NPASS Compound

Structure

CID306973 OpenBabel06191716112D 23 23 0 0 1 0 0 0 0 0999 V2000 8.6603 -4.0000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 7.7942 -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 8.6603 -1.0000 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 9.5263 -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 9.5263 -2.5000 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 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 17 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 22 2 0 0 0 0 18 2 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 14 1 1 0 0 0 19 21 1 0 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.3
Volume:	371.86
LogP:	4.166
LogD:	3.935
LogS:	-4.809
# Rotatable Bonds:	13
TPSA:	49.33
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	3.436
Fsp3:	0.95
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.878
MDCK Permeability:	2.632857285789214e-05
Pgp-inhibitor:	0.207
Pgp-substrate:	0.971
Human Intestinal Absorption (HIA):	0.12
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	88.93634033203125%
Volume Distribution (VD):	1.131
Pgp-substrate:	6.445255279541016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.22
CYP1A2-substrate:	0.762
CYP2C19-inhibitor:	0.311
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.601
CYP2D6-inhibitor:	0.918
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.127
CYP3A4-substrate:	0.083

ADMET: Excretion

Clearance (CL):	2.631
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.75
Skin Sensitization:	0.943
Carcinogencity:	0.047
Eye Corrosion:	0.299
Eye Irritation:	0.159
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC306973

Natural Product ID:	NPC306973
*Common Name:**	(-)-Spectaline
IUPAC Name:	14-[(2S,5R,6R)-5-hydroxy-6-methylpiperidin-2-yl]tetradecan-2-one
Synonyms:	(-)-Spectaline
Standard InCHIKey:	SMOKZFNZPZHGMX-HSALFYBXSA-N
Standard InCHI:	InChI=1S/C20H39NO2/c1-17(22)13-11-9-7-5-3-4-6-8-10-12-14-19-15-16-20(23)18(2)21-19/h18-21,23H,3-16H2,1-2H3/t18-,19+,20-/m1/s1
SMILES:	CC(=O)CCCCCCCCCCCC[C@H]1CC[C@H]([C@H](N1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL249464
PubChem CID:	10019240
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives

*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
NPO32445	cassia spectabilis	Species	Fabaceae	Eukaryota	flowers and green fruits	n.a.	n.a.	PMID[15165164]
NPO32445	cassia spectabilis	Species	Fabaceae	Eukaryota	green fruits	n.a.	n.a.	PMID[18047293]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[30413343]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22441	Senna spectabilis	Species	Fabaceae	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
IC50	2
Others	9

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	40.0	%	PMID[542399]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	66.67	ug.mL-1	PMID[542401]
NPT35	Others	n.a.		deltaA	<	10.0	%	PMID[542399]
NPT2	Others	Unspecified		Inhibition	=	75.0	%	PMID[542399]
NPT2	Others	Unspecified		Inhibition	=	50.0	%	PMID[542399]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	125.0	ug ml-1	PMID[542400]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	16.0	ug ml-1	PMID[542400]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	17.0	ug ml-1	PMID[542400]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	15.81	ug.mL-1	PMID[542401]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	0.62	n.a.	PMID[542401]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	24.9	ug.mL-1	PMID[542401]

