NPASS Compound

Structure

CID161864 OpenBabel06191715532D 30 33 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 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 2.5981 -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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 25 1 0 0 0 0 4 25 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 15 2 0 0 0 0 9 15 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 15 17 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 18 26 2 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.16
Volume:	424.317
LogP:	5.988
LogD:	4.574
LogS:	-4.152
# Rotatable Bonds:	4
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	2.939
Fsp3:	0.28
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:	-4.685
MDCK Permeability:	1.72006621141918e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.106

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	100.09577178955078%
Volume Distribution (VD):	0.465
Pgp-substrate:	0.9556109309196472%

ADMET: Metabolism

CYP1A2-inhibitor:	0.408
CYP1A2-substrate:	0.313
CYP2C19-inhibitor:	0.914
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.913
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.269
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.337
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	3.381
Half-life (T1/2):	0.124

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.846
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.388
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.534
Skin Sensitization:	0.411
Carcinogencity:	0.869
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.576

Download Data

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

Natural Product: NPC161864

Natural Product ID:	NPC161864
*Common Name:**	Mammeigin
IUPAC Name:	5-hydroxy-8,8-dimethyl-6-(3-methylbutanoyl)-4-phenylpyrano[2,3-h]chromen-2-one
Synonyms:	Mammeigin
Standard InCHIKey:	VSDJRZADBKXDHP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O5/c1-14(2)12-18(26)21-22(28)20-17(15-8-6-5-7-9-15)13-19(27)29-23(20)16-10-11-25(3,4)30-24(16)21/h5-11,13-14,28H,12H2,1-4H3
SMILES:	CC(C)CC(=O)c1c(c2c(cc(=O)oc2c2C=CC(C)(C)Oc12)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL195013
PubChem CID:	5319255
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]
NPO4557	Kayea assamica	Species	Calophyllaceae	Eukaryota	flower	Myanmar	n.a.	PMID[18640837]
NPO4557	Kayea assamica	Species	Calophyllaceae	Eukaryota	flowers	Myanmar	n.a.	PMID[18725180]
NPO24185	Diospyros lotus	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24185	Diospyros lotus	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24185	Diospyros lotus	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4557	Kayea assamica	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24185	Diospyros lotus	Species	Ebenaceae	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
GI50	3
IC50	1
Others	6

Activity Type	# Activity
Cell Line	7
Individual Protein	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	123800.0	nM	PMID[523771]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	2.0	%	PMID[523771]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	3.0	%	PMID[523771]
NPT460	Cell Line	MT2	Homo sapiens	Cell death	=	4.7	%	PMID[523771]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[523772]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[523772]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[523772]
NPT461	Cell Line	PANC-1	Homo sapiens	Cytotoxicity	=	32.0	uM	PMID[523773]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	5.9	%	PMID[523771]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	15.7	%	PMID[523771]

☑ 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 NPC161864 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	1605
0.2-0.3	3799
0.3-0.4	9357
0.4-0.5	9349
0.5-0.6	3893
0.6-0.7	5962
0.7-0.8	4866
0.8-0.85	2020
0.85-0.9	1212
0.9-0.95	199
0.95-1	53

