NPASS Compound

Structure

NPC17262 OpenBabel07101718202D 23 26 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 -8.6369 0.1340 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 6 1 0 0 0 0 4 13 2 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 16 2 0 0 0 0 7 16 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 18 1 0 0 0 0 12 19 2 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.13
Volume:	325.529
LogP:	5.848
LogD:	4.451
LogS:	-6.594
# Rotatable Bonds:	2
TPSA:	31.6
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	2.517
Fsp3:	0.2
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:	-4.735
MDCK Permeability:	1.3102938282827381e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.765

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	99.94783782958984%
Volume Distribution (VD):	0.76
Pgp-substrate:	2.20947003364563%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.92
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.79
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.925
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.868
CYP3A4-substrate:	0.578

ADMET: Excretion

Clearance (CL):	5.686
Half-life (T1/2):	0.1

ADMET: Toxicity

hERG Blockers:	0.799
Human Hepatotoxicity (H-HT):	0.898
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.317
Rat Oral Acute Toxicity:	0.153
Maximum Recommended Daily Dose:	0.707
Skin Sensitization:	0.248
Carcinogencity:	0.827
Eye Corrosion:	0.003
Eye Irritation:	0.429
Respiratory Toxicity:	0.503

Download Data

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

Natural Product: NPC17262

Natural Product ID:	NPC17262
*Common Name:**	Gramniphenol G
IUPAC Name:	2-(4-methoxyphenyl)-7,7-dimethylfuro[3,2-g]chromene
Synonyms:	Gramniphenol G
Standard InCHIKey:	UDHFTJHEOIOAAC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O3/c1-20(2)9-8-14-10-15-11-17(22-18(15)12-19(14)23-20)13-4-6-16(21-3)7-5-13/h4-12H,1-3H3
SMILES:	CC1(C)C=Cc2cc3cc(c4ccc(cc4)OC)oc3cc2O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333781
PubChem CID:	71579378
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	=	88.7	ug.mL-1	PMID[465017]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	IC50	=	57700.0	nM	PMID[465017]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	36.1	%	PMID[465017]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	32.1	%	PMID[465017]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	13.9	n.a.	PMID[465017]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	6.38	ug.mL-1	PMID[465017]

