NPASS Compound

Structure

NPC201069 OpenBabel07101719522D 23 25 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 23 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 16 21 1 1 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 21 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.24
Volume:	355.774
LogP:	6.287
LogD:	4.694
LogS:	-5.596
# Rotatable Bonds:	2
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	3.593
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.902
MDCK Permeability:	1.5346553482231684e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.176
Plasma Protein Binding (PPB):	98.54816436767578%
Volume Distribution (VD):	4.295
Pgp-substrate:	2.139784097671509%

ADMET: Metabolism

CYP1A2-inhibitor:	0.341
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.446
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.29
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.448
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.51
CYP3A4-substrate:	0.658

ADMET: Excretion

Clearance (CL):	6.015
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.457
Maximum Recommended Daily Dose:	0.553
Skin Sensitization:	0.88
Carcinogencity:	0.121
Eye Corrosion:	0.004
Eye Irritation:	0.723
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC201069

Natural Product ID:	NPC201069
*Common Name:**	11-Hydroxy-12-Methoxyabietatriene
IUPAC Name:	(4bS,8aS)-3-methoxy-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-4-ol
Synonyms:
Standard InCHIKey:	NCQBQRRNDYBXHO-KKSFZXQISA-N
Standard InCHI:	InChI=1S/C21H32O2/c1-13(2)15-12-14-8-9-16-20(3,4)10-7-11-21(16,5)17(14)18(22)19(15)23-6/h12-13,16,22H,7-11H2,1-6H3/t16-,21-/m0/s1
SMILES:	COc1c(O)c2c(cc1C(C)C)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252751
PubChem CID:	14827262
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO13465	Salvia broussonetii	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[15969497]
NPO13465	Salvia broussonetii	Species	Lamiaceae	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
LD50	2
Others	3

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1161	Cell Line	CHO	Cricetulus griseus	LD50	>	100.0	ug ml-1	PMID[571418]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LD50	=	0.15	ug ml-1	PMID[571418]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	102.0	%	PMID[571418]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	91.0	%	PMID[571418]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	mortality	=	14.0	%	PMID[571418]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	EC50	=	10.2	microg/cm2	PMID[571418]

