NPASS Compound

Structure

NPC15837 OpenBabel07101718182D 36 37 0 0 0 0 0 0 0 0999 V2000 3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 -3.0000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 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 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 25 1 0 0 0 0 22 27 1 0 0 0 0 23 25 2 0 0 0 0 23 26 1 0 0 0 0 24 26 2 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 26 33 1 0 0 0 0 27 30 1 0 0 0 0 27 31 2 0 0 0 0 28 29 2 0 0 0 0 28 30 1 0 0 0 0 29 32 1 0 0 0 0 30 34 2 0 0 0 0 31 32 1 0 0 0 0 31 35 1 0 0 0 0 32 36 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	564.257
LogP:	10.41
LogD:	4.988
LogS:	-2.845
# Rotatable Bonds:	19
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.067
Synthetic Accessibility Score:	2.898
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.289
MDCK Permeability:	9.723391485749744e-06
Pgp-inhibitor:	0.02
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	101.79605865478516%
Volume Distribution (VD):	8.02
Pgp-substrate:	1.3117175102233887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.247
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.518
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.353
CYP2D6-substrate:	0.459
CYP3A4-inhibitor:	0.115
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	5.104
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.005
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.277
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.26
Skin Sensitization:	0.978
Carcinogencity:	0.034
Eye Corrosion:	0.004
Eye Irritation:	0.923
Respiratory Toxicity:	0.687

Download Data

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

Natural Product: NPC15837

Natural Product ID:	NPC15837
*Common Name:**	IOIMKKFMGZPICM-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IOIMKKFMGZPICM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-3-5-7-9-11-13-15-17-19-21-25-23-26(33)24-28-29(25)32(36)31(35)27(30(28)34)22-20-18-16-14-12-10-8-6-4-2/h23-24,33,35H,3-22H2,1-2H3/p-1
SMILES:	CCCCCCCCCCCc1cc(cc2c1C(=O)C(=C(CCCCCCCCCCC)C2=O)O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463077
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778454]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[476201]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[476201]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[476201]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[476201]

