NPASS Compound

Natural Product: NPC472758

Natural Product ID	NPC472758
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LJNNQVFOVQWDMN-CBVZBMKRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3582005
PubChem CID	n.a.
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 73 76 0 0 0 0 0 0 0 0999 V2000 -0.7335 -3.7697 3.2459 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0213 -3.2645 3.2242 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0642 -1.9485 2.5303 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8664 -1.5293 2.0761 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6350 -0.2603 1.3545 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7813 0.2157 1.3789 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0409 1.6674 1.6711 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2120 1.1083 0.3238 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5763 1.1257 -0.0830 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2674 0.0627 -0.5792 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6886 -1.0325 -0.6997 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6987 0.1651 -0.9845 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1896 -1.1705 -1.4899 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4296 -1.6723 -2.6767 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5160 0.5228 0.2273 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2892 1.3238 -0.8264 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1190 0.8563 -0.7200 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1746 -0.4606 -0.0607 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4825 -1.1418 0.0825 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4492 -0.5781 1.0427 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3803 -1.2608 2.4174 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5258 0.7791 1.1511 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7430 -1.0391 0.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8510 -1.1091 1.0387 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4869 -1.3948 -0.9369 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1969 -1.4528 -1.1444 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5788 -1.6516 -1.9585 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3625 -1.3509 -0.7956 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6534 0.8484 -2.1660 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4443 2.5913 -1.4074 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9650 2.8929 -2.6265 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3555 1.9431 -3.3201 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0859 4.2706 -3.1547 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3109 1.8470 2.5355 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0123 2.6195 2.1055 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4331 -3.9622 4.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3824 -3.1188 4.2527 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6569 -3.9993 2.6618 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0153 -2.1503 2.2438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3062 0.5045 1.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4885 -0.5756 1.7657 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7745 0.9092 -1.7916 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0223 -1.9233 -0.6641 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2581 -1.1854 -1.6940 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1280 -2.2247 -3.3462 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8965 -0.8772 -3.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6421 -2.4174 -2.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0390 0.0209 1.1051 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5188 0.0869 0.1051 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6024 1.6150 0.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6973 0.6365 -1.6434 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8085 1.5494 -0.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2103 -2.1658 0.5130 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1739 -1.9867 2.5793 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4109 -0.4360 3.1852 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4647 1.0490 1.3228 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7570 -1.6986 -2.0923 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2541 -2.3799 -2.7127 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7239 -0.6855 -2.4675 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4511 -2.0263 -1.4232 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8957 -1.9979 -1.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3037 1.7522 -2.7043 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1577 -0.0128 -2.6577 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7292 0.6930 -2.2187 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7780 4.2858 -4.0270 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4240 4.9220 -2.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1133 4.6846 -3.5037 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1702 1.3408 2.0601 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5509 2.9030 2.6572 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 1.3277 3.5026 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0075 2.5114 1.7941 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3866 3.6616 1.8745 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0215 2.6178 3.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 8 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 1 20 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 25 27 1 0 18 28 1 6 17 29 1 0 16 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 7 34 1 0 7 35 1 0 21 3 1 0 18 5 1 0 26 19 1 0 8 6 1 0 1 36 1 0 2 37 1 0 2 38 1 0 4 39 1 0 5 40 1 1 6 41 1 1 12 42 1 0 13 43 1 0 13 44 1 0 14 45 1 0 14 46 1 0 14 47 1 0 15 48 1 0 15 49 1 0 15 50 1 0 16 51 1 6 17 52 1 1 19 53 1 1 21 54 1 0 21 55 1 0 22 56 1 0 26 57 1 0 27 58 1 0 27 59 1 0 27 60 1 0 28 61 1 0 29 62 1 0 29 63 1 0 29 64 1 0 33 65 1 0 33 66 1 0 33 67 1 0 34 68 1 0 34 69 1 0 34 70 1 0 35 71 1 0 35 72 1 0 35 73 1 0 M END

Standard InCHIKey	LJNNQVFOVQWDMN-CBVZBMKRSA-N
Standard InCHI	InChI=1S/C27H38O8/c1-8-13(2)23(31)35-27-20(24(27,6)7)18-10-17(12-28)11-25(32)19(9-14(3)21(25)30)26(18,33)15(4)22(27)34-16(5)29/h9-10,13,15,18-20,22,28,32-33H,8,11-12H2,1-7H3/t13?,15-,18+,19-,20-,22-,25-,26-,27-/m1/s1
SMILES	OCC1=C[C@H]2[C@@H]3C([C@]3(OC(=O)C(CC)C)[C@@H]([C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C)OC(=O)C)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	490.26	Volume:	498.462 ? Van der Waals volume.
Dense:	0.984	LogP:	2.1 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.447 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.324 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	21.0
TPSA:	130.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.395	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.181	Fsp³:	0.741
MCE-18:	84.894 ? 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:	0.18	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.302	Promiscuous compounds:	0.366

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.054	MDCK Permeability:	-4.693
Pgp-inhibitor:	0.947	Pgp-substrate:	0.99
PAMPA:	0.935 ? 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):	0.484
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.912
Plasma Protein Binding (PPB):	59.413%	Volume Distribution (VD):	-0.142
Fu:	43.086% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	0.8	BCRP inhibitor:	0.005
BSEP inhibitor:	0.94

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.014	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.693	CYP3A4-substrate:	0.151
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.556 ? 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):

6.894

Half-life (T1/2):

