NPASS Compound

Structure

CID222047 OpenBabel06191716012D 35 39 0 0 1 0 0 0 0 0999 V2000 -0.9749 -3.5263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5264 -3.2177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4713 -0.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7707 2.7262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8238 1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8238 -1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6476 -0.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6476 1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1189 0.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2951 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8238 1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4713 -2.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4713 -1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8238 -2.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8238 0.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8195 2.7262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8238 -1.4268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4713 1.4268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6476 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1189 1.4268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6476 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2951 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6476 -2.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4713 0.4756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2951 1.9024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8238 0.4756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6476 -0.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2951 3.5500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9427 1.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4713 0.4756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2951 0.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1189 -0.4756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 18 2 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 26 1 0 0 0 0 12 28 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 30 1 0 0 0 0 15 19 1 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 16 29 1 0 0 0 0 17 27 1 0 0 0 0 17 31 2 0 0 0 0 18 19 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 6 0 0 0 20 26 1 1 0 0 0 20 27 1 0 0 0 0 21 26 1 1 0 0 0 21 28 1 0 0 0 0 22 27 1 1 0 0 0 22 32 1 0 0 0 0 23 30 1 6 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 6 0 0 0 29 6 1 6 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	520.695
LogP:	3.902
LogD:	3.675
LogS:	-3.956
# Rotatable Bonds:	2
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	5.047
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.381
MDCK Permeability:	1.9160057490807958e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.077
30% Bioavailability (F30%):	0.746

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	70.1961898803711%
Volume Distribution (VD):	0.632
Pgp-substrate:	21.521129608154297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.608
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.668
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	2.788
Half-life (T1/2):	0.288

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.909
Carcinogencity:	0.321
Eye Corrosion:	0.309
Eye Irritation:	0.073
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC222047

Natural Product ID:	NPC222047
*Common Name:**	Quillaic Acid
IUPAC Name:	(4aR,5R,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	Quillaic Acid
Standard InCHIKey:	MQUFAARYGOUYEV-UAWZMHPWSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,17,19-23,32-33H,8-16H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1
SMILES:	O=C[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)C[C@@H](O)[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL260060
PubChem CID:	101810
