NPASS Compound

Structure

CID161045 OpenBabel06191715532D 31 31 0 0 1 0 0 0 0 0999 V2000 -2.7667 0.3034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3747 -0.3404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8413 -5.5350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3413 -6.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 -3.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3271 0.9450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9556 -1.8995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8413 -3.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8413 0.5406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2731 -1.8995 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 1.8413 -3.8030 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 0.8413 0.5406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0132 -1.4111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0877 -0.7673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3849 -0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8413 -5.5350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0979 -0.9096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3413 -4.6690 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6825 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4154 -0.9096 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0234 -1.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3413 -2.9369 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 4.7059 -1.5534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3413 -4.6690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4383 0.6549 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6517 -2.4817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9819 0.1893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4052 -0.7673 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 18 2 0 0 0 0 4 18 1 0 0 0 0 7 11 1 0 0 0 0 7 19 2 0 0 0 0 8 12 1 0 0 0 0 8 20 1 0 0 0 0 9 14 2 0 0 0 0 9 21 1 0 0 0 0 10 13 2 0 0 0 0 10 22 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 23 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 27 1 0 0 0 0 21 28 2 0 0 0 0 22 25 1 1 0 0 0 22 31 1 0 0 0 0 23 29 2 0 0 0 0 23 31 1 0 0 0 0 24 5 1 1 0 0 0 25 6 1 1 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.25
Volume:	466.686
LogP:	2.334
LogD:	1.291
LogS:	-3.678
# Rotatable Bonds:	8
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	5.582
Fsp3:	0.52
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:	-4.705
MDCK Permeability:	1.201369559566956e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.896
Human Intestinal Absorption (HIA):	0.603
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.848
Plasma Protein Binding (PPB):	75.00879669189453%
Volume Distribution (VD):	0.813
Pgp-substrate:	18.75211524963379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.469
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.713
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.881
CYP3A4-substrate:	0.322

ADMET: Excretion

Clearance (CL):	2.287
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.51
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.311
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.359
Carcinogencity:	0.165
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC161045

Natural Product ID:	NPC161045
*Common Name:**	Vibsanol B
IUPAC Name:	[(1R,2E,4S,6Z,9E,11R)-11-hydroxy-7-(hydroxymethyl)-4-(3-hydroxy-4-methylpent-4-enyl)-4,11-dimethyl-8-oxocycloundeca-2,6,9-trien-1-yl] 3-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	NROSZFYAWYCTMA-XZHYIBAESA-N
Standard InCHI:	InChI=1S/C25H36O6/c1-17(2)15-23(29)31-22-10-13-24(5,12-8-20(27)18(3)4)11-7-19(16-26)21(28)9-14-25(22,6)30/h7,9-10,13-15,20,22,26-27,30H,3,8,11-12,16H2,1-2,4-6H3/b13-10+,14-9+,19-7-/t20?,22-,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)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454851
PubChem CID:	11144536
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
