NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.21
Volume:	297.783
LogP:	4.624
LogD:	4.5
LogS:	-4.118
# Rotatable Bonds:	4
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	4.367
Fsp3:	0.824
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.481
MDCK Permeability:	2.2197153157321736e-05
Pgp-inhibitor:	0.358
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.926
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	91.69056701660156%
Volume Distribution (VD):	1.461
Pgp-substrate:	5.5268707275390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.38
CYP2C19-inhibitor:	0.692
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.472
CYP2C9-substrate:	0.086
CYP2D6-inhibitor:	0.099
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.437

ADMET: Excretion

Clearance (CL):	4.628
Half-life (T1/2):	0.599

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.799
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.14
Carcinogencity:	0.055
Eye Corrosion:	0.635
Eye Irritation:	0.898
Respiratory Toxicity:	0.859

Download Data

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

Natural Product: NPC469723

Natural Product ID:	NPC469723
*Common Name:**	Guai-2-En-10Alpha-Methyl Methanoate
IUPAC Name:	[(1S,3aS,4R,8S,8aR)-8-ethyl-1,4-dimethyl-3a,5,6,7,8,8a-hexahydro-1H-azulen-4-yl]methyl acetate
Synonyms:
Standard InCHIKey:	NCEKMDWUHDFBPC-SRQBIAJPSA-N
Standard InCHI:	InChI=1S/C17H28O2/c1-5-14-7-6-10-17(4,11-19-13(3)18)15-9-8-12(2)16(14)15/h8-9,12,14-16H,5-7,10-11H2,1-4H3/t12-,14-,15-,16-,17-/m0/s1
SMILES:	CCC1CCCC(C2C1C(C=C2)C)(C)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163439
PubChem CID:	46703007
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0001238] Carboxylic acid esters

*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
NPO32882	ulva fasciata delile	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20163893]

☑ 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
MIC	3
Others	9

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	IZ	=	15.29	mm	PMID[554025]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	IZ	=	15.85	mm	PMID[554025]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	IZ	=	16.65	mm	PMID[554025]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	=	25.0	ug.mL-1	PMID[554025]
NPT1726	Organism	Vibrio harveyi	Vibrio harveyi	IZ	=	11.73	mm	PMID[554025]
NPT1726	Organism	Vibrio harveyi	Vibrio harveyi	IZ	=	12.34	mm	PMID[554025]
NPT1726	Organism	Vibrio harveyi	Vibrio harveyi	IZ	=	12.59	mm	PMID[554025]
NPT1726	Organism	Vibrio harveyi	Vibrio harveyi	MIC	=	30.0	ug.mL-1	PMID[554025]
NPT5711	Organism	Vibrio vulnificus	Vibrio vulnificus	IZ	=	14.1	mm	PMID[554025]
NPT5711	Organism	Vibrio vulnificus	Vibrio vulnificus	IZ	=	14.93	mm	PMID[554025]
NPT5711	Organism	Vibrio vulnificus	Vibrio vulnificus	IZ	=	15.08	mm	PMID[554025]
NPT5711	Organism	Vibrio vulnificus	Vibrio vulnificus	MIC	=	25.0	ug.mL-1	PMID[554025]

