NPASS Compound

Structure

NPC244407 OpenBabel07101719512D 32 35 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 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 -0.0000 -2.0000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 -1.7321 0.0000 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 -1.7321 -2.0000 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 -1.5000 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 -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 0.8660 -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 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 30 1 0 0 0 0 6 11 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 26 1 0 0 0 0 15 23 1 0 0 0 0 16 30 1 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 28 2 0 0 0 0 22 23 2 0 0 0 0 22 29 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.17
Volume:	450.403
LogP:	6.659
LogD:	4.117
LogS:	-2.751
# Rotatable Bonds:	4
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.522
Synthetic Accessibility Score:	3.108
Fsp3:	0.269
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.725
MDCK Permeability:	1.4116773854766507e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	92.20421600341797%
Volume Distribution (VD):	0.569
Pgp-substrate:	9.168882369995117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.457
CYP1A2-substrate:	0.323
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.915
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.32
CYP2D6-substrate:	0.375
CYP3A4-inhibitor:	0.375
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	1.662
Half-life (T1/2):	0.096

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.201
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.287
Skin Sensitization:	0.537
Carcinogencity:	0.48
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.541

Download Data

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

Natural Product: NPC244407

Natural Product ID:	NPC244407
*Common Name:**	Khonklonginol F
IUPAC Name:	5,7-dihydroxy-8-(4-methoxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
Synonyms:	khonklonginol F
Standard InCHIKey:	GHEBWBVTFSMHIJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H26O6/c1-14(2)6-11-18-24-17(12-13-26(3,4)32-24)20(27)19-21(28)22(29)23(31-25(18)19)15-7-9-16(30-5)10-8-15/h6-10,12-13,27,29H,11H2,1-5H3
SMILES:	COc1ccc(cc1)c1oc2c(CC=C(C)C)c3OC(C)(C)C=Cc3c(c2c(=O)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562377
PubChem CID:	44178659
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO12525	Eriosema chinense	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[19555123]
NPO12525	Eriosema chinense	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	3
MIC	1

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.7	ug.mL-1	PMID[525875]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	2.4	ug.mL-1	PMID[525875]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	7.0	ug.mL-1	PMID[525875]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	100.0	ug.mL-1	PMID[525875]

