NPASS Compound

Structure

NPC476332 OpenBabel07101719132D 24 25 0 0 1 0 0 0 0 0999 V2000 -1.2247 -1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 0.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -0.9659 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 3.4641 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 12 2 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 19 2 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 13 21 2 0 0 0 0 13 23 1 0 0 0 0 14 22 2 0 0 0 0 14 24 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 1 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.17
Volume:	354.069
LogP:	3.813
LogD:	3.068
LogS:	-5.165
# Rotatable Bonds:	6
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	3.843
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.895
MDCK Permeability:	3.004305654030759e-05
Pgp-inhibitor:	0.954
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.148
20% Bioavailability (F20%):	0.352
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.615
Plasma Protein Binding (PPB):	78.41983795166016%
Volume Distribution (VD):	0.501
Pgp-substrate:	33.7635498046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.788
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.511
CYP2C19-substrate:	0.552
CYP2C9-inhibitor:	0.433
CYP2C9-substrate:	0.767
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.494
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	2.011
Half-life (T1/2):	0.347

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.003
Drug-inuced Liver Injury (DILI):	0.322
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.151
Skin Sensitization:	0.93
Carcinogencity:	0.23
Eye Corrosion:	0.35
Eye Irritation:	0.424
Respiratory Toxicity:	0.739

Download Data

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

Natural Product: NPC476332

Natural Product ID:	NPC476332
*Common Name:**	[(6S,7R)-4-Acetyloxy-6-Ethenyl-6-Methyl-7-Prop-1-En-2-Yl-7,8-Dihydro-5H-Naphthalen-1-Yl] Acetate
IUPAC Name:	[(6S,7R)-4-acetyloxy-6-ethenyl-6-methyl-7-prop-1-en-2-yl-7,8-dihydro-5H-naphthalen-1-yl] acetate
Synonyms:
Standard InCHIKey:	SRGHBWCDQWJMPC-YLJYHZDGSA-N
Standard InCHI:	InChI=1S/C20H24O4/c1-7-20(6)11-16-15(10-17(20)12(2)3)18(23-13(4)21)8-9-19(16)24-14(5)22/h7-9,17H,1-2,10-11H2,3-6H3/t17-,20-/m1/s1
SMILES:	C=C[C@]1(C)Cc2c(ccc(c2C[C@@H]1C(=C)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL569139
PubChem CID:	45272200
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO22854	Cordia globifera	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19368377]
NPO22854	Cordia globifera	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384317]
NPO22854	Cordia globifera	Species	Cordiaceae	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	6
MIC	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	7.3	ug.mL-1	PMID[479662]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	8.5	ug.mL-1	PMID[479662]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	5.1	ug.mL-1	PMID[479662]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	25.0	ug.mL-1	PMID[479662]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.4	ug.mL-1	PMID[479662]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	20.0	ug.mL-1	PMID[479662]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9.2	ug.mL-1	PMID[479662]

☑ 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 NPC476332 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	326