☑ 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 NPC15837 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	290
0.1-0.2	1520
0.2-0.3	3459
0.3-0.4	9718
0.4-0.5	9602
0.5-0.6	6719
0.6-0.7	8693
0.7-0.8	2410
0.8-0.85	231
0.85-0.9	48
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9113	High Similarity	NPC123506
0.9024	High Similarity	NPC282577
0.8976	High Similarity	NPC171460
0.8889	High Similarity	NPC254492
0.888	High Similarity	NPC199273
0.8871	High Similarity	NPC91478
0.8819	High Similarity	NPC324209
0.8819	High Similarity	NPC72667
0.88	High Similarity	NPC273683
0.879	High Similarity	NPC120545
0.876	High Similarity	NPC27659
0.875	High Similarity	NPC96024
0.875	High Similarity	NPC24869
0.874	High Similarity	NPC231774
0.873	High Similarity	NPC310540
0.8702	High Similarity	NPC4170
0.8672	High Similarity	NPC176130
0.8672	High Similarity	NPC69424
0.8672	High Similarity	NPC78364
0.8672	High Similarity	NPC84672
0.8636	High Similarity	NPC50924
0.8615	High Similarity	NPC198305
0.8615	High Similarity	NPC108129
0.8594	High Similarity	NPC306765
0.8583	High Similarity	NPC231717
0.8583	High Similarity	NPC474766
0.8582	High Similarity	NPC36868
0.8582	High Similarity	NPC475957
0.8571	High Similarity	NPC307174
0.8571	High Similarity	NPC164947
0.8561	High Similarity	NPC78307
0.856	High Similarity	NPC190971
0.855	High Similarity	NPC244699
0.8538	High Similarity	NPC25736
0.8538	High Similarity	NPC278928
0.8519	High Similarity	NPC230811
0.8507	High Similarity	NPC86524
0.8507	High Similarity	NPC7464
0.8507	High Similarity	NPC474311
0.8507	High Similarity	NPC38158
0.8496	Intermediate Similarity	NPC202225
0.8485	Intermediate Similarity	NPC309430
0.848	Intermediate Similarity	NPC285829
0.848	Intermediate Similarity	NPC206778
0.8473	Intermediate Similarity	NPC117609
0.8473	Intermediate Similarity	NPC253488
0.8462	Intermediate Similarity	NPC234175
0.8462	Intermediate Similarity	NPC237225
0.8462	Intermediate Similarity	NPC3009
0.8444	Intermediate Similarity	NPC119542
0.8444	Intermediate Similarity	NPC471452
0.8444	Intermediate Similarity	NPC264022
0.8438	Intermediate Similarity	NPC164014
0.8433	Intermediate Similarity	NPC283088
0.8433	Intermediate Similarity	NPC22644
0.8421	Intermediate Similarity	NPC53896
0.8421	Intermediate Similarity	NPC171968
0.8421	Intermediate Similarity	NPC138472
0.8409	Intermediate Similarity	NPC93015
0.8409	Intermediate Similarity	NPC471851
0.8397	Intermediate Similarity	NPC303910
0.8397	Intermediate Similarity	NPC276238
0.8397	Intermediate Similarity	NPC34414
0.8397	Intermediate Similarity	NPC99731
0.8397	Intermediate Similarity	NPC146647
0.8382	Intermediate Similarity	NPC297797
0.8382	Intermediate Similarity	NPC28592
0.8382	Intermediate Similarity	NPC91887
0.8382	Intermediate Similarity	NPC245760
0.8382	Intermediate Similarity	NPC157284
0.8382	Intermediate Similarity	NPC477849
0.8382	Intermediate Similarity	NPC87723
0.8382	Intermediate Similarity	NPC149773
0.8382	Intermediate Similarity	NPC165191
0.8382	Intermediate Similarity	NPC289358
0.8382	Intermediate Similarity	NPC469857
0.8382	Intermediate Similarity	NPC473779
0.8382	Intermediate Similarity	NPC42384
0.8382	Intermediate Similarity	NPC51531
0.8382	Intermediate Similarity	NPC23667
0.8382	Intermediate Similarity	NPC50615
0.8382	Intermediate Similarity	NPC114333
0.8382	Intermediate Similarity	NPC46242
0.8382	Intermediate Similarity	NPC473479
0.8382	Intermediate Similarity	NPC5014
0.8374	Intermediate Similarity	NPC322197
0.8361	Intermediate Similarity	NPC242136
0.8359	Intermediate Similarity	NPC275145
0.8359	Intermediate Similarity	NPC135062
0.8358	Intermediate Similarity	NPC282780
0.8358	Intermediate Similarity	NPC166480
0.8346	Intermediate Similarity	NPC154696
0.8333	Intermediate Similarity	NPC95172
0.8321	Intermediate Similarity	NPC242994
0.8321	Intermediate Similarity	NPC179898
0.8321	Intermediate Similarity	NPC294330
0.8321	Intermediate Similarity	NPC48248
0.8321	Intermediate Similarity	NPC138099
0.8309	Intermediate Similarity	NPC277559
0.8309	Intermediate Similarity	NPC53001
