NPASS Compound

Structure

NPC165483 OpenBabel07101719132D 35 38 0 0 1 0 0 0 0 0999 V2000 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 11 2 0 0 0 0 6 18 1 0 0 0 0 7 12 2 0 0 0 0 7 19 1 0 0 0 0 8 14 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 17 2 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 13 9 1 6 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 25 2 0 0 0 0 15 18 2 0 0 0 0 15 26 1 0 0 0 0 16 19 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 23 2 0 0 0 0 20 31 1 0 0 0 0 21 24 1 0 0 0 0 21 32 1 6 0 0 0 22 33 2 0 0 0 0 22 34 1 0 0 0 0 23 25 1 0 0 0 0 24 12 1 6 0 0 0 24 35 1 0 0 0 0 25 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.14
Volume:	468.268
LogP:	1.787
LogD:	1.258
LogS:	-3.861
# Rotatable Bonds:	6
TPSA:	177.14
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	3.985
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.417
MDCK Permeability:	4.229066689731553e-06
Pgp-inhibitor:	0.019
Pgp-substrate:	0.445
Human Intestinal Absorption (HIA):	0.092
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	93.73899841308594%
Volume Distribution (VD):	0.464
Pgp-substrate:	5.440676689147949%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.71
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.508

ADMET: Excretion

Clearance (CL):	12.851
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.201
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.541
Rat Oral Acute Toxicity:	0.733
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.929
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.872
Respiratory Toxicity:	0.036

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC165483

Natural Product ID:	NPC165483
*Common Name:**	3-(3,4-Dihydroxy-Phenyl)-3-[(2R,3R)-2-(3,4-Dihydroxy-Phenyl)-3,5,7-Trihydroxy-Chroman-8-Yl]-Propionic Acid Methyl Ester
IUPAC Name:	methyl (3R)-3-(3,4-dihydroxyphenyl)-3-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]propanoate
Synonyms:
Standard InCHIKey:	QNAHIWNQXWCADO-KTICBNGHSA-N
Standard InCHI:	InChI=1S/C25H24O10/c1-34-22(33)9-13(11-2-4-15(26)18(29)6-11)23-20(31)10-17(28)14-8-21(32)24(35-25(14)23)12-3-5-16(27)19(30)7-12/h2-7,10,13,21,24,26-32H,8-9H2,1H3/t13-,21-,24-/m1/s1
SMILES:	COC(=O)C[C@H](c1ccc(c(c1)O)O)c1c(cc(c2C[C@H]([C@@H](c3ccc(c(c3)O)O)Oc12)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2304274
PubChem CID:	11755072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32903	antirhea acutata	Species	Rubiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[11412982]

☑ 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	NP ID	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	29100.0	nM	PMID[488789]
NPT2	Others	Unspecified		IC50	=	16300.0	nM	PMID[488789]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC165483 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	1466
0.2-0.3	3336
0.3-0.4	8104
0.4-0.5	10382
0.5-0.6	3691
0.6-0.7	5229
0.7-0.8	7493
0.8-0.85	2276
0.85-0.9	325
0.9-0.95	30
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC109061
0.9737	High Similarity	NPC124747
0.9737	High Similarity	NPC155754
0.9735	High Similarity	NPC166456
0.9735	High Similarity	NPC94220
0.9735	High Similarity	NPC24339
0.9735	High Similarity	NPC98083
0.9735	High Similarity	NPC7543
0.9481	High Similarity	NPC139540
0.9481	High Similarity	NPC177100
0.9363	High Similarity	NPC9309
0.9167	High Similarity	NPC53889
0.9167	High Similarity	NPC24164
0.9161	High Similarity	NPC68324
0.9161	High Similarity	NPC38779
0.9161	High Similarity	NPC160512
0.9161	High Similarity	NPC289322
0.9161	High Similarity	NPC156818
0.9161	High Similarity	NPC114179
