NPASS Compound

Natural Product: NPC150767

Natural Product ID	NPC150767
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Farobin A
IUPAC Name	6-[(2R,4S,5R,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1224895
PubChem CID	46938449
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 71 75 0 0 0 0 0 0 0 0999 V2000 -3.8155 3.5841 -2.3376 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0741 4.1171 -1.0854 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8339 3.0145 -0.0683 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5027 2.6321 -0.2056 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2177 1.5220 0.6283 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9474 1.1810 0.4589 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0024 0.3099 0.1916 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3313 0.7738 0.1596 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3957 -0.0361 -0.1081 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6251 0.4012 -0.1357 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6811 -0.3622 -0.3931 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5234 -1.6928 -0.6511 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2323 -2.2188 -0.6358 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0420 -3.4478 -0.8698 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1747 -1.3773 -0.3622 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8814 -1.8386 -0.3330 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1947 -1.0140 -0.0607 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5404 -1.6317 -0.0306 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3266 -1.4385 -1.2963 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5208 -2.7644 -1.9711 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2092 -2.5958 -3.1690 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2747 -3.6734 -1.0196 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7041 -3.4951 0.3677 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3996 -3.0375 0.2315 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7975 -4.7450 1.1952 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1769 -4.9828 -1.4384 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6963 -3.1952 -0.5935 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0225 0.2148 -0.4028 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1533 -0.5061 -0.6586 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3899 0.1333 -0.6455 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4985 1.4654 -0.3826 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3564 2.2077 -0.1214 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1416 1.5683 -0.1366 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4696 3.5826 0.1497 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7520 2.0896 -0.3743 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4253 1.9443 2.0910 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7791 2.5286 2.3149 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0187 3.6252 1.2963 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3470 4.0589 1.4245 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7773 3.1429 3.5682 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2720 0.8373 2.8960 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8320 3.6692 -2.4863 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3328 4.9173 -0.8762 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1065 4.5067 -0.9908 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5339 2.1714 -0.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9810 0.7625 0.4111 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5207 1.8185 0.3559 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3356 -2.3689 -0.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1348 -1.2928 0.8274 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3661 -1.0440 -1.1058 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8516 -0.6917 -1.9671 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5431 -3.2383 -2.1839 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9946 -3.2201 -3.2363 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3367 -3.3531 -1.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2827 -2.7038 0.8836 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0745 -4.6530 2.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8097 -4.7522 1.6722 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6753 -5.6697 0.6165 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9274 -5.4871 -1.0076 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7874 -3.4604 -1.5821 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1180 -1.5542 -0.8701 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2651 -0.4443 -0.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2383 2.1485 0.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6277 3.9407 1.0733 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4999 1.7132 -0.9189 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6413 2.6696 2.3378 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5945 1.8088 2.2426 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2927 4.4357 1.4655 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3977 4.8552 2.0061 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8542 3.4125 3.7872 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0391 0.2218 2.8930 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 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 22 26 1 0 16 27 1 0 11 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 31 35 1 0 5 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 36 41 1 0 38 3 1 0 17 7 1 0 24 18 1 0 33 28 1 0 15 9 2 0 1 42 1 0 2 43 1 0 2 44 1 0 3 45 1 6 5 46 1 6 8 47 1 0 12 48 1 0 18 49 1 1 19 50 1 0 19 51 1 0 20 52 1 6 21 53 1 0 22 54 1 1 23 55 1 1 25 56 1 0 25 57 1 0 25 58 1 0 26 59 1 0 27 60 1 0 29 61 1 0 30 62 1 0 33 63 1 0 34 64 1 0 35 65 1 0 36 66 1 1 37 67 1 1 38 68 1 1 39 69 1 0 40 70 1 0 41 71 1 0 M END

