NPASS Compound

Structure

CID158525 OpenBabel06191715532D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.8327 1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7943 -2.4038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3135 -3.2366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -2.4038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1776 1.1776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8072 0.6481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2489 0.9288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2438 -0.2086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 -0.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -0.4520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 0.4808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8575 0.4977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6654 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 -1.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8327 -2.4038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9615 0.0000 C 0 0 2 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 -2.4982 0.4808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5257 -1.1707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5639 -0.8885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 17 2 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 1 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 20 1 1 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	3.805
LogD:	3.758
LogS:	-4.706
# Rotatable Bonds:	3
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.904
Synthetic Accessibility Score:	4.319
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.735
MDCK Permeability:	1.9583427274483256e-05
Pgp-inhibitor:	0.861
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.802

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	96.51702117919922%
Volume Distribution (VD):	2.238
Pgp-substrate:	4.182182788848877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.68
CYP2C19-inhibitor:	0.736
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.59
CYP2C9-substrate:	0.252
CYP2D6-inhibitor:	0.303
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.666
CYP3A4-substrate:	0.555

ADMET: Excretion

Clearance (CL):	9.678
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.321
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.926
Maximum Recommended Daily Dose:	0.678
Skin Sensitization:	0.107
Carcinogencity:	0.927
Eye Corrosion:	0.004
Eye Irritation:	0.029
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC158525

Natural Product ID:	NPC158525
*Common Name:**	Leoleorin A
IUPAC Name:	(3S,4R,4aS)-4-[2-(furan-3-yl)ethyl]-4-hydroxy-3,4a,8,8-tetramethyl-3,5,6,7-tetrahydronaphthalen-2-one
Synonyms:
Standard InCHIKey:	LNSHYHLTQFBCDL-VOBQZIQPSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-14-16(21)12-17-18(2,3)8-5-9-19(17,4)20(14,22)10-6-15-7-11-23-13-15/h7,11-14,22H,5-6,8-10H2,1-4H3/t14-,19+,20-/m1/s1
SMILES:	C[C@@H]1C(=O)C=C2C(C)(C)CCC[C@]2(C)[C@]1(CCc1ccoc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234609
PubChem CID:	86302558
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	=	14900.0	nM	PMID[512686]

☑ 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 NPC158525 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	260
0.1-0.2	1285
0.2-0.3	2813
0.3-0.4	6435
0.4-0.5	12389
0.5-0.6	8871
0.6-0.7	8188
0.7-0.8	2231
0.8-0.85	176
0.85-0.9	44
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC46896
0.9474	High Similarity	NPC90296
0.9051	High Similarity	NPC263337
0.9044	High Similarity	NPC67003
0.8992	High Similarity	NPC23086
0.8986	High Similarity	NPC243577
0.8939	High Similarity	NPC61788
0.8913	High Similarity	NPC121158
0.8905	High Similarity	NPC148374
0.8855	High Similarity	NPC112706
