NPASS Compound

Structure

NPC130485 OpenBabel07101718312D 21 22 0 0 1 0 0 0 0 0999 V2000 1.7321 -2.0000 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 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 4.3301 -0.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 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 -0.8660 -0.5000 0.0000 C 0 0 1 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 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 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 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 7 1 0 0 0 0 5 9 2 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 2 1 6 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 1 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 6 0 0 0 13 14 1 0 0 0 0 13 19 1 1 0 0 0 14 21 1 6 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.13
Volume:	293.079
LogP:	1.654
LogD:	1.42
LogS:	-2.056
# Rotatable Bonds:	3
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.587
Synthetic Accessibility Score:	3.752
Fsp3:	0.533
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:	-5.467
MDCK Permeability:	1.4932772501197178e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.766
Human Intestinal Absorption (HIA):	0.539
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.611
Plasma Protein Binding (PPB):	84.85114288330078%
Volume Distribution (VD):	0.842
Pgp-substrate:	14.160738945007324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.303
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.483
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.111

ADMET: Excretion

Clearance (CL):	10.914
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.553
AMES Toxicity:	0.187
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.391
Carcinogencity:	0.31
Eye Corrosion:	0.03
Eye Irritation:	0.515
Respiratory Toxicity:	0.526

Download Data

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

Natural Product: NPC130485

Natural Product ID:	NPC130485
*Common Name:**	Ampelomin G
IUPAC Name:	[(1R,2R,3S,4S,6S)-2,3,6-trihydroxy-4-methylcyclohexyl] 2-hydroxy-6-methylbenzoate
Synonyms:	Ampelomin G
Standard InCHIKey:	VGBCTBWNONOTSR-XUNJKSNWSA-N
Standard InCHI:	InChI=1S/C15H20O6/c1-7-4-3-5-9(16)11(7)15(20)21-14-10(17)6-8(2)12(18)13(14)19/h3-5,8,10,12-14,16-19H,6H2,1-2H3/t8-,10-,12-,13+,14+/m0/s1
SMILES:	Cc1cccc(c1C(=O)O[C@@H]1[C@H](C[C@H](C)[C@@H]([C@H]1O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550967
PubChem CID:	25227594
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004700] o-Hydroxybenzoic acid esters

*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
NPO32705	ampelomyces sp.	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19193024]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1740000.0	nM	PMID[529913]

