NPASS Compound

Structure

NPC472405 OpenBabel07101718182D 25 26 0 0 1 0 0 0 0 0999 V2000 -0.6072 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 -3.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9392 -2.5731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 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 -2.7321 -2.7321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 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 -3.2321 -1.8660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3660 -3.3660 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6072 -4.1980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1980 -1.6072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 18 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 2 0 0 0 0 6 18 1 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 10 25 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.1
Volume:	354.905
LogP:	3.517
LogD:	2.147
LogS:	-3.503
# Rotatable Bonds:	0
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.608
Synthetic Accessibility Score:	4.496
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.691
MDCK Permeability:	2.326310823264066e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.115
Plasma Protein Binding (PPB):	96.0564193725586%
Volume Distribution (VD):	0.67
Pgp-substrate:	5.360220909118652%

ADMET: Metabolism

CYP1A2-inhibitor:	0.89
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.456
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.751
CYP2C9-substrate:	0.771
CYP2D6-inhibitor:	0.664
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.599
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	13.161
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.64
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.865
Skin Sensitization:	0.612
Carcinogencity:	0.404
Eye Corrosion:	0.004
Eye Irritation:	0.211
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC472405

Natural Product ID:	NPC472405
*Common Name:**	14-Chloro-5,11,13-Trihydroxy-4,5,9-Trimethyl-4,5,6,7-Tetrahydro-1H-Benzo[D][1]Oxacyclododecine-2,10-Dione
IUPAC Name:	(9E)-16-chloro-6,13,15-trihydroxy-5,6,10-trimethyl-4-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraene-3,11-dione
Synonyms:
Standard InCHIKey:	CKSXTSLBLCBNFG-WEVVVXLNSA-N
Standard InCHI:	InChI=1S/C18H21ClO6/c1-9-5-4-6-18(3,24)10(2)25-14(22)7-11-15(17(9)23)12(20)8-13(21)16(11)19/h5,8,10,20-21,24H,4,6-7H2,1-3H3/b9-5+
SMILES:	O=C1Cc2c(Cl)c(O)cc(c2C(=O)/C(=C/CCC(C(O1)C)(C)O)/C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3400936
PubChem CID:	24863018
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO30056	Exserohilum rostratum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332857]
NPO30056	Exserohilum rostratum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18774863]
NPO30056	Exserohilum rostratum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25537529]

☑ 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	2
Others	1

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	>	70.0	%	PMID[522886]
NPT2	Others	Unspecified		IC50	=	136.0	nM	PMID[522886]

