NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	3.876
LogD:	3.011
LogS:	-3.898
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	4.481
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.423
MDCK Permeability:	1.7625963664613664e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.069
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.913
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.337
Plasma Protein Binding (PPB):	87.91638946533203%
Volume Distribution (VD):	1.176
Pgp-substrate:	11.422947883605957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.233
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	8.532
Half-life (T1/2):	0.34

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.807
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.471
Carcinogencity:	0.08
Eye Corrosion:	0.085
Eye Irritation:	0.453
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC41886

Natural Product ID:	NPC41886
*Common Name:**	(1R,2S,3As,8Ar)-3A,6-Dimethyl-1-Propan-2-Yl-2,3,4,7,8,8A-Hexahydroazulene-1,2-Diol
IUPAC Name:	(1R,2S,3aS,8aR)-3a,6-dimethyl-1-propan-2-yl-2,3,4,7,8,8a-hexahydroazulene-1,2-diol
Synonyms:	CAF-603
Standard InCHIKey:	WBVHJGBFCZGJRZ-CBBWQLFWSA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-10(2)15(17)12-6-5-11(3)7-8-14(12,4)9-13(15)16/h7,10,12-13,16-17H,5-6,8-9H2,1-4H3/t12-,13+,14+,15-/m1/s1
SMILES:	CC(C)[C@]1([C@@H]2CCC(=CC[C@@]2(C)C[C@@H]1O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL163989
PubChem CID:	10376935
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
NPO31340	Gliocladium virens	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[2292685]

☑ 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	29
Others	1

Activity Type	# Activity
Organism	29
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	200.0	nM	PMID[519955]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	12.5	ug.mL-1	PMID[519956]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1.56	ug.mL-1	PMID[519956]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.8	ug.mL-1	PMID[519956]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.4	ug.mL-1	PMID[519956]
NPT2578	Organism	Pichia guilliermondii	Meyerozyma guilliermondii	MIC	>	100.0	ug.mL-1	PMID[519956]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	25.0	ug.mL-1	PMID[519956]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	>	100.0	ug.mL-1	PMID[519956]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	=	50.0	ug.mL-1	PMID[519956]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	6.25	ug.mL-1	PMID[519956]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	3.13	ug.mL-1	PMID[519956]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	100.0	ug.mL-1	PMID[519956]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	3.13	ug.mL-1	PMID[519956]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	1.56	ug.mL-1	PMID[519956]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	50.0	ug.mL-1	PMID[519956]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	25.0	ug.mL-1	PMID[519956]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	12.5	ug.mL-1	PMID[519956]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	100.0	ug.mL-1	PMID[519956]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	12.5	ug.mL-1	PMID[519956]
NPT923	Organism	Rhizopus oryzae	Rhizopus oryzae	MIC	>	100.0	ug.mL-1	PMID[519956]

☑ 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 NPC41886 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	175
0.1-0.2	2092
0.2-0.3	12497
0.3-0.4	13137
0.4-0.5	8127
0.5-0.6	5416
0.6-0.7	1141
0.7-0.8	91
0.8-0.85	18
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC126969
0.8986	High Similarity	NPC471781
0.8286	Intermediate Similarity	NPC136813
0.8261	Intermediate Similarity	NPC205618
0.8261	Intermediate Similarity	NPC469326