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[16880670]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[17409564]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	roots	n.a.	n.a.	PMID[18194870]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[21070025]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10187	Protoblastenia incrustans	Species	Psoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10820	Galium spurium	Species	Rubiaceae	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
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	59700.0	nM	PMID[527967]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	0.0	%	PMID[527968]

☑ 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 NPC222047 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	215
0.1-0.2	1395
0.2-0.3	5087
0.3-0.4	13760
0.4-0.5	9498
0.5-0.6	5581
0.6-0.7	4710
0.7-0.8	1903
0.8-0.85	243
0.85-0.9	125
0.9-0.95	151
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
0.9885	High Similarity	NPC298554
0.9773	High Similarity	NPC209868
0.977	High Similarity	NPC324341
0.977	High Similarity	NPC282616
0.977	High Similarity	NPC966
0.977	High Similarity	NPC288833
0.977	High Similarity	NPC228784
0.977	High Similarity	NPC155120
0.9655	High Similarity	NPC172361
0.9655	High Similarity	NPC86372
0.9545	High Similarity	NPC6255
0.9545	High Similarity	NPC471588
0.954	High Similarity	NPC61543
0.954	High Similarity	NPC130520
0.954	High Similarity	NPC225585
0.954	High Similarity	NPC121798
0.954	High Similarity	NPC59263
0.954	High Similarity	NPC234346
0.954	High Similarity	NPC127689
0.954	High Similarity	NPC263393
0.954	High Similarity	NPC293048
0.954	High Similarity	NPC270768
0.9451	High Similarity	NPC187933
0.9444	High Similarity	NPC148523
0.9432	High Similarity	NPC126369
0.9432	High Similarity	NPC130278
0.9432	High Similarity	NPC470589
0.9432	High Similarity	NPC111110
0.9425	High Similarity	NPC52169
0.9425	High Similarity	NPC182797
0.9348	High Similarity	NPC188833
0.9341	High Similarity	NPC132824
0.9341	High Similarity	NPC201657
0.9341	High Similarity	NPC98874
0.9333	High Similarity	NPC474529
0.9333	High Similarity	NPC78580
0.9333	High Similarity	NPC23621
0.9333	High Similarity	NPC184006
0.9318	High Similarity	NPC25906
0.9318	High Similarity	NPC274330
0.9318	High Similarity	NPC64872
0.9318	High Similarity	NPC198664
0.9318	High Similarity	NPC143232
0.9318	High Similarity	NPC290972
0.931	High Similarity	NPC307426
0.931	High Similarity	NPC142415
0.931	High Similarity	NPC171203
0.931	High Similarity	NPC51700
0.931	High Similarity	NPC68160
0.931	High Similarity	NPC242468
0.931	High Similarity	NPC18064
0.931	High Similarity	NPC293564
0.931	High Similarity	NPC98442
0.931	High Similarity	NPC88716
0.931	High Similarity	NPC102683
0.931	High Similarity	NPC130577
0.9239	High Similarity	NPC21728
0.9239	High Similarity	NPC106112
0.9239	High Similarity	NPC261935
0.9231	High Similarity	NPC195715
0.9231	High Similarity	NPC23241
0.9222	High Similarity	NPC86368
0.9222	High Similarity	NPC229281
0.9213	High Similarity	NPC210037
0.9213	High Similarity	NPC477872
0.9213	High Similarity	NPC120968
0.9213	High Similarity	NPC7260
0.9213	High Similarity	NPC227467
0.9213	High Similarity	NPC273621
0.9213	High Similarity	NPC18872
0.9213	High Similarity	NPC290614
0.9213	High Similarity	NPC291028
0.9205	High Similarity	NPC246708
0.9205	High Similarity	NPC473242
0.9205	High Similarity	NPC470629
0.9205	High Similarity	NPC181225
0.9205	High Similarity	NPC17733
0.9205	High Similarity	NPC40552
0.9205	High Similarity	NPC474512
0.9205	High Similarity	NPC290690
0.9195	High Similarity	NPC235341
0.9195	High Similarity	NPC477579
0.9195	High Similarity	NPC72638
0.9195	High Similarity	NPC95594
0.914	High Similarity	NPC29765
0.914	High Similarity	NPC174663
0.914	High Similarity	NPC111214
0.914	High Similarity	NPC271614
0.914	High Similarity	NPC164349
0.9121	High Similarity	NPC263548
0.9121	High Similarity	NPC145667
0.9121	High Similarity	NPC299996
0.9121	High Similarity	NPC159365
0.9121	High Similarity	NPC114159
