NPASS Compound

Structure

NPC290160 OpenBabel07101719512D 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 -2.5981 -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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -2.8640 2.7763 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 0.0000 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 -3.0383 2.0741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2063 3.0777 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 -2.5981 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 2 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 -1.5605 2.7515 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 -0.1715 2.7515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 3.0860 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 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0173 1.8702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1873 4.0776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6103 3.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.0860 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 4 1 0 0 0 0 2 7 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 14 2 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 17 1 0 0 0 0 12 25 1 0 0 0 0 13 18 2 0 0 0 0 13 26 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 16 9 1 6 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 20 19 1 6 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 6 0 0 0 22 28 2 0 0 0 0 23 10 1 1 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.09
Volume:	381.402
LogP:	4.436
LogD:	2.347
LogS:	-5.424
# Rotatable Bonds:	0
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.199
Synthetic Accessibility Score:	3.927
Fsp3:	0.13
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.638
MDCK Permeability:	7.293060207302915e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.873
20% Bioavailability (F20%):	0.234
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	99.2705307006836%
Volume Distribution (VD):	0.428
Pgp-substrate:	4.195239067077637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.575
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.362
CYP2C9-substrate:	0.723
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	2.779
Half-life (T1/2):	0.413

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.014
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.78
Rat Oral Acute Toxicity:	0.375
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.924
Carcinogencity:	0.767
Eye Corrosion:	0.003
Eye Irritation:	0.835
Respiratory Toxicity:	0.294

Download Data

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

Natural Product: NPC290160

Natural Product ID:	NPC290160
*Common Name:**	Ohioensin G
IUPAC Name:	n.a.
Synonyms:	Ohioensin G
Standard InCHIKey:	JFOHOILWNMBZGW-QSABTFIQSA-N
Standard InCHI:	InChI=1S/C23H16O6/c24-11-6-3-5-10-15(11)17-12(25)8-13(26)18-19(17)20-16(21(27)22(18)28)9-4-1-2-7-14(9)29-23(10)20/h1-8,16,20-21,23-27H/t16-,20+,21-,23+/m1/s1
SMILES:	c1ccc2c(c1)[C@@H]1[C@H]3c4c(-c5c(cccc5O)[C@@H]3O2)c(cc(c4C(=O)[C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403411
PubChem CID:	25033201
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

Activity Type	# Activity
Individual Protein	2

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	=	5600.0	nM	PMID[572959]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	3500.0	nM	PMID[572960]

