NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.19
Volume:	274.618
LogP:	2.195
LogD:	1.669
LogS:	-2.35
# Rotatable Bonds:	2
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.659
Synthetic Accessibility Score:	4.464
Fsp3:	0.867
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:	-4.31
MDCK Permeability:	9.83825339062605e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.109
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.902
Plasma Protein Binding (PPB):	78.23307037353516%
Volume Distribution (VD):	1.136
Pgp-substrate:	18.495285034179688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.25
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.149
CYP3A4-substrate:	0.388

ADMET: Excretion

Clearance (CL):	8.637
Half-life (T1/2):	0.459

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.161
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.145
Maximum Recommended Daily Dose:	0.181
Skin Sensitization:	0.044
Carcinogencity:	0.541
Eye Corrosion:	0.003
Eye Irritation:	0.048
Respiratory Toxicity:	0.177

Download Data

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

Natural Product: NPC471781

Natural Product ID:	NPC471781
*Common Name:**	(1S,4R)-4-(Hydroxymethyl)-1-Methyl-7-Propan-2-Yl-2,3,3A,5,6,8A-Hexahydroazulene-1,4-Diol
IUPAC Name:	(1S,4R)-4-(hydroxymethyl)-1-methyl-7-propan-2-yl-2,3,3a,5,6,8a-hexahydroazulene-1,4-diol
Synonyms:
Standard InCHIKey:	IBEULDMGWROYNC-WUCCLRPBSA-N
Standard InCHI:	InChI=1S/C15H26O3/c1-10(2)11-4-7-15(18,9-16)12-5-6-14(3,17)13(12)8-11/h8,10,12-13,16-18H,4-7,9H2,1-3H3/t12?,13?,14-,15-/m0/s1
SMILES:	OC[C@@]1(O)CCC(=CC2C1CC[C@]2(C)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL320240
PubChem CID:	44335287
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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	-4.3	%	PMID[473498]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	-3.1	%	PMID[473498]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	4.8	%	PMID[473498]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	21.2	%	PMID[473498]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	64.1	%	PMID[473498]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	68000.0	nM	PMID[473498]