0.8855	High Similarity	NPC207294
0.8806	High Similarity	NPC218838
0.8786	High Similarity	NPC251865
0.8779	High Similarity	NPC83178
0.8777	High Similarity	NPC473152
0.8732	High Similarity	NPC471174
0.8732	High Similarity	NPC250228
0.8723	High Similarity	NPC5676
0.8702	High Similarity	NPC138139
0.8702	High Similarity	NPC46536
0.8699	High Similarity	NPC264943
0.8696	High Similarity	NPC90953
0.869	High Similarity	NPC75906
0.8682	High Similarity	NPC477967
0.8676	High Similarity	NPC476947
0.8662	High Similarity	NPC346
0.8661	High Similarity	NPC243704
0.8657	High Similarity	NPC89133
0.8643	High Similarity	NPC52412
0.8636	High Similarity	NPC246392
0.8636	High Similarity	NPC290955
0.863	High Similarity	NPC30222
0.863	High Similarity	NPC57998
0.863	High Similarity	NPC178932
0.8623	High Similarity	NPC471996
0.8611	High Similarity	NPC195325
0.8611	High Similarity	NPC472654
0.8601	High Similarity	NPC255414
0.8601	High Similarity	NPC216755
0.8593	High Similarity	NPC471995
0.8582	High Similarity	NPC223415
0.8571	High Similarity	NPC44675
0.8571	High Similarity	NPC26532
0.8571	High Similarity	NPC469336
0.8571	High Similarity	NPC214541
0.8571	High Similarity	NPC35000
0.8571	High Similarity	NPC477123
0.8571	High Similarity	NPC205765
0.8571	High Similarity	NPC477966
0.8571	High Similarity	NPC279877
0.8562	High Similarity	NPC469503
0.8552	High Similarity	NPC212257
0.8552	High Similarity	NPC228842
0.8551	High Similarity	NPC310830
0.8529	High Similarity	NPC471006
0.8523	High Similarity	NPC477403
0.8521	High Similarity	NPC476944
0.8514	High Similarity	NPC469485
0.8507	High Similarity	NPC59502
0.8503	High Similarity	NPC282445
0.8489	Intermediate Similarity	NPC476943
0.8489	Intermediate Similarity	NPC220094
0.8485	Intermediate Similarity	NPC179354
0.8483	Intermediate Similarity	NPC69647
0.8483	Intermediate Similarity	NPC211625
0.8483	Intermediate Similarity	NPC125182
0.8478	Intermediate Similarity	NPC146872
0.8473	Intermediate Similarity	NPC272899
0.8473	Intermediate Similarity	NPC16922
0.8472	Intermediate Similarity	NPC221809
0.8472	Intermediate Similarity	NPC470941
0.8467	Intermediate Similarity	NPC477402
0.8462	Intermediate Similarity	NPC185456
0.8456	Intermediate Similarity	NPC249021
0.8456	Intermediate Similarity	NPC472772
0.8456	Intermediate Similarity	NPC261597
0.8456	Intermediate Similarity	NPC173544
0.8451	Intermediate Similarity	NPC267632
0.8451	Intermediate Similarity	NPC470741
0.8451	Intermediate Similarity	NPC476946
0.8451	Intermediate Similarity	NPC103134
0.8435	Intermediate Similarity	NPC246164
0.8435	Intermediate Similarity	NPC44577
0.8433	Intermediate Similarity	NPC477039
0.8433	Intermediate Similarity	NPC477040
0.8429	Intermediate Similarity	NPC202260
0.8425	Intermediate Similarity	NPC469335
0.8425	Intermediate Similarity	NPC196864
0.8425	Intermediate Similarity	NPC159927
0.8425	Intermediate Similarity	NPC477404
0.8425	Intermediate Similarity	NPC156189
0.8425	Intermediate Similarity	NPC196846
0.8425	Intermediate Similarity	NPC150895
0.8421	Intermediate Similarity	NPC74612
0.8417	Intermediate Similarity	NPC4764
0.8411	Intermediate Similarity	NPC5079
0.8403	Intermediate Similarity	NPC470999
0.8394	Intermediate Similarity	NPC293253
0.8394	Intermediate Similarity	NPC470740
0.8382	Intermediate Similarity	NPC298190
0.838	Intermediate Similarity	NPC20578
0.838	Intermediate Similarity	NPC62103
0.8369	Intermediate Similarity	NPC56197
0.8367	Intermediate Similarity	NPC272590
0.8357	Intermediate Similarity	NPC236532
0.8356	Intermediate Similarity	NPC470791
0.8356	Intermediate Similarity	NPC470790
0.8356	Intermediate Similarity	NPC470998
0.8355	Intermediate Similarity	NPC224394
0.8355	Intermediate Similarity	NPC234660
0.8355	Intermediate Similarity	NPC165218
0.8355	Intermediate Similarity	NPC663
0.8355	Intermediate Similarity	NPC51568
