NPASS Compound

Structure

NPC473149 OpenBabel07101719512D 34 37 0 0 1 0 0 0 0 0999 V2000 -10.5820 -2.7725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6476 -2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0077 -0.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6257 -2.3567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9859 -0.6625 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0029 1.7213 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 -7.3386 -1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2949 -1.6136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0733 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3604 -0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0247 1.5134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6913 -1.7330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2730 -1.8215 0.0000 O 0 0 0 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 -6.0514 -0.0388 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 4 1 0 0 0 0 2 11 2 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 13 2 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 7 31 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 21 1 0 0 0 0 13 30 1 0 0 0 0 14 6 1 1 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 32 1 6 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 16 33 1 0 0 0 0 17 12 1 1 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 20 1 0 0 0 0 19 27 1 6 0 0 0 20 23 1 0 0 0 0 20 28 1 1 0 0 0 21 29 2 0 0 0 0 21 32 1 0 0 0 0 22 31 1 0 0 0 0 22 34 1 6 0 0 0 23 33 1 0 0 0 0 23 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.16
Volume:	453.012
LogP:	0.756
LogD:	0.589
LogS:	-2.576
# Rotatable Bonds:	8
TPSA:	164.37
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	4.629
Fsp3:	0.522
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:	-5.83
MDCK Permeability:	8.639206498628482e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.228
Human Intestinal Absorption (HIA):	0.885
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	34.606056213378906%
Volume Distribution (VD):	0.578
Pgp-substrate:	24.52776336669922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.238
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.182
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	1.969
Half-life (T1/2):	0.892

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.074
Carcinogencity:	0.878
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC473149

Natural Product ID:	NPC473149
*Common Name:**	GPKKBMBIACLQOM-DRRAMYCQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GPKKBMBIACLQOM-DRRAMYCQSA-N
Standard InCHI:	InChI=1S/C23H28O11/c1-30-13-4-2-11(3-5-13)21(29)32-15-8-12(9-24)17-14(15)6-7-31-22(17)34-23-20(28)19(27)18(26)16(10-25)33-23/h2-8,14-20,22-28H,9-10H2,1H3/t14-,15+,16+,17+,18+,19-,20+,22-,23-/m0/s1
SMILES:	COC1=CC=C(C=C1)C(=O)OC2C=C(C3C2C=COC3OC4C(C(C(C(O4)CO)O)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622808
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO33356	vitex mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33113	castilleja tenuiflora	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33328	cresentia alata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	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	6

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	35.0	%	PMID[480573]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	34.3	%	PMID[480573]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	32.8	%	PMID[480573]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<=	30.0	%	PMID[480573]

☑ 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 NPC473149 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	300
0.1-0.2	1194
0.2-0.3	2804
0.3-0.4	6337
0.4-0.5	10722
0.5-0.6	6426
0.6-0.7	8206
0.7-0.8	6333
0.8-0.85	305
0.85-0.9	60
