NPASS Compound

Structure

CID166137 OpenBabel06191715532D 26 29 0 0 1 0 0 0 0 0999 V2000 2.0981 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7248 2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9328 3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4190 2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2851 5.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8838 4.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6270 3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 5.5388 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 -3.2905 5.1081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4930 4.0254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 5 2 0 0 0 0 3 13 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 11 26 1 0 0 0 0 14 6 1 1 0 0 0 14 15 1 0 0 0 0 15 7 1 6 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 20 22 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	354.536
LogP:	3.197
LogD:	3.238
LogS:	-4.607
# Rotatable Bonds:	5
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	3.192
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.851
MDCK Permeability:	2.4484068489982747e-05
Pgp-inhibitor:	0.385
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	97.83270263671875%
Volume Distribution (VD):	0.756
Pgp-substrate:	3.194699764251709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.599
CYP2C19-inhibitor:	0.977
CYP2C19-substrate:	0.387
CYP2C9-inhibitor:	0.906
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.982
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.969
CYP3A4-substrate:	0.702

ADMET: Excretion

Clearance (CL):	17.836
Half-life (T1/2):	0.484

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.375
Drug-inuced Liver Injury (DILI):	0.735
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.666
Skin Sensitization:	0.87
Carcinogencity:	0.799
Eye Corrosion:	0.003
Eye Irritation:	0.32
Respiratory Toxicity:	0.365

Download Data

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

Natural Product: NPC166137

Natural Product ID:	NPC166137
*Common Name:**	NFAAULYTGYCSKM-LSDHHAIUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NFAAULYTGYCSKM-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-23-18-8-12(2-4-16(18)21)6-14-10-24-20(22)15(14)7-13-3-5-17-19(9-13)26-11-25-17/h2-5,8-9,14-15,21H,6-7,10-11H2,1H3/t14-,15+/m0/s1
SMILES:	COc1cc(ccc1O)C[C@H]1COC(=O)[C@@H]1Cc1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3309442
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

*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
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9031	Euonymus europaeus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9031	Euonymus europaeus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28392	Macrosiphum liriodendri	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28510	Aspergillus pseudodeflectus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO617	Vicia balansae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9031	Euonymus europaeus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO103	Stereocaulon salazinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1040	Ficus conraui	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28218	Asplenium adiantum-nigrum	Species	Aspleniaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	273.0	nM	PMID[534769]