☑ 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 NPC17262 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	465
0.1-0.2	1827
0.2-0.3	4542
0.3-0.4	11811
0.4-0.5	6209
0.5-0.6	4493
0.6-0.7	6193
0.7-0.8	4255
0.8-0.85	1798
0.85-0.9	975
0.9-0.95	123
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC272194
0.951	High Similarity	NPC221868
0.951	High Similarity	NPC37208
0.9437	High Similarity	NPC51641
0.9437	High Similarity	NPC300267
0.9371	High Similarity	NPC12148
0.9371	High Similarity	NPC130581
0.9348	High Similarity	NPC161196
0.931	High Similarity	NPC135303
0.931	High Similarity	NPC148423
0.9306	High Similarity	NPC135325
0.9306	High Similarity	NPC306788
0.9301	High Similarity	NPC210826
0.9296	High Similarity	NPC225884
0.9281	High Similarity	NPC157855
0.927	High Similarity	NPC292998
0.9252	High Similarity	NPC472462
0.9241	High Similarity	NPC39929
0.9241	High Similarity	NPC226644
0.9241	High Similarity	NPC296030
0.9241	High Similarity	NPC37226
0.9236	High Similarity	NPC198427
0.922	High Similarity	NPC472409
0.9214	High Similarity	NPC17848
0.9209	High Similarity	NPC254741
0.9209	High Similarity	NPC29638
0.9197	High Similarity	NPC229646
0.9195	High Similarity	NPC65504
0.9184	High Similarity	NPC38361
0.9184	High Similarity	NPC130015
0.9178	High Similarity	NPC472406
0.9161	High Similarity	NPC302181
0.9155	High Similarity	NPC103362
0.9155	High Similarity	NPC254010
0.9149	High Similarity	NPC11566
0.9149	High Similarity	NPC262635
0.9137	High Similarity	NPC46869
0.9124	High Similarity	NPC284424
0.9122	High Similarity	NPC1477
0.9122	High Similarity	NPC122365
0.9122	High Similarity	NPC213608
0.9122	High Similarity	NPC41719
0.9116	High Similarity	NPC472407
0.9116	High Similarity	NPC170169
0.9097	High Similarity	NPC179970
0.9097	High Similarity	NPC230943
0.9097	High Similarity	NPC311741
0.9097	High Similarity	NPC234629
0.9091	High Similarity	NPC11561
0.9091	High Similarity	NPC53192
0.9091	High Similarity	NPC226636
0.9091	High Similarity	NPC313036
0.9085	High Similarity	NPC150522
0.9085	High Similarity	NPC305355
0.9085	High Similarity	NPC475680
0.9067	High Similarity	NPC268360
0.906	High Similarity	NPC233776
0.9058	High Similarity	NPC473655
0.9058	High Similarity	NPC101294
0.9054	High Similarity	NPC5871
0.9048	High Similarity	NPC230713
0.9048	High Similarity	NPC78335
0.9048	High Similarity	NPC191104
0.9041	High Similarity	NPC168085
0.9041	High Similarity	NPC266743
0.9034	High Similarity	NPC190572
0.9028	High Similarity	NPC18585
0.9028	High Similarity	NPC166138
0.9028	High Similarity	NPC106985
0.9028	High Similarity	NPC59522
0.9021	High Similarity	NPC205006
0.9021	High Similarity	NPC118840
0.9021	High Similarity	NPC110969
0.9021	High Similarity	NPC147688
0.9021	High Similarity	NPC64908
0.9021	High Similarity	NPC156590
0.9007	High Similarity	NPC259685
0.8993	High Similarity	NPC72370
0.8993	High Similarity	NPC247743
0.8993	High Similarity	NPC223354
0.8986	High Similarity	NPC278556
0.898	High Similarity	NPC88445
0.898	High Similarity	NPC317492
0.898	High Similarity	NPC178202
0.8973	High Similarity	NPC201731
0.8973	High Similarity	NPC97716
0.8973	High Similarity	NPC237635
0.8973	High Similarity	NPC104406
0.8973	High Similarity	NPC79469
0.8973	High Similarity	NPC471285
0.8973	High Similarity	NPC24673
0.8958	High Similarity	NPC144499
0.8958	High Similarity	NPC51146
0.8958	High Similarity	NPC147145
0.8958	High Similarity	NPC166858
0.8954	High Similarity	NPC219861
