NPASS Compound

Natural Product: NPC267965

Natural Product ID	NPC267965
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cheatoglobosin G
IUPAC Name	n.a.
Synonyms	Cheatoglobosin G
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL486257
PubChem CID	23259924
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001819] Isoindoles and derivatives [CHEMONTID:0002496] Isoindolines [CHEMONTID:0001820] Isoindolones

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 75 79 0 0 0 0 0 0 0 0999 V2000 -5.5917 0.5329 -2.4600 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8630 -0.2045 -1.4476 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5495 -0.8707 -2.0099 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7594 -1.2551 -0.7745 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5811 -0.7370 -0.5485 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7341 -1.0130 0.6082 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1154 -2.1950 0.4133 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7425 -3.3215 0.5485 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1435 -2.3618 1.4678 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7141 -1.2605 1.9338 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3512 0.0830 1.4329 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0721 0.2727 1.0761 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8540 0.8550 2.1632 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0929 2.0859 1.9979 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4387 0.3479 3.3966 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6756 1.2269 3.7850 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5667 0.9693 2.6016 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9078 -0.2121 2.4712 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0233 1.9299 1.6470 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0081 3.1089 2.0100 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4910 1.6279 0.2684 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4833 0.4021 -0.1709 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9295 2.8035 -0.5314 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0125 1.2423 -0.0735 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1850 1.2094 -0.5298 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0852 0.3219 0.1144 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4368 0.9143 0.4002 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1951 1.1910 -0.8177 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3726 2.4746 -1.3308 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1050 2.3803 -2.4459 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4131 1.0746 -2.6818 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8406 0.3416 -1.6614 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9698 -1.0512 -1.6175 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6832 -1.6553 -2.6234 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2617 -0.9212 -3.6560 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1302 0.4612 -3.6949 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0863 2.0213 -0.5003 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7483 -1.3623 2.9815 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4970 -3.6981 1.9680 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3443 1.2320 -1.9839 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0020 1.0628 -3.2199 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2512 -0.1712 -3.0491 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4694 -1.1261 -1.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8396 -1.7747 -2.5231 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0076 -0.1910 -2.6526 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1966 -1.9765 -0.1168 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1878 -0.0587 -1.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4442 -1.2803 1.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5094 -2.2827 -0.6176 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9234 -3.7541 -0.3023 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6452 0.8651 2.1697 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7502 0.5141 4.2517 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7153 -0.7216 3.4069 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0372 0.9082 4.7304 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4275 2.2801 3.7655 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1009 -0.3995 0.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9820 3.0287 -0.4600 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5575 2.7391 -1.5813 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3673 3.6979 -0.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1458 -0.6128 -0.4334 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9944 0.1731 1.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3062 1.7952 1.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0033 3.4073 -0.9321 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4379 3.1280 -3.0958 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5279 -1.6329 -0.8148 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8251 -2.7468 -2.6565 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8243 -1.3634 -4.4595 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5727 1.0472 -4.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8750 2.6988 -1.2329 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6113 -1.9381 2.5447 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1917 -0.3728 3.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3169 -1.8584 3.8594 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8690 -4.5054 1.5703 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2856 -3.6721 3.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6027 -3.8975 1.9261 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 2 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 1 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 21 23 1 0 12 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 24 37 1 0 10 38 1 0 9 39 1 0 22 2 1 0 32 28 1 0 12 6 1 0 36 31 1 0 26 11 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 1 3 44 1 0 3 45 1 0 4 46 1 0 5 47 1 0 6 48 1 1 7 49 1 6 8 50 1 0 11 51 1 1 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 22 56 1 0 23 57 1 0 23 58 1 0 23 59 1 0 26 60 1 6 27 61 1 0 27 62 1 0 29 63 1 0 30 64 1 0 33 65 1 0 34 66 1 0 35 67 1 0 36 68 1 0 37 69 1 0 38 70 1 0 38 71 1 0 38 72 1 0 39 73 1 0 39 74 1 0 39 75 1 0 M END

Standard InCHIKey	COZBDBUQXIMMKP-RWFPWACCSA-N
Standard InCHI	InChI=1S/C32H36N2O5/c1-17-8-7-10-23-30(38)20(4)19(3)28-25(15-21-16-33-24-11-6-5-9-22(21)24)34-31(39)32(23,28)27(36)13-12-26(35)29(37)18(2)14-17/h5-7,9-11,14,16-17,23,25,28,30,33,38H,8,12-13,15H2,1-4H3,(H,34,39)/b10-7+,18-14+/t17-,23-,25-,28-,30+,32+/m0/s1
SMILES	C[C@H]1C/C=C/[C@H]2[C@H](O)C(=C([C@@H]3[C@@]2(C(=O)CCC(=O)C(=O)/C(=C/1)/C)C(=N[C@H]3Cc1c[nH]c2c1cccc2)O)C)C

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
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	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 Type	# Activity
Cell line	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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	3.2	ug.mL-1	PMID[15497948]

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 NPC267965 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	11889
0.1-0.2	36462
0.2-0.3	1261
0.3-0.4	196
0.4-0.5	19
0.5-0.6	12
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8736	High Similarity	NPC132211
0.7634	Intermediate Similarity	NPC87856
0.7553	Intermediate Similarity	NPC151976
0.75	Intermediate Similarity	NPC271862
0.7396	Intermediate Similarity	NPC2395
0.7053	Intermediate Similarity	NPC266192
0.6701	Remote Similarity	NPC487662
0.6566	Remote Similarity	NPC203614
0.65	Remote Similarity	NPC204491
0.6465	Remote Similarity	NPC487661
0.64	Remote Similarity	NPC487664
0.6373	Remote Similarity	NPC235885
0.6275	Remote Similarity	NPC267926
0.6238	Remote Similarity	NPC487665
0.6078	Remote Similarity	NPC141428
0.604	Remote Similarity	NPC98715
0.6019	Remote Similarity	NPC147446
0.6019	Remote Similarity	NPC487657
0.598	Remote Similarity	NPC225821
0.5922	Remote Similarity	NPC46225
0.5905	Remote Similarity	NPC487658
0.5865	Remote Similarity	NPC487663
0.5859	Remote Similarity	NPC157828
0.5743	Remote Similarity	NPC195239
0.5607	Remote Similarity	NPC57690
0.5607	Remote Similarity	NPC487660
0.5481	Remote Similarity	NPC606897
0.5437	Remote Similarity	NPC605975
0.5225	Remote Similarity	NPC487659
0.5045	Remote Similarity	NPC290529

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC267965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3500
0.1-0.2	5457
0.2-0.3	156
0.3-0.4	37
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