NPASS Compound

Natural Product: NPC472577

Natural Product ID	NPC472577
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WNVNFNRMEDUIMJ-WTDCVXMASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3577224
PubChem CID	49831747
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

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 82 0 0 0 0 0 0 0 0999 V2000 -2.9112 2.3066 2.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9354 1.1575 2.1134 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5971 -0.1589 2.2300 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2530 -1.1818 1.2385 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9035 -1.1236 0.5735 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1124 0.1227 0.7541 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0557 1.3106 0.8952 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2604 2.5657 0.9102 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0895 2.7110 -0.6174 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9273 1.6959 -0.9828 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7187 0.3070 -0.4986 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0474 -0.1690 -0.1925 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7250 -1.1349 -0.8506 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2097 -1.7003 -1.8262 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0754 -1.5008 -0.3917 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6256 -0.8588 0.6943 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8842 -1.1662 1.1602 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5971 -2.1452 0.5092 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0534 -2.7946 -0.5810 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7856 -2.4845 -1.0498 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9675 1.6438 -2.4204 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0874 2.0380 -3.1236 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0848 2.4470 -2.5197 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0583 1.9573 -4.6044 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4675 2.3484 -1.0523 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9032 1.3623 -0.2092 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3078 3.6198 -1.0126 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5191 1.9192 -2.5205 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8777 0.0549 1.8583 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6167 -0.1385 3.1441 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1508 -1.1663 3.8972 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1407 -2.2774 3.3983 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0365 -1.0055 5.3896 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2181 -1.2799 -0.8328 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8436 -2.4178 -1.4756 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2264 -3.3441 -0.8685 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1185 -2.6760 -2.9236 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3129 -1.2629 0.2663 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0832 -2.4058 0.1645 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8850 -3.4097 0.9151 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1765 -2.4654 -0.8522 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6709 2.0141 3.0018 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4522 3.2693 2.4700 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5401 2.3768 1.2829 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2419 1.2700 2.9990 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7138 0.0495 2.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5738 -0.5719 3.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2926 -2.1844 1.7590 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2893 -2.0028 0.8121 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8001 3.4429 1.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7375 2.5471 1.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2421 3.7035 -0.8897 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9205 2.0920 -0.6122 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4120 -0.3801 -1.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0430 -0.0779 1.2040 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2514 -0.6228 2.0157 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5973 -2.3857 0.8836 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6552 -3.5720 -1.0745 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3632 -3.0072 -1.9178 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5201 2.8758 -5.0641 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6220 1.0620 -4.9795 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0312 1.9102 -5.0166 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1351 4.2139 -0.1060 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3711 3.3756 -1.1876 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9818 4.2323 -1.8792 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6040 1.9780 -2.8302 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2263 0.8876 -2.6742 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0033 2.6693 -3.1413 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5598 -0.8462 1.5320 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6668 0.8789 1.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9971 -0.8761 5.7879 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5696 -0.0592 5.5597 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5773 -1.8478 5.8187 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1627 -3.0274 -3.3830 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8522 -3.5107 -3.0329 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4921 -1.7454 -3.4113 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5160 -1.4242 -1.0173 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9838 -3.1302 -0.5214 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7045 -2.8766 -1.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 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 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 10 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 9 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 6 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 5 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 4 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 7 2 1 0 11 6 1 0 26 7 1 0 20 15 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 5 49 1 0 8 50 1 0 8 51 1 0 9 52 1 0 10 53 1 0 11 54 1 0 16 55 1 0 17 56 1 0 18 57 1 0 19 58 1 0 20 59 1 0 24 60 1 0 24 61 1 0 24 62 1 0 27 63 1 0 27 64 1 0 27 65 1 0 28 66 1 0 28 67 1 0 28 68 1 0 29 69 1 0 29 70 1 0 33 71 1 0 33 72 1 0 33 73 1 0 37 74 1 0 37 75 1 0 37 76 1 0 41 77 1 0 41 78 1 0 41 79 1 0 M END

Standard InCHIKey	WNVNFNRMEDUIMJ-WTDCVXMASA-N
Standard InCHI	InChI=1S/C30H38O11/c1-16-13-23(37-18(3)32)25(39-20(5)34)29(15-36-17(2)31)26(40-27(35)21-11-9-8-10-12-21)24(38-19(4)33)22-14-30(16,29)41-28(22,6)7/h8-12,16,22-26H,13-15H2,1-7H3/t16-,22+,23+,24+,25+,26+,29+,30+/m1/s1
SMILES	CC1CC(C(C2(C13CC(C(C2OC(=O)C4=CC=CC=C4)OC(=O)C)C(O3)(C)C)COC(=O)C)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	574.24	Volume:	568.811 ? Van der Waals volume.
Dense:	1.01	LogP:	3.116 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.11 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.848 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	25.0
TPSA:	140.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.35	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.841	Fsp³:	0.633
MCE-18:	146.816 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.051	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.244 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.133	Promiscuous compounds:	0.032