0.1-0.2	1658
0.2-0.3	3892
0.3-0.4	11480
0.4-0.5	7535
0.5-0.6	7429
0.6-0.7	9261
0.7-0.8	1040
0.8-0.85	56
0.85-0.9	14
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473464
0.9339	High Similarity	NPC128321
0.9187	High Similarity	NPC176590
0.8879	High Similarity	NPC280760
0.88	High Similarity	NPC156298
0.877	High Similarity	NPC475839
0.8712	High Similarity	NPC476191
0.8689	High Similarity	NPC322569
0.8667	High Similarity	NPC238075
0.8594	High Similarity	NPC249425
0.8583	High Similarity	NPC81261
0.8561	High Similarity	NPC471542
0.856	High Similarity	NPC248557
0.8537	High Similarity	NPC212559
0.8525	High Similarity	NPC98748
0.85	High Similarity	NPC283169
0.8496	Intermediate Similarity	NPC265335
0.8433	Intermediate Similarity	NPC79372
0.8417	Intermediate Similarity	NPC87563
0.8413	Intermediate Similarity	NPC474237
0.84	Intermediate Similarity	NPC302211
0.8385	Intermediate Similarity	NPC258073
0.8374	Intermediate Similarity	NPC471449
0.8374	Intermediate Similarity	NPC234956
0.8346	Intermediate Similarity	NPC170749
0.8346	Intermediate Similarity	NPC265515
0.8333	Intermediate Similarity	NPC27394
0.8333	Intermediate Similarity	NPC248786
0.832	Intermediate Similarity	NPC48623
0.832	Intermediate Similarity	NPC168707
0.8308	Intermediate Similarity	NPC475102
0.8295	Intermediate Similarity	NPC47288
0.8284	Intermediate Similarity	NPC474530
0.8284	Intermediate Similarity	NPC474540
0.8284	Intermediate Similarity	NPC474521
0.8279	Intermediate Similarity	NPC312105
0.8268	Intermediate Similarity	NPC61685
0.8261	Intermediate Similarity	NPC292256
0.824	Intermediate Similarity	NPC45663
0.8226	Intermediate Similarity	NPC51341
0.8209	Intermediate Similarity	NPC115861
0.8205	Intermediate Similarity	NPC30416
0.8203	Intermediate Similarity	NPC279118
0.8201	Intermediate Similarity	NPC475896
0.8189	Intermediate Similarity	NPC470887
0.8188	Intermediate Similarity	NPC474599
0.816	Intermediate Similarity	NPC14177
0.814	Intermediate Similarity	NPC329272
0.8134	Intermediate Similarity	NPC291119
0.8134	Intermediate Similarity	NPC281169
0.8125	Intermediate Similarity	NPC75432
0.812	Intermediate Similarity	NPC211352
0.812	Intermediate Similarity	NPC473393
0.8106	Intermediate Similarity	NPC153019
0.8106	Intermediate Similarity	NPC474200
0.8095	Intermediate Similarity	NPC129176
0.8092	Intermediate Similarity	NPC206028
0.8077	Intermediate Similarity	NPC95034
0.8077	Intermediate Similarity	NPC142087
0.8074	Intermediate Similarity	NPC474610
0.8071	Intermediate Similarity	NPC475872
0.8065	Intermediate Similarity	NPC187993
0.8065	Intermediate Similarity	NPC471503
0.8065	Intermediate Similarity	NPC471498
0.8065	Intermediate Similarity	NPC238176
0.8049	Intermediate Similarity	NPC473718
0.8047	Intermediate Similarity	NPC320287
0.803	Intermediate Similarity	NPC474617
0.8017	Intermediate Similarity	NPC470723
0.8017	Intermediate Similarity	NPC275627
0.8015	Intermediate Similarity	NPC306365
0.8015	Intermediate Similarity	NPC474636
0.8	Intermediate Similarity	NPC139047
0.8	Intermediate Similarity	NPC51087
0.8	Intermediate Similarity	NPC101894
0.8	Intermediate Similarity	NPC161856
0.7984	Intermediate Similarity	NPC33900
0.7984	Intermediate Similarity	NPC163398
0.7984	Intermediate Similarity	NPC69539
0.7971	Intermediate Similarity	NPC472523
0.7969	Intermediate Similarity	NPC152946
0.7969	Intermediate Similarity	NPC188997
0.7951	Intermediate Similarity	NPC474920
