NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	3.331
LogD:	2.998
LogS:	-3.384
# 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:	4.352
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:	-4.284
MDCK Permeability:	1.699665153864771e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.57
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.234
Plasma Protein Binding (PPB):	88.38326263427734%
Volume Distribution (VD):	1.122
Pgp-substrate:	11.563942909240723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.174
CYP1A2-substrate:	0.326
CYP2C19-inhibitor:	0.104
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.215
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.249
CYP3A4-substrate:	0.601

ADMET: Excretion

Clearance (CL):	8.258
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.2
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.254
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.05
Carcinogencity:	0.622
Eye Corrosion:	0.021
Eye Irritation:	0.429
Respiratory Toxicity:	0.33

Download Data

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

Natural Product: NPC205618

Natural Product ID:	NPC205618
*Common Name:**	Guaianediol
IUPAC Name:	(1R,3aS,4S,8aR)-1,4-dimethyl-7-propan-2-yl-2,3,3a,5,6,8a-hexahydroazulene-1,4-diol
Synonyms:	(-)-Alismoxide; Guaianediol
Standard InCHIKey:	IWQURBSTAIRNAE-LJISPDSOSA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-10(2)11-5-7-14(3,16)12-6-8-15(4,17)13(12)9-11/h9-10,12-13,16-17H,5-8H2,1-4H3/t12-,13+,14-,15+/m0/s1
SMILES:	CC(C)C1=C[C@@H]2[C@H](CC[C@@]2(C)O)[C@](C)(CC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456292
PubChem CID:	10243299
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002874] Guaianes

*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
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	Whole plants	Mountain Emei, Sichuan Province, China	2008-OCT	PMID[21561060]
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21561060]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23022271]
NPO40347	Sinularia gardineri	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759167]
NPO7730	Commiphora myrrha	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14364.1	Alisma plantago-aquatica subsp. orientale	Subspecies	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7730	Commiphora myrrha	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO60	Neoshirakia japonica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3061	Alisma orientalis	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14364.1	Alisma plantago-aquatica subsp. orientale	Subspecies	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10306	Alisma orienatale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3061	Alisma orientalis	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14364.1	Alisma plantago-aquatica subsp. orientale	Subspecies	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4048	Inga longispica	Species	Oecophoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO791	Laburnum anagyroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO60	Neoshirakia japonica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7730	Commiphora myrrha	Species	Burseraceae	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
EC50	1
IC50	6
Others	5

Activity Type	# Activity
Cell Line	11
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	Activity	=	1.0	ug ml-1	PMID[564080]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	2.5	ug ml-1	PMID[564080]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	Activity	=	5.0	ug ml-1	PMID[564080]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	5.0	ug ml-1	PMID[564080]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	64400.0	nM	PMID[564081]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	64400.0	nM	PMID[564081]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	64400.0	nM	PMID[564081]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	64400.0	nM	PMID[564081]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	64400.0	nM	PMID[564081]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	420200.0	nM	PMID[564081]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	64400.0	nM	PMID[564081]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	420200.0	nM	PMID[564081]

