NPASS Compound

Structure

CID113639 OpenBabel06191715472D 25 26 0 0 1 0 0 0 0 0999 V2000 3.0350 1.7434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5551 -3.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8347 -3.8279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2726 -2.7255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3866 -1.7320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9021 -0.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4143 -0.8283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2251 0.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0426 -1.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5632 1.1131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5794 -0.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6182 0.7861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9174 0.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 -2.3843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5350 0.8774 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2281 -2.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1248 -3.5462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0712 -1.2127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3632 -1.8843 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0951 -0.9955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4692 -2.1301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8485 -4.2363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8737 -2.9334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3606 -2.5744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 1 1 6 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 6 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 22 1 1 0 0 0 21 24 1 0 0 0 0 22 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.27
Volume:	390.417
LogP:	5.126
LogD:	4.412
LogS:	-4.523
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.561
Synthetic Accessibility Score:	5.016
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.644
MDCK Permeability:	3.135490260319784e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.581
20% Bioavailability (F20%):	0.496
30% Bioavailability (F30%):	0.604

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.249
Plasma Protein Binding (PPB):	90.5406265258789%
Volume Distribution (VD):	1.108
Pgp-substrate:	3.961962938308716%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.407
CYP2D6-inhibitor:	0.422
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.755
CYP3A4-substrate:	0.459

ADMET: Excretion

Clearance (CL):	2.248
Half-life (T1/2):	0.356

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.421
Drug-inuced Liver Injury (DILI):	0.616
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.942
Carcinogencity:	0.03
Eye Corrosion:	0.027
Eye Irritation:	0.429
Respiratory Toxicity:	0.132

Download Data

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

Natural Product: NPC113639

Natural Product ID:	NPC113639
*Common Name:**	QPIUBKNTZMBLLI-ASFQSAAXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QPIUBKNTZMBLLI-ASFQSAAXSA-N
Standard InCHI:	InChI=1S/C22H36O3/c1-15-8-7-9-16(2)14-19(25-17(3)23)20-18(21(4,5)24)11-13-22(20,6)12-10-15/h9-10,12,15,18-20,24H,7-8,11,13-14H2,1-6H3/b12-10+,16-9+/t15-,18-,19+,20-,22+/m1/s1
SMILES:	C[C@@H]1CC/C=C(C)/C[C@@H]([C@H]2[C@@H](CC[C@]2(C)/C=C/1)C(C)(C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689087
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane 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
NPO21169	Salvia blepharochlaena	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[11325249]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190330]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	Elafonissos Island (GPS coordinates 3630' N, 2258' E), south of Peloponnese, Greece	2004-APR	PMID[21190330]
NPO31140	Dilophus spiralis	Species	Dictyotaceae	Eukaryota	n.a.	at a depth of 0.1-1 m, Elafonissos Island (3630' N, 2258' E), south of Peloponnese, Greece	2004-APR	PMID[21190330]
NPO21306	Alpinia pinnanensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18865	Tetracentron sinense	Species	Trochodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18865	Tetracentron sinense	Species	Trochodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21306	Alpinia pinnanensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17838	Aster flaccidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21306	Alpinia pinnanensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21169	Salvia blepharochlaena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20558	Pseudevernia ericetorum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18865	Tetracentron sinense	Species	Trochodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20221	Maytenus truncata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21494	Eryngium maritimum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27967	Betula glandulosa	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19911	Arachniodes festina	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17330	Pseudopotamilla occelata	Species	Sabellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20420	Helenium brevifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16565	Lindera oldhami	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20488	Abies homolepis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20838	Cleome pentaphylla	Species	Cleomaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[486594]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[486594]

