NPASS Compound

Structure

CID186851 OpenBabel06191715562D 25 28 0 0 1 0 0 0 0 0999 V2000 -4.1225 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7624 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 1.4781 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4533 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 14 1 0 0 0 0 5 20 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 14 23 2 0 0 0 0 14 25 1 0 0 0 0 15 19 1 1 0 0 0 16 19 1 1 0 0 0 16 22 1 0 0 0 0 17 21 1 1 0 0 0 17 22 1 0 0 0 0 18 20 1 1 0 0 0 18 25 1 0 0 0 0 19 4 1 1 0 0 0 20 22 1 1 0 0 0 21 6 1 1 0 0 0 21 24 1 0 0 0 0 22 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.27
Volume:	378.577
LogP:	3.758
LogD:	3.849
LogS:	-5.022
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.744
Synthetic Accessibility Score:	5.353
Fsp3:	0.955
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:	-4.89
MDCK Permeability:	5.094995140098035e-05
Pgp-inhibitor:	0.579
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.739

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	93.63943481445312%
Volume Distribution (VD):	1.189
Pgp-substrate:	3.297022819519043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.158
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.23
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.507
CYP3A4-substrate:	0.576

ADMET: Excretion

Clearance (CL):	3.959
Half-life (T1/2):	0.396

ADMET: Toxicity

hERG Blockers:	0.114
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.094
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.126
Skin Sensitization:	0.792
Carcinogencity:	0.027
Eye Corrosion:	0.954
Eye Irritation:	0.919
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC186851

Natural Product ID:	NPC186851
*Common Name:**	Azorellanol
IUPAC Name:	n.a.
Synonyms:	Azorellanol
Standard InCHIKey:	KLONPCIQOJGNBV-NBWOUMIXSA-N
Standard InCHI:	InChI=1S/C22H36O3/c1-13(2)15-7-8-16-19(15,4)12-18(25-14(3)23)20(5)9-10-21(6,24)17-11-22(16,17)20/h13,15-18,24H,7-12H2,1-6H3/t15-,16-,17+,18+,19-,20-,21-,22-/m1/s1
SMILES:	CC(C)[C@H]1CC[C@@H]2[C@]1(C)C[C@@H]([C@@]1(C)CC[C@](C)([C@@H]3C[C@]213)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2205117
PubChem CID:	10383143
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003548] Valparane and mulinane 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
NPO26599	Azorella yareta	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26599	Azorella yareta	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	ug.mL-1	PMID[522527]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	12.5	ug.mL-1	PMID[522527]