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141874]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	leaves and flowers	n.a.	n.a.	PMID[14738390]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18814	Viburnum odoratissimum	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4162	Cell Line	NUGC	Homo sapiens	Activity	>	50.0	%	PMID[455746]

☑ 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 NPC161045 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	188
0.1-0.2	1224
0.2-0.3	5067
0.3-0.4	12365
0.4-0.5	13103
0.5-0.6	6680
0.6-0.7	3449
0.7-0.8	601
0.8-0.85	16
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC11804
0.9351	High Similarity	NPC279532
0.9091	High Similarity	NPC203277
0.8452	Intermediate Similarity	NPC160517
0.8452	Intermediate Similarity	NPC186155
0.8452	Intermediate Similarity	NPC78673
0.8313	Intermediate Similarity	NPC112868
0.8256	Intermediate Similarity	NPC61527
0.8222	Intermediate Similarity	NPC65829
0.8205	Intermediate Similarity	NPC469660
0.814	Intermediate Similarity	NPC261380
0.814	Intermediate Similarity	NPC471494
0.8125	Intermediate Similarity	NPC160540
0.8118	Intermediate Similarity	NPC474809
0.8118	Intermediate Similarity	NPC16488
0.8118	Intermediate Similarity	NPC44261
0.8095	Intermediate Similarity	NPC474980
0.8046	Intermediate Similarity	NPC316426
0.8046	Intermediate Similarity	NPC311163
0.8046	Intermediate Similarity	NPC315395
0.8025	Intermediate Similarity	NPC260396
0.8	Intermediate Similarity	NPC85772
0.7978	Intermediate Similarity	NPC83423
0.7975	Intermediate Similarity	NPC4299
0.7952	Intermediate Similarity	NPC474816
0.7952	Intermediate Similarity	NPC209135
0.7952	Intermediate Similarity	NPC473471
0.7917	Intermediate Similarity	NPC472755
0.7912	Intermediate Similarity	NPC469645
0.7912	Intermediate Similarity	NPC469692
0.7907	Intermediate Similarity	NPC23748
0.7907	Intermediate Similarity	NPC49208
0.7901	Intermediate Similarity	NPC315843
0.7901	Intermediate Similarity	NPC107654
0.7895	Intermediate Similarity	NPC472753
0.7889	Intermediate Similarity	NPC145666
0.7882	Intermediate Similarity	NPC475944
0.7857	Intermediate Similarity	NPC471537
0.7848	Intermediate Similarity	NPC101622
0.7831	Intermediate Similarity	NPC51809
0.7831	Intermediate Similarity	NPC176329
0.7831	Intermediate Similarity	NPC49302
0.7831	Intermediate Similarity	NPC262747
0.7831	Intermediate Similarity	NPC474818
0.7831	Intermediate Similarity	NPC125365
0.7826	Intermediate Similarity	NPC121825
0.7816	Intermediate Similarity	NPC70424
0.7816	Intermediate Similarity	NPC31086
0.7816	Intermediate Similarity	NPC243618
0.7816	Intermediate Similarity	NPC474865
0.7812	Intermediate Similarity	NPC472754
0.7791	Intermediate Similarity	NPC474291
0.7778	Intermediate Similarity	NPC79027
0.7753	Intermediate Similarity	NPC72513
0.775	Intermediate Similarity	NPC473361
0.775	Intermediate Similarity	NPC329904
0.7738	Intermediate Similarity	NPC279214
0.7738	Intermediate Similarity	NPC221095
0.7727	Intermediate Similarity	NPC475034
0.7722	Intermediate Similarity	NPC310210
0.7711	Intermediate Similarity	NPC209113
0.7711	Intermediate Similarity	NPC301207
0.7711	Intermediate Similarity	NPC477202
0.7711	Intermediate Similarity	NPC127118
0.7701	Intermediate Similarity	NPC284472
0.7701	Intermediate Similarity	NPC286770
0.7701	Intermediate Similarity	NPC229799
0.77	Intermediate Similarity	NPC47951
0.7692	Intermediate Similarity	NPC474761
0.7692	Intermediate Similarity	NPC473448
0.7692	Intermediate Similarity	NPC3952
0.7692	Intermediate Similarity	NPC476004
0.7684	Intermediate Similarity	NPC161855
0.7684	Intermediate Similarity	NPC278386
0.7684	Intermediate Similarity	NPC124512
0.7684	Intermediate Similarity	NPC316598
0.7684	Intermediate Similarity	NPC159763
0.7684	Intermediate Similarity	NPC475653
0.7683	Intermediate Similarity	NPC227814
0.7683	Intermediate Similarity	NPC144995
0.7674	Intermediate Similarity	NPC474894
0.7674	Intermediate Similarity	NPC315731
0.766	Intermediate Similarity	NPC255410
0.766	Intermediate Similarity	NPC473291
0.7654	Intermediate Similarity	NPC316185
0.7654	Intermediate Similarity	NPC472254
0.7653	Intermediate Similarity	NPC472756
0.7647	Intermediate Similarity	NPC139712
0.764	Intermediate Similarity	NPC472009
0.764	Intermediate Similarity	NPC469483
0.764	Intermediate Similarity	NPC261721
0.7634	Intermediate Similarity	NPC167219
