NPASS Compound

Structure

CID297886 OpenBabel06191716102D 29 32 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 3.4641 -1.0000 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 3.4641 3.0000 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 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 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 1.7321 -1.0000 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 2.5981 4.5000 0.0000 O 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 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 24 1 0 0 0 0 4 24 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 14 2 0 0 0 0 9 14 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 24 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 17 25 2 0 0 0 0 17 28 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 26 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.15
Volume:	407.021
LogP:	5.355
LogD:	4.057
LogS:	-4.39
# 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:	0.492
Synthetic Accessibility Score:	2.945
Fsp3:	0.25
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:	-4.713
MDCK Permeability:	1.8528180589783005e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.329

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	100.68476104736328%
Volume Distribution (VD):	0.38
Pgp-substrate:	1.041441559791565%

ADMET: Metabolism

CYP1A2-inhibitor:	0.733
CYP1A2-substrate:	0.621
CYP2C19-inhibitor:	0.836
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.696
CYP2D6-inhibitor:	0.461
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.433
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	1.535
Half-life (T1/2):	0.105

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.826
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.292
Rat Oral Acute Toxicity:	0.903
Maximum Recommended Daily Dose:	0.211
Skin Sensitization:	0.334
Carcinogencity:	0.87
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.705

Download Data

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

Natural Product: NPC297886

Natural Product ID:	NPC297886
*Common Name:**	Mesuagin
IUPAC Name:	5-hydroxy-8,8-dimethyl-6-(2-methylpropanoyl)-4-phenylpyrano[2,3-h]chromen-2-one
Synonyms:	Mesuagin
Standard InCHIKey:	SVCPILBFQWTZFW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H22O5/c1-13(2)20(26)19-21(27)18-16(14-8-6-5-7-9-14)12-17(25)28-22(18)15-10-11-24(3,4)29-23(15)19/h5-13,27H,1-4H3
SMILES:	CC(C)C(=O)c1c(c2c(cc(=O)oc2c2C=CC(C)(C)Oc12)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL198546
PubChem CID:	5319380
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
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)83306-8]
NPO33501	marila pluricostata	Species	Calophyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787438]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO681	Mesua ferrea	Species	Calophyllaceae	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	2
Others	5

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	=	32100.0	nM	PMID[468099]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	0.0	%	PMID[468099]
NPT460	Cell Line	MT2	Homo sapiens	Cell death	=	4.5	%	PMID[468099]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	10.8	ug.mL-1	PMID[468100]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[468101]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[468101]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[468101]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	10.8	%	PMID[468099]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	20.2	%	PMID[468099]