☑ 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 NPC186851 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	343
0.1-0.2	3550
0.2-0.3	14164
0.3-0.4	10225
0.4-0.5	5470
0.5-0.6	5876
0.6-0.7	2568
0.7-0.8	462
0.8-0.85	33
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8933	High Similarity	NPC476176
0.8919	High Similarity	NPC212453
0.8816	High Similarity	NPC474714
0.8701	High Similarity	NPC73515
0.8684	High Similarity	NPC220379
0.8625	High Similarity	NPC131365
0.8553	High Similarity	NPC471045
0.8519	High Similarity	NPC5943
0.8514	High Similarity	NPC272359
0.8462	Intermediate Similarity	NPC190940
0.8354	Intermediate Similarity	NPC60018
0.8354	Intermediate Similarity	NPC154043
0.8354	Intermediate Similarity	NPC286719
0.8354	Intermediate Similarity	NPC202688
0.8354	Intermediate Similarity	NPC477286
0.8333	Intermediate Similarity	NPC472951
0.8333	Intermediate Similarity	NPC472943
0.8312	Intermediate Similarity	NPC471769
0.8272	Intermediate Similarity	NPC266651
0.825	Intermediate Similarity	NPC477285
0.825	Intermediate Similarity	NPC111582
0.8243	Intermediate Similarity	NPC473279
0.8243	Intermediate Similarity	NPC187471
0.8243	Intermediate Similarity	NPC470071
0.8243	Intermediate Similarity	NPC195530
0.8243	Intermediate Similarity	NPC252182
0.8243	Intermediate Similarity	NPC1340
0.8205	Intermediate Similarity	NPC201276
0.8205	Intermediate Similarity	NPC80891
0.8205	Intermediate Similarity	NPC477287
0.8194	Intermediate Similarity	NPC476928
0.8182	Intermediate Similarity	NPC476233
0.8171	Intermediate Similarity	NPC155531
0.8171	Intermediate Similarity	NPC477283
0.8171	Intermediate Similarity	NPC215968
0.8148	Intermediate Similarity	NPC473336
0.8148	Intermediate Similarity	NPC471044
0.8125	Intermediate Similarity	NPC472504
0.8118	Intermediate Similarity	NPC473066
0.8101	Intermediate Similarity	NPC206735
0.8101	Intermediate Similarity	NPC477851
0.8077	Intermediate Similarity	NPC171426
0.8077	Intermediate Similarity	NPC324700
0.8077	Intermediate Similarity	NPC34046
0.8077	Intermediate Similarity	NPC224802
0.8077	Intermediate Similarity	NPC80089
0.8026	Intermediate Similarity	NPC472945
0.8026	Intermediate Similarity	NPC472944
0.8	Intermediate Similarity	NPC58631
0.8	Intermediate Similarity	NPC127283
0.8	Intermediate Similarity	NPC8004
0.8	Intermediate Similarity	NPC470154
0.8	Intermediate Similarity	NPC10274
0.8	Intermediate Similarity	NPC77756
0.8	Intermediate Similarity	NPC12933
0.7973	Intermediate Similarity	NPC254037
0.7973	Intermediate Similarity	NPC299948
0.7973	Intermediate Similarity	NPC470830
0.7973	Intermediate Similarity	NPC66407
0.7973	Intermediate Similarity	NPC129829
0.7973	Intermediate Similarity	NPC241085
0.7971	Intermediate Similarity	NPC95958
0.7952	Intermediate Similarity	NPC103782
0.7952	Intermediate Similarity	NPC114378
0.7949	Intermediate Similarity	NPC171658
0.7945	Intermediate Similarity	NPC475884
0.7945	Intermediate Similarity	NPC473230
0.7931	Intermediate Similarity	NPC151214
0.7931	Intermediate Similarity	NPC191915
0.7927	Intermediate Similarity	NPC299963
0.7927	Intermediate Similarity	NPC319909
0.7922	Intermediate Similarity	NPC91387
0.7922	Intermediate Similarity	NPC231680
0.7922	Intermediate Similarity	NPC212733
0.7922	Intermediate Similarity	NPC270306
0.7917	Intermediate Similarity	NPC474380
0.7917	Intermediate Similarity	NPC41577
0.7917	Intermediate Similarity	NPC473276
0.7907	Intermediate Similarity	NPC52756
0.7901	Intermediate Similarity	NPC477284
0.7901	Intermediate Similarity	NPC477446
0.7901	Intermediate Similarity	NPC470155
0.7901	Intermediate Similarity	NPC477447
0.7895	Intermediate Similarity	NPC472341
0.7895	Intermediate Similarity	NPC473238
0.7875	Intermediate Similarity	NPC16449
0.7875	Intermediate Similarity	NPC261616
0.7867	Intermediate Similarity	NPC282454
0.7867	Intermediate Similarity	NPC192192
0.7838	Intermediate Similarity	NPC474756
0.7831	Intermediate Similarity	NPC235402
0.7821	Intermediate Similarity	NPC4209
0.7805	Intermediate Similarity	NPC69953
0.7805	Intermediate Similarity	NPC29342
0.7805	Intermediate Similarity	NPC2572
0.7792	Intermediate Similarity	NPC55508
0.7792	Intermediate Similarity	NPC280026
0.7792	Intermediate Similarity	NPC74639