☑ 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 NPC130485 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	299
0.1-0.2	1170
0.2-0.3	2743
0.3-0.4	6202
0.4-0.5	10999
0.5-0.6	5545
0.6-0.7	6023
0.7-0.8	9030
0.8-0.85	559
0.85-0.9	121
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9203	High Similarity	NPC197666
0.9203	High Similarity	NPC126739
0.9071	High Similarity	NPC158472
0.8986	High Similarity	NPC142027
0.898	High Similarity	NPC167903
0.8889	High Similarity	NPC83272
0.8873	High Similarity	NPC158634
0.8865	High Similarity	NPC32360
0.8865	High Similarity	NPC247409
0.8849	High Similarity	NPC27407
0.8832	High Similarity	NPC214702
0.8832	High Similarity	NPC470831
0.8819	High Similarity	NPC210425
0.8819	High Similarity	NPC86373
0.8819	High Similarity	NPC280404
0.8819	High Similarity	NPC277426
0.8794	High Similarity	NPC33144
0.8794	High Similarity	NPC94248
0.8794	High Similarity	NPC478200
0.8794	High Similarity	NPC212693
0.8786	High Similarity	NPC235115
0.8784	High Similarity	NPC70016
0.8784	High Similarity	NPC215921
0.8767	High Similarity	NPC81835
0.8767	High Similarity	NPC476463
0.8741	High Similarity	NPC244923
0.8733	High Similarity	NPC478230
0.8733	High Similarity	NPC170189
0.8733	High Similarity	NPC208173
0.8733	High Similarity	NPC69043
0.8732	High Similarity	NPC105456
0.8732	High Similarity	NPC139634
0.8732	High Similarity	NPC268052
0.8732	High Similarity	NPC134969
0.8725	High Similarity	NPC184284
0.8725	High Similarity	NPC76041
0.8723	High Similarity	NPC261292
0.8723	High Similarity	NPC70380
0.8723	High Similarity	NPC301915
0.8705	High Similarity	NPC153783
0.8699	High Similarity	NPC85734
0.8699	High Similarity	NPC473023
0.8699	High Similarity	NPC32058
0.869	High Similarity	NPC103910
0.8684	High Similarity	NPC470339
0.8681	High Similarity	NPC474385
0.8681	High Similarity	NPC82913
0.8671	High Similarity	NPC155205
0.8667	High Similarity	NPC281477
0.8662	High Similarity	NPC472602
0.8662	High Similarity	NPC191835
0.8658	High Similarity	NPC200773
0.8658	High Similarity	NPC240768
0.8652	High Similarity	NPC291454
0.8649	High Similarity	NPC237440
0.8649	High Similarity	NPC270160
0.8639	High Similarity	NPC210320
0.8639	High Similarity	NPC53362
0.8639	High Similarity	NPC166583
0.863	High Similarity	NPC257558
0.8627	High Similarity	NPC472055
0.8621	High Similarity	NPC469542
0.8621	High Similarity	NPC471731
0.8621	High Similarity	NPC478202
0.8621	High Similarity	NPC51106
0.8611	High Similarity	NPC472604
0.8611	High Similarity	NPC313123
0.8611	High Similarity	NPC478217
0.8611	High Similarity	NPC53649
0.8611	High Similarity	NPC472035
0.8611	High Similarity	NPC478201
0.8611	High Similarity	NPC472605
0.8609	High Similarity	NPC16082
0.8609	High Similarity	NPC472890
0.8609	High Similarity	NPC82592
0.8601	High Similarity	NPC471819
0.8601	High Similarity	NPC88269
0.86	High Similarity	NPC478224
0.86	High Similarity	NPC295646
0.86	High Similarity	NPC115249
0.86	High Similarity	NPC478220
0.8592	High Similarity	NPC71256
0.8591	High Similarity	NPC56204
0.8591	High Similarity	NPC472891
0.8591	High Similarity	NPC469619
0.8591	High Similarity	NPC469670
0.8581	High Similarity	NPC215711
0.8581	High Similarity	NPC73411
0.8562	High Similarity	NPC478203
0.8562	High Similarity	NPC257025
0.8562	High Similarity	NPC151607
0.8562	High Similarity	NPC42540
0.8562	High Similarity	NPC210966
0.8562	High Similarity	NPC126882
0.8561	High Similarity	NPC219892
0.8561	High Similarity	NPC189823
0.8561	High Similarity	NPC7012
0.8553	High Similarity	NPC227062
0.8552	High Similarity	NPC471733
0.8543	High Similarity	NPC478231
0.8543	High Similarity	NPC185103
0.8543	High Similarity	NPC137301
0.8542	High Similarity	NPC37992
0.8542	High Similarity	NPC147542
0.8542	High Similarity	NPC472601
