NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.18
Volume:	298.067
LogP:	2.875
LogD:	2.447
LogS:	-3.611
# Rotatable Bonds:	8
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	3.934
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.712
MDCK Permeability:	3.479147926555015e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.316
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.591
30% Bioavailability (F30%):	0.171

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.966
Plasma Protein Binding (PPB):	83.0904312133789%
Volume Distribution (VD):	1.831
Pgp-substrate:	21.40120506286621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.296
CYP2C19-inhibitor:	0.199
CYP2C19-substrate:	0.404
CYP2C9-inhibitor:	0.269
CYP2C9-substrate:	0.492
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.442
CYP3A4-substrate:	0.199

ADMET: Excretion

Clearance (CL):	7.461
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.295
Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.711
Skin Sensitization:	0.924
Carcinogencity:	0.127
Eye Corrosion:	0.005
Eye Irritation:	0.089
Respiratory Toxicity:	0.61

Download Data

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

Natural Product: NPC474252

Natural Product ID:	NPC474252
*Common Name:**	(3Ar,7Ar)-6-Hydroxy-2,3,3A,6,7,7A-Hexahydrobenzofuran-3A-Yl Octanoate
IUPAC Name:	[(3aR,7aR)-6-hydroxy-3,6,7,7a-tetrahydro-2H-1-benzofuran-3a-yl] octanoate
Synonyms:
Standard InCHIKey:	AINNINVYAFDFKK-VVRWDSKXSA-N
Standard InCHI:	InChI=1S/C16H26O4/c1-2-3-4-5-6-7-15(18)20-16-9-8-13(17)12-14(16)19-11-10-16/h8-9,13-14,17H,2-7,10-12H2,1H3/t13?,14-,16+/m1/s1
SMILES:	CCCCCCCC(=O)OC12CCOC1CC(C=C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464277
PubChem CID:	44567100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO33459	cornus controversa	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3236014]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	8.4	ug.mL-1	PMID[461126]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.5	ug.mL-1	PMID[461126]

