NPASS Compound

Structure

NPC470422 OpenBabel07101719402D 25 26 0 0 0 0 0 0 0 0999 V2000 -2.5019 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1698 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3358 -0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1698 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3358 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3358 1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5019 1.4444 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 -1.4444 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 5.0037 -0.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -0.4815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1698 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -0.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 25 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 8 2 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 19 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 25 1 0 0 0 0 9 13 1 0 0 0 0 10 13 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 20 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.0
Volume:	339.041
LogP:	4.359
LogD:	1.766
LogS:	-3.145
# Rotatable Bonds:	4
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	2.778
Fsp3:	0.125
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:	-5.3
MDCK Permeability:	1.2093657460354734e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.158
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	100.83842468261719%
Volume Distribution (VD):	0.385
Pgp-substrate:	1.5688741207122803%

ADMET: Metabolism

CYP1A2-inhibitor:	0.266
CYP1A2-substrate:	0.783
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.624
CYP2C9-substrate:	0.141
CYP2D6-inhibitor:	0.145
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	3.958
Half-life (T1/2):	0.658

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.456
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.724
Skin Sensitization:	0.217
Carcinogencity:	0.103
Eye Corrosion:	0.003
Eye Irritation:	0.738
Respiratory Toxicity:	0.613

Download Data

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

Natural Product: NPC470422

Natural Product ID:	NPC470422
*Common Name:**	2-(3,5-Dichloro-2,6-Dihydroxy-4-Methylbenzoyl)-5-Hydroxy-3-Methoxybenzoic Acid
IUPAC Name:	2-(3,5-dichloro-2,6-dihydroxy-4-methylbenzoyl)-5-hydroxy-3-methoxybenzoic acid
Synonyms:
Standard InCHIKey:	YEEFNWGKVFZRKL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12Cl2O7/c1-5-11(17)14(21)10(15(22)12(5)18)13(20)9-7(16(23)24)3-6(19)4-8(9)25-2/h3-4,19,21-22H,1-2H3,(H,23,24)
SMILES:	CC1=C(C(=C(C(=C1Cl)O)C(=O)C2=C(C=C(C=C2OC)O)C(=O)O)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2035566
PubChem CID:	70696431
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	from the rhizosphere of Opuntia versicolor of the Sonoran Desert	n.a.	PMID[14695798]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124769]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271552]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22360613]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24534845]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25671343]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2921224]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30207465]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32163285]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32897070]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984154]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	42.0	nM	PMID[449451]

