NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	464.26
Volume:	492.854
LogP:	5.278
LogD:	4.705
LogS:	-5.621
# Rotatable Bonds:	4
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	5.175
Fsp3:	0.586
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.868
MDCK Permeability:	3.4528748074080795e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.187
30% Bioavailability (F30%):	0.135

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.615
Plasma Protein Binding (PPB):	96.23992156982422%
Volume Distribution (VD):	2.111
Pgp-substrate:	4.3470611572265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.119
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.533
CYP2C19-substrate:	0.446
CYP2C9-inhibitor:	0.743
CYP2C9-substrate:	0.446
CYP2D6-inhibitor:	0.619
CYP2D6-substrate:	0.297
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.547

ADMET: Excretion

Clearance (CL):	6.746
Half-life (T1/2):	0.055

ADMET: Toxicity

hERG Blockers:	0.876
Human Hepatotoxicity (H-HT):	0.86
Drug-inuced Liver Injury (DILI):	0.233
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.189
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.958
Carcinogencity:	0.079
Eye Corrosion:	0.018
Eye Irritation:	0.055
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC477357

Natural Product ID:	NPC477357
*Common Name:**	[(1R,2R,4R,7S,9S,10E,13R,15S,16S)-13-hydroxy-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.02,4.07,9]hexadec-10-en-16-yl] (E)-3-phenylprop-2-enoate
IUPAC Name:	[(1R,2R,4R,7S,9S,10E,13R,15S,16S)-13-hydroxy-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.02,4.07,9]hexadec-10-en-16-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	QWCWFWSASCMKEX-FYQBYZSOSA-N
Standard InCHI:	InChI=1S/C29H36O5/c1-17-15-21-20(27(21,3)4)13-14-28(5)26(34-28)23-24(18(2)16-29(23,32)25(17)31)33-22(30)12-11-19-9-7-6-8-10-19/h6-12,15,18,20-21,23-24,26,32H,13-14,16H2,1-5H3/b12-11+,17-15+/t18-,20-,21-,23+,24-,26+,28+,29+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)/C=C/C3=CC=CC=C3)[C@@H]4[C@](O4)(CC[C@H]5[C@@H](C5(C)C)/C=C(/C2=O)\C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56662975
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 NPC477357 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	257
0.1-0.2	1014
0.2-0.3	2321
0.3-0.4	6657
0.4-0.5	13315
0.5-0.6	15857
0.6-0.7	2963
0.7-0.8	217
0.8-0.85	47
0.85-0.9	32
0.9-0.95	12
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9835	High Similarity	NPC37968
0.975	High Similarity	NPC477366
0.9748	High Similarity	NPC477362
0.9669	High Similarity	NPC477365
0.959	High Similarity	NPC477370
0.9587	High Similarity	NPC477363
0.9444	High Similarity	NPC477359
0.9421	High Similarity	NPC8990
0.9344	High Similarity	NPC477369
0.928	High Similarity	NPC475452
0.928	High Similarity	NPC475671
0.9141	High Similarity	NPC477368
0.9134	High Similarity	NPC477360
0.907	High Similarity	NPC477367
0.907	High Similarity	NPC232888
0.9062	High Similarity	NPC477364
0.8976	High Similarity	NPC272946
0.8976	High Similarity	NPC42234
0.8855	High Similarity	NPC477358
0.8682	High Similarity	NPC122504
0.8682	High Similarity	NPC3450
0.8636	High Similarity	NPC270364
0.8593	High Similarity	NPC473654
0.85	High Similarity	NPC477101
0.85	High Similarity	NPC477097
0.85	High Similarity	NPC477099
0.8496	Intermediate Similarity	NPC472247
0.8467	Intermediate Similarity	NPC477094
0.8467	Intermediate Similarity	NPC477096
0.8456	Intermediate Similarity	NPC473497
0.8444	Intermediate Similarity	NPC276652
0.8358	Intermediate Similarity	NPC290833
0.8358	Intermediate Similarity	NPC475262
0.8358	Intermediate Similarity	NPC265459
0.8345	Intermediate Similarity	NPC471162
0.8333	Intermediate Similarity	NPC45307
0.8333	Intermediate Similarity	NPC153214
