NPASS Compound

Structure

CID292863 OpenBabel06191716102D 28 33 0 0 1 0 0 0 0 0999 V2000 -2.3515 1.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3582 0.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3298 -1.3629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5601 1.8272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5543 -0.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1120 -0.9191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5734 0.0071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0186 2.7106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1411 2.6947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7753 1.3664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5611 -0.0081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0113 1.8127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1188 -0.0198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8008 3.1544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 3.1515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1462 1.7850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7819 0.4564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3433 0.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7912 1.3489 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5844 2.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3596 1.3388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5734 1.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7865 0.4463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9047 0.4261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8028 4.0584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3729 4.0555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9286 1.3323 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 10 2 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 7 17 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 8 1 1 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 24 1 0 0 0 0 14 20 1 0 0 0 0 14 25 2 0 0 0 0 15 20 1 0 0 0 0 15 26 1 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 1 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 21 22 1 0 0 0 0 23 11 1 6 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.1
Volume:	372.612
LogP:	5.108
LogD:	3.3
LogS:	-5.922
# Rotatable Bonds:	0
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.545
Synthetic Accessibility Score:	3.843
Fsp3:	0.174
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.57
MDCK Permeability:	8.412800525547937e-06
Pgp-inhibitor:	0.02
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.414
20% Bioavailability (F20%):	0.762
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	98.82343292236328%
Volume Distribution (VD):	0.457
Pgp-substrate:	1.4553459882736206%

ADMET: Metabolism

CYP1A2-inhibitor:	0.48
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.898
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.906
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.78
CYP2D6-substrate:	0.425
CYP3A4-inhibitor:	0.33
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	3.755
Half-life (T1/2):	0.071

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.373
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.931
Rat Oral Acute Toxicity:	0.844
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.705
Carcinogencity:	0.498
Eye Corrosion:	0.003
Eye Irritation:	0.65
Respiratory Toxicity:	0.303

Download Data

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

Natural Product: NPC292863

Natural Product ID:	NPC292863
*Common Name:**	Ohioensin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VYRXNKPPFHPOIN-BTPUUTEISA-N
Standard InCHI:	InChI=1S/C23H16O5/c24-13-6-3-5-11-18(13)21-16(27)9-15(26)20-14(25)8-12-10-4-1-2-7-17(10)28-23(11)19(12)22(20)21/h1-7,9,12,19,23-24,26-27H,8H2/t12-,19+,23+/m1/s1
SMILES:	c1ccc2c(c1)[C@H]1CC(=O)c3c(cc(c4-c5c(cccc5O)[C@@H]([C@@H]1c34)O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL257644
PubChem CID:	9976521
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
NPO3518	Polytrichum ohioense	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3518	Polytrichum ohioense	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3518	Polytrichum ohioense	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
ED50	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	8.0	ug ml-1	PMID[448597]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[448597]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	7.0	ug ml-1	PMID[448597]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.0	ug ml-1	PMID[448597]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[448597]

