NPASS Compound

Natural Product: NPC482454

Natural Product ID	NPC482454
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AZEXNJIEBDRVJS-SPMDBHELSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44575629
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 [CHEMONTID:0002906] Phorbol esters

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 78 81 0 0 0 0 0 0 0 0999 V2000 9.4138 0.1129 2.4155 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2152 -1.1514 1.6241 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2859 -2.1300 2.2919 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9045 -1.5818 2.5236 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2559 -1.1876 1.2625 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1307 -1.6951 0.7916 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5826 -1.2220 -0.4735 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4658 -1.6871 -1.0060 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9412 -1.1708 -2.3060 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5597 -0.5867 -2.1411 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0221 0.0968 -3.0158 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9019 -0.8224 -1.0093 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3322 -0.4766 -0.4942 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5094 1.0106 -0.3379 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5219 1.5063 -1.3366 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3882 3.0067 -1.5678 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9133 1.0875 -1.0250 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8542 -0.2707 -0.3626 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0893 -1.0335 -0.7802 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3402 -0.6249 -0.9322 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9131 0.7368 -0.7322 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0632 1.4709 0.2161 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8003 2.0419 -0.3710 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3437 2.8975 0.7040 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4127 3.3657 1.3293 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4484 4.2991 2.5100 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6292 2.7928 0.6870 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7583 3.2751 0.5831 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9120 0.7401 1.3650 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3344 -1.6555 -1.3732 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8693 -1.1978 -2.5972 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 -1.0775 -0.7331 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7859 -1.4538 0.5286 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2272 -2.8464 0.4315 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3083 -1.0646 1.8507 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5213 0.8088 -2.2919 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9429 -0.1433 3.3720 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4884 0.6665 2.6219 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0545 0.7905 1.7995 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8432 -0.9186 0.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2119 -1.6150 1.5001 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1961 -3.0366 1.6832 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6930 -2.4407 3.2836 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9202 -0.7370 3.2591 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3092 -2.3955 2.9897 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7403 -0.4077 0.6533 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6331 -2.4718 1.3806 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1136 -0.4447 -1.0167 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9431 -2.4604 -0.4639 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6191 -0.3993 -2.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9069 -2.0510 -2.9851 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7729 1.2772 0.7038 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4299 1.5755 -0.5531 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2367 1.0738 -2.3300 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8334 3.5184 -0.7501 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3742 3.4586 -1.7984 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7538 3.2346 -2.4774 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9028 -0.1586 0.7428 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9262 -2.0991 -0.9925 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1193 1.2583 -1.6909 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9332 0.6150 -0.2600 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1780 2.7587 -1.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3512 3.1921 1.0563 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3600 4.9001 2.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5852 5.0219 2.4533 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3341 3.7772 3.4669 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7754 1.2751 2.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1309 -1.8297 -0.6326 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7843 -2.5917 -1.5842 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0940 -1.9763 -3.1455 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8062 -1.8861 -1.4749 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1197 -3.2515 1.4007 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5945 -2.8951 -0.3170 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0179 -3.5442 0.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6335 -1.5119 2.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3858 -0.0128 2.0968 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2793 -1.6207 2.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9624 0.1924 -2.8114 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 13 12 1 6 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 25 27 1 0 27 28 2 0 22 29 1 1 20 30 1 0 30 31 1 0 18 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 17 36 1 6 32 13 1 0 33 13 1 0 23 17 1 0 27 22 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 0 2 41 1 0 3 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 5 46 1 0 6 47 1 0 7 48 1 0 8 49 1 0 9 50 1 0 9 51 1 0 14 52 1 0 14 53 1 0 15 54 1 6 16 55 1 0 16 56 1 0 16 57 1 0 18 58 1 1 19 59 1 0 21 60 1 0 21 61 1 0 23 62 1 6 24 63 1 0 26 64 1 0 26 65 1 0 26 66 1 0 29 67 1 0 30 68 1 0 30 69 1 0 31 70 1 0 32 71 1 6 34 72 1 0 34 73 1 0 34 74 1 0 35 75 1 0 35 76 1 0 35 77 1 0 36 78 1 0 M END

Standard InCHIKey	AZEXNJIEBDRVJS-SPMDBHELSA-N
Standard InCHI	InChI=1S/C30H42O6/c1-6-7-8-9-10-11-12-13-24(32)36-29-16-20(3)30(35)22(25(29)27(29,4)5)15-21(18-31)17-28(34)23(30)14-19(2)26(28)33/h9-12,14-15,20,22-23,25,31,34-35H,6-8,13,16-18H2,1-5H3/b10-9+,12-11+/t20-,22-,23+,25+,28+,29-,30+/m0/s1
SMILES	CCCC/C=C/C=C/CC(=O)O[C@@]12C[C@H](C)[C@]3([C@@H](C=C(C[C@]4([C@H]3C=C(C)C4=O)O)CO)[C@@H]1C2(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	498.3	Volume:	530.133 ? Van der Waals volume.
Dense:	0.94	LogP:	3.621 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.596 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.569 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	22.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.201	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.225	Fsp³:	0.667
MCE-18:	76.8 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.415	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.027 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.361	Promiscuous compounds:	0.642

