NPASS Compound

Natural Product: NPC475495

Natural Product ID	NPC475495
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UZRKPVBMUCEXBL-SKGWOQKVSA-N
IUPAC Name	n.a.
Synonyms	Ingol-3,7,8,12-Triacetate,Tiglate
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL506709
PubChem CID	44559782
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 83 86 0 0 0 0 0 0 0 0999 V2000 -7.0596 -3.1884 1.5368 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7583 -3.3977 0.8798 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8826 -2.4354 0.8113 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1988 -1.1168 1.3992 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5985 -2.6053 0.1747 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3219 -3.7189 -0.3329 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6173 -1.6167 0.0719 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3617 -1.7849 -0.5544 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3286 -1.9774 0.5547 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0257 -2.0660 0.0529 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2112 -2.2579 -1.1341 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2184 -1.9283 0.9172 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1828 -3.0872 1.0102 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4785 -2.4053 1.3821 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4013 -1.1393 0.5170 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9751 -0.7501 0.6639 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3573 -0.9638 1.8690 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2678 0.0322 -0.3867 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5980 1.1135 -0.1279 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8881 1.8709 -1.1819 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 1.5394 -1.1317 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8141 0.3489 -1.9679 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0197 -0.9920 -1.7013 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1721 -0.2080 -2.3035 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5881 -0.4561 -3.7307 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2672 0.3529 -1.4496 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1782 2.6187 -1.9588 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0574 3.5495 -1.4571 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3623 3.4045 -0.2287 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6433 4.6577 -2.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0424 3.2543 -0.7875 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6312 4.1626 -1.6798 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9994 3.7008 -2.8010 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8409 5.5885 -1.3945 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5698 1.5608 1.2560 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2949 -0.1944 1.0784 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3784 0.2394 0.3391 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5915 -0.1854 -0.8226 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3149 1.2370 0.9413 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4525 -2.0899 2.8453 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6325 -1.0941 1.7197 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9978 -3.2068 2.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7686 -3.9962 1.2443 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5044 -2.1839 1.2996 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5376 -4.3563 0.4548 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8454 -0.5872 0.6410 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7192 -1.1734 2.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2827 -0.4618 1.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4497 -2.8810 -0.9189 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4879 -3.0313 1.0133 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8053 -3.7469 1.8329 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2457 -3.6527 0.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3245 -3.0505 1.0884 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6931 -1.4327 -0.5017 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2955 -0.2615 -1.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2897 1.7750 -2.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0754 1.6571 -0.1830 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2848 0.5795 -2.9839 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5551 -1.6814 -2.5402 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6681 -0.2835 -3.8996 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4389 -1.5574 -3.9199 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0439 0.1645 -4.4546 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1867 -0.3073 -1.4218 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6701 1.2485 -2.0214 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9706 0.7368 -0.4782 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9372 5.1767 -2.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0049 5.4423 -1.4917 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5657 4.3695 -2.7841 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3254 5.9576 -0.5063 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9293 5.7826 -1.3720 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4187 6.1770 -2.2606 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5321 1.2850 1.7556 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5995 2.7123 1.2034 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6830 1.3527 1.8191 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2198 1.3296 0.3288 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8402 2.2234 0.9922 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6397 0.9385 1.9560 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5494 -2.4962 3.3601 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4494 -0.9710 2.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3260 -2.4397 3.4047 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1716 -1.0059 2.4367 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4751 -1.5934 2.3118 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0907 -0.1230 1.4057 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 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 2 3 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 21 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 20 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 19 35 1 0 15 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 14 40 1 0 9 41 1 0 23 8 1 0 16 12 1 0 17 12 1 0 24 22 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 4 46 1 0 4 47 1 0 4 48 1 0 8 49 1 0 9 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 15 54 1 0 18 55 1 0 20 56 1 0 21 57 1 0 22 58 1 0 23 59 1 0 25 60 1 0 25 61 1 0 25 62 1 0 26 63 1 0 26 64 1 0 26 65 1 0 30 66 1 0 30 67 1 0 30 68 1 0 34 69 1 0 34 70 1 0 34 71 1 0 35 72 1 0 35 73 1 0 35 74 1 0 39 75 1 0 39 76 1 0 39 77 1 0 40 78 1 0 40 79 1 0 40 80 1 0 41 81 1 0 41 82 1 0 41 83 1 0 M END

Standard InCHIKey	UZRKPVBMUCEXBL-SKGWOQKVSA-N
Standard InCHI	InChI=1S/C31H42O10/c1-11-14(2)28(36)40-24-17(5)26(35)30-13-16(4)27(39-20(8)34)31(30,41-30)12-15(3)23(37-18(6)32)25(38-19(7)33)22-21(24)29(22,9)10/h11-12,16-17,21-25,27H,13H2,1-10H3/b14-11+,15-12+/t16-,17+,21-,22+,23+,24-,25-,27-,30-,31-/m0/s1
SMILES	CC=C(C)C(=O)OC1C(C(=O)C23CC(C(C2(O3)C=C(C(C(C4C1C4(C)C)OC(=O)C)OC(=O)C)C)OC(=O)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
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	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
Activity	1

Activity Type	# Activity
Organism	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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	>	1000.0	ug	PMID[20415462]

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 NPC475495 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	23391
0.1-0.2	24809
0.2-0.3	1611
0.3-0.4	2
0.4-0.5	8
0.5-0.6	13
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC475277
0.9298	High Similarity	NPC482193
0.8966	High Similarity	NPC477093
0.8852	High Similarity	NPC473522
0.85	High Similarity	NPC482192
0.7742	Intermediate Similarity	NPC482184
0.7742	Intermediate Similarity	NPC482185
0.7344	Intermediate Similarity	NPC482179
0.7188	Intermediate Similarity	NPC482178
0.7188	Intermediate Similarity	NPC482177
0.7121	Intermediate Similarity	NPC482176
0.7077	Intermediate Similarity	NPC81761
0.7015	Intermediate Similarity	NPC482180
0.6912	Remote Similarity	NPC482174
0.6818	Remote Similarity	NPC189556
0.6818	Remote Similarity	NPC477092
0.6757	Remote Similarity	NPC477094
0.6528	Remote Similarity	NPC29922
0.6528	Remote Similarity	NPC477096
0.6418	Remote Similarity	NPC475401
0.6316	Remote Similarity	NPC482402
0.625	Remote Similarity	NPC475305
0.6234	Remote Similarity	NPC482400
0.6081	Remote Similarity	NPC477095
0.597	Remote Similarity	NPC479266
0.5634	Remote Similarity	NPC29905
0.5634	Remote Similarity	NPC482194
0.5634	Remote Similarity	NPC482190
0.5634	Remote Similarity	NPC482186
0.5634	Remote Similarity	NPC482191
0.5432	Remote Similarity	NPC272004
0.5432	Remote Similarity	NPC477101
0.5432	Remote Similarity	NPC477099
0.5432	Remote Similarity	NPC477097
0.5211	Remote Similarity	NPC482187
0.5172	Remote Similarity	NPC482195
0.5122	Remote Similarity	NPC482175

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7171
0.1-0.2	1968
0.2-0.3	11
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