NPASS Compound

Natural Product: NPC193222

Natural Product ID	NPC193222
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IZKKHVXIKQNASF-ATRGYWGZSA-N
IUPAC Name	n.a.
Synonyms	1-O-Methylbractatin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL527024
PubChem CID	44583733
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

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 69 73 0 0 0 0 0 0 0 0999 V2000 -2.2161 4.3113 -0.0720 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 3.1705 -0.7109 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3094 1.8657 -0.0202 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4679 1.7743 1.1886 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7672 1.9678 0.3864 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1995 0.8089 -1.0115 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0618 0.9313 -2.1105 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0791 0.0209 -3.1365 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2099 -1.0611 -3.0838 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3707 -1.1730 -2.0069 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4382 -2.2884 -1.9495 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4057 -3.1692 -2.8741 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4653 -2.3836 -0.8096 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3851 -3.3503 -0.7703 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0294 -3.4440 0.5968 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8152 -3.5171 1.5393 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2103 -2.1324 1.6699 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9592 -1.2712 2.6220 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0252 -0.4610 3.4346 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7621 -2.0694 3.6327 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7546 -0.3897 1.9159 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8617 -0.9174 0.6242 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2809 0.0935 -0.3698 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6066 0.6486 0.0067 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7941 1.9380 0.2661 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6402 2.8623 0.1780 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1217 2.4824 0.6410 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7037 -2.1236 0.7318 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8782 -2.0773 0.9189 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4359 -1.4439 0.3459 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4709 -0.4082 0.1279 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3288 -0.2661 -0.9477 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2128 -1.9955 -4.1156 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1031 -1.8187 -5.1941 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9545 1.9970 -2.2158 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6257 4.3449 0.9343 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0005 5.2680 -0.5311 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5837 3.2053 -1.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6301 2.7373 1.7662 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9201 1.0064 1.8563 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3919 1.7095 1.0554 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8848 1.8908 1.4885 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2307 2.9311 0.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3850 1.1666 -0.0708 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7451 0.1074 -3.9933 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6538 -3.9885 -1.5759 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6769 -4.3024 0.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0651 -4.1375 1.0176 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0477 -3.9956 2.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8808 -2.1879 1.9189 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0723 -0.7648 3.2164 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0867 -0.6292 4.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1190 0.6262 3.3102 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4906 -2.7429 3.1944 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3399 -1.3099 4.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0460 -2.5168 4.3330 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5492 0.9431 -0.3153 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2929 -0.2764 -1.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4730 0.0017 0.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8769 2.5297 0.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9620 3.8631 0.4905 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2238 2.8966 -0.8541 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1165 3.5892 0.5709 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3883 2.2273 1.6950 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9279 2.1281 -0.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9572 -2.5638 -5.9914 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1551 -1.9038 -4.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0144 -0.8145 -5.6632 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9529 1.8507 -2.3703 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 3 5 1 0 3 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 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 1 0 22 23 1 6 23 24 1 0 24 25 2 3 25 26 1 0 25 27 1 0 22 28 1 0 28 29 2 0 22 30 1 0 30 31 1 6 31 32 1 0 9 33 1 0 33 34 1 0 7 35 1 0 32 6 2 0 32 10 1 0 30 13 1 0 28 15 1 0 30 17 1 0 1 36 1 0 1 37 1 0 2 38 1 0 4 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 5 44 1 0 8 45 1 0 14 46 1 0 15 47 1 6 16 48 1 0 16 49 1 0 17 50 1 1 19 51 1 0 19 52 1 0 19 53 1 0 20 54 1 0 20 55 1 0 20 56 1 0 23 57 1 0 23 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 27 65 1 0 34 66 1 0 34 67 1 0 34 68 1 0 35 69 1 0 M END

Standard InCHIKey	IZKKHVXIKQNASF-ATRGYWGZSA-N
Standard InCHI	InChI=1S/C29H34O6/c1-9-26(4,5)22-18(30)14-19(33-8)21-23(31)17-12-16-13-20-27(6,7)35-28(25(16)32,11-10-15(2)3)29(17,20)34-24(21)22/h9-10,12,14,16,20,30H,1,11,13H2,2-8H3/t16-,20+,28+,29-/m1/s1
SMILES	C=CC(C)(C)c1c(cc(c2C(=O)C3=C[C@@H]4C[C@H]5C(C)(C)O[C@@](CC=C(C)C)(C4=O)[C@@]35Oc12)OC)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO21229	Garcinia bracteata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785410]
NPO21229	Garcinia bracteata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21229	Garcinia bracteata	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
IC50	1
Activity	1

Activity Type	# Activity
Cell line	1
Others	1

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
NPT91	Cell line	KB	Homo sapiens	IC50	=	0.3	ug.mL-1	DOI[10.6019/CHEMBL1201861]
NPT2	Others	Unspecified	n.a.	Activity	>	10.0	ug ml-1	PMID[23062825]

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 NPC193222 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	9097
0.1-0.2	38375
0.2-0.3	2301
0.3-0.4	34
0.4-0.5	23
0.5-0.6	9
0.6-0.7	15
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
0.7945	Intermediate Similarity	NPC488724
0.7671	Intermediate Similarity	NPC476056
0.7671	Intermediate Similarity	NPC488723
0.6835	Remote Similarity	NPC488712
0.6835	Remote Similarity	NPC475080
0.6835	Remote Similarity	NPC488719
0.6667	Remote Similarity	NPC475109
0.6585	Remote Similarity	NPC488714
0.6585	Remote Similarity	NPC488713
0.6447	Remote Similarity	NPC475107
0.6447	Remote Similarity	NPC43490
0.6447	Remote Similarity	NPC605777
0.642	Remote Similarity	NPC608101
0.6375	Remote Similarity	NPC118128
0.6375	Remote Similarity	NPC488720
0.6203	Remote Similarity	NPC94796
0.6203	Remote Similarity	NPC611777
0.6049	Remote Similarity	NPC607281
0.5976	Remote Similarity	NPC479154
0.5843	Remote Similarity	NPC476255
0.5783	Remote Similarity	NPC475106
0.5455	Remote Similarity	NPC131578
0.5455	Remote Similarity	NPC611483
0.5333	Remote Similarity	NPC286422
0.5333	Remote Similarity	NPC603867
0.5057	Remote Similarity	NPC488715
0.5052	Remote Similarity	NPC610447

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC193222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3658
0.1-0.2	5457
0.2-0.3	35
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