☑ 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 NPC113639 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	161
0.1-0.2	1125
0.2-0.3	7207
0.3-0.4	15068
0.4-0.5	7280
0.5-0.6	7494
0.6-0.7	4032
0.7-0.8	319
0.8-0.85	6
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8919	High Similarity	NPC476439
0.8732	High Similarity	NPC22301
0.8533	High Similarity	NPC476317
0.8462	Intermediate Similarity	NPC472471
0.8421	Intermediate Similarity	NPC186109
0.825	Intermediate Similarity	NPC472473
0.8116	Intermediate Similarity	NPC323153
0.8028	Intermediate Similarity	NPC287744
0.8028	Intermediate Similarity	NPC140233
0.8	Intermediate Similarity	NPC472466
0.7975	Intermediate Similarity	NPC100906
0.7975	Intermediate Similarity	NPC44083
0.7975	Intermediate Similarity	NPC153987
0.7971	Intermediate Similarity	NPC5698
0.7952	Intermediate Similarity	NPC474970
0.7949	Intermediate Similarity	NPC283619
0.7922	Intermediate Similarity	NPC328104
0.7922	Intermediate Similarity	NPC319090
0.7917	Intermediate Similarity	NPC477009
0.7917	Intermediate Similarity	NPC238352
0.7907	Intermediate Similarity	NPC472468
0.7875	Intermediate Similarity	NPC472470
0.7821	Intermediate Similarity	NPC472472
0.7805	Intermediate Similarity	NPC477667
0.7805	Intermediate Similarity	NPC49208
0.7805	Intermediate Similarity	NPC23748
0.7792	Intermediate Similarity	NPC27395
0.7792	Intermediate Similarity	NPC329090
0.7792	Intermediate Similarity	NPC104644
0.7778	Intermediate Similarity	NPC309300
0.7778	Intermediate Similarity	NPC142163
0.7778	Intermediate Similarity	NPC469723
0.775	Intermediate Similarity	NPC325869
0.7738	Intermediate Similarity	NPC477668
0.7733	Intermediate Similarity	NPC101622
0.7727	Intermediate Similarity	NPC472467
0.7703	Intermediate Similarity	NPC472253
0.7703	Intermediate Similarity	NPC472255
0.7701	Intermediate Similarity	NPC177641
0.7674	Intermediate Similarity	NPC473647
0.7662	Intermediate Similarity	NPC92909
0.7662	Intermediate Similarity	NPC107783
0.7662	Intermediate Similarity	NPC474140
0.7654	Intermediate Similarity	NPC80622
0.7654	Intermediate Similarity	NPC206735
0.7647	Intermediate Similarity	NPC128644
0.7647	Intermediate Similarity	NPC167877
0.7647	Intermediate Similarity	NPC45957
0.7647	Intermediate Similarity	NPC471657
0.764	Intermediate Similarity	NPC472469
0.7632	Intermediate Similarity	NPC470041
0.7632	Intermediate Similarity	NPC4299
0.7625	Intermediate Similarity	NPC474005
0.7619	Intermediate Similarity	NPC471795
0.7606	Intermediate Similarity	NPC252809
0.76	Intermediate Similarity	NPC224532
0.7595	Intermediate Similarity	NPC315261
0.7595	Intermediate Similarity	NPC310643
0.759	Intermediate Similarity	NPC475622
0.759	Intermediate Similarity	NPC474809
0.759	Intermediate Similarity	NPC108045
0.7568	Intermediate Similarity	NPC272125
0.7564	Intermediate Similarity	NPC71152
