NPASS Compound

Structure

CID157113 OpenBabel06191715522D 35 39 0 0 1 0 0 0 0 0999 V2000 5.0662 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5081 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0206 0.6181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8650 0.8444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5331 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5331 2.4375 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5331 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 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 3.3775 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5331 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6887 3.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8900 0.8444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 30 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 6 0 0 0 18 22 1 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 31 2 0 0 0 0 20 25 1 0 0 0 0 20 26 1 1 0 0 0 21 26 1 1 0 0 0 21 28 1 0 0 0 0 22 29 1 6 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 1 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 29 35 1 0 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	520.695
LogP:	4.397
LogD:	3.818
LogS:	-4.028
# Rotatable Bonds:	1
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.432
Synthetic Accessibility Score:	5.061
Fsp3:	0.867
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:	-5.474
MDCK Permeability:	1.967848038475495e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.631
Plasma Protein Binding (PPB):	89.93277740478516%
Volume Distribution (VD):	0.616
Pgp-substrate:	9.733559608459473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.467
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.129
CYP2C9-substrate:	0.363
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.235
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	2.475
Half-life (T1/2):	0.299

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.797
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.113
Carcinogencity:	0.02
Eye Corrosion:	0.355
Eye Irritation:	0.135
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: NPC157113

Natural Product ID:	NPC157113
*Common Name:**	2-Oxopomolic Acid
IUPAC Name:	(1R,2R,4aS,6aR,6aS,6bR,8aR,10R,12aR,14bS)-1,10-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-11-oxo-3,4,5,6,6a,7,8,8a,10,12,13,14b-dodecahydro-2H-picene-4a-carboxylic acid
Synonyms:	2-Oxopomolic Acid
Standard InCHIKey:	HQZKQSIAHGHXDL-SGOBLLPSSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,20-23,32,35H,9-16H2,1-7H3,(H,33,34)/t17-,20+,21-,22-,23+,26+,27-,28-,29-,30+/m1/s1
SMILES:	O=C1C[C@@]2(C)[C@H](C([C@H]1O)(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@H](C)CC1)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461703
PubChem CID:	44593379
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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473413]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16765	Knoxia valerianoides	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
EC50	1
IC50	2
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	EC50	=	20.0	ug.mL-1	PMID[542515]
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	Inhibition	<	10.0	%	PMID[542516]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	38100.0	nM	PMID[542514]
NPT27	Others	Unspecified		Ratio IC50/EC50	=	2.0	n.a.	PMID[542515]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	40.0	ug.mL-1	PMID[542515]

☑ 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 NPC157113 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	221
0.1-0.2	1423
0.2-0.3	4961
0.3-0.4	13198
0.4-0.5	9400
0.5-0.6	5799
0.6-0.7	4945
0.7-0.8	2272
0.8-0.85	177
0.85-0.9	170
0.9-0.95	115
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC62516
