NPASS Compound

Structure

NPC471587 OpenBabel07101718272D 32 33 0 0 1 0 0 0 0 0999 V2000 -4.3301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1340 2.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 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 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 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 -3.5000 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 -3.4641 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 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 -1.5000 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 -1.7321 -2.0000 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 -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 3 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 28 1 0 0 0 0 8 10 1 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 19 2 0 0 0 0 11 20 2 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 21 2 0 0 0 0 15 28 1 0 0 0 0 16 28 1 0 0 0 0 17 31 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 22 26 1 0 0 0 0 22 29 2 0 0 0 0 23 25 2 0 0 0 0 23 27 1 0 0 0 0 24 26 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 26 27 2 0 0 0 0 27 32 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.28
Volume:	489.8
LogP:	7.991
LogD:	5.928
LogS:	-4.293
# Rotatable Bonds:	10
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	3.823
Fsp3:	0.464
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.766
MDCK Permeability:	2.196817695221398e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.92
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	94.45892333984375%
Volume Distribution (VD):	3.418
Pgp-substrate:	7.530319690704346%

ADMET: Metabolism

CYP1A2-inhibitor:	0.894
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.855
CYP2C19-substrate:	0.353
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.972
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.839
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	8.012
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.355
Human Hepatotoxicity (H-HT):	0.96
Drug-inuced Liver Injury (DILI):	0.065
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.133
Skin Sensitization:	0.903
Carcinogencity:	0.085
Eye Corrosion:	0.003
Eye Irritation:	0.12
Respiratory Toxicity:	0.575

Download Data

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

Natural Product: NPC471587

Natural Product ID:	NPC471587
*Common Name:**	1-[5-[(2E)-3,7-Dimethylocta-2,6-Dienoxy]-7-Hydroxy-2-Methyl-2-(4-Methylpent-3-Enyl)Chromen-8-Yl]Ethanone
IUPAC Name:	1-[5-[(2E)-3,7-dimethylocta-2,6-dienoxy]-7-hydroxy-2-methyl-2-(4-methylpent-3-enyl)chromen-8-yl]ethanone
Synonyms:
Standard InCHIKey:	XSSCFVOPJZDLBW-KGENOOAVSA-N
Standard InCHI:	InChI=1S/C28H38O4/c1-19(2)10-8-12-21(5)14-17-31-25-18-24(30)26(22(6)29)27-23(25)13-16-28(7,32-27)15-9-11-20(3)4/h10-11,13-14,16,18,30H,8-9,12,15,17H2,1-7H3/b21-14+
SMILES:	C/C(=CCOc1cc(O)c(c2c1C=CC(O2)(C)CCC=C(C)C)C(=O)C)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL267701
PubChem CID:	24770582
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575945]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163582]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	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
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	23.24	%	PMID[528882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	26.62	%	PMID[528882]