☑ 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 NPC470422 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	429
0.1-0.2	2246
0.2-0.3	5746
0.3-0.4	12351
0.4-0.5	5383
0.5-0.6	5981
0.6-0.7	6738
0.7-0.8	3659
0.8-0.85	114
0.85-0.9	40
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC277865
0.9226	High Similarity	NPC264922
0.9107	High Similarity	NPC474857
0.8947	High Similarity	NPC45072
0.8929	High Similarity	NPC472032
0.8824	High Similarity	NPC470565
0.8713	High Similarity	NPC470562
0.8686	High Similarity	NPC151292
0.8663	High Similarity	NPC470560
0.8644	High Similarity	NPC191606
0.8642	High Similarity	NPC172329
0.8642	High Similarity	NPC2569
0.8639	High Similarity	NPC470081
0.8631	High Similarity	NPC298401
0.8629	High Similarity	NPC306240
0.8588	High Similarity	NPC173352
0.8588	High Similarity	NPC58653
0.858	High Similarity	NPC474096
0.858	High Similarity	NPC473696
0.8571	High Similarity	NPC28160
0.8547	High Similarity	NPC316091
0.8547	High Similarity	NPC471804
0.8547	High Similarity	NPC471812
0.8547	High Similarity	NPC313386
0.8538	High Similarity	NPC474061
0.8538	High Similarity	NPC28669
0.8523	High Similarity	NPC471801
0.8508	High Similarity	NPC220369
0.85	High Similarity	NPC39409
0.85	High Similarity	NPC121100
0.8492	Intermediate Similarity	NPC474499
0.8471	Intermediate Similarity	NPC470561
0.8462	Intermediate Similarity	NPC214901
0.8453	Intermediate Similarity	NPC471806
0.8453	Intermediate Similarity	NPC471810
0.8453	Intermediate Similarity	NPC471807
0.8452	Intermediate Similarity	NPC472404
0.8448	Intermediate Similarity	NPC188618
0.8421	Intermediate Similarity	NPC470563
0.8407	Intermediate Similarity	NPC221185
0.8398	Intermediate Similarity	NPC471813
0.8398	Intermediate Similarity	NPC471805
0.8378	Intermediate Similarity	NPC154720
0.8361	Intermediate Similarity	NPC247104
0.8354	Intermediate Similarity	NPC477569
0.8343	Intermediate Similarity	NPC471803
0.8343	Intermediate Similarity	NPC197326
0.8304	Intermediate Similarity	NPC472405
0.8297	Intermediate Similarity	NPC470100
0.8297	Intermediate Similarity	NPC470099
0.8284	Intermediate Similarity	NPC470564
0.8278	Intermediate Similarity	NPC99937
0.827	Intermediate Similarity	NPC198163
0.827	Intermediate Similarity	NPC313541
0.8253	Intermediate Similarity	NPC477566
0.8253	Intermediate Similarity	NPC477567
0.8242	Intermediate Similarity	NPC190648
0.8242	Intermediate Similarity	NPC56433
0.8242	Intermediate Similarity	NPC312929
0.8242	Intermediate Similarity	NPC118027
0.8242	Intermediate Similarity	NPC126767
0.8242	Intermediate Similarity	NPC289042
0.8242	Intermediate Similarity	NPC245584
0.8235	Intermediate Similarity	NPC263483
0.8221	Intermediate Similarity	NPC200207
0.8204	Intermediate Similarity	NPC470107
0.8204	Intermediate Similarity	NPC294646
0.8204	Intermediate Similarity	NPC295036
0.8204	Intermediate Similarity	NPC147735
0.8202	Intermediate Similarity	NPC108278
0.8187	Intermediate Similarity	NPC470559
0.8182	Intermediate Similarity	NPC225173
0.8182	Intermediate Similarity	NPC163846
0.8177	Intermediate Similarity	NPC195675
0.8171	Intermediate Similarity	NPC19896
0.816	Intermediate Similarity	NPC49108
0.816	Intermediate Similarity	NPC250755
0.8156	Intermediate Similarity	NPC471802
0.8146	Intermediate Similarity	NPC477568
0.8138	Intermediate Similarity	NPC108744
0.8133	Intermediate Similarity	NPC125801
0.8132	Intermediate Similarity	NPC471811
0.8132	Intermediate Similarity	NPC471809
0.8118	Intermediate Similarity	NPC48822
0.8107	Intermediate Similarity	NPC175978
0.8095	Intermediate Similarity	NPC255641
0.8095	Intermediate Similarity	NPC290954
0.8095	Intermediate Similarity	NPC119929
0.8095	Intermediate Similarity	NPC470568
0.8084	Intermediate Similarity	NPC153417
0.8077	Intermediate Similarity	NPC471814
0.8077	Intermediate Similarity	NPC471808
0.807	Intermediate Similarity	NPC280497
0.8057	Intermediate Similarity	NPC68850
0.8049	Intermediate Similarity	NPC182255
0.8049	Intermediate Similarity	NPC94076
0.8047	Intermediate Similarity	NPC39819
0.8047	Intermediate Similarity	NPC470569
0.8037	Intermediate Similarity	NPC165172
