NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	2.699
LogD:	2.879
LogS:	-1.746
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.726
Synthetic Accessibility Score:	4.092
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:	-4.405
MDCK Permeability:	1.1137634828628507e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.882
30% Bioavailability (F30%):	0.113

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12
Plasma Protein Binding (PPB):	87.79714965820312%
Volume Distribution (VD):	0.701
Pgp-substrate:	14.394840240478516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.747
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.159
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	6.447
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.283
Skin Sensitization:	0.93
Carcinogencity:	0.418
Eye Corrosion:	0.255
Eye Irritation:	0.959
Respiratory Toxicity:	0.146

Download Data

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

Natural Product: NPC136813

Natural Product ID:	NPC136813
*Common Name:**	Schisanwilsonene A
IUPAC Name:	2-[(1R,3aS,8aR)-6-(hydroxymethyl)-3a-methyl-2,3,4,5,8,8a-hexahydro-1H-azulen-1-yl]propan-2-ol
Synonyms:
Standard InCHIKey:	QNYUIPNTIJJURA-UMVBOHGHSA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-14(2,17)12-7-9-15(3)8-6-11(10-16)4-5-13(12)15/h4,12-13,16-17H,5-10H2,1-3H3/t12-,13-,15-/m1/s1
SMILES:	OCC1=CC[C@H]2[C@@](CC1)(C)CC[C@H]2C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL539964
PubChem CID:	42638973
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
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19228000]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[19228000]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20462233]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23327759]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	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
Others	6

Activity Type	# Activity
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Inhibition	>=	25.0	%	PMID[540363]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	76.5	%	PMID[540363]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	27.5	%	PMID[540363]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	28.9	%	PMID[540363]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	11.3	%	PMID[540363]

☑ 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 NPC136813 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	146
0.1-0.2	1652
0.2-0.3	11067
0.3-0.4	14688
0.4-0.5	8008
0.5-0.6	5281
0.6-0.7	1561
0.7-0.8	265
0.8-0.85	20
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9531	High Similarity	NPC167527
0.8857	High Similarity	NPC126969
0.8841	High Similarity	NPC471659
0.8824	High Similarity	NPC471662
0.8788	High Similarity	NPC477791
0.8636	High Similarity	NPC162309
0.8615	High Similarity	NPC309300
0.8592	High Similarity	NPC471658
0.8571	High Similarity	NPC309178
0.8548	High Similarity	NPC278550
0.8485	Intermediate Similarity	NPC19569
0.8485	Intermediate Similarity	NPC187619
0.8429	Intermediate Similarity	NPC234527
0.8429	Intermediate Similarity	NPC14352
0.8382	Intermediate Similarity	NPC224532
0.8333	Intermediate Similarity	NPC476317
0.8333	Intermediate Similarity	NPC310643
0.8308	Intermediate Similarity	NPC210346
0.8286	Intermediate Similarity	NPC471660
0.8286	Intermediate Similarity	NPC41886
0.8281	Intermediate Similarity	NPC5698
0.8209	Intermediate Similarity	NPC477009
0.8209	Intermediate Similarity	NPC238352
0.8194	Intermediate Similarity	NPC313185
0.8182	Intermediate Similarity	NPC133368
0.8182	Intermediate Similarity	NPC211291
0.8182	Intermediate Similarity	NPC474480
