NPASS Compound

Natural Product: NPC134481

Natural Product ID	NPC134481
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QVDQRPBOZUHTCX-CPGXJQKCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2205087
PubChem CID	10718718
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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 83 87 0 0 0 0 0 0 0 0999 V2000 7.5088 1.3998 1.6536 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4666 0.2041 2.2373 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0776 -0.6938 1.2436 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7172 -0.3041 0.7030 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0944 -1.0779 -0.1617 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7603 -0.8177 -0.7746 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2002 0.4569 -0.3633 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8756 0.9340 -0.8028 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6197 1.1108 -2.2655 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0998 0.9113 -2.4671 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4018 1.1366 -1.0670 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6403 0.2763 -0.3756 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6269 -1.1087 -1.0018 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2916 0.1720 1.0296 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9364 -0.6600 1.1551 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0146 -0.3934 0.1589 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7910 0.7957 -0.7326 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5984 1.8837 -0.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0678 1.5693 -0.4000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3983 0.4490 0.5475 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3618 -0.5733 0.6949 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9355 -1.5223 -0.3127 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5799 -1.2031 2.0818 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9134 -1.9129 1.9776 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0307 -1.0684 1.4900 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7189 -0.2226 0.2826 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7724 0.8750 0.2265 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7712 -0.9763 -1.0012 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1384 -1.8829 1.2903 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2444 2.6226 -0.9171 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2084 1.5316 -0.8906 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1042 -0.6008 0.1343 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0380 -2.0621 1.8784 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6866 1.9066 1.7605 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2692 0.6108 1.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6588 -1.9993 -0.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1485 -1.6896 -0.3792 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9055 -0.9818 -1.8592 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2557 0.5558 0.7377 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8313 1.9520 -0.2654 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0850 0.3712 -2.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9185 2.1086 -2.6689 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2710 1.7180 -3.1404 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1488 -0.0313 -2.9304 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8437 -1.8677 -0.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3417 -1.3612 -1.4763 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3535 -1.2242 -1.8292 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1137 -0.3615 1.5848 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1757 1.1704 1.4977 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -0.5210 2.2177 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6741 -1.7369 1.1095 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3154 0.5455 -1.7043 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4374 2.8960 -0.3289 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4637 1.7990 1.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6405 2.4796 -0.1561 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0787 1.2840 -1.4515 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5275 0.9565 1.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5332 -2.5227 -0.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1477 -1.4613 -1.3884 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8031 -1.9655 2.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5920 -0.4224 2.8716 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7397 -2.8260 1.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1626 -2.2620 3.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3108 -0.3599 2.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6657 1.5421 1.0893 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5242 1.4747 -0.6923 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7916 0.4601 0.1155 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8589 -1.0502 -1.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4380 -2.0360 -0.9103 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2761 -0.4326 -1.8043 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6346 -1.7004 0.4764 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9985 3.0278 -1.6743 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3596 3.0247 0.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6709 3.0610 -1.3768 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7612 1.9887 -1.8267 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1380 1.0627 -1.2468 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3160 2.3612 -0.2013 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9895 0.0034 0.4209 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6402 -0.0931 -0.7496 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4286 -1.5985 -0.2218 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0852 -2.3957 2.0024 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6122 -1.9314 2.9065 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4931 -2.7767 1.2633 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 2 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 6 12 14 1 0 14 15 1 0 16 15 1 1 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 25 29 1 0 11 30 1 1 7 31 1 0 3 32 1 0 3 33 1 0 12 8 1 0 22 16 1 0 17 11 1 0 26 20 1 0 21 16 1 0 1 34 1 0 4 35 1 0 5 36 1 0 6 37 1 0 6 38 1 0 7 39 1 1 8 40 1 1 9 41 1 0 9 42 1 0 10 43 1 0 10 44 1 0 13 45 1 0 13 46 1 0 13 47 1 0 14 48 1 0 14 49 1 0 15 50 1 0 15 51 1 0 17 52 1 6 18 53 1 0 18 54 1 0 19 55 1 0 19 56 1 0 20 57 1 1 22 58 1 0 22 59 1 0 23 60 1 0 23 61 1 0 24 62 1 0 24 63 1 0 25 64 1 1 27 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 32 80 1 0 33 81 1 0 33 82 1 0 33 83 1 0 M END

