NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	444.14
Volume:	436.079
LogP:	2.534
LogD:	0.875
LogS:	-2.286
# Rotatable Bonds:	10
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.203
Synthetic Accessibility Score:	4.638
Fsp3:	0.391
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.055
MDCK Permeability:	3.5628916521091014e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.471
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.896
Plasma Protein Binding (PPB):	90.46326446533203%
Volume Distribution (VD):	0.459
Pgp-substrate:	16.220277786254883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.273
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.498
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.634
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	10.958
Half-life (T1/2):	0.956

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.524
Skin Sensitization:	0.381
Carcinogencity:	0.307
Eye Corrosion:	0.034
Eye Irritation:	0.035
Respiratory Toxicity:	0.478

Download Data

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

Natural Product: NPC477279

Natural Product ID:	NPC477279
*Common Name:**	Brevipolide E
IUPAC Name:	[1-[(1S,2S)-2-[(S)-acetyloxy-[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	Brevipolide E
Standard InCHIKey:	AYUDDNXPNFAQHF-AILWCWHNSA-N
Standard InCHI:	InChI=1S/C23H24O9/c1-12(30-21(28)9-7-14-6-8-17(25)18(26)10-14)22(29)15-11-16(15)23(31-13(2)24)19-4-3-5-20(27)32-19/h3,5-10,12,15-16,19,23,25-26H,4,11H2,1-2H3/b9-7+/t12?,15-,16-,19+,23-/m0/s1
SMILES:	CC(C(=O)[C@H]1C[C@@H]1[C@@H]([C@H]2CC=CC(=O)O2)OC(=O)C)OC(=O)/C=C/C3=CC(=C(C=C3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44178668
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	Whole Plant	Tawangmangu village, Karanganyar, Central Java, Indonesia	2003-FEB	PMID[19422206]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19422206]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23282042]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28099005]
NPO25696	Hyptis brevipes	Species	Lamiaceae	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	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	10	nM	PMID[19422206]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	ED50	>	50	nM	PMID[19422206]

☑ 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 NPC477279 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	317
0.1-0.2	1243
0.2-0.3	3137
0.3-0.4	7216
0.4-0.5	10402
0.5-0.6	6108
0.6-0.7	10923
0.7-0.8	3187
0.8-0.85	133
0.85-0.9	22
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC477278
0.9925	High Similarity	NPC477277
0.95	High Similarity	NPC98009
0.9398	High Similarity	NPC327204
0.9398	High Similarity	NPC323379
0.9328	High Similarity	NPC477280
0.9328	High Similarity	NPC19719
0.9328	High Similarity	NPC477281
0.9185	High Similarity	NPC155209
0.9185	High Similarity	NPC168799
0.9111	High Similarity	NPC25581
0.9111	High Similarity	NPC61
0.9111	High Similarity	NPC18074
0.9111	High Similarity	NPC5419
0.9037	High Similarity	NPC198388
0.8929	High Similarity	NPC476820
0.8929	High Similarity	NPC26241
0.8929	High Similarity	NPC303683
0.8929	High Similarity	NPC295492
0.8929	High Similarity	NPC205751
0.8929	High Similarity	NPC274891
0.8929	High Similarity	NPC474875
0.8929	High Similarity	NPC476819
0.8857	High Similarity	NPC152942
0.8857	High Similarity	NPC37250
0.8857	High Similarity	NPC219428
0.8857	High Similarity	NPC142703
0.8857	High Similarity	NPC278068
0.8857	High Similarity	NPC302857
0.8849	High Similarity	NPC71638
0.8849	High Similarity	NPC64230
0.8794	High Similarity	NPC288452
0.8794	High Similarity	NPC179505
0.8794	High Similarity	NPC156709