0.9663	High Similarity	NPC158059
0.9663	High Similarity	NPC202728
0.9663	High Similarity	NPC118519
0.957	High Similarity	NPC118964
0.9556	High Similarity	NPC6818
0.9556	High Similarity	NPC191412
0.9556	High Similarity	NPC114159
0.9551	High Similarity	NPC38754
0.9551	High Similarity	NPC187722
0.9551	High Similarity	NPC474525
0.9551	High Similarity	NPC105189
0.9444	High Similarity	NPC118490
0.9444	High Similarity	NPC229281
0.9438	High Similarity	NPC291028
0.9438	High Similarity	NPC46441
0.9438	High Similarity	NPC120968
0.9438	High Similarity	NPC290614
0.9438	High Similarity	NPC193750
0.9438	High Similarity	NPC227467
0.9438	High Similarity	NPC210037
0.9438	High Similarity	NPC477872
0.9438	High Similarity	NPC18872
0.9438	High Similarity	NPC7260
0.9438	High Similarity	NPC273621
0.9348	High Similarity	NPC132824
0.9348	High Similarity	NPC116457
0.9348	High Similarity	NPC207922
0.9348	High Similarity	NPC259733
0.9348	High Similarity	NPC327179
0.9348	High Similarity	NPC158371
0.9341	High Similarity	NPC148964
0.9326	High Similarity	NPC25906
0.9326	High Similarity	NPC274330
0.9326	High Similarity	NPC64872
0.9326	High Similarity	NPC198664
0.9326	High Similarity	NPC290972
0.9326	High Similarity	NPC143232
0.9271	High Similarity	NPC284865
0.9247	High Similarity	NPC247139
0.9247	High Similarity	NPC255589
0.9247	High Similarity	NPC9613
0.9247	High Similarity	NPC259788
0.9247	High Similarity	NPC187933
0.9239	High Similarity	NPC96916
0.9222	High Similarity	NPC126369
0.9222	High Similarity	NPC470589
0.9222	High Similarity	NPC130278
0.9222	High Similarity	NPC111110
0.9213	High Similarity	NPC17733
0.9213	High Similarity	NPC182797
0.9213	High Similarity	NPC181225
0.9213	High Similarity	NPC473242
0.9213	High Similarity	NPC52169
0.9213	High Similarity	NPC474512
0.9213	High Similarity	NPC470629
0.9213	High Similarity	NPC290690
0.9149	High Similarity	NPC174663
0.914	High Similarity	NPC73004
0.914	High Similarity	NPC173744
0.914	High Similarity	NPC204961
0.913	High Similarity	NPC60692
0.9121	High Similarity	NPC233455
0.9121	High Similarity	NPC235704
0.9121	High Similarity	NPC158030
0.9121	High Similarity	NPC145067
0.9121	High Similarity	NPC4036
0.9121	High Similarity	NPC65120
0.9111	High Similarity	NPC127689
0.9111	High Similarity	NPC470588
0.9111	High Similarity	NPC293048
0.9111	High Similarity	NPC61543
0.9111	High Similarity	NPC234346
0.9111	High Similarity	NPC225585
0.9111	High Similarity	NPC130520
0.9111	High Similarity	NPC270768
0.9111	High Similarity	NPC59263
0.9111	High Similarity	NPC121798
0.9111	High Similarity	NPC263393
0.9101	High Similarity	NPC102683
0.9101	High Similarity	NPC88716
0.9101	High Similarity	NPC51700
0.9101	High Similarity	NPC68160
0.9101	High Similarity	NPC130577
0.9101	High Similarity	NPC242468
0.9101	High Similarity	NPC18064
0.9101	High Similarity	NPC171203
0.9101	High Similarity	NPC73064
0.9101	High Similarity	NPC98442
0.9101	High Similarity	NPC293564
0.9101	High Similarity	NPC307426
0.9101	High Similarity	NPC142415
0.9053	High Similarity	NPC35239
0.9043	High Similarity	NPC43686
0.9032	High Similarity	NPC290481
0.9032	High Similarity	NPC473240
0.9032	High Similarity	NPC139570
0.9032	High Similarity	NPC83693
0.9022	High Similarity	NPC214756
0.9022	High Similarity	NPC275809
0.9022	High Similarity	NPC295643
0.9022	High Similarity	NPC272075
0.9011	High Similarity	NPC474728
0.9	High Similarity	NPC246708
0.9	High Similarity	NPC40552
0.8989	High Similarity	NPC475862
0.8989	High Similarity	NPC74363
0.8989	High Similarity	NPC72638
0.8958	High Similarity	NPC256247
0.8958	High Similarity	NPC54909
0.8958	High Similarity	NPC233012
0.8947	High Similarity	NPC111214
0.8947	High Similarity	NPC271614
0.8947	High Similarity	NPC29765
0.8936	High Similarity	NPC476318
0.8936	High Similarity	NPC476327
0.8925	High Similarity	NPC282395
0.8925	High Similarity	NPC474529
