NPASS Compound

Structure

NPC45072 OpenBabel07101718292D 27 29 0 0 0 0 0 0 0 0999 V2000 2.6228 -4.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 -4.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9916 -1.5777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -3.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -2.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -0.4010 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 3.4888 -4.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9944 -1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -2.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -0.8262 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 -0.5633 -2.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1238 -3.3797 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.8650 0.0747 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 -1.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 1.0990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 -2.9994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 -3.5291 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 5 1 0 0 0 0 4 8 2 0 0 0 0 5 10 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 27 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 14 2 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 15 18 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 25 2 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.05
Volume:	382.088
LogP:	6.136
LogD:	3.509
LogS:	-4.316
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.605
Synthetic Accessibility Score:	3.325
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:	-5.004
MDCK Permeability:	1.6405867427238263e-05
Pgp-inhibitor:	0.379
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.881
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	101.28217315673828%
Volume Distribution (VD):	1.485
Pgp-substrate:	1.3046636581420898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.643
CYP1A2-substrate:	0.496
CYP2C19-inhibitor:	0.41
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.813
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.131
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.145
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	12.196
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.44
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.679
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.866
Carcinogencity:	0.364
Eye Corrosion:	0.003
Eye Irritation:	0.903
Respiratory Toxicity:	0.594

Download Data

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

Natural Product: NPC45072

Natural Product ID:	NPC45072
*Common Name:**	Pestalachloride B
IUPAC Name:	2,4-dichloro-1,7,9-trihydroxy-3-methyl-10-(3-methylbut-2-enyl)-6H-benzo[c][1]benzoxepin-11-one
Synonyms:
Standard InCHIKey:	XCFFTGALQWABRD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18Cl2O5/c1-8(2)4-5-10-12(23)6-13(24)11-7-27-20-15(18(25)14(10)11)19(26)16(21)9(3)17(20)22/h4,6,23-24,26H,5,7H2,1-3H3
SMILES:	CC(=CCc1c(cc(c2COc3c(C(=O)c12)c(c(c(C)c3Cl)Cl)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513378
PubChem CID:	44562122
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001910] Benzoxepines [CHEMONTID:0001988] Dibenzoxepines

*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
NPO5567	Pestalotiopsis adusta	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18694644]
NPO40280	Pestalotiopsis neglecta	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31829592]
NPO40280	Pestalotiopsis neglecta	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32283019]
NPO5567	Pestalotiopsis adusta	Species	Sporocadaceae	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	4
MIC	3

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	50000.0	nM	PMID[511219]
NPT1278	Organism	Fusarium culmorum	Fusarium culmorum	IC50	=	4700.0	nM	PMID[511218]
NPT1278	Organism	Fusarium culmorum	Fusarium culmorum	MIC	=	49000.0	nM	PMID[511218]
NPT1276	Organism	Gibberella zeae	Gibberella zeae	IC50	=	1100.0	nM	PMID[511218]
NPT1276	Organism	Gibberella zeae	Gibberella zeae	MIC	=	12200.0	nM	PMID[511218]
NPT6600	Organism	Verticillium albo-atrum	Verticillium albo-atrum	IC50	=	7900.0	nM	PMID[511218]
NPT6600	Organism	Verticillium albo-atrum	Verticillium albo-atrum	MIC	=	12200.0	nM	PMID[511218]

