NPASS Compound

Structure

NPC114183 OpenBabel07101718192D 25 27 0 0 0 0 0 0 0 0999 V2000 -5.1962 0.0000 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 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -1.7321 2.0000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -3.4641 3.0000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 16 1 0 0 0 0 9 19 2 0 0 0 0 10 13 1 0 0 0 0 10 21 2 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 17 2 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 22 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.13
Volume:	351.666
LogP:	3.967
LogD:	2.095
LogS:	-3.949
# Rotatable Bonds:	1
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.613
Synthetic Accessibility Score:	3.567
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.846
MDCK Permeability:	1.4554977497027721e-05
Pgp-inhibitor:	0.531
Pgp-substrate:	0.409
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	0.742
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	98.30622100830078%
Volume Distribution (VD):	0.491
Pgp-substrate:	1.3883225917816162%

ADMET: Metabolism

CYP1A2-inhibitor:	0.941
CYP1A2-substrate:	0.872
CYP2C19-inhibitor:	0.473
CYP2C19-substrate:	0.219
CYP2C9-inhibitor:	0.79
CYP2C9-substrate:	0.525
CYP2D6-inhibitor:	0.52
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.523
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	0.801
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.331
Skin Sensitization:	0.496
Carcinogencity:	0.459
Eye Corrosion:	0.003
Eye Irritation:	0.418
Respiratory Toxicity:	0.688

Download Data

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

Natural Product: NPC114183

Natural Product ID:	NPC114183
*Common Name:**	Garveatin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QBGFUEPOOHBTEK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-8-6-11-7-12-15(16(22)9(2)19(25)20(12,4)5)18(24)14(11)17(23)13(8)10(3)21/h6-7,23-25H,1-5H3
SMILES:	CC1=C(O)C(c2c(C1=O)c(O)c1c(c2)cc(c(c1O)C(=O)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505821
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO2240	Garveia annulata	Species	Bougainvilliidae	Eukaryota	n.a.	Northeastern Pacific	n.a.	PMID[17067170]
NPO2240	Garveia annulata	Species	Bougainvilliidae	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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	Ki	=	3200.0	nM	PMID[538825]