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC473281
0.9643	High Similarity	NPC77922
0.9433	High Similarity	NPC475213
0.9433	High Similarity	NPC152796
0.931	High Similarity	NPC478234
0.9257	High Similarity	NPC478232
0.9184	High Similarity	NPC289021
0.9184	High Similarity	NPC158546
0.9178	High Similarity	NPC478236
0.9155	High Similarity	NPC80098
0.9149	High Similarity	NPC31745
0.9149	High Similarity	NPC220936
0.9054	High Similarity	NPC475379
0.8993	High Similarity	NPC194705
0.8973	High Similarity	NPC291153
0.8966	High Similarity	NPC296659
0.8966	High Similarity	NPC202391
0.8961	High Similarity	NPC476011
0.8954	High Similarity	NPC474936
0.8929	High Similarity	NPC114116
0.8926	High Similarity	NPC474620
0.8897	High Similarity	NPC293154
0.8889	High Similarity	NPC79908
0.8867	High Similarity	NPC203664
0.8859	High Similarity	NPC182350
0.8844	High Similarity	NPC143246
0.8844	High Similarity	NPC474268
0.8844	High Similarity	NPC475539
0.8844	High Similarity	NPC119773
0.8839	High Similarity	NPC206815
0.8836	High Similarity	NPC471028
0.8792	High Similarity	NPC96599
0.879	High Similarity	NPC130730
0.879	High Similarity	NPC301910
0.8786	High Similarity	NPC254819
0.8776	High Similarity	NPC475528
0.8767	High Similarity	NPC237872
0.8767	High Similarity	NPC116104
0.8767	High Similarity	NPC478250
0.8767	High Similarity	NPC88754
0.8767	High Similarity	NPC302286
0.8767	High Similarity	NPC263397
0.8766	High Similarity	NPC179914
0.8742	High Similarity	NPC36130
0.8742	High Similarity	NPC134905
0.8742	High Similarity	NPC478235
0.8741	High Similarity	NPC294470
0.8741	High Similarity	NPC471345
0.8733	High Similarity	NPC240592
0.8733	High Similarity	NPC117346
0.8726	High Similarity	NPC180586
0.8707	High Similarity	NPC63304
0.8701	High Similarity	NPC475663
0.8701	High Similarity	NPC286919
0.8699	High Similarity	NPC31081
0.8699	High Similarity	NPC65833
0.8699	High Similarity	NPC245219
0.8684	High Similarity	NPC229354
0.8679	High Similarity	NPC21956
0.8671	High Similarity	NPC212729
0.8671	High Similarity	NPC282551
0.8667	High Similarity	NPC111785
0.8645	High Similarity	NPC469384
0.8639	High Similarity	NPC242756
0.8627	High Similarity	NPC194095
0.8627	High Similarity	NPC327032
0.8627	High Similarity	NPC191046
0.8609	High Similarity	NPC104172
0.8609	High Similarity	NPC88886
0.8601	High Similarity	NPC169398
0.86	High Similarity	NPC189631
0.8599	High Similarity	NPC145847
0.8591	High Similarity	NPC37838
0.8591	High Similarity	NPC473147
0.8591	High Similarity	NPC474044
0.859	High Similarity	NPC138993
0.8581	High Similarity	NPC226759
0.8581	High Similarity	NPC187205
0.8581	High Similarity	NPC478240
0.8571	High Similarity	NPC10205
0.8562	High Similarity	NPC157898
0.8562	High Similarity	NPC137813
0.8544	High Similarity	NPC109990
0.8516	High Similarity	NPC471405
0.8514	High Similarity	NPC469367
0.8511	High Similarity	NPC295970
0.8497	Intermediate Similarity	NPC134819
0.8493	Intermediate Similarity	NPC49597
0.8487	Intermediate Similarity	NPC69367
0.8483	Intermediate Similarity	NPC472132
0.8472	Intermediate Similarity	NPC34456
0.8467	Intermediate Similarity	NPC212808
0.8467	Intermediate Similarity	NPC473867
0.8462	Intermediate Similarity	NPC472860
0.8462	Intermediate Similarity	NPC43638
0.8462	Intermediate Similarity	NPC133984
0.8457	Intermediate Similarity	NPC470685
0.8456	Intermediate Similarity	NPC251062
0.8456	Intermediate Similarity	NPC184464
0.8452	Intermediate Similarity	NPC475484
0.8442	Intermediate Similarity	NPC257847
0.8431	Intermediate Similarity	NPC213723
0.8431	Intermediate Similarity	NPC191154
0.8428	Intermediate Similarity	NPC120012
0.8425	Intermediate Similarity	NPC101686
0.8425	Intermediate Similarity	NPC469364
0.8425	Intermediate Similarity	NPC65262
0.8421	Intermediate Similarity	NPC161955
0.8408	Intermediate Similarity	NPC160780
0.8408	Intermediate Similarity	NPC289811
0.8408	Intermediate Similarity	NPC43761
