NPASS Compound

Natural Product: NPC286174

Natural Product ID	NPC286174
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lucidenic Acid P
IUPAC Name	(4R)-4-[(3S,5R,7S,10S,12S,13R,14R,17R)-12-acetyloxy-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]pentanoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL469283
PubChem CID	11203160
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 79 82 0 0 0 0 0 0 0 0999 V2000 4.1452 1.7065 -1.4265 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0698 1.1447 -0.0379 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4128 0.8580 0.5051 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3123 -0.0811 -0.1878 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8982 -1.4539 -0.3836 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3909 -1.8259 -1.4621 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0421 -2.4088 0.6011 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0002 0.1589 0.1188 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0327 -0.4405 1.5650 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6840 -1.0410 1.7623 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3683 -1.5465 2.8131 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9846 -0.8413 0.4609 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5397 -1.8976 -0.4703 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4643 -0.8772 0.5362 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1935 0.1364 0.1213 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5692 1.3288 -0.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0418 2.4531 -0.5414 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8714 1.1474 -0.9570 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5777 0.5626 0.1584 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2857 1.3529 1.4453 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2721 2.3290 -1.5449 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3311 2.6028 -2.8818 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0009 1.7342 -3.6815 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7864 3.9272 -3.3457 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6848 0.2265 0.1801 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9872 1.3499 1.1245 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2004 0.5452 -1.2301 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5009 -0.1830 -1.5019 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4074 -0.2307 -0.3127 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7384 -1.1170 0.7269 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2357 -0.8587 2.1197 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2099 -2.5437 0.3790 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2754 -1.0938 0.5401 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4643 -1.6330 1.6986 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1537 -2.0785 1.0307 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4523 -2.9512 1.7908 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7592 1.0073 0.1522 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2039 1.6597 -1.8262 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6032 1.0578 -2.1676 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9027 2.7825 -1.5136 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7077 2.0566 0.5849 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3907 0.5729 1.5800 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9662 1.8495 0.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7632 0.3726 -1.1359 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2535 -0.1362 0.4565 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4275 -3.2352 0.6589 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1590 -0.6661 -0.5665 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7902 -1.2243 1.6348 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1578 0.3389 2.3100 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7471 -2.7153 -0.5210 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6794 -1.5990 -1.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4143 -2.4414 -0.0674 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6910 0.4329 -1.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3398 1.9458 1.2553 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0092 0.7097 2.2967 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1085 1.9856 1.7641 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4713 3.7889 -4.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4024 4.4451 -2.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9137 4.5839 -3.6089 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6764 1.1250 1.9323 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0683 1.7618 1.6399 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3221 2.2257 0.4943 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4349 1.6323 -1.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4854 0.1920 -2.0022 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0207 0.3697 -2.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3152 -1.2001 -1.8873 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3615 -0.7130 -0.6817 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4233 -0.9324 2.8912 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9839 -1.6327 2.4685 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8131 0.0981 2.2107 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1111 -3.1418 1.2816 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5033 -2.9722 -0.3740 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2148 -2.5301 -0.0688 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0622 -1.7515 -0.3625 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9194 -2.5249 2.1646 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2200 -0.8333 2.4289 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5487 -2.6967 0.1489 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7101 -3.8858 1.6597 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5753 1.3774 -0.2413 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 5 7 1 0 2 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 6 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 1 18 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 15 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 30 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 29 37 1 0 19 8 1 0 33 25 1 0 19 12 1 0 35 14 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 1 3 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 7 46 1 0 8 47 1 6 9 48 1 0 9 49 1 0 13 50 1 0 13 51 1 0 13 52 1 0 18 53 1 6 20 54 1 0 20 55 1 0 20 56 1 0 24 57 1 0 24 58 1 0 24 59 1 0 26 60 1 0 26 61 1 0 26 62 1 0 27 63 1 0 27 64 1 0 28 65 1 0 28 66 1 0 29 67 1 6 31 68 1 0 31 69 1 0 31 70 1 0 32 71 1 0 32 72 1 0 32 73 1 0 33 74 1 6 34 75 1 0 34 76 1 0 35 77 1 6 36 78 1 0 37 79 1 0 M END