☑ 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 NPC471781 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	174
0.1-0.2	1753
0.2-0.3	10185
0.3-0.4	15449
0.4-0.5	8617
0.5-0.6	5362
0.6-0.7	1046
0.7-0.8	93
0.8-0.85	8
0.85-0.9	5
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC205618
0.9231	High Similarity	NPC469326
0.9231	High Similarity	NPC261782
0.8986	High Similarity	NPC41886
0.8971	High Similarity	NPC144647
0.8769	High Similarity	NPC63111
0.875	High Similarity	NPC126969
0.8462	Intermediate Similarity	NPC469321
0.831	Intermediate Similarity	NPC470041
0.8182	Intermediate Similarity	NPC52431
0.8182	Intermediate Similarity	NPC310228
0.8154	Intermediate Similarity	NPC278550
0.8143	Intermediate Similarity	NPC136813
0.8116	Intermediate Similarity	NPC471200
0.8028	Intermediate Similarity	NPC224532
0.7887	Intermediate Similarity	NPC472253
0.7887	Intermediate Similarity	NPC472255
0.7857	Intermediate Similarity	NPC238352
0.7857	Intermediate Similarity	NPC477009
0.7848	Intermediate Similarity	NPC472465
0.7826	Intermediate Similarity	NPC211291
0.7826	Intermediate Similarity	NPC133368
0.7792	Intermediate Similarity	NPC469324
0.7778	Intermediate Similarity	NPC167527
0.7761	Intermediate Similarity	NPC475830
0.775	Intermediate Similarity	NPC471340
0.7746	Intermediate Similarity	NPC311736
0.7746	Intermediate Similarity	NPC272125
0.7733	Intermediate Similarity	NPC471659
0.7681	Intermediate Similarity	NPC274704
0.7639	Intermediate Similarity	NPC163290
0.7625	Intermediate Similarity	NPC133844
0.76	Intermediate Similarity	NPC476709
0.7595	Intermediate Similarity	NPC30675
0.7571	Intermediate Similarity	NPC279200
0.7536	Intermediate Similarity	NPC252809
0.7532	Intermediate Similarity	NPC471658
0.7532	Intermediate Similarity	NPC315261
0.7529	Intermediate Similarity	NPC470832
0.75	Intermediate Similarity	NPC469328
0.75	Intermediate Similarity	NPC267027
0.75	Intermediate Similarity	NPC309178
0.7432	Intermediate Similarity	NPC474900
0.7407	Intermediate Similarity	NPC470614
0.7407	Intermediate Similarity	NPC1272
0.7403	Intermediate Similarity	NPC60818
0.7403	Intermediate Similarity	NPC23231
0.7403	Intermediate Similarity	NPC328104
0.7403	Intermediate Similarity	NPC319090
0.7397	Intermediate Similarity	NPC477791
0.7397	Intermediate Similarity	NPC82337
0.7391	Intermediate Similarity	NPC5698
0.7375	Intermediate Similarity	NPC26117
0.7368	Intermediate Similarity	NPC234527
0.7368	Intermediate Similarity	NPC469320
0.7368	Intermediate Similarity	NPC14352
0.7361	Intermediate Similarity	NPC61503
0.7361	Intermediate Similarity	NPC187619
0.7342	Intermediate Similarity	NPC470944
0.7333	Intermediate Similarity	NPC254845
0.7324	Intermediate Similarity	NPC474480
0.7324	Intermediate Similarity	NPC473508
0.7317	Intermediate Similarity	NPC320548
0.7308	Intermediate Similarity	NPC310643
0.7308	Intermediate Similarity	NPC170148
0.7286	Intermediate Similarity	NPC323153
0.7284	Intermediate Similarity	NPC471661
0.7273	Intermediate Similarity	NPC27395
0.7273	Intermediate Similarity	NPC192962
0.7273	Intermediate Similarity	NPC329090
0.7273	Intermediate Similarity	NPC190859
0.7273	Intermediate Similarity	NPC473258
0.725	Intermediate Similarity	NPC476701
0.725	Intermediate Similarity	NPC328714
0.7237	Intermediate Similarity	NPC471660
0.7237	Intermediate Similarity	NPC471662
0.7229	Intermediate Similarity	NPC242016
0.7229	Intermediate Similarity	NPC124172
0.7222	Intermediate Similarity	NPC300593
0.7222	Intermediate Similarity	NPC309300
0.7215	Intermediate Similarity	NPC471454
0.7215	Intermediate Similarity	NPC476703
0.7209	Intermediate Similarity	NPC105495
0.7209	Intermediate Similarity	NPC299527
0.7206	Intermediate Similarity	NPC274396
0.72	Intermediate Similarity	NPC16964
0.7179	Intermediate Similarity	NPC12696
0.7179	Intermediate Similarity	NPC113639
0.7179	Intermediate Similarity	NPC313185
0.7162	Intermediate Similarity	NPC73603
0.716	Intermediate Similarity	NPC324772
0.7143	Intermediate Similarity	NPC310608
0.7143	Intermediate Similarity	NPC300940
