NPASS Compound

Structure

NPC77179 OpenBabel07101719242D 26 29 0 0 1 0 0 0 0 0999 V2000 5.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 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 -1.0000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 -0.8660 0.5000 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 0.0000 -0.0000 0.0000 C 0 0 1 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 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 20 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 26 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 10 21 2 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 23 2 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	354.536
LogP:	3.161
LogD:	2.154
LogS:	-4.285
# Rotatable Bonds:	0
TPSA:	104.81
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	4.182
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.798
MDCK Permeability:	1.701907967799343e-05
Pgp-inhibitor:	0.119
Pgp-substrate:	0.1
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	91.65094757080078%
Volume Distribution (VD):	0.521
Pgp-substrate:	8.466591835021973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.272
CYP2C19-substrate:	0.582
CYP2C9-inhibitor:	0.722
CYP2C9-substrate:	0.742
CYP2D6-inhibitor:	0.482
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.374
CYP3A4-substrate:	0.399

ADMET: Excretion

Clearance (CL):	12.206
Half-life (T1/2):	0.305

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.5
Rat Oral Acute Toxicity:	0.299
Maximum Recommended Daily Dose:	0.408
Skin Sensitization:	0.479
Carcinogencity:	0.587
Eye Corrosion:	0.003
Eye Irritation:	0.561
Respiratory Toxicity:	0.84

Download Data

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

Natural Product: NPC77179

Natural Product ID:	NPC77179
*Common Name:**	(11Br)-5,7,11-Trihydroxy-4,4,9,11B-Tetramethyl-1,2-Dihydronaphtho[2,1-F][1]Benzofuran-3,6-Dione
IUPAC Name:	(11bR)-5,7,11-trihydroxy-4,4,9,11b-tetramethyl-1,2-dihydronaphtho[2,1-f][1]benzofuran-3,6-dione
Synonyms:
Standard InCHIKey:	HFFLVZDJWZPGCS-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-8-7-9-13(22)11-12(15(24)17(9)26-8)20(4)6-5-10(21)19(2,3)18(20)16(25)14(11)23/h7,22,24-25H,5-6H2,1-4H3/t20-/m1/s1
SMILES:	Cc1cc2c(o1)c(O)c1c(c2O)C(=O)C(=C2[C@]1(C)CCC(=O)C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1287938
PubChem CID:	50899164
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[21084196]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29924604]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24239	Teucrium polium	Species	Lamiaceae	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
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[561315]
NPT1	Others	Radical scavenging activity		IC50	=	64000.0	nM	PMID[561314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	50.0	%	PMID[561314]

