NPASS Compound

Structure

CID4200 OpenBabel06191715322D 31 36 0 0 1 0 0 0 0 0999 V2000 3.9413 -2.3139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8410 1.6861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3860 1.3982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3928 0.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5830 1.8540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5965 0.0072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5771 -0.9207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3640 -1.3829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0188 2.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1872 2.7342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7866 1.3865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5840 -0.0082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0114 1.8393 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8125 3.2007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4057 3.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 0.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1577 -0.9326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1923 1.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3777 0.4421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8028 1.3687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6076 2.7449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3943 1.3584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5965 1.8190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1645 -0.0201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7981 0.4528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8146 4.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4078 4.1149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9620 0.4324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9482 -1.3970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9866 1.3517 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 29 1 0 0 0 0 2 30 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 11 2 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 19 2 0 0 0 0 13 9 1 1 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 14 26 2 0 0 0 0 15 21 1 0 0 0 0 15 27 1 0 0 0 0 16 31 1 0 0 0 0 17 24 2 0 0 0 0 17 29 1 0 0 0 0 18 22 2 0 0 0 0 18 30 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 1 0 0 0 20 25 1 0 0 0 0 21 23 2 0 0 0 0 22 23 1 0 0 0 0 24 28 1 0 0 0 0 25 12 1 6 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.13
Volume:	415.994
LogP:	4.576
LogD:	3.152
LogS:	-5.408
# Rotatable Bonds:	2
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	3.856
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.198
MDCK Permeability:	2.450824831612408e-05
Pgp-inhibitor:	0.059
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.166

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	95.64729309082031%
Volume Distribution (VD):	0.449
Pgp-substrate:	3.995889902114868%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.949
CYP2C19-substrate:	0.695
CYP2C9-inhibitor:	0.927
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.444
CYP2D6-substrate:	0.795
CYP3A4-inhibitor:	0.459
CYP3A4-substrate:	0.638

ADMET: Excretion

Clearance (CL):	2.141
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.816
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.736
Skin Sensitization:	0.378
Carcinogencity:	0.401
Eye Corrosion:	0.003
Eye Irritation:	0.252
Respiratory Toxicity:	0.587

Download Data

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

Natural Product: NPC4200

Natural Product ID:	NPC4200
*Common Name:**	Ohioensin E
IUPAC Name:	n.a.
Synonyms:	Ohioensin E
Standard InCHIKey:	UFSFBNPOCJFHOB-NXPBYULISA-N
Standard InCHI:	InChI=1S/C25H20O6/c1-29-17-8-7-12-19(24(17)28)22-18(30-2)10-15(27)21-14(26)9-13-11-5-3-4-6-16(11)31-25(12)20(13)23(21)22/h3-8,10,13,20,25,27-28H,9H2,1-2H3/t13-,20+,25+/m1/s1
SMILES:	COc1ccc2c(-c3c(cc(c4C(=O)C[C@@H]5c6ccccc6O[C@@H]2[C@@H]5c34)O)OC)c1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465070
PubChem CID:	10432048
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans

*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
NPO3518	Polytrichum ohioense	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3518	Polytrichum ohioense	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3518	Polytrichum ohioense	Species	Polytrichaceae	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
ED50	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	6.0	ug ml-1	PMID[571018]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[571018]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[571018]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.0	ug ml-1	PMID[571018]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[571018]