☑ 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 NPC244407 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	433
0.1-0.2	1717
0.2-0.3	4332
0.3-0.4	10579
0.4-0.5	7486
0.5-0.6	3790
0.6-0.7	5433
0.7-0.8	4319
0.8-0.85	2262
0.85-0.9	1720
0.9-0.95	578
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC166757
0.9929	High Similarity	NPC14001
0.9859	High Similarity	NPC296869
0.9858	High Similarity	NPC124729
0.9858	High Similarity	NPC220418
0.9787	High Similarity	NPC216538
0.9787	High Similarity	NPC273538
0.9718	High Similarity	NPC5820
0.9718	High Similarity	NPC178343
0.9718	High Similarity	NPC306488
0.9716	High Similarity	NPC293053
0.9716	High Similarity	NPC190637
0.9716	High Similarity	NPC24821
0.9716	High Similarity	NPC212932
0.9716	High Similarity	NPC9117
0.9653	High Similarity	NPC5173
0.965	High Similarity	NPC24673
0.965	High Similarity	NPC201731
0.965	High Similarity	NPC104406
0.965	High Similarity	NPC97716
0.965	High Similarity	NPC237635
0.965	High Similarity	NPC79469
0.9648	High Similarity	NPC326500
0.9645	High Similarity	NPC293852
0.9645	High Similarity	NPC200694
0.9645	High Similarity	NPC299080
0.9645	High Similarity	NPC62840
0.9645	High Similarity	NPC78803
0.9645	High Similarity	NPC59739
0.9645	High Similarity	NPC473042
0.9645	High Similarity	NPC214236
0.9645	High Similarity	NPC217083
0.9589	High Similarity	NPC45934
0.9586	High Similarity	NPC61258
0.9583	High Similarity	NPC6511
0.9583	High Similarity	NPC266572
0.9577	High Similarity	NPC158874
0.9577	High Similarity	NPC219915
0.9524	High Similarity	NPC311579
0.9524	High Similarity	NPC236756
0.9517	High Similarity	NPC470461
0.9514	High Similarity	NPC296998
0.9514	High Similarity	NPC473077
0.951	High Similarity	NPC319752
0.951	High Similarity	NPC311741
0.951	High Similarity	NPC234629
0.9507	High Similarity	NPC226636
0.9507	High Similarity	NPC11561
0.9504	High Similarity	NPC241100
0.9504	High Similarity	NPC159275
0.9504	High Similarity	NPC150522
0.9459	High Similarity	NPC48579
0.9459	High Similarity	NPC304207
0.9459	High Similarity	NPC217706
0.9459	High Similarity	NPC476169
0.9459	High Similarity	NPC207809
0.9459	High Similarity	NPC259710
0.9456	High Similarity	NPC142527
0.9452	High Similarity	NPC471115
0.9452	High Similarity	NPC29777
0.9452	High Similarity	NPC188403
0.9452	High Similarity	NPC472633
0.9448	High Similarity	NPC161191
0.9448	High Similarity	NPC321623
0.9448	High Similarity	NPC470460
0.9448	High Similarity	NPC189087
0.9444	High Similarity	NPC474161
0.9444	High Similarity	NPC214774
0.9444	High Similarity	NPC142405
0.9444	High Similarity	NPC20488
0.9444	High Similarity	NPC267375
0.9444	High Similarity	NPC301276
0.9444	High Similarity	NPC475052
0.9444	High Similarity	NPC83357
0.9444	High Similarity	NPC67805
0.9444	High Similarity	NPC476088
0.9444	High Similarity	NPC470647
0.9444	High Similarity	NPC176229
0.9444	High Similarity	NPC88964
0.9444	High Similarity	NPC111786
0.9444	High Similarity	NPC312973
0.9444	High Similarity	NPC54577
0.9444	High Similarity	NPC329678
0.9444	High Similarity	NPC195621
0.9444	High Similarity	NPC246948
0.9444	High Similarity	NPC470458
0.9441	High Similarity	NPC38219
0.9441	High Similarity	NPC166138
0.9441	High Similarity	NPC106985
0.9441	High Similarity	NPC18585
0.9437	High Similarity	NPC262094
0.9437	High Similarity	NPC90582
0.9437	High Similarity	NPC156590
0.9437	High Similarity	NPC110969
0.9437	High Similarity	NPC103362
0.9437	High Similarity	NPC205006