☑ 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 NPC77179 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	485
0.1-0.2	1952
0.2-0.3	3983
0.3-0.4	10248
0.4-0.5	8159
0.5-0.6	3954
0.6-0.7	5463
0.7-0.8	5766
0.8-0.85	1751
0.85-0.9	827
0.9-0.95	94
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC23553
0.9879	High Similarity	NPC221820
0.982	High Similarity	NPC246153
0.982	High Similarity	NPC228209
0.9702	High Similarity	NPC240508
0.9702	High Similarity	NPC8927
0.9647	High Similarity	NPC240808
0.9467	High Similarity	NPC476273
0.9235	High Similarity	NPC49667
0.9235	High Similarity	NPC8127
0.9226	High Similarity	NPC28042
0.9212	High Similarity	NPC470694
0.9191	High Similarity	NPC476170
0.9176	High Similarity	NPC227906
0.9176	High Similarity	NPC289244
0.9176	High Similarity	NPC245975
0.9157	High Similarity	NPC133065
0.9157	High Similarity	NPC270837
0.9118	High Similarity	NPC82217
0.9118	High Similarity	NPC30550
0.9118	High Similarity	NPC65885
0.9118	High Similarity	NPC216842
0.9118	High Similarity	NPC476640
0.9107	High Similarity	NPC95715
0.9107	High Similarity	NPC470704
0.9102	High Similarity	NPC39306
0.9096	High Similarity	NPC294965
0.9091	High Similarity	NPC295436
0.9064	High Similarity	NPC287243
0.9059	High Similarity	NPC54098
0.9059	High Similarity	NPC230619
0.9053	High Similarity	NPC247136
0.9053	High Similarity	NPC202470
0.9042	High Similarity	NPC173587
0.9042	High Similarity	NPC220313
0.9042	High Similarity	NPC236132
0.9042	High Similarity	NPC208120
0.904	High Similarity	NPC60848
0.9036	High Similarity	NPC66288
0.903	High Similarity	NPC100123
0.9006	High Similarity	NPC277510
0.9	High Similarity	NPC476641
0.8994	High Similarity	NPC126204
0.8994	High Similarity	NPC247973
0.8988	High Similarity	NPC146584
0.8988	High Similarity	NPC36320
0.8988	High Similarity	NPC37183
0.8988	High Similarity	NPC326520
0.8988	High Similarity	NPC21016
0.8988	High Similarity	NPC473286
0.8988	High Similarity	NPC45449
0.8982	High Similarity	NPC312056
0.8982	High Similarity	NPC84515
0.8976	High Similarity	NPC56085
0.8976	High Similarity	NPC14353
0.8976	High Similarity	NPC119224
0.8976	High Similarity	NPC45146
0.8976	High Similarity	NPC228785
0.8976	High Similarity	NPC235018
0.8976	High Similarity	NPC320359
0.896	High Similarity	NPC246877
0.896	High Similarity	NPC297807
0.8935	High Similarity	NPC37870
0.8935	High Similarity	NPC170245
0.8935	High Similarity	NPC277480
0.8929	High Similarity	NPC59295
0.8929	High Similarity	NPC472278
0.8929	High Similarity	NPC197168
0.8929	High Similarity	NPC1706
0.8929	High Similarity	NPC473313
0.8929	High Similarity	NPC18100
0.8929	High Similarity	NPC475055
0.8929	High Similarity	NPC329669
0.8929	High Similarity	NPC1755
0.8929	High Similarity	NPC263092
0.8929	High Similarity	NPC39305
0.8922	High Similarity	NPC258331
0.8922	High Similarity	NPC32694
0.8922	High Similarity	NPC61010
0.8922	High Similarity	NPC278052
0.8922	High Similarity	NPC40491
0.8922	High Similarity	NPC188486
0.8916	High Similarity	NPC196879
0.8916	High Similarity	NPC185258
0.8916	High Similarity	NPC172770
0.8916	High Similarity	NPC235448
0.8914	High Similarity	NPC471842
0.8909	High Similarity	NPC138243
0.8909	High Similarity	NPC274730
0.8909	High Similarity	NPC142339
0.8895	High Similarity	NPC310794
0.8889	High Similarity	NPC124470
0.8889	High Similarity	NPC101107
0.8889	High Similarity	NPC109827
0.8882	High Similarity	NPC470374
0.8882	High Similarity	NPC478059