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.97	MDCK Permeability:	-4.594
Pgp-inhibitor:	0.997	Pgp-substrate:	0.211
PAMPA:	0.201 ? 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):	0.007
20% Bioavailability (F20%):	0.03	30% Bioavailability (F30%):	0.88
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.211	MRP1:	0.997
Plasma Protein Binding (PPB):	70.585%	Volume Distribution (VD):	-0.252
Fu:	28.562% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.947
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.071
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.252
CYP2C19-inhibitor:	0.032	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.669
CYP3A4-inhibitor:	0.669	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

1.06

Half-life (T1/2):

0.99

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.373
Human Hepatotoxicity (H-HT):	0.121	Drug-induced Liver Injury (DILI):	0.813
AMES Toxicity:	0.383	Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.306	Skin Sensitization:	0.454
Carcinogencity:	0.48	Eye Corrosion:	0.0
Eye Irritation:	0.029	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.416	Ototoxicity:	0.604
Hematotoxicity:	0.031	Drug-induced Nephrotoxicity:	0.212
Genotoxicity:	0.349	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.012	Hek293 Cytotoxicity:	0.284
BCF:	0.863 ? 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:	3.813 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.689 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.213 ? 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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18616221]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	stems	Montecristo National Park, province of Santa Ana, El Salvador	2004-JUN	PMID[20873773]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21419633]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25695368]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25272	Celastrus angulatus	Species	Celastraceae	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
Activity	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	68.2	%	PMID[20402524]

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 NPC472577 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	19389
0.1-0.2	28488
0.2-0.3	1393
0.3-0.4	429
0.4-0.5	95
0.5-0.6	51
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC483902
0.7101	Intermediate Similarity	NPC481061
0.7	Intermediate Similarity	NPC488918
0.7	Intermediate Similarity	NPC488913
0.6933	Remote Similarity	NPC473089
0.6667	Remote Similarity	NPC147880
0.6522	Remote Similarity	NPC473060
0.6438	Remote Similarity	NPC481071
0.6429	Remote Similarity	NPC479047
0.6429	Remote Similarity	NPC291638
0.6338	Remote Similarity	NPC148062
0.6029	Remote Similarity	NPC481066
0.5972	Remote Similarity	NPC4341
0.5972	Remote Similarity	NPC191082
0.5946	Remote Similarity	NPC479044
0.589	Remote Similarity	NPC147217
0.589	Remote Similarity	NPC137718
0.5867	Remote Similarity	NPC16912
0.5867	Remote Similarity	NPC472570
0.5833	Remote Similarity	NPC51314
0.5823	Remote Similarity	NPC473109
0.5811	Remote Similarity	NPC471100
0.5811	Remote Similarity	NPC605884
0.5694	Remote Similarity	NPC481067
0.5676	Remote Similarity	NPC43241
0.5676	Remote Similarity	NPC177340
0.5658	Remote Similarity	NPC479043
0.5658	Remote Similarity	NPC472569
0.5658	Remote Similarity	NPC11685
0.5634	Remote Similarity	NPC481047
0.5634	Remote Similarity	NPC481045
0.56	Remote Similarity	NPC254558
0.56	Remote Similarity	NPC471107
0.5584	Remote Similarity	NPC95265
0.5584	Remote Similarity	NPC97667
0.5443	Remote Similarity	NPC481489
0.5385	Remote Similarity	NPC70716
0.5385	Remote Similarity	NPC184747
0.5333	Remote Similarity	NPC90257
0.5333	Remote Similarity	NPC69357
0.5316	Remote Similarity	NPC481490
0.5278	Remote Similarity	NPC195647
0.5278	Remote Similarity	NPC200592
0.5278	Remote Similarity	NPC610542
0.5263	Remote Similarity	NPC67777
0.5263	Remote Similarity	NPC139067
0.5244	Remote Similarity	NPC479040
0.5185	Remote Similarity	NPC481488
0.5132	Remote Similarity	NPC483845
0.5128	Remote Similarity	NPC473110
0.5128	Remote Similarity	NPC481057
0.5128	Remote Similarity	NPC305403
0.5125	Remote Similarity	NPC36021
0.5119	Remote Similarity	NPC6576
0.5119	Remote Similarity	NPC610134
0.5067	Remote Similarity	NPC152440
0.5067	Remote Similarity	NPC483888
0.5065	Remote Similarity	NPC483846
0.5063	Remote Similarity	NPC57628
0.5062	Remote Similarity	NPC481068
0.5062	Remote Similarity	NPC479042
0.5059	Remote Similarity	NPC75600
0.5059	Remote Similarity	NPC483884

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4225
0.1-0.2	4754
0.2-0.3	171
0.3-0.4	0
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