☑ 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 NPC45072 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	466
0.1-0.2	2136
0.2-0.3	5648
0.3-0.4	13365
0.4-0.5	4583
0.5-0.6	5947
0.6-0.7	6938
0.7-0.8	3485
0.8-0.85	93
0.85-0.9	29
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9029	High Similarity	NPC474499
0.9	High Similarity	NPC474857
0.8947	High Similarity	NPC470422
0.8941	High Similarity	NPC277865
0.8895	High Similarity	NPC264922
0.8721	High Similarity	NPC470562
0.8721	High Similarity	NPC470565
0.8693	High Similarity	NPC151292
0.8674	High Similarity	NPC214901
0.8671	High Similarity	NPC470560
0.8652	High Similarity	NPC191606
0.8619	High Similarity	NPC220369
0.8596	High Similarity	NPC68850
0.8587	High Similarity	NPC154720
0.8571	High Similarity	NPC477568
0.8556	High Similarity	NPC471804
0.8556	High Similarity	NPC471812
0.8497	Intermediate Similarity	NPC472032
0.8478	Intermediate Similarity	NPC198163
0.8475	Intermediate Similarity	NPC28160
0.8462	Intermediate Similarity	NPC471810
0.8462	Intermediate Similarity	NPC471806
0.8462	Intermediate Similarity	NPC471807
0.843	Intermediate Similarity	NPC470563
0.8427	Intermediate Similarity	NPC471801
0.8407	Intermediate Similarity	NPC471813
0.8407	Intermediate Similarity	NPC121100
0.8407	Intermediate Similarity	NPC471805
0.8372	Intermediate Similarity	NPC470561
0.8352	Intermediate Similarity	NPC471803
0.8343	Intermediate Similarity	NPC148480
0.8324	Intermediate Similarity	NPC470081
0.8306	Intermediate Similarity	NPC39409
0.8251	Intermediate Similarity	NPC316091
0.8249	Intermediate Similarity	NPC188618
0.8225	Intermediate Similarity	NPC40356
0.8225	Intermediate Similarity	NPC154683
0.8208	Intermediate Similarity	NPC298401
0.8204	Intermediate Similarity	NPC5537
0.8192	Intermediate Similarity	NPC474004
0.8187	Intermediate Similarity	NPC280497
0.8187	Intermediate Similarity	NPC99937
0.8182	Intermediate Similarity	NPC193676
0.8176	Intermediate Similarity	NPC135522
0.8167	Intermediate Similarity	NPC472606
0.8167	Intermediate Similarity	NPC471802
0.8166	Intermediate Similarity	NPC149526
0.8166	Intermediate Similarity	NPC72958
0.8166	Intermediate Similarity	NPC232645
0.8166	Intermediate Similarity	NPC474417
0.8166	Intermediate Similarity	NPC478148
0.8161	Intermediate Similarity	NPC473696
0.8161	Intermediate Similarity	NPC474096
0.8161	Intermediate Similarity	NPC245122
0.8155	Intermediate Similarity	NPC158338
0.8155	Intermediate Similarity	NPC100985
0.8155	Intermediate Similarity	NPC288036
0.8155	Intermediate Similarity	NPC97028
0.8155	Intermediate Similarity	NPC65589
0.8155	Intermediate Similarity	NPC97029
0.8152	Intermediate Similarity	NPC313386
0.8142	Intermediate Similarity	NPC471811
0.8142	Intermediate Similarity	NPC471809
0.8125	Intermediate Similarity	NPC474061
0.8122	Intermediate Similarity	NPC306240
0.8121	Intermediate Similarity	NPC200207
0.8118	Intermediate Similarity	NPC221185
0.8118	Intermediate Similarity	NPC87708
0.8111	Intermediate Similarity	NPC108278
0.8108	Intermediate Similarity	NPC470099
0.8108	Intermediate Similarity	NPC470100
0.8107	Intermediate Similarity	NPC202595
0.8095	Intermediate Similarity	NPC7025
0.8095	Intermediate Similarity	NPC256672
0.8095	Intermediate Similarity	NPC27221
0.8092	Intermediate Similarity	NPC470559
0.8087	Intermediate Similarity	NPC195675
0.8087	Intermediate Similarity	NPC471814
0.8087	Intermediate Similarity	NPC471808
0.8081	Intermediate Similarity	NPC470564
0.8075	Intermediate Similarity	NPC247104
0.807	Intermediate Similarity	NPC210942
0.807	Intermediate Similarity	NPC169990
0.8068	Intermediate Similarity	NPC58653
0.8068	Intermediate Similarity	NPC173352
0.8047	Intermediate Similarity	NPC233267
0.8047	Intermediate Similarity	NPC291049
0.8036	Intermediate Similarity	NPC123202
0.8036	Intermediate Similarity	NPC22005
0.8036	Intermediate Similarity	NPC477569
0.8036	Intermediate Similarity	NPC71055
0.8036	Intermediate Similarity	NPC7943
0.8035	Intermediate Similarity	NPC472404
0.8035	Intermediate Similarity	NPC44199
0.8023	Intermediate Similarity	NPC28669
0.8012	Intermediate Similarity	NPC273483
0.8012	Intermediate Similarity	NPC473967
0.8012	Intermediate Similarity	NPC84266
