NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.2
Volume:	257.037
LogP:	3.982
LogD:	3.869
LogS:	-4.62
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.667
Synthetic Accessibility Score:	4.095
Fsp3:	0.867
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:	-4.554
MDCK Permeability:	2.1069103240733966e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.134
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.748
Plasma Protein Binding (PPB):	82.50113677978516%
Volume Distribution (VD):	1.444
Pgp-substrate:	15.113268852233887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.751
CYP2C19-inhibitor:	0.17
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.143
CYP2C9-substrate:	0.681
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.853
CYP3A4-inhibitor:	0.209
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	6.52
Half-life (T1/2):	0.258

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.332
Carcinogencity:	0.051
Eye Corrosion:	0.966
Eye Irritation:	0.978
Respiratory Toxicity:	0.627

Download Data

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

Natural Product: NPC474769

Natural Product ID:	NPC474769
*Common Name:**	(-)-Selin-11-En-4Alpha-Ol
IUPAC Name:	(1R,4aR,8aR)-1,4a-dimethyl-7-prop-1-en-2-yl-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-ol
Synonyms:
Standard InCHIKey:	DPQYOKVMVCQHMY-KBUZWXASSA-N
Standard InCHI:	InChI=1S/C15H26O/c1-11(2)12-6-9-14(3)7-5-8-15(4,16)13(14)10-12/h12-13,16H,1,5-10H2,2-4H3/t12?,13-,14-,15-/m1/s1
SMILES:	CC(=C)C1CCC2(CCCC(C2C1)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481844
PubChem CID:	44575320
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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
NPO24464	Nephthea brassica	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[10579864]
NPO24464	Nephthea brassica	Species	Nephtheidae	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[480184]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[480184]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[480184]
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.86	ug ml-1	PMID[480184]

☑ 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 NPC474769 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	184
0.1-0.2	2707
0.2-0.3	14637
0.3-0.4	12340
0.4-0.5	6586
0.5-0.6	4383
0.6-0.7	1506
0.7-0.8	302
0.8-0.85	28
0.85-0.9	17
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC189290
0.963	High Similarity	NPC264779
0.9153	High Similarity	NPC101128
0.9	High Similarity	NPC258595
0.9	High Similarity	NPC64123
0.8929	High Similarity	NPC39068
0.871	High Similarity	NPC253303
0.871	High Similarity	NPC269077
0.871	High Similarity	NPC185874
0.871	High Similarity	NPC139207
0.8689	High Similarity	NPC208198
0.8689	High Similarity	NPC60837
0.8689	High Similarity	NPC282619
0.8689	High Similarity	NPC2728
0.8689	High Similarity	NPC11555
0.8689	High Similarity	NPC172613
0.8571	High Similarity	NPC244790
0.8571	High Similarity	NPC94192
0.8548	High Similarity	NPC473929
0.8525	High Similarity	NPC68656
0.8525	High Similarity	NPC144650
0.85	High Similarity	NPC79576
0.85	High Similarity	NPC41160
0.85	High Similarity	NPC282694
0.85	High Similarity	NPC194208
0.8438	Intermediate Similarity	NPC476431
0.8308	Intermediate Similarity	NPC283316
0.8281	Intermediate Similarity	NPC276616
0.8281	Intermediate Similarity	NPC245795
0.8276	Intermediate Similarity	NPC179024