0.8355	Intermediate Similarity	NPC292389
0.8355	Intermediate Similarity	NPC469338
0.8345	Intermediate Similarity	NPC302987
0.8344	Intermediate Similarity	NPC287559
0.8344	Intermediate Similarity	NPC25255
0.8333	Intermediate Similarity	NPC470118
0.8333	Intermediate Similarity	NPC45101
0.8333	Intermediate Similarity	NPC187149
0.8333	Intermediate Similarity	NPC81405
0.8333	Intermediate Similarity	NPC36655
0.8333	Intermediate Similarity	NPC471998
0.8333	Intermediate Similarity	NPC299038
0.8322	Intermediate Similarity	NPC64568
0.8322	Intermediate Similarity	NPC155939
0.8322	Intermediate Similarity	NPC469850
0.8322	Intermediate Similarity	NPC141538
0.8322	Intermediate Similarity	NPC92979
0.8322	Intermediate Similarity	NPC296807
0.8311	Intermediate Similarity	NPC268905
0.8311	Intermediate Similarity	NPC294511
0.8311	Intermediate Similarity	NPC470996
0.8311	Intermediate Similarity	NPC121615
0.8309	Intermediate Similarity	NPC476925
0.8301	Intermediate Similarity	NPC276551
0.8301	Intermediate Similarity	NPC470940
0.8301	Intermediate Similarity	NPC469849
0.8299	Intermediate Similarity	NPC476122
0.8296	Intermediate Similarity	NPC327527
0.8296	Intermediate Similarity	NPC329707
0.8296	Intermediate Similarity	NPC476917
0.8289	Intermediate Similarity	NPC329938
0.8289	Intermediate Similarity	NPC472771
0.8289	Intermediate Similarity	NPC149896
0.8289	Intermediate Similarity	NPC18986
0.8289	Intermediate Similarity	NPC69028
0.8289	Intermediate Similarity	NPC193798
0.8289	Intermediate Similarity	NPC82851
0.8288	Intermediate Similarity	NPC476942
0.8288	Intermediate Similarity	NPC476941
0.8286	Intermediate Similarity	NPC42400
0.8286	Intermediate Similarity	NPC470742
0.8286	Intermediate Similarity	NPC307401
0.8278	Intermediate Similarity	NPC474611
0.8278	Intermediate Similarity	NPC262872
0.8278	Intermediate Similarity	NPC140952
0.8278	Intermediate Similarity	NPC475967
0.8278	Intermediate Similarity	NPC307383
0.8276	Intermediate Similarity	NPC276676
0.8276	Intermediate Similarity	NPC97904
0.8273	Intermediate Similarity	NPC92941
0.8271	Intermediate Similarity	NPC477038
0.8271	Intermediate Similarity	NPC477965
0.8271	Intermediate Similarity	NPC130275
0.8271	Intermediate Similarity	NPC118853
0.8267	Intermediate Similarity	NPC60973
0.8267	Intermediate Similarity	NPC41880
0.8267	Intermediate Similarity	NPC209364
0.8267	Intermediate Similarity	NPC104736
0.8264	Intermediate Similarity	NPC142113
0.8258	Intermediate Similarity	NPC317217
0.8255	Intermediate Similarity	NPC114880
0.8247	Intermediate Similarity	NPC470875
0.8247	Intermediate Similarity	NPC478178
0.8243	Intermediate Similarity	NPC18135
0.8235	Intermediate Similarity	NPC472773
0.8235	Intermediate Similarity	NPC477405
0.8235	Intermediate Similarity	NPC223063
0.8235	Intermediate Similarity	NPC419
0.8235	Intermediate Similarity	NPC120836
0.8231	Intermediate Similarity	NPC87466
0.8231	Intermediate Similarity	NPC471001
0.8231	Intermediate Similarity	NPC234494
0.8227	Intermediate Similarity	NPC472376
0.8224	Intermediate Similarity	NPC472653
0.8224	Intermediate Similarity	NPC470789
0.8224	Intermediate Similarity	NPC335761
0.8219	Intermediate Similarity	NPC71821
0.8219	Intermediate Similarity	NPC476937
0.8219	Intermediate Similarity	NPC10088
0.8219	Intermediate Similarity	NPC476938
0.8212	Intermediate Similarity	NPC472778
0.8212	Intermediate Similarity	NPC197137
0.8212	Intermediate Similarity	NPC194499
0.8212	Intermediate Similarity	NPC472777
0.8212	Intermediate Similarity	NPC286722
0.8212	Intermediate Similarity	NPC195954
0.8212	Intermediate Similarity	NPC472776

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 NPC158525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	914
0.2-0.3	1799
0.3-0.4	2707
0.4-0.5	2140
0.5-0.6	1032
0.6-0.7	259
0.7-0.8	35