☑ 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 NPC166137 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	289
0.1-0.2	1266
0.2-0.3	2844
0.3-0.4	7494
0.4-0.5	11770
0.5-0.6	4377
0.6-0.7	10670
0.7-0.8	3503
0.8-0.85	342
0.85-0.9	106
0.9-0.95	34
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC282291
0.9549	High Similarity	NPC5310
0.9549	High Similarity	NPC300776
0.9549	High Similarity	NPC4982
0.9549	High Similarity	NPC176814
0.9549	High Similarity	NPC68779
0.9489	High Similarity	NPC52664
0.9474	High Similarity	NPC205915
0.9433	High Similarity	NPC145569
0.9433	High Similarity	NPC216223
0.9296	High Similarity	NPC474965
0.9296	High Similarity	NPC293757
0.9296	High Similarity	NPC477695
0.9296	High Similarity	NPC668
0.9296	High Similarity	NPC174512
0.9265	High Similarity	NPC90431
0.9259	High Similarity	NPC19890
0.9259	High Similarity	NPC110958
0.9167	High Similarity	NPC477700
0.9149	High Similarity	NPC223185
0.9137	High Similarity	NPC100675
0.9137	High Similarity	NPC29599
0.9103	High Similarity	NPC477699
0.9085	High Similarity	NPC3982
0.9071	High Similarity	NPC253481
0.9071	High Similarity	NPC31751
0.9071	High Similarity	NPC253722
0.9051	High Similarity	NPC113295
0.9044	High Similarity	NPC169973
0.9034	High Similarity	NPC32079
0.9023	High Similarity	NPC223807
0.9007	High Similarity	NPC273657
0.9007	High Similarity	NPC106920
0.8986	High Similarity	NPC478055
0.8986	High Similarity	NPC102260
0.8986	High Similarity	NPC230968
0.898	High Similarity	NPC136757
0.898	High Similarity	NPC103197
0.898	High Similarity	NPC30009
0.8963	High Similarity	NPC275950
0.8947	High Similarity	NPC274356
0.8944	High Similarity	NPC46880
0.8936	High Similarity	NPC176586
0.8936	High Similarity	NPC210354
0.8913	High Similarity	NPC135777
0.8913	High Similarity	NPC142547
0.8912	High Similarity	NPC61604
0.8912	High Similarity	NPC299706
0.8912	High Similarity	NPC245615
0.8912	High Similarity	NPC115466
0.8897	High Similarity	NPC476345
0.8889	High Similarity	NPC241354
0.8889	High Similarity	NPC476748
0.8873	High Similarity	NPC477697
0.8873	High Similarity	NPC477696
0.8873	High Similarity	NPC470811
0.8872	High Similarity	NPC280767
0.8865	High Similarity	NPC162851
0.8865	High Similarity	NPC218092
0.8865	High Similarity	NPC246474
0.8844	High Similarity	NPC56184
0.8824	High Similarity	NPC173308
0.8824	High Similarity	NPC181079
0.8811	High Similarity	NPC191158
0.8811	High Similarity	NPC177644
0.8803	High Similarity	NPC151423
0.8803	High Similarity	NPC40237
0.88	High Similarity	NPC163527
0.88	High Similarity	NPC115281
0.88	High Similarity	NPC181168
0.8792	High Similarity	NPC38699
0.8786	High Similarity	NPC281780
0.8767	High Similarity	NPC125570
0.8767	High Similarity	NPC477698
0.875	High Similarity	NPC477702
0.8733	High Similarity	NPC163635
0.8732	High Similarity	NPC28398
0.8731	High Similarity	NPC53305
0.8731	High Similarity	NPC257589
0.8723	High Similarity	NPC123526
0.8723	High Similarity	NPC193666
0.8723	High Similarity	NPC88640
0.8722	High Similarity	NPC317769
0.8722	High Similarity	NPC249788
0.8722	High Similarity	NPC31344
0.8707	High Similarity	NPC158635
0.8707	High Similarity	NPC229882
0.8705	High Similarity	NPC67247
0.8696	High Similarity	NPC471505
0.8696	High Similarity	NPC106739
0.869	High Similarity	NPC212890
0.8684	High Similarity	NPC150943
0.8684	High Similarity	NPC91634
0.8684	High Similarity	NPC268718
0.8681	High Similarity	NPC475000
0.8681	High Similarity	NPC218841
0.8681	High Similarity	NPC92693
0.8676	High Similarity	NPC226661
0.8667	High Similarity	NPC213711
0.8667	High Similarity	NPC92207
0.8667	High Similarity	NPC40352
0.8667	High Similarity	NPC186316
