NPASS Compound

Natural Product: NPC293753

Natural Product ID	NPC293753
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ganoderic Acid Beta
IUPAC Name	(E,6R)-6-[(3S,5R,7S,10S,13R,14R,17R)-3,7-dihydroxy-4,4,10,13,14-pentamethyl-11,15-dioxo-2,3,5,6,7,12,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoic acid
Synonyms	Ganoderic Acid Beta
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL474065
PubChem CID	10097521
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 3.2019 -1.0982 -2.5635 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5623 -0.6880 -1.1423 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1572 -1.8131 -0.3634 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5790 -1.4814 1.0142 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6155 -0.5257 1.2909 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7033 -0.2161 0.6211 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0457 -0.8811 -0.6271 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5767 0.8429 1.1840 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6130 1.1341 0.5405 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3153 1.5077 2.3490 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4921 0.1116 -0.4807 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3466 1.3626 -1.3574 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8760 1.4864 -1.5554 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3945 2.0244 -2.5345 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2919 0.8542 -0.3811 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4938 1.7647 0.8133 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1549 0.5599 -0.4665 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5884 -0.3053 0.4862 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5828 -0.7842 1.4143 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0447 -1.1484 2.5643 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8697 -0.8804 1.1546 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1428 -0.4260 -0.2611 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6269 -1.4789 -1.1640 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0165 -0.6479 0.4630 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2432 -1.5862 -0.7084 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6098 -1.2637 1.6583 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1665 -0.2361 2.6477 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4186 0.4075 2.0533 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1325 0.7661 0.6241 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1083 0.0778 -0.2841 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4919 2.2709 0.5260 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7090 0.6907 0.2304 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4806 1.1938 -1.1556 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0004 1.1890 -1.4663 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7887 0.6465 -2.7219 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5038 -0.4668 2.1440 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2722 -2.2036 -2.7186 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9827 -0.7260 -3.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2773 -0.6422 -2.9374 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3700 0.0703 -1.2623 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4323 -2.6833 -0.2777 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9823 -2.2461 -0.9391 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7854 -2.4586 1.5970 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6548 -1.1240 1.5804 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4805 0.0609 2.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1307 -0.5495 -0.8437 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5054 -0.5881 -1.5302 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1720 -1.9848 -0.5443 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6373 2.4797 2.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9057 0.4616 0.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6557 2.2782 -0.8114 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9027 1.3103 -2.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2819 1.6481 1.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4338 2.8145 0.4031 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4721 1.6845 1.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1531 -1.9350 1.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4558 -0.2623 1.8696 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1307 -1.1335 -2.0904 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3684 -2.2587 -1.3202 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 -2.0208 -0.6262 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3279 -2.6284 -0.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4270 -1.6432 -1.4195 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2172 -1.4035 -1.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0598 -2.0015 2.2207 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5543 -1.8182 1.3258 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4213 0.4941 2.9603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5092 -0.8055 3.5371 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6446 1.2722 2.7097 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1075 0.5752 -0.0860 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9253 0.2656 -1.3513 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2971 -0.9846 -0.0403 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8000 2.5117 -0.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6420 2.8979 0.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3275 2.4910 1.2219 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1675 1.4189 0.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8937 2.2201 -1.2217 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0073 0.6067 -1.9334 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6847 2.2749 -1.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1591 1.2874 -3.3860 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3524 0.0140 2.3686 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 2 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 2 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 1 15 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 6 18 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 28 36 1 0 22 11 1 0 32 24 1 0 22 15 1 0 34 17 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 6 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 0 7 46 1 0 7 47 1 0 7 48 1 0 10 49 1 0 11 50 1 1 12 51 1 0 12 52 1 0 16 53 1 0 16 54 1 0 16 55 1 0 21 56 1 0 21 57 1 0 23 58 1 0 23 59 1 0 23 60 1 0 25 61 1 0 25 62 1 0 25 63 1 0 26 64 1 0 26 65 1 0 27 66 1 0 27 67 1 0 28 68 1 1 30 69 1 0 30 70 1 0 30 71 1 0 31 72 1 0 31 73 1 0 31 74 1 0 32 75 1 1 33 76 1 0 33 77 1 0 34 78 1 6 35 79 1 0 36 80 1 0 M END