0.8261	Intermediate Similarity	NPC238352
0.8261	Intermediate Similarity	NPC261782
0.8261	Intermediate Similarity	NPC477009
0.8169	Intermediate Similarity	NPC167527
0.8101	Intermediate Similarity	NPC471340
0.8088	Intermediate Similarity	NPC63111
0.806	Intermediate Similarity	NPC469321
0.8056	Intermediate Similarity	NPC144647
0.7975	Intermediate Similarity	NPC472465
0.7941	Intermediate Similarity	NPC252809
0.7917	Intermediate Similarity	NPC224532
0.7867	Intermediate Similarity	NPC471659
0.7794	Intermediate Similarity	NPC475968
0.7778	Intermediate Similarity	NPC477791
0.7761	Intermediate Similarity	NPC278550
0.7746	Intermediate Similarity	NPC471200
0.7733	Intermediate Similarity	NPC234527
0.7733	Intermediate Similarity	NPC14352
0.7714	Intermediate Similarity	NPC474480
0.7703	Intermediate Similarity	NPC254845
0.7703	Intermediate Similarity	NPC470041
0.7662	Intermediate Similarity	NPC315261
0.7662	Intermediate Similarity	NPC310643
0.7662	Intermediate Similarity	NPC471658
0.7647	Intermediate Similarity	NPC470832
0.7632	Intermediate Similarity	NPC309178
0.7625	Intermediate Similarity	NPC471661
0.7606	Intermediate Similarity	NPC309300
0.76	Intermediate Similarity	NPC471662
0.7571	Intermediate Similarity	NPC274704
0.7536	Intermediate Similarity	NPC310228
0.7536	Intermediate Similarity	NPC5698
0.7536	Intermediate Similarity	NPC52431
0.7534	Intermediate Similarity	NPC472255
0.7534	Intermediate Similarity	NPC472253
0.7532	Intermediate Similarity	NPC60818
0.7532	Intermediate Similarity	NPC313185
0.7532	Intermediate Similarity	NPC23231
0.75	Intermediate Similarity	NPC300442
0.75	Intermediate Similarity	NPC30675
0.75	Intermediate Similarity	NPC26117
0.75	Intermediate Similarity	NPC61503
0.7465	Intermediate Similarity	NPC211291
0.7465	Intermediate Similarity	NPC133368
0.7465	Intermediate Similarity	NPC279200
0.7439	Intermediate Similarity	NPC320548
0.7429	Intermediate Similarity	NPC323153
0.7403	Intermediate Similarity	NPC329090
0.7403	Intermediate Similarity	NPC27395
0.7397	Intermediate Similarity	NPC272125
0.7397	Intermediate Similarity	NPC311736
0.7391	Intermediate Similarity	NPC475830
0.7386	Intermediate Similarity	NPC473258
0.7375	Intermediate Similarity	NPC328714
0.7368	Intermediate Similarity	NPC471660
0.7361	Intermediate Similarity	NPC219940
0.7342	Intermediate Similarity	NPC471454
0.7317	Intermediate Similarity	NPC1272
0.7317	Intermediate Similarity	NPC133844
0.7317	Intermediate Similarity	NPC470614
0.7308	Intermediate Similarity	NPC328104
0.7308	Intermediate Similarity	NPC77501
0.7308	Intermediate Similarity	NPC319090
0.7297	Intermediate Similarity	NPC163290
0.7286	Intermediate Similarity	NPC99480
0.7286	Intermediate Similarity	NPC184049
0.7284	Intermediate Similarity	NPC13554
0.7284	Intermediate Similarity	NPC324772
0.7273	Intermediate Similarity	NPC98193
0.7273	Intermediate Similarity	NPC474140
0.7273	Intermediate Similarity	NPC310608
0.7273	Intermediate Similarity	NPC476709
0.726	Intermediate Similarity	NPC165069
0.726	Intermediate Similarity	NPC187619
0.726	Intermediate Similarity	NPC19569
0.725	Intermediate Similarity	NPC477514
0.725	Intermediate Similarity	NPC477522
0.725	Intermediate Similarity	NPC87604
0.7241	Intermediate Similarity	NPC472466
0.7241	Intermediate Similarity	NPC107189
0.7237	Intermediate Similarity	NPC133873
0.7229	Intermediate Similarity	NPC110778
0.7229	Intermediate Similarity	NPC477667
0.7229	Intermediate Similarity	NPC260852
0.7229	Intermediate Similarity	NPC477818
0.7222	Intermediate Similarity	NPC473508
0.7215	Intermediate Similarity	NPC215481
0.7215	Intermediate Similarity	NPC96319
0.7215	Intermediate Similarity	NPC476317
0.7195	Intermediate Similarity	NPC320525
0.7183	Intermediate Similarity	NPC135648
0.7176	Intermediate Similarity	NPC94462
0.7176	Intermediate Similarity	NPC152808