0.8542	High Similarity	NPC42262
0.8542	High Similarity	NPC64664
0.8542	High Similarity	NPC327916
0.8542	High Similarity	NPC472600
0.8542	High Similarity	NPC241349
0.8542	High Similarity	NPC220496
0.8542	High Similarity	NPC32749
0.8533	High Similarity	NPC205918
0.8533	High Similarity	NPC207346
0.8533	High Similarity	NPC46564
0.8531	High Similarity	NPC221104
0.8523	High Similarity	NPC476684
0.8514	High Similarity	NPC472036
0.8511	High Similarity	NPC175943
0.8511	High Similarity	NPC474097
0.85	High Similarity	NPC17843
0.8497	Intermediate Similarity	NPC478225
0.8497	Intermediate Similarity	NPC77679
0.8497	Intermediate Similarity	NPC190020
0.8497	Intermediate Similarity	NPC472889
0.8497	Intermediate Similarity	NPC84935
0.8497	Intermediate Similarity	NPC257309
0.8493	Intermediate Similarity	NPC258307
0.8493	Intermediate Similarity	NPC476473
0.8493	Intermediate Similarity	NPC159721
0.8487	Intermediate Similarity	NPC199926
0.8487	Intermediate Similarity	NPC478221
0.8487	Intermediate Similarity	NPC175192
0.8483	Intermediate Similarity	NPC472603
0.8483	Intermediate Similarity	NPC475730
0.8483	Intermediate Similarity	NPC67650
0.8483	Intermediate Similarity	NPC1704
0.8483	Intermediate Similarity	NPC470842
0.8483	Intermediate Similarity	NPC257003
0.8478	Intermediate Similarity	NPC247250
0.8478	Intermediate Similarity	NPC767
0.8477	Intermediate Similarity	NPC474533
0.8477	Intermediate Similarity	NPC474534
0.8472	Intermediate Similarity	NPC216312
0.8472	Intermediate Similarity	NPC471602
0.8472	Intermediate Similarity	NPC256463
0.8472	Intermediate Similarity	NPC29771
0.8472	Intermediate Similarity	NPC299405
0.8472	Intermediate Similarity	NPC111422
0.8472	Intermediate Similarity	NPC52358
0.8472	Intermediate Similarity	NPC476477
0.8472	Intermediate Similarity	NPC306835
0.8467	Intermediate Similarity	NPC96501
0.8467	Intermediate Similarity	NPC179178
0.8462	Intermediate Similarity	NPC135837
0.8462	Intermediate Similarity	NPC62907
0.8456	Intermediate Similarity	NPC265910
0.8456	Intermediate Similarity	NPC221352
0.8456	Intermediate Similarity	NPC94781
0.8456	Intermediate Similarity	NPC91475
0.8451	Intermediate Similarity	NPC254832
0.8451	Intermediate Similarity	NPC229638
0.8451	Intermediate Similarity	NPC71108
0.8451	Intermediate Similarity	NPC29317
0.8451	Intermediate Similarity	NPC176102
0.8451	Intermediate Similarity	NPC267539
0.8451	Intermediate Similarity	NPC204257
0.8446	Intermediate Similarity	NPC120536
0.8446	Intermediate Similarity	NPC63918
0.844	Intermediate Similarity	NPC43627
0.844	Intermediate Similarity	NPC289572
0.844	Intermediate Similarity	NPC157478
0.844	Intermediate Similarity	NPC295406
0.844	Intermediate Similarity	NPC200422
0.8431	Intermediate Similarity	NPC150227
0.8425	Intermediate Similarity	NPC250755
0.8425	Intermediate Similarity	NPC322112
0.8425	Intermediate Similarity	NPC469579
0.8425	Intermediate Similarity	NPC474300
0.8421	Intermediate Similarity	NPC478218
0.8414	Intermediate Similarity	NPC168471
0.8411	Intermediate Similarity	NPC204350
0.8403	Intermediate Similarity	NPC9121
0.8403	Intermediate Similarity	NPC472403
0.8403	Intermediate Similarity	NPC177307
0.8403	Intermediate Similarity	NPC475974
0.84	Intermediate Similarity	NPC44378
0.84	Intermediate Similarity	NPC280753
0.8394	Intermediate Similarity	NPC240744
0.8394	Intermediate Similarity	NPC167055
0.8389	Intermediate Similarity	NPC471734
0.838	Intermediate Similarity	NPC474394
0.838	Intermediate Similarity	NPC106406
0.8378	Intermediate Similarity	NPC472034
0.8377	Intermediate Similarity	NPC302258
0.8377	Intermediate Similarity	NPC246466
0.8377	Intermediate Similarity	NPC478226
0.8369	Intermediate Similarity	NPC470160
0.8367	Intermediate Similarity	NPC21873
0.8367	Intermediate Similarity	NPC472610