0.8322	Intermediate Similarity	NPC477098
0.8322	Intermediate Similarity	NPC477100
0.8321	Intermediate Similarity	NPC475413
0.8321	Intermediate Similarity	NPC474303
0.8296	Intermediate Similarity	NPC285221
0.8296	Intermediate Similarity	NPC194769
0.8286	Intermediate Similarity	NPC477095
0.8284	Intermediate Similarity	NPC472250
0.8239	Intermediate Similarity	NPC25484
0.8239	Intermediate Similarity	NPC232583
0.8239	Intermediate Similarity	NPC125033
0.8235	Intermediate Similarity	NPC86772
0.8201	Intermediate Similarity	NPC82467
0.8175	Intermediate Similarity	NPC272523
0.8175	Intermediate Similarity	NPC325805
0.8156	Intermediate Similarity	NPC170668
0.8134	Intermediate Similarity	NPC233860
0.8134	Intermediate Similarity	NPC239358
0.8134	Intermediate Similarity	NPC233692
0.8116	Intermediate Similarity	NPC475660
0.8116	Intermediate Similarity	NPC251294
0.8099	Intermediate Similarity	NPC205389
0.8074	Intermediate Similarity	NPC472248
0.8015	Intermediate Similarity	NPC311492
0.8015	Intermediate Similarity	NPC28836
0.7956	Intermediate Similarity	NPC79699
0.7956	Intermediate Similarity	NPC200154
0.7929	Intermediate Similarity	NPC242355
0.7899	Intermediate Similarity	NPC52523
0.7899	Intermediate Similarity	NPC217673
0.7899	Intermediate Similarity	NPC202729
0.7895	Intermediate Similarity	NPC472706
0.7872	Intermediate Similarity	NPC183540
0.7857	Intermediate Similarity	NPC473440
0.7852	Intermediate Similarity	NPC475508
0.7842	Intermediate Similarity	NPC27721
0.7836	Intermediate Similarity	NPC472707
0.7829	Intermediate Similarity	NPC472708
0.7803	Intermediate Similarity	NPC472704
0.7801	Intermediate Similarity	NPC187566
0.7786	Intermediate Similarity	NPC473301
0.7754	Intermediate Similarity	NPC153617
0.7754	Intermediate Similarity	NPC471911
0.7754	Intermediate Similarity	NPC329913
0.7754	Intermediate Similarity	NPC4242
0.7746	Intermediate Similarity	NPC63737
0.7727	Intermediate Similarity	NPC472703
0.7669	Intermediate Similarity	NPC140118
0.7669	Intermediate Similarity	NPC12881
0.7656	Intermediate Similarity	NPC9274
0.7647	Intermediate Similarity	NPC477355
0.7634	Intermediate Similarity	NPC474223
0.7634	Intermediate Similarity	NPC475827
0.7626	Intermediate Similarity	NPC324898
0.7626	Intermediate Similarity	NPC298547
0.7626	Intermediate Similarity	NPC470143
0.7626	Intermediate Similarity	NPC126516
0.7626	Intermediate Similarity	NPC322503
0.7626	Intermediate Similarity	NPC134937
0.7622	Intermediate Similarity	NPC140021
0.76	Intermediate Similarity	NPC70344
0.7589	Intermediate Similarity	NPC184109
0.7586	Intermediate Similarity	NPC134131
0.7586	Intermediate Similarity	NPC25043
0.7581	Intermediate Similarity	NPC20485
0.7571	Intermediate Similarity	NPC149401
0.7571	Intermediate Similarity	NPC279637
0.7561	Intermediate Similarity	NPC321670
0.7557	Intermediate Similarity	NPC204784
0.7556	Intermediate Similarity	NPC476599
0.7552	Intermediate Similarity	NPC471862
0.7535	Intermediate Similarity	NPC170718
0.7533	Intermediate Similarity	NPC469456
0.7521	Intermediate Similarity	NPC477356
0.7517	Intermediate Similarity	NPC138641
0.7517	Intermediate Similarity	NPC80895
0.7517	Intermediate Similarity	NPC471912
0.7517	Intermediate Similarity	NPC283875
0.7517	Intermediate Similarity	NPC469648
0.7517	Intermediate Similarity	NPC469647
0.7517	Intermediate Similarity	NPC22571
0.75	Intermediate Similarity	NPC203486
0.75	Intermediate Similarity	NPC473243
0.75	Intermediate Similarity	NPC474222
0.75	Intermediate Similarity	NPC475804
0.75	Intermediate Similarity	NPC51181
0.7468	Intermediate Similarity	NPC165234
0.7468	Intermediate Similarity	NPC55744
0.7468	Intermediate Similarity	NPC475536
0.7466	Intermediate Similarity	NPC277053
0.7466	Intermediate Similarity	NPC301946
0.7465	Intermediate Similarity	NPC205305
