NPASS Compound

Natural Product: NPC166745

Natural Product ID	NPC166745
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ganoderic Acid Tr 1
IUPAC Name	(E,6R)-6-[(5R,10S,13R,14R,15R,17R)-15-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoic acid
Synonyms	Ganoderic Acid Tr 1
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1095857
PubChem CID	46830516
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 78 81 0 0 0 0 0 0 0 0999 V2000 3.1995 2.1618 -1.6652 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4014 1.0137 -0.7118 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2775 0.7468 0.2020 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1130 2.0381 1.0246 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6174 2.3673 0.9777 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0304 1.0644 0.7343 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9583 0.3584 -0.2760 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5546 0.7370 -1.6597 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6056 -1.1100 -0.0718 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 -1.3559 -0.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7753 -0.4353 -0.0545 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3291 0.9447 0.2496 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2013 1.9018 0.0574 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5548 1.5680 -0.4510 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0451 0.3429 0.2427 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1941 -0.8141 -0.1960 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4303 -1.2188 -1.6187 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5792 -1.9849 0.6953 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9926 -2.3744 0.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7244 -1.2951 -0.3500 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4693 -1.5845 -1.2662 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5190 0.1106 0.0958 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1443 1.0917 -0.8727 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2632 0.2921 1.4225 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1152 0.2740 2.0507 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3351 3.4186 0.1705 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0194 -0.1091 -1.4501 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3120 -1.3449 -0.6280 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 -1.0418 0.4859 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4096 -1.6702 0.5390 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3496 -1.3881 1.6245 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4474 -1.9741 1.6885 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0363 -0.4660 2.5988 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7582 -2.6518 -0.4866 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2476 2.6655 -1.6230 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3527 1.8292 -2.7356 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9800 2.9732 -1.5545 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2314 1.3764 -0.0135 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6408 -0.0291 0.9402 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4844 1.9195 2.0516 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6189 2.8958 0.5716 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3703 2.6871 2.0340 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0458 1.7467 -1.6768 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3151 0.6141 -2.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2890 0.0522 -1.9819 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0889 -1.7594 -0.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9680 -1.4832 0.9203 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1724 -2.3753 -0.4213 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8945 2.9084 0.2840 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4341 1.3173 -1.5382 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2598 2.4307 -0.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8510 0.4803 1.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0957 -0.5347 -2.1742 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4708 -1.2387 -2.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8385 -2.2479 -1.7160 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4862 -1.7107 1.7780 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9022 -2.8380 0.5272 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0000 -3.3259 -0.2261 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5461 -2.5874 1.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0781 0.6396 -1.2758 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4679 1.4004 -1.6802 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4103 1.9991 -0.2907 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8089 1.2597 1.4481 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0139 -0.5216 1.5651 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5706 0.2905 2.2733 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6168 -0.5277 2.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1375 -0.0007 2.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2002 1.0285 2.8323 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1990 4.2790 0.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -0.4549 -2.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0292 0.1864 -1.8687 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3850 -1.6973 -0.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6644 -2.1642 -1.2608 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0229 -0.3226 1.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7588 -0.0501 3.1848 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8266 -2.9248 -0.3791 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1787 -3.5909 -0.4313 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6838 -2.2077 -1.5197 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 6 7 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 22 24 1 0 6 25 1 1 5 26 1 0 2 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 7 3 1 0 16 11 1 0 12 6 1 0 22 15 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 0 4 41 1 0 5 42 1 1 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 13 49 1 0 14 50 1 0 14 51 1 0 15 52 1 1 17 53 1 0 17 54 1 0 17 55 1 0 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 23 60 1 0 23 61 1 0 23 62 1 0 24 63 1 0 24 64 1 0 24 65 1 0 25 66 1 0 25 67 1 0 25 68 1 0 26 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 28 73 1 0 29 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 34 78 1 0 M END