☑ 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 NPC471587 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	350
0.1-0.2	1467
0.2-0.3	3821
0.3-0.4	10065
0.4-0.5	8509
0.5-0.6	3699
0.6-0.7	6117
0.7-0.8	5420
0.8-0.85	1795
0.85-0.9	938
0.9-0.95	491
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC23257
0.9704	High Similarity	NPC470668
0.9704	High Similarity	NPC131130
0.9704	High Similarity	NPC470669
0.9701	High Similarity	NPC174999
0.9632	High Similarity	NPC139554
0.9627	High Similarity	NPC101752
0.9627	High Similarity	NPC60667
0.9571	High Similarity	NPC283234
0.9565	High Similarity	NPC226636
0.9565	High Similarity	NPC11561
0.9562	High Similarity	NPC150522
0.9562	High Similarity	NPC241100
0.9562	High Similarity	NPC159275
0.9556	High Similarity	NPC156910
0.9556	High Similarity	NPC187826
0.9552	High Similarity	NPC125920
0.9504	High Similarity	NPC132592
0.9504	High Similarity	NPC160821
0.95	High Similarity	NPC475052
0.95	High Similarity	NPC312973
0.95	High Similarity	NPC246948
0.95	High Similarity	NPC176229
0.95	High Similarity	NPC285630
0.95	High Similarity	NPC301276
0.95	High Similarity	NPC214774
0.95	High Similarity	NPC54577
0.95	High Similarity	NPC83357
0.95	High Similarity	NPC267375
0.95	High Similarity	NPC470647
0.95	High Similarity	NPC111786
0.95	High Similarity	NPC195621
0.95	High Similarity	NPC127059
0.95	High Similarity	NPC20488
0.95	High Similarity	NPC88964
0.95	High Similarity	NPC67805
0.95	High Similarity	NPC142405
0.9496	High Similarity	NPC185276
0.9496	High Similarity	NPC478086
0.9496	High Similarity	NPC214166
0.9496	High Similarity	NPC316816
0.9493	High Similarity	NPC147688
0.9493	High Similarity	NPC110969
0.9493	High Similarity	NPC205006
0.9493	High Similarity	NPC103362
0.9493	High Similarity	NPC156590
0.9493	High Similarity	NPC118840
0.9493	High Similarity	NPC64908
0.9493	High Similarity	NPC282300
0.9489	High Similarity	NPC216978
0.9489	High Similarity	NPC301217
0.9489	High Similarity	NPC303633
0.9489	High Similarity	NPC53181
0.9489	High Similarity	NPC217186
0.9489	High Similarity	NPC55018
0.9489	High Similarity	NPC18260
0.9489	High Similarity	NPC220062
0.9489	High Similarity	NPC96565
0.9489	High Similarity	NPC473076
0.9489	High Similarity	NPC78913
0.9481	High Similarity	NPC151113
0.9478	High Similarity	NPC93756
0.9478	High Similarity	NPC108113
0.9433	High Similarity	NPC296998
0.9433	High Similarity	NPC237635
0.9433	High Similarity	NPC473077
0.9433	High Similarity	NPC79469
0.9433	High Similarity	NPC23728
0.9433	High Similarity	NPC104406
0.9433	High Similarity	NPC201731
0.9433	High Similarity	NPC110303
0.9433	High Similarity	NPC24673
0.9433	High Similarity	NPC97716
0.9429	High Similarity	NPC234629
0.9429	High Similarity	NPC319752
0.9429	High Similarity	NPC235217
0.9429	High Similarity	NPC473014
0.9429	High Similarity	NPC311741
0.9429	High Similarity	NPC197252
0.9429	High Similarity	NPC236766
0.9429	High Similarity	NPC131568
0.9429	High Similarity	NPC209040
0.9429	High Similarity	NPC131579
0.9424	High Similarity	NPC148757
0.9424	High Similarity	NPC76372
0.9424	High Similarity	NPC32739
0.9424	High Similarity	NPC66515
0.9424	High Similarity	NPC217083
0.9424	High Similarity	NPC107572
0.9424	High Similarity	NPC325346
0.9424	High Similarity	NPC299080
0.9424	High Similarity	NPC324134
0.9424	High Similarity	NPC161506
0.9424	High Similarity	NPC324436
0.9424	High Similarity	NPC194432
0.9424	High Similarity	NPC214236