0.7143	Intermediate Similarity	NPC475968
0.7143	Intermediate Similarity	NPC184049
0.7143	Intermediate Similarity	NPC474140
0.7143	Intermediate Similarity	NPC99480
0.7126	Intermediate Similarity	NPC472466
0.7126	Intermediate Similarity	NPC473956
0.7126	Intermediate Similarity	NPC475751
0.7126	Intermediate Similarity	NPC107189
0.7125	Intermediate Similarity	NPC87604
0.7125	Intermediate Similarity	NPC475980
0.7125	Intermediate Similarity	NPC477522
0.7123	Intermediate Similarity	NPC300442
0.7108	Intermediate Similarity	NPC260852
0.7108	Intermediate Similarity	NPC110778
0.7108	Intermediate Similarity	NPC477818
0.7105	Intermediate Similarity	NPC133873
0.7101	Intermediate Similarity	NPC119425
0.7093	Intermediate Similarity	NPC474668
0.7093	Intermediate Similarity	NPC475664
0.7089	Intermediate Similarity	NPC476317
0.7089	Intermediate Similarity	NPC215481
0.7089	Intermediate Similarity	NPC152017
0.7089	Intermediate Similarity	NPC96319
0.7079	Intermediate Similarity	NPC298919
0.7073	Intermediate Similarity	NPC320525
0.7059	Intermediate Similarity	NPC293287
0.7059	Intermediate Similarity	NPC201273
0.7059	Intermediate Similarity	NPC94462
0.7059	Intermediate Similarity	NPC152808
0.7059	Intermediate Similarity	NPC24277
0.7045	Intermediate Similarity	NPC472468
0.7045	Intermediate Similarity	NPC94127
0.7042	Intermediate Similarity	NPC99487
0.7042	Intermediate Similarity	NPC66020
0.7042	Intermediate Similarity	NPC135648
0.7027	Intermediate Similarity	NPC326310
0.7027	Intermediate Similarity	NPC162309
0.7024	Intermediate Similarity	NPC209802
0.7024	Intermediate Similarity	NPC127606
0.7024	Intermediate Similarity	NPC116613
0.7024	Intermediate Similarity	NPC475798
0.7013	Intermediate Similarity	NPC242992
0.7013	Intermediate Similarity	NPC469343
0.7011	Intermediate Similarity	NPC470361
0.7011	Intermediate Similarity	NPC109744
0.7	Intermediate Similarity	NPC155986
0.7	Intermediate Similarity	NPC52044
0.7	Intermediate Similarity	NPC198968
0.7	Intermediate Similarity	NPC186109
0.7	Intermediate Similarity	NPC10017
0.7	Intermediate Similarity	NPC318495
0.7	Intermediate Similarity	NPC261341
0.6986	Remote Similarity	NPC219940
0.6977	Remote Similarity	NPC271967
0.6977	Remote Similarity	NPC186145
0.6977	Remote Similarity	NPC474657
0.6974	Remote Similarity	NPC304690
0.6974	Remote Similarity	NPC217570
0.6974	Remote Similarity	NPC473893
0.6974	Remote Similarity	NPC74722
0.6974	Remote Similarity	NPC90115
0.6966	Remote Similarity	NPC98193
0.6962	Remote Similarity	NPC265921
0.6962	Remote Similarity	NPC77501
0.6962	Remote Similarity	NPC215215
0.6962	Remote Similarity	NPC85831
0.6951	Remote Similarity	NPC13554
0.6951	Remote Similarity	NPC471656
0.6951	Remote Similarity	NPC186072
0.6941	Remote Similarity	NPC474189
0.6941	Remote Similarity	NPC474349
0.6932	Remote Similarity	NPC11216
0.6932	Remote Similarity	NPC37607
0.6932	Remote Similarity	NPC291484
0.6932	Remote Similarity	NPC3345
0.6932	Remote Similarity	NPC329596
0.6932	Remote Similarity	NPC301969
0.6932	Remote Similarity	NPC204188
0.6932	Remote Similarity	NPC80561
0.6923	Remote Similarity	NPC143576
0.6914	Remote Similarity	NPC477514
0.6914	Remote Similarity	NPC477089
0.6905	Remote Similarity	NPC207013
0.6905	Remote Similarity	NPC477667
0.6905	Remote Similarity	NPC474634
0.6905	Remote Similarity	NPC141941
0.6905	Remote Similarity	NPC193870
0.6901	Remote Similarity	NPC122239
0.6897	Remote Similarity	NPC22376
0.6897	Remote Similarity	NPC470542
0.6897	Remote Similarity	NPC2158
0.6897	Remote Similarity	NPC133588
0.6892	Remote Similarity	NPC19569
0.6889	Remote Similarity	NPC472467
0.6883	Remote Similarity	NPC280256
0.6875	Remote Similarity	NPC141346
0.6875	Remote Similarity	NPC25908
0.6875	Remote Similarity	NPC124289
0.6875	Remote Similarity	NPC321381
0.6875	Remote Similarity	NPC115719
0.6875	Remote Similarity	NPC473437
0.6875	Remote Similarity	NPC321016
0.6875	Remote Similarity	NPC142759
0.6875	Remote Similarity	NPC107059
0.6867	Remote Similarity	NPC15978
0.6867	Remote Similarity	NPC474531
0.6867	Remote Similarity	NPC23852

