NPASS Compound

Structure

NPC92805 OpenBabel07101719512D 26 29 0 0 1 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8301 0.6340 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 6.8301 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 0.6340 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 -1.0000 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 6.8301 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 7.3301 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 5.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 2.3660 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3301 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3301 1.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 24 1 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 21 1 0 0 0 0 12 25 1 0 0 0 0 13 19 2 0 0 0 0 14 24 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	363.042
LogP:	4.259
LogD:	3.871
LogS:	-4.297
# Rotatable Bonds:	2
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.865
Synthetic Accessibility Score:	3.576
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.731
MDCK Permeability:	1.6727924958104268e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	99.38927459716797%
Volume Distribution (VD):	0.756
Pgp-substrate:	1.5570974349975586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.752
CYP2C19-inhibitor:	0.768
CYP2C19-substrate:	0.747
CYP2C9-inhibitor:	0.737
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.972
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.666

ADMET: Excretion

Clearance (CL):	12.262
Half-life (T1/2):	0.152

ADMET: Toxicity

hERG Blockers:	0.197
Human Hepatotoxicity (H-HT):	0.822
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.411
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.355
Carcinogencity:	0.865
Eye Corrosion:	0.003
Eye Irritation:	0.039
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC92805

Natural Product ID:	NPC92805
*Common Name:**	(3S)-3-(2-Hydroxy-4-Methoxyphenyl)-8,8-Dimethyl-2,4-Dihydropyrano[2,3-F]Chromen-3-Ol
IUPAC Name:	(3S)-3-(2-hydroxy-4-methoxyphenyl)-8,8-dimethyl-2,4-dihydropyrano[2,3-f]chromen-3-ol
Synonyms:
Standard InCHIKey:	NHWGLCDIXCJLLD-OAQYLSRUSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-20(2)9-8-15-18(26-20)7-4-13-11-21(23,12-25-19(13)15)16-6-5-14(24-3)10-17(16)22/h4-10,22-23H,11-12H2,1-3H3/t21-/m1/s1
SMILES:	CC1(C)C=Cc2c(ccc3C[C@@](COc23)(c2ccc(cc2O)OC)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463101
PubChem CID:	44566457
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0003530] Pyranoisoflavonoids

*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
NPO401	Berchemia discolor	Species	Rhamnaceae	Eukaryota	n.a.	Tanzanian	n.a.	PMID[17125241]
NPO401	Berchemia discolor	Species	Rhamnaceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[468506]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[468506]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[468506]