0.9424	High Similarity	NPC167624
0.9424	High Similarity	NPC37496
0.9424	High Similarity	NPC166934
0.9424	High Similarity	NPC1089
0.9424	High Similarity	NPC220998
0.9424	High Similarity	NPC78803
0.9424	High Similarity	NPC76338
0.9424	High Similarity	NPC227579
0.9424	High Similarity	NPC228504
0.9424	High Similarity	NPC59739
0.9424	High Similarity	NPC78
0.9424	High Similarity	NPC166482
0.9424	High Similarity	NPC293852
0.9424	High Similarity	NPC223500
0.9424	High Similarity	NPC328164
0.9424	High Similarity	NPC177354
0.9424	High Similarity	NPC64915
0.9424	High Similarity	NPC10937
0.9424	High Similarity	NPC265040
0.9424	High Similarity	NPC40833
0.9424	High Similarity	NPC125855
0.9424	High Similarity	NPC182852
0.9424	High Similarity	NPC296917
0.9424	High Similarity	NPC62840
0.9424	High Similarity	NPC306829
0.942	High Similarity	NPC172986
0.942	High Similarity	NPC270883
0.942	High Similarity	NPC305355
0.942	High Similarity	NPC235239
0.942	High Similarity	NPC475680
0.942	High Similarity	NPC261227
0.942	High Similarity	NPC477272
0.9416	High Similarity	NPC470672
0.9416	High Similarity	NPC474487
0.9416	High Similarity	NPC470671
0.9416	High Similarity	NPC474504
0.9416	High Similarity	NPC201395
0.9416	High Similarity	NPC124269
0.9407	High Similarity	NPC144027
0.9407	High Similarity	NPC236974
0.9403	High Similarity	NPC203817
0.9403	High Similarity	NPC10971
0.9371	High Similarity	NPC188403
0.9366	High Similarity	NPC6511
0.9366	High Similarity	NPC189087
0.9366	High Similarity	NPC321623
0.9366	High Similarity	NPC266572
0.9366	High Similarity	NPC161191
0.9362	High Similarity	NPC124729
0.9362	High Similarity	NPC474161
0.9362	High Similarity	NPC476088
0.9357	High Similarity	NPC169591
0.9357	High Similarity	NPC255133
0.9357	High Similarity	NPC149026
0.9357	High Similarity	NPC257097
0.9357	High Similarity	NPC85162
0.9357	High Similarity	NPC310130
0.9357	High Similarity	NPC150408
0.9357	High Similarity	NPC39329
0.9357	High Similarity	NPC106985
0.9357	High Similarity	NPC68104
0.9357	High Similarity	NPC81697
0.9357	High Similarity	NPC166138
0.9357	High Similarity	NPC91560
0.9357	High Similarity	NPC143896
0.9357	High Similarity	NPC18585
0.9357	High Similarity	NPC278249
0.9357	High Similarity	NPC38219
0.9357	High Similarity	NPC75049
0.9357	High Similarity	NPC221432
0.9357	High Similarity	NPC219915
0.9357	High Similarity	NPC125894
0.9357	High Similarity	NPC107177
0.9357	High Similarity	NPC223812
0.9357	High Similarity	NPC175504
0.9357	High Similarity	NPC77794
0.9357	High Similarity	NPC164980
0.9357	High Similarity	NPC242100
0.9353	High Similarity	NPC96408
0.9353	High Similarity	NPC248372
0.9353	High Similarity	NPC4743
0.9353	High Similarity	NPC213322
0.9353	High Similarity	NPC156190
0.9353	High Similarity	NPC258630
0.9353	High Similarity	NPC17170
0.9353	High Similarity	NPC279650
0.9353	High Similarity	NPC110038
0.9353	High Similarity	NPC312391
0.9353	High Similarity	NPC166689
0.9353	High Similarity	NPC324386
0.9353	High Similarity	NPC3188
0.9348	High Similarity	NPC471697
0.9343	High Similarity	NPC188879
0.9343	High Similarity	NPC317119
0.9338	High Similarity	NPC46869
0.9338	High Similarity	NPC13575
0.9333	High Similarity	NPC223457
0.9328	High Similarity	NPC473584
0.9328	High Similarity	NPC475589
0.9328	High Similarity	NPC31872
0.9301	High Similarity	NPC5173
0.9301	High Similarity	NPC472628
0.9296	High Similarity	NPC91902
0.9296	High Similarity	NPC472627

