NPASS Compound

Structure

NPC167873 OpenBabel07101718232D 21 21 0 0 1 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -0.8660 -1.5000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 14 19 2 0 0 0 0 15 17 1 0 0 0 0 15 18 1 6 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 18 5 1 6 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.24
Volume:	332.425
LogP:	2.643
LogD:	2.871
LogS:	-2.586
# Rotatable Bonds:	6
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	3.927
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.574
MDCK Permeability:	2.302677785337437e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.809
30% Bioavailability (F30%):	0.783

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.832
Plasma Protein Binding (PPB):	71.85724639892578%
Volume Distribution (VD):	0.783
Pgp-substrate:	26.976573944091797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.743
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.513
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	9.685
Half-life (T1/2):	0.701

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.201
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.522
Carcinogencity:	0.162
Eye Corrosion:	0.524
Eye Irritation:	0.423
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC167873

Natural Product ID:	NPC167873
*Common Name:**	Moniliforminol A
IUPAC Name:	(E)-8-[(1S,3S,6S)-3,6-dihydroxy-2,2,6-trimethylcyclohexyl]-6-methyloct-5-en-2-one
Synonyms:
Standard InCHIKey:	SKDGJZCQTPSFAG-KTBDZKMFSA-N
Standard InCHI:	InChI=1S/C18H32O3/c1-13(7-6-8-14(2)19)9-10-15-17(3,4)16(20)11-12-18(15,5)21/h7,15-16,20-21H,6,8-12H2,1-5H3/b13-7+/t15-,16-,18-/m0/s1
SMILES:	C/C(=CCCC(=O)C)/CC[C@H]1C(C)(C)[C@H](CC[C@]1(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500148
PubChem CID:	25015885
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO15949	Cystophora moniliformis	Species	Sargassaceae	Eukaryota	n.a.	southern Australian	n.a.	PMID[18687007]
NPO15949	Cystophora moniliformis	Species	Sargassaceae	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
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	40000.0	nM	PMID[483399]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	1.0	mm	PMID[483399]

☑ 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 NPC167873 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	161
0.1-0.2	1199
0.2-0.3	5507
0.3-0.4	15959
0.4-0.5	7929
0.5-0.6	6929
0.6-0.7	4015
0.7-0.8	961
0.8-0.85	33
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC1973
0.8649	High Similarity	NPC78527
0.863	High Similarity	NPC167706
0.863	High Similarity	NPC164022
0.8481	Intermediate Similarity	NPC48362
0.8429	Intermediate Similarity	NPC225415
0.8378	Intermediate Similarity	NPC471272
0.8333	Intermediate Similarity	NPC470429
0.8333	Intermediate Similarity	NPC96962
0.8312	Intermediate Similarity	NPC85105
0.8312	Intermediate Similarity	NPC149550
0.8312	Intermediate Similarity	NPC470428
0.8289	Intermediate Similarity	NPC291503
0.8267	Intermediate Similarity	NPC68443
0.8243	Intermediate Similarity	NPC92801
0.8205	Intermediate Similarity	NPC476949
0.8182	Intermediate Similarity	NPC265588
0.8182	Intermediate Similarity	NPC250621
0.8171	Intermediate Similarity	NPC470574
0.8171	Intermediate Similarity	NPC133954
0.8158	Intermediate Similarity	NPC91858
0.8158	Intermediate Similarity	NPC476366
0.8158	Intermediate Similarity	NPC243342
0.8158	Intermediate Similarity	NPC201048
0.8158	Intermediate Similarity	NPC477138
0.8148	Intermediate Similarity	NPC64600
0.8125	Intermediate Similarity	NPC473420
0.8101	Intermediate Similarity	NPC80530
0.8101	Intermediate Similarity	NPC273410