0.8154	Intermediate Similarity	NPC323153
0.8154	Intermediate Similarity	NPC66020
0.8143	Intermediate Similarity	NPC471781
0.806	Intermediate Similarity	NPC300593
0.8028	Intermediate Similarity	NPC477792
0.8	Intermediate Similarity	NPC90115
0.8	Intermediate Similarity	NPC469321
0.8	Intermediate Similarity	NPC217570
0.7971	Intermediate Similarity	NPC472253
0.7971	Intermediate Similarity	NPC472255
0.7945	Intermediate Similarity	NPC23231
0.7945	Intermediate Similarity	NPC60818
0.7941	Intermediate Similarity	NPC205618
0.7941	Intermediate Similarity	NPC469326
0.7941	Intermediate Similarity	NPC261782
0.791	Intermediate Similarity	NPC473759
0.791	Intermediate Similarity	NPC474155
0.791	Intermediate Similarity	NPC124112
0.7887	Intermediate Similarity	NPC254845
0.7879	Intermediate Similarity	NPC135648
0.7879	Intermediate Similarity	NPC240506
0.7879	Intermediate Similarity	NPC234264
0.7879	Intermediate Similarity	NPC47840
0.7879	Intermediate Similarity	NPC252809
0.7846	Intermediate Similarity	NPC475830
0.7846	Intermediate Similarity	NPC10017
0.7838	Intermediate Similarity	NPC244488
0.7838	Intermediate Similarity	NPC247325
0.7838	Intermediate Similarity	NPC215481
0.7826	Intermediate Similarity	NPC267027
0.7826	Intermediate Similarity	NPC272125
0.7808	Intermediate Similarity	NPC27395
0.7808	Intermediate Similarity	NPC329090
0.7794	Intermediate Similarity	NPC110241
0.7794	Intermediate Similarity	NPC219940
0.7792	Intermediate Similarity	NPC264245
0.7792	Intermediate Similarity	NPC471661
0.7763	Intermediate Similarity	NPC47982
0.7763	Intermediate Similarity	NPC209430
0.7763	Intermediate Similarity	NPC84694
0.7763	Intermediate Similarity	NPC143182
0.7763	Intermediate Similarity	NPC30986
0.7763	Intermediate Similarity	NPC81306
0.7763	Intermediate Similarity	NPC28862
0.7763	Intermediate Similarity	NPC109546
0.7761	Intermediate Similarity	NPC63111
0.7761	Intermediate Similarity	NPC274704
0.7746	Intermediate Similarity	NPC471560
0.7746	Intermediate Similarity	NPC144647
0.7746	Intermediate Similarity	NPC473893
0.7727	Intermediate Similarity	NPC309825
0.7727	Intermediate Similarity	NPC122239
0.7727	Intermediate Similarity	NPC475931
0.7714	Intermediate Similarity	NPC69649
0.7714	Intermediate Similarity	NPC68703
0.7703	Intermediate Similarity	NPC319090
0.7703	Intermediate Similarity	NPC328104
0.7692	Intermediate Similarity	NPC49964
0.7692	Intermediate Similarity	NPC87489
0.7692	Intermediate Similarity	NPC133844
0.7692	Intermediate Similarity	NPC472465
0.7692	Intermediate Similarity	NPC218616
0.7692	Intermediate Similarity	NPC296701
0.7671	Intermediate Similarity	NPC474140
0.7671	Intermediate Similarity	NPC329763
0.7662	Intermediate Similarity	NPC209944
0.7662	Intermediate Similarity	NPC241290
0.7662	Intermediate Similarity	NPC164840
0.7662	Intermediate Similarity	NPC324772
0.7662	Intermediate Similarity	NPC234193
0.7647	Intermediate Similarity	NPC473508
0.7647	Intermediate Similarity	NPC279200
0.7639	Intermediate Similarity	NPC133873
0.7639	Intermediate Similarity	NPC34834
0.7639	Intermediate Similarity	NPC470041
0.7632	Intermediate Similarity	NPC474216
0.7632	Intermediate Similarity	NPC470944
0.7619	Intermediate Similarity	NPC192962
0.7612	Intermediate Similarity	NPC99487
0.7612	Intermediate Similarity	NPC471081
0.7606	Intermediate Similarity	NPC160209
0.7606	Intermediate Similarity	NPC96484
0.7606	Intermediate Similarity	NPC471238
0.76	Intermediate Similarity	NPC315261
0.7595	Intermediate Similarity	NPC474634
0.7595	Intermediate Similarity	NPC475789
0.7576	Intermediate Similarity	NPC155025
0.7571	Intermediate Similarity	NPC135650
0.7571	Intermediate Similarity	NPC230107
