NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	544.32
Volume:	597.277
LogP:	6.455
LogD:	5.148
LogS:	-5.525
# Rotatable Bonds:	8
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.153
Synthetic Accessibility Score:	5.527
Fsp3:	0.486
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.841
MDCK Permeability:	1.0750999535957817e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.792

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.871
Plasma Protein Binding (PPB):	92.27764129638672%
Volume Distribution (VD):	3.09
Pgp-substrate:	5.979878902435303%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.755
CYP2C19-substrate:	0.236
CYP2C9-inhibitor:	0.931
CYP2C9-substrate:	0.183
CYP2D6-inhibitor:	0.818
CYP2D6-substrate:	0.33
CYP3A4-inhibitor:	0.975
CYP3A4-substrate:	0.712

ADMET: Excretion

Clearance (CL):	8.465
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.865
Human Hepatotoxicity (H-HT):	0.867
Drug-inuced Liver Injury (DILI):	0.688
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.231
Maximum Recommended Daily Dose:	0.582
Skin Sensitization:	0.969
Carcinogencity:	0.083
Eye Corrosion:	0.004
Eye Irritation:	0.025
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC477369

Natural Product ID:	NPC477369
*Common Name:**	[(1R,3E,5S,7S,9Z,11R,12R,13S,14S)-3,6,6,10,14-pentamethyl-2-oxo-11,13-bis(prop-1-en-2-yloxy)-1-tricyclo[10.3.0.05,7]pentadeca-3,9-dienyl] (E)-3-phenylprop-2-enoate
IUPAC Name:	[(1R,3E,5S,7S,9Z,11R,12R,13S,14S)-3,6,6,10,14-pentamethyl-2-oxo-11,13-bis(prop-1-en-2-yloxy)-1-tricyclo[10.3.0.05,7]pentadeca-3,9-dienyl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	MXEVRBCQVDKHEV-HAYWDCGVSA-N
Standard InCHI:	InChI=1S/C35H44O5/c1-21(2)38-31-23(5)15-17-27-28(34(27,8)9)19-24(6)33(37)35(20-25(7)32(30(31)35)39-22(3)4)40-29(36)18-16-26-13-11-10-12-14-26/h10-16,18-19,25,27-28,30-32H,1,3,17,20H2,2,4-9H3/b18-16+,23-15-,24-19+/t25-,27-,28-,30-,31-,32-,35+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1OC(=C)C)[C@H](/C(=C\C[C@H]3[C@@H](C3(C)C)/C=C(/C2=O)\C)/C)OC(=C)C)OC(=O)/C=C/C4=CC=CC=C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56666458
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19036584]
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	stems	Botanical Garden, Osmania University, Hyderabad, Andhra Pradesh	2006-AUG	PMID[21534583]
NPO28682	Jatropha multifida	Species	Euphorbiaceae	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
Others	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	<	30	%	PMID[21534583]

☑ 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 NPC477369 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	286
0.1-0.2	1172
0.2-0.3	2311
0.3-0.4	6983
0.4-0.5	13057
0.5-0.6	15538
0.6-0.7	3013
0.7-0.8	226
0.8-0.85	64
0.85-0.9	30
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9915	High Similarity	NPC8990
0.9431	High Similarity	NPC475671
0.9431	High Similarity	NPC475452
0.9426	High Similarity	NPC477370
0.9421	High Similarity	NPC477363
0.9421	High Similarity	NPC477366
0.9417	High Similarity	NPC477362
0.935	High Similarity	NPC37968
0.9344	High Similarity	NPC477357
0.9344	High Similarity	NPC477365
0.9274	High Similarity	NPC42234