0.7951	Intermediate Similarity	NPC98372
0.7949	Intermediate Similarity	NPC24327
0.7949	Intermediate Similarity	NPC12870
0.7939	Intermediate Similarity	NPC474821
0.7939	Intermediate Similarity	NPC474670
0.7923	Intermediate Similarity	NPC320847
0.792	Intermediate Similarity	NPC25648
0.7914	Intermediate Similarity	NPC93640
0.7914	Intermediate Similarity	NPC20631
0.791	Intermediate Similarity	NPC27578
0.791	Intermediate Similarity	NPC289624
0.7907	Intermediate Similarity	NPC261992
0.7899	Intermediate Similarity	NPC473049
0.7899	Intermediate Similarity	NPC76312
0.7899	Intermediate Similarity	NPC472794
0.7895	Intermediate Similarity	NPC196193
0.7883	Intermediate Similarity	NPC14697
0.7883	Intermediate Similarity	NPC131198
0.7879	Intermediate Similarity	NPC474616
0.7874	Intermediate Similarity	NPC474131
0.7874	Intermediate Similarity	NPC471504
0.7874	Intermediate Similarity	NPC473290
0.7869	Intermediate Similarity	NPC77772
0.7869	Intermediate Similarity	NPC266937
0.7869	Intermediate Similarity	NPC470770
0.7863	Intermediate Similarity	NPC474632
0.7863	Intermediate Similarity	NPC307425
0.7852	Intermediate Similarity	NPC472524
0.7846	Intermediate Similarity	NPC89630
0.7846	Intermediate Similarity	NPC140521
0.7842	Intermediate Similarity	NPC472792
0.7842	Intermediate Similarity	NPC138149
0.7842	Intermediate Similarity	NPC472791
0.784	Intermediate Similarity	NPC242580
0.784	Intermediate Similarity	NPC126759
0.784	Intermediate Similarity	NPC236070
0.7833	Intermediate Similarity	NPC320439
0.7826	Intermediate Similarity	NPC307883
0.7817	Intermediate Similarity	NPC471608
0.7815	Intermediate Similarity	NPC473855
0.7815	Intermediate Similarity	NPC139891
0.7812	Intermediate Similarity	NPC100108
0.7812	Intermediate Similarity	NPC277798
0.781	Intermediate Similarity	NPC286843
0.781	Intermediate Similarity	NPC194847
0.781	Intermediate Similarity	NPC21797
0.781	Intermediate Similarity	NPC92932
0.7805	Intermediate Similarity	NPC177962
0.7805	Intermediate Similarity	NPC62867
0.7795	Intermediate Similarity	NPC32152
0.7794	Intermediate Similarity	NPC213122
0.7794	Intermediate Similarity	NPC474600
0.7787	Intermediate Similarity	NPC473809
0.7786	Intermediate Similarity	NPC471828
0.7786	Intermediate Similarity	NPC249836
0.7786	Intermediate Similarity	NPC4286
0.7786	Intermediate Similarity	NPC252962
0.7786	Intermediate Similarity	NPC76119
0.7786	Intermediate Similarity	NPC471827
0.7786	Intermediate Similarity	NPC133407
0.7786	Intermediate Similarity	NPC28476
0.7778	Intermediate Similarity	NPC474635
0.7778	Intermediate Similarity	NPC183154
0.7778	Intermediate Similarity	NPC329427
0.7778	Intermediate Similarity	NPC107101
0.7778	Intermediate Similarity	NPC317601
0.7778	Intermediate Similarity	NPC263754
0.7769	Intermediate Similarity	NPC279379
0.7761	Intermediate Similarity	NPC473048
0.7761	Intermediate Similarity	NPC11089
0.7761	Intermediate Similarity	NPC325003
0.7761	Intermediate Similarity	NPC475880
0.7754	Intermediate Similarity	NPC476171
0.7754	Intermediate Similarity	NPC105493
0.775	Intermediate Similarity	NPC326801
0.7744	Intermediate Similarity	NPC223912
0.7742	Intermediate Similarity	NPC303522
0.7737	Intermediate Similarity	NPC234865
0.7734	Intermediate Similarity	NPC168050
0.7734	Intermediate Similarity	NPC232295
0.7731	Intermediate Similarity	NPC283546
0.7724	Intermediate Similarity	NPC233238
0.7717	Intermediate Similarity	NPC159916
