NPASS Compound

Natural Product: NPC323595

Natural Product ID	NPC323595
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DAUPWJBRVZCBQB-AWEZNQCLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	440591
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

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 44 46 0 0 0 0 0 0 0 0999 V2000 0.4210 -3.9816 -1.1514 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2104 -2.6876 -1.1649 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5995 -2.7826 -0.9869 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2253 -1.4293 -1.4015 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7426 -0.5232 -0.2824 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6257 0.3815 0.2547 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2157 1.1912 1.3181 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9269 1.0202 1.7617 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0438 0.1057 1.2132 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4472 -0.7057 0.1491 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4547 -1.6675 -0.4903 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4475 -0.9209 -1.3904 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1628 0.1612 -0.7356 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7024 1.4845 -0.7379 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4152 2.4809 -0.1030 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5857 2.1970 0.5417 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0709 0.8926 0.5629 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3445 -0.0848 -0.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2939 3.2098 1.1773 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9749 3.8175 -0.0904 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4988 1.8105 2.8146 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0956 2.1046 1.8658 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4058 2.2997 1.4372 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8616 -4.2363 -0.1628 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1465 -4.0929 -1.9766 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3779 -4.7311 -1.3318 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8981 -3.0042 0.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1163 -3.5278 -1.6102 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8467 -1.1370 -2.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3179 -1.4712 -1.3252 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6414 0.5055 -0.1061 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9562 -0.0317 1.5651 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1283 -2.0648 0.3350 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1467 -1.6271 -1.8692 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -0.4819 -2.2222 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7822 1.7385 -1.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9966 0.7045 1.0802 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7086 -1.1014 -0.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0962 3.0391 1.7486 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1660 4.1070 -0.6248 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1608 1.9274 3.5809 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8213 3.2630 1.7910 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0687 1.4704 1.7117 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4097 2.3783 0.3106 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 16 19 1 0 15 20 1 0 8 21 1 0 7 22 1 0 22 23 1 0 11 2 1 0 10 5 1 0 18 13 1 0 1 24 1 0 1 25 1 0 1 26 1 0 3 27 1 0 3 28 1 0 4 29 1 0 4 30 1 0 6 31 1 0 9 32 1 0 11 33 1 0 12 34 1 0 12 35 1 0 14 36 1 0 17 37 1 0 18 38 1 0 19 39 1 0 20 40 1 0 21 41 1 0 23 42 1 0 23 43 1 0 23 44 1 0 M END

Standard InCHIKey	DAUPWJBRVZCBQB-AWEZNQCLSA-N
Standard InCHI	InChI=1S/C18H21NO4/c1-19-6-5-12-9-18(23-2)17(22)10-13(12)14(19)7-11-3-4-15(20)16(21)8-11/h3-4,8-10,14,20-22H,5-7H2,1-2H3/t14-/m0/s1
SMILES	CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)O)O)O)OC

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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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 NPC323595 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	26460
0.1-0.2	19939
0.2-0.3	2833
0.3-0.4	474
0.4-0.5	109
0.5-0.6	29
0.6-0.7	8
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8302	Intermediate Similarity	NPC321505
0.8302	Intermediate Similarity	NPC179825
0.8113	Intermediate Similarity	NPC147390
0.8113	Intermediate Similarity	NPC428
0.7143	Intermediate Similarity	NPC191376
0.6769	Remote Similarity	NPC480592
0.6724	Remote Similarity	NPC135538
0.6724	Remote Similarity	NPC24233
0.6471	Remote Similarity	NPC240841
0.6471	Remote Similarity	NPC610959
0.6429	Remote Similarity	NPC609914
0.6207	Remote Similarity	NPC185838
0.6087	Remote Similarity	NPC603603
0.5893	Remote Similarity	NPC484289
0.589	Remote Similarity	NPC600872
0.5738	Remote Similarity	NPC103379
0.5714	Remote Similarity	NPC189266
0.5714	Remote Similarity	NPC2413
0.5714	Remote Similarity	NPC110416
0.5676	Remote Similarity	NPC286119
0.5667	Remote Similarity	NPC88249
0.5625	Remote Similarity	NPC249797
0.5625	Remote Similarity	NPC193949
0.5513	Remote Similarity	NPC601489
0.5513	Remote Similarity	NPC604804
0.5441	Remote Similarity	NPC317272
0.5441	Remote Similarity	NPC268503
0.5323	Remote Similarity	NPC609731
0.5303	Remote Similarity	NPC295691
0.5303	Remote Similarity	NPC207757
0.5303	Remote Similarity	NPC54379
0.5263	Remote Similarity	NPC192768
0.5254	Remote Similarity	NPC314682
0.5211	Remote Similarity	NPC256012
0.5211	Remote Similarity	NPC610965
0.5167	Remote Similarity	NPC213206
0.5167	Remote Similarity	NPC188163
0.5167	Remote Similarity	NPC328750
0.5152	Remote Similarity	NPC212794
0.5152	Remote Similarity	NPC609009
0.5085	Remote Similarity	NPC34559
0.5077	Remote Similarity	NPC158376

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC323595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4087
0.1-0.2	4807
0.2-0.3	232
0.3-0.4	18
0.4-0.5	4
0.5-0.6	1
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
0.629	Remote Similarity	NPD4010	Discontinued
0.5167	Remote Similarity	NPD4664	Clinical (unspecified phase)

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