NPASS Compound

Natural Product: NPC482195

Natural Product ID	NPC482195
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YLABXLIBUBLBLD-NPVFZVCGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	90645381
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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 89 94 0 0 0 0 0 0 0 0999 V2000 0.1800 0.2896 2.1766 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0147 0.9816 0.8767 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0958 1.3046 0.1628 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4433 0.9626 0.6717 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5312 1.9648 0.7445 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7894 1.1615 0.9753 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9555 0.7441 2.4063 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5710 -0.0141 0.0577 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0654 -0.2267 0.0527 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4014 -0.5977 -1.1918 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2017 0.2643 -2.0310 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9821 -1.9907 -1.4500 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9312 -2.1626 -2.9709 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5423 -2.2669 -0.9149 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4551 -1.5459 -1.6905 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3817 -0.5802 -1.3310 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9596 -0.1708 -0.0672 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3526 1.2160 0.3609 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4148 2.0096 -0.7667 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 3.1183 -0.8881 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9510 3.3986 0.1013 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2134 3.8730 -2.1155 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0166 4.9775 -2.2563 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0399 5.7369 -3.4082 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2163 5.3540 -4.4472 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3984 4.2546 -4.3439 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4052 3.5158 -3.1644 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9270 -0.9370 1.0628 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0789 -1.1907 1.8096 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1378 -0.6812 1.3955 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0555 -2.0000 3.0012 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2331 -2.2054 3.7042 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2978 -2.9672 4.8502 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1279 -3.5422 5.3017 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9893 -3.3554 4.6394 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9318 -2.6000 3.5051 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8777 -1.9557 -1.8164 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6082 -1.9606 -3.1432 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3983 -2.9520 -0.8449 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4490 -3.6992 -0.9733 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5732 -4.5411 0.0884 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7875 -4.0362 1.2191 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4710 -6.0248 -0.0063 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5206 -0.2735 1.2975 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3362 2.9846 1.6695 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3021 4.3098 1.2607 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4483 4.6253 0.0303 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0982 5.4531 2.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7236 0.4120 2.8196 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3969 -0.7835 2.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0156 0.7129 2.7762 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0365 1.8196 -0.7881 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6413 2.4107 -0.2818 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7065 1.6823 0.6508 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4132 -0.1705 2.6787 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6676 1.5786 3.0754 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0444 0.5252 2.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9628 0.2126 -0.9458 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1136 -0.9019 0.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6537 -2.7600 -1.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9441 -2.5296 -3.2492 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2249 -2.9423 -3.2468 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8304 -1.1984 -3.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6893 -2.0497 0.1429 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0413 -1.4274 -2.7674 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5781 0.2681 -2.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0168 0.1293 -0.2430 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0287 1.5768 1.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6621 5.2724 -1.4337 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6895 6.5918 -3.4617 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1948 5.9139 -5.3743 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7679 3.9871 -5.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7639 2.6693 -3.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1512 -1.7517 3.3460 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2301 -3.1200 5.3920 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1372 -4.1562 6.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9824 -2.4822 3.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6570 -2.9932 -3.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0252 -1.3511 -3.8623 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6114 -1.4909 -3.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4899 -2.7389 -0.6418 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8369 -3.0671 0.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -3.9383 -1.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5579 -6.3863 0.0271 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9013 -6.3128 -1.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1284 -6.5300 0.7458 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0990 5.8522 2.4973 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5034 5.1466 3.0505 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5866 6.2983 1.6824 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 17 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 16 37 1 0 37 38 1 0 37 39 1 0 14 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 9 44 1 1 5 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 18 2 1 0 27 22 1 0 36 31 1 0 9 4 1 0 37 15 1 0 4 44 1 1 1 49 1 0 1 50 1 0 1 51 1 0 3 52 1 0 5 53 1 6 6 54 1 6 7 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 12 60 1 1 13 61 1 0 13 62 1 0 13 63 1 0 14 64 1 1 15 65 1 6 16 66 1 6 17 67 1 6 18 68 1 1 23 69 1 0 24 70 1 0 25 71 1 0 26 72 1 0 27 73 1 0 32 74 1 0 33 75 1 0 34 76 1 0 36 77 1 0 38 78 1 0 38 79 1 0 38 80 1 0 39 81 1 0 39 82 1 0 39 83 1 0 43 84 1 0 43 85 1 0 43 86 1 0 48 87 1 0 48 88 1 0 48 89 1 0 M END