0.8667	High Similarity	NPC127937
0.8662	High Similarity	NPC147379
0.8658	High Similarity	NPC473236
0.8652	High Similarity	NPC52968
0.8652	High Similarity	NPC231719
0.8652	High Similarity	NPC308976
0.8649	High Similarity	NPC164082
0.8643	High Similarity	NPC477301
0.8643	High Similarity	NPC101624
0.8643	High Similarity	NPC184938
0.8618	High Similarity	NPC76211
0.8611	High Similarity	NPC474288
0.8582	High Similarity	NPC471988
0.8571	High Similarity	NPC301641
0.8571	High Similarity	NPC177291
0.8571	High Similarity	NPC80241
0.8571	High Similarity	NPC76687
0.8571	High Similarity	NPC194416
0.8562	High Similarity	NPC193779
0.8561	High Similarity	NPC104077
0.8561	High Similarity	NPC227002
0.8561	High Similarity	NPC147616
0.8561	High Similarity	NPC219671
0.8561	High Similarity	NPC259742
0.8552	High Similarity	NPC27159
0.8551	High Similarity	NPC171550
0.8551	High Similarity	NPC311419
0.8551	High Similarity	NPC134764
0.8551	High Similarity	NPC319282
0.8551	High Similarity	NPC65935
0.8551	High Similarity	NPC123196
0.8551	High Similarity	NPC137427
0.8551	High Similarity	NPC275724
0.8551	High Similarity	NPC215941
0.8551	High Similarity	NPC244246
0.8531	High Similarity	NPC177868
0.8529	High Similarity	NPC120225
0.8529	High Similarity	NPC303680
0.8529	High Similarity	NPC84076
0.8529	High Similarity	NPC90128
0.8529	High Similarity	NPC213552
0.8516	High Similarity	NPC116759
0.8516	High Similarity	NPC14294
0.8511	High Similarity	NPC211386
0.8511	High Similarity	NPC470990
0.8503	High Similarity	NPC304687
0.8503	High Similarity	NPC80230
0.8503	High Similarity	NPC104024
0.8503	High Similarity	NPC101755
0.8503	High Similarity	NPC65574
0.8493	Intermediate Similarity	NPC327052
0.8489	Intermediate Similarity	NPC161557
0.8489	Intermediate Similarity	NPC27843
0.8489	Intermediate Similarity	NPC40432
0.8489	Intermediate Similarity	NPC7171
0.8489	Intermediate Similarity	NPC115207
0.8489	Intermediate Similarity	NPC228346
0.8489	Intermediate Similarity	NPC158079
0.8487	Intermediate Similarity	NPC237946
0.8487	Intermediate Similarity	NPC32373
0.8483	Intermediate Similarity	NPC255566
0.8483	Intermediate Similarity	NPC298317
0.8483	Intermediate Similarity	NPC477898
0.8483	Intermediate Similarity	NPC265154
0.8478	Intermediate Similarity	NPC304622
0.8472	Intermediate Similarity	NPC323601
0.8467	Intermediate Similarity	NPC5018
0.8467	Intermediate Similarity	NPC151167
0.8467	Intermediate Similarity	NPC123228
0.8467	Intermediate Similarity	NPC476434
0.8467	Intermediate Similarity	NPC276466
0.8467	Intermediate Similarity	NPC123722
0.8467	Intermediate Similarity	NPC158737
0.8462	Intermediate Similarity	NPC284409
0.8456	Intermediate Similarity	NPC261322
0.8456	Intermediate Similarity	NPC289459
0.8456	Intermediate Similarity	NPC3221
0.8444	Intermediate Similarity	NPC163083
0.8435	Intermediate Similarity	NPC472560
0.8433	Intermediate Similarity	NPC201777
0.8431	Intermediate Similarity	NPC207584
0.8431	Intermediate Similarity	NPC19947
0.8429	Intermediate Similarity	NPC207400
0.8429	Intermediate Similarity	NPC181049
0.8425	Intermediate Similarity	NPC84181
0.8421	Intermediate Similarity	NPC232316
0.8421	Intermediate Similarity	NPC95614
0.8421	Intermediate Similarity	NPC344161
0.8421	Intermediate Similarity	NPC227217
0.8421	Intermediate Similarity	NPC238834
0.8421	Intermediate Similarity	NPC117780
0.8421	Intermediate Similarity	NPC242885
0.8421	Intermediate Similarity	NPC56214
0.8421	Intermediate Similarity	NPC165133
0.8417	Intermediate Similarity	NPC477694
0.8417	Intermediate Similarity	NPC477705
0.8414	Intermediate Similarity	NPC287124
0.8411	Intermediate Similarity	NPC44730

