NPASS Compound

Structure

NPC470983 OpenBabel07101718292D 29 31 0 0 0 0 0 0 0 0999 V2000 -5.8727 3.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8727 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 4.3594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3233 -1.3233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3546 -1.3233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8727 2.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0338 0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 0.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0338 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 2.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 2.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 4.3594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 -0.4844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6779 2.9063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 2.9063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 2.4219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1948 2.4219 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 6 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 23 2 0 0 0 0 12 18 1 0 0 0 0 12 20 2 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 28 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 29 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.23
Volume:	481.579
LogP:	5.771
LogD:	3.028
LogS:	-4.281
# Rotatable Bonds:	8
TPSA:	128.2
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.308
Synthetic Accessibility Score:	3.902
Fsp3:	0.462
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:	-4.905
MDCK Permeability:	1.322010484727798e-05
Pgp-inhibitor:	0.852
Pgp-substrate:	0.822
Human Intestinal Absorption (HIA):	0.34
20% Bioavailability (F20%):	0.888
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	100.70746612548828%
Volume Distribution (VD):	0.589
Pgp-substrate:	2.363823413848877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.172
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.414
CYP2C19-substrate:	0.526
CYP2C9-inhibitor:	0.843
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.178
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	0.623
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.965
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.868
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.194
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC470983

Natural Product ID:	NPC470983
*Common Name:**	Cycloarzanol B
IUPAC Name:	3-[(6-acetyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydrochromen-8-yl)methyl]-6-ethyl-4-hydroxy-5-methylpyran-2-one
Synonyms:	Cycloarzanol B
Standard InCHIKey:	VAHYIAJNXUYRCA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-6-15-10(2)17(24)14(21(27)28-15)9-13-19(26)16(11(3)23)18(25)12-7-8-22(4,5)29-20(12)13/h24-26H,6-9H2,1-5H3
SMILES:	CCC1=C(C(=C(C(=O)O1)CC2=C3C(=C(C(=C2O)C(=O)C)O)CCC(O3)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334815
PubChem CID:	54682569
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO25148.1	Helichrysum italicum	Under-species	n.a.	n.a.	Flowered aerial parts	Arzana, Sardinia	2010-Jul	PMID[23265253]

☑ 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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[474626]

☑ 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 NPC470983 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	361
0.1-0.2	1872
0.2-0.3	4826
0.3-0.4	11047
0.4-0.5	7810
0.5-0.6	4990
0.6-0.7	5599
0.7-0.8	4574
0.8-0.85	1231
0.85-0.9	341
0.9-0.95	42
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470982
0.9481	High Similarity	NPC472343
0.942	High Similarity	NPC71184
0.942	High Similarity	NPC206212
0.9412	High Similarity	NPC221173
0.9407	High Similarity	NPC199458
0.9407	High Similarity	NPC183639
0.9343	High Similarity	NPC470555
0.9338	High Similarity	NPC241975
0.9338	High Similarity	NPC19476
0.9333	High Similarity	NPC131782
0.9333	High Similarity	NPC474624
0.9333	High Similarity	NPC138047
0.9286	High Similarity	NPC140120
0.9286	High Similarity	NPC474108
0.9286	High Similarity	NPC177995
0.9265	High Similarity	NPC470083
0.9265	High Similarity	NPC219584
0.922	High Similarity	NPC472345
0.9185	High Similarity	NPC101752
0.9149	High Similarity	NPC285748
0.9143	High Similarity	NPC1886
0.9143	High Similarity	NPC196137
0.9143	High Similarity	NPC469953
0.9137	High Similarity	NPC36181
0.9137	High Similarity	NPC470556
0.9137	High Similarity	NPC112829
0.9137	High Similarity	NPC472344