0.9121	High Similarity	NPC88116
0.9121	High Similarity	NPC191412
0.9121	High Similarity	NPC6818
0.9121	High Similarity	NPC32407
0.9121	High Similarity	NPC231063
0.9121	High Similarity	NPC282395
0.9121	High Similarity	NPC20235
0.9111	High Similarity	NPC84319
0.9111	High Similarity	NPC145067
0.9111	High Similarity	NPC71074
0.9111	High Similarity	NPC4036
0.9111	High Similarity	NPC65120
0.9111	High Similarity	NPC474525
0.9111	High Similarity	NPC235884
0.9111	High Similarity	NPC475708
0.9111	High Similarity	NPC300351
0.9111	High Similarity	NPC187722
0.9111	High Similarity	NPC306541
0.9111	High Similarity	NPC233455
0.9111	High Similarity	NPC472149
0.9111	High Similarity	NPC25299
0.9111	High Similarity	NPC52021
0.9111	High Similarity	NPC105189
0.9111	High Similarity	NPC158030
0.9101	High Similarity	NPC161751
0.9101	High Similarity	NPC470588
0.9101	High Similarity	NPC474972
0.9101	High Similarity	NPC95246
0.9091	High Similarity	NPC173089
0.9091	High Similarity	NPC158141
0.9043	High Similarity	NPC35239
0.9032	High Similarity	NPC26413
0.9011	High Similarity	NPC118490
0.9011	High Similarity	NPC118519
0.9011	High Similarity	NPC202728
0.9011	High Similarity	NPC214756
0.9011	High Similarity	NPC74855
0.9011	High Similarity	NPC136313
0.9011	High Similarity	NPC158059
0.9011	High Similarity	NPC275809
0.9011	High Similarity	NPC272075
0.9011	High Similarity	NPC307335
0.9011	High Similarity	NPC295643
0.9	High Similarity	NPC474728
0.9	High Similarity	NPC120840
0.9	High Similarity	NPC49320
0.9	High Similarity	NPC193750
0.9	High Similarity	NPC46441
0.9	High Similarity	NPC113989
0.8989	High Similarity	NPC1753
0.8989	High Similarity	NPC474511
0.8977	High Similarity	NPC213412
0.8936	High Similarity	NPC471966
0.8925	High Similarity	NPC476318
0.8925	High Similarity	NPC305464
0.8925	High Similarity	NPC472806
0.8925	High Similarity	NPC173744
0.8925	High Similarity	NPC19376
0.8925	High Similarity	NPC73004
0.8925	High Similarity	NPC116457
0.8925	High Similarity	NPC167193
0.8925	High Similarity	NPC476327
0.8925	High Similarity	NPC25848
0.8925	High Similarity	NPC204961
0.8925	High Similarity	NPC307282
0.8913	High Similarity	NPC148964
0.8913	High Similarity	NPC91010
0.8913	High Similarity	NPC80365
0.8901	High Similarity	NPC60755
0.8901	High Similarity	NPC470590
0.8901	High Similarity	NPC285184
0.8901	High Similarity	NPC38754
0.8901	High Similarity	NPC77099
0.8889	High Similarity	NPC474686
0.8889	High Similarity	NPC30522
0.8889	High Similarity	NPC69627
0.8876	High Similarity	NPC71507
0.8864	High Similarity	NPC133954
0.883	High Similarity	NPC476878
0.883	High Similarity	NPC89225
0.883	High Similarity	NPC9613
0.883	High Similarity	NPC247139
0.883	High Similarity	NPC476879
0.8817	High Similarity	NPC139570
0.8817	High Similarity	NPC83693
0.8817	High Similarity	NPC198245
0.8817	High Similarity	NPC473240
0.8817	High Similarity	NPC32118
0.8817	High Similarity	NPC96916
0.8817	High Similarity	NPC474727
0.8804	High Similarity	NPC63118
0.8804	High Similarity	NPC133579
0.8804	High Similarity	NPC474806
0.8804	High Similarity	NPC49776
0.8804	High Similarity	NPC474436
0.8791	High Similarity	NPC169933
0.8778	High Similarity	NPC224145
0.8778	High Similarity	NPC474474
0.8776	High Similarity	NPC80566
0.8764	High Similarity	NPC475862
0.8764	High Similarity	NPC73038
0.8764	High Similarity	NPC74363
0.875	High Similarity	NPC171789
0.8723	High Similarity	NPC327179
0.8723	High Similarity	NPC230151
0.8723	High Similarity	NPC259733

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 NPC222047 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1784
0.2-0.3	3861
0.3-0.4	2223
0.4-0.5	656
0.5-0.6	203
0.6-0.7	190
0.7-0.8	33
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9111	High Similarity	NPD7515	Phase 2
0.871	High Similarity	NPD7748	Approved
0.8438	Intermediate Similarity	NPD7902	Approved
0.8242	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7645	Phase 2
0.8125	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7900	Approved