0.8882	High Similarity	NPC478060
0.8882	High Similarity	NPC471975
0.8882	High Similarity	NPC470377
0.8882	High Similarity	NPC50394
0.8882	High Similarity	NPC232936
0.8876	High Similarity	NPC25361
0.8876	High Similarity	NPC472277
0.8869	High Similarity	NPC238995
0.8869	High Similarity	NPC25152
0.8869	High Similarity	NPC272722
0.8869	High Similarity	NPC81679
0.8862	High Similarity	NPC246478
0.8862	High Similarity	NPC84571
0.8862	High Similarity	NPC80375
0.8855	High Similarity	NPC262286
0.8855	High Similarity	NPC217677
0.8855	High Similarity	NPC304008
0.8855	High Similarity	NPC236796
0.8855	High Similarity	NPC36852
0.8855	High Similarity	NPC187745
0.8855	High Similarity	NPC165977
0.8855	High Similarity	NPC300727
0.8855	High Similarity	NPC161960
0.8855	High Similarity	NPC241904
0.8855	High Similarity	NPC79053
0.8851	High Similarity	NPC98546
0.8837	High Similarity	NPC158226
0.8837	High Similarity	NPC307286
0.883	High Similarity	NPC163130
0.883	High Similarity	NPC476637
0.883	High Similarity	NPC213416
0.883	High Similarity	NPC165979
0.883	High Similarity	NPC475805
0.8817	High Similarity	NPC189473
0.8817	High Similarity	NPC41301
0.8817	High Similarity	NPC236521
0.8817	High Similarity	NPC475985
0.8817	High Similarity	NPC29055
0.8817	High Similarity	NPC306321
0.8817	High Similarity	NPC248638
0.8817	High Similarity	NPC152659
0.8817	High Similarity	NPC23298
0.8817	High Similarity	NPC205265
0.8817	High Similarity	NPC303460
0.8817	High Similarity	NPC472281
0.8817	High Similarity	NPC7483
0.8817	High Similarity	NPC207690
0.881	High Similarity	NPC187354
0.881	High Similarity	NPC278427
0.881	High Similarity	NPC472275
0.881	High Similarity	NPC311740
0.8802	High Similarity	NPC16935
0.8802	High Similarity	NPC195832
0.8802	High Similarity	NPC476242
0.88	High Similarity	NPC104682
0.8795	High Similarity	NPC472461
0.8795	High Similarity	NPC45131
0.8795	High Similarity	NPC475799
0.8795	High Similarity	NPC68093
0.8795	High Similarity	NPC180924
0.8795	High Similarity	NPC3980
0.8795	High Similarity	NPC115853
0.8795	High Similarity	NPC13779
0.8795	High Similarity	NPC191146
0.8793	High Similarity	NPC471841
0.8788	High Similarity	NPC89474
0.8786	High Similarity	NPC473834
0.8779	High Similarity	NPC472276
0.8779	High Similarity	NPC78830
0.8779	High Similarity	NPC218533
0.8779	High Similarity	NPC315306
0.8779	High Similarity	NPC131866
0.8779	High Similarity	NPC313717
0.8772	High Similarity	NPC241820
0.8765	High Similarity	NPC472450
0.8765	High Similarity	NPC26386
0.8765	High Similarity	NPC275780
0.8765	High Similarity	NPC239752
0.8764	High Similarity	NPC174486
0.8757	High Similarity	NPC71260
0.8757	High Similarity	NPC329760
0.8757	High Similarity	NPC78332
0.875	High Similarity	NPC474287
0.875	High Similarity	NPC200746
0.875	High Similarity	NPC475996
0.875	High Similarity	NPC476980
0.875	High Similarity	NPC475886
0.875	High Similarity	NPC47883
0.8743	High Similarity	NPC37543
0.8743	High Similarity	NPC164110
0.8743	High Similarity	NPC246647
0.8743	High Similarity	NPC273843
0.8743	High Similarity	NPC201127
0.8743	High Similarity	NPC96342
0.8743	High Similarity	NPC219867
0.8743	High Similarity	NPC136674
0.8743	High Similarity	NPC212967
0.8743	High Similarity	NPC199463
0.8743	High Similarity	NPC180011
0.8743	High Similarity	NPC78225
0.8735	High Similarity	NPC113906
0.8735	High Similarity	NPC234485
0.8728	High Similarity	NPC174700
0.8728	High Similarity	NPC248593