0.9137	High Similarity	NPC294432
0.913	High Similarity	NPC469818
0.9124	High Similarity	NPC272844
0.9124	High Similarity	NPC474504
0.9124	High Similarity	NPC54820
0.9124	High Similarity	NPC180501
0.9124	High Similarity	NPC474487
0.9124	High Similarity	NPC254168
0.9124	High Similarity	NPC248995
0.9124	High Similarity	NPC470672
0.9124	High Similarity	NPC470671
0.9124	High Similarity	NPC131130
0.9124	High Similarity	NPC268178
0.9091	High Similarity	NPC180351
0.9085	High Similarity	NPC208303
0.9085	High Similarity	NPC161864
0.9078	High Similarity	NPC154217
0.9078	High Similarity	NPC57470
0.9078	High Similarity	NPC470322
0.9078	High Similarity	NPC181388
0.9071	High Similarity	NPC184738
0.9071	High Similarity	NPC188632
0.9071	High Similarity	NPC94794
0.9071	High Similarity	NPC96216
0.9071	High Similarity	NPC87609
0.9071	High Similarity	NPC470296
0.9071	High Similarity	NPC470553
0.9071	High Similarity	NPC33653
0.9071	High Similarity	NPC470909
0.9071	High Similarity	NPC219915
0.9071	High Similarity	NPC474939
0.9071	High Similarity	NPC196459
0.9071	High Similarity	NPC307895
0.9071	High Similarity	NPC112791
0.9058	High Similarity	NPC240305
0.9023	High Similarity	NPC21378
0.9023	High Similarity	NPC470987
0.9021	High Similarity	NPC469932
0.9021	High Similarity	NPC104236
0.9021	High Similarity	NPC164205
0.9014	High Similarity	NPC180477
0.9014	High Similarity	NPC297886
0.9014	High Similarity	NPC249942
0.9007	High Similarity	NPC470554
0.9007	High Similarity	NPC133060
0.9007	High Similarity	NPC178627
0.9007	High Similarity	NPC469935
0.9007	High Similarity	NPC288910
0.9007	High Similarity	NPC118059
0.9	High Similarity	NPC144499
0.8993	High Similarity	NPC477272
0.8986	High Similarity	NPC470669
0.8986	High Similarity	NPC470668
0.8978	High Similarity	NPC174999
0.8966	High Similarity	NPC256141
0.8963	High Similarity	NPC470988
0.8951	High Similarity	NPC469933
0.8944	High Similarity	NPC470910
0.8936	High Similarity	NPC166138
0.8936	High Similarity	NPC38219
0.8936	High Similarity	NPC112749
0.8936	High Similarity	NPC18585
0.8936	High Similarity	NPC106985
0.8929	High Similarity	NPC147688
0.8929	High Similarity	NPC205006
0.8929	High Similarity	NPC316911
0.8929	High Similarity	NPC64908
0.8929	High Similarity	NPC316560
0.8929	High Similarity	NPC156590
0.8929	High Similarity	NPC118840
0.8921	High Similarity	NPC96565
0.8921	High Similarity	NPC220062
0.8921	High Similarity	NPC216978
0.8921	High Similarity	NPC55018
0.8921	High Similarity	NPC301217
0.8921	High Similarity	NPC217186
0.8921	High Similarity	NPC23257
0.8921	High Similarity	NPC53181
0.8921	High Similarity	NPC303633
0.8913	High Similarity	NPC38153
0.8897	High Similarity	NPC93756
0.8897	High Similarity	NPC470984
0.8897	High Similarity	NPC108113
0.8889	High Similarity	NPC185624
0.8889	High Similarity	NPC19238
0.8881	High Similarity	NPC296998
0.8881	High Similarity	NPC186628
0.8881	High Similarity	NPC473077
0.8873	High Similarity	NPC234629
0.8873	High Similarity	NPC470673
0.8873	High Similarity	NPC470674
0.8873	High Similarity	NPC311741
0.8873	High Similarity	NPC117716
0.8865	High Similarity	NPC59739
0.8865	High Similarity	NPC62840
0.8865	High Similarity	NPC326193
0.8865	High Similarity	NPC276565
0.8865	High Similarity	NPC217083
0.8865	High Similarity	NPC214236
0.8865	High Similarity	NPC321629
0.8865	High Similarity	NPC323884
0.8865	High Similarity	NPC299080
0.8865	High Similarity	NPC11561
0.8865	High Similarity	NPC266725
0.8865	High Similarity	NPC293852
0.8865	High Similarity	NPC321148
0.8865	High Similarity	NPC226636
0.8865	High Similarity	NPC78803
0.8857	High Similarity	NPC241100
0.8857	High Similarity	NPC159275
0.8857	High Similarity	NPC305355
0.8857	High Similarity	NPC172986
0.8857	High Similarity	NPC261227
0.8857	High Similarity	NPC471587
0.8857	High Similarity	NPC16455
0.8857	High Similarity	NPC150522
0.8857	High Similarity	NPC235239
0.8857	High Similarity	NPC69769
0.8857	High Similarity	NPC475680
0.8857	High Similarity	NPC270883
0.8857	High Similarity	NPC307990
0.8849	High Similarity	NPC201395
0.8832	High Similarity	NPC125920
0.8828	High Similarity	NPC150928
0.8828	High Similarity	NPC327059
0.8828	High Similarity	NPC151973
0.8828	High Similarity	NPC321387
0.8828	High Similarity	NPC158866
0.8828	High Similarity	NPC474735
0.8828	High Similarity	NPC470908
0.8824	High Similarity	NPC10971
0.8819	High Similarity	NPC37139
0.8819	High Similarity	NPC211811
0.8819	High Similarity	NPC296869
0.8815	High Similarity	NPC279566
0.8811	High Similarity	NPC473132
0.8811	High Similarity	NPC20488