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC208303
0.993	High Similarity	NPC469932
0.9929	High Similarity	NPC249942
0.9929	High Similarity	NPC297886
0.9859	High Similarity	NPC469933
0.9858	High Similarity	NPC57470
0.9789	High Similarity	NPC140120
0.9789	High Similarity	NPC180477
0.9787	High Similarity	NPC1886
0.9787	High Similarity	NPC196137
0.9718	High Similarity	NPC181388
0.9718	High Similarity	NPC470322
0.9718	High Similarity	NPC154217
0.9716	High Similarity	NPC87609
0.9716	High Similarity	NPC470296
0.9716	High Similarity	NPC112791
0.9716	High Similarity	NPC196459
0.9716	High Similarity	NPC188632
0.9716	High Similarity	NPC94794
0.9648	High Similarity	NPC469935
0.9648	High Similarity	NPC178627
0.9645	High Similarity	NPC36181
0.9586	High Similarity	NPC151973
0.9574	High Similarity	NPC470555
0.9517	High Similarity	NPC164205
0.9517	High Similarity	NPC104236
0.9517	High Similarity	NPC19238
0.951	High Similarity	NPC469953
0.9507	High Similarity	NPC293852
0.9507	High Similarity	NPC59739
0.9507	High Similarity	NPC299080
0.9507	High Similarity	NPC217083
0.9507	High Similarity	NPC62840
0.9507	High Similarity	NPC78803
0.9507	High Similarity	NPC214236
0.9504	High Similarity	NPC221173
0.9452	High Similarity	NPC474735
0.9444	High Similarity	NPC220418
0.9441	High Similarity	NPC219915
0.9433	High Similarity	NPC473209
0.9433	High Similarity	NPC472343
0.9388	High Similarity	NPC209142
0.9388	High Similarity	NPC312549
0.9388	High Similarity	NPC290671
0.9379	High Similarity	NPC237635
0.9379	High Similarity	NPC14001
0.9379	High Similarity	NPC166757
0.9379	High Similarity	NPC79469
0.9379	High Similarity	NPC24673
0.9379	High Similarity	NPC97716
0.9379	High Similarity	NPC104406
0.9379	High Similarity	NPC201731
0.9362	High Similarity	NPC199458
0.9362	High Similarity	NPC183639
0.9329	High Similarity	NPC469934
0.9315	High Similarity	NPC244407
0.9315	High Similarity	NPC266572
0.9315	High Similarity	NPC6511
0.931	High Similarity	NPC474161
0.931	High Similarity	NPC476088
0.9306	High Similarity	NPC38219
0.9301	High Similarity	NPC282300
0.9301	High Similarity	NPC118840
0.9301	High Similarity	NPC156590
0.9301	High Similarity	NPC205006
0.9301	High Similarity	NPC64908
0.9301	High Similarity	NPC147688
0.9296	High Similarity	NPC301217
0.9296	High Similarity	NPC303633
0.9296	High Similarity	NPC53181
0.9296	High Similarity	NPC96565
0.9296	High Similarity	NPC216978
0.9296	High Similarity	NPC55018
0.9296	High Similarity	NPC19476
0.9296	High Similarity	NPC217186
0.9296	High Similarity	NPC241975
0.9296	High Similarity	NPC220062
0.9291	High Similarity	NPC138047
0.9291	High Similarity	NPC131782
0.9291	High Similarity	NPC474624
0.9267	High Similarity	NPC474609
0.9267	High Similarity	NPC78554
0.9267	High Similarity	NPC321372
0.9267	High Similarity	NPC469936
0.9267	High Similarity	NPC475797
0.9267	High Similarity	NPC109967
0.9267	High Similarity	NPC129053
0.9267	High Similarity	NPC474738
0.9252	High Similarity	NPC5173
0.9247	High Similarity	NPC296998
0.9247	High Similarity	NPC218300
0.9247	High Similarity	NPC285748
0.9247	High Similarity	NPC473077
0.9247	High Similarity	NPC282335
0.9241	High Similarity	NPC326500
0.9241	High Similarity	NPC234629
0.9241	High Similarity	NPC278175
0.9241	High Similarity	NPC319752
0.9241	High Similarity	NPC311741
0.9241	High Similarity	NPC257236
