NPASS Compound

Structure

CID243704 OpenBabel06191716042D 22 24 0 0 1 0 0 0 0 0999 V2000 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.19
Volume:	333.205
LogP:	4.847
LogD:	4.619
LogS:	-5.117
# Rotatable Bonds:	3
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	3.728
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.894
MDCK Permeability:	1.982331923500169e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.097
30% Bioavailability (F30%):	0.679

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	94.64539337158203%
Volume Distribution (VD):	2.378
Pgp-substrate:	3.5163052082061768%

ADMET: Metabolism

CYP1A2-inhibitor:	0.883
CYP1A2-substrate:	0.81
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.89
CYP2C9-substrate:	0.404
CYP2D6-inhibitor:	0.928
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.702

ADMET: Excretion

Clearance (CL):	12.833
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.643
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.897
Maximum Recommended Daily Dose:	0.618
Skin Sensitization:	0.041
Carcinogencity:	0.933
Eye Corrosion:	0.022
Eye Irritation:	0.097
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC243704

Natural Product ID:	NPC243704
*Common Name:**	Leoleorin B
IUPAC Name:	(4aR)-4-[2-(furan-3-yl)ethyl]-3,4a,8,8-tetramethyl-6,7-dihydro-5H-naphthalen-2-one
Synonyms:
Standard InCHIKey:	QWRWJNFMCJNXSU-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H26O2/c1-14-16(7-6-15-8-11-22-13-15)20(4)10-5-9-19(2,3)18(20)12-17(14)21/h8,11-13H,5-7,9-10H2,1-4H3/t20-/m1/s1
SMILES:	CC1=C(CCc2ccoc2)[C@@]2(C)CCCC(C)(C)C2=CC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234611
PubChem CID:	86302559
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO28209	Muricea austera	Species	Plexauridae	Eukaryota	n.a.	Pacific coast of Panama	n.a.	PMID[17067146]
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24707938]
NPO27706	Uncaria hirsuta	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27706	Uncaria hirsuta	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27965	Ballota undulata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28209	Muricea austera	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20245	Cimex lectularius	Species	Cimicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27706	Uncaria hirsuta	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27382	Helichrysum coriaceum	Species	Asteraceae	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
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34000.0	nM	PMID[539065]