☑ 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 NPC474252 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	155
0.1-0.2	984
0.2-0.3	4433
0.3-0.4	11956
0.4-0.5	12604
0.5-0.6	7484
0.6-0.7	4032
0.7-0.8	973
0.8-0.85	70
0.85-0.9	2
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC475210
0.9342	High Similarity	NPC474278
0.8947	High Similarity	NPC474280
0.8313	Intermediate Similarity	NPC475690
0.8272	Intermediate Similarity	NPC267231
0.8235	Intermediate Similarity	NPC255307
0.8214	Intermediate Similarity	NPC473390
0.8214	Intermediate Similarity	NPC40746
0.8214	Intermediate Similarity	NPC131669
0.8214	Intermediate Similarity	NPC169575
0.8202	Intermediate Similarity	NPC475912
0.8193	Intermediate Similarity	NPC24417
0.8193	Intermediate Similarity	NPC52861
0.8148	Intermediate Similarity	NPC320630
0.8148	Intermediate Similarity	NPC116177
0.8148	Intermediate Similarity	NPC7563
0.814	Intermediate Similarity	NPC469910
0.814	Intermediate Similarity	NPC305475
0.814	Intermediate Similarity	NPC475461
0.8118	Intermediate Similarity	NPC96259
0.8118	Intermediate Similarity	NPC295799
0.8118	Intermediate Similarity	NPC158756
0.8118	Intermediate Similarity	NPC141193
0.8118	Intermediate Similarity	NPC191476
0.8118	Intermediate Similarity	NPC476804
0.8118	Intermediate Similarity	NPC70424
0.8118	Intermediate Similarity	NPC114979
0.8118	Intermediate Similarity	NPC243618
0.8095	Intermediate Similarity	NPC89555
0.8095	Intermediate Similarity	NPC229825
0.8068	Intermediate Similarity	NPC218927
0.8068	Intermediate Similarity	NPC206001
0.8049	Intermediate Similarity	NPC93763
0.8049	Intermediate Similarity	NPC108816
0.8025	Intermediate Similarity	NPC190400
0.8025	Intermediate Similarity	NPC49392
0.8023	Intermediate Similarity	NPC21469
0.8023	Intermediate Similarity	NPC470755
0.8023	Intermediate Similarity	NPC165162
0.8022	Intermediate Similarity	NPC270013
0.8022	Intermediate Similarity	NPC14961
0.8022	Intermediate Similarity	NPC36954
0.8	Intermediate Similarity	NPC52923
0.8	Intermediate Similarity	NPC162205
0.8	Intermediate Similarity	NPC295204
0.8	Intermediate Similarity	NPC273579
0.8	Intermediate Similarity	NPC288240
0.7978	Intermediate Similarity	NPC476004
0.7978	Intermediate Similarity	NPC474232
0.7978	Intermediate Similarity	NPC474761
0.7978	Intermediate Similarity	NPC475855
0.7978	Intermediate Similarity	NPC473448
0.7955	Intermediate Similarity	NPC476803
0.7955	Intermediate Similarity	NPC136879
0.7955	Intermediate Similarity	NPC477302
0.7952	Intermediate Similarity	NPC98557
0.7952	Intermediate Similarity	NPC167881
0.7952	Intermediate Similarity	NPC473981
0.7952	Intermediate Similarity	NPC473980
0.7935	Intermediate Similarity	NPC279621
0.7935	Intermediate Similarity	NPC476315
0.7931	Intermediate Similarity	NPC116575
0.7931	Intermediate Similarity	NPC478112
0.7917	Intermediate Similarity	NPC220964
0.7917	Intermediate Similarity	NPC475676
0.7912	Intermediate Similarity	NPC57405
0.7912	Intermediate Similarity	NPC474035
0.7912	Intermediate Similarity	NPC81386
0.7912	Intermediate Similarity	NPC303942
0.7907	Intermediate Similarity	NPC31086
0.7889	Intermediate Similarity	NPC30515
0.7889	Intermediate Similarity	NPC184463
0.7889	Intermediate Similarity	NPC473321
0.7865	Intermediate Similarity	NPC474032
0.7841	Intermediate Similarity	NPC179659
0.7831	Intermediate Similarity	NPC218817
0.7831	Intermediate Similarity	NPC196653
0.7831	Intermediate Similarity	NPC127526
0.7831	Intermediate Similarity	NPC475699
0.7831	Intermediate Similarity	NPC471465
0.7831	Intermediate Similarity	NPC11796
0.7826	Intermediate Similarity	NPC304886
0.7812	Intermediate Similarity	NPC4620
0.7802	Intermediate Similarity	NPC469692
0.7802	Intermediate Similarity	NPC179746
0.7802	Intermediate Similarity	NPC125674
0.7802	Intermediate Similarity	NPC212486
0.7802	Intermediate Similarity	NPC475838
0.7802	Intermediate Similarity	NPC228451
0.7802	Intermediate Similarity	NPC81419
0.7802	Intermediate Similarity	NPC476300
0.7802	Intermediate Similarity	NPC469645
0.7791	Intermediate Similarity	NPC474809
0.7791	Intermediate Similarity	NPC44261
0.7791	Intermediate Similarity	NPC59097
0.7791	Intermediate Similarity	NPC250315
0.7778	Intermediate Similarity	NPC144133
