NPASS Compound

Structure

NPC82503 OpenBabel07101718322D 26 27 0 0 1 0 0 0 0 0999 V2000 -6.8510 0.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0758 -0.6387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0567 -1.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4368 -0.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4028 -1.0870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7297 -1.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5050 -0.3105 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 -1.8320 -0.7588 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1099 -0.3799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7638 -1.2765 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 0.8660 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 6 25 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 16 2 0 0 0 0 10 17 1 0 0 0 0 11 17 2 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 23 1 0 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 18 21 1 0 0 0 0 19 20 2 0 0 0 0 19 22 1 0 0 0 0 20 25 1 0 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 23 5 1 6 0 0 0 23 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.24
Volume:	399.803
LogP:	6.527
LogD:	5.104
LogS:	-5.272
# Rotatable Bonds:	7
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	3.619
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.753
MDCK Permeability:	2.2044045181246474e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.825
30% Bioavailability (F30%):	0.076

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.104
Plasma Protein Binding (PPB):	98.97954559326172%
Volume Distribution (VD):	3.89
Pgp-substrate:	3.958808183670044%

ADMET: Metabolism

CYP1A2-inhibitor:	0.88
CYP1A2-substrate:	0.725
CYP2C19-inhibitor:	0.666
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.761
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.927
CYP2D6-substrate:	0.578
CYP3A4-inhibitor:	0.885
CYP3A4-substrate:	0.43

ADMET: Excretion

Clearance (CL):	6.94
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.917
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.133
Skin Sensitization:	0.939
Carcinogencity:	0.064
Eye Corrosion:	0.004
Eye Irritation:	0.618
Respiratory Toxicity:	0.173

Download Data

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

Natural Product: NPC82503

Natural Product ID:	NPC82503
*Common Name:**	Albatrelin B
IUPAC Name:	(2R)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-5-methoxy-2,7-dimethylchromen-8-ol
Synonyms:	Albatrelin B
Standard InCHIKey:	MYIDCWYCVAPNOL-XMQQHFNTSA-N
Standard InCHI:	InChI=1S/C23H32O3/c1-16(2)9-7-10-17(3)11-8-13-23(5)14-12-19-20(25-6)15-18(4)21(24)22(19)26-23/h9,11-12,14-15,24H,7-8,10,13H2,1-6H3/b17-11+/t23-/m1/s1
SMILES:	CC(=CCC/C(=C/CC[C@]1(C)C=Cc2c(cc(C)c(c2O1)O)OC)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332229
PubChem CID:	71524349
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23305465]
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10941	Albatrellus ovinus	Species	Albatrellaceae	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	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[515553]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[515553]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[515553]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[515553]