0.7176	Intermediate Similarity	NPC293287
0.7176	Intermediate Similarity	NPC201273
0.7162	Intermediate Similarity	NPC162309
0.7162	Intermediate Similarity	NPC469328
0.7162	Intermediate Similarity	NPC267027
0.716	Intermediate Similarity	NPC1319
0.716	Intermediate Similarity	NPC261125
0.716	Intermediate Similarity	NPC181195
0.7159	Intermediate Similarity	NPC94127
0.7159	Intermediate Similarity	NPC472468
0.7143	Intermediate Similarity	NPC116613
0.7143	Intermediate Similarity	NPC124172
0.7143	Intermediate Similarity	NPC242016
0.7143	Intermediate Similarity	NPC10017
0.7143	Intermediate Similarity	NPC209802
0.7143	Intermediate Similarity	NPC469343
0.7126	Intermediate Similarity	NPC105495
0.7126	Intermediate Similarity	NPC299527
0.7126	Intermediate Similarity	NPC109744
0.7125	Intermediate Similarity	NPC318495
0.7125	Intermediate Similarity	NPC186109
0.7125	Intermediate Similarity	NPC155986
0.7125	Intermediate Similarity	NPC198968
0.7125	Intermediate Similarity	NPC276769
0.7125	Intermediate Similarity	NPC31037
0.7123	Intermediate Similarity	NPC287744
0.7123	Intermediate Similarity	NPC140233
0.7108	Intermediate Similarity	NPC30166
0.7105	Intermediate Similarity	NPC217570
0.7105	Intermediate Similarity	NPC90115
0.7105	Intermediate Similarity	NPC167272
0.7105	Intermediate Similarity	NPC473893
0.7105	Intermediate Similarity	NPC16964
0.7105	Intermediate Similarity	NPC22301
0.7105	Intermediate Similarity	NPC269877
0.7093	Intermediate Similarity	NPC186145
0.7093	Intermediate Similarity	NPC474657
0.7089	Intermediate Similarity	NPC113639
0.7083	Intermediate Similarity	NPC475251
0.7083	Intermediate Similarity	NPC210346
0.7073	Intermediate Similarity	NPC471656
0.7073	Intermediate Similarity	NPC236112
0.7067	Intermediate Similarity	NPC82337
0.7051	Intermediate Similarity	NPC300940
0.7051	Intermediate Similarity	NPC469320
0.7045	Intermediate Similarity	NPC475751
0.7045	Intermediate Similarity	NPC473956
0.7045	Intermediate Similarity	NPC197107
0.7037	Intermediate Similarity	NPC285761
0.7037	Intermediate Similarity	NPC469324
0.7037	Intermediate Similarity	NPC475980
0.7024	Intermediate Similarity	NPC474634
0.7024	Intermediate Similarity	NPC207013
0.7024	Intermediate Similarity	NPC193870
0.7024	Intermediate Similarity	NPC141941
0.7013	Intermediate Similarity	NPC49422
0.7013	Intermediate Similarity	NPC9161
0.7011	Intermediate Similarity	NPC475664
0.7011	Intermediate Similarity	NPC133588
0.7011	Intermediate Similarity	NPC22376
0.7011	Intermediate Similarity	NPC474668
0.7	Intermediate Similarity	NPC321381
0.7	Intermediate Similarity	NPC52012
0.7	Intermediate Similarity	NPC298919
0.7	Intermediate Similarity	NPC107059
0.7	Intermediate Similarity	NPC472467
0.7	Intermediate Similarity	NPC321016
0.6988	Remote Similarity	NPC23852
0.6988	Remote Similarity	NPC474531
0.6988	Remote Similarity	NPC209620
0.6988	Remote Similarity	NPC470383
0.6988	Remote Similarity	NPC6707
0.6986	Remote Similarity	NPC474155
0.6986	Remote Similarity	NPC473759
0.6977	Remote Similarity	NPC477668
0.6977	Remote Similarity	NPC145245
0.6977	Remote Similarity	NPC269058
0.6977	Remote Similarity	NPC24277
0.6977	Remote Similarity	NPC71520
0.6977	Remote Similarity	NPC6605
0.6974	Remote Similarity	NPC160209
0.6966	Remote Similarity	NPC210268
0.6962	Remote Similarity	NPC190859
0.6957	Remote Similarity	NPC227135
0.6957	Remote Similarity	NPC281590
0.6951	Remote Similarity	NPC273410
0.6951	Remote Similarity	NPC80530
0.6941	Remote Similarity	NPC475798
0.6941	Remote Similarity	NPC127606
0.6933	Remote Similarity	NPC326310
0.6933	Remote Similarity	NPC250977
0.6932	Remote Similarity	NPC470361
0.6923	Remote Similarity	NPC261341
0.6923	Remote Similarity	NPC477792
0.6914	Remote Similarity	NPC130136
0.6914	Remote Similarity	NPC476703
0.6914	Remote Similarity	NPC214570