1.296

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.238
Human Hepatotoxicity (H-HT):	0.676	Drug-induced Liver Injury (DILI):	0.446
AMES Toxicity:	0.425	Rat Oral Acute Toxicity:	0.262
Maximum Recommended Daily Dose:	0.191	Skin Sensitization:	0.877
Carcinogencity:	0.474	Eye Corrosion:	0.034
Eye Irritation:	0.579	Respiratory Toxicity:	0.589
Drug-induced Neurotoxicity:	0.144	Ototoxicity:	0.639
Hematotoxicity:	0.727	Drug-induced Nephrotoxicity:	0.556
Genotoxicity:	0.437	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.048	Hek293 Cytotoxicity:	0.112
BCF:	0.479 ? 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:	3.234 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.021 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.206 ? 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
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	Leaves	Langevin, La Reunion, France	2009-Nov	PMID[25946116]
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
EC50	5
Inhibition	3
Ratio CC50/EC50	3
CC50	2

Activity Type	# Activity
Cell line	5
Organism	4
Non-molecular	1
Others	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
NPT393	Cell line	HCT-116	Homo sapiens	Inhibition	<	40.0	%	PMID[17844994]
NPT83	Cell line	MCF7	Homo sapiens	Inhibition	<	40.0	%	PMID[23398362]
NPT306	Cell line	PC-3	Homo sapiens	Inhibition	<	40.0	%	PMID[2614419]
NPT189	Cell line	Vero	Chlorocebus aethiops	CC50	=	134000.0	nM	PMID[21911291]
NPT25	Cell line	MT4	Homo sapiens	CC50	=	102000.0	nM	PMID[20805391]
NPT856	Organism	Semliki forest virus	Semliki forest virus	EC50	>	255000.0	nM	PMID[19813743]
NPT332	Organism	Human immunodeficiency virus type 2 (ISOLATE ROD)	Human immunodeficiency virus type 2 (ISOLATE ROD)	EC50	=	107.0	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	3300.0	nM	PMID[25946116]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	271.0	nM	PubChem BioAssay data set
NPT338	Organism	Sindbis virus	Sindbis virus	EC50	>	255000.0	nM	PMID[19029333]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	376.0	n.a.	PMID[18500841]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	949.0	n.a.	PMID[17181158]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	41.0	n.a.	DrugMatrix in vivo data: Hematology

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 NPC472758 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	14948
0.1-0.2	32959
0.2-0.3	1779
0.3-0.4	35
0.4-0.5	67
0.5-0.6	33
0.6-0.7	14
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC472397
0.8871	High Similarity	NPC471125
0.875	High Similarity	NPC471126
0.8182	Intermediate Similarity	NPC471128
0.7941	Intermediate Similarity	NPC22628
0.7879	Intermediate Similarity	NPC275696
0.7879	Intermediate Similarity	NPC145182
0.7879	Intermediate Similarity	NPC255081
0.7812	Intermediate Similarity	NPC171905
0.7576	Intermediate Similarity	NPC157252
0.7568	Intermediate Similarity	NPC482198
0.75	Intermediate Similarity	NPC5991
0.75	Intermediate Similarity	NPC196500
0.75	Intermediate Similarity	NPC471108
0.75	Intermediate Similarity	NPC5989
0.7397	Intermediate Similarity	NPC472398
0.7397	Intermediate Similarity	NPC600915
0.7286	Intermediate Similarity	NPC243902
0.7183	Intermediate Similarity	NPC478999
0.7083	Intermediate Similarity	NPC484333
0.6986	Remote Similarity	NPC145238
0.6944	Remote Similarity	NPC600005
0.6842	Remote Similarity	NPC482199
0.6842	Remote Similarity	NPC482197
0.6716	Remote Similarity	NPC475937
0.6667	Remote Similarity	NPC472757
0.6375	Remote Similarity	NPC479001
0.6375	Remote Similarity	NPC479002
0.6338	Remote Similarity	NPC472401
0.6197	Remote Similarity	NPC481522
0.6125	Remote Similarity	NPC138641
0.6125	Remote Similarity	NPC611243
0.6119	Remote Similarity	NPC153036
0.6098	Remote Similarity	NPC601964
0.5942	Remote Similarity	NPC158523
0.5915	Remote Similarity	NPC482406
0.5904	Remote Similarity	NPC601392
0.589	Remote Similarity	NPC481520
0.589	Remote Similarity	NPC605797
0.5867	Remote Similarity	NPC471127
0.5867	Remote Similarity	NPC481531
0.5833	Remote Similarity	NPC601559
0.5797	Remote Similarity	NPC156252
0.5765	Remote Similarity	NPC283875
0.5765	Remote Similarity	NPC22571
0.5584	Remote Similarity	NPC472399
0.5556	Remote Similarity	NPC71889
0.55	Remote Similarity	NPC609983
0.5455	Remote Similarity	NPC488610
0.5443	Remote Similarity	NPC611949
0.5333	Remote Similarity	NPC485736
0.5333	Remote Similarity	NPC260786
0.5333	Remote Similarity	NPC277477
0.5333	Remote Similarity	NPC479003
0.5333	Remote Similarity	NPC485735
0.5333	Remote Similarity	NPC606275
0.5195	Remote Similarity	NPC234858
0.5195	Remote Similarity	NPC482454
0.5195	Remote Similarity	NPC179207
0.5185	Remote Similarity	NPC607335
0.5185	Remote Similarity	NPC610849
0.5132	Remote Similarity	NPC154363
0.5063	Remote Similarity	NPC481528
0.5063	Remote Similarity	NPC474872
0.5063	Remote Similarity	NPC481525
0.5062	Remote Similarity	NPC488611
0.506	Remote Similarity	NPC481523

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472758 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6423
0.1-0.2	2707
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