NPASS Compound

Structure

NPC234052 OpenBabel07101718312D 25 28 0 0 1 0 0 0 0 0999 V2000 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 -2.5981 -0.5000 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 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 1.0000 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 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 1.7321 0.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 0.0000 0.0000 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 8 24 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 25 1 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 6 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	328.735
LogP:	2.04
LogD:	2.408
LogS:	-3.828
# Rotatable Bonds:	2
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.855
Synthetic Accessibility Score:	3.449
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.915
MDCK Permeability:	2.240321373392362e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.075
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.54
Plasma Protein Binding (PPB):	87.21198272705078%
Volume Distribution (VD):	0.957
Pgp-substrate:	12.68744945526123%

ADMET: Metabolism

CYP1A2-inhibitor:	0.477
CYP1A2-substrate:	0.818
CYP2C19-inhibitor:	0.74
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.586
CYP2C9-substrate:	0.739
CYP2D6-inhibitor:	0.131
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.675

ADMET: Excretion

Clearance (CL):	6.448
Half-life (T1/2):	0.82

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.562
AMES Toxicity:	0.487
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.467
Skin Sensitization:	0.705
Carcinogencity:	0.61
Eye Corrosion:	0.003
Eye Irritation:	0.086
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC234052

Natural Product ID:	NPC234052
*Common Name:**	2-Methoxygliricidol
IUPAC Name:	(6aR,12aR)-9,12a-dihydroxy-2,3-dimethoxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one
Synonyms:	2-Methoxygliricidol
Standard InCHIKey:	BFLVWZBVOBQBNK-SJLPKXTDSA-N
Standard InCHI:	InChI=1S/C18H16O7/c1-22-14-6-11-13(7-15(14)23-2)24-8-16-18(11,21)17(20)10-4-3-9(19)5-12(10)25-16/h3-7,16,19,21H,8H2,1-2H3/t16-,18-/m1/s1
SMILES:	COc1cc2c(cc1OC)OC[C@@H]1[C@@]2(O)C(=O)c2c(O1)cc(cc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455085
PubChem CID:	10593523
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001607] Rotenoids [CHEMONTID:0003528] Rotenones

*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
NPO14052	Gliricidia sepium	Species	Fabaceae	Eukaryota	bark	n.a.	n.a.	PMID[9917318]
NPO14052	Gliricidia sepium	Species	Fabaceae	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	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	284.5	ug.mL-1	PMID[507585]