Standard InCHIKey	SNZQBBATMLGADX-CDVAXDTMSA-N
Standard InCHI	InChI=1S/C30H44O4/c1-18(9-8-10-19(2)26(33)34)22-17-25(32)30(7)21-11-12-23-27(3,4)24(31)14-15-28(23,5)20(21)13-16-29(22,30)6/h10-11,13,18,22-23,25,32H,8-9,12,14-17H2,1-7H3,(H,33,34)/b19-10+/t18-,22-,23+,25-,28-,29-,30-/m1/s1
SMILES	C[C@@H]([C@H]1C[C@H]([C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)O)CC/C=C(/C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.32	Volume:	515.189 ? Van der Waals volume.
Dense:	0.909	LogP:	4.064 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.31 ? 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:	23.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.452	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.01	Fsp³:	0.733
MCE-18:	81.231 ? 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:	0.832	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.08 ? 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:	0.444	Promiscuous compounds:	0.201

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.32	MDCK Permeability:	-4.888
Pgp-inhibitor:	0.817	Pgp-substrate:	0.0
PAMPA:	0.868 ? 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%):	0.243	30% Bioavailability (F30%):	0.268
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.983
Plasma Protein Binding (PPB):	85.544%	Volume Distribution (VD):	-0.152
Fu:	16.893% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.017
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.18	CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.549
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.976 ? 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):

5.715

Half-life (T1/2):

0.912

ADMET: Toxicity

hERG Blockers:	0.04	hERG Blockers (10um):	0.074
Human Hepatotoxicity (H-HT):	0.704	Drug-induced Liver Injury (DILI):	0.436
AMES Toxicity:	0.1	Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.741	Skin Sensitization:	0.836
Carcinogencity:	0.281	Eye Corrosion:	0.002
Eye Irritation:	0.199	Respiratory Toxicity:	0.748
Drug-induced Neurotoxicity:	0.127	Ototoxicity:	0.878
Hematotoxicity:	0.294	Drug-induced Nephrotoxicity:	0.854
Genotoxicity:	0.844	RPMI-8226 Immunitoxicity:	0.081
A549 Cytotoxicity:	0.018	Hek293 Cytotoxicity:	0.097
BCF:	0.515 ? 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:	3.416 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.092 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.071 ? 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
Organism	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
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	18000.0	nM	PMID[20384295]

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 NPC166745 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	20975
0.1-0.2	24521
0.2-0.3	3889
0.3-0.4	345
0.4-0.5	86
0.5-0.6	28
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC285702
1.0	High Similarity	NPC235464
0.7727	Intermediate Similarity	NPC69622
0.7727	Intermediate Similarity	NPC607637
0.7612	Intermediate Similarity	NPC138536
0.7463	Intermediate Similarity	NPC472942
0.7463	Intermediate Similarity	NPC250575
0.7206	Intermediate Similarity	NPC87552
0.7162	Intermediate Similarity	NPC166120
0.7027	Intermediate Similarity	NPC94393
0.6447	Remote Similarity	NPC137552
0.6447	Remote Similarity	NPC99411
0.64	Remote Similarity	NPC604630
0.6125	Remote Similarity	NPC489806
0.5946	Remote Similarity	NPC479655
0.5811	Remote Similarity	NPC212948
0.5714	Remote Similarity	NPC489798
0.5714	Remote Similarity	NPC147568
0.5641	Remote Similarity	NPC489791
0.5616	Remote Similarity	NPC4166
0.557	Remote Similarity	NPC39082
0.557	Remote Similarity	NPC610107
0.5443	Remote Similarity	NPC478312
0.5405	Remote Similarity	NPC89077
0.5405	Remote Similarity	NPC311092
0.5333	Remote Similarity	NPC142253
0.5333	Remote Similarity	NPC3511
0.5195	Remote Similarity	NPC8571
0.5195	Remote Similarity	NPC44181
0.5195	Remote Similarity	NPC606857
0.519	Remote Similarity	NPC456
0.519	Remote Similarity	NPC472941
0.519	Remote Similarity	NPC483394
0.519	Remote Similarity	NPC202814
0.5176	Remote Similarity	NPC198442
0.5135	Remote Similarity	NPC201852
0.5135	Remote Similarity	NPC170793
0.5132	Remote Similarity	NPC83569
0.5128	Remote Similarity	NPC66429
0.5128	Remote Similarity	NPC472239
0.5065	Remote Similarity	NPC162703
0.506	Remote Similarity	NPC92022

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC166745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6405
0.1-0.2	2607
0.2-0.3	138
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