0.8254	Intermediate Similarity	NPC103734
0.8254	Intermediate Similarity	NPC475897
0.8182	Intermediate Similarity	NPC167706
0.8125	Intermediate Similarity	NPC101307
0.8125	Intermediate Similarity	NPC117607
0.8125	Intermediate Similarity	NPC88454
0.8095	Intermediate Similarity	NPC474768
0.807	Intermediate Similarity	NPC36002
0.807	Intermediate Similarity	NPC102336
0.8065	Intermediate Similarity	NPC81615
0.806	Intermediate Similarity	NPC95165
0.803	Intermediate Similarity	NPC163020
0.803	Intermediate Similarity	NPC45296
0.8	Intermediate Similarity	NPC266578
0.8	Intermediate Similarity	NPC2648
0.7969	Intermediate Similarity	NPC476406
0.7969	Intermediate Similarity	NPC279434
0.7963	Intermediate Similarity	NPC14552
0.7941	Intermediate Similarity	NPC476366
0.7941	Intermediate Similarity	NPC201048
0.7937	Intermediate Similarity	NPC219940
0.791	Intermediate Similarity	NPC164022
0.791	Intermediate Similarity	NPC301226
0.791	Intermediate Similarity	NPC111234
0.7879	Intermediate Similarity	NPC210323
0.7879	Intermediate Similarity	NPC9942
0.7879	Intermediate Similarity	NPC234511
0.7846	Intermediate Similarity	NPC263161
0.7826	Intermediate Similarity	NPC3403
0.7826	Intermediate Similarity	NPC39362
0.7826	Intermediate Similarity	NPC32832
0.7818	Intermediate Similarity	NPC100445
0.7812	Intermediate Similarity	NPC27243
0.7812	Intermediate Similarity	NPC476737
0.7797	Intermediate Similarity	NPC67508
0.7797	Intermediate Similarity	NPC84824
0.7794	Intermediate Similarity	NPC182717
0.7794	Intermediate Similarity	NPC211009
0.7778	Intermediate Similarity	NPC174956
0.7761	Intermediate Similarity	NPC475728
0.7761	Intermediate Similarity	NPC92801
0.7742	Intermediate Similarity	NPC135648
0.7727	Intermediate Similarity	NPC139785
0.7714	Intermediate Similarity	NPC470749
0.7714	Intermediate Similarity	NPC63958
0.7714	Intermediate Similarity	NPC470766
0.7714	Intermediate Similarity	NPC91573
0.7681	Intermediate Similarity	NPC192638
0.7681	Intermediate Similarity	NPC476736
0.7681	Intermediate Similarity	NPC49168
0.7681	Intermediate Similarity	NPC62657
0.7681	Intermediate Similarity	NPC100334
0.7681	Intermediate Similarity	NPC25511
0.7681	Intermediate Similarity	NPC308440
0.7681	Intermediate Similarity	NPC254509
0.7681	Intermediate Similarity	NPC145552
0.7681	Intermediate Similarity	NPC472503
0.7681	Intermediate Similarity	NPC22134
0.7681	Intermediate Similarity	NPC196358
0.7681	Intermediate Similarity	NPC5046
0.7667	Intermediate Similarity	NPC3025
0.7656	Intermediate Similarity	NPC225415
0.7619	Intermediate Similarity	NPC147524
0.7606	Intermediate Similarity	NPC470758
0.7606	Intermediate Similarity	NPC132542
0.7606	Intermediate Similarity	NPC470711
0.7576	Intermediate Similarity	NPC197805
0.7571	Intermediate Similarity	NPC200243
0.7571	Intermediate Similarity	NPC231256
0.7571	Intermediate Similarity	NPC185536
0.7571	Intermediate Similarity	NPC212879
0.7571	Intermediate Similarity	NPC240235
0.7571	Intermediate Similarity	NPC104387
0.7571	Intermediate Similarity	NPC144075
0.7571	Intermediate Similarity	NPC70982
0.7571	Intermediate Similarity	NPC178383
0.7571	Intermediate Similarity	NPC230704
0.7541	Intermediate Similarity	NPC236588
0.7541	Intermediate Similarity	NPC135438
0.7538	Intermediate Similarity	NPC300442
0.7536	Intermediate Similarity	NPC195489
0.75	Intermediate Similarity	NPC285761
0.75	Intermediate Similarity	NPC472342
0.75	Intermediate Similarity	NPC145498
0.75	Intermediate Similarity	NPC31828
