NPASS Compound

Structure

NPC137232 OpenBabel07101719522D 29 34 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 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 -2.9916 -0.3961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9340 0.3726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6602 -0.4959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9703 2.5921 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 -2.3547 -0.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 0.2728 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 -2.9025 1.8718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4494 3.0942 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 1.4757 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4294 -1.8275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7589 1.3555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7622 4.0440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 13 2 0 0 0 0 4 17 2 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 27 2 0 0 0 0 17 29 1 0 0 0 0 18 20 2 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 6 0 0 0 22 12 1 1 0 0 0 22 29 1 0 0 0 0 23 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.09
Volume:	381.402
LogP:	2.295
LogD:	1.321
LogS:	-3.645
# Rotatable Bonds:	0
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	4.261
Fsp3:	0.217
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.582
MDCK Permeability:	1.5491177691728808e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.176
30% Bioavailability (F30%):	0.34

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	69.07097625732422%
Volume Distribution (VD):	3.628
Pgp-substrate:	21.349769592285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.16
CYP1A2-substrate:	0.741
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.335
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	3.072
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.706
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.501
Carcinogencity:	0.123
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.4

Download Data

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

Natural Product: NPC137232

Natural Product ID:	NPC137232
*Common Name:**	Ohioensin F
IUPAC Name:	n.a.
Synonyms:	Ohioensin F
Standard InCHIKey:	CJDAIJHZTKDLTJ-VABKMULXSA-N
Standard InCHI:	InChI=1S/C23H16O6/c24-10-5-6-11-12(7-10)22-21-20-18(11)14(25)8-15(26)19(20)16(27)9-23(21,28)13-3-1-2-4-17(13)29-22/h1-8,21-22,24-26,28H,9H2/t21-,22-,23-/m0/s1
SMILES:	c1ccc2c(c1)[C@]1(CC(=O)c3c(cc(c4-c5ccc(cc5[C@@H]([C@@H]1c34)O2)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403094
PubChem CID:	25033124
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans

*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
NPO15696	Polytrichastrum alpinum	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18053716]
NPO40840	Eremophila spp.	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26960032]
NPO15696	Polytrichastrum alpinum	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Ki	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	3500.0	nM	PMID[568794]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	1500.0	nM	PMID[568794]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	3500.0	nM	PMID[568795]