0.8951	High Similarity	NPC261227
0.8951	High Similarity	NPC159275
0.8951	High Similarity	NPC171094
0.8951	High Similarity	NPC172986
0.8951	High Similarity	NPC235239
0.8951	High Similarity	NPC270883
0.8951	High Similarity	NPC241100
0.894	High Similarity	NPC260902
0.894	High Similarity	NPC296957
0.8933	High Similarity	NPC99199
0.8933	High Similarity	NPC198490
0.8933	High Similarity	NPC148938
0.8929	High Similarity	NPC125269
0.8926	High Similarity	NPC285623
0.8926	High Similarity	NPC31627
0.8926	High Similarity	NPC327269
0.8926	High Similarity	NPC476238
0.8926	High Similarity	NPC263676
0.8921	High Similarity	NPC182428
0.8912	High Similarity	NPC266572
0.8912	High Similarity	NPC6511
0.8904	High Similarity	NPC124729
0.8904	High Similarity	NPC477955
0.8897	High Similarity	NPC189650
0.8897	High Similarity	NPC38219
0.8897	High Similarity	NPC219915
0.8889	High Similarity	NPC282300
0.8889	High Similarity	NPC52576
0.8882	High Similarity	NPC40583
0.8881	High Similarity	NPC220062
0.8881	High Similarity	NPC217186
0.8881	High Similarity	NPC18260
0.8881	High Similarity	NPC78913
0.8881	High Similarity	NPC136095
0.8881	High Similarity	NPC55018
0.8881	High Similarity	NPC301217
0.8881	High Similarity	NPC96565
0.8881	High Similarity	NPC473209
0.8881	High Similarity	NPC303633
0.8881	High Similarity	NPC53181
0.8881	High Similarity	NPC216978
0.8874	High Similarity	NPC160015
0.8874	High Similarity	NPC247677
0.8873	High Similarity	NPC253616
0.8873	High Similarity	NPC228661
0.8873	High Similarity	NPC103001
0.8867	High Similarity	NPC183874
0.8867	High Similarity	NPC131725
0.8867	High Similarity	NPC235333
0.8865	High Similarity	NPC99854
0.8859	High Similarity	NPC471675
0.8859	High Similarity	NPC116604
0.8859	High Similarity	NPC472580
0.8844	High Similarity	NPC304443
0.8844	High Similarity	NPC110303
0.8844	High Similarity	NPC74539
0.8844	High Similarity	NPC23728
0.8844	High Similarity	NPC17816
0.8844	High Similarity	NPC473077
0.8844	High Similarity	NPC296998
0.8836	High Similarity	NPC257236
0.8836	High Similarity	NPC209040
0.8836	High Similarity	NPC246903
0.8836	High Similarity	NPC216538
0.8836	High Similarity	NPC278175
0.8836	High Similarity	NPC469953
0.8836	High Similarity	NPC273538
0.8832	High Similarity	NPC125887
0.8828	High Similarity	NPC78803
0.8828	High Similarity	NPC59739
0.8828	High Similarity	NPC214236
0.8828	High Similarity	NPC62840
0.8828	High Similarity	NPC293852
0.8828	High Similarity	NPC299080
0.8828	High Similarity	NPC217083
0.8824	High Similarity	NPC115432
0.8824	High Similarity	NPC260296
0.8819	High Similarity	NPC172250
0.8819	High Similarity	NPC28337
0.8819	High Similarity	NPC215311
0.8819	High Similarity	NPC144118
0.8819	High Similarity	NPC80962
0.8819	High Similarity	NPC213659
0.8819	High Similarity	NPC48624
0.8819	High Similarity	NPC69769
0.8819	High Similarity	NPC219917
0.8819	High Similarity	NPC326109
0.8819	High Similarity	NPC204985
0.8819	High Similarity	NPC259166
0.8816	High Similarity	NPC96342
0.8816	High Similarity	NPC246647
0.8816	High Similarity	NPC212967
0.8816	High Similarity	NPC164110
0.8811	High Similarity	NPC21350
0.8811	High Similarity	NPC36414
0.8811	High Similarity	NPC131130
0.8811	High Similarity	NPC201395
0.8808	High Similarity	NPC213936
0.8808	High Similarity	NPC297531
0.8803	High Similarity	NPC61546
0.8803	High Similarity	NPC268081
0.8803	High Similarity	NPC72452
0.88	High Similarity	NPC473996
0.88	High Similarity	NPC207624