0.8811	High Similarity	NPC67805
0.8811	High Similarity	NPC176229
0.8811	High Similarity	NPC88964
0.8811	High Similarity	NPC312973
0.8811	High Similarity	NPC142405
0.8811	High Similarity	NPC246948
0.8811	High Similarity	NPC111786
0.8811	High Similarity	NPC83357
0.8811	High Similarity	NPC82534
0.8811	High Similarity	NPC54577
0.8811	High Similarity	NPC220418
0.8811	High Similarity	NPC473135
0.8811	High Similarity	NPC195621
0.8811	High Similarity	NPC470647
0.8811	High Similarity	NPC477955
0.8811	High Similarity	NPC301276
0.8811	High Similarity	NPC124729
0.8811	High Similarity	NPC267375
0.8811	High Similarity	NPC475052
0.8811	High Similarity	NPC470676
0.8811	High Similarity	NPC214774
0.8803	High Similarity	NPC190637
0.8803	High Similarity	NPC11700
0.8803	High Similarity	NPC316816
0.8803	High Similarity	NPC293053
0.8803	High Similarity	NPC24821
0.8803	High Similarity	NPC18886
0.8803	High Similarity	NPC212932
0.8803	High Similarity	NPC5990
0.8803	High Similarity	NPC9117
0.8803	High Similarity	NPC478086
0.8803	High Similarity	NPC214166
0.8794	High Similarity	NPC110969
0.8794	High Similarity	NPC157497
0.8794	High Similarity	NPC81337

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 NPC470983 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	1104
0.2-0.3	2051
0.3-0.4	2744
0.4-0.5	1778
0.5-0.6	800
0.6-0.7	243
0.7-0.8	81
0.8-0.85	24
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD7410	Clinical (unspecified phase)
0.8741	High Similarity	NPD4378	Clinical (unspecified phase)
0.8652	High Similarity	NPD2800	Approved
0.8623	High Similarity	NPD6651	Approved
0.8514	High Similarity	NPD7411	Suspended
0.8477	Intermediate Similarity	NPD7075	Discontinued
0.84	Intermediate Similarity	NPD7819	Suspended
0.84	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD2534	Approved
0.8356	Intermediate Similarity	NPD2533	Approved
0.8356	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8322	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1549	Phase 2
0.8278	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD1243	Approved
0.8239	Intermediate Similarity	NPD1510	Phase 2
0.8224	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD3750	Approved
0.82	Intermediate Similarity	NPD4380	Phase 2
0.8182	Intermediate Similarity	NPD2796	Approved
0.8153	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD3749	Approved
0.8085	Intermediate Similarity	NPD1240	Approved
0.8052	Intermediate Similarity	NPD7768	Phase 2
0.8041	Intermediate Similarity	NPD6799	Approved
0.8041	Intermediate Similarity	NPD1511	Approved
0.8028	Intermediate Similarity	NPD5124	Phase 1
0.8028	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1934	Approved
0.7972	Intermediate Similarity	NPD1607	Approved
0.7962	Intermediate Similarity	NPD6959	Discontinued
0.7959	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD2313	Discontinued
0.7933	Intermediate Similarity	NPD1512	Approved
0.7922	Intermediate Similarity	NPD2801	Approved
0.7888	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD3817	Phase 2
0.7862	Intermediate Similarity	NPD2799	Discontinued
0.7862	Intermediate Similarity	NPD3748	Approved
0.7852	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6599	Discontinued
0.7838	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1551	Phase 2
0.7808	Intermediate Similarity	NPD2935	Discontinued
0.7799	Intermediate Similarity	NPD5711	Approved
0.7799	Intermediate Similarity	NPD5710	Approved
0.7748	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6232	Discontinued
0.7687	Intermediate Similarity	NPD6100	Approved
0.7687	Intermediate Similarity	NPD6099	Approved
0.7683	Intermediate Similarity	NPD5953	Discontinued
0.7681	Intermediate Similarity	NPD422	Phase 1
0.7669	Intermediate Similarity	NPD7286	Phase 2
0.7654	Intermediate Similarity	NPD7473	Discontinued
0.7647	Intermediate Similarity	NPD5403	Approved
0.7635	Intermediate Similarity	NPD2346	Discontinued
0.7626	Intermediate Similarity	NPD9717	Approved
0.7595	Intermediate Similarity	NPD3882	Suspended
0.7593	Intermediate Similarity	NPD6166	Phase 2
0.7593	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1203	Approved
0.7569	Intermediate Similarity	NPD3268	Approved
0.7561	Intermediate Similarity	NPD7054	Approved
0.7548	Intermediate Similarity	NPD3226	Approved
0.753	Intermediate Similarity	NPD6559	Discontinued
0.7516	Intermediate Similarity	NPD5401	Approved
0.7515	Intermediate Similarity	NPD7074	Phase 3
0.7515	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7485	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6797	Phase 2