☑ 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 NPC201069 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	400
0.1-0.2	1750
0.2-0.3	3754
0.3-0.4	10606
0.4-0.5	8431
0.5-0.6	5970
0.6-0.7	8722
0.7-0.8	2718
0.8-0.85	292
0.85-0.9	47
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9603	High Similarity	NPC227719
0.938	High Similarity	NPC68292
0.912	High Similarity	NPC228771
0.912	High Similarity	NPC29008
0.912	High Similarity	NPC266705
0.907	High Similarity	NPC228843
0.8992	High Similarity	NPC312341
0.8968	High Similarity	NPC9067
0.8923	High Similarity	NPC321502
0.8906	High Similarity	NPC277458
0.8906	High Similarity	NPC307050
0.888	High Similarity	NPC30462
0.8828	High Similarity	NPC471077
0.876	High Similarity	NPC23012
0.8731	High Similarity	NPC242715
0.8731	High Similarity	NPC56329
0.8731	High Similarity	NPC22902
0.8722	High Similarity	NPC252343
0.8722	High Similarity	NPC313081
0.871	High Similarity	NPC310338
0.871	High Similarity	NPC281298
0.8699	High Similarity	NPC16030
0.8696	High Similarity	NPC196941
0.8696	High Similarity	NPC309169
0.8678	High Similarity	NPC317869
0.8667	High Similarity	NPC275061
0.8667	High Similarity	NPC132804
0.8667	High Similarity	NPC220344
0.8667	High Similarity	NPC243996
0.8667	High Similarity	NPC132723
0.8667	High Similarity	NPC76032
0.8657	High Similarity	NPC30632
0.8651	High Similarity	NPC474115
0.8647	High Similarity	NPC311256
0.8647	High Similarity	NPC125649
0.8647	High Similarity	NPC141023
0.8647	High Similarity	NPC209199
0.8643	High Similarity	NPC470757
0.864	High Similarity	NPC165133
0.864	High Similarity	NPC232316
0.864	High Similarity	NPC56214
0.864	High Similarity	NPC95614
0.864	High Similarity	NPC242885
0.864	High Similarity	NPC227217
0.864	High Similarity	NPC117780
0.8636	High Similarity	NPC14224
0.8636	High Similarity	NPC161958
0.8636	High Similarity	NPC227002
0.8626	High Similarity	NPC99795
0.8603	High Similarity	NPC12668
0.8603	High Similarity	NPC308768
0.8595	High Similarity	NPC471179
0.8593	High Similarity	NPC200935
0.8593	High Similarity	NPC230919
0.8593	High Similarity	NPC266453
0.8583	High Similarity	NPC152946
0.8582	High Similarity	NPC294884
0.8582	High Similarity	NPC158142
0.8582	High Similarity	NPC200557
0.8582	High Similarity	NPC108198
0.8582	High Similarity	NPC241241
0.8582	High Similarity	NPC69029
0.8582	High Similarity	NPC10314
0.8571	High Similarity	NPC58752
0.8561	High Similarity	NPC78575
0.8538	High Similarity	NPC21563
0.8529	High Similarity	NPC105847
0.8529	High Similarity	NPC243759
0.8529	High Similarity	NPC114171
0.8529	High Similarity	NPC218131
0.8529	High Similarity	NPC6300
0.8529	High Similarity	NPC184613
0.8529	High Similarity	NPC230124
0.8527	High Similarity	NPC76119
0.8527	High Similarity	NPC4286
0.8521	High Similarity	NPC183380
0.8519	High Similarity	NPC202846
0.8519	High Similarity	NPC143139
0.8511	High Similarity	NPC52692
0.8507	High Similarity	NPC471942
0.8504	High Similarity	NPC38996
0.8504	High Similarity	NPC160380
0.8496	Intermediate Similarity	NPC189482
0.8496	Intermediate Similarity	NPC73656
0.8496	Intermediate Similarity	NPC59239
0.8492	Intermediate Similarity	NPC103916
0.8492	Intermediate Similarity	NPC135467
0.8492	Intermediate Similarity	NPC260832
0.8489	Intermediate Similarity	NPC164183
0.848	Intermediate Similarity	NPC470626
0.8478	Intermediate Similarity	NPC175838
0.8478	Intermediate Similarity	NPC183709
0.8473	Intermediate Similarity	NPC472968
0.8468	Intermediate Similarity	NPC312105
0.8467	Intermediate Similarity	NPC234568
0.8467	Intermediate Similarity	NPC198038
0.8462	Intermediate Similarity	NPC470724
0.8456	Intermediate Similarity	NPC266006
0.8456	Intermediate Similarity	NPC151656
0.8438	Intermediate Similarity	NPC471794
0.8438	Intermediate Similarity	NPC85488
0.8425	Intermediate Similarity	NPC129176
0.8421	Intermediate Similarity	NPC15543
0.8406	Intermediate Similarity	NPC472089
0.84	Intermediate Similarity	NPC293619