0.6912	Remote Similarity	NPC192962
0.6905	Remote Similarity	NPC7988
0.6905	Remote Similarity	NPC50964
0.6905	Remote Similarity	NPC201852
0.6897	Remote Similarity	NPC271967

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 NPC41886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	2741
0.2-0.3	4253
0.3-0.4	1423
0.4-0.5	288
0.5-0.6	215
0.6-0.7	64
0.7-0.8	4
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
0.7662	Intermediate Similarity	NPD6933	Approved
0.7403	Intermediate Similarity	NPD6926	Approved
0.7403	Intermediate Similarity	NPD6924	Approved
0.7342	Intermediate Similarity	NPD6932	Approved
0.7284	Intermediate Similarity	NPD6930	Phase 2
0.7284	Intermediate Similarity	NPD6931	Approved
0.7215	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6683	Phase 2
0.716	Intermediate Similarity	NPD6929	Approved
0.7125	Intermediate Similarity	NPD6925	Approved
0.7125	Intermediate Similarity	NPD5776	Phase 2
0.7105	Intermediate Similarity	NPD6922	Approved
0.7105	Intermediate Similarity	NPD6923	Approved
0.7093	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7524	Approved
0.7073	Intermediate Similarity	NPD7514	Phase 3
0.7037	Intermediate Similarity	NPD7145	Approved
0.7024	Intermediate Similarity	NPD6695	Phase 3
0.7013	Intermediate Similarity	NPD7144	Approved
0.7013	Intermediate Similarity	NPD7143	Approved
0.6941	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7151	Approved
0.6923	Remote Similarity	NPD7152	Approved
0.6923	Remote Similarity	NPD7150	Approved
0.6923	Remote Similarity	NPD4243	Approved
0.6875	Remote Similarity	NPD6942	Approved
0.6875	Remote Similarity	NPD7339	Approved
0.6867	Remote Similarity	NPD7525	Registered
0.6867	Remote Similarity	NPD7332	Phase 2
0.686	Remote Similarity	NPD6893	Approved
0.6786	Remote Similarity	NPD6898	Phase 1
0.6786	Remote Similarity	NPD6902	Approved
0.675	Remote Similarity	NPD4784	Approved
0.675	Remote Similarity	NPD4785	Approved
0.6705	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD4190	Phase 3
0.6667	Remote Similarity	NPD5275	Approved
0.6667	Remote Similarity	NPD4748	Discontinued
0.6627	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD368	Approved
0.6552	Remote Similarity	NPD3666	Approved
0.6552	Remote Similarity	NPD3665	Phase 1
0.6552	Remote Similarity	NPD3133	Approved
0.6548	Remote Similarity	NPD4195	Approved
0.6471	Remote Similarity	NPD4821	Approved
0.6471	Remote Similarity	NPD4820	Approved
0.6471	Remote Similarity	NPD4819	Approved
0.6471	Remote Similarity	NPD4822	Approved
0.6437	Remote Similarity	NPD5332	Approved
0.6437	Remote Similarity	NPD5362	Discontinued
0.6437	Remote Similarity	NPD5331	Approved
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7087	Discontinued
0.6395	Remote Similarity	NPD5369	Approved
0.6395	Remote Similarity	NPD4790	Discontinued
0.6374	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD4786	Approved
0.6344	Remote Similarity	NPD4202	Approved
0.6322	Remote Similarity	NPD3667	Approved
0.6322	Remote Similarity	NPD4221	Approved
0.6322	Remote Similarity	NPD4223	Phase 3
0.6292	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5368	Approved
0.6235	Remote Similarity	NPD4271	Approved
0.6235	Remote Similarity	NPD4268	Approved
0.6222	Remote Similarity	NPD5279	Phase 3
0.6214	Remote Similarity	NPD4634	Approved
0.618	Remote Similarity	NPD4197	Approved
0.6136	Remote Similarity	NPD4269	Approved
0.6136	Remote Similarity	NPD4270	Approved
0.6136	Remote Similarity	NPD6435	Approved
0.6111	Remote Similarity	NPD5329	Approved
0.6092	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4755	Approved
0.6071	Remote Similarity	NPD8264	Approved
0.6067	Remote Similarity	NPD4788	Approved
0.6064	Remote Similarity	NPD7637	Suspended
0.6058	Remote Similarity	NPD6371	Approved
0.6044	Remote Similarity	NPD4138	Approved
0.6044	Remote Similarity	NPD4693	Phase 3