0.7634	Intermediate Similarity	NPC469491
0.7625	Intermediate Similarity	NPC151481
0.7625	Intermediate Similarity	NPC475982
0.7624	Intermediate Similarity	NPC29133
0.7619	Intermediate Similarity	NPC475711
0.7619	Intermediate Similarity	NPC40049
0.7619	Intermediate Similarity	NPC84360
0.7619	Intermediate Similarity	NPC477203
0.7614	Intermediate Similarity	NPC471301
0.7614	Intermediate Similarity	NPC9868
0.7609	Intermediate Similarity	NPC303697
0.7609	Intermediate Similarity	NPC158061
0.7586	Intermediate Similarity	NPC11383
0.7586	Intermediate Similarity	NPC310450
0.7586	Intermediate Similarity	NPC474959
0.7586	Intermediate Similarity	NPC471298
0.7586	Intermediate Similarity	NPC471296
0.7586	Intermediate Similarity	NPC323251
0.7586	Intermediate Similarity	NPC475046
0.7586	Intermediate Similarity	NPC26624
0.7582	Intermediate Similarity	NPC133450
0.7582	Intermediate Similarity	NPC20946
0.7579	Intermediate Similarity	NPC73911
0.7579	Intermediate Similarity	NPC40812
0.7579	Intermediate Similarity	NPC120299
0.7564	Intermediate Similarity	NPC19769
0.7561	Intermediate Similarity	NPC477085
0.7556	Intermediate Similarity	NPC472007
0.7556	Intermediate Similarity	NPC475037
0.7556	Intermediate Similarity	NPC471738
0.7556	Intermediate Similarity	NPC199382
0.7553	Intermediate Similarity	NPC300710
0.7553	Intermediate Similarity	NPC214694
0.7549	Intermediate Similarity	NPC470961
0.7529	Intermediate Similarity	NPC182292
0.7529	Intermediate Similarity	NPC248775
0.7528	Intermediate Similarity	NPC137033
0.7527	Intermediate Similarity	NPC238090
0.7527	Intermediate Similarity	NPC282644
0.7527	Intermediate Similarity	NPC29798
0.7527	Intermediate Similarity	NPC472195
0.7527	Intermediate Similarity	NPC53555
0.7527	Intermediate Similarity	NPC472196
0.7526	Intermediate Similarity	NPC185141
0.7526	Intermediate Similarity	NPC128733
0.7526	Intermediate Similarity	NPC110443
0.7526	Intermediate Similarity	NPC133907
0.7526	Intermediate Similarity	NPC46998
0.75	Intermediate Similarity	NPC16279
0.75	Intermediate Similarity	NPC475068
0.75	Intermediate Similarity	NPC166554
0.75	Intermediate Similarity	NPC471297
0.75	Intermediate Similarity	NPC265856
0.75	Intermediate Similarity	NPC187761
0.75	Intermediate Similarity	NPC256640
0.75	Intermediate Similarity	NPC477786
0.75	Intermediate Similarity	NPC477785
0.75	Intermediate Similarity	NPC141191
0.75	Intermediate Similarity	NPC83895
0.75	Intermediate Similarity	NPC177668
0.75	Intermediate Similarity	NPC469880
0.75	Intermediate Similarity	NPC205615
0.75	Intermediate Similarity	NPC473455
0.75	Intermediate Similarity	NPC477784
0.75	Intermediate Similarity	NPC475879
0.7476	Intermediate Similarity	NPC191620
0.7476	Intermediate Similarity	NPC138757
0.7475	Intermediate Similarity	NPC203659
0.7474	Intermediate Similarity	NPC473153
0.7474	Intermediate Similarity	NPC472995
0.7473	Intermediate Similarity	NPC472008
0.7473	Intermediate Similarity	NPC153805
0.7473	Intermediate Similarity	NPC227379
0.7473	Intermediate Similarity	NPC476803
0.7473	Intermediate Similarity	NPC474471
0.7473	Intermediate Similarity	NPC60765
0.7473	Intermediate Similarity	NPC260343
0.7471	Intermediate Similarity	NPC325031
0.7471	Intermediate Similarity	NPC184208
0.7471	Intermediate Similarity	NPC8538
0.7471	Intermediate Similarity	NPC150502
0.7468	Intermediate Similarity	NPC201356
0.7451	Intermediate Similarity	NPC257240
0.7449	Intermediate Similarity	NPC473596
0.7447	Intermediate Similarity	NPC159698
0.7447	Intermediate Similarity	NPC472467
0.7447	Intermediate Similarity	NPC477241
0.7447	Intermediate Similarity	NPC53685
0.7444	Intermediate Similarity	NPC469910
0.7444	Intermediate Similarity	NPC164393
0.7442	Intermediate Similarity	NPC1180
0.7442	Intermediate Similarity	NPC86971
0.7442	Intermediate Similarity	NPC470148
0.7442	Intermediate Similarity	NPC470149
0.7442	Intermediate Similarity	NPC99651
0.7442	Intermediate Similarity	NPC180725
0.7439	Intermediate Similarity	NPC477086
0.7439	Intermediate Similarity	NPC293114
0.7439	Intermediate Similarity	NPC477087
0.7419	Intermediate Similarity	NPC261607
0.7419	Intermediate Similarity	NPC30515
0.7419	Intermediate Similarity	NPC300312
0.7419	Intermediate Similarity	NPC111114