0.9437	High Similarity	NPC118840
0.9437	High Similarity	NPC147688
0.9437	High Similarity	NPC64908
0.9437	High Similarity	NPC282300
0.9433	High Similarity	NPC18260
0.9433	High Similarity	NPC152042
0.9433	High Similarity	NPC143799
0.9433	High Similarity	NPC96565
0.9433	High Similarity	NPC241838
0.9433	High Similarity	NPC220062
0.9433	High Similarity	NPC78913
0.9433	High Similarity	NPC53181
0.9433	High Similarity	NPC55018
0.9433	High Similarity	NPC216978
0.9433	High Similarity	NPC301217
0.9433	High Similarity	NPC303633
0.9433	High Similarity	NPC217186
0.9392	High Similarity	NPC248793
0.9392	High Similarity	NPC180301
0.9384	High Similarity	NPC269420
0.9379	High Similarity	NPC23728
0.9379	High Similarity	NPC110303
0.9379	High Similarity	NPC283234
0.9375	High Similarity	NPC224714
0.9371	High Similarity	NPC144499
0.9366	High Similarity	NPC475680
0.9366	High Similarity	NPC270883
0.9366	High Similarity	NPC269652
0.9366	High Similarity	NPC235239
0.9366	High Similarity	NPC172986
0.9366	High Similarity	NPC305355
0.9366	High Similarity	NPC230285
0.9366	High Similarity	NPC184536
0.9366	High Similarity	NPC281207
0.9366	High Similarity	NPC261227
0.9366	High Similarity	NPC103342
0.9366	High Similarity	NPC103904
0.9366	High Similarity	NPC146679
0.9366	High Similarity	NPC59951
0.9362	High Similarity	NPC276905
0.9362	High Similarity	NPC17848
0.9362	High Similarity	NPC131130
0.9362	High Similarity	NPC201395
0.9333	High Similarity	NPC237418
0.9333	High Similarity	NPC281137
0.9333	High Similarity	NPC282390
0.9329	High Similarity	NPC111341
0.9329	High Similarity	NPC304745
0.9329	High Similarity	NPC470681
0.9329	High Similarity	NPC275575
0.9324	High Similarity	NPC210597
0.932	High Similarity	NPC471984
0.9315	High Similarity	NPC160821
0.9315	High Similarity	NPC161864
0.9315	High Similarity	NPC168085
0.9315	High Similarity	NPC132592
0.9315	High Similarity	NPC208303
0.931	High Similarity	NPC472629
0.931	High Similarity	NPC477955
0.931	High Similarity	NPC57470
0.9306	High Similarity	NPC316816
0.9306	High Similarity	NPC11700
0.9306	High Similarity	NPC478086
0.9306	High Similarity	NPC214166
0.9301	High Similarity	NPC136840
0.9301	High Similarity	NPC469404
0.9301	High Similarity	NPC14871
0.9296	High Similarity	NPC23257
0.9262	High Similarity	NPC290830
0.9262	High Similarity	NPC88983
0.9262	High Similarity	NPC7989
0.9262	High Similarity	NPC100134
0.9262	High Similarity	NPC472583
0.9262	High Similarity	NPC193200
0.9262	High Similarity	NPC71061
0.9262	High Similarity	NPC303485
0.9262	High Similarity	NPC170492
0.9262	High Similarity	NPC194593
0.9262	High Similarity	NPC72425
0.9262	High Similarity	NPC223701
0.9262	High Similarity	NPC268193
0.9262	High Similarity	NPC209760
0.9257	High Similarity	NPC278476
0.9257	High Similarity	NPC81474
0.9257	High Similarity	NPC319910
0.9257	High Similarity	NPC471675
0.9257	High Similarity	NPC262038
0.9257	High Similarity	NPC262039
0.9257	High Similarity	NPC254412
0.9252	High Similarity	NPC317492
0.9252	High Similarity	NPC473016
0.9252	High Similarity	NPC474052
0.9252	High Similarity	NPC469932
0.9247	High Similarity	NPC308200
0.9247	High Similarity	NPC472918
0.9247	High Similarity	NPC249942
0.9247	High Similarity	NPC180477
0.9247	High Similarity	NPC297886
0.9247	High Similarity	NPC140120
0.9241	High Similarity	NPC470890
0.9241	High Similarity	NPC328623
0.9241	High Similarity	NPC271288
0.9241	High Similarity	NPC131568
0.9241	High Similarity	NPC278175