☑ 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 NPC234052 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	422
0.1-0.2	1758
0.2-0.3	4392
0.3-0.4	10324
0.4-0.5	7436
0.5-0.6	3617
0.6-0.7	4951
0.7-0.8	5334
0.8-0.85	2633
0.85-0.9	1488
0.9-0.95	332
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC224280
0.9686	High Similarity	NPC152477
0.9679	High Similarity	NPC173137
0.9677	High Similarity	NPC152904
0.9623	High Similarity	NPC8965
0.962	High Similarity	NPC62261
0.9565	High Similarity	NPC121333
0.9563	High Similarity	NPC177480
0.9563	High Similarity	NPC242395
0.956	High Similarity	NPC477517
0.9554	High Similarity	NPC308992
0.9551	High Similarity	NPC55738
0.9548	High Similarity	NPC303255
0.9503	High Similarity	NPC74559
0.949	High Similarity	NPC263449
0.9487	High Similarity	NPC162869
0.9487	High Similarity	NPC99597
0.9487	High Similarity	NPC156057
0.9487	High Similarity	NPC210084
0.9487	High Similarity	NPC474836
0.9487	High Similarity	NPC181960
0.9487	High Similarity	NPC475267
0.9487	High Similarity	NPC67876
0.9487	High Similarity	NPC474208
0.9487	High Similarity	NPC48208
0.9484	High Similarity	NPC37392
0.9441	High Similarity	NPC326877
0.9437	High Similarity	NPC173292
0.9437	High Similarity	NPC120593
0.9434	High Similarity	NPC41301
0.943	High Similarity	NPC134783
0.9423	High Similarity	NPC255106
0.9423	High Similarity	NPC235165
0.9423	High Similarity	NPC472916
0.9423	High Similarity	NPC474638
0.9419	High Similarity	NPC203080
0.9419	High Similarity	NPC472915
0.939	High Similarity	NPC156635
0.9383	High Similarity	NPC103307
0.9379	High Similarity	NPC477154
0.9379	High Similarity	NPC117854
0.9379	High Similarity	NPC6588
0.9379	High Similarity	NPC14662
0.9371	High Similarity	NPC472448
0.9371	High Similarity	NPC83922
0.9371	High Similarity	NPC474034
0.9371	High Similarity	NPC474033
0.9367	High Similarity	NPC470183
0.9367	High Similarity	NPC471976
0.9367	High Similarity	NPC200746
0.9363	High Similarity	NPC245758
0.9363	High Similarity	NPC96167
0.9363	High Similarity	NPC472914
0.9363	High Similarity	NPC469584
0.9363	High Similarity	NPC129684
0.9363	High Similarity	NPC472911
0.9363	High Similarity	NPC472913
0.9363	High Similarity	NPC222814
0.9363	High Similarity	NPC471479
0.9363	High Similarity	NPC52530
0.9363	High Similarity	NPC472910
0.9363	High Similarity	NPC471515
0.9363	High Similarity	NPC299520
0.9359	High Similarity	NPC31018
0.9359	High Similarity	NPC472909
0.9359	High Similarity	NPC255807
0.9359	High Similarity	NPC2928
0.9317	High Similarity	NPC471213
0.9317	High Similarity	NPC128293
0.9313	High Similarity	NPC236521
0.9313	High Similarity	NPC152659
0.9313	High Similarity	NPC273959
0.9313	High Similarity	NPC475985
0.9313	High Similarity	NPC248638
0.9313	High Similarity	NPC472625
0.9308	High Similarity	NPC29876
0.9308	High Similarity	NPC167678
0.9308	High Similarity	NPC472632
0.9308	High Similarity	NPC3629
0.9308	High Similarity	NPC471210
0.9304	High Similarity	NPC473990
0.9304	High Similarity	NPC250214
0.9304	High Similarity	NPC95936
0.9304	High Similarity	NPC476242
0.9299	High Similarity	NPC320825
0.9299	High Similarity	NPC49824
0.9299	High Similarity	NPC201837
0.9299	High Similarity	NPC326037
0.9299	High Similarity	NPC471500
0.9299	High Similarity	NPC13858
0.9295	High Similarity	NPC206238
0.9295	High Similarity	NPC280937
0.9295	High Similarity	NPC18727
0.9295	High Similarity	NPC141212
0.9295	High Similarity	NPC292214
0.9295	High Similarity	NPC86485