☑ 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 NPC205618 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	159
0.1-0.2	2006
0.2-0.3	12960
0.3-0.4	14537
0.4-0.5	8445
0.5-0.6	3884
0.6-0.7	616
0.7-0.8	72
0.8-0.85	5
0.85-0.9	4
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC261782
1.0	High Similarity	NPC469326
0.95	High Similarity	NPC63111
0.9375	High Similarity	NPC144647
0.9231	High Similarity	NPC471781
0.9167	High Similarity	NPC469321
0.8852	High Similarity	NPC52431
0.8852	High Similarity	NPC310228
0.8833	High Similarity	NPC278550
0.8333	Intermediate Similarity	NPC469324
0.8261	Intermediate Similarity	NPC41886
0.8125	Intermediate Similarity	NPC252809
0.8116	Intermediate Similarity	NPC470041
0.8056	Intermediate Similarity	NPC126969
0.7971	Intermediate Similarity	NPC474900
0.7969	Intermediate Similarity	NPC5698
0.7941	Intermediate Similarity	NPC136813
0.7887	Intermediate Similarity	NPC469320
0.7879	Intermediate Similarity	NPC474480
0.7869	Intermediate Similarity	NPC192962
0.7846	Intermediate Similarity	NPC323153
0.7826	Intermediate Similarity	NPC224532
0.7778	Intermediate Similarity	NPC274396
0.7746	Intermediate Similarity	NPC471660
0.7692	Intermediate Similarity	NPC184049
0.7692	Intermediate Similarity	NPC99480
0.7681	Intermediate Similarity	NPC472255
0.7681	Intermediate Similarity	NPC472253
0.7647	Intermediate Similarity	NPC238352
0.7647	Intermediate Similarity	NPC477009
0.7639	Intermediate Similarity	NPC300940
0.7632	Intermediate Similarity	NPC30675
0.7612	Intermediate Similarity	NPC211291
0.7612	Intermediate Similarity	NPC133368
0.7576	Intermediate Similarity	NPC135648
0.7571	Intermediate Similarity	NPC167527
0.7568	Intermediate Similarity	NPC152017
0.7538	Intermediate Similarity	NPC475830
0.7536	Intermediate Similarity	NPC469328
0.7536	Intermediate Similarity	NPC272125
0.7534	Intermediate Similarity	NPC471659
0.7463	Intermediate Similarity	NPC274704
0.7436	Intermediate Similarity	NPC133844
0.7432	Intermediate Similarity	NPC77501
0.7432	Intermediate Similarity	NPC85831
0.7432	Intermediate Similarity	NPC265921
0.7432	Intermediate Similarity	NPC215215
0.7391	Intermediate Similarity	NPC471200
0.7353	Intermediate Similarity	NPC279200
0.7342	Intermediate Similarity	NPC471340
0.7333	Intermediate Similarity	NPC115719
0.7333	Intermediate Similarity	NPC471658
0.7333	Intermediate Similarity	NPC124289
0.7333	Intermediate Similarity	NPC142759
0.7333	Intermediate Similarity	NPC25908
0.7333	Intermediate Similarity	NPC473437
0.7333	Intermediate Similarity	NPC141346
0.7308	Intermediate Similarity	NPC471661
0.7297	Intermediate Similarity	NPC309178
0.7273	Intermediate Similarity	NPC471890
0.7273	Intermediate Similarity	NPC66677
0.7273	Intermediate Similarity	NPC84185
0.726	Intermediate Similarity	NPC469737
0.7237	Intermediate Similarity	NPC471454
0.7215	Intermediate Similarity	NPC470614
0.7215	Intermediate Similarity	NPC472465
0.7215	Intermediate Similarity	NPC1272
0.7206	Intermediate Similarity	NPC15152
0.7206	Intermediate Similarity	NPC210346
0.72	Intermediate Similarity	NPC319090
0.72	Intermediate Similarity	NPC113639
0.72	Intermediate Similarity	NPC23231
0.72	Intermediate Similarity	NPC60818
0.72	Intermediate Similarity	NPC328104
0.7183	Intermediate Similarity	NPC477791
0.7179	Intermediate Similarity	NPC26117
0.7162	Intermediate Similarity	NPC14352
0.7162	Intermediate Similarity	NPC234527
0.716	Intermediate Similarity	NPC146850
0.716	Intermediate Similarity	NPC287015
0.7143	Intermediate Similarity	NPC157781
0.7143	Intermediate Similarity	NPC179169
0.7143	Intermediate Similarity	NPC35519
0.7143	Intermediate Similarity	NPC61503
0.7143	Intermediate Similarity	NPC470944
0.7143	Intermediate Similarity	NPC306195
0.7143	Intermediate Similarity	NPC187619
0.7143	Intermediate Similarity	NPC181255
0.7123	Intermediate Similarity	NPC254845
0.7105	Intermediate Similarity	NPC215481
0.7105	Intermediate Similarity	NPC476317