Standard InCHIKey	QVDQRPBOZUHTCX-CPGXJQKCSA-N
Standard InCHI	InChI=1S/C30H50O3/c1-20(9-8-14-25(2,3)33-32)21-12-15-28(7)23-11-10-22-26(4,5)24(31)13-16-29(22)19-30(23,29)18-17-27(21,28)6/h8,14,20-24,31-32H,9-13,15-19H2,1-7H3/b14-8+/t20-,21-,22+,23+,24+,27-,28+,29-,30+/m1/s1
SMILES	OOC(/C=C/C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C)C)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	458.38	Volume:	508.388 ? Van der Waals volume.
Dense:	0.902	LogP:	4.433 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.042 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.944 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	49.69 ? 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:	0.253	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.739	Fsp³:	0.933
MCE-18:	137.586 ? 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:	0.803	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.545	Promiscuous compounds:	0.15

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.269	MDCK Permeability:	-4.94
Pgp-inhibitor:	0.94	Pgp-substrate:	0.019
PAMPA:	0.054 ? 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%):	0.17	30% Bioavailability (F30%):	0.197
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.194	MRP1:	0.12
Plasma Protein Binding (PPB):	92.252%	Volume Distribution (VD):	-0.036
Fu:	7.113% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.981
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.991	CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.284
CYP2D6-inhibitor:	0.61	CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.931
HLM stability:	0.6 ? 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):

15.271

Half-life (T1/2):

0.851

ADMET: Toxicity

hERG Blockers:	0.113	hERG Blockers (10um):	0.289
Human Hepatotoxicity (H-HT):	0.621	Drug-induced Liver Injury (DILI):	0.314
AMES Toxicity:	0.689	Rat Oral Acute Toxicity:	0.478
Maximum Recommended Daily Dose:	0.674	Skin Sensitization:	0.991
Carcinogencity:	0.913	Eye Corrosion:	0.0
Eye Irritation:	0.026	Respiratory Toxicity:	0.693
Drug-induced Neurotoxicity:	0.029	Ototoxicity:	0.717
Hematotoxicity:	0.496	Drug-induced Nephrotoxicity:	0.425
Genotoxicity:	0.891	RPMI-8226 Immunitoxicity:	0.131
A549 Cytotoxicity:	0.179	Hek293 Cytotoxicity:	0.67
BCF:	2.605 ? 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:	4.909 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.066 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.757 ? 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
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27447736]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32233482]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	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
MIC	2

Activity Type	# Activity
Organism	2

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
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	ug.mL-1	PMID[22280816]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	25.0	ug.mL-1	PMID[22280816]

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 NPC134481 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	24981
0.1-0.2	22363
0.2-0.3	2085
0.3-0.4	335
0.4-0.5	52
0.5-0.6	24
0.6-0.7	16
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
0.7222	Intermediate Similarity	NPC22133
0.717	Intermediate Similarity	NPC82623
0.6545	Remote Similarity	NPC604180
0.6491	Remote Similarity	NPC472341
0.6429	Remote Similarity	NPC195530
0.6296	Remote Similarity	NPC41577
0.625	Remote Similarity	NPC85346
0.625	Remote Similarity	NPC65897
0.625	Remote Similarity	NPC80237
0.6182	Remote Similarity	NPC299948
0.6182	Remote Similarity	NPC241085
0.6182	Remote Similarity	NPC607543
0.614	Remote Similarity	NPC273366
0.6071	Remote Similarity	NPC331618
0.6071	Remote Similarity	NPC257191
0.6071	Remote Similarity	NPC196358
0.6	Remote Similarity	NPC89747
0.6	Remote Similarity	NPC473238
0.5965	Remote Similarity	NPC200243
0.5965	Remote Similarity	NPC254509
0.5932	Remote Similarity	NPC76518
0.5862	Remote Similarity	NPC470830
0.5862	Remote Similarity	NPC472342
0.5862	Remote Similarity	NPC479659
0.5806	Remote Similarity	NPC18384
0.5806	Remote Similarity	NPC110923
0.5806	Remote Similarity	NPC74296
0.5763	Remote Similarity	NPC473279
0.5625	Remote Similarity	NPC195366
0.5625	Remote Similarity	NPC85379
0.5625	Remote Similarity	NPC144909
0.5625	Remote Similarity	NPC476304
0.5625	Remote Similarity	NPC114743
0.5574	Remote Similarity	NPC12722
0.5556	Remote Similarity	NPC476186
0.55	Remote Similarity	NPC470558
0.5484	Remote Similarity	NPC606508
0.5469	Remote Similarity	NPC483817
0.541	Remote Similarity	NPC67872
0.5352	Remote Similarity	NPC285298
0.5246	Remote Similarity	NPC70982
0.5231	Remote Similarity	NPC307776

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC134481 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7823
0.1-0.2	1294
0.2-0.3	32
0.3-0.4	1
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