0.7561	Intermediate Similarity	NPC112868
0.7558	Intermediate Similarity	NPC294480
0.7556	Intermediate Similarity	NPC471903
0.7532	Intermediate Similarity	NPC471662
0.7532	Intermediate Similarity	NPC472254
0.7531	Intermediate Similarity	NPC170561
0.7529	Intermediate Similarity	NPC137253
0.7529	Intermediate Similarity	NPC264127
0.7529	Intermediate Similarity	NPC155011
0.75	Intermediate Similarity	NPC74722
0.75	Intermediate Similarity	NPC318495
0.75	Intermediate Similarity	NPC222634
0.75	Intermediate Similarity	NPC155986
0.75	Intermediate Similarity	NPC198968
0.75	Intermediate Similarity	NPC304690
0.75	Intermediate Similarity	NPC165064
0.75	Intermediate Similarity	NPC40049
0.75	Intermediate Similarity	NPC26888
0.75	Intermediate Similarity	NPC234335
0.75	Intermediate Similarity	NPC144647
0.75	Intermediate Similarity	NPC329656
0.7471	Intermediate Similarity	NPC128496
0.7467	Intermediate Similarity	NPC136813
0.7442	Intermediate Similarity	NPC312215
0.7439	Intermediate Similarity	NPC209944
0.7439	Intermediate Similarity	NPC164840
0.7439	Intermediate Similarity	NPC233332
0.7439	Intermediate Similarity	NPC241290
0.7436	Intermediate Similarity	NPC470237
0.7432	Intermediate Similarity	NPC19569
0.7412	Intermediate Similarity	NPC474349
0.7412	Intermediate Similarity	NPC474189
0.7412	Intermediate Similarity	NPC329738
0.7412	Intermediate Similarity	NPC474694
0.7412	Intermediate Similarity	NPC475860
0.7412	Intermediate Similarity	NPC473659
0.7412	Intermediate Similarity	NPC269638
0.7412	Intermediate Similarity	NPC476602
0.7407	Intermediate Similarity	NPC39547
0.7407	Intermediate Similarity	NPC260814
0.7407	Intermediate Similarity	NPC3852
0.7407	Intermediate Similarity	NPC323249
0.7407	Intermediate Similarity	NPC27949
0.7403	Intermediate Similarity	NPC9161
0.7403	Intermediate Similarity	NPC49422
0.7397	Intermediate Similarity	NPC211291
0.7397	Intermediate Similarity	NPC474480
0.7397	Intermediate Similarity	NPC133368
0.7397	Intermediate Similarity	NPC279200
0.7391	Intermediate Similarity	NPC477355
0.7386	Intermediate Similarity	NPC46281
0.7386	Intermediate Similarity	NPC148414
0.7386	Intermediate Similarity	NPC175628
0.7386	Intermediate Similarity	NPC123854
0.7386	Intermediate Similarity	NPC111585
0.7386	Intermediate Similarity	NPC471896
0.7386	Intermediate Similarity	NPC44240
0.7381	Intermediate Similarity	NPC139206
0.7381	Intermediate Similarity	NPC52108
0.7381	Intermediate Similarity	NPC474789
0.7375	Intermediate Similarity	NPC226242
0.7375	Intermediate Similarity	NPC279537
0.7375	Intermediate Similarity	NPC107059
0.7375	Intermediate Similarity	NPC321016
0.7375	Intermediate Similarity	NPC113733
0.7375	Intermediate Similarity	NPC321381
0.7368	Intermediate Similarity	NPC167527
0.7363	Intermediate Similarity	NPC253115
0.7363	Intermediate Similarity	NPC304899
