NPASS Compound

Natural Product: NPC487914

Natural Product ID	NPC487914
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TURTULDFIIAPTC-FNAGZWQBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10260646
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

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 82 86 0 0 0 0 0 0 0 0999 V2000 -14.4436 0.6675 1.9058 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3264 -0.0124 2.4545 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1174 -0.0882 1.7745 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0052 -0.9612 0.8068 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7754 -1.1127 0.0373 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6756 -0.2220 0.4250 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9021 0.7183 1.5176 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0304 0.8005 2.1626 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2457 2.0704 3.5962 Br 0 0 0 0 0 0 0 0 0 0 0 0 -8.4023 -1.0450 0.7936 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3815 0.0246 0.5271 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8609 0.8422 -0.3335 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.1202 0.4689 -0.7113 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0383 0.1068 1.1505 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6736 -0.7392 1.9871 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1865 1.1609 0.7738 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8580 1.4052 1.2398 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9413 0.2593 0.8292 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0399 0.1667 -0.6680 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2620 -0.7161 -1.3581 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8852 -0.6838 -1.3878 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2732 0.2108 -2.3008 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0859 0.2775 -2.3727 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9106 -0.5122 -1.5711 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3407 -1.3870 -0.6787 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0665 -1.4335 -0.6281 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7717 -2.7373 0.5817 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.3999 -0.3846 -1.7248 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9407 0.8757 -1.1345 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3521 0.9948 -1.4192 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2576 0.0228 -0.9464 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8352 -0.9483 -0.2669 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7046 0.1147 -1.2325 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3001 1.0319 -1.9085 N 0 0 0 0 0 0 0 0 0 0 0 0 9.6466 0.8050 -1.9771 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9842 -0.0066 -0.8302 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0262 0.8898 0.3148 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0517 1.0229 1.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2456 0.2297 0.8817 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3027 -0.6147 -0.1303 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1919 -0.8298 -1.0865 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8686 -2.2056 -0.9949 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9031 -1.6176 -0.3804 Br 0 0 0 0 0 0 0 0 0 0 0 0 13.3081 0.4083 1.7643 O 0 0 0 0 0 0 0 0 0 0 0 0 14.3093 1.3857 1.5379 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0016 2.2400 2.6055 Br 0 0 0 0 0 0 0 0 0 0 0 0 8.7100 -0.8624 -0.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6080 -0.3623 -3.1268 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3694 1.2973 -3.4050 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.3340 -0.9262 1.3821 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3039 -2.4440 0.0693 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.5178 -2.1032 0.3654 Br 0 0 0 0 0 0 0 0 0 0 0 0 -15.3154 0.6231 2.5607 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1278 1.7241 1.8101 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6758 0.2120 0.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0429 -0.8678 -1.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0580 1.3699 1.7805 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4242 -1.3746 1.8292 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3534 -1.8469 0.0323 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5593 1.8677 0.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8147 1.4861 2.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4486 2.3259 0.7683 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8805 0.4969 1.0951 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8979 1.2414 -1.0461 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1144 -0.0329 -0.9585 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5707 0.9542 -3.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9579 -2.0087 -0.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8672 -1.3100 -1.3711 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3783 1.7665 -1.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8504 0.7703 -0.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7580 1.7865 -1.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1350 1.4963 0.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5645 -0.6083 -2.1208 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6996 -2.6003 -1.8947 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0272 1.3529 2.3634 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7956 2.3681 1.5453 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7821 1.2647 0.5368 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7676 -1.6575 -1.5488 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5373 -1.2492 0.2442 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5025 -1.2776 -3.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9343 -1.0430 2.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0233 -3.1014 0.0278 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 6 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 11 14 1 0 14 15 2 0 14 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 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 24 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 36 35 1 6 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 44 45 1 0 38 46 1 0 36 47 1 0 28 48 1 0 22 49 1 0 18 50 1 0 5 51 1 0 4 52 1 0 8 3 1 0 26 21 1 0 47 33 1 0 6 13 1 6 41 36 1 0 1 53 1 0 1 54 1 0 1 55 1 0 5 56 1 6 7 57 1 0 10 58 1 0 10 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 23 66 1 0 25 67 1 0 28 68 1 0 29 69 1 0 29 70 1 0 30 71 1 0 37 72 1 0 41 73 1 6 42 74 1 0 45 75 1 0 45 76 1 0 45 77 1 0 47 78 1 0 47 79 1 0 48 80 1 0 50 81 1 0 51 82 1 0 M END

Standard InCHIKey	TURTULDFIIAPTC-FNAGZWQBSA-N
Standard InCHI	InChI=1S/C31H30Br6N4O11/c1-48-24-16(34)5-30(26(44)21(24)36)7-18(40-51-30)28(46)38-9-13(42)11-50-23-14(32)3-12(4-15(23)33)20(43)10-39-29(47)19-8-31(52-41-19)6-17(35)25(49-2)22(37)27(31)45/h3-6,13,20,26-27,42-45H,7-11H2,1-2H3,(H,38,46)(H,39,47)/t13?,20?,26-,27+,30+,31-/m0/s1
SMILES	COC1=C([C@@H]([C@@]2(C=C1Br)CC(=NO2)C(=O)NCC(COc1c(cc(cc1Br)C(CNC(=O)C1=NO[C@@]2(C=C(C(=C([C@H]2O)Br)OC)Br)C1)O)Br)O)O)Br

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
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3261	Aplysina archeri	Species	Aplysinidae	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
ED50	1
Ratio	1
ID50	1

Activity Type	# Activity
Organism	1
Others	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
NPT15412	Organism	Feline leukemia virus	Feline leukemia virus	ED50	=	22.0	uM	PMID[1324982]
NPT2	Others	Unspecified	n.a.	Ratio	>	20.0	n.a.	PMID[1324982]
NPT27	Others	Unspecified	n.a.	ID50	>	449.0	uM	PMID[1324982]

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 NPC487914 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	17416
0.1-0.2	32268
0.2-0.3	105
0.3-0.4	20
0.4-0.5	14
0.5-0.6	17
0.6-0.7	9
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC489611
1.0	High Similarity	NPC604329
0.8101	Intermediate Similarity	NPC487915
0.8	Intermediate Similarity	NPC483876
0.8	Intermediate Similarity	NPC600925
0.7442	Intermediate Similarity	NPC489612
0.6667	Remote Similarity	NPC480151
0.6517	Remote Similarity	NPC77435
0.6517	Remote Similarity	NPC259071
0.6477	Remote Similarity	NPC202866
0.6237	Remote Similarity	NPC606574
0.6196	Remote Similarity	NPC603425
0.6061	Remote Similarity	NPC227953
0.6	Remote Similarity	NPC607066
0.6	Remote Similarity	NPC611077
0.5938	Remote Similarity	NPC607100
0.5876	Remote Similarity	NPC609979
0.5814	Remote Similarity	NPC487872
0.5814	Remote Similarity	NPC608122
0.5743	Remote Similarity	NPC603698
0.5714	Remote Similarity	NPC1702
0.5618	Remote Similarity	NPC487873
0.557	Remote Similarity	NPC158672
0.5408	Remote Similarity	NPC174607
0.5408	Remote Similarity	NPC147847
0.5377	Remote Similarity	NPC606635
0.5366	Remote Similarity	NPC487917
0.5227	Remote Similarity	NPC313173
0.5222	Remote Similarity	NPC66855
0.5057	Remote Similarity	NPC473262
0.5057	Remote Similarity	NPC202166
0.5055	Remote Similarity	NPC181086

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC487914 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3348
0.1-0.2	5786
0.2-0.3	16
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