0.9295	High Similarity	NPC88645
0.9295	High Similarity	NPC167091
0.9295	High Similarity	NPC271779
0.929	High Similarity	NPC117579
0.929	High Similarity	NPC149614
0.929	High Similarity	NPC471229
0.9264	High Similarity	NPC44558
0.9264	High Similarity	NPC472276
0.9259	High Similarity	NPC243877
0.9259	High Similarity	NPC150131
0.9259	High Similarity	NPC295082
0.9255	High Similarity	NPC275780
0.9255	High Similarity	NPC125039
0.9255	High Similarity	NPC7688
0.9255	High Similarity	NPC472450
0.9255	High Similarity	NPC58223
0.9255	High Similarity	NPC72787
0.9255	High Similarity	NPC7154
0.9255	High Similarity	NPC239752
0.9255	High Similarity	NPC36916
0.9255	High Similarity	NPC293319
0.9255	High Similarity	NPC36
0.925	High Similarity	NPC261470
0.925	High Similarity	NPC474162
0.925	High Similarity	NPC472964
0.925	High Similarity	NPC474150
0.925	High Similarity	NPC220912
0.925	High Similarity	NPC25152
0.925	High Similarity	NPC229632
0.9245	High Similarity	NPC192686
0.9245	High Similarity	NPC475784
0.9245	High Similarity	NPC174953
0.9245	High Similarity	NPC476980
0.9245	High Similarity	NPC119209
0.9245	High Similarity	NPC282009
0.9245	High Similarity	NPC204290
0.9245	High Similarity	NPC139036
0.9245	High Similarity	NPC474960
0.9245	High Similarity	NPC118256
0.9245	High Similarity	NPC287328
0.9245	High Similarity	NPC472902
0.9241	High Similarity	NPC473272
0.9241	High Similarity	NPC471209
0.9241	High Similarity	NPC284820
0.9241	High Similarity	NPC78225
0.9241	High Similarity	NPC223787
0.9241	High Similarity	NPC224137
0.9241	High Similarity	NPC93376
0.9241	High Similarity	NPC291508
0.9241	High Similarity	NPC300727
0.9241	High Similarity	NPC75215
0.9241	High Similarity	NPC227192
0.9241	High Similarity	NPC476981
0.9241	High Similarity	NPC203891
0.9241	High Similarity	NPC262286
0.9241	High Similarity	NPC36852
0.9241	High Similarity	NPC110070
0.9241	High Similarity	NPC101830
0.9241	High Similarity	NPC189179
0.9241	High Similarity	NPC27337
0.9241	High Similarity	NPC470402
0.9241	High Similarity	NPC241904
0.9236	High Similarity	NPC256612
0.9236	High Similarity	NPC32557
0.9236	High Similarity	NPC20830
0.9236	High Similarity	NPC26227
0.9236	High Similarity	NPC189960
0.9236	High Similarity	NPC213622
0.9236	High Similarity	NPC44079
0.9236	High Similarity	NPC201451
0.9231	High Similarity	NPC101996
0.9231	High Similarity	NPC236637
0.9231	High Similarity	NPC180234
0.9231	High Similarity	NPC120537
0.9231	High Similarity	NPC301123
0.9231	High Similarity	NPC477231
0.9231	High Similarity	NPC161277
0.9231	High Similarity	NPC302950
0.9231	High Similarity	NPC39007
0.9231	High Similarity	NPC257648
0.9231	High Similarity	NPC219582
0.9231	High Similarity	NPC199100
0.9226	High Similarity	NPC179183
0.9226	High Similarity	NPC267117
0.9226	High Similarity	NPC338131
0.9217	High Similarity	NPC67302
0.9212	High Similarity	NPC108202
0.9202	High Similarity	NPC472383
0.9202	High Similarity	NPC288813
0.9202	High Similarity	NPC472381
0.9198	High Similarity	NPC472449
0.9198	High Similarity	NPC39091
0.9198	High Similarity	NPC170245
0.9193	High Similarity	NPC186686
0.9193	High Similarity	NPC303460
0.9193	High Similarity	NPC124038
0.9193	High Similarity	NPC189473
0.9193	High Similarity	NPC23298
0.9193	High Similarity	NPC306321
0.9187	High Similarity	NPC165549
0.9187	High Similarity	NPC471212
0.9187	High Similarity	NPC474038
0.9187	High Similarity	NPC228383
0.9187	High Similarity	NPC266314