0.8397	Intermediate Similarity	NPC252131
0.8397	Intermediate Similarity	NPC186889
0.8394	Intermediate Similarity	NPC79622
0.8394	Intermediate Similarity	NPC212942
0.8394	Intermediate Similarity	NPC29868
0.8392	Intermediate Similarity	NPC195561
0.8387	Intermediate Similarity	NPC35797
0.8387	Intermediate Similarity	NPC192948
0.8372	Intermediate Similarity	NPC317769
0.8372	Intermediate Similarity	NPC31344
0.8372	Intermediate Similarity	NPC280704
0.837	Intermediate Similarity	NPC160697
0.8361	Intermediate Similarity	NPC176279
0.8361	Intermediate Similarity	NPC260323
0.8358	Intermediate Similarity	NPC85595
0.8358	Intermediate Similarity	NPC303144
0.8357	Intermediate Similarity	NPC469795
0.8357	Intermediate Similarity	NPC473845
0.8357	Intermediate Similarity	NPC133251
0.8346	Intermediate Similarity	NPC143483
0.8346	Intermediate Similarity	NPC126836
0.8346	Intermediate Similarity	NPC249425
0.8345	Intermediate Similarity	NPC472087
0.8345	Intermediate Similarity	NPC470917
0.8345	Intermediate Similarity	NPC475227
0.8345	Intermediate Similarity	NPC106669
0.8345	Intermediate Similarity	NPC472088
0.8345	Intermediate Similarity	NPC191231
0.8345	Intermediate Similarity	NPC200645
0.8333	Intermediate Similarity	NPC165026
0.8333	Intermediate Similarity	NPC2745
0.8333	Intermediate Similarity	NPC295719
0.8333	Intermediate Similarity	NPC73505
0.8333	Intermediate Similarity	NPC28765
0.8333	Intermediate Similarity	NPC34431
0.8322	Intermediate Similarity	NPC471852
0.832	Intermediate Similarity	NPC477137
0.832	Intermediate Similarity	NPC471668
0.832	Intermediate Similarity	NPC308311
0.832	Intermediate Similarity	NPC38893
0.8298	Intermediate Similarity	NPC307205
0.8286	Intermediate Similarity	NPC474104
0.8281	Intermediate Similarity	NPC207613
0.8276	Intermediate Similarity	NPC157783
0.8273	Intermediate Similarity	NPC35216
0.8271	Intermediate Similarity	NPC206028
0.8264	Intermediate Similarity	NPC158784
0.8258	Intermediate Similarity	NPC106511
0.8258	Intermediate Similarity	NPC476536
0.8254	Intermediate Similarity	NPC164386
0.8254	Intermediate Similarity	NPC304510
0.8254	Intermediate Similarity	NPC172219
0.8254	Intermediate Similarity	NPC25648
0.8252	Intermediate Similarity	NPC212142
0.8252	Intermediate Similarity	NPC474940
0.8252	Intermediate Similarity	NPC303013
0.8252	Intermediate Similarity	NPC159697
0.8252	Intermediate Similarity	NPC474795
0.8252	Intermediate Similarity	NPC130959
0.8248	Intermediate Similarity	NPC300846
0.8248	Intermediate Similarity	NPC476639
0.8248	Intermediate Similarity	NPC205442
0.8248	Intermediate Similarity	NPC114155
0.8244	Intermediate Similarity	NPC148627
0.8244	Intermediate Similarity	NPC470726
0.8235	Intermediate Similarity	NPC469659
0.8235	Intermediate Similarity	NPC193026
0.8235	Intermediate Similarity	NPC187616
0.8235	Intermediate Similarity	NPC7515
0.8235	Intermediate Similarity	NPC49603
0.8235	Intermediate Similarity	NPC289258
0.8235	Intermediate Similarity	NPC206737
0.8235	Intermediate Similarity	NPC56764
0.8235	Intermediate Similarity	NPC276026
0.8235	Intermediate Similarity	NPC188378
0.8235	Intermediate Similarity	NPC555
0.8227	Intermediate Similarity	NPC209085
0.8227	Intermediate Similarity	NPC224884
0.8217	Intermediate Similarity	NPC470212
0.8217	Intermediate Similarity	NPC312675
0.8217	Intermediate Similarity	NPC343720
0.8217	Intermediate Similarity	NPC324571
0.8217	Intermediate Similarity	NPC54872
0.8217	Intermediate Similarity	NPC113865
0.8217	Intermediate Similarity	NPC184651
0.8217	Intermediate Similarity	NPC262156
0.8217	Intermediate Similarity	NPC473853
0.8214	Intermediate Similarity	NPC323126
0.8214	Intermediate Similarity	NPC186033
0.8211	Intermediate Similarity	NPC257124
0.8211	Intermediate Similarity	NPC173746
0.8211	Intermediate Similarity	NPC8547
0.8211	Intermediate Similarity	NPC195873
0.8211	Intermediate Similarity	NPC156840
0.8211	Intermediate Similarity	NPC470723

