NPASS Compound

Natural Product: NPC546702

Natural Product ID	NPC546702
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1~{R},2~{R},5~{S},8~{R},9~{S},10~{R},13~{R},14~{R},15~{S},16~{R},18~{R})-15-formyl-16-hydroxy-8-isopropenyl-1,2,14,17,17-pentamethyl-pentacyclo[11.7.0.0^{2,10}.0^{5,9}.0^{14,18}]icosane-5-carboxylic acid
IUPAC Name	(1~{R},2~{R},5~{S},8~{R},9~{S},10~{R},13~{R},14~{R},15~{S},16~{R},18~{R})-15-formyl-16-hydroxy-8-isopropenyl-1,2,14,17,17-pentamethyl-pentacyclo[11.7.0.0^{2,10}.0^{5,9}.0^{14,18}]icosane-5-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 84 0 0 0 0 0 0 0 0999 V2000 3.4973 0.4501 -3.3147 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8558 0.0653 -2.0634 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2254 -1.3835 -1.9844 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8717 1.0393 -1.0128 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2890 0.9549 -0.3841 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1175 0.1200 0.8506 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6640 0.2216 1.2857 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7128 1.0628 2.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3069 0.6310 3.6380 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2357 2.3302 2.3971 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0717 -1.0792 1.6204 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8172 -1.5204 1.0068 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0242 -0.5658 0.1777 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8333 -1.1631 -1.1915 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5876 0.8231 0.1629 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8503 1.7578 -0.7348 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5818 1.8921 -0.2225 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1472 0.5281 -0.0980 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6545 0.4855 0.1062 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1304 0.9795 1.4202 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3908 1.2356 -0.9771 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8025 2.5933 -0.5235 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9638 2.8900 -0.5334 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6601 0.4276 -1.1479 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9801 0.3184 -2.5100 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4587 -0.9219 -0.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3849 -1.2757 0.5618 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6825 -1.9811 -1.6414 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0131 -0.9241 -0.2288 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5238 -1.8239 0.8114 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0398 -1.7485 0.9720 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4043 -0.4193 0.7760 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2195 0.1447 2.1957 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0569 1.0042 0.1781 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2074 1.4855 -3.4931 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4810 -0.2101 -4.1518 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8597 -1.7646 -1.0197 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7739 -1.9874 -2.7930 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3317 -1.5149 -1.9703 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9090 2.0675 -1.5001 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6434 1.9569 -0.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0162 0.5584 -1.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8314 0.4283 1.6472 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3483 -0.9449 0.6558 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0574 3.0503 3.0880 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8967 -1.8521 1.4741 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9663 -1.1396 2.7448 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1277 -1.9626 1.7833 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0512 -2.4519 0.3976 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9865 -0.4483 -2.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1523 -1.6386 -1.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5141 -2.0645 -1.3177 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2951 1.2135 1.1991 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9170 1.5721 -1.7969 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3017 2.7819 -0.5672 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6937 2.5630 0.6129 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1163 2.3779 -1.0975 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0616 0.1300 -1.1610 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1926 1.3526 1.2844 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1005 0.2961 2.2608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5836 1.9124 1.6825 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7886 1.2803 -1.9070 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0786 3.3087 -0.1884 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5281 0.9257 -0.6701 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9361 0.2137 -2.6617 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3210 -1.7242 0.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7302 -0.4701 1.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9422 -2.1216 1.1460 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4283 -1.5357 -2.6234 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0008 -2.8482 -1.4732 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7471 -2.2849 -1.6396 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4648 -1.1657 -1.1889 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7772 -2.8865 0.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0617 -1.6849 1.7885 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5556 -2.5758 0.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8761 -2.1512 2.0260 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4029 1.2032 2.2903 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9121 -0.3579 2.9231 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7940 -0.1412 2.6090 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1629 2.1011 0.5527 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 8 9 2 0 8 10 1 0 7 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 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 2 0 21 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 26 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 1 15 34 1 0 34 4 1 0 34 7 1 0 32 13 1 0 32 18 1 0 29 19 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 6 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 14 50 1 0 14 51 1 0 14 52 1 0 15 53 1 1 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 18 58 1 6 20 59 1 0 20 60 1 0 20 61 1 0 21 62 1 6 22 63 1 0 24 64 1 1 25 65 1 0 27 66 1 0 27 67 1 0 27 68 1 0 28 69 1 0 28 70 1 0 28 71 1 0 29 72 1 6 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 1 M END