0.8794	High Similarity	NPC289690
0.8759	High Similarity	NPC229264
0.8741	High Similarity	NPC192831
0.8741	High Similarity	NPC258469
0.8741	High Similarity	NPC303090
0.8741	High Similarity	NPC472016
0.8741	High Similarity	NPC277315
0.8741	High Similarity	NPC284948
0.8741	High Similarity	NPC37331
0.8741	High Similarity	NPC319628
0.8741	High Similarity	NPC43158
0.8741	High Similarity	NPC220664
0.8699	High Similarity	NPC471076
0.8699	High Similarity	NPC192568
0.8671	High Similarity	NPC297517
0.8671	High Similarity	NPC477335
0.8671	High Similarity	NPC13818
0.8671	High Similarity	NPC206095
0.8671	High Similarity	NPC35702
0.8671	High Similarity	NPC471027
0.8671	High Similarity	NPC224389
0.8662	High Similarity	NPC322021
0.8652	High Similarity	NPC279676
0.8652	High Similarity	NPC67349
0.8643	High Similarity	NPC233350
0.8643	High Similarity	NPC70680
0.8643	High Similarity	NPC182217
0.8633	High Similarity	NPC471749
0.8611	High Similarity	NPC285550
0.8601	High Similarity	NPC38473
0.8592	High Similarity	NPC284409
0.8581	High Similarity	NPC32197
0.8571	High Similarity	NPC68517
0.8571	High Similarity	NPC106406
0.8571	High Similarity	NPC474895
0.8562	High Similarity	NPC98356
0.8552	High Similarity	NPC183824
0.8552	High Similarity	NPC474692
0.8503	High Similarity	NPC143892
0.8503	High Similarity	NPC221383
0.8503	High Similarity	NPC299090
0.8503	High Similarity	NPC322660
0.8503	High Similarity	NPC283081
0.8493	Intermediate Similarity	NPC477333
0.8489	Intermediate Similarity	NPC318799
0.8478	Intermediate Similarity	NPC226855
0.8472	Intermediate Similarity	NPC9218
0.8462	Intermediate Similarity	NPC283560
0.8462	Intermediate Similarity	NPC24295
0.8446	Intermediate Similarity	NPC1580
0.8425	Intermediate Similarity	NPC160378
0.8425	Intermediate Similarity	NPC469615
0.8411	Intermediate Similarity	NPC327225
0.8411	Intermediate Similarity	NPC44730
0.8382	Intermediate Similarity	NPC85565
0.8367	Intermediate Similarity	NPC469683
0.8367	Intermediate Similarity	NPC258671
0.8367	Intermediate Similarity	NPC53884
0.8355	Intermediate Similarity	NPC281703
0.8355	Intermediate Similarity	NPC125487
0.8355	Intermediate Similarity	NPC477299
0.8344	Intermediate Similarity	NPC95498
0.8344	Intermediate Similarity	NPC246566
0.8333	Intermediate Similarity	NPC158654
0.8333	Intermediate Similarity	NPC306343
0.8322	Intermediate Similarity	NPC90431
0.8322	Intermediate Similarity	NPC475111
0.8322	Intermediate Similarity	NPC472969
0.8322	Intermediate Similarity	NPC156892
0.8301	Intermediate Similarity	NPC475484
0.8299	Intermediate Similarity	NPC304956
0.8299	Intermediate Similarity	NPC114242
0.8299	Intermediate Similarity	NPC50221
0.8298	Intermediate Similarity	NPC239302
0.8296	Intermediate Similarity	NPC472271
0.8296	Intermediate Similarity	NPC147654
0.8296	Intermediate Similarity	NPC322332
0.8289	Intermediate Similarity	NPC475595
0.8289	Intermediate Similarity	NPC83663
0.8289	Intermediate Similarity	NPC473544
0.8289	Intermediate Similarity	NPC475162
0.8289	Intermediate Similarity	NPC475216
0.8289	Intermediate Similarity	NPC475145
0.8289	Intermediate Similarity	NPC266084
0.8288	Intermediate Similarity	NPC253481
0.8288	Intermediate Similarity	NPC296643
0.8288	Intermediate Similarity	NPC253722
0.8288	Intermediate Similarity	NPC31751
0.8286	Intermediate Similarity	NPC237506
0.8286	Intermediate Similarity	NPC285361
0.8286	Intermediate Similarity	NPC329344
0.8286	Intermediate Similarity	NPC32626
0.8286	Intermediate Similarity	NPC172673
0.8286	Intermediate Similarity	NPC217052
0.8278	Intermediate Similarity	NPC477334
0.8278	Intermediate Similarity	NPC243891
0.8276	Intermediate Similarity	NPC147379
0.8276	Intermediate Similarity	NPC225036