Standard InCHIKey	NJZMSAAKSXZIEC-UQOIKQOMSA-N
Standard InCHI	InChI=1S/C30H44O6/c1-16(9-8-10-17(2)26(35)36)18-13-23(34)30(7)25-19(31)14-21-27(3,4)22(33)11-12-28(21,5)24(25)20(32)15-29(18,30)6/h10,16,18-19,21-22,31,33H,8-9,11-15H2,1-7H3,(H,35,36)/b17-10+/t16-,18-,19+,21+,22+,28+,29-,30+/m1/s1
SMILES	C[C@H](CC/C=C(C)/C(=O)O)[C@H]1CC(=O)[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1C[C@@H]3O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	500.31	Volume:	532.769 ? Van der Waals volume.
Dense:	0.939	LogP:	2.644 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.482 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.15 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	111.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.464	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.082	Fsp³:	0.767
MCE-18:	87.17 ? 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:	0.684	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? 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:	0.309	Promiscuous compounds:	0.319

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.348	MDCK Permeability:	-4.997
Pgp-inhibitor:	0.012	Pgp-substrate:	0.017
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):	0.016
20% Bioavailability (F20%):	0.479	30% Bioavailability (F30%):	0.354
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.984
Plasma Protein Binding (PPB):	77.872%	Volume Distribution (VD):	-0.549
Fu:	21.196% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.663

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.785	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.521 ? 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):

5.39

Half-life (T1/2):

1.084

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.014
Human Hepatotoxicity (H-HT):	0.859	Drug-induced Liver Injury (DILI):	0.67
AMES Toxicity:	0.675	Rat Oral Acute Toxicity:	0.632
Maximum Recommended Daily Dose:	0.655	Skin Sensitization:	1.0
Carcinogencity:	0.843	Eye Corrosion:	0.01
Eye Irritation:	0.67	Respiratory Toxicity:	0.925
Drug-induced Neurotoxicity:	0.044	Ototoxicity:	0.746
Hematotoxicity:	0.843	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.99	RPMI-8226 Immunitoxicity:	0.142
A549 Cytotoxicity:	0.364	Hek293 Cytotoxicity:	0.189
BCF:	0.591 ? 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:	3.379 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.057 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.168 ? 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]
NPO32479	gleophyllum lucidum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[Title]
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
IC50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual protein	Protease	Human immunodeficiency virus 1	IC50	=	20000.0	nM	PMID[14987072]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC293753 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	18134
0.1-0.2	27261
0.2-0.3	4063
0.3-0.4	288
0.4-0.5	77
0.5-0.6	23
0.6-0.7	8
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
0.7391	Intermediate Similarity	NPC122294
0.7083	Intermediate Similarity	NPC16021
0.6622	Remote Similarity	NPC307954
0.6351	Remote Similarity	NPC144660
0.6269	Remote Similarity	NPC297199
0.6267	Remote Similarity	NPC287833
0.6234	Remote Similarity	NPC472924
0.6154	Remote Similarity	NPC472928
0.6026	Remote Similarity	NPC21358
0.6026	Remote Similarity	NPC234892
0.5875	Remote Similarity	NPC281702
0.5854	Remote Similarity	NPC472927
0.5789	Remote Similarity	NPC601194
0.5658	Remote Similarity	NPC37646
0.56	Remote Similarity	NPC3772
0.5526	Remote Similarity	NPC255809
0.5455	Remote Similarity	NPC251017
0.5443	Remote Similarity	NPC243525
0.5443	Remote Similarity	NPC55872
0.5443	Remote Similarity	NPC40765
0.5402	Remote Similarity	NPC472935
0.5385	Remote Similarity	NPC264404
0.5316	Remote Similarity	NPC295244
0.5309	Remote Similarity	NPC604630
0.5256	Remote Similarity	NPC607625
0.525	Remote Similarity	NPC51452
0.525	Remote Similarity	NPC286174
0.5185	Remote Similarity	NPC121339
0.5122	Remote Similarity	NPC472925
0.5116	Remote Similarity	NPC198442
0.5063	Remote Similarity	NPC77947
0.5062	Remote Similarity	NPC489798
0.5053	Remote Similarity	NPC472933

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC293753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5956
0.1-0.2	3082
0.2-0.3	108
0.3-0.4	4
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