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 NPC77179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	986
0.2-0.3	1845
0.3-0.4	2780
0.4-0.5	1790
0.5-0.6	850
0.6-0.7	329
0.7-0.8	132
0.8-0.85	17
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD3882	Suspended
0.8563	High Similarity	NPD2801	Approved
0.848	Intermediate Similarity	NPD1247	Approved
0.8343	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD6232	Discontinued
0.8314	Intermediate Similarity	NPD5494	Approved
0.8286	Intermediate Similarity	NPD7473	Discontinued
0.8284	Intermediate Similarity	NPD1934	Approved
0.8253	Intermediate Similarity	NPD1512	Approved
0.8192	Intermediate Similarity	NPD5844	Phase 1
0.8136	Intermediate Similarity	NPD3818	Discontinued
0.8133	Intermediate Similarity	NPD1511	Approved
0.8125	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6166	Phase 2
0.8084	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD3926	Phase 2
0.8023	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD2800	Approved
0.7977	Intermediate Similarity	NPD3817	Phase 2
0.7956	Intermediate Similarity	NPD6559	Discontinued
0.7955	Intermediate Similarity	NPD6959	Discontinued
0.7953	Intermediate Similarity	NPD6599	Discontinued
0.7943	Intermediate Similarity	NPD919	Approved
0.7912	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7075	Discontinued
0.7886	Intermediate Similarity	NPD3749	Approved
0.787	Intermediate Similarity	NPD2533	Approved
0.787	Intermediate Similarity	NPD2532	Approved
0.787	Intermediate Similarity	NPD2534	Approved
0.7849	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD8434	Phase 2
0.7829	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7819	Suspended
0.7816	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3226	Approved
0.7747	Intermediate Similarity	NPD7074	Phase 3
0.7746	Intermediate Similarity	NPD4380	Phase 2
0.7705	Intermediate Similarity	NPD6797	Phase 2
0.7692	Intermediate Similarity	NPD7054	Approved
0.767	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD7251	Discontinued
0.7661	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6801	Discontinued
0.7651	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7472	Approved
0.7622	Intermediate Similarity	NPD7808	Phase 3
0.7609	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6799	Approved
0.76	Intermediate Similarity	NPD7411	Suspended
0.7579	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1243	Approved
0.7571	Intermediate Similarity	NPD5402	Approved
0.756	Intermediate Similarity	NPD1471	Phase 3
0.756	Intermediate Similarity	NPD2344	Approved
0.7545	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6234	Discontinued
0.753	Intermediate Similarity	NPD1607	Approved
0.7529	Intermediate Similarity	NPD3750	Approved
0.7527	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD943	Approved
0.7515	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6099	Approved
0.7487	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD920	Approved
0.7456	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2346	Discontinued
0.7446	Intermediate Similarity	NPD3751	Discontinued
0.744	Intermediate Similarity	NPD1510	Phase 2
0.7427	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1240	Approved
0.7396	Intermediate Similarity	NPD2796	Approved
0.7396	Intermediate Similarity	NPD2935	Discontinued
0.7384	Intermediate Similarity	NPD2309	Approved
0.7377	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD37	Approved
0.7356	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7768	Phase 2
0.7333	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD4966	Approved
0.7326	Intermediate Similarity	NPD4628	Phase 3
0.7322	Intermediate Similarity	NPD5711	Approved
0.7322	Intermediate Similarity	NPD5710	Approved
0.731	Intermediate Similarity	NPD6776	Approved
0.731	Intermediate Similarity	NPD6779	Approved
0.731	Intermediate Similarity	NPD6780	Approved
0.731	Intermediate Similarity	NPD6781	Approved
0.731	Intermediate Similarity	NPD6778	Approved
0.731	Intermediate Similarity	NPD6782	Approved
0.731	Intermediate Similarity	NPD6777	Approved
0.7308	Intermediate Similarity	NPD7907	Approved