☑ 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 NPC292863 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	1723
0.2-0.3	3668
0.3-0.4	9357
0.4-0.5	9114
0.5-0.6	3487
0.6-0.7	5359
0.7-0.8	5563
0.8-0.85	2489
0.85-0.9	1306
0.9-0.95	187
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC184326
0.9934	High Similarity	NPC137232
0.9934	High Similarity	NPC18380
0.9934	High Similarity	NPC195167
0.9805	High Similarity	NPC290160
0.9557	High Similarity	NPC300307
0.9487	High Similarity	NPC15374
0.9437	High Similarity	NPC4200
0.9351	High Similarity	NPC134171
0.9351	High Similarity	NPC182555
0.9351	High Similarity	NPC300668
0.9351	High Similarity	NPC66441
0.9346	High Similarity	NPC87708
0.9338	High Similarity	NPC106328
0.9338	High Similarity	NPC35150
0.9299	High Similarity	NPC312273
0.9299	High Similarity	NPC301256
0.9295	High Similarity	NPC51760
0.929	High Similarity	NPC32867
0.929	High Similarity	NPC69531
0.9286	High Similarity	NPC121568
0.9281	High Similarity	NPC232645
0.9281	High Similarity	NPC72958
0.9245	High Similarity	NPC469664
0.9241	High Similarity	NPC473012
0.9241	High Similarity	NPC473011
0.9236	High Similarity	NPC186325
0.9231	High Similarity	NPC475184
0.9226	High Similarity	NPC254351
0.9211	High Similarity	NPC122894
0.9187	High Similarity	NPC251336
0.9182	High Similarity	NPC473009
0.9177	High Similarity	NPC189552
0.9177	High Similarity	NPC273467
0.9172	High Similarity	NPC105584
0.9172	High Similarity	NPC295090
0.9172	High Similarity	NPC472617
0.9172	High Similarity	NPC177650
0.9172	High Similarity	NPC55443
0.9172	High Similarity	NPC18699
0.9161	High Similarity	NPC329844
0.9156	High Similarity	NPC309512
0.9156	High Similarity	NPC474417
0.9156	High Similarity	NPC148945
0.9156	High Similarity	NPC317715
0.9156	High Similarity	NPC149526
0.9156	High Similarity	NPC204561
0.9156	High Similarity	NPC78835
0.9156	High Similarity	NPC178484
0.9156	High Similarity	NPC316960
0.915	High Similarity	NPC3642
0.9139	High Similarity	NPC470136
0.9139	High Similarity	NPC470135
0.9139	High Similarity	NPC39045
0.9125	High Similarity	NPC473010
0.9114	High Similarity	NPC472618
0.9114	High Similarity	NPC312993
0.9114	High Similarity	NPC98023
0.9114	High Similarity	NPC226462
0.9114	High Similarity	NPC195136
0.9114	High Similarity	NPC42965
0.9108	High Similarity	NPC1796
0.9108	High Similarity	NPC257166
0.9103	High Similarity	NPC201227
0.9103	High Similarity	NPC258474
0.9097	High Similarity	NPC39154
0.9097	High Similarity	NPC115601
0.9097	High Similarity	NPC78324
0.9097	High Similarity	NPC208011
0.9097	High Similarity	NPC174086
0.9091	High Similarity	NPC472633
0.9079	High Similarity	NPC470134
0.9079	High Similarity	NPC24136
0.9079	High Similarity	NPC470131
0.9079	High Similarity	NPC470132
0.9079	High Similarity	NPC290133
0.9079	High Similarity	NPC187282
0.9079	High Similarity	NPC470133
0.9079	High Similarity	NPC109183
0.9079	High Similarity	NPC473078
0.9068	High Similarity	NPC224851
0.9068	High Similarity	NPC320741
0.9068	High Similarity	NPC477835
0.9068	High Similarity	NPC171985
0.9051	High Similarity	NPC324736
0.9051	High Similarity	NPC15815
0.9051	High Similarity	NPC186113
0.9051	High Similarity	NPC51247
0.9045	High Similarity	NPC309648
0.9045	High Similarity	NPC198489
0.9045	High Similarity	NPC61112
0.9045	High Similarity	NPC208152
0.9045	High Similarity	NPC78492
0.9038	High Similarity	NPC72425
0.9038	High Similarity	NPC194593
0.9038	High Similarity	NPC71061
