NPASS Compound

Natural Product: NPC329080

Natural Product ID	NPC329080
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NKOQECBSAYYRBF-NTAHFFFWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1927846
PubChem CID	57398868
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

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 88 91 0 0 0 0 0 0 0 0999 V2000 8.3009 -2.6089 2.9976 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0847 -2.9557 1.5385 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1564 -1.7084 0.6759 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1432 -0.7143 1.0477 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2462 -0.3269 0.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2231 0.6563 0.4935 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3231 1.0309 -0.4153 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3055 2.0094 -0.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4351 2.3597 -1.0070 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3951 3.3606 -0.6717 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1530 2.7895 -0.8392 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0874 1.6826 -0.0684 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2791 0.5183 -1.0658 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8755 -0.7041 -0.5087 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4594 -1.5367 -1.6159 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8953 -1.4677 -1.7704 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3289 -2.6233 -2.2424 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2078 -3.5438 -2.4343 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1037 -4.5428 -3.1767 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1645 -2.9858 -1.4915 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3069 -3.6126 -0.1624 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1699 -3.0079 0.8292 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3976 -1.7526 1.1322 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8930 -0.4913 0.6129 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2607 0.4454 1.5498 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3242 1.7706 0.6987 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5662 1.7007 2.1176 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5176 2.4194 2.9790 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9462 1.9510 2.6463 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4855 1.9705 -0.0544 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7212 3.1099 -0.7748 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9145 4.0710 -0.7968 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9662 3.2835 -1.5889 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2044 3.2103 -0.7613 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8430 4.5584 -2.3812 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9577 -3.9831 1.6803 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7343 -3.2933 2.5802 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7481 -3.0220 -2.5672 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1781 -1.4923 0.0160 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8907 1.0157 -2.3617 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4055 -2.0374 3.3386 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1744 -1.9250 3.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4373 -3.5157 3.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8612 -3.6481 1.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0733 -3.3806 1.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1560 -1.2357 0.7312 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0063 -2.0418 -0.3689 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1295 -0.2921 2.0574 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2625 -0.7411 -0.8181 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1625 1.1248 1.4781 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3784 0.5846 -1.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2484 2.4530 0.8861 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4770 1.9228 -1.9972 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5044 3.6713 0.3701 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5422 4.2025 -1.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7986 1.4331 0.5783 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7955 0.2840 -1.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0157 -1.2166 -2.6078 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6205 -0.6795 -1.5773 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1599 -3.2008 -1.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7361 -4.6524 -0.3729 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2946 -3.9187 0.2624 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1251 -1.5925 1.9557 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7846 0.0179 0.1288 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2178 0.0809 1.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4632 1.9142 2.7676 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4919 3.4832 2.6678 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8061 2.3046 4.0361 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9795 1.5987 3.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1046 3.0476 2.6990 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7495 1.5062 2.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9391 2.4476 -2.3392 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6204 4.2468 -0.6789 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9718 2.6373 -1.3530 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0573 2.7560 0.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7551 4.6987 -2.6012 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3709 4.5225 -3.3526 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1460 5.4578 -1.7936 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6411 -4.4996 0.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2886 -4.7326 2.1461 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5746 -3.0226 2.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1650 -3.6097 -1.7358 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7185 -3.7057 -3.4520 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3510 -2.1292 -2.8335 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0980 -1.6915 0.9546 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9632 0.8623 -2.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3924 0.5650 -3.2649 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6288 2.1059 -2.4549 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 3 5 6 1 0 6 7 2 3 7 8 1 0 8 9 2 3 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 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 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 33 35 1 0 22 36 1 0 36 37 1 0 17 38 1 0 14 39 1 0 13 40 1 0 26 12 1 0 24 14 1 0 20 15 1 0 27 25 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 2 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 5 49 1 0 6 50 1 0 7 51 1 0 8 52 1 0 9 53 1 0 10 54 1 0 10 55 1 0 12 56 1 0 13 57 1 0 15 58 1 0 16 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 23 63 1 0 24 64 1 0 25 65 1 0 28 66 1 0 28 67 1 0 28 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 33 72 1 0 34 73 1 0 34 74 1 0 34 75 1 0 35 76 1 0 35 77 1 0 35 78 1 0 36 79 1 0 36 80 1 0 37 81 1 0 38 82 1 0 38 83 1 0 38 84 1 0 39 85 1 0 40 86 1 0 40 87 1 0 40 88 1 0 M END