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 NPC244407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	950
0.2-0.3	1692
0.3-0.4	2691
0.4-0.5	1856
0.5-0.6	1035
0.6-0.7	357
0.7-0.8	126
0.8-0.85	42
0.85-0.9	16
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9787	High Similarity	NPD4378	Clinical (unspecified phase)
0.9241	High Similarity	NPD7410	Clinical (unspecified phase)
0.8933	High Similarity	NPD4380	Phase 2
0.8889	High Similarity	NPD1550	Clinical (unspecified phase)
0.8889	High Similarity	NPD1552	Clinical (unspecified phase)
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8881	High Similarity	NPD1510	Phase 2
0.8831	High Similarity	NPD7075	Discontinued
0.8828	High Similarity	NPD1549	Phase 2
0.8824	High Similarity	NPD8443	Clinical (unspecified phase)
0.8819	High Similarity	NPD2796	Approved
0.8792	High Similarity	NPD1512	Approved
0.8758	High Similarity	NPD7096	Clinical (unspecified phase)
0.875	High Similarity	NPD7411	Suspended
0.8732	High Similarity	NPD1240	Approved
0.8693	High Similarity	NPD6801	Discontinued
0.8688	High Similarity	NPD7804	Clinical (unspecified phase)
0.8658	High Similarity	NPD1511	Approved
0.8636	High Similarity	NPD2801	Approved
0.8611	High Similarity	NPD1607	Approved
0.859	High Similarity	NPD4381	Clinical (unspecified phase)
0.8571	High Similarity	NPD1934	Approved
0.8533	High Similarity	NPD6799	Approved
0.8516	High Similarity	NPD7819	Suspended
0.85	High Similarity	NPD6166	Phase 2
0.85	High Similarity	NPD6168	Clinical (unspecified phase)
0.85	High Similarity	NPD6167	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3817	Phase 2
0.8456	Intermediate Similarity	NPD3750	Approved
0.8428	Intermediate Similarity	NPD6959	Discontinued
0.8408	Intermediate Similarity	NPD7768	Phase 2
0.8408	Intermediate Similarity	NPD3882	Suspended
0.8389	Intermediate Similarity	NPD2800	Approved
0.8385	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD5403	Approved
0.8323	Intermediate Similarity	NPD6599	Discontinued
0.8267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6797	Phase 2
0.8239	Intermediate Similarity	NPD3749	Approved
0.8235	Intermediate Similarity	NPD5401	Approved
0.8228	Intermediate Similarity	NPD5402	Approved
0.82	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD7251	Discontinued
0.8188	Intermediate Similarity	NPD2935	Discontinued
0.8146	Intermediate Similarity	NPD1243	Approved
0.8144	Intermediate Similarity	NPD7808	Phase 3
0.8137	Intermediate Similarity	NPD5494	Approved
0.8129	Intermediate Similarity	NPD920	Approved
0.8121	Intermediate Similarity	NPD3748	Approved
0.8121	Intermediate Similarity	NPD7054	Approved
0.8108	Intermediate Similarity	NPD6651	Approved
0.8082	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD2313	Discontinued
0.8072	Intermediate Similarity	NPD7074	Phase 3
0.8072	Intermediate Similarity	NPD7472	Approved
0.8067	Intermediate Similarity	NPD1551	Phase 2
0.8061	Intermediate Similarity	NPD3818	Discontinued
0.8037	Intermediate Similarity	NPD6232	Discontinued
0.8036	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD2799	Discontinued
0.8	Intermediate Similarity	NPD2532	Approved
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5953	Discontinued
0.7904	Intermediate Similarity	NPD7286	Phase 2
0.7895	Intermediate Similarity	NPD2344	Approved
0.787	Intermediate Similarity	NPD6559	Discontinued
0.7866	Intermediate Similarity	NPD1247	Approved
0.7857	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD919	Approved
0.7829	Intermediate Similarity	NPD6099	Approved
0.7829	Intermediate Similarity	NPD6100	Approved
0.7823	Intermediate Similarity	NPD4908	Phase 1
0.7821	Intermediate Similarity	NPD7390	Discontinued
0.78	Intermediate Similarity	NPD5124	Phase 1
0.78	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3226	Approved
0.7798	Intermediate Similarity	NPD5844	Phase 1
0.7784	Intermediate Similarity	NPD4360	Phase 2
0.7784	Intermediate Similarity	NPD4363	Phase 3
0.7763	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7033	Discontinued
0.774	Intermediate Similarity	NPD1203	Approved
0.7718	Intermediate Similarity	NPD3268	Approved
0.7706	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2309	Approved
0.7687	Intermediate Similarity	NPD2798	Approved
0.7676	Intermediate Similarity	NPD1548	Phase 1
0.7671	Intermediate Similarity	NPD3225	Approved
