NPASS Compound

Structure

NPC272194 OpenBabel07101719242D 22 25 0 0 0 0 0 0 0 0999 V2000 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6369 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6369 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6369 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6369 -1.8660 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 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 5.1369 -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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1369 -1.0000 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 -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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1369 -1.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 11 18 2 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 14 17 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.11
Volume:	308.233
LogP:	5.392
LogD:	4.23
LogS:	-4.046
# Rotatable Bonds:	1
TPSA:	42.6
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	2.637
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.729
MDCK Permeability:	1.2938051440869458e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.104
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.599

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	100.21923065185547%
Volume Distribution (VD):	0.823
Pgp-substrate:	1.2312840223312378%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.325
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.781
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.958
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.886
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	6.795
Half-life (T1/2):	0.206

ADMET: Toxicity

hERG Blockers:	0.432
Human Hepatotoxicity (H-HT):	0.732
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.771
Skin Sensitization:	0.53
Carcinogencity:	0.776
Eye Corrosion:	0.003
Eye Irritation:	0.687
Respiratory Toxicity:	0.812

Download Data

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

Natural Product: NPC272194

Natural Product ID:	NPC272194
*Common Name:**	Gramniphenol F
IUPAC Name:	4-(7,7-dimethylfuro[3,2-g]chromen-2-yl)phenol
Synonyms:	Gramniphenol F
Standard InCHIKey:	GQRJEBZESAXFAK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O3/c1-19(2)8-7-13-9-14-10-16(12-3-5-15(20)6-4-12)21-17(14)11-18(13)22-19/h3-11,20H,1-2H3
SMILES:	Oc1ccc(cc1)c1oc2c(c1)cc1c(c2)OC(C=C1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333780
PubChem CID:	71579377
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO33109	arundina gramnifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23368966]

☑ 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
EC50	1
IC50	1
Others	4

Activity Type	# Activity
Cell Line	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	102.5	ug.mL-1	PMID[496118]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	IC50	=	40800.0	nM	PMID[496118]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	35.8	%	PMID[496118]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	33.8	%	PMID[496118]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	19.6	n.a.	PMID[496118]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5.22	ug.mL-1	PMID[496118]

