NPASS Compound

Structure

CID179970 OpenBabel06191715552D 31 35 0 0 0 0 0 0 0 0999 V2000 9.6262 -2.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5297 -3.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 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 1.7321 -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 7.7942 -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 8.6603 -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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 6.9282 -2.0000 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 -0.0000 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 3.4641 -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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 4.3301 -3.5000 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 7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 28 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 20 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 21 2 0 0 0 0 13 22 1 0 0 0 0 14 19 2 0 0 0 0 14 29 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 24 2 0 0 0 0 17 20 2 0 0 0 0 17 24 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 22 29 1 0 0 0 0 23 27 2 0 0 0 0 24 28 1 0 0 0 0 25 31 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.16
Volume:	433.056
LogP:	6.341
LogD:	4.987
LogS:	-3.238
# Rotatable Bonds:	2
TPSA:	57.9
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.525
Synthetic Accessibility Score:	3.265
Fsp3:	0.269
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.031
MDCK Permeability:	1.6158985090442002e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.646
30% Bioavailability (F30%):	0.802

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	99.42317962646484%
Volume Distribution (VD):	0.382
Pgp-substrate:	2.730720043182373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.541
CYP1A2-substrate:	0.753
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.903
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.954
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.919
CYP3A4-substrate:	0.538

ADMET: Excretion

Clearance (CL):	1.961
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.793
Human Hepatotoxicity (H-HT):	0.952
Drug-inuced Liver Injury (DILI):	0.799
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.705
Maximum Recommended Daily Dose:	0.434
Skin Sensitization:	0.171
Carcinogencity:	0.899
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC179970

Natural Product ID:	NPC179970
*Common Name:**	Munetone
IUPAC Name:	7-(5-methoxy-2,2-dimethylchromen-6-yl)-2,2-dimethylpyrano[3,2-g]chromen-6-one
Synonyms:	Munetone
Standard InCHIKey:	JANOATQYNVFIDV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H24O5/c1-25(2)10-8-15-12-18-22(13-21(15)31-25)29-14-19(23(18)27)16-6-7-20-17(24(16)28-5)9-11-26(3,4)30-20/h6-14H,1-5H3
SMILES:	COc1c2C=CC(Oc2ccc1c1coc2c(c1=O)cc1c(c2)OC(C=C1)(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463492
PubChem CID:	12312999
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	bark	an elevation of 850 m (171725? S; 484030? E), Toamasina, Madagascar	2002-JAN	PMID[15043430]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15043430]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	flower	n.a.	PMID[15043430]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15043430]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23002924]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29799195]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14502	Pogonolepis muelleriana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9663	Artemisia igniaria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	20.0	ug.mL-1	PMID[520913]

