NPASS Compound

Structure

NPC38153 OpenBabel07101719132D 28 30 0 0 0 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 -5.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 0.8660 -2.5000 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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 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 7 1 0 0 0 0 2 8 1 0 0 0 0 3 13 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 26 1 0 0 0 0 7 9 1 0 0 0 0 8 13 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 23 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 24 2 0 0 0 0 16 27 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 21 28 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.18
Volume:	403.554
LogP:	5.008
LogD:	4.63
LogS:	-5.721
# Rotatable Bonds:	5
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	3.294
Fsp3:	0.391
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:	-4.774
MDCK Permeability:	1.3323213352123275e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.096

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	95.94811248779297%
Volume Distribution (VD):	0.928
Pgp-substrate:	4.027380466461182%

ADMET: Metabolism

CYP1A2-inhibitor:	0.755
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.404
CYP2C9-inhibitor:	0.912
CYP2C9-substrate:	0.62
CYP2D6-inhibitor:	0.822
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.717
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	3.882
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.898
Drug-inuced Liver Injury (DILI):	0.648
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.671
Skin Sensitization:	0.351
Carcinogencity:	0.891
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.854

Download Data

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

Natural Product: NPC38153

Natural Product ID:	NPC38153
*Common Name:**	5-Methoxy-2,2-Dimethyl-6-[(E)-2-Methylbut-2-Enoyl]-10-Propylpyrano[2,3-F]Chromen-8-One
IUPAC Name:	5-methoxy-2,2-dimethyl-6-[(E)-2-methylbut-2-enoyl]-10-propylpyrano[2,3-f]chromen-8-one
Synonyms:
Standard InCHIKey:	RMUWCAYGHBNRQJ-MDWZMJQESA-N
Standard InCHI:	InChI=1S/C23H26O5/c1-7-9-14-12-16(24)27-22-17(14)21-15(10-11-23(4,5)28-21)20(26-6)18(22)19(25)13(3)8-2/h8,10-12H,7,9H2,1-6H3/b13-8+
SMILES:	CCCc1cc(=O)oc2c1c1c(C=CC(C)(C)O1)c(c2C(=O)/C(=C/C)/C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478978
PubChem CID:	11100998
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[11908963]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662094]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104480]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15340243]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25528	Calophyllum brasiliense	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
EC50	3
IC50	5
Others	11

Activity Type	# Activity
Cell Line	7
Organism	3
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[493129]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[493129]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	>	10000.0	nM	PMID[493130]
NPT6286	Cell Line	U1	Homo sapiens	IC50	=	8440.0	nM	PMID[493130]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[493129]
NPT2	Others	Unspecified		Activity	=	19.5	%	PMID[493129]
NPT2	Others	Unspecified		Activity	=	62.5	%	PMID[493129]
NPT2	Others	Unspecified		Activity	=	90.8	%	PMID[493129]
NPT2	Others	Unspecified		IC50	=	268.0	molar ratio	PMID[493129]
NPT2	Others	Unspecified		Ratio IC50/EC50	>	2.93	n.a.	PMID[493130]
NPT2	Others	Unspecified		Ratio IC50/EC50	=	2.43	n.a.	PMID[493130]
NPT2	Others	Unspecified		Ratio IC50/EC50	=	1.95	n.a.	PMID[493130]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[493130]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3410.0	nM	PMID[493130]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	4320.0	nM	PMID[493130]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3480.0	nM	PMID[493130]