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 NPC130485 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	781
0.2-0.3	1577
0.3-0.4	2550
0.4-0.5	2103
0.5-0.6	1131
0.6-0.7	574
0.7-0.8	178
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8472	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD2935	Discontinued
0.8056	Intermediate Similarity	NPD230	Phase 1
0.8013	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD1934	Approved
0.7949	Intermediate Similarity	NPD2801	Approved
0.7949	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6232	Discontinued
0.7926	Intermediate Similarity	NPD9493	Approved
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7898	Intermediate Similarity	NPD3817	Phase 2
0.7895	Intermediate Similarity	NPD2532	Approved
0.7895	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD2534	Approved
0.7871	Intermediate Similarity	NPD4380	Phase 2
0.7857	Intermediate Similarity	NPD8150	Discontinued
0.7838	Intermediate Similarity	NPD1551	Phase 2
0.7834	Intermediate Similarity	NPD7819	Suspended
0.7829	Intermediate Similarity	NPD1511	Approved
0.7829	Intermediate Similarity	NPD6799	Approved
0.7815	Intermediate Similarity	NPD6190	Approved
0.7808	Intermediate Similarity	NPD447	Suspended
0.7805	Intermediate Similarity	NPD5844	Phase 1
0.7799	Intermediate Similarity	NPD7075	Discontinued
0.7792	Intermediate Similarity	NPD5403	Approved
0.7748	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD4628	Phase 3
0.7736	Intermediate Similarity	NPD3882	Suspended
0.7736	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6166	Phase 2
0.7727	Intermediate Similarity	NPD1512	Approved
0.7725	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7054	Approved
0.7688	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD9545	Approved
0.7674	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD5401	Approved
0.7658	Intermediate Similarity	NPD6801	Discontinued
0.7651	Intermediate Similarity	NPD7074	Phase 3
0.7651	Intermediate Similarity	NPD1510	Phase 2
0.7651	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7472	Approved
0.7643	Intermediate Similarity	NPD6599	Discontinued
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.7632	Intermediate Similarity	NPD3750	Approved
0.7622	Intermediate Similarity	NPD1203	Approved
0.7619	Intermediate Similarity	NPD943	Approved
0.7619	Intermediate Similarity	NPD1240	Approved
0.7616	Intermediate Similarity	NPD1549	Phase 2
0.7605	Intermediate Similarity	NPD6797	Phase 2
0.7603	Intermediate Similarity	NPD3764	Approved
0.76	Intermediate Similarity	NPD5404	Approved
0.76	Intermediate Similarity	NPD5408	Approved
0.76	Intermediate Similarity	NPD5406	Approved
0.76	Intermediate Similarity	NPD5405	Approved
0.7589	Intermediate Similarity	NPD1201	Approved
0.7574	Intermediate Similarity	NPD8313	Approved
0.7574	Intermediate Similarity	NPD8312	Approved
0.756	Intermediate Similarity	NPD6559	Discontinued
0.756	Intermediate Similarity	NPD7251	Discontinued
0.7548	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD37	Approved
0.7535	Intermediate Similarity	NPD9717	Approved
0.7531	Intermediate Similarity	NPD6234	Discontinued
0.7517	Intermediate Similarity	NPD1607	Approved
0.7516	Intermediate Similarity	NPD7768	Phase 2
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD4965	Approved
0.7516	Intermediate Similarity	NPD4966	Approved
0.7515	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD5494	Approved
0.7468	Intermediate Similarity	NPD3226	Approved
0.7468	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6832	Phase 2
0.7457	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6959	Discontinued
0.7436	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2346	Discontinued
0.7434	Intermediate Similarity	NPD7266	Discontinued
0.7425	Intermediate Similarity	NPD3751	Discontinued
0.7417	Intermediate Similarity	NPD2799	Discontinued
0.7417	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3787	Discontinued
0.7383	Intermediate Similarity	NPD4060	Phase 1
0.7381	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1164	Approved
0.7375	Intermediate Similarity	NPD7411	Suspended
0.7368	Intermediate Similarity	NPD2796	Approved
0.7365	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD411	Approved
