NPASS Compound

Natural Product: NPC293564

Natural Product ID	NPC293564
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-Hydroxyrus-12,19(29)-Dien-28-Oic Acid
IUPAC Name	(2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,6a,6b,9,9,12a-hexamethyl-1-methylidene-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL517522
PubChem CID	21670092
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 79 83 0 0 0 0 0 0 0 0999 V2000 3.5879 2.2329 -0.9784 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0197 1.1762 -0.3199 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3238 0.5976 -0.7295 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3360 0.5190 -2.2476 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5559 -0.7614 -0.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0450 -0.8306 1.2311 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5115 -0.7011 1.2682 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1763 0.6485 0.7779 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7393 0.7723 0.4775 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0127 1.8163 0.8503 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4156 2.0165 0.5927 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0738 0.8302 -0.0059 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3207 -0.4413 0.3205 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0557 -0.2983 -0.2827 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9462 0.3019 -1.7041 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8316 -1.5558 -0.4084 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8575 -1.8516 0.6167 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2362 -0.6534 1.8142 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0040 -1.6637 -0.2346 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5051 -1.6588 -0.0394 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0500 -0.3886 -0.6304 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5608 0.7547 0.2211 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9866 0.7591 1.6307 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1441 2.0113 -0.4459 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6315 2.0516 -0.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3150 0.7213 -0.4727 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4844 -0.3980 -0.9665 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7012 -0.5160 -2.4876 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0940 -1.6946 -0.4116 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0109 0.4155 0.7239 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2031 -0.7371 2.7463 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6401 0.1924 3.3450 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5713 -1.8662 3.4550 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1657 2.6479 -1.7763 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6601 2.6918 -0.7272 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1795 1.2409 -0.4399 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0730 -0.2744 -2.5194 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7101 1.5105 -2.6287 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3465 0.2678 -2.6571 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6449 -0.9802 -0.1278 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1275 -1.4962 -0.8688 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2545 -1.8399 1.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4782 -0.0111 1.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3586 1.3675 1.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5393 2.6058 1.4070 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4973 2.8861 -0.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8798 2.3924 1.5289 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9898 0.9353 -1.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2089 -0.2174 -2.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8995 1.3909 -1.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9506 0.0668 -2.1695 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1436 -2.4240 -0.4765 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3622 -1.5882 -1.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6790 -2.4830 0.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4825 -2.5878 1.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0647 0.2106 2.3973 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5025 -1.4605 2.0354 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1978 -1.1159 2.2025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6669 -2.5419 0.3950 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7410 -1.7886 -1.2903 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8766 -2.5312 -0.6564 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7005 -1.7985 1.0196 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4826 -0.2757 -1.6086 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1759 1.0613 2.3605 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7756 1.5448 1.8398 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3976 -0.1735 2.0293 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8422 1.9661 -1.5161 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7198 2.9224 -0.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0071 2.5485 0.5631 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9654 2.7688 -1.1894 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1717 0.8711 -1.2018 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9808 0.5099 -2.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7472 -0.7714 -2.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5407 -1.1660 -2.7308 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8580 -2.5147 -1.1407 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6655 -1.9975 0.5398 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2031 -1.6221 -0.3853 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6410 -0.3397 1.2014 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0128 -2.2083 4.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 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 13 18 1 1 13 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 26 30 1 0 7 31 1 1 31 32 2 0 31 33 1 0 8 2 1 0 14 9 1 0 27 21 1 0 17 7 1 0 22 12 1 0 1 34 1 0 1 35 1 0 3 36 1 6 4 37 1 0 4 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 8 44 1 1 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 6 15 49 1 0 15 50 1 0 15 51 1 0 16 52 1 0 16 53 1 0 17 54 1 0 17 55 1 0 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 6 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 26 71 1 6 28 72 1 0 28 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 M END

