NPASS Compound

Structure

CID25127 OpenBabel06191715352D 27 29 0 0 1 0 0 0 0 0999 V2000 -2.7026 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5173 5.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8739 1.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2807 2.6943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2916 2.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8794 1.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6929 3.5033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6984 3.3988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4727 0.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2738 3.0485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0996 4.4168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0605 -0.0464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1106 4.2078 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 25 1 0 0 0 0 2 26 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 17 1 0 0 0 0 5 12 2 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 6 14 2 0 0 0 0 7 11 2 0 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 10 27 1 0 0 0 0 11 19 1 0 0 0 0 13 22 1 0 0 0 0 14 25 1 0 0 0 0 15 9 1 1 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 1 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 20 12 1 6 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.14
Volume:	371.883
LogP:	1.914
LogD:	2.072
LogS:	-3.855
# Rotatable Bonds:	6
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	3.57
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.839
MDCK Permeability:	7.901218850747682e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.801

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	92.19564819335938%
Volume Distribution (VD):	0.851
Pgp-substrate:	6.810477256774902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.513
CYP1A2-substrate:	0.721
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.247
CYP2C9-inhibitor:	0.375
CYP2C9-substrate:	0.759
CYP2D6-inhibitor:	0.429
CYP2D6-substrate:	0.784
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.368

ADMET: Excretion

Clearance (CL):	11.53
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.17
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.317
AMES Toxicity:	0.105
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.395
Skin Sensitization:	0.813
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.163
Respiratory Toxicity:	0.051

Download Data

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

Natural Product: NPC25127

Natural Product ID:	NPC25127
*Common Name:**	Forsythialan A
IUPAC Name:	(4-hydroxy-3-methoxyphenyl)-[(3R,4R,5S)-5-(3-hydroxy-5-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methanone
Synonyms:
Standard InCHIKey:	PSOMGRNIAXLWFK-TWOQFEAHSA-N
Standard InCHI:	InChI=1S/C20H22O7/c1-25-14-6-12(5-13(22)8-14)20-15(9-21)16(10-27-20)19(24)11-3-4-17(23)18(7-11)26-2/h3-8,15-16,20-23H,9-10H2,1-2H3/t15-,16-,20+/m0/s1
SMILES:	COc1cc(O)cc(c1)[C@H]1OC[C@@H]([C@@H]1CO)C(=O)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL257069
PubChem CID:	44453412
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003422] 7,9'-epoxylignans

*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
NPO30739	Forsythia suspense	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT857	Cell Line	LLC-PK1	Sus scrofa	Activity	=	95.0	%	PMID[461058]