0.8095	Intermediate Similarity	NPC193360
0.8082	Intermediate Similarity	NPC185874
0.8082	Intermediate Similarity	NPC139207
0.8077	Intermediate Similarity	NPC470711
0.8077	Intermediate Similarity	NPC470758
0.8077	Intermediate Similarity	NPC197659
0.8077	Intermediate Similarity	NPC283619
0.8077	Intermediate Similarity	NPC325946
0.8072	Intermediate Similarity	NPC74363
0.8072	Intermediate Similarity	NPC73038
0.8072	Intermediate Similarity	NPC213412
0.8072	Intermediate Similarity	NPC475862
0.8052	Intermediate Similarity	NPC477923
0.8052	Intermediate Similarity	NPC66566
0.8049	Intermediate Similarity	NPC251170
0.8046	Intermediate Similarity	NPC103527
0.8026	Intermediate Similarity	NPC182717
0.8	Intermediate Similarity	NPC322313
0.8	Intermediate Similarity	NPC472983
0.8	Intermediate Similarity	NPC157895
0.8	Intermediate Similarity	NPC104120
0.8	Intermediate Similarity	NPC148685
0.8	Intermediate Similarity	NPC281880
0.8	Intermediate Similarity	NPC236237
0.8	Intermediate Similarity	NPC102253
0.8	Intermediate Similarity	NPC472973
0.7976	Intermediate Similarity	NPC141292
0.7976	Intermediate Similarity	NPC73064
0.7975	Intermediate Similarity	NPC244385
0.7975	Intermediate Similarity	NPC138621
0.7975	Intermediate Similarity	NPC300499
0.7975	Intermediate Similarity	NPC6978
0.7975	Intermediate Similarity	NPC297996
0.7975	Intermediate Similarity	NPC167037
0.7975	Intermediate Similarity	NPC285761
0.7973	Intermediate Similarity	NPC471238
0.7973	Intermediate Similarity	NPC208999
0.7955	Intermediate Similarity	NPC134067
0.7952	Intermediate Similarity	NPC79573
0.7949	Intermediate Similarity	NPC470749
0.7949	Intermediate Similarity	NPC477925
0.7949	Intermediate Similarity	NPC274079
0.7949	Intermediate Similarity	NPC106432
0.7927	Intermediate Similarity	NPC105173
0.7927	Intermediate Similarity	NPC312480
0.7922	Intermediate Similarity	NPC306727
0.7922	Intermediate Similarity	NPC100334
0.7917	Intermediate Similarity	NPC290367
0.7907	Intermediate Similarity	NPC128672
0.7907	Intermediate Similarity	NPC134321
0.7901	Intermediate Similarity	NPC14151
0.7901	Intermediate Similarity	NPC473217
0.7901	Intermediate Similarity	NPC142163
0.7901	Intermediate Similarity	NPC159148
0.7895	Intermediate Similarity	NPC242001
0.7895	Intermediate Similarity	NPC110799
0.7895	Intermediate Similarity	NPC23954
0.7895	Intermediate Similarity	NPC477792
0.7887	Intermediate Similarity	NPC475251
0.7882	Intermediate Similarity	NPC471722
0.7882	Intermediate Similarity	NPC310752
0.7882	Intermediate Similarity	NPC472802
0.7882	Intermediate Similarity	NPC292491
0.7875	Intermediate Similarity	NPC291379
0.7875	Intermediate Similarity	NPC229204
0.7875	Intermediate Similarity	NPC308038
0.7867	Intermediate Similarity	NPC9942
0.7857	Intermediate Similarity	NPC158393
0.7857	Intermediate Similarity	NPC179591
0.7857	Intermediate Similarity	NPC72133
0.7857	Intermediate Similarity	NPC470955
0.7857	Intermediate Similarity	NPC473226
0.7857	Intermediate Similarity	NPC94755
0.7857	Intermediate Similarity	NPC477579
0.7857	Intermediate Similarity	NPC472986
0.7857	Intermediate Similarity	NPC325594
0.7857	Intermediate Similarity	NPC235341
0.7857	Intermediate Similarity	NPC95594
0.7857	Intermediate Similarity	NPC472985
0.7857	Intermediate Similarity	NPC472974
0.7848	Intermediate Similarity	NPC477924
0.7848	Intermediate Similarity	NPC90979
0.7848	Intermediate Similarity	NPC472746
0.7848	Intermediate Similarity	NPC157996
0.7848	Intermediate Similarity	NPC101475
0.7848	Intermediate Similarity	NPC130136
0.7848	Intermediate Similarity	NPC471798
0.7848	Intermediate Similarity	NPC74995
0.7848	Intermediate Similarity	NPC40394