0.7792	Intermediate Similarity	NPC475458
0.7792	Intermediate Similarity	NPC167702
0.7778	Intermediate Similarity	NPC69149
0.7778	Intermediate Similarity	NPC470156
0.7765	Intermediate Similarity	NPC201607
0.7765	Intermediate Similarity	NPC56777
0.7763	Intermediate Similarity	NPC100586
0.7763	Intermediate Similarity	NPC157422
0.7763	Intermediate Similarity	NPC109457
0.7763	Intermediate Similarity	NPC157777
0.7763	Intermediate Similarity	NPC131506
0.7763	Intermediate Similarity	NPC127094
0.7753	Intermediate Similarity	NPC156377
0.7753	Intermediate Similarity	NPC252056
0.775	Intermediate Similarity	NPC47808
0.7746	Intermediate Similarity	NPC95804
0.7746	Intermediate Similarity	NPC185547
0.7738	Intermediate Similarity	NPC64862
0.7738	Intermediate Similarity	NPC302111
0.7733	Intermediate Similarity	NPC477820
0.7722	Intermediate Similarity	NPC11907
0.7722	Intermediate Similarity	NPC474404
0.7722	Intermediate Similarity	NPC207010
0.7722	Intermediate Similarity	NPC475031
0.7722	Intermediate Similarity	NPC317913
0.7722	Intermediate Similarity	NPC298168
0.7722	Intermediate Similarity	NPC474574
0.7722	Intermediate Similarity	NPC143133
0.7722	Intermediate Similarity	NPC64081
0.7722	Intermediate Similarity	NPC133596
0.7711	Intermediate Similarity	NPC477434
0.7711	Intermediate Similarity	NPC18953
0.7703	Intermediate Similarity	NPC41542
0.7703	Intermediate Similarity	NPC48079
0.7701	Intermediate Similarity	NPC219516
0.7692	Intermediate Similarity	NPC478105
0.7692	Intermediate Similarity	NPC273366
0.7692	Intermediate Similarity	NPC472952
0.7692	Intermediate Similarity	NPC472950
0.7683	Intermediate Similarity	NPC102156
0.7683	Intermediate Similarity	NPC61107
0.7683	Intermediate Similarity	NPC121121
0.7683	Intermediate Similarity	NPC289486
0.7683	Intermediate Similarity	NPC475388
0.7683	Intermediate Similarity	NPC2096
0.7683	Intermediate Similarity	NPC242771
0.7683	Intermediate Similarity	NPC148740
0.7683	Intermediate Similarity	NPC100366
0.7683	Intermediate Similarity	NPC164289
0.7683	Intermediate Similarity	NPC311642
0.7683	Intermediate Similarity	NPC208912
0.7674	Intermediate Similarity	NPC24705
0.7674	Intermediate Similarity	NPC56962
0.7662	Intermediate Similarity	NPC153719
0.7647	Intermediate Similarity	NPC239938
0.7639	Intermediate Similarity	NPC209686
0.7639	Intermediate Similarity	NPC249078
0.7639	Intermediate Similarity	NPC236099
0.7639	Intermediate Similarity	NPC114891
0.7632	Intermediate Similarity	NPC251201
0.7632	Intermediate Similarity	NPC63588
0.7632	Intermediate Similarity	NPC232925
0.7625	Intermediate Similarity	NPC147993
0.7619	Intermediate Similarity	NPC477445
0.7619	Intermediate Similarity	NPC473350
0.7614	Intermediate Similarity	NPC182740
0.7614	Intermediate Similarity	NPC122083
0.7614	Intermediate Similarity	NPC211845
0.7614	Intermediate Similarity	NPC256104
0.7606	Intermediate Similarity	NPC204173
0.76	Intermediate Similarity	NPC472741
0.7595	Intermediate Similarity	NPC470145
0.7595	Intermediate Similarity	NPC136424
0.759	Intermediate Similarity	NPC475820
0.759	Intermediate Similarity	NPC213737
0.759	Intermediate Similarity	NPC474253
0.759	Intermediate Similarity	NPC474346
0.759	Intermediate Similarity	NPC473742
0.759	Intermediate Similarity	NPC474284
0.759	Intermediate Similarity	NPC5280
0.7568	Intermediate Similarity	NPC142712
0.7564	Intermediate Similarity	NPC192501
0.7564	Intermediate Similarity	NPC304499
0.7564	Intermediate Similarity	NPC10476
0.7564	Intermediate Similarity	NPC228994
0.7564	Intermediate Similarity	NPC477508
0.7561	Intermediate Similarity	NPC469745
0.7558	Intermediate Similarity	NPC477614
0.7558	Intermediate Similarity	NPC470872
0.7558	Intermediate Similarity	NPC226491
0.7556	Intermediate Similarity	NPC54248
0.7556	Intermediate Similarity	NPC276103
0.7532	Intermediate Similarity	NPC469940
0.7531	Intermediate Similarity	NPC287452
0.7531	Intermediate Similarity	NPC477282
0.7531	Intermediate Similarity	NPC269333
0.7531	Intermediate Similarity	NPC81074
0.7531	Intermediate Similarity	NPC320144
0.7529	Intermediate Similarity	NPC471410
0.7529	Intermediate Similarity	NPC472272
0.7529	Intermediate Similarity	NPC471411
0.7528	Intermediate Similarity	NPC470424

