NPASS Compound

Natural Product: NPC473435

Natural Product ID	NPC473435
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	13E,17Z-Globostellatic Acid X Methyl Ester
IUPAC Name	methyl (3E,3aS,5aR,6R,7R,9aR,9bS)-7-acetyloxy-3-[(3E,5Z,7E)-6,10-dimethylundeca-3,5,7,9-tetraen-2-ylidene]-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalene-6-carboxylate
Synonyms	13E,17Z-Globostellatic Acid X Methyl Ester
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL430365
PubChem CID	44434366
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 84 86 0 0 0 0 0 0 0 0999 V2000 7.5962 5.4839 -0.3160 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3021 5.9221 -0.9052 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4049 4.9919 -1.2753 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6748 3.6187 -1.1108 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9567 2.5908 -1.3860 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6394 2.5051 -1.9558 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1140 1.2893 -2.0978 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8807 0.8530 -2.6112 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5905 -0.4580 -2.5168 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3828 -1.0274 -3.0004 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2005 -2.1147 -2.4243 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4141 -2.7865 -2.8495 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2143 -2.3577 -3.7243 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5434 -4.0701 -2.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0114 -3.5785 -0.7549 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1206 -2.6557 -1.0546 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0282 -1.3985 -0.1312 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3744 -0.7871 -0.4712 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5191 -1.6944 0.0259 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0725 -3.0869 0.2076 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6609 -3.4673 1.6054 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1899 -2.6128 2.6909 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3484 -1.1710 2.4434 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1542 -0.9890 1.1970 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2230 0.5250 0.8626 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5375 -1.3737 1.4166 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2145 -2.0417 0.6304 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1499 -0.9621 2.5967 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4947 -1.3133 2.8419 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0350 -0.5811 3.5378 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4891 0.4011 4.3276 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3023 0.7873 4.0452 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2037 1.0365 5.4883 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2174 -4.0856 -0.0889 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4539 -3.2342 -0.9238 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2952 -0.4831 -4.1992 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8473 3.6836 -2.3647 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0534 7.3674 -1.0268 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2394 5.1421 -1.1258 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1110 6.3697 0.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4570 4.7437 0.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5072 5.3950 -1.6957 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6942 3.3614 -0.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4090 1.5584 -1.1553 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8006 0.4604 -1.7246 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1968 1.5021 -3.1379 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3927 -1.0389 -2.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5199 -4.5044 -2.0890 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8507 -4.8250 -2.5312 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5363 -4.4913 -0.2741 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7512 -0.7109 -0.4236 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1162 -1.6779 0.8983 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4363 -0.5933 -1.5511 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4153 0.1556 0.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2667 -1.6164 -0.7777 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5851 -3.6039 1.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0485 -4.5149 1.8588 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2043 -2.9803 3.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5406 -2.6882 3.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3638 -0.6715 2.4165 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3025 0.6659 -0.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4528 1.0998 1.4013 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1884 0.8874 1.3170 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0298 -0.4116 3.2033 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9824 -1.8330 1.9978 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5241 -2.0346 3.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5291 2.0554 5.2801 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4307 1.0701 6.3012 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0017 0.3639 5.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7958 -4.2117 0.8707 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 -3.7812 -0.8680 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7688 -5.1150 -0.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9176 -3.5060 -1.8834 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1730 -2.5411 -0.4013 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4366 -4.2091 -0.3134 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2747 -1.3157 -4.9471 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3471 -0.1794 -3.9771 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2395 0.4086 -4.5665 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8721 3.3012 -2.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3655 4.2147 -3.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5338 4.3049 -1.5132 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9909 7.5702 -1.2360 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6561 7.8043 -1.8714 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2998 7.8951 -0.0630 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 2 3 5 6 1 0 6 7 2 3 7 8 1 0 8 9 2 3 9 10 1 0 10 11 2 3 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 23 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 20 34 1 0 16 35 1 0 10 36 1 0 6 37 1 0 2 38 1 0 16 11 1 0 20 15 1 0 24 19 1 0 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 4 43 1 0 5 44 1 0 7 45 1 0 8 46 1 0 9 47 1 0 14 48 1 0 14 49 1 0 15 50 1 0 17 51 1 0 17 52 1 0 18 53 1 0 18 54 1 0 19 55 1 0 21 56 1 0 21 57 1 0 22 58 1 0 22 59 1 0 23 60 1 0 25 61 1 0 25 62 1 0 25 63 1 0 29 64 1 0 29 65 1 0 29 66 1 0 33 67 1 0 33 68 1 0 33 69 1 0 34 70 1 0 34 71 1 0 34 72 1 0 35 73 1 0 35 74 1 0 35 75 1 0 36 76 1 0 36 77 1 0 36 78 1 0 37 79 1 0 37 80 1 0 37 81 1 0 38 82 1 0 38 83 1 0 38 84 1 0 M END