☑ 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 NPC137232 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	436
0.1-0.2	1732
0.2-0.3	3632
0.3-0.4	9178
0.4-0.5	9295
0.5-0.6	3545
0.6-0.7	5406
0.7-0.8	5644
0.8-0.85	2385
0.85-0.9	1305
0.9-0.95	131
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC292863
0.9934	High Similarity	NPC184326
0.9869	High Similarity	NPC18380
0.9868	High Similarity	NPC195167
0.9742	High Similarity	NPC290160
0.9497	High Similarity	NPC300307
0.9427	High Similarity	NPC15374
0.9379	High Similarity	NPC4200
0.929	High Similarity	NPC134171
0.929	High Similarity	NPC66441
0.929	High Similarity	NPC182555
0.929	High Similarity	NPC300668
0.9286	High Similarity	NPC87708
0.9276	High Similarity	NPC106328
0.9276	High Similarity	NPC35150
0.9245	High Similarity	NPC473009
0.9241	High Similarity	NPC301256
0.9241	High Similarity	NPC312273
0.9236	High Similarity	NPC51760
0.9236	High Similarity	NPC472617
0.9231	High Similarity	NPC32867
0.9231	High Similarity	NPC69531
0.9226	High Similarity	NPC329844
0.9226	High Similarity	NPC121568
0.9221	High Similarity	NPC149526
0.9221	High Similarity	NPC232645
0.9221	High Similarity	NPC474417
0.9221	High Similarity	NPC72958
0.9187	High Similarity	NPC469664
0.9187	High Similarity	NPC473010
0.9182	High Similarity	NPC473012
0.9182	High Similarity	NPC473011
0.9177	High Similarity	NPC472618
0.9177	High Similarity	NPC186325
0.9172	High Similarity	NPC475184
0.9167	High Similarity	NPC254351
0.9156	High Similarity	NPC472633
0.915	High Similarity	NPC122894
0.913	High Similarity	NPC251336
0.9119	High Similarity	NPC273467
0.9119	High Similarity	NPC189552
0.9114	High Similarity	NPC295090
0.9114	High Similarity	NPC55443
0.9114	High Similarity	NPC18699
0.9114	High Similarity	NPC177650
0.9114	High Similarity	NPC105584
0.9103	High Similarity	NPC169990
0.9103	High Similarity	NPC210942
0.9097	High Similarity	NPC317715
0.9097	High Similarity	NPC316960
0.9097	High Similarity	NPC478148
0.9097	High Similarity	NPC148945
0.9097	High Similarity	NPC178484
0.9097	High Similarity	NPC309512
0.9097	High Similarity	NPC78835
0.9097	High Similarity	NPC204561
0.9091	High Similarity	NPC3642
0.9091	High Similarity	NPC329933
0.9091	High Similarity	NPC473016
0.9079	High Similarity	NPC470135
0.9079	High Similarity	NPC470136
0.9079	High Similarity	NPC39045
0.9057	High Similarity	NPC312993
0.9057	High Similarity	NPC42965
0.9057	High Similarity	NPC195136
0.9057	High Similarity	NPC98023
0.9057	High Similarity	NPC226462
0.9051	High Similarity	NPC257166
0.9051	High Similarity	NPC272196
0.9051	High Similarity	NPC1796
0.9045	High Similarity	NPC258474
0.9045	High Similarity	NPC201227
0.9038	High Similarity	NPC78324
0.9038	High Similarity	NPC115601
0.9038	High Similarity	NPC39154
0.9038	High Similarity	NPC208011
0.9038	High Similarity	NPC174086
0.9032	High Similarity	NPC29777
0.9032	High Similarity	NPC471115
0.902	High Similarity	NPC470133
0.902	High Similarity	NPC473078
0.902	High Similarity	NPC470134
0.902	High Similarity	NPC24136
0.902	High Similarity	NPC290133
0.902	High Similarity	NPC470132
0.902	High Similarity	NPC109183
0.902	High Similarity	NPC187282
0.902	High Similarity	NPC470131
0.9012	High Similarity	NPC272502
0.9012	High Similarity	NPC171985
0.9012	High Similarity	NPC477835
0.9012	High Similarity	NPC224851
0.9012	High Similarity	NPC320741
0.9	High Similarity	NPC472261
0.8994	High Similarity	NPC186113
0.8994	High Similarity	NPC15815