0.7568	Intermediate Similarity	NPC206875
0.7568	Intermediate Similarity	NPC201048
0.7568	Intermediate Similarity	NPC476366
0.7564	Intermediate Similarity	NPC23852
0.7564	Intermediate Similarity	NPC209620
0.7564	Intermediate Similarity	NPC320525
0.7564	Intermediate Similarity	NPC47761
0.7536	Intermediate Similarity	NPC140233
0.7536	Intermediate Similarity	NPC475704
0.7536	Intermediate Similarity	NPC107540
0.7536	Intermediate Similarity	NPC287744
0.7534	Intermediate Similarity	NPC469343
0.7534	Intermediate Similarity	NPC471272
0.7532	Intermediate Similarity	NPC181195
0.7532	Intermediate Similarity	NPC261125
0.75	Intermediate Similarity	NPC476439
0.75	Intermediate Similarity	NPC474248
0.75	Intermediate Similarity	NPC198968
0.75	Intermediate Similarity	NPC321867
0.75	Intermediate Similarity	NPC474047
0.75	Intermediate Similarity	NPC318495
0.75	Intermediate Similarity	NPC68679
0.75	Intermediate Similarity	NPC207007
0.75	Intermediate Similarity	NPC15152
0.75	Intermediate Similarity	NPC155986
0.75	Intermediate Similarity	NPC225342
0.75	Intermediate Similarity	NPC238485
0.75	Intermediate Similarity	NPC471454
0.75	Intermediate Similarity	NPC231310
0.75	Intermediate Similarity	NPC31037
0.75	Intermediate Similarity	NPC474900
0.75	Intermediate Similarity	NPC205845
0.7468	Intermediate Similarity	NPC101462
0.7468	Intermediate Similarity	NPC189972
0.7468	Intermediate Similarity	NPC50964
0.7468	Intermediate Similarity	NPC202389
0.7467	Intermediate Similarity	NPC263698
0.7467	Intermediate Similarity	NPC32832
0.7467	Intermediate Similarity	NPC113639
0.7465	Intermediate Similarity	NPC171225
0.7465	Intermediate Similarity	NPC308522
0.7465	Intermediate Similarity	NPC114651
0.7465	Intermediate Similarity	NPC74885
0.7463	Intermediate Similarity	NPC184049
0.7463	Intermediate Similarity	NPC99480
0.7432	Intermediate Similarity	NPC130665
0.7432	Intermediate Similarity	NPC474743
0.7429	Intermediate Similarity	NPC300442
0.7429	Intermediate Similarity	NPC61503
0.7429	Intermediate Similarity	NPC308844
0.7407	Intermediate Similarity	NPC274448
0.7403	Intermediate Similarity	NPC297996
0.7403	Intermediate Similarity	NPC473943
0.7403	Intermediate Similarity	NPC477514
0.7403	Intermediate Similarity	NPC285761
0.7391	Intermediate Similarity	NPC81615
0.7385	Intermediate Similarity	NPC148216
0.7385	Intermediate Similarity	NPC148163
0.7385	Intermediate Similarity	NPC298299
0.7385	Intermediate Similarity	NPC130209
0.7375	Intermediate Similarity	NPC471340
0.7375	Intermediate Similarity	NPC82623
0.7375	Intermediate Similarity	NPC320548
0.7375	Intermediate Similarity	NPC470384
0.7375	Intermediate Similarity	NPC317458
0.7368	Intermediate Similarity	NPC469646
0.7368	Intermediate Similarity	NPC107059
0.7368	Intermediate Similarity	NPC321016
0.7368	Intermediate Similarity	NPC470749
0.7368	Intermediate Similarity	NPC321381
0.7342	Intermediate Similarity	NPC474683
0.7342	Intermediate Similarity	NPC474759
0.7342	Intermediate Similarity	NPC7505
0.7342	Intermediate Similarity	NPC474752
0.7342	Intermediate Similarity	NPC472471
0.7342	Intermediate Similarity	NPC82986
0.7342	Intermediate Similarity	NPC474731
0.7333	Intermediate Similarity	NPC469534
0.7333	Intermediate Similarity	NPC306727
0.7333	Intermediate Similarity	NPC469533
0.7333	Intermediate Similarity	NPC469593
0.7324	Intermediate Similarity	NPC202017
0.7324	Intermediate Similarity	NPC311736
0.7324	Intermediate Similarity	NPC476406

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 NPC136813 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	2269
0.2-0.3	4398
0.3-0.4	1671
0.4-0.5	386
0.5-0.6	202
0.6-0.7	71
0.7-0.8	11