0.7778	Intermediate Similarity	NPC51004
0.7778	Intermediate Similarity	NPC469368
0.7778	Intermediate Similarity	NPC473619
0.7778	Intermediate Similarity	NPC179394
0.7778	Intermediate Similarity	NPC166554
0.7766	Intermediate Similarity	NPC187268
0.7765	Intermediate Similarity	NPC470241
0.7765	Intermediate Similarity	NPC325031
0.7765	Intermediate Similarity	NPC141810
0.7765	Intermediate Similarity	NPC88735
0.7753	Intermediate Similarity	NPC476805
0.7753	Intermediate Similarity	NPC475819
0.7753	Intermediate Similarity	NPC202672
0.7753	Intermediate Similarity	NPC473715
0.7742	Intermediate Similarity	NPC473859
0.7738	Intermediate Similarity	NPC89128
0.7738	Intermediate Similarity	NPC471537
0.7727	Intermediate Similarity	NPC279267
0.7727	Intermediate Similarity	NPC469483
0.7727	Intermediate Similarity	NPC472009
0.7727	Intermediate Similarity	NPC278283
0.7727	Intermediate Similarity	NPC69082
0.7727	Intermediate Similarity	NPC150755
0.7717	Intermediate Similarity	NPC121825
0.7717	Intermediate Similarity	NPC474247
0.7711	Intermediate Similarity	NPC97516
0.7711	Intermediate Similarity	NPC281296
0.7711	Intermediate Similarity	NPC171204
0.7711	Intermediate Similarity	NPC476028
0.7711	Intermediate Similarity	NPC141789
0.7701	Intermediate Similarity	NPC9868
0.7701	Intermediate Similarity	NPC163093
0.7701	Intermediate Similarity	NPC474776
0.7692	Intermediate Similarity	NPC208886
0.7692	Intermediate Similarity	NPC330426
0.7692	Intermediate Similarity	NPC271921
0.7692	Intermediate Similarity	NPC26500
0.7692	Intermediate Similarity	NPC104537
0.7692	Intermediate Similarity	NPC22101
0.7692	Intermediate Similarity	NPC12172
0.7692	Intermediate Similarity	NPC148192
0.7692	Intermediate Similarity	NPC127091
0.7692	Intermediate Similarity	NPC99619
0.7684	Intermediate Similarity	NPC288876
0.7683	Intermediate Similarity	NPC60718
0.7677	Intermediate Similarity	NPC474664
0.7677	Intermediate Similarity	NPC233379
0.7677	Intermediate Similarity	NPC14862
0.7674	Intermediate Similarity	NPC474291
0.7667	Intermediate Similarity	NPC212598
0.7667	Intermediate Similarity	NPC307411
0.7667	Intermediate Similarity	NPC83423
0.7667	Intermediate Similarity	NPC473564
0.7662	Intermediate Similarity	NPC473722
0.766	Intermediate Similarity	NPC266842
0.766	Intermediate Similarity	NPC40812
0.7653	Intermediate Similarity	NPC472749
0.7653	Intermediate Similarity	NPC472751
0.7653	Intermediate Similarity	NPC475802
0.7647	Intermediate Similarity	NPC233377
0.7647	Intermediate Similarity	NPC469920
0.764	Intermediate Similarity	NPC72513
0.764	Intermediate Similarity	NPC160138
0.764	Intermediate Similarity	NPC178215
0.764	Intermediate Similarity	NPC472007
0.764	Intermediate Similarity	NPC312561
0.7634	Intermediate Similarity	NPC107476
0.7634	Intermediate Similarity	NPC477922
0.7634	Intermediate Similarity	NPC475659
0.7634	Intermediate Similarity	NPC471142
0.7629	Intermediate Similarity	NPC472747
0.7629	Intermediate Similarity	NPC472750
0.7629	Intermediate Similarity	NPC474165
0.7629	Intermediate Similarity	NPC69171
0.7625	Intermediate Similarity	NPC4299
0.7619	Intermediate Similarity	NPC260814
0.7619	Intermediate Similarity	NPC27949
0.7619	Intermediate Similarity	NPC39547
0.7619	Intermediate Similarity	NPC323249
0.7619	Intermediate Similarity	NPC121200
0.7614	Intermediate Similarity	NPC182383
0.7614	Intermediate Similarity	NPC471156
0.7614	Intermediate Similarity	NPC283085
0.7614	Intermediate Similarity	NPC322529
0.7614	Intermediate Similarity	NPC473669
0.7614	Intermediate Similarity	NPC473478
0.7614	Intermediate Similarity	NPC103284
0.7614	Intermediate Similarity	NPC107986
0.7614	Intermediate Similarity	NPC66346
0.7614	Intermediate Similarity	NPC120398
0.7614	Intermediate Similarity	NPC474369
0.7614	Intermediate Similarity	NPC473651
0.7614	Intermediate Similarity	NPC110710
0.7614	Intermediate Similarity	NPC477014
0.7614	Intermediate Similarity	NPC286338
0.7614	Intermediate Similarity	NPC477013
0.7614	Intermediate Similarity	NPC471567
0.7614	Intermediate Similarity	NPC1083
0.7614	Intermediate Similarity	NPC231009
0.7614	Intermediate Similarity	NPC261380
0.7614	Intermediate Similarity	NPC223871
0.7614	Intermediate Similarity	NPC132496
0.7614	Intermediate Similarity	NPC82795

