NPASS Compound

Structure

NPC140120 OpenBabel07101719142D 28 31 0 0 0 0 0 0 0 0999 V2000 2.5981 -2.5000 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 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 -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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 3.4641 3.0000 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 0.8660 1.5000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 1.7321 -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 1.7321 2.0000 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 -0.8660 0.5000 0.0000 C 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 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 16 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 13 2 0 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 23 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 24 2 0 0 0 0 17 25 2 0 0 0 0 17 27 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.15
Volume:	392.361
LogP:	5.55
LogD:	3.766
LogS:	-4.41
# Rotatable Bonds:	3
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.52
Synthetic Accessibility Score:	2.822
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.729
MDCK Permeability:	2.0467517970246263e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	100.0033950805664%
Volume Distribution (VD):	0.399
Pgp-substrate:	0.8780242204666138%

ADMET: Metabolism

CYP1A2-inhibitor:	0.628
CYP1A2-substrate:	0.812
CYP2C19-inhibitor:	0.797
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.788
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.228
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	3.623
Half-life (T1/2):	0.116

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.495
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.231
Rat Oral Acute Toxicity:	0.378
Maximum Recommended Daily Dose:	0.382
Skin Sensitization:	0.254
Carcinogencity:	0.401
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.182

Download Data

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

Natural Product: NPC140120

Natural Product ID:	NPC140120
*Common Name:**	5-Hydroxy-8,8-Dimethyl-4-Phenyl-6-Propanoyl-9,10-Dihydropyrano[2,3-H]Chromen-2-One
IUPAC Name:	5-hydroxy-8,8-dimethyl-4-phenyl-6-propanoyl-9,10-dihydropyrano[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	SXMWAVZXRLTFTM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H22O5/c1-4-16(24)19-20(26)18-15(13-8-6-5-7-9-13)12-17(25)27-21(18)14-10-11-23(2,3)28-22(14)19/h5-9,12,26H,4,10-11H2,1-3H3
SMILES:	CCC(=O)c1c(c2c(cc(=O)oc2c2CCC(C)(C)Oc12)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469714
PubChem CID:	11234299
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO33501	marila pluricostata	Species	Calophyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787438]

☑ 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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	4.7	ug.mL-1	PMID[531724]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	5.7	ug.mL-1	PMID[531724]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	6.8	ug.mL-1	PMID[531724]

☑ 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 NPC140120 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	382
0.1-0.2	1665
0.2-0.3	3918
0.3-0.4	9869
0.4-0.5	8699
0.5-0.6	3887
0.6-0.7	5971
0.7-0.8	4653
0.8-0.85	2109
0.85-0.9	1256
0.9-0.95	247
0.95-1	41