0.7848	Intermediate Similarity	NPC472805
0.7848	Intermediate Similarity	NPC214570
0.7848	Intermediate Similarity	NPC34177
0.7848	Intermediate Similarity	NPC203403
0.7841	Intermediate Similarity	NPC293086
0.7831	Intermediate Similarity	NPC40687
0.7831	Intermediate Similarity	NPC221758
0.7831	Intermediate Similarity	NPC472265
0.7831	Intermediate Similarity	NPC180834
0.7831	Intermediate Similarity	NPC59453
0.7821	Intermediate Similarity	NPC114236
0.7821	Intermediate Similarity	NPC32832
0.7816	Intermediate Similarity	NPC472975
0.7816	Intermediate Similarity	NPC472978
0.7816	Intermediate Similarity	NPC105189
0.7805	Intermediate Similarity	NPC151519
0.7805	Intermediate Similarity	NPC2524
0.7805	Intermediate Similarity	NPC212083
0.7805	Intermediate Similarity	NPC93590
0.7792	Intermediate Similarity	NPC471799
0.7792	Intermediate Similarity	NPC474140
0.7791	Intermediate Similarity	NPC25906
0.7791	Intermediate Similarity	NPC32830
0.7791	Intermediate Similarity	NPC86319
0.7791	Intermediate Similarity	NPC69627
0.7791	Intermediate Similarity	NPC290972
0.7791	Intermediate Similarity	NPC275740
0.7791	Intermediate Similarity	NPC64872
0.7791	Intermediate Similarity	NPC472971
0.7791	Intermediate Similarity	NPC474245
0.7791	Intermediate Similarity	NPC472970
0.7778	Intermediate Similarity	NPC287749
0.7778	Intermediate Similarity	NPC2482
0.7778	Intermediate Similarity	NPC254496
0.7778	Intermediate Similarity	NPC13554
0.7778	Intermediate Similarity	NPC285513
0.7778	Intermediate Similarity	NPC306095
0.7778	Intermediate Similarity	NPC96362
0.7778	Intermediate Similarity	NPC272451
0.7778	Intermediate Similarity	NPC172013
0.7765	Intermediate Similarity	NPC187376
0.7765	Intermediate Similarity	NPC475740
0.7765	Intermediate Similarity	NPC298904
0.7765	Intermediate Similarity	NPC51700
0.7765	Intermediate Similarity	NPC474684
0.7765	Intermediate Similarity	NPC18064
0.7765	Intermediate Similarity	NPC242468
0.7765	Intermediate Similarity	NPC98442
0.7765	Intermediate Similarity	NPC102683
0.7765	Intermediate Similarity	NPC159046
0.7765	Intermediate Similarity	NPC171203
0.7765	Intermediate Similarity	NPC130577
0.7765	Intermediate Similarity	NPC307426
0.7765	Intermediate Similarity	NPC233836
0.7765	Intermediate Similarity	NPC88716
0.7765	Intermediate Similarity	NPC293564
0.7765	Intermediate Similarity	NPC142415
0.7765	Intermediate Similarity	NPC68160
0.7765	Intermediate Similarity	NPC142361
0.7765	Intermediate Similarity	NPC477926
0.7763	Intermediate Similarity	NPC34834
0.7763	Intermediate Similarity	NPC145498
0.775	Intermediate Similarity	NPC275910
0.775	Intermediate Similarity	NPC230295
0.775	Intermediate Similarity	NPC253807
0.775	Intermediate Similarity	NPC470396
0.775	Intermediate Similarity	NPC196753
0.775	Intermediate Similarity	NPC22955
0.775	Intermediate Similarity	NPC474989
0.775	Intermediate Similarity	NPC158662
0.775	Intermediate Similarity	NPC98386
0.775	Intermediate Similarity	NPC99168
0.7738	Intermediate Similarity	NPC476602
0.7738	Intermediate Similarity	NPC197823
0.7738	Intermediate Similarity	NPC290731
0.7738	Intermediate Similarity	NPC280203
0.7733	Intermediate Similarity	NPC94192
0.7727	Intermediate Similarity	NPC475255
0.7727	Intermediate Similarity	NPC202728
0.7727	Intermediate Similarity	NPC118519
0.7727	Intermediate Similarity	NPC158059
0.7727	Intermediate Similarity	NPC118490

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 NPC167873 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1781
0.2-0.3	4074
0.3-0.4	2218
0.4-0.5	514
0.5-0.6	216
0.6-0.7	184
0.7-0.8	17
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
0.8	Intermediate Similarity	NPD7525	Registered
