NPASS Compound

Structure

CID11804 OpenBabel06191715342D 32 32 0 0 1 0 0 0 0 0999 V2000 0.0935 -2.7817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9595 -4.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0641 3.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4460 4.5284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6445 1.3739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8888 -0.4582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4595 3.1958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7972 1.7456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3599 3.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9190 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3007 2.6552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5022 2.3637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5738 0.7557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6549 0.7557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8255 -2.7817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1778 4.1553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9595 -3.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4595 3.1958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3818 2.6552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1460 3.9717 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9595 -0.2817 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8255 -1.7817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0743 3.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7162 1.7456 0.0000 C 0 0 1 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 0.8678 4.8791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1375 3.3101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0036 4.9615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6915 -1.2817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2166 2.6102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0476 -0.9989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9595 -1.2817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 7 11 1 0 0 0 0 7 18 2 0 0 0 0 8 14 2 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 24 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 18 19 1 0 0 0 0 19 27 2 0 0 0 0 20 23 1 0 0 0 0 20 28 1 0 0 0 0 21 25 1 1 0 0 0 21 32 1 0 0 0 0 22 29 2 0 0 0 0 22 32 1 0 0 0 0 23 30 1 0 0 0 0 24 5 1 1 0 0 0 25 6 1 1 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.26
Volume:	478.112
LogP:	1.865
LogD:	0.764
LogS:	-3.074
# Rotatable Bonds:	8
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.267
Synthetic Accessibility Score:	5.533
Fsp3:	0.6
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:	-4.668
MDCK Permeability:	3.939783346140757e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.942
Human Intestinal Absorption (HIA):	0.821
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.13

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.954
Plasma Protein Binding (PPB):	76.41073608398438%
Volume Distribution (VD):	0.505
Pgp-substrate:	16.627962112426758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.218
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.381
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.701
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.322

ADMET: Excretion

Clearance (CL):	2.186
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.069
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.401
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.25
Carcinogencity:	0.12
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.777

Download Data

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

Natural Product: NPC11804

Natural Product ID:	NPC11804
*Common Name:**	Vibsanin U
IUPAC Name:	[(1R,2E,4S,6Z,9E,11R)-4-(3,4-dihydroxy-4-methylpentyl)-11-hydroxy-7-(hydroxymethyl)-4,11-dimethyl-8-oxocycloundeca-2,6,9-trien-1-yl] 3-methylbut-2-enoate
Synonyms:	Vibsanin U
Standard InCHIKey:	GFAQUYIQNBAVAL-WQPDWFRBSA-N
Standard InCHI:	InChI=1S/C25H38O7/c1-17(2)15-22(29)32-21-10-13-24(5,12-9-20(28)23(3,4)30)11-7-18(16-26)19(27)8-14-25(21,6)31/h7-8,10,13-15,20-21,26,28,30-31H,9,11-12,16H2,1-6H3/b13-10+,14-8+,18-7-/t20?,21-,24-,25-/m1/s1
SMILES:	CC(=CC(=O)O[C@@H]1/C=C/[C@](C)(C/C=C(/CO)C(=O)/C=C/[C@@]1(C)O)CCC(C(C)(C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511824
PubChem CID:	11282367
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
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043405]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6717	Viburnum awabuki	Species	Adoxaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	<	10.0	ug ml-1	PMID[449036]