☑ 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 NPC114183 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	362
0.1-0.2	1557
0.2-0.3	3334
0.3-0.4	9009
0.4-0.5	10653
0.5-0.6	5561
0.6-0.7	7175
0.7-0.8	4419
0.8-0.85	461
0.85-0.9	149
0.9-0.95	11
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC270899
0.9921	High Similarity	NPC12070
0.9844	High Similarity	NPC249272
0.9692	High Similarity	NPC53001
0.9618	High Similarity	NPC87723
0.9173	High Similarity	NPC191976
0.9141	High Similarity	NPC160499
0.9091	High Similarity	NPC267205
0.8993	High Similarity	NPC12402
0.8971	High Similarity	NPC242994
0.8971	High Similarity	NPC138099
0.8963	High Similarity	NPC471905
0.8939	High Similarity	NPC17083
0.8905	High Similarity	NPC181560
0.8905	High Similarity	NPC169452
0.8889	High Similarity	NPC118919
0.8889	High Similarity	NPC254847
0.8881	High Similarity	NPC282780
0.8881	High Similarity	NPC166480
0.8881	High Similarity	NPC475088
0.8872	High Similarity	NPC58685
0.8872	High Similarity	NPC175738
0.8855	High Similarity	NPC48248
0.8849	High Similarity	NPC163948
0.8849	High Similarity	NPC296752
0.8846	High Similarity	NPC254492
0.8841	High Similarity	NPC246638
0.8841	High Similarity	NPC110810
0.8837	High Similarity	NPC173978
0.8824	High Similarity	NPC53414
0.8824	High Similarity	NPC53206
0.8815	High Similarity	NPC290803
0.8815	High Similarity	NPC283088
0.8788	High Similarity	NPC276238
0.8788	High Similarity	NPC92624
0.8788	High Similarity	NPC109123
0.8786	High Similarity	NPC227841
0.8779	High Similarity	NPC72667
0.8777	High Similarity	NPC135524
0.8777	High Similarity	NPC193555
0.8777	High Similarity	NPC474961
0.8741	High Similarity	NPC50924
0.8722	High Similarity	NPC259942
0.8722	High Similarity	NPC55949
0.8714	High Similarity	NPC451542
0.8714	High Similarity	NPC293545
0.8714	High Similarity	NPC174905
0.8714	High Similarity	NPC313047
0.8714	High Similarity	NPC474203
0.8714	High Similarity	NPC295712
0.8712	High Similarity	NPC96024
0.8712	High Similarity	NPC282923
0.8705	High Similarity	NPC305845
0.8705	High Similarity	NPC204045
0.8696	High Similarity	NPC143438
0.8692	High Similarity	NPC199273
0.8667	High Similarity	NPC115458
0.8667	High Similarity	NPC37299
0.8667	High Similarity	NPC180261
0.8667	High Similarity	NPC225051
0.8662	High Similarity	NPC143685
0.8657	High Similarity	NPC72669
0.8657	High Similarity	NPC474517
0.8657	High Similarity	NPC41847
0.8647	High Similarity	NPC171460
0.8647	High Similarity	NPC303910
0.8647	High Similarity	NPC34414
0.8647	High Similarity	NPC146647
0.8636	High Similarity	NPC69424
0.8636	High Similarity	NPC176130
0.8636	High Similarity	NPC78364
0.8636	High Similarity	NPC471530
0.8636	High Similarity	NPC84672
0.8633	High Similarity	NPC168471
0.8626	High Similarity	NPC477454
0.8623	High Similarity	NPC473622
0.8613	High Similarity	NPC474311
0.8603	High Similarity	NPC161964
0.8603	High Similarity	NPC472262
0.8603	High Similarity	NPC44437
0.8603	High Similarity	NPC287604
0.8601	High Similarity	NPC37709
0.8601	High Similarity	NPC290194
0.8601	High Similarity	NPC34802
0.8592	High Similarity	NPC34482
0.8582	High Similarity	NPC31799
0.8582	High Similarity	NPC84266
0.8582	High Similarity	NPC471682
0.8561	High Similarity	NPC190457
0.8561	High Similarity	NPC3224
0.8561	High Similarity	NPC267846
0.8561	High Similarity	NPC473691
0.8551	High Similarity	NPC245923
0.8551	High Similarity	NPC62272
0.855	High Similarity	NPC142956
0.855	High Similarity	NPC236189
0.854	High Similarity	NPC161632
0.8531	High Similarity	NPC470570
0.8529	High Similarity	NPC48036
0.8529	High Similarity	NPC314048
0.8521	High Similarity	NPC10764
0.8521	High Similarity	NPC193703
0.8521	High Similarity	NPC471906
0.8521	High Similarity	NPC48762
0.8521	High Similarity	NPC244691
0.8521	High Similarity	NPC21599