☑ 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 NPC25127 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	372
0.1-0.2	1281
0.2-0.3	3081
0.3-0.4	7629
0.4-0.5	10570
0.5-0.6	4227
0.6-0.7	5074
0.7-0.8	7216
0.8-0.85	2666
0.85-0.9	558
0.9-0.95	19
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC287504
0.9863	High Similarity	NPC151425
0.966	High Similarity	NPC62354
0.9658	High Similarity	NPC474903
0.9452	High Similarity	NPC30890
0.9315	High Similarity	NPC239608
0.9315	High Similarity	NPC46161
0.9295	High Similarity	NPC475738
0.9281	High Similarity	NPC129684
0.9281	High Similarity	NPC299520
0.9231	High Similarity	NPC124038
0.9172	High Similarity	NPC472277
0.9161	High Similarity	NPC472962
0.9161	High Similarity	NPC472961
0.915	High Similarity	NPC255807
0.915	High Similarity	NPC31018
0.9139	High Similarity	NPC472279
0.9122	High Similarity	NPC207732
0.9114	High Similarity	NPC235610
0.9108	High Similarity	NPC18100
0.9108	High Similarity	NPC205265
0.9108	High Similarity	NPC472281
0.9085	High Similarity	NPC124714
0.9085	High Similarity	NPC18727
0.9085	High Similarity	NPC469550
0.9079	High Similarity	NPC75695
0.9073	High Similarity	NPC92722
0.9073	High Similarity	NPC264550
0.9073	High Similarity	NPC102003
0.9073	High Similarity	NPC69430
0.9073	High Similarity	NPC40290
0.9073	High Similarity	NPC264289
0.9073	High Similarity	NPC195763
0.9073	High Similarity	NPC142876
0.9073	High Similarity	NPC200060
0.9073	High Similarity	NPC333691
0.9073	High Similarity	NPC139293
0.9057	High Similarity	NPC247973
0.9051	High Similarity	NPC300053
0.9051	High Similarity	NPC108433
0.9045	High Similarity	NPC472964
0.9045	High Similarity	NPC472635
0.9045	High Similarity	NPC84515
0.9045	High Similarity	NPC312056
0.9045	High Similarity	NPC76687
0.9045	High Similarity	NPC81679
0.9041	High Similarity	NPC4796
0.9038	High Similarity	NPC472624
0.9038	High Similarity	NPC328102
0.9038	High Similarity	NPC472902
0.9032	High Similarity	NPC472598
0.9032	High Similarity	NPC48208
0.9032	High Similarity	NPC210084
0.9032	High Similarity	NPC190020
0.9032	High Similarity	NPC162869
0.9032	High Similarity	NPC472911
0.9032	High Similarity	NPC77679
0.9032	High Similarity	NPC472914
0.9032	High Similarity	NPC245758
0.9032	High Similarity	NPC99597
0.9032	High Similarity	NPC475267
0.9032	High Similarity	NPC52530
0.9032	High Similarity	NPC84935
0.9032	High Similarity	NPC156057
0.9032	High Similarity	NPC291508
0.9032	High Similarity	NPC474055
0.9032	High Similarity	NPC96167
0.9032	High Similarity	NPC222814
0.9032	High Similarity	NPC474836
0.9032	High Similarity	NPC472913
0.9032	High Similarity	NPC472910
0.9032	High Similarity	NPC181960
0.9032	High Similarity	NPC469584
0.9032	High Similarity	NPC470402
0.9032	High Similarity	NPC474208
0.9026	High Similarity	NPC79998
0.9026	High Similarity	NPC180901
0.9026	High Similarity	NPC300757
0.902	High Similarity	NPC100971
0.902	High Similarity	NPC121522
0.902	High Similarity	NPC260979
0.902	High Similarity	NPC236637
0.902	High Similarity	NPC302950
0.902	High Similarity	NPC291802
0.902	High Similarity	NPC131266
0.902	High Similarity	NPC209487
0.902	High Similarity	NPC60972
0.902	High Similarity	NPC269451
0.902	High Similarity	NPC472912
0.902	High Similarity	NPC477231
0.902	High Similarity	NPC257648
0.902	High Similarity	NPC181209
0.902	High Similarity	NPC35763
0.902	High Similarity	NPC39732
0.902	High Similarity	NPC324233
0.902	High Similarity	NPC323626