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 NPC186851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	3824
0.2-0.3	3455
0.3-0.4	892
0.4-0.5	265
0.5-0.6	253
0.6-0.7	77
0.7-0.8	13
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
0.8077	Intermediate Similarity	NPD6114	Approved
0.8077	Intermediate Similarity	NPD6115	Approved
0.8077	Intermediate Similarity	NPD6118	Approved
0.8077	Intermediate Similarity	NPD6697	Approved
0.7821	Intermediate Similarity	NPD6117	Approved
0.7792	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3702	Approved
0.7439	Intermediate Similarity	NPD6928	Phase 2
0.7308	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3703	Phase 2
0.7179	Intermediate Similarity	NPD4787	Phase 1
0.7143	Intermediate Similarity	NPD5360	Phase 3
0.7143	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5777	Approved
0.7051	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8035	Phase 2
0.6923	Remote Similarity	NPD8034	Phase 2
0.6883	Remote Similarity	NPD4224	Phase 2
0.6875	Remote Similarity	NPD6081	Approved
0.6842	Remote Similarity	NPD7638	Approved
0.6771	Remote Similarity	NPD7639	Approved
0.6771	Remote Similarity	NPD7640	Approved
0.675	Remote Similarity	NPD4245	Approved
0.675	Remote Similarity	NPD4244	Approved
0.675	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD4758	Discontinued
0.6633	Remote Similarity	NPD7632	Discontinued
0.6628	Remote Similarity	NPD7525	Registered
0.6625	Remote Similarity	NPD3698	Phase 2
0.6531	Remote Similarity	NPD1700	Approved
0.6489	Remote Similarity	NPD6399	Phase 3
0.6489	Remote Similarity	NPD8171	Discontinued
0.6429	Remote Similarity	NPD8418	Phase 2
0.641	Remote Similarity	NPD371	Approved
0.6404	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3669	Approved
0.6395	Remote Similarity	NPD5364	Discontinued
0.6395	Remote Similarity	NPD3671	Phase 1
0.6374	Remote Similarity	NPD8308	Discontinued
0.6296	Remote Similarity	NPD6705	Phase 1
0.6275	Remote Similarity	NPD6402	Approved
0.6275	Remote Similarity	NPD5739	Approved
0.6275	Remote Similarity	NPD7128	Approved
0.6275	Remote Similarity	NPD6675	Approved
0.6275	Remote Similarity	NPD6008	Approved
0.6235	Remote Similarity	NPD6942	Approved
0.6235	Remote Similarity	NPD7339	Approved
0.6222	Remote Similarity	NPD6695	Phase 3
0.6186	Remote Similarity	NPD7991	Discontinued
0.6186	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6051	Approved
0.617	Remote Similarity	NPD5328	Approved
0.6154	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6881	Approved
0.6154	Remote Similarity	NPD4786	Approved
0.6154	Remote Similarity	NPD7320	Approved
0.6154	Remote Similarity	NPD6899	Approved
0.6145	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1811	Approved
0.6118	Remote Similarity	NPD6924	Approved
0.6118	Remote Similarity	NPD6926	Approved
0.6118	Remote Similarity	NPD1810	Approved
0.6106	Remote Similarity	NPD7604	Phase 2
0.6105	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6700	Approved
0.6104	Remote Similarity	NPD3198	Approved
0.6095	Remote Similarity	NPD6373	Approved
0.6095	Remote Similarity	NPD6372	Approved
0.6095	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7328	Approved
0.6091	Remote Similarity	NPD7327	Approved
0.6087	Remote Similarity	NPD386	Approved
0.6087	Remote Similarity	NPD388	Approved
0.6082	Remote Similarity	NPD7748	Approved
0.6067	Remote Similarity	NPD6930	Phase 2
0.6067	Remote Similarity	NPD6931	Approved
0.6067	Remote Similarity	NPD4748	Discontinued
0.6061	Remote Similarity	NPD6084	Phase 2
0.6061	Remote Similarity	NPD6083	Phase 2
0.6058	Remote Similarity	NPD5697	Approved
0.6058	Remote Similarity	NPD5701	Approved
0.6044	Remote Similarity	NPD4788	Approved
0.6042	Remote Similarity	NPD6079	Approved
0.6042	Remote Similarity	NPD6702	Approved
0.6042	Remote Similarity	NPD7637	Suspended
0.6042	Remote Similarity	NPD6703	Approved
0.6038	Remote Similarity	NPD7102	Approved
0.6038	Remote Similarity	NPD6883	Approved
0.6038	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7290	Approved
0.6036	Remote Similarity	NPD7516	Approved
0.6023	Remote Similarity	NPD4238	Approved
0.6023	Remote Similarity	NPD4802	Phase 2
