NPASS Compound

Structure

NPC185777 OpenBabel07101718302D 32 34 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 5.1962 -2.0000 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 5 1 0 0 0 0 2 14 2 0 0 0 0 3 15 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 8 1 0 0 0 0 6 16 2 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 11 22 2 0 0 0 0 12 18 2 0 0 0 0 12 23 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 14 31 1 0 0 0 0 15 24 2 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 17 26 1 0 0 0 0 18 30 1 0 0 0 0 19 10 1 1 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 27 1 0 0 0 0 21 25 2 0 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 0 0 0 0 23 29 2 0 0 0 0 23 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.17
Volume:	450.454
LogP:	4.287
LogD:	3.165
LogS:	-3.683
# Rotatable Bonds:	8
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	3.557
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.938
MDCK Permeability:	1.3517475963453762e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.767
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.541
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	99.53839874267578%
Volume Distribution (VD):	0.355
Pgp-substrate:	1.0838158130645752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.672
CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.888
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.925
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.81
CYP2D6-substrate:	0.827
CYP3A4-inhibitor:	0.739
CYP3A4-substrate:	0.626

ADMET: Excretion

Clearance (CL):	5.511
Half-life (T1/2):	0.523

ADMET: Toxicity

hERG Blockers:	0.168
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.858
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.266
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.061
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.511
Respiratory Toxicity:	0.327

Download Data

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

Natural Product: NPC185777

Natural Product ID:	NPC185777
*Common Name:**	6-[3-[(1R)-3-Ethoxy-1-(4-Hydroxyphenyl)But-3-Enyl]-4,6-Dihydroxy-2-Methylphenyl]-4-Methoxypyran-2-One
IUPAC Name:	6-[3-[(1R)-3-ethoxy-1-(4-hydroxyphenyl)but-3-enyl]-4,6-dihydroxy-2-methylphenyl]-4-methoxypyran-2-one
Synonyms:
Standard InCHIKey:	ILEJZSIVWGEINV-LJQANCHMSA-N
Standard InCHI:	InChI=1S/C25H26O7/c1-5-31-14(2)10-19(16-6-8-17(26)9-7-16)24-15(3)25(21(28)13-20(24)27)22-11-18(30-4)12-23(29)32-22/h6-9,11-13,19,26-28H,2,5,10H2,1,3-4H3/t19-/m1/s1
SMILES:	CCOC(=C)C[C@@H](c1c(O)cc(c(c1C)c1cc(OC)cc(=O)o1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL202694
PubChem CID:	44407788
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	Flowers	Tantempango, Hidalgo, Mexico	2019-May	DOI[10.1007/s11130-020-00822-2]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16297615]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18543151]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24358188]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778246]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	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
Others	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Inhibition	=	42.33	%	PMID[567562]
NPT1	Others	Radical scavenging activity		Inhibition	=	30.33	%	PMID[567562]