☑ 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 NPC38153 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	439
0.1-0.2	1772
0.2-0.3	4512
0.3-0.4	10630
0.4-0.5	7632
0.5-0.6	4436
0.6-0.7	6013
0.7-0.8	4968
0.8-0.85	1534
0.85-0.9	536
0.9-0.95	204
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9559	High Similarity	NPC201820
0.9552	High Similarity	NPC253616
0.9485	High Similarity	NPC221173
0.9478	High Similarity	NPC268081
0.9416	High Similarity	NPC470555
0.9403	High Similarity	NPC46869
0.9338	High Similarity	NPC36414
0.927	High Similarity	NPC472515
0.927	High Similarity	NPC473209
0.927	High Similarity	NPC472343
0.922	High Similarity	NPC218300
0.922	High Similarity	NPC285748
0.922	High Similarity	NPC180477
0.922	High Similarity	NPC282335
0.9214	High Similarity	NPC469953
0.9197	High Similarity	NPC17848
0.9191	High Similarity	NPC161196
0.9179	High Similarity	NPC229646
0.9149	High Similarity	NPC57470
0.913	High Similarity	NPC136095
0.9124	High Similarity	NPC157855
0.9124	High Similarity	NPC474624
0.9124	High Similarity	NPC131782
0.9124	High Similarity	NPC103001
0.9124	High Similarity	NPC138047
0.9118	High Similarity	NPC101752
0.9085	High Similarity	NPC297886
0.9085	High Similarity	NPC249942
0.9078	High Similarity	NPC71184
0.9078	High Similarity	NPC206212
0.9078	High Similarity	NPC171656
0.9071	High Similarity	NPC36181
0.9058	High Similarity	NPC183639
0.9058	High Similarity	NPC199458
0.9058	High Similarity	NPC470083
0.9058	High Similarity	NPC219584
0.9051	High Similarity	NPC472516
0.9028	High Similarity	NPC151973
0.9021	High Similarity	NPC161864
0.9021	High Similarity	NPC208303
0.9021	High Similarity	NPC469933
0.9014	High Similarity	NPC470322
0.9007	High Similarity	NPC196459
0.9007	High Similarity	NPC188632
0.9007	High Similarity	NPC112791
0.9007	High Similarity	NPC59522
0.9007	High Similarity	NPC470296
0.9007	High Similarity	NPC87609
0.9007	High Similarity	NPC94794
0.9	High Similarity	NPC103362
0.9	High Similarity	NPC52576
0.8993	High Similarity	NPC241975
0.8993	High Similarity	NPC11566
0.8993	High Similarity	NPC19476
0.8958	High Similarity	NPC469932
0.8951	High Similarity	NPC140120
0.8951	High Similarity	NPC129650
0.8951	High Similarity	NPC474108
0.8951	High Similarity	NPC177995
0.8944	High Similarity	NPC178627
0.8944	High Similarity	NPC294365
0.8944	High Similarity	NPC196137
0.8944	High Similarity	NPC179970
0.8944	High Similarity	NPC469935
0.8944	High Similarity	NPC1886
0.8936	High Similarity	NPC11561
0.8936	High Similarity	NPC112829
0.8936	High Similarity	NPC226636
0.8936	High Similarity	NPC470556
0.8936	High Similarity	NPC294432
0.8929	High Similarity	NPC150522
0.8929	High Similarity	NPC470856
0.8929	High Similarity	NPC472409
0.8921	High Similarity	NPC248995
0.8921	High Similarity	NPC272844
0.8921	High Similarity	NPC254168
0.8913	High Similarity	NPC254741
0.8913	High Similarity	NPC470982
0.8913	High Similarity	NPC470983
0.8905	High Similarity	NPC66705
0.8897	High Similarity	NPC101294
0.8897	High Similarity	NPC473655
0.8889	High Similarity	NPC211811
0.8881	High Similarity	NPC154217
0.8881	High Similarity	NPC181388
0.8873	High Similarity	NPC470553
0.8873	High Similarity	NPC33653
0.8873	High Similarity	NPC307895
0.8873	High Similarity	NPC474939
0.8873	High Similarity	NPC184738
0.8873	High Similarity	NPC470909
0.8873	High Similarity	NPC96216
0.8872	High Similarity	NPC37512
0.8865	High Similarity	NPC110969
0.8865	High Similarity	NPC205006
