NPASS Compound

Natural Product: NPC69279

Natural Product ID	NPC69279
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dehydroeburiconic Acid
IUPAC Name	6-methyl-5-methylidene-2-[(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]heptanoic acid
Synonyms	Dehydroeburiconic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL449350
PubChem CID	12133302
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

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 8.1780 0.4307 0.2949 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9409 1.0771 0.8644 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6594 2.3340 0.1088 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8237 0.0765 0.8266 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9877 -1.1320 0.3095 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5294 0.4610 1.3735 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2943 -0.1915 0.8696 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9215 0.1614 -0.4913 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6598 -0.4578 -1.0085 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5961 -1.9420 -1.0717 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0823 -2.2577 -1.1704 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5528 -0.9063 -1.2819 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4038 -0.4400 -2.7092 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9128 -0.7632 -0.7736 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9186 -1.5660 -1.1249 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2956 -1.4414 -0.6296 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5453 0.0028 -0.2387 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9421 0.3281 0.1077 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9486 -0.6735 -0.4189 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3051 1.6595 -0.5674 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0989 0.5587 1.5560 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9799 0.0091 2.1601 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1560 1.4742 2.2459 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8179 1.5693 1.5958 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5342 0.3017 0.8377 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4661 -0.8262 1.8572 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2116 0.3145 0.1649 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3455 1.2730 0.4327 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0028 1.2990 -0.2210 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3934 -0.1416 -0.3260 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1878 -0.8121 1.0159 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9533 -0.0661 -1.5178 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7301 0.8323 -1.9585 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1688 -1.3267 -2.1252 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3933 -0.4720 0.8654 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9634 0.1549 -0.7575 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0298 1.1649 0.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0867 1.3105 1.9514 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3411 3.1223 0.5495 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8807 2.2347 -0.9826 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6545 2.7129 0.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1595 -1.8422 0.2978 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9513 -1.4001 -0.0994 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4274 1.6042 1.3312 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6314 0.3212 2.5018 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3776 -1.2925 1.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4763 0.1935 1.5904 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7312 1.2816 -0.5164 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5544 -0.0960 -2.0766 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9635 -2.4932 -0.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0497 -2.2893 -2.0245 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2651 -2.8521 -0.3291 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1139 -2.8777 -2.0920 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4141 -0.6204 -3.1927 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1687 0.6107 -2.8408 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2861 -1.0670 -3.3041 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6846 -2.3521 -1.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5931 -2.1673 0.1410 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9715 -1.6399 -1.5124 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2285 0.5926 -1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8513 -1.6480 0.0808 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8009 -0.7322 -1.5165 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9530 -0.2343 -0.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3471 1.6656 -0.9173 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6081 1.8642 -1.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1933 2.5082 0.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6021 2.4796 2.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 1.0509 3.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6567 2.4807 1.0102 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0539 1.5951 2.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0868 -1.7758 1.4319 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3979 -0.9769 2.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6994 -0.5383 2.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6005 2.0438 1.1198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1114 1.8082 -1.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7546 1.8189 0.3700 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7611 -1.4376 1.0367 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1442 -0.0593 1.8283 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9664 -1.5498 1.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7151 -1.4234 -2.9687 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 30 31 1 1 8 32 1 0 32 33 2 0 32 34 1 0 30 9 1 0 30 12 1 0 27 14 1 0 25 17 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 9 49 1 6 10 50 1 0 10 51 1 0 11 52 1 0 11 53 1 0 13 54 1 0 13 55 1 0 13 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 6 19 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 20 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 26 71 1 0 26 72 1 0 26 73 1 0 28 74 1 0 29 75 1 0 29 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 34 80 1 0 M END

Standard InCHIKey	DVXFDXIVWQWLIU-IZARGIBGSA-N
Standard InCHI	InChI=1S/C31H46O3/c1-19(2)20(3)9-10-21(27(33)34)22-13-17-31(8)24-11-12-25-28(4,5)26(32)15-16-29(25,6)23(24)14-18-30(22,31)7/h11,14,19,21-22,25H,3,9-10,12-13,15-18H2,1-2,4-8H3,(H,33,34)/t21?,22-,25+,29-,30-,31+/m1/s1
SMILES	CC(C)C(=C)CCC([C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	466.34	Volume:	523.695 ? Van der Waals volume.
Dense:	0.89	LogP:	5.209 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.955 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.472 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	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:	0.407	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.873	Fsp³:	0.742
MCE-18:	80.667 ? 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:	0.936	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.028 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.557	Promiscuous compounds:	0.007