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC208303
0.9789	High Similarity	NPC161864
0.9787	High Similarity	NPC57470
0.972	High Similarity	NPC469932
0.9718	High Similarity	NPC180477
0.9718	High Similarity	NPC249942
0.9718	High Similarity	NPC297886
0.9716	High Similarity	NPC1886
0.9716	High Similarity	NPC196137
0.9714	High Similarity	NPC36181
0.965	High Similarity	NPC469933
0.9648	High Similarity	NPC154217
0.9648	High Similarity	NPC181388
0.9648	High Similarity	NPC470322
0.9645	High Similarity	NPC188632
0.9645	High Similarity	NPC112791
0.9645	High Similarity	NPC87609
0.9645	High Similarity	NPC94794
0.9645	High Similarity	NPC219915
0.9645	High Similarity	NPC470296
0.9645	High Similarity	NPC196459
0.9583	High Similarity	NPC104236
0.9583	High Similarity	NPC19238
0.9583	High Similarity	NPC164205
0.9577	High Similarity	NPC178627
0.9577	High Similarity	NPC469935
0.9577	High Similarity	NPC469953
0.9517	High Similarity	NPC151973
0.9507	High Similarity	NPC38219
0.9452	High Similarity	NPC312549
0.9452	High Similarity	NPC209142
0.9444	High Similarity	NPC473077
0.9444	High Similarity	NPC296998
0.9437	High Similarity	NPC78803
0.9437	High Similarity	NPC59739
0.9437	High Similarity	NPC293852
0.9437	High Similarity	NPC214236
0.9437	High Similarity	NPC144499
0.9437	High Similarity	NPC217083
0.9437	High Similarity	NPC299080
0.9437	High Similarity	NPC62840
0.9433	High Similarity	NPC221173
0.9384	High Similarity	NPC474735
0.9379	High Similarity	NPC296869
0.9375	High Similarity	NPC312973
0.9375	High Similarity	NPC88964
0.9375	High Similarity	NPC470647
0.9375	High Similarity	NPC142405
0.9375	High Similarity	NPC220418
0.9375	High Similarity	NPC246948
0.9375	High Similarity	NPC54577
0.9375	High Similarity	NPC475052
0.9375	High Similarity	NPC83357
0.9375	High Similarity	NPC67805
0.9375	High Similarity	NPC301276
0.9375	High Similarity	NPC111786
0.9375	High Similarity	NPC195621
0.9375	High Similarity	NPC20488
0.9375	High Similarity	NPC267375
0.9375	High Similarity	NPC176229
0.9375	High Similarity	NPC214774
0.9371	High Similarity	NPC106985
0.9371	High Similarity	NPC166138
0.9371	High Similarity	NPC18585
0.9366	High Similarity	NPC64908
0.9366	High Similarity	NPC156590
0.9366	High Similarity	NPC205006
0.9366	High Similarity	NPC118840
0.9366	High Similarity	NPC147688
0.9366	High Similarity	NPC470555
0.9362	High Similarity	NPC217186
0.9362	High Similarity	NPC96565
0.9362	High Similarity	NPC301217
0.9362	High Similarity	NPC220062
0.9362	High Similarity	NPC216978
0.9362	High Similarity	NPC303633
0.9362	High Similarity	NPC53181
0.9362	High Similarity	NPC473209
0.9362	High Similarity	NPC55018
0.932	High Similarity	NPC290671
0.931	High Similarity	NPC104406
0.931	High Similarity	NPC97716
0.931	High Similarity	NPC237635
0.931	High Similarity	NPC79469
0.931	High Similarity	NPC14001
0.931	High Similarity	NPC24673
0.931	High Similarity	NPC23728
0.931	High Similarity	NPC166757
0.931	High Similarity	NPC201731
0.931	High Similarity	NPC283234
0.931	High Similarity	NPC110303
0.9306	High Similarity	NPC206212
0.9306	High Similarity	NPC234629
0.9306	High Similarity	NPC311741
0.9306	High Similarity	NPC71184
0.9306	High Similarity	NPC257236
0.9306	High Similarity	NPC278175
0.9301	High Similarity	NPC226636
0.9301	High Similarity	NPC11561
0.9301	High Similarity	NPC266725