0.8	Intermediate Similarity	NPC470568
0.7989	Intermediate Similarity	NPC107283
0.7989	Intermediate Similarity	NPC313541
0.7989	Intermediate Similarity	NPC186113
0.7988	Intermediate Similarity	NPC105415
0.7977	Intermediate Similarity	NPC180924
0.7976	Intermediate Similarity	NPC469758
0.7976	Intermediate Similarity	NPC99454
0.7976	Intermediate Similarity	NPC130176
0.7965	Intermediate Similarity	NPC329844
0.7953	Intermediate Similarity	NPC470569
0.7953	Intermediate Similarity	NPC133856
0.7952	Intermediate Similarity	NPC182255
0.7952	Intermediate Similarity	NPC94076
0.7943	Intermediate Similarity	NPC470810
0.7941	Intermediate Similarity	NPC10027
0.7941	Intermediate Similarity	NPC65775
0.7941	Intermediate Similarity	NPC477567
0.7941	Intermediate Similarity	NPC477566
0.7937	Intermediate Similarity	NPC48822
0.7931	Intermediate Similarity	NPC246647
0.7931	Intermediate Similarity	NPC164110
0.7931	Intermediate Similarity	NPC212967
0.7931	Intermediate Similarity	NPC96342
0.7929	Intermediate Similarity	NPC245584
0.7929	Intermediate Similarity	NPC126767
0.7929	Intermediate Similarity	NPC289042
0.7929	Intermediate Similarity	NPC118027
0.7929	Intermediate Similarity	NPC190648
0.7929	Intermediate Similarity	NPC56433
0.7929	Intermediate Similarity	NPC34802
0.7929	Intermediate Similarity	NPC312929
0.7919	Intermediate Similarity	NPC89625
0.7919	Intermediate Similarity	NPC149618
0.7917	Intermediate Similarity	NPC469764
0.7904	Intermediate Similarity	NPC310340
0.7898	Intermediate Similarity	NPC472405
0.7895	Intermediate Similarity	NPC227122
0.7895	Intermediate Similarity	NPC147735
0.7895	Intermediate Similarity	NPC325983
0.7895	Intermediate Similarity	NPC290954
0.7895	Intermediate Similarity	NPC255641
0.7886	Intermediate Similarity	NPC85121
0.7874	Intermediate Similarity	NPC146211
0.787	Intermediate Similarity	NPC225173
0.787	Intermediate Similarity	NPC290133
0.787	Intermediate Similarity	NPC187282
0.787	Intermediate Similarity	NPC24136
0.787	Intermediate Similarity	NPC163846
0.7865	Intermediate Similarity	NPC108744
0.7861	Intermediate Similarity	NPC214632
0.7857	Intermediate Similarity	NPC189650
0.7853	Intermediate Similarity	NPC473961
0.7849	Intermediate Similarity	NPC258249
0.7844	Intermediate Similarity	NPC49108
0.7841	Intermediate Similarity	NPC143050
0.7836	Intermediate Similarity	NPC329933
0.7829	Intermediate Similarity	NPC272196
0.7829	Intermediate Similarity	NPC201127
0.7824	Intermediate Similarity	NPC125801
0.7824	Intermediate Similarity	NPC308200
0.7816	Intermediate Similarity	NPC148938
0.7814	Intermediate Similarity	NPC175804
0.7811	Intermediate Similarity	NPC271288
0.7811	Intermediate Similarity	NPC134621
0.7809	Intermediate Similarity	NPC156082
0.7809	Intermediate Similarity	NPC197168
0.7803	Intermediate Similarity	NPC217447
0.7803	Intermediate Similarity	NPC474843
0.7797	Intermediate Similarity	NPC66288
0.7791	Intermediate Similarity	NPC294646
0.7791	Intermediate Similarity	NPC158866
0.7791	Intermediate Similarity	NPC13282
0.7791	Intermediate Similarity	NPC119929
0.779	Intermediate Similarity	NPC20543
0.779	Intermediate Similarity	NPC239440
0.7784	Intermediate Similarity	NPC275734
0.7778	Intermediate Similarity	NPC39195
0.7778	Intermediate Similarity	NPC145467
0.7778	Intermediate Similarity	NPC172329
0.7778	Intermediate Similarity	NPC2569
0.7778	Intermediate Similarity	NPC37139
0.7765	Intermediate Similarity	NPC112981
0.7765	Intermediate Similarity	NPC473927
0.7765	Intermediate Similarity	NPC234053
0.7765	Intermediate Similarity	NPC25361
0.7765	Intermediate Similarity	NPC237208
0.7765	Intermediate Similarity	NPC470570
0.7765	Intermediate Similarity	NPC196114
0.7759	Intermediate Similarity	NPC95842
0.7759	Intermediate Similarity	NPC472799
0.7759	Intermediate Similarity	NPC93552
0.7759	Intermediate Similarity	NPC183874
0.7759	Intermediate Similarity	NPC193200
0.7759	Intermediate Similarity	NPC280530
0.7759	Intermediate Similarity	NPC208806
0.7759	Intermediate Similarity	NPC235333
0.7759	Intermediate Similarity	NPC178964
0.7754	Intermediate Similarity	NPC470103
0.7751	Intermediate Similarity	NPC95123
0.7751	Intermediate Similarity	NPC66404
0.7751	Intermediate Similarity	NPC19896

