NPASS Compound

Natural Product: NPC193197

Natural Product ID	NPC193197
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BVVVHQJFODXUQX-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21721851
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

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 57 60 0 0 0 0 0 0 0 0999 V2000 5.1561 0.6332 3.3482 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4891 0.6061 1.9033 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7811 -0.1472 1.0421 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6619 -0.9653 1.4903 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3058 -0.6463 1.0175 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0446 -0.7003 -0.4726 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8973 0.2992 -1.2526 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4412 -2.0288 -0.9793 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6112 -2.8602 -1.5309 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2136 -2.5339 -1.6892 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7095 -3.3746 -2.2650 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0285 -2.9932 -2.3815 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4121 -1.7490 -1.9095 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5183 -0.8809 -1.3279 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9513 0.4697 -0.8202 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3575 0.3265 0.6154 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8302 0.3718 0.8109 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4446 -0.3200 1.6507 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5890 1.2797 -0.0314 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7959 1.8294 0.3565 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4983 2.6905 -0.4622 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9995 3.0230 -1.7033 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7985 2.4824 -2.1021 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0875 1.6094 -1.2707 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8873 1.0630 -1.6574 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6964 3.8985 -2.5564 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2646 1.4611 1.6303 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2002 -1.2862 -1.2223 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6881 -0.4312 -0.6475 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2757 -4.6091 -2.7217 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6225 1.4253 1.4057 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7253 1.4081 3.8579 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0755 0.8572 3.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3774 -0.3895 3.7559 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0905 -0.1394 0.0133 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8529 -2.0746 1.2929 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6425 -0.9293 2.6186 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0695 0.4181 1.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5143 -1.2962 1.4722 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1967 0.7124 -2.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6616 -0.2248 -1.7977 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2711 1.1272 -0.6643 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5203 -2.3106 -0.8703 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9671 -3.8380 -1.8900 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7712 -3.6612 -2.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4612 -1.4395 -1.9991 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0465 1.1495 -0.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9215 -0.6189 1.0270 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9168 1.1806 1.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4314 3.1083 -0.1478 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3888 2.7283 -3.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2157 4.7424 -2.8423 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1223 1.9061 1.9288 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9687 -5.3250 -2.8959 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6487 2.4033 1.9700 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5104 1.7041 0.3286 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5528 0.8591 1.5956 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 22 26 1 0 20 27 1 0 14 28 2 0 28 29 1 0 11 30 1 0 2 31 1 0 29 6 1 0 28 10 1 0 25 15 1 0 24 19 1 0 1 32 1 0 1 33 1 0 1 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 7 40 1 0 7 41 1 0 7 42 1 0 8 43 1 0 9 44 1 0 12 45 1 0 13 46 1 0 15 47 1 0 16 48 1 0 16 49 1 0 21 50 1 0 23 51 1 0 26 52 1 0 27 53 1 0 30 54 1 0 31 55 1 0 31 56 1 0 31 57 1 0 M END

Standard InCHIKey	BVVVHQJFODXUQX-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C25H26O6/c1-14(2)5-4-9-25(3)10-8-16-18(27)7-6-17(24(16)31-25)21-13-20(29)23-19(28)11-15(26)12-22(23)30-21/h5-8,10-12,21,26-28H,4,9,13H2,1-3H3
SMILES	CC(=CCCC1(C)C=Cc2c(ccc(C3CC(=O)c4c(cc(cc4O3)O)O)c2O1)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	422.17	Volume:	435.743 ? Van der Waals volume.
Dense:	0.969	LogP:	4.81 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.707 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.837 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	96.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.569	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.044	Fsp³:	0.32
MCE-18:	82.727 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.914	Fluc inhibitor:	0.518 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.729 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.761 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.235	Promiscuous compounds:	0.028

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.922	MDCK Permeability:	-4.75
Pgp-inhibitor:	0.914	Pgp-substrate:	0.014
PAMPA:	0.098 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.047	30% Bioavailability (F30%):	0.856
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202	MRP1:	0.968
Plasma Protein Binding (PPB):	95.977%	Volume Distribution (VD):	0.472
Fu:	4.256% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.967
BSEP inhibitor:	0.993

ADMET: Metabolism

CYP1A2-inhibitor:	0.343	CYP1A2-substrate:	0.997
CYP2C19-inhibitor:	0.091	CYP2C19-substrate:	0.972
CYP2C9-inhibitor:	0.975	CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.329	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.168
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.998 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

4.697

Half-life (T1/2):

1.282

ADMET: Toxicity

hERG Blockers:	0.175	hERG Blockers (10um):	0.64
Human Hepatotoxicity (H-HT):	0.656	Drug-induced Liver Injury (DILI):	0.48
AMES Toxicity:	0.662	Rat Oral Acute Toxicity:	0.596
Maximum Recommended Daily Dose:	0.55	Skin Sensitization:	0.842
Carcinogencity:	0.617	Eye Corrosion:	0.001
Eye Irritation:	0.926	Respiratory Toxicity:	0.919
Drug-induced Neurotoxicity:	0.199	Ototoxicity:	0.459
Hematotoxicity:	0.145	Drug-induced Nephrotoxicity:	0.317
Genotoxicity:	0.837	RPMI-8226 Immunitoxicity:	0.151
A549 Cytotoxicity:	0.541	Hek293 Cytotoxicity:	0.775
BCF:	1.961 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.874 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.345 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.717 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	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 NPC193197 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	19342
0.1-0.2	26609
0.2-0.3	3173
0.3-0.4	575
0.4-0.5	129
0.5-0.6	26
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	Natural Product ID
0.7681	Intermediate Similarity	NPC88964
0.5823	Remote Similarity	NPC475052
0.5811	Remote Similarity	NPC109223
0.5811	Remote Similarity	NPC10937
0.5625	Remote Similarity	NPC472633
0.5616	Remote Similarity	NPC470669
0.5488	Remote Similarity	NPC58805
0.5479	Remote Similarity	NPC470668
0.5476	Remote Similarity	NPC488550
0.5422	Remote Similarity	NPC111786
0.5357	Remote Similarity	NPC186686
0.5238	Remote Similarity	NPC67396
0.52	Remote Similarity	NPC258630
0.5195	Remote Similarity	NPC17170
0.5143	Remote Similarity	NPC32441
0.5143	Remote Similarity	NPC79943
0.5139	Remote Similarity	NPC321011
0.5139	Remote Similarity	NPC294852
0.5139	Remote Similarity	NPC188679
0.5125	Remote Similarity	NPC312973
0.5122	Remote Similarity	NPC474021
0.5122	Remote Similarity	NPC96408
0.5122	Remote Similarity	NPC610511
0.5119	Remote Similarity	NPC488549
0.5119	Remote Similarity	NPC214166
0.5116	Remote Similarity	NPC43319
0.506	Remote Similarity	NPC279650

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC193197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4429
0.1-0.2	4667
0.2-0.3	43
0.3-0.4	8
0.4-0.5	2
0.5-0.6	1
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
0.5143	Remote Similarity	NPD1552	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