0.9038	High Similarity	NPC169990
0.9038	High Similarity	NPC210942
0.9038	High Similarity	NPC303485
0.9038	High Similarity	NPC290830
0.9032	High Similarity	NPC67322
0.9032	High Similarity	NPC138299
0.9032	High Similarity	NPC222713
0.9032	High Similarity	NPC478148
0.9032	High Similarity	NPC111112
0.9026	High Similarity	NPC288036
0.9026	High Similarity	NPC132345
0.9026	High Similarity	NPC97028
0.9026	High Similarity	NPC100985
0.9026	High Similarity	NPC97029
0.9026	High Similarity	NPC473016
0.9026	High Similarity	NPC158338
0.9026	High Similarity	NPC329933
0.9026	High Similarity	NPC65589
0.902	High Similarity	NPC308200
0.9013	High Similarity	NPC271288
0.9006	High Similarity	NPC474591
0.8994	High Similarity	NPC470342
0.8994	High Similarity	NPC472052
0.8994	High Similarity	NPC472060
0.8987	High Similarity	NPC271741
0.8987	High Similarity	NPC323627
0.8987	High Similarity	NPC272196
0.8987	High Similarity	NPC208258
0.8987	High Similarity	NPC287789
0.8987	High Similarity	NPC322459
0.8987	High Similarity	NPC318527
0.8987	High Similarity	NPC324358
0.8981	High Similarity	NPC265624
0.8981	High Similarity	NPC158027
0.8981	High Similarity	NPC159707
0.8981	High Similarity	NPC226656
0.8981	High Similarity	NPC215203
0.8981	High Similarity	NPC52611
0.8981	High Similarity	NPC186227
0.8981	High Similarity	NPC66508
0.8981	High Similarity	NPC37253
0.8981	High Similarity	NPC14606
0.8981	High Similarity	NPC205026
0.8981	High Similarity	NPC79375
0.8981	High Similarity	NPC100049
0.8981	High Similarity	NPC150908
0.8981	High Similarity	NPC121649
0.8981	High Similarity	NPC248739
0.8974	High Similarity	NPC154683
0.8974	High Similarity	NPC474843
0.8974	High Similarity	NPC40356
0.897	High Similarity	NPC300657
0.8968	High Similarity	NPC202595
0.8968	High Similarity	NPC29777
0.8968	High Similarity	NPC471115
0.8968	High Similarity	NPC227122
0.8963	High Similarity	NPC477836
0.8961	High Similarity	NPC256672
0.8961	High Similarity	NPC7025
0.8961	High Similarity	NPC145467
0.8961	High Similarity	NPC39195
0.8961	High Similarity	NPC27221
0.8957	High Similarity	NPC107627
0.8954	High Similarity	NPC228779
0.8954	High Similarity	NPC472629
0.8951	High Similarity	NPC272502
0.8947	High Similarity	NPC77794
0.8947	High Similarity	NPC223812
0.8947	High Similarity	NPC85162
0.8947	High Similarity	NPC125894
0.8947	High Similarity	NPC81697
0.8947	High Similarity	NPC107177
0.8947	High Similarity	NPC278249
0.8944	High Similarity	NPC38591
0.8944	High Similarity	NPC63438
0.8938	High Similarity	NPC97812
0.8938	High Similarity	NPC472261
0.8931	High Similarity	NPC210459
0.8931	High Similarity	NPC123544
0.8931	High Similarity	NPC85121
0.8922	High Similarity	NPC114257
0.8922	High Similarity	NPC277710
0.8922	High Similarity	NPC299149
0.8922	High Similarity	NPC153578
0.8917	High Similarity	NPC95842
0.8917	High Similarity	NPC20907
0.8917	High Similarity	NPC135522
0.8917	High Similarity	NPC244250
0.8917	High Similarity	NPC178964
0.8917	High Similarity	NPC280530
0.891	High Similarity	NPC305965
0.8903	High Similarity	NPC471114
0.8896	High Similarity	NPC123202
0.8896	High Similarity	NPC300988
0.8896	High Similarity	NPC22005
0.8896	High Similarity	NPC296998
0.8896	High Similarity	NPC473077
0.8896	High Similarity	NPC34802
0.8896	High Similarity	NPC7943
0.8896	High Similarity	NPC10990
0.8896	High Similarity	NPC225419
0.8889	High Similarity	NPC473014
0.8889	High Similarity	NPC131568
0.8889	High Similarity	NPC131579