☑ 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 NPC290160 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	431
0.1-0.2	1748
0.2-0.3	3673
0.3-0.4	9210
0.4-0.5	9277
0.5-0.6	3648
0.6-0.7	5401
0.7-0.8	5462
0.8-0.85	2705
0.85-0.9	1068
0.9-0.95	66
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC184326
0.9805	High Similarity	NPC292863
0.9742	High Similarity	NPC137232
0.9742	High Similarity	NPC18380
0.974	High Similarity	NPC195167
0.9379	High Similarity	NPC300307
0.9308	High Similarity	NPC15374
0.9264	High Similarity	NPC4200
0.9241	High Similarity	NPC295090
0.9193	High Similarity	NPC469664
0.9177	High Similarity	NPC475184
0.9172	High Similarity	NPC300668
0.9172	High Similarity	NPC66441
0.9172	High Similarity	NPC134171
0.9172	High Similarity	NPC182555
0.9167	High Similarity	NPC87708
0.9156	High Similarity	NPC35150
0.9156	High Similarity	NPC106328
0.913	High Similarity	NPC63438
0.9125	High Similarity	NPC312273
0.9125	High Similarity	NPC301256
0.9119	High Similarity	NPC51760
0.9119	High Similarity	NPC472617
0.9119	High Similarity	NPC123544
0.9114	High Similarity	NPC32867
0.9114	High Similarity	NPC69531
0.9108	High Similarity	NPC244250
0.9108	High Similarity	NPC121568
0.9108	High Similarity	NPC20907
0.9103	High Similarity	NPC72958
0.9103	High Similarity	NPC232645
0.9068	High Similarity	NPC473011
0.9068	High Similarity	NPC473012
0.9062	High Similarity	NPC472618
0.9062	High Similarity	NPC186325
0.9057	High Similarity	NPC281137
0.9057	High Similarity	NPC282390
0.9057	High Similarity	NPC257166
0.9051	High Similarity	NPC254351
0.9032	High Similarity	NPC122894
0.903	High Similarity	NPC472454
0.903	High Similarity	NPC257667
0.903	High Similarity	NPC186847
0.9024	High Similarity	NPC107627
0.9018	High Similarity	NPC251336
0.9012	High Similarity	NPC473009
0.9006	High Similarity	NPC273467
0.9006	High Similarity	NPC189552
0.9	High Similarity	NPC55443
0.9	High Similarity	NPC186113
0.9	High Similarity	NPC18699
0.9	High Similarity	NPC15815
0.9	High Similarity	NPC51247
0.9	High Similarity	NPC324736
0.9	High Similarity	NPC105584
0.9	High Similarity	NPC177650
0.8994	High Similarity	NPC78492
0.8994	High Similarity	NPC208152
0.8987	High Similarity	NPC193200
0.8987	High Similarity	NPC329844
0.8981	High Similarity	NPC316960
0.8981	High Similarity	NPC309512
0.8981	High Similarity	NPC149526
0.8981	High Similarity	NPC474417
0.8981	High Similarity	NPC148945
0.8981	High Similarity	NPC178484
0.8981	High Similarity	NPC204561
0.8981	High Similarity	NPC78835
0.8981	High Similarity	NPC317715
0.8974	High Similarity	NPC3642
0.8961	High Similarity	NPC470136
0.8961	High Similarity	NPC39045
0.8961	High Similarity	NPC470135
0.8957	High Similarity	NPC473010
0.8957	High Similarity	NPC474591
0.8944	High Similarity	NPC312993
0.8944	High Similarity	NPC42965
0.8944	High Similarity	NPC226462
0.8944	High Similarity	NPC98023
0.8944	High Similarity	NPC195136
0.8938	High Similarity	NPC1796
0.8938	High Similarity	NPC208258
0.8931	High Similarity	NPC201227
0.8931	High Similarity	NPC258474
0.8924	High Similarity	NPC474843
0.8924	High Similarity	NPC115601
0.8924	High Similarity	NPC216035
0.8924	High Similarity	NPC78324
0.8924	High Similarity	NPC208011
0.8924	High Similarity	NPC217149
0.8924	High Similarity	NPC174086
0.8924	High Similarity	NPC39154
0.8917	High Similarity	NPC202595
0.8917	High Similarity	NPC472633
0.8903	High Similarity	NPC472629
0.8903	High Similarity	NPC470134