0.7356	Intermediate Similarity	NPC470612
0.7356	Intermediate Similarity	NPC470613
0.7356	Intermediate Similarity	NPC48866
0.7356	Intermediate Similarity	NPC97884
0.7356	Intermediate Similarity	NPC183546
0.7356	Intermediate Similarity	NPC472220
0.7356	Intermediate Similarity	NPC247406
0.7349	Intermediate Similarity	NPC327002
0.7349	Intermediate Similarity	NPC191711
0.7349	Intermediate Similarity	NPC88735
0.7349	Intermediate Similarity	NPC325031
0.7349	Intermediate Similarity	NPC264245
0.7349	Intermediate Similarity	NPC471661
0.7349	Intermediate Similarity	NPC474894
0.7349	Intermediate Similarity	NPC47761
0.7342	Intermediate Similarity	NPC167049
0.7342	Intermediate Similarity	NPC469691
0.7342	Intermediate Similarity	NPC471659
0.7342	Intermediate Similarity	NPC472966
0.7333	Intermediate Similarity	NPC474922
0.7333	Intermediate Similarity	NPC7165
0.7326	Intermediate Similarity	NPC286153
0.7326	Intermediate Similarity	NPC212843
0.7317	Intermediate Similarity	NPC80530
0.7317	Intermediate Similarity	NPC242767
0.7317	Intermediate Similarity	NPC82488
0.7317	Intermediate Similarity	NPC476438
0.7317	Intermediate Similarity	NPC328714
0.7317	Intermediate Similarity	NPC471537
0.7317	Intermediate Similarity	NPC192999
0.7317	Intermediate Similarity	NPC226226
0.7317	Intermediate Similarity	NPC55304
0.7317	Intermediate Similarity	NPC308545
0.7317	Intermediate Similarity	NPC477371
0.7317	Intermediate Similarity	NPC273410
0.7317	Intermediate Similarity	NPC469690
0.7312	Intermediate Similarity	NPC473510
0.7312	Intermediate Similarity	NPC241221
0.7312	Intermediate Similarity	NPC227865
0.7312	Intermediate Similarity	NPC290802
0.7308	Intermediate Similarity	NPC471660
0.7303	Intermediate Similarity	NPC45269
0.7303	Intermediate Similarity	NPC154101
0.7294	Intermediate Similarity	NPC100391
0.7294	Intermediate Similarity	NPC102048
0.7294	Intermediate Similarity	NPC474693
0.7294	Intermediate Similarity	NPC33913
0.7284	Intermediate Similarity	NPC84360
0.7283	Intermediate Similarity	NPC475033
0.7283	Intermediate Similarity	NPC202705
0.7283	Intermediate Similarity	NPC87090
0.7283	Intermediate Similarity	NPC469432
0.7283	Intermediate Similarity	NPC107243
0.7283	Intermediate Similarity	NPC210337
0.7283	Intermediate Similarity	NPC57416
0.7283	Intermediate Similarity	NPC475032
0.7273	Intermediate Similarity	NPC146554
0.7273	Intermediate Similarity	NPC477215
0.7273	Intermediate Similarity	NPC476388
0.7273	Intermediate Similarity	NPC474889
0.7273	Intermediate Similarity	NPC474570
0.7273	Intermediate Similarity	NPC167272
0.7273	Intermediate Similarity	NPC177141
0.7273	Intermediate Similarity	NPC269877
0.7273	Intermediate Similarity	NPC155479
0.7263	Intermediate Similarity	NPC280566
0.7263	Intermediate Similarity	NPC183570
0.7262	Intermediate Similarity	NPC472465