0.8276	Intermediate Similarity	NPC75763
0.8276	Intermediate Similarity	NPC105525
0.8276	Intermediate Similarity	NPC12218
0.8276	Intermediate Similarity	NPC191280
0.8271	Intermediate Similarity	NPC309434
0.8267	Intermediate Similarity	NPC42464
0.8258	Intermediate Similarity	NPC471750
0.8252	Intermediate Similarity	NPC139519
0.8252	Intermediate Similarity	NPC18646
0.8247	Intermediate Similarity	NPC470896
0.8247	Intermediate Similarity	NPC473275
0.8239	Intermediate Similarity	NPC239855
0.8239	Intermediate Similarity	NPC307006
0.8239	Intermediate Similarity	NPC129889
0.8239	Intermediate Similarity	NPC475468
0.8227	Intermediate Similarity	NPC108553
0.8224	Intermediate Similarity	NPC267091
0.8224	Intermediate Similarity	NPC93498
0.8224	Intermediate Similarity	NPC163883
0.8222	Intermediate Similarity	NPC470848
0.8222	Intermediate Similarity	NPC470849
0.8214	Intermediate Similarity	NPC64111
0.8214	Intermediate Similarity	NPC94810
0.8207	Intermediate Similarity	NPC325625
0.8207	Intermediate Similarity	NPC257173
0.8207	Intermediate Similarity	NPC239943
0.82	Intermediate Similarity	NPC43123
0.8188	Intermediate Similarity	NPC473867
0.8188	Intermediate Similarity	NPC132921
0.8188	Intermediate Similarity	NPC197832
0.8182	Intermediate Similarity	NPC471110
0.8182	Intermediate Similarity	NPC248150
0.8176	Intermediate Similarity	NPC470130
0.8176	Intermediate Similarity	NPC226738
0.8176	Intermediate Similarity	NPC190587
0.8176	Intermediate Similarity	NPC239608
0.8176	Intermediate Similarity	NPC46161
0.8176	Intermediate Similarity	NPC473090
0.8176	Intermediate Similarity	NPC22176
0.8176	Intermediate Similarity	NPC121573
0.817	Intermediate Similarity	NPC146277
0.817	Intermediate Similarity	NPC19380
0.817	Intermediate Similarity	NPC161159
0.8165	Intermediate Similarity	NPC223006
0.8165	Intermediate Similarity	NPC134047
0.8165	Intermediate Similarity	NPC272750
0.8165	Intermediate Similarity	NPC173729
0.8158	Intermediate Similarity	NPC300329
0.8151	Intermediate Similarity	NPC474784
0.8146	Intermediate Similarity	NPC98809
0.8146	Intermediate Similarity	NPC476394
0.8143	Intermediate Similarity	NPC167463
0.8143	Intermediate Similarity	NPC46192
0.8141	Intermediate Similarity	NPC76211
0.8138	Intermediate Similarity	NPC308976
0.8138	Intermediate Similarity	NPC471152
0.8134	Intermediate Similarity	NPC63126
0.8134	Intermediate Similarity	NPC203124
0.8129	Intermediate Similarity	NPC118584
0.8129	Intermediate Similarity	NPC147192
0.8129	Intermediate Similarity	NPC251407
0.8129	Intermediate Similarity	NPC168653
0.8129	Intermediate Similarity	NPC475695
0.8121	Intermediate Similarity	NPC228940
0.812	Intermediate Similarity	NPC281277
0.8116	Intermediate Similarity	NPC469568
0.8116	Intermediate Similarity	NPC288945
0.8112	Intermediate Similarity	NPC156124

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 NPC477279 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	830
0.2-0.3	1764
0.3-0.4	2701
0.4-0.5	2005
0.5-0.6	1094
0.6-0.7	446
0.7-0.8	40
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD6190	Approved
0.8112	Intermediate Similarity	NPD230	Phase 1
0.7919	Intermediate Similarity	NPD8166	Discontinued
0.7838	Intermediate Similarity	NPD7266	Discontinued
0.7785	Intermediate Similarity	NPD3882	Suspended
0.7785	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD9545	Approved
0.7722	Intermediate Similarity	NPD3817	Phase 2
0.7682	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7075	Discontinued
0.7569	Intermediate Similarity	NPD9494	Approved
0.756	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD6355	Discontinued
0.7484	Intermediate Similarity	NPD1934	Approved
0.7484	Intermediate Similarity	NPD6801	Discontinued