0.8519	High Similarity	NPC244699
0.8519	High Similarity	NPC205992
0.8511	High Similarity	NPC182255
0.8511	High Similarity	NPC94076
0.8511	High Similarity	NPC257644
0.8511	High Similarity	NPC239136
0.8511	High Similarity	NPC19631
0.8507	High Similarity	NPC278928
0.8507	High Similarity	NPC474998
0.8507	High Similarity	NPC99731
0.85	High Similarity	NPC315578
0.8496	Intermediate Similarity	NPC266689
0.8496	Intermediate Similarity	NPC72158
0.8496	Intermediate Similarity	NPC169250
0.8496	Intermediate Similarity	NPC162612
0.8496	Intermediate Similarity	NPC100067
0.8496	Intermediate Similarity	NPC116513
0.8496	Intermediate Similarity	NPC23126
0.8496	Intermediate Similarity	NPC190043
0.8496	Intermediate Similarity	NPC105157
0.8496	Intermediate Similarity	NPC103356
0.8496	Intermediate Similarity	NPC30501
0.8496	Intermediate Similarity	NPC98254
0.8489	Intermediate Similarity	NPC13715
0.8489	Intermediate Similarity	NPC230811
0.8489	Intermediate Similarity	NPC4214
0.8485	Intermediate Similarity	NPC103540
0.8483	Intermediate Similarity	NPC100985
0.8483	Intermediate Similarity	NPC158338
0.8483	Intermediate Similarity	NPC97028
0.8483	Intermediate Similarity	NPC329933
0.8483	Intermediate Similarity	NPC65589
0.8483	Intermediate Similarity	NPC288036
0.8483	Intermediate Similarity	NPC97029
0.8478	Intermediate Similarity	NPC315275
0.8478	Intermediate Similarity	NPC155211
0.8478	Intermediate Similarity	NPC474813
0.8478	Intermediate Similarity	NPC272268
0.8478	Intermediate Similarity	NPC472308
0.8467	Intermediate Similarity	NPC474519
0.8462	Intermediate Similarity	NPC471683
0.8462	Intermediate Similarity	NPC154696
0.8456	Intermediate Similarity	NPC70622
0.8444	Intermediate Similarity	NPC62219
0.8444	Intermediate Similarity	NPC108129
0.844	Intermediate Similarity	NPC187843
0.844	Intermediate Similarity	NPC290550
0.8433	Intermediate Similarity	NPC21305
0.8433	Intermediate Similarity	NPC221777
0.8433	Intermediate Similarity	NPC473017
0.8429	Intermediate Similarity	NPC162939
0.8429	Intermediate Similarity	NPC26924
0.8425	Intermediate Similarity	NPC205766
0.8425	Intermediate Similarity	NPC477914
0.8421	Intermediate Similarity	NPC231774
0.8421	Intermediate Similarity	NPC328983
0.8421	Intermediate Similarity	NPC62952
0.8417	Intermediate Similarity	NPC290030
0.8417	Intermediate Similarity	NPC36868
0.8417	Intermediate Similarity	NPC305060
0.8417	Intermediate Similarity	NPC471452
0.8414	Intermediate Similarity	NPC27221
0.8414	Intermediate Similarity	NPC7025
0.8414	Intermediate Similarity	NPC256672
0.8406	Intermediate Similarity	NPC153088
0.8406	Intermediate Similarity	NPC80035
0.8403	Intermediate Similarity	NPC85393
0.8403	Intermediate Similarity	NPC271944
0.8403	Intermediate Similarity	NPC110882
0.8397	Intermediate Similarity	NPC91105
0.8397	Intermediate Similarity	NPC176208
0.8397	Intermediate Similarity	NPC307174
0.8397	Intermediate Similarity	NPC282577
0.8394	Intermediate Similarity	NPC138472
0.8394	Intermediate Similarity	NPC53896
0.8382	Intermediate Similarity	NPC471851
0.838	Intermediate Similarity	NPC73061
0.8369	Intermediate Similarity	NPC96421
0.8367	Intermediate Similarity	NPC149526
0.8367	Intermediate Similarity	NPC474417
0.8367	Intermediate Similarity	NPC72958
0.8367	Intermediate Similarity	NPC35
0.8367	Intermediate Similarity	NPC232645
0.8358	Intermediate Similarity	NPC316625
0.8358	Intermediate Similarity	NPC329205
0.8357	Intermediate Similarity	NPC416
0.8357	Intermediate Similarity	NPC61398
0.8356	Intermediate Similarity	NPC477221
0.8346	Intermediate Similarity	NPC475733
0.8346	Intermediate Similarity	NPC10926
0.8345	Intermediate Similarity	NPC245584
0.8345	Intermediate Similarity	NPC289042
0.8345	Intermediate Similarity	NPC312929
0.8345	Intermediate Similarity	NPC65005