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 NPC471781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	2514
0.2-0.3	4273
0.3-0.4	1593
0.4-0.5	342
0.5-0.6	203
0.6-0.7	63
0.7-0.8	1
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
0.7532	Intermediate Similarity	NPD6933	Approved
0.7273	Intermediate Similarity	NPD6926	Approved
0.7273	Intermediate Similarity	NPD6924	Approved
0.716	Intermediate Similarity	NPD6931	Approved
0.716	Intermediate Similarity	NPD6930	Phase 2
0.7089	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6929	Approved
0.7024	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6932	Approved
0.6977	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7524	Approved
0.6905	Remote Similarity	NPD6695	Phase 3
0.6835	Remote Similarity	NPD4785	Approved
0.6835	Remote Similarity	NPD4784	Approved
0.6829	Remote Similarity	NPD6683	Phase 2
0.6795	Remote Similarity	NPD4243	Approved
0.679	Remote Similarity	NPD5776	Phase 2
0.679	Remote Similarity	NPD6925	Approved
0.6753	Remote Similarity	NPD6922	Approved
0.6753	Remote Similarity	NPD6923	Approved
0.675	Remote Similarity	NPD6942	Approved
0.675	Remote Similarity	NPD7339	Approved
0.6747	Remote Similarity	NPD7509	Discontinued
0.6747	Remote Similarity	NPD4820	Approved
0.6747	Remote Similarity	NPD4819	Approved
0.6747	Remote Similarity	NPD4822	Approved
0.6747	Remote Similarity	NPD7514	Phase 3
0.6747	Remote Similarity	NPD4821	Approved
0.6747	Remote Similarity	NPD7525	Registered
0.6744	Remote Similarity	NPD6893	Approved
0.6712	Remote Similarity	NPD368	Approved
0.6707	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6591	Remote Similarity	NPD7750	Discontinued
0.6582	Remote Similarity	NPD7150	Approved
0.6582	Remote Similarity	NPD7151	Approved
0.6582	Remote Similarity	NPD7152	Approved
0.6548	Remote Similarity	NPD7332	Phase 2
0.6548	Remote Similarity	NPD4748	Discontinued
0.6543	Remote Similarity	NPD5275	Approved
0.6543	Remote Similarity	NPD4190	Phase 3
0.6512	Remote Similarity	NPD5362	Discontinued
0.6512	Remote Similarity	NPD5332	Approved
0.6512	Remote Similarity	NPD5331	Approved
0.6506	Remote Similarity	NPD4268	Approved
0.6506	Remote Similarity	NPD4271	Approved
0.6471	Remote Similarity	NPD4790	Discontinued
0.6471	Remote Similarity	NPD6902	Approved
0.6471	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD6898	Phase 1
0.6429	Remote Similarity	NPD4195	Approved
0.6364	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5368	Approved
0.6338	Remote Similarity	NPD342	Phase 1
0.631	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7087	Discontinued
0.6292	Remote Similarity	NPD4249	Approved
0.6264	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3133	Approved
0.6237	Remote Similarity	NPD4202	Approved
0.6222	Remote Similarity	NPD4250	Approved
0.6222	Remote Similarity	NPD4251	Approved
0.6207	Remote Similarity	NPD4221	Approved
0.6207	Remote Similarity	NPD6435	Approved
0.6207	Remote Similarity	NPD4269	Approved
0.6207	Remote Similarity	NPD4223	Phase 3
0.6207	Remote Similarity	NPD3667	Approved
0.6207	Remote Similarity	NPD4270	Approved
0.6117	Remote Similarity	NPD6371	Approved