☑ 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 NPC179970 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	493
0.1-0.2	1809
0.2-0.3	4471
0.3-0.4	11376
0.4-0.5	7006
0.5-0.6	4409
0.6-0.7	5913
0.7-0.8	4619
0.8-0.85	1947
0.85-0.9	562
0.9-0.95	90
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC59522
0.9565	High Similarity	NPC17848
0.951	High Similarity	NPC266572
0.95	High Similarity	NPC52576
0.9493	High Similarity	NPC157855
0.9441	High Similarity	NPC104406
0.9441	High Similarity	NPC24673
0.9441	High Similarity	NPC201731
0.9441	High Similarity	NPC97716
0.9441	High Similarity	NPC237635
0.9441	High Similarity	NPC79469
0.9429	High Similarity	NPC472409
0.942	High Similarity	NPC161196
0.942	High Similarity	NPC254741
0.9375	High Similarity	NPC321623
0.9375	High Similarity	NPC189087
0.9375	High Similarity	NPC6511
0.9357	High Similarity	NPC11566
0.9348	High Similarity	NPC46869
0.9301	High Similarity	NPC311741
0.9301	High Similarity	NPC234629
0.9257	High Similarity	NPC477530
0.9247	High Similarity	NPC188403
0.9247	High Similarity	NPC5840
0.9247	High Similarity	NPC189270
0.9241	High Similarity	NPC161191
0.9225	High Similarity	NPC103362
0.9214	High Similarity	NPC259685
0.9203	High Similarity	NPC223354
0.9203	High Similarity	NPC292998
0.9195	High Similarity	NPC180340
0.9178	High Similarity	NPC5173
0.9172	High Similarity	NPC282335
0.9172	High Similarity	NPC471285
0.9172	High Similarity	NPC296998
0.9172	High Similarity	NPC23728
0.9172	High Similarity	NPC218300
0.9172	High Similarity	NPC110303
0.9172	High Similarity	NPC473077
0.9167	High Similarity	NPC319752
0.9161	High Similarity	NPC62840
0.9161	High Similarity	NPC214236
0.9161	High Similarity	NPC299080
0.9161	High Similarity	NPC147145
0.9161	High Similarity	NPC78803
0.9161	High Similarity	NPC59739
0.9161	High Similarity	NPC293852
0.9161	High Similarity	NPC11561
0.9161	High Similarity	NPC226636
0.9161	High Similarity	NPC217083
0.9155	High Similarity	NPC150522
0.9137	High Similarity	NPC125269
0.913	High Similarity	NPC473655
0.913	High Similarity	NPC229646
0.913	High Similarity	NPC182428
0.913	High Similarity	NPC101294
0.9116	High Similarity	NPC29777
0.9116	High Similarity	NPC471115
0.911	High Similarity	NPC160821
0.911	High Similarity	NPC244407
0.911	High Similarity	NPC132592
0.9103	High Similarity	NPC214774
0.9103	High Similarity	NPC312973
0.9103	High Similarity	NPC20488
0.9103	High Similarity	NPC475052
0.9103	High Similarity	NPC474161
0.9103	High Similarity	NPC83357
0.9103	High Similarity	NPC246948
0.9103	High Similarity	NPC267375
0.9103	High Similarity	NPC54577
0.9103	High Similarity	NPC142405
0.9103	High Similarity	NPC476088
0.9103	High Similarity	NPC470647
0.9103	High Similarity	NPC195621
0.9103	High Similarity	NPC67805
0.9103	High Similarity	NPC176229
0.9103	High Similarity	NPC88964
0.9103	High Similarity	NPC111786
0.9103	High Similarity	NPC301276
0.9097	High Similarity	NPC106985
0.9097	High Similarity	NPC38219
0.9097	High Similarity	NPC219915
0.9097	High Similarity	NPC18585
0.9097	High Similarity	NPC17262
0.9097	High Similarity	NPC166138
0.9091	High Similarity	NPC268204
0.9091	High Similarity	NPC64908
0.9091	High Similarity	NPC147688
0.9091	High Similarity	NPC55832
0.9091	High Similarity	NPC52789
0.9091	High Similarity	NPC26051
0.9091	High Similarity	NPC205006
0.9091	High Similarity	NPC110969
0.9091	High Similarity	NPC156590
0.9091	High Similarity	NPC118840
0.9085	High Similarity	NPC136095
0.9071	High Similarity	NPC99854
0.906	High Similarity	NPC472408
0.906	High Similarity	NPC128961
0.9058	High Similarity	NPC278556
0.9058	High Similarity	NPC284424
0.9048	High Similarity	NPC474052
0.9048	High Similarity	NPC164299
0.9048	High Similarity	NPC317492
0.9041	High Similarity	NPC283234
0.9041	High Similarity	NPC14001
0.9041	High Similarity	NPC166757