☑ 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 NPC4200 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	440
0.1-0.2	1727
0.2-0.3	3680
0.3-0.4	9745
0.4-0.5	8741
0.5-0.6	3265
0.6-0.7	4884
0.7-0.8	5526
0.8-0.85	2884
0.85-0.9	1566
0.9-0.95	235
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC300307
0.95	High Similarity	NPC18380
0.9437	High Similarity	NPC36217
0.9437	High Similarity	NPC184326
0.9437	High Similarity	NPC292863
0.939	High Similarity	NPC188079
0.9387	High Similarity	NPC43319
0.9383	High Similarity	NPC186686
0.9379	High Similarity	NPC137232
0.9375	High Similarity	NPC195167
0.9329	High Similarity	NPC218226
0.9325	High Similarity	NPC293319
0.9321	High Similarity	NPC201800
0.9321	High Similarity	NPC476247
0.9273	High Similarity	NPC475212
0.9268	High Similarity	NPC320741
0.9268	High Similarity	NPC272502
0.9268	High Similarity	NPC224851
0.9268	High Similarity	NPC171985
0.9264	High Similarity	NPC290160
0.9259	High Similarity	NPC142252
0.9255	High Similarity	NPC85121
0.9255	High Similarity	NPC210459
0.925	High Similarity	NPC278778
0.925	High Similarity	NPC291878
0.925	High Similarity	NPC35038
0.925	High Similarity	NPC195796
0.9217	High Similarity	NPC279209
0.9217	High Similarity	NPC102277
0.9212	High Similarity	NPC474024
0.9207	High Similarity	NPC477840
0.9207	High Similarity	NPC25361
0.9202	High Similarity	NPC219927
0.9202	High Similarity	NPC474150
0.9202	High Similarity	NPC477841
0.9202	High Similarity	NPC474162
0.9198	High Similarity	NPC118256
0.9198	High Similarity	NPC299436
0.9198	High Similarity	NPC192686
0.9198	High Similarity	NPC119209
0.9198	High Similarity	NPC321399
0.9193	High Similarity	NPC474055
0.9193	High Similarity	NPC472598
0.9193	High Similarity	NPC27337
0.9193	High Similarity	NPC291508
0.9187	High Similarity	NPC67396
0.9187	High Similarity	NPC470327
0.9187	High Similarity	NPC45849
0.9187	High Similarity	NPC200761
0.9187	High Similarity	NPC477503
0.9162	High Similarity	NPC257667
0.9162	High Similarity	NPC186847
0.9162	High Similarity	NPC472454
0.9157	High Similarity	NPC107627
0.9146	High Similarity	NPC12461
0.9146	High Similarity	NPC197168
0.9146	High Similarity	NPC476295
0.9141	High Similarity	NPC165970
0.9141	High Similarity	NPC474038
0.9141	High Similarity	NPC66618
0.9141	High Similarity	NPC113163
0.9141	High Similarity	NPC472632
0.9141	High Similarity	NPC158188
0.9141	High Similarity	NPC471210
0.9141	High Similarity	NPC305987
0.9141	High Similarity	NPC84324
0.9141	High Similarity	NPC288131
0.9141	High Similarity	NPC26326
0.913	High Similarity	NPC24640
0.913	High Similarity	NPC472626
0.913	High Similarity	NPC209614
0.913	High Similarity	NPC470328
0.9125	High Similarity	NPC192083
0.9125	High Similarity	NPC18727
0.9125	High Similarity	NPC213896
0.9123	High Similarity	NPC150977
0.9118	High Similarity	NPC324742
0.9112	High Similarity	NPC216307
0.9096	High Similarity	NPC6588
0.9096	High Similarity	NPC477154
0.9096	High Similarity	NPC150131
0.9096	High Similarity	NPC476306
0.9096	High Similarity	NPC117854
0.9091	High Similarity	NPC72787
0.9091	High Similarity	NPC36
0.9091	High Similarity	NPC326520
0.9091	High Similarity	NPC62261
0.9091	High Similarity	NPC475888
0.9091	High Similarity	NPC7688
0.9091	High Similarity	NPC303174
0.9091	High Similarity	NPC7154
0.9091	High Similarity	NPC125039
0.9091	High Similarity	NPC275780
0.9091	High Similarity	NPC472450
0.9091	High Similarity	NPC239752
0.9091	High Similarity	NPC58223