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 NPC474252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	1451
0.2-0.3	3695
0.3-0.4	2592
0.4-0.5	803
0.5-0.6	374
0.6-0.7	74
0.7-0.8	26
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
0.7857	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7154	Phase 3
0.7778	Intermediate Similarity	NPD6698	Approved
0.7778	Intermediate Similarity	NPD46	Approved
0.7647	Intermediate Similarity	NPD4821	Approved
0.7647	Intermediate Similarity	NPD4820	Approved
0.7647	Intermediate Similarity	NPD4819	Approved
0.7647	Intermediate Similarity	NPD4822	Approved
0.7619	Intermediate Similarity	NPD4268	Approved
0.7619	Intermediate Similarity	NPD4271	Approved
0.7528	Intermediate Similarity	NPD4249	Approved
0.75	Intermediate Similarity	NPD7983	Approved
0.7444	Intermediate Similarity	NPD4250	Approved
0.7444	Intermediate Similarity	NPD4251	Approved
0.7386	Intermediate Similarity	NPD5362	Discontinued
0.7282	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6435	Approved
0.7273	Intermediate Similarity	NPD4270	Approved
0.7273	Intermediate Similarity	NPD4269	Approved
0.7241	Intermediate Similarity	NPD4252	Approved
0.7234	Intermediate Similarity	NPD5778	Approved
0.7234	Intermediate Similarity	NPD5779	Approved
0.7209	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5785	Approved
0.7159	Intermediate Similarity	NPD5369	Approved
0.7143	Intermediate Similarity	NPD5786	Approved
0.7083	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8039	Approved
0.7045	Intermediate Similarity	NPD5368	Approved
0.7041	Intermediate Similarity	NPD4225	Approved
0.7041	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5363	Approved
0.7021	Intermediate Similarity	NPD7838	Discovery
0.6923	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6101	Approved
0.6915	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3197	Phase 1
0.6857	Remote Similarity	NPD6371	Approved
0.6848	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8515	Approved
0.6847	Remote Similarity	NPD8517	Approved
0.6847	Remote Similarity	NPD8516	Approved
0.6847	Remote Similarity	NPD8513	Phase 3
0.6837	Remote Similarity	NPD7839	Suspended
0.6813	Remote Similarity	NPD5331	Approved
0.6813	Remote Similarity	NPD5332	Approved
0.6789	Remote Similarity	NPD7115	Discovery
0.6778	Remote Similarity	NPD4790	Discontinued
0.6771	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6411	Approved
0.6737	Remote Similarity	NPD5370	Suspended
0.6733	Remote Similarity	NPD5344	Discontinued
0.6709	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6627	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7637	Suspended
0.6585	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6053	Discontinued
0.6562	Remote Similarity	NPD1695	Approved
0.6552	Remote Similarity	NPD8074	Phase 3
0.6531	Remote Similarity	NPD6399	Phase 3
0.6522	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6648	Approved
0.6465	Remote Similarity	NPD5282	Discontinued
0.6449	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3172	Approved
0.6389	Remote Similarity	NPD6421	Discontinued
0.6364	Remote Similarity	NPD3196	Approved
0.6364	Remote Similarity	NPD4266	Approved
0.6364	Remote Similarity	NPD3194	Approved
0.6364	Remote Similarity	NPD3195	Phase 2
0.6344	Remote Similarity	NPD5209	Approved
0.6311	Remote Similarity	NPD7640	Approved
0.6311	Remote Similarity	NPD7639	Approved
0.631	Remote Similarity	NPD7331	Phase 2
0.6275	Remote Similarity	NPD6084	Phase 2
0.6275	Remote Similarity	NPD6083	Phase 2
0.6273	Remote Similarity	NPD8297	Approved
0.6262	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD6422	Discontinued
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5695	Phase 3
0.622	Remote Similarity	NPD368	Approved
0.6214	Remote Similarity	NPD7638	Approved
0.6204	Remote Similarity	NPD6881	Approved
0.6204	Remote Similarity	NPD6899	Approved
0.6186	Remote Similarity	NPD8273	Phase 1
0.6182	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3667	Approved
0.6168	Remote Similarity	NPD7128	Approved
0.6168	Remote Similarity	NPD5739	Approved
0.6168	Remote Similarity	NPD6675	Approved