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 NPC201069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	986
0.2-0.3	1534
0.3-0.4	2819
0.4-0.5	1775
0.5-0.6	1017
0.6-0.7	555
0.7-0.8	105
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8923	High Similarity	NPD3619	Clinical (unspecified phase)
0.8923	High Similarity	NPD3620	Phase 2
0.8211	Intermediate Similarity	NPD228	Approved
0.8143	Intermediate Similarity	NPD6674	Discontinued
0.8102	Intermediate Similarity	NPD4097	Suspended
0.8092	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.808	Intermediate Similarity	NPD5283	Phase 1
0.7956	Intermediate Similarity	NPD4060	Phase 1
0.7923	Intermediate Similarity	NPD4626	Approved
0.791	Intermediate Similarity	NPD4624	Approved
0.7899	Intermediate Similarity	NPD5735	Approved
0.7899	Intermediate Similarity	NPD3657	Discovery
0.782	Intermediate Similarity	NPD5327	Phase 3
0.7778	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD6696	Suspended
0.776	Intermediate Similarity	NPD3022	Approved
0.776	Intermediate Similarity	NPD3021	Approved
0.7752	Intermediate Similarity	NPD7340	Approved
0.7737	Intermediate Similarity	NPD3027	Phase 3
0.7717	Intermediate Similarity	NPD7635	Approved
0.7687	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3092	Approved
0.7634	Intermediate Similarity	NPD3091	Approved
0.7609	Intermediate Similarity	NPD4625	Phase 3
0.76	Intermediate Similarity	NPD2342	Discontinued
0.7591	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6353	Approved
0.7576	Intermediate Similarity	NPD5691	Approved
0.7571	Intermediate Similarity	NPD4140	Approved
0.7538	Intermediate Similarity	NPD7157	Approved
0.7536	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1398	Phase 1
0.75	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD8651	Approved
0.7482	Intermediate Similarity	NPD7095	Approved
0.7466	Intermediate Similarity	NPD8166	Discontinued
0.7466	Intermediate Similarity	NPD7003	Approved
0.7447	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1613	Approved
0.7445	Intermediate Similarity	NPD3094	Phase 2
0.7444	Intermediate Similarity	NPD1651	Approved
0.7444	Intermediate Similarity	NPD1357	Approved
0.7429	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4749	Approved
0.7419	Intermediate Similarity	NPD7833	Phase 2
0.7419	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7831	Phase 2
0.7405	Intermediate Similarity	NPD6671	Approved
0.7397	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD3019	Approved
0.7388	Intermediate Similarity	NPD4059	Approved
0.7383	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6234	Discontinued
0.7358	Intermediate Similarity	NPD27	Approved
0.7358	Intermediate Similarity	NPD2489	Approved
0.7355	Intermediate Similarity	NPD1809	Phase 2
0.7338	Intermediate Similarity	NPD2861	Phase 2
0.7338	Intermediate Similarity	NPD5736	Approved
0.7315	Intermediate Similarity	NPD7041	Phase 2
0.7315	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7473	Discontinued
0.731	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD5110	Phase 2
0.7305	Intermediate Similarity	NPD5111	Phase 2
0.7305	Intermediate Similarity	NPD5109	Approved
0.7286	Intermediate Similarity	NPD4908	Phase 1
0.7279	Intermediate Similarity	NPD1281	Approved
0.7279	Intermediate Similarity	NPD3705	Approved
0.7273	Intermediate Similarity	NPD37	Approved
0.7266	Intermediate Similarity	NPD2684	Approved
0.726	Intermediate Similarity	NPD5763	Approved
0.726	Intermediate Similarity	NPD5762	Approved
0.7259	Intermediate Similarity	NPD3095	Discontinued
0.7259	Intermediate Similarity	NPD2932	Approved
0.7254	Intermediate Similarity	NPD2674	Phase 3
0.7254	Intermediate Similarity	NPD8032	Phase 2
0.7233	Intermediate Similarity	NPD6232	Discontinued
0.7233	Intermediate Similarity	NPD3051	Approved
0.723	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4110	Phase 3
0.723	Intermediate Similarity	NPD6331	Phase 2
0.7226	Intermediate Similarity	NPD2230	Approved
0.7226	Intermediate Similarity	NPD2233	Approved
0.7226	Intermediate Similarity	NPD2232	Approved
0.7219	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7458	Discontinued
0.7188	Intermediate Similarity	NPD2970	Approved
0.7188	Intermediate Similarity	NPD2969	Approved
0.7183	Intermediate Similarity	NPD3145	Approved
