NPASS Compound

Natural Product: NPC262264

Natural Product ID	NPC262264
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IUZNOAOULJFDJI-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	20978310
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 63 65 0 0 0 0 0 0 0 0999 V2000 6.1320 -0.3216 -3.4961 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9045 -0.3176 -2.0061 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7479 -0.7310 -1.5481 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3709 -0.7871 -0.1151 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1671 0.0595 0.1332 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2821 1.4329 0.1785 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1748 2.2198 0.4097 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9387 1.6173 0.5973 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8498 0.2424 0.5472 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9515 -0.5483 0.3167 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8092 -1.9339 0.2753 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4050 -0.3625 0.7370 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4491 -1.6112 0.6908 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4785 0.4543 0.9618 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7307 -0.1227 1.1564 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9178 -1.5800 1.0672 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0159 -2.1801 -0.2846 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1635 -3.6698 -0.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3159 -4.5309 -0.5839 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3237 -4.1544 0.6933 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2281 -1.8386 -0.9560 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7969 0.7540 1.3963 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6591 2.1290 1.4412 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4194 2.6656 1.2431 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3378 1.8433 1.0065 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1314 2.3377 0.8195 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7866 2.9470 1.6878 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7062 4.3342 1.7428 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0706 0.2782 1.6080 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0951 0.0793 0.7028 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5335 2.0425 -0.0115 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6209 3.4310 0.0393 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0248 0.1564 -1.1801 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3738 -0.9072 -4.0222 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2200 0.7270 -3.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1385 -0.7804 -3.6360 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9730 -1.0696 -2.2467 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1426 -0.4587 0.5813 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1292 -1.8417 0.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2744 3.2942 0.4434 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2938 -2.5229 0.9629 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9765 -1.7283 1.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3524 -2.1805 1.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2673 -1.9392 -1.0328 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4654 -5.5854 -0.4175 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4511 -4.2356 -1.1643 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2905 -4.1103 0.1524 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2093 -5.2487 0.9437 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4599 -3.6663 1.6671 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0036 -2.2732 -0.5842 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3051 3.7404 1.2753 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7063 4.7964 0.7314 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8177 4.6238 2.3425 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5879 4.6827 2.3574 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9767 0.7443 0.9635 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4494 -0.9853 0.8057 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8638 0.2633 -0.3534 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1673 3.8702 0.9646 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1860 3.8874 -0.8700 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7110 3.7047 0.0511 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8015 -0.6339 -1.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7781 0.4781 -0.1690 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5173 1.0200 -1.6852 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 9 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 17 21 1 0 15 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 23 27 1 0 27 28 1 0 22 29 1 0 29 30 1 0 6 31 1 0 31 32 1 0 2 33 1 0 10 5 1 0 25 14 1 0 26 8 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 7 40 1 0 11 41 1 0 16 42 1 0 16 43 1 0 17 44 1 0 19 45 1 0 19 46 1 0 20 47 1 0 20 48 1 0 20 49 1 0 21 50 1 0 24 51 1 0 28 52 1 0 28 53 1 0 28 54 1 0 30 55 1 0 30 56 1 0 30 57 1 0 32 58 1 0 32 59 1 0 32 60 1 0 33 61 1 0 33 62 1 0 33 63 1 0 M END

Standard InCHIKey	IUZNOAOULJFDJI-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C26H30O7/c1-13(2)8-9-15-18(30-5)11-20-23(24(15)28)25(29)22-16(10-17(27)14(3)4)26(32-7)21(31-6)12-19(22)33-20/h8,11-12,17,27-28H,3,9-10H2,1-2,4-7H3
SMILES	CC(=CCc1c(cc2c(c1O)c(=O)c1c(CC(C(=C)C)O)c(c(cc1o2)OC)OC)OC)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.2	Volume:	470.386 ? Van der Waals volume.
Dense:	0.966	LogP:	4.335 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.375 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.326 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	19.0
TPSA:	98.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.377	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.594	Fsp³:	0.346
MCE-18:	46.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.486	Fluc inhibitor:	0.203 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.847 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.806 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.051	Promiscuous compounds:	0.11

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.989	MDCK Permeability:	-4.654
Pgp-inhibitor:	0.361	Pgp-substrate:	0.021
PAMPA:	0.063 ? 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):	0.246
20% Bioavailability (F20%):	0.793	30% Bioavailability (F30%):	0.953
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.934
Plasma Protein Binding (PPB):	94.893%	Volume Distribution (VD):	0.174
Fu:	4.984% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.996
BSEP inhibitor:	0.961

ADMET: Metabolism

CYP1A2-inhibitor:	0.023	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.966	CYP2C19-substrate:	0.985
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.044	CYP2D6-substrate:	0.72
CYP3A4-inhibitor:	0.892	CYP3A4-substrate:	0.869
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
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):

6.416

Half-life (T1/2):

1.05

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.457
Human Hepatotoxicity (H-HT):	0.373	Drug-induced Liver Injury (DILI):	0.548
AMES Toxicity:	0.321	Rat Oral Acute Toxicity:	0.548
Maximum Recommended Daily Dose:	0.671	Skin Sensitization:	0.706
Carcinogencity:	0.74	Eye Corrosion:	0.001
Eye Irritation:	0.698	Respiratory Toxicity:	0.856
Drug-induced Neurotoxicity:	0.247	Ototoxicity:	0.612
Hematotoxicity:	0.21	Drug-induced Nephrotoxicity:	0.186
Genotoxicity:	0.455	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.071	Hek293 Cytotoxicity:	0.234
BCF:	1.911 ? 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:	4.38 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.627 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.508 ? 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

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

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 NPC262264 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	18519
0.1-0.2	26222
0.2-0.3	4675
0.3-0.4	367
0.4-0.5	52
0.5-0.6	10
0.6-0.7	7
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
0.8226	Intermediate Similarity	NPC165977
0.7463	Intermediate Similarity	NPC474186
0.7206	Intermediate Similarity	NPC475886
0.7042	Intermediate Similarity	NPC475883
0.7042	Intermediate Similarity	NPC474187
0.7	Intermediate Similarity	NPC474350
0.6806	Remote Similarity	NPC474287
0.6765	Remote Similarity	NPC14353
0.6765	Remote Similarity	NPC56085
0.6622	Remote Similarity	NPC474351
0.6197	Remote Similarity	NPC604618
0.6133	Remote Similarity	NPC229632
0.6056	Remote Similarity	NPC602307
0.5974	Remote Similarity	NPC117854
0.5844	Remote Similarity	NPC152659
0.5833	Remote Similarity	NPC266499
0.5769	Remote Similarity	NPC170245
0.5541	Remote Similarity	NPC152951
0.5507	Remote Similarity	NPC174999
0.55	Remote Similarity	NPC239752
0.5443	Remote Similarity	NPC236521
0.5062	Remote Similarity	NPC472450
0.5062	Remote Similarity	NPC275780

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC262264 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3448
0.1-0.2	5590
0.2-0.3	111
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