Standard InCHIKey	QPEKELRREXLZJP-WGULIUFBSA-N
Standard InCHI	InChI=1S/C29H42O8/c1-14(8-9-21(34)35)16-12-20(33)29(7)22-17(31)13-18-26(3,4)19(32)10-11-27(18,5)23(22)24(36)25(28(16,29)6)37-15(2)30/h14,16-19,25,31-32H,8-13H2,1-7H3,(H,34,35)/t14-,16-,17+,18+,19+,25-,27+,28+,29+/m1/s1
SMILES	C[C@H](CCC(=O)O)[C@H]1CC(=O)[C@@]2(C)C3=C(C(=O)[C@H]([C@]12C)OC(=O)C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1C[C@@H]3O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.29	Volume:	533.054 ? Van der Waals volume.
Dense:	0.972	LogP:	2.143 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.129 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.611 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	138.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.471	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.113	Fsp³:	0.793
MCE-18:	90.0 ? 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:	0.764	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.049 ? 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:	0.26	Promiscuous compounds:	0.413

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.313	MDCK Permeability:	-4.999
Pgp-inhibitor:	0.605	Pgp-substrate:	0.282
PAMPA:	0.998 ? 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):	0.003
20% Bioavailability (F20%):	0.236	30% Bioavailability (F30%):	0.139
50% Bioavailability (F50%):	0.835

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.979
Plasma Protein Binding (PPB):	82.766%	Volume Distribution (VD):	-0.485
Fu:	16.104% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.001
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.141	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.709	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.879
HLM stability:	0.134 ? 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):

7.483

Half-life (T1/2):

1.626

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.022
Human Hepatotoxicity (H-HT):	0.633	Drug-induced Liver Injury (DILI):	0.491
AMES Toxicity:	0.212	Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.835	Skin Sensitization:	0.76
Carcinogencity:	0.712	Eye Corrosion:	0.0
Eye Irritation:	0.369	Respiratory Toxicity:	0.283
Drug-induced Neurotoxicity:	0.032	Ototoxicity:	0.76
Hematotoxicity:	0.496	Drug-induced Nephrotoxicity:	0.902
Genotoxicity:	0.852	RPMI-8226 Immunitoxicity:	0.133
A549 Cytotoxicity:	0.01	Hek293 Cytotoxicity:	0.045
BCF:	0.326 ? 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:	2.937 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.271 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.42 ? 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]
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
Activity	5
IC50	1

Activity Type	# Activity
Cell line	1
Others	5

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[14695801]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	PMID[14695801]
NPT2	Others	Unspecified	n.a.	Activity	=	27.5	%	PMID[14695801]
NPT2	Others	Unspecified	n.a.	Activity	=	74.2	%	PMID[14695801]
NPT2	Others	Unspecified	n.a.	Activity	=	96.6	%	PMID[14695801]
NPT2	Others	Unspecified	n.a.	IC50	=	286.0	molar ratio	PMID[14695801]

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 NPC286174 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	17208
0.1-0.2	28023
0.2-0.3	4448
0.3-0.4	135
0.4-0.5	23
0.5-0.6	11
0.6-0.7	4
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	NPC33973
0.7714	Intermediate Similarity	NPC115303
0.7463	Intermediate Similarity	NPC77947
0.7206	Intermediate Similarity	NPC251017
0.7143	Intermediate Similarity	NPC600026
0.7101	Intermediate Similarity	NPC122294
0.6849	Remote Similarity	NPC129689
0.6267	Remote Similarity	NPC2436
0.6203	Remote Similarity	NPC472927
0.6111	Remote Similarity	NPC70967
0.5733	Remote Similarity	NPC135854
0.5513	Remote Similarity	NPC216245
0.5495	Remote Similarity	NPC472933
0.5395	Remote Similarity	NPC37646
0.5385	Remote Similarity	NPC51452
0.5316	Remote Similarity	NPC16021
0.5309	Remote Similarity	NPC470251
0.525	Remote Similarity	NPC293753
0.5244	Remote Similarity	NPC604894
0.5063	Remote Similarity	NPC144660
0.506	Remote Similarity	NPC472929

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC286174 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5655
0.1-0.2	3392
0.2-0.3	95
0.3-0.4	8
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