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 NPC292863 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	988
0.2-0.3	1542
0.3-0.4	2601
0.4-0.5	1868
0.5-0.6	1051
0.6-0.7	483
0.7-0.8	164
0.8-0.85	37
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9423	High Similarity	NPD6959	Discontinued
0.8981	High Similarity	NPD8443	Clinical (unspecified phase)
0.8797	High Similarity	NPD2393	Clinical (unspecified phase)
0.8679	High Similarity	NPD7819	Suspended
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8659	High Similarity	NPD7852	Clinical (unspecified phase)
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8618	High Similarity	NPD1549	Phase 2
0.8608	High Similarity	NPD4380	Phase 2
0.8581	High Similarity	NPD7390	Discontinued
0.8553	High Similarity	NPD7411	Suspended
0.8545	High Similarity	NPD6166	Phase 2
0.8545	High Similarity	NPD6168	Clinical (unspecified phase)
0.8545	High Similarity	NPD6167	Clinical (unspecified phase)
0.8526	High Similarity	NPD7410	Clinical (unspecified phase)
0.8503	High Similarity	NPD5844	Phase 1
0.85	High Similarity	NPD1934	Approved
0.8494	Intermediate Similarity	NPD7473	Discontinued
0.8457	Intermediate Similarity	NPD7768	Phase 2
0.8424	Intermediate Similarity	NPD6232	Discontinued
0.8405	Intermediate Similarity	NPD3749	Approved
0.8303	Intermediate Similarity	NPD5494	Approved
0.8301	Intermediate Similarity	NPD1510	Phase 2
0.8293	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7075	Discontinued
0.8256	Intermediate Similarity	NPD8312	Approved
0.8256	Intermediate Similarity	NPD8313	Approved
0.8247	Intermediate Similarity	NPD2796	Approved
0.8232	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1511	Approved
0.8221	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD2534	Approved
0.8176	Intermediate Similarity	NPD2533	Approved
0.8176	Intermediate Similarity	NPD2532	Approved
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD3750	Approved
0.8141	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD6559	Discontinued
0.8129	Intermediate Similarity	NPD7074	Phase 3
0.8125	Intermediate Similarity	NPD1512	Approved
0.811	Intermediate Similarity	NPD2801	Approved
0.807	Intermediate Similarity	NPD7054	Approved
0.8063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1607	Approved
0.8039	Intermediate Similarity	NPD1240	Approved
0.8026	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7472	Approved
0.7977	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6797	Phase 2
0.7975	Intermediate Similarity	NPD3226	Approved
0.7975	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6801	Discontinued
0.7933	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7251	Discontinued
0.7925	Intermediate Similarity	NPD7003	Approved
0.7921	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3818	Discontinued
0.7904	Intermediate Similarity	NPD3882	Suspended
0.7898	Intermediate Similarity	NPD6100	Approved
0.7898	Intermediate Similarity	NPD5405	Approved
0.7898	Intermediate Similarity	NPD5404	Approved
0.7898	Intermediate Similarity	NPD5408	Approved
0.7898	Intermediate Similarity	NPD5406	Approved
0.7898	Intermediate Similarity	NPD6099	Approved
0.7895	Intermediate Similarity	NPD4908	Phase 1
0.7886	Intermediate Similarity	NPD7808	Phase 3
0.7882	Intermediate Similarity	NPD3787	Discontinued
0.7862	Intermediate Similarity	NPD2800	Approved
0.7848	Intermediate Similarity	NPD2346	Discontinued
0.7844	Intermediate Similarity	NPD3817	Phase 2
0.7834	Intermediate Similarity	NPD3748	Approved
0.7818	Intermediate Similarity	NPD6599	Discontinued
0.7803	Intermediate Similarity	NPD3751	Discontinued
0.7785	Intermediate Similarity	NPD1551	Phase 2
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7784	Intermediate Similarity	NPD1465	Phase 2
0.7784	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6799	Approved
0.7778	Intermediate Similarity	NPD8151	Discontinued
0.7778	Intermediate Similarity	NPD7229	Phase 3
0.7738	Intermediate Similarity	NPD5402	Approved
0.7727	Intermediate Similarity	NPD4625	Phase 3
0.7684	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5711	Approved
0.7674	Intermediate Similarity	NPD5710	Approved
0.766	Intermediate Similarity	NPD7870	Phase 2
0.766	Intermediate Similarity	NPD7871	Phase 2