0.8036	Intermediate Similarity	NPC291049
0.8036	Intermediate Similarity	NPC233267
0.8033	Intermediate Similarity	NPC470103
0.8023	Intermediate Similarity	NPC148480
0.8012	Intermediate Similarity	NPC134621
0.8	Intermediate Similarity	NPC273483
0.8	Intermediate Similarity	NPC154683
0.8	Intermediate Similarity	NPC84266
0.8	Intermediate Similarity	NPC472006
0.8	Intermediate Similarity	NPC40356
0.7979	Intermediate Similarity	NPC193676
0.7978	Intermediate Similarity	NPC107283
0.7976	Intermediate Similarity	NPC105415
0.7965	Intermediate Similarity	NPC146211
0.7964	Intermediate Similarity	NPC237208
0.7964	Intermediate Similarity	NPC107625
0.7956	Intermediate Similarity	NPC472606
0.7953	Intermediate Similarity	NPC208806
0.7953	Intermediate Similarity	NPC107109
0.7952	Intermediate Similarity	NPC95123
0.7952	Intermediate Similarity	NPC66404
0.795	Intermediate Similarity	NPC182496
0.795	Intermediate Similarity	NPC180905
0.7943	Intermediate Similarity	NPC245122
0.7941	Intermediate Similarity	NPC133856
0.7939	Intermediate Similarity	NPC105648
0.7929	Intermediate Similarity	NPC70764
0.7927	Intermediate Similarity	NPC109232
0.7917	Intermediate Similarity	NPC34802
0.791	Intermediate Similarity	NPC29160
0.7907	Intermediate Similarity	NPC66508
0.7907	Intermediate Similarity	NPC38898
0.7907	Intermediate Similarity	NPC226656
0.7904	Intermediate Similarity	NPC29577
0.7904	Intermediate Similarity	NPC28632
0.7901	Intermediate Similarity	NPC175804
0.7895	Intermediate Similarity	NPC217447
0.7895	Intermediate Similarity	NPC281272
0.7892	Intermediate Similarity	NPC167663
0.7892	Intermediate Similarity	NPC310340
0.7892	Intermediate Similarity	NPC51106
0.7882	Intermediate Similarity	NPC474660
0.7882	Intermediate Similarity	NPC60413
0.7882	Intermediate Similarity	NPC202595
0.7879	Intermediate Similarity	NPC1704
0.7879	Intermediate Similarity	NPC220106
0.7879	Intermediate Similarity	NPC90411
0.7879	Intermediate Similarity	NPC67650
0.7874	Intermediate Similarity	NPC324736
0.787	Intermediate Similarity	NPC7025
0.787	Intermediate Similarity	NPC27221
0.787	Intermediate Similarity	NPC216624
0.787	Intermediate Similarity	NPC256672
0.7866	Intermediate Similarity	NPC472368
0.7865	Intermediate Similarity	NPC234331
0.7865	Intermediate Similarity	NPC76647
0.7861	Intermediate Similarity	NPC472050
0.7861	Intermediate Similarity	NPC77807
0.7861	Intermediate Similarity	NPC180924
0.7861	Intermediate Similarity	NPC14561
0.7861	Intermediate Similarity	NPC5379
0.7857	Intermediate Similarity	NPC267509
0.7857	Intermediate Similarity	NPC138978
0.7857	Intermediate Similarity	NPC472033
0.7853	Intermediate Similarity	NPC473391
0.7853	Intermediate Similarity	NPC472367
0.7853	Intermediate Similarity	NPC476333
0.7853	Intermediate Similarity	NPC472364
0.7853	Intermediate Similarity	NPC135837
0.7849	Intermediate Similarity	NPC136411
0.7849	Intermediate Similarity	NPC214632
0.7844	Intermediate Similarity	NPC21599
0.7844	Intermediate Similarity	NPC475201
0.7844	Intermediate Similarity	NPC48762
0.7844	Intermediate Similarity	NPC193703
0.7836	Intermediate Similarity	NPC115324
0.7836	Intermediate Similarity	NPC58668
0.7836	Intermediate Similarity	NPC106372
0.7831	Intermediate Similarity	NPC18714
0.7829	Intermediate Similarity	NPC84571
0.7829	Intermediate Similarity	NPC470342
0.7829	Intermediate Similarity	NPC472060
0.7829	Intermediate Similarity	NPC472052
0.7829	Intermediate Similarity	NPC143050
0.7824	Intermediate Similarity	NPC80370
0.7824	Intermediate Similarity	NPC158338
0.7824	Intermediate Similarity	NPC329933
0.7824	Intermediate Similarity	NPC65589
0.7824	Intermediate Similarity	NPC97028
0.7824	Intermediate Similarity	NPC288036
0.7824	Intermediate Similarity	NPC100985
0.7824	Intermediate Similarity	NPC6923
0.7824	Intermediate Similarity	NPC97029
0.7821	Intermediate Similarity	NPC99613
0.7821	Intermediate Similarity	NPC163130
0.7821	Intermediate Similarity	NPC49487
0.7821	Intermediate Similarity	NPC165979
0.7818	Intermediate Similarity	NPC472366
0.7816	Intermediate Similarity	NPC199463
0.7816	Intermediate Similarity	NPC246647
0.7816	Intermediate Similarity	NPC37543

