NPASS Compound

Structure

CID198163 OpenBabel06191715582D 31 33 0 0 0 0 0 0 0 0999 V2000 -5.1120 -3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 -4.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8399 -0.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 0.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 -3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1044 -3.7517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 -3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4060 -1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5382 -2.8507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 -2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4088 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9693 -1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 -2.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 -0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9665 -1.8003 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.6677 -4.5779 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2459 -1.6235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0988 -3.6022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 0.8765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5984 0.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3799 -0.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.2470 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 8 1 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 29 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 24 2 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 19 2 0 0 0 0 12 13 1 0 0 0 0 12 25 2 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 17 27 1 0 0 0 0 18 21 2 0 0 0 0 18 30 1 0 0 0 0 19 30 1 0 0 0 0 20 29 1 0 0 0 0 21 31 1 0 0 0 0 22 28 2 0 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.08
Volume:	422.567
LogP:	5.056
LogD:	2.217
LogS:	-4.686
# Rotatable Bonds:	4
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	3.611
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.968
MDCK Permeability:	1.8018719856627285e-05
Pgp-inhibitor:	0.12
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.692
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	99.41136932373047%
Volume Distribution (VD):	0.476
Pgp-substrate:	1.6568114757537842%

ADMET: Metabolism

CYP1A2-inhibitor:	0.53
CYP1A2-substrate:	0.78
CYP2C19-inhibitor:	0.564
CYP2C19-substrate:	0.508
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.851
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.214
CYP3A4-inhibitor:	0.234
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	1.174
Half-life (T1/2):	0.337

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.016
Drug-inuced Liver Injury (DILI):	0.34
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.998
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.797
Carcinogencity:	0.705
Eye Corrosion:	0.02
Eye Irritation:	0.951
Respiratory Toxicity:	0.74

Download Data

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

Natural Product: NPC198163

Natural Product ID:	NPC198163
*Common Name:**	Mollicellin E
IUPAC Name:	8-chloro-4,9-dihydroxy-3-methoxy-1,7-dimethyl-2-(3-methylbut-2-enoyl)-6-oxobenzo[b][1,4]benzodioxepine-10-carbaldehyde
Synonyms:	Mollicellin E
Standard InCHIKey:	JTGLZOMMRQOKBM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H19ClO8/c1-8(2)6-12(25)13-10(4)18-21(17(27)20(13)29-5)31-22(28)14-9(3)15(23)16(26)11(7-24)19(14)30-18/h6-7,26-27H,1-5H3
SMILES:	COc1c(O)c2OC(=O)c3c(Oc2c(c1C(=O)C=C(C)C)C)c(C=O)c(c(c3C)Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081162
PubChem CID:	50201
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO30621	Chaetomium brasiliense	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19663417]
NPO30621	Chaetomium brasiliense	Species	Chaetomiaceae	Eukaryota	n.a.	Doi Inthanon, Jomtong District, Chiangmai Province, Thailand	2006-JUN	PMID[19663417]
NPO30621	Chaetomium brasiliense	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]

☑ 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	8

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	5
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[501059]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.83	ug.mL-1	PMID[501059]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.03	ug.mL-1	PMID[501059]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.22	ug.mL-1	PMID[501059]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.44	ug.mL-1	PMID[501059]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.81	ug.mL-1	PMID[501059]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3.2	ug.mL-1	PMID[501059]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	39.7	ug.mL-1	PMID[501059]