☑ 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 NPC82503 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	433
0.1-0.2	1805
0.2-0.3	6317
0.3-0.4	13216
0.4-0.5	3691
0.5-0.6	5038
0.6-0.7	8108
0.7-0.8	3364
0.8-0.85	496
0.85-0.9	203
0.9-0.95	23
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC476006
0.938	High Similarity	NPC37196
0.938	High Similarity	NPC94236
0.9302	High Similarity	NPC161203
0.9297	High Similarity	NPC220935
0.9237	High Similarity	NPC201357
0.9237	High Similarity	NPC255147
0.9237	High Similarity	NPC281521
0.9231	High Similarity	NPC36661
0.9213	High Similarity	NPC216836
0.9173	High Similarity	NPC19869
0.9147	High Similarity	NPC229231
0.9147	High Similarity	NPC214860
0.9134	High Similarity	NPC112596
0.912	High Similarity	NPC474864
0.912	High Similarity	NPC246967
0.9098	High Similarity	NPC476171
0.9084	High Similarity	NPC269528
0.907	High Similarity	NPC45824
0.9015	High Similarity	NPC106215
0.9	High Similarity	NPC474481
0.8992	High Similarity	NPC19694
0.8992	High Similarity	NPC266691
0.8984	High Similarity	NPC245060
0.8976	High Similarity	NPC183446
0.8968	High Similarity	NPC135414
0.8968	High Similarity	NPC194626
0.8952	High Similarity	NPC85895
0.8952	High Similarity	NPC137294
0.8947	High Similarity	NPC327382
0.8947	High Similarity	NPC472337
0.8947	High Similarity	NPC252095
0.8947	High Similarity	NPC134968
0.8939	High Similarity	NPC474810
0.8939	High Similarity	NPC168059
0.8939	High Similarity	NPC229442
0.8923	High Similarity	NPC10225
0.8923	High Similarity	NPC158477
0.8923	High Similarity	NPC58164
0.8915	High Similarity	NPC236760
0.8898	High Similarity	NPC95168
0.8889	High Similarity	NPC212965
0.8881	High Similarity	NPC476698
0.8881	High Similarity	NPC472336
0.8881	High Similarity	NPC472334
0.8872	High Similarity	NPC103967
0.8855	High Similarity	NPC234488
0.8855	High Similarity	NPC51840
0.8855	High Similarity	NPC299221
0.8855	High Similarity	NPC311680
0.8846	High Similarity	NPC63179
0.8832	High Similarity	NPC323126
0.8819	High Similarity	NPC120638
0.8815	High Similarity	NPC276490
0.8815	High Similarity	NPC326797
0.8815	High Similarity	NPC103976
0.8815	High Similarity	NPC102904
0.8815	High Similarity	NPC107551
0.8815	High Similarity	NPC176051
0.8815	High Similarity	NPC474282
0.881	High Similarity	NPC218753
0.8806	High Similarity	NPC283009
0.8806	High Similarity	NPC261873
0.8788	High Similarity	NPC142530
0.8788	High Similarity	NPC474356
0.8788	High Similarity	NPC12275
0.8788	High Similarity	NPC147317
0.8788	High Similarity	NPC45715
0.8788	High Similarity	NPC469907
0.8769	High Similarity	NPC50368
0.8769	High Similarity	NPC210355
0.8768	High Similarity	NPC477616
0.876	High Similarity	NPC299584
0.876	High Similarity	NPC82483
0.876	High Similarity	NPC234400
0.876	High Similarity	NPC131397
0.876	High Similarity	NPC60885
0.876	High Similarity	NPC476254
0.876	High Similarity	NPC265483
0.875	High Similarity	NPC127218
0.875	High Similarity	NPC319647
0.875	High Similarity	NPC25966
0.875	High Similarity	NPC292882
0.875	High Similarity	NPC245207
0.8741	High Similarity	NPC474639
0.8741	High Similarity	NPC227503
0.8741	High Similarity	NPC230734
0.874	High Similarity	NPC75713
0.874	High Similarity	NPC285289
0.8731	High Similarity	NPC310854
0.8722	High Similarity	NPC6451
0.8722	High Similarity	NPC127624
0.8722	High Similarity	NPC86655
0.8722	High Similarity	NPC218884
0.8722	High Similarity	NPC202762
0.872	High Similarity	NPC474612
