NPASS Compound

Structure

CID109240 OpenBabel06191715462D 23 25 0 0 0 0 0 0 0 0999 V2000 -1.8588 -2.3311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6759 0.8474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4977 2.8191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4310 2.5702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2501 1.2104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9288 1.2104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8903 2.5702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3214 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6799 -0.6799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3214 0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1776 2.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6799 1.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6414 1.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4990 2.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8191 2.8191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6414 -0.6799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1064 2.3880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4278 2.3880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0680 3.7479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2735 -1.5683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4726 -0.0924 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 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 6 16 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 17 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.11
Volume:	313.841
LogP:	2.305
LogD:	2.718
LogS:	-2.964
# Rotatable Bonds:	2
TPSA:	88.38
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.582
Synthetic Accessibility Score:	2.98
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.611
MDCK Permeability:	1.8993081539520063e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.339

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	91.66693878173828%
Volume Distribution (VD):	0.718
Pgp-substrate:	4.535842418670654%

ADMET: Metabolism

CYP1A2-inhibitor:	0.894
CYP1A2-substrate:	0.676
CYP2C19-inhibitor:	0.38
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.45
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.795
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.743
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	14.383
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.261
AMES Toxicity:	0.841
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.168
Skin Sensitization:	0.945
Carcinogencity:	0.164
Eye Corrosion:	0.003
Eye Irritation:	0.299
Respiratory Toxicity:	0.216

Download Data

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

Natural Product: NPC109240

Natural Product ID:	NPC109240
*Common Name:**	Protosappaninadimethylacetal
IUPAC Name:	n.a.
Synonyms:	Protosappaninadimethylacetal
Standard InCHIKey:	SVSDBMDJWUPWHK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O6/c1-21-17(22-2)8-10-5-14(19)15(20)7-13(10)12-4-3-11(18)6-16(12)23-9-17/h3-7,18-20H,8-9H2,1-2H3
SMILES:	COC1(Cc2cc(c(cc2-c2ccc(cc2OC1)O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2207726
PubChem CID:	11347693
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0000128] Alkyl aryl ethers

*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
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2554	Biancaea sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2554	Biancaea sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2554	Biancaea sappan	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[486319]