0.75	Intermediate Similarity	NPC472501
0.75	Intermediate Similarity	NPC42853
0.75	Intermediate Similarity	NPC301707
0.7465	Intermediate Similarity	NPC122418
0.7465	Intermediate Similarity	NPC265328
0.7465	Intermediate Similarity	NPC189883
0.7465	Intermediate Similarity	NPC93662
0.7465	Intermediate Similarity	NPC278091
0.7465	Intermediate Similarity	NPC265588
0.7465	Intermediate Similarity	NPC237460
0.7465	Intermediate Similarity	NPC30590
0.7465	Intermediate Similarity	NPC30575
0.7465	Intermediate Similarity	NPC290598
0.7465	Intermediate Similarity	NPC27765
0.7465	Intermediate Similarity	NPC86305
0.7465	Intermediate Similarity	NPC78067
0.7465	Intermediate Similarity	NPC14112
0.7465	Intermediate Similarity	NPC120098
0.7463	Intermediate Similarity	NPC160209
0.7463	Intermediate Similarity	NPC96484
0.7463	Intermediate Similarity	NPC208999
0.7429	Intermediate Similarity	NPC162164
0.7429	Intermediate Similarity	NPC477138
0.7429	Intermediate Similarity	NPC71152
0.7429	Intermediate Similarity	NPC91858
0.7429	Intermediate Similarity	NPC38426
0.7429	Intermediate Similarity	NPC243342
0.7424	Intermediate Similarity	NPC149680
0.7424	Intermediate Similarity	NPC42630
0.7424	Intermediate Similarity	NPC286669
0.7424	Intermediate Similarity	NPC222366
0.7424	Intermediate Similarity	NPC476039
0.7397	Intermediate Similarity	NPC49599
0.7397	Intermediate Similarity	NPC291379
0.7397	Intermediate Similarity	NPC80530
0.7397	Intermediate Similarity	NPC49627
0.7397	Intermediate Similarity	NPC263951
0.7397	Intermediate Similarity	NPC273410
0.7391	Intermediate Similarity	NPC110799
0.7391	Intermediate Similarity	NPC242001
0.7391	Intermediate Similarity	NPC164045
0.7391	Intermediate Similarity	NPC23954
0.7391	Intermediate Similarity	NPC475077
0.7391	Intermediate Similarity	NPC242992
0.7385	Intermediate Similarity	NPC323424
0.7385	Intermediate Similarity	NPC96793
0.7368	Intermediate Similarity	NPC316035
0.7361	Intermediate Similarity	NPC130136
0.7361	Intermediate Similarity	NPC212241
0.7361	Intermediate Similarity	NPC90979
0.7361	Intermediate Similarity	NPC257191
0.7361	Intermediate Similarity	NPC91594
0.7361	Intermediate Similarity	NPC119355
0.7361	Intermediate Similarity	NPC157996
0.7361	Intermediate Similarity	NPC138502
0.7361	Intermediate Similarity	NPC471798
0.7361	Intermediate Similarity	NPC34177
0.7361	Intermediate Similarity	NPC472805
0.7361	Intermediate Similarity	NPC40394
0.7361	Intermediate Similarity	NPC101475
0.7361	Intermediate Similarity	NPC260301
0.7361	Intermediate Similarity	NPC331618
0.7361	Intermediate Similarity	NPC202540
0.7361	Intermediate Similarity	NPC307336
0.7361	Intermediate Similarity	NPC248830
0.7353	Intermediate Similarity	NPC474248
0.7324	Intermediate Similarity	NPC471723
0.7324	Intermediate Similarity	NPC257347
0.7324	Intermediate Similarity	NPC34700
0.7324	Intermediate Similarity	NPC141071
0.7324	Intermediate Similarity	NPC66566
0.7324	Intermediate Similarity	NPC322353
0.7324	Intermediate Similarity	NPC118508
0.7324	Intermediate Similarity	NPC291503
0.7324	Intermediate Similarity	NPC477923
0.7324	Intermediate Similarity	NPC138374
0.7324	Intermediate Similarity	NPC133580
0.7324	Intermediate Similarity	NPC121744
0.7313	Intermediate Similarity	NPC308522
0.7313	Intermediate Similarity	NPC171225
0.7313	Intermediate Similarity	NPC68703
0.7313	Intermediate Similarity	NPC74885
0.7313	Intermediate Similarity	NPC69649
0.7302	Intermediate Similarity	NPC95958