0.9236	High Similarity	NPC226636
0.9236	High Similarity	NPC144499
0.9236	High Similarity	NPC11561
0.9231	High Similarity	NPC305355
0.9231	High Similarity	NPC270883
0.9231	High Similarity	NPC150522
0.9231	High Similarity	NPC235239
0.9231	High Similarity	NPC475680
0.9231	High Similarity	NPC241100
0.9231	High Similarity	NPC159275
0.9231	High Similarity	NPC172986
0.9231	High Similarity	NPC261227
0.9225	High Similarity	NPC470083
0.9225	High Similarity	NPC219584
0.9225	High Similarity	NPC470669
0.9225	High Similarity	NPC470668
0.9225	High Similarity	NPC201395
0.92	High Similarity	NPC279218
0.92	High Similarity	NPC108937
0.9189	High Similarity	NPC29777
0.9189	High Similarity	NPC471115
0.9189	High Similarity	NPC188403
0.9189	High Similarity	NPC471984
0.9184	High Similarity	NPC321623
0.9184	High Similarity	NPC189087
0.9184	High Similarity	NPC161191
0.9184	High Similarity	NPC296869
0.9178	High Similarity	NPC88964
0.9178	High Similarity	NPC54577
0.9178	High Similarity	NPC246948
0.9178	High Similarity	NPC142405
0.9178	High Similarity	NPC67805
0.9178	High Similarity	NPC470647
0.9178	High Similarity	NPC176229
0.9178	High Similarity	NPC111786
0.9178	High Similarity	NPC195621
0.9178	High Similarity	NPC477955
0.9178	High Similarity	NPC329678
0.9178	High Similarity	NPC124729
0.9178	High Similarity	NPC301276
0.9178	High Similarity	NPC214774
0.9178	High Similarity	NPC475052
0.9178	High Similarity	NPC20488
0.9178	High Similarity	NPC312973
0.9178	High Similarity	NPC83357
0.9178	High Similarity	NPC267375
0.9172	High Similarity	NPC24821
0.9172	High Similarity	NPC11700
0.9172	High Similarity	NPC9117
0.9172	High Similarity	NPC190637
0.9172	High Similarity	NPC293053
0.9172	High Similarity	NPC212932
0.9172	High Similarity	NPC166138
0.9172	High Similarity	NPC18585
0.9172	High Similarity	NPC106985
0.9167	High Similarity	NPC103362
0.9167	High Similarity	NPC110969
0.9167	High Similarity	NPC14871
0.9161	High Similarity	NPC240305
0.9161	High Similarity	NPC470986
0.9161	High Similarity	NPC18260
0.9161	High Similarity	NPC78913
0.9161	High Similarity	NPC170812
0.9128	High Similarity	NPC78835
0.9128	High Similarity	NPC317715
0.9128	High Similarity	NPC316960
0.9128	High Similarity	NPC309512
0.9128	High Similarity	NPC148945
0.9128	High Similarity	NPC204561
0.9122	High Similarity	NPC473016
0.9116	High Similarity	NPC23728
0.9116	High Similarity	NPC474108
0.9116	High Similarity	NPC177995
0.9116	High Similarity	NPC110303
0.9116	High Similarity	NPC283234
0.911	High Similarity	NPC131568
0.911	High Similarity	NPC131579
0.911	High Similarity	NPC216538
0.911	High Similarity	NPC271288
0.911	High Similarity	NPC273538
0.911	High Similarity	NPC206212
0.911	High Similarity	NPC71184
0.9103	High Similarity	NPC473042
0.9103	High Similarity	NPC200694
0.9103	High Similarity	NPC266725
0.9103	High Similarity	NPC470556
0.9097	High Similarity	NPC69769
0.9091	High Similarity	NPC248995
0.9091	High Similarity	NPC17848
0.9091	High Similarity	NPC470671
0.9091	High Similarity	NPC474487
0.9091	High Similarity	NPC254168
0.9091	High Similarity	NPC131130
0.9091	High Similarity	NPC71903
0.9091	High Similarity	NPC272844
0.9091	High Similarity	NPC470672
0.9091	High Similarity	NPC474504
0.9085	High Similarity	NPC470983
0.9085	High Similarity	NPC470982
0.9085	High Similarity	NPC13408