☑ 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 NPC198163 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	472
0.1-0.2	2298
0.2-0.3	5766
0.3-0.4	12081
0.4-0.5	6095
0.5-0.6	5469
0.6-0.7	6825
0.7-0.8	3583
0.8-0.85	75
0.85-0.9	28
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC193676
0.9556	High Similarity	NPC214901
0.95	High Similarity	NPC220369
0.9454	High Similarity	NPC154720
0.9	High Similarity	NPC471801
0.8833	High Similarity	NPC139350
0.871	High Similarity	NPC471804
0.871	High Similarity	NPC471812
0.871	High Similarity	NPC471803
0.8689	High Similarity	NPC113446
0.8667	High Similarity	NPC20543
0.8667	High Similarity	NPC239440
0.8667	High Similarity	NPC246716
0.8634	High Similarity	NPC471802
0.8626	High Similarity	NPC477568
0.8619	High Similarity	NPC188618
0.8617	High Similarity	NPC471806
0.8617	High Similarity	NPC471810
0.8617	High Similarity	NPC471807
0.8611	High Similarity	NPC26568
0.8602	High Similarity	NPC471811
0.8602	High Similarity	NPC471809
0.8571	High Similarity	NPC181523
0.8564	High Similarity	NPC121100
0.8564	High Similarity	NPC1827
0.8564	High Similarity	NPC471805
0.8564	High Similarity	NPC39409
0.8564	High Similarity	NPC471813
0.8564	High Similarity	NPC10576
0.8556	High Similarity	NPC272485
0.8556	High Similarity	NPC292788
0.8548	High Similarity	NPC471808
0.8548	High Similarity	NPC195675
0.8548	High Similarity	NPC471814
0.8525	High Similarity	NPC289147
0.8478	Intermediate Similarity	NPC45072
0.8478	Intermediate Similarity	NPC108278
0.8432	Intermediate Similarity	NPC28160
0.8398	Intermediate Similarity	NPC20216
0.8389	Intermediate Similarity	NPC156082
0.8361	Intermediate Similarity	NPC17219
0.8361	Intermediate Similarity	NPC124470
0.8361	Intermediate Similarity	NPC109827
0.8343	Intermediate Similarity	NPC112981
0.8343	Intermediate Similarity	NPC8070
0.8315	Intermediate Similarity	NPC158226
0.8315	Intermediate Similarity	NPC474857
0.8289	Intermediate Similarity	NPC240887
0.8289	Intermediate Similarity	NPC329161
0.8289	Intermediate Similarity	NPC470091
0.828	Intermediate Similarity	NPC175804
0.827	Intermediate Similarity	NPC470422
0.8242	Intermediate Similarity	NPC267153
0.8232	Intermediate Similarity	NPC93739
0.8226	Intermediate Similarity	NPC264922
0.8222	Intermediate Similarity	NPC143050
0.8207	Intermediate Similarity	NPC163130
0.8207	Intermediate Similarity	NPC49487
0.8207	Intermediate Similarity	NPC99613
0.8207	Intermediate Similarity	NPC165979
0.8187	Intermediate Similarity	NPC300984
0.8187	Intermediate Similarity	NPC284007
0.8187	Intermediate Similarity	NPC474350
0.8167	Intermediate Similarity	NPC168616
0.8167	Intermediate Similarity	NPC83763
0.8167	Intermediate Similarity	NPC238381
0.8162	Intermediate Similarity	NPC277865
0.8152	Intermediate Similarity	NPC472032
0.8144	Intermediate Similarity	NPC247104
0.8098	Intermediate Similarity	NPC29160
0.8093	Intermediate Similarity	NPC221185
0.8087	Intermediate Similarity	NPC236132
0.8087	Intermediate Similarity	NPC270837
0.8077	Intermediate Similarity	NPC303565
0.8073	Intermediate Similarity	NPC474499
0.8061	Intermediate Similarity	NPC313541
0.8056	Intermediate Similarity	NPC54928
0.8054	Intermediate Similarity	NPC234331
0.8033	Intermediate Similarity	NPC294965
0.8031	Intermediate Similarity	NPC316091
0.803	Intermediate Similarity	NPC108744
0.8022	Intermediate Similarity	NPC14353
0.8022	Intermediate Similarity	NPC56085
0.8022	Intermediate Similarity	NPC200594
0.8022	Intermediate Similarity	NPC228785
0.8021	Intermediate Similarity	NPC191606
0.8	Intermediate Similarity	NPC89625
0.8	Intermediate Similarity	NPC471800
0.8	Intermediate Similarity	NPC149618
0.799	Intermediate Similarity	NPC470099
0.799	Intermediate Similarity	NPC470100
0.7989	Intermediate Similarity	NPC470081
0.7989	Intermediate Similarity	NPC234004
0.7989	Intermediate Similarity	NPC29055
0.7989	Intermediate Similarity	NPC197168
0.7989	Intermediate Similarity	NPC7483
0.7978	Intermediate Similarity	NPC61010
0.7978	Intermediate Similarity	NPC66288
0.7978	Intermediate Similarity	NPC40491
0.7978	Intermediate Similarity	NPC278052