0.747	Intermediate Similarity	NPD3818	Discontinued
0.7465	Intermediate Similarity	NPD9269	Phase 2
0.7455	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6166	Phase 2
0.7455	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6797	Phase 2
0.7438	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2801	Approved
0.7432	Intermediate Similarity	NPD943	Approved
0.7419	Intermediate Similarity	NPD6799	Approved
0.7415	Intermediate Similarity	NPD6798	Discontinued
0.7405	Intermediate Similarity	NPD3455	Phase 2
0.7396	Intermediate Similarity	NPD7251	Discontinued
0.7362	Intermediate Similarity	NPD6234	Discontinued
0.7325	Intermediate Similarity	NPD1512	Approved
0.7315	Intermediate Similarity	NPD4060	Phase 1
0.7315	Intermediate Similarity	NPD825	Approved
0.7315	Intermediate Similarity	NPD826	Approved
0.7297	Intermediate Similarity	NPD3764	Approved
0.7289	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5402	Approved
0.7278	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7808	Phase 3
0.725	Intermediate Similarity	NPD6599	Discontinued
0.725	Intermediate Similarity	NPD4380	Phase 2
0.7248	Intermediate Similarity	NPD4062	Phase 3
0.7248	Intermediate Similarity	NPD6233	Phase 2
0.7237	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3027	Phase 3
0.7226	Intermediate Similarity	NPD4110	Phase 3
0.7226	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1608	Approved
0.7219	Intermediate Similarity	NPD7054	Approved
0.7208	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3022	Approved
0.7206	Intermediate Similarity	NPD3021	Approved
0.7202	Intermediate Similarity	NPD7473	Discontinued
0.72	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1511	Approved
0.7194	Intermediate Similarity	NPD2629	Approved
0.7183	Intermediate Similarity	NPD9268	Approved
0.7176	Intermediate Similarity	NPD7074	Phase 3
0.7176	Intermediate Similarity	NPD7472	Approved
0.717	Intermediate Similarity	NPD5403	Approved
0.716	Intermediate Similarity	NPD37	Approved
0.7152	Intermediate Similarity	NPD919	Approved
0.7152	Intermediate Similarity	NPD3146	Approved
0.7152	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4966	Approved
0.7134	Intermediate Similarity	NPD4965	Approved
0.7134	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD6232	Discontinued
0.7125	Intermediate Similarity	NPD1653	Approved
0.7117	Intermediate Similarity	NPD1465	Phase 2
0.7114	Intermediate Similarity	NPD7095	Approved
0.7102	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6386	Approved
0.7099	Intermediate Similarity	NPD6385	Approved
0.7091	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8150	Discontinued
0.708	Intermediate Similarity	NPD2067	Discontinued
0.7071	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3887	Approved
0.707	Intermediate Similarity	NPD2354	Approved
0.7067	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7066	Intermediate Similarity	NPD8127	Discontinued
0.7059	Intermediate Similarity	NPD7228	Approved
0.7059	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5401	Approved
0.7042	Intermediate Similarity	NPD5536	Phase 2
0.7039	Intermediate Similarity	NPD555	Phase 2
0.7039	Intermediate Similarity	NPD4340	Discontinued
0.7027	Intermediate Similarity	NPD257	Approved
0.7027	Intermediate Similarity	NPD258	Approved
0.702	Intermediate Similarity	NPD6663	Approved
0.7018	Intermediate Similarity	NPD5844	Phase 1
0.7018	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD17	Approved
0.7013	Intermediate Similarity	NPD1510	Phase 2
0.7012	Intermediate Similarity	NPD7819	Suspended
0.6987	Remote Similarity	NPD5958	Discontinued
0.6987	Remote Similarity	NPD4534	Discontinued
0.698	Remote Similarity	NPD5736	Approved