Standard InCHIKey	VPMTUSRUIJFRMW-XCYSCKFXSA-N
Standard InCHI	InChI=1S/C30H46O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18,21-24,31H,2,9-17H2,1,3-7H3,(H,32,33)/t18-,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
SMILES	C=C1[C@H](C)CC[C@]2([C@@H]1C1=CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.34	Volume:	503.115 ? Van der Waals volume.
Dense:	0.903	LogP:	3.983 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.55 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.89 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	28.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.419	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.955	Fsp³:	0.833
MCE-18:	102.255 ? 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:	0.794	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.127 ? 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:	0.41	Promiscuous compounds:	0.066

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.557	MDCK Permeability:	-5.094
Pgp-inhibitor:	0.002	Pgp-substrate:	0.009
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):	0.001
20% Bioavailability (F20%):	0.78	30% Bioavailability (F30%):	0.348
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056	MRP1:	0.939
Plasma Protein Binding (PPB):	96.868%	Volume Distribution (VD):	-0.205
Fu:	3.32% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.908	BCRP inhibitor:	0.775
BSEP inhibitor:	0.866

ADMET: Metabolism

CYP1A2-inhibitor:	0.165	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.829	CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.112	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.059	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.009	CYP3A4-substrate:	0.814
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.018
HLM stability:	0.461 ? 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):

3.896

Half-life (T1/2):

0.704

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.017
Human Hepatotoxicity (H-HT):	0.509	Drug-induced Liver Injury (DILI):	0.475
AMES Toxicity:	0.304	Rat Oral Acute Toxicity:	0.274
Maximum Recommended Daily Dose:	0.438	Skin Sensitization:	0.95
Carcinogencity:	0.911	Eye Corrosion:	0.099
Eye Irritation:	0.827	Respiratory Toxicity:	0.898
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.6
Hematotoxicity:	0.598	Drug-induced Nephrotoxicity:	0.9
Genotoxicity:	0.322	RPMI-8226 Immunitoxicity:	0.025
A549 Cytotoxicity:	0.45	Hek293 Cytotoxicity:	0.217
BCF:	1.552 ? 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:	4.075 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.528 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.953 ? 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
NPO928	Baeckea gunniana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654412]
NPO928	Baeckea gunniana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	2
Inhibition	2