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 NPC114183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	959
0.2-0.3	1404
0.3-0.4	2723
0.4-0.5	2208
0.5-0.6	1095
0.6-0.7	342
0.7-0.8	87
0.8-0.85	1
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD1509	Clinical (unspecified phase)
0.8786	High Similarity	NPD7390	Discontinued
0.8605	High Similarity	NPD1201	Approved
0.8551	High Similarity	NPD5405	Approved
0.8551	High Similarity	NPD5404	Approved
0.8551	High Similarity	NPD5406	Approved
0.8551	High Similarity	NPD5408	Approved
0.8485	Intermediate Similarity	NPD1470	Approved
0.7959	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD943	Approved
0.7863	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6959	Discontinued
0.782	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6232	Discontinued
0.7761	Intermediate Similarity	NPD2932	Approved
0.7736	Intermediate Similarity	NPD7473	Discontinued
0.7724	Intermediate Similarity	NPD2346	Discontinued
0.7718	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2534	Approved
0.7718	Intermediate Similarity	NPD2533	Approved
0.7718	Intermediate Similarity	NPD2532	Approved
0.7703	Intermediate Similarity	NPD3300	Phase 2
0.7692	Intermediate Similarity	NPD1607	Approved
0.7681	Intermediate Similarity	NPD1164	Approved
0.7662	Intermediate Similarity	NPD7819	Suspended
0.7655	Intermediate Similarity	NPD6100	Approved
0.7655	Intermediate Similarity	NPD6099	Approved
0.7632	Intermediate Similarity	NPD3226	Approved
0.763	Intermediate Similarity	NPD3019	Approved
0.7619	Intermediate Similarity	NPD2800	Approved
0.76	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1510	Phase 2
0.7576	Intermediate Similarity	NPD5951	Approved
0.7569	Intermediate Similarity	NPD6651	Approved
0.7552	Intermediate Similarity	NPD1240	Approved
0.7551	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2935	Discontinued
0.7462	Intermediate Similarity	NPD4750	Phase 3
0.745	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2342	Discontinued
0.7424	Intermediate Similarity	NPD7635	Approved
0.7389	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4380	Phase 2
0.7347	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3750	Approved
0.7333	Intermediate Similarity	NPD7003	Approved
0.7315	Intermediate Similarity	NPD1549	Phase 2
0.7303	Intermediate Similarity	NPD1511	Approved
0.7261	Intermediate Similarity	NPD1934	Approved
0.7254	Intermediate Similarity	NPD2798	Approved
0.7244	Intermediate Similarity	NPD6599	Discontinued
0.7222	Intermediate Similarity	NPD4625	Phase 3
0.7215	Intermediate Similarity	NPD2801	Approved
0.7208	Intermediate Similarity	NPD1512	Approved
0.7197	Intermediate Similarity	NPD7411	Suspended
0.7194	Intermediate Similarity	NPD3023	Approved
0.7194	Intermediate Similarity	NPD3026	Approved
0.7188	Intermediate Similarity	NPD3749	Approved
0.7188	Intermediate Similarity	NPD7075	Discontinued
0.7181	Intermediate Similarity	NPD2796	Approved
0.7179	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8150	Discontinued
0.7174	Intermediate Similarity	NPD3025	Approved
0.7174	Intermediate Similarity	NPD3024	Approved
0.7172	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2344	Approved
0.7125	Intermediate Similarity	NPD7768	Phase 2
0.7122	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD9266	Approved
0.7121	Intermediate Similarity	NPD74	Approved
0.7117	Intermediate Similarity	NPD5710	Approved
0.7117	Intermediate Similarity	NPD5711	Approved
0.7114	Intermediate Similarity	NPD2799	Discontinued
0.7108	Intermediate Similarity	NPD6020	Phase 2
0.7108	Intermediate Similarity	NPD5844	Phase 1
0.7107	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3972	Approved
0.708	Intermediate Similarity	NPD9493	Approved
0.707	Intermediate Similarity	NPD7458	Discontinued
0.7067	Intermediate Similarity	NPD1551	Phase 2
0.7063	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3764	Approved
0.705	Intermediate Similarity	NPD1651	Approved
0.7045	Intermediate Similarity	NPD9264	Approved
0.7045	Intermediate Similarity	NPD9267	Approved