0.8925	High Similarity	NPC263548
0.8925	High Similarity	NPC145667
0.8925	High Similarity	NPC209868
0.8925	High Similarity	NPC88116
0.8925	High Similarity	NPC32407
0.8925	High Similarity	NPC20235
0.8925	High Similarity	NPC299996
0.8925	High Similarity	NPC159365
0.8925	High Similarity	NPC231063
0.8913	High Similarity	NPC228784
0.8913	High Similarity	NPC471588
0.8913	High Similarity	NPC282616
0.8913	High Similarity	NPC324341
0.8913	High Similarity	NPC6255
0.8913	High Similarity	NPC71074
0.8913	High Similarity	NPC285184
0.8913	High Similarity	NPC25299
0.8913	High Similarity	NPC60755
0.8913	High Similarity	NPC300351
0.8913	High Similarity	NPC77099
0.8913	High Similarity	NPC52021
0.8913	High Similarity	NPC155120
0.8913	High Similarity	NPC84319
0.8913	High Similarity	NPC306541
0.8913	High Similarity	NPC472149
0.8913	High Similarity	NPC235884
0.8913	High Similarity	NPC966
0.8913	High Similarity	NPC288833
0.8913	High Similarity	NPC470590
0.8901	High Similarity	NPC474686
0.8901	High Similarity	NPC95246
0.8901	High Similarity	NPC474972
0.8901	High Similarity	NPC161751
0.8889	High Similarity	NPC71507
0.8876	High Similarity	NPC133954
0.8842	High Similarity	NPC261935
0.8842	High Similarity	NPC312075
0.8842	High Similarity	NPC106112
0.8842	High Similarity	NPC189880
0.8842	High Similarity	NPC203343
0.883	High Similarity	NPC148523
0.883	High Similarity	NPC32118
0.883	High Similarity	NPC147232
0.8817	High Similarity	NPC474806
0.8817	High Similarity	NPC474436
0.8817	High Similarity	NPC86368
0.8817	High Similarity	NPC74855
0.8817	High Similarity	NPC63118
0.8817	High Similarity	NPC298554
0.8817	High Similarity	NPC133579
0.8817	High Similarity	NPC136313
0.8817	High Similarity	NPC49776
0.8817	High Similarity	NPC307335
0.8804	High Similarity	NPC86372
0.8804	High Similarity	NPC172361
0.8804	High Similarity	NPC120840
0.8804	High Similarity	NPC49320
0.8804	High Similarity	NPC113989
0.8791	High Similarity	NPC474511
0.8791	High Similarity	NPC230387
0.8791	High Similarity	NPC1753
0.8778	High Similarity	NPC73038
0.8778	High Similarity	NPC56588
0.8778	High Similarity	NPC213412
0.8764	High Similarity	NPC180834
0.875	High Similarity	NPC471966
0.875	High Similarity	NPC164349
0.875	High Similarity	NPC260149
0.875	High Similarity	NPC58942
0.8737	High Similarity	NPC307282
0.8737	High Similarity	NPC305464
0.8737	High Similarity	NPC98874
0.8737	High Similarity	NPC201657
0.8737	High Similarity	NPC19376
0.8737	High Similarity	NPC25848
0.8723	High Similarity	NPC74751
0.8723	High Similarity	NPC222047
0.8723	High Similarity	NPC91010
0.8723	High Similarity	NPC80365
0.8723	High Similarity	NPC87095
0.8723	High Similarity	NPC23170
0.871	High Similarity	NPC301244

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 NPC157113 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1743
0.2-0.3	3826
0.3-0.4	2214
0.4-0.5	707
0.5-0.6	208
0.6-0.7	164
0.7-0.8	84
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9121	High Similarity	NPD7515	Phase 2
0.8842	High Similarity	NPD7902	Approved
0.8723	High Similarity	NPD7748	Approved
0.8526	High Similarity	NPD7901	Clinical (unspecified phase)
0.8526	High Similarity	NPD7900	Approved
0.8229	Intermediate Similarity	NPD6399	Phase 3
0.8105	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD6402	Approved
0.8058	Intermediate Similarity	NPD5739	Approved
0.8058	Intermediate Similarity	NPD6675	Approved
0.8058	Intermediate Similarity	NPD7128	Approved
0.8	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD6373	Approved
0.7979	Intermediate Similarity	NPD3618	Phase 1
0.7957	Intermediate Similarity	NPD4786	Approved
0.7938	Intermediate Similarity	NPD8035	Phase 2
0.7938	Intermediate Similarity	NPD8034	Phase 2
0.7935	Intermediate Similarity	NPD3667	Approved
0.7905	Intermediate Similarity	NPD6899	Approved
0.7905	Intermediate Similarity	NPD6881	Approved