0.7651	Intermediate Similarity	NPD7458	Discontinued
0.765	Intermediate Similarity	NPD4363	Phase 3
0.765	Intermediate Similarity	NPD4360	Phase 2
0.7636	Intermediate Similarity	NPD920	Approved
0.7636	Intermediate Similarity	NPD5403	Approved
0.7634	Intermediate Similarity	NPD6777	Approved
0.7634	Intermediate Similarity	NPD6778	Approved
0.7634	Intermediate Similarity	NPD6782	Approved
0.7634	Intermediate Similarity	NPD6776	Approved
0.7634	Intermediate Similarity	NPD6781	Approved
0.7634	Intermediate Similarity	NPD6779	Approved
0.7634	Intermediate Similarity	NPD6780	Approved
0.7625	Intermediate Similarity	NPD2344	Approved
0.7622	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2799	Discontinued
0.7607	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7177	Discontinued
0.7595	Intermediate Similarity	NPD6651	Approved
0.7593	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6273	Approved
0.7574	Intermediate Similarity	NPD8455	Phase 2
0.7564	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1201	Approved
0.755	Intermediate Similarity	NPD1610	Phase 2
0.7531	Intermediate Similarity	NPD1243	Approved
0.7515	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.7513	Intermediate Similarity	NPD7783	Phase 2
0.7513	Intermediate Similarity	NPD7698	Approved
0.7513	Intermediate Similarity	NPD7697	Approved
0.7513	Intermediate Similarity	NPD7696	Phase 3
0.7513	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7468	Intermediate Similarity	NPD1470	Approved
0.7458	Intermediate Similarity	NPD7286	Phase 2
0.7452	Intermediate Similarity	NPD2313	Discontinued
0.7439	Intermediate Similarity	NPD2309	Approved
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4287	Approved
0.7429	Intermediate Similarity	NPD3926	Phase 2
0.7414	Intermediate Similarity	NPD7199	Phase 2
0.7414	Intermediate Similarity	NPD1247	Approved
0.7412	Intermediate Similarity	NPD37	Approved
0.7401	Intermediate Similarity	NPD7228	Approved
0.7399	Intermediate Similarity	NPD919	Approved
0.7399	Intermediate Similarity	NPD6234	Discontinued
0.7384	Intermediate Similarity	NPD4966	Approved
0.7384	Intermediate Similarity	NPD4965	Approved
0.7384	Intermediate Similarity	NPD4967	Phase 2
0.7372	Intermediate Similarity	NPD2861	Phase 2
0.7368	Intermediate Similarity	NPD6823	Phase 2
0.7366	Intermediate Similarity	NPD6535	Approved
0.7366	Intermediate Similarity	NPD6534	Approved
0.7358	Intermediate Similarity	NPD1613	Approved
0.7358	Intermediate Similarity	NPD943	Approved
0.7358	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7701	Phase 2
0.7354	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7801	Approved
0.733	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5124	Phase 1
0.7287	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7874	Approved
0.7282	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5760	Phase 2
0.7267	Intermediate Similarity	NPD5761	Phase 2
0.7249	Intermediate Similarity	NPD7700	Phase 2
0.7249	Intermediate Similarity	NPD7699	Phase 2
0.7244	Intermediate Similarity	NPD1203	Approved
0.7234	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4361	Phase 2
0.7233	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD3764	Approved
0.7233	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4749	Approved
0.7225	Intermediate Similarity	NPD4288	Approved
0.7219	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8320	Phase 1
0.7202	Intermediate Similarity	NPD8319	Approved
0.7197	Intermediate Similarity	NPD2798	Approved
0.7195	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1283	Approved
0.7178	Intermediate Similarity	NPD7033	Discontinued
0.7178	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.7161	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD2797	Approved
0.7128	Intermediate Similarity	NPD6213	Phase 3
0.7128	Intermediate Similarity	NPD6212	Phase 3
0.7128	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1651	Approved
0.7118	Intermediate Similarity	NPD7427	Discontinued
0.7111	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6844	Discontinued
0.7107	Intermediate Similarity	NPD6832	Phase 2
0.7099	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8155	Clinical (unspecified phase)

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