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 NPC471587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	944
0.2-0.3	1626
0.3-0.4	2585
0.4-0.5	1872
0.5-0.6	1174
0.6-0.7	462
0.7-0.8	137
0.8-0.85	26
0.85-0.9	13
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9291	High Similarity	NPD4378	Clinical (unspecified phase)
0.9155	High Similarity	NPD7410	Clinical (unspecified phase)
0.9065	High Similarity	NPD1550	Clinical (unspecified phase)
0.9065	High Similarity	NPD1552	Clinical (unspecified phase)
0.9	High Similarity	NPD1549	Phase 2
0.8921	High Similarity	NPD1510	Phase 2
0.8905	High Similarity	NPD1240	Approved
0.8859	High Similarity	NPD8443	Clinical (unspecified phase)
0.8857	High Similarity	NPD2796	Approved
0.8792	High Similarity	NPD2393	Clinical (unspecified phase)
0.8784	High Similarity	NPD7411	Suspended
0.8777	High Similarity	NPD1607	Approved
0.8742	High Similarity	NPD7075	Discontinued
0.8716	High Similarity	NPD4380	Phase 2
0.8667	High Similarity	NPD7096	Clinical (unspecified phase)
0.8667	High Similarity	NPD7819	Suspended
0.8643	High Similarity	NPD6651	Approved
0.86	High Similarity	NPD6801	Discontinued
0.8562	High Similarity	NPD6799	Approved
0.8542	High Similarity	NPD2800	Approved
0.8489	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1934	Approved
0.8472	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1511	Approved
0.8431	Intermediate Similarity	NPD7768	Phase 2
0.8421	Intermediate Similarity	NPD2801	Approved
0.8414	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8322	Intermediate Similarity	NPD1512	Approved
0.8312	Intermediate Similarity	NPD3882	Suspended
0.8291	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD1243	Approved
0.8267	Intermediate Similarity	NPD920	Approved
0.8255	Intermediate Similarity	NPD2533	Approved
0.8255	Intermediate Similarity	NPD2534	Approved
0.8255	Intermediate Similarity	NPD2532	Approved
0.8243	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD3750	Approved
0.8217	Intermediate Similarity	NPD6959	Discontinued
0.8207	Intermediate Similarity	NPD1551	Phase 2
0.8137	Intermediate Similarity	NPD7286	Phase 2
0.8133	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3817	Phase 2
0.8082	Intermediate Similarity	NPD2935	Discontinued
0.8063	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6166	Phase 2
0.8063	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5953	Discontinued
0.8026	Intermediate Similarity	NPD5403	Approved
0.8025	Intermediate Similarity	NPD3749	Approved
0.8025	Intermediate Similarity	NPD7054	Approved
0.8014	Intermediate Similarity	NPD2799	Discontinued
0.7975	Intermediate Similarity	NPD7472	Approved
0.7975	Intermediate Similarity	NPD7074	Phase 3
0.7971	Intermediate Similarity	NPD422	Phase 1
0.7963	Intermediate Similarity	NPD3818	Discontinued
0.7959	Intermediate Similarity	NPD6099	Approved
0.7959	Intermediate Similarity	NPD6100	Approved
0.7958	Intermediate Similarity	NPD6832	Phase 2
0.7931	Intermediate Similarity	NPD5124	Phase 1
0.7931	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5494	Approved
0.7914	Intermediate Similarity	NPD9717	Approved
0.7905	Intermediate Similarity	NPD2344	Approved
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7895	Intermediate Similarity	NPD5401	Approved
0.7891	Intermediate Similarity	NPD3748	Approved
0.7891	Intermediate Similarity	NPD7033	Discontinued
0.7879	Intermediate Similarity	NPD7251	Discontinued
0.7872	Intermediate Similarity	NPD1203	Approved
0.7867	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD919	Approved
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD2313	Discontinued
0.7831	Intermediate Similarity	NPD7808	Phase 3
0.7826	Intermediate Similarity	NPD6232	Discontinued
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.781	Intermediate Similarity	NPD1548	Phase 1
0.78	Intermediate Similarity	NPD2654	Approved
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7764	Intermediate Similarity	NPD1247	Approved
0.7748	Intermediate Similarity	NPD4628	Phase 3
0.7736	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3268	Approved
0.7714	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.7697	Intermediate Similarity	NPD2309	Approved
0.7681	Intermediate Similarity	NPD9545	Approved
0.7673	Intermediate Similarity	NPD5402	Approved