0.7665	Intermediate Similarity	NPD3926	Phase 2
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7647	Intermediate Similarity	NPD4308	Phase 3
0.7628	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD2797	Approved
0.7616	Intermediate Similarity	NPD943	Approved
0.7586	Intermediate Similarity	NPD422	Phase 1
0.7586	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1610	Phase 2
0.7584	Intermediate Similarity	NPD6832	Phase 2
0.7571	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4361	Phase 2
0.7534	Intermediate Similarity	NPD9717	Approved
0.7533	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4288	Approved
0.7452	Intermediate Similarity	NPD2654	Approved
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7419	Intermediate Similarity	NPD7584	Approved
0.7412	Intermediate Similarity	NPD2403	Approved
0.7412	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3787	Discontinued
0.7396	Intermediate Similarity	NPD5710	Approved
0.7396	Intermediate Similarity	NPD5711	Approved
0.7386	Intermediate Similarity	NPD4307	Phase 2
0.7383	Intermediate Similarity	NPD3267	Approved
0.7383	Intermediate Similarity	NPD3266	Approved
0.7368	Intermediate Similarity	NPD6798	Discontinued
0.7362	Intermediate Similarity	NPD7458	Discontinued
0.7351	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD1729	Discontinued
0.7338	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1471	Phase 3
0.7317	Intermediate Similarity	NPD6585	Discontinued
0.7308	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3972	Approved
0.7297	Intermediate Similarity	NPD1608	Approved
0.7296	Intermediate Similarity	NPD7003	Approved
0.7294	Intermediate Similarity	NPD7229	Phase 3
0.7285	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5049	Phase 3
0.7283	Intermediate Similarity	NPD6777	Approved
0.7283	Intermediate Similarity	NPD6779	Approved
0.7283	Intermediate Similarity	NPD6780	Approved
0.7283	Intermediate Similarity	NPD6778	Approved
0.7283	Intermediate Similarity	NPD6776	Approved
0.7283	Intermediate Similarity	NPD6781	Approved
0.7283	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5890	Approved
0.7273	Intermediate Similarity	NPD5889	Approved
0.7273	Intermediate Similarity	NPD1613	Approved
0.7263	Intermediate Similarity	NPD4287	Approved
0.7261	Intermediate Similarity	NPD5405	Approved
0.7261	Intermediate Similarity	NPD5406	Approved
0.7261	Intermediate Similarity	NPD5404	Approved
0.7261	Intermediate Similarity	NPD5408	Approved
0.7256	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3764	Approved
0.7255	Intermediate Similarity	NPD1296	Phase 2
0.725	Intermediate Similarity	NPD2354	Approved
0.7248	Intermediate Similarity	NPD4749	Approved
0.7247	Intermediate Similarity	NPD8434	Phase 2
0.723	Intermediate Similarity	NPD1201	Approved
0.7229	Intermediate Similarity	NPD6844	Discontinued
0.7226	Intermediate Similarity	NPD230	Phase 1
0.7226	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD1933	Approved
0.7226	Intermediate Similarity	NPD447	Suspended
0.7215	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6233	Phase 2
0.7192	Intermediate Similarity	NPD9545	Approved
0.7189	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8312	Approved
0.7175	Intermediate Similarity	NPD8313	Approved
0.7172	Intermediate Similarity	NPD9493	Approved
0.717	Intermediate Similarity	NPD2424	Discontinued
0.7166	Intermediate Similarity	NPD7435	Discontinued
0.7166	Intermediate Similarity	NPD7698	Approved
0.7166	Intermediate Similarity	NPD7696	Phase 3
0.7166	Intermediate Similarity	NPD7697	Approved
0.7161	Intermediate Similarity	NPD4060	Phase 1
0.716	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1164	Approved
0.7152	Intermediate Similarity	NPD1470	Approved
0.7151	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8150	Discontinued
0.7143	Intermediate Similarity	NPD2296	Approved
0.7143	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7871	Phase 2
0.7128	Intermediate Similarity	NPD7870	Phase 2
0.7126	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7447	Phase 1
0.7107	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2353	Approved
0.7105	Intermediate Similarity	NPD1019	Discontinued
0.7095	Intermediate Similarity	NPD8055	Clinical (unspecified phase)

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