☑ 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 NPC243704 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	307
0.1-0.2	1433
0.2-0.3	3598
0.3-0.4	9465
0.4-0.5	11805
0.5-0.6	10512
0.6-0.7	4944
0.7-0.8	514
0.8-0.85	69
0.85-0.9	41
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9068	High Similarity	NPC16922
0.9035	High Similarity	NPC150895
0.9035	High Similarity	NPC28054
0.9	High Similarity	NPC23086
0.8983	High Similarity	NPC317217
0.8983	High Similarity	NPC477967
0.8917	High Similarity	NPC179354
0.887	High Similarity	NPC205523
0.8852	High Similarity	NPC477966
0.8852	High Similarity	NPC112706
0.8852	High Similarity	NPC207294
0.8852	High Similarity	NPC477123
0.8843	High Similarity	NPC74612
0.8843	High Similarity	NPC138139
0.8843	High Similarity	NPC46536
0.8833	High Similarity	NPC477038
0.8833	High Similarity	NPC477965
0.8803	High Similarity	NPC87466
0.88	High Similarity	NPC471006
0.879	High Similarity	NPC61788
0.878	High Similarity	NPC59502
0.877	High Similarity	NPC83178
0.876	High Similarity	NPC471074
0.876	High Similarity	NPC473885
0.8718	High Similarity	NPC312525
0.8718	High Similarity	NPC217180
0.8699	High Similarity	NPC477039
0.8699	High Similarity	NPC477040
0.8699	High Similarity	NPC476917
0.8699	High Similarity	NPC327527
0.8661	High Similarity	NPC158525
0.8651	High Similarity	NPC218838
0.8651	High Similarity	NPC470740
0.864	High Similarity	NPC298190
0.8632	High Similarity	NPC45536
0.8618	High Similarity	NPC246392
0.8618	High Similarity	NPC290955
0.8594	High Similarity	NPC146872
0.8583	High Similarity	NPC97566
0.8571	High Similarity	NPC471817
0.8571	High Similarity	NPC473982
0.8571	High Similarity	NPC473969
0.856	High Similarity	NPC476925
0.8559	High Similarity	NPC144745
0.8559	High Similarity	NPC208906
0.8559	High Similarity	NPC212918
0.8548	High Similarity	NPC279877
0.8548	High Similarity	NPC26532
0.8525	High Similarity	NPC188377
0.8525	High Similarity	NPC65735
0.8522	High Similarity	NPC105249
0.8492	Intermediate Similarity	NPC89133
0.848	Intermediate Similarity	NPC208389
0.8468	Intermediate Similarity	NPC319140
0.8468	Intermediate Similarity	NPC95567
0.845	Intermediate Similarity	NPC46896
0.8421	Intermediate Similarity	NPC471521
0.8421	Intermediate Similarity	NPC473356
0.8403	Intermediate Similarity	NPC131801
0.8385	Intermediate Similarity	NPC307401
0.8385	Intermediate Similarity	NPC310830
0.8385	Intermediate Similarity	NPC42400
0.8374	Intermediate Similarity	NPC118853
0.8374	Intermediate Similarity	NPC243269
0.8372	Intermediate Similarity	NPC92941
0.8372	Intermediate Similarity	NPC476947
0.8361	Intermediate Similarity	NPC471549
0.8361	Intermediate Similarity	NPC473379
0.8361	Intermediate Similarity	NPC36255
0.8348	Intermediate Similarity	NPC177331
0.8333	Intermediate Similarity	NPC56197
0.8333	Intermediate Similarity	NPC90296
0.8321	Intermediate Similarity	NPC476943
0.8321	Intermediate Similarity	NPC220094
0.8321	Intermediate Similarity	NPC236532
0.8293	Intermediate Similarity	NPC272899
0.8279	Intermediate Similarity	NPC79557
0.8268	Intermediate Similarity	NPC21460
0.8264	Intermediate Similarity	NPC137710
0.8258	Intermediate Similarity	NPC202260
0.8258	Intermediate Similarity	NPC90953
0.8254	Intermediate Similarity	NPC329707
0.8244	Intermediate Similarity	NPC215109
0.8244	Intermediate Similarity	NPC470742
0.8244	Intermediate Similarity	NPC170604
0.8226	Intermediate Similarity	NPC130275
0.8226	Intermediate Similarity	NPC83115
0.8226	Intermediate Similarity	NPC178382
0.8209	Intermediate Similarity	NPC473152
0.8205	Intermediate Similarity	NPC277525
0.8195	Intermediate Similarity	NPC148374
0.8182	Intermediate Similarity	NPC206007
0.816	Intermediate Similarity	NPC71274
0.816	Intermediate Similarity	NPC471559
0.816	Intermediate Similarity	NPC474829
0.816	Intermediate Similarity	NPC230979
0.816	Intermediate Similarity	NPC75557
0.816	Intermediate Similarity	NPC303010
0.814	Intermediate Similarity	NPC471995
0.8136	Intermediate Similarity	NPC1811
0.8136	Intermediate Similarity	NPC22678
0.8136	Intermediate Similarity	NPC26157
