NPASS Compound

Natural Product: NPC86354

Natural Product ID	NPC86354
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DBIFLQJICIZXPC-VARCGREHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6324947
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 87 0 0 0 0 0 0 0 0999 V2000 -4.7068 2.0462 2.3181 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6007 0.7047 3.0103 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8607 0.3047 3.6924 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8104 -0.4163 2.7948 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1102 -1.3794 1.8654 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9127 -0.6699 1.1958 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3241 -1.5829 0.3687 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3992 -1.2695 -0.9826 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6192 0.0116 -1.2404 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7228 0.4192 -2.6958 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1659 1.8380 -2.7719 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7550 1.8412 -2.2494 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6182 1.0528 -0.9635 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3129 0.9926 -0.6214 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8545 0.4091 -0.9417 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9892 0.7812 -0.1706 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2342 0.2770 -0.3862 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 -0.6380 -1.4097 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6299 -1.1536 -1.6324 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7826 -1.9789 -2.5448 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6816 -0.7243 -0.8210 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4893 0.1926 0.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5793 0.6598 1.0543 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8527 0.1692 0.9201 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8988 0.6162 1.7445 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6699 1.5642 2.7139 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3742 2.0638 2.8498 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3696 1.6082 2.0291 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6972 2.0149 3.5382 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9897 1.4800 3.3609 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 0.6416 0.3466 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2867 -1.0195 -2.1729 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0034 -0.5001 -1.9515 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0239 -0.9595 -2.7835 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6661 -2.2133 -2.6048 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4527 -1.9522 -3.2069 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3966 -3.3029 -2.8155 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2121 -3.6480 -1.6208 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5563 -4.3951 -3.8172 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2899 -0.1338 -0.9307 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4398 3.1730 -1.9368 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1751 2.3185 -4.0741 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0440 0.4131 -3.1369 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0673 -0.2628 2.1975 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9667 -1.7530 0.8501 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6169 0.4731 2.0934 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5184 1.4395 4.1714 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8199 2.8627 3.0826 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4742 2.0813 1.5407 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7233 2.2312 1.8344 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8372 0.8677 3.8329 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6086 -0.2860 4.6201 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4969 -1.0309 3.4300 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7548 -2.2244 2.4977 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3897 0.1923 0.6567 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9901 -2.1102 -1.5726 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4674 -1.1033 -1.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0019 0.8446 -0.6191 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1307 -0.2549 -3.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8184 2.4512 -2.1213 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0701 1.5401 -3.0367 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1478 1.6998 -0.1771 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8654 1.4991 0.6288 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6604 -1.1377 -1.0115 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1210 -0.5768 0.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9034 0.2130 1.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2391 2.8072 3.6223 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3578 2.0055 2.1451 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9821 0.3623 3.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4215 1.8858 2.4209 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6898 1.8200 4.1697 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7452 -2.0747 -2.7049 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3473 -2.6755 -1.6691 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3889 -2.9178 -3.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3105 -4.0486 -4.5767 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9827 -5.3052 -3.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5879 -4.6514 -4.3040 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3228 3.3195 -0.9818 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7408 1.7138 -4.6379 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4645 1.3079 -2.9972 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6474 -2.5135 0.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3961 -0.0551 1.7351 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2481 1.7077 3.5289 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 29 30 1 0 22 31 1 0 18 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 32 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 13 40 1 0 12 41 1 0 11 42 1 0 10 43 1 0 6 44 1 0 5 45 1 0 4 46 1 0 3 47 1 0 44 2 1 0 40 9 1 0 33 15 1 0 31 17 1 0 28 23 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 1 3 52 1 1 4 53 1 1 5 54 1 1 6 55 1 6 8 56 1 0 8 57 1 0 9 58 1 1 10 59 1 6 11 60 1 1 12 61 1 6 13 62 1 1 16 63 1 0 21 64 1 0 24 65 1 0 25 66 1 0 27 67 1 0 28 68 1 0 30 69 1 0 30 70 1 0 30 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 41 78 1 0 42 79 1 0 43 80 1 0 45 81 1 0 46 82 1 0 47 83 1 0 M END

