NPASS Compound

Natural Product: NPC610636

Natural Product ID	NPC610636
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UXPCJXXUGGXVGI-PQYLUDDISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL4467432
PubChem CID	n.a.
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 2D 97101 0 0 0 0 0 0 0 0999 V2000 2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 -3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8296 -2.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0796 -1.4772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8296 -0.1782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2931 1.2484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7931 1.2484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2566 -0.1782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0066 -1.4772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6269 0.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9972 1.0420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0431 -1.0599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0394 -2.1746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9786 -3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7286 -2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2286 -2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7286 -2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2286 -2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9786 -1.1424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4786 -1.1424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2286 -2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7286 -2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4786 -3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2286 -5.0395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9786 -3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7181 -5.2176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 -5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 -7.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8086 -8.3287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -4.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4095 -6.0655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -7.3646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6150 -7.7275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4095 -8.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -9.9626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4095 -11.2617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -12.5607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4095 -13.8598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0905 -13.8598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8405 -15.1588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8405 -12.5607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3405 -12.5607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0905 -11.2617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6849 -2.1132 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7461 0.0588 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7981 -1.9284 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7580 0.8169 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3114 -2.7335 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9312 -3.4721 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1778 -2.1188 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6476 0.7454 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6363 2.7402 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2113 1.7368 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5066 -1.4772 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1884 1.8664 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5505 -0.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1540 2.5338 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2867 -1.8986 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8343 -3.4466 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3151 -4.4215 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5916 -0.9860 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4115 -3.9302 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7286 -3.9414 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0916 -0.9860 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2286 0.1567 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2286 0.1567 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.4786 -3.7404 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4786 -6.3385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2286 -5.0395 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4270 -6.9442 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3576 -6.2797 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9797 -8.0718 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 -8.3287 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -4.2535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0905 -8.6636 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 -9.9626 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 -12.5607 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -15.1588 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3405 -15.1588 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0905 -11.2617 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8405 -9.9626 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8482 -0.6575 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1344 1.1731 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 3.4573 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6715 2.7970 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5078 1.1546 0.0000 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 6 12 14 1 0 14 15 1 0 12 16 1 0 16 17 1 0 7 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 25 27 1 0 27 28 1 0 27 29 2 0 18 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 43 45 1 0 45 46 1 0 45 47 2 0 4 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 50 52 1 0 52 53 1 0 52 2 1 0 34 6 1 0 47 40 1 0 16 9 1 0 29 22 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 1 4 58 1 6 6 59 1 6 7 60 1 1 9 61 1 6 11 62 1 0 11 63 1 0 13 64 1 0 14 65 1 0 14 66 1 0 15 67 1 0 16 68 1 1 17 69 1 0 18 70 1 6 20 71 1 0 20 72 1 0 21 73 1 0 21 74 1 0 23 75 1 0 24 76 1 0 26 77 1 0 28 78 1 0 29 79 1 0 31 80 1 6 32 81 1 0 32 82 1 0 33 83 1 0 34 84 1 1 38 85 1 0 39 86 1 0 41 87 1 0 42 88 1 0 44 89 1 0 46 90 1 0 47 91 1 0 48 92 1 1 49 93 1 0 50 94 1 1 51 95 1 0 52 96 1 6 53 97 1 0 M END

Standard InCHIKey	UXPCJXXUGGXVGI-PQYLUDDISA-N
Standard InCHI	InChI=1S/C34H44O19/c1-15-24(42)25(43)26(44)31(49-15)52-28-27(51-23(41)7-4-16-2-5-18(37)20(39)10-16)22(12-35)50-32(47-9-8-17-3-6-19(38)21(40)11-17)29(28)53-33-30(45)34(46,13-36)14-48-33/h2-7,10-11,15,22,24-33,35-40,42-46H,8-9,12-14H2,1H3/b7-4+/t15-,22+,24-,25+,26+,27+,28-,29+,30-,31-,32+,33-,34+/m0/s1
SMILES	C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O[C@@H]3OC[C@](O)(CO)[C@H]3O)[C@H](OCCc3ccc(O)c(O)c3)O[C@H](CO)[C@H]2OC(=O)/C=C/c2ccc(O)c(O)c2)[C@H](O)[C@H](O)[C@H]1O