0.7651	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1729	Discontinued
0.7622	Intermediate Similarity	NPD2797	Approved
0.7619	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD943	Approved
0.7607	Intermediate Similarity	NPD5710	Approved
0.7607	Intermediate Similarity	NPD5711	Approved
0.7603	Intermediate Similarity	NPD1296	Phase 2
0.76	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5844	Phase 1
0.7589	Intermediate Similarity	NPD1610	Phase 2
0.7586	Intermediate Similarity	NPD4360	Phase 2
0.7586	Intermediate Similarity	NPD4363	Phase 3
0.758	Intermediate Similarity	NPD3226	Approved
0.7574	Intermediate Similarity	NPD1241	Discontinued
0.7569	Intermediate Similarity	NPD2798	Approved
0.756	Intermediate Similarity	NPD6104	Discontinued
0.7543	Intermediate Similarity	NPD4361	Phase 2
0.7543	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD9493	Approved
0.7533	Intermediate Similarity	NPD4308	Phase 3
0.7484	Intermediate Similarity	NPD7390	Discontinued
0.7483	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3926	Phase 2
0.745	Intermediate Similarity	NPD230	Phase 1
0.7448	Intermediate Similarity	NPD1019	Discontinued
0.7434	Intermediate Similarity	NPD2346	Discontinued
0.7431	Intermediate Similarity	NPD3225	Approved
0.7415	Intermediate Similarity	NPD4625	Phase 3
0.7413	Intermediate Similarity	NPD3972	Approved
0.7386	Intermediate Similarity	NPD2424	Discontinued
0.7379	Intermediate Similarity	NPD3267	Approved
0.7379	Intermediate Similarity	NPD3266	Approved
0.7365	Intermediate Similarity	NPD411	Approved
0.7361	Intermediate Similarity	NPD4749	Approved
0.7358	Intermediate Similarity	NPD7458	Discontinued
0.7333	Intermediate Similarity	NPD447	Suspended
0.7333	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7584	Approved
0.7305	Intermediate Similarity	NPD2403	Approved
0.7294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1608	Approved
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7278	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5889	Approved
0.7267	Intermediate Similarity	NPD3142	Approved
0.7267	Intermediate Similarity	NPD3140	Approved
0.7267	Intermediate Similarity	NPD4307	Phase 2
0.7267	Intermediate Similarity	NPD5890	Approved
0.7254	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6798	Discontinued
0.7239	Intermediate Similarity	NPD4288	Approved
0.7233	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1652	Phase 2
0.7219	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1933	Approved
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6005	Phase 3
0.7208	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6004	Phase 3
0.7208	Intermediate Similarity	NPD6002	Phase 3
0.7208	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6585	Discontinued
0.7202	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5761	Phase 2
0.7178	Intermediate Similarity	NPD1465	Phase 2
0.7178	Intermediate Similarity	NPD5760	Phase 2
0.717	Intermediate Similarity	NPD5049	Phase 3
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7134	Intermediate Similarity	NPD2296	Approved
0.7134	Intermediate Similarity	NPD2354	Approved
0.7134	Intermediate Similarity	NPD3887	Approved
0.7133	Intermediate Similarity	NPD3764	Approved
0.7117	Intermediate Similarity	NPD6844	Discontinued
0.7117	Intermediate Similarity	NPD7577	Discontinued
0.7114	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7447	Phase 1
0.7107	Intermediate Similarity	NPD4661	Approved
0.7107	Intermediate Similarity	NPD4662	Approved
0.7103	Intermediate Similarity	NPD1201	Approved
0.7097	Intermediate Similarity	NPD1471	Phase 3
0.7095	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6671	Approved
0.7083	Intermediate Similarity	NPD17	Approved
0.7083	Intermediate Similarity	NPD1778	Approved
0.7075	Intermediate Similarity	NPD8651	Approved
0.707	Intermediate Similarity	NPD7003	Approved
0.7069	Intermediate Similarity	NPD8312	Approved
0.7069	Intermediate Similarity	NPD8313	Approved
0.7067	Intermediate Similarity	NPD3027	Phase 3
0.7063	Intermediate Similarity	NPD1894	Discontinued
0.7062	Intermediate Similarity	NPD4287	Approved
0.7055	Intermediate Similarity	NPD1481	Phase 2
0.7047	Intermediate Similarity	NPD9494	Approved
0.7047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8434	Phase 2

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