0.813	Intermediate Similarity	NPC1848
0.8099	Intermediate Similarity	NPC227660
0.8095	Intermediate Similarity	NPC474260
0.8095	Intermediate Similarity	NPC329694
0.8095	Intermediate Similarity	NPC329922
0.8095	Intermediate Similarity	NPC81912
0.8088	Intermediate Similarity	NPC238843
0.8088	Intermediate Similarity	NPC199044
0.8088	Intermediate Similarity	NPC142113
0.8087	Intermediate Similarity	NPC42471
0.8077	Intermediate Similarity	NPC293253
0.8074	Intermediate Similarity	NPC52412
0.8074	Intermediate Similarity	NPC263337
0.8065	Intermediate Similarity	NPC263870
0.806	Intermediate Similarity	NPC67003
0.806	Intermediate Similarity	NPC201370
0.806	Intermediate Similarity	NPC473983
0.8047	Intermediate Similarity	NPC198904
0.8045	Intermediate Similarity	NPC472376
0.8033	Intermediate Similarity	NPC187547
0.8033	Intermediate Similarity	NPC21831
0.8031	Intermediate Similarity	NPC137570
0.8031	Intermediate Similarity	NPC474830
0.8031	Intermediate Similarity	NPC476016
0.8029	Intermediate Similarity	NPC185456
0.8017	Intermediate Similarity	NPC59035
0.8017	Intermediate Similarity	NPC79202
0.8016	Intermediate Similarity	NPC290193
0.8016	Intermediate Similarity	NPC300098
0.8015	Intermediate Similarity	NPC267632
0.8015	Intermediate Similarity	NPC243577
0.8015	Intermediate Similarity	NPC223415
0.8	Intermediate Similarity	NPC476351
0.8	Intermediate Similarity	NPC205765
0.7971	Intermediate Similarity	NPC470999
0.7971	Intermediate Similarity	NPC276676
0.7971	Intermediate Similarity	NPC471292
0.7969	Intermediate Similarity	NPC474438
0.7969	Intermediate Similarity	NPC474279
0.7953	Intermediate Similarity	NPC470858
0.7941	Intermediate Similarity	NPC121158
0.7937	Intermediate Similarity	NPC11799
0.7937	Intermediate Similarity	NPC141252
0.7923	Intermediate Similarity	NPC477645
0.792	Intermediate Similarity	NPC289911
0.792	Intermediate Similarity	NPC283284
0.7914	Intermediate Similarity	NPC302987
0.7914	Intermediate Similarity	NPC471174
0.7914	Intermediate Similarity	NPC10088
0.7907	Intermediate Similarity	NPC120836
0.7907	Intermediate Similarity	NPC50583
0.7907	Intermediate Similarity	NPC223063
0.7903	Intermediate Similarity	NPC246214
0.7899	Intermediate Similarity	NPC34056
0.7891	Intermediate Similarity	NPC471573
0.7891	Intermediate Similarity	NPC471554
0.7891	Intermediate Similarity	NPC471501
0.7891	Intermediate Similarity	NPC141059
0.7891	Intermediate Similarity	NPC473355
0.7883	Intermediate Similarity	NPC470741
0.7883	Intermediate Similarity	NPC476946
0.7869	Intermediate Similarity	NPC476014
0.7869	Intermediate Similarity	NPC476031
0.7868	Intermediate Similarity	NPC20500
0.7863	Intermediate Similarity	NPC471544
0.7863	Intermediate Similarity	NPC140688
0.7863	Intermediate Similarity	NPC473344
0.7857	Intermediate Similarity	NPC475818
0.7852	Intermediate Similarity	NPC474722
0.7851	Intermediate Similarity	NPC252004
0.7842	Intermediate Similarity	NPC262198
0.7842	Intermediate Similarity	NPC346
0.784	Intermediate Similarity	NPC474136
0.7836	Intermediate Similarity	NPC278832
0.7836	Intermediate Similarity	NPC64157
0.7836	Intermediate Similarity	NPC186626
0.7826	Intermediate Similarity	NPC476944
0.7826	Intermediate Similarity	NPC251865
0.7823	Intermediate Similarity	NPC4898
0.782	Intermediate Similarity	NPC209858
0.782	Intermediate Similarity	NPC265793
0.7812	Intermediate Similarity	NPC83301
0.7805	Intermediate Similarity	NPC469954
0.7801	Intermediate Similarity	NPC234494
0.7801	Intermediate Similarity	NPC470998
0.7801	Intermediate Similarity	NPC471001
0.7786	Intermediate Similarity	NPC282230
0.7786	Intermediate Similarity	NPC216755
0.7786	Intermediate Similarity	NPC17681
0.7786	Intermediate Similarity	NPC71821
0.7786	Intermediate Similarity	NPC476937
0.7786	Intermediate Similarity	NPC475092
0.7786	Intermediate Similarity	NPC476938
0.7786	Intermediate Similarity	NPC250228
0.7786	Intermediate Similarity	NPC183348
0.7778	Intermediate Similarity	NPC130976
0.7778	Intermediate Similarity	NPC471996
0.777	Intermediate Similarity	NPC290038