0.8712	High Similarity	NPC91291
0.8702	High Similarity	NPC474616
0.8692	High Similarity	NPC78974
0.8692	High Similarity	NPC223136
0.8692	High Similarity	NPC18924
0.8692	High Similarity	NPC103823
0.8692	High Similarity	NPC28730
0.8692	High Similarity	NPC244364
0.8692	High Similarity	NPC214406
0.8692	High Similarity	NPC44748
0.8686	High Similarity	NPC254759
0.8686	High Similarity	NPC160283
0.8682	High Similarity	NPC270030
0.8682	High Similarity	NPC228972
0.8682	High Similarity	NPC122792
0.8676	High Similarity	NPC139548
0.8676	High Similarity	NPC272157
0.8676	High Similarity	NPC35550
0.8676	High Similarity	NPC76336
0.8676	High Similarity	NPC148835
0.8676	High Similarity	NPC201145
0.8676	High Similarity	NPC95162
0.8676	High Similarity	NPC73535
0.8676	High Similarity	NPC90615
0.8676	High Similarity	NPC25111
0.8676	High Similarity	NPC20511
0.8676	High Similarity	NPC6262
0.8676	High Similarity	NPC52086
0.8667	High Similarity	NPC121812
0.8667	High Similarity	NPC470356
0.8667	High Similarity	NPC195022
0.8667	High Similarity	NPC474206
0.8667	High Similarity	NPC112939
0.8667	High Similarity	NPC94750
0.8667	High Similarity	NPC112246
0.8667	High Similarity	NPC151224
0.8657	High Similarity	NPC475840
0.8647	High Similarity	NPC232275
0.8647	High Similarity	NPC472597
0.8636	High Similarity	NPC190144
0.8626	High Similarity	NPC246620
0.8626	High Similarity	NPC470699
0.8626	High Similarity	NPC124452
0.8626	High Similarity	NPC293054
0.8626	High Similarity	NPC324112
0.8626	High Similarity	NPC82679
0.8626	High Similarity	NPC236791
0.8626	High Similarity	NPC159968
0.8626	High Similarity	NPC169474
0.8626	High Similarity	NPC74817
0.8626	High Similarity	NPC282000
0.8623	High Similarity	NPC471389
0.8613	High Similarity	NPC13067
0.8611	High Similarity	NPC160196
0.8605	High Similarity	NPC121115
0.8603	High Similarity	NPC302701
0.8603	High Similarity	NPC248727
0.8603	High Similarity	NPC16435
0.8603	High Similarity	NPC173660
0.8603	High Similarity	NPC306441
0.8603	High Similarity	NPC270456
0.8603	High Similarity	NPC269091
0.8603	High Similarity	NPC265433
0.8603	High Similarity	NPC300846
0.8603	High Similarity	NPC126682
0.8603	High Similarity	NPC104167
0.8603	High Similarity	NPC476639
0.8603	High Similarity	NPC82271
0.8603	High Similarity	NPC162659
0.8603	High Similarity	NPC114155
0.8593	High Similarity	NPC317380
0.8582	High Similarity	NPC16208
0.8582	High Similarity	NPC7903
0.8582	High Similarity	NPC474635
0.8582	High Similarity	NPC184447
0.8582	High Similarity	NPC470752
0.8582	High Similarity	NPC233980
0.8582	High Similarity	NPC35932
0.8582	High Similarity	NPC160991
0.8571	High Similarity	NPC472338
0.8571	High Similarity	NPC50250
0.8571	High Similarity	NPC224157
0.8571	High Similarity	NPC192687
0.8561	High Similarity	NPC2613
0.8561	High Similarity	NPC472335
0.8561	High Similarity	NPC475891
0.8561	High Similarity	NPC469564
0.8561	High Similarity	NPC107161
0.8561	High Similarity	NPC59841
0.8561	High Similarity	NPC204347
0.8561	High Similarity	NPC472332
0.8551	High Similarity	NPC295719
0.8551	High Similarity	NPC165026
0.8551	High Similarity	NPC34431
0.8551	High Similarity	NPC259519
0.8551	High Similarity	NPC73505
0.855	High Similarity	NPC181361
0.854	High Similarity	NPC211549
0.8529	High Similarity	NPC260898
0.8529	High Similarity	NPC164787
0.8529	High Similarity	NPC47398
0.8529	High Similarity	NPC234333
0.8529	High Similarity	NPC61946
0.8529	High Similarity	NPC111655