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.129	MDCK Permeability:	-4.763
Pgp-inhibitor:	0.039	Pgp-substrate:	0.737
PAMPA:	0.689 ? 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):	0.01
20% Bioavailability (F20%):	0.961	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.564
Plasma Protein Binding (PPB):	83.928%	Volume Distribution (VD):	-0.193
Fu:	15.961% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.976
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.027
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.193	CYP3A4-substrate:	0.706
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.02 ? 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):

3.358

Half-life (T1/2):

1.372

ADMET: Toxicity

hERG Blockers:	0.153	hERG Blockers (10um):	0.367
Human Hepatotoxicity (H-HT):	0.746	Drug-induced Liver Injury (DILI):	0.416
AMES Toxicity:	0.694	Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.608	Skin Sensitization:	0.981
Carcinogencity:	0.305	Eye Corrosion:	0.004
Eye Irritation:	0.558	Respiratory Toxicity:	0.918
Drug-induced Neurotoxicity:	0.177	Ototoxicity:	0.727
Hematotoxicity:	0.655	Drug-induced Nephrotoxicity:	0.597
Genotoxicity:	0.243	RPMI-8226 Immunitoxicity:	0.136
A549 Cytotoxicity:	0.163	Hek293 Cytotoxicity:	0.389
BCF:	1.367 ? 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:	4.048 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.837 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.069 ? 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
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190854]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	stems and twigs	Beihai, Guangxi province, China	2008-Jan	PMID[22196120]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	bark	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22608	Excoecaria agallocha	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
IC50	2

Activity Type	# Activity
Organism	1
Protein family	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1284	Protein family	Protein kinase C (PKC)	Rattus norvegicus	IC50	=	17.0	nM	PMID[7623051]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	6.0	nM	PMID[7623051]

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 NPC482454 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	16410
0.1-0.2	32298
0.2-0.3	973
0.3-0.4	85
0.4-0.5	31
0.5-0.6	36
0.6-0.7	14
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.806	Intermediate Similarity	NPC485732
0.7887	Intermediate Similarity	NPC153651
0.7869	Intermediate Similarity	NPC153036
0.7846	Intermediate Similarity	NPC485736
0.7846	Intermediate Similarity	NPC277477
0.7846	Intermediate Similarity	NPC479003
0.7846	Intermediate Similarity	NPC485735
0.7619	Intermediate Similarity	NPC158523
0.7385	Intermediate Similarity	NPC71889
0.7385	Intermediate Similarity	NPC475937
0.6711	Remote Similarity	NPC472760
0.6575	Remote Similarity	NPC485731
0.6351	Remote Similarity	NPC477091
0.6338	Remote Similarity	NPC485733
0.6324	Remote Similarity	NPC96739
0.6316	Remote Similarity	NPC479000
0.6301	Remote Similarity	NPC17138
0.6301	Remote Similarity	NPC101825
0.6301	Remote Similarity	NPC215643
0.6301	Remote Similarity	NPC265499
0.6269	Remote Similarity	NPC91189
0.6216	Remote Similarity	NPC221511
0.6081	Remote Similarity	NPC170212
0.6056	Remote Similarity	NPC174471
0.5974	Remote Similarity	NPC151216
0.5974	Remote Similarity	NPC89227
0.5926	Remote Similarity	NPC482199
0.5926	Remote Similarity	NPC482197
0.589	Remote Similarity	NPC474871
0.589	Remote Similarity	NPC260786
0.5833	Remote Similarity	NPC601392
0.5823	Remote Similarity	NPC145238
0.5789	Remote Similarity	NPC474872
0.5783	Remote Similarity	NPC482198
0.5714	Remote Similarity	NPC185876
0.5714	Remote Similarity	NPC19336
0.5696	Remote Similarity	NPC484333
0.5595	Remote Similarity	NPC180640
0.5541	Remote Similarity	NPC171905
0.5493	Remote Similarity	NPC156252
0.5455	Remote Similarity	NPC275696
0.5455	Remote Similarity	NPC255081
0.5385	Remote Similarity	NPC5991
0.5385	Remote Similarity	NPC196500
0.5385	Remote Similarity	NPC471108
0.5385	Remote Similarity	NPC5989
0.5333	Remote Similarity	NPC472397
0.5227	Remote Similarity	NPC601559
0.5195	Remote Similarity	NPC157252
0.5195	Remote Similarity	NPC472758
0.5185	Remote Similarity	NPC183540
0.5185	Remote Similarity	NPC22628
0.5185	Remote Similarity	NPC600005
0.5181	Remote Similarity	NPC222307
0.5181	Remote Similarity	NPC602538
0.5132	Remote Similarity	NPC478681
0.5128	Remote Similarity	NPC471125
0.5119	Remote Similarity	NPC159692
0.5063	Remote Similarity	NPC145182
0.5059	Remote Similarity	NPC236999

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6588
0.1-0.2	2542
0.2-0.3	20
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