NPASS Compound

Natural Product: NPC474351

Natural Product ID	NPC474351
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Di-O-Butylmangostin
IUPAC Name	3,6-dibutoxy-1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
Synonyms	Di-O-Butylmangostin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL465560
PubChem CID	10768348
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

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 82 0 0 0 0 0 0 0 0999 V2000 -6.7100 4.1372 -1.8830 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2048 4.2645 -1.8478 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5817 2.8594 -1.8267 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0727 2.1629 -0.6057 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6371 0.8815 -0.3813 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4287 0.3265 -0.1694 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2556 1.0377 -0.1231 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0327 0.3857 0.1038 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0911 1.0211 0.1536 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2539 0.4322 0.3657 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4179 1.1752 0.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6592 0.6571 0.6090 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8305 1.3657 0.6494 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0019 2.7380 0.4897 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4767 3.0524 0.6154 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7325 4.5362 0.4499 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2913 5.0543 -0.8772 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7438 -0.7317 0.7988 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6315 -1.5402 0.7801 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3825 -0.9408 0.5590 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1986 -1.6426 0.5092 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2011 -2.8719 0.6637 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0055 -0.9669 0.2808 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1894 -1.6679 0.2324 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3884 -1.0621 0.0141 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6387 -1.8936 -0.0202 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4115 -1.7449 1.2253 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6341 -1.3007 1.3068 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4354 -0.8745 0.1409 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2338 -1.2329 2.6994 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1640 -3.0581 0.4146 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7240 -3.0023 1.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0800 -3.7284 -0.2190 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0396 -4.6110 -0.3462 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2872 -5.2647 -1.6651 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8776 -5.0139 0.7866 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9881 -1.2952 1.0120 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8574 -1.6752 -0.0362 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1405 4.2872 -0.8642 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1798 4.8955 -2.5428 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0004 3.1416 -2.2609 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9213 4.7565 -0.9158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8295 4.8314 -2.7120 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9252 2.3897 -2.7738 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5030 2.9888 -1.9279 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2055 2.1224 -0.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8993 2.8541 0.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1800 2.1038 -0.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3251 2.2419 0.2543 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3892 3.3328 1.1787 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6849 3.0221 -0.5402 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0272 2.5225 -0.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7987 2.7151 1.6068 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8143 4.7418 0.5506 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2046 5.0730 1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2165 5.0483 -1.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6293 6.1187 -0.9487 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7504 4.4341 -1.6998 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1724 -1.6728 -0.9471 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3098 -2.9757 -0.0845 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8446 -2.0564 2.1401 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8478 -0.6939 -0.7706 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1937 -1.6746 -0.1059 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0218 0.0405 0.4231 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3146 -1.0126 2.6242 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1397 -2.2378 3.1444 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6720 -0.5136 3.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0038 -3.6426 -0.4004 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6534 -3.1660 1.7086 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8837 -3.4880 1.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -3.4939 -1.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9951 -4.6263 -2.2494 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3097 -5.2650 -2.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6844 -6.2809 -1.5326 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6884 -5.7310 0.4677 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3211 -4.1699 1.3011 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3038 -5.5932 1.5462 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3540 -2.1302 -0.8986 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4846 -0.7987 -0.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5754 -2.4065 0.3771 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 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 12 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 2 3 28 29 1 0 28 30 1 0 24 31 1 0 19 32 1 0 32 33 1 0 33 34 2 3 34 35 1 0 34 36 1 0 18 37 1 0 37 38 1 0 25 6 1 0 23 8 2 0 20 10 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 0 2 43 1 0 3 44 1 0 3 45 1 0 4 46 1 0 4 47 1 0 7 48 1 0 11 49 1 0 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 17 58 1 0 26 59 1 0 26 60 1 0 27 61 1 0 29 62 1 0 29 63 1 0 29 64 1 0 30 65 1 0 30 66 1 0 30 67 1 0 31 68 1 0 32 69 1 0 32 70 1 0 33 71 1 0 35 72 1 0 35 73 1 0 35 74 1 0 36 75 1 0 36 76 1 0 36 77 1 0 38 78 1 0 38 79 1 0 38 80 1 0 M END

