NPASS Compound

Natural Product: NPC477577

Natural Product ID	NPC477577
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(20S,28S)-28-Methoxy-20,28-epoxytaraxasterane-3beta-ol
IUPAC Name	(1R,4R,5R,8R,10S,13R,14R,17R,18S,19S,20S,22S)-22-methoxy-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.01,18.04,17.05,14.08,13]tetracosan-10-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	16083124
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 86 91 0 0 0 0 0 0 0 0999 V2000 -3.3167 -0.0301 2.8750 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5336 0.4407 1.4307 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6591 -0.3531 0.5143 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4115 0.3819 0.0703 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8135 1.1350 1.1835 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6012 1.5701 1.0202 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3896 0.5150 0.3534 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8778 0.8418 0.2087 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5217 1.1974 1.5063 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0369 -0.0284 2.2611 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2534 -0.5164 1.4621 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9452 -0.6102 -0.0038 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4765 -0.4666 -0.2461 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0488 -0.8264 -1.6271 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5698 -0.8683 -1.7551 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7828 0.0514 -0.9245 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5214 -0.6674 -0.5338 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1980 -1.3439 -1.6615 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6073 -0.9769 -1.9257 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4532 -0.6093 -0.7695 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4160 -1.7517 -0.4131 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0134 -1.4645 0.9699 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9834 0.0659 1.0913 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3794 0.5574 -0.1302 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2767 0.6456 -0.9883 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6365 0.8640 -2.2927 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2077 2.1199 -2.7310 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9180 0.5400 2.1561 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2251 -1.7282 0.5363 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3210 1.2124 -1.8160 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8136 0.2575 -0.8607 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2730 -2.0617 -0.4095 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3438 0.3354 1.7096 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1163 1.9783 -0.7387 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6827 -0.9431 2.8813 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8889 0.7914 3.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2648 -0.3126 3.3652 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3935 1.5199 1.3950 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4669 -1.3243 0.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6965 1.0969 -0.7373 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4282 2.0669 1.3466 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9434 0.5246 2.1237 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7199 2.5874 0.5839 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9778 1.6950 2.0823 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3851 -0.3805 1.0475 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9853 1.8847 2.1549 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4735 1.7572 1.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4491 0.3660 3.2209 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2850 -0.8000 2.3925 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5257 -1.4879 1.9255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0179 -1.2598 0.4244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4713 -1.8580 -1.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5413 -0.1981 -2.4205 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2378 -1.9375 -1.5909 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3503 -0.7092 -2.8556 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6231 -1.1318 -2.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1218 -2.4699 -1.5770 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7139 -0.1579 -2.6984 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1050 -1.8553 -2.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2159 -1.8431 -1.1483 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7907 -2.6476 -0.3033 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4181 -1.9261 1.7645 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0792 -1.7628 1.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7156 1.5534 -0.6172 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7100 2.8705 -2.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1262 2.1903 -2.4957 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4332 2.3055 -3.7799 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3378 -0.3160 2.7437 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4202 1.2818 2.8147 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8147 1.0635 1.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7653 -2.1993 0.3756 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3387 -1.3467 1.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9610 -2.5769 0.4075 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0056 2.0875 -1.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0948 1.4349 -2.6036 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5769 0.8970 -2.4269 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3732 0.4794 -1.8337 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1316 1.2002 -0.3923 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7773 -0.2922 -1.0852 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4852 -2.0982 -1.4780 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2025 -2.3161 0.1414 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4599 -2.7412 -0.0899 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1745 -0.2035 1.7287 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2625 2.7133 -0.7448 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9935 2.6068 -0.3993 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3200 1.7144 -1.7668 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 20 19 1 6 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 23 28 1 1 17 29 1 1 16 30 1 6 12 31 1 0 12 32 1 0 11 33 1 0 8 34 1 6 23 2 1 0 20 3 1 0 17 4 1 0 16 7 1 0 13 8 1 0 25 20 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 1 3 39 1 1 4 40 1 6 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 7 45 1 1 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 1 13 51 1 1 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 25 64 1 1 27 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 33 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 M END