0.8309	Intermediate Similarity	NPC471905
0.8308	Intermediate Similarity	NPC1991
0.8308	Intermediate Similarity	NPC3224
0.8308	Intermediate Similarity	NPC51037
0.8296	Intermediate Similarity	NPC80035
0.8284	Intermediate Similarity	NPC477139
0.8284	Intermediate Similarity	NPC59459
0.8284	Intermediate Similarity	NPC52407
0.8284	Intermediate Similarity	NPC225051
0.8284	Intermediate Similarity	NPC263817
0.8284	Intermediate Similarity	NPC111845
0.8284	Intermediate Similarity	NPC254603
0.8281	Intermediate Similarity	NPC139171
0.8273	Intermediate Similarity	NPC291078
0.8271	Intermediate Similarity	NPC17083
0.8261	Intermediate Similarity	NPC473527
0.8261	Intermediate Similarity	NPC169452
0.8261	Intermediate Similarity	NPC181560
0.8258	Intermediate Similarity	NPC117899
0.8248	Intermediate Similarity	NPC4214
0.8248	Intermediate Similarity	NPC471974
0.8248	Intermediate Similarity	NPC469681
0.8248	Intermediate Similarity	NPC13715
0.8248	Intermediate Similarity	NPC469680
0.8235	Intermediate Similarity	NPC191976
0.8235	Intermediate Similarity	NPC471670
0.8235	Intermediate Similarity	NPC475549
0.8235	Intermediate Similarity	NPC315275
0.8235	Intermediate Similarity	NPC254847
0.8217	Intermediate Similarity	NPC174991
0.8217	Intermediate Similarity	NPC375356
0.8209	Intermediate Similarity	NPC477407
0.8209	Intermediate Similarity	NPC242358
0.8209	Intermediate Similarity	NPC58685
0.8209	Intermediate Similarity	NPC312560
0.8209	Intermediate Similarity	NPC110609
0.8209	Intermediate Similarity	NPC246693
0.8195	Intermediate Similarity	NPC55949
0.8182	Intermediate Similarity	NPC282923
0.8182	Intermediate Similarity	NPC193203
0.8182	Intermediate Similarity	NPC165257
0.8175	Intermediate Similarity	NPC53206
0.8175	Intermediate Similarity	NPC49911
0.8175	Intermediate Similarity	NPC53414
0.8168	Intermediate Similarity	NPC473691
0.8167	Intermediate Similarity	NPC226699
0.8167	Intermediate Similarity	NPC34715
0.8162	Intermediate Similarity	NPC249272
0.8162	Intermediate Similarity	NPC258502
0.8162	Intermediate Similarity	NPC290803
0.816	Intermediate Similarity	NPC28951
0.816	Intermediate Similarity	NPC325646
0.816	Intermediate Similarity	NPC108288
0.816	Intermediate Similarity	NPC477453
0.8156	Intermediate Similarity	NPC471906
0.8154	Intermediate Similarity	NPC142956
0.8148	Intermediate Similarity	NPC180261
0.8148	Intermediate Similarity	NPC37299
0.8148	Intermediate Similarity	NPC115458
0.8148	Intermediate Similarity	NPC294226
0.8143	Intermediate Similarity	NPC135524
0.8143	Intermediate Similarity	NPC30846
0.8143	Intermediate Similarity	NPC19631
0.8143	Intermediate Similarity	NPC471971
0.8143	Intermediate Similarity	NPC248068
0.8143	Intermediate Similarity	NPC239136
0.8143	Intermediate Similarity	NPC469855
0.8143	Intermediate Similarity	NPC193555
0.8143	Intermediate Similarity	NPC471972
0.814	Intermediate Similarity	NPC300274
0.8134	Intermediate Similarity	NPC18798
0.8125	Intermediate Similarity	NPC32322
0.8125	Intermediate Similarity	NPC259703
0.8116	Intermediate Similarity	NPC61398
0.8116	Intermediate Similarity	NPC173980
0.8116	Intermediate Similarity	NPC416
0.8115	Intermediate Similarity	NPC116842
0.811	Intermediate Similarity	NPC473767
0.8106	Intermediate Similarity	NPC471530
0.8106	Intermediate Similarity	NPC209959
0.8102	Intermediate Similarity	NPC155211
0.8095	Intermediate Similarity	NPC150919
0.8092	Intermediate Similarity	NPC477454
0.8092	Intermediate Similarity	NPC103540
0.8088	Intermediate Similarity	NPC270899
0.8088	Intermediate Similarity	NPC12070
0.8088	Intermediate Similarity	NPC44437
0.8083	Intermediate Similarity	NPC6984
0.8074	Intermediate Similarity	NPC88864
0.8071	Intermediate Similarity	NPC246638
0.8071	Intermediate Similarity	NPC305845
0.8071	Intermediate Similarity	NPC204045
0.8065	Intermediate Similarity	NPC11824
0.806	Intermediate Similarity	NPC199253
0.806	Intermediate Similarity	NPC136588
0.806	Intermediate Similarity	NPC259942
0.8058	Intermediate Similarity	NPC114620
0.8058	Intermediate Similarity	NPC477408
0.8058	Intermediate Similarity	NPC143438
0.8058	Intermediate Similarity	NPC103337