0.7857	Intermediate Similarity	NPD3618	Phase 1
0.7831	Intermediate Similarity	NPD4786	Approved
0.7805	Intermediate Similarity	NPD3667	Approved
0.7791	Intermediate Similarity	NPD5328	Approved
0.7727	Intermediate Similarity	NPD4202	Approved
0.7654	Intermediate Similarity	NPD7645	Phase 2
0.7614	Intermediate Similarity	NPD7515	Phase 2
0.7614	Intermediate Similarity	NPD6079	Approved
0.7468	Intermediate Similarity	NPD6926	Approved
0.7468	Intermediate Similarity	NPD6924	Approved
0.7412	Intermediate Similarity	NPD3665	Phase 1
0.7412	Intermediate Similarity	NPD3133	Approved
0.7412	Intermediate Similarity	NPD3666	Approved
0.7391	Intermediate Similarity	NPD4755	Approved
0.7375	Intermediate Similarity	NPD6942	Approved
0.7375	Intermediate Similarity	NPD7339	Approved
0.7349	Intermediate Similarity	NPD7509	Discontinued
0.7284	Intermediate Similarity	NPD6933	Approved
0.7284	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7748	Approved
0.7241	Intermediate Similarity	NPD5279	Phase 3
0.7234	Intermediate Similarity	NPD4696	Approved
0.7234	Intermediate Similarity	NPD5285	Approved
0.7234	Intermediate Similarity	NPD5286	Approved
0.7234	Intermediate Similarity	NPD4700	Approved
0.7204	Intermediate Similarity	NPD7902	Approved
0.716	Intermediate Similarity	NPD8264	Approved
0.7158	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7126	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5222	Approved
0.7097	Intermediate Similarity	NPD5221	Approved
0.7097	Intermediate Similarity	NPD4697	Phase 3
0.7097	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5211	Phase 2
0.7083	Intermediate Similarity	NPD5226	Approved
0.7083	Intermediate Similarity	NPD5224	Approved
0.7083	Intermediate Similarity	NPD4633	Approved
0.7083	Intermediate Similarity	NPD5225	Approved
0.7041	Intermediate Similarity	NPD6675	Approved
0.7041	Intermediate Similarity	NPD6402	Approved
0.7041	Intermediate Similarity	NPD7128	Approved
0.7041	Intermediate Similarity	NPD5739	Approved
0.7021	Intermediate Similarity	NPD5173	Approved
0.7011	Intermediate Similarity	NPD3668	Phase 3
0.701	Intermediate Similarity	NPD5174	Approved
0.701	Intermediate Similarity	NPD5175	Approved
0.701	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD4753	Phase 2
0.7	Intermediate Similarity	NPD7152	Approved
0.7	Intermediate Similarity	NPD7150	Approved
0.7	Intermediate Similarity	NPD7151	Approved
0.6977	Remote Similarity	NPD4223	Phase 3
0.6977	Remote Similarity	NPD4221	Approved
0.6962	Remote Similarity	NPD6923	Approved
0.6962	Remote Similarity	NPD6922	Approved
0.6947	Remote Similarity	NPD7638	Approved
0.6941	Remote Similarity	NPD6931	Approved
0.6941	Remote Similarity	NPD6930	Phase 2
0.6941	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4695	Discontinued
0.6939	Remote Similarity	NPD5141	Approved
0.6933	Remote Similarity	NPD368	Approved
0.6932	Remote Similarity	NPD5329	Approved
0.69	Remote Similarity	NPD7320	Approved
0.69	Remote Similarity	NPD6881	Approved
0.69	Remote Similarity	NPD6899	Approved
0.6897	Remote Similarity	NPD4788	Approved
0.6882	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7900	Approved
0.6875	Remote Similarity	NPD7144	Approved
0.6875	Remote Similarity	NPD7143	Approved
0.6875	Remote Similarity	NPD7640	Approved
0.6875	Remote Similarity	NPD7639	Approved
0.6869	Remote Similarity	NPD4767	Approved
0.6869	Remote Similarity	NPD4768	Approved
0.6854	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6373	Approved
0.6832	Remote Similarity	NPD6372	Approved
0.6824	Remote Similarity	NPD4195	Approved
0.6824	Remote Similarity	NPD6929	Approved
0.6818	Remote Similarity	NPD4197	Approved
0.6818	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5697	Approved