0.7717	Intermediate Similarity	NPC283616
0.7714	Intermediate Similarity	NPC155552
0.771	Intermediate Similarity	NPC27671
0.771	Intermediate Similarity	NPC73413
0.771	Intermediate Similarity	NPC78446
0.771	Intermediate Similarity	NPC10154
0.771	Intermediate Similarity	NPC276962
0.771	Intermediate Similarity	NPC111088
0.771	Intermediate Similarity	NPC147896
0.771	Intermediate Similarity	NPC190086
0.771	Intermediate Similarity	NPC201667
0.771	Intermediate Similarity	NPC265413
0.7705	Intermediate Similarity	NPC149545
0.7704	Intermediate Similarity	NPC142530
0.7698	Intermediate Similarity	NPC132723
0.7698	Intermediate Similarity	NPC33717
0.7698	Intermediate Similarity	NPC76032
0.7692	Intermediate Similarity	NPC46586
0.7692	Intermediate Similarity	NPC204535
0.7692	Intermediate Similarity	NPC478058
0.7692	Intermediate Similarity	NPC121168
0.7686	Intermediate Similarity	NPC233320
0.768	Intermediate Similarity	NPC471534
0.768	Intermediate Similarity	NPC470837
0.7676	Intermediate Similarity	NPC251372
0.7676	Intermediate Similarity	NPC36732
0.7674	Intermediate Similarity	NPC241001
0.7674	Intermediate Similarity	NPC267064
0.7669	Intermediate Similarity	NPC98745
0.7669	Intermediate Similarity	NPC186889
0.7664	Intermediate Similarity	NPC71372
0.7661	Intermediate Similarity	NPC26615
0.7655	Intermediate Similarity	NPC475848
0.7655	Intermediate Similarity	NPC95526

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 NPC476332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	1024
0.2-0.3	1490
0.3-0.4	2715
0.4-0.5	1838
0.5-0.6	1126
0.6-0.7	526
0.7-0.8	101
0.8-0.85	9
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9244	High Similarity	NPD1611	Approved
0.8667	High Similarity	NPD7644	Approved
0.8387	Intermediate Similarity	NPD3496	Discontinued
0.8385	Intermediate Similarity	NPD8032	Phase 2
0.8374	Intermediate Similarity	NPD5585	Approved
0.8374	Intermediate Similarity	NPD5691	Approved
0.8321	Intermediate Similarity	NPD4140	Approved
0.825	Intermediate Similarity	NPD5535	Approved
0.8217	Intermediate Similarity	NPD2237	Approved
0.8182	Intermediate Similarity	NPD4060	Phase 1
0.816	Intermediate Similarity	NPD4626	Approved
0.8049	Intermediate Similarity	NPD6671	Approved
0.8047	Intermediate Similarity	NPD4359	Approved
0.8047	Intermediate Similarity	NPD5327	Phase 3
0.7984	Intermediate Similarity	NPD6696	Suspended
0.7956	Intermediate Similarity	NPD5762	Approved
0.7956	Intermediate Similarity	NPD5763	Approved
0.791	Intermediate Similarity	NPD2979	Phase 3
0.7895	Intermediate Similarity	NPD7985	Registered
0.7891	Intermediate Similarity	NPD1281	Approved
0.7874	Intermediate Similarity	NPD1778	Approved
0.7874	Intermediate Similarity	NPD17	Approved
0.784	Intermediate Similarity	NPD7340	Approved
0.782	Intermediate Similarity	NPD7095	Approved
0.7815	Intermediate Similarity	NPD9697	Approved
0.7786	Intermediate Similarity	NPD2797	Approved
0.7786	Intermediate Similarity	NPD3266	Approved
0.7786	Intermediate Similarity	NPD3267	Approved
0.7742	Intermediate Similarity	NPD1398	Phase 1
0.771	Intermediate Similarity	NPD1283	Approved
0.7704	Intermediate Similarity	NPD4870	Approved
0.7698	Intermediate Similarity	NPD2346	Discontinued
0.7692	Intermediate Similarity	NPD1608	Approved
0.7656	Intermediate Similarity	NPD1651	Approved
0.7634	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3268	Approved
0.76	Intermediate Similarity	NPD5283	Phase 1
0.7569	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4625	Phase 3