☑ 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 NPC185777 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	363
0.1-0.2	1571
0.2-0.3	3577
0.3-0.4	8341
0.4-0.5	10206
0.5-0.6	3595
0.6-0.7	5392
0.7-0.8	5404
0.8-0.85	2636
0.85-0.9	1417
0.9-0.95	187
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.938	High Similarity	NPC191395
0.8865	High Similarity	NPC142863
0.8864	High Similarity	NPC315769
0.8864	High Similarity	NPC32463
0.8849	High Similarity	NPC36732
0.8768	High Similarity	NPC472523
0.8741	High Similarity	NPC131950
0.8741	High Similarity	NPC473107
0.8686	High Similarity	NPC131198
0.8652	High Similarity	NPC475719
0.8652	High Similarity	NPC101255
0.8652	High Similarity	NPC43716
0.8652	High Similarity	NPC86069
0.8633	High Similarity	NPC138149
0.8626	High Similarity	NPC105031
0.8626	High Similarity	NPC113495
0.8605	High Similarity	NPC476633
0.8594	High Similarity	NPC282255
0.8594	High Similarity	NPC3239
0.8582	High Similarity	NPC254000
0.8571	High Similarity	NPC93640
0.8571	High Similarity	NPC219923
0.8571	High Similarity	NPC20631
0.8571	High Similarity	NPC53986
0.8571	High Similarity	NPC38664
0.8561	High Similarity	NPC101894
0.8561	High Similarity	NPC170485
0.8551	High Similarity	NPC474886
0.8529	High Similarity	NPC472524
0.8529	High Similarity	NPC31849
0.8527	High Similarity	NPC102639
0.8519	High Similarity	NPC68205
0.8519	High Similarity	NPC118683
0.8519	High Similarity	NPC164804
0.8519	High Similarity	NPC282508
0.8519	High Similarity	NPC293203
0.8519	High Similarity	NPC244888
0.8519	High Similarity	NPC211413
0.8507	High Similarity	NPC471518
0.8507	High Similarity	NPC471519
0.8507	High Similarity	NPC93962
0.85	High Similarity	NPC155552
0.8496	Intermediate Similarity	NPC257947
0.8496	Intermediate Similarity	NPC66331
0.8496	Intermediate Similarity	NPC243688
0.8489	Intermediate Similarity	NPC278600
0.8489	Intermediate Similarity	NPC137262
0.8489	Intermediate Similarity	NPC144512
0.8489	Intermediate Similarity	NPC47040
0.8489	Intermediate Similarity	NPC35501
0.8489	Intermediate Similarity	NPC37428
0.8485	Intermediate Similarity	NPC168259
0.8462	Intermediate Similarity	NPC471608
0.8456	Intermediate Similarity	NPC194277
0.8456	Intermediate Similarity	NPC476389
0.8451	Intermediate Similarity	NPC471824
0.844	Intermediate Similarity	NPC158634
0.8435	Intermediate Similarity	NPC223720
0.8433	Intermediate Similarity	NPC148366
0.8433	Intermediate Similarity	NPC215300
0.8433	Intermediate Similarity	NPC185066
0.8433	Intermediate Similarity	NPC311293
0.8421	Intermediate Similarity	NPC283049
0.8421	Intermediate Similarity	NPC26879
0.8421	Intermediate Similarity	NPC50315
0.8421	Intermediate Similarity	NPC230479
0.8417	Intermediate Similarity	NPC306365
0.8413	Intermediate Similarity	NPC107240
0.8409	Intermediate Similarity	NPC138248
0.8409	Intermediate Similarity	NPC228503
0.8403	Intermediate Similarity	NPC163846
0.8403	Intermediate Similarity	NPC225173
0.8397	Intermediate Similarity	NPC57199
0.8394	Intermediate Similarity	NPC24913
0.8394	Intermediate Similarity	NPC163557
0.8394	Intermediate Similarity	NPC469610
0.8394	Intermediate Similarity	NPC77196
0.8394	Intermediate Similarity	NPC177712
0.8392	Intermediate Similarity	NPC106126
0.8392	Intermediate Similarity	NPC151607
0.8392	Intermediate Similarity	NPC71739
0.8392	Intermediate Similarity	NPC42540
0.8392	Intermediate Similarity	NPC108994
0.8382	Intermediate Similarity	NPC150011
0.8382	Intermediate Similarity	NPC280653
0.8382	Intermediate Similarity	NPC236014
0.8382	Intermediate Similarity	NPC207892
0.8382	Intermediate Similarity	NPC300875
0.8382	Intermediate Similarity	NPC129784
0.8382	Intermediate Similarity	NPC473309
0.8382	Intermediate Similarity	NPC237424
0.8382	Intermediate Similarity	NPC228369
0.8382	Intermediate Similarity	NPC196765
0.8382	Intermediate Similarity	NPC15543
0.8382	Intermediate Similarity	NPC206224
0.8382	Intermediate Similarity	NPC476166
0.8382	Intermediate Similarity	NPC238168
0.8382	Intermediate Similarity	NPC12875
0.8382	Intermediate Similarity	NPC129106
0.8382	Intermediate Similarity	NPC17343
