NPASS Compound

Natural Product: NPC156941

Natural Product ID	NPC156941
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KVALLMPODLLLKE-PUSCYMQSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10887145
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 97102 0 0 0 0 0 0 0 0999 V2000 -3.9405 3.1976 -0.6195 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9209 2.2974 -1.2392 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 2.5450 -2.3364 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5776 1.1590 -0.5720 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6146 0.1960 -1.0397 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4566 0.2943 -0.1189 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3172 -0.9852 -0.0886 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8174 -1.2143 -1.4954 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5484 -0.9834 0.7690 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2997 -1.2575 2.2104 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4034 -2.4265 2.3968 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0331 -3.1108 1.0579 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6742 -1.9819 0.4249 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6738 -2.3217 -0.6178 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1905 -3.3755 -1.6199 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2360 -1.1076 -1.2974 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6228 -0.9974 -1.0284 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5899 -1.1802 -1.9995 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1936 -1.4550 -3.1615 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0074 -1.0729 -1.7484 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5193 -0.7738 -0.5025 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9024 -0.6811 -0.3097 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7412 -0.8938 -1.3848 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2470 -1.1812 -2.5812 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9167 -1.2694 -2.7628 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7412 -2.9696 0.0583 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4217 -1.3984 1.4753 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9982 -1.8491 2.6748 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8897 -0.7276 3.7066 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8141 -2.9217 3.3371 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8194 -4.1915 1.3831 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5248 -5.4974 1.1137 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5594 -5.7851 0.5448 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4534 -6.6212 1.4726 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3868 0.1343 0.5666 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6588 0.0474 0.0230 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0690 -1.0951 -0.3013 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5037 1.2451 -0.1703 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7136 1.1453 -0.6916 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6090 2.2722 -0.9156 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8503 2.0464 -1.4701 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7465 3.0820 -1.7063 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3951 4.3732 -1.3812 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1624 4.6379 -0.8249 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2944 3.5764 -0.6041 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3497 1.4347 -0.4215 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5248 2.4795 0.4871 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0773 2.3436 1.5914 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3318 3.6439 0.2086 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4482 4.6193 1.1756 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2074 5.7501 0.9545 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8454 5.8770 -0.2591 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7254 4.8976 -1.2236 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9675 3.7731 -0.9974 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3562 3.9198 -1.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7924 2.5443 -0.2754 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5520 3.6667 0.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2683 0.6319 -2.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8515 0.4589 0.9028 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3181 -2.1836 -1.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1326 -0.8959 -2.2799 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6797 -0.4758 -1.5913 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1519 -1.8741 0.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2946 -1.5100 2.6771 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9687 -0.3295 2.6939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7049 -3.1516 3.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9161 -3.5027 0.5664 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2814 -3.9036 -1.2721 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0561 -2.9368 -2.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9502 -4.1804 -1.7783 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2077 -1.3549 -2.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8155 -0.6190 0.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2893 -0.4438 0.6816 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8229 -0.8111 -1.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4952 -1.5080 -3.7540 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3450 -2.2988 0.4587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0275 -0.8826 4.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9233 0.2804 3.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7930 -0.7574 4.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1112 -3.6666 3.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5577 -3.4193 2.7327 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3793 -2.5350 4.2393 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8941 -7.5776 1.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9559 -6.4275 2.4389 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2534 -6.7301 0.7187 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1374 2.2130 0.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0209 0.1423 -0.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1463 1.0451 -1.7323 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7218 2.9167 -2.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1072 5.1602 -1.5737 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9152 5.6597 -0.5807 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3490 3.8099 -0.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9535 4.5342 2.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3084 6.5284 1.7087 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4583 6.7503 -0.4875 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2221 4.9903 -2.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8437 2.9815 -1.7197 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 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 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 14 26 1 1 13 27 1 1 27 28 1 0 28 29 1 0 28 30 1 0 12 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 9 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 44 45 2 0 6 46 1 0 46 47 1 0 47 48 2 0 47 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 16 5 1 0 25 20 1 0 45 40 1 0 54 49 1 0 13 7 1 0 28 11 1 0 1 55 1 0 1 56 1 0 1 57 1 0 5 58 1 6 6 59 1 1 8 60 1 0 8 61 1 0 8 62 1 0 9 63 1 6 10 64 1 0 10 65 1 0 11 66 1 1 12 67 1 6 15 68 1 0 15 69 1 0 15 70 1 0 16 71 1 6 21 72 1 0 22 73 1 0 23 74 1 0 25 75 1 0 26 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 30 81 1 0 30 82 1 0 34 83 1 0 34 84 1 0 34 85 1 0 38 86 1 0 39 87 1 0 41 88 1 0 42 89 1 0 43 90 1 0 44 91 1 0 45 92 1 0 50 93 1 0 51 94 1 0 52 95 1 0 53 96 1 0 54 97 1 0 M END