0.9296	High Similarity	NPC270883
0.9296	High Similarity	NPC241100
0.9296	High Similarity	NPC475680
0.9296	High Similarity	NPC235239
0.9296	High Similarity	NPC69769
0.9296	High Similarity	NPC159275
0.9296	High Similarity	NPC150522
0.9296	High Similarity	NPC305355
0.9296	High Similarity	NPC172986
0.9296	High Similarity	NPC261227
0.9291	High Similarity	NPC183639
0.9291	High Similarity	NPC201395
0.9291	High Similarity	NPC199458
0.9286	High Similarity	NPC470982
0.9286	High Similarity	NPC470983
0.9262	High Similarity	NPC108937
0.9262	High Similarity	NPC279218
0.9262	High Similarity	NPC469934
0.9252	High Similarity	NPC29777
0.9252	High Similarity	NPC471115
0.9252	High Similarity	NPC472633
0.9247	High Similarity	NPC160821
0.9247	High Similarity	NPC132592
0.9247	High Similarity	NPC244407
0.9247	High Similarity	NPC266572
0.9247	High Similarity	NPC6511
0.9247	High Similarity	NPC161191
0.9241	High Similarity	NPC124729
0.9241	High Similarity	NPC477955
0.9236	High Similarity	NPC9117
0.9236	High Similarity	NPC190637
0.9236	High Similarity	NPC212932
0.9236	High Similarity	NPC11700
0.9236	High Similarity	NPC478086
0.9236	High Similarity	NPC24821
0.9236	High Similarity	NPC293053
0.9236	High Similarity	NPC214166
0.9236	High Similarity	NPC316816
0.9231	High Similarity	NPC14871
0.9231	High Similarity	NPC248372
0.9231	High Similarity	NPC103362
0.9231	High Similarity	NPC110969
0.9231	High Similarity	NPC110038
0.9231	High Similarity	NPC282300
0.9225	High Similarity	NPC19476
0.9225	High Similarity	NPC18260
0.9225	High Similarity	NPC241975
0.9225	High Similarity	NPC472343
0.9225	High Similarity	NPC78913
0.922	High Similarity	NPC138047
0.922	High Similarity	NPC131782
0.922	High Similarity	NPC474624
0.92	High Similarity	NPC78554
0.92	High Similarity	NPC475797
0.92	High Similarity	NPC109967
0.92	High Similarity	NPC321372
0.92	High Similarity	NPC474738
0.92	High Similarity	NPC474609
0.92	High Similarity	NPC469936
0.92	High Similarity	NPC129053
0.9189	High Similarity	NPC78835
0.9189	High Similarity	NPC309512
0.9189	High Similarity	NPC204561
0.9189	High Similarity	NPC316960
0.9189	High Similarity	NPC317715
0.9189	High Similarity	NPC148945
0.9184	High Similarity	NPC473016
0.9184	High Similarity	NPC5173
0.9178	High Similarity	NPC282335
0.9178	High Similarity	NPC218300
0.9178	High Similarity	NPC474108
0.9178	High Similarity	NPC285748
0.9178	High Similarity	NPC177995
0.9172	High Similarity	NPC131568
0.9172	High Similarity	NPC131579
0.9172	High Similarity	NPC271288
0.9172	High Similarity	NPC216538
0.9172	High Similarity	NPC319752
0.9172	High Similarity	NPC273538
0.9172	High Similarity	NPC326500
0.9172	High Similarity	NPC209040
0.9167	High Similarity	NPC220998
0.9167	High Similarity	NPC32739
0.9167	High Similarity	NPC10937
0.9167	High Similarity	NPC328164
0.9167	High Similarity	NPC228504
0.9167	High Similarity	NPC227579
0.9167	High Similarity	NPC64915
0.9167	High Similarity	NPC324436
0.9167	High Similarity	NPC223500
0.9167	High Similarity	NPC296917
0.9167	High Similarity	NPC167624
0.9167	High Similarity	NPC66515
0.9167	High Similarity	NPC324134
0.9167	High Similarity	NPC182852
0.9167	High Similarity	NPC161506
0.9167	High Similarity	NPC200694
0.9167	High Similarity	NPC37496
0.9167	High Similarity	NPC107572
0.9167	High Similarity	NPC78