☑ 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 NPC109240 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	413
0.1-0.2	1761
0.2-0.3	4857
0.3-0.4	12748
0.4-0.5	5053
0.5-0.6	4032
0.6-0.7	6612
0.7-0.8	5564
0.8-0.85	1027
0.85-0.9	515
0.9-0.95	114
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9191	High Similarity	NPC234952
0.9173	High Similarity	NPC126836
0.9111	High Similarity	NPC32778
0.9111	High Similarity	NPC475840
0.9058	High Similarity	NPC32630
0.9058	High Similarity	NPC471183
0.9051	High Similarity	NPC265433
0.9051	High Similarity	NPC162659
0.9051	High Similarity	NPC270456
0.9051	High Similarity	NPC133025
0.9051	High Similarity	NPC248727
0.9044	High Similarity	NPC469659
0.9044	High Similarity	NPC317380
0.9044	High Similarity	NPC188378
0.9044	High Similarity	NPC276026
0.9044	High Similarity	NPC56764
0.9044	High Similarity	NPC555
0.9044	High Similarity	NPC7515
0.9044	High Similarity	NPC289258
0.9044	High Similarity	NPC206737
0.9023	High Similarity	NPC154866
0.9014	High Similarity	NPC99515
0.9014	High Similarity	NPC190714
0.9007	High Similarity	NPC121661
0.9007	High Similarity	NPC73467
0.9	High Similarity	NPC133934
0.9	High Similarity	NPC41782
0.9	High Similarity	NPC184641
0.9	High Similarity	NPC184684
0.8986	High Similarity	NPC86605
0.8986	High Similarity	NPC35550
0.8986	High Similarity	NPC301765
0.8986	High Similarity	NPC156948
0.8986	High Similarity	NPC46277
0.8986	High Similarity	NPC3072
0.8978	High Similarity	NPC112939
0.8978	High Similarity	NPC474206
0.8978	High Similarity	NPC151224
0.8978	High Similarity	NPC214853
0.8978	High Similarity	NPC69029
0.8978	High Similarity	NPC180602
0.8978	High Similarity	NPC158142
0.8978	High Similarity	NPC94750
0.8978	High Similarity	NPC294884
0.8978	High Similarity	NPC121812
0.8978	High Similarity	NPC200557
0.8978	High Similarity	NPC108198
0.8978	High Similarity	NPC240279
0.8978	High Similarity	NPC112246
0.8978	High Similarity	NPC10314
0.8978	High Similarity	NPC55239
0.8978	High Similarity	NPC470356
0.8971	High Similarity	NPC229442
0.8971	High Similarity	NPC11060
0.8971	High Similarity	NPC168059
0.8963	High Similarity	NPC15543
0.8947	High Similarity	NPC124452
0.8947	High Similarity	NPC324112
0.8947	High Similarity	NPC236791
0.8947	High Similarity	NPC282000
0.8947	High Similarity	NPC159968
0.8947	High Similarity	NPC74817
0.8947	High Similarity	NPC210355
0.8947	High Similarity	NPC293054
0.8947	High Similarity	NPC82679
0.8947	High Similarity	NPC169474
0.8947	High Similarity	NPC266555
0.8947	High Similarity	NPC246620
0.8944	High Similarity	NPC166506
0.8944	High Similarity	NPC110763
0.8944	High Similarity	NPC189239
0.8944	High Similarity	NPC197352
0.8936	High Similarity	NPC81638
0.8936	High Similarity	NPC473044
0.8936	High Similarity	NPC469630
0.8929	High Similarity	NPC265075
0.8921	High Similarity	NPC127218
0.8921	High Similarity	NPC260741
0.8921	High Similarity	NPC319647
0.8921	High Similarity	NPC70682
0.8921	High Similarity	NPC55947
0.8921	High Similarity	NPC25966
0.8921	High Similarity	NPC245207
0.8913	High Similarity	NPC472336
0.8913	High Similarity	NPC202846
0.8913	High Similarity	NPC143139
0.8913	High Similarity	NPC227503
0.8913	High Similarity	NPC474639
0.8913	High Similarity	NPC306441
0.8913	High Similarity	NPC16435
0.8913	High Similarity	NPC230734
0.8913	High Similarity	NPC472334
0.8905	High Similarity	NPC125649
0.8904	High Similarity	NPC21902
0.8897	High Similarity	NPC127624
0.8897	High Similarity	NPC86655