0.7105	Intermediate Similarity	NPC310643
0.7101	Intermediate Similarity	NPC473508
0.7097	Intermediate Similarity	NPC329773
0.7077	Intermediate Similarity	NPC218525
0.7077	Intermediate Similarity	NPC45387
0.7067	Intermediate Similarity	NPC329090
0.7067	Intermediate Similarity	NPC27395
0.7059	Intermediate Similarity	NPC162109
0.7042	Intermediate Similarity	NPC311736
0.7042	Intermediate Similarity	NPC230107
0.7037	Intermediate Similarity	NPC90446
0.7037	Intermediate Similarity	NPC116613
0.7037	Intermediate Similarity	NPC124172
0.7027	Intermediate Similarity	NPC471662
0.7013	Intermediate Similarity	NPC186109
0.7	Intermediate Similarity	NPC300593
0.7	Intermediate Similarity	NPC309300
0.6988	Remote Similarity	NPC191283
0.6986	Remote Similarity	NPC74722
0.6986	Remote Similarity	NPC304690
0.6984	Remote Similarity	NPC214584
0.6984	Remote Similarity	NPC26906
0.6974	Remote Similarity	NPC251435
0.6974	Remote Similarity	NPC313185
0.6974	Remote Similarity	NPC89374
0.6962	Remote Similarity	NPC186072
0.6962	Remote Similarity	NPC324772
0.6962	Remote Similarity	NPC471656
0.6962	Remote Similarity	NPC164218
0.6944	Remote Similarity	NPC73603
0.6944	Remote Similarity	NPC163290
0.6941	Remote Similarity	NPC301969
0.6941	Remote Similarity	NPC470832
0.6941	Remote Similarity	NPC37607
0.6933	Remote Similarity	NPC310608
0.6933	Remote Similarity	NPC474140
0.6933	Remote Similarity	NPC476709
0.6923	Remote Similarity	NPC87604
0.6923	Remote Similarity	NPC477522
0.6914	Remote Similarity	NPC110778
0.6914	Remote Similarity	NPC477818
0.6901	Remote Similarity	NPC300442
0.6892	Remote Similarity	NPC475728
0.6892	Remote Similarity	NPC133873
0.6883	Remote Similarity	NPC315261
0.6883	Remote Similarity	NPC96319
0.6875	Remote Similarity	NPC177112
0.6875	Remote Similarity	NPC15978
0.6875	Remote Similarity	NPC71506
0.6875	Remote Similarity	NPC320525
0.6867	Remote Similarity	NPC152808
0.6867	Remote Similarity	NPC201273
0.6867	Remote Similarity	NPC293287
0.6867	Remote Similarity	NPC24277
0.6866	Remote Similarity	NPC119425
0.686	Remote Similarity	NPC94127
0.6835	Remote Similarity	NPC204270
0.6829	Remote Similarity	NPC475798
0.6829	Remote Similarity	NPC209802
0.6829	Remote Similarity	NPC127606
0.6818	Remote Similarity	NPC67584
0.6818	Remote Similarity	NPC52044
0.6812	Remote Similarity	NPC99487
0.6812	Remote Similarity	NPC66020
0.6806	Remote Similarity	NPC162309
0.6806	Remote Similarity	NPC267027
0.68	Remote Similarity	NPC469343
0.6795	Remote Similarity	NPC318495
0.6795	Remote Similarity	NPC198968
0.6795	Remote Similarity	NPC476439
0.6795	Remote Similarity	NPC155986
0.6786	Remote Similarity	NPC271967
0.6782	Remote Similarity	NPC40821
0.6782	Remote Similarity	NPC32862
0.6782	Remote Similarity	NPC272293
0.6765	Remote Similarity	NPC10017
0.6761	Remote Similarity	NPC219940
0.6761	Remote Similarity	NPC287744
0.6761	Remote Similarity	NPC140233
0.6757	Remote Similarity	NPC90115
0.6757	Remote Similarity	NPC22301
0.6757	Remote Similarity	NPC217570
0.6753	Remote Similarity	NPC12696
0.675	Remote Similarity	NPC156658
0.675	Remote Similarity	NPC258965
0.6747	Remote Similarity	NPC474349
0.6747	Remote Similarity	NPC471185
0.6747	Remote Similarity	NPC474189
0.6742	Remote Similarity	NPC213078
0.6714	Remote Similarity	NPC79576
0.6714	Remote Similarity	NPC194208
0.6714	Remote Similarity	NPC282694
0.6712	Remote Similarity	NPC82337
0.6709	Remote Similarity	NPC477514
0.6707	Remote Similarity	NPC193870
0.6707	Remote Similarity	NPC320548
0.6707	Remote Similarity	NPC141941
0.6707	Remote Similarity	NPC477667
0.6706	Remote Similarity	NPC2158
0.6706	Remote Similarity	NPC470542
0.6705	Remote Similarity	NPC473258
0.6667	Remote Similarity	NPC170148
0.6667	Remote Similarity	NPC321381
0.6667	Remote Similarity	NPC209620
0.6667	Remote Similarity	NPC6605
0.6667	Remote Similarity	NPC122239
0.6667	Remote Similarity	NPC23852
0.6667	Remote Similarity	NPC161493
0.6667	Remote Similarity	NPC321016