Standard InCHIKey	KODHIHGBCAPDKG-GCWNOTCBSA-N
Standard InCHI	InChI=1S/C31H52O3/c1-19-24-20-9-10-22-27(4)13-12-23(32)26(2,3)21(27)11-14-29(22,6)28(20,5)15-17-31(24)18-16-30(19,7)34-25(31)33-8/h19-25,32H,9-18H2,1-8H3/t19-,20+,21-,22+,23-,24+,25-,27-,28+,29+,30-,31+/m0/s1
SMILES	C[C@H]1[C@@H]2[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC[C@@]26CC[C@@]1(O[C@@H]6OC)C)C)C)(C)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.39	Volume:	519.764 ? Van der Waals volume.
Dense:	0.909	LogP:	4.35 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.106 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.923 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	29.0
TPSA:	38.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	7.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.438	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.29	Fsp³:	1.0
MCE-18:	160.903 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.952	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.295	Promiscuous compounds:	0.133

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.279	MDCK Permeability:	-4.99
Pgp-inhibitor:	0.91	Pgp-substrate:	0.116
PAMPA:	0.723 ? 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):	0.002
20% Bioavailability (F20%):	0.775	30% Bioavailability (F30%):	0.261
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.854	MRP1:	0.85
Plasma Protein Binding (PPB):	98.081%	Volume Distribution (VD):	0.083
Fu:	3.054% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.872
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.171	CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.013
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.995	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.922	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.162
HLM stability:	0.602 ? 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):

13.664

Half-life (T1/2):

0.524

ADMET: Toxicity

hERG Blockers:	0.071	hERG Blockers (10um):	0.225
Human Hepatotoxicity (H-HT):	0.579	Drug-induced Liver Injury (DILI):	0.189
AMES Toxicity:	0.599	Rat Oral Acute Toxicity:	0.583
Maximum Recommended Daily Dose:	0.495	Skin Sensitization:	0.985
Carcinogencity:	0.865	Eye Corrosion:	0.064
Eye Irritation:	0.672	Respiratory Toxicity:	0.8
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.575
Hematotoxicity:	0.488	Drug-induced Nephrotoxicity:	0.769
Genotoxicity:	0.362	RPMI-8226 Immunitoxicity:	0.063
A549 Cytotoxicity:	0.506	Hek293 Cytotoxicity:	0.43
BCF:	2.507 ? 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:	4.207 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.106 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.846 ? 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	5

Activity Type	# Activity
Cell line	3
Others	2

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	=	11700	nM	PMID[16933868]
NPT81	Cell line	A549	Homo sapiens	IC50	=	80000	nM	PMID[16933868]
NPT81	Cell line	A549	Homo sapiens	IC50	=	76000	nM	PMID[16933868]
NPT27	Others	Unspecified	n.a.	IC50	=	11800	nM	PMID[16933868]
NPT2	Others	Unspecified	n.a.	IC50	=	10300	nM	PMID[16933868]

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 NPC477577 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	25939
0.1-0.2	21277
0.2-0.3	2188
0.3-0.4	367
0.4-0.5	51
0.5-0.6	35
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	Natural Product ID
0.5593	Remote Similarity	NPC142712
0.5574	Remote Similarity	NPC97534
0.5574	Remote Similarity	NPC195155
0.55	Remote Similarity	NPC480925
0.55	Remote Similarity	NPC48079
0.5484	Remote Similarity	NPC144075
0.5455	Remote Similarity	NPC477578
0.541	Remote Similarity	NPC192638
0.541	Remote Similarity	NPC25511
0.541	Remote Similarity	NPC600137
0.5397	Remote Similarity	NPC58631
0.5397	Remote Similarity	NPC248830
0.5397	Remote Similarity	NPC212241
0.5345	Remote Similarity	NPC232112
0.5312	Remote Similarity	NPC5767
0.5312	Remote Similarity	NPC475742
0.5303	Remote Similarity	NPC12774
0.5303	Remote Similarity	NPC477508
0.5294	Remote Similarity	NPC481321
0.5238	Remote Similarity	NPC301226
0.5231	Remote Similarity	NPC91387
0.5231	Remote Similarity	NPC74595
0.5231	Remote Similarity	NPC231680
0.5231	Remote Similarity	NPC119355
0.5231	Remote Similarity	NPC270306
0.5231	Remote Similarity	NPC264665
0.5231	Remote Similarity	NPC269396
0.5156	Remote Similarity	NPC231256
0.5156	Remote Similarity	NPC178383
0.5152	Remote Similarity	NPC298168
0.5152	Remote Similarity	NPC143133
0.5077	Remote Similarity	NPC201725
0.5075	Remote Similarity	NPC49599
0.5075	Remote Similarity	NPC49627
0.5072	Remote Similarity	NPC483720

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7500
0.1-0.2	1611
0.2-0.3	37
0.3-0.4	1
0.4-0.5	1
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