0.8865	High Similarity	NPC156590
0.8865	High Similarity	NPC118840
0.8865	High Similarity	NPC64908
0.8865	High Similarity	NPC147688
0.8857	High Similarity	NPC240305
0.8857	High Similarity	NPC53181
0.8857	High Similarity	NPC473076
0.8857	High Similarity	NPC217186
0.8857	High Similarity	NPC23257
0.8855	High Similarity	NPC50720
0.8849	High Similarity	NPC259685
0.8849	High Similarity	NPC332594
0.8832	High Similarity	NPC292998
0.8828	High Similarity	NPC19238
0.8828	High Similarity	NPC104236
0.8828	High Similarity	NPC164299
0.8828	High Similarity	NPC164205
0.8824	High Similarity	NPC278556
0.8824	High Similarity	NPC284424
0.8819	High Similarity	NPC97716
0.8819	High Similarity	NPC24673
0.8819	High Similarity	NPC104406
0.8819	High Similarity	NPC237635
0.8819	High Similarity	NPC79469
0.8819	High Similarity	NPC201731
0.8811	High Similarity	NPC288910
0.8811	High Similarity	NPC118059
0.8811	High Similarity	NPC311741
0.8811	High Similarity	NPC470554
0.8811	High Similarity	NPC133060
0.8811	High Similarity	NPC234629
0.8806	High Similarity	NPC473907
0.8803	High Similarity	NPC78803
0.8803	High Similarity	NPC214236
0.8803	High Similarity	NPC59739
0.8803	High Similarity	NPC147145
0.8803	High Similarity	NPC293852
0.8803	High Similarity	NPC217083
0.8803	High Similarity	NPC299080
0.8803	High Similarity	NPC62840
0.8794	High Similarity	NPC305355
0.8794	High Similarity	NPC172986
0.8794	High Similarity	NPC235239
0.8794	High Similarity	NPC471587
0.8794	High Similarity	NPC241100
0.8794	High Similarity	NPC474037
0.8794	High Similarity	NPC159275
0.8794	High Similarity	NPC261227
0.8794	High Similarity	NPC475680
0.8794	High Similarity	NPC270883
0.8786	High Similarity	NPC54820
0.8786	High Similarity	NPC268178
0.8786	High Similarity	NPC180501
0.8786	High Similarity	NPC470668
0.8786	High Similarity	NPC470669
0.8786	High Similarity	NPC131130
0.8779	High Similarity	NPC150214
0.8777	High Similarity	NPC174999
0.8768	High Similarity	NPC125269
0.8767	High Similarity	NPC191104
0.8767	High Similarity	NPC474735
0.8767	High Similarity	NPC180351
0.8759	High Similarity	NPC6511
0.8759	High Similarity	NPC54503
0.8759	High Similarity	NPC55147
0.8759	High Similarity	NPC266572
0.875	High Similarity	NPC470910
0.8741	High Similarity	NPC166138
0.8741	High Similarity	NPC17262
0.8741	High Similarity	NPC106985
0.8741	High Similarity	NPC38219
0.8741	High Similarity	NPC18585
0.8741	High Similarity	NPC473894
0.8732	High Similarity	NPC24075
0.8732	High Similarity	NPC316911
0.8732	High Similarity	NPC254010
0.8732	High Similarity	NPC282300
0.8732	High Similarity	NPC316560
0.8731	High Similarity	NPC475496
0.8731	High Similarity	NPC49852
0.8723	High Similarity	NPC220062
0.8723	High Similarity	NPC262635
0.8723	High Similarity	NPC303633
0.8723	High Similarity	NPC216978
0.8723	High Similarity	NPC78913
0.8723	High Similarity	NPC96565
0.8723	High Similarity	NPC301217
0.8723	High Similarity	NPC55018
0.8723	High Similarity	NPC18260
0.8707	High Similarity	NPC290671
0.8705	High Similarity	NPC99854
0.8705	High Similarity	NPC151113
0.8699	High Similarity	NPC88445
0.8696	High Similarity	NPC223354
0.869	High Similarity	NPC23728
0.869	High Similarity	NPC110303
0.8681	High Similarity	NPC257236
0.8681	High Similarity	NPC209040
0.8681	High Similarity	NPC319752
0.8681	High Similarity	NPC278175
0.8676	High Similarity	NPC470987
0.8676	High Similarity	NPC21378
0.8671	High Similarity	NPC313036
0.8671	High Similarity	NPC144499
0.8671	High Similarity	NPC472344