0.7905	Intermediate Similarity	NPD7320	Approved
0.79	Intermediate Similarity	NPD4755	Approved
0.785	Intermediate Similarity	NPD6650	Approved
0.785	Intermediate Similarity	NPD6649	Approved
0.781	Intermediate Similarity	NPD5701	Approved
0.781	Intermediate Similarity	NPD5697	Approved
0.7802	Intermediate Similarity	NPD7645	Phase 2
0.78	Intermediate Similarity	NPD4697	Phase 3
0.7757	Intermediate Similarity	NPD7290	Approved
0.7757	Intermediate Similarity	NPD6883	Approved
0.7757	Intermediate Similarity	NPD7102	Approved
0.7745	Intermediate Similarity	NPD5286	Approved
0.7745	Intermediate Similarity	NPD4700	Approved
0.7745	Intermediate Similarity	NPD4696	Approved
0.7745	Intermediate Similarity	NPD5285	Approved
0.7736	Intermediate Similarity	NPD6011	Approved
0.7732	Intermediate Similarity	NPD5328	Approved
0.7723	Intermediate Similarity	NPD6083	Phase 2
0.7723	Intermediate Similarity	NPD6084	Phase 2
0.7685	Intermediate Similarity	NPD6847	Approved
0.7685	Intermediate Similarity	NPD8130	Phase 1
0.7685	Intermediate Similarity	NPD6869	Approved
0.7685	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6617	Approved
0.7677	Intermediate Similarity	NPD4202	Approved
0.767	Intermediate Similarity	NPD5223	Approved
0.7664	Intermediate Similarity	NPD6013	Approved
0.7664	Intermediate Similarity	NPD6012	Approved
0.7664	Intermediate Similarity	NPD6014	Approved
0.7624	Intermediate Similarity	NPD5221	Approved
0.7624	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5222	Approved
0.7615	Intermediate Similarity	NPD6882	Approved
0.7615	Intermediate Similarity	NPD8297	Approved
0.7596	Intermediate Similarity	NPD5224	Approved
0.7596	Intermediate Similarity	NPD5225	Approved
0.7596	Intermediate Similarity	NPD4633	Approved
0.7596	Intermediate Similarity	NPD5226	Approved
0.7596	Intermediate Similarity	NPD5211	Phase 2
0.7576	Intermediate Similarity	NPD6079	Approved
0.7565	Intermediate Similarity	NPD8328	Phase 3
0.7551	Intermediate Similarity	NPD4753	Phase 2
0.7549	Intermediate Similarity	NPD5173	Approved
0.7527	Intermediate Similarity	NPD7525	Registered
0.7527	Intermediate Similarity	NPD4695	Discontinued
0.7524	Intermediate Similarity	NPD5175	Approved
0.7524	Intermediate Similarity	NPD4754	Approved
0.7524	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD5696	Approved
0.7453	Intermediate Similarity	NPD5141	Approved
0.7449	Intermediate Similarity	NPD5737	Approved
0.7449	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6672	Approved
0.7396	Intermediate Similarity	NPD3133	Approved
0.7396	Intermediate Similarity	NPD3668	Phase 3
0.7396	Intermediate Similarity	NPD3666	Approved
0.7396	Intermediate Similarity	NPD3665	Phase 1
0.7387	Intermediate Similarity	NPD4632	Approved
0.7383	Intermediate Similarity	NPD4767	Approved
0.7383	Intermediate Similarity	NPD4768	Approved
0.7353	Intermediate Similarity	NPD4629	Approved
0.7353	Intermediate Similarity	NPD5695	Phase 3
0.7353	Intermediate Similarity	NPD5210	Approved
0.7347	Intermediate Similarity	NPD3573	Approved
0.7345	Intermediate Similarity	NPD7115	Discovery
0.7339	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5329	Approved
0.7308	Intermediate Similarity	NPD7638	Approved
0.7281	Intermediate Similarity	NPD6335	Approved
0.7257	Intermediate Similarity	NPD6274	Approved
0.7248	Intermediate Similarity	NPD4730	Approved
0.7248	Intermediate Similarity	NPD4729	Approved
0.7248	Intermediate Similarity	NPD5128	Approved
0.7245	Intermediate Similarity	NPD7334	Approved
0.7245	Intermediate Similarity	NPD6684	Approved
0.7245	Intermediate Similarity	NPD7521	Approved
0.7245	Intermediate Similarity	NPD5279	Phase 3
0.7245	Intermediate Similarity	NPD7146	Approved
0.7245	Intermediate Similarity	NPD6409	Approved
0.7245	Intermediate Similarity	NPD6098	Approved
0.7245	Intermediate Similarity	NPD5330	Approved
0.7245	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD7639	Approved