0.9127	High Similarity	NPC477360
0.9062	High Similarity	NPC270364
0.8992	High Similarity	NPC477358
0.8984	High Similarity	NPC477368
0.8915	High Similarity	NPC477367
0.8915	High Similarity	NPC232888
0.8906	High Similarity	NPC477364
0.8855	High Similarity	NPC276652
0.8837	High Similarity	NPC477359
0.8819	High Similarity	NPC122504
0.8819	High Similarity	NPC3450
0.8769	High Similarity	NPC475262
0.8769	High Similarity	NPC265459
0.8769	High Similarity	NPC290833
0.8722	High Similarity	NPC473654
0.8702	High Similarity	NPC285221
0.8702	High Similarity	NPC194769
0.8692	High Similarity	NPC472250
0.8672	High Similarity	NPC272946
0.8636	High Similarity	NPC86772
0.8593	High Similarity	NPC477094
0.8593	High Similarity	NPC477096
0.8571	High Similarity	NPC272523
0.8571	High Similarity	NPC325805
0.8507	High Similarity	NPC251294
0.8507	High Similarity	NPC475660
0.8485	Intermediate Similarity	NPC472247
0.8467	Intermediate Similarity	NPC471162
0.8456	Intermediate Similarity	NPC82467
0.8444	Intermediate Similarity	NPC473497
0.8406	Intermediate Similarity	NPC477095
0.8346	Intermediate Similarity	NPC79699
0.8321	Intermediate Similarity	NPC153214
0.8321	Intermediate Similarity	NPC45307
0.8309	Intermediate Similarity	NPC475413
0.8309	Intermediate Similarity	NPC474303
0.8227	Intermediate Similarity	NPC125033
0.8227	Intermediate Similarity	NPC477097
0.8227	Intermediate Similarity	NPC477101
0.8227	Intermediate Similarity	NPC477099
0.8143	Intermediate Similarity	NPC170668
0.8106	Intermediate Similarity	NPC475508
0.8099	Intermediate Similarity	NPC232583
0.8099	Intermediate Similarity	NPC25484
0.8085	Intermediate Similarity	NPC205389
0.8056	Intermediate Similarity	NPC477100
0.8056	Intermediate Similarity	NPC477098
0.8043	Intermediate Similarity	NPC187566
0.8	Intermediate Similarity	NPC153617
0.8	Intermediate Similarity	NPC4242
0.8	Intermediate Similarity	NPC471911
0.7985	Intermediate Similarity	NPC233860
0.7926	Intermediate Similarity	NPC472248
0.7883	Intermediate Similarity	NPC202729
0.7868	Intermediate Similarity	NPC28836
0.7868	Intermediate Similarity	NPC298547
0.7868	Intermediate Similarity	NPC134937
0.7868	Intermediate Similarity	NPC324898
0.7852	Intermediate Similarity	NPC233692
0.7852	Intermediate Similarity	NPC239358
0.7826	Intermediate Similarity	NPC27721
0.7826	Intermediate Similarity	NPC184109
0.781	Intermediate Similarity	NPC149401
0.781	Intermediate Similarity	NPC200154
0.781	Intermediate Similarity	NPC279637
0.7803	Intermediate Similarity	NPC476599
0.7786	Intermediate Similarity	NPC242355
0.7752	Intermediate Similarity	NPC473243
0.7737	Intermediate Similarity	NPC311492
0.7714	Intermediate Similarity	NPC473440
0.7698	Intermediate Similarity	NPC327511
0.7698	Intermediate Similarity	NPC205305
0.7676	Intermediate Similarity	NPC191387
0.7676	Intermediate Similarity	NPC131966
0.7656	Intermediate Similarity	NPC94425
0.7647	Intermediate Similarity	NPC470278
0.7643	Intermediate Similarity	NPC53361
0.7643	Intermediate Similarity	NPC121268
0.7643	Intermediate Similarity	NPC473301
0.7626	Intermediate Similarity	NPC217673
0.7626	Intermediate Similarity	NPC52523
0.7612	Intermediate Similarity	NPC473423
0.7612	Intermediate Similarity	NPC472706