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 NPC113639 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1727
0.2-0.3	4161
0.3-0.4	2156
0.4-0.5	535
0.5-0.6	243
0.6-0.7	162
0.7-0.8	17
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
0.7792	Intermediate Similarity	NPD6924	Approved
0.7792	Intermediate Similarity	NPD6926	Approved
0.7654	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4821	Approved
0.7654	Intermediate Similarity	NPD4819	Approved
0.7654	Intermediate Similarity	NPD4820	Approved
0.7654	Intermediate Similarity	NPD4822	Approved
0.7625	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6399	Phase 3
0.7595	Intermediate Similarity	NPD6933	Approved
0.759	Intermediate Similarity	NPD5362	Discontinued
0.7561	Intermediate Similarity	NPD5369	Approved
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6435	Approved
0.7412	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4268	Approved
0.7407	Intermediate Similarity	NPD4271	Approved
0.7403	Intermediate Similarity	NPD7143	Approved
0.7403	Intermediate Similarity	NPD7144	Approved
0.7381	Intermediate Similarity	NPD6695	Phase 3
0.7381	Intermediate Similarity	NPD5331	Approved
0.7381	Intermediate Similarity	NPD5332	Approved
0.7349	Intermediate Similarity	NPD4790	Discontinued
0.7308	Intermediate Similarity	NPD7152	Approved
0.7308	Intermediate Similarity	NPD7150	Approved
0.7308	Intermediate Similarity	NPD7151	Approved
0.7303	Intermediate Similarity	NPD7637	Suspended
0.7284	Intermediate Similarity	NPD6932	Approved
0.7273	Intermediate Similarity	NPD6922	Approved
0.7273	Intermediate Similarity	NPD6923	Approved
0.725	Intermediate Similarity	NPD6942	Approved
0.725	Intermediate Similarity	NPD7339	Approved
0.7229	Intermediate Similarity	NPD7525	Registered
0.7229	Intermediate Similarity	NPD5368	Approved
0.7229	Intermediate Similarity	NPD6930	Phase 2
0.7229	Intermediate Similarity	NPD7509	Discontinued
0.7229	Intermediate Similarity	NPD6931	Approved
0.7176	Intermediate Similarity	NPD7154	Phase 3
0.7125	Intermediate Similarity	NPD4784	Approved
0.7125	Intermediate Similarity	NPD4785	Approved
0.7108	Intermediate Similarity	NPD6929	Approved
0.7093	Intermediate Similarity	NPD4786	Approved
0.7079	Intermediate Similarity	NPD6051	Approved
0.7059	Intermediate Similarity	NPD4269	Approved
0.7059	Intermediate Similarity	NPD4270	Approved
0.7045	Intermediate Similarity	NPD4250	Approved
0.7045	Intermediate Similarity	NPD4251	Approved
0.7045	Intermediate Similarity	NPD7524	Approved
0.7045	Intermediate Similarity	NPD7750	Discontinued
0.7024	Intermediate Similarity	NPD7514	Phase 3
0.7	Intermediate Similarity	NPD5785	Approved
0.6988	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7145	Approved
0.6951	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7521	Approved
0.6932	Remote Similarity	NPD4249	Approved
0.6932	Remote Similarity	NPD6684	Approved
0.6932	Remote Similarity	NPD5786	Approved
0.6932	Remote Similarity	NPD7334	Approved
0.6932	Remote Similarity	NPD6409	Approved
0.6932	Remote Similarity	NPD7146	Approved
0.6932	Remote Similarity	NPD5330	Approved
0.6923	Remote Similarity	NPD6411	Approved
0.6915	Remote Similarity	NPD6083	Phase 2
0.6915	Remote Similarity	NPD6084	Phase 2
0.6905	Remote Similarity	NPD6683	Phase 2
0.6905	Remote Similarity	NPD4195	Approved
0.6882	Remote Similarity	NPD5695	Phase 3
0.6875	Remote Similarity	NPD4243	Approved
0.6867	Remote Similarity	NPD5776	Phase 2
0.6867	Remote Similarity	NPD6925	Approved
0.686	Remote Similarity	NPD3667	Approved
0.6824	Remote Similarity	NPD7332	Phase 2
0.6824	Remote Similarity	NPD4252	Approved
0.6818	Remote Similarity	NPD5363	Approved
0.6818	Remote Similarity	NPD6893	Approved
0.68	Remote Similarity	NPD6881	Approved
0.68	Remote Similarity	NPD6899	Approved
0.6778	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6903	Approved
0.6778	Remote Similarity	NPD6672	Approved
0.6778	Remote Similarity	NPD5737	Approved
0.6768	Remote Similarity	NPD6402	Approved
0.6768	Remote Similarity	NPD7128	Approved
0.6768	Remote Similarity	NPD5739	Approved
0.6768	Remote Similarity	NPD6675	Approved
0.6753	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6902	Approved
0.6742	Remote Similarity	NPD6098	Approved
0.6739	Remote Similarity	NPD8034	Phase 2
0.6739	Remote Similarity	NPD8035	Phase 2
