NPASS Compound

Natural Product: NPC271784

Natural Product ID	NPC271784
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Methyl Lucidenate F
IUPAC Name	methyl (4R)-4-[(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3,7,11,15-tetraoxo-2,5,6,12,16,17-hexahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Synonyms	Methyl Lucidenate F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL462240
PubChem CID	21633085
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 72 75 0 0 0 0 0 0 0 0999 V2000 8.8765 1.1161 1.2326 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5439 0.6360 1.4620 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7595 0.2061 0.3749 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3078 0.2787 -0.7576 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3719 -0.2990 0.5750 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8431 -0.6643 -0.7980 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4335 -1.1966 -0.7403 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4793 -0.1876 -0.1594 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5468 1.0343 -1.0877 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1998 1.6809 -0.9471 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8679 2.7258 -1.4709 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3932 0.8311 -0.0790 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0433 -0.5445 -0.3154 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7118 -0.9678 -1.7095 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5441 -1.5564 0.6762 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8790 -1.2503 1.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4010 -1.8035 1.9724 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6603 -0.3174 0.2013 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0351 0.7175 -0.3396 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8415 1.6204 -1.1347 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4502 2.1667 -2.1776 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2498 1.9394 -0.7003 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7662 0.8435 0.2171 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1176 -0.4741 -0.0294 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2614 -0.9973 -1.4313 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6944 -1.5229 0.9015 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1707 -1.6565 0.6195 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7713 -0.3482 0.9694 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6836 -0.2937 1.7664 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2493 0.8692 0.3414 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0051 1.0999 -0.9219 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5830 2.0255 1.3064 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5892 1.2190 1.3936 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4501 -2.5054 -0.0349 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0649 1.9170 1.9665 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0204 1.4058 0.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5588 0.2593 1.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7977 0.5134 1.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4568 -1.1995 1.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9495 0.2413 -1.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5067 -1.4617 -1.1908 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1268 -1.3699 -1.7992 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7344 0.0741 0.8660 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6674 0.7219 -2.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2999 1.7592 -0.7384 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3943 -1.1859 -1.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1829 -1.9398 -1.9643 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8799 -0.2004 -2.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4956 -2.5385 0.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1093 -1.6374 1.6003 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1817 2.9291 -0.2028 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8328 2.0729 -1.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 1.1491 1.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7171 -0.4056 -2.1964 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7748 -2.0155 -1.4818 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2687 -1.1346 -1.7980 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2549 -2.5161 0.7559 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6391 -1.1672 1.9731 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5951 -2.4497 1.3087 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4178 -2.0061 -0.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9797 0.5266 -0.9017 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4828 0.9143 -1.8555 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3194 2.1663 -0.9546 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3569 2.9738 0.8040 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0212 1.8633 2.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6525 1.9789 1.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3408 1.7167 1.7084 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4016 1.9628 1.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7386 0.3165 1.9775 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7226 -3.2432 -0.4244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3020 -2.4480 1.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4571 -2.9678 -0.1878 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 3 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 2 0 10 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 30 32 1 0 12 33 1 1 7 34 1 0 13 8 1 0 24 18 1 0 19 12 1 0 30 23 1 0 1 35 1 0 1 36 1 0 1 37 1 0 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 7 42 1 6 8 43 1 1 9 44 1 0 9 45 1 0 14 46 1 0 14 47 1 0 14 48 1 0 15 49 1 0 15 50 1 0 22 51 1 0 22 52 1 0 23 53 1 1 25 54 1 0 25 55 1 0 25 56 1 0 26 57 1 0 26 58 1 0 27 59 1 0 27 60 1 0 31 61 1 0 31 62 1 0 31 63 1 0 32 64 1 0 32 65 1 0 32 66 1 0 33 67 1 0 33 68 1 0 33 69 1 0 34 70 1 0 34 71 1 0 34 72 1 0 M END