0.7465	Intermediate Similarity	NPC327511
0.7464	Intermediate Similarity	NPC49272
0.7464	Intermediate Similarity	NPC82712
0.7463	Intermediate Similarity	NPC474254
0.7463	Intermediate Similarity	NPC474159
0.7459	Intermediate Similarity	NPC118405
0.745	Intermediate Similarity	NPC472398
0.7448	Intermediate Similarity	NPC191387
0.7448	Intermediate Similarity	NPC95449
0.7448	Intermediate Similarity	NPC131966
0.7445	Intermediate Similarity	NPC115797
0.7445	Intermediate Similarity	NPC51448
0.7429	Intermediate Similarity	NPC15850
0.7419	Intermediate Similarity	NPC475300
0.7419	Intermediate Similarity	NPC475437
0.7419	Intermediate Similarity	NPC473641
0.7419	Intermediate Similarity	NPC473797
0.7419	Intermediate Similarity	NPC475505
0.7419	Intermediate Similarity	NPC475464
0.7417	Intermediate Similarity	NPC471176
0.7413	Intermediate Similarity	NPC53361
0.7413	Intermediate Similarity	NPC121268
0.741	Intermediate Similarity	NPC470278
0.741	Intermediate Similarity	NPC72915
0.741	Intermediate Similarity	NPC472418
0.7405	Intermediate Similarity	NPC152812
0.74	Intermediate Similarity	NPC233581
0.74	Intermediate Similarity	NPC145649
0.7391	Intermediate Similarity	NPC225103
0.7381	Intermediate Similarity	NPC469636
0.7379	Intermediate Similarity	NPC471856
0.7379	Intermediate Similarity	NPC475135
0.7372	Intermediate Similarity	NPC473423
0.7372	Intermediate Similarity	NPC169913
0.7368	Intermediate Similarity	NPC11410
0.7364	Intermediate Similarity	NPC307651
0.7357	Intermediate Similarity	NPC80599
0.7357	Intermediate Similarity	NPC209851
0.7353	Intermediate Similarity	NPC246166
0.7353	Intermediate Similarity	NPC284022
0.7347	Intermediate Similarity	NPC127857
0.7347	Intermediate Similarity	NPC478264
0.7338	Intermediate Similarity	NPC473443
0.7338	Intermediate Similarity	NPC472388
0.7338	Intermediate Similarity	NPC475138
0.7333	Intermediate Similarity	NPC161955
0.7333	Intermediate Similarity	NPC477354
0.7329	Intermediate Similarity	NPC284957
0.7329	Intermediate Similarity	NPC477894
0.7313	Intermediate Similarity	NPC50872
0.7303	Intermediate Similarity	NPC251139
0.7299	Intermediate Similarity	NPC470818
0.7299	Intermediate Similarity	NPC275576
0.7297	Intermediate Similarity	NPC478263
0.7293	Intermediate Similarity	NPC202015
0.7292	Intermediate Similarity	NPC9905
0.7285	Intermediate Similarity	NPC240592
0.7285	Intermediate Similarity	NPC117346
0.7279	Intermediate Similarity	NPC328107
0.7279	Intermediate Similarity	NPC471466
0.7278	Intermediate Similarity	NPC161151
0.7273	Intermediate Similarity	NPC87090
0.7273	Intermediate Similarity	NPC94425
0.7273	Intermediate Similarity	NPC159692
0.7266	Intermediate Similarity	NPC477247
0.726	Intermediate Similarity	NPC182869
0.7255	Intermediate Similarity	NPC154675
0.7254	Intermediate Similarity	NPC48929
0.7252	Intermediate Similarity	NPC475305
0.7248	Intermediate Similarity	NPC132652
0.7244	Intermediate Similarity	NPC40178

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 NPC477357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	760
0.2-0.3	1732
0.3-0.4	3160
0.4-0.5	2181
0.5-0.6	939
0.6-0.7	150
0.7-0.8	9
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
0.7958	Intermediate Similarity	NPD7236	Approved
0.7787	Intermediate Similarity	NPD6685	Approved
0.7687	Intermediate Similarity	NPD7239	Suspended
0.7686	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6647	Phase 2
0.7541	Intermediate Similarity	NPD5765	Approved
0.746	Intermediate Similarity	NPD2067	Discontinued
0.7422	Intermediate Similarity	NPD7094	Approved
0.7422	Intermediate Similarity	NPD6858	Approved
0.7357	Intermediate Similarity	NPD7961	Discontinued
0.7344	Intermediate Similarity	NPD6912	Phase 3
0.7313	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6085	Phase 2