0.9091	High Similarity	NPC36916
0.9085	High Similarity	NPC474033
0.9085	High Similarity	NPC472964
0.9085	High Similarity	NPC474034
0.9085	High Similarity	NPC206605
0.9085	High Similarity	NPC211107
0.9085	High Similarity	NPC15374
0.908	High Similarity	NPC56085
0.908	High Similarity	NPC282009
0.908	High Similarity	NPC474960
0.908	High Similarity	NPC471973
0.908	High Similarity	NPC101731
0.908	High Similarity	NPC228785
0.908	High Similarity	NPC472902
0.908	High Similarity	NPC287328
0.908	High Similarity	NPC472624
0.908	High Similarity	NPC174953
0.908	High Similarity	NPC475784
0.908	High Similarity	NPC297212
0.908	High Similarity	NPC14353
0.9074	High Similarity	NPC284820
0.9074	High Similarity	NPC473272
0.9074	High Similarity	NPC471209
0.9074	High Similarity	NPC299520
0.9074	High Similarity	NPC129684
0.9074	High Similarity	NPC136674
0.9074	High Similarity	NPC223787
0.9068	High Similarity	NPC321779
0.9068	High Similarity	NPC226025
0.9062	High Similarity	NPC219582
0.9062	High Similarity	NPC302950
0.9062	High Similarity	NPC472912
0.9062	High Similarity	NPC106976
0.9062	High Similarity	NPC236637
0.9062	High Similarity	NPC260979
0.9042	High Similarity	NPC476637
0.9036	High Similarity	NPC272560
0.9036	High Similarity	NPC120593
0.9036	High Similarity	NPC39091
0.9036	High Similarity	NPC477517
0.9036	High Similarity	NPC472449
0.9036	High Similarity	NPC170245
0.9036	High Similarity	NPC37870
0.903	High Similarity	NPC474240
0.903	High Similarity	NPC7483
0.903	High Similarity	NPC152659
0.903	High Similarity	NPC270837
0.903	High Similarity	NPC220313
0.903	High Similarity	NPC236132
0.903	High Similarity	NPC189473
0.903	High Similarity	NPC236521
0.903	High Similarity	NPC248638
0.903	High Similarity	NPC472625
0.903	High Similarity	NPC23298
0.9024	High Similarity	NPC266314
0.9024	High Similarity	NPC472634
0.9024	High Similarity	NPC278052
0.9024	High Similarity	NPC472906
0.9024	High Similarity	NPC61010
0.9024	High Similarity	NPC474186
0.9024	High Similarity	NPC471211
0.9024	High Similarity	NPC471212
0.9024	High Similarity	NPC474187
0.9024	High Similarity	NPC471499
0.9024	High Similarity	NPC40491
0.9024	High Similarity	NPC134783
0.9018	High Similarity	NPC22192
0.9018	High Similarity	NPC53545
0.9018	High Similarity	NPC235448
0.9018	High Similarity	NPC100123
0.9018	High Similarity	NPC250214
0.9018	High Similarity	NPC46736
0.9018	High Similarity	NPC476410
0.9018	High Similarity	NPC284127
0.9018	High Similarity	NPC172202
0.9018	High Similarity	NPC117418
0.9018	High Similarity	NPC473990
0.9018	High Similarity	NPC95936
0.9012	High Similarity	NPC208152
0.9012	High Similarity	NPC78492
0.9006	High Similarity	NPC185275
0.9006	High Similarity	NPC469550
0.9006	High Similarity	NPC298692
0.9006	High Similarity	NPC244903
0.9006	High Similarity	NPC74924
0.8988	High Similarity	NPC101107
0.8988	High Similarity	NPC131866
0.8988	High Similarity	NPC476365
0.8982	High Similarity	NPC14662
0.8982	High Similarity	NPC243877
0.8982	High Similarity	NPC260266
0.8976	High Similarity	NPC472277
0.8976	High Similarity	NPC156432
0.897	High Similarity	NPC25152
0.897	High Similarity	NPC472635
0.897	High Similarity	NPC294965
0.897	High Similarity	NPC229632
0.8966	High Similarity	NPC105591
0.8963	High Similarity	NPC472631
0.8963	High Similarity	NPC470326
0.8963	High Similarity	NPC475886
0.8963	High Similarity	NPC320359
0.8963	High Similarity	NPC474287
0.8963	High Similarity	NPC476280