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 NPC166137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	774
0.2-0.3	1524
0.3-0.4	2512
0.4-0.5	2161
0.5-0.6	1191
0.6-0.7	638
0.7-0.8	94
0.8-0.85	6
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD6234	Discontinued
0.8621	High Similarity	NPD6143	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD4965	Approved
0.8487	Intermediate Similarity	NPD4966	Approved
0.8487	Intermediate Similarity	NPD4967	Phase 2
0.8354	Intermediate Similarity	NPD7228	Approved
0.8289	Intermediate Similarity	NPD37	Approved
0.8163	Intermediate Similarity	NPD4110	Phase 3
0.8163	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7199	Phase 2
0.8112	Intermediate Similarity	NPD6355	Discontinued
0.805	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD7028	Phase 2
0.7917	Intermediate Similarity	NPD4060	Phase 1
0.7895	Intermediate Similarity	NPD5283	Phase 1
0.7844	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7240	Approved
0.781	Intermediate Similarity	NPD1357	Approved
0.7778	Intermediate Similarity	NPD6798	Discontinued
0.777	Intermediate Similarity	NPD3705	Approved
0.7744	Intermediate Similarity	NPD228	Approved
0.773	Intermediate Similarity	NPD1283	Approved
0.7727	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7685	Pre-registration
0.7708	Intermediate Similarity	NPD3027	Phase 3
0.7708	Intermediate Similarity	NPD7095	Approved
0.7692	Intermediate Similarity	NPD9494	Approved
0.7683	Intermediate Similarity	NPD3818	Discontinued
0.7682	Intermediate Similarity	NPD8166	Discontinued
0.7658	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4062	Phase 3
0.7603	Intermediate Similarity	NPD6233	Phase 2
0.76	Intermediate Similarity	NPD7266	Discontinued
0.7594	Intermediate Similarity	NPD3021	Approved
0.7594	Intermediate Similarity	NPD3022	Approved
0.7589	Intermediate Similarity	NPD1608	Approved
0.7566	Intermediate Similarity	NPD4628	Phase 3
0.7562	Intermediate Similarity	NPD3882	Suspended
0.7551	Intermediate Similarity	NPD2979	Phase 3
0.7551	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3620	Phase 2
0.755	Intermediate Similarity	NPD5958	Discontinued
0.7536	Intermediate Similarity	NPD5536	Phase 2
0.7533	Intermediate Similarity	NPD2438	Suspended
0.7518	Intermediate Similarity	NPD1281	Approved
0.7516	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD5647	Approved
0.7482	Intermediate Similarity	NPD1894	Discontinued
0.7458	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6653	Approved
0.7447	Intermediate Similarity	NPD3847	Discontinued
0.7434	Intermediate Similarity	NPD4534	Discontinued
0.7431	Intermediate Similarity	NPD2797	Approved
0.7429	Intermediate Similarity	NPD5585	Approved
0.7417	Intermediate Similarity	NPD2935	Discontinued
0.7412	Intermediate Similarity	NPD7281	Phase 3
0.7412	Intermediate Similarity	NPD7280	Phase 3
0.7403	Intermediate Similarity	NPD6190	Approved
0.74	Intermediate Similarity	NPD7097	Phase 1
0.7394	Intermediate Similarity	NPD1535	Discovery
0.7389	Intermediate Similarity	NPD7680	Approved
0.7381	Intermediate Similarity	NPD7074	Phase 3
0.7376	Intermediate Similarity	NPD17	Approved
0.7375	Intermediate Similarity	NPD1934	Approved
0.7365	Intermediate Similarity	NPD6663	Approved
0.7353	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2799	Discontinued
0.7343	Intermediate Similarity	NPD1481	Phase 2
0.7329	Intermediate Similarity	NPD2801	Approved
0.7321	Intermediate Similarity	NPD7054	Approved
0.7315	Intermediate Similarity	NPD825	Approved
0.7315	Intermediate Similarity	NPD826	Approved
0.7305	Intermediate Similarity	NPD1651	Approved
0.7303	Intermediate Similarity	NPD2531	Phase 2
0.7299	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3268	Approved
0.7297	Intermediate Similarity	NPD3764	Approved
0.7297	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3455	Phase 2
0.7278	Intermediate Similarity	NPD7472	Approved
0.7273	Intermediate Similarity	NPD8127	Discontinued
0.7267	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD1933	Approved
0.7267	Intermediate Similarity	NPD230	Phase 1
0.7248	Intermediate Similarity	NPD8032	Phase 2
0.7233	Intermediate Similarity	NPD1653	Approved