0.6087	Remote Similarity	NPD1695	Approved
0.6067	Remote Similarity	NPD4197	Approved
0.6	Remote Similarity	NPD5363	Approved
0.6	Remote Similarity	NPD5329	Approved
0.598	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4755	Approved
0.5978	Remote Similarity	NPD4518	Approved
0.5977	Remote Similarity	NPD4252	Approved
0.5962	Remote Similarity	NPD4634	Approved
0.5955	Remote Similarity	NPD4788	Approved
0.5938	Remote Similarity	NPD4629	Approved
0.5938	Remote Similarity	NPD5210	Approved
0.5934	Remote Similarity	NPD4693	Phase 3
0.5934	Remote Similarity	NPD5280	Approved
0.5934	Remote Similarity	NPD5205	Approved
0.5934	Remote Similarity	NPD4690	Approved
0.5934	Remote Similarity	NPD4138	Approved
0.5934	Remote Similarity	NPD4689	Approved
0.5934	Remote Similarity	NPD4688	Approved
0.5934	Remote Similarity	NPD4694	Approved
0.5934	Remote Similarity	NPD5690	Phase 2
0.5934	Remote Similarity	NPD5279	Phase 3
0.5934	Remote Similarity	NPD5786	Approved
0.593	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5285	Approved
0.5859	Remote Similarity	NPD5286	Approved
0.5859	Remote Similarity	NPD4696	Approved
0.5859	Remote Similarity	NPD4700	Approved
0.5851	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7838	Discovery
0.5849	Remote Similarity	NPD6053	Discontinued
0.5825	Remote Similarity	NPD6412	Phase 2
0.5816	Remote Similarity	NPD6084	Phase 2
0.5816	Remote Similarity	NPD6083	Phase 2
0.5806	Remote Similarity	NPD4722	Approved
0.5806	Remote Similarity	NPD4723	Approved
0.58	Remote Similarity	NPD5223	Approved
0.5794	Remote Similarity	NPD4632	Approved
0.5789	Remote Similarity	NPD5281	Approved
0.5789	Remote Similarity	NPD5284	Approved
0.5789	Remote Similarity	NPD7637	Suspended
0.5778	Remote Similarity	NPD7154	Phase 3
0.5773	Remote Similarity	NPD5695	Phase 3
0.5765	Remote Similarity	NPD8264	Approved
0.5761	Remote Similarity	NPD3618	Phase 1
0.5745	Remote Similarity	NPD5328	Approved
0.5743	Remote Similarity	NPD4633	Approved
0.5743	Remote Similarity	NPD5224	Approved
0.5743	Remote Similarity	NPD5226	Approved
0.5743	Remote Similarity	NPD5211	Phase 2
0.5743	Remote Similarity	NPD5225	Approved
0.573	Remote Similarity	NPD4692	Approved
0.573	Remote Similarity	NPD4139	Approved
0.5729	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD1145	Discontinued
0.5714	Remote Similarity	NPD4732	Discontinued
0.5698	Remote Similarity	NPD1346	Approved
0.5686	Remote Similarity	NPD5174	Approved
0.5686	Remote Similarity	NPD5175	Approved
0.5686	Remote Similarity	NPD4754	Approved
0.5684	Remote Similarity	NPD4096	Approved
0.5684	Remote Similarity	NPD3168	Discontinued
0.5684	Remote Similarity	NPD5785	Approved
0.5684	Remote Similarity	NPD46	Approved
0.5684	Remote Similarity	NPD7136	Phase 2
0.5684	Remote Similarity	NPD6698	Approved
0.5682	Remote Similarity	NPD7645	Phase 2
0.567	Remote Similarity	NPD5282	Discontinued
0.5644	Remote Similarity	NPD5344	Discontinued
0.5631	Remote Similarity	NPD5141	Approved
0.5625	Remote Similarity	NPD6079	Approved
0.5625	Remote Similarity	NPD7983	Approved
0.56	Remote Similarity	NPD7638	Approved
0.56	Remote Similarity	NPD5696	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