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8446	Intermediate Similarity	NPD5760	Phase 2
0.8446	Intermediate Similarity	NPD5761	Phase 2
0.7651	Intermediate Similarity	NPD8434	Phase 2
0.7551	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD6765	Approved
0.7455	Intermediate Similarity	NPD6764	Approved
0.7432	Intermediate Similarity	NPD1471	Phase 3
0.7432	Intermediate Similarity	NPD2344	Approved
0.7312	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1608	Approved
0.7286	Intermediate Similarity	NPD3972	Approved
0.7278	Intermediate Similarity	NPD7819	Suspended
0.7278	Intermediate Similarity	NPD6785	Approved
0.7278	Intermediate Similarity	NPD6784	Approved
0.7273	Intermediate Similarity	NPD6273	Approved
0.7248	Intermediate Similarity	NPD6099	Approved
0.7248	Intermediate Similarity	NPD2796	Approved
0.7248	Intermediate Similarity	NPD6100	Approved
0.7237	Intermediate Similarity	NPD2309	Approved
0.7226	Intermediate Similarity	NPD920	Approved
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2800	Approved
0.7208	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6599	Discontinued
0.7181	Intermediate Similarity	NPD2799	Discontinued
0.7171	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3226	Approved
0.7105	Intermediate Similarity	NPD1243	Approved
0.7097	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2346	Discontinued
0.7083	Intermediate Similarity	NPD2798	Approved
0.7071	Intermediate Similarity	NPD17	Approved
0.7071	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1241	Discontinued
0.7047	Intermediate Similarity	NPD1607	Approved
0.7039	Intermediate Similarity	NPD1549	Phase 2
0.7037	Intermediate Similarity	NPD3749	Approved
0.7027	Intermediate Similarity	NPD1240	Approved
0.702	Intermediate Similarity	NPD1551	Phase 2
0.7019	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD919	Approved
0.6987	Remote Similarity	NPD2532	Approved
0.6987	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2533	Approved
0.6987	Remote Similarity	NPD2534	Approved
0.6987	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3882	Suspended
0.6974	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1510	Phase 2
0.6951	Remote Similarity	NPD5494	Approved
0.695	Remote Similarity	NPD1778	Approved
0.6944	Remote Similarity	NPD1876	Approved
0.6941	Remote Similarity	NPD6559	Discontinued
0.6937	Remote Similarity	NPD7411	Suspended
0.6928	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6799	Approved
0.6909	Remote Similarity	NPD1247	Approved
0.6897	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2313	Discontinued
0.6846	Remote Similarity	NPD8032	Phase 2
0.6842	Remote Similarity	NPD7033	Discontinued
0.6839	Remote Similarity	NPD3750	Approved
0.6839	Remote Similarity	NPD7003	Approved
0.6829	Remote Similarity	NPD7075	Discontinued
0.6821	Remote Similarity	NPD6651	Approved
0.6813	Remote Similarity	NPD7458	Discontinued
0.6809	Remote Similarity	NPD9545	Approved
0.6807	Remote Similarity	NPD6959	Discontinued
0.6805	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1934	Approved
0.679	Remote Similarity	NPD6279	Approved
0.679	Remote Similarity	NPD6280	Approved
0.6788	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3764	Approved
0.677	Remote Similarity	NPD4380	Phase 2
0.6757	Remote Similarity	NPD6832	Phase 2
0.6732	Remote Similarity	NPD3748	Approved
0.6726	Remote Similarity	NPD3926	Phase 2
0.6712	Remote Similarity	NPD6696	Suspended
0.6712	Remote Similarity	NPD1283	Approved
0.6708	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2296	Approved
0.669	Remote Similarity	NPD9717	Approved
0.6689	Remote Similarity	NPD3140	Approved
0.6689	Remote Similarity	NPD3142	Approved
0.6689	Remote Similarity	NPD4140	Approved
0.6689	Remote Similarity	NPD9494	Approved
0.6688	Remote Similarity	NPD2935	Discontinued
0.6687	Remote Similarity	NPD6801	Discontinued