☑ 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 NPC11804 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	195
0.1-0.2	1235
0.2-0.3	4728
0.3-0.4	10394
0.4-0.5	14148
0.5-0.6	7210
0.6-0.7	3992
0.7-0.8	767
0.8-0.85	24
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC161045
0.9114	High Similarity	NPC279532
0.8861	High Similarity	NPC203277
0.8554	High Similarity	NPC112868
0.8471	Intermediate Similarity	NPC160517
0.8471	Intermediate Similarity	NPC186155
0.8471	Intermediate Similarity	NPC78673
0.8444	Intermediate Similarity	NPC65829
0.8372	Intermediate Similarity	NPC261380
0.8353	Intermediate Similarity	NPC474809
0.8276	Intermediate Similarity	NPC61527
0.8276	Intermediate Similarity	NPC311163
0.8228	Intermediate Similarity	NPC469660
0.8161	Intermediate Similarity	NPC471494
0.814	Intermediate Similarity	NPC23748
0.814	Intermediate Similarity	NPC49208
0.814	Intermediate Similarity	NPC44261
0.8132	Intermediate Similarity	NPC469692
0.8132	Intermediate Similarity	NPC469645
0.8125	Intermediate Similarity	NPC472755
0.8111	Intermediate Similarity	NPC145666
0.8105	Intermediate Similarity	NPC472753
0.8043	Intermediate Similarity	NPC121825
0.8023	Intermediate Similarity	NPC474291
0.8023	Intermediate Similarity	NPC85772
0.8021	Intermediate Similarity	NPC472754
0.8	Intermediate Similarity	NPC83423
0.8	Intermediate Similarity	NPC4299
0.7931	Intermediate Similarity	NPC16488
0.7927	Intermediate Similarity	NPC160540
0.7912	Intermediate Similarity	NPC3952
0.7912	Intermediate Similarity	NPC474761
0.7912	Intermediate Similarity	NPC476004
0.7912	Intermediate Similarity	NPC473448
0.7907	Intermediate Similarity	NPC474980
0.7907	Intermediate Similarity	NPC475944
0.7907	Intermediate Similarity	NPC474894
0.79	Intermediate Similarity	NPC47951
0.7895	Intermediate Similarity	NPC316598
0.7895	Intermediate Similarity	NPC159763
0.7895	Intermediate Similarity	NPC124512
0.7895	Intermediate Similarity	NPC475653
0.7895	Intermediate Similarity	NPC278386
0.7882	Intermediate Similarity	NPC471537
0.7875	Intermediate Similarity	NPC101622
0.7865	Intermediate Similarity	NPC261721
0.7865	Intermediate Similarity	NPC315395
0.7865	Intermediate Similarity	NPC316426
0.7857	Intermediate Similarity	NPC40049
0.7857	Intermediate Similarity	NPC472756
0.7849	Intermediate Similarity	NPC167219
0.7849	Intermediate Similarity	NPC469491
0.7841	Intermediate Similarity	NPC243618
0.7841	Intermediate Similarity	NPC471301
0.7841	Intermediate Similarity	NPC9868
0.7841	Intermediate Similarity	NPC70424
0.7831	Intermediate Similarity	NPC260396
0.7826	Intermediate Similarity	NPC303697
0.7826	Intermediate Similarity	NPC158061
0.7822	Intermediate Similarity	NPC29133
0.7802	Intermediate Similarity	NPC133450
0.7802	Intermediate Similarity	NPC20946
0.7789	Intermediate Similarity	NPC120299
0.7789	Intermediate Similarity	NPC40812
0.7789	Intermediate Similarity	NPC73911
0.7778	Intermediate Similarity	NPC72513
0.7765	Intermediate Similarity	NPC209135
0.7765	Intermediate Similarity	NPC473471
0.7765	Intermediate Similarity	NPC474816
0.7753	Intermediate Similarity	NPC137033
0.7745	Intermediate Similarity	NPC470961
0.7742	Intermediate Similarity	NPC53555
0.7738	Intermediate Similarity	NPC477202
0.7732	Intermediate Similarity	NPC133907
0.7732	Intermediate Similarity	NPC110443
0.7732	Intermediate Similarity	NPC46998
0.7732	Intermediate Similarity	NPC128733
0.7732	Intermediate Similarity	NPC185141
0.7717	Intermediate Similarity	NPC177668
0.7711	Intermediate Similarity	NPC315843
0.7711	Intermediate Similarity	NPC107654
0.7711	Intermediate Similarity	NPC144995
0.7711	Intermediate Similarity	NPC227814
0.7708	Intermediate Similarity	NPC161855
0.7708	Intermediate Similarity	NPC141191
0.7708	Intermediate Similarity	NPC83895
0.7708	Intermediate Similarity	NPC187761
0.7708	Intermediate Similarity	NPC475068
0.7701	Intermediate Similarity	NPC315731
0.7701	Intermediate Similarity	NPC325031
0.7692	Intermediate Similarity	NPC227379
0.7692	Intermediate Similarity	NPC260343
0.7692	Intermediate Similarity	NPC153805
0.7692	Intermediate Similarity	NPC474471
0.7684	Intermediate Similarity	NPC472995
0.7684	Intermediate Similarity	NPC255410
0.7684	Intermediate Similarity	NPC473291