☑ 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 NPC272194 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	409
0.1-0.2	1744
0.2-0.3	4232
0.3-0.4	11430
0.4-0.5	6688
0.5-0.6	4104
0.6-0.7	5996
0.7-0.8	4455
0.8-0.85	1977
0.85-0.9	1216
0.9-0.95	421
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC221868
0.993	High Similarity	NPC37208
0.9718	High Similarity	NPC210826
0.9718	High Similarity	NPC300267
0.9718	High Similarity	NPC51641
0.9716	High Similarity	NPC225884
0.9658	High Similarity	NPC472462
0.965	High Similarity	NPC130581
0.965	High Similarity	NPC12148
0.9583	High Similarity	NPC135325
0.9577	High Similarity	NPC17262
0.9517	High Similarity	NPC296030
0.9517	High Similarity	NPC37226
0.9517	High Similarity	NPC39929
0.9517	High Similarity	NPC226644
0.9504	High Similarity	NPC475680
0.9504	High Similarity	NPC305355
0.9463	High Similarity	NPC268360
0.9463	High Similarity	NPC65504
0.9452	High Similarity	NPC230713
0.9452	High Similarity	NPC78335
0.9441	High Similarity	NPC302181
0.9437	High Similarity	NPC118840
0.9437	High Similarity	NPC156590
0.9437	High Similarity	NPC205006
0.9437	High Similarity	NPC147688
0.9437	High Similarity	NPC64908
0.9392	High Similarity	NPC122365
0.9392	High Similarity	NPC213608
0.9392	High Similarity	NPC72370
0.9392	High Similarity	NPC1477
0.9388	High Similarity	NPC170169
0.9384	High Similarity	NPC178202
0.9375	High Similarity	NPC230943
0.9375	High Similarity	NPC311741
0.9375	High Similarity	NPC234629
0.9371	High Similarity	NPC11561
0.9371	High Similarity	NPC53192
0.9371	High Similarity	NPC144499
0.9371	High Similarity	NPC226636
0.9366	High Similarity	NPC270883
0.9366	High Similarity	NPC172986
0.9366	High Similarity	NPC261227
0.9366	High Similarity	NPC235239
0.9329	High Similarity	NPC99199
0.9324	High Similarity	NPC5871
0.9315	High Similarity	NPC168085
0.9306	High Similarity	NPC38219
0.9306	High Similarity	NPC18585
0.9306	High Similarity	NPC219915
0.9306	High Similarity	NPC106985
0.9306	High Similarity	NPC166138
0.9301	High Similarity	NPC110969
0.9301	High Similarity	NPC103362
0.9296	High Similarity	NPC301217
0.9296	High Similarity	NPC303633
0.9296	High Similarity	NPC96565
0.9296	High Similarity	NPC216978
0.9296	High Similarity	NPC220062
0.9296	High Similarity	NPC55018
0.9291	High Similarity	NPC228661
0.9262	High Similarity	NPC235333
0.9252	High Similarity	NPC317492
0.9247	High Similarity	NPC237635
0.9247	High Similarity	NPC79469
0.9247	High Similarity	NPC24673
0.9247	High Similarity	NPC201731
0.9247	High Similarity	NPC104406
0.9247	High Similarity	NPC97716
0.9241	High Similarity	NPC278175
0.9241	High Similarity	NPC257236
0.9236	High Similarity	NPC299080
0.9236	High Similarity	NPC217083
0.9236	High Similarity	NPC293852
0.9236	High Similarity	NPC78803
0.9236	High Similarity	NPC62840
0.9236	High Similarity	NPC59739
0.9236	High Similarity	NPC214236
0.9231	High Similarity	NPC28337
0.9231	High Similarity	NPC69769
0.9231	High Similarity	NPC150522
0.9231	High Similarity	NPC241100
0.9231	High Similarity	NPC159275
0.9225	High Similarity	NPC201395
0.9216	High Similarity	NPC219861
0.9205	High Similarity	NPC260902
0.9205	High Similarity	NPC296957
0.92	High Similarity	NPC198490
0.92	High Similarity	NPC148938
0.92	High Similarity	NPC297531
0.92	High Similarity	NPC213936
0.9195	High Similarity	NPC31627
0.9195	High Similarity	NPC476238
0.9195	High Similarity	NPC327269
0.9195	High Similarity	NPC285623
0.9189	High Similarity	NPC167576