☑ 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 NPC92805 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	405
0.1-0.2	1544
0.2-0.3	4102
0.3-0.4	11781
0.4-0.5	6699
0.5-0.6	4013
0.6-0.7	7086
0.7-0.8	5682
0.8-0.85	1007
0.85-0.9	258
0.9-0.95	94
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC20829
0.9767	High Similarity	NPC262585
0.9767	High Similarity	NPC18189
0.9685	High Similarity	NPC118683
0.9685	High Similarity	NPC164804
0.9685	High Similarity	NPC211413
0.9685	High Similarity	NPC244888
0.9685	High Similarity	NPC293203
0.9685	High Similarity	NPC68205
0.9612	High Similarity	NPC124085
0.9612	High Similarity	NPC117048
0.9535	High Similarity	NPC85435
0.9535	High Similarity	NPC77196
0.9531	High Similarity	NPC103799
0.9528	High Similarity	NPC134360
0.947	High Similarity	NPC475836
0.9466	High Similarity	NPC3049
0.9462	High Similarity	NPC225696
0.9462	High Similarity	NPC296915
0.9462	High Similarity	NPC115335
0.9462	High Similarity	NPC223008
0.9462	High Similarity	NPC198154
0.9462	High Similarity	NPC97834
0.9449	High Similarity	NPC38664
0.9449	High Similarity	NPC53986
0.9449	High Similarity	NPC222572
0.9449	High Similarity	NPC87224
0.9403	High Similarity	NPC204347
0.9403	High Similarity	NPC2613
0.9403	High Similarity	NPC59841
0.9403	High Similarity	NPC475891
0.9394	High Similarity	NPC474687
0.938	High Similarity	NPC162801
0.9375	High Similarity	NPC93962
0.937	High Similarity	NPC149796
0.9308	High Similarity	NPC13005
0.9297	High Similarity	NPC274717
0.9291	High Similarity	NPC26879
0.9291	High Similarity	NPC50315
0.9291	High Similarity	NPC283049
0.9291	High Similarity	NPC230479
0.9231	High Similarity	NPC236014
0.9231	High Similarity	NPC476166
0.9231	High Similarity	NPC300875
0.9231	High Similarity	NPC280653
0.9231	High Similarity	NPC17343
0.9231	High Similarity	NPC164574
0.9231	High Similarity	NPC150011
0.9231	High Similarity	NPC12875
0.9231	High Similarity	NPC129784
0.9231	High Similarity	NPC129106
0.9231	High Similarity	NPC118114
0.9231	High Similarity	NPC268917
0.9231	High Similarity	NPC196765
0.9231	High Similarity	NPC207892
0.9231	High Similarity	NPC206224
0.9231	High Similarity	NPC228369
0.9213	High Similarity	NPC102540
0.9213	High Similarity	NPC188022
0.9213	High Similarity	NPC17809
0.9213	High Similarity	NPC285040
0.9213	High Similarity	NPC103420
0.9179	High Similarity	NPC260741
0.9179	High Similarity	NPC70682
0.9154	High Similarity	NPC27187
0.9154	High Similarity	NPC470225
0.9141	High Similarity	NPC276212
0.9134	High Similarity	NPC86502
0.9134	High Similarity	NPC134195
0.9134	High Similarity	NPC106914
0.9134	High Similarity	NPC197351
0.9134	High Similarity	NPC246648
0.913	High Similarity	NPC233980
0.9124	High Similarity	NPC475492
0.9098	High Similarity	NPC473413
0.9098	High Similarity	NPC151224
0.9084	High Similarity	NPC271945
0.9084	High Similarity	NPC181497
0.9065	High Similarity	NPC21776
0.9065	High Similarity	NPC16269
0.9062	High Similarity	NPC278552
0.9062	High Similarity	NPC207179
0.9062	High Similarity	NPC167571
0.9058	High Similarity	NPC469557
0.9055	High Similarity	NPC38761
0.9055	High Similarity	NPC76465
0.9055	High Similarity	NPC474160
0.9048	High Similarity	NPC97432
0.9048	High Similarity	NPC190454
0.9044	High Similarity	NPC277331
0.9044	High Similarity	NPC5155
0.9044	High Similarity	NPC100482
0.9044	High Similarity	NPC35216
0.9037	High Similarity	NPC32630
0.903	High Similarity	NPC230734
0.903	High Similarity	NPC265433