0.6686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7236	Approved
0.6646	Remote Similarity	NPD2801	Approved
0.6645	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6004	Phase 3
0.6645	Remote Similarity	NPD6005	Phase 3
0.6645	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6002	Phase 3
0.6643	Remote Similarity	NPD1651	Approved
0.6643	Remote Similarity	NPD5585	Approved
0.663	Remote Similarity	NPD3057	Approved
0.6627	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4110	Phase 3
0.6623	Remote Similarity	NPD4308	Phase 3
0.6622	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1201	Approved
0.662	Remote Similarity	NPD9092	Discovery
0.6615	Remote Similarity	NPD8404	Phase 2
0.6609	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7177	Discontinued
0.6608	Remote Similarity	NPD3818	Discontinued
0.6607	Remote Similarity	NPD8127	Discontinued
0.6606	Remote Similarity	NPD3817	Phase 2
0.6604	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1511	Approved
0.66	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2932	Approved
0.6585	Remote Similarity	NPD7577	Discontinued
0.657	Remote Similarity	NPD5844	Phase 1
0.6556	Remote Similarity	NPD411	Approved
0.6554	Remote Similarity	NPD1203	Approved
0.6554	Remote Similarity	NPD1470	Approved
0.6552	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7473	Discontinued
0.6541	Remote Similarity	NPD3533	Approved
0.6541	Remote Similarity	NPD2972	Approved
0.6536	Remote Similarity	NPD5735	Approved
0.6536	Remote Similarity	NPD6355	Discontinued
0.6536	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4749	Approved
0.6531	Remote Similarity	NPD5327	Phase 3
0.6522	Remote Similarity	NPD1512	Approved
0.6519	Remote Similarity	NPD8166	Discontinued
0.651	Remote Similarity	NPD5647	Approved
0.6507	Remote Similarity	NPD1281	Approved
0.6494	Remote Similarity	NPD6353	Approved
0.6491	Remote Similarity	NPD6166	Phase 2
0.6491	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD3019	Approved
0.6481	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3873	Phase 3
0.6481	Remote Similarity	NPD5403	Approved
0.6481	Remote Similarity	NPD3869	Phase 3
0.6478	Remote Similarity	NPD2354	Approved
0.6478	Remote Similarity	NPD3887	Approved
0.6477	Remote Similarity	NPD8312	Approved
0.6477	Remote Similarity	NPD8313	Approved
0.6475	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4476	Approved
0.6474	Remote Similarity	NPD4477	Approved
0.6471	Remote Similarity	NPD5711	Approved
0.6471	Remote Similarity	NPD6232	Discontinued
0.6471	Remote Similarity	NPD2979	Phase 3
0.6471	Remote Similarity	NPD6808	Phase 2
0.6471	Remote Similarity	NPD5710	Approved
0.6471	Remote Similarity	NPD4307	Phase 2
0.646	Remote Similarity	NPD4662	Approved
0.646	Remote Similarity	NPD5401	Approved
0.646	Remote Similarity	NPD4661	Approved
0.6457	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2491	Approved
0.6443	Remote Similarity	NPD3266	Approved
0.6443	Remote Similarity	NPD3267	Approved
0.6442	Remote Similarity	NPD7239	Suspended
0.6434	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD5763	Approved
0.6433	Remote Similarity	NPD5762	Approved
0.6432	Remote Similarity	NPD4107	Approved
0.6429	Remote Similarity	NPD447	Suspended
0.6419	Remote Similarity	NPD4359	Approved
0.6416	Remote Similarity	NPD7799	Discontinued
0.6416	Remote Similarity	NPD2163	Approved
0.6414	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5691	Approved
0.6407	Remote Similarity	NPD5402	Approved
0.6404	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD2649	Approved
0.6402	Remote Similarity	NPD2651	Approved
0.64	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4624	Approved
0.64	Remote Similarity	NPD5953	Discontinued
0.64	Remote Similarity	NPD1019	Discontinued
0.6395	Remote Similarity	NPD2403	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