0.7045	Intermediate Similarity	NPD9263	Approved
0.7039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD3748	Approved
0.6993	Remote Similarity	NPD1283	Approved
0.6993	Remote Similarity	NPD4628	Phase 3
0.6986	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7008	Discontinued
0.6982	Remote Similarity	NPD6559	Discontinued
0.6948	Remote Similarity	NPD2309	Approved
0.6944	Remote Similarity	NPD1203	Approved
0.6939	Remote Similarity	NPD3268	Approved
0.6937	Remote Similarity	NPD6801	Discontinued
0.6928	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1243	Approved
0.6928	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6166	Phase 2
0.6923	Remote Similarity	NPD1755	Approved
0.6914	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6663	Approved
0.689	Remote Similarity	NPD5494	Approved
0.6887	Remote Similarity	NPD4308	Phase 3
0.6883	Remote Similarity	NPD8166	Discontinued
0.6883	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6799	Approved
0.6853	Remote Similarity	NPD9269	Phase 2
0.6853	Remote Similarity	NPD4878	Approved
0.6852	Remote Similarity	NPD3817	Phase 2
0.6849	Remote Similarity	NPD5736	Approved
0.6845	Remote Similarity	NPD7177	Discontinued
0.6836	Remote Similarity	NPD6535	Approved
0.6836	Remote Similarity	NPD6534	Approved
0.6828	Remote Similarity	NPD2797	Approved
0.6824	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD411	Approved
0.6812	Remote Similarity	NPD9281	Approved
0.6809	Remote Similarity	NPD9268	Approved
0.6806	Remote Similarity	NPD4749	Approved
0.6805	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8312	Approved
0.6802	Remote Similarity	NPD8313	Approved
0.6797	Remote Similarity	NPD1809	Phase 2
0.6797	Remote Similarity	NPD844	Approved
0.6797	Remote Similarity	NPD1471	Phase 3
0.6791	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1465	Phase 2
0.6784	Remote Similarity	NPD5029	Approved
0.6784	Remote Similarity	NPD5031	Approved
0.6784	Remote Similarity	NPD5027	Approved
0.6783	Remote Similarity	NPD1281	Approved
0.678	Remote Similarity	NPD6212	Phase 3
0.678	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6213	Phase 3
0.6765	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7074	Phase 3
0.6761	Remote Similarity	NPD4626	Approved
0.6746	Remote Similarity	NPD3818	Discontinued
0.6744	Remote Similarity	NPD5028	Approved
0.6744	Remote Similarity	NPD288	Approved
0.6744	Remote Similarity	NPD5026	Approved
0.6744	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5034	Approved
0.6744	Remote Similarity	NPD4955	Approved
0.6744	Remote Similarity	NPD36	Approved
0.6744	Remote Similarity	NPD3495	Discontinued
0.6744	Remote Similarity	NPD4954	Approved
0.6742	Remote Similarity	NPD1930	Approved
0.6742	Remote Similarity	NPD1929	Approved
0.6742	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD9261	Approved
0.6738	Remote Similarity	NPD3091	Approved
0.6736	Remote Similarity	NPD9717	Approved
0.6736	Remote Similarity	NPD1608	Approved
0.6722	Remote Similarity	NPD7700	Phase 2
0.6722	Remote Similarity	NPD7699	Phase 2
0.6718	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3094	Phase 2
0.6707	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7054	Approved
0.6691	Remote Similarity	NPD497	Approved
0.6689	Remote Similarity	NPD230	Phase 1
0.6689	Remote Similarity	NPD6832	Phase 2
0.6686	Remote Similarity	NPD5037	Approved
0.6686	Remote Similarity	NPD5038	Approved
0.6686	Remote Similarity	NPD5030	Phase 2
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD846	Approved
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD3092	Approved
0.6667	Remote Similarity	NPD940	Approved
0.6648	Remote Similarity	NPD6781	Approved
0.6648	Remote Similarity	NPD6782	Approved
0.6648	Remote Similarity	NPD6779	Approved
0.6648	Remote Similarity	NPD6778	Approved
0.6648	Remote Similarity	NPD6777	Approved
0.6648	Remote Similarity	NPD6780	Approved
0.6648	Remote Similarity	NPD6776	Approved
0.6646	Remote Similarity	NPD5402	Approved
0.6644	Remote Similarity	NPD6696	Suspended
0.6643	Remote Similarity	NPD4059	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