NPASS Compound

Natural Product: NPC87552

Natural Product ID	NPC87552
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ganoderic Acid S
IUPAC Name	(Z,6R)-2-methyl-6-[(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-17-yl]hept-2-enoic acid
Synonyms	Ganoderic Acid S
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1097154
PubChem CID	46888171
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 77 80 0 0 0 0 0 0 0 0999 V2000 4.1024 -2.2905 0.6045 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1132 -1.3398 -0.0830 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8057 -1.5205 0.5361 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7233 -1.2404 2.0151 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2604 -0.8640 2.3060 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4142 -1.2662 1.0240 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6467 -0.7549 0.0269 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7362 0.7310 0.2807 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1944 -1.0025 -1.3519 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0562 -0.1795 -1.5520 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9260 -0.0271 -0.5561 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7028 -0.6450 0.7516 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6520 -0.6343 1.6497 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9921 -0.0201 1.4434 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2699 -0.0403 -0.0507 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1731 0.7713 -0.6935 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9716 2.0478 0.1341 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4627 1.1982 -2.0856 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6380 2.1545 -2.0391 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7205 1.6392 -1.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7447 2.2971 -1.0960 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6468 0.3913 -0.3968 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4976 0.5502 0.8535 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3465 -0.6899 -1.2339 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4705 -2.7823 1.0148 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7208 0.0062 -0.0857 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0549 -0.1100 -0.8725 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7329 1.1637 -0.9358 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9117 1.4113 -0.4747 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7896 0.4790 0.1929 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9377 0.9005 0.5904 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5643 -0.8469 0.4754 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4621 2.8297 -0.6375 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6368 -1.6935 1.3708 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5345 -3.0743 1.1311 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8013 -2.7280 -0.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0612 -1.7016 -1.1374 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5412 -2.6156 0.4299 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3824 -0.4343 2.3526 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9257 -2.1585 2.6040 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1630 0.2050 2.5510 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1275 -1.4344 3.1811 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2018 1.1274 0.7718 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5337 0.9662 1.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8123 1.2981 -0.6585 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9357 -0.6494 -2.0801 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0692 -2.0293 -1.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2445 0.2862 -2.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4658 -1.0977 2.6090 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1025 0.9607 1.9039 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7329 -0.7094 1.9113 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1197 -1.0930 -0.3757 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4599 1.8436 1.0899 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9515 2.5478 0.3048 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3373 2.7624 -0.4300 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5983 1.7949 -2.4442 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7369 0.3728 -2.7665 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9989 2.4086 -3.0599 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3271 3.1497 -1.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7301 -0.4507 1.3169 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5018 0.9115 0.4833 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0901 1.2676 1.5649 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6775 -1.0269 -2.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2673 -0.2339 -1.6586 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6134 -1.5627 -0.6277 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -3.2367 1.7995 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5246 -3.0341 1.3377 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3586 -3.2218 0.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9950 0.4285 0.8767 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1290 0.7142 -0.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7862 -0.4160 -1.9273 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6311 -0.8845 -0.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1911 1.9943 -1.4221 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1853 -1.4095 1.0418 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9690 3.3185 -1.5039 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2414 3.4272 0.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5412 2.7937 -0.8549 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 1 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 2 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 29 33 1 0 7 3 1 0 16 11 1 0 12 6 1 0 22 15 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 1 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 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 6 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 26 70 1 0 27 71 1 0 27 72 1 0 28 73 1 0 32 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 M END

Standard InCHIKey	AQUHIKXTCOSRFY-GOEVOFJGSA-N
Standard InCHI	InChI=1S/C30H44O3/c1-19(9-8-10-20(2)26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h10-11,14,19,21,24H,8-9,12-13,15-18H2,1-7H3,(H,32,33)/b20-10-/t19-,21-,24+,28-,29-,30+/m1/s1
SMILES	C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)CC/C=C(C(=O)O)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	452.33	Volume:	506.399 ? Van der Waals volume.
Dense:	0.893	LogP:	5.717 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.198 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.262 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	54.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.439	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.744	Fsp³:	0.733
MCE-18:	78.769 ? 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:	0.924	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.653	Promiscuous compounds:	0.121

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.058	MDCK Permeability:	-4.889
Pgp-inhibitor:	0.17	Pgp-substrate:	0.0
PAMPA:	0.813 ? 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%):	0.102	30% Bioavailability (F30%):	0.25
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.94
Plasma Protein Binding (PPB):	89.427%	Volume Distribution (VD):	-0.027
Fu:	11.585% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.131
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.496	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.676
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.913 ? 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):