0.7684	Intermediate Similarity	NPC473153
0.7677	Intermediate Similarity	NPC203659
0.7674	Intermediate Similarity	NPC139712
0.767	Intermediate Similarity	NPC138757
0.767	Intermediate Similarity	NPC191620
0.7667	Intermediate Similarity	NPC469483
0.7667	Intermediate Similarity	NPC472009
0.766	Intermediate Similarity	NPC472467
0.766	Intermediate Similarity	NPC53685
0.766	Intermediate Similarity	NPC477241
0.7653	Intermediate Similarity	NPC473596
0.7647	Intermediate Similarity	NPC475711
0.7647	Intermediate Similarity	NPC51809
0.7647	Intermediate Similarity	NPC257240
0.7647	Intermediate Similarity	NPC84360
0.7647	Intermediate Similarity	NPC176329
0.7647	Intermediate Similarity	NPC477203
0.7647	Intermediate Similarity	NPC125365
0.7647	Intermediate Similarity	NPC49302
0.7647	Intermediate Similarity	NPC474818
0.7647	Intermediate Similarity	NPC476007
0.7647	Intermediate Similarity	NPC262747
0.764	Intermediate Similarity	NPC474865
0.764	Intermediate Similarity	NPC31086
0.7634	Intermediate Similarity	NPC111114
0.7634	Intermediate Similarity	NPC300312
0.7634	Intermediate Similarity	NPC30515
0.7634	Intermediate Similarity	NPC261607
0.7614	Intermediate Similarity	NPC471298
0.7609	Intermediate Similarity	NPC82876
0.7609	Intermediate Similarity	NPC79027
0.7609	Intermediate Similarity	NPC212598
0.7604	Intermediate Similarity	NPC53844
0.7604	Intermediate Similarity	NPC169205
0.7604	Intermediate Similarity	NPC287668
0.7604	Intermediate Similarity	NPC205143
0.76	Intermediate Similarity	NPC472749
0.76	Intermediate Similarity	NPC472751
0.7596	Intermediate Similarity	NPC46269
0.7596	Intermediate Similarity	NPC106395
0.759	Intermediate Similarity	NPC477085
0.7586	Intermediate Similarity	NPC472948
0.7582	Intermediate Similarity	NPC248602
0.7582	Intermediate Similarity	NPC131329
0.7582	Intermediate Similarity	NPC478145
0.7582	Intermediate Similarity	NPC472007
0.7582	Intermediate Similarity	NPC471738
0.7582	Intermediate Similarity	NPC478144
0.7582	Intermediate Similarity	NPC199382
0.7582	Intermediate Similarity	NPC245004
0.7579	Intermediate Similarity	NPC300710
0.7579	Intermediate Similarity	NPC36954
0.7579	Intermediate Similarity	NPC272050
0.7579	Intermediate Similarity	NPC209355
0.7579	Intermediate Similarity	NPC476488
0.7579	Intermediate Similarity	NPC472469
0.7579	Intermediate Similarity	NPC476487
0.7576	Intermediate Similarity	NPC110989
0.7576	Intermediate Similarity	NPC475945
0.7576	Intermediate Similarity	NPC472747
0.7576	Intermediate Similarity	NPC475871
0.7576	Intermediate Similarity	NPC472750
0.7573	Intermediate Similarity	NPC324683
0.7561	Intermediate Similarity	NPC473361
0.7561	Intermediate Similarity	NPC329904
0.7558	Intermediate Similarity	NPC221095
0.7558	Intermediate Similarity	NPC248775
0.7558	Intermediate Similarity	NPC279214
0.7556	Intermediate Similarity	NPC475034
0.7553	Intermediate Similarity	NPC59646
0.7553	Intermediate Similarity	NPC472196
0.7553	Intermediate Similarity	NPC238090
0.7553	Intermediate Similarity	NPC475912
0.7553	Intermediate Similarity	NPC472195
0.7551	Intermediate Similarity	NPC474742
0.7549	Intermediate Similarity	NPC475065
0.7531	Intermediate Similarity	NPC310210
0.7529	Intermediate Similarity	NPC209113
0.7529	Intermediate Similarity	NPC301207
0.7529	Intermediate Similarity	NPC469880
0.7529	Intermediate Similarity	NPC127118
0.7528	Intermediate Similarity	NPC229799
0.7528	Intermediate Similarity	NPC477784
0.7528	Intermediate Similarity	NPC477786
0.7528	Intermediate Similarity	NPC471297
0.7528	Intermediate Similarity	NPC284472
0.7528	Intermediate Similarity	NPC11620
0.7528	Intermediate Similarity	NPC477785
0.7528	Intermediate Similarity	NPC286770
0.7527	Intermediate Similarity	NPC51486
0.7527	Intermediate Similarity	NPC265856
0.7527	Intermediate Similarity	NPC182136
0.7527	Intermediate Similarity	NPC51004
0.7527	Intermediate Similarity	NPC472466
0.7527	Intermediate Similarity	NPC166554
0.7527	Intermediate Similarity	NPC475879
0.7526	Intermediate Similarity	NPC308567
0.7526	Intermediate Similarity	NPC65700
0.7526	Intermediate Similarity	NPC261377
0.7526	Intermediate Similarity	NPC255592
0.7525	Intermediate Similarity	NPC329048
0.7525	Intermediate Similarity	NPC330011
0.7524	Intermediate Similarity	NPC138303