☑ 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 NPC306973 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	112
0.1-0.2	6421
0.2-0.3	22135
0.3-0.4	11563
0.4-0.5	2000
0.5-0.6	368
0.6-0.7	68
0.7-0.8	26
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8592	High Similarity	NPC208657
0.7808	Intermediate Similarity	NPC476695
0.7808	Intermediate Similarity	NPC476696
0.7808	Intermediate Similarity	NPC476694
0.7534	Intermediate Similarity	NPC268922
0.7403	Intermediate Similarity	NPC477002
0.7397	Intermediate Similarity	NPC107224
0.7397	Intermediate Similarity	NPC471418
0.7123	Intermediate Similarity	NPC303798
0.7123	Intermediate Similarity	NPC286851
0.7121	Intermediate Similarity	NPC474322
0.7121	Intermediate Similarity	NPC123814
0.7101	Intermediate Similarity	NPC204709
0.7	Intermediate Similarity	NPC268927
0.7	Intermediate Similarity	NPC290106
0.7	Intermediate Similarity	NPC193593
0.7	Intermediate Similarity	NPC233364
0.7	Intermediate Similarity	NPC76726
0.7	Intermediate Similarity	NPC143809
0.7	Intermediate Similarity	NPC64250
0.7	Intermediate Similarity	NPC276928
0.7	Intermediate Similarity	NPC471421
0.6986	Remote Similarity	NPC471780
0.6986	Remote Similarity	NPC142290
0.6986	Remote Similarity	NPC75435
0.6986	Remote Similarity	NPC471892
0.6986	Remote Similarity	NPC198341
0.6986	Remote Similarity	NPC223386
0.6813	Remote Similarity	NPC174117
0.6795	Remote Similarity	NPC185084
0.6769	Remote Similarity	NPC121062
0.6769	Remote Similarity	NPC96966
0.6769	Remote Similarity	NPC29222
0.6757	Remote Similarity	NPC472609
0.6714	Remote Similarity	NPC8979
0.6712	Remote Similarity	NPC69669
0.6712	Remote Similarity	NPC150680
0.6712	Remote Similarity	NPC218150
0.6712	Remote Similarity	NPC2432
0.6712	Remote Similarity	NPC22774
0.6712	Remote Similarity	NPC306462
0.6628	Remote Similarity	NPC125253
0.6628	Remote Similarity	NPC192025
0.6628	Remote Similarity	NPC253975
0.6622	Remote Similarity	NPC163134
0.6622	Remote Similarity	NPC471419
0.6582	Remote Similarity	NPC474468
0.6548	Remote Similarity	NPC219340
0.6538	Remote Similarity	NPC473710
0.6538	Remote Similarity	NPC475694
0.6506	Remote Similarity	NPC473971
0.6506	Remote Similarity	NPC475363
0.6506	Remote Similarity	NPC473972
0.65	Remote Similarity	NPC26932
0.6479	Remote Similarity	NPC278209
0.6456	Remote Similarity	NPC255535
0.6456	Remote Similarity	NPC137554
0.6456	Remote Similarity	NPC285014
0.6456	Remote Similarity	NPC28959
0.6456	Remote Similarity	NPC299603
0.6447	Remote Similarity	NPC315980
0.6438	Remote Similarity	NPC319131
0.6324	Remote Similarity	NPC50457
0.6316	Remote Similarity	NPC474928
0.6316	Remote Similarity	NPC233034
0.6308	Remote Similarity	NPC469781
0.6286	Remote Similarity	NPC277072
0.6286	Remote Similarity	NPC270041
0.6286	Remote Similarity	NPC178263
0.6267	Remote Similarity	NPC17455
0.625	Remote Similarity	NPC220111
0.625	Remote Similarity	NPC471605
0.625	Remote Similarity	NPC471443
0.6234	Remote Similarity	NPC326651
0.6234	Remote Similarity	NPC325117
0.6234	Remote Similarity	NPC322319
0.6222	Remote Similarity	NPC168017
0.6216	Remote Similarity	NPC68974
0.6196	Remote Similarity	NPC312637
0.618	Remote Similarity	NPC83839
0.6154	Remote Similarity	NPC196359
0.6154	Remote Similarity	NPC78312
0.6154	Remote Similarity	NPC135539
0.6154	Remote Similarity	NPC221764
0.6133	Remote Similarity	NPC474014
0.6133	Remote Similarity	NPC57846
0.6133	Remote Similarity	NPC30126
0.6092	Remote Similarity	NPC271772
0.6092	Remote Similarity	NPC36927