0.903	High Similarity	NPC248727
0.903	High Similarity	NPC470802
0.903	High Similarity	NPC474639
0.903	High Similarity	NPC227503
0.903	High Similarity	NPC270456
0.903	High Similarity	NPC162659
0.9023	High Similarity	NPC473107
0.9	High Similarity	NPC39064
0.9	High Similarity	NPC47283
0.8986	High Similarity	NPC473108
0.8984	High Similarity	NPC159132
0.8976	High Similarity	NPC100099
0.8976	High Similarity	NPC36016
0.8971	High Similarity	NPC259519
0.8963	High Similarity	NPC211549
0.8955	High Similarity	NPC61946
0.8955	High Similarity	NPC94750
0.8955	High Similarity	NPC121812
0.8955	High Similarity	NPC164787
0.8955	High Similarity	NPC112246
0.8955	High Similarity	NPC474206
0.8955	High Similarity	NPC470356
0.8955	High Similarity	NPC112939
0.8947	High Similarity	NPC11060
0.8947	High Similarity	NPC168059
0.8947	High Similarity	NPC215037
0.8947	High Similarity	NPC229442
0.8929	High Similarity	NPC474397
0.8905	High Similarity	NPC265075
0.8898	High Similarity	NPC193364
0.8898	High Similarity	NPC54972
0.8897	High Similarity	NPC319647
0.8897	High Similarity	NPC25966
0.8897	High Similarity	NPC245207
0.8897	High Similarity	NPC127218
0.8889	High Similarity	NPC306441
0.8889	High Similarity	NPC234952
0.8889	High Similarity	NPC269091
0.8889	High Similarity	NPC471522
0.8889	High Similarity	NPC173660
0.8889	High Similarity	NPC16435
0.8889	High Similarity	NPC302701
0.8881	High Similarity	NPC131950
0.8881	High Similarity	NPC317380
0.8872	High Similarity	NPC127624
0.8872	High Similarity	NPC202762
0.8872	High Similarity	NPC86655
0.8865	High Similarity	NPC473876
0.8849	High Similarity	NPC50250
0.8849	High Similarity	NPC280092
0.8849	High Similarity	NPC93323
0.8849	High Similarity	NPC12641
0.8849	High Similarity	NPC45257
0.8849	High Similarity	NPC471824
0.8846	High Similarity	NPC471215
0.8846	High Similarity	NPC262573
0.8841	High Similarity	NPC230718
0.8841	High Similarity	NPC49542
0.8841	High Similarity	NPC5253
0.8841	High Similarity	NPC84207
0.8841	High Similarity	NPC472353
0.8841	High Similarity	NPC139976
0.8841	High Similarity	NPC128337
0.8832	High Similarity	NPC184797
0.8832	High Similarity	NPC309124
0.8824	High Similarity	NPC326797
0.8824	High Similarity	NPC176051
0.8824	High Similarity	NPC262328
0.8824	High Similarity	NPC474282
0.8824	High Similarity	NPC470308
0.8824	High Similarity	NPC276490
0.8824	High Similarity	NPC470307
0.8824	High Similarity	NPC87777
0.8824	High Similarity	NPC103976
0.8824	High Similarity	NPC102904
0.8824	High Similarity	NPC107551
0.8815	High Similarity	NPC260898
0.8815	High Similarity	NPC234333
0.8815	High Similarity	NPC195022
0.8815	High Similarity	NPC47398
0.881	High Similarity	NPC295259
0.8806	High Similarity	NPC263064
0.8797	High Similarity	NPC160623
0.8794	High Similarity	NPC101376
0.8786	High Similarity	NPC469701
0.8779	High Similarity	NPC473134
0.8779	High Similarity	NPC46978
0.8777	High Similarity	NPC102044
0.8777	High Similarity	NPC85264
0.8777	High Similarity	NPC47633
0.8768	High Similarity	NPC178054
0.8768	High Similarity	NPC87725
0.8768	High Similarity	NPC263261
0.8768	High Similarity	NPC152771
0.8768	High Similarity	NPC195357
0.8768	High Similarity	NPC471389
0.8759	High Similarity	NPC471388
0.8759	High Similarity	NPC232164
0.8759	High Similarity	NPC236306
0.8759	High Similarity	NPC279573
0.8759	High Similarity	NPC473739
0.875	High Similarity	NPC472800
0.875	High Similarity	NPC126101
0.875	High Similarity	NPC160196