0.7766	Intermediate Similarity	NPD3618	Phase 1
0.7742	Intermediate Similarity	NPD4786	Approved
0.7732	Intermediate Similarity	NPD6411	Approved
0.7732	Intermediate Similarity	NPD8034	Phase 2
0.7732	Intermediate Similarity	NPD8035	Phase 2
0.7717	Intermediate Similarity	NPD3667	Approved
0.7708	Intermediate Similarity	NPD5328	Approved
0.7653	Intermediate Similarity	NPD6399	Phase 3
0.76	Intermediate Similarity	NPD4697	Phase 3
0.7551	Intermediate Similarity	NPD6079	Approved
0.7526	Intermediate Similarity	NPD6101	Approved
0.7526	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7128	Approved
0.7524	Intermediate Similarity	NPD6402	Approved
0.7524	Intermediate Similarity	NPD5739	Approved
0.7524	Intermediate Similarity	NPD6675	Approved
0.7451	Intermediate Similarity	NPD7638	Approved
0.7423	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8328	Phase 3
0.7383	Intermediate Similarity	NPD6881	Approved
0.7383	Intermediate Similarity	NPD6899	Approved
0.7383	Intermediate Similarity	NPD7320	Approved
0.7379	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7368	Intermediate Similarity	NPD3665	Phase 1
0.7368	Intermediate Similarity	NPD3666	Approved
0.7368	Intermediate Similarity	NPD3133	Approved
0.7353	Intermediate Similarity	NPD6083	Phase 2
0.7353	Intermediate Similarity	NPD4755	Approved
0.7353	Intermediate Similarity	NPD6084	Phase 2
0.7321	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7115	Discovery
0.7315	Intermediate Similarity	NPD6372	Approved
0.7315	Intermediate Similarity	NPD6373	Approved
0.7312	Intermediate Similarity	NPD7525	Registered
0.73	Intermediate Similarity	NPD4202	Approved
0.729	Intermediate Similarity	NPD5697	Approved
0.729	Intermediate Similarity	NPD5701	Approved
0.7255	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5221	Approved
0.7255	Intermediate Similarity	NPD5222	Approved
0.7253	Intermediate Similarity	NPD6117	Approved
0.7248	Intermediate Similarity	NPD7102	Approved
0.7248	Intermediate Similarity	NPD7290	Approved
0.7248	Intermediate Similarity	NPD6883	Approved
0.7216	Intermediate Similarity	NPD6409	Approved
0.7216	Intermediate Similarity	NPD6684	Approved
0.7216	Intermediate Similarity	NPD7146	Approved
0.7216	Intermediate Similarity	NPD5330	Approved
0.7216	Intermediate Similarity	NPD7521	Approved
0.7216	Intermediate Similarity	NPD7334	Approved
0.7216	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5286	Approved
0.7212	Intermediate Similarity	NPD5285	Approved
0.7212	Intermediate Similarity	NPD4700	Approved
0.7212	Intermediate Similarity	NPD4696	Approved
0.7188	Intermediate Similarity	NPD3668	Phase 3
0.7184	Intermediate Similarity	NPD5173	Approved
0.7182	Intermediate Similarity	NPD6649	Approved
0.7182	Intermediate Similarity	NPD6617	Approved
0.7182	Intermediate Similarity	NPD6847	Approved
0.7182	Intermediate Similarity	NPD6650	Approved
0.7182	Intermediate Similarity	NPD8130	Phase 1
0.7182	Intermediate Similarity	NPD6869	Approved
0.7174	Intermediate Similarity	NPD6116	Phase 1
0.7172	Intermediate Similarity	NPD4753	Phase 2
0.7156	Intermediate Similarity	NPD6012	Approved
0.7156	Intermediate Similarity	NPD6013	Approved
0.7156	Intermediate Similarity	NPD6014	Approved
0.7156	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3573	Approved
0.7129	Intermediate Similarity	NPD5779	Approved
0.7129	Intermediate Similarity	NPD5778	Approved
0.7117	Intermediate Similarity	NPD8297	Approved
0.7117	Intermediate Similarity	NPD6882	Approved
0.7115	Intermediate Similarity	NPD4225	Approved
0.7097	Intermediate Similarity	NPD6697	Approved
0.7097	Intermediate Similarity	NPD6115	Approved
0.7097	Intermediate Similarity	NPD6118	Approved
0.7097	Intermediate Similarity	NPD6114	Approved
0.7087	Intermediate Similarity	NPD7614	Phase 1
0.7075	Intermediate Similarity	NPD5211	Phase 2
0.7075	Intermediate Similarity	NPD4633	Approved
0.7075	Intermediate Similarity	NPD5225	Approved
0.7075	Intermediate Similarity	NPD5226	Approved
0.7075	Intermediate Similarity	NPD5224	Approved
0.7071	Intermediate Similarity	NPD6672	Approved