0.6978	Remote Similarity	NPD228	Approved
0.697	Remote Similarity	NPD5353	Approved
0.6968	Remote Similarity	NPD2935	Discontinued
0.6959	Remote Similarity	NPD3751	Discontinued
0.6954	Remote Similarity	NPD3268	Approved
0.6937	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD447	Suspended
0.6927	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5762	Approved
0.6923	Remote Similarity	NPD5763	Approved
0.6913	Remote Similarity	NPD5647	Approved
0.6908	Remote Similarity	NPD259	Phase 1
0.6905	Remote Similarity	NPD5494	Approved
0.6903	Remote Similarity	NPD2799	Discontinued
0.6903	Remote Similarity	NPD7033	Discontinued
0.6899	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3750	Approved
0.6893	Remote Similarity	NPD8434	Phase 2
0.689	Remote Similarity	NPD7411	Suspended
0.6879	Remote Similarity	NPD1549	Phase 2
0.6871	Remote Similarity	NPD7458	Discontinued
0.6864	Remote Similarity	NPD1247	Approved
0.6863	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1613	Approved
0.6863	Remote Similarity	NPD1240	Approved
0.6859	Remote Similarity	NPD9570	Approved
0.6859	Remote Similarity	NPD2796	Approved
0.6859	Remote Similarity	NPD2438	Suspended
0.6846	Remote Similarity	NPD987	Approved
0.6846	Remote Similarity	NPD2797	Approved
0.6832	Remote Similarity	NPD2534	Approved
0.6832	Remote Similarity	NPD2532	Approved
0.6832	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2533	Approved
0.6824	Remote Similarity	NPD3787	Discontinued
0.6815	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2353	Approved
0.6812	Remote Similarity	NPD1358	Approved
0.6784	Remote Similarity	NPD3926	Phase 2
0.6784	Remote Similarity	NPD5242	Approved
0.6783	Remote Similarity	NPD4198	Discontinued
0.6781	Remote Similarity	NPD2932	Approved
0.6781	Remote Similarity	NPD3019	Approved
0.6781	Remote Similarity	NPD1778	Approved
0.6779	Remote Similarity	NPD1283	Approved
0.6774	Remote Similarity	NPD6653	Approved
0.6774	Remote Similarity	NPD1607	Approved
0.6768	Remote Similarity	NPD3226	Approved
0.6766	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1241	Discontinued
0.6761	Remote Similarity	NPD5283	Phase 1
0.6755	Remote Similarity	NPD9569	Approved
0.6739	Remote Similarity	NPD3134	Approved
0.6736	Remote Similarity	NPD9493	Approved
0.6731	Remote Similarity	NPD7097	Phase 1
0.6728	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5585	Approved
0.6711	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.671	Remote Similarity	NPD275	Approved
0.671	Remote Similarity	NPD274	Approved
0.6708	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6559	Discontinued
0.6689	Remote Similarity	NPD422	Phase 1
0.6687	Remote Similarity	NPD6273	Approved
0.6687	Remote Similarity	NPD5049	Phase 3
0.6687	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2163	Approved
0.6667	Remote Similarity	NPD4626	Approved
0.6647	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6100	Approved
0.6646	Remote Similarity	NPD6099	Approved
0.6645	Remote Similarity	NPD3620	Phase 2
0.6645	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2979	Phase 3
0.6645	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3972	Approved
0.6644	Remote Similarity	NPD1894	Discontinued
0.6629	Remote Similarity	NPD8312	Approved
0.6629	Remote Similarity	NPD8313	Approved
0.6627	Remote Similarity	NPD7028	Phase 2
0.6623	Remote Similarity	NPD1470	Approved
0.6623	Remote Similarity	NPD3266	Approved
0.6623	Remote Similarity	NPD3267	Approved
0.6623	Remote Similarity	NPD2313	Discontinued
0.6622	Remote Similarity	NPD3496	Discontinued
0.6622	Remote Similarity	NPD3847	Discontinued
0.6614	Remote Similarity	NPD4582	Approved
0.6614	Remote Similarity	NPD8320	Phase 1

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