0.8382	Intermediate Similarity	NPC268917
0.8382	Intermediate Similarity	NPC8899
0.8382	Intermediate Similarity	NPC118114
0.8382	Intermediate Similarity	NPC164574
0.838	Intermediate Similarity	NPC250755
0.8378	Intermediate Similarity	NPC268484
0.837	Intermediate Similarity	NPC134360
0.8369	Intermediate Similarity	NPC310370
0.8369	Intermediate Similarity	NPC472601
0.8369	Intermediate Similarity	NPC470986
0.8369	Intermediate Similarity	NPC183642
0.8369	Intermediate Similarity	NPC472600
0.8369	Intermediate Similarity	NPC170812
0.8369	Intermediate Similarity	NPC155205
0.8358	Intermediate Similarity	NPC473221
0.8358	Intermediate Similarity	NPC53781
0.8357	Intermediate Similarity	NPC32630
0.8357	Intermediate Similarity	NPC279573
0.8346	Intermediate Similarity	NPC278955
0.8346	Intermediate Similarity	NPC102540
0.8346	Intermediate Similarity	NPC188022
0.8346	Intermediate Similarity	NPC103420
0.8346	Intermediate Similarity	NPC244495
0.8346	Intermediate Similarity	NPC285040
0.8346	Intermediate Similarity	NPC471828
0.8346	Intermediate Similarity	NPC293801
0.8346	Intermediate Similarity	NPC105718
0.8346	Intermediate Similarity	NPC471827
0.8346	Intermediate Similarity	NPC17809
0.8346	Intermediate Similarity	NPC93219
0.8345	Intermediate Similarity	NPC50455
0.8345	Intermediate Similarity	NPC26954
0.8345	Intermediate Similarity	NPC125801
0.8345	Intermediate Similarity	NPC38099
0.8345	Intermediate Similarity	NPC81835
0.8333	Intermediate Similarity	NPC225696
0.8333	Intermediate Similarity	NPC315807
0.8333	Intermediate Similarity	NPC296915
0.8333	Intermediate Similarity	NPC50896
0.8333	Intermediate Similarity	NPC326600
0.8333	Intermediate Similarity	NPC223008
0.8333	Intermediate Similarity	NPC97834
0.8333	Intermediate Similarity	NPC204353
0.8333	Intermediate Similarity	NPC115335
0.8333	Intermediate Similarity	NPC198154
0.8322	Intermediate Similarity	NPC471731
0.8322	Intermediate Similarity	NPC159721
0.8322	Intermediate Similarity	NPC478202
0.8322	Intermediate Similarity	NPC87883
0.8321	Intermediate Similarity	NPC13005
0.8321	Intermediate Similarity	NPC19157
0.8321	Intermediate Similarity	NPC469611
0.8311	Intermediate Similarity	NPC475141
0.831	Intermediate Similarity	NPC472603
0.831	Intermediate Similarity	NPC472605
0.831	Intermediate Similarity	NPC472604
0.831	Intermediate Similarity	NPC53649
0.8309	Intermediate Similarity	NPC27187
0.8309	Intermediate Similarity	NPC470225
0.8298	Intermediate Similarity	NPC71903
0.8298	Intermediate Similarity	NPC88269
0.8298	Intermediate Similarity	NPC32360
0.8296	Intermediate Similarity	NPC38017
0.8296	Intermediate Similarity	NPC274717
0.8295	Intermediate Similarity	NPC131118
0.8288	Intermediate Similarity	NPC474347
0.8288	Intermediate Similarity	NPC474393
0.8286	Intermediate Similarity	NPC70380
0.8286	Intermediate Similarity	NPC194579
0.8284	Intermediate Similarity	NPC82299
0.8284	Intermediate Similarity	NPC276212
0.8281	Intermediate Similarity	NPC123559
0.8276	Intermediate Similarity	NPC178129
0.8276	Intermediate Similarity	NPC51513
0.8276	Intermediate Similarity	NPC202112
0.8273	Intermediate Similarity	NPC15109
0.8273	Intermediate Similarity	NPC258780
0.8273	Intermediate Similarity	NPC313081
0.8273	Intermediate Similarity	NPC125579
0.8273	Intermediate Similarity	NPC37410
0.8273	Intermediate Similarity	NPC11727
0.8271	Intermediate Similarity	NPC27671
0.8271	Intermediate Similarity	NPC140521
0.8271	Intermediate Similarity	NPC134195
0.8271	Intermediate Similarity	NPC106914
0.8271	Intermediate Similarity	NPC197351
0.8271	Intermediate Similarity	NPC86502
0.8271	Intermediate Similarity	NPC201667
0.8271	Intermediate Similarity	NPC246648
0.8271	Intermediate Similarity	NPC10154
0.8271	Intermediate Similarity	NPC73413
0.8271	Intermediate Similarity	NPC265413
0.8264	Intermediate Similarity	NPC469701
0.8264	Intermediate Similarity	NPC295696
0.8261	Intermediate Similarity	NPC141822
0.8261	Intermediate Similarity	NPC241165
0.8261	Intermediate Similarity	NPC205797
0.8261	Intermediate Similarity	NPC469965
0.8261	Intermediate Similarity	NPC142563
0.8261	Intermediate Similarity	NPC92805