0.8897	High Similarity	NPC202762
0.8889	High Similarity	NPC91291
0.8889	High Similarity	NPC472338
0.8889	High Similarity	NPC175976
0.8881	High Similarity	NPC154971
0.8881	High Similarity	NPC252286
0.8873	High Similarity	NPC473045
0.8873	High Similarity	NPC473108
0.8873	High Similarity	NPC50250
0.8873	High Similarity	NPC25292
0.8873	High Similarity	NPC87883
0.8872	High Similarity	NPC214406
0.8872	High Similarity	NPC44748
0.8872	High Similarity	NPC18924
0.8872	High Similarity	NPC78974
0.8872	High Similarity	NPC223136
0.8872	High Similarity	NPC28730
0.8872	High Similarity	NPC223953
0.8872	High Similarity	NPC103823
0.8857	High Similarity	NPC309124
0.8857	High Similarity	NPC160283
0.8857	High Similarity	NPC184797
0.8857	High Similarity	NPC254759
0.8849	High Similarity	NPC103976
0.8849	High Similarity	NPC276490
0.8849	High Similarity	NPC94994
0.8849	High Similarity	NPC326797
0.8849	High Similarity	NPC56329
0.8849	High Similarity	NPC474282
0.8849	High Similarity	NPC211549
0.8849	High Similarity	NPC242715
0.8849	High Similarity	NPC102904
0.8849	High Similarity	NPC107551
0.8849	High Similarity	NPC176051
0.8841	High Similarity	NPC260898
0.8841	High Similarity	NPC47398
0.8841	High Similarity	NPC164787
0.8841	High Similarity	NPC241241
0.8841	High Similarity	NPC61946
0.8841	High Similarity	NPC234333
0.8841	High Similarity	NPC313081
0.8841	High Similarity	NPC472337
0.8841	High Similarity	NPC473413
0.8841	High Similarity	NPC256262
0.8832	High Similarity	NPC471391
0.8832	High Similarity	NPC471390
0.8824	High Similarity	NPC469907
0.8824	High Similarity	NPC472597
0.8815	High Similarity	NPC212015
0.8811	High Similarity	NPC475096
0.8811	High Similarity	NPC307466
0.8806	High Similarity	NPC470699
0.8806	High Similarity	NPC127587
0.8803	High Similarity	NPC472451
0.8803	High Similarity	NPC474104
0.8797	High Similarity	NPC117214
0.8797	High Similarity	NPC208950
0.8797	High Similarity	NPC60885
0.8797	High Similarity	NPC233410
0.8797	High Similarity	NPC57490
0.8797	High Similarity	NPC475169
0.8797	High Similarity	NPC17943
0.8797	High Similarity	NPC193544
0.8797	High Similarity	NPC105925
0.8797	High Similarity	NPC299584
0.8797	High Similarity	NPC203133
0.8797	High Similarity	NPC221077
0.8797	High Similarity	NPC234400
0.8797	High Similarity	NPC251855
0.8797	High Similarity	NPC298757
0.8797	High Similarity	NPC265483
0.8797	High Similarity	NPC82483
0.8797	High Similarity	NPC472093
0.8797	High Similarity	NPC116907
0.8794	High Similarity	NPC263261
0.8794	High Similarity	NPC87725
0.8794	High Similarity	NPC471389
0.8794	High Similarity	NPC35216
0.8788	High Similarity	NPC84086
0.8788	High Similarity	NPC136319
0.8786	High Similarity	NPC236306
0.8786	High Similarity	NPC79622
0.8786	High Similarity	NPC212942
0.8786	High Similarity	NPC473739
0.8786	High Similarity	NPC22517
0.8786	High Similarity	NPC220344
0.8786	High Similarity	NPC132804
0.8786	High Similarity	NPC292882
0.8786	High Similarity	NPC243996
0.8786	High Similarity	NPC275061
0.8786	High Similarity	NPC184613
0.8786	High Similarity	NPC232164
0.8786	High Similarity	NPC29868
0.8777	High Similarity	NPC173660
0.8777	High Similarity	NPC269091
0.8777	High Similarity	NPC30632
0.8777	High Similarity	NPC302701
0.8777	High Similarity	NPC470802
0.8768	High Similarity	NPC160697
0.8768	High Similarity	NPC106215
0.8768	High Similarity	NPC478085
0.8768	High Similarity	NPC209199
0.8759	High Similarity	NPC7903
0.8759	High Similarity	NPC6451