Standard InCHIKey	GRNXZFQSLPDVMF-DNPGXBGVSA-N
Standard InCHI	InChI=1S/C33H46O5/c1-21(2)12-10-13-22(3)14-11-15-23(4)29-25(35)20-27-31(6)19-17-28(38-24(5)34)33(8,30(36)37-9)26(31)16-18-32(27,29)7/h10-15,26-28H,16-20H2,1-9H3/b13-10+,15-11+,22-14-,29-23-/t26-,27+,28-,31+,32+,33-/m1/s1
SMILES	CC(=CC=CC(=CC=CC(=C1C(=O)CC2C1(CCC3C2(CCC(C3(C)C(=O)OC)OC(=O)C)C)C)C)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
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	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	4
Ratio IC50	4

Activity Type	# Activity
Cell line	6
Non-molecular	2

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
NPT737	Cell line	HUVEC	Homo sapiens	IC50	=	60.0	nM	PMID[27096049]
NPT111	Cell line	K562	Homo sapiens	IC50	=	22000.0	nM	PMID[26091285]
NPT737	Cell line	HUVEC	Homo sapiens	Ratio IC50	=	200.0	n.a.	PMID[24020806]
NPT111	Cell line	K562	Homo sapiens	Ratio IC50	=	360.0	n.a.	PMID[25479041]
NPT737	Cell line	HUVEC	Homo sapiens	Ratio IC50	=	75.0	n.a.	DrugMatrix in vivo data: Pathology
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	18000.0	nM	PMID[17524651]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	4700.0	nM	PMID[17524651]

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 NPC473435 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	18847
0.1-0.2	26848
0.2-0.3	3997
0.3-0.4	98
0.4-0.5	23
0.5-0.6	21
0.6-0.7	11
0.7-0.8	0
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473280
1.0	High Similarity	NPC471078
0.8667	High Similarity	NPC106425
0.8667	High Similarity	NPC122324
0.8305	Intermediate Similarity	NPC151725
0.8254	Intermediate Similarity	NPC473482
0.8254	Intermediate Similarity	NPC473284
0.75	Intermediate Similarity	NPC2049
0.7313	Intermediate Similarity	NPC473283
0.7313	Intermediate Similarity	NPC475526
0.6667	Remote Similarity	NPC161638
0.6667	Remote Similarity	NPC80335
0.6667	Remote Similarity	NPC471153
0.6143	Remote Similarity	NPC266955
0.6119	Remote Similarity	NPC474842
0.6119	Remote Similarity	NPC474790
0.6119	Remote Similarity	NPC474976
0.6119	Remote Similarity	NPC475965
0.6119	Remote Similarity	NPC604299
0.6056	Remote Similarity	NPC155332
0.6056	Remote Similarity	NPC114540
0.5972	Remote Similarity	NPC115899
0.5942	Remote Similarity	NPC57079
0.5942	Remote Similarity	NPC108368
0.5915	Remote Similarity	NPC110937
0.5821	Remote Similarity	NPC310752
0.5775	Remote Similarity	NPC605871
0.5385	Remote Similarity	NPC318363
0.5333	Remote Similarity	NPC474018
0.5333	Remote Similarity	NPC473986
0.5244	Remote Similarity	NPC473617
0.5244	Remote Similarity	NPC473828
0.5135	Remote Similarity	NPC6206
0.5135	Remote Similarity	NPC469874
0.5132	Remote Similarity	NPC32577
0.5068	Remote Similarity	NPC474785
0.5068	Remote Similarity	NPC3856
0.5068	Remote Similarity	NPC279639
0.5067	Remote Similarity	NPC250757
0.5067	Remote Similarity	NPC10064
0.5067	Remote Similarity	NPC170221
0.5067	Remote Similarity	NPC301534

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6689
0.1-0.2	2379
0.2-0.3	82
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