Standard InCHIKey	NKOQECBSAYYRBF-NTAHFFFWSA-N
Standard InCHI	InChI=1S/C34H48O6/c1-8-9-10-11-12-13-14-15-16-39-30-23(5)33(38)26-17-22(4)28(36)25(26)18-24(20-35)19-27(33)29-32(6,7)34(29,30)40-31(37)21(2)3/h10-15,17,19,21,23,25-27,29-30,35,38H,8-9,16,18,20H2,1-7H3/b11-10+,13-12+,15-14-/t23-,25+,26-,27+,29-,30-,33+,34-/m1/s1
SMILES	CCCC=CC=CC=CCOC1C(C2(C3C=C(C(=O)C3CC(=CC2C4C1(C4(C)C)OC(=O)C(C)C)CO)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.35	Volume:	596.68 ? Van der Waals volume.
Dense:	0.926	LogP:	5.072 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.319 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.074 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
TPSA:	93.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.211	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.507	Fsp³:	0.647
MCE-18:	75.429 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.206	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.033 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.223 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.32	Promiscuous compounds:	0.043

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.119	MDCK Permeability:	-4.784
Pgp-inhibitor:	0.692	Pgp-substrate:	0.036
PAMPA:	0.286 ? 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):	0.033
20% Bioavailability (F20%):	0.323	30% Bioavailability (F30%):	0.804
50% Bioavailability (F50%):	0.671

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.996
Plasma Protein Binding (PPB):	90.83%	Volume Distribution (VD):	0.072
Fu:	8.269% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.181
OATP1B3 inhibitor:	0.513	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.928	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.981	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.902	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.01	CYP2C8-inhibitor:	0.957
HLM stability:	0.998 ? 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):

9.954

Half-life (T1/2):

0.532

ADMET: Toxicity

hERG Blockers:	0.241	hERG Blockers (10um):	0.514
Human Hepatotoxicity (H-HT):	0.619	Drug-induced Liver Injury (DILI):	0.231
AMES Toxicity:	0.612	Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.462	Skin Sensitization:	0.857
Carcinogencity:	0.346	Eye Corrosion:	0.0
Eye Irritation:	0.011	Respiratory Toxicity:	0.843
Drug-induced Neurotoxicity:	0.458	Ototoxicity:	0.955
Hematotoxicity:	0.188	Drug-induced Nephrotoxicity:	0.257
Genotoxicity:	0.048	RPMI-8226 Immunitoxicity:	0.139
A549 Cytotoxicity:	0.203	Hek293 Cytotoxicity:	0.554
BCF:	1.78 ? 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:	4.255 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.091 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.346 ? 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
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	Roots	Kunming, Yunnan Province, China	2010-JUL	PMID[21928782]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[21928782]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22560584]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7775985]
NPO12377	Euphorbia prolifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12377	Euphorbia prolifera	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
Activity	3

Activity Type	# Activity
Cell line	3

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
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	69.6	%	PMID[21928782]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	77.3	%	PMID[21928782]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	84.1	%	PMID[21928782]

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 NPC329080 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	19798
0.1-0.2	29427
0.2-0.3	506
0.3-0.4	61
0.4-0.5	33
0.5-0.6	8
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
0.7763	Intermediate Similarity	NPC482220
0.7632	Intermediate Similarity	NPC482221
0.7125	Intermediate Similarity	NPC482219
0.7083	Intermediate Similarity	NPC482406
0.6923	Remote Similarity	NPC236918
0.6923	Remote Similarity	NPC156745
0.68	Remote Similarity	NPC481520
0.6711	Remote Similarity	NPC234858
0.6711	Remote Similarity	NPC179207
0.6585	Remote Similarity	NPC482222
0.6456	Remote Similarity	NPC608501
0.6447	Remote Similarity	NPC472757
0.6447	Remote Similarity	NPC481522
0.6341	Remote Similarity	NPC472759
0.6125	Remote Similarity	NPC471127
0.6125	Remote Similarity	NPC476111
0.6125	Remote Similarity	NPC481525
0.6125	Remote Similarity	NPC481531
0.6026	Remote Similarity	NPC154363
0.6	Remote Similarity	NPC485737
0.5714	Remote Similarity	NPC10721
0.5698	Remote Similarity	NPC481523
0.5663	Remote Similarity	NPC90814
0.5663	Remote Similarity	NPC189393
0.5488	Remote Similarity	NPC482405
0.5275	Remote Similarity	NPC140021
0.5238	Remote Similarity	NPC475885
0.519	Remote Similarity	NPC481521

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC329080 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6783
0.1-0.2	2349
0.2-0.3	18
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