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 NPC82503 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	962
0.2-0.3	2184
0.3-0.4	2740
0.4-0.5	1447
0.5-0.6	895
0.6-0.7	483
0.7-0.8	52
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD3027	Phase 3
0.8346	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD4749	Approved
0.8309	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1613	Approved
0.8189	Intermediate Similarity	NPD6671	Approved
0.8162	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD4625	Phase 3
0.8027	Intermediate Similarity	NPD1653	Approved
0.8	Intermediate Similarity	NPD2801	Approved
0.7874	Intermediate Similarity	NPD228	Approved
0.7863	Intermediate Similarity	NPD1548	Phase 1
0.7852	Intermediate Similarity	NPD6696	Suspended
0.781	Intermediate Similarity	NPD3018	Phase 2
0.7737	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2982	Phase 2
0.7647	Intermediate Similarity	NPD2983	Phase 2
0.7639	Intermediate Similarity	NPD6100	Approved
0.7639	Intermediate Similarity	NPD6099	Approved
0.763	Intermediate Similarity	NPD1091	Approved
0.763	Intermediate Similarity	NPD422	Phase 1
0.763	Intermediate Similarity	NPD1610	Phase 2
0.7626	Intermediate Similarity	NPD4908	Phase 1
0.7582	Intermediate Similarity	NPD1934	Approved
0.7574	Intermediate Similarity	NPD2981	Phase 2
0.7559	Intermediate Similarity	NPD290	Approved
0.7554	Intermediate Similarity	NPD2861	Phase 2
0.7518	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1511	Approved
0.748	Intermediate Similarity	NPD968	Approved
0.7444	Intermediate Similarity	NPD7340	Approved
0.7442	Intermediate Similarity	NPD4750	Phase 3
0.7436	Intermediate Similarity	NPD3882	Suspended
0.7432	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1512	Approved
0.7413	Intermediate Similarity	NPD1558	Phase 1
0.7391	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1778	Approved
0.7348	Intermediate Similarity	NPD1398	Phase 1
0.7301	Intermediate Similarity	NPD7054	Approved
0.7299	Intermediate Similarity	NPD3496	Discontinued
0.7273	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3817	Phase 2
0.7256	Intermediate Similarity	NPD7472	Approved
0.7248	Intermediate Similarity	NPD6674	Discontinued
0.7231	Intermediate Similarity	NPD2684	Approved
0.723	Intermediate Similarity	NPD3540	Phase 1
0.7226	Intermediate Similarity	NPD4675	Approved
0.7226	Intermediate Similarity	NPD4678	Approved
0.7222	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6166	Phase 2
0.7222	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD5283	Phase 1
0.7215	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5844	Phase 1
0.719	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3539	Phase 1
0.7152	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD7843	Approved
0.7134	Intermediate Similarity	NPD3818	Discontinued
0.7133	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1652	Phase 2
0.7126	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6234	Discontinued
0.7123	Intermediate Similarity	NPD447	Suspended
0.7122	Intermediate Similarity	NPD3705	Approved
0.7111	Intermediate Similarity	NPD7157	Approved
0.7097	Intermediate Similarity	NPD9296	Approved
0.7092	Intermediate Similarity	NPD8651	Approved
0.7066	Intermediate Similarity	NPD7251	Discontinued
0.7055	Intermediate Similarity	NPD4060	Phase 1
0.7055	Intermediate Similarity	NPD3620	Phase 2
0.7055	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1551	Phase 2
0.7044	Intermediate Similarity	NPD5402	Approved
0.7039	Intermediate Similarity	NPD2219	Phase 1
0.7031	Intermediate Similarity	NPD291	Approved
0.7031	Intermediate Similarity	NPD940	Approved
0.7031	Intermediate Similarity	NPD846	Approved
0.7029	Intermediate Similarity	NPD1357	Approved
0.7024	Intermediate Similarity	NPD7808	Phase 3
0.7024	Intermediate Similarity	NPD7549	Discontinued
0.7013	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7447	Phase 1
0.7007	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD230	Phase 1
0.7007	Intermediate Similarity	NPD5124	Phase 1
0.7006	Intermediate Similarity	NPD6797	Phase 2
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5763	Approved
0.6994	Remote Similarity	NPD6232	Discontinued
0.6986	Remote Similarity	NPD2674	Phase 3
0.697	Remote Similarity	NPD7473	Discontinued