0.7606	Intermediate Similarity	NPC183540
0.7606	Intermediate Similarity	NPC63737
0.7606	Intermediate Similarity	NPC475135
0.7584	Intermediate Similarity	NPC70344
0.7556	Intermediate Similarity	NPC472707
0.7538	Intermediate Similarity	NPC472708
0.7519	Intermediate Similarity	NPC472704
0.7519	Intermediate Similarity	NPC152812
0.7518	Intermediate Similarity	NPC472418
0.75	Intermediate Similarity	NPC471912
0.75	Intermediate Similarity	NPC80895
0.75	Intermediate Similarity	NPC40178
0.75	Intermediate Similarity	NPC469636
0.7483	Intermediate Similarity	NPC140021
0.7482	Intermediate Similarity	NPC322503
0.7482	Intermediate Similarity	NPC329913
0.7482	Intermediate Similarity	NPC470143
0.7481	Intermediate Similarity	NPC475804
0.7481	Intermediate Similarity	NPC475827
0.7481	Intermediate Similarity	NPC48992
0.7481	Intermediate Similarity	NPC474223
0.7481	Intermediate Similarity	NPC474222
0.748	Intermediate Similarity	NPC307651
0.7451	Intermediate Similarity	NPC55744
0.7448	Intermediate Similarity	NPC277053
0.7448	Intermediate Similarity	NPC134131
0.7448	Intermediate Similarity	NPC301946
0.7448	Intermediate Similarity	NPC25043
0.7444	Intermediate Similarity	NPC474254
0.7444	Intermediate Similarity	NPC474159
0.7444	Intermediate Similarity	NPC472703
0.7426	Intermediate Similarity	NPC195224
0.7424	Intermediate Similarity	NPC50872
0.7419	Intermediate Similarity	NPC47536
0.7413	Intermediate Similarity	NPC471862
0.741	Intermediate Similarity	NPC472656
0.7407	Intermediate Similarity	NPC470818
0.7402	Intermediate Similarity	NPC161611
0.7397	Intermediate Similarity	NPC475552
0.7388	Intermediate Similarity	NPC473881
0.7388	Intermediate Similarity	NPC12881
0.7388	Intermediate Similarity	NPC469742
0.7388	Intermediate Similarity	NPC140118
0.7383	Intermediate Similarity	NPC138641
0.7383	Intermediate Similarity	NPC22571
0.7383	Intermediate Similarity	NPC283875
0.7383	Intermediate Similarity	NPC469648
0.7383	Intermediate Similarity	NPC469647
0.7381	Intermediate Similarity	NPC477247
0.7364	Intermediate Similarity	NPC9274
0.7361	Intermediate Similarity	NPC51181
0.7361	Intermediate Similarity	NPC471856
0.7357	Intermediate Similarity	NPC203486
0.7357	Intermediate Similarity	NPC126516
0.735	Intermediate Similarity	NPC202824
0.735	Intermediate Similarity	NPC477361
0.7339	Intermediate Similarity	NPC470192
0.7338	Intermediate Similarity	NPC475536
0.7338	Intermediate Similarity	NPC469499
0.7338	Intermediate Similarity	NPC165234
0.7333	Intermediate Similarity	NPC472693
0.7333	Intermediate Similarity	NPC145052
0.7333	Intermediate Similarity	NPC472694
0.7329	Intermediate Similarity	NPC471100
0.7329	Intermediate Similarity	NPC471107
0.7323	Intermediate Similarity	NPC270699
0.7323	Intermediate Similarity	NPC82899
0.7319	Intermediate Similarity	NPC471832
0.7319	Intermediate Similarity	NPC49272
0.7315	Intermediate Similarity	NPC472398
0.7311	Intermediate Similarity	NPC477354
0.731	Intermediate Similarity	NPC284957
0.731	Intermediate Similarity	NPC95449
0.7297	Intermediate Similarity	NPC473403
0.7295	Intermediate Similarity	NPC118405
0.729	Intermediate Similarity	NPC473641
0.729	Intermediate Similarity	NPC475505
0.729	Intermediate Similarity	NPC475464
0.729	Intermediate Similarity	NPC473797