0.9108	High Similarity	NPC142252
0.9103	High Similarity	NPC87317
0.9097	High Similarity	NPC250436
0.9097	High Similarity	NPC300845
0.9097	High Similarity	NPC88803
0.9097	High Similarity	NPC291948
0.9097	High Similarity	NPC104983
0.9068	High Similarity	NPC180768
0.9057	High Similarity	NPC471788
0.9026	High Similarity	NPC474656
0.9012	High Similarity	NPC65333
0.9	High Similarity	NPC207575
0.9	High Similarity	NPC13481
0.9	High Similarity	NPC471823
0.8986	High Similarity	NPC178054
0.8974	High Similarity	NPC318432
0.8963	High Similarity	NPC79736
0.8963	High Similarity	NPC67629
0.8957	High Similarity	NPC98583
0.8951	High Similarity	NPC279209
0.8951	High Similarity	NPC102277
0.894	High Similarity	NPC40222
0.894	High Similarity	NPC268515
0.8931	High Similarity	NPC476372
0.8931	High Similarity	NPC476247
0.8931	High Similarity	NPC476371
0.8931	High Similarity	NPC55121
0.8909	High Similarity	NPC267549
0.8903	High Similarity	NPC178574
0.8903	High Similarity	NPC65591
0.8896	High Similarity	NPC212038
0.8896	High Similarity	NPC81332
0.8896	High Similarity	NPC262580
0.8896	High Similarity	NPC100251
0.8896	High Similarity	NPC289396
0.8896	High Similarity	NPC271848
0.8889	High Similarity	NPC211561
0.8882	High Similarity	NPC43065
0.8882	High Similarity	NPC58190
0.8882	High Similarity	NPC236202
0.8882	High Similarity	NPC170103
0.8882	High Similarity	NPC204770
0.8882	High Similarity	NPC82917
0.8882	High Similarity	NPC108811
0.8882	High Similarity	NPC202742
0.8882	High Similarity	NPC263940
0.8882	High Similarity	NPC18185
0.8882	High Similarity	NPC262911
0.8882	High Similarity	NPC294558
0.8882	High Similarity	NPC70409
0.8875	High Similarity	NPC45943
0.8868	High Similarity	NPC158188
0.8868	High Similarity	NPC26326
0.8868	High Similarity	NPC473106
0.8868	High Similarity	NPC103201
0.8868	High Similarity	NPC469889
0.8861	High Similarity	NPC53545
0.8861	High Similarity	NPC117418
0.8846	High Similarity	NPC268484
0.8846	High Similarity	NPC8712
0.8839	High Similarity	NPC476434
0.8831	High Similarity	NPC477612
0.8824	High Similarity	NPC227516
0.8824	High Similarity	NPC20757
0.882	High Similarity	NPC142614
0.8816	High Similarity	NPC96576
0.8816	High Similarity	NPC260397
0.8812	High Similarity	NPC174311
0.8805	High Similarity	NPC292415
0.8805	High Similarity	NPC24627
0.8805	High Similarity	NPC476373
0.8797	High Similarity	NPC472598
0.8797	High Similarity	NPC474055
0.8797	High Similarity	NPC125495
0.879	High Similarity	NPC155015
0.879	High Similarity	NPC142479
0.879	High Similarity	NPC125709
0.879	High Similarity	NPC292385
0.879	High Similarity	NPC321779
0.8782	High Similarity	NPC473236
0.8782	High Similarity	NPC223720
0.878	High Similarity	NPC472454
0.878	High Similarity	NPC257667
0.878	High Similarity	NPC186847
0.8773	High Similarity	NPC475212
0.8765	High Similarity	NPC224851
0.8765	High Similarity	NPC320741
0.8765	High Similarity	NPC171985
0.8758	High Similarity	NPC121290
0.8758	High Similarity	NPC476295
0.875	High Similarity	NPC349525
0.875	High Similarity	NPC165970
0.875	High Similarity	NPC289771
0.875	High Similarity	NPC113163
0.875	High Similarity	NPC474038
0.875	High Similarity	NPC84324
0.875	High Similarity	NPC288131
0.875	High Similarity	NPC472632
0.875	High Similarity	NPC472634
0.875	High Similarity	NPC216916
0.875	High Similarity	NPC97812
0.875	High Similarity	NPC305987
0.875	High Similarity	NPC112418
0.875	High Similarity	NPC471499
0.875	High Similarity	NPC66618
0.8742	High Similarity	NPC172202
0.8742	High Similarity	NPC284127
0.8742	High Similarity	NPC22192
0.8742	High Similarity	NPC476410
0.8734	High Similarity	NPC195796
0.8734	High Similarity	NPC78492
0.8734	High Similarity	NPC291878
