NPASS Compound

Natural Product: NPC125622

Natural Product ID	NPC125622
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Methyl Ganoderate J
IUPAC Name	methyl (6R)-6-[(5R,10S,13R,14R,15S,17R)-15-hydroxy-4,4,10,13,14-pentamethyl-3,7,11-trioxo-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoate
Synonyms	Methyl Ganoderate J
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2337652
PubChem CID	21636085
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 82 85 0 0 0 0 0 0 0 0999 V2000 8.9710 2.2476 1.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6369 1.3584 0.0421 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3911 0.7115 0.0780 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6566 0.9677 1.0427 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0877 -0.2050 -1.0367 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7642 -0.8865 -0.9465 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6372 0.0415 -0.9081 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8478 1.2476 -0.8375 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2018 -0.3644 -0.9482 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6914 -0.9434 0.3342 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3013 -1.3169 0.3134 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8553 -1.9960 1.6494 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 -2.2261 1.3953 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9784 -1.3990 0.1734 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1671 -0.3694 0.2195 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0555 0.4129 1.5148 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0260 0.5357 -0.9141 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3054 1.2367 -0.7994 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4618 2.3964 -1.2449 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3896 0.5312 -0.1631 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2519 -0.7056 0.2945 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4255 -1.3494 0.8718 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3527 -2.1911 1.7867 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8011 -1.0227 0.3805 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7239 0.1776 -0.5508 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7414 1.1531 0.0523 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9514 1.3165 1.5661 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8577 2.5343 -0.5152 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2381 3.0647 -0.0957 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3057 2.0882 -0.4233 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4609 2.4360 -0.2732 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0420 0.7257 -0.9192 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1860 0.8117 -2.4469 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1838 -0.1732 -0.4560 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9668 -2.2297 -1.0552 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8591 -3.5950 1.1474 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2133 -0.1439 1.4826 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1547 -1.3167 -1.0099 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8299 2.8958 0.7958 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1042 2.9510 1.2366 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1977 1.7104 2.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1694 0.3218 -2.0245 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7305 -1.5311 -0.0274 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6503 -1.5093 -1.8608 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2052 -1.2314 -1.7097 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5830 0.3825 -1.4443 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2803 -1.9348 0.4195 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1389 -2.1426 -0.4192 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1055 -1.4300 2.5203 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3716 -2.9927 1.7129 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1588 -1.9761 2.3004 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8493 0.4855 2.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4374 1.4455 1.2548 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8458 -0.0084 2.1592 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7609 1.3897 -0.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0448 0.1106 -1.9254 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4724 -0.8983 1.2275 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1405 -1.8890 -0.2182 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2293 -0.2264 -1.4833 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6269 2.3683 1.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2596 0.6863 2.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9708 1.1048 1.8814 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1553 3.1784 0.0629 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8008 2.6208 -1.5949 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2823 3.2023 1.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4401 4.0650 -0.5261 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2009 0.5779 -2.7798 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3997 0.1656 -2.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9476 1.8445 -2.7954 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9652 -1.1774 -0.8767 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2752 -0.1531 0.6332 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1092 0.2672 -0.8777 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5363 -3.2367 -0.7966 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4038 -1.8715 -1.9024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0050 -2.4543 -1.4119 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2234 -4.0419 1.9684 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3385 -0.2966 1.4761 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0890 0.9304 1.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9250 -0.6306 2.4444 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8417 -2.0202 -0.2123 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1144 -0.8222 -0.7815 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1095 -1.7906 -2.0068 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 2 0 7 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 1 15 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 32 34 1 0 14 35 1 6 13 36 1 0 10 37 1 0 5 38 1 0 15 11 1 0 26 20 1 0 21 14 1 0 32 25 1 0 1 39 1 0 1 40 1 0 1 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 9 45 1 0 9 46 1 0 10 47 1 1 11 48 1 6 12 49 1 0 12 50 1 0 13 51 1 1 16 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 24 57 1 0 24 58 1 0 25 59 1 6 27 60 1 0 27 61 1 0 27 62 1 0 28 63 1 0 28 64 1 0 29 65 1 0 29 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 35 73 1 0 35 74 1 0 35 75 1 0 36 76 1 0 37 77 1 0 37 78 1 0 37 79 1 0 38 80 1 0 38 81 1 0 38 82 1 0 M END