Standard InCHIKey	DBIFLQJICIZXPC-VARCGREHSA-N
Standard InCHI	InChI=1S/C31H36O16/c1-12-22(34)24(36)26(38)30(43-12)42-11-20-23(35)25(37)27(39)31(47-20)46-19-10-18-21(29(28(19)41-4)44-13(2)32)16(33)9-17(45-18)14-5-7-15(40-3)8-6-14/h5-10,12,20,22-27,30-31,34-39H,11H2,1-4H3/t12-,20+,22+,23+,24+,25-,26+,27+,30+,31+/m0/s1
SMILES	C[C@H]1[C@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3cc4c(c(=O)cc(c5ccc(cc5)OC)o4)c(c3OC)OC(=O)C)O2)O)O)O)O1)O)O)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
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	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 NPC86354 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	16831
0.1-0.2	28957
0.2-0.3	3234
0.3-0.4	602
0.4-0.5	162
0.5-0.6	40
0.6-0.7	12
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
0.75	Intermediate Similarity	NPC204693
0.7222	Intermediate Similarity	NPC475366
0.7191	Intermediate Similarity	NPC22062
0.7191	Intermediate Similarity	NPC473634
0.7191	Intermediate Similarity	NPC138811
0.6813	Remote Similarity	NPC475155
0.6778	Remote Similarity	NPC295613
0.6778	Remote Similarity	NPC473657
0.6354	Remote Similarity	NPC209296
0.6196	Remote Similarity	NPC211594
0.6186	Remote Similarity	NPC483707
0.617	Remote Similarity	NPC44931
0.6146	Remote Similarity	NPC284277
0.6146	Remote Similarity	NPC475497
0.6122	Remote Similarity	NPC488089
0.602	Remote Similarity	NPC473623
0.6	Remote Similarity	NPC15358
0.5938	Remote Similarity	NPC473512
0.5938	Remote Similarity	NPC129827
0.5938	Remote Similarity	NPC210073
0.5882	Remote Similarity	NPC475261
0.5825	Remote Similarity	NPC11468
0.5607	Remote Similarity	NPC311850
0.5567	Remote Similarity	NPC187379
0.5514	Remote Similarity	NPC473644
0.5455	Remote Similarity	NPC68592
0.5455	Remote Similarity	NPC473895
0.54	Remote Similarity	NPC473571
0.54	Remote Similarity	NPC110941
0.5392	Remote Similarity	NPC473327
0.5385	Remote Similarity	NPC114740
0.5361	Remote Similarity	NPC172807
0.5347	Remote Similarity	NPC46202
0.5347	Remote Similarity	NPC126784
0.5347	Remote Similarity	NPC241423
0.5312	Remote Similarity	NPC99957
0.5294	Remote Similarity	NPC470443
0.5248	Remote Similarity	NPC186816
0.5238	Remote Similarity	NPC101636
0.5213	Remote Similarity	NPC186807
0.52	Remote Similarity	NPC67105
0.519	Remote Similarity	NPC14958
0.5172	Remote Similarity	NPC262222
0.5152	Remote Similarity	NPC254540
0.5143	Remote Similarity	NPC475382
0.514	Remote Similarity	NPC244875
0.5135	Remote Similarity	NPC488087
0.5114	Remote Similarity	NPC479450
0.5053	Remote Similarity	NPC181712
0.505	Remote Similarity	NPC173582
0.505	Remote Similarity	NPC265885
0.505	Remote Similarity	NPC181465
0.505	Remote Similarity	NPC215710
0.505	Remote Similarity	NPC473438
0.505	Remote Similarity	NPC227508
0.505	Remote Similarity	NPC253788
0.5044	Remote Similarity	NPC488086

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC86354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4664
0.1-0.2	4397
0.2-0.3	78
0.3-0.4	5
0.4-0.5	1
0.5-0.6	1
0.6-0.7	2
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
0.6465	Remote Similarity	NPD7472	Pre-clinical
0.6354	Remote Similarity	NPD7054	Phase 4
0.5234	Remote Similarity	NPD7808	Phase 3

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