0.7295	Intermediate Similarity	NPD4111	Phase 1
0.7295	Intermediate Similarity	NPD4665	Approved
0.7277	Intermediate Similarity	NPD8150	Discontinued
0.7273	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7199	Phase 2
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7228	Approved
0.7257	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD2403	Approved
0.7241	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3748	Approved
0.7228	Intermediate Similarity	NPD3787	Discontinued
0.7219	Intermediate Similarity	NPD6651	Approved
0.7212	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7435	Discontinued
0.7175	Intermediate Similarity	NPD5403	Approved
0.7169	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD447	Suspended
0.716	Intermediate Similarity	NPD230	Phase 1
0.7135	Intermediate Similarity	NPD2799	Discontinued
0.7126	Intermediate Similarity	NPD4625	Phase 3
0.712	Intermediate Similarity	NPD8312	Approved
0.712	Intermediate Similarity	NPD8313	Approved
0.7114	Intermediate Similarity	NPD7697	Approved
0.7114	Intermediate Similarity	NPD7698	Approved
0.7114	Intermediate Similarity	NPD7696	Phase 3
0.7108	Intermediate Similarity	NPD8151	Discontinued
0.7093	Intermediate Similarity	NPD1551	Phase 2
0.7079	Intermediate Similarity	NPD7870	Phase 2
0.7079	Intermediate Similarity	NPD7871	Phase 2
0.7074	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5401	Approved
0.7059	Intermediate Similarity	NPD7701	Phase 2
0.7056	Intermediate Similarity	NPD6535	Approved
0.7056	Intermediate Similarity	NPD6534	Approved
0.7043	Intermediate Similarity	NPD7229	Phase 3
0.7033	Intermediate Similarity	NPD5760	Phase 2
0.7033	Intermediate Similarity	NPD5761	Phase 2
0.7026	Intermediate Similarity	NPD4287	Approved
0.7015	Intermediate Similarity	NPD2493	Approved
0.7015	Intermediate Similarity	NPD2494	Approved
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1613	Approved
0.6994	Remote Similarity	NPD5404	Approved
0.6994	Remote Similarity	NPD5406	Approved
0.6994	Remote Similarity	NPD5405	Approved
0.6994	Remote Similarity	NPD5408	Approved
0.699	Remote Similarity	NPD7874	Approved
0.699	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6190	Approved
0.6984	Remote Similarity	NPD2163	Approved
0.6982	Remote Similarity	NPD2313	Discontinued
0.698	Remote Similarity	NPD3057	Approved
0.698	Remote Similarity	NPD2491	Approved
0.6966	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5953	Discontinued
0.6957	Remote Similarity	NPD7801	Approved
0.6957	Remote Similarity	NPD7783	Phase 2
0.6957	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7699	Phase 2
0.695	Remote Similarity	NPD7700	Phase 2
0.6947	Remote Similarity	NPD7286	Phase 2
0.6932	Remote Similarity	NPD7003	Approved
0.6931	Remote Similarity	NPD3450	Approved
0.6931	Remote Similarity	NPD3452	Approved
0.6928	Remote Similarity	NPD6696	Suspended
0.6927	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3027	Phase 3
0.6916	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4582	Approved
0.6912	Remote Similarity	NPD4583	Approved
0.6906	Remote Similarity	NPD7458	Discontinued
0.6906	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD2296	Approved
0.6897	Remote Similarity	NPD3533	Approved
0.6897	Remote Similarity	NPD3448	Approved
0.6897	Remote Similarity	NPD6823	Phase 2
0.6897	Remote Similarity	NPD2972	Approved
0.6886	Remote Similarity	NPD1470	Approved
0.6863	Remote Similarity	NPD4004	Approved
0.6863	Remote Similarity	NPD4002	Approved
0.6857	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3300	Phase 2
0.6851	Remote Similarity	NPD1653	Approved
0.6839	Remote Similarity	NPD6764	Approved
0.6839	Remote Similarity	NPD6765	Approved
0.6839	Remote Similarity	NPD7240	Approved
0.6821	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2488	Approved
0.6818	Remote Similarity	NPD2490	Approved
0.6816	Remote Similarity	NPD2975	Approved
0.6816	Remote Similarity	NPD2973	Approved
0.6816	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2974	Approved
0.6809	Remote Similarity	NPD8127	Discontinued
0.6805	Remote Similarity	NPD9494	Approved
0.6802	Remote Similarity	NPD4060	Phase 1

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