0.7246	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7057	Phase 3
0.7226	Intermediate Similarity	NPD7058	Phase 2
0.7132	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2629	Approved
0.7045	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7305	Phase 1
0.6977	Remote Similarity	NPD2182	Approved
0.6933	Remote Similarity	NPD7799	Discontinued
0.6929	Remote Similarity	NPD5909	Discontinued
0.688	Remote Similarity	NPD2066	Phase 3
0.6866	Remote Similarity	NPD4198	Discontinued
0.6842	Remote Similarity	NPD6010	Discontinued
0.6829	Remote Similarity	NPD1693	Approved
0.6809	Remote Similarity	NPD6362	Approved
0.6783	Remote Similarity	NPD7055	Discontinued
0.6779	Remote Similarity	NPD6002	Phase 3
0.6779	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6004	Phase 3
0.6779	Remote Similarity	NPD6005	Phase 3
0.6779	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6663	Approved
0.6744	Remote Similarity	NPD5048	Discontinued
0.6736	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6653	Approved
0.6719	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1929	Approved
0.6719	Remote Similarity	NPD1930	Approved
0.6718	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2652	Approved
0.6716	Remote Similarity	NPD2650	Approved
0.6715	Remote Similarity	NPD7741	Discontinued
0.6715	Remote Similarity	NPD7009	Phase 2
0.6714	Remote Similarity	NPD6637	Approved
0.6713	Remote Similarity	NPD5736	Approved
0.6711	Remote Similarity	NPD7137	Phase 2
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD164	Approved
0.6667	Remote Similarity	NPD1088	Approved
0.6643	Remote Similarity	NPD5647	Approved
0.6642	Remote Similarity	NPD7610	Discontinued
0.6641	Remote Similarity	NPD6881	Approved
0.6641	Remote Similarity	NPD6899	Approved
0.6639	Remote Similarity	NPD3672	Approved
0.6639	Remote Similarity	NPD3673	Approved
0.6619	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6649	Approved
0.6617	Remote Similarity	NPD6650	Approved
0.6565	Remote Similarity	NPD5697	Approved
0.6557	Remote Similarity	NPD5346	Phase 2
0.6557	Remote Similarity	NPD5347	Phase 2
0.6544	Remote Similarity	NPD4766	Approved
0.6541	Remote Similarity	NPD7102	Approved
0.6541	Remote Similarity	NPD7290	Approved
0.6541	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD6273	Approved
0.6538	Remote Similarity	NPD1237	Approved
0.6535	Remote Similarity	NPD9495	Approved
0.6525	Remote Similarity	NPD6287	Discontinued
0.6525	Remote Similarity	NPD4807	Approved
0.6525	Remote Similarity	NPD4806	Approved
0.6515	Remote Similarity	NPD6406	Approved
0.6512	Remote Similarity	NPD1932	Approved
0.6507	Remote Similarity	NPD7008	Discontinued
0.6504	Remote Similarity	NPD1089	Approved
0.6504	Remote Similarity	NPD1086	Approved
0.6504	Remote Similarity	NPD1090	Approved
0.6504	Remote Similarity	NPD5785	Approved
0.65	Remote Similarity	NPD5306	Approved
0.65	Remote Similarity	NPD5305	Approved
0.6493	Remote Similarity	NPD6847	Approved
0.6493	Remote Similarity	NPD6617	Approved
0.6493	Remote Similarity	NPD8130	Phase 1
0.6493	Remote Similarity	NPD6869	Approved
0.6489	Remote Similarity	NPD6675	Approved
0.6489	Remote Similarity	NPD6402	Approved
0.6489	Remote Similarity	NPD5739	Approved
0.6489	Remote Similarity	NPD7128	Approved
0.6484	Remote Similarity	NPD7798	Approved
0.6483	Remote Similarity	NPD3662	Phase 3
0.6483	Remote Similarity	NPD3661	Approved
0.6483	Remote Similarity	NPD3664	Approved
0.6483	Remote Similarity	NPD7084	Phase 3
0.6483	Remote Similarity	NPD3663	Approved
0.6471	Remote Similarity	NPD7685	Pre-registration
0.6466	Remote Similarity	NPD6012	Approved
0.6466	Remote Similarity	NPD6372	Approved
0.6466	Remote Similarity	NPD6373	Approved
0.6466	Remote Similarity	NPD2329	Discontinued
0.6466	Remote Similarity	NPD6014	Approved
0.6466	Remote Similarity	NPD6013	Approved