0.6168	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD3730	Approved
0.6154	Remote Similarity	NPD3728	Approved
0.6147	Remote Similarity	NPD6012	Approved
0.6147	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD6013	Approved
0.6121	Remote Similarity	NPD8444	Approved
0.6118	Remote Similarity	NPD3704	Approved
0.6111	Remote Similarity	NPD5701	Approved
0.6105	Remote Similarity	NPD6110	Phase 1
0.6091	Remote Similarity	NPD2067	Discontinued
0.6091	Remote Similarity	NPD7102	Approved
0.6091	Remote Similarity	NPD7290	Approved
0.6091	Remote Similarity	NPD6883	Approved
0.6087	Remote Similarity	NPD3732	Approved
0.6071	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5696	Approved
0.6055	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7320	Approved
0.6055	Remote Similarity	NPD6011	Approved
0.605	Remote Similarity	NPD8451	Approved
0.6049	Remote Similarity	NPD6109	Phase 1
0.6049	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4786	Approved
0.6038	Remote Similarity	NPD5211	Phase 2
0.6036	Remote Similarity	NPD6847	Approved
0.6036	Remote Similarity	NPD6617	Approved
0.6036	Remote Similarity	NPD8130	Phase 1
0.6036	Remote Similarity	NPD6650	Approved
0.6036	Remote Similarity	NPD6649	Approved
0.6036	Remote Similarity	NPD6869	Approved
0.602	Remote Similarity	NPD7524	Approved
0.6017	Remote Similarity	NPD7829	Approved
0.6017	Remote Similarity	NPD7642	Approved
0.6017	Remote Similarity	NPD7830	Approved
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5982	Remote Similarity	NPD6882	Approved
0.5981	Remote Similarity	NPD6647	Phase 2
0.5981	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7748	Approved
0.5974	Remote Similarity	NPD28	Approved
0.5974	Remote Similarity	NPD29	Approved
0.5966	Remote Similarity	NPD8341	Approved
0.5966	Remote Similarity	NPD8342	Approved
0.5966	Remote Similarity	NPD8299	Approved
0.5966	Remote Similarity	NPD8340	Approved
0.5963	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6412	Phase 2
0.5962	Remote Similarity	NPD7902	Approved
0.5957	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6420	Discontinued
0.5941	Remote Similarity	NPD5693	Phase 1
0.5941	Remote Similarity	NPD7515	Phase 2
0.5941	Remote Similarity	NPD5284	Approved
0.5941	Remote Similarity	NPD5281	Approved
0.5938	Remote Similarity	NPD6695	Phase 3
0.5929	Remote Similarity	NPD4632	Approved
0.5926	Remote Similarity	NPD5141	Approved
0.5921	Remote Similarity	NPD3173	Approved
0.5918	Remote Similarity	NPD6684	Approved
0.5918	Remote Similarity	NPD5330	Approved
0.5918	Remote Similarity	NPD7146	Approved
0.5918	Remote Similarity	NPD7521	Approved
0.5918	Remote Similarity	NPD6409	Approved
0.5918	Remote Similarity	NPD4519	Discontinued
0.5918	Remote Similarity	NPD7334	Approved
0.5918	Remote Similarity	NPD4623	Approved
0.5917	Remote Similarity	NPD7507	Approved
0.5913	Remote Similarity	NPD7505	Discontinued
0.5913	Remote Similarity	NPD7500	Approved
0.59	Remote Similarity	NPD6051	Approved
0.59	Remote Similarity	NPD4753	Phase 2
0.5897	Remote Similarity	NPD6319	Approved
0.5893	Remote Similarity	NPD2204	Approved
0.5893	Remote Similarity	NPD1719	Phase 1
0.5889	Remote Similarity	NPD4732	Discontinued
0.5882	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD3666	Approved
0.5876	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD3665	Phase 1
0.5876	Remote Similarity	NPD3133	Approved
0.5875	Remote Similarity	NPD342	Phase 1
0.5865	Remote Similarity	NPD4228	Discovery
0.5854	Remote Similarity	NPD8390	Approved
0.5854	Remote Similarity	NPD8392	Approved
0.5854	Remote Similarity	NPD8391	Approved
0.5849	Remote Similarity	NPD4696	Approved
0.5849	Remote Similarity	NPD5285	Approved
0.5849	Remote Similarity	NPD5286	Approved
0.5833	Remote Similarity	NPD7492	Approved
0.5826	Remote Similarity	NPD2629	Approved
0.5816	Remote Similarity	NPD1696	Phase 3
0.5814	Remote Similarity	NPD7341	Phase 2
0.581	Remote Similarity	NPD4755	Approved
0.58	Remote Similarity	NPD5737	Approved
0.58	Remote Similarity	NPD6672	Approved
0.58	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6903	Approved
0.5789	Remote Similarity	NPD7332	Phase 2

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