NPASS Compound

Natural Product: NPC476071

Natural Product ID	NPC476071
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oleanderic Acid
IUPAC Name	(1R,2R,4aR,6aR,6aR,6bR,8aR,10S,12aR,14aR,14bR)-2,10-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a,14b-hexadecahydropicene-4a-carboxylic acid
Synonyms	oleanderic acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL524527
PubChem CID	44583857
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 84 88 0 0 0 0 0 0 0 0999 V2000 -3.2186 -2.5547 0.6144 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6574 -1.0874 0.6837 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8601 -0.3253 -0.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4022 -0.3485 -0.1736 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7605 -0.5155 -1.5426 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7190 -0.4627 -1.5356 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3129 0.6655 -0.7564 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7885 0.5192 -0.7452 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2134 -0.0346 -2.1184 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6991 -0.1321 -2.2713 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4686 -0.5342 -1.0801 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7331 -0.8001 0.1679 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2929 -0.5271 0.2009 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7482 -0.2174 1.5738 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2516 -0.2437 1.4718 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6803 0.8340 0.6056 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8177 0.7862 0.6023 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3997 2.1258 0.2497 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4887 2.1387 -0.7549 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4572 1.0044 -0.7129 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6144 1.3488 0.2411 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6540 0.2755 -0.0037 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1255 -1.0747 0.3944 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5372 -2.0783 -0.6611 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7854 -1.4396 1.5796 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1218 1.0174 -2.0656 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1050 -0.0246 -2.7313 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7085 2.1897 -2.4798 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2086 0.5534 2.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0565 2.1797 1.2025 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3831 -0.0766 1.3620 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9296 -2.2853 0.5394 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2667 -1.6552 -1.4369 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4690 1.8475 -0.6255 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0699 -3.2271 0.8466 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9591 -2.7429 -0.4482 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3245 -2.7385 1.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5004 -0.7630 1.6981 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0835 -0.9746 -1.2894 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1451 -1.2882 0.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0727 -1.5519 -1.8750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1615 0.1571 -2.3011 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0279 -0.3037 -2.6121 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0806 -1.4689 -1.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0711 1.6088 -1.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8417 -1.1009 -2.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8292 0.5882 -2.9403 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8560 -0.8514 -3.1362 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1172 0.8255 -2.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2630 0.2449 -0.8578 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7563 -1.4785 -0.1026 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1896 0.6410 2.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0243 -1.1110 2.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8639 -0.3522 2.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0051 -1.2160 0.9461 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6001 2.8090 -0.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7770 2.6931 1.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0745 2.3084 -1.7943 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1094 3.0743 -0.6004 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9983 2.3215 -0.0596 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3242 1.2748 1.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8865 0.2945 -1.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5763 0.5653 0.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3989 -1.6601 -1.2583 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7346 -2.3288 -1.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9659 -3.0033 -0.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2581 -1.0220 2.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2443 2.1471 -3.3548 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2154 -0.4982 2.3486 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4956 1.0961 2.7686 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1664 1.1047 2.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1776 2.6818 1.7106 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8216 2.1311 1.9774 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3340 2.9281 0.4330 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9300 -0.3859 2.3062 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4346 -0.4921 1.3858 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4919 0.9903 1.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4191 -2.8754 -0.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9817 -2.5639 0.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4084 -2.4948 1.4951 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0987 -1.6816 -0.9088 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6071 2.2218 0.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5082 1.8529 -1.0716 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9133 2.5462 -1.3147 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 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 0 13 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 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 20 26 1 0 26 27 2 0 26 28 1 0 17 29 1 0 16 30 1 0 12 31 1 0 12 32 1 0 11 33 1 0 8 34 1 0 23 2 1 0 20 3 1 0 17 4 1 0 16 7 1 0 13 8 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 3 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 7 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 21 60 1 0 21 61 1 0 22 62 1 0 22 63 1 0 24 64 1 0 24 65 1 0 24 66 1 0 25 67 1 0 28 68 1 0 29 69 1 0 29 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 34 82 1 0 34 83 1 0 34 84 1 0 M END