0.8994	High Similarity	NPC324736
0.8994	High Similarity	NPC51247
0.8987	High Similarity	NPC208152
0.8987	High Similarity	NPC78492
0.8987	High Similarity	NPC61112
0.8987	High Similarity	NPC309648
0.8987	High Similarity	NPC198489
0.8981	High Similarity	NPC194593
0.8981	High Similarity	NPC280530
0.8981	High Similarity	NPC71061
0.8981	High Similarity	NPC303485
0.8981	High Similarity	NPC72425
0.8981	High Similarity	NPC178964
0.8981	High Similarity	NPC290830
0.8981	High Similarity	NPC95842
0.8974	High Similarity	NPC111112
0.8974	High Similarity	NPC138299
0.8974	High Similarity	NPC305965
0.8974	High Similarity	NPC222713
0.8974	High Similarity	NPC67322
0.8968	High Similarity	NPC288036
0.8968	High Similarity	NPC97029
0.8968	High Similarity	NPC65589
0.8968	High Similarity	NPC158338
0.8968	High Similarity	NPC132345
0.8968	High Similarity	NPC100985
0.8968	High Similarity	NPC97028
0.8961	High Similarity	NPC296998
0.8961	High Similarity	NPC308200
0.8961	High Similarity	NPC34802
0.8961	High Similarity	NPC473077
0.8957	High Similarity	NPC225419
0.8954	High Similarity	NPC131568
0.8954	High Similarity	NPC131579
0.8954	High Similarity	NPC271288
0.8951	High Similarity	NPC474591
0.8944	High Similarity	NPC473022
0.8944	High Similarity	NPC473961
0.8938	High Similarity	NPC470810
0.8938	High Similarity	NPC472060
0.8938	High Similarity	NPC470342
0.8938	High Similarity	NPC121647
0.8938	High Similarity	NPC472052
0.8931	High Similarity	NPC322459
0.8931	High Similarity	NPC281137
0.8931	High Similarity	NPC318527
0.8931	High Similarity	NPC323627
0.8931	High Similarity	NPC287789
0.8931	High Similarity	NPC282390
0.8931	High Similarity	NPC324358
0.8931	High Similarity	NPC271741
0.8931	High Similarity	NPC208258
0.8924	High Similarity	NPC121649
0.8924	High Similarity	NPC248739
0.8924	High Similarity	NPC186227
0.8924	High Similarity	NPC55662
0.8924	High Similarity	NPC66508
0.8924	High Similarity	NPC226656
0.8924	High Similarity	NPC37253
0.8924	High Similarity	NPC159707
0.8924	High Similarity	NPC52611
0.8924	High Similarity	NPC215203
0.8924	High Similarity	NPC166054
0.8924	High Similarity	NPC158027
0.8924	High Similarity	NPC100049
0.8924	High Similarity	NPC150908
0.8924	High Similarity	NPC14606
0.8924	High Similarity	NPC205026
0.8924	High Similarity	NPC79375
0.8924	High Similarity	NPC265624
0.8917	High Similarity	NPC217447
0.8917	High Similarity	NPC474843
0.8917	High Similarity	NPC154683
0.8917	High Similarity	NPC40356
0.8916	High Similarity	NPC300657
0.891	High Similarity	NPC227122
0.891	High Similarity	NPC202595
0.8909	High Similarity	NPC477836
0.8903	High Similarity	NPC256672
0.8903	High Similarity	NPC7025
0.8903	High Similarity	NPC145467
0.8903	High Similarity	NPC27221
0.8903	High Similarity	NPC161191
0.8903	High Similarity	NPC39195
0.8902	High Similarity	NPC107627
0.8896	High Similarity	NPC111786
0.8896	High Similarity	NPC475052
0.8896	High Similarity	NPC285630
0.8896	High Similarity	NPC470676
0.8896	High Similarity	NPC127059
0.8896	High Similarity	NPC301276
0.8896	High Similarity	NPC473132
0.8896	High Similarity	NPC246948
0.8896	High Similarity	NPC176229
0.8896	High Similarity	NPC178173
0.8896	High Similarity	NPC20488
0.8896	High Similarity	NPC54577
0.8896	High Similarity	NPC83357
0.8896	High Similarity	NPC473135
0.8896	High Similarity	NPC470647
0.8896	High Similarity	NPC43319
0.8896	High Similarity	NPC477955
0.8896	High Similarity	NPC267375
0.8896	High Similarity	NPC214774