Standard InCHIKey	ZXYSCJISDAKHPX-IRFVERNZSA-N
Standard InCHI	InChI=1S/C28H38O6/c1-15(8-9-22(33)34-7)16-12-21(32)28(6)24-17(29)13-19-25(2,3)20(31)10-11-26(19,4)23(24)18(30)14-27(16,28)5/h15-16,19H,8-14H2,1-7H3/t15-,16-,19+,26+,27-,28+/m1/s1
SMILES	COC(=O)CC[C@H]([C@H]1CC(=O)[C@@]2([C@]1(C)CC(=O)C1=C2C(=O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.27	Volume:	495.541 ? Van der Waals volume.
Dense:	0.949	LogP:	2.017 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.45 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.16 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	25.0
TPSA:	94.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.564	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.744	Fsp³:	0.75
MCE-18:	83.265 ? 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:	0.745	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.124 ? 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:	0.445	Promiscuous compounds:	0.36

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.761	MDCK Permeability:	-4.7
Pgp-inhibitor:	0.948	Pgp-substrate:	0.001
PAMPA:	0.877 ? 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%):	0.004	30% Bioavailability (F30%):	0.101
50% Bioavailability (F50%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.98
Plasma Protein Binding (PPB):	82.51%	Volume Distribution (VD):	0.226
Fu:	22.625% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.02
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.87	CYP1A2-substrate:	0.013
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.998
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):

8.584

Half-life (T1/2):

0.335

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.048
Human Hepatotoxicity (H-HT):	0.769	Drug-induced Liver Injury (DILI):	0.396
AMES Toxicity:	0.696	Rat Oral Acute Toxicity:	0.461
Maximum Recommended Daily Dose:	0.699	Skin Sensitization:	0.996
Carcinogencity:	0.986	Eye Corrosion:	0.006
Eye Irritation:	0.37	Respiratory Toxicity:	0.227
Drug-induced Neurotoxicity:	0.254	Ototoxicity:	0.469
Hematotoxicity:	0.902	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.19
A549 Cytotoxicity:	0.01	Hek293 Cytotoxicity:	0.193
BCF:	0.586 ? 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:	3.296 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.953 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.243 ? 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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	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
Ratio	1
Activity	5
IC50	1
Inhibition	1

Activity Type	# Activity
Cell line	2
Individual protein	1
Others	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	3.0	n.a.	PMID[26222905]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[14695801]
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	22.0	%	PMID[20039640]
NPT2	Others	Unspecified	n.a.	Activity	=	2.1	%	PMID[14695801]
NPT2	Others	Unspecified	n.a.	Activity	=	26.8	%	PMID[14695801]
NPT2	Others	Unspecified	n.a.	Activity	=	75.4	%	PMID[14695801]
NPT2	Others	Unspecified	n.a.	Activity	=	98.3	%	PMID[14695801]
NPT2	Others	Unspecified	n.a.	IC50	=	285.0	molar ratio	PMID[14695801]

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 NPC271784 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	23789
0.1-0.2	24289
0.2-0.3	1545
0.3-0.4	175
0.4-0.5	37
0.5-0.6	13
0.6-0.7	6
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
0.8491	Intermediate Similarity	NPC249212
0.7458	Intermediate Similarity	NPC3772
0.7368	Intermediate Similarity	NPC469561
0.6721	Remote Similarity	NPC216904
0.6562	Remote Similarity	NPC264404
0.6515	Remote Similarity	NPC121339
0.6129	Remote Similarity	NPC209882
0.6129	Remote Similarity	NPC607131
0.6102	Remote Similarity	NPC473039
0.5909	Remote Similarity	NPC607625
0.5846	Remote Similarity	NPC18319
0.5735	Remote Similarity	NPC106557
0.5593	Remote Similarity	NPC473038
0.5588	Remote Similarity	NPC275439
0.5441	Remote Similarity	NPC125622
0.5385	Remote Similarity	NPC480122
0.5231	Remote Similarity	NPC484799
0.5211	Remote Similarity	NPC184870
0.5152	Remote Similarity	NPC88198
0.5139	Remote Similarity	NPC307954
0.5075	Remote Similarity	NPC472931
0.5072	Remote Similarity	NPC112753

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC271784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7204
0.1-0.2	1845
0.2-0.3	101
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