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 NPC109240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	954
0.2-0.3	1884
0.3-0.4	2704
0.4-0.5	1594
0.5-0.6	852
0.6-0.7	652
0.7-0.8	137
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8759	High Similarity	NPD1612	Clinical (unspecified phase)
0.8759	High Similarity	NPD1613	Approved
0.8741	High Similarity	NPD1529	Clinical (unspecified phase)
0.8676	High Similarity	NPD3027	Phase 3
0.8667	High Similarity	NPD1530	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4908	Phase 1
0.8273	Intermediate Similarity	NPD4625	Phase 3
0.8222	Intermediate Similarity	NPD1610	Phase 2
0.8214	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD4060	Phase 1
0.806	Intermediate Similarity	NPD1548	Phase 1
0.7975	Intermediate Similarity	NPD7199	Phase 2
0.7962	Intermediate Similarity	NPD6234	Discontinued
0.7875	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD3018	Phase 2
0.7871	Intermediate Similarity	NPD1934	Approved
0.7843	Intermediate Similarity	NPD1653	Approved
0.7842	Intermediate Similarity	NPD4749	Approved
0.7826	Intermediate Similarity	NPD3705	Approved
0.7821	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6674	Discontinued
0.7756	Intermediate Similarity	NPD37	Approved
0.7746	Intermediate Similarity	NPD2861	Phase 2
0.7722	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3882	Suspended
0.7722	Intermediate Similarity	NPD4967	Phase 2
0.7722	Intermediate Similarity	NPD4966	Approved
0.7722	Intermediate Similarity	NPD4965	Approved
0.7714	Intermediate Similarity	NPD2982	Phase 2
0.7714	Intermediate Similarity	NPD2983	Phase 2
0.7708	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2801	Approved
0.7698	Intermediate Similarity	NPD1091	Approved
0.7687	Intermediate Similarity	NPD5283	Phase 1
0.7669	Intermediate Similarity	NPD228	Approved
0.7667	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2981	Phase 2
0.7636	Intermediate Similarity	NPD7074	Phase 3
0.7622	Intermediate Similarity	NPD3818	Discontinued
0.7622	Intermediate Similarity	NPD7228	Approved
0.7597	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1465	Phase 2
0.7589	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1511	Approved
0.7576	Intermediate Similarity	NPD7054	Approved
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7571	Intermediate Similarity	NPD422	Phase 1
0.7552	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7472	Approved
0.7519	Intermediate Similarity	NPD3021	Approved
0.7519	Intermediate Similarity	NPD3022	Approved
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD3892	Phase 2
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD6232	Discontinued
0.7484	Intermediate Similarity	NPD1512	Approved
0.7483	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3620	Phase 2
0.7483	Intermediate Similarity	NPD1558	Phase 1
0.7465	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD7157	Approved
0.7444	Intermediate Similarity	NPD2684	Approved
0.744	Intermediate Similarity	NPD7251	Discontinued
0.7438	Intermediate Similarity	NPD3817	Phase 2
0.7417	Intermediate Similarity	NPD5763	Approved
0.7417	Intermediate Similarity	NPD5762	Approved
0.7417	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7266	Discontinued
0.7413	Intermediate Similarity	NPD8651	Approved
0.7378	Intermediate Similarity	NPD3787	Discontinued
0.7375	Intermediate Similarity	NPD7819	Suspended
0.7353	Intermediate Similarity	NPD7843	Approved
0.7351	Intermediate Similarity	NPD6100	Approved
0.7351	Intermediate Similarity	NPD6099	Approved
0.7349	Intermediate Similarity	NPD7473	Discontinued
0.7346	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4005	Discontinued
0.7338	Intermediate Similarity	NPD2677	Approved
0.7338	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6671	Approved
0.7315	Intermediate Similarity	NPD6355	Discontinued
0.731	Intermediate Similarity	NPD8053	Approved
0.731	Intermediate Similarity	NPD8054	Approved
0.7308	Intermediate Similarity	NPD7447	Phase 1
0.7303	Intermediate Similarity	NPD3540	Phase 1
0.7296	Intermediate Similarity	NPD4678	Approved
0.7296	Intermediate Similarity	NPD4675	Approved
0.7294	Intermediate Similarity	NPD7808	Phase 3
0.7294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7095	Approved
0.7261	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7212	Phase 2