0.9034	High Similarity	NPC209040
0.9028	High Similarity	NPC144499
0.9021	High Similarity	NPC253822
0.9021	High Similarity	NPC326109
0.9021	High Similarity	NPC171094
0.9021	High Similarity	NPC259166
0.9021	High Similarity	NPC204985
0.9021	High Similarity	NPC159275
0.9021	High Similarity	NPC172986
0.9021	High Similarity	NPC270883
0.9021	High Similarity	NPC172250
0.9021	High Similarity	NPC235239
0.9021	High Similarity	NPC241100
0.9021	High Similarity	NPC305355
0.9021	High Similarity	NPC80962
0.9021	High Similarity	NPC475680
0.9021	High Similarity	NPC215311
0.9021	High Similarity	NPC213659
0.9021	High Similarity	NPC144118
0.9021	High Similarity	NPC101366
0.9021	High Similarity	NPC48624
0.9021	High Similarity	NPC219917
0.9021	High Similarity	NPC261227
0.9	High Similarity	NPC470681
0.8993	High Similarity	NPC40033
0.8986	High Similarity	NPC61258
0.8986	High Similarity	NPC472633
0.898	High Similarity	NPC168085
0.898	High Similarity	NPC39195
0.898	High Similarity	NPC296869
0.8973	High Similarity	NPC477955
0.8973	High Similarity	NPC220418
0.8973	High Similarity	NPC124729
0.8966	High Similarity	NPC175504
0.8966	High Similarity	NPC478086
0.8966	High Similarity	NPC143896
0.8966	High Similarity	NPC149026
0.8966	High Similarity	NPC214166
0.8966	High Similarity	NPC91560
0.8966	High Similarity	NPC316816
0.8966	High Similarity	NPC75049
0.8966	High Similarity	NPC150408
0.8966	High Similarity	NPC310130
0.8966	High Similarity	NPC257097
0.8966	High Similarity	NPC221432
0.8966	High Similarity	NPC169591
0.8966	High Similarity	NPC68104
0.8966	High Similarity	NPC39329
0.8966	High Similarity	NPC164980
0.8958	High Similarity	NPC22467
0.8958	High Similarity	NPC469404
0.8958	High Similarity	NPC3188
0.8958	High Similarity	NPC282300
0.8951	High Similarity	NPC295384
0.8951	High Similarity	NPC473209
0.8951	High Similarity	NPC303633
0.8951	High Similarity	NPC473076
0.8951	High Similarity	NPC472515
0.8951	High Similarity	NPC96565
0.8951	High Similarity	NPC216978
0.8951	High Similarity	NPC283429
0.8951	High Similarity	NPC220062
0.8951	High Similarity	NPC55018
0.8951	High Similarity	NPC78913
0.8951	High Similarity	NPC301217
0.8951	High Similarity	NPC18260
0.8951	High Similarity	NPC217186
0.8951	High Similarity	NPC53181
0.8951	High Similarity	NPC23257
0.8944	High Similarity	NPC103001
0.8944	High Similarity	NPC253616
0.8944	High Similarity	NPC38153
0.894	High Similarity	NPC282307
0.894	High Similarity	NPC170026
0.8933	High Similarity	NPC7989
0.8933	High Similarity	NPC469405
0.8933	High Similarity	NPC88983
0.8933	High Similarity	NPC223701
0.8933	High Similarity	NPC472583
0.8926	High Similarity	NPC472407
0.8919	High Similarity	NPC291746
0.8919	High Similarity	NPC288840
0.8919	High Similarity	NPC10027
0.8919	High Similarity	NPC473016
0.8919	High Similarity	NPC65775
0.8912	High Similarity	NPC308200
0.8912	High Similarity	NPC180477
0.8904	High Similarity	NPC216538
0.8904	High Similarity	NPC131579
0.8904	High Similarity	NPC473013
0.8904	High Similarity	NPC471590
0.8904	High Similarity	NPC273538
0.8904	High Similarity	NPC87486

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 NPC179970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	413
0.1-0.2	1005
0.2-0.3	1571
0.3-0.4	2749
0.4-0.5	1972
0.5-0.6	979
0.6-0.7	316
0.7-0.8	112
0.8-0.85	28
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9281	High Similarity	NPD2796	Approved
0.8904	High Similarity	NPD7410	Clinical (unspecified phase)
0.8904	High Similarity	NPD4378	Clinical (unspecified phase)
0.8675	High Similarity	NPD7411	Suspended
0.8671	High Similarity	NPD1510	Phase 2
0.8621	High Similarity	NPD1549	Phase 2
0.8609	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8562	High Similarity	NPD7819	Suspended
0.8552	High Similarity	NPD1550	Clinical (unspecified phase)