☑ 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 NPC297886 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	NPC249942
0.9929	High Similarity	NPC161864
0.9929	High Similarity	NPC469933
0.9929	High Similarity	NPC208303
0.9929	High Similarity	NPC57470
0.9859	High Similarity	NPC469932
0.9858	High Similarity	NPC180477
0.9786	High Similarity	NPC112791
0.9786	High Similarity	NPC94794
0.9786	High Similarity	NPC188632
0.9786	High Similarity	NPC87609
0.9786	High Similarity	NPC470296
0.9786	High Similarity	NPC196459
0.9718	High Similarity	NPC140120
0.9716	High Similarity	NPC1886
0.9716	High Similarity	NPC178627
0.9716	High Similarity	NPC469935
0.9716	High Similarity	NPC196137
0.9714	High Similarity	NPC36181
0.9653	High Similarity	NPC151973
0.9648	High Similarity	NPC154217
0.9648	High Similarity	NPC181388
0.9648	High Similarity	NPC470322
0.9643	High Similarity	NPC470555
0.9583	High Similarity	NPC104236
0.9583	High Similarity	NPC19238
0.9583	High Similarity	NPC164205
0.9577	High Similarity	NPC469953
0.9574	High Similarity	NPC78803
0.9574	High Similarity	NPC214236
0.9574	High Similarity	NPC217083
0.9574	High Similarity	NPC62840
0.9574	High Similarity	NPC59739
0.9574	High Similarity	NPC299080
0.9574	High Similarity	NPC293852
0.9571	High Similarity	NPC221173
0.95	High Similarity	NPC472343
0.9384	High Similarity	NPC474735
0.9375	High Similarity	NPC220418
0.9375	High Similarity	NPC474161
0.9375	High Similarity	NPC476088
0.9371	High Similarity	NPC38219
0.9371	High Similarity	NPC219915
0.9366	High Similarity	NPC64908
0.9366	High Similarity	NPC282300
0.9366	High Similarity	NPC147688
0.9366	High Similarity	NPC156590
0.9366	High Similarity	NPC205006
0.9366	High Similarity	NPC118840
0.9362	High Similarity	NPC217186
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	NPC96565
0.9362	High Similarity	NPC473209
0.9362	High Similarity	NPC55018
0.9357	High Similarity	NPC474624
0.9357	High Similarity	NPC131782
0.9357	High Similarity	NPC138047
0.932	High Similarity	NPC209142
0.932	High Similarity	NPC290671
0.932	High Similarity	NPC312549
0.931	High Similarity	NPC104406
0.931	High Similarity	NPC97716
0.931	High Similarity	NPC79469
0.931	High Similarity	NPC14001
0.931	High Similarity	NPC24673
0.931	High Similarity	NPC218300
0.931	High Similarity	NPC237635
0.931	High Similarity	NPC166757
0.931	High Similarity	NPC282335
0.931	High Similarity	NPC201731
0.9306	High Similarity	NPC319752
0.9306	High Similarity	NPC257236
0.9306	High Similarity	NPC278175
0.9301	High Similarity	NPC226636
0.9301	High Similarity	NPC11561
0.9296	High Similarity	NPC475680
0.9296	High Similarity	NPC235239
0.9296	High Similarity	NPC159275
0.9296	High Similarity	NPC241100
0.9296	High Similarity	NPC150522
0.9296	High Similarity	NPC305355
0.9296	High Similarity	NPC172986
0.9296	High Similarity	NPC261227
0.9296	High Similarity	NPC270883
0.9291	High Similarity	NPC183639
0.9291	High Similarity	NPC201395
0.9291	High Similarity	NPC470668
0.9291	High Similarity	NPC470083
0.9291	High Similarity	NPC199458
0.9291	High Similarity	NPC219584
0.9291	High Similarity	NPC470669
0.9262	High Similarity	NPC469934
0.9252	High Similarity	NPC471984
0.9247	High Similarity	NPC244407
0.9247	High Similarity	NPC266572
0.9247	High Similarity	NPC6511