0.6044	Remote Similarity	NPD5205	Approved
0.6044	Remote Similarity	NPD4694	Approved
0.6044	Remote Similarity	NPD5690	Phase 2
0.6044	Remote Similarity	NPD3618	Phase 1
0.6044	Remote Similarity	NPD4249	Approved
0.6044	Remote Similarity	NPD5280	Approved
0.6044	Remote Similarity	NPD4689	Approved
0.6044	Remote Similarity	NPD4688	Approved
0.6044	Remote Similarity	NPD4690	Approved
0.6042	Remote Similarity	NPD5210	Approved
0.6042	Remote Similarity	NPD4629	Approved
0.6027	Remote Similarity	NPD342	Phase 1
0.6024	Remote Similarity	NPD4732	Discontinued
0.6022	Remote Similarity	NPD5328	Approved
0.5978	Remote Similarity	NPD4251	Approved
0.5978	Remote Similarity	NPD4250	Approved
0.5977	Remote Similarity	NPD7645	Phase 2
0.596	Remote Similarity	NPD4700	Approved
0.596	Remote Similarity	NPD5285	Approved
0.596	Remote Similarity	NPD5286	Approved
0.596	Remote Similarity	NPD4696	Approved
0.5957	Remote Similarity	NPD5785	Approved
0.5957	Remote Similarity	NPD7136	Phase 2
0.5934	Remote Similarity	NPD5363	Approved
0.5922	Remote Similarity	NPD6412	Phase 2
0.5918	Remote Similarity	NPD6084	Phase 2
0.5918	Remote Similarity	NPD6083	Phase 2
0.5914	Remote Similarity	NPD4518	Approved
0.5914	Remote Similarity	NPD4722	Approved
0.5914	Remote Similarity	NPD4723	Approved
0.5909	Remote Similarity	NPD4252	Approved
0.59	Remote Similarity	NPD5223	Approved
0.5895	Remote Similarity	NPD6079	Approved
0.5888	Remote Similarity	NPD4632	Approved
0.5876	Remote Similarity	NPD5695	Phase 3
0.587	Remote Similarity	NPD5786	Approved
0.5859	Remote Similarity	NPD7638	Approved
0.5851	Remote Similarity	NPD6051	Approved
0.5843	Remote Similarity	NPD4692	Approved
0.5843	Remote Similarity	NPD4139	Approved
0.5842	Remote Similarity	NPD5226	Approved
0.5842	Remote Similarity	NPD4633	Approved
0.5842	Remote Similarity	NPD5211	Phase 2
0.5842	Remote Similarity	NPD5225	Approved
0.5842	Remote Similarity	NPD5224	Approved
0.5824	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7640	Approved
0.58	Remote Similarity	NPD7639	Approved
0.5789	Remote Similarity	NPD4096	Approved
0.5789	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5175	Approved
0.5784	Remote Similarity	NPD4754	Approved
0.5784	Remote Similarity	NPD5174	Approved
0.5766	Remote Similarity	NPD4522	Approved
0.5729	Remote Similarity	NPD5281	Approved
0.5729	Remote Similarity	NPD5284	Approved
0.5728	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD7154	Phase 3
0.5714	Remote Similarity	NPD6319	Approved
0.57	Remote Similarity	NPD5696	Approved
0.5699	Remote Similarity	NPD5330	Approved
0.5699	Remote Similarity	NPD7521	Approved
0.5699	Remote Similarity	NPD6409	Approved
0.5699	Remote Similarity	NPD6684	Approved
0.5699	Remote Similarity	NPD7146	Approved
0.5699	Remote Similarity	NPD7334	Approved
0.5684	Remote Similarity	NPD1695	Approved
0.5676	Remote Similarity	NPD7327	Approved
0.5676	Remote Similarity	NPD7328	Approved
0.5673	Remote Similarity	NPD7128	Approved
0.5673	Remote Similarity	NPD6402	Approved
0.5673	Remote Similarity	NPD4767	Approved
0.5673	Remote Similarity	NPD6640	Phase 3
0.5673	Remote Similarity	NPD6675	Approved
0.5673	Remote Similarity	NPD5739	Approved
0.5673	Remote Similarity	NPD4768	Approved
0.567	Remote Similarity	NPD6399	Phase 3
0.5663	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD1082	Approved
0.5657	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4697	Phase 3
0.5657	Remote Similarity	NPD5221	Approved
0.5657	Remote Similarity	NPD5222	Approved
0.5652	Remote Similarity	NPD3668	Phase 3
0.5632	Remote Similarity	NPD1346	Approved
0.5625	Remote Similarity	NPD7516	Approved
0.5619	Remote Similarity	NPD5697	Approved
0.5619	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5701	Approved
0.5612	Remote Similarity	NPD5282	Discontinued
0.56	Remote Similarity	NPD5173	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