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.978	MDCK Permeability:	-4.742
Pgp-inhibitor:	0.536	Pgp-substrate:	0.0
PAMPA:	0.23 ? 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%):	0.154	30% Bioavailability (F30%):	0.307
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011	MRP1:	0.997
Plasma Protein Binding (PPB):	91.25%	Volume Distribution (VD):	-0.007
Fu:	8.634% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.81
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.265	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.434 ? 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):

6.103

Half-life (T1/2):

0.433

ADMET: Toxicity

hERG Blockers:	0.041	hERG Blockers (10um):	0.116
Human Hepatotoxicity (H-HT):	0.663	Drug-induced Liver Injury (DILI):	0.207
AMES Toxicity:	0.118	Rat Oral Acute Toxicity:	0.282
Maximum Recommended Daily Dose:	0.567	Skin Sensitization:	0.728
Carcinogencity:	0.646	Eye Corrosion:	0.043
Eye Irritation:	0.711	Respiratory Toxicity:	0.538
Drug-induced Neurotoxicity:	0.222	Ototoxicity:	0.627
Hematotoxicity:	0.519	Drug-induced Nephrotoxicity:	0.665
Genotoxicity:	0.778	RPMI-8226 Immunitoxicity:	0.079
A549 Cytotoxicity:	0.067	Hek293 Cytotoxicity:	0.204
BCF:	1.265 ? 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:	4.046 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.626 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.87 ? 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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO33546	Poria coco	Species	n.a.	Eukaryota	n.a.	Yunnan, Kunming, China	n.a.	PMID[17488130]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3354	Fomes officinalis	Species	Coriolaceae	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	10
Inhibition	4
Activity	1

Activity Type	# Activity
Individual protein	1
Cell line	8
Organism	4
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	4600.0	nM	PMID[23092389]

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[17488130]
NPT461	Cell line	PANC-1	Homo sapiens	IC50	=	5500.0	nM	PMID[21250700]
NPT81	Cell line	A549	Homo sapiens	IC50	=	10000.0	nM	PMID[21250700]
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	=	12200.0	nM	PMID[21250700]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	29200.0	nM	PMID[21250700]
NPT377	Cell line	OVCAR-3	Homo sapiens	IC50	=	37700.0	nM	PMID[21250700]
NPT90	Cell line	DU-145	Homo sapiens	IC50	>	100000.0	nM	PMID[21250700]
NPT2477	Cell line	NUGC-3	Homo sapiens	IC50	=	38400.0	nM	PMID[23092389]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	89700.0	nM	PMID[21250700]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[21250700]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	9.5	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	43.9	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	79.5	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	100.0	%	PMID[17488130]

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 NPC69279 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	27062
0.1-0.2	20578
0.2-0.3	1956
0.3-0.4	189
0.4-0.5	41
0.5-0.6	24
0.6-0.7	5
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
0.8033	Intermediate Similarity	NPC83569
0.7164	Intermediate Similarity	NPC152897
0.6866	Remote Similarity	NPC77168
0.6377	Remote Similarity	NPC296367
0.6111	Remote Similarity	NPC155676
0.6027	Remote Similarity	NPC263347
0.6	Remote Similarity	NPC87552
0.5694	Remote Similarity	NPC66429
0.5571	Remote Similarity	NPC201912
0.5571	Remote Similarity	NPC38350
0.5571	Remote Similarity	NPC601139
0.5507	Remote Similarity	NPC170793
0.5417	Remote Similarity	NPC84271
0.5417	Remote Similarity	NPC102414
0.5405	Remote Similarity	NPC608955
0.5395	Remote Similarity	NPC478312
0.5352	Remote Similarity	NPC89077
0.5352	Remote Similarity	NPC4166
0.5352	Remote Similarity	NPC311092
0.527	Remote Similarity	NPC206810
0.527	Remote Similarity	NPC310470
0.52	Remote Similarity	NPC469406
0.5139	Remote Similarity	NPC196827
0.5135	Remote Similarity	NPC44181
0.5135	Remote Similarity	NPC54689
0.5135	Remote Similarity	NPC606857
0.5068	Remote Similarity	NPC470048
0.5067	Remote Similarity	NPC45324
0.5067	Remote Similarity	NPC162001
0.5067	Remote Similarity	NPC203035
0.5065	Remote Similarity	NPC42042

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC69279 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6874
0.1-0.2	2215
0.2-0.3	61
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