0.8903	High Similarity	NPC187282
0.8903	High Similarity	NPC290133
0.8903	High Similarity	NPC470133
0.8903	High Similarity	NPC24136
0.8903	High Similarity	NPC470132
0.8903	High Similarity	NPC473078
0.8903	High Similarity	NPC109183
0.8903	High Similarity	NPC470131
0.8902	High Similarity	NPC224851
0.8902	High Similarity	NPC171985
0.8902	High Similarity	NPC320741
0.8902	High Similarity	NPC477835
0.8896	High Similarity	NPC469395
0.8889	High Similarity	NPC97812
0.8876	High Similarity	NPC153578
0.8876	High Similarity	NPC299149
0.8876	High Similarity	NPC114257
0.8876	High Similarity	NPC277710
0.8875	High Similarity	NPC61112
0.8875	High Similarity	NPC192587
0.8875	High Similarity	NPC309648
0.8875	High Similarity	NPC198489
0.8868	High Similarity	NPC290830
0.8868	High Similarity	NPC303485
0.8868	High Similarity	NPC135522
0.8868	High Similarity	NPC268193
0.8868	High Similarity	NPC71061
0.8868	High Similarity	NPC72425
0.8868	High Similarity	NPC169990
0.8868	High Similarity	NPC210942
0.8868	High Similarity	NPC194593
0.8861	High Similarity	NPC478148
0.8861	High Similarity	NPC254412
0.8861	High Similarity	NPC138299
0.8861	High Similarity	NPC262038
0.8861	High Similarity	NPC319910
0.8861	High Similarity	NPC278476
0.8861	High Similarity	NPC111112
0.8861	High Similarity	NPC67322
0.8861	High Similarity	NPC222713
0.8861	High Similarity	NPC262039
0.8855	High Similarity	NPC279209
0.8855	High Similarity	NPC102277
0.8854	High Similarity	NPC100985
0.8854	High Similarity	NPC473016
0.8854	High Similarity	NPC158338
0.8854	High Similarity	NPC132345
0.8854	High Similarity	NPC97028
0.8854	High Similarity	NPC65589
0.8854	High Similarity	NPC288036
0.8854	High Similarity	NPC97029
0.8854	High Similarity	NPC329933
0.8854	High Similarity	NPC470461
0.8848	High Similarity	NPC225419
0.8848	High Similarity	NPC260266
0.8846	High Similarity	NPC308200
0.8839	High Similarity	NPC470890
0.8839	High Similarity	NPC124780
0.8839	High Similarity	NPC271288
0.8839	High Similarity	NPC87486
0.8834	High Similarity	NPC473961
0.8834	High Similarity	NPC211107
0.8827	High Similarity	NPC472060
0.8827	High Similarity	NPC472052
0.8827	High Similarity	NPC321399
0.8827	High Similarity	NPC470342
0.882	High Similarity	NPC287789
0.882	High Similarity	NPC271741
0.882	High Similarity	NPC318527
0.882	High Similarity	NPC272196
0.882	High Similarity	NPC324358
0.882	High Similarity	NPC322459
0.882	High Similarity	NPC323627
0.8812	High Similarity	NPC14606
0.8812	High Similarity	NPC205026
0.8812	High Similarity	NPC79375
0.8812	High Similarity	NPC217706
0.8812	High Similarity	NPC275575
0.8812	High Similarity	NPC158027
0.8812	High Similarity	NPC121649
0.8812	High Similarity	NPC248739
0.8812	High Similarity	NPC66508
0.8812	High Similarity	NPC37253
0.8812	High Similarity	NPC265624
0.8812	High Similarity	NPC226656
0.8812	High Similarity	NPC259710
0.8812	High Similarity	NPC159707
0.8812	High Similarity	NPC215203
0.8812	High Similarity	NPC52611
0.8812	High Similarity	NPC111341
0.8812	High Similarity	NPC304207
0.8812	High Similarity	NPC207809
0.8812	High Similarity	NPC304745
0.8812	High Similarity	NPC48579
0.8812	High Similarity	NPC186227
0.8812	High Similarity	NPC100049
0.8812	High Similarity	NPC150908
0.881	High Similarity	NPC300657
0.8805	High Similarity	NPC142527
0.8805	High Similarity	NPC138288
0.8805	High Similarity	NPC40356
0.8805	High Similarity	NPC243171
0.8805	High Similarity	NPC154683
0.8805	High Similarity	NPC35567

