NPASS Compound

Natural Product: NPC232210

Natural Product ID	NPC232210
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DJSISFGPUUYILV-AGRFSFNASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0002934] Flavonoid O-glucuronides [CHEMONTID:0003534] Flavonoid-7-O-glucuronides

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 50 53 0 0 0 0 0 0 0 0999 V2000 3.9209 -0.8215 -1.9945 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7087 -1.3724 -2.9833 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0810 -1.1725 -2.9345 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6342 -0.4363 -1.9132 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7965 0.1048 -0.9300 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4454 -0.0720 -0.9475 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5704 0.4903 0.0754 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0057 1.2412 1.1409 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1473 1.7656 2.1028 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5544 2.4464 3.0666 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8068 1.4902 1.9334 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3997 0.7352 0.8563 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0363 0.4894 0.7363 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9048 0.9565 1.6264 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4558 1.7089 2.6915 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8876 1.9725 2.8425 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3764 2.7273 3.9039 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3630 2.2029 3.6162 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2512 0.7316 1.5352 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9350 0.0090 0.5593 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9998 0.8690 -0.1362 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0842 0.0236 -0.7426 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4818 -1.3014 -1.1550 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9381 -1.9676 0.0883 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7363 -2.7585 -0.2219 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7796 -3.6485 -1.1417 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5732 -2.5290 0.4866 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6472 -1.0747 1.1060 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5091 -1.0632 -2.1154 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1243 -0.2129 0.1625 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3439 1.5299 -1.1882 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2660 0.2787 -0.0034 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8917 -1.7290 -3.9362 O 0 0 0 0 0 1 0 0 0 0 0 0 2.8584 -0.9939 -2.0592 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3286 -1.9486 -3.7924 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7036 -0.3041 -1.9110 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2667 0.6709 -0.1529 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0591 1.4412 1.2490 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2896 -0.1009 -0.1044 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5873 2.2282 4.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0702 2.8499 3.2454 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2909 -0.4279 -0.2296 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4475 1.5956 0.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4953 0.4974 -1.6568 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2534 -1.9493 -1.6570 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7152 -2.6983 0.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6831 -2.8953 0.1228 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9648 -0.7036 -2.9046 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0989 -1.1566 0.5091 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8967 2.2819 -1.5037 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 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 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 15 18 1 0 14 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 24 28 1 0 23 29 1 0 22 30 1 0 21 31 1 0 12 32 1 0 3 33 1 0 6 1 1 0 32 7 1 0 16 11 1 0 28 20 1 0 1 34 1 0 2 35 1 0 4 36 1 0 5 37 1 0 8 38 1 0 13 39 1 0 17 40 1 0 18 41 1 0 20 42 1 6 21 43 1 1 22 44 1 6 23 45 1 6 24 46 1 1 27 47 1 0 29 48 1 0 30 49 1 0 31 50 1 0 M CHG 1 33 -1 M END

Standard InCHIKey	DJSISFGPUUYILV-AGRFSFNASA-N
Standard InCHI	InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/p-1/t16-,17-,18+,19+,21+/m1/s1
SMILES	c1cc(ccc1c1cc(=O)c2c(cc(c(c2O)O)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H](C(=O)O)O2)O)O)O)o1)[O-]

Calculated Properties

Physi-Chem Properties

Molecular Weight:	462.08	Volume:	419.301 ? Van der Waals volume.
Dense:	1.102	LogP:	1.078 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.335 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.009 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	25.0
TPSA:	207.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.253	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.997	Fsp³:	0.238
MCE-18:	91.385 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.398	Fluc inhibitor:	0.321 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.926 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.875 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.293	Promiscuous compounds:	0.493

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.483	MDCK Permeability:	-5.107
Pgp-inhibitor:	0.0	Pgp-substrate:	0.336
PAMPA:	1.0 ? 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):	0.126
20% Bioavailability (F20%):	0.402	30% Bioavailability (F30%):	0.769
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.974
Plasma Protein Binding (PPB):	82.022%	Volume Distribution (VD):	-0.06
Fu:	13.52% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.016
OATP1B3 inhibitor:	0.167	BCRP inhibitor:	0.125
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.33
HLM stability:	0.002 ? 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):

1.919

Half-life (T1/2):

3.968

ADMET: Toxicity

hERG Blockers:	0.015	hERG Blockers (10um):	0.086
Human Hepatotoxicity (H-HT):	0.4	Drug-induced Liver Injury (DILI):	0.905
AMES Toxicity:	0.643	Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.099	Skin Sensitization:	0.968
Carcinogencity:	0.09	Eye Corrosion:	0.0
Eye Irritation:	0.636	Respiratory Toxicity:	0.024
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.641
Hematotoxicity:	0.089	Drug-induced Nephrotoxicity:	0.392
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.04	Hek293 Cytotoxicity:	0.21
BCF:	0.208 ? 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:	2.77 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.121 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.358 ? 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
NPO2878	Conyza pyrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8112	Acacia intertexta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7568	Mora excelsa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8112	Acacia intertexta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2878	Conyza pyrifolia	Species	Asteraceae	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 NPC232210 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	23450
0.1-0.2	24236
0.2-0.3	1707
0.3-0.4	380
0.4-0.5	63
0.5-0.6	13
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8649	High Similarity	NPC237435
0.8533	High Similarity	NPC43211
0.7821	Intermediate Similarity	NPC115760
0.6951	Remote Similarity	NPC608742
0.6627	Remote Similarity	NPC282169
0.6512	Remote Similarity	NPC600989
0.6429	Remote Similarity	NPC20505
0.593	Remote Similarity	NPC101191
0.5862	Remote Similarity	NPC210094
0.5765	Remote Similarity	NPC45618
0.5698	Remote Similarity	NPC146792
0.5682	Remote Similarity	NPC135277
0.5632	Remote Similarity	NPC58716
0.5467	Remote Similarity	NPC57030
0.5275	Remote Similarity	NPC264735
0.5256	Remote Similarity	NPC283600
0.5132	Remote Similarity	NPC275722
0.5128	Remote Similarity	NPC212678
0.5065	Remote Similarity	NPC198826
0.5062	Remote Similarity	NPC485299

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC232210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4280
0.1-0.2	4798
0.2-0.3	65
0.3-0.4	6
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	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8649	High Similarity	NPD4338	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