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 NPC15837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	971
0.2-0.3	1420
0.3-0.4	2648
0.4-0.5	2169
0.5-0.6	1154
0.6-0.7	437
0.7-0.8	55
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1470	Approved
0.8047	Intermediate Similarity	NPD2932	Approved
0.7907	Intermediate Similarity	NPD3019	Approved
0.7786	Intermediate Similarity	NPD1201	Approved
0.7655	Intermediate Similarity	NPD7390	Discontinued
0.7589	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD5408	Approved
0.7535	Intermediate Similarity	NPD5404	Approved
0.7535	Intermediate Similarity	NPD5405	Approved
0.7535	Intermediate Similarity	NPD5406	Approved
0.752	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3300	Phase 2
0.7448	Intermediate Similarity	NPD8166	Discontinued
0.7444	Intermediate Similarity	NPD3023	Approved
0.7444	Intermediate Similarity	NPD3026	Approved
0.744	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD943	Approved
0.7424	Intermediate Similarity	NPD3025	Approved
0.7424	Intermediate Similarity	NPD3024	Approved
0.741	Intermediate Similarity	NPD3764	Approved
0.7333	Intermediate Similarity	NPD3972	Approved
0.7308	Intermediate Similarity	NPD5951	Approved
0.7299	Intermediate Similarity	NPD1164	Approved
0.7293	Intermediate Similarity	NPD1651	Approved
0.7292	Intermediate Similarity	NPD2935	Discontinued
0.7248	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1471	Phase 3
0.7241	Intermediate Similarity	NPD2346	Discontinued
0.7241	Intermediate Similarity	NPD2344	Approved
0.7234	Intermediate Similarity	NPD6663	Approved
0.7226	Intermediate Similarity	NPD1283	Approved
0.7226	Intermediate Similarity	NPD1876	Approved
0.7222	Intermediate Similarity	NPD2799	Discontinued
0.7218	Intermediate Similarity	NPD9545	Approved
0.7209	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7819	Suspended
0.7206	Intermediate Similarity	NPD9269	Phase 2
0.7194	Intermediate Similarity	NPD5736	Approved
0.7171	Intermediate Similarity	NPD3226	Approved
0.7164	Intermediate Similarity	NPD9268	Approved
0.7154	Intermediate Similarity	NPD7635	Approved
0.7154	Intermediate Similarity	NPD3020	Approved
0.7153	Intermediate Similarity	NPD1755	Approved
0.7133	Intermediate Similarity	NPD2533	Approved
0.7133	Intermediate Similarity	NPD2534	Approved
0.7133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2532	Approved
0.7132	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4626	Approved
0.7095	Intermediate Similarity	NPD7003	Approved
0.7081	Intermediate Similarity	NPD7473	Discontinued
0.708	Intermediate Similarity	NPD4878	Approved
0.7075	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD9494	Approved
0.7063	Intermediate Similarity	NPD1237	Approved
0.7059	Intermediate Similarity	NPD7458	Discontinued
0.7054	Intermediate Similarity	NPD3021	Approved
0.7054	Intermediate Similarity	NPD3022	Approved
0.7049	Intermediate Similarity	NPD2859	Approved
0.7049	Intermediate Similarity	NPD2860	Approved
0.7047	Intermediate Similarity	NPD2309	Approved
0.7027	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD230	Phase 1
0.7007	Intermediate Similarity	NPD1281	Approved
0.7	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD7609	Phase 3
0.6985	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1929	Approved
0.6984	Remote Similarity	NPD1930	Approved
0.698	Remote Similarity	NPD3750	Approved
0.698	Remote Similarity	NPD4628	Phase 3
0.6967	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2934	Approved
0.6967	Remote Similarity	NPD2933	Approved
0.6966	Remote Similarity	NPD1607	Approved
0.6963	Remote Similarity	NPD3091	Approved
0.6944	Remote Similarity	NPD1240	Approved
0.6942	Remote Similarity	NPD7631	Approved
0.6934	Remote Similarity	NPD4879	Approved
0.6923	Remote Similarity	NPD4750	Phase 3
0.6913	Remote Similarity	NPD2800	Approved
0.6911	Remote Similarity	NPD844	Approved
0.6911	Remote Similarity	NPD1809	Phase 2
0.6899	Remote Similarity	NPD2342	Discontinued
0.6879	Remote Similarity	NPD2798	Approved
0.6875	Remote Similarity	NPD8032	Phase 2
0.6871	Remote Similarity	NPD1510	Phase 2