0.7967	Intermediate Similarity	NPC45846
0.7967	Intermediate Similarity	NPC100123
0.7967	Intermediate Similarity	NPC315157
0.7958	Intermediate Similarity	NPC151292
0.7956	Intermediate Similarity	NPC472456
0.7956	Intermediate Similarity	NPC280497
0.7956	Intermediate Similarity	NPC197751
0.7947	Intermediate Similarity	NPC207467
0.7946	Intermediate Similarity	NPC25361
0.7946	Intermediate Similarity	NPC326520
0.7935	Intermediate Similarity	NPC245122
0.7935	Intermediate Similarity	NPC474096
0.7935	Intermediate Similarity	NPC108767
0.7935	Intermediate Similarity	NPC144843
0.7935	Intermediate Similarity	NPC8300
0.7923	Intermediate Similarity	NPC474287
0.7923	Intermediate Similarity	NPC320359
0.7923	Intermediate Similarity	NPC475886
0.7923	Intermediate Similarity	NPC119224
0.7919	Intermediate Similarity	NPC48822
0.7912	Intermediate Similarity	NPC300727
0.7912	Intermediate Similarity	NPC241904
0.7912	Intermediate Similarity	NPC165977
0.7912	Intermediate Similarity	NPC217677
0.791	Intermediate Similarity	NPC477569
0.7906	Intermediate Similarity	NPC473785
0.7903	Intermediate Similarity	NPC170245
0.7903	Intermediate Similarity	NPC472452
0.7903	Intermediate Similarity	NPC37870
0.7901	Intermediate Similarity	NPC16286
0.7892	Intermediate Similarity	NPC475055
0.7892	Intermediate Similarity	NPC248638
0.7892	Intermediate Similarity	NPC101769
0.7892	Intermediate Similarity	NPC152659
0.7892	Intermediate Similarity	NPC220313
0.7892	Intermediate Similarity	NPC236521
0.7892	Intermediate Similarity	NPC41301
0.7889	Intermediate Similarity	NPC289968
0.788	Intermediate Similarity	NPC474186
0.788	Intermediate Similarity	NPC474187
0.788	Intermediate Similarity	NPC472405
0.788	Intermediate Similarity	NPC475883
0.788	Intermediate Similarity	NPC266314
0.788	Intermediate Similarity	NPC474351
0.788	Intermediate Similarity	NPC298401
0.7876	Intermediate Similarity	NPC99937
0.7872	Intermediate Similarity	NPC470565
0.7872	Intermediate Similarity	NPC470562
0.7869	Intermediate Similarity	NPC250214
0.7869	Intermediate Similarity	NPC476242
0.7869	Intermediate Similarity	NPC85121
0.7869	Intermediate Similarity	NPC95936
0.7861	Intermediate Similarity	NPC474024
0.7861	Intermediate Similarity	NPC117854
0.7861	Intermediate Similarity	NPC6588
0.7861	Intermediate Similarity	NPC477154
0.7857	Intermediate Similarity	NPC274730
0.7857	Intermediate Similarity	NPC142339
0.7849	Intermediate Similarity	NPC85057
0.7849	Intermediate Similarity	NPC239752
0.7849	Intermediate Similarity	NPC275780
0.7849	Intermediate Similarity	NPC173352
0.7849	Intermediate Similarity	NPC58653
0.7849	Intermediate Similarity	NPC327652
0.7849	Intermediate Similarity	NPC130920
0.7849	Intermediate Similarity	NPC472450
0.7846	Intermediate Similarity	NPC313386
0.7842	Intermediate Similarity	NPC245975
0.7838	Intermediate Similarity	NPC473696
0.7838	Intermediate Similarity	NPC25152
0.7838	Intermediate Similarity	NPC470694
0.7833	Intermediate Similarity	NPC133856
0.7831	Intermediate Similarity	NPC470560
0.7826	Intermediate Similarity	NPC36217
0.7826	Intermediate Similarity	NPC47623
0.7826	Intermediate Similarity	NPC84571
0.7821	Intermediate Similarity	NPC477567
0.7821	Intermediate Similarity	NPC477566
0.7814	Intermediate Similarity	NPC223787
0.7814	Intermediate Similarity	NPC36852
0.7814	Intermediate Similarity	NPC78225
0.7814	Intermediate Similarity	NPC302258
0.7814	Intermediate Similarity	NPC262286
0.7814	Intermediate Similarity	NPC469584
0.7814	Intermediate Similarity	NPC236796
0.7812	Intermediate Similarity	NPC306240
0.7809	Intermediate Similarity	NPC251188
0.7807	Intermediate Similarity	NPC28669
0.7807	Intermediate Similarity	NPC39091
0.7807	Intermediate Similarity	NPC43319
0.7807	Intermediate Similarity	NPC329119
0.7806	Intermediate Similarity	NPC295436
0.7796	Intermediate Similarity	NPC173587
0.7796	Intermediate Similarity	NPC23298
0.7796	Intermediate Similarity	NPC477689
0.7796	Intermediate Similarity	NPC317781
0.7796	Intermediate Similarity	NPC207690
0.7796	Intermediate Similarity	NPC475985
0.7796	Intermediate Similarity	NPC470459
0.7796	Intermediate Similarity	NPC189473