0.729	Intermediate Similarity	NPC475300
0.729	Intermediate Similarity	NPC475437
0.7286	Intermediate Similarity	NPC15850
0.7285	Intermediate Similarity	NPC469456
0.728	Intermediate Similarity	NPC20485
0.7279	Intermediate Similarity	NPC473082
0.7273	Intermediate Similarity	NPC204784
0.7273	Intermediate Similarity	NPC170718
0.7267	Intermediate Similarity	NPC233581
0.7267	Intermediate Similarity	NPC145649
0.7258	Intermediate Similarity	NPC321670
0.7248	Intermediate Similarity	NPC254558
0.7246	Intermediate Similarity	NPC225103
0.7244	Intermediate Similarity	NPC305912
0.7244	Intermediate Similarity	NPC1082
0.7237	Intermediate Similarity	NPC11410
0.7231	Intermediate Similarity	NPC216387
0.7231	Intermediate Similarity	NPC476476
0.7214	Intermediate Similarity	NPC475493
0.7214	Intermediate Similarity	NPC238370
0.7214	Intermediate Similarity	NPC209851
0.7214	Intermediate Similarity	NPC475569
0.7206	Intermediate Similarity	NPC246166
0.7206	Intermediate Similarity	NPC284022
0.72	Intermediate Similarity	NPC51602
0.72	Intermediate Similarity	NPC477251
0.72	Intermediate Similarity	NPC329705

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 NPC477369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	802
0.2-0.3	1681
0.3-0.4	3181
0.4-0.5	2156
0.5-0.6	923
0.6-0.7	152
0.7-0.8	10
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
0.7869	Intermediate Similarity	NPD2067	Discontinued
0.7817	Intermediate Similarity	NPD7236	Approved
0.7551	Intermediate Similarity	NPD7239	Suspended
0.754	Intermediate Similarity	NPD7094	Approved
0.754	Intermediate Similarity	NPD6858	Approved
0.7536	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD6685	Approved
0.7424	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7961	Discontinued
0.7244	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6647	Phase 2
0.7236	Intermediate Similarity	NPD5765	Approved
0.7154	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7058	Phase 2
0.7097	Intermediate Similarity	NPD7057	Phase 3
0.7087	Intermediate Similarity	NPD2182	Approved
0.7054	Intermediate Similarity	NPD6912	Phase 3
0.6978	Remote Similarity	NPD6085	Phase 2
0.6978	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7799	Discontinued
0.6905	Remote Similarity	NPD5909	Discontinued
0.6879	Remote Similarity	NPD7055	Discontinued
0.6838	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6637	Approved
0.6772	Remote Similarity	NPD164	Approved
0.6767	Remote Similarity	NPD2629	Approved
0.675	Remote Similarity	NPD3672	Approved
0.675	Remote Similarity	NPD3673	Approved
0.6735	Remote Similarity	NPD7305	Phase 1
0.6721	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7798	Approved
0.6716	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD6362	Approved
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6005	Phase 3
0.6644	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6004	Phase 3
0.6644	Remote Similarity	NPD6355	Discontinued
0.6644	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6002	Phase 3
0.6642	Remote Similarity	NPD4766	Approved
0.6619	Remote Similarity	NPD6287	Discontinued
0.6599	Remote Similarity	NPD6653	Approved
0.6587	Remote Similarity	NPD2066	Phase 3