0.9184	High Similarity	NPC266572
0.9184	High Similarity	NPC6511
0.9178	High Similarity	NPC477955
0.9178	High Similarity	NPC124729
0.9172	High Similarity	NPC24821
0.9172	High Similarity	NPC11700
0.9172	High Similarity	NPC9117
0.9172	High Similarity	NPC293053
0.9172	High Similarity	NPC212932
0.9172	High Similarity	NPC190637
0.9167	High Similarity	NPC282300
0.9167	High Similarity	NPC14871
0.9161	High Similarity	NPC53181
0.9161	High Similarity	NPC18260
0.9161	High Similarity	NPC78913
0.9161	High Similarity	NPC217186
0.9155	High Similarity	NPC62735
0.9149	High Similarity	NPC151113
0.9149	High Similarity	NPC163029
0.9145	High Similarity	NPC40583
0.9145	High Similarity	NPC244750
0.9139	High Similarity	NPC160015
0.9139	High Similarity	NPC247677
0.9133	High Similarity	NPC183874
0.9128	High Similarity	NPC193976
0.9128	High Similarity	NPC471675
0.9128	High Similarity	NPC23668
0.9128	High Similarity	NPC472580
0.9128	High Similarity	NPC116604
0.9122	High Similarity	NPC65775
0.9122	High Similarity	NPC10027
0.9116	High Similarity	NPC23728
0.9116	High Similarity	NPC296998
0.9116	High Similarity	NPC14001
0.9116	High Similarity	NPC166757
0.9116	High Similarity	NPC110303
0.9116	High Similarity	NPC17816
0.9116	High Similarity	NPC473077
0.911	High Similarity	NPC155144
0.911	High Similarity	NPC209040
0.911	High Similarity	NPC469953
0.911	High Similarity	NPC326500
0.911	High Similarity	NPC216538
0.911	High Similarity	NPC273538
0.9103	High Similarity	NPC200694
0.9103	High Similarity	NPC473042
0.9097	High Similarity	NPC219917
0.9097	High Similarity	NPC213659
0.9097	High Similarity	NPC326109
0.9097	High Similarity	NPC204088
0.9097	High Similarity	NPC144118
0.9097	High Similarity	NPC80962
0.9097	High Similarity	NPC259166
0.9097	High Similarity	NPC329215
0.9097	High Similarity	NPC259007
0.9097	High Similarity	NPC172250
0.9097	High Similarity	NPC215311
0.9097	High Similarity	NPC204985
0.9097	High Similarity	NPC48624
0.9091	High Similarity	NPC470668
0.9091	High Similarity	NPC21350
0.9091	High Similarity	NPC470669
0.9091	High Similarity	NPC131130
0.9085	High Similarity	NPC260296
0.9085	High Similarity	NPC115432
0.9085	High Similarity	NPC13408
0.9079	High Similarity	NPC246647
0.9079	High Similarity	NPC96342
0.9079	High Similarity	NPC212967
0.9079	High Similarity	NPC164110
0.9067	High Similarity	NPC263676
0.9067	High Similarity	NPC207624
0.9067	High Similarity	NPC142308
0.9067	High Similarity	NPC473996
0.9067	High Similarity	NPC477957
0.906	High Similarity	NPC476185
0.906	High Similarity	NPC188403
0.906	High Similarity	NPC321896
0.906	High Similarity	NPC472421
0.906	High Similarity	NPC61258
0.9054	High Similarity	NPC160821
0.9054	High Similarity	NPC132592
0.9054	High Similarity	NPC244407
0.9054	High Similarity	NPC296869
0.9048	High Similarity	NPC178343
0.9048	High Similarity	NPC20488
0.9048	High Similarity	NPC306488
0.9048	High Similarity	NPC5820
0.9048	High Similarity	NPC83357
0.9048	High Similarity	NPC267375
0.9048	High Similarity	NPC111786
0.9048	High Similarity	NPC88964
0.9048	High Similarity	NPC301276
0.9048	High Similarity	NPC195621
0.9048	High Similarity	NPC214774
0.9048	High Similarity	NPC54577
0.9048	High Similarity	NPC176229
0.9048	High Similarity	NPC154217
0.9048	High Similarity	NPC475052
0.9048	High Similarity	NPC67805
0.9048	High Similarity	NPC470647
0.9048	High Similarity	NPC312973
0.9048	High Similarity	NPC246948
0.9048	High Similarity	NPC142405