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 NPC234052 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	954
0.2-0.3	1839
0.3-0.4	2605
0.4-0.5	1769
0.5-0.6	980
0.6-0.7	417
0.7-0.8	140
0.8-0.85	34
0.85-0.9	11
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9255	High Similarity	NPD6168	Clinical (unspecified phase)
0.9255	High Similarity	NPD6167	Clinical (unspecified phase)
0.9255	High Similarity	NPD6166	Phase 2
0.9231	High Similarity	NPD1934	Approved
0.9172	High Similarity	NPD2801	Approved
0.9125	High Similarity	NPD5494	Approved
0.9057	High Similarity	NPD3882	Suspended
0.9051	High Similarity	NPD2393	Clinical (unspecified phase)
0.8869	High Similarity	NPD4338	Clinical (unspecified phase)
0.8802	High Similarity	NPD7074	Phase 3
0.8758	High Similarity	NPD3817	Phase 2
0.8757	High Similarity	NPD7808	Phase 3
0.875	High Similarity	NPD6797	Phase 2
0.8743	High Similarity	NPD7054	Approved
0.8726	High Similarity	NPD1512	Approved
0.8704	High Similarity	NPD4868	Clinical (unspecified phase)
0.8698	High Similarity	NPD7251	Discontinued
0.869	High Similarity	NPD7472	Approved
0.8683	High Similarity	NPD3818	Discontinued
0.865	High Similarity	NPD7075	Discontinued
0.8625	High Similarity	NPD4380	Phase 2
0.8599	High Similarity	NPD1511	Approved
0.858	High Similarity	NPD7096	Clinical (unspecified phase)
0.8544	High Similarity	NPD4378	Clinical (unspecified phase)
0.8537	High Similarity	NPD4381	Clinical (unspecified phase)
0.8529	High Similarity	NPD7993	Clinical (unspecified phase)
0.8528	High Similarity	NPD5402	Approved
0.8521	High Similarity	NPD5844	Phase 1
0.8516	High Similarity	NPD1549	Phase 2
0.8452	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD6799	Approved
0.8354	Intermediate Similarity	NPD1465	Phase 2
0.8303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6801	Discontinued
0.8282	Intermediate Similarity	NPD6599	Discontinued
0.8274	Intermediate Similarity	NPD1247	Approved
0.8274	Intermediate Similarity	NPD6959	Discontinued
0.8269	Intermediate Similarity	NPD2796	Approved
0.8242	Intermediate Similarity	NPD7819	Suspended
0.8225	Intermediate Similarity	NPD6232	Discontinued
0.8205	Intermediate Similarity	NPD1510	Phase 2
0.8199	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7473	Discontinued
0.8176	Intermediate Similarity	NPD3926	Phase 2
0.814	Intermediate Similarity	NPD3751	Discontinued
0.8121	Intermediate Similarity	NPD7411	Suspended
0.8098	Intermediate Similarity	NPD5403	Approved
0.8065	Intermediate Similarity	NPD1240	Approved
0.8056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3787	Discontinued
0.7988	Intermediate Similarity	NPD3749	Approved
0.7978	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5401	Approved
0.7962	Intermediate Similarity	NPD1607	Approved
0.7955	Intermediate Similarity	NPD6559	Discontinued
0.7949	Intermediate Similarity	NPD943	Approved
0.7941	Intermediate Similarity	NPD919	Approved
0.7919	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3750	Approved
0.7834	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1613	Approved
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7812	Intermediate Similarity	NPD2935	Discontinued
0.7791	Intermediate Similarity	NPD6190	Approved
0.7754	Intermediate Similarity	NPD6776	Approved
0.7754	Intermediate Similarity	NPD6779	Approved
0.7754	Intermediate Similarity	NPD6778	Approved
0.7754	Intermediate Similarity	NPD6777	Approved
0.7754	Intermediate Similarity	NPD6781	Approved
0.7754	Intermediate Similarity	NPD6780	Approved
0.7754	Intermediate Similarity	NPD6782	Approved
0.775	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4628	Phase 3
0.7716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD447	Suspended
0.7673	Intermediate Similarity	NPD230	Phase 1
0.7669	Intermediate Similarity	NPD2800	Approved
0.7665	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2534	Approved
0.7651	Intermediate Similarity	NPD2532	Approved
0.7651	Intermediate Similarity	NPD2533	Approved
0.7643	Intermediate Similarity	NPD3027	Phase 3
0.7637	Intermediate Similarity	NPD8150	Discontinued
0.7637	Intermediate Similarity	NPD8434	Phase 2
0.7632	Intermediate Similarity	NPD7697	Approved
0.7632	Intermediate Similarity	NPD7696	Phase 3
0.7632	Intermediate Similarity	NPD7698	Approved
0.7632	Intermediate Similarity	NPD7435	Discontinued