0.8552	High Similarity	NPD1552	Clinical (unspecified phase)
0.8533	High Similarity	NPD920	Approved
0.8526	High Similarity	NPD5494	Approved
0.8506	High Similarity	NPD8443	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD6801	Discontinued
0.8456	Intermediate Similarity	NPD6799	Approved
0.8442	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1243	Approved
0.8414	Intermediate Similarity	NPD3748	Approved
0.84	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD7075	Discontinued
0.8392	Intermediate Similarity	NPD1240	Approved
0.8389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1607	Approved
0.8247	Intermediate Similarity	NPD6599	Discontinued
0.8217	Intermediate Similarity	NPD7768	Phase 2
0.8205	Intermediate Similarity	NPD2801	Approved
0.8188	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD5403	Approved
0.816	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD5401	Approved
0.8153	Intermediate Similarity	NPD3817	Phase 2
0.8141	Intermediate Similarity	NPD1934	Approved
0.8133	Intermediate Similarity	NPD3750	Approved
0.8125	Intermediate Similarity	NPD6959	Discontinued
0.8101	Intermediate Similarity	NPD3882	Suspended
0.8092	Intermediate Similarity	NPD1511	Approved
0.805	Intermediate Similarity	NPD3749	Approved
0.8041	Intermediate Similarity	NPD2799	Discontinued
0.8038	Intermediate Similarity	NPD5402	Approved
0.8012	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD919	Approved
0.7987	Intermediate Similarity	NPD1512	Approved
0.7986	Intermediate Similarity	NPD6832	Phase 2
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7947	Intermediate Similarity	NPD2800	Approved
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7867	Intermediate Similarity	NPD1551	Phase 2
0.7844	Intermediate Similarity	NPD5953	Discontinued
0.7831	Intermediate Similarity	NPD7054	Approved
0.7805	Intermediate Similarity	NPD3926	Phase 2
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7784	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2935	Discontinued
0.7738	Intermediate Similarity	NPD6797	Phase 2
0.7725	Intermediate Similarity	NPD7286	Phase 2
0.7724	Intermediate Similarity	NPD2798	Approved
0.7697	Intermediate Similarity	NPD2344	Approved
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7667	Intermediate Similarity	NPD6651	Approved
0.7651	Intermediate Similarity	NPD4307	Phase 2
0.7647	Intermediate Similarity	NPD7808	Phase 3
0.7636	Intermediate Similarity	NPD6232	Discontinued
0.7635	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD5889	Approved
0.7625	Intermediate Similarity	NPD5890	Approved
0.7619	Intermediate Similarity	NPD5844	Phase 1
0.761	Intermediate Similarity	NPD3226	Approved
0.7605	Intermediate Similarity	NPD7473	Discontinued
0.76	Intermediate Similarity	NPD5124	Phase 1
0.76	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2654	Approved
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6559	Discontinued
0.7582	Intermediate Similarity	NPD2346	Discontinued
0.7569	Intermediate Similarity	NPD3972	Approved
0.7566	Intermediate Similarity	NPD7033	Discontinued
0.7566	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6585	Discontinued
0.7548	Intermediate Similarity	NPD4628	Phase 3
0.7545	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3267	Approved
0.7534	Intermediate Similarity	NPD3266	Approved
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7483	Intermediate Similarity	NPD1933	Approved
0.7482	Intermediate Similarity	NPD1241	Discontinued
0.7468	Intermediate Similarity	NPD1471	Phase 3
0.7456	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4308	Phase 3
0.7427	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD943	Approved
0.7416	Intermediate Similarity	NPD4363	Phase 3
0.7416	Intermediate Similarity	NPD4360	Phase 2