0.7229	Intermediate Similarity	NPD6232	Discontinued
0.7222	Intermediate Similarity	NPD2977	Approved
0.7222	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2978	Approved
0.7222	Intermediate Similarity	NPD8455	Phase 2
0.7215	Intermediate Similarity	NPD6273	Approved
0.7211	Intermediate Similarity	NPD5736	Approved
0.7202	Intermediate Similarity	NPD7473	Discontinued
0.72	Intermediate Similarity	NPD4140	Approved
0.72	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1613	Approved
0.719	Intermediate Similarity	NPD6032	Approved
0.719	Intermediate Similarity	NPD4476	Approved
0.719	Intermediate Similarity	NPD4477	Approved
0.7179	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3817	Phase 2
0.7174	Intermediate Similarity	NPD5535	Approved
0.7172	Intermediate Similarity	NPD4359	Approved
0.7172	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2614	Approved
0.7161	Intermediate Similarity	NPD6674	Discontinued
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6797	Phase 2
0.7133	Intermediate Similarity	NPD4626	Approved
0.7132	Intermediate Similarity	NPD2684	Approved
0.7125	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7296	Approved
0.7117	Intermediate Similarity	NPD1465	Phase 2
0.7114	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6385	Approved
0.7099	Intermediate Similarity	NPD6873	Phase 2
0.7099	Intermediate Similarity	NPD6386	Approved
0.7095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2861	Phase 2
0.7093	Intermediate Similarity	NPD6559	Discontinued
0.7093	Intermediate Similarity	NPD7251	Discontinued
0.7063	Intermediate Similarity	NPD5691	Approved
0.7059	Intermediate Similarity	NPD1358	Approved
0.7052	Intermediate Similarity	NPD7808	Phase 3
0.7051	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7843	Approved
0.7041	Intermediate Similarity	NPD6166	Phase 2
0.7041	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD555	Phase 2
0.7032	Intermediate Similarity	NPD2344	Approved
0.7027	Intermediate Similarity	NPD257	Approved
0.7027	Intermediate Similarity	NPD258	Approved
0.7018	Intermediate Similarity	NPD5844	Phase 1
0.7014	Intermediate Similarity	NPD1778	Approved
0.7014	Intermediate Similarity	NPD3019	Approved
0.7014	Intermediate Similarity	NPD2932	Approved
0.7013	Intermediate Similarity	NPD7033	Discontinued
0.7013	Intermediate Similarity	NPD4108	Discontinued
0.7012	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1876	Approved
0.7006	Intermediate Similarity	NPD6331	Phase 2
0.7006	Intermediate Similarity	NPD7003	Approved
0.7006	Intermediate Similarity	NPD5494	Approved
0.6988	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3134	Approved
0.6984	Remote Similarity	NPD7827	Phase 1
0.6981	Remote Similarity	NPD1511	Approved
0.6974	Remote Similarity	NPD1558	Phase 1
0.6968	Remote Similarity	NPD2161	Phase 2
0.6968	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3496	Discontinued
0.6959	Remote Similarity	NPD987	Approved
0.6959	Remote Similarity	NPD3267	Approved
0.6959	Remote Similarity	NPD3266	Approved
0.6954	Remote Similarity	NPD5111	Phase 2
0.6954	Remote Similarity	NPD5110	Phase 2
0.6954	Remote Similarity	NPD5109	Approved
0.6951	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2629	Approved
0.6946	Remote Similarity	NPD6315	Phase 2
0.6937	Remote Similarity	NPD2532	Approved
0.6937	Remote Similarity	NPD2534	Approved
0.6937	Remote Similarity	NPD2533	Approved
0.6937	Remote Similarity	NPD3146	Approved
0.6937	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4908	Phase 1
0.6928	Remote Similarity	NPD4622	Approved
0.6928	Remote Similarity	NPD5735	Approved
0.6928	Remote Similarity	NPD4618	Approved
0.6923	Remote Similarity	NPD7315	Approved
0.6923	Remote Similarity	NPD7229	Phase 3
0.6923	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD1375	Discontinued
0.6918	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD3020	Approved
0.6914	Remote Similarity	NPD8313	Approved
0.6914	Remote Similarity	NPD8312	Approved
0.6913	Remote Similarity	NPD6584	Phase 3
0.6908	Remote Similarity	NPD259	Phase 1
0.6908	Remote Similarity	NPD4870	Approved
0.6908	Remote Similarity	NPD2674	Phase 3
0.6899	Remote Similarity	NPD1878	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