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 NPC243704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	1018
0.2-0.3	1685
0.3-0.4	2853
0.4-0.5	2128
0.5-0.6	939
0.6-0.7	219
0.7-0.8	14
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
0.8067	Intermediate Similarity	NPD1241	Discontinued
0.7721	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD3972	Approved
0.7638	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6832	Phase 2
0.7328	Intermediate Similarity	NPD1876	Approved
0.7297	Intermediate Similarity	NPD5760	Phase 2
0.7297	Intermediate Similarity	NPD5761	Phase 2
0.7279	Intermediate Similarity	NPD3140	Approved
0.7279	Intermediate Similarity	NPD3142	Approved
0.7214	Intermediate Similarity	NPD1471	Phase 3
0.7214	Intermediate Similarity	NPD2344	Approved
0.7209	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2796	Approved
0.7133	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD920	Approved
0.7113	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD2798	Approved
0.7071	Intermediate Similarity	NPD2799	Discontinued
0.7063	Intermediate Similarity	NPD4628	Phase 3
0.7055	Intermediate Similarity	NPD6273	Approved
0.7014	Intermediate Similarity	NPD2309	Approved
0.7007	Intermediate Similarity	NPD3873	Phase 3
0.7007	Intermediate Similarity	NPD3869	Phase 3
0.7007	Intermediate Similarity	NPD2313	Discontinued
0.7	Intermediate Similarity	NPD5585	Approved
0.6993	Remote Similarity	NPD1243	Approved
0.6963	Remote Similarity	NPD1019	Discontinued
0.6957	Remote Similarity	NPD8032	Phase 2
0.6917	Remote Similarity	NPD9717	Approved
0.6911	Remote Similarity	NPD3134	Approved
0.6906	Remote Similarity	NPD4307	Phase 2
0.6905	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3887	Approved
0.6889	Remote Similarity	NPD3266	Approved
0.6889	Remote Similarity	NPD2797	Approved
0.6889	Remote Similarity	NPD3267	Approved
0.6887	Remote Similarity	NPD6279	Approved
0.6887	Remote Similarity	NPD6280	Approved
0.687	Remote Similarity	NPD1651	Approved
0.6857	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3748	Approved
0.6818	Remote Similarity	NPD17	Approved
0.68	Remote Similarity	NPD2684	Approved
0.6794	Remote Similarity	NPD1894	Discontinued
0.6774	Remote Similarity	NPD919	Approved
0.6765	Remote Similarity	NPD1203	Approved
0.6763	Remote Similarity	NPD3268	Approved
0.6757	Remote Similarity	NPD4662	Approved
0.6757	Remote Similarity	NPD4661	Approved
0.6755	Remote Similarity	NPD6599	Discontinued
0.6741	Remote Similarity	NPD4359	Approved
0.6738	Remote Similarity	NPD1933	Approved
0.6736	Remote Similarity	NPD2353	Approved
0.6736	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2346	Discontinued
0.6728	Remote Similarity	NPD6765	Approved
0.6728	Remote Similarity	NPD6764	Approved
0.672	Remote Similarity	NPD1358	Approved
0.6719	Remote Similarity	NPD5535	Approved
0.6713	Remote Similarity	NPD4308	Phase 3
0.6712	Remote Similarity	NPD7003	Approved
0.6694	Remote Similarity	NPD9697	Approved
0.6694	Remote Similarity	NPD1238	Approved
0.6692	Remote Similarity	NPD7157	Approved
0.6692	Remote Similarity	NPD1778	Approved
0.669	Remote Similarity	NPD1549	Phase 2
0.6689	Remote Similarity	NPD6799	Approved
0.6688	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD9545	Approved
0.6644	Remote Similarity	NPD2800	Approved
0.6644	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6798	Discontinued
0.6642	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD3496	Discontinued
0.6627	Remote Similarity	NPD8434	Phase 2
0.6621	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4618	Approved
0.662	Remote Similarity	NPD4622	Approved
0.662	Remote Similarity	NPD6355	Discontinued
0.6618	Remote Similarity	NPD5327	Phase 3
0.6617	Remote Similarity	NPD5691	Approved
0.6601	Remote Similarity	NPD7411	Suspended
0.6599	Remote Similarity	NPD3750	Approved
0.6599	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6287	Discontinued
0.6593	Remote Similarity	NPD1281	Approved
0.6591	Remote Similarity	NPD9092	Discovery
0.6591	Remote Similarity	NPD5536	Phase 2