0.7415	Intermediate Similarity	NPD1203	Approved
0.7405	Intermediate Similarity	NPD7390	Discontinued
0.7403	Intermediate Similarity	NPD6099	Approved
0.7403	Intermediate Similarity	NPD6100	Approved
0.74	Intermediate Similarity	NPD1296	Phase 2
0.74	Intermediate Similarity	NPD3268	Approved
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7378	Intermediate Similarity	NPD4288	Approved
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7362	Intermediate Similarity	NPD6280	Approved
0.7362	Intermediate Similarity	NPD6279	Approved
0.7347	Intermediate Similarity	NPD3225	Approved
0.7343	Intermediate Similarity	NPD1548	Phase 1
0.7337	Intermediate Similarity	NPD2403	Approved
0.7333	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD9717	Approved
0.7325	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2797	Approved
0.7278	Intermediate Similarity	NPD3887	Approved
0.7278	Intermediate Similarity	NPD4361	Phase 2
0.7278	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1610	Phase 2
0.7256	Intermediate Similarity	NPD6844	Discontinued
0.7251	Intermediate Similarity	NPD3751	Discontinued
0.7244	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD17	Approved
0.723	Intermediate Similarity	NPD1876	Approved
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD6808	Phase 2
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7215	Intermediate Similarity	NPD7003	Approved
0.7212	Intermediate Similarity	NPD1465	Phase 2
0.719	Intermediate Similarity	NPD3142	Approved
0.719	Intermediate Similarity	NPD3140	Approved
0.7178	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1729	Discontinued
0.7166	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7134	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2353	Approved
0.712	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5710	Approved
0.7118	Intermediate Similarity	NPD5711	Approved
0.7105	Intermediate Similarity	NPD4625	Phase 3
0.7102	Intermediate Similarity	NPD8313	Approved
0.7102	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD1608	Approved
0.7095	Intermediate Similarity	NPD4287	Approved
0.7089	Intermediate Similarity	NPD2424	Discontinued
0.7086	Intermediate Similarity	NPD6104	Discontinued
0.7076	Intermediate Similarity	NPD5242	Approved
0.7065	Intermediate Similarity	NPD8285	Discontinued
0.7059	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7055	Intermediate Similarity	NPD1651	Approved
0.7039	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4662	Approved
0.7037	Intermediate Similarity	NPD4661	Approved
0.7032	Intermediate Similarity	NPD447	Suspended
0.7032	Intermediate Similarity	NPD230	Phase 1
0.7027	Intermediate Similarity	NPD6782	Approved
0.7027	Intermediate Similarity	NPD6781	Approved
0.7027	Intermediate Similarity	NPD6780	Approved
0.7027	Intermediate Similarity	NPD6778	Approved
0.7027	Intermediate Similarity	NPD6779	Approved
0.7027	Intermediate Similarity	NPD6776	Approved
0.7027	Intermediate Similarity	NPD6777	Approved
0.7006	Intermediate Similarity	NPD8455	Phase 2
0.7006	Intermediate Similarity	NPD5761	Phase 2
0.7006	Intermediate Similarity	NPD5760	Phase 2
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5049	Phase 3
0.6994	Remote Similarity	NPD6273	Approved
0.6986	Remote Similarity	NPD9545	Approved
0.6983	Remote Similarity	NPD8434	Phase 2
0.697	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2296	Approved
0.6962	Remote Similarity	NPD4476	Approved
0.6962	Remote Similarity	NPD5408	Approved
0.6962	Remote Similarity	NPD4477	Approved
0.6962	Remote Similarity	NPD5404	Approved
0.6962	Remote Similarity	NPD5406	Approved
0.6962	Remote Similarity	NPD5405	Approved
0.6959	Remote Similarity	NPD7199	Phase 2
0.6957	Remote Similarity	NPD2354	Approved
0.6954	Remote Similarity	NPD7177	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