☑ 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 NPC469723 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	181
0.1-0.2	2145
0.2-0.3	13896
0.3-0.4	12682
0.4-0.5	8205
0.5-0.6	4948
0.6-0.7	610
0.7-0.8	29
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8088	Intermediate Similarity	NPC22301
0.7937	Intermediate Similarity	NPC10017
0.7778	Intermediate Similarity	NPC113639
0.7746	Intermediate Similarity	NPC470237
0.7703	Intermediate Similarity	NPC474005
0.7671	Intermediate Similarity	NPC476317
0.7627	Intermediate Similarity	NPC207815
0.75	Intermediate Similarity	NPC289388
0.75	Intermediate Similarity	NPC142103
0.7463	Intermediate Similarity	NPC211291
0.7463	Intermediate Similarity	NPC133368
0.7432	Intermediate Similarity	NPC41017
0.7377	Intermediate Similarity	NPC244452
0.7375	Intermediate Similarity	NPC70422
0.7375	Intermediate Similarity	NPC104961
0.7375	Intermediate Similarity	NPC70555
0.7368	Intermediate Similarity	NPC170561
0.7333	Intermediate Similarity	NPC186109
0.7324	Intermediate Similarity	NPC296522
0.7324	Intermediate Similarity	NPC144511
0.7324	Intermediate Similarity	NPC199557
0.7286	Intermediate Similarity	NPC472266
0.7258	Intermediate Similarity	NPC170167
0.725	Intermediate Similarity	NPC471795
0.725	Intermediate Similarity	NPC33570
0.725	Intermediate Similarity	NPC21471
0.725	Intermediate Similarity	NPC161957
0.7237	Intermediate Similarity	NPC184737
0.7222	Intermediate Similarity	NPC472955
0.7179	Intermediate Similarity	NPC472471
0.7162	Intermediate Similarity	NPC166797
0.7162	Intermediate Similarity	NPC472966
0.7143	Intermediate Similarity	NPC100906
0.7143	Intermediate Similarity	NPC44083
0.7143	Intermediate Similarity	NPC153987
0.7125	Intermediate Similarity	NPC222634
0.7105	Intermediate Similarity	NPC195785
0.7105	Intermediate Similarity	NPC283619
0.7105	Intermediate Similarity	NPC15975
0.7105	Intermediate Similarity	NPC476439
0.7101	Intermediate Similarity	NPC34883
0.7101	Intermediate Similarity	NPC329698
0.7101	Intermediate Similarity	NPC140233
0.7101	Intermediate Similarity	NPC287744
0.7083	Intermediate Similarity	NPC329656
0.7083	Intermediate Similarity	NPC265574
0.7077	Intermediate Similarity	NPC252860
0.7077	Intermediate Similarity	NPC96663
0.7077	Intermediate Similarity	NPC141699
0.7077	Intermediate Similarity	NPC274396
0.7073	Intermediate Similarity	NPC471796
0.7067	Intermediate Similarity	NPC475771
0.7067	Intermediate Similarity	NPC469678
0.7067	Intermediate Similarity	NPC469669
0.7059	Intermediate Similarity	NPC125312
0.7059	Intermediate Similarity	NPC174560
0.7051	Intermediate Similarity	NPC276356
0.7051	Intermediate Similarity	NPC473685
0.7051	Intermediate Similarity	NPC233332
0.7051	Intermediate Similarity	NPC472470
0.7027	Intermediate Similarity	NPC92909
0.7027	Intermediate Similarity	NPC472956
0.7027	Intermediate Similarity	NPC107783
0.7024	Intermediate Similarity	NPC253144
0.7013	Intermediate Similarity	NPC4827
0.7013	Intermediate Similarity	NPC35574
0.7013	Intermediate Similarity	NPC253749
0.7	Intermediate Similarity	NPC215294
0.7	Intermediate Similarity	NPC39588
0.6986	Remote Similarity	NPC469660
0.6974	Remote Similarity	NPC266159
0.6974	Remote Similarity	NPC472967
0.697	Remote Similarity	NPC165808
0.6962	Remote Similarity	NPC142163
0.6962	Remote Similarity	NPC255580
0.6962	Remote Similarity	NPC39411
0.6944	Remote Similarity	NPC476614
0.6941	Remote Similarity	NPC123177
0.6941	Remote Similarity	NPC284185
0.6941	Remote Similarity	NPC150978
0.6941	Remote Similarity	NPC70595
0.6941	Remote Similarity	NPC74103
0.6933	Remote Similarity	NPC167049
0.6933	Remote Similarity	NPC469691
0.6933	Remote Similarity	NPC306928
0.6933	Remote Similarity	NPC71152
0.6923	Remote Similarity	NPC128061
0.6923	Remote Similarity	NPC200845
0.6923	Remote Similarity	NPC10316
0.6923	Remote Similarity	NPC28779