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 NPC198163 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	1234
0.2-0.3	2346
0.3-0.4	2753
0.4-0.5	1526
0.5-0.6	617
0.6-0.7	211
0.7-0.8	43
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7742	Intermediate Similarity	NPD6232	Discontinued
0.7713	Intermediate Similarity	NPD7473	Discontinued
0.765	Intermediate Similarity	NPD2801	Approved
0.7632	Intermediate Similarity	NPD5844	Phase 1
0.7598	Intermediate Similarity	NPD2534	Approved
0.7598	Intermediate Similarity	NPD2533	Approved
0.7598	Intermediate Similarity	NPD2532	Approved
0.7554	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1934	Approved
0.7474	Intermediate Similarity	NPD2403	Approved
0.7419	Intermediate Similarity	NPD3817	Phase 2
0.7385	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD3882	Suspended
0.738	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD1465	Phase 2
0.7366	Intermediate Similarity	NPD7819	Suspended
0.7337	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD3818	Discontinued
0.7292	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6166	Phase 2
0.7263	Intermediate Similarity	NPD5494	Approved
0.7249	Intermediate Similarity	NPD7075	Discontinued
0.7231	Intermediate Similarity	NPD7074	Phase 3
0.7225	Intermediate Similarity	NPD6959	Discontinued
0.7179	Intermediate Similarity	NPD7054	Approved
0.7174	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD1511	Approved
0.7157	Intermediate Similarity	NPD6559	Discontinued
0.7151	Intermediate Similarity	NPD3226	Approved
0.7143	Intermediate Similarity	NPD7472	Approved
0.7135	Intermediate Similarity	NPD1247	Approved
0.712	Intermediate Similarity	NPD919	Approved
0.7112	Intermediate Similarity	NPD6599	Discontinued
0.7107	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD5711	Approved
0.7098	Intermediate Similarity	NPD5710	Approved
0.709	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1512	Approved
0.7074	Intermediate Similarity	NPD7411	Suspended
0.7037	Intermediate Similarity	NPD6801	Discontinued
0.7031	Intermediate Similarity	NPD6234	Discontinued
0.7027	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4380	Phase 2
0.702	Intermediate Similarity	NPD6797	Phase 2
0.701	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7251	Discontinued
0.6978	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6799	Approved
0.6963	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5402	Approved
0.695	Remote Similarity	NPD7808	Phase 3
0.694	Remote Similarity	NPD2800	Approved
0.6939	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD2935	Discontinued
0.6868	Remote Similarity	NPD1551	Phase 2
0.6862	Remote Similarity	NPD920	Approved
0.686	Remote Similarity	NPD4363	Phase 3
0.686	Remote Similarity	NPD4360	Phase 2
0.6859	Remote Similarity	NPD37	Approved
0.6847	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4965	Approved
0.6839	Remote Similarity	NPD4967	Phase 2
0.6839	Remote Similarity	NPD4966	Approved
0.6834	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2346	Discontinued
0.6814	Remote Similarity	NPD8434	Phase 2
0.6804	Remote Similarity	NPD3749	Approved
0.6786	Remote Similarity	NPD7199	Phase 2
0.6784	Remote Similarity	NPD7228	Approved
0.6777	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7768	Phase 2
0.6749	Remote Similarity	NPD8312	Approved
0.6749	Remote Similarity	NPD8313	Approved
0.6746	Remote Similarity	NPD4361	Phase 2
0.6746	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.674	Remote Similarity	NPD230	Phase 1
0.6739	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2799	Discontinued
0.672	Remote Similarity	NPD4628	Phase 3
0.672	Remote Similarity	NPD3750	Approved
0.6717	Remote Similarity	NPD3926	Phase 2
0.6717	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1607	Approved
0.6703	Remote Similarity	NPD1549	Phase 2
0.6697	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7783	Phase 2
0.6683	Remote Similarity	NPD5953	Discontinued
0.6682	Remote Similarity	NPD8151	Discontinued