0.7228	Intermediate Similarity	NPD5281	Approved
0.7228	Intermediate Similarity	NPD6411	Approved
0.7228	Intermediate Similarity	NPD5284	Approved
0.7222	Intermediate Similarity	NPD6008	Approved
0.7217	Intermediate Similarity	NPD7100	Approved
0.7217	Intermediate Similarity	NPD7101	Approved
0.7216	Intermediate Similarity	NPD4197	Approved
0.7204	Intermediate Similarity	NPD6116	Phase 1
0.72	Intermediate Similarity	NPD6904	Approved
0.72	Intermediate Similarity	NPD6080	Approved
0.72	Intermediate Similarity	NPD6673	Approved
0.7193	Intermediate Similarity	NPD6317	Approved
0.7193	Intermediate Similarity	NPD6009	Approved
0.7184	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6313	Approved
0.713	Intermediate Similarity	NPD6314	Approved
0.7117	Intermediate Similarity	NPD5251	Approved
0.7117	Intermediate Similarity	NPD4634	Approved
0.7117	Intermediate Similarity	NPD5169	Approved
0.7117	Intermediate Similarity	NPD5249	Phase 3
0.7117	Intermediate Similarity	NPD5250	Approved
0.7117	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5247	Approved
0.7117	Intermediate Similarity	NPD5248	Approved
0.7117	Intermediate Similarity	NPD5135	Approved
0.7115	Intermediate Similarity	NPD7614	Phase 1
0.7105	Intermediate Similarity	NPD6868	Approved
0.71	Intermediate Similarity	NPD6903	Approved
0.7097	Intermediate Similarity	NPD6117	Approved
0.7094	Intermediate Similarity	NPD6909	Approved
0.7094	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6908	Approved
0.7091	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5217	Approved
0.7054	Intermediate Similarity	NPD5127	Approved
0.7054	Intermediate Similarity	NPD5216	Approved
0.7054	Intermediate Similarity	NPD5215	Approved
0.703	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7736	Approved
0.701	Intermediate Similarity	NPD4223	Phase 3
0.701	Intermediate Similarity	NPD4221	Approved
0.7009	Intermediate Similarity	NPD6319	Approved
0.6989	Remote Similarity	NPD6942	Approved
0.6989	Remote Similarity	NPD7339	Approved
0.6979	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7604	Phase 2
0.6949	Remote Similarity	NPD5983	Phase 2
0.6947	Remote Similarity	NPD6115	Approved
0.6947	Remote Similarity	NPD6114	Approved
0.6947	Remote Similarity	NPD3617	Approved
0.6947	Remote Similarity	NPD6697	Approved
0.6947	Remote Similarity	NPD6118	Approved
0.6939	Remote Similarity	NPD4788	Approved
0.6937	Remote Similarity	NPD5168	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.6915	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5280	Approved
0.69	Remote Similarity	NPD4694	Approved
0.69	Remote Similarity	NPD5690	Phase 2
0.6893	Remote Similarity	NPD6050	Approved
0.6893	Remote Similarity	NPD5693	Phase 1
0.6882	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5167	Approved
0.6864	Remote Similarity	NPD6054	Approved
0.6864	Remote Similarity	NPD6059	Approved
0.686	Remote Similarity	NPD6616	Approved
0.686	Remote Similarity	NPD6336	Discontinued
0.6847	Remote Similarity	NPD6412	Phase 2
0.6822	Remote Similarity	NPD4225	Approved
0.6803	Remote Similarity	NPD8293	Discontinued
0.6803	Remote Similarity	NPD7078	Approved
0.6796	Remote Similarity	NPD5692	Phase 3
0.6792	Remote Similarity	NPD7732	Phase 3
0.6762	Remote Similarity	NPD6001	Approved
0.675	Remote Similarity	NPD6370	Approved
0.6735	Remote Similarity	NPD5369	Approved
0.6733	Remote Similarity	NPD4138	Approved
0.6733	Remote Similarity	NPD4693	Phase 3
0.6733	Remote Similarity	NPD4689	Approved
0.6733	Remote Similarity	NPD4688	Approved
0.6733	Remote Similarity	NPD4623	Approved
0.6733	Remote Similarity	NPD4690	Approved
0.6733	Remote Similarity	NPD5205	Approved
0.6733	Remote Similarity	NPD4519	Discontinued
0.6731	Remote Similarity	NPD5694	Approved
0.6726	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6015	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