0.6923	Remote Similarity	NPC223677
0.6923	Remote Similarity	NPC469690
0.6923	Remote Similarity	NPC477984
0.6923	Remote Similarity	NPC327674
0.6923	Remote Similarity	NPC325869
0.6923	Remote Similarity	NPC242767
0.6914	Remote Similarity	NPC139566
0.6905	Remote Similarity	NPC117405
0.6905	Remote Similarity	NPC52198
0.6901	Remote Similarity	NPC304665
0.6901	Remote Similarity	NPC126899
0.6901	Remote Similarity	NPC272125
0.6901	Remote Similarity	NPC154728
0.6883	Remote Similarity	NPC189206
0.6883	Remote Similarity	NPC476794
0.6883	Remote Similarity	NPC470240
0.6875	Remote Similarity	NPC142683
0.6875	Remote Similarity	NPC200513
0.6875	Remote Similarity	NPC71761
0.6867	Remote Similarity	NPC45957
0.6867	Remote Similarity	NPC471657
0.6866	Remote Similarity	NPC240206
0.6857	Remote Similarity	NPC226066
0.6849	Remote Similarity	NPC232812
0.6849	Remote Similarity	NPC101622
0.6849	Remote Similarity	NPC269841
0.6849	Remote Similarity	NPC5714
0.6842	Remote Similarity	NPC324762
0.6842	Remote Similarity	NPC475861
0.6842	Remote Similarity	NPC228978
0.6842	Remote Similarity	NPC93213
0.6842	Remote Similarity	NPC201027
0.6835	Remote Similarity	NPC469802
0.6835	Remote Similarity	NPC69271
0.6835	Remote Similarity	NPC268827
0.6835	Remote Similarity	NPC269791
0.6835	Remote Similarity	NPC195424
0.6835	Remote Similarity	NPC74673
0.6835	Remote Similarity	NPC304795
0.6829	Remote Similarity	NPC476602
0.6806	Remote Similarity	NPC469868
0.6806	Remote Similarity	NPC472253
0.6806	Remote Similarity	NPC472255
0.68	Remote Similarity	NPC12680
0.68	Remote Similarity	NPC135703
0.6795	Remote Similarity	NPC471220
0.679	Remote Similarity	NPC23748
0.679	Remote Similarity	NPC12283
0.679	Remote Similarity	NPC474193
0.679	Remote Similarity	NPC30502
0.679	Remote Similarity	NPC311070
0.679	Remote Similarity	NPC477124
0.679	Remote Similarity	NPC475622
0.679	Remote Similarity	NPC472473
0.679	Remote Similarity	NPC49208
0.679	Remote Similarity	NPC193198
0.679	Remote Similarity	NPC472440
0.679	Remote Similarity	NPC108045
0.679	Remote Similarity	NPC139206
0.6782	Remote Similarity	NPC289004
0.6774	Remote Similarity	NPC234597
0.6761	Remote Similarity	NPC474768
0.6757	Remote Similarity	NPC37929
0.6757	Remote Similarity	NPC4299
0.6757	Remote Similarity	NPC64234
0.6757	Remote Similarity	NPC475310
0.6753	Remote Similarity	NPC471726
0.6753	Remote Similarity	NPC226242
0.6753	Remote Similarity	NPC474527
0.6753	Remote Similarity	NPC110461
0.6753	Remote Similarity	NPC12740
0.6753	Remote Similarity	NPC899
0.6753	Remote Similarity	NPC472959
0.675	Remote Similarity	NPC108476
0.675	Remote Similarity	NPC195334
0.675	Remote Similarity	NPC290495
0.675	Remote Similarity	NPC327002
0.675	Remote Similarity	NPC170303
0.675	Remote Similarity	NPC475665
0.675	Remote Similarity	NPC229584
0.675	Remote Similarity	NPC474955
0.675	Remote Similarity	NPC14203
0.675	Remote Similarity	NPC476101
0.6747	Remote Similarity	NPC264127
0.6719	Remote Similarity	NPC216407
0.6714	Remote Similarity	NPC279200
0.6712	Remote Similarity	NPC470040
0.6712	Remote Similarity	NPC276290
0.6712	Remote Similarity	NPC476945
0.6711	Remote Similarity	NPC283908
0.6711	Remote Similarity	NPC237591
0.6711	Remote Similarity	NPC103958
0.6711	Remote Similarity	NPC330016
0.6711	Remote Similarity	NPC183503
0.6711	Remote Similarity	NPC3753
0.6711	Remote Similarity	NPC104644
0.6711	Remote Similarity	NPC161923
0.6711	Remote Similarity	NPC475517
0.6711	Remote Similarity	NPC474524
0.6709	Remote Similarity	NPC182550
0.6709	Remote Similarity	NPC469620
0.6707	Remote Similarity	NPC318515
0.6707	Remote Similarity	NPC100391
0.6707	Remote Similarity	NPC96055
0.6707	Remote Similarity	NPC475100
0.6667	Remote Similarity	NPC478144
0.6667	Remote Similarity	NPC129665
0.6667	Remote Similarity	NPC473825
0.6667	Remote Similarity	NPC286786
0.6667	Remote Similarity	NPC472300