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 NPC45072 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	1119
0.2-0.3	1913
0.3-0.4	2814
0.4-0.5	1723
0.5-0.6	838
0.6-0.7	273
0.7-0.8	54
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
0.7765	Intermediate Similarity	NPD2403	Approved
0.7697	Intermediate Similarity	NPD6959	Discontinued
0.7674	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7819	Suspended
0.7602	Intermediate Similarity	NPD2532	Approved
0.7602	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD2533	Approved
0.7602	Intermediate Similarity	NPD2534	Approved
0.7557	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1607	Approved
0.7363	Intermediate Similarity	NPD6232	Discontinued
0.7358	Intermediate Similarity	NPD4360	Phase 2
0.7358	Intermediate Similarity	NPD4363	Phase 3
0.7353	Intermediate Similarity	NPD1549	Phase 2
0.7353	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7473	Discontinued
0.732	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4361	Phase 2
0.7303	Intermediate Similarity	NPD1934	Approved
0.7299	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7278	Intermediate Similarity	NPD1510	Phase 2
0.7278	Intermediate Similarity	NPD3882	Suspended
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7267	Intermediate Similarity	NPD3750	Approved
0.7263	Intermediate Similarity	NPD2801	Approved
0.7247	Intermediate Similarity	NPD7411	Suspended
0.7246	Intermediate Similarity	NPD1240	Approved
0.7238	Intermediate Similarity	NPD7075	Discontinued
0.7235	Intermediate Similarity	NPD2796	Approved
0.7235	Intermediate Similarity	NPD1551	Phase 2
0.7232	Intermediate Similarity	NPD3226	Approved
0.7209	Intermediate Similarity	NPD2800	Approved
0.7193	Intermediate Similarity	NPD2346	Discontinued
0.7191	Intermediate Similarity	NPD4380	Phase 2
0.7191	Intermediate Similarity	NPD6599	Discontinued
0.7167	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD1511	Approved
0.7135	Intermediate Similarity	NPD2935	Discontinued
0.7102	Intermediate Similarity	NPD1578	Phase 2
0.7101	Intermediate Similarity	NPD1184	Approved
0.7097	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5710	Approved
0.7081	Intermediate Similarity	NPD5711	Approved
0.7074	Intermediate Similarity	NPD5844	Phase 1
0.7065	Intermediate Similarity	NPD5494	Approved
0.7062	Intermediate Similarity	NPD1512	Approved
0.7049	Intermediate Similarity	NPD3749	Approved
0.7045	Intermediate Similarity	NPD6799	Approved
0.7045	Intermediate Similarity	NPD7390	Discontinued
0.7035	Intermediate Similarity	NPD6099	Approved
0.7035	Intermediate Similarity	NPD6100	Approved
0.7017	Intermediate Similarity	NPD6801	Discontinued
0.7005	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6166	Phase 2
0.7005	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3748	Approved
0.6971	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4625	Phase 3
0.6957	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3817	Phase 2
0.6931	Remote Similarity	NPD3818	Discontinued
0.6919	Remote Similarity	NPD6312	Discontinued
0.6914	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5953	Discontinued
0.6902	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3303	Discontinued
0.686	Remote Similarity	NPD6651	Approved
0.6859	Remote Similarity	NPD7074	Phase 3
0.6851	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5402	Approved
0.6845	Remote Similarity	NPD454	Approved
0.6839	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD920	Approved
0.6824	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1243	Approved
0.6806	Remote Similarity	NPD7054	Approved
0.6806	Remote Similarity	NPD7286	Phase 2
0.6804	Remote Similarity	NPD8312	Approved
0.6804	Remote Similarity	NPD8313	Approved
0.68	Remote Similarity	NPD2344	Approved
0.6791	Remote Similarity	NPD3365	Discontinued
0.678	Remote Similarity	NPD4628	Phase 3
0.6776	Remote Similarity	NPD958	Approved
0.6771	Remote Similarity	NPD7472	Approved
0.6743	Remote Similarity	NPD5405	Approved