0.8734	High Similarity	NPC278778
0.8734	High Similarity	NPC208152
0.8734	High Similarity	NPC35038
0.8734	High Similarity	NPC471787
0.8727	High Similarity	NPC316539
0.8726	High Similarity	NPC213896
0.8726	High Similarity	NPC192083
0.8726	High Similarity	NPC62903
0.8726	High Similarity	NPC7178
0.8725	High Similarity	NPC260741
0.8725	High Similarity	NPC70682
0.872	High Similarity	NPC476365
0.872	High Similarity	NPC91043
0.8718	High Similarity	NPC322899
0.8718	High Similarity	NPC226108
0.8718	High Similarity	NPC134911
0.8718	High Similarity	NPC46283
0.8718	High Similarity	NPC44192
0.8718	High Similarity	NPC469944
0.8718	High Similarity	NPC75695
0.8718	High Similarity	NPC272552
0.8716	High Similarity	NPC470802
0.8712	High Similarity	NPC473818
0.8712	High Similarity	NPC260266
0.8704	High Similarity	NPC125039
0.8704	High Similarity	NPC7688
0.8704	High Similarity	NPC58223
0.8704	High Similarity	NPC7154
0.8704	High Similarity	NPC36
0.8704	High Similarity	NPC72787
0.8704	High Similarity	NPC36916
0.8701	High Similarity	NPC142863
0.8701	High Similarity	NPC187398
0.8701	High Similarity	NPC476348
0.8696	High Similarity	NPC474162
0.8696	High Similarity	NPC474034
0.8696	High Similarity	NPC285108
0.8696	High Similarity	NPC471745
0.8696	High Similarity	NPC33298
0.8696	High Similarity	NPC474150
0.8696	High Similarity	NPC472635
0.8696	High Similarity	NPC474033
0.8696	High Similarity	NPC12326
0.8696	High Similarity	NPC192258
0.8696	High Similarity	NPC476200
0.8693	High Similarity	NPC474799
0.869	High Similarity	NPC208797
0.869	High Similarity	NPC53680
0.8688	High Similarity	NPC475784
0.8688	High Similarity	NPC470326
0.8688	High Similarity	NPC471744
0.8688	High Similarity	NPC36217
0.8688	High Similarity	NPC321399
0.8688	High Similarity	NPC101731
0.8688	High Similarity	NPC119209
0.8688	High Similarity	NPC287328
0.8688	High Similarity	NPC118256
0.8688	High Similarity	NPC282009
0.8688	High Similarity	NPC192686
0.8688	High Similarity	NPC174953
0.8688	High Similarity	NPC289346
0.8688	High Similarity	NPC472631
0.8688	High Similarity	NPC472630
0.8684	High Similarity	NPC473108
0.8679	High Similarity	NPC108456
0.8679	High Similarity	NPC291508
0.8679	High Similarity	NPC27337
0.8679	High Similarity	NPC63454
0.8679	High Similarity	NPC222689

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC165483 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	876
0.2-0.3	1740
0.3-0.4	2593
0.4-0.5	1829
0.5-0.6	1002
0.6-0.7	608
0.7-0.8	153
0.8-0.85	29
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9097	High Similarity	NPD4868	Clinical (unspecified phase)
0.8773	High Similarity	NPD5844	Phase 1
0.8726	High Similarity	NPD2393	Clinical (unspecified phase)
0.8704	High Similarity	NPD6167	Clinical (unspecified phase)
0.8704	High Similarity	NPD6166	Phase 2
0.8704	High Similarity	NPD6168	Clinical (unspecified phase)
0.8634	High Similarity	NPD7199	Phase 2
0.8554	High Similarity	NPD7993	Clinical (unspecified phase)
0.8544	High Similarity	NPD1934	Approved
0.8509	High Similarity	NPD6234	Discontinued
0.8485	Intermediate Similarity	NPD7228	Approved
0.8446	Intermediate Similarity	NPD1613	Approved
0.8446	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD37	Approved
0.8415	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD4967	Phase 2
0.8385	Intermediate Similarity	NPD4965	Approved
0.8385	Intermediate Similarity	NPD4966	Approved
0.8383	Intermediate Similarity	NPD7074	Phase 3
0.8354	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7075	Discontinued
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7054	Approved
