NPASS Compound

Natural Product: NPC262920

Natural Product ID	NPC262920
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CHTCCKSXBYVSBJ-OGKPSKQVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 85 0 0 0 0 0 0 0 0999 V2000 -5.7510 -0.2989 -0.1759 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7314 0.7416 -0.4560 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9733 1.2369 -1.8966 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3104 0.2949 -0.4403 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0514 -0.8769 -1.3885 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5703 -0.8087 -1.6384 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7485 -1.0783 -0.4005 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8659 -2.5588 -0.1267 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2115 -0.1948 0.6793 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5401 -0.6654 1.9556 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9096 -0.5492 1.6910 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5184 -0.6105 0.5333 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9896 -0.4672 0.5234 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4693 0.9656 0.6823 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9704 0.9145 0.8353 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4993 2.3041 0.4737 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3717 0.6290 2.2741 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8669 1.6489 3.1038 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6295 -0.0738 -0.0730 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6739 -0.2344 -1.2663 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6666 -1.1972 -0.5993 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8002 -1.7372 -1.6538 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3792 -2.0419 -1.3258 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7114 -0.8182 -0.6783 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8038 0.2732 -1.7013 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6816 -2.1734 -0.1079 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6591 -3.4119 -0.1504 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6913 -1.3895 0.4249 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6626 0.0651 0.8699 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3539 -0.9573 1.7388 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7642 1.3910 1.6425 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5473 2.4209 0.8868 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8888 1.9449 0.4236 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7255 1.7206 1.5077 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4140 -1.3376 -0.3739 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6232 -0.1419 -0.8541 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2169 -0.2029 0.8502 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3205 0.3528 -2.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8023 1.9703 -1.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0312 1.6669 -2.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7392 1.1489 -0.9229 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5597 -0.6679 -2.3396 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3966 -1.8309 -0.9789 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3415 -1.4838 -2.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4038 0.2741 -1.9181 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1838 -2.9022 0.6790 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6092 -3.0616 -1.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8650 -2.9032 0.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7517 0.8214 0.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8152 -1.7210 2.2098 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8951 -0.0449 2.7802 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5267 -0.3924 2.5993 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4328 -0.9233 1.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0753 1.2918 1.6896 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1080 1.6464 -0.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6766 3.0241 0.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0857 2.2681 -0.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1095 2.7187 1.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9627 -0.3117 2.6600 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4732 0.6877 2.3796 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5356 2.4142 2.5662 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5920 0.3023 -0.4482 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1720 -0.7410 -2.1066 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1864 0.7024 -1.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2556 -2.7143 -2.0048 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7997 -1.1144 -2.5979 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3700 -2.9135 -0.6388 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8752 -2.2988 -2.2815 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3117 1.2123 -1.4220 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8483 0.5637 -1.9438 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4252 -0.1628 -2.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7027 -1.8469 1.2243 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7049 -1.1469 2.6243 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2767 -0.4991 2.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2527 1.2678 2.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7689 1.8293 1.8547 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9615 2.9133 0.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7466 3.2525 1.6263 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3517 2.8225 -0.1194 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6830 1.8039 1.1981 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 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 15 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 22 23 1 0 23 24 1 0 24 25 1 6 21 26 1 0 26 27 2 0 26 28 1 0 9 29 1 0 29 30 1 1 29 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 2 1 0 29 4 1 0 24 7 1 0 24 12 1 0 21 13 1 0 28 19 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 6 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 8 46 1 0 8 47 1 0 8 48 1 0 9 49 1 6 10 50 1 0 10 51 1 0 11 52 1 0 13 53 1 1 14 54 1 0 14 55 1 0 16 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 19 62 1 6 20 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 23 67 1 0 23 68 1 0 25 69 1 0 25 70 1 0 25 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 32 77 1 0 32 78 1 0 33 79 1 6 34 80 1 0 M END

Standard InCHIKey	CHTCCKSXBYVSBJ-OGKPSKQVSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-25(2)20-9-12-29(6)21(27(20,4)11-10-22(25)32)8-7-18-19-15-26(3,17-31)23-16-30(19,24(33)34-23)14-13-28(18,29)5/h7,19-23,31-32H,8-17H2,1-6H3/t19-,20-,21+,22-,23-,26-,27-,28+,29+,30+/m0/s1
SMILES	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC=C4[C@@H]5C[C@@](C)(CO)[C@@H]6C[C@@]5(CC[C@@]34C)C(=O)O6)[C@@]2(C)CC[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	505.985 ? Van der Waals volume.
Dense:	0.93	LogP:	3.913 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.693 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.239 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	30.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.383	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.285	Fsp³:	0.9
MCE-18:	159.175 ? 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:	0.777	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.025 ? 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:	0.177