0.7468	Intermediate Similarity	NPD1465	Phase 2
0.7465	Intermediate Similarity	NPD2797	Approved
0.7455	Intermediate Similarity	NPD5844	Phase 1
0.7453	Intermediate Similarity	NPD5494	Approved
0.7425	Intermediate Similarity	NPD7251	Discontinued
0.7421	Intermediate Similarity	NPD5402	Approved
0.74	Intermediate Similarity	NPD2344	Approved
0.7383	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7808	Phase 3
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7329	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1296	Phase 2
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6832	Phase 2
0.7292	Intermediate Similarity	NPD2798	Approved
0.7278	Intermediate Similarity	NPD6585	Discontinued
0.7273	Intermediate Similarity	NPD3225	Approved
0.7262	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4307	Phase 2
0.7226	Intermediate Similarity	NPD7390	Discontinued
0.7225	Intermediate Similarity	NPD4287	Approved
0.7222	Intermediate Similarity	NPD3267	Approved
0.7222	Intermediate Similarity	NPD3266	Approved
0.7211	Intermediate Similarity	NPD411	Approved
0.7208	Intermediate Similarity	NPD2309	Approved
0.7205	Intermediate Similarity	NPD4288	Approved
0.7203	Intermediate Similarity	NPD4749	Approved
0.7192	Intermediate Similarity	NPD4908	Phase 1
0.719	Intermediate Similarity	NPD2654	Approved
0.7181	Intermediate Similarity	NPD230	Phase 1
0.7181	Intermediate Similarity	NPD447	Suspended
0.7175	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4360	Phase 2
0.7159	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD9545	Approved
0.7133	Intermediate Similarity	NPD1608	Approved
0.7125	Intermediate Similarity	NPD5890	Approved
0.7125	Intermediate Similarity	NPD5889	Approved
0.7122	Intermediate Similarity	NPD9493	Approved
0.7114	Intermediate Similarity	NPD943	Approved
0.7105	Intermediate Similarity	NPD5408	Approved
0.7105	Intermediate Similarity	NPD5405	Approved
0.7105	Intermediate Similarity	NPD5404	Approved
0.7105	Intermediate Similarity	NPD5406	Approved
0.7095	Intermediate Similarity	NPD3764	Approved
0.7091	Intermediate Similarity	NPD1247	Approved
0.7089	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1933	Approved
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1610	Phase 2
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5049	Phase 3
0.7022	Intermediate Similarity	NPD4361	Phase 2
0.7022	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD1729	Discontinued
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6986	Remote Similarity	NPD1164	Approved
0.698	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1652	Phase 2
0.6964	Remote Similarity	NPD2403	Approved
0.6959	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6005	Phase 3
0.6948	Remote Similarity	NPD6004	Phase 3
0.6948	Remote Similarity	NPD6002	Phase 3
0.6948	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7229	Phase 3
0.6939	Remote Similarity	NPD1019	Discontinued
0.6923	Remote Similarity	NPD7003	Approved
0.6923	Remote Similarity	NPD17	Approved
0.6919	Remote Similarity	NPD6104	Discontinued
0.6919	Remote Similarity	NPD7584	Approved
0.6905	Remote Similarity	NPD3926	Phase 2
0.6899	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2354	Approved
0.6867	Remote Similarity	NPD6798	Discontinued
0.6867	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8313	Approved
0.6839	Remote Similarity	NPD8312	Approved
0.6795	Remote Similarity	NPD2424	Discontinued
0.6786	Remote Similarity	NPD1398	Phase 1
0.6786	Remote Similarity	NPD7199	Phase 2
0.6784	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1481	Phase 2
0.6776	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4476	Approved
0.6774	Remote Similarity	NPD4477	Approved
0.6765	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7340	Approved
0.6732	Remote Similarity	NPD6355	Discontinued
0.6731	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2353	Approved
0.6728	Remote Similarity	NPD1653	Approved
0.6727	Remote Similarity	NPD8455	Phase 2
0.6723	Remote Similarity	NPD8434	Phase 2
0.6713	Remote Similarity	NPD7644	Approved
0.6712	Remote Similarity	NPD1535	Discovery
0.6712	Remote Similarity	NPD1201	Approved
0.671	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6971	Discontinued
0.6706	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7585	Approved
0.669	Remote Similarity	NPD4626	Approved
0.669	Remote Similarity	NPD1778	Approved
0.6687	Remote Similarity	NPD2296	Approved
0.6686	Remote Similarity	NPD7177	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