NPASS Compound

Natural Product: NPC155253

Natural Product ID	NPC155253
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OZHIKCIPCFAOPM-MZNNUVDVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10006762
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003509] 3-prenylated chalcones

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 66 68 0 0 0 0 0 0 0 0999 V2000 0.6236 -1.9163 1.8273 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5725 -0.9138 0.6671 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0415 0.2422 0.8132 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1075 1.3405 -0.1508 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5305 1.3721 -0.6751 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7866 0.9367 -1.9479 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0785 0.7518 -2.4065 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1169 1.0305 -1.5043 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 1.4596 -0.2383 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9211 1.7678 0.7257 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5820 2.5620 1.7028 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2766 1.2981 0.7525 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8007 0.4374 -0.0526 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2152 0.0052 0.0547 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7201 -0.8924 -0.8957 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0029 -1.3875 -0.8099 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8358 -1.0086 0.2293 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3618 -0.1229 1.1807 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0497 0.3661 1.0666 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1306 -1.4920 0.3464 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5393 1.6469 0.2036 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2938 2.0958 1.4914 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6905 0.6848 -2.7831 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1005 -1.4219 -0.5913 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4635 -1.7242 -0.4992 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4409 -0.7908 -0.2444 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1097 0.4087 -0.0709 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8630 -1.2074 -0.1894 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8297 -0.3335 -0.0014 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2514 -0.6848 0.0635 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7217 -1.9753 0.0117 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0983 -2.2366 0.0442 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9470 -1.1793 0.1289 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5167 0.1325 0.1841 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1600 0.3435 0.1504 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4478 1.1465 0.2671 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2097 2.5173 0.3166 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3177 -1.4308 0.1587 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1246 -2.7046 1.6243 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3417 -1.3765 2.7792 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6386 -2.2885 1.9352 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3716 0.4416 1.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0371 2.3191 0.3478 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6213 1.2991 -0.9869 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2937 0.4176 -3.3883 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0947 0.9538 -1.9123 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9340 1.7214 1.5500 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2418 -0.0634 -0.7996 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0482 -1.1873 -1.7218 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3500 -2.0714 -1.5630 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9637 0.2220 2.0197 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7019 1.0666 1.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3265 -2.3463 0.8876 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0193 3.0526 1.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7975 0.4495 -3.7419 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5553 -2.4002 -0.7928 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9948 -0.7444 -1.4441 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1262 -2.2404 -0.3003 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5571 0.7008 0.1111 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0256 -2.7828 -0.0543 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4037 -3.2787 0.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8093 1.3903 0.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9338 3.0578 -0.3604 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1894 2.8152 0.0298 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4393 2.9286 1.3387 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8077 -1.1793 -0.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 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 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 17 20 1 0 9 21 2 0 21 22 1 0 6 23 1 0 2 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 33 38 1 0 21 5 1 0 35 30 1 0 19 14 1 0 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 7 45 1 0 8 46 1 0 12 47 1 0 13 48 1 0 15 49 1 0 16 50 1 0 18 51 1 0 19 52 1 0 20 53 1 0 22 54 1 0 23 55 1 0 24 56 1 0 24 57 1 0 28 58 1 0 29 59 1 0 31 60 1 0 32 61 1 0 35 62 1 0 37 63 1 0 37 64 1 0 37 65 1 0 38 66 1 0 M END

Standard InCHIKey	OZHIKCIPCFAOPM-MZNNUVDVSA-N
Standard InCHI	InChI=1S/C30H28O8/c1-19(18-38-29(35)16-8-21-7-14-27(34)28(17-21)37-2)3-11-23-26(33)15-12-24(30(23)36)25(32)13-6-20-4-9-22(31)10-5-20/h3-10,12-17,31,33-34,36H,11,18H2,1-2H3/b13-6+,16-8+,19-3-
SMILES	C/C(=C/Cc1c(ccc(C(=O)/C=C/c2ccc(cc2)O)c1O)O)/COC(=O)/C=C/c1ccc(c(c1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.18	Volume:	535.178 ? Van der Waals volume.
Dense:	0.965	LogP:	4.083 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.071 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.463 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
TPSA:	133.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.126	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.859	Fsp³:	0.133
MCE-18:	21.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.618 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.979 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.527	Promiscuous compounds:	0.242

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.37	MDCK Permeability:	-4.856
Pgp-inhibitor:	0.926	Pgp-substrate:	0.0
PAMPA:	0.018 ? 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):	0.005
20% Bioavailability (F20%):	0.959	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.006
Plasma Protein Binding (PPB):	97.459%	Volume Distribution (VD):	-0.172
Fu:	2.465% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.768
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.014	CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.985
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.876	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.934 ? 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):

3.682

Half-life (T1/2):

1.45

ADMET: Toxicity

hERG Blockers:	0.208	hERG Blockers (10um):	0.564
Human Hepatotoxicity (H-HT):	0.518	Drug-induced Liver Injury (DILI):	0.216
AMES Toxicity:	0.571	Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.791	Skin Sensitization:	0.994
Carcinogencity:	0.125	Eye Corrosion:	0.0
Eye Irritation:	0.886	Respiratory Toxicity:	0.647
Drug-induced Neurotoxicity:	0.293	Ototoxicity:	0.158
Hematotoxicity:	0.029	Drug-induced Nephrotoxicity:	0.256
Genotoxicity:	0.822	RPMI-8226 Immunitoxicity:	0.214
A549 Cytotoxicity:	0.551	Hek293 Cytotoxicity:	0.927
BCF:	1.161 ? 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:	4.662 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.928 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.581 ? 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
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(95)00135-T]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Wood	n.a.	n.a.	PMID[23113717]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17767	Artocarpus heterophyllus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17767	Artocarpus heterophyllus	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

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Individual protein	2
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3102	Individual protein	Beta-glucuronidase	Rattus norvegicus	IC50	=	6600.0	nM	PMID[31835168]
NPT3102	Individual protein	Beta-glucuronidase	Rattus norvegicus	IC50	=	70000.0	nM	PMID[31835168]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	IC50	=	73600.0	nM	PMID[23113717]

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 NPC155253 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	16959
0.1-0.2	27109
0.2-0.3	5065
0.3-0.4	599
0.4-0.5	95
0.5-0.6	19
0.6-0.7	1
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC479646
0.8889	High Similarity	NPC35598
0.8889	High Similarity	NPC222689
0.8857	High Similarity	NPC479647
0.8333	Intermediate Similarity	NPC19622
0.8333	Intermediate Similarity	NPC112789
0.75	Intermediate Similarity	NPC275903
0.6029	Remote Similarity	NPC72158
0.5806	Remote Similarity	NPC479644
0.5694	Remote Similarity	NPC213552
0.5694	Remote Similarity	NPC479645
0.5694	Remote Similarity	NPC479648
0.5672	Remote Similarity	NPC202474
0.56	Remote Similarity	NPC266689
0.5571	Remote Similarity	NPC254659
0.5513	Remote Similarity	NPC470210
0.5385	Remote Similarity	NPC21305
0.5375	Remote Similarity	NPC484872
0.5278	Remote Similarity	NPC204466
0.5205	Remote Similarity	NPC59319
0.5143	Remote Similarity	NPC66905
0.5139	Remote Similarity	NPC62952
0.5135	Remote Similarity	NPC100067
0.5125	Remote Similarity	NPC475042
0.507	Remote Similarity	NPC246704
0.5068	Remote Similarity	NPC70752
0.5067	Remote Similarity	NPC120225

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC155253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3579
0.1-0.2	5454
0.2-0.3	112
0.3-0.4	5
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