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 NPC11804 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1707
0.2-0.3	3704
0.3-0.4	2417
0.4-0.5	769
0.5-0.6	308
0.6-0.7	55
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
0.7912	Intermediate Similarity	NPD5785	Approved
0.7912	Intermediate Similarity	NPD7838	Discovery
0.7895	Intermediate Similarity	NPD4225	Approved
0.7647	Intermediate Similarity	NPD6371	Approved
0.7396	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7115	Discovery
0.7374	Intermediate Similarity	NPD5344	Discontinued
0.7363	Intermediate Similarity	NPD5363	Approved
0.7347	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD46	Approved
0.734	Intermediate Similarity	NPD6698	Approved
0.7263	Intermediate Similarity	NPD7983	Approved
0.7253	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5209	Approved
0.716	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4269	Approved
0.7033	Intermediate Similarity	NPD4270	Approved
0.7019	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7154	Phase 3
0.6931	Remote Similarity	NPD6648	Approved
0.6923	Remote Similarity	NPD5369	Approved
0.6915	Remote Similarity	NPD5786	Approved
0.6907	Remote Similarity	NPD7637	Suspended
0.6837	Remote Similarity	NPD5779	Approved
0.6837	Remote Similarity	NPD5778	Approved
0.6813	Remote Similarity	NPD4820	Approved
0.6813	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4252	Approved
0.6813	Remote Similarity	NPD4822	Approved
0.6813	Remote Similarity	NPD4821	Approved
0.6813	Remote Similarity	NPD4819	Approved
0.6792	Remote Similarity	NPD6686	Approved
0.6774	Remote Similarity	NPD5362	Discontinued
0.6765	Remote Similarity	NPD7640	Approved
0.6765	Remote Similarity	NPD7639	Approved
0.6735	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7638	Approved
0.6632	Remote Similarity	NPD1694	Approved
0.6632	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8039	Approved
0.6596	Remote Similarity	NPD5332	Approved
0.6596	Remote Similarity	NPD5331	Approved
0.6593	Remote Similarity	NPD4268	Approved
0.6593	Remote Similarity	NPD4271	Approved
0.6559	Remote Similarity	NPD4790	Discontinued
0.6531	Remote Similarity	NPD5370	Suspended
0.6531	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6101	Approved
0.6495	Remote Similarity	NPD7524	Approved
0.6471	Remote Similarity	NPD7839	Suspended
0.6471	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5282	Discontinued
0.6429	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4251	Approved
0.6327	Remote Similarity	NPD4250	Approved
0.6316	Remote Similarity	NPD6435	Approved
0.6306	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4756	Discovery
0.6289	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7748	Approved
0.6265	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6110	Phase 1
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD6695	Phase 3
0.6239	Remote Similarity	NPD7503	Approved
0.6238	Remote Similarity	NPD7515	Phase 2
0.6235	Remote Similarity	NPD3197	Phase 1
0.6224	Remote Similarity	NPD4249	Approved
0.62	Remote Similarity	NPD6051	Approved
0.6196	Remote Similarity	NPD6933	Approved
0.619	Remote Similarity	NPD4194	Approved
0.619	Remote Similarity	NPD4193	Approved
0.619	Remote Similarity	NPD4191	Approved
0.619	Remote Similarity	NPD4192	Approved
0.6186	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6899	Approved
0.6182	Remote Similarity	NPD6881	Approved
0.6182	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6399	Phase 3
0.6174	Remote Similarity	NPD7505	Discontinued
0.6168	Remote Similarity	NPD7632	Discontinued
0.6154	Remote Similarity	NPD6319	Approved
0.6134	Remote Similarity	NPD7642	Approved
0.6126	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD1696	Phase 3
0.6121	Remote Similarity	NPD7327	Approved
0.6121	Remote Similarity	NPD7328	Approved
0.6111	Remote Similarity	NPD6647	Phase 2
0.6105	Remote Similarity	NPD5368	Approved
0.6102	Remote Similarity	NPD8513	Phase 3
0.6102	Remote Similarity	NPD8515	Approved
0.6102	Remote Similarity	NPD8033	Approved