0.6867	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8150	Discontinued
0.6863	Remote Similarity	NPD6273	Approved
0.6861	Remote Similarity	NPD4059	Approved
0.6855	Remote Similarity	NPD288	Approved
0.6855	Remote Similarity	NPD7075	Discontinued
0.6849	Remote Similarity	NPD6651	Approved
0.6846	Remote Similarity	NPD74	Approved
0.6846	Remote Similarity	NPD9266	Approved
0.6842	Remote Similarity	NPD1241	Discontinued
0.6835	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6959	Discontinued
0.6828	Remote Similarity	NPD2979	Phase 3
0.6828	Remote Similarity	NPD4060	Phase 1
0.6824	Remote Similarity	NPD6100	Approved
0.6824	Remote Similarity	NPD6099	Approved
0.6821	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD9493	Approved
0.6806	Remote Similarity	NPD2313	Discontinued
0.6802	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3882	Suspended
0.6788	Remote Similarity	NPD5691	Approved
0.6786	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7236	Approved
0.6772	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1932	Approved
0.6772	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD9264	Approved
0.6769	Remote Similarity	NPD9267	Approved
0.6769	Remote Similarity	NPD9263	Approved
0.6763	Remote Similarity	NPD3092	Approved
0.6748	Remote Similarity	NPD845	Approved
0.6746	Remote Similarity	NPD2066	Phase 3
0.6739	Remote Similarity	NPD3095	Discontinued
0.6739	Remote Similarity	NPD2286	Discontinued
0.6736	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2182	Approved
0.6714	Remote Similarity	NPD1608	Approved
0.6713	Remote Similarity	NPD4208	Discontinued
0.6711	Remote Similarity	NPD2354	Approved
0.6711	Remote Similarity	NPD6190	Approved
0.6693	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3094	Phase 2
0.6688	Remote Similarity	NPD4380	Phase 2
0.6686	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD650	Approved
0.6667	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4093	Discontinued
0.6667	Remote Similarity	NPD164	Approved
0.6667	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1512	Approved
0.6644	Remote Similarity	NPD7961	Discontinued
0.6644	Remote Similarity	NPD3748	Approved
0.6642	Remote Similarity	NPD7610	Discontinued
0.6625	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1549	Phase 2
0.6621	Remote Similarity	NPD7095	Approved
0.6621	Remote Similarity	NPD7008	Discontinued
0.6619	Remote Similarity	NPD1751	Approved
0.6618	Remote Similarity	NPD255	Approved
0.6618	Remote Similarity	NPD256	Approved
0.6617	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2531	Phase 2
0.66	Remote Similarity	NPD2438	Suspended
0.6593	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2329	Discontinued
0.6587	Remote Similarity	NPD3495	Discontinued
0.6587	Remote Similarity	NPD5844	Phase 1
0.6585	Remote Similarity	NPD5711	Approved
0.6585	Remote Similarity	NPD5710	Approved
0.6584	Remote Similarity	NPD7768	Phase 2
0.6582	Remote Similarity	NPD6599	Discontinued
0.6575	Remote Similarity	NPD3268	Approved
0.657	Remote Similarity	NPD8434	Phase 2
0.6569	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5031	Approved
0.6568	Remote Similarity	NPD5029	Approved
0.6568	Remote Similarity	NPD5027	Approved
0.6562	Remote Similarity	NPD2801	Approved
0.6561	Remote Similarity	NPD7239	Suspended
0.6556	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2353	Approved
0.6556	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6355	Discontinued
0.6549	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD2629	Approved
0.6544	Remote Similarity	NPD9281	Approved
0.6543	Remote Similarity	NPD3749	Approved
0.6541	Remote Similarity	NPD7411	Suspended
0.6541	Remote Similarity	NPD1792	Phase 2
0.6538	Remote Similarity	NPD5049	Phase 3
0.6536	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4308	Phase 3
0.6529	Remote Similarity	NPD4954	Approved
0.6529	Remote Similarity	NPD5026	Approved
0.6529	Remote Similarity	NPD4955	Approved
0.6529	Remote Similarity	NPD5034	Approved
0.6529	Remote Similarity	NPD36	Approved
0.6529	Remote Similarity	NPD5028	Approved

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