Standard InCHIKey	KVALLMPODLLLKE-PUSCYMQSSA-N
Standard InCHI	InChI=1S/C41H43NO12/c1-24(43)49-32-34(52-36(46)27-16-11-8-12-17-27)39(5)30(51-31(45)20-19-26-14-9-7-10-15-26)22-29-33(50-25(2)44)41(39,54-38(29,3)4)40(6,48)35(32)53-37(47)28-18-13-21-42-23-28/h7-21,23,29-30,32-35,48H,22H2,1-6H3/b20-19+/t29-,30+,32+,33-,34+,35+,39-,40+,41-/m1/s1
SMILES	CC(=O)O[C@H]1[C@@H]([C@@]2(C)[C@H](C[C@@H]3[C@H]([C@@]2([C@](C)([C@H]1OC(=O)c1cccnc1)O)OC3(C)C)OC(=O)C)OC(=O)/C=C/c1ccccc1)OC(=O)c1ccccc1

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
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20146433]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	fruits	n.a.	n.a.	PMID[21856049]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27541714]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26437	Maytenus jelskii	Species	Celastraceae	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
Others	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
NPT2	Others	Unspecified	n.a.	Activity	>	60.0	%	PMID[27541714]

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 NPC156941 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	12821
0.1-0.2	34062
0.2-0.3	2339
0.3-0.4	480
0.4-0.5	111
0.5-0.6	33
0.6-0.7	6
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC483880
0.8214	Intermediate Similarity	NPC127026
0.8214	Intermediate Similarity	NPC483890
0.8095	Intermediate Similarity	NPC188865
0.6947	Remote Similarity	NPC483891
0.6771	Remote Similarity	NPC471980
0.6703	Remote Similarity	NPC184817
0.6129	Remote Similarity	NPC25768
0.6129	Remote Similarity	NPC483889
0.6	Remote Similarity	NPC483859
0.598	Remote Similarity	NPC6981
0.5895	Remote Similarity	NPC483881
0.5833	Remote Similarity	NPC171525
0.5729	Remote Similarity	NPC483865
0.56	Remote Similarity	NPC86800
0.5591	Remote Similarity	NPC127720
0.5577	Remote Similarity	NPC294579
0.5577	Remote Similarity	NPC144779
0.5567	Remote Similarity	NPC125106
0.5567	Remote Similarity	NPC472573
0.5532	Remote Similarity	NPC473085
0.5521	Remote Similarity	NPC483867
0.551	Remote Similarity	NPC301368
0.551	Remote Similarity	NPC84815
0.5437	Remote Similarity	NPC96801
0.5437	Remote Similarity	NPC150698
0.5408	Remote Similarity	NPC610927
0.5392	Remote Similarity	NPC483885
0.5385	Remote Similarity	NPC488902
0.5385	Remote Similarity	NPC488903
0.5361	Remote Similarity	NPC483878
0.5354	Remote Similarity	NPC56953
0.5312	Remote Similarity	NPC609309
0.5253	Remote Similarity	NPC469349
0.5253	Remote Similarity	NPC483861
0.5243	Remote Similarity	NPC479045
0.5208	Remote Similarity	NPC473112
0.5161	Remote Similarity	NPC158663
0.51	Remote Similarity	NPC174982
0.51	Remote Similarity	NPC483860
0.51	Remote Similarity	NPC611111
0.5052	Remote Similarity	NPC476970
0.5052	Remote Similarity	NPC607428

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC156941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3785
0.1-0.2	5250
0.2-0.3	113
0.3-0.4	2
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