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8311	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD4380	Phase 2
0.8274	Intermediate Similarity	NPD7472	Approved
0.8261	Intermediate Similarity	NPD1465	Phase 2
0.825	Intermediate Similarity	NPD7411	Suspended
0.8235	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD6797	Phase 2
0.821	Intermediate Similarity	NPD3817	Phase 2
0.8188	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7251	Discontinued
0.8176	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4908	Phase 1
0.8155	Intermediate Similarity	NPD3818	Discontinued
0.8148	Intermediate Similarity	NPD8455	Phase 2
0.8148	Intermediate Similarity	NPD2801	Approved
0.8148	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD3027	Phase 3
0.8121	Intermediate Similarity	NPD5494	Approved
0.811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6801	Discontinued
0.8072	Intermediate Similarity	NPD6959	Discontinued
0.8038	Intermediate Similarity	NPD1511	Approved
0.8036	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6190	Approved
0.8024	Intermediate Similarity	NPD7229	Phase 3
0.8023	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7240	Approved
0.7965	Intermediate Similarity	NPD6559	Discontinued
0.795	Intermediate Similarity	NPD1653	Approved
0.7947	Intermediate Similarity	NPD6798	Discontinued
0.7939	Intermediate Similarity	NPD7768	Phase 2
0.7939	Intermediate Similarity	NPD3882	Suspended
0.7937	Intermediate Similarity	NPD1512	Approved
0.7914	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4628	Phase 3
0.7843	Intermediate Similarity	NPD4060	Phase 1
0.7821	Intermediate Similarity	NPD6099	Approved
0.7821	Intermediate Similarity	NPD6100	Approved
0.7812	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3787	Discontinued
0.7792	Intermediate Similarity	NPD5124	Phase 1
0.7792	Intermediate Similarity	NPD6355	Discontinued
0.7792	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6233	Phase 2
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5402	Approved
0.7751	Intermediate Similarity	NPD8127	Discontinued
0.7736	Intermediate Similarity	NPD3750	Approved
0.7722	Intermediate Similarity	NPD1549	Phase 2
0.7703	Intermediate Similarity	NPD1610	Phase 2
0.7702	Intermediate Similarity	NPD6799	Approved
0.7677	Intermediate Similarity	NPD230	Phase 1
0.7673	Intermediate Similarity	NPD6674	Discontinued
0.767	Intermediate Similarity	NPD8313	Approved
0.767	Intermediate Similarity	NPD8312	Approved
0.7669	Intermediate Similarity	NPD5403	Approved
0.7658	Intermediate Similarity	NPD7266	Discontinued
0.7657	Intermediate Similarity	NPD7685	Pre-registration
0.7654	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1608	Approved
0.7643	Intermediate Similarity	NPD7033	Discontinued
0.7636	Intermediate Similarity	NPD6599	Discontinued
0.7634	Intermediate Similarity	NPD7680	Approved
0.763	Intermediate Similarity	NPD3751	Discontinued
0.761	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7097	Phase 1
0.7574	Intermediate Similarity	NPD3749	Approved
0.7569	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6005	Phase 3
0.7547	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6002	Phase 3
0.7547	Intermediate Similarity	NPD6004	Phase 3
0.7547	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5401	Approved
0.7546	Intermediate Similarity	NPD2534	Approved
0.7546	Intermediate Similarity	NPD2532	Approved
0.7546	Intermediate Similarity	NPD2533	Approved
0.7532	Intermediate Similarity	NPD4625	Phase 3
0.7516	Intermediate Similarity	NPD4110	Phase 3
0.7516	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2861	Phase 2
0.7514	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD2797	Approved