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 NPC161864 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	962
0.2-0.3	1540
0.3-0.4	2576
0.4-0.5	1990
0.5-0.6	1163
0.6-0.7	376
0.7-0.8	129
0.8-0.85	39
0.85-0.9	16
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9241	High Similarity	NPD7410	Clinical (unspecified phase)
0.911	High Similarity	NPD4378	Clinical (unspecified phase)
0.8874	High Similarity	NPD7411	Suspended
0.871	High Similarity	NPD7075	Discontinued
0.8707	High Similarity	NPD3750	Approved
0.8701	High Similarity	NPD8443	Clinical (unspecified phase)
0.8636	High Similarity	NPD7096	Clinical (unspecified phase)
0.8636	High Similarity	NPD7819	Suspended
0.863	High Similarity	NPD1550	Clinical (unspecified phase)
0.863	High Similarity	NPD1552	Clinical (unspecified phase)
0.8621	High Similarity	NPD1510	Phase 2
0.859	High Similarity	NPD3749	Approved
0.8571	High Similarity	NPD1549	Phase 2
0.8571	High Similarity	NPD6801	Discontinued
0.8562	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD2796	Approved
0.8526	High Similarity	NPD7768	Phase 2
0.8516	High Similarity	NPD2393	Clinical (unspecified phase)
0.8514	High Similarity	NPD1243	Approved
0.85	High Similarity	NPD7852	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1240	Approved
0.8446	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD6799	Approved
0.8411	Intermediate Similarity	NPD1511	Approved
0.8389	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD2799	Discontinued
0.8367	Intermediate Similarity	NPD3748	Approved
0.8356	Intermediate Similarity	NPD1607	Approved
0.8354	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2313	Discontinued
0.8301	Intermediate Similarity	NPD1512	Approved
0.8288	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD5124	Phase 1
0.828	Intermediate Similarity	NPD2801	Approved
0.8267	Intermediate Similarity	NPD2800	Approved
0.8247	Intermediate Similarity	NPD920	Approved
0.8247	Intermediate Similarity	NPD5403	Approved
0.8232	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD3817	Phase 2
0.8224	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1934	Approved
0.8207	Intermediate Similarity	NPD3268	Approved
0.8207	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6599	Discontinued
0.8188	Intermediate Similarity	NPD2935	Discontinued
0.8188	Intermediate Similarity	NPD1551	Phase 2
0.8117	Intermediate Similarity	NPD5401	Approved
0.8117	Intermediate Similarity	NPD2532	Approved
0.8117	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2534	Approved
0.8117	Intermediate Similarity	NPD2533	Approved
0.8112	Intermediate Similarity	NPD1203	Approved
0.8112	Intermediate Similarity	NPD2797	Approved
0.811	Intermediate Similarity	NPD7473	Discontinued
0.8108	Intermediate Similarity	NPD6651	Approved
0.8086	Intermediate Similarity	NPD6959	Discontinued
0.8042	Intermediate Similarity	NPD3225	Approved
0.8037	Intermediate Similarity	NPD6232	Discontinued
0.8025	Intermediate Similarity	NPD3226	Approved
0.8024	Intermediate Similarity	NPD5953	Discontinued
0.8	Intermediate Similarity	NPD4308	Phase 3
0.8	Intermediate Similarity	NPD5402	Approved
0.7974	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD422	Phase 1
0.795	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3882	Suspended
0.7939	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6166	Phase 2
0.7939	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD5494	Approved
0.7904	Intermediate Similarity	NPD5844	Phase 1
0.7904	Intermediate Similarity	NPD7054	Approved
0.7904	Intermediate Similarity	NPD7286	Phase 2
0.7902	Intermediate Similarity	NPD9717	Approved
0.7895	Intermediate Similarity	NPD2346	Discontinued
0.7881	Intermediate Similarity	NPD7033	Discontinued
0.7862	Intermediate Similarity	NPD3267	Approved
0.7862	Intermediate Similarity	NPD3266	Approved
0.7857	Intermediate Similarity	NPD7074	Phase 3
0.7857	Intermediate Similarity	NPD7472	Approved
0.7853	Intermediate Similarity	NPD919	Approved
0.7844	Intermediate Similarity	NPD3818	Discontinued
0.7838	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6099	Approved
0.7829	Intermediate Similarity	NPD6100	Approved
0.7824	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6832	Phase 2
0.7811	Intermediate Similarity	NPD6797	Phase 2
0.7808	Intermediate Similarity	NPD2798	Approved