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 NPC38153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	988
0.2-0.3	1652
0.3-0.4	2673
0.4-0.5	1920
0.5-0.6	1056
0.6-0.7	335
0.7-0.8	107
0.8-0.85	26
0.85-0.9	15
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8777	High Similarity	NPD2796	Approved
0.8723	High Similarity	NPD1243	Approved
0.8681	High Similarity	NPD7410	Clinical (unspecified phase)
0.8581	High Similarity	NPD7411	Suspended
0.8562	High Similarity	NPD920	Approved
0.8552	High Similarity	NPD4378	Clinical (unspecified phase)
0.8542	High Similarity	NPD643	Clinical (unspecified phase)
0.8523	High Similarity	NPD6801	Discontinued
0.8483	Intermediate Similarity	NPD6799	Approved
0.8467	Intermediate Similarity	NPD7819	Suspended
0.8467	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD3748	Approved
0.8301	Intermediate Similarity	NPD7075	Discontinued
0.8267	Intermediate Similarity	NPD6599	Discontinued
0.8264	Intermediate Similarity	NPD1549	Phase 2
0.8227	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD5124	Phase 1
0.8207	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8156	Intermediate Similarity	NPD1240	Approved
0.8129	Intermediate Similarity	NPD919	Approved
0.8129	Intermediate Similarity	NPD6832	Phase 2
0.8082	Intermediate Similarity	NPD2800	Approved
0.8067	Intermediate Similarity	NPD5403	Approved
0.8054	Intermediate Similarity	NPD5401	Approved
0.8054	Intermediate Similarity	NPD2532	Approved
0.8054	Intermediate Similarity	NPD2534	Approved
0.8054	Intermediate Similarity	NPD2533	Approved
0.8052	Intermediate Similarity	NPD3817	Phase 2
0.8042	Intermediate Similarity	NPD1607	Approved
0.8042	Intermediate Similarity	NPD6651	Approved
0.8027	Intermediate Similarity	NPD3750	Approved
0.8026	Intermediate Similarity	NPD4380	Phase 2
0.8014	Intermediate Similarity	NPD2313	Discontinued
0.8014	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7987	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD3749	Approved
0.7935	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD2799	Discontinued
0.7887	Intermediate Similarity	NPD1296	Phase 2
0.7848	Intermediate Similarity	NPD5494	Approved
0.7834	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD9717	Approved
0.7786	Intermediate Similarity	NPD3266	Approved
0.7786	Intermediate Similarity	NPD3267	Approved
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4307	Phase 2
0.7756	Intermediate Similarity	NPD2801	Approved
0.7755	Intermediate Similarity	NPD2935	Discontinued
0.7755	Intermediate Similarity	NPD1551	Phase 2
0.7748	Intermediate Similarity	NPD1511	Approved
0.773	Intermediate Similarity	NPD1019	Discontinued
0.7707	Intermediate Similarity	NPD5402	Approved
0.7692	Intermediate Similarity	NPD1934	Approved
0.7677	Intermediate Similarity	NPD6585	Discontinued
0.766	Intermediate Similarity	NPD1203	Approved
0.7647	Intermediate Similarity	NPD1512	Approved
0.7639	Intermediate Similarity	NPD3268	Approved
0.7636	Intermediate Similarity	NPD5953	Discontinued
0.7628	Intermediate Similarity	NPD5889	Approved
0.7628	Intermediate Similarity	NPD5890	Approved
0.7626	Intermediate Similarity	NPD422	Phase 1
0.7626	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7286	Phase 2
0.7613	Intermediate Similarity	NPD3226	Approved
0.7603	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1933	Approved
0.76	Intermediate Similarity	NPD2654	Approved
0.7597	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD1247	Approved
0.7568	Intermediate Similarity	NPD7033	Discontinued
0.7568	Intermediate Similarity	NPD4308	Phase 3
0.755	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD3882	Suspended
0.7535	Intermediate Similarity	NPD2797	Approved
0.7531	Intermediate Similarity	NPD6232	Discontinued
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2798	Approved
0.7469	Intermediate Similarity	NPD6959	Discontinued
0.7465	Intermediate Similarity	NPD3225	Approved
0.7455	Intermediate Similarity	NPD3818	Discontinued
0.7439	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4628	Phase 3
0.7423	Intermediate Similarity	NPD5711	Approved