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 NPC469723 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	2728
0.2-0.3	4167
0.3-0.4	1483
0.4-0.5	416
0.5-0.6	170
0.6-0.7	12
0.7-0.8	0
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
0.6875	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8039	Approved
0.6761	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5209	Approved
0.6582	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7521	Approved
0.6548	Remote Similarity	NPD7334	Approved
0.6548	Remote Similarity	NPD7146	Approved
0.6548	Remote Similarity	NPD6684	Approved
0.6548	Remote Similarity	NPD5330	Approved
0.6548	Remote Similarity	NPD6409	Approved
0.6517	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6435	Approved
0.6429	Remote Similarity	NPD1694	Approved
0.642	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6903	Approved
0.6395	Remote Similarity	NPD5737	Approved
0.6395	Remote Similarity	NPD6672	Approved
0.6386	Remote Similarity	NPD7154	Phase 3
0.6386	Remote Similarity	NPD5362	Discontinued
0.6349	Remote Similarity	NPD5343	Approved
0.6341	Remote Similarity	NPD5369	Approved
0.6322	Remote Similarity	NPD6051	Approved
0.6322	Remote Similarity	NPD1695	Approved
0.6308	Remote Similarity	NPD29	Approved
0.6308	Remote Similarity	NPD28	Approved
0.622	Remote Similarity	NPD4822	Approved
0.622	Remote Similarity	NPD4820	Approved
0.622	Remote Similarity	NPD5368	Approved
0.622	Remote Similarity	NPD4821	Approved
0.622	Remote Similarity	NPD4819	Approved
0.618	Remote Similarity	NPD6411	Approved
0.6173	Remote Similarity	NPD4271	Approved
0.6173	Remote Similarity	NPD4268	Approved
0.6163	Remote Similarity	NPD6098	Approved
0.6145	Remote Similarity	NPD857	Phase 3
0.6129	Remote Similarity	NPD6096	Approved
0.6129	Remote Similarity	NPD6097	Approved
0.6119	Remote Similarity	NPD3172	Approved
0.6111	Remote Similarity	NPD4194	Approved
0.6111	Remote Similarity	NPD4192	Approved
0.6111	Remote Similarity	NPD4193	Approved
0.6111	Remote Similarity	NPD4191	Approved
0.6111	Remote Similarity	NPD6399	Phase 3
0.6092	Remote Similarity	NPD3573	Approved
0.6076	Remote Similarity	NPD6926	Approved
0.6076	Remote Similarity	NPD6924	Approved
0.6071	Remote Similarity	NPD4270	Approved
0.6071	Remote Similarity	NPD4269	Approved
0.6067	Remote Similarity	NPD5207	Approved
0.6067	Remote Similarity	NPD5785	Approved
0.6047	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD3174	Discontinued
0.6029	Remote Similarity	NPD4266	Approved
0.6029	Remote Similarity	NPD3194	Approved
0.6029	Remote Similarity	NPD3196	Approved
0.6029	Remote Similarity	NPD3195	Phase 2
0.6023	Remote Similarity	NPD5208	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD5332	Approved
0.5978	Remote Similarity	NPD5695	Phase 3
0.5977	Remote Similarity	NPD4249	Approved
0.5977	Remote Similarity	NPD5786	Approved
0.5972	Remote Similarity	NPD1145	Discontinued
0.5955	Remote Similarity	NPD6080	Approved
0.5955	Remote Similarity	NPD6904	Approved
0.5955	Remote Similarity	NPD6673	Approved
0.5955	Remote Similarity	NPD6101	Approved
0.5955	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4790	Discontinued
0.5926	Remote Similarity	NPD6933	Approved