0.6743	Remote Similarity	NPD5408	Approved
0.6743	Remote Similarity	NPD5406	Approved
0.6743	Remote Similarity	NPD5404	Approved
0.674	Remote Similarity	NPD5403	Approved
0.6737	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6797	Phase 2
0.6734	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1470	Approved
0.6725	Remote Similarity	NPD2313	Discontinued
0.6722	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4908	Phase 1
0.6704	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD957	Approved
0.6703	Remote Similarity	NPD1465	Phase 2
0.6701	Remote Similarity	NPD7251	Discontinued
0.6687	Remote Similarity	NPD1201	Approved
0.6685	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7041	Phase 2
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7808	Phase 3
0.6649	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD37	Approved
0.6649	Remote Similarity	NPD6234	Discontinued
0.6649	Remote Similarity	NPD919	Approved
0.6648	Remote Similarity	NPD2309	Approved
0.6648	Remote Similarity	NPD4476	Approved
0.6648	Remote Similarity	NPD4477	Approved
0.6647	Remote Similarity	NPD943	Approved
0.6633	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7229	Phase 3
0.6631	Remote Similarity	NPD4967	Phase 2
0.6631	Remote Similarity	NPD4965	Approved
0.6631	Remote Similarity	NPD4966	Approved
0.663	Remote Similarity	NPD5401	Approved
0.663	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4972	Discontinued
0.6629	Remote Similarity	NPD4536	Approved
0.6629	Remote Similarity	NPD4538	Approved
0.6629	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1203	Approved
0.6615	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6832	Phase 2
0.6607	Remote Similarity	NPD4749	Approved
0.6606	Remote Similarity	NPD1651	Approved
0.6592	Remote Similarity	NPD7003	Approved
0.6587	Remote Similarity	NPD1610	Phase 2
0.6568	Remote Similarity	NPD1283	Approved
0.6556	Remote Similarity	NPD3887	Approved
0.6556	Remote Similarity	NPD2354	Approved
0.6552	Remote Similarity	NPD4060	Phase 1
0.6538	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD411	Approved
0.6517	Remote Similarity	NPD1471	Phase 3
0.6514	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6778	Approved
0.6505	Remote Similarity	NPD6779	Approved
0.6505	Remote Similarity	NPD6780	Approved
0.6505	Remote Similarity	NPD6782	Approved
0.6505	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6777	Approved
0.6505	Remote Similarity	NPD6781	Approved
0.6505	Remote Similarity	NPD6776	Approved
0.6503	Remote Similarity	NPD6273	Approved
0.6497	Remote Similarity	NPD4308	Phase 3
0.6497	Remote Similarity	NPD5588	Approved
0.6497	Remote Similarity	NPD5960	Phase 3
0.6497	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7177	Discontinued
0.6493	Remote Similarity	NPD8151	Discontinued
0.6491	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2798	Approved
0.6489	Remote Similarity	NPD4288	Approved
0.6488	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4534	Discontinued
0.6467	Remote Similarity	NPD4626	Approved
0.6457	Remote Similarity	NPD2979	Phase 3
0.645	Remote Similarity	NPD9717	Approved
0.6446	Remote Similarity	NPD1548	Phase 1
0.6444	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6823	Phase 2
0.6441	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3764	Approved
0.6437	Remote Similarity	NPD3268	Approved
0.6433	Remote Similarity	NPD2797	Approved
0.6429	Remote Similarity	NPD5058	Phase 3
0.6425	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2353	Approved
0.6425	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.642	Remote Similarity	NPD447	Suspended
0.642	Remote Similarity	NPD230	Phase 1
0.6411	Remote Similarity	NPD7698	Approved
0.6411	Remote Similarity	NPD7696	Phase 3
0.6411	Remote Similarity	NPD7697	Approved
0.6411	Remote Similarity	NPD7435	Discontinued
0.641	Remote Similarity	NPD3751	Discontinued
0.641	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7228	Approved
0.6407	Remote Similarity	NPD5691	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