0.7423	Intermediate Similarity	NPD5710	Approved
0.7381	Intermediate Similarity	NPD6559	Discontinued
0.7378	Intermediate Similarity	NPD3926	Phase 2
0.7353	Intermediate Similarity	NPD1241	Discontinued
0.7337	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6166	Phase 2
0.7324	Intermediate Similarity	NPD3972	Approved
0.7305	Intermediate Similarity	NPD7054	Approved
0.7279	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD3887	Approved
0.7267	Intermediate Similarity	NPD4288	Approved
0.7262	Intermediate Similarity	NPD7074	Phase 3
0.7262	Intermediate Similarity	NPD7472	Approved
0.7248	Intermediate Similarity	NPD447	Suspended
0.7246	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2344	Approved
0.7237	Intermediate Similarity	NPD2353	Approved
0.7235	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD17	Approved
0.7232	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6797	Phase 2
0.7214	Intermediate Similarity	NPD9545	Approved
0.7197	Intermediate Similarity	NPD5049	Phase 3
0.7194	Intermediate Similarity	NPD9493	Approved
0.7188	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7251	Discontinued
0.7171	Intermediate Similarity	NPD6100	Approved
0.7171	Intermediate Similarity	NPD6099	Approved
0.7153	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7135	Intermediate Similarity	NPD7808	Phase 3
0.7126	Intermediate Similarity	NPD2403	Approved
0.7124	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1465	Phase 2
0.7086	Intermediate Similarity	NPD4287	Approved
0.7083	Intermediate Similarity	NPD1608	Approved
0.7067	Intermediate Similarity	NPD3140	Approved
0.7067	Intermediate Similarity	NPD3142	Approved
0.7063	Intermediate Similarity	NPD7458	Discontinued
0.7051	Intermediate Similarity	NPD2354	Approved
0.7051	Intermediate Similarity	NPD2309	Approved
0.7047	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6798	Discontinued
0.7047	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD230	Phase 1
0.7018	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD9697	Approved
0.7013	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD6808	Phase 2
0.7006	Intermediate Similarity	NPD7229	Phase 3
0.6987	Remote Similarity	NPD7003	Approved
0.6981	Remote Similarity	NPD2186	Approved
0.6977	Remote Similarity	NPD6104	Discontinued
0.6972	Remote Similarity	NPD1548	Phase 1
0.6959	Remote Similarity	NPD1729	Discontinued
0.6957	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD943	Approved
0.6948	Remote Similarity	NPD5405	Approved
0.6948	Remote Similarity	NPD5406	Approved
0.6948	Remote Similarity	NPD5404	Approved
0.6948	Remote Similarity	NPD5408	Approved
0.6943	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4360	Phase 2
0.6927	Remote Similarity	NPD4363	Phase 3
0.6923	Remote Similarity	NPD5691	Approved
0.6918	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4908	Phase 1
0.691	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6004	Phase 3
0.6903	Remote Similarity	NPD6005	Phase 3
0.6903	Remote Similarity	NPD6002	Phase 3
0.6889	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4361	Phase 2
0.6887	Remote Similarity	NPD8032	Phase 2
0.6875	Remote Similarity	NPD6273	Approved
0.6871	Remote Similarity	NPD1876	Approved
0.6868	Remote Similarity	NPD8285	Discontinued
0.6867	Remote Similarity	NPD6971	Discontinued
0.6866	Remote Similarity	NPD9261	Approved
0.6864	Remote Similarity	NPD5242	Approved
0.6855	Remote Similarity	NPD7390	Discontinued
0.6855	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1894	Discontinued
0.6852	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5353	Approved
0.6845	Remote Similarity	NPD7199	Phase 2
0.6839	Remote Similarity	NPD4477	Approved
0.6839	Remote Similarity	NPD4476	Approved
0.6838	Remote Similarity	NPD3134	Approved
0.6835	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6279	Approved
0.6829	Remote Similarity	NPD6280	Approved
0.6824	Remote Similarity	NPD1164	Approved
0.6797	Remote Similarity	NPD6355	Discontinued
0.6792	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7584	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