Standard InCHIKey	YJECLZOANRGWIU-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C32H42O6/c1-8-10-16-36-24-18-26-29(30(33)22(24)14-12-20(3)4)31(34)28-23(15-13-21(5)6)32(35-7)27(19-25(28)38-26)37-17-11-9-2/h12-13,18-19,33H,8-11,14-17H2,1-7H3
SMILES	CCCCOc1cc2oc3cc(OCCCC)c(c(c3c(=O)c2c(c1CC=C(C)C)O)CC=C(C)C)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	522.3	Volume:	565.372 ? Van der Waals volume.
Dense:	0.924	LogP:	8.641 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.168 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.238 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	19.0
TPSA:	78.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.139	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.125	Fsp³:	0.469
MCE-18:	22.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.994	Fluc inhibitor:	0.267 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.964 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.809 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.152	Promiscuous compounds:	0.151

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.666	MDCK Permeability:	-4.669
Pgp-inhibitor:	1.0	Pgp-substrate:	0.211
PAMPA:	0.047 ? 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):	0.194
20% Bioavailability (F20%):	0.922	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.913
Plasma Protein Binding (PPB):	96.968%	Volume Distribution (VD):	0.334
Fu:	3.507% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.999
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.129	CYP2C9-substrate:	0.319
CYP2D6-inhibitor:	0.229	CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

7.197

Half-life (T1/2):

0.549

ADMET: Toxicity

hERG Blockers:	0.242	hERG Blockers (10um):	0.73
Human Hepatotoxicity (H-HT):	0.316	Drug-induced Liver Injury (DILI):	0.886
AMES Toxicity:	0.331	Rat Oral Acute Toxicity:	0.808
Maximum Recommended Daily Dose:	0.248	Skin Sensitization:	0.673
Carcinogencity:	0.679	Eye Corrosion:	0.0
Eye Irritation:	0.289	Respiratory Toxicity:	0.904
Drug-induced Neurotoxicity:	0.091	Ototoxicity:	0.301
Hematotoxicity:	0.1	Drug-induced Nephrotoxicity:	0.517
Genotoxicity:	0.126	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.48	Hek293 Cytotoxicity:	0.782
BCF:	2.46 ? 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:	5.303 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.773 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.619 ? 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
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	stem bark	Pangradin village, Jasinga, West Java, Indonesia	2005-AUG	PMID[19839614]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6249	Garcinia mangostana	Species	Clusiaceae	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
Inhibition	12

Activity Type	# Activity
Organism	12

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
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	-38.0	%	PMID[19128055]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	-66.0	%	PMID[20483615]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	-69.0	%	PMID[18458131]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	-7.0	%	PMID[23013292]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	-4.0	%	PMID[18052327]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	-3.0	%	PMID[11325232]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	1.0	%	PMID[12713408]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	4.0	%	PMID[15844962]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	-2.0	%	PMID[15771418]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	-5.0	%	DrugMatrix in vivo data: Pathology

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 NPC474351 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	19550
0.1-0.2	26561
0.2-0.3	3404
0.3-0.4	281
0.4-0.5	42
0.5-0.6	9
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC474287
0.8462	Intermediate Similarity	NPC475886
0.7971	Intermediate Similarity	NPC475883
0.7971	Intermediate Similarity	NPC474187
0.7846	Intermediate Similarity	NPC165977
0.7391	Intermediate Similarity	NPC474186
0.7183	Intermediate Similarity	NPC474350
0.625	Remote Similarity	NPC14353
0.6104	Remote Similarity	NPC229632
0.6027	Remote Similarity	NPC56085
0.6027	Remote Similarity	NPC602307
0.5733	Remote Similarity	NPC604618
0.5625	Remote Similarity	NPC152659
0.5432	Remote Similarity	NPC236521
0.5395	Remote Similarity	NPC266499
0.5366	Remote Similarity	NPC170245
0.5181	Remote Similarity	NPC117854
0.5128	Remote Similarity	NPC152951
0.5119	Remote Similarity	NPC239752
0.5068	Remote Similarity	NPC174999

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3076
0.1-0.2	5920
0.2-0.3	153
0.3-0.4	1
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