0.7183	Intermediate Similarity	NPD3144	Approved
0.7181	Intermediate Similarity	NPD5241	Discontinued
0.7181	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3020	Approved
0.7176	Intermediate Similarity	NPD7843	Approved
0.7174	Intermediate Similarity	NPD1669	Approved
0.7172	Intermediate Similarity	NPD6896	Approved
0.7172	Intermediate Similarity	NPD6895	Approved
0.7164	Intermediate Similarity	NPD5536	Phase 2
0.716	Intermediate Similarity	NPD7228	Approved
0.7154	Intermediate Similarity	NPD288	Approved
0.7153	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2898	Approved
0.7143	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD7028	Phase 2
0.7134	Intermediate Similarity	NPD4966	Approved
0.7134	Intermediate Similarity	NPD4965	Approved
0.7134	Intermediate Similarity	NPD4967	Phase 2
0.7133	Intermediate Similarity	NPD6663	Approved
0.7123	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7037	Approved
0.7092	Intermediate Similarity	NPD3018	Phase 2
0.7083	Intermediate Similarity	NPD1558	Phase 1
0.7083	Intermediate Similarity	NPD3109	Approved
0.7083	Intermediate Similarity	NPD3110	Approved
0.7077	Intermediate Similarity	NPD5451	Approved
0.7077	Intermediate Similarity	NPD4750	Phase 3
0.7073	Intermediate Similarity	NPD844	Approved
0.7063	Intermediate Similarity	NPD8127	Discontinued
0.7063	Intermediate Similarity	NPD7294	Phase 1
0.7063	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7985	Registered
0.7049	Intermediate Similarity	NPD845	Approved
0.7047	Intermediate Similarity	NPD5177	Phase 3
0.7039	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7644	Approved
0.7034	Intermediate Similarity	NPD6355	Discontinued
0.7029	Intermediate Similarity	NPD1611	Approved
0.7015	Intermediate Similarity	NPD709	Approved
0.7015	Intermediate Similarity	NPD6387	Discontinued
0.7007	Intermediate Similarity	NPD6516	Phase 2
0.7007	Intermediate Similarity	NPD2668	Approved
0.7007	Intermediate Similarity	NPD2286	Discontinued
0.7007	Intermediate Similarity	NPD2667	Approved
0.7007	Intermediate Similarity	NPD5846	Approved
0.7006	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5929	Approved
0.7006	Intermediate Similarity	NPD4578	Approved
0.7006	Intermediate Similarity	NPD7312	Approved
0.7006	Intermediate Similarity	NPD7311	Approved
0.7006	Intermediate Similarity	NPD4577	Approved
0.7006	Intermediate Similarity	NPD7310	Approved
0.7006	Intermediate Similarity	NPD7313	Approved
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6090	Discontinued
0.6992	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9296	Approved
0.6986	Remote Similarity	NPD2157	Approved
0.6984	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9494	Approved
0.6966	Remote Similarity	NPD2979	Phase 3
0.6964	Remote Similarity	NPD7309	Approved
0.6963	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2438	Suspended
0.6944	Remote Similarity	NPD5718	Phase 2
0.6944	Remote Similarity	NPD6798	Discontinued
0.6943	Remote Similarity	NPD5722	Discontinued
0.6941	Remote Similarity	NPD7906	Approved
0.6939	Remote Similarity	NPD6111	Discontinued
0.6935	Remote Similarity	NPD2859	Approved
0.6935	Remote Similarity	NPD2860	Approved
0.6934	Remote Similarity	NPD4093	Discontinued
0.6929	Remote Similarity	NPD2983	Phase 2
0.6929	Remote Similarity	NPD6583	Phase 3
0.6929	Remote Similarity	NPD6582	Phase 2
0.6929	Remote Similarity	NPD2982	Phase 2
0.6928	Remote Similarity	NPD3645	Discontinued
0.6923	Remote Similarity	NPD290	Approved
0.6923	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1138	Approved
0.6909	Remote Similarity	NPD5844	Phase 1
0.6901	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4108	Discontinued
0.6889	Remote Similarity	NPD4198	Discontinued
0.6887	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1778	Approved
0.6884	Remote Similarity	NPD1751	Approved
0.6883	Remote Similarity	NPD6273	Approved
0.6882	Remote Similarity	NPD4663	Approved
0.6879	Remote Similarity	NPD2922	Phase 1
0.6875	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2420	Approved
0.6863	Remote Similarity	NPD2421	Approved
0.6861	Remote Similarity	NPD1548	Phase 1
0.686	Remote Similarity	NPD2490	Approved
0.686	Remote Similarity	NPD2488	Approved
0.6857	Remote Similarity	NPD2981	Phase 2

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