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 NPC185777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	963
0.2-0.3	1553
0.3-0.4	2501
0.4-0.5	1976
0.5-0.6	1149
0.6-0.7	457
0.7-0.8	151
0.8-0.85	49
0.85-0.9	17
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8444	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD4060	Phase 1
0.8296	Intermediate Similarity	NPD4908	Phase 1
0.8261	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD5124	Phase 1
0.8235	Intermediate Similarity	NPD4625	Phase 3
0.8182	Intermediate Similarity	NPD422	Phase 1
0.8182	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD1610	Phase 2
0.8169	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD4626	Approved
0.8133	Intermediate Similarity	NPD7819	Suspended
0.8092	Intermediate Similarity	NPD5691	Approved
0.8015	Intermediate Similarity	NPD1548	Phase 1
0.7931	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2534	Approved
0.7838	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2532	Approved
0.7838	Intermediate Similarity	NPD2533	Approved
0.7832	Intermediate Similarity	NPD3748	Approved
0.781	Intermediate Similarity	NPD2797	Approved
0.7794	Intermediate Similarity	NPD4749	Approved
0.7792	Intermediate Similarity	NPD7768	Phase 2
0.7786	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7771	Intermediate Similarity	NPD6232	Discontinued
0.7754	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7473	Discontinued
0.7714	Intermediate Similarity	NPD3027	Phase 3
0.7712	Intermediate Similarity	NPD37	Approved
0.7708	Intermediate Similarity	NPD1510	Phase 2
0.7698	Intermediate Similarity	NPD2861	Phase 2
0.7692	Intermediate Similarity	NPD6234	Discontinued
0.7677	Intermediate Similarity	NPD4965	Approved
0.7677	Intermediate Similarity	NPD4966	Approved
0.7677	Intermediate Similarity	NPD4967	Phase 2
0.7676	Intermediate Similarity	NPD1613	Approved
0.7676	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD3764	Approved
0.766	Intermediate Similarity	NPD3268	Approved
0.7658	Intermediate Similarity	NPD7229	Phase 3
0.7647	Intermediate Similarity	NPD7411	Suspended
0.7643	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5844	Phase 1
0.7628	Intermediate Similarity	NPD7075	Discontinued
0.7619	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1283	Approved
0.7597	Intermediate Similarity	NPD4750	Phase 3
0.7582	Intermediate Similarity	NPD4380	Phase 2
0.7571	Intermediate Similarity	NPD5736	Approved
0.7571	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4140	Approved
0.7548	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD5408	Approved
0.7534	Intermediate Similarity	NPD5406	Approved
0.7534	Intermediate Similarity	NPD6099	Approved
0.7534	Intermediate Similarity	NPD5405	Approved
0.7534	Intermediate Similarity	NPD6100	Approved
0.7534	Intermediate Similarity	NPD5404	Approved
0.7532	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7484	Intermediate Similarity	NPD6801	Discontinued
0.7484	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD6959	Discontinued
0.7483	Intermediate Similarity	NPD7266	Discontinued
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5762	Approved
0.7483	Intermediate Similarity	NPD5763	Approved
0.7483	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3225	Approved
0.7466	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD846	Approved
0.746	Intermediate Similarity	NPD940	Approved
0.7453	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1653	Approved
0.745	Intermediate Similarity	NPD7003	Approved
0.7445	Intermediate Similarity	NPD3496	Discontinued
0.7432	Intermediate Similarity	NPD1549	Phase 2
0.7431	Intermediate Similarity	NPD2979	Phase 3
0.7431	Intermediate Similarity	NPD1240	Approved
0.7415	Intermediate Similarity	NPD1551	Phase 2
0.7415	Intermediate Similarity	NPD2796	Approved
0.7397	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1281	Approved
0.7391	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1611	Approved
0.7389	Intermediate Similarity	NPD3817	Phase 2
0.7381	Intermediate Similarity	NPD1242	Phase 1
0.7379	Intermediate Similarity	NPD230	Phase 1
0.7372	Intermediate Similarity	NPD1934	Approved
0.7368	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7228	Approved
0.7361	Intermediate Similarity	NPD6663	Approved
0.7351	Intermediate Similarity	NPD6667	Approved
0.7351	Intermediate Similarity	NPD6666	Approved