4.227

Half-life (T1/2):

0.621

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.076
Human Hepatotoxicity (H-HT):	0.715	Drug-induced Liver Injury (DILI):	0.757
AMES Toxicity:	0.125	Rat Oral Acute Toxicity:	0.36
Maximum Recommended Daily Dose:	0.409	Skin Sensitization:	0.901
Carcinogencity:	0.503	Eye Corrosion:	0.061
Eye Irritation:	0.482	Respiratory Toxicity:	0.639
Drug-induced Neurotoxicity:	0.323	Ototoxicity:	0.635
Hematotoxicity:	0.654	Drug-induced Nephrotoxicity:	0.843
Genotoxicity:	0.9	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.038	Hek293 Cytotoxicity:	0.14
BCF:	1.197 ? 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:	4.154 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.628 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.931 ? 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]
NPO33020	ganoderma leucocontextum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Tibetan	n.a.	PMID[26287401]
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	5

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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1088	Individual protein	3-hydroxy-3-methylglutaryl-coenzyme A reductase	Sus scrofa	IC50	=	12500.0	nM	PMID[26287401]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell line	K562	Homo sapiens	IC50	=	65200.0	nM	PMID[26287401]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	75200.0	nM	PMID[26287401]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	11000.0	nM	PMID[20384295]
NPT2	Others	Unspecified	n.a.	IC50	>	50000.0	nM	PMID[26287401]

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 NPC87552 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	26841
0.1-0.2	20146
0.2-0.3	2459
0.3-0.4	275
0.4-0.5	83
0.5-0.6	29
0.6-0.7	18
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
0.7302	Intermediate Similarity	NPC4166
0.7258	Intermediate Similarity	NPC170793
0.7206	Intermediate Similarity	NPC285702
0.7206	Intermediate Similarity	NPC166745
0.7206	Intermediate Similarity	NPC478312
0.7206	Intermediate Similarity	NPC235464
0.7031	Intermediate Similarity	NPC311092
0.697	Remote Similarity	NPC212948
0.6901	Remote Similarity	NPC137552
0.6901	Remote Similarity	NPC99411
0.6812	Remote Similarity	NPC478313
0.6812	Remote Similarity	NPC489790
0.6769	Remote Similarity	NPC89077
0.6667	Remote Similarity	NPC142253
0.6667	Remote Similarity	NPC3511
0.6471	Remote Similarity	NPC8571
0.6471	Remote Similarity	NPC44181
0.6471	Remote Similarity	NPC606857
0.6418	Remote Similarity	NPC83569
0.6377	Remote Similarity	NPC472239
0.6324	Remote Similarity	NPC162703
0.6176	Remote Similarity	NPC470048
0.6111	Remote Similarity	NPC489798
0.6027	Remote Similarity	NPC489789
0.6	Remote Similarity	NPC69279
0.5753	Remote Similarity	NPC456
0.5753	Remote Similarity	NPC472941
0.5753	Remote Similarity	NPC202814
0.5735	Remote Similarity	NPC16287
0.5479	Remote Similarity	NPC66429
0.5405	Remote Similarity	NPC214697
0.5385	Remote Similarity	NPC92022
0.5342	Remote Similarity	NPC69622
0.5342	Remote Similarity	NPC607637
0.5316	Remote Similarity	NPC484794
0.527	Remote Similarity	NPC138536
0.5263	Remote Similarity	NPC276127
0.5263	Remote Similarity	NPC141401
0.5263	Remote Similarity	NPC478307
0.525	Remote Similarity	NPC166120
0.5205	Remote Similarity	NPC483383
0.5195	Remote Similarity	NPC136044
0.5139	Remote Similarity	NPC475772
0.5135	Remote Similarity	NPC472942
0.5135	Remote Similarity	NPC250575
0.5132	Remote Similarity	NPC152897
0.5132	Remote Similarity	NPC483394
0.5128	Remote Similarity	NPC489802
0.5128	Remote Similarity	NPC39082
0.5128	Remote Similarity	NPC610107
0.5072	Remote Similarity	NPC205455
0.507	Remote Similarity	NPC202389
0.5067	Remote Similarity	NPC489792
0.5065	Remote Similarity	NPC155676

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC87552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6794
0.1-0.2	2250
0.2-0.3	106
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