Standard InCHIKey	SLWJVQQNDGLXTK-PYIFJILSSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-17(2)18-10-13-30(25(33)34)15-14-27(5)19(23(18)30)8-9-22-28(27,6)12-11-21-26(3,4)24(32)20(16-31)29(21,22)7/h16,18-24,32H,1,8-15H2,2-7H3,(H,33,34)/t18-,19+,20+,21-,22-,23-,24+,27+,28+,29-,30-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)[C@H](C=O)[C@@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	3.533 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.012 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.579 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.385	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.075	Fsp³:	0.867
MCE-18:	105.857 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.885	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.323	Promiscuous compounds:	0.098

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.356	MDCK Permeability:	-5.028
Pgp-inhibitor:	0.007	Pgp-substrate:	0.002
PAMPA:	0.917 ? 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%):	0.378	30% Bioavailability (F30%):	0.353
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.52	MRP1:	0.875
Plasma Protein Binding (PPB):	95.58%	Volume Distribution (VD):	-0.308
Fu:	5.102% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.776	BCRP inhibitor:	0.03
BSEP inhibitor:	0.979

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.182	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.11	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.022	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.046
HLM stability:	0.014 ? 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):

5.395

Half-life (T1/2):

1.048

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.038
Human Hepatotoxicity (H-HT):	0.547	Drug-induced Liver Injury (DILI):	0.407
AMES Toxicity:	0.301	Rat Oral Acute Toxicity:	0.299
Maximum Recommended Daily Dose:	0.232	Skin Sensitization:	0.973
Carcinogencity:	0.793	Eye Corrosion:	0.06
Eye Irritation:	0.439	Respiratory Toxicity:	0.741
Drug-induced Neurotoxicity:	0.057	Ototoxicity:	0.837
Hematotoxicity:	0.632	Drug-induced Nephrotoxicity:	0.854
Genotoxicity:	0.846	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.067	Hek293 Cytotoxicity:	0.128
BCF:	0.711 ? 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:	3.551 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.046 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.494 ? 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
NPO50707	Zizyphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23278	Colubrina granulosa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO60556	Zizphus cambodiana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23278	Colubrina granulosa	Species	Rhamnaceae	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

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

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 NPC546702 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	21154
0.1-0.2	25236
0.2-0.3	3031
0.3-0.4	331
0.4-0.5	53
0.5-0.6	27
0.6-0.7	17
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC24772
0.7797	Intermediate Similarity	NPC80590
0.746	Intermediate Similarity	NPC486704
0.7333	Intermediate Similarity	NPC116146
0.6825	Remote Similarity	NPC488506
0.6825	Remote Similarity	NPC220498
0.6667	Remote Similarity	NPC264317
0.6667	Remote Similarity	NPC294438
0.6562	Remote Similarity	NPC211162
0.6562	Remote Similarity	NPC183374
0.6308	Remote Similarity	NPC488164
0.6308	Remote Similarity	NPC264005
0.625	Remote Similarity	NPC119743
0.6212	Remote Similarity	NPC195395
0.6212	Remote Similarity	NPC201655
0.6061	Remote Similarity	NPC291373
0.6061	Remote Similarity	NPC213832
0.6032	Remote Similarity	NPC246445
0.6032	Remote Similarity	NPC68828
0.6029	Remote Similarity	NPC474719
0.6	Remote Similarity	NPC192744
0.5942	Remote Similarity	NPC488165
0.5882	Remote Similarity	NPC2783
0.5882	Remote Similarity	NPC16377
0.5857	Remote Similarity	NPC169933
0.5797	Remote Similarity	NPC475061
0.5797	Remote Similarity	NPC488213
0.5735	Remote Similarity	NPC277399
0.5652	Remote Similarity	NPC4309
0.5652	Remote Similarity	NPC151191
0.5634	Remote Similarity	NPC601176
0.5571	Remote Similarity	NPC269360
0.5571	Remote Similarity	NPC601275
0.5513	Remote Similarity	NPC486709
0.5507	Remote Similarity	NPC271974
0.5507	Remote Similarity	NPC247312
0.5493	Remote Similarity	NPC160506
0.5417	Remote Similarity	NPC607677
0.5366	Remote Similarity	NPC290349
0.5309	Remote Similarity	NPC486699
0.5278	Remote Similarity	NPC611139
0.5244	Remote Similarity	NPC486695
0.5217	Remote Similarity	NPC30583
0.5205	Remote Similarity	NPC478841
0.5205	Remote Similarity	NPC488166
0.5205	Remote Similarity	NPC600004
0.5205	Remote Similarity	NPC608379
0.5122	Remote Similarity	NPC486708

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC546702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5429
0.1-0.2	3629
0.2-0.3	87
0.3-0.4	2
0.4-0.5	1
0.5-0.6	1
0.6-0.7	1
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
0.6667	Remote Similarity	NPD7520	Phase 1
0.5493	Remote Similarity	NPD8035	Phase 2

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