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 NPC272194 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	973
0.2-0.3	1443
0.3-0.4	2683
0.4-0.5	1943
0.5-0.6	1172
0.6-0.7	366
0.7-0.8	123
0.8-0.85	41
0.85-0.9	22
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9241	High Similarity	NPD7410	Clinical (unspecified phase)
0.911	High Similarity	NPD4378	Clinical (unspecified phase)
0.8897	High Similarity	NPD1243	Approved
0.8831	High Similarity	NPD3749	Approved
0.8819	High Similarity	NPD2796	Approved
0.8759	High Similarity	NPD2344	Approved
0.875	High Similarity	NPD1510	Phase 2
0.8732	High Similarity	NPD1240	Approved
0.8699	High Similarity	NPD1549	Phase 2
0.863	High Similarity	NPD1550	Clinical (unspecified phase)
0.863	High Similarity	NPD1552	Clinical (unspecified phase)
0.8627	High Similarity	NPD7411	Suspended
0.8611	High Similarity	NPD1607	Approved
0.8591	High Similarity	NPD643	Clinical (unspecified phase)
0.8581	High Similarity	NPD8443	Clinical (unspecified phase)
0.8562	High Similarity	NPD4380	Phase 2
0.8523	High Similarity	NPD2309	Approved
0.8516	High Similarity	NPD2393	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD920	Approved
0.8477	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7075	Discontinued
0.8411	Intermediate Similarity	NPD1511	Approved
0.8408	Intermediate Similarity	NPD7768	Phase 2
0.8397	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD2800	Approved
0.8385	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD3750	Approved
0.8303	Intermediate Similarity	NPD6559	Discontinued
0.8301	Intermediate Similarity	NPD1512	Approved
0.8291	Intermediate Similarity	NPD3882	Suspended
0.828	Intermediate Similarity	NPD2801	Approved
0.8267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1934	Approved
0.8199	Intermediate Similarity	NPD6959	Discontinued
0.817	Intermediate Similarity	NPD6799	Approved
0.8075	Intermediate Similarity	NPD919	Approved
0.8061	Intermediate Similarity	NPD3818	Discontinued
0.8036	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5494	Approved
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2799	Discontinued
0.8	Intermediate Similarity	NPD3748	Approved
0.7988	Intermediate Similarity	NPD3926	Phase 2
0.7975	Intermediate Similarity	NPD1247	Approved
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7961	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD2313	Discontinued
0.7947	Intermediate Similarity	NPD2935	Discontinued
0.7947	Intermediate Similarity	NPD1551	Phase 2
0.7939	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6166	Phase 2
0.7939	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6232	Discontinued
0.7892	Intermediate Similarity	NPD7473	Discontinued
0.7888	Intermediate Similarity	NPD2296	Approved
0.7888	Intermediate Similarity	NPD3817	Phase 2
0.7885	Intermediate Similarity	NPD2532	Approved
0.7885	Intermediate Similarity	NPD2534	Approved
0.7885	Intermediate Similarity	NPD2533	Approved
0.7867	Intermediate Similarity	NPD6651	Approved
0.7838	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6099	Approved
0.7829	Intermediate Similarity	NPD6100	Approved
0.7811	Intermediate Similarity	NPD5953	Discontinued
0.7808	Intermediate Similarity	NPD2798	Approved
0.7785	Intermediate Similarity	NPD5403	Approved
0.7778	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD4287	Approved
0.7742	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1203	Approved
0.773	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7390	Discontinued
0.7692	Intermediate Similarity	NPD5844	Phase 1
0.7692	Intermediate Similarity	NPD7054	Approved
0.7692	Intermediate Similarity	NPD7286	Phase 2
0.7688	Intermediate Similarity	NPD3226	Approved
0.7658	Intermediate Similarity	NPD5401	Approved
0.7651	Intermediate Similarity	NPD4625	Phase 3
0.7647	Intermediate Similarity	NPD4308	Phase 3
0.7647	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD1729	Discontinued
0.7647	Intermediate Similarity	NPD7033	Discontinued
0.7647	Intermediate Similarity	NPD7074	Phase 3
0.7628	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2797	Approved
0.7616	Intermediate Similarity	NPD943	Approved
0.7602	Intermediate Similarity	NPD6797	Phase 2
0.76	Intermediate Similarity	NPD3764	Approved
0.76	Intermediate Similarity	NPD3268	Approved
0.7586	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD422	Phase 1
0.7584	Intermediate Similarity	NPD4908	Phase 1
0.7562	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5402	Approved
0.7558	Intermediate Similarity	NPD7251	Discontinued
0.7552	Intermediate Similarity	NPD1548	Phase 1
0.7548	Intermediate Similarity	NPD2346	Discontinued
0.7548	Intermediate Similarity	NPD1471	Phase 3
0.7546	Intermediate Similarity	NPD6280	Approved
0.7546	Intermediate Similarity	NPD6279	Approved
0.7542	Intermediate Similarity	NPD4361	Phase 2
0.7542	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD9717	Approved
0.7529	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD7808	Phase 3
0.7467	Intermediate Similarity	NPD6832	Phase 2
0.7466	Intermediate Similarity	NPD1610	Phase 2
0.7452	Intermediate Similarity	NPD2654	Approved
0.7414	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7003	Approved
0.7403	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7229	Phase 3
0.7394	Intermediate Similarity	NPD1465	Phase 2
0.7389	Intermediate Similarity	NPD4363	Phase 3
0.7389	Intermediate Similarity	NPD4360	Phase 2
0.7386	Intermediate Similarity	NPD4307	Phase 2
0.7383	Intermediate Similarity	NPD1164	Approved
0.7372	Intermediate Similarity	NPD5405	Approved
0.7372	Intermediate Similarity	NPD5408	Approved
0.7372	Intermediate Similarity	NPD5406	Approved
0.7372	Intermediate Similarity	NPD5404	Approved
0.7349	Intermediate Similarity	NPD4288	Approved
0.7338	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3225	Approved
0.7299	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3972	Approved
0.7297	Intermediate Similarity	NPD1608	Approved
0.7294	Intermediate Similarity	NPD5710	Approved
0.7294	Intermediate Similarity	NPD6808	Phase 2
0.7294	Intermediate Similarity	NPD5711	Approved
0.7289	Intermediate Similarity	NPD5761	Phase 2
0.7289	Intermediate Similarity	NPD5760	Phase 2
0.7267	Intermediate Similarity	NPD3267	Approved
0.7267	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3266	Approved
0.7256	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4749	Approved
0.7247	Intermediate Similarity	NPD8434	Phase 2
0.723	Intermediate Similarity	NPD1201	Approved
0.7212	Intermediate Similarity	NPD6585	Discontinued
0.7209	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD9545	Approved
0.7172	Intermediate Similarity	NPD9493	Approved
0.7169	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7135	Intermediate Similarity	NPD7199	Phase 2
0.7126	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1933	Approved
0.7115	Intermediate Similarity	NPD447	Suspended
0.711	Intermediate Similarity	NPD2403	Approved
0.7097	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD17	Approved
0.7088	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1876	Approved
0.7083	Intermediate Similarity	NPD1241	Discontinued
0.7073	Intermediate Similarity	NPD5049	Phase 3
0.7069	Intermediate Similarity	NPD3446	Phase 1
0.7066	Intermediate Similarity	NPD5889	Approved
0.7066	Intermediate Similarity	NPD5890	Approved
0.7062	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6971	Discontinued
0.7059	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2354	Approved
0.7032	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6798	Discontinued
0.7029	Intermediate Similarity	NPD7177	Discontinued
0.7029	Intermediate Similarity	NPD3751	Discontinued
0.7027	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7577	Discontinued
0.7006	Intermediate Similarity	NPD230	Phase 1
0.7	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8312	Approved
0.6983	Remote Similarity	NPD8313	Approved
0.6981	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6273	Approved
0.6966	Remote Similarity	NPD6104	Discontinued
0.6957	Remote Similarity	NPD2424	Discontinued
0.6948	Remote Similarity	NPD2861	Phase 2
0.6943	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1613	Approved
0.6941	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4477	Approved
0.6937	Remote Similarity	NPD4476	Approved

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