0.7244	Intermediate Similarity	NPD7213	Phase 3
0.7244	Intermediate Similarity	NPD6799	Approved
0.7244	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4055	Discovery
0.7239	Intermediate Similarity	NPD290	Approved
0.7239	Intermediate Similarity	NPD7075	Discontinued
0.7237	Intermediate Similarity	NPD3539	Phase 1
0.7235	Intermediate Similarity	NPD6559	Discontinued
0.7234	Intermediate Similarity	NPD1357	Approved
0.723	Intermediate Similarity	NPD6798	Discontinued
0.7209	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1652	Phase 2
0.7202	Intermediate Similarity	NPD3751	Discontinued
0.72	Intermediate Similarity	NPD5124	Phase 1
0.72	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5735	Approved
0.7197	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD709	Approved
0.7192	Intermediate Similarity	NPD6584	Phase 3
0.719	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1375	Discontinued
0.7188	Intermediate Similarity	NPD6599	Discontinued
0.7183	Intermediate Similarity	NPD4626	Approved
0.7179	Intermediate Similarity	NPD5058	Phase 3
0.7178	Intermediate Similarity	NPD7768	Phase 2
0.7176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6696	Suspended
0.7171	Intermediate Similarity	NPD4108	Discontinued
0.7171	Intermediate Similarity	NPD3748	Approved
0.7169	Intermediate Similarity	NPD7229	Phase 3
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4628	Phase 3
0.716	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7135	Intermediate Similarity	NPD7240	Approved
0.7132	Intermediate Similarity	NPD4750	Phase 3
0.7121	Intermediate Similarity	NPD940	Approved
0.7121	Intermediate Similarity	NPD846	Approved
0.7117	Intermediate Similarity	NPD2560	Approved
0.7117	Intermediate Similarity	NPD2563	Approved
0.7113	Intermediate Similarity	NPD5691	Approved
0.7108	Intermediate Similarity	NPD6959	Discontinued
0.7107	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4536	Approved
0.7105	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4538	Approved
0.7093	Intermediate Similarity	NPD7549	Discontinued
0.7089	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD230	Phase 1
0.7083	Intermediate Similarity	NPD1611	Approved
0.7081	Intermediate Similarity	NPD4380	Phase 2
0.707	Intermediate Similarity	NPD7124	Phase 2
0.7063	Intermediate Similarity	NPD5846	Approved
0.7063	Intermediate Similarity	NPD6516	Phase 2
0.7059	Intermediate Similarity	NPD2154	Approved
0.7059	Intermediate Similarity	NPD2155	Approved
0.7059	Intermediate Similarity	NPD2156	Approved
0.7059	Intermediate Similarity	NPD1510	Phase 2
0.7059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD8455	Phase 2
0.7051	Intermediate Similarity	NPD4110	Phase 3
0.7051	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5494	Approved
0.7048	Intermediate Similarity	NPD4666	Phase 3
0.7045	Intermediate Similarity	NPD1242	Phase 1
0.7037	Intermediate Similarity	NPD968	Approved
0.7037	Intermediate Similarity	NPD6072	Discontinued
0.7034	Intermediate Similarity	NPD1608	Approved
0.7025	Intermediate Similarity	NPD4357	Discontinued
0.702	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1240	Approved
0.702	Intermediate Similarity	NPD4140	Approved
0.702	Intermediate Similarity	NPD2238	Phase 2
0.7019	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3496	Discontinued
0.7013	Intermediate Similarity	NPD2796	Approved
0.7013	Intermediate Similarity	NPD1551	Phase 2
0.7012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2797	Approved
0.7	Intermediate Similarity	NPD5111	Phase 2
0.7	Intermediate Similarity	NPD5110	Phase 2
0.7	Intermediate Similarity	NPD5109	Approved
0.6994	Remote Similarity	NPD6801	Discontinued
0.6993	Remote Similarity	NPD3445	Approved
0.6993	Remote Similarity	NPD3444	Approved
0.6993	Remote Similarity	NPD3443	Approved
0.6989	Remote Similarity	NPD6841	Approved
0.6989	Remote Similarity	NPD6842	Approved
0.6989	Remote Similarity	NPD6843	Phase 3
0.6988	Remote Similarity	NPD5709	Phase 3
0.6987	Remote Similarity	NPD3060	Approved
0.6986	Remote Similarity	NPD6583	Phase 3
0.6986	Remote Similarity	NPD6582	Phase 2
0.6986	Remote Similarity	NPD5327	Phase 3
0.6982	Remote Similarity	NPD27	Approved
0.6982	Remote Similarity	NPD2489	Approved
0.6981	Remote Similarity	NPD4123	Phase 3
0.6981	Remote Similarity	NPD2532	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