☑ 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 NPC472405 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	381
0.1-0.2	1769
0.2-0.3	4857
0.3-0.4	11632
0.4-0.5	7799
0.5-0.6	6722
0.6-0.7	8104
0.7-0.8	1366
0.8-0.85	47
0.85-0.9	6
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9673	High Similarity	NPC472404
0.9487	High Similarity	NPC298401
0.9427	High Similarity	NPC473696
0.9308	High Similarity	NPC58653
0.9308	High Similarity	NPC173352
0.925	High Similarity	NPC28669
0.925	High Similarity	NPC474061
0.9245	High Similarity	NPC470081
0.9193	High Similarity	NPC472032
0.9182	High Similarity	NPC474096
0.8608	High Similarity	NPC477566
0.8608	High Similarity	NPC477567
0.8599	High Similarity	NPC477569
0.8555	High Similarity	NPC470103
0.8497	Intermediate Similarity	NPC9121
0.8497	Intermediate Similarity	NPC472403
0.8497	Intermediate Similarity	NPC177307
0.8431	Intermediate Similarity	NPC474771
0.8431	Intermediate Similarity	NPC178467
0.8431	Intermediate Similarity	NPC149372
0.8431	Intermediate Similarity	NPC474849
0.8431	Intermediate Similarity	NPC65837
0.8409	Intermediate Similarity	NPC470100
0.8377	Intermediate Similarity	NPC475974
0.8373	Intermediate Similarity	NPC245122
0.8371	Intermediate Similarity	NPC247104
0.8333	Intermediate Similarity	NPC478201
0.8333	Intermediate Similarity	NPC472035
0.8315	Intermediate Similarity	NPC221185
0.8305	Intermediate Similarity	NPC470099
0.8304	Intermediate Similarity	NPC470422
0.8256	Intermediate Similarity	NPC477568
0.8249	Intermediate Similarity	NPC136411
0.8222	Intermediate Similarity	NPC48822
0.8218	Intermediate Similarity	NPC471801
0.8217	Intermediate Similarity	NPC478217
0.8217	Intermediate Similarity	NPC313123
0.8205	Intermediate Similarity	NPC474655
0.8182	Intermediate Similarity	NPC280497
0.8176	Intermediate Similarity	NPC478203
0.8176	Intermediate Similarity	NPC126882
0.8176	Intermediate Similarity	NPC210966
0.8153	Intermediate Similarity	NPC158472
0.8142	Intermediate Similarity	NPC108744
0.8141	Intermediate Similarity	NPC191835
0.8141	Intermediate Similarity	NPC33144
0.8141	Intermediate Similarity	NPC478200
0.814	Intermediate Similarity	NPC474857
0.8125	Intermediate Similarity	NPC257558
0.8125	Intermediate Similarity	NPC472034
0.8113	Intermediate Similarity	NPC354984
0.8113	Intermediate Similarity	NPC478202
0.8107	Intermediate Similarity	NPC470563
0.8084	Intermediate Similarity	NPC470559
0.8081	Intermediate Similarity	NPC277865
0.8079	Intermediate Similarity	NPC99937
0.8077	Intermediate Similarity	NPC70380
0.8075	Intermediate Similarity	NPC472033
0.8066	Intermediate Similarity	NPC214901
0.8047	Intermediate Similarity	NPC470561
0.8046	Intermediate Similarity	NPC264922
0.8025	Intermediate Similarity	NPC94248
0.8025	Intermediate Similarity	NPC212693
0.8025	Intermediate Similarity	NPC472036
0.8024	Intermediate Similarity	NPC197326
0.8011	Intermediate Similarity	NPC220369
0.8	Intermediate Similarity	NPC39409
0.7989	Intermediate Similarity	NPC154720
0.7988	Intermediate Similarity	NPC472891
0.7978	Intermediate Similarity	NPC313541
0.7975	Intermediate Similarity	NPC92655
0.7975	Intermediate Similarity	NPC215711
0.7975	Intermediate Similarity	NPC73411
0.7964	Intermediate Similarity	NPC470564
0.7963	Intermediate Similarity	NPC473023
0.7962	Intermediate Similarity	NPC71256
0.7961	Intermediate Similarity	NPC41263
0.7952	Intermediate Similarity	NPC55092
0.795	Intermediate Similarity	NPC86373
0.795	Intermediate Similarity	NPC277426
0.795	Intermediate Similarity	NPC280404
0.795	Intermediate Similarity	NPC210425
0.7944	Intermediate Similarity	NPC471812
0.7944	Intermediate Similarity	NPC471803
0.7944	Intermediate Similarity	NPC471804
0.7944	Intermediate Similarity	NPC316091
0.7935	Intermediate Similarity	NPC153783
0.7914	Intermediate Similarity	NPC210320
0.7911	Intermediate Similarity	NPC472602
0.7904	Intermediate Similarity	NPC478221
0.7904	Intermediate Similarity	NPC472890
0.7901	Intermediate Similarity	NPC83272
0.7898	Intermediate Similarity	NPC45072
0.7898	Intermediate Similarity	NPC235115
0.7892	Intermediate Similarity	NPC478224
0.7892	Intermediate Similarity	NPC76041
0.7892	Intermediate Similarity	NPC184284
0.7892	Intermediate Similarity	NPC115249