0.6682	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8150	Discontinued
0.6649	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD447	Suspended
0.663	Remote Similarity	NPD1510	Phase 2
0.663	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6779	Approved
0.662	Remote Similarity	NPD6777	Approved
0.662	Remote Similarity	NPD6782	Approved
0.662	Remote Similarity	NPD6776	Approved
0.662	Remote Similarity	NPD6781	Approved
0.662	Remote Similarity	NPD6778	Approved
0.662	Remote Similarity	NPD6780	Approved
0.6614	Remote Similarity	NPD7390	Discontinued
0.6612	Remote Similarity	NPD6651	Approved
0.6597	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5403	Approved
0.6595	Remote Similarity	NPD2796	Approved
0.6593	Remote Similarity	NPD943	Approved
0.6593	Remote Similarity	NPD1240	Approved
0.6584	Remote Similarity	NPD7286	Phase 2
0.6579	Remote Similarity	NPD1578	Phase 2
0.6578	Remote Similarity	NPD1243	Approved
0.6562	Remote Similarity	NPD1653	Approved
0.6546	Remote Similarity	NPD958	Approved
0.6541	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD2354	Approved
0.65	Remote Similarity	NPD7874	Approved
0.65	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD5401	Approved
0.6484	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6534	Approved
0.6462	Remote Similarity	NPD6535	Approved
0.6455	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD3751	Discontinued
0.6452	Remote Similarity	NPD7696	Phase 3
0.6452	Remote Similarity	NPD7697	Approved
0.6452	Remote Similarity	NPD7698	Approved
0.6452	Remote Similarity	NPD3748	Approved
0.6447	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6785	Approved
0.6442	Remote Similarity	NPD6784	Approved
0.6422	Remote Similarity	NPD7871	Phase 2
0.6422	Remote Similarity	NPD7870	Phase 2
0.6421	Remote Similarity	NPD6190	Approved
0.6421	Remote Similarity	NPD3887	Approved
0.6418	Remote Similarity	NPD3787	Discontinued
0.6418	Remote Similarity	NPD7229	Phase 3
0.6417	Remote Similarity	NPD6100	Approved
0.6417	Remote Similarity	NPD6099	Approved
0.6409	Remote Similarity	NPD7701	Phase 2
0.6408	Remote Similarity	NPD7240	Approved
0.6406	Remote Similarity	NPD6823	Phase 2
0.6393	Remote Similarity	NPD2313	Discontinued
0.6392	Remote Similarity	NPD957	Approved
0.6386	Remote Similarity	NPD5242	Approved
0.6372	Remote Similarity	NPD7700	Phase 2
0.6372	Remote Similarity	NPD7699	Phase 2
0.6364	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.635	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD1852	Discontinued
0.6343	Remote Similarity	NPD8285	Discontinued
0.6339	Remote Similarity	NPD3027	Phase 3
0.633	Remote Similarity	NPD5405	Approved
0.633	Remote Similarity	NPD5404	Approved
0.633	Remote Similarity	NPD5408	Approved
0.633	Remote Similarity	NPD5406	Approved
0.6329	Remote Similarity	NPD7685	Pre-registration
0.6327	Remote Similarity	NPD4972	Discontinued
0.6326	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD1613	Approved
0.6324	Remote Similarity	NPD4060	Phase 1
0.6324	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD7801	Approved
0.6319	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD9494	Approved
0.6316	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6674	Discontinued
0.6304	Remote Similarity	NPD7985	Registered
0.6298	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2353	Approved
0.6296	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.629	Remote Similarity	NPD1184	Approved
0.6287	Remote Similarity	NPD8127	Discontinued
0.6284	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6832	Phase 2
0.6276	Remote Similarity	NPD7458	Discontinued
0.6263	Remote Similarity	NPD4534	Discontinued
0.6262	Remote Similarity	NPD6212	Phase 3
0.6262	Remote Similarity	NPD6213	Phase 3
0.6262	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD6312	Discontinued
0.623	Remote Similarity	NPD454	Approved
0.6223	Remote Similarity	NPD4536	Approved
0.6223	Remote Similarity	NPD4538	Approved
0.6223	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD7907	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