0.8397	Intermediate Similarity	NPC127406
0.8397	Intermediate Similarity	NPC475378
0.8389	Intermediate Similarity	NPC186296
0.8378	Intermediate Similarity	NPC154262
0.8378	Intermediate Similarity	NPC7518
0.8378	Intermediate Similarity	NPC159387
0.8378	Intermediate Similarity	NPC137501
0.8377	Intermediate Similarity	NPC23253
0.8375	Intermediate Similarity	NPC294722
0.8366	Intermediate Similarity	NPC227980
0.8366	Intermediate Similarity	NPC205054
0.8366	Intermediate Similarity	NPC147224
0.8365	Intermediate Similarity	NPC41009
0.8355	Intermediate Similarity	NPC140722
0.8355	Intermediate Similarity	NPC308178
0.8355	Intermediate Similarity	NPC4958
0.8355	Intermediate Similarity	NPC218685
0.8355	Intermediate Similarity	NPC92054
0.8354	Intermediate Similarity	NPC203020
0.8354	Intermediate Similarity	NPC239966
0.8345	Intermediate Similarity	NPC471029
0.8344	Intermediate Similarity	NPC1913
0.8333	Intermediate Similarity	NPC269421
0.8333	Intermediate Similarity	NPC95090
0.8333	Intermediate Similarity	NPC27408
0.8333	Intermediate Similarity	NPC99233
0.8323	Intermediate Similarity	NPC310661
0.8323	Intermediate Similarity	NPC105827
0.8323	Intermediate Similarity	NPC259767
0.8323	Intermediate Similarity	NPC88484
0.8322	Intermediate Similarity	NPC184053
0.8312	Intermediate Similarity	NPC214454
0.8312	Intermediate Similarity	NPC106025
0.8312	Intermediate Similarity	NPC269914
0.8312	Intermediate Similarity	NPC478249
0.8312	Intermediate Similarity	NPC477240
0.8302	Intermediate Similarity	NPC224530
0.8302	Intermediate Similarity	NPC216496
0.8302	Intermediate Similarity	NPC195685
0.8302	Intermediate Similarity	NPC159579
0.8302	Intermediate Similarity	NPC85707
0.8302	Intermediate Similarity	NPC270675
0.8302	Intermediate Similarity	NPC129217
0.8302	Intermediate Similarity	NPC101636
0.8302	Intermediate Similarity	NPC477628
0.8302	Intermediate Similarity	NPC311803
0.8302	Intermediate Similarity	NPC477629
0.8302	Intermediate Similarity	NPC472859
0.8302	Intermediate Similarity	NPC210961
0.8302	Intermediate Similarity	NPC25389
0.8302	Intermediate Similarity	NPC48093
0.8302	Intermediate Similarity	NPC472994
0.8302	Intermediate Similarity	NPC259957
0.8301	Intermediate Similarity	NPC22137
0.8301	Intermediate Similarity	NPC199335
0.8293	Intermediate Similarity	NPC195972
0.8291	Intermediate Similarity	NPC76211
0.8291	Intermediate Similarity	NPC73511
0.8291	Intermediate Similarity	NPC287872
0.8291	Intermediate Similarity	NPC74319
0.828	Intermediate Similarity	NPC265480
0.828	Intermediate Similarity	NPC45165
0.828	Intermediate Similarity	NPC149368
0.8278	Intermediate Similarity	NPC210330
0.8269	Intermediate Similarity	NPC108706
0.8269	Intermediate Similarity	NPC472128
0.8269	Intermediate Similarity	NPC211158
0.8269	Intermediate Similarity	NPC83283
0.8269	Intermediate Similarity	NPC472127
0.8269	Intermediate Similarity	NPC106625
0.8269	Intermediate Similarity	NPC29763
0.8269	Intermediate Similarity	NPC87304
0.8269	Intermediate Similarity	NPC78021
0.8269	Intermediate Similarity	NPC39360
0.8269	Intermediate Similarity	NPC143851
0.8269	Intermediate Similarity	NPC210003
0.8269	Intermediate Similarity	NPC268950
0.8269	Intermediate Similarity	NPC185103
0.8264	Intermediate Similarity	NPC281798
0.8261	Intermediate Similarity	NPC139060
0.8261	Intermediate Similarity	NPC475979
0.8261	Intermediate Similarity	NPC72016
0.8258	Intermediate Similarity	NPC190217
0.8258	Intermediate Similarity	NPC267091
0.8258	Intermediate Similarity	NPC289438
0.8255	Intermediate Similarity	NPC46644
0.825	Intermediate Similarity	NPC33298
0.825	Intermediate Similarity	NPC27942
0.825	Intermediate Similarity	NPC285108

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 NPC473149 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	755
0.2-0.3	1598
0.3-0.4	2526
0.4-0.5	2214
0.5-0.6	1211
0.6-0.7	474
0.7-0.8	120
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD7685	Pre-registration