0.6087	Remote Similarity	NPC178632
0.6081	Remote Similarity	NPC476537
0.6081	Remote Similarity	NPC170172
0.6081	Remote Similarity	NPC216415
0.6076	Remote Similarity	NPC126664
0.6076	Remote Similarity	NPC34291
0.6067	Remote Similarity	NPC277918
0.6056	Remote Similarity	NPC272396
0.6053	Remote Similarity	NPC470665
0.6026	Remote Similarity	NPC473952
0.6026	Remote Similarity	NPC101746
0.6026	Remote Similarity	NPC116377
0.6026	Remote Similarity	NPC77191
0.6026	Remote Similarity	NPC69798
0.6	Remote Similarity	NPC469363
0.6	Remote Similarity	NPC248956
0.5972	Remote Similarity	NPC471423
0.5972	Remote Similarity	NPC471442
0.5955	Remote Similarity	NPC320936
0.5949	Remote Similarity	NPC113224
0.5946	Remote Similarity	NPC176164
0.5946	Remote Similarity	NPC168308
0.5946	Remote Similarity	NPC302569
0.5946	Remote Similarity	NPC189301
0.5941	Remote Similarity	NPC475239
0.5938	Remote Similarity	NPC471635
0.5938	Remote Similarity	NPC25033
0.5938	Remote Similarity	NPC119225
0.5938	Remote Similarity	NPC470382
0.5938	Remote Similarity	NPC476261
0.593	Remote Similarity	NPC98750
0.5921	Remote Similarity	NPC8087
0.5921	Remote Similarity	NPC62507
0.5882	Remote Similarity	NPC324004
0.5882	Remote Similarity	NPC328497
0.5867	Remote Similarity	NPC319991
0.5867	Remote Similarity	NPC254541
0.5862	Remote Similarity	NPC70574
0.5854	Remote Similarity	NPC170963
0.5854	Remote Similarity	NPC114640
0.5854	Remote Similarity	NPC33267
0.5854	Remote Similarity	NPC324165
0.5854	Remote Similarity	NPC169976
0.5854	Remote Similarity	NPC126366
0.5833	Remote Similarity	NPC78562
0.5833	Remote Similarity	NPC473588
0.5814	Remote Similarity	NPC316242
0.5811	Remote Similarity	NPC10262
0.5811	Remote Similarity	NPC65832
0.5811	Remote Similarity	NPC311668
0.5806	Remote Similarity	NPC322966
0.5802	Remote Similarity	NPC473419
0.5802	Remote Similarity	NPC23721
0.5802	Remote Similarity	NPC475127
0.5802	Remote Similarity	NPC475715
0.5797	Remote Similarity	NPC106872
0.5795	Remote Similarity	NPC471420
0.5795	Remote Similarity	NPC209232
0.5784	Remote Similarity	NPC477000
0.5784	Remote Similarity	NPC477001
0.5778	Remote Similarity	NPC124359
0.5761	Remote Similarity	NPC306838
0.575	Remote Similarity	NPC59221
0.5747	Remote Similarity	NPC315131
0.5747	Remote Similarity	NPC478017
0.5747	Remote Similarity	NPC315535
0.5733	Remote Similarity	NPC302003
0.5733	Remote Similarity	NPC245346
0.5733	Remote Similarity	NPC11433
0.5714	Remote Similarity	NPC47076
0.5714	Remote Similarity	NPC316231
0.5714	Remote Similarity	NPC112890
0.5714	Remote Similarity	NPC134504
0.5714	Remote Similarity	NPC473994
0.5714	Remote Similarity	NPC324825
0.5714	Remote Similarity	NPC302188
0.5696	Remote Similarity	NPC278881
0.5694	Remote Similarity	NPC471607
0.5679	Remote Similarity	NPC306763
0.5679	Remote Similarity	NPC266242
0.5679	Remote Similarity	NPC254617
0.5679	Remote Similarity	NPC171850
0.5679	Remote Similarity	NPC474469
0.5679	Remote Similarity	NPC74555
0.5673	Remote Similarity	NPC244982
0.5673	Remote Similarity	NPC476756
0.5672	Remote Similarity	NPC76051
0.5667	Remote Similarity	NPC165119
0.5658	Remote Similarity	NPC320598
0.5657	Remote Similarity	NPC472736
0.5647	Remote Similarity	NPC474467
0.5647	Remote Similarity	NPC470993
0.5647	Remote Similarity	NPC470992
0.5641	Remote Similarity	NPC145627
0.5641	Remote Similarity	NPC47333
0.5634	Remote Similarity	NPC90904
0.5631	Remote Similarity	NPC128303
0.561	Remote Similarity	NPC15864
0.5603	Remote Similarity	NPC96010
0.5603	Remote Similarity	NPC317654