0.7892	Intermediate Similarity	NPC213224
0.7888	Intermediate Similarity	NPC472006
0.788	Intermediate Similarity	NPC198163
0.7879	Intermediate Similarity	NPC56204
0.7875	Intermediate Similarity	NPC1704
0.7875	Intermediate Similarity	NPC158634
0.7875	Intermediate Similarity	NPC53649
0.7875	Intermediate Similarity	NPC472603
0.7875	Intermediate Similarity	NPC244923
0.7875	Intermediate Similarity	NPC67650
0.7874	Intermediate Similarity	NPC107283
0.7874	Intermediate Similarity	NPC470562
0.7866	Intermediate Similarity	NPC471641
0.7866	Intermediate Similarity	NPC240622
0.7866	Intermediate Similarity	NPC471642
0.7866	Intermediate Similarity	NPC240253
0.7862	Intermediate Similarity	NPC268052
0.7862	Intermediate Similarity	NPC247409
0.7862	Intermediate Similarity	NPC52358
0.7862	Intermediate Similarity	NPC32360
0.7862	Intermediate Similarity	NPC105456
0.7862	Intermediate Similarity	NPC139634
0.7857	Intermediate Similarity	NPC471810
0.7857	Intermediate Similarity	NPC471807
0.7857	Intermediate Similarity	NPC472050
0.7857	Intermediate Similarity	NPC471806
0.7853	Intermediate Similarity	NPC471802
0.7845	Intermediate Similarity	NPC313386
0.7844	Intermediate Similarity	NPC478231
0.7844	Intermediate Similarity	NPC137301
0.7844	Intermediate Similarity	NPC275837
0.7829	Intermediate Similarity	NPC470560
0.7829	Intermediate Similarity	NPC188618
0.7826	Intermediate Similarity	NPC474385
0.7821	Intermediate Similarity	NPC43627
0.7812	Intermediate Similarity	NPC472600
0.7812	Intermediate Similarity	NPC472601
0.7811	Intermediate Similarity	NPC478225
0.7811	Intermediate Similarity	NPC472889
0.7806	Intermediate Similarity	NPC219892
0.7806	Intermediate Similarity	NPC189823
0.7802	Intermediate Similarity	NPC471805
0.7802	Intermediate Similarity	NPC121100
0.7802	Intermediate Similarity	NPC471813
0.7798	Intermediate Similarity	NPC478230
0.7798	Intermediate Similarity	NPC208173
0.7798	Intermediate Similarity	NPC170189
0.7798	Intermediate Similarity	NPC69043
0.7791	Intermediate Similarity	NPC312789
0.7778	Intermediate Similarity	NPC51106
0.7778	Intermediate Similarity	NPC159721
0.7771	Intermediate Similarity	NPC470565
0.7771	Intermediate Similarity	NPC474097
0.7765	Intermediate Similarity	NPC151292
0.7764	Intermediate Similarity	NPC472605
0.7764	Intermediate Similarity	NPC472604
0.7764	Intermediate Similarity	NPC475730
0.7763	Intermediate Similarity	NPC262671
0.7763	Intermediate Similarity	NPC201728
0.7746	Intermediate Similarity	NPC68850
0.7744	Intermediate Similarity	NPC107625
0.7742	Intermediate Similarity	NPC17840
0.7742	Intermediate Similarity	NPC247477
0.7736	Intermediate Similarity	NPC135837
0.7736	Intermediate Similarity	NPC194579
0.7735	Intermediate Similarity	NPC191606
0.773	Intermediate Similarity	NPC42540
0.773	Intermediate Similarity	NPC151607
0.7725	Intermediate Similarity	NPC240768
0.7725	Intermediate Similarity	NPC215921
0.7725	Intermediate Similarity	NPC200773
0.7725	Intermediate Similarity	NPC70016
0.7716	Intermediate Similarity	NPC82913
0.7711	Intermediate Similarity	NPC270160
0.7711	Intermediate Similarity	NPC237440
0.7711	Intermediate Similarity	NPC84142
0.7709	Intermediate Similarity	NPC306240
0.7707	Intermediate Similarity	NPC48036
0.7706	Intermediate Similarity	NPC246466
0.7706	Intermediate Similarity	NPC478226
0.7697	Intermediate Similarity	NPC108278
0.7697	Intermediate Similarity	NPC53362
0.7697	Intermediate Similarity	NPC166583
0.7692	Intermediate Similarity	NPC474499
0.7692	Intermediate Similarity	NPC99381
0.7692	Intermediate Similarity	NPC317585
0.7692	Intermediate Similarity	NPC79998
0.7692	Intermediate Similarity	NPC320819
0.7688	Intermediate Similarity	NPC193676
0.7673	Intermediate Similarity	NPC474726
0.7673	Intermediate Similarity	NPC475955
0.7669	Intermediate Similarity	NPC472610
0.7669	Intermediate Similarity	NPC469542
0.7669	Intermediate Similarity	NPC471731
0.7665	Intermediate Similarity	NPC179178
0.7665	Intermediate Similarity	NPC164762
0.7665	Intermediate Similarity	NPC469670
0.7665	Intermediate Similarity	NPC469619
0.7661	Intermediate Similarity	NPC470339
0.7658	Intermediate Similarity	NPC175943
0.7654	Intermediate Similarity	NPC28160
0.7654	Intermediate Similarity	NPC472904