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
0.7808	Intermediate Similarity	NPD6926	Approved
0.7808	Intermediate Similarity	NPD6924	Approved
0.7662	Intermediate Similarity	NPD6931	Approved
0.7662	Intermediate Similarity	NPD6930	Phase 2
0.76	Intermediate Similarity	NPD6933	Approved
0.7532	Intermediate Similarity	NPD6929	Approved
0.75	Intermediate Similarity	NPD368	Approved
0.7436	Intermediate Similarity	NPD7514	Phase 3
0.7403	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD342	Phase 1
0.7375	Intermediate Similarity	NPD6695	Phase 3
0.7284	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5776	Phase 2
0.7273	Intermediate Similarity	NPD6925	Approved
0.726	Intermediate Similarity	NPD6923	Approved
0.726	Intermediate Similarity	NPD6922	Approved
0.7237	Intermediate Similarity	NPD6942	Approved
0.7237	Intermediate Similarity	NPD7339	Approved
0.7229	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7332	Phase 2
0.7215	Intermediate Similarity	NPD7525	Registered
0.7195	Intermediate Similarity	NPD6893	Approved
0.7179	Intermediate Similarity	NPD7145	Approved
0.7179	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7143	Approved
0.7162	Intermediate Similarity	NPD7144	Approved
0.7143	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6902	Approved
0.7067	Intermediate Similarity	NPD7152	Approved
0.7067	Intermediate Similarity	NPD4243	Approved
0.7067	Intermediate Similarity	NPD7151	Approved
0.7067	Intermediate Similarity	NPD7150	Approved
0.7051	Intermediate Similarity	NPD6932	Approved
0.7024	Intermediate Similarity	NPD7750	Discontinued
0.7024	Intermediate Similarity	NPD7524	Approved
0.7	Intermediate Similarity	NPD7509	Discontinued
0.6914	Remote Similarity	NPD6898	Phase 1
0.6883	Remote Similarity	NPD4785	Approved
0.6883	Remote Similarity	NPD4784	Approved
0.6875	Remote Similarity	NPD6683	Phase 2
0.6795	Remote Similarity	NPD8264	Approved
0.6795	Remote Similarity	NPD4190	Phase 3
0.6795	Remote Similarity	NPD5275	Approved
0.679	Remote Similarity	NPD4821	Approved
0.679	Remote Similarity	NPD4819	Approved
0.679	Remote Similarity	NPD4822	Approved
0.679	Remote Similarity	NPD4820	Approved
0.6747	Remote Similarity	NPD5362	Discontinued
0.6747	Remote Similarity	NPD5332	Approved
0.6747	Remote Similarity	NPD5331	Approved
0.6707	Remote Similarity	NPD4790	Discontinued
0.6705	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6627	Remote Similarity	NPD3667	Approved
0.6585	Remote Similarity	NPD4748	Discontinued
0.6543	Remote Similarity	NPD4268	Approved
0.6543	Remote Similarity	NPD4271	Approved
0.6522	Remote Similarity	NPD4219	Approved
0.6512	Remote Similarity	NPD5279	Phase 3
0.6477	Remote Similarity	NPD4753	Phase 2
0.6471	Remote Similarity	NPD3133	Approved
0.6471	Remote Similarity	NPD3665	Phase 1
0.6471	Remote Similarity	NPD3666	Approved
0.6429	Remote Similarity	NPD4270	Approved
0.6429	Remote Similarity	NPD4269	Approved
0.6429	Remote Similarity	NPD4223	Phase 3
0.6429	Remote Similarity	NPD4221	Approved
0.6395	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7637	Suspended
0.6329	Remote Similarity	NPD4732	Discontinued
0.6322	Remote Similarity	NPD3618	Phase 1
0.6292	Remote Similarity	NPD5328	Approved
0.6279	Remote Similarity	NPD4197	Approved
0.6265	Remote Similarity	NPD7645	Phase 2
0.6264	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD4265	Approved
0.6222	Remote Similarity	NPD5785	Approved
0.6207	Remote Similarity	NPD1696	Phase 3
0.6207	Remote Similarity	NPD5329	Approved
0.6207	Remote Similarity	NPD5363	Approved
0.619	Remote Similarity	NPD4252	Approved
0.6163	Remote Similarity	NPD7154	Phase 3
0.6163	Remote Similarity	NPD4788	Approved
0.6154	Remote Similarity	NPD6079	Approved