0.6569	Remote Similarity	NPD7741	Discontinued
0.6567	Remote Similarity	NPD6010	Discontinued
0.6532	Remote Similarity	NPD1693	Approved
0.6522	Remote Similarity	NPD5585	Approved
0.6507	Remote Similarity	NPD6663	Approved
0.6507	Remote Similarity	NPD8032	Phase 2
0.6503	Remote Similarity	NPD5647	Approved
0.65	Remote Similarity	NPD1282	Approved
0.6489	Remote Similarity	NPD6899	Approved
0.6489	Remote Similarity	NPD6881	Approved
0.6483	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.648	Remote Similarity	NPD1989	Approved
0.6474	Remote Similarity	NPD7606	Phase 3
0.6467	Remote Similarity	NPD7137	Phase 2
0.6466	Remote Similarity	NPD6649	Approved
0.6466	Remote Similarity	NPD8130	Phase 1
0.6466	Remote Similarity	NPD6650	Approved
0.6462	Remote Similarity	NPD5048	Discontinued
0.6458	Remote Similarity	NPD5736	Approved
0.6458	Remote Similarity	NPD7084	Phase 3
0.6457	Remote Similarity	NPD1238	Approved
0.6449	Remote Similarity	NPD7009	Phase 2
0.6444	Remote Similarity	NPD2650	Approved
0.6444	Remote Similarity	NPD2652	Approved
0.6439	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1929	Approved
0.6434	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1930	Approved
0.6418	Remote Similarity	NPD8297	Approved
0.6412	Remote Similarity	NPD5697	Approved
0.641	Remote Similarity	NPD6273	Approved
0.6391	Remote Similarity	NPD7102	Approved
0.6391	Remote Similarity	NPD4233	Approved
0.6391	Remote Similarity	NPD7290	Approved
0.6391	Remote Similarity	NPD4234	Approved
0.6391	Remote Similarity	NPD6883	Approved
0.6378	Remote Similarity	NPD5926	Approved
0.6377	Remote Similarity	NPD6065	Approved
0.6377	Remote Similarity	NPD7610	Discontinued
0.6371	Remote Similarity	NPD1088	Approved
0.6364	Remote Similarity	NPD1087	Approved
0.6364	Remote Similarity	NPD5667	Approved
0.6364	Remote Similarity	NPD3887	Approved
0.6364	Remote Similarity	NPD1876	Approved
0.6353	Remote Similarity	NPD7685	Pre-registration
0.6353	Remote Similarity	NPD6765	Approved
0.6353	Remote Similarity	NPD6764	Approved
0.635	Remote Similarity	NPD3317	Approved
0.6343	Remote Similarity	NPD6847	Approved
0.6343	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6617	Approved
0.6343	Remote Similarity	NPD6869	Approved
0.6338	Remote Similarity	NPD3972	Approved
0.6336	Remote Similarity	NPD5739	Approved
0.6336	Remote Similarity	NPD6675	Approved
0.6336	Remote Similarity	NPD7128	Approved
0.6336	Remote Similarity	NPD6402	Approved
0.6319	Remote Similarity	NPD3267	Approved
0.6319	Remote Similarity	NPD3266	Approved
0.6316	Remote Similarity	NPD6373	Approved
0.6316	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6014	Approved
0.6316	Remote Similarity	NPD6372	Approved
0.6316	Remote Similarity	NPD5762	Approved
0.6316	Remote Similarity	NPD5763	Approved
0.6316	Remote Similarity	NPD6012	Approved
0.6316	Remote Similarity	NPD6013	Approved
0.6299	Remote Similarity	NPD4628	Phase 3
0.6299	Remote Similarity	NPD8166	Discontinued
0.6296	Remote Similarity	NPD6882	Approved
0.6294	Remote Similarity	NPD4359	Approved
0.629	Remote Similarity	NPD6050	Approved
0.629	Remote Similarity	NPD5694	Approved
0.629	Remote Similarity	NPD5693	Phase 1
0.6282	Remote Similarity	NPD7478	Approved
0.6268	Remote Similarity	NPD4806	Approved