0.7341	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD74	Approved
0.7333	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD9266	Approved
0.7333	Intermediate Similarity	NPD7199	Phase 2
0.7325	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7228	Approved
0.7308	Intermediate Similarity	NPD3300	Phase 2
0.7303	Intermediate Similarity	NPD3748	Approved
0.7297	Intermediate Similarity	NPD3027	Phase 3
0.7296	Intermediate Similarity	NPD1653	Approved
0.7294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD9269	Phase 2
0.7292	Intermediate Similarity	NPD1608	Approved
0.729	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD8166	Discontinued
0.7289	Intermediate Similarity	NPD5710	Approved
0.7289	Intermediate Similarity	NPD5711	Approved
0.7288	Intermediate Similarity	NPD6535	Approved
0.7288	Intermediate Similarity	NPD6534	Approved
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7390	Discontinued
0.726	Intermediate Similarity	NPD2797	Approved
0.7259	Intermediate Similarity	NPD9267	Approved
0.7259	Intermediate Similarity	NPD9263	Approved
0.7259	Intermediate Similarity	NPD9264	Approved
0.7256	Intermediate Similarity	NPD3749	Approved
0.7253	Intermediate Similarity	NPD7435	Discontinued
0.725	Intermediate Similarity	NPD3455	Phase 2
0.7248	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1933	Approved
0.7213	Intermediate Similarity	NPD8319	Approved
0.7213	Intermediate Similarity	NPD8320	Phase 1
0.7211	Intermediate Similarity	NPD1019	Discontinued
0.7211	Intermediate Similarity	NPD2798	Approved
0.7208	Intermediate Similarity	NPD5762	Approved
0.7208	Intermediate Similarity	NPD5763	Approved
0.7202	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6233	Phase 2
0.7192	Intermediate Similarity	NPD1283	Approved
0.719	Intermediate Similarity	NPD7033	Discontinued
0.7184	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6782	Approved
0.7182	Intermediate Similarity	NPD6777	Approved
0.7182	Intermediate Similarity	NPD6781	Approved
0.7182	Intermediate Similarity	NPD6778	Approved
0.7182	Intermediate Similarity	NPD6776	Approved
0.7182	Intermediate Similarity	NPD6780	Approved
0.7182	Intermediate Similarity	NPD6779	Approved
0.7171	Intermediate Similarity	NPD6653	Approved
0.717	Intermediate Similarity	NPD6273	Approved
0.7167	Intermediate Similarity	NPD7699	Phase 2
0.7167	Intermediate Similarity	NPD7700	Phase 2
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2438	Suspended
0.7133	Intermediate Similarity	NPD2313	Discontinued
0.7133	Intermediate Similarity	NPD3268	Approved
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD9268	Approved
0.7115	Intermediate Similarity	NPD1652	Phase 2
0.7108	Intermediate Similarity	NPD919	Approved
0.7107	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6823	Phase 2
0.7103	Intermediate Similarity	NPD422	Phase 1
0.7097	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6005	Phase 3
0.7097	Intermediate Similarity	NPD6004	Phase 3
0.7097	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6002	Phase 3
0.7095	Intermediate Similarity	NPD5647	Approved
0.7095	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6663	Approved
0.7086	Intermediate Similarity	NPD520	Approved
0.7083	Intermediate Similarity	NPD17	Approved
0.707	Intermediate Similarity	NPD7003	Approved
0.7047	Intermediate Similarity	NPD9494	Approved
0.7047	Intermediate Similarity	NPD5736	Approved
0.7039	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6212	Phase 3
0.7039	Intermediate Similarity	NPD6213	Phase 3
0.7039	Intermediate Similarity	NPD2979	Phase 3
0.7034	Intermediate Similarity	NPD3496	Discontinued
0.7032	Intermediate Similarity	NPD6099	Approved
0.7032	Intermediate Similarity	NPD6100	Approved
0.7024	Intermediate Similarity	NPD8127	Discontinued
0.7021	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9281	Approved
0.7021	Intermediate Similarity	NPD7874	Approved
0.7021	Intermediate Similarity	NPD2629	Approved
0.7019	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD920	Approved
0.7006	Intermediate Similarity	NPD2800	Approved
0.7	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1091	Approved
0.6986	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1281	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