Activity Type	# Activity
Individual protein	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	IC50	=	5300.0	nM	PMID[22734800]
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	IC50	=	3200.0	nM	DOI[10.1007/s00044-012-0222-8]
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	80.0	%	Open TG-GATES in vivo data: Biochemistry
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	65.0	%	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC293564 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	22040
0.1-0.2	23129
0.2-0.3	3548
0.3-0.4	757
0.4-0.5	264
0.5-0.6	72
0.6-0.7	26
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
0.7538	Intermediate Similarity	NPC51700
0.7538	Intermediate Similarity	NPC88716
0.7538	Intermediate Similarity	NPC68160
0.7121	Intermediate Similarity	NPC480946
0.7121	Intermediate Similarity	NPC187722
0.7121	Intermediate Similarity	NPC130577
0.7121	Intermediate Similarity	NPC142415
0.7121	Intermediate Similarity	NPC102683
0.7059	Intermediate Similarity	NPC202728
0.7059	Intermediate Similarity	NPC158059
0.7015	Intermediate Similarity	NPC182797
0.7015	Intermediate Similarity	NPC52169
0.7015	Intermediate Similarity	NPC488562
0.6618	Remote Similarity	NPC274330
0.6522	Remote Similarity	NPC606443
0.6429	Remote Similarity	NPC61543
0.6429	Remote Similarity	NPC293048
0.6429	Remote Similarity	NPC225585
0.6286	Remote Similarity	NPC171203
0.6286	Remote Similarity	NPC307426
0.6286	Remote Similarity	NPC98442
0.6286	Remote Similarity	NPC242468
0.6232	Remote Similarity	NPC477872
0.6143	Remote Similarity	NPC198664
0.6111	Remote Similarity	NPC136697
0.6056	Remote Similarity	NPC7260
0.6056	Remote Similarity	NPC270768
0.6056	Remote Similarity	NPC59263
0.6056	Remote Similarity	NPC210037
0.6056	Remote Similarity	NPC210106
0.6056	Remote Similarity	NPC229281
0.6056	Remote Similarity	NPC120968
0.6056	Remote Similarity	NPC121798
0.6056	Remote Similarity	NPC234346
0.6056	Remote Similarity	NPC227467
0.6056	Remote Similarity	NPC273621
0.6027	Remote Similarity	NPC191412
0.6027	Remote Similarity	NPC114159
0.6027	Remote Similarity	NPC6818
0.5946	Remote Similarity	NPC127689
0.5946	Remote Similarity	NPC130520
0.589	Remote Similarity	NPC228784
0.589	Remote Similarity	NPC324341
0.589	Remote Similarity	NPC298554
0.589	Remote Similarity	NPC601810
0.5867	Remote Similarity	NPC187933
0.5867	Remote Similarity	NPC116457
0.5833	Remote Similarity	NPC195019
0.5833	Remote Similarity	NPC112866
0.5811	Remote Similarity	NPC610635
0.5753	Remote Similarity	NPC71074
0.5753	Remote Similarity	NPC605937
0.5694	Remote Similarity	NPC610937
0.5625	Remote Similarity	NPC603645
0.56	Remote Similarity	NPC118519
0.56	Remote Similarity	NPC263393
0.5541	Remote Similarity	NPC18872
0.5541	Remote Similarity	NPC290614
0.5541	Remote Similarity	NPC37221
0.5467	Remote Similarity	NPC259733
0.5467	Remote Similarity	NPC158371
0.5467	Remote Similarity	NPC207922
0.5467	Remote Similarity	NPC173089
0.5467	Remote Similarity	NPC87095
0.5467	Remote Similarity	NPC29765
0.5405	Remote Similarity	NPC64872
0.5405	Remote Similarity	NPC84319
0.5405	Remote Similarity	NPC25906
0.5405	Remote Similarity	NPC52021
0.5405	Remote Similarity	NPC599947
0.5342	Remote Similarity	NPC242631
0.5333	Remote Similarity	NPC88116
0.5333	Remote Similarity	NPC472149
0.5325	Remote Similarity	NPC25299
0.5325	Remote Similarity	NPC481322
0.5316	Remote Similarity	NPC474727
0.5294	Remote Similarity	NPC290598
0.5294	Remote Similarity	NPC27765
0.5294	Remote Similarity	NPC30590
0.5294	Remote Similarity	NPC122418
0.5294	Remote Similarity	NPC491014
0.5286	Remote Similarity	NPC101475
0.5278	Remote Similarity	NPC264317
0.5278	Remote Similarity	NPC294438
0.527	Remote Similarity	NPC477289
0.5263	Remote Similarity	NPC32407
0.5263	Remote Similarity	NPC263548
0.5263	Remote Similarity	NPC606320
0.5256	Remote Similarity	NPC157113
0.525	Remote Similarity	NPC230151
0.5222	Remote Similarity	NPC488215
0.5211	Remote Similarity	NPC235341
0.52	Remote Similarity	NPC282616
0.52	Remote Similarity	NPC275809
0.5195	Remote Similarity	NPC485589
0.5195	Remote Similarity	NPC91010
0.5195	Remote Similarity	NPC132824
0.5185	Remote Similarity	NPC54909
0.5135	Remote Similarity	NPC274050
0.5135	Remote Similarity	NPC162632
0.5132	Remote Similarity	NPC38754
0.5132	Remote Similarity	NPC158141
0.5128	Remote Similarity	NPC137072
0.5128	Remote Similarity	NPC148964
0.5072	Remote Similarity	NPC120098
0.507	Remote Similarity	NPC311078
0.5067	Remote Similarity	NPC18064
0.5067	Remote Similarity	NPC151191
0.5067	Remote Similarity	NPC16377
0.5065	Remote Similarity	NPC477288
0.5063	Remote Similarity	NPC174663

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC293564 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6518
0.1-0.2	2571
0.2-0.3	52
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
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
0.5278	Remote Similarity	NPD7520	Phase 1

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