0.68	Remote Similarity	NPD5701	Approved
0.6795	Remote Similarity	NPD7331	Phase 2
0.679	Remote Similarity	NPD4243	Approved
0.6786	Remote Similarity	NPD6932	Approved
0.6771	Remote Similarity	NPD4225	Approved
0.6765	Remote Similarity	NPD7102	Approved
0.6765	Remote Similarity	NPD7290	Approved
0.6765	Remote Similarity	NPD6883	Approved
0.6744	Remote Similarity	NPD4748	Discontinued
0.6742	Remote Similarity	NPD1696	Phase 3
0.6733	Remote Similarity	NPD5128	Approved
0.6733	Remote Similarity	NPD4730	Approved
0.6733	Remote Similarity	NPD6011	Approved
0.6733	Remote Similarity	NPD4729	Approved
0.6706	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6695	Phase 3
0.6699	Remote Similarity	NPD6650	Approved
0.6699	Remote Similarity	NPD6617	Approved
0.6699	Remote Similarity	NPD6869	Approved
0.6699	Remote Similarity	NPD6649	Approved
0.6699	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6847	Approved
0.6699	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6635	Remote Similarity	NPD6882	Approved
0.6635	Remote Similarity	NPD8297	Approved
0.6632	Remote Similarity	NPD4629	Approved
0.6632	Remote Similarity	NPD5210	Approved
0.6628	Remote Similarity	NPD6683	Phase 2
0.6627	Remote Similarity	NPD4784	Approved
0.6627	Remote Similarity	NPD4785	Approved
0.6602	Remote Similarity	NPD5251	Approved
0.6602	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5249	Phase 3
0.6602	Remote Similarity	NPD5247	Approved
0.6602	Remote Similarity	NPD5135	Approved
0.6602	Remote Similarity	NPD5248	Approved
0.6602	Remote Similarity	NPD5169	Approved
0.6602	Remote Similarity	NPD5250	Approved
0.6602	Remote Similarity	NPD4634	Approved
0.6598	Remote Similarity	NPD5290	Discontinued
0.6593	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3573	Approved
0.6588	Remote Similarity	NPD5776	Phase 2
0.6588	Remote Similarity	NPD6925	Approved
0.6585	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6893	Approved
0.6552	Remote Similarity	NPD7332	Phase 2
0.6552	Remote Similarity	NPD4821	Approved
0.6552	Remote Similarity	NPD4822	Approved
0.6552	Remote Similarity	NPD4819	Approved
0.6552	Remote Similarity	NPD4820	Approved
0.6552	Remote Similarity	NPD5368	Approved
0.6552	Remote Similarity	NPD7514	Phase 3
0.6543	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5127	Approved
0.6538	Remote Similarity	NPD5215	Approved
0.6538	Remote Similarity	NPD5217	Approved
0.6538	Remote Similarity	NPD5216	Approved
0.6522	Remote Similarity	NPD6903	Approved
0.6522	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3617	Approved
0.6512	Remote Similarity	NPD7145	Approved
0.6489	Remote Similarity	NPD5281	Approved
0.6489	Remote Similarity	NPD5284	Approved
0.6477	Remote Similarity	NPD6898	Phase 1
0.6477	Remote Similarity	NPD4139	Approved
0.6477	Remote Similarity	NPD5369	Approved
0.6477	Remote Similarity	NPD4692	Approved
0.6465	Remote Similarity	NPD5344	Discontinued
0.6458	Remote Similarity	NPD5695	Phase 3
0.6452	Remote Similarity	NPD6101	Approved
0.6452	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4632	Approved
0.6413	Remote Similarity	NPD7750	Discontinued
0.6413	Remote Similarity	NPD7524	Approved
0.6408	Remote Similarity	NPD5168	Approved
0.6404	Remote Similarity	NPD6435	Approved
0.6395	Remote Similarity	NPD6116	Phase 1
0.6383	Remote Similarity	NPD4096	Approved
0.6355	Remote Similarity	NPD5167	Approved
0.6354	Remote Similarity	NPD5282	Discontinued
0.6353	Remote Similarity	NPD3703	Phase 2
0.6353	Remote Similarity	NPD5275	Approved
0.6353	Remote Similarity	NPD4190	Phase 3
0.6344	Remote Similarity	NPD6672	Approved
0.6344	Remote Similarity	NPD5737	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