0.7297	Intermediate Similarity	NPC236237

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 NPC474769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	3021
0.2-0.3	4065
0.3-0.4	1331
0.4-0.5	289
0.5-0.6	188
0.6-0.7	68
0.7-0.8	8
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
0.7647	Intermediate Similarity	NPD4243	Approved
0.7429	Intermediate Similarity	NPD4784	Approved
0.7429	Intermediate Similarity	NPD4785	Approved
0.7324	Intermediate Similarity	NPD5275	Approved
0.7324	Intermediate Similarity	NPD4190	Phase 3
0.7297	Intermediate Similarity	NPD7525	Registered
0.7162	Intermediate Similarity	NPD7645	Phase 2
0.7083	Intermediate Similarity	NPD6942	Approved
0.7083	Intermediate Similarity	NPD7339	Approved
0.6986	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6926	Approved
0.6944	Remote Similarity	NPD6924	Approved
0.6933	Remote Similarity	NPD4195	Approved
0.6757	Remote Similarity	NPD6933	Approved
0.6724	Remote Similarity	NPD385	Approved
0.6724	Remote Similarity	NPD384	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6625	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7509	Discontinued
0.662	Remote Similarity	NPD6923	Approved
0.662	Remote Similarity	NPD6922	Approved
0.6607	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4788	Approved
0.6552	Remote Similarity	NPD386	Approved
0.6552	Remote Similarity	NPD388	Approved
0.6543	Remote Similarity	NPD3618	Phase 1
0.6543	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7143	Approved
0.6528	Remote Similarity	NPD7144	Approved
0.65	Remote Similarity	NPD4197	Approved
0.6456	Remote Similarity	NPD3667	Approved
0.6438	Remote Similarity	NPD7152	Approved
0.6438	Remote Similarity	NPD7150	Approved
0.6438	Remote Similarity	NPD7151	Approved
0.642	Remote Similarity	NPD5329	Approved
0.641	Remote Similarity	NPD6931	Approved
0.641	Remote Similarity	NPD6930	Phase 2
0.641	Remote Similarity	NPD4695	Discontinued
0.641	Remote Similarity	NPD4748	Discontinued
0.6389	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3617	Approved
0.6341	Remote Similarity	NPD4519	Discontinued
0.6341	Remote Similarity	NPD4138	Approved
0.6341	Remote Similarity	NPD4690	Approved
0.6341	Remote Similarity	NPD5205	Approved
0.6341	Remote Similarity	NPD4623	Approved
0.6341	Remote Similarity	NPD4689	Approved
0.6341	Remote Similarity	NPD4688	Approved
0.6341	Remote Similarity	NPD4693	Phase 3
0.6324	Remote Similarity	NPD368	Approved
0.631	Remote Similarity	NPD5328	Approved
0.6296	Remote Similarity	NPD3666	Approved
0.6296	Remote Similarity	NPD4786	Approved
0.6296	Remote Similarity	NPD3665	Phase 1
0.6296	Remote Similarity	NPD3133	Approved
0.6282	Remote Similarity	NPD6929	Approved
0.6279	Remote Similarity	NPD4202	Approved
0.6265	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5360	Phase 3
0.625	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6932	Approved
0.619	Remote Similarity	NPD4723	Approved
0.619	Remote Similarity	NPD4722	Approved
0.6184	Remote Similarity	NPD8264	Approved
0.6176	Remote Similarity	NPD1145	Discontinued
0.6173	Remote Similarity	NPD6695	Phase 3
0.6163	Remote Similarity	NPD8034	Phase 2
0.6163	Remote Similarity	NPD8035	Phase 2
0.6163	Remote Similarity	NPD6079	Approved
0.6163	Remote Similarity	NPD7515	Phase 2
0.6154	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD342	Phase 1
0.6145	Remote Similarity	NPD4694	Approved
0.6145	Remote Similarity	NPD5280	Approved
0.6145	Remote Similarity	NPD5690	Phase 2
