NPASS Compound

Natural Product: NPC25750

Natural Product ID	NPC25750
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ganolucidic Acid A
IUPAC Name	(6R)-6-[(5R,10S,13R,14R,15S,17R)-15-hydroxy-4,4,10,13,14-pentamethyl-3,11-dioxo-2,5,6,7,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1087131
PubChem CID	20055993
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 80 83 0 0 0 0 0 0 0 0999 V2000 4.1217 -0.5286 -0.9033 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3260 0.1491 0.0883 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1028 1.4109 -0.1772 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5602 1.1121 -0.4347 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2365 2.4088 -0.6820 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8068 2.6043 -1.7808 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2587 3.4215 0.2717 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7891 0.2094 -1.6016 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8671 -0.2042 1.4483 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1010 -1.4656 1.4483 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8628 -1.5576 0.6529 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2759 -2.9372 0.8555 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2409 -2.7639 0.6964 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3548 -1.4000 0.0810 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7421 -0.6535 0.8287 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2811 -0.3881 2.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 0.6829 0.1259 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4600 1.1795 -0.3508 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4816 2.2171 -1.0623 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7067 0.5538 -0.0547 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6726 -0.7744 0.1714 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8728 -1.5605 0.4757 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0915 -1.0947 -0.2754 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9233 0.2815 -0.8623 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0255 1.1755 0.0056 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5583 1.0808 1.4114 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1232 2.5895 -0.4522 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5095 2.6923 -1.9275 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9369 2.1953 -1.9688 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8024 2.8365 -2.5357 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1894 0.9104 -1.2879 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7849 -0.0139 -2.3668 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2365 1.0775 -0.2550 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0274 -1.5725 -1.3846 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6805 -3.7352 -0.2164 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0409 -2.0421 2.8397 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0292 2.0295 0.7221 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7120 1.9124 -1.0799 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0303 0.6271 0.4547 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4088 4.3588 -0.0562 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8808 0.2860 -1.8633 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2523 0.5621 -2.5221 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6142 -0.8617 -1.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3877 0.6374 1.9791 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8123 -0.4015 2.0399 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8142 -2.2039 0.9169 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1116 -1.5442 -0.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6615 -3.6701 0.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4330 -3.2591 1.8956 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7809 -2.8314 1.6385 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0581 0.0638 2.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1283 -1.2601 2.7516 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5531 0.3747 2.2044 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5930 0.6305 -0.7209 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2445 1.4836 0.7942 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6762 -2.6256 0.1863 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0249 -1.5979 1.5714 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9624 -1.2049 0.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2887 -1.7815 -1.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3073 0.1307 -1.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8204 2.1149 1.7980 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8466 0.7002 2.1610 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4468 0.4127 1.4940 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3147 3.2587 -0.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0259 3.0334 0.0792 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4358 3.7352 -2.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9364 2.0040 -2.5607 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0318 -0.2431 -3.1242 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6697 0.4948 -2.8052 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0779 -0.9734 -1.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0656 1.8711 0.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5268 0.1403 0.2615 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1784 1.4007 -0.7934 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9424 -1.7513 -1.9226 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6417 -2.4741 -1.5537 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4800 -0.6811 -1.8147 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0136 -4.5373 0.2769 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0668 -2.0012 3.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5177 -3.0541 2.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7100 -1.4021 3.4927 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 4 8 1 0 2 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 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 31 33 1 0 14 34 1 6 13 35 1 0 10 36 1 0 15 11 1 0 25 20 1 0 21 14 1 0 31 24 1 0 3 37 1 0 3 38 1 0 4 39 1 0 7 40 1 0 8 41 1 0 8 42 1 0 8 43 1 0 9 44 1 0 9 45 1 0 10 46 1 6 11 47 1 6 12 48 1 0 12 49 1 0 13 50 1 1 16 51 1 0 16 52 1 0 16 53 1 0 17 54 1 0 17 55 1 0 22 56 1 0 22 57 1 0 23 58 1 0 23 59 1 0 24 60 1 6 26 61 1 0 26 62 1 0 26 63 1 0 27 64 1 0 27 65 1 0 28 66 1 0 28 67 1 0 32 68 1 0 32 69 1 0 32 70 1 0 33 71 1 0 33 72 1 0 33 73 1 0 34 74 1 0 34 75 1 0 34 76 1 0 35 77 1 0 36 78 1 0 36 79 1 0 36 80 1 0 M END