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 NPC17262 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	997
0.2-0.3	1438
0.3-0.4	2768
0.4-0.5	1904
0.5-0.6	1104
0.6-0.7	365
0.7-0.8	111
0.8-0.85	40
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9209	High Similarity	NPD2796	Approved
0.9149	High Similarity	NPD1243	Approved
0.8958	High Similarity	NPD643	Clinical (unspecified phase)
0.8844	High Similarity	NPD920	Approved
0.8836	High Similarity	NPD642	Clinical (unspecified phase)
0.8836	High Similarity	NPD7410	Clinical (unspecified phase)
0.8836	High Similarity	NPD4378	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD7411	Suspended
0.8472	Intermediate Similarity	NPD1510	Phase 2
0.8452	Intermediate Similarity	NPD3749	Approved
0.8451	Intermediate Similarity	NPD1240	Approved
0.8425	Intermediate Similarity	NPD1549	Phase 2
0.8397	Intermediate Similarity	NPD919	Approved
0.8377	Intermediate Similarity	NPD7819	Suspended
0.8377	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD2344	Approved
0.8356	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD1607	Approved
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD6801	Discontinued
0.8302	Intermediate Similarity	NPD3926	Phase 2
0.8301	Intermediate Similarity	NPD4380	Phase 2
0.8291	Intermediate Similarity	NPD1247	Approved
0.8267	Intermediate Similarity	NPD6799	Approved
0.8258	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD3748	Approved
0.8217	Intermediate Similarity	NPD7075	Discontinued
0.8153	Intermediate Similarity	NPD7768	Phase 2
0.8137	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2309	Approved
0.8121	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6599	Discontinued
0.8061	Intermediate Similarity	NPD6559	Discontinued
0.8038	Intermediate Similarity	NPD3882	Suspended
0.8026	Intermediate Similarity	NPD1511	Approved
0.8025	Intermediate Similarity	NPD2801	Approved
0.8	Intermediate Similarity	NPD2800	Approved
0.7987	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3817	Phase 2
0.7962	Intermediate Similarity	NPD1934	Approved
0.795	Intermediate Similarity	NPD6959	Discontinued
0.7947	Intermediate Similarity	NPD3750	Approved
0.7929	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1512	Approved
0.7871	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD2799	Discontinued
0.7848	Intermediate Similarity	NPD6280	Approved
0.7848	Intermediate Similarity	NPD6279	Approved
0.7818	Intermediate Similarity	NPD3818	Discontinued
0.7818	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD2313	Discontinued
0.7798	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6832	Phase 2
0.7778	Intermediate Similarity	NPD2798	Approved
0.7771	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2654	Approved
0.7756	Intermediate Similarity	NPD5403	Approved
0.7748	Intermediate Similarity	NPD1471	Phase 3
0.7748	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5401	Approved
0.7697	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6166	Phase 2
0.7697	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6232	Discontinued
0.7682	Intermediate Similarity	NPD2935	Discontinued
0.7682	Intermediate Similarity	NPD1551	Phase 2
0.7651	Intermediate Similarity	NPD7473	Discontinued
0.7628	Intermediate Similarity	NPD2533	Approved
0.7628	Intermediate Similarity	NPD2534	Approved
0.7628	Intermediate Similarity	NPD2532	Approved
0.7622	Intermediate Similarity	NPD3972	Approved
0.76	Intermediate Similarity	NPD6651	Approved
0.7584	Intermediate Similarity	NPD4307	Phase 2
0.7576	Intermediate Similarity	NPD6808	Phase 2
0.7574	Intermediate Similarity	NPD5953	Discontinued
0.756	Intermediate Similarity	NPD5844	Phase 1
0.7531	Intermediate Similarity	NPD5402	Approved
0.7531	Intermediate Similarity	NPD2296	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3267	Approved
0.7466	Intermediate Similarity	NPD3266	Approved
0.7456	Intermediate Similarity	NPD7054	Approved
0.7456	Intermediate Similarity	NPD7286	Phase 2
0.7451	Intermediate Similarity	NPD6100	Approved
0.7451	Intermediate Similarity	NPD6099	Approved
0.745	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3226	Approved
0.7429	Intermediate Similarity	NPD4287	Approved
0.7417	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1933	Approved
0.7412	Intermediate Similarity	NPD1729	Discontinued
0.7412	Intermediate Similarity	NPD7472	Approved
0.7412	Intermediate Similarity	NPD7074	Phase 3
0.741	Intermediate Similarity	NPD1241	Discontinued
0.7403	Intermediate Similarity	NPD2346	Discontinued
0.7397	Intermediate Similarity	NPD1876	Approved
0.7391	Intermediate Similarity	NPD6585	Discontinued
0.7386	Intermediate Similarity	NPD4308	Phase 3
0.7386	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2403	Approved
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7368	Intermediate Similarity	NPD6797	Phase 2
0.7365	Intermediate Similarity	NPD7229	Phase 3
0.7347	Intermediate Similarity	NPD2797	Approved
0.7347	Intermediate Similarity	NPD1203	Approved
0.7346	Intermediate Similarity	NPD5889	Approved
0.7346	Intermediate Similarity	NPD5890	Approved
0.7342	Intermediate Similarity	NPD7390	Discontinued
0.7333	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD1296	Phase 2
0.7326	Intermediate Similarity	NPD7251	Discontinued
0.7318	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4361	Phase 2
0.7315	Intermediate Similarity	NPD4908	Phase 1
0.7292	Intermediate Similarity	NPD17	Approved
0.7283	Intermediate Similarity	NPD7808	Phase 3
0.7273	Intermediate Similarity	NPD1548	Phase 1
0.7267	Intermediate Similarity	NPD4625	Phase 3
0.7261	Intermediate Similarity	NPD7003	Approved
0.7261	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD9717	Approved
0.7237	Intermediate Similarity	NPD943	Approved
0.7222	Intermediate Similarity	NPD1651	Approved
0.7219	Intermediate Similarity	NPD3764	Approved
0.7215	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4288	Approved
0.7192	Intermediate Similarity	NPD422	Phase 1
0.7192	Intermediate Similarity	NPD1610	Phase 2
0.719	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5124	Phase 1
0.7188	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1019	Discontinued
0.7176	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4360	Phase 2
0.7167	Intermediate Similarity	NPD4363	Phase 3
0.7152	Intermediate Similarity	NPD5760	Phase 2
0.7152	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7125	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3142	Approved
0.7124	Intermediate Similarity	NPD3140	Approved
0.7119	Intermediate Similarity	NPD8434	Phase 2
0.7117	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3887	Approved
0.7101	Intermediate Similarity	NPD7199	Phase 2
0.7099	Intermediate Similarity	NPD3869	Phase 3
0.7099	Intermediate Similarity	NPD3873	Phase 3
0.7076	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2353	Approved
0.707	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5710	Approved
0.7059	Intermediate Similarity	NPD5711	Approved
0.7048	Intermediate Similarity	NPD1465	Phase 2
0.7047	Intermediate Similarity	NPD3225	Approved
0.7044	Intermediate Similarity	NPD7466	Approved
0.703	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6971	Discontinued
0.7018	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD1164	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.6975	Remote Similarity	NPD4662	Approved
0.6975	Remote Similarity	NPD4661	Approved
0.6974	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1281	Approved
0.6933	Remote Similarity	NPD5049	Phase 3
0.6933	Remote Similarity	NPD6273	Approved
0.6932	Remote Similarity	NPD6104	Discontinued
0.6931	Remote Similarity	NPD7584	Approved
0.6918	Remote Similarity	NPD9545	Approved
0.6918	Remote Similarity	NPD2424	Discontinued
0.6899	Remote Similarity	NPD4476	Approved
0.6899	Remote Similarity	NPD4477	Approved
0.6897	Remote Similarity	NPD9493	Approved
0.6897	Remote Similarity	NPD3751	Discontinued
0.6897	Remote Similarity	NPD7177	Discontinued
0.6894	Remote Similarity	NPD2354	Approved
0.6886	Remote Similarity	NPD6844	Discontinued
0.6886	Remote Similarity	NPD7577	Discontinued
0.6883	Remote Similarity	NPD411	Approved
0.6882	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4749	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