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 NPC472405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	1049
0.2-0.3	2143
0.3-0.4	2914
0.4-0.5	1800
0.5-0.6	691
0.6-0.7	214
0.7-0.8	14
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
0.7644	Intermediate Similarity	NPD2403	Approved
0.7531	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD230	Phase 1
0.7262	Intermediate Similarity	NPD2534	Approved
0.7262	Intermediate Similarity	NPD2532	Approved
0.7262	Intermediate Similarity	NPD2533	Approved
0.7239	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7819	Suspended
0.7202	Intermediate Similarity	NPD6799	Approved
0.72	Intermediate Similarity	NPD7075	Discontinued
0.7134	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD943	Approved
0.7069	Intermediate Similarity	NPD1934	Approved
0.7052	Intermediate Similarity	NPD4380	Phase 2
0.7052	Intermediate Similarity	NPD6599	Discontinued
0.7045	Intermediate Similarity	NPD3882	Suspended
0.7029	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7411	Suspended
0.7011	Intermediate Similarity	NPD958	Approved
0.6989	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3817	Phase 2
0.6971	Remote Similarity	NPD6801	Discontinued
0.6949	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6232	Discontinued
0.6932	Remote Similarity	NPD2801	Approved
0.6928	Remote Similarity	NPD1510	Phase 2
0.6923	Remote Similarity	NPD7473	Discontinued
0.691	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1549	Phase 2
0.6901	Remote Similarity	NPD7390	Discontinued
0.6899	Remote Similarity	NPD9269	Phase 2
0.6893	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1240	Approved
0.6868	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD957	Approved
0.6824	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3750	Approved
0.6816	Remote Similarity	NPD3749	Approved
0.6807	Remote Similarity	NPD1607	Approved
0.6802	Remote Similarity	NPD1511	Approved
0.6798	Remote Similarity	NPD5402	Approved
0.6796	Remote Similarity	NPD6959	Discontinued
0.6795	Remote Similarity	NPD9545	Approved
0.6793	Remote Similarity	NPD3818	Discontinued
0.6786	Remote Similarity	NPD5406	Approved
0.6786	Remote Similarity	NPD5408	Approved
0.6786	Remote Similarity	NPD5404	Approved
0.6786	Remote Similarity	NPD2796	Approved
0.6786	Remote Similarity	NPD5405	Approved
0.6782	Remote Similarity	NPD5403	Approved
0.6776	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6166	Phase 2
0.6763	Remote Similarity	NPD1578	Phase 2
0.6763	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7054	Approved
0.6757	Remote Similarity	NPD5844	Phase 1
0.6752	Remote Similarity	NPD9268	Approved
0.6743	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4628	Phase 3
0.6724	Remote Similarity	NPD1512	Approved
0.672	Remote Similarity	NPD7074	Phase 3
0.672	Remote Similarity	NPD7472	Approved
0.6702	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4360	Phase 2
0.6701	Remote Similarity	NPD4363	Phase 3
0.6686	Remote Similarity	NPD2354	Approved
0.6686	Remote Similarity	NPD3887	Approved
0.6686	Remote Similarity	NPD1551	Phase 2
0.6686	Remote Similarity	NPD6190	Approved
0.6686	Remote Similarity	NPD2935	Discontinued
0.6684	Remote Similarity	NPD6797	Phase 2
0.6684	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9493	Approved
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD5711	Approved
0.6667	Remote Similarity	NPD5710	Approved
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8150	Discontinued
0.6649	Remote Similarity	NPD7251	Discontinued
0.6649	Remote Similarity	NPD6559	Discontinued
0.6648	Remote Similarity	NPD1465	Phase 2
0.6614	Remote Similarity	NPD7808	Phase 3
0.661	Remote Similarity	NPD3226	Approved
0.6596	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD454	Approved
0.6582	Remote Similarity	NPD4361	Phase 2
0.6582	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3764	Approved
0.6564	Remote Similarity	NPD1470	Approved
0.6561	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5494	Approved
0.6533	Remote Similarity	NPD4914	Approved
0.6532	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3748	Approved