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 NPC205618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	2723
0.2-0.3	4340
0.3-0.4	1392
0.4-0.5	336
0.5-0.6	145
0.6-0.7	61
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
0.7297	Intermediate Similarity	NPD4784	Approved
0.7297	Intermediate Similarity	NPD4785	Approved
0.726	Intermediate Similarity	NPD4243	Approved
0.7067	Intermediate Similarity	NPD6924	Approved
0.7067	Intermediate Similarity	NPD6926	Approved
0.6974	Remote Similarity	NPD4190	Phase 3
0.6974	Remote Similarity	NPD5275	Approved
0.6962	Remote Similarity	NPD6931	Approved
0.6962	Remote Similarity	NPD6930	Phase 2
0.6883	Remote Similarity	NPD6933	Approved
0.6883	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6929	Approved
0.6835	Remote Similarity	NPD4195	Approved
0.6829	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6932	Approved
0.6786	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6695	Phase 3
0.6625	Remote Similarity	NPD6683	Phase 2
0.6585	Remote Similarity	NPD4221	Approved
0.6585	Remote Similarity	NPD4223	Phase 3
0.6582	Remote Similarity	NPD5776	Phase 2
0.6582	Remote Similarity	NPD6925	Approved
0.6548	Remote Similarity	NPD6893	Approved
0.6543	Remote Similarity	NPD4820	Approved
0.6543	Remote Similarity	NPD7525	Registered
0.6543	Remote Similarity	NPD7509	Discontinued
0.6543	Remote Similarity	NPD4822	Approved
0.6543	Remote Similarity	NPD7514	Phase 3
0.6543	Remote Similarity	NPD4819	Approved
0.6543	Remote Similarity	NPD4821	Approved
0.6538	Remote Similarity	NPD7339	Approved
0.6538	Remote Similarity	NPD6942	Approved
0.6533	Remote Similarity	NPD6923	Approved
0.6533	Remote Similarity	NPD6922	Approved
0.65	Remote Similarity	NPD7145	Approved
0.6479	Remote Similarity	NPD368	Approved
0.6447	Remote Similarity	NPD7143	Approved
0.6447	Remote Similarity	NPD7144	Approved
0.6429	Remote Similarity	NPD4197	Approved
0.6395	Remote Similarity	NPD7750	Discontinued
0.6395	Remote Similarity	NPD7524	Approved
0.6364	Remote Similarity	NPD7150	Approved
0.6364	Remote Similarity	NPD7151	Approved
0.6364	Remote Similarity	NPD7152	Approved
0.6353	Remote Similarity	NPD5329	Approved
0.6341	Remote Similarity	NPD4748	Discontinued
0.6341	Remote Similarity	NPD7332	Phase 2
0.6322	Remote Similarity	NPD4518	Approved
0.631	Remote Similarity	NPD5331	Approved
0.631	Remote Similarity	NPD5332	Approved
0.631	Remote Similarity	NPD5362	Discontinued
0.6296	Remote Similarity	NPD4271	Approved
0.6296	Remote Similarity	NPD4268	Approved
0.6279	Remote Similarity	NPD4688	Approved
0.6279	Remote Similarity	NPD5280	Approved
0.6279	Remote Similarity	NPD4690	Approved
0.6279	Remote Similarity	NPD4138	Approved
0.6279	Remote Similarity	NPD4693	Phase 3
0.6279	Remote Similarity	NPD5205	Approved