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.868	MDCK Permeability:	-4.684
Pgp-inhibitor:	0.515	Pgp-substrate:	0.067
PAMPA:	0.994 ? 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):	0.002
20% Bioavailability (F20%):	0.249	30% Bioavailability (F30%):	0.078
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.764	MRP1:	0.298
Plasma Protein Binding (PPB):	86.217%	Volume Distribution (VD):	-0.15
Fu:	13.108% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.873	BCRP inhibitor:	0.993
BSEP inhibitor:	0.967

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.014	CYP2C19-substrate:	0.012
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.978
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.993 ? 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):

11.092

Half-life (T1/2):

1.053

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.197
Human Hepatotoxicity (H-HT):	0.642	Drug-induced Liver Injury (DILI):	0.147
AMES Toxicity:	0.426	Rat Oral Acute Toxicity:	0.441
Maximum Recommended Daily Dose:	0.841	Skin Sensitization:	0.991
Carcinogencity:	0.942	Eye Corrosion:	0.0
Eye Irritation:	0.13	Respiratory Toxicity:	0.555
Drug-induced Neurotoxicity:	0.084	Ototoxicity:	0.548
Hematotoxicity:	0.511	Drug-induced Nephrotoxicity:	0.881
Genotoxicity:	0.69	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	0.55	Hek293 Cytotoxicity:	0.457
BCF:	1.421 ? 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:	3.964 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.582 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.88 ? 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
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579873]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26225905]
NPO23254	Monoclea forsteri	Species	Monocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18498	Arundo donax	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23254	Monoclea forsteri	Species	Monocleaceae	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 NPC262920 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	18740
0.1-0.2	24806
0.2-0.3	4995
0.3-0.4	1018
0.4-0.5	225
0.5-0.6	56
0.6-0.7	10
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
0.697	Remote Similarity	NPC246708
0.6957	Remote Similarity	NPC49776
0.6957	Remote Similarity	NPC63118
0.6957	Remote Similarity	NPC474436
0.6479	Remote Similarity	NPC164349
0.6301	Remote Similarity	NPC294360
0.6232	Remote Similarity	NPC40552
0.6119	Remote Similarity	NPC101475
0.6076	Remote Similarity	NPC167383
0.6029	Remote Similarity	NPC235341
0.5909	Remote Similarity	NPC290598
0.5909	Remote Similarity	NPC30590
0.5844	Remote Similarity	NPC273668
0.5844	Remote Similarity	NPC283343
0.5652	Remote Similarity	NPC311078
0.5641	Remote Similarity	NPC88349
0.5571	Remote Similarity	NPC253807
0.5571	Remote Similarity	NPC158662
0.557	Remote Similarity	NPC473160
0.5542	Remote Similarity	NPC237503
0.5541	Remote Similarity	NPC488519
0.5526	Remote Similarity	NPC480919
0.5513	Remote Similarity	NPC475263
0.5493	Remote Similarity	NPC159168
0.5493	Remote Similarity	NPC470588
0.5488	Remote Similarity	NPC474190
0.5441	Remote Similarity	NPC27765
0.5441	Remote Similarity	NPC122418
0.5441	Remote Similarity	NPC491014
0.5432	Remote Similarity	NPC191763
0.5429	Remote Similarity	NPC237344
0.5429	Remote Similarity	NPC196753
0.5405	Remote Similarity	NPC136313
0.5352	Remote Similarity	NPC40394
0.5352	Remote Similarity	NPC480924
0.5333	Remote Similarity	NPC7260
0.5333	Remote Similarity	NPC210037
0.5333	Remote Similarity	NPC120968
0.5333	Remote Similarity	NPC171203
0.5333	Remote Similarity	NPC307426
0.5333	Remote Similarity	NPC98442
0.5333	Remote Similarity	NPC242468
0.5333	Remote Similarity	NPC227467
0.5333	Remote Similarity	NPC273621
0.5309	Remote Similarity	NPC476132
0.5309	Remote Similarity	NPC480921
0.5309	Remote Similarity	NPC480920
0.5278	Remote Similarity	NPC238992
0.5278	Remote Similarity	NPC95594
0.527	Remote Similarity	NPC162107
0.527	Remote Similarity	NPC46912
0.5238	Remote Similarity	NPC46388
0.5217	Remote Similarity	NPC120098
0.5211	Remote Similarity	NPC34177
0.52	Remote Similarity	NPC213412
0.52	Remote Similarity	NPC191965
0.5185	Remote Similarity	NPC258547
0.5132	Remote Similarity	NPC182797
0.5132	Remote Similarity	NPC52169
0.5132	Remote Similarity	NPC488562
0.5125	Remote Similarity	NPC488518
0.5068	Remote Similarity	NPC230295
0.5068	Remote Similarity	NPC98386
0.5067	Remote Similarity	NPC477579
0.5062	Remote Similarity	NPC471433
0.5062	Remote Similarity	NPC471432

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC262920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6904
0.1-0.2	2180
0.2-0.3	61
0.3-0.4	4
0.4-0.5	0
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
0.5753	Remote Similarity	NPD7645	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