0.7416	Intermediate Similarity	NPC475035
0.7416	Intermediate Similarity	NPC471302
0.7416	Intermediate Similarity	NPC161670
0.7416	Intermediate Similarity	NPC126518
0.7416	Intermediate Similarity	NPC474776

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 NPC161045 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1710
0.2-0.3	3848
0.3-0.4	2409
0.4-0.5	679
0.5-0.6	271
0.6-0.7	50
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
0.7889	Intermediate Similarity	NPD5785	Approved
0.7692	Intermediate Similarity	NPD7838	Discovery
0.7684	Intermediate Similarity	NPD4225	Approved
0.7451	Intermediate Similarity	NPD6371	Approved
0.7416	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5209	Approved
0.7342	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5363	Approved
0.732	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD46	Approved
0.7312	Intermediate Similarity	NPD6698	Approved
0.7234	Intermediate Similarity	NPD7983	Approved
0.7196	Intermediate Similarity	NPD7115	Discovery
0.7188	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5344	Discontinued
0.7126	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7637	Suspended
0.7	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD4270	Approved
0.6966	Remote Similarity	NPD4252	Approved
0.6923	Remote Similarity	NPD7154	Phase 3
0.6889	Remote Similarity	NPD5369	Approved
0.6882	Remote Similarity	NPD5786	Approved
0.6827	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4819	Approved
0.6778	Remote Similarity	NPD4821	Approved
0.6778	Remote Similarity	NPD4820	Approved
0.6778	Remote Similarity	NPD4822	Approved
0.6778	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5362	Discontinued
0.6733	Remote Similarity	NPD6648	Approved
0.6633	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD5779	Approved
0.6604	Remote Similarity	NPD6686	Approved
0.6596	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8039	Approved
0.6585	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7640	Approved
0.6569	Remote Similarity	NPD7639	Approved
0.6559	Remote Similarity	NPD5332	Approved
0.6559	Remote Similarity	NPD5331	Approved
0.6556	Remote Similarity	NPD4271	Approved
0.6556	Remote Similarity	NPD4268	Approved
0.6531	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD4790	Discontinued
0.6495	Remote Similarity	NPD5370	Suspended
0.6471	Remote Similarity	NPD7638	Approved
0.6452	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7839	Suspended
0.6421	Remote Similarity	NPD1694	Approved
0.642	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6110	Phase 1
0.6364	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4191	Approved
0.6341	Remote Similarity	NPD4192	Approved
0.6341	Remote Similarity	NPD4193	Approved
0.6341	Remote Similarity	NPD4194	Approved
0.6327	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6101	Approved
0.6289	Remote Similarity	NPD7524	Approved
0.6289	Remote Similarity	NPD4251	Approved
0.6289	Remote Similarity	NPD4250	Approved
0.6277	Remote Similarity	NPD6435	Approved
0.6273	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4756	Discovery
0.625	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5282	Discontinued
0.6222	Remote Similarity	NPD8264	Approved
0.6196	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3197	Phase 1
0.6186	Remote Similarity	NPD4249	Approved
0.6173	Remote Similarity	NPD6109	Phase 1
0.6163	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7642	Approved
0.6082	Remote Similarity	NPD1696	Phase 3
0.6078	Remote Similarity	NPD7748	Approved
0.6075	Remote Similarity	NPD6647	Phase 2
0.6071	Remote Similarity	NPD8297	Approved
0.6068	Remote Similarity	NPD8513	Phase 3
0.6068	Remote Similarity	NPD7503	Approved
0.6068	Remote Similarity	NPD8515	Approved
0.6068	Remote Similarity	NPD8517	Approved
0.6068	Remote Similarity	NPD8516	Approved
0.6064	Remote Similarity	NPD7332	Phase 2
0.6064	Remote Similarity	NPD5368	Approved
0.6064	Remote Similarity	NPD7514	Phase 3
0.6058	Remote Similarity	NPD6083	Phase 2
0.6058	Remote Similarity	NPD6084	Phase 2
0.6047	Remote Similarity	NPD7331	Phase 2
0.6042	Remote Similarity	NPD6695	Phase 3
0.604	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD4732	Discontinued