Standard InCHIKey	CLSQDKKKSJPJCC-CTGWKFNOSA-N
Standard InCHI	InChI=1S/C31H44O7/c1-16(11-18(32)12-17(2)27(37)38-8)19-13-24(36)31(7)26-20(33)14-22-28(3,4)23(35)9-10-29(22,5)25(26)21(34)15-30(19,31)6/h16-17,19,22,24,36H,9-15H2,1-8H3/t16-,17?,19-,22+,24+,29+,30-,31+/m1/s1
SMILES	COC(=O)C(CC(=O)C[C@H]([C@H]1C[C@@H]([C@@]2([C@]1(C)CC(=O)C1=C2C(=O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	528.31	Volume:	556.219 ? Van der Waals volume.
Dense:	0.95	LogP:	1.888 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.125 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.807 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	25.0
TPSA:	114.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.507	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.05	Fsp³:	0.774
MCE-18:	87.709 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.922	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.094 ? 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:	0.321	Promiscuous compounds:	0.391

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.91	MDCK Permeability:	-4.645
Pgp-inhibitor:	0.812	Pgp-substrate:	0.003
PAMPA:	0.847 ? 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%):	0.015	30% Bioavailability (F30%):	0.155
50% Bioavailability (F50%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.995
Plasma Protein Binding (PPB):	82.429%	Volume Distribution (VD):	0.225
Fu:	22.803% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.004
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.277	CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.847	CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.011
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.883
HLM stability:	0.663 ? 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):

9.242

Half-life (T1/2):

0.475

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.057
Human Hepatotoxicity (H-HT):	0.763	Drug-induced Liver Injury (DILI):	0.456
AMES Toxicity:	0.384	Rat Oral Acute Toxicity:	0.444
Maximum Recommended Daily Dose:	0.642	Skin Sensitization:	0.997
Carcinogencity:	0.939	Eye Corrosion:	0.0
Eye Irritation:	0.119	Respiratory Toxicity:	0.232
Drug-induced Neurotoxicity:	0.355	Ototoxicity:	0.611
Hematotoxicity:	0.936	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.996	RPMI-8226 Immunitoxicity:	0.123
A549 Cytotoxicity:	0.029	Hek293 Cytotoxicity:	0.198
BCF:	0.541 ? 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:	3.215 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.776 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.111 ? 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]
NPO16609	Ganoderma sinense	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]
NPO16609	Ganoderma sinense	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[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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
IC50	1

Activity Type	# Activity
Cell line	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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	9200.0	nM	PMID[23357630]

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 NPC125622 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	19484
0.1-0.2	27754
0.2-0.3	2402
0.3-0.4	147
0.4-0.5	31
0.5-0.6	22
0.6-0.7	15
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
0.8	Intermediate Similarity	NPC205899
0.7143	Intermediate Similarity	NPC469561
0.6912	Remote Similarity	NPC241156
0.6912	Remote Similarity	NPC488419
0.6912	Remote Similarity	NPC600288
0.6849	Remote Similarity	NPC56498
0.6571	Remote Similarity	NPC106557
0.6506	Remote Similarity	NPC600080
0.6429	Remote Similarity	NPC28656
0.6429	Remote Similarity	NPC611554
0.6111	Remote Similarity	NPC488423
0.6111	Remote Similarity	NPC603740
0.6111	Remote Similarity	NPC607298
0.6044	Remote Similarity	NPC488417
0.6044	Remote Similarity	NPC610721
0.6	Remote Similarity	NPC18319
0.6	Remote Similarity	NPC604793
0.5955	Remote Similarity	NPC604929
0.5797	Remote Similarity	NPC480122
0.5745	Remote Similarity	NPC600997
0.5745	Remote Similarity	NPC601439
0.5745	Remote Similarity	NPC605557
0.5676	Remote Similarity	NPC10364
0.5625	Remote Similarity	NPC488418
0.5625	Remote Similarity	NPC610358
0.56	Remote Similarity	NPC236390
0.5526	Remote Similarity	NPC606047
0.5479	Remote Similarity	NPC488420
0.5479	Remote Similarity	NPC470254
0.5479	Remote Similarity	NPC112753
0.5479	Remote Similarity	NPC600686
0.5467	Remote Similarity	NPC144660
0.5455	Remote Similarity	NPC25750
0.5455	Remote Similarity	NPC119493
0.5455	Remote Similarity	NPC610087
0.5441	Remote Similarity	NPC271784
0.5316	Remote Similarity	NPC488422
0.5211	Remote Similarity	NPC484799
0.5065	Remote Similarity	NPC488421

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC125622 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7021
0.1-0.2	2051
0.2-0.3	78
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