0.7778	Intermediate Similarity	NPD2344	Approved
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7765	Intermediate Similarity	NPD7251	Discontinued
0.7742	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD4307	Phase 2
0.7719	Intermediate Similarity	NPD7808	Phase 3
0.7716	Intermediate Similarity	NPD1465	Phase 2
0.7703	Intermediate Similarity	NPD4908	Phase 1
0.7669	Intermediate Similarity	NPD4288	Approved
0.7657	Intermediate Similarity	NPD4287	Approved
0.7655	Intermediate Similarity	NPD1608	Approved
0.7647	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6585	Discontinued
0.76	Intermediate Similarity	NPD1296	Phase 2
0.7598	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5408	Approved
0.7597	Intermediate Similarity	NPD5405	Approved
0.7597	Intermediate Similarity	NPD5404	Approved
0.7597	Intermediate Similarity	NPD5406	Approved
0.7595	Intermediate Similarity	NPD7390	Discontinued
0.7593	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4360	Phase 2
0.7584	Intermediate Similarity	NPD4363	Phase 3
0.758	Intermediate Similarity	NPD2309	Approved
0.7578	Intermediate Similarity	NPD7458	Discontinued
0.7547	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD5890	Approved
0.7485	Intermediate Similarity	NPD5889	Approved
0.7483	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7469	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1610	Phase 2
0.7453	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD447	Suspended
0.7451	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD17	Approved
0.7444	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4361	Phase 2
0.7436	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7417	Intermediate Similarity	NPD4625	Phase 3
0.7396	Intermediate Similarity	NPD7229	Phase 3
0.7391	Intermediate Similarity	NPD5049	Phase 3
0.7383	Intermediate Similarity	NPD1164	Approved
0.7374	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1933	Approved
0.7337	Intermediate Similarity	NPD1247	Approved
0.731	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD9545	Approved
0.7292	Intermediate Similarity	NPD9493	Approved
0.7284	Intermediate Similarity	NPD6273	Approved
0.7273	Intermediate Similarity	NPD8312	Approved
0.7273	Intermediate Similarity	NPD8313	Approved
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6798	Discontinued
0.7251	Intermediate Similarity	NPD3926	Phase 2
0.725	Intermediate Similarity	NPD2354	Approved
0.7248	Intermediate Similarity	NPD4749	Approved
0.7237	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7199	Phase 2
0.7234	Intermediate Similarity	NPD7584	Approved
0.7233	Intermediate Similarity	NPD2654	Approved
0.7226	Intermediate Similarity	NPD230	Phase 1
0.7226	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD1019	Discontinued
0.7215	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6002	Phase 3
0.7215	Intermediate Similarity	NPD6004	Phase 3
0.7215	Intermediate Similarity	NPD6005	Phase 3
0.7181	Intermediate Similarity	NPD1481	Phase 2
0.7167	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD4476	Approved
0.7152	Intermediate Similarity	NPD4477	Approved
0.7151	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD1729	Discontinued
0.7133	Intermediate Similarity	NPD5535	Approved
0.7126	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7177	Discontinued
0.7125	Intermediate Similarity	NPD1652	Phase 2
0.7124	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1201	Approved
0.7114	Intermediate Similarity	NPD1535	Discovery
0.7107	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2353	Approved
0.7105	Intermediate Similarity	NPD7585	Approved
0.7086	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD8455	Phase 2
0.7075	Intermediate Similarity	NPD1894	Discontinued
0.7067	Intermediate Similarity	NPD3972	Approved
0.7059	Intermediate Similarity	NPD6971	Discontinued
0.7059	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8150	Discontinued
0.7053	Intermediate Similarity	NPD7583	Approved
0.7041	Intermediate Similarity	NPD2296	Approved
0.7039	Intermediate Similarity	NPD1470	Approved
0.7037	Intermediate Similarity	NPD3887	Approved
0.7032	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3751	Discontinued
0.7024	Intermediate Similarity	NPD37	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