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 NPC4200 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	950
0.2-0.3	1727
0.3-0.4	2651
0.4-0.5	1800
0.5-0.6	956
0.6-0.7	461
0.7-0.8	155
0.8-0.85	30
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9125	High Similarity	NPD2393	Clinical (unspecified phase)
0.9091	High Similarity	NPD6167	Clinical (unspecified phase)
0.9091	High Similarity	NPD6168	Clinical (unspecified phase)
0.9091	High Similarity	NPD6166	Phase 2
0.9062	High Similarity	NPD1934	Approved
0.9024	High Similarity	NPD6959	Discontinued
0.8817	High Similarity	NPD5844	Phase 1
0.881	High Similarity	NPD7473	Discontinued
0.8743	High Similarity	NPD6232	Discontinued
0.8659	High Similarity	NPD2801	Approved
0.8655	High Similarity	NPD7074	Phase 3
0.8623	High Similarity	NPD5494	Approved
0.8606	High Similarity	NPD8443	Clinical (unspecified phase)
0.8596	High Similarity	NPD7054	Approved
0.8554	High Similarity	NPD4868	Clinical (unspecified phase)
0.8547	High Similarity	NPD7472	Approved
0.8476	Intermediate Similarity	NPD4380	Phase 2
0.8447	Intermediate Similarity	NPD1511	Approved
0.8443	Intermediate Similarity	NPD3882	Suspended
0.8427	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD6797	Phase 2
0.8344	Intermediate Similarity	NPD1512	Approved
0.8343	Intermediate Similarity	NPD7251	Discontinued
0.8324	Intermediate Similarity	NPD3818	Discontinued
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8314	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD7808	Phase 3
0.8286	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7075	Discontinued
0.8282	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD3817	Phase 2
0.8221	Intermediate Similarity	NPD7390	Discontinued
0.8214	Intermediate Similarity	NPD1465	Phase 2
0.8214	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7411	Suspended
0.8192	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD8312	Approved
0.8146	Intermediate Similarity	NPD8313	Approved
0.8137	Intermediate Similarity	NPD1549	Phase 2
0.8136	Intermediate Similarity	NPD6559	Discontinued
0.8118	Intermediate Similarity	NPD7768	Phase 2
0.7965	Intermediate Similarity	NPD3749	Approved
0.7952	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6801	Discontinued
0.7935	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6234	Discontinued
0.791	Intermediate Similarity	NPD7228	Approved
0.7901	Intermediate Similarity	NPD2796	Approved
0.7886	Intermediate Similarity	NPD3787	Discontinued
0.7876	Intermediate Similarity	NPD8151	Discontinued
0.7844	Intermediate Similarity	NPD2533	Approved
0.7844	Intermediate Similarity	NPD2532	Approved
0.7844	Intermediate Similarity	NPD2534	Approved
0.784	Intermediate Similarity	NPD1510	Phase 2
0.7829	Intermediate Similarity	NPD7199	Phase 2
0.7824	Intermediate Similarity	NPD6599	Discontinued
0.7809	Intermediate Similarity	NPD3751	Discontinued
0.7805	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6799	Approved
0.7765	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3926	Phase 2
0.774	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD37	Approved
0.7727	Intermediate Similarity	NPD1247	Approved
0.7716	Intermediate Similarity	NPD1607	Approved
0.7714	Intermediate Similarity	NPD919	Approved
0.7711	Intermediate Similarity	NPD3750	Approved
0.7702	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1240	Approved
0.7702	Intermediate Similarity	NPD1613	Approved
0.7701	Intermediate Similarity	NPD4967	Phase 2
0.7701	Intermediate Similarity	NPD4966	Approved
0.7701	Intermediate Similarity	NPD4965	Approved
0.7688	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3226	Approved
0.7651	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6777	Approved
0.7644	Intermediate Similarity	NPD6781	Approved
0.7644	Intermediate Similarity	NPD6778	Approved
0.7644	Intermediate Similarity	NPD6776	Approved
0.7644	Intermediate Similarity	NPD6779	Approved
0.7644	Intermediate Similarity	NPD5402	Approved
0.7644	Intermediate Similarity	NPD6782	Approved
0.7644	Intermediate Similarity	NPD6780	Approved
0.7644	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD8150	Discontinued
0.7605	Intermediate Similarity	NPD7003	Approved
0.7593	Intermediate Similarity	NPD943	Approved
0.7577	Intermediate Similarity	NPD7871	Phase 2
0.7577	Intermediate Similarity	NPD7870	Phase 2
0.7576	Intermediate Similarity	NPD6100	Approved
0.7576	Intermediate Similarity	NPD6099	Approved