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 NPC470422 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	1105
0.2-0.3	1970
0.3-0.4	2837
0.4-0.5	1745
0.5-0.6	774
0.6-0.7	253
0.7-0.8	57
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
0.7866	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6232	Discontinued
0.7809	Intermediate Similarity	NPD7473	Discontinued
0.7798	Intermediate Similarity	NPD2533	Approved
0.7798	Intermediate Similarity	NPD2534	Approved
0.7798	Intermediate Similarity	NPD2532	Approved
0.7778	Intermediate Similarity	NPD1607	Approved
0.7661	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1240	Approved
0.7654	Intermediate Similarity	NPD2403	Approved
0.7644	Intermediate Similarity	NPD7819	Suspended
0.7576	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1510	Phase 2
0.7514	Intermediate Similarity	NPD3226	Approved
0.7456	Intermediate Similarity	NPD3750	Approved
0.7425	Intermediate Similarity	NPD2935	Discontinued
0.7416	Intermediate Similarity	NPD3749	Approved
0.7389	Intermediate Similarity	NPD6959	Discontinued
0.7384	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6599	Discontinued
0.7353	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1549	Phase 2
0.7321	Intermediate Similarity	NPD1551	Phase 2
0.7288	Intermediate Similarity	NPD1934	Approved
0.7278	Intermediate Similarity	NPD2346	Discontinued
0.7278	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5710	Approved
0.7253	Intermediate Similarity	NPD5711	Approved
0.7247	Intermediate Similarity	NPD2801	Approved
0.7247	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7411	Suspended
0.7225	Intermediate Similarity	NPD1511	Approved
0.7225	Intermediate Similarity	NPD6799	Approved
0.7222	Intermediate Similarity	NPD7075	Discontinued
0.7207	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1184	Approved
0.7184	Intermediate Similarity	NPD1578	Phase 2
0.7175	Intermediate Similarity	NPD4380	Phase 2
0.7167	Intermediate Similarity	NPD3882	Suspended
0.7167	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3748	Approved
0.7151	Intermediate Similarity	NPD5844	Phase 1
0.7151	Intermediate Similarity	NPD1465	Phase 2
0.7151	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1512	Approved
0.7126	Intermediate Similarity	NPD7390	Discontinued
0.7118	Intermediate Similarity	NPD2796	Approved
0.7111	Intermediate Similarity	NPD3817	Phase 2
0.7111	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2800	Approved
0.7086	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4360	Phase 2
0.7077	Intermediate Similarity	NPD4363	Phase 3
0.7072	Intermediate Similarity	NPD7768	Phase 2
0.7062	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD943	Approved
0.7017	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD920	Approved
0.7005	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD6801	Discontinued
0.6994	Remote Similarity	NPD1243	Approved
0.6989	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5953	Discontinued
0.6982	Remote Similarity	NPD230	Phase 1
0.6977	Remote Similarity	NPD2344	Approved
0.6959	Remote Similarity	NPD2799	Discontinued
0.6954	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4361	Phase 2
0.6954	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4628	Phase 3
0.6947	Remote Similarity	NPD6559	Discontinued
0.6944	Remote Similarity	NPD958	Approved
0.6923	Remote Similarity	NPD5402	Approved
0.6919	Remote Similarity	NPD6100	Approved
0.6919	Remote Similarity	NPD5406	Approved
0.6919	Remote Similarity	NPD5408	Approved
0.6919	Remote Similarity	NPD5405	Approved
0.6919	Remote Similarity	NPD6099	Approved
0.6919	Remote Similarity	NPD5404	Approved
0.6914	Remote Similarity	NPD2354	Approved
0.6909	Remote Similarity	NPD1470	Approved
0.6905	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6166	Phase 2
0.6898	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7286	Phase 2
0.6872	Remote Similarity	NPD957	Approved
0.6865	Remote Similarity	NPD5494	Approved
0.686	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6651	Approved
0.6842	Remote Similarity	NPD7074	Phase 3