0.7628	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1653	Approved
0.7593	Intermediate Similarity	NPD6099	Approved
0.7593	Intermediate Similarity	NPD6100	Approved
0.7593	Intermediate Similarity	NPD1551	Phase 2
0.7569	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD8312	Approved
0.7565	Intermediate Similarity	NPD7701	Phase 2
0.7561	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7685	Pre-registration
0.7546	Intermediate Similarity	NPD2344	Approved
0.7543	Intermediate Similarity	NPD7199	Phase 2
0.7531	Intermediate Similarity	NPD3748	Approved
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.7528	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD7871	Phase 2
0.7487	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD6535	Approved
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3226	Approved
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.746	Intermediate Similarity	NPD7700	Phase 2
0.746	Intermediate Similarity	NPD7699	Phase 2
0.7456	Intermediate Similarity	NPD920	Approved
0.7453	Intermediate Similarity	NPD1933	Approved
0.7442	Intermediate Similarity	NPD37	Approved
0.7442	Intermediate Similarity	NPD6844	Discontinued
0.7439	Intermediate Similarity	NPD2346	Discontinued
0.7423	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2799	Discontinued
0.7414	Intermediate Similarity	NPD4965	Approved
0.7414	Intermediate Similarity	NPD4967	Phase 2
0.7414	Intermediate Similarity	NPD4966	Approved
0.741	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD9494	Approved
0.7403	Intermediate Similarity	NPD5953	Discontinued
0.7398	Intermediate Similarity	NPD7874	Approved
0.7398	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7286	Phase 2
0.7381	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2309	Approved
0.736	Intermediate Similarity	NPD7783	Phase 2
0.736	Intermediate Similarity	NPD7801	Approved
0.736	Intermediate Similarity	NPD5242	Approved
0.736	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8151	Discontinued
0.7337	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6233	Phase 2
0.7322	Intermediate Similarity	NPD7549	Discontinued
0.7322	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD2403	Approved
0.7306	Intermediate Similarity	NPD6823	Phase 2
0.7302	Intermediate Similarity	NPD4363	Phase 3
0.7302	Intermediate Similarity	NPD4360	Phase 2
0.7296	Intermediate Similarity	NPD2861	Phase 2
0.7278	Intermediate Similarity	NPD7390	Discontinued
0.7267	Intermediate Similarity	NPD6798	Discontinued
0.7267	Intermediate Similarity	NPD2313	Discontinued
0.7261	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5353	Approved
0.7246	Intermediate Similarity	NPD1243	Approved
0.7245	Intermediate Similarity	NPD7584	Approved
0.7244	Intermediate Similarity	NPD1610	Phase 2
0.7239	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7207	Intermediate Similarity	NPD5710	Approved
0.7207	Intermediate Similarity	NPD5711	Approved
0.7206	Intermediate Similarity	NPD7907	Approved
0.7195	Intermediate Similarity	NPD6651	Approved
0.7192	Intermediate Similarity	NPD4665	Approved
0.7192	Intermediate Similarity	NPD4111	Phase 1
0.7174	Intermediate Similarity	NPD7240	Approved
0.717	Intermediate Similarity	NPD1203	Approved
0.7168	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2493	Approved
0.7165	Intermediate Similarity	NPD2494	Approved
0.7143	Intermediate Similarity	NPD8319	Approved
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD8320	Phase 1
0.7135	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7266	Discontinued
0.7125	Intermediate Similarity	NPD2798	Approved
0.7102	Intermediate Similarity	NPD8455	Phase 2
0.7099	Intermediate Similarity	NPD4625	Phase 3
0.709	Intermediate Similarity	NPD4287	Approved
0.7086	Intermediate Similarity	NPD6386	Approved
0.7086	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6385	Approved
0.7083	Intermediate Similarity	NPD2424	Discontinued
0.7077	Intermediate Similarity	NPD3450	Approved
0.7077	Intermediate Similarity	NPD3452	Approved
0.7073	Intermediate Similarity	NPD4060	Phase 1
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD2354	Approved
0.7059	Intermediate Similarity	NPD3887	Approved
0.7056	Intermediate Similarity	NPD4582	Approved
0.7056	Intermediate Similarity	NPD8127	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