0.6102	Remote Similarity	NPD8516	Approved
0.6102	Remote Similarity	NPD8517	Approved
0.6095	Remote Similarity	NPD7902	Approved
0.6092	Remote Similarity	NPD7331	Phase 2
0.6091	Remote Similarity	NPD5697	Approved
0.6087	Remote Similarity	NPD8264	Approved
0.6071	Remote Similarity	NPD7290	Approved
0.6071	Remote Similarity	NPD7102	Approved
0.6071	Remote Similarity	NPD6883	Approved
0.6068	Remote Similarity	NPD7516	Approved
0.6064	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7146	Approved
0.6061	Remote Similarity	NPD5330	Approved
0.6061	Remote Similarity	NPD7521	Approved
0.6061	Remote Similarity	NPD6409	Approved
0.6061	Remote Similarity	NPD6684	Approved
0.6061	Remote Similarity	NPD7334	Approved
0.6058	Remote Similarity	NPD5695	Phase 3
0.6053	Remote Similarity	NPD4632	Approved
0.6036	Remote Similarity	NPD6011	Approved
0.6034	Remote Similarity	NPD7500	Approved
0.6033	Remote Similarity	NPD8273	Phase 1
0.6024	Remote Similarity	NPD6109	Phase 1
0.6023	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6650	Approved
0.6018	Remote Similarity	NPD6869	Approved
0.6018	Remote Similarity	NPD8130	Phase 1
0.6018	Remote Similarity	NPD6617	Approved
0.6018	Remote Similarity	NPD6847	Approved
0.6018	Remote Similarity	NPD6649	Approved
0.6017	Remote Similarity	NPD8294	Approved
0.6017	Remote Similarity	NPD8377	Approved
0.6016	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD7830	Approved
0.6	Remote Similarity	NPD6402	Approved
0.5982	Remote Similarity	NPD6014	Approved
0.5982	Remote Similarity	NPD6413	Approved
0.5982	Remote Similarity	NPD6012	Approved
0.5982	Remote Similarity	NPD6013	Approved
0.5979	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6926	Approved
0.5978	Remote Similarity	NPD6924	Approved
0.5966	Remote Similarity	NPD8335	Approved
0.5966	Remote Similarity	NPD8296	Approved
0.5966	Remote Similarity	NPD8379	Approved
0.5966	Remote Similarity	NPD8380	Approved
0.5966	Remote Similarity	NPD8378	Approved
0.5965	Remote Similarity	NPD6882	Approved
0.5965	Remote Similarity	NPD6053	Discontinued
0.595	Remote Similarity	NPD7492	Approved
0.5946	Remote Similarity	NPD6412	Phase 2
0.5941	Remote Similarity	NPD6903	Approved
0.5941	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6672	Approved
0.5941	Remote Similarity	NPD5737	Approved
0.5938	Remote Similarity	NPD7332	Phase 2
0.5938	Remote Similarity	NPD4695	Discontinued
0.5938	Remote Similarity	NPD6931	Approved
0.5938	Remote Similarity	NPD7514	Phase 3
0.5938	Remote Similarity	NPD6930	Phase 2
0.5922	Remote Similarity	NPD6079	Approved
0.5922	Remote Similarity	NPD5693	Phase 1
0.5902	Remote Similarity	NPD7507	Approved
0.5902	Remote Similarity	NPD6616	Approved
0.59	Remote Similarity	NPD4519	Discontinued
0.59	Remote Similarity	NPD4623	Approved
0.5897	Remote Similarity	NPD4198	Discontinued
0.5893	Remote Similarity	NPD7320	Approved
0.5888	Remote Similarity	NPD5696	Approved
0.5882	Remote Similarity	NPD1695	Approved
0.5882	Remote Similarity	NPD6054	Approved
0.5872	Remote Similarity	NPD5211	Phase 2
0.587	Remote Similarity	NPD4732	Discontinued
0.5859	Remote Similarity	NPD4786	Approved
0.5859	Remote Similarity	NPD3665	Phase 1
0.5859	Remote Similarity	NPD3133	Approved
0.5859	Remote Similarity	NPD3666	Approved
0.5854	Remote Similarity	NPD7078	Approved
0.5854	Remote Similarity	NPD8074	Phase 3
0.5842	Remote Similarity	NPD3573	Approved
0.5841	Remote Similarity	NPD6372	Approved
0.5841	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD6929	Approved
0.5833	Remote Similarity	NPD4195	Approved
0.5833	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8444	Approved
0.5816	Remote Similarity	NPD3667	Approved
0.5814	Remote Similarity	NPD368	Approved
0.5812	Remote Similarity	NPD2629	Approved
0.581	Remote Similarity	NPD7900	Approved
0.581	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7736	Approved
0.5804	Remote Similarity	NPD5701	Approved
0.5795	Remote Similarity	NPD7341	Phase 2
0.5794	Remote Similarity	NPD7260	Phase 2
0.5789	Remote Similarity	NPD5955	Clinical (unspecified phase)

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