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 NPC140120 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	972
0.2-0.3	1543
0.3-0.4	2590
0.4-0.5	1975
0.5-0.6	1158
0.6-0.7	373
0.7-0.8	126
0.8-0.85	40
0.85-0.9	20
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9306	High Similarity	NPD7410	Clinical (unspecified phase)
0.9172	High Similarity	NPD4378	Clinical (unspecified phase)
0.906	High Similarity	NPD7411	Suspended
0.8889	High Similarity	NPD7075	Discontinued
0.8819	High Similarity	NPD1550	Clinical (unspecified phase)
0.8819	High Similarity	NPD1552	Clinical (unspecified phase)
0.8816	High Similarity	NPD7096	Clinical (unspecified phase)
0.8816	High Similarity	NPD7819	Suspended
0.8767	High Similarity	NPD3750	Approved
0.8766	High Similarity	NPD3749	Approved
0.8759	High Similarity	NPD1549	Phase 2
0.8758	High Similarity	NPD8443	Clinical (unspecified phase)
0.8742	High Similarity	NPD4380	Phase 2
0.8693	High Similarity	NPD2393	Clinical (unspecified phase)
0.8681	High Similarity	NPD1510	Phase 2
0.8671	High Similarity	NPD7852	Clinical (unspecified phase)
0.8627	High Similarity	NPD6801	Discontinued
0.8621	High Similarity	NPD2796	Approved
0.8581	High Similarity	NPD7768	Phase 2
0.8571	High Similarity	NPD1243	Approved
0.8531	High Similarity	NPD1240	Approved
0.8526	High Similarity	NPD4381	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1511	Approved
0.8467	Intermediate Similarity	NPD6799	Approved
0.8446	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD3748	Approved
0.8414	Intermediate Similarity	NPD1607	Approved
0.8395	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2313	Discontinued
0.8387	Intermediate Similarity	NPD1934	Approved
0.8378	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD2801	Approved
0.8322	Intermediate Similarity	NPD2800	Approved
0.8301	Intermediate Similarity	NPD920	Approved
0.8299	Intermediate Similarity	NPD2799	Discontinued
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8278	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6599	Discontinued
0.825	Intermediate Similarity	NPD6959	Discontinued
0.8243	Intermediate Similarity	NPD1551	Phase 2
0.8243	Intermediate Similarity	NPD2935	Discontinued
0.8219	Intermediate Similarity	NPD5124	Phase 1
0.8219	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5403	Approved
0.817	Intermediate Similarity	NPD2532	Approved
0.817	Intermediate Similarity	NPD2534	Approved
0.817	Intermediate Similarity	NPD2533	Approved
0.817	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD1203	Approved
0.8138	Intermediate Similarity	NPD3268	Approved
0.8113	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6166	Phase 2
0.8098	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6232	Discontinued
0.8077	Intermediate Similarity	NPD3226	Approved
0.8072	Intermediate Similarity	NPD5953	Discontinued
0.8067	Intermediate Similarity	NPD2346	Discontinued
0.8061	Intermediate Similarity	NPD5844	Phase 1
0.8061	Intermediate Similarity	NPD7054	Approved
0.8054	Intermediate Similarity	NPD4308	Phase 3
0.8052	Intermediate Similarity	NPD5401	Approved
0.8049	Intermediate Similarity	NPD7473	Discontinued
0.8042	Intermediate Similarity	NPD2797	Approved
0.8041	Intermediate Similarity	NPD6651	Approved
0.8026	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD422	Phase 1
0.8012	Intermediate Similarity	NPD7472	Approved
0.8012	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD3882	Suspended
0.7976	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD3225	Approved
0.7964	Intermediate Similarity	NPD6797	Phase 2
0.7963	Intermediate Similarity	NPD5494	Approved
0.7958	Intermediate Similarity	NPD9717	Approved
0.7952	Intermediate Similarity	NPD7286	Phase 2
0.7937	Intermediate Similarity	NPD5402	Approved
0.7933	Intermediate Similarity	NPD7033	Discontinued
0.7917	Intermediate Similarity	NPD6559	Discontinued
0.7917	Intermediate Similarity	NPD7251	Discontinued
0.7901	Intermediate Similarity	NPD919	Approved
0.7892	Intermediate Similarity	NPD3818	Discontinued
0.7891	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6099	Approved
0.7881	Intermediate Similarity	NPD6100	Approved
0.7877	Intermediate Similarity	NPD6832	Phase 2
0.7875	Intermediate Similarity	NPD1465	Phase 2