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 NPC137232 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	992
0.2-0.3	1565
0.3-0.4	2604
0.4-0.5	1869
0.5-0.6	1049
0.6-0.7	452
0.7-0.8	170
0.8-0.85	34
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9363	High Similarity	NPD6959	Discontinued
0.8924	High Similarity	NPD8443	Clinical (unspecified phase)
0.8742	High Similarity	NPD2393	Clinical (unspecified phase)
0.8625	High Similarity	NPD7819	Suspended
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.8606	High Similarity	NPD7852	Clinical (unspecified phase)
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.859	High Similarity	NPD7410	Clinical (unspecified phase)
0.8562	High Similarity	NPD1549	Phase 2
0.8553	High Similarity	NPD4380	Phase 2
0.8526	High Similarity	NPD7390	Discontinued
0.85	High Similarity	NPD7411	Suspended
0.8494	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6166	Phase 2
0.8494	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD3749	Approved
0.8452	Intermediate Similarity	NPD5844	Phase 1
0.8447	Intermediate Similarity	NPD1934	Approved
0.8443	Intermediate Similarity	NPD7473	Discontinued
0.8405	Intermediate Similarity	NPD7768	Phase 2
0.8373	Intermediate Similarity	NPD6232	Discontinued
0.8253	Intermediate Similarity	NPD5494	Approved
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8242	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7075	Discontinued
0.8208	Intermediate Similarity	NPD8312	Approved
0.8208	Intermediate Similarity	NPD8313	Approved
0.8194	Intermediate Similarity	NPD2796	Approved
0.8182	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1511	Approved
0.8171	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD2533	Approved
0.8125	Intermediate Similarity	NPD2532	Approved
0.8125	Intermediate Similarity	NPD2534	Approved
0.8101	Intermediate Similarity	NPD3750	Approved
0.8092	Intermediate Similarity	NPD6559	Discontinued
0.8089	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7074	Phase 3
0.8075	Intermediate Similarity	NPD1512	Approved
0.8061	Intermediate Similarity	NPD2801	Approved
0.8023	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1607	Approved
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1240	Approved
0.7977	Intermediate Similarity	NPD7472	Approved
0.7974	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6100	Approved
0.7962	Intermediate Similarity	NPD6099	Approved
0.7941	Intermediate Similarity	NPD3787	Discontinued
0.7931	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6797	Phase 2
0.7927	Intermediate Similarity	NPD3226	Approved
0.7925	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6801	Discontinued
0.7886	Intermediate Similarity	NPD7251	Discontinued
0.7877	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7003	Approved
0.7861	Intermediate Similarity	NPD3751	Discontinued
0.7861	Intermediate Similarity	NPD3818	Discontinued
0.7857	Intermediate Similarity	NPD3882	Suspended
0.7848	Intermediate Similarity	NPD5406	Approved
0.7848	Intermediate Similarity	NPD5404	Approved
0.7848	Intermediate Similarity	NPD5405	Approved
0.7848	Intermediate Similarity	NPD5408	Approved
0.7843	Intermediate Similarity	NPD4908	Phase 1
0.7841	Intermediate Similarity	NPD7808	Phase 3
0.7812	Intermediate Similarity	NPD2800	Approved
0.7799	Intermediate Similarity	NPD2346	Discontinued
0.7798	Intermediate Similarity	NPD3817	Phase 2
0.7792	Intermediate Similarity	NPD4625	Phase 3
0.7785	Intermediate Similarity	NPD3748	Approved
0.7771	Intermediate Similarity	NPD6599	Discontinued
0.774	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD1465	Phase 2
0.7737	Intermediate Similarity	NPD8151	Discontinued
0.7736	Intermediate Similarity	NPD2935	Discontinued
0.7736	Intermediate Similarity	NPD1551	Phase 2
0.7733	Intermediate Similarity	NPD7229	Phase 3
0.773	Intermediate Similarity	NPD6799	Approved
0.7713	Intermediate Similarity	NPD7871	Phase 2
0.7713	Intermediate Similarity	NPD7870	Phase 2
0.7692	Intermediate Similarity	NPD5402	Approved
0.7688	Intermediate Similarity	NPD6776	Approved
0.7688	Intermediate Similarity	NPD6779	Approved
0.7688	Intermediate Similarity	NPD6782	Approved
0.7688	Intermediate Similarity	NPD6781	Approved
0.7688	Intermediate Similarity	NPD6778	Approved
0.7688	Intermediate Similarity	NPD6777	Approved