0.6136	Remote Similarity	NPD4138	Approved
0.6136	Remote Similarity	NPD4694	Approved
0.6136	Remote Similarity	NPD4623	Approved
0.6136	Remote Similarity	NPD4693	Phase 3
0.6136	Remote Similarity	NPD4689	Approved
0.6136	Remote Similarity	NPD4519	Discontinued
0.6136	Remote Similarity	NPD5690	Phase 2
0.6136	Remote Similarity	NPD5280	Approved
0.6136	Remote Similarity	NPD5786	Approved
0.6136	Remote Similarity	NPD4690	Approved
0.6136	Remote Similarity	NPD4688	Approved
0.6136	Remote Similarity	NPD5205	Approved
0.6129	Remote Similarity	NPD5210	Approved
0.6129	Remote Similarity	NPD4629	Approved
0.6118	Remote Similarity	NPD5369	Approved
0.6111	Remote Similarity	NPD6051	Approved
0.6098	Remote Similarity	NPD1346	Approved
0.6082	Remote Similarity	NPD5211	Phase 2
0.6044	Remote Similarity	NPD7136	Phase 2
0.6042	Remote Similarity	NPD7639	Approved
0.6042	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD4723	Approved
0.6	Remote Similarity	NPD4518	Approved
0.6	Remote Similarity	NPD4722	Approved
0.6	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD6083	Phase 2
0.596	Remote Similarity	NPD5141	Approved
0.5957	Remote Similarity	NPD5695	Phase 3
0.5955	Remote Similarity	NPD4249	Approved
0.5949	Remote Similarity	NPD1082	Approved
0.5938	Remote Similarity	NPD7638	Approved
0.593	Remote Similarity	NPD4139	Approved
0.593	Remote Similarity	NPD4692	Approved
0.5914	Remote Similarity	NPD6399	Phase 3
0.5909	Remote Similarity	NPD3668	Phase 3
0.5895	Remote Similarity	NPD4697	Phase 3
0.5895	Remote Similarity	NPD5222	Approved
0.5895	Remote Similarity	NPD5221	Approved
0.5895	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD4250	Approved
0.5889	Remote Similarity	NPD4251	Approved
0.5876	Remote Similarity	NPD4700	Approved
0.5876	Remote Similarity	NPD5286	Approved
0.5876	Remote Similarity	NPD4696	Approved
0.5876	Remote Similarity	NPD5285	Approved
0.587	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4096	Approved
0.5862	Remote Similarity	NPD6435	Approved
0.5844	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5173	Approved
0.5825	Remote Similarity	NPD6371	Approved
0.5816	Remote Similarity	NPD5223	Approved
0.5806	Remote Similarity	NPD5281	Approved
0.5806	Remote Similarity	NPD5284	Approved
0.5789	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4225	Approved
0.5773	Remote Similarity	NPD5696	Approved
0.5769	Remote Similarity	NPD7331	Phase 2
0.5765	Remote Similarity	NPD3617	Approved
0.5758	Remote Similarity	NPD5226	Approved
0.5758	Remote Similarity	NPD4633	Approved
0.5758	Remote Similarity	NPD5224	Approved
0.5758	Remote Similarity	NPD5225	Approved
0.5747	Remote Similarity	NPD857	Phase 3
0.5733	Remote Similarity	NPD1145	Discontinued
0.573	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4754	Approved
0.57	Remote Similarity	NPD5175	Approved
0.57	Remote Similarity	NPD5174	Approved
0.5682	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD4191	Approved
0.5658	Remote Similarity	NPD4194	Approved
0.5658	Remote Similarity	NPD4193	Approved
0.5658	Remote Similarity	NPD4192	Approved
0.5652	Remote Similarity	NPD6672	Approved
0.5652	Remote Similarity	NPD5737	Approved
0.5641	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD7341	Phase 2
0.5632	Remote Similarity	NPD4695	Discontinued
0.5612	Remote Similarity	NPD5290	Discontinued
0.5604	Remote Similarity	NPD6409	Approved
0.5604	Remote Similarity	NPD6098	Approved
0.5604	Remote Similarity	NPD5330	Approved
0.5604	Remote Similarity	NPD7146	Approved
0.5604	Remote Similarity	NPD7521	Approved
0.5604	Remote Similarity	NPD6684	Approved
0.5604	Remote Similarity	NPD7334	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