Standard InCHIKey	XRXBNTYHQXKSAO-SXTFGQQDSA-N
Standard InCHI	InChI=1S/C30H44O6/c1-16(12-18(31)13-17(2)26(35)36)20-14-24(34)30(7)19-8-9-22-27(3,4)23(33)10-11-28(22,5)25(19)21(32)15-29(20,30)6/h16-17,20,22,24,34H,8-15H2,1-7H3,(H,35,36)/t16-,17?,20-,22+,24+,28+,29-,30-/m1/s1
SMILES	O=C(CC(C(=O)O)C)C[C@H]([C@H]1C[C@@H]([C@@]2([C@]1(C)CC(=O)C1=C2CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	500.31	Volume:	532.769 ? Van der Waals volume.
Dense:	0.939	LogP:	2.27 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.2 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.603 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	108.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.521	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.998	Fsp³:	0.8
MCE-18:	86.852 ? 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:	0.889	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.05 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.346	Promiscuous compounds:	0.139

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.001	MDCK Permeability:	-4.746
Pgp-inhibitor:	0.001	Pgp-substrate:	0.0
PAMPA:	1.0 ? 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%):	0.001	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.205

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.981
Plasma Protein Binding (PPB):	92.492%	Volume Distribution (VD):	-0.155
Fu:	8.431% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.957

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.029	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.979	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.018
HLM stability:	0.1 ? 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):

2.118

Half-life (T1/2):

1.279

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.02
Human Hepatotoxicity (H-HT):	0.654	Drug-induced Liver Injury (DILI):	0.324
AMES Toxicity:	0.108	Rat Oral Acute Toxicity:	0.428
Maximum Recommended Daily Dose:	0.493	Skin Sensitization:	0.977
Carcinogencity:	0.692	Eye Corrosion:	0.001
Eye Irritation:	0.294	Respiratory Toxicity:	0.504
Drug-induced Neurotoxicity:	0.18	Ototoxicity:	0.685
Hematotoxicity:	0.782	Drug-induced Nephrotoxicity:	0.98
Genotoxicity:	0.952	RPMI-8226 Immunitoxicity:	0.05
A549 Cytotoxicity:	0.016	Hek293 Cytotoxicity:	0.045
BCF:	0.402 ? 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:	3.09 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.545 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.631 ? 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	4
Inhibition	1

Activity Type	# Activity
Individual protein	2
Cell line	2
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	IC50	=	22970.0	nM	PMID[21924611]
NPT439	Individual protein	Butyrylcholinesterase	Homo sapiens	IC50	>	200000.0	nM	PMID[21924611]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell line	3T3-L1	Mus musculus	Inhibition	=	22.0	%	PMID[20039640]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	101000.0	nM	PMID[23092389]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	25340.0	nM	PMID[27335254]

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 NPC25750 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	22786
0.1-0.2	24426
0.2-0.3	2335
0.3-0.4	219
0.4-0.5	57
0.5-0.6	13
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC610087
0.791	Intermediate Similarity	NPC241156
0.791	Intermediate Similarity	NPC488419
0.791	Intermediate Similarity	NPC600288
0.7826	Intermediate Similarity	NPC95565
0.7826	Intermediate Similarity	NPC609201
0.7571	Intermediate Similarity	NPC606047
0.7042	Intermediate Similarity	NPC488423
0.6986	Remote Similarity	NPC604630
0.6494	Remote Similarity	NPC480124
0.6438	Remote Similarity	NPC472932
0.6389	Remote Similarity	NPC488420
0.6389	Remote Similarity	NPC600686
0.6351	Remote Similarity	NPC488421
0.6267	Remote Similarity	NPC243525
0.6267	Remote Similarity	NPC40765
0.6133	Remote Similarity	NPC10364
0.6056	Remote Similarity	NPC209882
0.6056	Remote Similarity	NPC607131
0.6053	Remote Similarity	NPC55872
0.5949	Remote Similarity	NPC488422
0.5455	Remote Similarity	NPC125622
0.5325	Remote Similarity	NPC255809
0.5269	Remote Similarity	NPC600080
0.5263	Remote Similarity	NPC141178
0.5256	Remote Similarity	NPC107690
0.5256	Remote Similarity	NPC206810
0.525	Remote Similarity	NPC204450
0.525	Remote Similarity	NPC205899
0.525	Remote Similarity	NPC195290
0.5213	Remote Similarity	NPC611554
0.5185	Remote Similarity	NPC16021
0.5059	Remote Similarity	NPC56498

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC25750 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6146
0.1-0.2	2911
0.2-0.3	93
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