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 NPC306973 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	73
0.1-0.2	1844
0.2-0.3	4849
0.3-0.4	1733
0.4-0.5	500
0.5-0.6	128
0.6-0.7	23
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7121	Intermediate Similarity	NPD3215	Phase 1
0.7077	Intermediate Similarity	NPD3214	Discontinued
0.6712	Remote Similarity	NPD9028	Phase 2
0.6712	Remote Similarity	NPD9029	Phase 3
0.6712	Remote Similarity	NPD9027	Phase 3
0.6712	Remote Similarity	NPD9026	Phase 2
0.6375	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD393	Approved
0.6316	Remote Similarity	NPD9440	Discontinued
0.631	Remote Similarity	NPD617	Approved
0.6304	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD9442	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD9455	Approved
0.6207	Remote Similarity	NPD882	Phase 2
0.6207	Remote Similarity	NPD883	Phase 2
0.6154	Remote Similarity	NPD8868	Approved
0.6125	Remote Similarity	NPD2694	Approved
0.6125	Remote Similarity	NPD2695	Approved
0.6125	Remote Similarity	NPD2696	Approved
0.6125	Remote Similarity	NPD2697	Approved
0.6076	Remote Similarity	NPD9451	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD9443	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD9676	Phase 3
0.6044	Remote Similarity	NPD621	Discontinued
0.6	Remote Similarity	NPD9240	Approved
0.6	Remote Similarity	NPD9239	Approved
0.5979	Remote Similarity	NPD3714	Approved
0.5979	Remote Similarity	NPD3713	Approved
0.5979	Remote Similarity	NPD3715	Approved
0.5976	Remote Similarity	NPD6704	Discontinued
0.5942	Remote Similarity	NPD9016	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD3176	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD9022	Phase 2
0.5921	Remote Similarity	NPD9024	Phase 2
0.5905	Remote Similarity	NPD2690	Discontinued
0.5904	Remote Similarity	NPD9217	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD355	Phase 2
0.589	Remote Similarity	NPD6706	Discontinued
0.5882	Remote Similarity	NPD399	Approved
0.5882	Remote Similarity	NPD400	Approved
0.5882	Remote Similarity	NPD398	Approved
0.5851	Remote Similarity	NPD2682	Approved
0.5851	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD6439	Phase 3
0.581	Remote Similarity	NPD8087	Discontinued
0.5773	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD8347	Approved
0.5766	Remote Similarity	NPD8345	Approved
0.5766	Remote Similarity	NPD8346	Approved
0.5747	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD8865	Approved
0.5728	Remote Similarity	NPD6920	Discontinued
0.5714	Remote Similarity	NPD9044	Approved
0.5714	Remote Similarity	NPD9656	Approved
0.5714	Remote Similarity	NPD9401	Discovery
0.5696	Remote Similarity	NPD9648	Approved
0.5663	Remote Similarity	NPD5382	Phase 2
0.5619	Remote Similarity	NPD6415	Discontinued
0.56	Remote Similarity	NPD4825	Clinical (unspecified phase)

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