0.7484	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2796	Approved
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7484	Intermediate Similarity	NPD3268	Approved
0.7453	Intermediate Similarity	NPD1652	Phase 2
0.7453	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD17	Approved
0.743	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD919	Approved
0.7421	Intermediate Similarity	NPD1510	Phase 2
0.7421	Intermediate Similarity	NPD3748	Approved
0.7419	Intermediate Similarity	NPD7095	Approved
0.7407	Intermediate Similarity	NPD8166	Discontinued
0.7405	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2438	Suspended
0.7368	Intermediate Similarity	NPD4749	Approved
0.7365	Intermediate Similarity	NPD7458	Discontinued
0.7365	Intermediate Similarity	NPD3226	Approved
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7344	Intermediate Similarity	NPD8151	Discontinued
0.7329	Intermediate Similarity	NPD5763	Approved
0.7329	Intermediate Similarity	NPD5762	Approved
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7296	Intermediate Similarity	NPD6653	Approved
0.7289	Intermediate Similarity	NPD6273	Approved
0.7283	Intermediate Similarity	NPD6746	Phase 2
0.7278	Intermediate Similarity	NPD1240	Approved
0.7268	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7783	Phase 2
0.7267	Intermediate Similarity	NPD1551	Phase 2
0.7257	Intermediate Similarity	NPD3926	Phase 2
0.7253	Intermediate Similarity	NPD8434	Phase 2
0.7246	Intermediate Similarity	NPD7427	Discontinued
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7229	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4062	Phase 3
0.7208	Intermediate Similarity	NPD3225	Approved
0.7208	Intermediate Similarity	NPD1283	Approved
0.7207	Intermediate Similarity	NPD5953	Discontinued
0.7205	Intermediate Similarity	NPD2799	Discontinued
0.7195	Intermediate Similarity	NPD7003	Approved
0.7188	Intermediate Similarity	NPD1607	Approved
0.7179	Intermediate Similarity	NPD3018	Phase 2
0.7178	Intermediate Similarity	NPD2424	Discontinued
0.7173	Intermediate Similarity	NPD7435	Discontinued
0.717	Intermediate Similarity	NPD2979	Phase 3
0.717	Intermediate Similarity	NPD943	Approved
0.717	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4140	Approved
0.717	Intermediate Similarity	NPD3620	Phase 2
0.7169	Intermediate Similarity	NPD7212	Phase 2
0.7169	Intermediate Similarity	NPD7390	Discontinued
0.7169	Intermediate Similarity	NPD7213	Phase 3
0.7161	Intermediate Similarity	NPD3266	Approved
0.7161	Intermediate Similarity	NPD3267	Approved
0.716	Intermediate Similarity	NPD4476	Approved
0.716	Intermediate Similarity	NPD4477	Approved
0.7159	Intermediate Similarity	NPD5242	Approved
0.7158	Intermediate Similarity	NPD2493	Approved
0.7158	Intermediate Similarity	NPD2494	Approved
0.7151	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD4536	Approved
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4538	Approved
0.7143	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD920	Approved
0.7135	Intermediate Similarity	NPD4582	Approved
0.7135	Intermediate Similarity	NPD4583	Approved
0.7135	Intermediate Similarity	NPD2490	Approved
0.7135	Intermediate Similarity	NPD7177	Discontinued
0.7135	Intermediate Similarity	NPD2488	Approved
0.7134	Intermediate Similarity	NPD2800	Approved
0.7127	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7447	Phase 1
0.7125	Intermediate Similarity	NPD447	Suspended
0.7124	Intermediate Similarity	NPD1091	Approved
0.7118	Intermediate Similarity	NPD6502	Phase 2
0.7117	Intermediate Similarity	NPD2346	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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