0.7537	Intermediate Similarity	NPD2861	Phase 2
0.7535	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD7635	Approved
0.7519	Intermediate Similarity	NPD3444	Approved
0.7519	Intermediate Similarity	NPD3443	Approved
0.7519	Intermediate Similarity	NPD3445	Approved
0.7517	Intermediate Similarity	NPD2676	Approved
0.7517	Intermediate Similarity	NPD6273	Approved
0.7517	Intermediate Similarity	NPD2675	Approved
0.75	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2531	Phase 2
0.75	Intermediate Similarity	NPD2438	Suspended
0.748	Intermediate Similarity	NPD7157	Approved
0.748	Intermediate Similarity	NPD709	Approved
0.748	Intermediate Similarity	NPD6387	Discontinued
0.7464	Intermediate Similarity	NPD5735	Approved
0.7464	Intermediate Similarity	NPD6355	Discontinued
0.7463	Intermediate Similarity	NPD4624	Approved
0.7459	Intermediate Similarity	NPD3134	Approved
0.7429	Intermediate Similarity	NPD2799	Discontinued
0.7413	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4110	Phase 3
0.741	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6353	Approved
0.7391	Intermediate Similarity	NPD4307	Phase 2
0.7376	Intermediate Similarity	NPD6100	Approved
0.7376	Intermediate Similarity	NPD6099	Approved
0.7376	Intermediate Similarity	NPD4477	Approved
0.7376	Intermediate Similarity	NPD4476	Approved
0.7376	Intermediate Similarity	NPD6032	Approved
0.7376	Intermediate Similarity	NPD2935	Discontinued
0.7372	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4749	Approved
0.7365	Intermediate Similarity	NPD3226	Approved
0.7353	Intermediate Similarity	NPD2614	Approved
0.7353	Intermediate Similarity	NPD6832	Phase 2
0.7348	Intermediate Similarity	NPD1535	Discovery
0.7338	Intermediate Similarity	NPD4622	Approved
0.7338	Intermediate Similarity	NPD4618	Approved
0.7338	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD498	Approved
0.7323	Intermediate Similarity	NPD495	Approved
0.7323	Intermediate Similarity	NPD496	Approved
0.7317	Intermediate Similarity	NPD968	Approved
0.7302	Intermediate Similarity	NPD1139	Approved
0.7302	Intermediate Similarity	NPD1137	Approved
0.7297	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1481	Phase 2
0.7293	Intermediate Similarity	NPD2230	Approved
0.7293	Intermediate Similarity	NPD2233	Approved
0.7293	Intermediate Similarity	NPD2232	Approved
0.7292	Intermediate Similarity	NPD7003	Approved
0.7286	Intermediate Similarity	NPD4097	Suspended
0.7279	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5736	Approved
0.7279	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD497	Approved
0.7258	Intermediate Similarity	NPD1358	Approved
0.7252	Intermediate Similarity	NPD3025	Approved
0.7252	Intermediate Similarity	NPD3024	Approved
0.7248	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2313	Discontinued
0.7246	Intermediate Similarity	NPD6798	Discontinued
0.7244	Intermediate Similarity	NPD1138	Approved
0.7234	Intermediate Similarity	NPD7097	Phase 1
0.7234	Intermediate Similarity	NPD5688	Approved
0.7234	Intermediate Similarity	NPD5689	Approved
0.7222	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD422	Phase 1
0.7209	Intermediate Similarity	NPD2557	Approved
0.72	Intermediate Similarity	NPD2684	Approved
0.7194	Intermediate Similarity	NPD6233	Phase 2
0.7185	Intermediate Similarity	NPD8651	Approved
0.7185	Intermediate Similarity	NPD3225	Approved
0.7183	Intermediate Similarity	NPD4308	Phase 3