0.902	High Similarity	NPC100263
0.902	High Similarity	NPC245382
0.902	High Similarity	NPC216769
0.902	High Similarity	NPC219582
0.9007	High Similarity	NPC203747
0.9007	High Similarity	NPC194653
0.9007	High Similarity	NPC131451
0.9007	High Similarity	NPC80710
0.9007	High Similarity	NPC15329
0.9007	High Similarity	NPC139364
0.9007	High Similarity	NPC254702
0.9007	High Similarity	NPC287395
0.9007	High Similarity	NPC183655
0.9	High Similarity	NPC165389
0.9	High Similarity	NPC288813
0.8994	High Similarity	NPC119589
0.8994	High Similarity	NPC43065
0.8994	High Similarity	NPC128293
0.8993	High Similarity	NPC142165
0.8987	High Similarity	NPC475985
0.8986	High Similarity	NPC312256
0.8981	High Similarity	NPC188486
0.8981	High Similarity	NPC308992
0.8974	High Similarity	NPC195832
0.8974	High Similarity	NPC55738
0.8968	High Similarity	NPC472916
0.8968	High Similarity	NPC195796
0.8968	High Similarity	NPC291878
0.8968	High Similarity	NPC469474
0.8968	High Similarity	NPC150227
0.8968	High Similarity	NPC255106
0.8968	High Similarity	NPC35038
0.8968	High Similarity	NPC278778
0.8968	High Similarity	NPC317383
0.8968	High Similarity	NPC13858
0.8968	High Similarity	NPC320825
0.8968	High Similarity	NPC235165
0.8968	High Similarity	NPC326037
0.8961	High Similarity	NPC250557
0.8954	High Similarity	NPC267091
0.8954	High Similarity	NPC45291
0.8954	High Similarity	NPC31363
0.8954	High Similarity	NPC262623
0.8954	High Similarity	NPC272566
0.8954	High Similarity	NPC19980
0.8954	High Similarity	NPC256406
0.8954	High Similarity	NPC476434
0.8947	High Similarity	NPC473091
0.8944	High Similarity	NPC102277
0.8944	High Similarity	NPC212748
0.8944	High Similarity	NPC131866
0.8944	High Similarity	NPC279209
0.894	High Similarity	NPC125449
0.894	High Similarity	NPC119660
0.894	High Similarity	NPC93034
0.894	High Similarity	NPC188074
0.8933	High Similarity	NPC9370
0.8933	High Similarity	NPC213482
0.8933	High Similarity	NPC157133
0.8933	High Similarity	NPC287495
0.8931	High Similarity	NPC326520
0.8926	High Similarity	NPC471417
0.8926	High Similarity	NPC287722
0.8926	High Similarity	NPC254659
0.8926	High Similarity	NPC119663
0.8924	High Similarity	NPC474162
0.8924	High Similarity	NPC272722
0.8924	High Similarity	NPC474033
0.8924	High Similarity	NPC474034
0.8924	High Similarity	NPC476247
0.8924	High Similarity	NPC474150
0.8919	High Similarity	NPC110419
0.8917	High Similarity	NPC282009
0.8917	High Similarity	NPC476283
0.8917	High Similarity	NPC263449
0.8917	High Similarity	NPC36217
0.8917	High Similarity	NPC287328
0.8917	High Similarity	NPC470183
0.8912	High Similarity	NPC474784
0.891	High Similarity	NPC27337
0.891	High Similarity	NPC471515
0.891	High Similarity	NPC471479
0.891	High Similarity	NPC67876
0.891	High Similarity	NPC78103
0.8903	High Similarity	NPC16082
0.8903	High Similarity	NPC67396
0.8903	High Similarity	NPC45849
0.8903	High Similarity	NPC200761
0.8903	High Similarity	NPC130589
0.8903	High Similarity	NPC57674
0.8903	High Similarity	NPC37392
0.8903	High Similarity	NPC477503
0.8903	High Similarity	NPC20830
0.8903	High Similarity	NPC230149
0.8903	High Similarity	NPC82592
0.8903	High Similarity	NPC39184
0.8903	High Similarity	NPC321779
0.8903	High Similarity	NPC168247
0.8903	High Similarity	NPC199926
0.8903	High Similarity	NPC152951
0.8903	High Similarity	NPC256612
0.8903	High Similarity	NPC472909
0.8903	High Similarity	NPC117992
0.8903	High Similarity	NPC134287