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 NPC290160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	983
0.2-0.3	1613
0.3-0.4	2609
0.4-0.5	1852
0.5-0.6	1039
0.6-0.7	442
0.7-0.8	161
0.8-0.85	37
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9245	High Similarity	NPD6959	Discontinued
0.8812	High Similarity	NPD8443	Clinical (unspecified phase)
0.8727	High Similarity	NPD6168	Clinical (unspecified phase)
0.8727	High Similarity	NPD6166	Phase 2
0.8727	High Similarity	NPD6167	Clinical (unspecified phase)
0.8718	High Similarity	NPD4378	Clinical (unspecified phase)
0.8634	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD4380	Phase 2
0.8519	High Similarity	NPD7819	Suspended
0.8506	High Similarity	NPD1550	Clinical (unspecified phase)
0.8506	High Similarity	NPD1552	Clinical (unspecified phase)
0.8503	High Similarity	NPD7852	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD5844	Phase 1
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8418	Intermediate Similarity	NPD7390	Discontinued
0.8395	Intermediate Similarity	NPD7411	Suspended
0.8365	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7075	Discontinued
0.8353	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1934	Approved
0.8343	Intermediate Similarity	NPD7473	Discontinued
0.8303	Intermediate Similarity	NPD7768	Phase 2
0.8293	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD6232	Discontinued
0.8253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD3749	Approved
0.8218	Intermediate Similarity	NPD8312	Approved
0.8218	Intermediate Similarity	NPD8313	Approved
0.8199	Intermediate Similarity	NPD1512	Approved
0.816	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD5494	Approved
0.815	Intermediate Similarity	NPD6797	Phase 2
0.815	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1510	Phase 2
0.8121	Intermediate Similarity	NPD6801	Discontinued
0.8103	Intermediate Similarity	NPD6559	Discontinued
0.8103	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7074	Phase 3
0.8089	Intermediate Similarity	NPD2796	Approved
0.8084	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1511	Approved
0.8059	Intermediate Similarity	NPD3787	Discontinued
0.8057	Intermediate Similarity	NPD7808	Phase 3
0.8035	Intermediate Similarity	NPD7054	Approved
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD3750	Approved
0.7989	Intermediate Similarity	NPD7472	Approved
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD3751	Discontinued
0.7976	Intermediate Similarity	NPD3882	Suspended
0.7964	Intermediate Similarity	NPD2801	Approved
0.7955	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5402	Approved
0.7917	Intermediate Similarity	NPD3817	Phase 2
0.7898	Intermediate Similarity	NPD1607	Approved
0.7892	Intermediate Similarity	NPD6599	Discontinued
0.7885	Intermediate Similarity	NPD1240	Approved
0.7874	Intermediate Similarity	NPD3818	Discontinued
0.7871	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6799	Approved
0.7831	Intermediate Similarity	NPD3226	Approved
0.7826	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD7870	Phase 2
0.7819	Intermediate Similarity	NPD7871	Phase 2
0.7818	Intermediate Similarity	NPD5403	Approved
0.7799	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD6782	Approved
0.7796	Intermediate Similarity	NPD6776	Approved
0.7796	Intermediate Similarity	NPD6777	Approved
0.7796	Intermediate Similarity	NPD6780	Approved
0.7796	Intermediate Similarity	NPD6778	Approved
0.7796	Intermediate Similarity	NPD6781	Approved
0.7796	Intermediate Similarity	NPD6779	Approved
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7003	Approved
0.775	Intermediate Similarity	NPD5404	Approved
0.775	Intermediate Similarity	NPD6099	Approved
0.775	Intermediate Similarity	NPD5406	Approved
0.775	Intermediate Similarity	NPD6100	Approved
0.775	Intermediate Similarity	NPD5405	Approved
0.775	Intermediate Similarity	NPD5408	Approved
0.7749	Intermediate Similarity	NPD8151	Discontinued
0.7742	Intermediate Similarity	NPD4908	Phase 1
0.7716	Intermediate Similarity	NPD2800	Approved
0.7702	Intermediate Similarity	NPD2346	Discontinued
0.7697	Intermediate Similarity	NPD5401	Approved
0.7688	Intermediate Similarity	NPD3748	Approved
0.768	Intermediate Similarity	NPD8150	Discontinued
0.7672	Intermediate Similarity	NPD7435	Discontinued