0.7071	Intermediate Similarity	NPD5737	Approved
0.7071	Intermediate Similarity	NPD6903	Approved
0.7064	Intermediate Similarity	NPD6011	Approved
0.7033	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5174	Approved
0.7009	Intermediate Similarity	NPD5175	Approved
0.699	Remote Similarity	NPD5695	Phase 3
0.6981	Remote Similarity	NPD5223	Approved
0.6957	Remote Similarity	NPD6942	Approved
0.6957	Remote Similarity	NPD7339	Approved
0.6952	Remote Similarity	NPD5696	Approved
0.6947	Remote Similarity	NPD4695	Discontinued
0.6944	Remote Similarity	NPD5141	Approved
0.6942	Remote Similarity	NPD7319	Approved
0.6937	Remote Similarity	NPD4634	Approved
0.6882	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4768	Approved
0.6881	Remote Similarity	NPD4767	Approved
0.6869	Remote Similarity	NPD5279	Phase 3
0.686	Remote Similarity	NPD7736	Approved
0.6852	Remote Similarity	NPD4754	Approved
0.6838	Remote Similarity	NPD6319	Approved
0.6833	Remote Similarity	NPD7507	Approved
0.6827	Remote Similarity	NPD5210	Approved
0.6827	Remote Similarity	NPD4629	Approved
0.6827	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6412	Phase 2
0.6804	Remote Similarity	NPD4223	Phase 3
0.6804	Remote Similarity	NPD4221	Approved
0.6783	Remote Similarity	NPD6274	Approved
0.6783	Remote Similarity	NPD6868	Approved
0.6768	Remote Similarity	NPD5329	Approved
0.6762	Remote Similarity	NPD7732	Phase 3
0.6759	Remote Similarity	NPD7632	Discontinued
0.6757	Remote Similarity	NPD4730	Approved
0.6757	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4729	Approved
0.6757	Remote Similarity	NPD5128	Approved
0.6754	Remote Similarity	NPD4632	Approved
0.6752	Remote Similarity	NPD7100	Approved
0.6752	Remote Similarity	NPD7101	Approved
0.675	Remote Similarity	NPD7492	Approved
0.6735	Remote Similarity	NPD4788	Approved
0.67	Remote Similarity	NPD6098	Approved
0.6699	Remote Similarity	NPD5281	Approved
0.6699	Remote Similarity	NPD7637	Suspended
0.6699	Remote Similarity	NPD5284	Approved
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6059	Approved
0.6695	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6639	Remote Similarity	NPD8293	Discontinued
0.6639	Remote Similarity	NPD7078	Approved
0.6639	Remote Similarity	NPD6908	Approved
0.6639	Remote Similarity	NPD6909	Approved
0.6637	Remote Similarity	NPD5248	Approved
0.6637	Remote Similarity	NPD5250	Approved
0.6637	Remote Similarity	NPD5249	Phase 3
0.6637	Remote Similarity	NPD5247	Approved
0.6637	Remote Similarity	NPD5251	Approved
0.6633	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8133	Approved
0.6607	Remote Similarity	NPD5168	Approved
0.6607	Remote Similarity	NPD6686	Approved
0.6593	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6370	Approved
0.6581	Remote Similarity	NPD6317	Approved
0.6581	Remote Similarity	NPD6009	Approved
0.6579	Remote Similarity	NPD5215	Approved
0.6579	Remote Similarity	NPD5217	Approved
0.6579	Remote Similarity	NPD5216	Approved
0.6577	Remote Similarity	NPD6008	Approved
0.6562	Remote Similarity	NPD3617	Approved
0.6562	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5205	Approved
0.6535	Remote Similarity	NPD4690	Approved
0.6535	Remote Similarity	NPD4519	Discontinued
0.6535	Remote Similarity	NPD4623	Approved
0.6535	Remote Similarity	NPD4138	Approved
0.6535	Remote Similarity	NPD4689	Approved
0.6535	Remote Similarity	NPD4693	Phase 3
0.6535	Remote Similarity	NPD4688	Approved
0.6531	Remote Similarity	NPD5369	Approved
0.6525	Remote Similarity	NPD6314	Approved
0.6525	Remote Similarity	NPD6313	Approved
0.65	Remote Similarity	NPD6015	Approved
0.65	Remote Similarity	NPD6016	Approved
0.6491	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5169	Approved
0.6491	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5135	Approved
0.6465	Remote Similarity	NPD4270	Approved
0.6465	Remote Similarity	NPD4269	Approved
0.6446	Remote Similarity	NPD5988	Approved
0.6436	Remote Similarity	NPD1694	Approved
0.6435	Remote Similarity	NPD5127	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