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 NPC92805 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	896
0.2-0.3	1664
0.3-0.4	2682
0.4-0.5	1761
0.5-0.6	983
0.6-0.7	667
0.7-0.8	146
0.8-0.85	5
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9302	High Similarity	NPD4907	Clinical (unspecified phase)
0.9147	High Similarity	NPD4908	Phase 1
0.8898	High Similarity	NPD1610	Phase 2
0.8731	High Similarity	NPD1612	Clinical (unspecified phase)
0.8731	High Similarity	NPD1613	Approved
0.873	High Similarity	NPD1548	Phase 1
0.8712	High Similarity	NPD1529	Clinical (unspecified phase)
0.8647	High Similarity	NPD4625	Phase 3
0.8636	High Similarity	NPD1530	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD3027	Phase 3
0.8333	Intermediate Similarity	NPD4749	Approved
0.8309	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD5124	Phase 1
0.8222	Intermediate Similarity	NPD2861	Phase 2
0.8176	Intermediate Similarity	NPD4380	Phase 2
0.8134	Intermediate Similarity	NPD8651	Approved
0.8112	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD7447	Phase 1
0.8058	Intermediate Similarity	NPD4060	Phase 1
0.8014	Intermediate Similarity	NPD7213	Phase 3
0.8014	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD7212	Phase 2
0.8014	Intermediate Similarity	NPD4536	Approved
0.8014	Intermediate Similarity	NPD4538	Approved
0.8013	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD422	Phase 1
0.791	Intermediate Similarity	NPD1091	Approved
0.7862	Intermediate Similarity	NPD1652	Phase 2
0.7857	Intermediate Similarity	NPD7075	Discontinued
0.7857	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD5588	Approved
0.7832	Intermediate Similarity	NPD5960	Phase 3
0.7829	Intermediate Similarity	NPD1934	Approved
0.7823	Intermediate Similarity	NPD5058	Phase 3
0.7808	Intermediate Similarity	NPD3750	Approved
0.7795	Intermediate Similarity	NPD2684	Approved
0.7786	Intermediate Similarity	NPD6671	Approved
0.7786	Intermediate Similarity	NPD7157	Approved
0.7778	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7843	Approved
0.7687	Intermediate Similarity	NPD7466	Approved
0.7677	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7768	Phase 2
0.7671	Intermediate Similarity	NPD1549	Phase 2
0.7671	Intermediate Similarity	NPD2424	Discontinued
0.7664	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2801	Approved
0.7655	Intermediate Similarity	NPD6100	Approved
0.7655	Intermediate Similarity	NPD6099	Approved
0.7647	Intermediate Similarity	NPD6072	Discontinued
0.7647	Intermediate Similarity	NPD7411	Suspended
0.7647	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6674	Discontinued
0.7597	Intermediate Similarity	NPD6801	Discontinued
0.7586	Intermediate Similarity	NPD1510	Phase 2
0.7578	Intermediate Similarity	NPD290	Approved
0.7571	Intermediate Similarity	NPD3018	Phase 2
0.7568	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1653	Approved
0.7562	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6166	Phase 2
0.7548	Intermediate Similarity	NPD7819	Suspended
0.7548	Intermediate Similarity	NPD8455	Phase 2
0.7535	Intermediate Similarity	NPD6798	Discontinued
0.7534	Intermediate Similarity	NPD2796	Approved
0.7533	Intermediate Similarity	NPD1511	Approved
0.7531	Intermediate Similarity	NPD5844	Phase 1
0.7517	Intermediate Similarity	NPD7097	Phase 1
0.75	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD6516	Phase 2
0.75	Intermediate Similarity	NPD5846	Approved
0.75	Intermediate Similarity	NPD6355	Discontinued
0.7484	Intermediate Similarity	NPD6959	Discontinued
0.7482	Intermediate Similarity	NPD6696	Suspended
0.7466	Intermediate Similarity	NPD7033	Discontinued
0.7466	Intermediate Similarity	NPD3748	Approved
0.7465	Intermediate Similarity	NPD7095	Approved
0.746	Intermediate Similarity	NPD940	Approved
0.746	Intermediate Similarity	NPD846	Approved
0.7453	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4535	Phase 3
0.7434	Intermediate Similarity	NPD1512	Approved
0.7429	Intermediate Similarity	NPD2797	Approved
0.7423	Intermediate Similarity	NPD7054	Approved
0.7421	Intermediate Similarity	NPD5494	Approved
0.7417	Intermediate Similarity	NPD6799	Approved
0.741	Intermediate Similarity	NPD2983	Phase 2
0.741	Intermediate Similarity	NPD6583	Phase 3
0.741	Intermediate Similarity	NPD6582	Phase 2
0.741	Intermediate Similarity	NPD2982	Phase 2
0.7394	Intermediate Similarity	NPD6559	Discontinued
0.7389	Intermediate Similarity	NPD3817	Phase 2