0.6268	Remote Similarity	NPD4807	Approved
0.6264	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5346	Phase 2
0.626	Remote Similarity	NPD1237	Approved
0.626	Remote Similarity	NPD5347	Phase 2
0.6259	Remote Similarity	NPD7008	Discontinued
0.6258	Remote Similarity	NPD6190	Approved
0.6257	Remote Similarity	NPD8368	Discontinued
0.625	Remote Similarity	NPD6599	Discontinued
0.625	Remote Similarity	NPD9495	Approved
0.6243	Remote Similarity	NPD8407	Phase 2
0.6241	Remote Similarity	NPD5306	Approved
0.6241	Remote Similarity	NPD5305	Approved
0.6241	Remote Similarity	NPD7320	Approved
0.6241	Remote Similarity	NPD6011	Approved
0.6241	Remote Similarity	NPD6406	Approved
0.6235	Remote Similarity	NPD5760	Phase 2
0.6235	Remote Similarity	NPD5761	Phase 2
0.6233	Remote Similarity	NPD3662	Phase 3
0.6233	Remote Similarity	NPD3664	Approved
0.6233	Remote Similarity	NPD3663	Approved
0.6233	Remote Similarity	NPD3661	Approved
0.6231	Remote Similarity	NPD1932	Approved
0.6221	Remote Similarity	NPD7962	Phase 2
0.6216	Remote Similarity	NPD3268	Approved
0.621	Remote Similarity	NPD1090	Approved
0.621	Remote Similarity	NPD1089	Approved
0.621	Remote Similarity	NPD5692	Phase 3
0.621	Remote Similarity	NPD5785	Approved
0.621	Remote Similarity	NPD1086	Approved
0.6209	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6785	Approved
0.6207	Remote Similarity	NPD6784	Approved
0.6205	Remote Similarity	NPD8127	Discontinued
0.6194	Remote Similarity	NPD2329	Discontinued
0.619	Remote Similarity	NPD6832	Phase 2
0.6187	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD969	Suspended
0.6174	Remote Similarity	NPD7713	Phase 3
0.6174	Remote Similarity	NPD6233	Phase 2
0.6174	Remote Similarity	NPD4870	Approved
0.6172	Remote Similarity	NPD6084	Phase 2
0.6172	Remote Similarity	NPD6083	Phase 2
0.6171	Remote Similarity	NPD8434	Phase 2
0.6165	Remote Similarity	NPD5701	Approved
0.6165	Remote Similarity	NPD3134	Approved
0.6164	Remote Similarity	NPD2788	Approved
0.6159	Remote Similarity	NPD5951	Approved
0.6154	Remote Similarity	NPD225	Approved
0.6154	Remote Similarity	NPD227	Approved
0.6149	Remote Similarity	NPD7095	Approved
0.6148	Remote Similarity	NPD1317	Discontinued
0.6148	Remote Similarity	NPD6371	Approved
0.6143	Remote Similarity	NPD2347	Approved
0.6142	Remote Similarity	NPD5695	Phase 3
0.6139	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD4140	Approved
0.6129	Remote Similarity	NPD6904	Approved
0.6129	Remote Similarity	NPD6673	Approved
0.6129	Remote Similarity	NPD800	Approved
0.6129	Remote Similarity	NPD6080	Approved
0.6127	Remote Similarity	NPD17	Approved
0.6124	Remote Similarity	NPD5696	Approved
0.6118	Remote Similarity	NPD2569	Approved
0.6118	Remote Similarity	NPD2567	Approved
0.6107	Remote Similarity	NPD6798	Discontinued
0.6104	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD2353	Approved
0.6099	Remote Similarity	NPD9545	Approved
0.6098	Remote Similarity	NPD4793	Discontinued
0.6096	Remote Similarity	NPD2797	Approved
0.609	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.609	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.609	Remote Similarity	NPD6008	Approved
0.609	Remote Similarity	NPD4110	Phase 3

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