0.6589	Remote Similarity	NPD7843	Approved
0.6579	Remote Similarity	NPD7458	Discontinued
0.6573	Remote Similarity	NPD1607	Approved
0.6571	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6785	Approved
0.6566	Remote Similarity	NPD6784	Approved
0.6554	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2354	Approved
0.6552	Remote Similarity	NPD4477	Approved
0.6552	Remote Similarity	NPD4476	Approved
0.6549	Remote Similarity	NPD2979	Phase 3
0.6543	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6808	Phase 2
0.6538	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5688	Approved
0.6528	Remote Similarity	NPD5689	Approved
0.6525	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6559	Discontinued
0.6519	Remote Similarity	NPD5494	Approved
0.6516	Remote Similarity	NPD7819	Suspended
0.6516	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD9493	Approved
0.651	Remote Similarity	NPD7440	Discontinued
0.6494	Remote Similarity	NPD5889	Approved
0.6494	Remote Similarity	NPD5890	Approved
0.6493	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5049	Phase 3
0.6486	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4110	Phase 3
0.6483	Remote Similarity	NPD1510	Phase 2
0.6481	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD4062	Phase 3
0.6479	Remote Similarity	NPD4870	Approved
0.6479	Remote Similarity	NPD6233	Phase 2
0.6475	Remote Similarity	NPD5647	Approved
0.6474	Remote Similarity	NPD2296	Approved
0.6471	Remote Similarity	NPD2649	Approved
0.6471	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2651	Approved
0.6463	Remote Similarity	NPD4534	Discontinued
0.6463	Remote Similarity	NPD2424	Discontinued
0.646	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7577	Discontinued
0.6452	Remote Similarity	NPD6801	Discontinued
0.6449	Remote Similarity	NPD1283	Approved
0.6447	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5403	Approved
0.6439	Remote Similarity	NPD2557	Approved
0.6438	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4140	Approved
0.6433	Remote Similarity	NPD3882	Suspended
0.6424	Remote Similarity	NPD5401	Approved
0.6423	Remote Similarity	NPD1481	Phase 2
0.641	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD411	Approved
0.6408	Remote Similarity	NPD3764	Approved
0.6398	Remote Similarity	NPD3926	Phase 2
0.6397	Remote Similarity	NPD3847	Discontinued
0.6395	Remote Similarity	NPD6005	Phase 3
0.6395	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6004	Phase 3
0.6395	Remote Similarity	NPD6002	Phase 3
0.6395	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7075	Discontinued
0.6391	Remote Similarity	NPD3596	Phase 2
0.6389	Remote Similarity	NPD447	Suspended
0.6378	Remote Similarity	NPD968	Approved
0.6376	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.637	Remote Similarity	NPD7033	Discontinued
0.6369	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3226	Approved
0.6364	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5451	Approved
0.6357	Remote Similarity	NPD2067	Discontinued
0.6351	Remote Similarity	NPD2897	Discontinued
0.635	Remote Similarity	NPD1535	Discovery
0.6349	Remote Similarity	NPD164	Approved
0.6349	Remote Similarity	NPD1237	Approved
0.6346	Remote Similarity	NPD7317	Phase 3
0.6346	Remote Similarity	NPD6844	Discontinued
0.6345	Remote Similarity	NPD6651	Approved
0.6338	Remote Similarity	NPD7095	Approved
0.6336	Remote Similarity	NPD821	Approved
0.6331	Remote Similarity	NPD8651	Approved
0.6329	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7768	Phase 2
0.6328	Remote Similarity	NPD290	Approved
0.6327	Remote Similarity	NPD2531	Phase 2
0.6327	Remote Similarity	NPD6099	Approved
0.6327	Remote Similarity	NPD2438	Suspended
0.6327	Remote Similarity	NPD6100	Approved
0.6324	Remote Similarity	NPD2932	Approved
0.6324	Remote Similarity	NPD4626	Approved
0.6323	Remote Similarity	NPD6585	Discontinued
0.6323	Remote Similarity	NPD7028	Phase 2
0.6323	Remote Similarity	NPD4380	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