0.7386	Intermediate Similarity	NPD5403	Approved
0.7383	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4340	Discontinued
0.7378	Intermediate Similarity	NPD7472	Approved
0.7378	Intermediate Similarity	NPD7074	Phase 3
0.7376	Intermediate Similarity	NPD6584	Phase 3
0.7368	Intermediate Similarity	NPD5283	Phase 1
0.7361	Intermediate Similarity	NPD6233	Phase 2
0.7358	Intermediate Similarity	NPD6234	Discontinued
0.7357	Intermediate Similarity	NPD3225	Approved
0.7355	Intermediate Similarity	NPD6599	Discontinued
0.7349	Intermediate Similarity	NPD7549	Discontinued
0.7342	Intermediate Similarity	NPD3882	Suspended
0.7338	Intermediate Similarity	NPD2981	Phase 2
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7333	Intermediate Similarity	NPD3892	Phase 2
0.7333	Intermediate Similarity	NPD6797	Phase 2
0.7325	Intermediate Similarity	NPD5929	Approved
0.731	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1240	Approved
0.7293	Intermediate Similarity	NPD5535	Approved
0.7292	Intermediate Similarity	NPD3268	Approved
0.7289	Intermediate Similarity	NPD7251	Discontinued
0.7278	Intermediate Similarity	NPD5402	Approved
0.7267	Intermediate Similarity	NPD7199	Phase 2
0.7261	Intermediate Similarity	NPD37	Approved
0.726	Intermediate Similarity	NPD5735	Approved
0.7256	Intermediate Similarity	NPD7228	Approved
0.7256	Intermediate Similarity	NPD3818	Discontinued
0.7255	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5401	Approved
0.7254	Intermediate Similarity	NPD3691	Phase 2
0.7254	Intermediate Similarity	NPD3690	Phase 2
0.7248	Intermediate Similarity	NPD5762	Approved
0.7248	Intermediate Similarity	NPD5763	Approved
0.7246	Intermediate Similarity	NPD7808	Phase 3
0.7246	Intermediate Similarity	NPD5126	Approved
0.7246	Intermediate Similarity	NPD5125	Phase 3
0.7239	Intermediate Similarity	NPD1398	Phase 1
0.7237	Intermediate Similarity	NPD6667	Approved
0.7237	Intermediate Similarity	NPD6666	Approved
0.7233	Intermediate Similarity	NPD4967	Phase 2
0.7233	Intermediate Similarity	NPD4966	Approved
0.7233	Intermediate Similarity	NPD4965	Approved
0.7222	Intermediate Similarity	NPD6232	Discontinued
0.7222	Intermediate Similarity	NPD7229	Phase 3
0.7222	Intermediate Similarity	NPD3787	Discontinued
0.7218	Intermediate Similarity	NPD228	Approved
0.7215	Intermediate Similarity	NPD1465	Phase 2
0.7211	Intermediate Similarity	NPD1607	Approved
0.7206	Intermediate Similarity	NPD7340	Approved
0.7197	Intermediate Similarity	NPD4750	Phase 3
0.7192	Intermediate Similarity	NPD2238	Phase 2
0.719	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7041	Phase 2
0.7188	Intermediate Similarity	NPD3749	Approved
0.7181	Intermediate Similarity	NPD2935	Discontinued
0.7181	Intermediate Similarity	NPD1551	Phase 2
0.7179	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2677	Approved
0.7171	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2415	Discontinued
0.7165	Intermediate Similarity	NPD3020	Approved
0.7162	Intermediate Similarity	NPD2200	Suspended
0.7152	Intermediate Similarity	NPD4433	Discontinued
0.7152	Intermediate Similarity	NPD2800	Approved
0.7143	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4675	Approved
0.7134	Intermediate Similarity	NPD4678	Approved
0.7133	Intermediate Similarity	NPD6002	Phase 3
0.7133	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7030	Discontinued
0.7133	Intermediate Similarity	NPD7266	Discontinued
0.7133	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6005	Phase 3
0.7133	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6004	Phase 3
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3122	Phase 3
0.7122	Intermediate Similarity	NPD4626	Approved
0.7114	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1242	Phase 1
0.7105	Intermediate Similarity	NPD6331	Phase 2
0.7095	Intermediate Similarity	NPD4097	Suspended
0.7091	Intermediate Similarity	NPD7473	Discontinued
0.7086	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3620	Phase 2
0.7075	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1558	Phase 1
0.7071	Intermediate Similarity	NPD3496	Discontinued
0.707	Intermediate Similarity	NPD4005	Discontinued
0.7068	Intermediate Similarity	NPD3022	Approved
0.7068	Intermediate Similarity	NPD3021	Approved
0.7068	Intermediate Similarity	NPD5451	Approved
0.7067	Intermediate Similarity	NPD4476	Approved
0.7067	Intermediate Similarity	NPD4477	Approved

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