0.6522	Remote Similarity	NPD1201	Approved
0.6503	Remote Similarity	NPD919	Approved
0.648	Remote Similarity	NPD4972	Discontinued
0.6474	Remote Similarity	NPD2800	Approved
0.6474	Remote Similarity	NPD1243	Approved
0.6471	Remote Similarity	NPD74	Approved
0.6471	Remote Similarity	NPD9266	Approved
0.6463	Remote Similarity	NPD1164	Approved
0.6453	Remote Similarity	NPD2353	Approved
0.6453	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.645	Remote Similarity	NPD447	Suspended
0.6441	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD3751	Discontinued
0.6429	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5953	Discontinued
0.6413	Remote Similarity	NPD6234	Discontinued
0.6412	Remote Similarity	NPD6651	Approved
0.641	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD9263	Approved
0.6405	Remote Similarity	NPD9264	Approved
0.6405	Remote Similarity	NPD9267	Approved
0.6405	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD920	Approved
0.6404	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6100	Approved
0.6395	Remote Similarity	NPD6099	Approved
0.6386	Remote Similarity	NPD4387	Approved
0.6386	Remote Similarity	NPD4386	Approved
0.6384	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD4915	Approved
0.638	Remote Similarity	NPD9717	Approved
0.6364	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6534	Approved
0.6364	Remote Similarity	NPD6535	Approved
0.6359	Remote Similarity	NPD8151	Discontinued
0.6355	Remote Similarity	NPD7435	Discontinued
0.6344	Remote Similarity	NPD1247	Approved
0.6344	Remote Similarity	NPD7199	Phase 2
0.634	Remote Similarity	NPD6784	Approved
0.634	Remote Similarity	NPD6785	Approved
0.6337	Remote Similarity	NPD2799	Discontinued
0.6335	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD8319	Approved
0.6324	Remote Similarity	NPD8320	Phase 1
0.6322	Remote Similarity	NPD4534	Discontinued
0.6321	Remote Similarity	NPD8313	Approved
0.6321	Remote Similarity	NPD8312	Approved
0.6319	Remote Similarity	NPD37	Approved
0.6318	Remote Similarity	NPD5544	Approved
0.6316	Remote Similarity	NPD7286	Phase 2
0.631	Remote Similarity	NPD3787	Discontinued
0.6308	Remote Similarity	NPD8434	Phase 2
0.6304	Remote Similarity	NPD4965	Approved
0.6304	Remote Similarity	NPD4966	Approved
0.6304	Remote Similarity	NPD4967	Phase 2
0.6292	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6776	Approved
0.6287	Remote Similarity	NPD6782	Approved
0.6287	Remote Similarity	NPD6779	Approved
0.6287	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6781	Approved
0.6287	Remote Similarity	NPD6778	Approved
0.6287	Remote Similarity	NPD6777	Approved
0.6287	Remote Similarity	NPD6780	Approved
0.6286	Remote Similarity	NPD2654	Approved
0.6277	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD3926	Phase 2
0.6272	Remote Similarity	NPD411	Approved
0.6271	Remote Similarity	NPD3300	Phase 2
0.6269	Remote Similarity	NPD7700	Phase 2
0.6269	Remote Similarity	NPD4974	Approved
0.6269	Remote Similarity	NPD7699	Phase 2
0.6269	Remote Similarity	NPD4975	Approved
0.6265	Remote Similarity	NPD1203	Approved
0.6264	Remote Similarity	NPD2346	Discontinued
0.6256	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6832	Phase 2
0.625	Remote Similarity	NPD8166	Discontinued
0.625	Remote Similarity	NPD4931	Phase 2
0.625	Remote Similarity	NPD5353	Approved
0.625	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD520	Approved
0.6229	Remote Similarity	NPD5958	Discontinued
0.6226	Remote Similarity	NPD9281	Approved
0.6219	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD4388	Approved
0.6213	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6312	Discontinued
0.619	Remote Similarity	NPD9494	Approved
0.6178	Remote Similarity	NPD7228	Approved
0.6178	Remote Similarity	NPD1852	Discontinued
0.6176	Remote Similarity	NPD3268	Approved
0.6173	Remote Similarity	NPD1163	Approved
0.6172	Remote Similarity	NPD7874	Approved
0.6172	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD7266	Discontinued
0.6171	Remote Similarity	NPD2344	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