0.7672	Intermediate Similarity	NPD7696	Phase 3
0.7672	Intermediate Similarity	NPD7698	Approved
0.7672	Intermediate Similarity	NPD7697	Approved
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1465	Phase 2
0.7644	Intermediate Similarity	NPD7229	Phase 3
0.764	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD2935	Discontinued
0.7622	Intermediate Similarity	NPD4360	Phase 2
0.7622	Intermediate Similarity	NPD4363	Phase 3
0.758	Intermediate Similarity	NPD4625	Phase 3
0.7545	Intermediate Similarity	NPD6273	Approved
0.7544	Intermediate Similarity	NPD8455	Phase 2
0.7543	Intermediate Similarity	NPD5710	Approved
0.7543	Intermediate Similarity	NPD5711	Approved
0.7527	Intermediate Similarity	NPD6534	Approved
0.7527	Intermediate Similarity	NPD6535	Approved
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.7513	Intermediate Similarity	NPD7701	Phase 2
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD920	Approved
0.7487	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7801	Approved
0.7487	Intermediate Similarity	NPD7783	Phase 2
0.7486	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2344	Approved
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7177	Discontinued
0.7471	Intermediate Similarity	NPD919	Approved
0.747	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7455	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6651	Approved
0.7447	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7874	Approved
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7699	Phase 2
0.7407	Intermediate Similarity	NPD7700	Phase 2
0.7403	Intermediate Similarity	NPD1201	Approved
0.7403	Intermediate Similarity	NPD1610	Phase 2
0.7401	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1243	Approved
0.7386	Intermediate Similarity	NPD7199	Phase 2
0.7384	Intermediate Similarity	NPD37	Approved
0.7374	Intermediate Similarity	NPD7228	Approved
0.7358	Intermediate Similarity	NPD8320	Phase 1
0.7358	Intermediate Similarity	NPD8319	Approved
0.7356	Intermediate Similarity	NPD4966	Approved
0.7356	Intermediate Similarity	NPD4967	Phase 2
0.7356	Intermediate Similarity	NPD4965	Approved
0.7348	Intermediate Similarity	NPD5953	Discontinued
0.7344	Intermediate Similarity	NPD6823	Phase 2
0.7337	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7286	Phase 2
0.7329	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1613	Approved
0.7325	Intermediate Similarity	NPD1470	Approved
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.7312	Intermediate Similarity	NPD4287	Approved
0.7305	Intermediate Similarity	NPD2309	Approved
0.7297	Intermediate Similarity	NPD8434	Phase 2
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5124	Phase 1
0.7284	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6234	Discontinued
0.7256	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5760	Phase 2
0.7241	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5761	Phase 2
0.724	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2861	Phase 2
0.7225	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD943	Approved
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7211	Intermediate Similarity	NPD4361	Phase 2
0.7211	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1471	Phase 3
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7107	Intermediate Similarity	NPD1203	Approved
0.7105	Intermediate Similarity	NPD6213	Phase 3
0.7105	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6212	Phase 3
0.7102	Intermediate Similarity	NPD4288	Approved
0.7099	Intermediate Similarity	NPD3764	Approved
0.7099	Intermediate Similarity	NPD6798	Discontinued
0.7099	Intermediate Similarity	NPD3268	Approved
0.7093	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4749	Approved
0.7086	Intermediate Similarity	NPD6844	Discontinued
0.7081	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2798	Approved
0.7059	Intermediate Similarity	NPD3300	Phase 2
0.7056	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1283	Approved
0.7032	Intermediate Similarity	NPD1548	Phase 1
0.7027	Intermediate Similarity	NPD7240	Approved
0.7025	Intermediate Similarity	NPD1608	Approved
0.702	Intermediate Similarity	NPD7584	Approved
0.7019	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2979	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