0.6125	Remote Similarity	NPD4692	Approved
0.6125	Remote Similarity	NPD4139	Approved
0.6118	Remote Similarity	NPD4753	Phase 2
0.6098	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD4787	Phase 1
0.6076	Remote Similarity	NPD6683	Phase 2
0.6071	Remote Similarity	NPD3573	Approved
0.6056	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD6925	Approved
0.6026	Remote Similarity	NPD5776	Phase 2
0.6024	Remote Similarity	NPD6893	Approved
0.6023	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD7332	Phase 2
0.6	Remote Similarity	NPD7514	Phase 3
0.6	Remote Similarity	NPD4758	Discontinued
0.6	Remote Similarity	NPD4755	Approved
0.5972	Remote Similarity	NPD4224	Phase 2
0.5949	Remote Similarity	NPD7145	Approved
0.5946	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD367	Approved
0.5926	Remote Similarity	NPD6898	Phase 1
0.5904	Remote Similarity	NPD3668	Phase 3
0.5889	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD5221	Approved
0.5889	Remote Similarity	NPD4697	Phase 3
0.5889	Remote Similarity	NPD5222	Approved
0.5882	Remote Similarity	NPD7750	Discontinued
0.5882	Remote Similarity	NPD7524	Approved
0.587	Remote Similarity	NPD4696	Approved
0.587	Remote Similarity	NPD5285	Approved
0.587	Remote Similarity	NPD4700	Approved
0.587	Remote Similarity	NPD5286	Approved
0.5824	Remote Similarity	NPD5173	Approved
0.5824	Remote Similarity	NPD7902	Approved
0.5811	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5223	Approved
0.5795	Remote Similarity	NPD5281	Approved
0.5795	Remote Similarity	NPD5284	Approved
0.5789	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5210	Approved
0.5778	Remote Similarity	NPD4629	Approved
0.5769	Remote Similarity	NPD3703	Phase 2
0.5765	Remote Similarity	NPD5279	Phase 3
0.5765	Remote Similarity	NPD6098	Approved
0.5761	Remote Similarity	NPD7638	Approved
0.5761	Remote Similarity	NPD5290	Discontinued
0.5747	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD4633	Approved
0.5745	Remote Similarity	NPD5224	Approved
0.5745	Remote Similarity	NPD5226	Approved
0.5745	Remote Similarity	NPD5211	Phase 2
0.5745	Remote Similarity	NPD5225	Approved
0.5733	Remote Similarity	NPD3698	Phase 2
0.5733	Remote Similarity	NPD4137	Phase 3
0.5732	Remote Similarity	NPD6902	Approved
0.573	Remote Similarity	NPD6399	Phase 3
0.5699	Remote Similarity	NPD7640	Approved
0.5699	Remote Similarity	NPD7639	Approved
0.5696	Remote Similarity	NPD1346	Approved
0.5696	Remote Similarity	NPD6117	Approved
0.5694	Remote Similarity	NPD371	Approved
0.5684	Remote Similarity	NPD5174	Approved
0.5684	Remote Similarity	NPD5175	Approved
0.5684	Remote Similarity	NPD4754	Approved
0.5682	Remote Similarity	NPD4096	Approved
0.5667	Remote Similarity	NPD6001	Approved
0.5658	Remote Similarity	NPD4691	Approved
0.5658	Remote Similarity	NPD4245	Approved
0.5658	Remote Similarity	NPD4789	Approved
0.5658	Remote Similarity	NPD4747	Approved
0.5658	Remote Similarity	NPD4244	Approved
0.5652	Remote Similarity	NPD6083	Phase 2
0.5652	Remote Similarity	NPD6084	Phase 2
0.5641	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD5208	Approved
0.5625	Remote Similarity	NPD5141	Approved
0.5625	Remote Similarity	NPD6116	Phase 1
0.5618	Remote Similarity	NPD7087	Discontinued
0.5616	Remote Similarity	NPD7341	Phase 2
0.5604	Remote Similarity	NPD5695	Phase 3
0.5604	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6705	Phase 1

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