0.7688	Intermediate Similarity	NPD6780	Approved
0.7654	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5710	Approved
0.763	Intermediate Similarity	NPD5711	Approved
0.7609	Intermediate Similarity	NPD4363	Phase 3
0.7609	Intermediate Similarity	NPD4360	Phase 2
0.7605	Intermediate Similarity	NPD7458	Discontinued
0.759	Intermediate Similarity	NPD5403	Approved
0.759	Intermediate Similarity	NPD920	Approved
0.7578	Intermediate Similarity	NPD2344	Approved
0.7576	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8150	Discontinued
0.7566	Intermediate Similarity	NPD7698	Approved
0.7566	Intermediate Similarity	NPD7696	Phase 3
0.7566	Intermediate Similarity	NPD7697	Approved
0.7566	Intermediate Similarity	NPD7435	Discontinued
0.7565	Intermediate Similarity	NPD7783	Phase 2
0.7565	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2799	Discontinued
0.7561	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7177	Discontinued
0.7547	Intermediate Similarity	NPD6651	Approved
0.753	Intermediate Similarity	NPD6273	Approved
0.7529	Intermediate Similarity	NPD8455	Phase 2
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7486	Intermediate Similarity	NPD4287	Approved
0.7485	Intermediate Similarity	NPD1243	Approved
0.747	Intermediate Similarity	NPD5401	Approved
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.743	Intermediate Similarity	NPD5953	Discontinued
0.7421	Intermediate Similarity	NPD6823	Phase 2
0.7419	Intermediate Similarity	NPD1470	Approved
0.7419	Intermediate Similarity	NPD6534	Approved
0.7419	Intermediate Similarity	NPD6535	Approved
0.7416	Intermediate Similarity	NPD7286	Phase 2
0.7409	Intermediate Similarity	NPD7701	Phase 2
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7394	Intermediate Similarity	NPD2309	Approved
0.7386	Intermediate Similarity	NPD3926	Phase 2
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7801	Approved
0.7375	Intermediate Similarity	NPD5124	Phase 1
0.7375	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7199	Phase 2
0.7371	Intermediate Similarity	NPD1247	Approved
0.7368	Intermediate Similarity	NPD37	Approved
0.736	Intermediate Similarity	NPD7228	Approved
0.7356	Intermediate Similarity	NPD6234	Discontinued
0.7356	Intermediate Similarity	NPD919	Approved
0.7341	Intermediate Similarity	NPD4967	Phase 2
0.7341	Intermediate Similarity	NPD4965	Approved
0.7341	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7874	Approved
0.7326	Intermediate Similarity	NPD5761	Phase 2
0.7326	Intermediate Similarity	NPD5760	Phase 2
0.7325	Intermediate Similarity	NPD2861	Phase 2
0.7322	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1613	Approved
0.7312	Intermediate Similarity	NPD943	Approved
0.7312	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7700	Phase 2
0.7302	Intermediate Similarity	NPD7699	Phase 2
0.7296	Intermediate Similarity	NPD3764	Approved
0.7296	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4749	Approved
0.7288	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD8319	Approved
0.7254	Intermediate Similarity	NPD8320	Phase 1
0.7249	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7033	Discontinued
0.7229	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1203	Approved
0.7196	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4361	Phase 2
0.7189	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD3268	Approved
0.7184	Intermediate Similarity	NPD4288	Approved
0.7176	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2798	Approved
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1283	Approved
0.7134	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7115	Intermediate Similarity	NPD1608	Approved
0.7107	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7099	Intermediate Similarity	NPD2979	Phase 3
0.7092	Intermediate Similarity	NPD7584	Approved
0.709	Intermediate Similarity	NPD6212	Phase 3
0.709	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6213	Phase 3
0.7089	Intermediate Similarity	NPD2797	Approved
0.7083	Intermediate Similarity	NPD8285	Discontinued
0.7078	Intermediate Similarity	NPD1651	Approved
0.7076	Intermediate Similarity	NPD7427	Discontinued
0.7072	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6844	Discontinued

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