0.7347	Intermediate Similarity	NPD2799	Discontinued
0.7347	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD1608	Approved
0.7333	Intermediate Similarity	NPD3892	Phase 2
0.7333	Intermediate Similarity	NPD8166	Discontinued
0.7333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1607	Approved
0.7329	Intermediate Similarity	NPD4097	Suspended
0.7325	Intermediate Similarity	NPD2801	Approved
0.7305	Intermediate Similarity	NPD3266	Approved
0.7305	Intermediate Similarity	NPD3267	Approved
0.7303	Intermediate Similarity	NPD6799	Approved
0.7303	Intermediate Similarity	NPD1511	Approved
0.7303	Intermediate Similarity	NPD7390	Discontinued
0.7302	Intermediate Similarity	NPD3020	Approved
0.7297	Intermediate Similarity	NPD4476	Approved
0.7297	Intermediate Similarity	NPD2438	Suspended
0.7297	Intermediate Similarity	NPD4477	Approved
0.7296	Intermediate Similarity	NPD3749	Approved
0.7293	Intermediate Similarity	NPD5535	Approved
0.7293	Intermediate Similarity	NPD7635	Approved
0.729	Intermediate Similarity	NPD3226	Approved
0.7278	Intermediate Similarity	NPD4288	Approved
0.7273	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4340	Discontinued
0.726	Intermediate Similarity	NPD6355	Discontinued
0.7255	Intermediate Similarity	NPD7447	Phase 1
0.7248	Intermediate Similarity	NPD2346	Discontinued
0.7246	Intermediate Similarity	NPD7549	Discontinued
0.7244	Intermediate Similarity	NPD6599	Discontinued
0.7231	Intermediate Similarity	NPD3134	Approved
0.723	Intermediate Similarity	NPD4108	Discontinued
0.7226	Intermediate Similarity	NPD3091	Approved
0.7226	Intermediate Similarity	NPD9545	Approved
0.7222	Intermediate Similarity	NPD5711	Approved
0.7222	Intermediate Similarity	NPD7095	Approved
0.7222	Intermediate Similarity	NPD5710	Approved
0.7219	Intermediate Similarity	NPD4628	Phase 3
0.7215	Intermediate Similarity	NPD1465	Phase 2
0.7211	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1512	Approved
0.7208	Intermediate Similarity	NPD6273	Approved
0.7203	Intermediate Similarity	NPD3018	Phase 2
0.7197	Intermediate Similarity	NPD3021	Approved
0.7197	Intermediate Similarity	NPD3022	Approved
0.719	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7041	Phase 2
0.719	Intermediate Similarity	NPD7212	Phase 2
0.719	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7213	Phase 3
0.7188	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6559	Discontinued
0.7183	Intermediate Similarity	NPD3094	Phase 2
0.7181	Intermediate Similarity	NPD2531	Phase 2
0.7176	Intermediate Similarity	NPD2342	Discontinued
0.7174	Intermediate Similarity	NPD1651	Approved
0.7172	Intermediate Similarity	NPD1296	Phase 2
0.7172	Intermediate Similarity	NPD6798	Discontinued
0.7171	Intermediate Similarity	NPD6190	Approved
0.717	Intermediate Similarity	NPD5402	Approved
0.7161	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD3092	Approved
0.7143	Intermediate Similarity	NPD5709	Phase 3
0.7133	Intermediate Similarity	NPD6002	Phase 3
0.7133	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6005	Phase 3
0.7133	Intermediate Similarity	NPD6004	Phase 3
0.7125	Intermediate Similarity	NPD3882	Suspended
0.7122	Intermediate Similarity	NPD1778	Approved
0.7122	Intermediate Similarity	NPD2932	Approved
0.7122	Intermediate Similarity	NPD17	Approved
0.7122	Intermediate Similarity	NPD3019	Approved
0.7114	Intermediate Similarity	NPD4308	Phase 3
0.7113	Intermediate Similarity	NPD6696	Suspended
0.7113	Intermediate Similarity	NPD8651	Approved
0.7111	Intermediate Similarity	NPD5283	Phase 1
0.7108	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7741	Discontinued
0.7099	Intermediate Similarity	NPD6746	Phase 2
0.7099	Intermediate Similarity	NPD4666	Phase 3
0.7099	Intermediate Similarity	NPD5494	Approved
0.7097	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2238	Phase 2
0.7071	Intermediate Similarity	NPD3847	Discontinued
0.707	Intermediate Similarity	NPD7458	Discontinued
0.7063	Intermediate Similarity	NPD1470	Approved
0.7063	Intermediate Similarity	NPD1164	Approved
0.7063	Intermediate Similarity	NPD2859	Approved
0.7063	Intermediate Similarity	NPD2860	Approved
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7051	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD920	Approved
0.705	Intermediate Similarity	NPD5585	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