0.5926	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4251	Approved
0.5909	Remote Similarity	NPD4250	Approved
0.5904	Remote Similarity	NPD4195	Approved
0.5897	Remote Similarity	NPD7144	Approved
0.5897	Remote Similarity	NPD7143	Approved
0.5889	Remote Similarity	NPD5692	Phase 3
0.5882	Remote Similarity	NPD3667	Approved
0.587	Remote Similarity	NPD5282	Discontinued
0.587	Remote Similarity	NPD7900	Approved
0.587	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7748	Approved
0.5862	Remote Similarity	NPD5363	Approved
0.5851	Remote Similarity	NPD6084	Phase 2
0.5851	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD4252	Approved
0.5833	Remote Similarity	NPD7509	Discontinued
0.5824	Remote Similarity	NPD6050	Approved
0.5824	Remote Similarity	NPD5693	Phase 1
0.5823	Remote Similarity	NPD7150	Approved
0.5823	Remote Similarity	NPD7152	Approved
0.5823	Remote Similarity	NPD7151	Approved
0.5821	Remote Similarity	NPD6927	Phase 3
0.5814	Remote Similarity	NPD6695	Phase 3
0.5806	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6942	Approved
0.5802	Remote Similarity	NPD7339	Approved
0.5789	Remote Similarity	NPD4225	Approved
0.5789	Remote Similarity	NPD7638	Approved
0.5789	Remote Similarity	NPD5696	Approved
0.5783	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6923	Approved
0.5769	Remote Similarity	NPD6922	Approved
0.5761	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD5778	Approved
0.5761	Remote Similarity	NPD5779	Approved
0.5758	Remote Similarity	NPD3173	Approved
0.5747	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD3665	Phase 1
0.5747	Remote Similarity	NPD3666	Approved
0.5747	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD3668	Phase 3
0.5747	Remote Similarity	NPD4786	Approved
0.5747	Remote Similarity	NPD3133	Approved
0.5745	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD3197	Phase 1
0.5729	Remote Similarity	NPD7639	Approved
0.5729	Remote Similarity	NPD7640	Approved
0.5714	Remote Similarity	NPD342	Phase 1
0.5714	Remote Similarity	NPD3673	Approved
0.5714	Remote Similarity	NPD6929	Approved
0.5714	Remote Similarity	NPD7645	Phase 2
0.5714	Remote Similarity	NPD7838	Discovery
0.5714	Remote Similarity	NPD3672	Approved
0.5699	Remote Similarity	NPD6001	Approved
0.5699	Remote Similarity	NPD5707	Approved
0.5686	Remote Similarity	NPD6371	Approved
0.5684	Remote Similarity	NPD7902	Approved
0.5682	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD4785	Approved
0.5679	Remote Similarity	NPD4784	Approved
0.5663	Remote Similarity	NPD6932	Approved
0.5652	Remote Similarity	NPD7515	Phase 2
0.5652	Remote Similarity	NPD5281	Approved
0.5652	Remote Similarity	NPD5284	Approved
0.5647	Remote Similarity	NPD6931	Approved
0.5647	Remote Similarity	NPD6930	Phase 2
0.5647	Remote Similarity	NPD7525	Registered
0.5647	Remote Similarity	NPD7332	Phase 2
0.5634	Remote Similarity	NPD4219	Approved
0.5625	Remote Similarity	NPD4243	Approved
0.5618	Remote Similarity	NPD4519	Discontinued
0.5618	Remote Similarity	NPD4623	Approved
0.5618	Remote Similarity	NPD5279	Phase 3
0.5618	Remote Similarity	NPD3618	Phase 1
0.561	Remote Similarity	NPD8264	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