0.6022	Remote Similarity	NPD7521	Approved
0.6022	Remote Similarity	NPD5330	Approved
0.6022	Remote Similarity	NPD7334	Approved
0.6022	Remote Similarity	NPD6409	Approved
0.6022	Remote Similarity	NPD6684	Approved
0.6022	Remote Similarity	NPD3618	Phase 1
0.6022	Remote Similarity	NPD7146	Approved
0.6019	Remote Similarity	NPD8133	Approved
0.6019	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD384	Approved
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD385	Approved
0.5982	Remote Similarity	NPD8377	Approved
0.5982	Remote Similarity	NPD8294	Approved
0.5981	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6650	Approved
0.5981	Remote Similarity	NPD6617	Approved
0.5981	Remote Similarity	NPD8130	Phase 1
0.5981	Remote Similarity	NPD6847	Approved
0.5981	Remote Similarity	NPD6649	Approved
0.5981	Remote Similarity	NPD6869	Approved
0.5979	Remote Similarity	NPD4202	Approved
0.5977	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD6933	Approved
0.5957	Remote Similarity	NPD7750	Discontinued
0.5957	Remote Similarity	NPD7524	Approved
0.5957	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD6929	Approved
0.5955	Remote Similarity	NPD7645	Phase 2
0.5952	Remote Similarity	NPD2254	Approved
0.5952	Remote Similarity	NPD2687	Approved
0.5952	Remote Similarity	NPD2686	Approved
0.5943	Remote Similarity	NPD6013	Approved
0.5943	Remote Similarity	NPD6014	Approved
0.5943	Remote Similarity	NPD6012	Approved
0.5934	Remote Similarity	NPD3667	Approved
0.5929	Remote Similarity	NPD8380	Approved
0.5929	Remote Similarity	NPD8378	Approved
0.5929	Remote Similarity	NPD8379	Approved
0.5929	Remote Similarity	NPD8335	Approved
0.5929	Remote Similarity	NPD8296	Approved
0.5929	Remote Similarity	NPD8033	Approved
0.5926	Remote Similarity	NPD8297	Approved
0.5926	Remote Similarity	NPD6882	Approved
0.5918	Remote Similarity	NPD6001	Approved
0.5909	Remote Similarity	NPD6940	Discontinued
0.5909	Remote Similarity	NPD6932	Approved
0.59	Remote Similarity	NPD7902	Approved
0.5895	Remote Similarity	NPD6672	Approved
0.5895	Remote Similarity	NPD5737	Approved
0.5895	Remote Similarity	NPD6903	Approved
0.5895	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4243	Approved
0.5876	Remote Similarity	NPD7515	Phase 2
0.5859	Remote Similarity	NPD5695	Phase 3
0.5856	Remote Similarity	NPD6009	Approved
0.5856	Remote Similarity	NPD7115	Discovery
0.5851	Remote Similarity	NPD6098	Approved
0.5842	Remote Similarity	NPD5696	Approved
0.5841	Remote Similarity	NPD6319	Approved
0.5824	Remote Similarity	NPD1780	Approved
0.5824	Remote Similarity	NPD6902	Approved
0.5824	Remote Similarity	NPD1779	Approved
0.5794	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5983	Phase 2
0.5789	Remote Similarity	NPD7503	Approved
0.5778	Remote Similarity	NPD4195	Approved
0.5778	Remote Similarity	NPD6683	Phase 2
0.5776	Remote Similarity	NPD7492	Approved
0.5755	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD4785	Approved
0.5747	Remote Similarity	NPD4784	Approved
0.5745	Remote Similarity	NPD6893	Approved
0.5743	Remote Similarity	NPD4755	Approved
0.573	Remote Similarity	NPD8143	Approved
0.573	Remote Similarity	NPD5776	Phase 2
0.573	Remote Similarity	NPD8144	Approved
0.573	Remote Similarity	NPD6925	Approved
0.5726	Remote Similarity	NPD7507	Approved
0.5726	Remote Similarity	NPD6336	Discontinued
0.5726	Remote Similarity	NPD6616	Approved
0.5714	Remote Similarity	NPD7514	Phase 3
0.5714	Remote Similarity	NPD7087	Discontinued
0.5714	Remote Similarity	NPD7509	Discontinued
0.5702	Remote Similarity	NPD6059	Approved
0.5702	Remote Similarity	NPD6054	Approved
0.5698	Remote Similarity	NPD7150	Approved
0.5698	Remote Similarity	NPD7152	Approved
0.5698	Remote Similarity	NPD7151	Approved
0.5686	Remote Similarity	NPD4225	Approved
0.5678	Remote Similarity	NPD8293	Discontinued
0.5678	Remote Similarity	NPD7078	Approved
0.567	Remote Similarity	NPD6080	Approved
0.567	Remote Similarity	NPD6673	Approved
0.567	Remote Similarity	NPD6904	Approved
0.5667	Remote Similarity	NPD7145	Approved
0.5664	Remote Similarity	NPD6335	Approved
0.566	Remote Similarity	NPD6920	Discontinued

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