Standard InCHIKey	YLABXLIBUBLBLD-NPVFZVCGSA-N
Standard InCHI	InChI=1S/C37H41NO10/c1-19-16-37-32(45-23(5)40)20(2)17-36(37,48-37)31(41)21(3)29(44-22(4)39)26-27(35(26,6)7)30(47-34(43)25-14-11-15-38-18-25)28(19)46-33(42)24-12-9-8-10-13-24/h8-16,18,20-21,26-30,32H,17H2,1-7H3/b19-16+/t20-,21+,26-,27+,28+,29-,30+,32-,36-,37-/m0/s1
SMILES	C/C/1=C[C@]23[C@H]([C@@H](C)C[C@@]2(C(=O)[C@H](C)[C@@H]([C@@H]2[C@H]([C@H]([C@@H]1OC(=O)c1ccccc1)OC(=O)c1cccnc1)C2(C)C)OC(=O)C)O3)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	659.27	Volume:	664.431 ? Van der Waals volume.
Dense:	0.992	LogP:	3.377 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.315 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.071 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
TPSA:	147.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.184	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.649	Fsp³:	0.514
MCE-18:	147.429 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.759	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.036	Promiscuous compounds:	0.056

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.184	MDCK Permeability:	-4.912
Pgp-inhibitor:	1.0	Pgp-substrate:	0.012
PAMPA:	0.299 ? 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):	0.0
20% Bioavailability (F20%):	0.439	30% Bioavailability (F30%):	0.604
50% Bioavailability (F50%):	0.833

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	1.0
Plasma Protein Binding (PPB):	90.027%	Volume Distribution (VD):	0.276
Fu:	8.582% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.895	BCRP inhibitor:	0.001
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.468
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.425
CYP3A4-inhibitor:	0.202	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

6.576

Half-life (T1/2):

0.605

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.538
Human Hepatotoxicity (H-HT):	0.089	Drug-induced Liver Injury (DILI):	0.947
AMES Toxicity:	0.487	Rat Oral Acute Toxicity:	0.407
Maximum Recommended Daily Dose:	0.201	Skin Sensitization:	0.994
Carcinogencity:	0.645	Eye Corrosion:	0.0
Eye Irritation:	0.176	Respiratory Toxicity:	0.257
Drug-induced Neurotoxicity:	0.518	Ototoxicity:	0.226
Hematotoxicity:	0.386	Drug-induced Nephrotoxicity:	0.735
Genotoxicity:	0.956	RPMI-8226 Immunitoxicity:	0.116
A549 Cytotoxicity:	0.247	Hek293 Cytotoxicity:	0.401
BCF:	0.843 ? 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:	3.778 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.765 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.567 ? 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
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24840014]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[31180680]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10031	Euphorbia antiquorum	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	4

Activity Type	# Activity
Individual protein	2
Cell line	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	<	10000.0	nM	PMID[24840014]
NPT4862	Individual protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	IC50	=	410.0	nM	PMID[24840014]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[24840014]
NPT81	Cell line	A549	Homo sapiens	IC50	<	10000.0	nM	PMID[24840014]

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 NPC482195 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	14026
0.1-0.2	33720
0.2-0.3	1626
0.3-0.4	393
0.4-0.5	62
0.5-0.6	24
0.6-0.7	2
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
0.7848	Intermediate Similarity	NPC29922
0.7848	Intermediate Similarity	NPC477096
0.7407	Intermediate Similarity	NPC477095
0.7176	Intermediate Similarity	NPC477094
0.6591	Remote Similarity	NPC482175
0.6	Remote Similarity	NPC482181
0.5778	Remote Similarity	NPC477100
0.5778	Remote Similarity	NPC477098
0.5638	Remote Similarity	NPC272004
0.5638	Remote Similarity	NPC477101
0.5638	Remote Similarity	NPC477099
0.5638	Remote Similarity	NPC477097
0.5543	Remote Similarity	NPC482182
0.5368	Remote Similarity	NPC482402
0.5349	Remote Similarity	NPC482178
0.5349	Remote Similarity	NPC482177
0.5349	Remote Similarity	NPC482185
0.5349	Remote Similarity	NPC482193
0.5287	Remote Similarity	NPC482192
0.5172	Remote Similarity	NPC475277
0.5172	Remote Similarity	NPC475495
0.5172	Remote Similarity	NPC482184
0.5172	Remote Similarity	NPC477093
0.5155	Remote Similarity	NPC482400
0.5149	Remote Similarity	NPC482258
0.5146	Remote Similarity	NPC482261
0.5114	Remote Similarity	NPC482179
0.5111	Remote Similarity	NPC482180
0.5055	Remote Similarity	NPC473522
0.5053	Remote Similarity	NPC482188

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482195 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3217
0.1-0.2	5837
0.2-0.3	95
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