0.9247	High Similarity	NPC321623
0.9247	High Similarity	NPC161191
0.9247	High Similarity	NPC189087
0.9241	High Similarity	NPC329678
0.9241	High Similarity	NPC195621
0.9241	High Similarity	NPC214774
0.9241	High Similarity	NPC20488
0.9241	High Similarity	NPC67805
0.9241	High Similarity	NPC111786
0.9241	High Similarity	NPC267375
0.9241	High Similarity	NPC312973
0.9241	High Similarity	NPC301276
0.9241	High Similarity	NPC142405
0.9241	High Similarity	NPC83357
0.9241	High Similarity	NPC176229
0.9241	High Similarity	NPC246948
0.9241	High Similarity	NPC54577
0.9241	High Similarity	NPC88964
0.9241	High Similarity	NPC470647
0.9241	High Similarity	NPC475052
0.9231	High Similarity	NPC14871
0.9231	High Similarity	NPC103362
0.9231	High Similarity	NPC110969
0.9225	High Similarity	NPC240305
0.9225	High Similarity	NPC19476
0.9225	High Similarity	NPC18260
0.9225	High Similarity	NPC241975
0.9225	High Similarity	NPC170812
0.9225	High Similarity	NPC78913
0.92	High Similarity	NPC78554
0.92	High Similarity	NPC475797
0.92	High Similarity	NPC321372
0.92	High Similarity	NPC129053
0.92	High Similarity	NPC474738
0.92	High Similarity	NPC109967
0.92	High Similarity	NPC474609
0.92	High Similarity	NPC469936
0.9184	High Similarity	NPC5173
0.9178	High Similarity	NPC110303
0.9178	High Similarity	NPC296998
0.9178	High Similarity	NPC23728
0.9178	High Similarity	NPC285748
0.9178	High Similarity	NPC473077
0.9178	High Similarity	NPC283234
0.9172	High Similarity	NPC234629
0.9172	High Similarity	NPC131568
0.9172	High Similarity	NPC131579
0.9172	High Similarity	NPC311741
0.9172	High Similarity	NPC326500
0.9167	High Similarity	NPC144499
0.9167	High Similarity	NPC266725
0.9167	High Similarity	NPC200694
0.9161	High Similarity	NPC69769
0.9155	High Similarity	NPC272844
0.9155	High Similarity	NPC17848
0.9155	High Similarity	NPC248995
0.9155	High Similarity	NPC254168
0.9155	High Similarity	NPC71903
0.9149	High Similarity	NPC13408
0.9133	High Similarity	NPC279218
0.9133	High Similarity	NPC108937
0.9122	High Similarity	NPC29777
0.9122	High Similarity	NPC471115
0.9122	High Similarity	NPC188403
0.9116	High Similarity	NPC296869
0.9116	High Similarity	NPC160821
0.9116	High Similarity	NPC132592
0.911	High Similarity	NPC153758
0.911	High Similarity	NPC477955
0.911	High Similarity	NPC127059
0.911	High Similarity	NPC124729
0.911	High Similarity	NPC285630
0.9103	High Similarity	NPC107177
0.9103	High Similarity	NPC293053
0.9103	High Similarity	NPC212932
0.9103	High Similarity	NPC85162
0.9103	High Similarity	NPC18585
0.9103	High Similarity	NPC278249
0.9103	High Similarity	NPC77794
0.9103	High Similarity	NPC106985
0.9103	High Similarity	NPC166138
0.9103	High Similarity	NPC478086
0.9103	High Similarity	NPC190637
0.9103	High Similarity	NPC9117
0.9103	High Similarity	NPC214166
0.9103	High Similarity	NPC316816
0.9103	High Similarity	NPC81697
0.9103	High Similarity	NPC24821
0.9103	High Similarity	NPC11700
0.9103	High Similarity	NPC125894
0.9103	High Similarity	NPC223812
0.9097	High Similarity	NPC201820
0.9097	High Similarity	NPC110038
0.9097	High Similarity	NPC248372
0.9091	High Similarity	NPC470986
0.9091	High Similarity	NPC23257
0.9085	High Similarity	NPC332594
0.9085	High Similarity	NPC157855
0.9085	High Similarity	NPC38153
0.9078	High Similarity	NPC101752