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 NPC25127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	798
0.2-0.3	1660
0.3-0.4	2583
0.4-0.5	2038
0.5-0.6	1086
0.6-0.7	493
0.7-0.8	141
0.8-0.85	24
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD3882	Suspended
0.902	High Similarity	NPD1934	Approved
0.8938	High Similarity	NPD3818	Discontinued
0.8839	High Similarity	NPD2801	Approved
0.8839	High Similarity	NPD2393	Clinical (unspecified phase)
0.8696	High Similarity	NPD6167	Clinical (unspecified phase)
0.8696	High Similarity	NPD6168	Clinical (unspecified phase)
0.8696	High Similarity	NPD6166	Phase 2
0.8679	High Similarity	NPD5494	Approved
0.8526	High Similarity	NPD4380	Phase 2
0.8497	Intermediate Similarity	NPD1511	Approved
0.8491	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD7074	Phase 3
0.8424	Intermediate Similarity	NPD7054	Approved
0.8387	Intermediate Similarity	NPD1512	Approved
0.8373	Intermediate Similarity	NPD7472	Approved
0.8356	Intermediate Similarity	NPD3027	Phase 3
0.8313	Intermediate Similarity	NPD3817	Phase 2
0.8303	Intermediate Similarity	NPD7473	Discontinued
0.8255	Intermediate Similarity	NPD230	Phase 1
0.8232	Intermediate Similarity	NPD6232	Discontinued
0.8225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6797	Phase 2
0.8212	Intermediate Similarity	NPD1510	Phase 2
0.821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD943	Approved
0.8188	Intermediate Similarity	NPD1240	Approved
0.817	Intermediate Similarity	NPD1549	Phase 2
0.8166	Intermediate Similarity	NPD7251	Discontinued
0.816	Intermediate Similarity	NPD6234	Discontinued
0.8118	Intermediate Similarity	NPD7808	Phase 3
0.8107	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7075	Discontinued
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8089	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1607	Approved
0.8075	Intermediate Similarity	NPD37	Approved
0.8072	Intermediate Similarity	NPD3926	Phase 2
0.8065	Intermediate Similarity	NPD4628	Phase 3
0.8039	Intermediate Similarity	NPD2796	Approved
0.8037	Intermediate Similarity	NPD4967	Phase 2
0.8037	Intermediate Similarity	NPD4966	Approved
0.8037	Intermediate Similarity	NPD4965	Approved
0.8025	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1465	Phase 2
0.8025	Intermediate Similarity	NPD6799	Approved
0.7977	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7975	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD9494	Approved
0.7963	Intermediate Similarity	NPD6801	Discontinued
0.7953	Intermediate Similarity	NPD7685	Pre-registration
0.7953	Intermediate Similarity	NPD6559	Discontinued
0.7952	Intermediate Similarity	NPD1247	Approved
0.795	Intermediate Similarity	NPD6599	Discontinued
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7228	Approved
0.7914	Intermediate Similarity	NPD7819	Suspended
0.7911	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6190	Approved
0.7866	Intermediate Similarity	NPD5402	Approved
0.7844	Intermediate Similarity	NPD7199	Phase 2
0.7831	Intermediate Similarity	NPD919	Approved
0.7829	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2800	Approved
0.7751	Intermediate Similarity	NPD5242	Approved
0.775	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6959	Discontinued
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7683	Intermediate Similarity	NPD7411	Suspended
0.7665	Intermediate Similarity	NPD3749	Approved
0.7654	Intermediate Similarity	NPD5403	Approved
0.7651	Intermediate Similarity	NPD5353	Approved
0.7647	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2344	Approved
0.764	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8434	Phase 2
0.761	Intermediate Similarity	NPD3750	Approved
0.761	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD447	Suspended
0.7546	Intermediate Similarity	NPD920	Approved
0.7531	Intermediate Similarity	NPD5401	Approved
0.7517	Intermediate Similarity	NPD9269	Phase 2
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7768	Phase 2
0.747	Intermediate Similarity	NPD6386	Approved
0.747	Intermediate Similarity	NPD6385	Approved
0.7469	Intermediate Similarity	NPD4357	Discontinued
0.7468	Intermediate Similarity	NPD1551	Phase 2
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2309	Approved
0.7443	Intermediate Similarity	NPD7240	Approved
0.7438	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2799	Discontinued
0.7394	Intermediate Similarity	NPD1653	Approved
0.7389	Intermediate Similarity	NPD6651	Approved
0.7384	Intermediate Similarity	NPD3787	Discontinued
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.7366	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6100	Approved
0.7358	Intermediate Similarity	NPD6099	Approved
0.7355	Intermediate Similarity	NPD3764	Approved
0.7347	Intermediate Similarity	NPD5536	Phase 2
0.7329	Intermediate Similarity	NPD1243	Approved
0.7318	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7266	Discontinued
0.7301	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3748	Approved
0.7288	Intermediate Similarity	NPD5953	Discontinued
0.7285	Intermediate Similarity	NPD1608	Approved
0.7285	Intermediate Similarity	NPD3972	Approved
0.7284	Intermediate Similarity	NPD4110	Phase 3
0.7284	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5761	Phase 2
0.7278	Intermediate Similarity	NPD5760	Phase 2
0.7273	Intermediate Similarity	NPD7286	Phase 2
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7248	Intermediate Similarity	NPD9268	Approved
0.7246	Intermediate Similarity	NPD3226	Approved
0.7238	Intermediate Similarity	NPD8150	Discontinued
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7225	Intermediate Similarity	NPD8127	Discontinued
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7212	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2798	Approved
0.72	Intermediate Similarity	NPD2403	Approved
0.7193	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5283	Phase 1
0.719	Intermediate Similarity	NPD1876	Approved
0.7188	Intermediate Similarity	NPD7033	Discontinued
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD9545	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7178	Intermediate Similarity	NPD8166	Discontinued
0.7178	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6273	Approved
0.7152	Intermediate Similarity	NPD3620	Phase 2
0.7152	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7390	Discontinued
0.715	Intermediate Similarity	NPD8151	Discontinued
0.7143	Intermediate Similarity	NPD3455	Phase 2
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD5978	Approved
0.7135	Intermediate Similarity	NPD5977	Approved
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.7119	Intermediate Similarity	NPD2163	Approved
0.7117	Intermediate Similarity	NPD2654	Approved
0.7107	Intermediate Similarity	NPD1933	Approved
0.7105	Intermediate Similarity	NPD1610	Phase 2
0.7099	Intermediate Similarity	NPD2346	Discontinued
0.7099	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4360	Phase 2
0.7097	Intermediate Similarity	NPD4363	Phase 3
0.7097	Intermediate Similarity	NPD5647	Approved
0.7086	Intermediate Similarity	NPD17	Approved
0.7068	Intermediate Similarity	NPD7680	Approved
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7059	Intermediate Similarity	NPD4361	Phase 2
0.7059	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7038	Approved
0.7056	Intermediate Similarity	NPD7039	Approved
0.7055	Intermediate Similarity	NPD228	Approved
0.7055	Intermediate Similarity	NPD2424	Discontinued
0.7051	Intermediate Similarity	NPD2861	Phase 2
0.7051	Intermediate Similarity	NPD3018	Phase 2
0.7041	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1203	Approved
0.7025	Intermediate Similarity	NPD2313	Discontinued
0.7025	Intermediate Similarity	NPD3268	Approved
0.7021	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4575	Clinical (unspecified phase)

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