0.6447	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD969	Suspended
0.6444	Remote Similarity	NPD6882	Approved
0.6444	Remote Similarity	NPD8297	Approved
0.6444	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4628	Phase 3
0.6429	Remote Similarity	NPD8166	Discontinued
0.6423	Remote Similarity	NPD800	Approved
0.6423	Remote Similarity	NPD5951	Approved
0.6418	Remote Similarity	NPD1317	Discontinued
0.6418	Remote Similarity	NPD6371	Approved
0.6393	Remote Similarity	NPD4793	Discontinued
0.6391	Remote Similarity	NPD7320	Approved
0.6391	Remote Similarity	NPD6011	Approved
0.6387	Remote Similarity	NPD6190	Approved
0.6378	Remote Similarity	NPD1989	Approved
0.6377	Remote Similarity	NPD7115	Discovery
0.6374	Remote Similarity	NPD6765	Approved
0.6374	Remote Similarity	NPD6764	Approved
0.6358	Remote Similarity	NPD5761	Phase 2
0.6358	Remote Similarity	NPD5760	Phase 2
0.6357	Remote Similarity	NPD9545	Approved
0.6357	Remote Similarity	NPD1238	Approved
0.6351	Remote Similarity	NPD3268	Approved
0.634	Remote Similarity	NPD5762	Approved
0.634	Remote Similarity	NPD5763	Approved
0.634	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD4136	Approved
0.6338	Remote Similarity	NPD4106	Approved
0.6338	Remote Similarity	NPD4135	Approved
0.6333	Remote Similarity	NPD4684	Phase 3
0.6333	Remote Similarity	NPD4686	Approved
0.6333	Remote Similarity	NPD4685	Phase 3
0.6328	Remote Similarity	NPD6084	Phase 2
0.6328	Remote Similarity	NPD6083	Phase 2
0.6316	Remote Similarity	NPD5701	Approved
0.6312	Remote Similarity	NPD5585	Approved
0.6303	Remote Similarity	NPD226	Approved
0.6299	Remote Similarity	NPD5695	Phase 3
0.6299	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4233	Approved
0.6296	Remote Similarity	NPD4234	Approved
0.6289	Remote Similarity	NPD7606	Phase 3
0.6286	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6065	Approved
0.6279	Remote Similarity	NPD5696	Approved
0.6279	Remote Similarity	NPD8368	Discontinued
0.6279	Remote Similarity	NPD5926	Approved
0.6267	Remote Similarity	NPD4140	Approved
0.6266	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8407	Phase 2
0.626	Remote Similarity	NPD1087	Approved
0.626	Remote Similarity	NPD1282	Approved
0.626	Remote Similarity	NPD5211	Phase 2
0.6259	Remote Similarity	NPD3317	Approved
0.6259	Remote Similarity	NPD5204	Approved
0.625	Remote Similarity	NPD6435	Approved
0.6243	Remote Similarity	NPD7962	Phase 2
0.6242	Remote Similarity	NPD3764	Approved
0.6241	Remote Similarity	NPD4479	Discontinued
0.6233	Remote Similarity	NPD2797	Approved
0.6231	Remote Similarity	NPD5285	Approved
0.6231	Remote Similarity	NPD5286	Approved
0.6231	Remote Similarity	NPD4696	Approved
0.623	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD6784	Approved
0.6229	Remote Similarity	NPD6785	Approved
0.6228	Remote Similarity	NPD8127	Discontinued
0.6218	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4110	Phase 3
0.6218	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD2575	Approved
0.6211	Remote Similarity	NPD7458	Discontinued
0.6209	Remote Similarity	NPD2799	Discontinued
0.6209	Remote Similarity	NPD7033	Discontinued
0.6204	Remote Similarity	NPD6053	Discontinued
0.62	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3090	Approved
0.62	Remote Similarity	NPD3088	Approved
0.62	Remote Similarity	NPD3614	Approved
0.62	Remote Similarity	NPD4746	Phase 3
0.62	Remote Similarity	NPD2571	Approved
0.62	Remote Similarity	NPD8032	Phase 2
0.62	Remote Similarity	NPD3087	Approved
0.62	Remote Similarity	NPD3615	Approved
0.62	Remote Similarity	NPD3089	Approved
0.62	Remote Similarity	NPD4745	Approved
0.62	Remote Similarity	NPD2566	Approved
0.62	Remote Similarity	NPD7715	Approved
0.62	Remote Similarity	NPD7714	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