0.6739	Remote Similarity	NPD7087	Discontinued
0.6739	Remote Similarity	NPD5281	Approved
0.6739	Remote Similarity	NPD5284	Approved
0.6705	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6101	Approved
0.6702	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6634	Remote Similarity	NPD7320	Approved
0.6634	Remote Similarity	NPD6011	Approved
0.663	Remote Similarity	NPD7838	Discovery
0.6629	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6847	Approved
0.6602	Remote Similarity	NPD8130	Phase 1
0.6602	Remote Similarity	NPD6650	Approved
0.6602	Remote Similarity	NPD6617	Approved
0.6602	Remote Similarity	NPD6869	Approved
0.6602	Remote Similarity	NPD6649	Approved
0.6598	Remote Similarity	NPD7640	Approved
0.6598	Remote Similarity	NPD7639	Approved
0.6596	Remote Similarity	NPD5282	Discontinued
0.6569	Remote Similarity	NPD6372	Approved
0.6569	Remote Similarity	NPD6012	Approved
0.6569	Remote Similarity	NPD6014	Approved
0.6569	Remote Similarity	NPD6013	Approved
0.6569	Remote Similarity	NPD6373	Approved
0.6559	Remote Similarity	NPD6079	Approved
0.6556	Remote Similarity	NPD5279	Phase 3
0.6552	Remote Similarity	NPD6898	Phase 1
0.6538	Remote Similarity	NPD6882	Approved
0.6538	Remote Similarity	NPD8297	Approved
0.6535	Remote Similarity	NPD5701	Approved
0.6522	Remote Similarity	NPD6673	Approved
0.6522	Remote Similarity	NPD5328	Approved
0.6522	Remote Similarity	NPD6904	Approved
0.6522	Remote Similarity	NPD6080	Approved
0.6522	Remote Similarity	NPD1695	Approved
0.6517	Remote Similarity	NPD3665	Phase 1
0.6517	Remote Similarity	NPD3666	Approved
0.6517	Remote Similarity	NPD3133	Approved
0.6517	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5778	Approved
0.6489	Remote Similarity	NPD4202	Approved
0.6489	Remote Similarity	NPD5779	Approved
0.6484	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4223	Phase 3
0.6477	Remote Similarity	NPD4221	Approved
0.6452	Remote Similarity	NPD5207	Approved
0.6444	Remote Similarity	NPD5329	Approved
0.6442	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4748	Discontinued
0.6429	Remote Similarity	NPD8039	Approved
0.6429	Remote Similarity	NPD4190	Phase 3
0.6429	Remote Similarity	NPD8264	Approved
0.6429	Remote Similarity	NPD5275	Approved
0.6421	Remote Similarity	NPD7748	Approved
0.6413	Remote Similarity	NPD4518	Approved
0.6413	Remote Similarity	NPD5208	Approved
0.641	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7902	Approved
0.6383	Remote Similarity	NPD6050	Approved
0.6383	Remote Similarity	NPD7983	Approved
0.6383	Remote Similarity	NPD5694	Approved
0.6374	Remote Similarity	NPD5690	Phase 2
0.6374	Remote Similarity	NPD3618	Phase 1
0.6364	Remote Similarity	NPD5344	Discontinued
0.6364	Remote Similarity	NPD368	Approved
0.6354	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6371	Approved
0.6344	Remote Similarity	NPD4753	Phase 2
0.6333	Remote Similarity	NPD3668	Phase 3
0.6333	Remote Similarity	NPD4197	Approved
0.6327	Remote Similarity	NPD4225	Approved
0.6322	Remote Similarity	NPD7645	Phase 2
0.6296	Remote Similarity	NPD7115	Discovery
0.6292	Remote Similarity	NPD5209	Approved
0.6292	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5692	Phase 3
0.6277	Remote Similarity	NPD46	Approved
0.6277	Remote Similarity	NPD6698	Approved
0.6275	Remote Similarity	NPD6008	Approved
0.6264	Remote Similarity	NPD1694	Approved
0.6263	Remote Similarity	NPD5286	Approved
0.6263	Remote Similarity	NPD4696	Approved
0.6263	Remote Similarity	NPD6648	Approved
0.6263	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD5707	Approved
0.6239	Remote Similarity	NPD6335	Approved
0.6226	Remote Similarity	NPD6053	Discontinued
0.6224	Remote Similarity	NPD4755	Approved
0.6222	Remote Similarity	NPD4788	Approved
0.6214	Remote Similarity	NPD6685	Approved
0.6214	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7515	Phase 2
0.6211	Remote Similarity	NPD5693	Phase 1
0.6203	Remote Similarity	NPD3197	Phase 1
0.62	Remote Similarity	NPD5223	Approved
0.6196	Remote Similarity	NPD4688	Approved
0.6196	Remote Similarity	NPD4690	Approved
0.6196	Remote Similarity	NPD5205	Approved
0.6196	Remote Similarity	NPD4694	Approved
0.6196	Remote Similarity	NPD5280	Approved
0.6196	Remote Similarity	NPD4693	Phase 3

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