8722 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7989 1.4366 1.2824 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4888 -0.3686 1.6181 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 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 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 24 28 1 0 10 29 1 1 9 30 1 0 6 31 1 0 31 32 2 0 31 33 1 0 2 34 1 0 11 7 1 0 20 15 1 0 16 10 1 0 25 19 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 6 7 44 1 1 8 45 1 0 8 46 1 0 9 47 1 6 12 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 1 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 24 67 1 1 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 M END

Standard InCHIKey	QQFMRSAZKNSIDN-JZTHNVADSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-18(2)9-8-10-19(26(33)34)22-17-25(32)30(7)21-11-12-23-27(3,4)24(31)14-15-28(23,5)20(21)13-16-29(22,30)6/h9,19,22-25,31-32H,8,10-17H2,1-7H3,(H,33,34)/t19-,22-,23+,24+,25+,28-,29-,30-/m1/s1
SMILES	CC(=CCC[C@H]([C@H]1C[C@@H]([C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)O)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	520.462 ? Van der Waals volume.
Dense:	0.908	LogP:	3.646 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.104 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.257 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.398	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.96	Fsp³:	0.833
MCE-18:	84.0 ? 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:	0.815	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.432	Promiscuous compounds:	0.174

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.321	MDCK Permeability:	-4.959
Pgp-inhibitor:	0.001	Pgp-substrate:	0.289
PAMPA:	1.0 ? 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):	0.009
20% Bioavailability (F20%):	0.501	30% Bioavailability (F30%):	0.051
50% Bioavailability (F50%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.412	MRP1:	0.995
Plasma Protein Binding (PPB):	89.658%	Volume Distribution (VD):	-0.391
Fu:	5.86% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.965	BCRP inhibitor:	0.012
BSEP inhibitor:	0.308

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.909	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.246	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.027	CYP3A4-substrate:	0.102
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.008
HLM stability:	0.008 ? 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):

7.525

Half-life (T1/2):

0.958

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.039
Human Hepatotoxicity (H-HT):	0.661	Drug-induced Liver Injury (DILI):	0.282
AMES Toxicity:	0.329	Rat Oral Acute Toxicity:	0.34
Maximum Recommended Daily Dose:	0.203	Skin Sensitization:	0.998
Carcinogencity:	0.844	Eye Corrosion:	0.044
Eye Irritation:	0.728	Respiratory Toxicity:	0.823
Drug-induced Neurotoxicity:	0.032	Ototoxicity:	0.672
Hematotoxicity:	0.453	Drug-induced Nephrotoxicity:	0.959
Genotoxicity:	0.089	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.247	Hek293 Cytotoxicity:	0.076
BCF:	1.066 ? 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:	3.941 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.571 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.766 ? 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
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620242]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19842686]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13025	Senecio lanceus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9732	Glochidion heyneanum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11286	Helichrysum bilobum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13025	Senecio lanceus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11286	Helichrysum bilobum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9732	Glochidion heyneanum	Species	Phyllanthaceae	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
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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	12000.0	nM	PMID[15620242]

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 NPC173272 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	19878
0.1-0.2	25151
0.2-0.3	4408
0.3-0.4	339
0.4-0.5	51
0.5-0.6	22
0.6-0.7	2
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
0.7869	Intermediate Similarity	NPC48330
0.7581	Intermediate Similarity	NPC233836
0.7581	Intermediate Similarity	NPC159046
0.7581	Intermediate Similarity	NPC187376
0.6923	Remote Similarity	NPC76895
0.6143	Remote Similarity	NPC482518
0.5882	Remote Similarity	NPC55309
0.5882	Remote Similarity	NPC28252
0.5797	Remote Similarity	NPC469400
0.5775	Remote Similarity	NPC206810
0.5714	Remote Similarity	NPC84271
0.5714	Remote Similarity	NPC102414
0.5556	Remote Similarity	NPC203035
0.5352	Remote Similarity	NPC484974
0.5352	Remote Similarity	NPC23434
0.5342	Remote Similarity	NPC484976
0.5224	Remote Similarity	NPC46160
0.5224	Remote Similarity	NPC202642
0.5205	Remote Similarity	NPC142361
0.5205	Remote Similarity	NPC474684
0.5143	Remote Similarity	NPC94755
0.5135	Remote Similarity	NPC148414
0.5135	Remote Similarity	NPC111585
0.5135	Remote Similarity	NPC175628
0.5072	Remote Similarity	NPC214570
0.5068	Remote Similarity	NPC222845
0.5068	Remote Similarity	NPC296577
0.5067	Remote Similarity	NPC469406

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC173272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6386
0.1-0.2	2669
0.2-0.3	91
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