0.6	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD7505	Discontinued
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6319	Approved
0.5981	Remote Similarity	NPD7632	Discontinued
0.598	Remote Similarity	NPD6399	Phase 3
0.5979	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6933	Approved
0.5976	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7830	Approved
0.5966	Remote Similarity	NPD7829	Approved
0.5952	Remote Similarity	NPD368	Approved
0.5948	Remote Similarity	NPD7327	Approved
0.5948	Remote Similarity	NPD7328	Approved
0.5946	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD8033	Approved
0.5909	Remote Similarity	NPD5697	Approved
0.5905	Remote Similarity	NPD7902	Approved
0.5897	Remote Similarity	NPD7516	Approved
0.5897	Remote Similarity	NPD6927	Phase 3
0.5893	Remote Similarity	NPD7102	Approved
0.5893	Remote Similarity	NPD7290	Approved
0.5893	Remote Similarity	NPD6883	Approved
0.5877	Remote Similarity	NPD4632	Approved
0.5868	Remote Similarity	NPD8273	Phase 1
0.5865	Remote Similarity	NPD5695	Phase 3
0.5859	Remote Similarity	NPD5330	Approved
0.5859	Remote Similarity	NPD6684	Approved
0.5859	Remote Similarity	NPD7146	Approved
0.5859	Remote Similarity	NPD7521	Approved
0.5859	Remote Similarity	NPD6409	Approved
0.5859	Remote Similarity	NPD7334	Approved
0.5856	Remote Similarity	NPD6011	Approved
0.5854	Remote Similarity	NPD7319	Approved
0.5851	Remote Similarity	NPD7145	Approved
0.5847	Remote Similarity	NPD8377	Approved
0.5847	Remote Similarity	NPD8294	Approved
0.5841	Remote Similarity	NPD6847	Approved
0.5841	Remote Similarity	NPD6617	Approved
0.5841	Remote Similarity	NPD6649	Approved
0.5841	Remote Similarity	NPD6869	Approved
0.5841	Remote Similarity	NPD6650	Approved
0.5841	Remote Similarity	NPD8130	Phase 1
0.5833	Remote Similarity	NPD6902	Approved
0.582	Remote Similarity	NPD8074	Phase 3
0.5818	Remote Similarity	NPD6675	Approved
0.5818	Remote Similarity	NPD7128	Approved
0.5818	Remote Similarity	NPD5739	Approved
0.5818	Remote Similarity	NPD6402	Approved
0.5816	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6013	Approved
0.5804	Remote Similarity	NPD6012	Approved
0.5804	Remote Similarity	NPD6413	Approved
0.5804	Remote Similarity	NPD6014	Approved
0.58	Remote Similarity	NPD7750	Discontinued
0.5798	Remote Similarity	NPD8444	Approved
0.5798	Remote Similarity	NPD8335	Approved
0.5798	Remote Similarity	NPD8380	Approved
0.5798	Remote Similarity	NPD8296	Approved
0.5798	Remote Similarity	NPD8378	Approved
0.5798	Remote Similarity	NPD8379	Approved
0.5789	Remote Similarity	NPD6053	Discontinued
0.5789	Remote Similarity	NPD6882	Approved
0.5785	Remote Similarity	NPD7492	Approved
0.5778	Remote Similarity	NPD7143	Approved
0.5778	Remote Similarity	NPD7144	Approved
0.5773	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6412	Phase 2
0.5761	Remote Similarity	NPD6926	Approved
0.5761	Remote Similarity	NPD6924	Approved
0.575	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7623	Phase 3
0.5745	Remote Similarity	NPD6932	Approved
0.5745	Remote Similarity	NPD6925	Approved
0.5745	Remote Similarity	NPD5776	Phase 2
0.5743	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6903	Approved
0.5743	Remote Similarity	NPD5737	Approved
0.5743	Remote Similarity	NPD6672	Approved
0.5738	Remote Similarity	NPD6616	Approved
0.5738	Remote Similarity	NPD7507	Approved
0.5732	Remote Similarity	NPD4219	Approved
0.5729	Remote Similarity	NPD6931	Approved
0.5729	Remote Similarity	NPD6930	Phase 2
0.5729	Remote Similarity	NPD4695	Discontinued
0.5728	Remote Similarity	NPD6079	Approved
0.5728	Remote Similarity	NPD5693	Phase 1
0.5726	Remote Similarity	NPD4198	Discontinued
0.5714	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7150	Approved
0.5714	Remote Similarity	NPD7152	Approved
0.5714	Remote Similarity	NPD6054	Approved
0.5714	Remote Similarity	NPD7151	Approved
0.5701	Remote Similarity	NPD5696	Approved
0.57	Remote Similarity	NPD4519	Discontinued
0.57	Remote Similarity	NPD4623	Approved
0.5691	Remote Similarity	NPD7078	Approved
0.5688	Remote Similarity	NPD5211	Phase 2
0.5686	Remote Similarity	NPD1695	Approved
0.5684	Remote Similarity	NPD3732	Approved
0.5678	Remote Similarity	NPD7641	Discontinued

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