0.8228	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD4628	Phase 3
0.7848	Intermediate Similarity	NPD4380	Phase 2
0.7831	Intermediate Similarity	NPD3818	Discontinued
0.7806	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD9545	Approved
0.7784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7054	Approved
0.775	Intermediate Similarity	NPD6801	Discontinued
0.7738	Intermediate Similarity	NPD7472	Approved
0.7706	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD8455	Phase 2
0.7692	Intermediate Similarity	NPD6797	Phase 2
0.7674	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7458	Discontinued
0.7669	Intermediate Similarity	NPD7075	Discontinued
0.7662	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7251	Discontinued
0.7647	Intermediate Similarity	NPD7266	Discontinued
0.7647	Intermediate Similarity	NPD6559	Discontinued
0.7636	Intermediate Similarity	NPD7199	Phase 2
0.7633	Intermediate Similarity	NPD7074	Phase 3
0.761	Intermediate Similarity	NPD1653	Approved
0.7607	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7808	Phase 3
0.7593	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6799	Approved
0.7569	Intermediate Similarity	NPD1091	Approved
0.7547	Intermediate Similarity	NPD5403	Approved
0.7531	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7411	Suspended
0.7458	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8313	Approved
0.7457	Intermediate Similarity	NPD8312	Approved
0.7452	Intermediate Similarity	NPD6190	Approved
0.744	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3817	Phase 2
0.7434	Intermediate Similarity	NPD230	Phase 1
0.7421	Intermediate Similarity	NPD5401	Approved
0.7417	Intermediate Similarity	NPD6233	Phase 2
0.7412	Intermediate Similarity	NPD7228	Approved
0.741	Intermediate Similarity	NPD6234	Discontinued
0.7407	Intermediate Similarity	NPD6599	Discontinued
0.7403	Intermediate Similarity	NPD7033	Discontinued
0.7378	Intermediate Similarity	NPD7819	Suspended
0.7372	Intermediate Similarity	NPD1549	Phase 2
0.7368	Intermediate Similarity	NPD5844	Phase 1
0.7351	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5402	Approved
0.732	Intermediate Similarity	NPD1933	Approved
0.732	Intermediate Similarity	NPD6355	Discontinued
0.7317	Intermediate Similarity	NPD1934	Approved
0.7315	Intermediate Similarity	NPD5647	Approved
0.7312	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1510	Phase 2
0.7278	Intermediate Similarity	NPD3750	Approved
0.7273	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6653	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7248	Intermediate Similarity	NPD2797	Approved
0.7244	Intermediate Similarity	NPD2796	Approved
0.7237	Intermediate Similarity	NPD3268	Approved
0.7237	Intermediate Similarity	NPD3764	Approved
0.7237	Intermediate Similarity	NPD6798	Discontinued
0.7229	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7097	Phase 1
0.7219	Intermediate Similarity	NPD8127	Discontinued
0.7215	Intermediate Similarity	NPD1652	Phase 2
0.7205	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2798	Approved
0.72	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6166	Phase 2
0.7193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2801	Approved
0.7162	Intermediate Similarity	NPD1608	Approved
0.7162	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1240	Approved
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD2935	Discontinued
0.7126	Intermediate Similarity	NPD5353	Approved
0.7122	Intermediate Similarity	NPD1358	Approved
0.7105	Intermediate Similarity	NPD6832	Phase 2
0.7099	Intermediate Similarity	NPD2533	Approved
0.7099	Intermediate Similarity	NPD2532	Approved
0.7099	Intermediate Similarity	NPD2534	Approved
0.7099	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5124	Phase 1
0.7097	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3882	Suspended