0.6823	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2309	Approved
0.6816	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD37	Approved
0.6807	Remote Similarity	NPD1203	Approved
0.6806	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3764	Approved
0.6805	Remote Similarity	NPD2313	Discontinued
0.6796	Remote Similarity	NPD8151	Discontinued
0.6789	Remote Similarity	NPD7054	Approved
0.6786	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2353	Approved
0.678	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7003	Approved
0.6755	Remote Similarity	NPD3926	Phase 2
0.6754	Remote Similarity	NPD7472	Approved
0.6747	Remote Similarity	NPD1283	Approved
0.6734	Remote Similarity	NPD6312	Discontinued
0.6726	Remote Similarity	NPD454	Approved
0.6723	Remote Similarity	NPD3887	Approved
0.6722	Remote Similarity	NPD5403	Approved
0.672	Remote Similarity	NPD919	Approved
0.672	Remote Similarity	NPD6234	Discontinued
0.6719	Remote Similarity	NPD6797	Phase 2
0.6716	Remote Similarity	NPD7435	Discontinued
0.6706	Remote Similarity	NPD411	Approved
0.6704	Remote Similarity	NPD5401	Approved
0.6703	Remote Similarity	NPD4965	Approved
0.6703	Remote Similarity	NPD4967	Phase 2
0.6703	Remote Similarity	NPD4966	Approved
0.6702	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD8313	Approved
0.6701	Remote Similarity	NPD8312	Approved
0.6686	Remote Similarity	NPD447	Suspended
0.6686	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7251	Discontinued
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1201	Approved
0.665	Remote Similarity	NPD6777	Approved
0.665	Remote Similarity	NPD6782	Approved
0.665	Remote Similarity	NPD6779	Approved
0.665	Remote Similarity	NPD6776	Approved
0.665	Remote Similarity	NPD6781	Approved
0.665	Remote Similarity	NPD6778	Approved
0.665	Remote Similarity	NPD6780	Approved
0.6649	Remote Similarity	NPD3751	Discontinued
0.6649	Remote Similarity	NPD7808	Phase 3
0.6649	Remote Similarity	NPD4288	Approved
0.6648	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7458	Discontinued
0.6627	Remote Similarity	NPD3972	Approved
0.6627	Remote Similarity	NPD9717	Approved
0.6627	Remote Similarity	NPD1608	Approved
0.6616	Remote Similarity	NPD4287	Approved
0.6614	Remote Similarity	NPD7229	Phase 3
0.6611	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD9493	Approved
0.6599	Remote Similarity	NPD8150	Discontinued
0.6591	Remote Similarity	NPD1471	Phase 3
0.6588	Remote Similarity	NPD6832	Phase 2
0.6566	Remote Similarity	NPD1281	Approved
0.6561	Remote Similarity	NPD1247	Approved
0.6553	Remote Similarity	NPD7697	Approved
0.6553	Remote Similarity	NPD7696	Phase 3
0.6553	Remote Similarity	NPD7698	Approved
0.6548	Remote Similarity	NPD1876	Approved
0.6545	Remote Similarity	NPD4626	Approved
0.6527	Remote Similarity	NPD9269	Phase 2
0.6524	Remote Similarity	NPD7874	Approved
0.6524	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD9545	Approved
0.6522	Remote Similarity	NPD7870	Phase 2
0.6522	Remote Similarity	NPD7871	Phase 2
0.6522	Remote Similarity	NPD4972	Discontinued
0.6517	Remote Similarity	NPD2654	Approved
0.6515	Remote Similarity	NPD8434	Phase 2
0.6514	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3268	Approved
0.6509	Remote Similarity	NPD1164	Approved
0.6503	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD5242	Approved
0.6485	Remote Similarity	NPD9268	Approved
0.648	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7177	Discontinued
0.6477	Remote Similarity	NPD7228	Approved
0.6477	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7199	Phase 2
0.6467	Remote Similarity	NPD422	Phase 1
0.6465	Remote Similarity	NPD6784	Approved
0.6465	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6785	Approved
0.6464	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD4625	Phase 3
0.6446	Remote Similarity	NPD17	Approved
0.6437	Remote Similarity	NPD2979	Phase 3
0.6437	Remote Similarity	NPD4307	Phase 2
0.6429	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7701	Phase 2
0.6412	Remote Similarity	NPD2797	Approved
0.6408	Remote Similarity	NPD7501	Clinical (unspecified phase)

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