0.7562	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4908	Phase 1
0.7558	Intermediate Similarity	NPD7458	Discontinued
0.7545	Intermediate Similarity	NPD2800	Approved
0.7544	Intermediate Similarity	NPD5403	Approved
0.7544	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2346	Discontinued
0.7526	Intermediate Similarity	NPD7435	Discontinued
0.7525	Intermediate Similarity	NPD7783	Phase 2
0.7525	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7486	Intermediate Similarity	NPD7229	Phase 3
0.7486	Intermediate Similarity	NPD8455	Phase 2
0.747	Intermediate Similarity	NPD5405	Approved
0.747	Intermediate Similarity	NPD2935	Discontinued
0.747	Intermediate Similarity	NPD5404	Approved
0.747	Intermediate Similarity	NPD5408	Approved
0.747	Intermediate Similarity	NPD5406	Approved
0.7446	Intermediate Similarity	NPD7240	Approved
0.7436	Intermediate Similarity	NPD7698	Approved
0.7436	Intermediate Similarity	NPD7697	Approved
0.7436	Intermediate Similarity	NPD7696	Phase 3
0.7427	Intermediate Similarity	NPD5401	Approved
0.741	Intermediate Similarity	NPD3748	Approved
0.741	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4625	Phase 3
0.7405	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8166	Discontinued
0.7389	Intermediate Similarity	NPD5711	Approved
0.7389	Intermediate Similarity	NPD5710	Approved
0.7385	Intermediate Similarity	NPD6823	Phase 2
0.7382	Intermediate Similarity	NPD4360	Phase 2
0.7382	Intermediate Similarity	NPD6534	Approved
0.7382	Intermediate Similarity	NPD4363	Phase 3
0.7382	Intermediate Similarity	NPD6535	Approved
0.7374	Intermediate Similarity	NPD7701	Phase 2
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1551	Phase 2
0.735	Intermediate Similarity	NPD7801	Approved
0.7341	Intermediate Similarity	NPD920	Approved
0.7337	Intermediate Similarity	NPD6674	Discontinued
0.7333	Intermediate Similarity	NPD8127	Discontinued
0.7333	Intermediate Similarity	NPD230	Phase 1
0.7322	Intermediate Similarity	NPD7177	Discontinued
0.7321	Intermediate Similarity	NPD2344	Approved
0.7306	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2799	Discontinued
0.73	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7874	Approved
0.7294	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6651	Approved
0.7283	Intermediate Similarity	NPD6273	Approved
0.7268	Intermediate Similarity	NPD7699	Phase 2
0.7268	Intermediate Similarity	NPD7700	Phase 2
0.7258	Intermediate Similarity	NPD7685	Pre-registration
0.7256	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD8434	Phase 2
0.7235	Intermediate Similarity	NPD1243	Approved
0.7229	Intermediate Similarity	NPD447	Suspended
0.7225	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8319	Approved
0.7222	Intermediate Similarity	NPD8320	Phase 1
0.7209	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5953	Discontinued
0.72	Intermediate Similarity	NPD1653	Approved
0.7189	Intermediate Similarity	NPD7286	Phase 2
0.7172	Intermediate Similarity	NPD7680	Approved
0.7169	Intermediate Similarity	NPD4060	Phase 1
0.7157	Intermediate Similarity	NPD2493	Approved
0.7157	Intermediate Similarity	NPD2494	Approved
0.7151	Intermediate Similarity	NPD6190	Approved
0.7151	Intermediate Similarity	NPD2309	Approved
0.715	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6212	Phase 3
0.715	Intermediate Similarity	NPD6213	Phase 3
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4582	Approved
0.7136	Intermediate Similarity	NPD4583	Approved
0.7135	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2490	Approved
0.7135	Intermediate Similarity	NPD2488	Approved
0.7128	Intermediate Similarity	NPD7549	Discontinued
0.7126	Intermediate Similarity	NPD1933	Approved
0.7125	Intermediate Similarity	NPD1610	Phase 2
0.7125	Intermediate Similarity	NPD1201	Approved
0.7115	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4665	Approved
0.7101	Intermediate Similarity	NPD4111	Phase 1
0.7085	Intermediate Similarity	NPD4004	Approved
0.7085	Intermediate Similarity	NPD4002	Approved
0.7083	Intermediate Similarity	NPD4287	Approved
0.7079	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD9494	Approved
0.7071	Intermediate Similarity	NPD3452	Approved
0.7071	Intermediate Similarity	NPD3450	Approved
0.7065	Intermediate Similarity	NPD7584	Approved
0.7055	Intermediate Similarity	NPD1470	Approved
0.7053	Intermediate Similarity	NPD7090	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