0.7183	Intermediate Similarity	NPD3748	Approved
0.7172	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6653	Approved
0.7162	Intermediate Similarity	NPD6090	Discontinued
0.7162	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1712	Approved
0.7153	Intermediate Similarity	NPD2897	Discontinued
0.7143	Intermediate Similarity	NPD3023	Approved
0.7143	Intermediate Similarity	NPD3026	Approved
0.7143	Intermediate Similarity	NPD3847	Discontinued
0.7132	Intermediate Similarity	NPD4098	Discontinued
0.7122	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8127	Discontinued
0.7109	Intermediate Similarity	NPD7843	Approved
0.7101	Intermediate Similarity	NPD4908	Phase 1
0.7092	Intermediate Similarity	NPD3657	Discovery
0.709	Intermediate Similarity	NPD3705	Approved
0.7089	Intermediate Similarity	NPD4481	Phase 3
0.7083	Intermediate Similarity	NPD6005	Phase 3
0.7083	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6004	Phase 3
0.7083	Intermediate Similarity	NPD6002	Phase 3
0.7083	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2798	Approved
0.7075	Intermediate Similarity	NPD6666	Approved
0.7075	Intermediate Similarity	NPD6667	Approved
0.7071	Intermediate Similarity	NPD6663	Approved
0.7068	Intermediate Similarity	NPD2932	Approved
0.7068	Intermediate Similarity	NPD3019	Approved
0.7068	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5754	Discontinued
0.7055	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4628	Phase 3
0.7045	Intermediate Similarity	NPD1894	Discontinued
0.7042	Intermediate Similarity	NPD2653	Approved
0.7042	Intermediate Similarity	NPD2157	Approved
0.7037	Intermediate Similarity	NPD2231	Phase 2
0.7037	Intermediate Similarity	NPD2235	Phase 2
0.7037	Intermediate Similarity	NPD1840	Phase 2
0.7037	Intermediate Similarity	NPD9717	Approved
0.7037	Intermediate Similarity	NPD3972	Approved
0.7032	Intermediate Similarity	NPD3453	Discontinued
0.7027	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3110	Approved
0.7021	Intermediate Similarity	NPD3109	Approved
0.7021	Intermediate Similarity	NPD3620	Phase 2
0.7021	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5451	Approved
0.7007	Intermediate Similarity	NPD6362	Approved
0.7007	Intermediate Similarity	NPD1203	Approved
0.7007	Intermediate Similarity	NPD987	Approved
0.7	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD7294	Phase 1
0.6992	Remote Similarity	NPD3049	Approved
0.6986	Remote Similarity	NPD6674	Discontinued
0.6985	Remote Similarity	NPD1669	Approved
0.6984	Remote Similarity	NPD290	Approved
0.6978	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD447	Suspended
0.6972	Remote Similarity	NPD5124	Phase 1
0.697	Remote Similarity	NPD5536	Phase 2
0.6963	Remote Similarity	NPD1610	Phase 2
0.6957	Remote Similarity	NPD5844	Phase 1
0.6957	Remote Similarity	NPD1019	Discontinued
0.695	Remote Similarity	NPD4474	Approved
0.695	Remote Similarity	NPD4475	Approved
0.6948	Remote Similarity	NPD7819	Suspended
0.6948	Remote Similarity	NPD5929	Approved
0.6944	Remote Similarity	NPD7033	Discontinued
0.6944	Remote Similarity	NPD4108	Discontinued
0.6942	Remote Similarity	NPD288	Approved
0.694	Remote Similarity	NPD3095	Discontinued
0.6939	Remote Similarity	NPD3750	Approved
0.6934	Remote Similarity	NPD1876	Approved
0.6923	Remote Similarity	NPD1241	Discontinued
0.6918	Remote Similarity	NPD7974	Phase 3
0.6918	Remote Similarity	NPD4534	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