Standard InCHIKey	UKNXXFWLEJRJCY-NCJQNZQYSA-N
Standard InCHI	InChI=1S/C27H30O14/c1-9-22(33)14(32)6-16(38-9)21-18(40-27-26(37)25(36)23(34)19(8-28)41-27)7-17-20(24(21)35)13(31)5-15(39-17)10-2-3-11(29)12(30)4-10/h2-5,7,9,14,16,19,22-23,25-30,32-37H,6,8H2,1H3/t9-,14+,16-,19-,22+,23-,25+,26-,27-/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2cc3oc(cc(=O)c3c(c2[C@H]2C[C@H](O)[C@H]([C@H](O2)C)O)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O

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
NPO33290	fargesia robusta	Species	Poaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20863141]

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	2

Activity Type	# Activity
Others	1
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.332	n.a.	PMID[20863141]
NPT35	Others	n.a.	n.a.	Activity	=	26.8	n.a.	PMID[20188576]

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 NPC150767 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	17999
0.1-0.2	28097
0.2-0.3	2740
0.3-0.4	750
0.4-0.5	208
0.5-0.6	53
0.6-0.7	8
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
0.7727	Intermediate Similarity	NPC607513
0.6701	Remote Similarity	NPC256760
0.6477	Remote Similarity	NPC189142
0.6477	Remote Similarity	NPC77660
0.6404	Remote Similarity	NPC58716
0.6404	Remote Similarity	NPC45638
0.6354	Remote Similarity	NPC606373
0.6333	Remote Similarity	NPC201292
0.6	Remote Similarity	NPC124155
0.5934	Remote Similarity	NPC168822
0.5824	Remote Similarity	NPC19709
0.5652	Remote Similarity	NPC39360
0.5652	Remote Similarity	NPC29763
0.5652	Remote Similarity	NPC210003
0.56	Remote Similarity	NPC3583
0.5591	Remote Similarity	NPC93337
0.5591	Remote Similarity	NPC146792
0.5532	Remote Similarity	NPC105025
0.5455	Remote Similarity	NPC8856
0.5426	Remote Similarity	NPC277205
0.5426	Remote Similarity	NPC37919
0.5392	Remote Similarity	NPC115674
0.5368	Remote Similarity	NPC245014
0.5368	Remote Similarity	NPC10807
0.5368	Remote Similarity	NPC161881
0.5361	Remote Similarity	NPC22832
0.5361	Remote Similarity	NPC601144
0.5361	Remote Similarity	NPC605067
0.5319	Remote Similarity	NPC58053
0.5319	Remote Similarity	NPC261866
0.5319	Remote Similarity	NPC45618
0.5312	Remote Similarity	NPC117260
0.5306	Remote Similarity	NPC311830
0.5306	Remote Similarity	NPC602805
0.5306	Remote Similarity	NPC605784
0.53	Remote Similarity	NPC254540
0.5263	Remote Similarity	NPC95090
0.5263	Remote Similarity	NPC27408
0.5263	Remote Similarity	NPC136042
0.5253	Remote Similarity	NPC190003
0.5248	Remote Similarity	NPC603300
0.5243	Remote Similarity	NPC257566
0.5208	Remote Similarity	NPC186807
0.5208	Remote Similarity	NPC84362
0.5208	Remote Similarity	NPC610763
0.5196	Remote Similarity	NPC78734
0.5161	Remote Similarity	NPC611357
0.5158	Remote Similarity	NPC83283
0.5149	Remote Similarity	NPC472607
0.5146	Remote Similarity	NPC218488
0.5146	Remote Similarity	NPC210073
0.5104	Remote Similarity	NPC609879
0.5102	Remote Similarity	NPC191306
0.5102	Remote Similarity	NPC488071
0.5102	Remote Similarity	NPC609451
0.5088	Remote Similarity	NPC132111
0.5053	Remote Similarity	NPC53545
0.5053	Remote Similarity	NPC473043
0.5053	Remote Similarity	NPC331652
0.5052	Remote Similarity	NPC602537
0.5051	Remote Similarity	NPC243930
0.5051	Remote Similarity	NPC601710

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC150767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4842
0.1-0.2	4232
0.2-0.3	61
0.3-0.4	12
0.4-0.5	3
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