0.6279	Remote Similarity	NPD4694	Approved
0.6279	Remote Similarity	NPD5690	Phase 2
0.6279	Remote Similarity	NPD4689	Approved
0.6265	Remote Similarity	NPD4790	Discontinued
0.6265	Remote Similarity	NPD6902	Approved
0.6265	Remote Similarity	NPD6898	Phase 1
0.6265	Remote Similarity	NPD5369	Approved
0.618	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5368	Approved
0.6145	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4723	Approved
0.6136	Remote Similarity	NPD4722	Approved
0.6111	Remote Similarity	NPD5281	Approved
0.6111	Remote Similarity	NPD5284	Approved
0.6111	Remote Similarity	NPD7087	Discontinued
0.6098	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4249	Approved
0.6087	Remote Similarity	NPD342	Phase 1
0.6071	Remote Similarity	NPD4139	Approved
0.6071	Remote Similarity	NPD4692	Approved
0.6067	Remote Similarity	NPD1695	Approved
0.6067	Remote Similarity	NPD4753	Phase 2
0.6049	Remote Similarity	NPD1346	Approved
0.6047	Remote Similarity	NPD3665	Phase 1
0.6047	Remote Similarity	NPD3133	Approved
0.6047	Remote Similarity	NPD3666	Approved
0.6047	Remote Similarity	NPD4786	Approved
0.6044	Remote Similarity	NPD4202	Approved
0.6023	Remote Similarity	NPD4251	Approved
0.6023	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD6435	Approved
0.6	Remote Similarity	NPD4096	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD3667	Approved
0.5938	Remote Similarity	NPD386	Approved
0.5938	Remote Similarity	NPD388	Approved
0.5921	Remote Similarity	NPD7331	Phase 2
0.5897	Remote Similarity	NPD1082	Approved
0.5795	Remote Similarity	NPD5363	Approved
0.5789	Remote Similarity	NPD7341	Phase 2
0.5789	Remote Similarity	NPD4755	Approved
0.5765	Remote Similarity	NPD4252	Approved
0.5747	Remote Similarity	NPD4788	Approved
0.5745	Remote Similarity	NPD5695	Phase 3
0.5745	Remote Similarity	NPD5210	Approved
0.5745	Remote Similarity	NPD4629	Approved
0.573	Remote Similarity	NPD5786	Approved
0.573	Remote Similarity	NPD6098	Approved
0.573	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.573	Remote Similarity	NPD5279	Phase 3
0.5714	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD6399	Phase 3
0.5699	Remote Similarity	NPD5133	Approved
0.5673	Remote Similarity	NPD6053	Discontinued
0.567	Remote Similarity	NPD5285	Approved
0.567	Remote Similarity	NPD4696	Approved
0.567	Remote Similarity	NPD4700	Approved
0.567	Remote Similarity	NPD5286	Approved
0.5644	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD5282	Discontinued
0.5631	Remote Similarity	NPD6371	Approved
0.5625	Remote Similarity	NPD6083	Phase 2
0.5625	Remote Similarity	NPD6084	Phase 2
0.5612	Remote Similarity	NPD5223	Approved
0.5604	Remote Similarity	NPD5208	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