0.787	Intermediate Similarity	NPD7808	Phase 3
0.787	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2344	Approved
0.7803	Intermediate Similarity	NPD4287	Approved
0.7799	Intermediate Similarity	NPD6585	Discontinued
0.7793	Intermediate Similarity	NPD3266	Approved
0.7793	Intermediate Similarity	NPD3267	Approved
0.7792	Intermediate Similarity	NPD4628	Phase 3
0.7785	Intermediate Similarity	NPD4307	Phase 2
0.7755	Intermediate Similarity	NPD4908	Phase 1
0.774	Intermediate Similarity	NPD2798	Approved
0.7716	Intermediate Similarity	NPD4288	Approved
0.7697	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5710	Approved
0.7651	Intermediate Similarity	NPD1296	Phase 2
0.7651	Intermediate Similarity	NPD5711	Approved
0.7647	Intermediate Similarity	NPD5405	Approved
0.7647	Intermediate Similarity	NPD5404	Approved
0.7647	Intermediate Similarity	NPD5406	Approved
0.7647	Intermediate Similarity	NPD5408	Approved
0.7647	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7390	Discontinued
0.764	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5890	Approved
0.764	Intermediate Similarity	NPD5889	Approved
0.7628	Intermediate Similarity	NPD2309	Approved
0.7627	Intermediate Similarity	NPD4360	Phase 2
0.7627	Intermediate Similarity	NPD4363	Phase 3
0.7595	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1608	Approved
0.7584	Intermediate Similarity	NPD4625	Phase 3
0.755	Intermediate Similarity	NPD943	Approved
0.7533	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD411	Approved
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7458	Discontinued
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1548	Phase 1
0.7452	Intermediate Similarity	NPD7003	Approved
0.7438	Intermediate Similarity	NPD5049	Phase 3
0.7432	Intermediate Similarity	NPD1164	Approved
0.7389	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4361	Phase 2
0.7381	Intermediate Similarity	NPD1247	Approved
0.7379	Intermediate Similarity	NPD17	Approved
0.7372	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7584	Approved
0.7361	Intermediate Similarity	NPD9545	Approved
0.7343	Intermediate Similarity	NPD9493	Approved
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.7314	Intermediate Similarity	NPD8312	Approved
0.7314	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7297	Intermediate Similarity	NPD4749	Approved
0.7296	Intermediate Similarity	NPD2354	Approved
0.7294	Intermediate Similarity	NPD3926	Phase 2
0.7285	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2654	Approved
0.7278	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7251	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7585	Approved
0.723	Intermediate Similarity	NPD1481	Phase 2
0.7229	Intermediate Similarity	NPD8455	Phase 2
0.7222	Intermediate Similarity	NPD6273	Approved
0.7219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4476	Approved
0.7197	Intermediate Similarity	NPD4477	Approved
0.7184	Intermediate Similarity	NPD1729	Discontinued
0.7183	Intermediate Similarity	NPD5535	Approved
0.7181	Intermediate Similarity	NPD7583	Approved
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7168	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3751	Discontinued
0.7168	Intermediate Similarity	NPD7177	Discontinued
0.7162	Intermediate Similarity	NPD1535	Discovery
0.7162	Intermediate Similarity	NPD1201	Approved
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD6002	Phase 3
0.7152	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD2353	Approved
0.7152	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6004	Phase 3
0.7152	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3787	Discontinued
0.7135	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1894	Discontinued
0.712	Intermediate Similarity	NPD7783	Phase 2
0.712	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3972	Approved
0.7112	Intermediate Similarity	NPD7435	Discontinued
0.7101	Intermediate Similarity	NPD6971	Discontinued
0.7097	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4060	Phase 1
0.7097	Intermediate Similarity	NPD1613	Approved
0.7095	Intermediate Similarity	NPD8150	Discontinued
0.7095	Intermediate Similarity	NPD8434	Phase 2

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