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
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO42447	Fernandoa adenophylla	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11625	Markhamia stipulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11625	Markhamia stipulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22788	Barnettia kerrii	n.a.	n.a.	n.a.	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
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual protein	Cyclooxygenase-2	Ovis aries	IC50	=	18200.0	nM	PMID[31255927]

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 NPC610636 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	13872
0.1-0.2	31625
0.2-0.3	3824
0.3-0.4	431
0.4-0.5	45
0.5-0.6	35
0.6-0.7	20
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8642	High Similarity	NPC40305
0.8488	Intermediate Similarity	NPC105005
0.8444	Intermediate Similarity	NPC196063
0.8444	Intermediate Similarity	NPC604195
0.7263	Intermediate Similarity	NPC141455
0.6979	Remote Similarity	NPC300894
0.6979	Remote Similarity	NPC23845
0.6889	Remote Similarity	NPC472350
0.6889	Remote Similarity	NPC197316
0.6889	Remote Similarity	NPC89105
0.6813	Remote Similarity	NPC68092
0.6778	Remote Similarity	NPC328273
0.6667	Remote Similarity	NPC296954
0.6667	Remote Similarity	NPC119537
0.6593	Remote Similarity	NPC171134
0.6489	Remote Similarity	NPC476377
0.6458	Remote Similarity	NPC269141
0.6452	Remote Similarity	NPC222433
0.6321	Remote Similarity	NPC188393
0.6105	Remote Similarity	NPC321184
0.6061	Remote Similarity	NPC298257
0.6061	Remote Similarity	NPC175214
0.6061	Remote Similarity	NPC252292
0.6042	Remote Similarity	NPC76406
0.6	Remote Similarity	NPC112
0.5979	Remote Similarity	NPC611289
0.5957	Remote Similarity	NPC46137
0.5941	Remote Similarity	NPC100998
0.5926	Remote Similarity	NPC229505
0.59	Remote Similarity	NPC205864
0.59	Remote Similarity	NPC247032
0.5895	Remote Similarity	NPC321638
0.5882	Remote Similarity	NPC96795
0.5882	Remote Similarity	NPC264632
0.5865	Remote Similarity	NPC476375
0.5865	Remote Similarity	NPC106818
0.5851	Remote Similarity	NPC81515
0.567	Remote Similarity	NPC483705
0.5648	Remote Similarity	NPC87403
0.5607	Remote Similarity	NPC476378
0.56	Remote Similarity	NPC263829
0.5577	Remote Similarity	NPC232992
0.5567	Remote Similarity	NPC64141
0.5567	Remote Similarity	NPC483706
0.5556	Remote Similarity	NPC886
0.5543	Remote Similarity	NPC473285
0.5505	Remote Similarity	NPC470934
0.5364	Remote Similarity	NPC64195
0.534	Remote Similarity	NPC34587
0.5333	Remote Similarity	NPC34927
0.53	Remote Similarity	NPC134405
0.5278	Remote Similarity	NPC476384
0.5217	Remote Similarity	NPC473924
0.5217	Remote Similarity	NPC287597
0.5133	Remote Similarity	NPC94871
0.5102	Remote Similarity	NPC475530
0.51	Remote Similarity	NPC205195
0.5055	Remote Similarity	NPC90318
0.5051	Remote Similarity	NPC260425
0.5045	Remote Similarity	NPC476380

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC610636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5192
0.1-0.2	3905
0.2-0.3	51
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
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
0.6889	Remote Similarity	NPD7266	Phase 2

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