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 NPC297886 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
0.9306	High Similarity	NPD7410	Clinical (unspecified phase)
0.9041	High Similarity	NPD4378	Clinical (unspecified phase)
0.8933	High Similarity	NPD7411	Suspended
0.869	High Similarity	NPD1552	Clinical (unspecified phase)
0.869	High Similarity	NPD1550	Clinical (unspecified phase)
0.8645	High Similarity	NPD7075	Discontinued
0.8639	High Similarity	NPD3750	Approved
0.8636	High Similarity	NPD8443	Clinical (unspecified phase)
0.863	High Similarity	NPD1549	Phase 2
0.8627	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD7096	Clinical (unspecified phase)
0.8571	High Similarity	NPD7819	Suspended
0.8552	High Similarity	NPD1510	Phase 2
0.8531	High Similarity	NPD1240	Approved
0.8526	High Similarity	NPD3749	Approved
0.8497	Intermediate Similarity	NPD4380	Phase 2
0.8493	Intermediate Similarity	NPD2796	Approved
0.8467	Intermediate Similarity	NPD6799	Approved
0.8462	Intermediate Similarity	NPD7768	Phase 2
0.8452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1243	Approved
0.8446	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1607	Approved
0.8378	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD5124	Phase 1
0.8344	Intermediate Similarity	NPD1511	Approved
0.8301	Intermediate Similarity	NPD5403	Approved
0.8299	Intermediate Similarity	NPD3748	Approved
0.8299	Intermediate Similarity	NPD2799	Discontinued
0.8291	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD2313	Discontinued
0.8264	Intermediate Similarity	NPD3268	Approved
0.8264	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6599	Discontinued
0.8235	Intermediate Similarity	NPD1512	Approved
0.8217	Intermediate Similarity	NPD2801	Approved
0.82	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD920	Approved
0.8171	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD5401	Approved
0.8169	Intermediate Similarity	NPD2797	Approved
0.8169	Intermediate Similarity	NPD1203	Approved
0.8165	Intermediate Similarity	NPD3817	Phase 2
0.8163	Intermediate Similarity	NPD6651	Approved
0.8158	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD1934	Approved
0.8121	Intermediate Similarity	NPD2935	Discontinued
0.8121	Intermediate Similarity	NPD1551	Phase 2
0.8099	Intermediate Similarity	NPD3225	Approved
0.8052	Intermediate Similarity	NPD2532	Approved
0.8052	Intermediate Similarity	NPD2534	Approved
0.8052	Intermediate Similarity	NPD2533	Approved
0.8052	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7473	Discontinued
0.8025	Intermediate Similarity	NPD6959	Discontinued
0.8014	Intermediate Similarity	NPD422	Phase 1
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7964	Intermediate Similarity	NPD5953	Discontinued
0.7962	Intermediate Similarity	NPD3226	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
0.7933	Intermediate Similarity	NPD4308	Phase 3
0.7917	Intermediate Similarity	NPD3267	Approved
0.7917	Intermediate Similarity	NPD3266	Approved
0.7908	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD3882	Suspended
0.7888	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6166	Phase 2
0.7879	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD6832	Phase 2
0.787	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD5494	Approved
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.7844	Intermediate Similarity	NPD7054	Approved
0.7829	Intermediate Similarity	NPD2346	Discontinued
0.7798	Intermediate Similarity	NPD7074	Phase 3
0.7798	Intermediate Similarity	NPD7472	Approved
0.7791	Intermediate Similarity	NPD919	Approved
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.777	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6099	Approved
0.7763	Intermediate Similarity	NPD6100	Approved
0.7751	Intermediate Similarity	NPD6797	Phase 2
0.774	Intermediate Similarity	NPD2798	Approved
0.7712	Intermediate Similarity	NPD2344	Approved
0.7706	Intermediate Similarity	NPD6559	Discontinued
0.7706	Intermediate Similarity	NPD7251	Discontinued
0.7688	Intermediate Similarity	NPD6585	Discontinued
0.7677	Intermediate Similarity	NPD4628	Phase 3
0.7667	Intermediate Similarity	NPD4307	Phase 2
0.7661	Intermediate Similarity	NPD7808	Phase 3
0.7654	Intermediate Similarity	NPD1465	Phase 2
0.7651	Intermediate Similarity	NPD1296	Phase 2
0.764	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4908	Phase 1
0.7607	Intermediate Similarity	NPD4288	Approved
0.76	Intermediate Similarity	NPD4287	Approved
0.7586	Intermediate Similarity	NPD1608	Approved
0.7582	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5408	Approved
0.7532	Intermediate Similarity	NPD5404	Approved
0.7532	Intermediate Similarity	NPD5405	Approved
0.7532	Intermediate Similarity	NPD7390	Discontinued
0.7532	Intermediate Similarity	NPD5406	Approved
0.7531	Intermediate Similarity	NPD5889	Approved
0.7531	Intermediate Similarity	NPD5890	Approved
0.7528	Intermediate Similarity	NPD4360	Phase 2
0.7528	Intermediate Similarity	NPD4363	Phase 3
0.7516	Intermediate Similarity	NPD7458	Discontinued
0.7516	Intermediate Similarity	NPD2309	Approved
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1548	Phase 1
0.7452	Intermediate Similarity	NPD7003	Approved
0.7442	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5711	Approved
0.744	Intermediate Similarity	NPD5710	Approved
0.7438	Intermediate Similarity	NPD5049	Phase 3
0.7434	Intermediate Similarity	NPD943	Approved
0.7417	Intermediate Similarity	NPD3764	Approved
0.7417	Intermediate Similarity	NPD411	Approved
0.7407	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1610	Phase 2
0.7397	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4361	Phase 2
0.7386	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD447	Suspended
0.7379	Intermediate Similarity	NPD17	Approved
0.7372	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD9545	Approved
0.7353	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4625	Phase 3
0.7343	Intermediate Similarity	NPD9493	Approved
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.7318	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1164	Approved
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7296	Intermediate Similarity	NPD2354	Approved
0.7285	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2654	Approved
0.7278	Intermediate Similarity	NPD1247	Approved
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.723	Intermediate Similarity	NPD1481	Phase 2
0.7222	Intermediate Similarity	NPD6273	Approved
0.7216	Intermediate Similarity	NPD8312	Approved
0.7216	Intermediate Similarity	NPD8313	Approved
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3926	Phase 2
0.7184	Intermediate Similarity	NPD1729	Discontinued
0.7183	Intermediate Similarity	NPD5535	Approved
0.7181	Intermediate Similarity	NPD4749	Approved
0.7181	Intermediate Similarity	NPD7584	Approved
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.717	Intermediate Similarity	NPD1652	Phase 2
0.7162	Intermediate Similarity	NPD1535	Discovery
0.7161	Intermediate Similarity	NPD230	Phase 1
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2353	Approved
0.7152	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD6002	Phase 3
0.7152	Intermediate Similarity	NPD6004	Phase 3
0.7123	Intermediate Similarity	NPD1894	Discontinued
0.7114	Intermediate Similarity	NPD3972	Approved
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4060	Phase 1
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7093	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4477	Approved
0.7089	Intermediate Similarity	NPD4476	Approved
0.7081	Intermediate Similarity	NPD3887	Approved
0.7069	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7177	Discontinued
0.7059	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7585	Approved
0.7048	Intermediate Similarity	NPD6502	Phase 2
0.7047	Intermediate Similarity	NPD1201	Approved
0.7032	Intermediate Similarity	NPD6233	Phase 2
0.7024	Intermediate Similarity	NPD8455	Phase 2
0.702	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD6971	Discontinued
0.7	Intermediate Similarity	NPD7583	Approved
0.7	Intermediate Similarity	NPD8150	Discontinued
0.6993	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2296	Approved
0.6974	Remote Similarity	NPD1470	Approved
0.6971	Remote Similarity	NPD3751	Discontinued

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