0.7078	Intermediate Similarity	NPD4062	Phase 3
0.7076	Intermediate Similarity	NPD6232	Discontinued
0.7074	Intermediate Similarity	NPD7999	Approved
0.707	Intermediate Similarity	NPD2799	Discontinued
0.707	Intermediate Similarity	NPD3748	Approved
0.7067	Intermediate Similarity	NPD3225	Approved
0.7067	Intermediate Similarity	NPD1876	Approved
0.7066	Intermediate Similarity	NPD1465	Phase 2
0.7059	Intermediate Similarity	NPD7435	Discontinued
0.7059	Intermediate Similarity	NPD5494	Approved
0.7056	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7473	Discontinued
0.7051	Intermediate Similarity	NPD1607	Approved
0.705	Intermediate Similarity	NPD3134	Approved
0.7047	Intermediate Similarity	NPD7930	Approved
0.7047	Intermediate Similarity	NPD3972	Approved
0.7037	Intermediate Similarity	NPD7583	Approved
0.7037	Intermediate Similarity	NPD1511	Approved
0.703	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1551	Phase 2
0.702	Intermediate Similarity	NPD1203	Approved
0.702	Intermediate Similarity	NPD6362	Approved
0.7019	Intermediate Similarity	NPD2354	Approved
0.7019	Intermediate Similarity	NPD3887	Approved
0.7011	Intermediate Similarity	NPD7799	Discontinued
0.7011	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7585	Approved
0.6989	Remote Similarity	NPD6779	Approved
0.6989	Remote Similarity	NPD6781	Approved
0.6989	Remote Similarity	NPD6776	Approved
0.6989	Remote Similarity	NPD6782	Approved
0.6989	Remote Similarity	NPD6780	Approved
0.6989	Remote Similarity	NPD6777	Approved
0.6989	Remote Similarity	NPD6778	Approved
0.6987	Remote Similarity	NPD447	Suspended
0.6987	Remote Similarity	NPD4340	Discontinued
0.6982	Remote Similarity	NPD7768	Phase 2
0.6975	Remote Similarity	NPD7440	Discontinued
0.6962	Remote Similarity	NPD4308	Phase 3
0.6959	Remote Similarity	NPD17	Approved
0.6957	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7003	Approved
0.6951	Remote Similarity	NPD1512	Approved
0.6948	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6386	Approved
0.6946	Remote Similarity	NPD6385	Approved
0.6944	Remote Similarity	NPD1241	Discontinued
0.6941	Remote Similarity	NPD3749	Approved
0.6937	Remote Similarity	NPD2424	Discontinued
0.6928	Remote Similarity	NPD3226	Approved
0.6918	Remote Similarity	NPD9493	Approved
0.6918	Remote Similarity	NPD2438	Suspended
0.6909	Remote Similarity	NPD920	Approved
0.6908	Remote Similarity	NPD3266	Approved
0.6908	Remote Similarity	NPD3267	Approved
0.6903	Remote Similarity	NPD2313	Discontinued
0.6899	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.689	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7028	Phase 2
0.6879	Remote Similarity	NPD3787	Discontinued
0.6875	Remote Similarity	NPD5762	Approved
0.6875	Remote Similarity	NPD8151	Discontinued
0.6875	Remote Similarity	NPD5763	Approved
0.6875	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5058	Phase 3
0.6871	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD422	Phase 1
0.6867	Remote Similarity	NPD3705	Approved
0.6864	Remote Similarity	NPD5760	Phase 2
0.6864	Remote Similarity	NPD5761	Phase 2
0.6863	Remote Similarity	NPD1019	Discontinued
0.6859	Remote Similarity	NPD7584	Approved
0.6854	Remote Similarity	NPD6765	Approved
0.6854	Remote Similarity	NPD6764	Approved
0.6852	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4110	Phase 3
0.6845	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7874	Approved
0.6832	Remote Similarity	NPD5958	Discontinued
0.6824	Remote Similarity	NPD1894	Discontinued
0.6821	Remote Similarity	NPD1481	Phase 2
0.6821	Remote Similarity	NPD6959	Discontinued
0.6818	Remote Similarity	NPD2861	Phase 2
0.6815	Remote Similarity	NPD3142	Approved
0.6815	Remote Similarity	NPD3140	Approved
0.6806	Remote Similarity	NPD969	Suspended
0.6804	Remote Similarity	NPD7783	Phase 2
0.6804	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3451	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data