Standard InCHIKey	WJCIWKNYROGCFD-XOVAVQBPSA-N
Standard InCHI	InChI=1S/C30H50O4/c1-18-23-19-8-9-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,6)27(19,5)14-16-30(23,24(32)33)17-15-29(18,7)34/h18-23,31,34H,8-17H2,1-7H3,(H,32,33)/t18-,19-,20+,21-,22+,23+,26+,27-,28-,29-,30-/m1/s1
SMILES	CC1C2C3CCC4C5(CCC(C(C5CCC4(C3(CCC2(CCC1(C)O)C(=O)O)C)C)(C)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	474.37	Volume:	517.178 ? Van der Waals volume.
Dense:	0.917	LogP:	3.161 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.225 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.559 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.418	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.888	Fsp³:	0.967
MCE-18:	109.831 ? 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:	0.065	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.022 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.276	Promiscuous compounds:	0.019

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.401	MDCK Permeability:	-4.922
Pgp-inhibitor:	0.0	Pgp-substrate:	0.054
PAMPA:	0.977 ? 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):	0.006
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.006
50% Bioavailability (F50%):	0.876

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.155	MRP1:	1.0
Plasma Protein Binding (PPB):	84.84%	Volume Distribution (VD):	-0.267
Fu:	11.671% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.004
OATP1B3 inhibitor:	0.783	BCRP inhibitor:	0.0
BSEP inhibitor:	0.27

ADMET: Metabolism

CYP1A2-inhibitor:	0.2	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.781	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.989	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.992	CYP2C8-inhibitor:	0.018
HLM stability:	0.03 ? 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):

5.791

Half-life (T1/2):

1.728

ADMET: Toxicity

hERG Blockers:	0.073	hERG Blockers (10um):	0.259
Human Hepatotoxicity (H-HT):	0.527	Drug-induced Liver Injury (DILI):	0.063
AMES Toxicity:	0.048	Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.561	Skin Sensitization:	0.202
Carcinogencity:	0.309	Eye Corrosion:	0.012
Eye Irritation:	0.375	Respiratory Toxicity:	0.736
Drug-induced Neurotoxicity:	0.055	Ototoxicity:	0.947
Hematotoxicity:	0.149	Drug-induced Nephrotoxicity:	0.208
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.063	Hek293 Cytotoxicity:	0.134
BCF:	1.612 ? 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:	4.526 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.96 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.15 ? 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
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	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
Cell line	1
Non-molecular	1

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
NPT1475	Cell line	WI-38 VA13	Homo sapiens	IC50	>	212000.0	nM	PMID[17958396]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	159000.0	nM	PMID[15730243]

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 NPC476071 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	24961
0.1-0.2	20967
0.2-0.3	3149
0.3-0.4	557
0.4-0.5	188
0.5-0.6	18
0.6-0.7	5
0.7-0.8	1
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
0.7213	Intermediate Similarity	NPC30583
0.7213	Intermediate Similarity	NPC264317
0.7213	Intermediate Similarity	NPC294438
0.7167	Intermediate Similarity	NPC472608
0.6875	Remote Similarity	NPC16377
0.6615	Remote Similarity	NPC18064
0.6119	Remote Similarity	NPC151191
0.6061	Remote Similarity	NPC488164
0.6061	Remote Similarity	NPC264005
0.5714	Remote Similarity	NPC488165
0.5652	Remote Similarity	NPC2783
0.5588	Remote Similarity	NPC474686
0.5479	Remote Similarity	NPC481311
0.5455	Remote Similarity	NPC298168
0.5455	Remote Similarity	NPC143133
0.5362	Remote Similarity	NPC181225
0.5362	Remote Similarity	NPC488506
0.5362	Remote Similarity	NPC220498
0.5323	Remote Similarity	NPC480925
0.5323	Remote Similarity	NPC48079
0.5286	Remote Similarity	NPC474512
0.5238	Remote Similarity	NPC212733
0.5167	Remote Similarity	NPC232112
0.5143	Remote Similarity	NPC213832
0.5077	Remote Similarity	NPC245869
0.507	Remote Similarity	NPC201655
0.5068	Remote Similarity	NPC252714

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476071 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6207
0.1-0.2	2856
0.2-0.3	77
0.3-0.4	6
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7213	Intermediate Similarity	NPD7520	Phase 1

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