0.6957	Remote Similarity	NPD7533	Approved
0.6957	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7534	Approved
0.6953	Remote Similarity	NPD1242	Phase 1
0.6948	Remote Similarity	NPD1774	Approved
0.6948	Remote Similarity	NPD4357	Discontinued
0.6933	Remote Similarity	NPD7199	Phase 2
0.6928	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7228	Approved
0.6928	Remote Similarity	NPD2677	Approved
0.6918	Remote Similarity	NPD3144	Approved
0.6918	Remote Similarity	NPD37	Approved
0.6918	Remote Similarity	NPD3145	Approved
0.6917	Remote Similarity	NPD3022	Approved
0.6917	Remote Similarity	NPD3021	Approved
0.6913	Remote Similarity	NPD6111	Discontinued
0.6908	Remote Similarity	NPD5177	Phase 3
0.6905	Remote Similarity	NPD844	Approved
0.6903	Remote Similarity	NPD4123	Phase 3
0.6903	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4967	Phase 2
0.6894	Remote Similarity	NPD4965	Approved
0.6894	Remote Similarity	NPD4966	Approved
0.6889	Remote Similarity	NPD7635	Approved
0.6887	Remote Similarity	NPD7266	Discontinued
0.6887	Remote Similarity	NPD1375	Discontinued
0.6884	Remote Similarity	NPD5536	Phase 2
0.6884	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1611	Approved
0.6875	Remote Similarity	NPD1465	Phase 2
0.6871	Remote Similarity	NPD5494	Approved
0.6863	Remote Similarity	NPD3892	Phase 2
0.6859	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4626	Approved
0.6853	Remote Similarity	NPD2922	Phase 1
0.6853	Remote Similarity	NPD3225	Approved
0.6849	Remote Similarity	NPD7095	Approved
0.6848	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1607	Approved
0.6846	Remote Similarity	NPD6653	Approved
0.6842	Remote Similarity	NPD8053	Approved
0.6842	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8054	Approved
0.6839	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7213	Phase 3
0.6839	Remote Similarity	NPD7212	Phase 2
0.6835	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2235	Phase 2
0.6831	Remote Similarity	NPD2232	Approved
0.6831	Remote Similarity	NPD2233	Approved
0.6831	Remote Similarity	NPD2231	Phase 2
0.6831	Remote Similarity	NPD2230	Approved
0.6828	Remote Similarity	NPD9494	Approved
0.6824	Remote Similarity	NPD2238	Phase 2
0.6822	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7906	Approved
0.6818	Remote Similarity	NPD6190	Approved
0.6806	Remote Similarity	NPD2797	Approved
0.6803	Remote Similarity	NPD7985	Registered
0.6792	Remote Similarity	NPD4380	Phase 2
0.6783	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD600	Approved
0.6781	Remote Similarity	NPD596	Approved
0.6779	Remote Similarity	NPD5735	Approved
0.6776	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7124	Phase 2
0.6763	Remote Similarity	NPD7644	Approved
0.6759	Remote Similarity	NPD6584	Phase 3
0.6757	Remote Similarity	NPD6233	Phase 2
0.6755	Remote Similarity	NPD7033	Discontinued
0.6753	Remote Similarity	NPD3750	Approved
0.6748	Remote Similarity	NPD7075	Discontinued
0.6748	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2424	Discontinued
0.6731	Remote Similarity	NPD6799	Approved
0.673	Remote Similarity	NPD4005	Discontinued
0.673	Remote Similarity	NPD3111	Phase 1
0.6728	Remote Similarity	NPD2563	Approved
0.6728	Remote Similarity	NPD2560	Approved
0.6727	Remote Similarity	NPD1247	Approved
0.6719	Remote Similarity	NPD288	Approved
0.6713	Remote Similarity	NPD1608	Approved
0.6712	Remote Similarity	NPD2237	Approved
0.6711	Remote Similarity	NPD2935	Discontinued
0.6711	Remote Similarity	NPD2796	Approved
0.6711	Remote Similarity	NPD1240	Approved
0.6709	Remote Similarity	NPD2122	Discontinued
0.6709	Remote Similarity	NPD5403	Approved
0.6706	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9295	Approved
0.6689	Remote Similarity	NPD4536	Approved
0.6689	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4538	Approved
0.6688	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4236	Phase 3
0.6688	Remote Similarity	NPD3060	Approved
0.6688	Remote Similarity	NPD1424	Approved
0.6688	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4237	Approved
0.6687	Remote Similarity	NPD3787	Discontinued
0.6687	Remote Similarity	NPD6599	Discontinued
0.6686	Remote Similarity	NPD4578	Approved
0.6686	Remote Similarity	NPD7311	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