NPASS Compound

Structure

CID51106 OpenBabel06191715382D 22 23 0 0 1 0 0 0 0 0999 V2000 -1.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -2.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 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 -3.3320 -2.6248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 0.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.1340 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 2 21 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 1 1 1 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 13 18 1 6 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.16
Volume:	318.881
LogP:	3.048
LogD:	2.788
LogS:	-2.819
# Rotatable Bonds:	1
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.78
Synthetic Accessibility Score:	3.619
Fsp3:	0.588
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:	-4.671
MDCK Permeability:	4.406086009112187e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.09
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.618

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.629
Plasma Protein Binding (PPB):	84.26435852050781%
Volume Distribution (VD):	1.177
Pgp-substrate:	8.164482116699219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.814
CYP2C19-inhibitor:	0.679
CYP2C19-substrate:	0.466
CYP2C9-inhibitor:	0.479
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.821
CYP2D6-substrate:	0.729
CYP3A4-inhibitor:	0.487
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	12.437
Half-life (T1/2):	0.722

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.179
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.791
Carcinogencity:	0.046
Eye Corrosion:	0.023
Eye Irritation:	0.738
Respiratory Toxicity:	0.364

Download Data

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

Natural Product: NPC51106

Natural Product ID:	NPC51106
*Common Name:**	DGMDZTUKWDQSTB-YPMHNXCESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DGMDZTUKWDQSTB-YPMHNXCESA-N
Standard InCHI:	InChI=1S/C17H24O5/c1-11-7-8-13(18)6-4-3-5-12-9-14(19)10-15(21-2)16(12)17(20)22-11/h9-11,13,18-19H,3-8H2,1-2H3/t11-,13+/m1/s1
SMILES:	COc1cc(O)cc2c1C(=O)O[C@H](C)CC[C@H](CCCC2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3319026
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO32516	ficus auriculata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25008455]
NPO16865.1	Prunus serrulata var. spontanea	Varieties	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16865.1	Prunus serrulata var. spontanea	Varieties	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16885	Phonus arborescens	Species	Asteraceae	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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	3.97	%	PMID[524979]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	-6.67	%	PMID[524979]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.1	%	PMID[524979]

☑ 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 NPC51106 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	323
0.1-0.2	1348
0.2-0.3	3574
0.3-0.4	7650
0.4-0.5	10862
0.5-0.6	3638
0.6-0.7	5546
0.7-0.8	7035
0.8-0.85	2137
0.85-0.9	435
0.9-0.95	122
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC67650
0.9853	High Similarity	NPC1704
0.9781	High Similarity	NPC474385
0.971	High Similarity	NPC469542
0.971	High Similarity	NPC472006
0.9643	High Similarity	NPC107625
0.964	High Similarity	NPC86373
0.964	High Similarity	NPC210425
0.964	High Similarity	NPC277426
0.964	High Similarity	NPC280404
0.9638	High Similarity	NPC469579
0.9632	High Similarity	NPC212693
0.9632	High Similarity	NPC94248
0.9574	High Similarity	NPC472036
0.9565	High Similarity	NPC475730
0.9559	High Similarity	NPC70380
0.9559	High Similarity	NPC135837
0.951	High Similarity	NPC469619
0.951	High Similarity	NPC469670
0.9489	High Similarity	NPC191835
0.9444	High Similarity	NPC200773
0.9444	High Similarity	NPC240768
0.9444	High Similarity	NPC70016
0.9444	High Similarity	NPC215921
0.9441	High Similarity	NPC237440
0.9441	High Similarity	NPC270160
0.9437	High Similarity	NPC210320
0.9433	High Similarity	NPC472034
0.9424	High Similarity	NPC90411
0.9424	High Similarity	NPC158634
0.942	High Similarity	NPC139634
0.942	High Similarity	NPC105456
0.942	High Similarity	NPC32360
0.9412	High Similarity	NPC182496
0.9412	High Similarity	NPC180905
0.9371	High Similarity	NPC240253
0.9371	High Similarity	NPC471642
0.9371	High Similarity	NPC73411
0.9371	High Similarity	NPC240622
0.9371	High Similarity	NPC471641
0.9371	High Similarity	NPC215711
0.9366	High Similarity	NPC472033
0.9357	High Similarity	NPC250755
0.9353	High Similarity	NPC158472
0.9348	High Similarity	NPC472602
0.9348	High Similarity	NPC33144
0.9348	High Similarity	NPC478200
0.9306	High Similarity	NPC476684
0.9301	High Similarity	NPC8817
0.9296	High Similarity	NPC134621
0.9296	High Similarity	NPC83272
0.9286	High Similarity	NPC478217
0.9286	High Similarity	NPC472605
0.9286	High Similarity	NPC472604
0.9286	High Similarity	NPC313123
0.9286	High Similarity	NPC53649
0.9286	High Similarity	NPC244923
0.9281	High Similarity	NPC268052
0.9275	High Similarity	NPC71256
0.9265	High Similarity	NPC153783
0.9252	High Similarity	NPC16082
0.9252	High Similarity	NPC99381
0.9252	High Similarity	NPC82592
0.9247	High Similarity	NPC273483
0.9247	High Similarity	NPC167903
0.9241	High Similarity	NPC179178
0.9236	High Similarity	NPC153417
0.9231	High Similarity	NPC470357
0.9231	High Similarity	NPC237208
0.9225	High Similarity	NPC95123
0.9225	High Similarity	NPC66404
0.9214	High Similarity	NPC165172
0.9214	High Similarity	NPC472600
0.9214	High Similarity	NPC472601
0.9209	High Similarity	NPC475974
0.9203	High Similarity	NPC235115
0.9184	High Similarity	NPC281477
0.9172	High Similarity	NPC77325
0.9172	High Similarity	NPC4423
0.9167	High Similarity	NPC14098
0.9161	High Similarity	NPC75694
0.9161	High Similarity	NPC257558
0.9161	High Similarity	NPC312789
0.9161	High Similarity	NPC29577
0.9155	High Similarity	NPC471731
0.9155	High Similarity	NPC478202
0.9155	High Similarity	NPC159721
0.9149	High Similarity	NPC478201
0.9149	High Similarity	NPC472035
0.9149	High Similarity	NPC472603
0.9137	High Similarity	NPC149372
0.9137	High Similarity	NPC474849
0.9137	High Similarity	NPC178467
0.9137	High Similarity	NPC474771
0.9137	High Similarity	NPC194579
0.9137	High Similarity	NPC65837
0.9128	High Similarity	NPC77679
0.9128	High Similarity	NPC84935
0.9128	High Similarity	NPC190020
0.9122	High Similarity	NPC79998
0.9118	High Similarity	NPC219892
0.9118	High Similarity	NPC189823
0.911	High Similarity	NPC475460
0.9103	High Similarity	NPC172329
0.9103	High Similarity	NPC2569
0.9097	High Similarity	NPC225173
0.9097	High Similarity	NPC163846
0.9097	High Similarity	NPC473023
0.9091	High Similarity	NPC210966
0.9091	High Similarity	NPC126882
0.9091	High Similarity	NPC478203
0.9091	High Similarity	NPC470932
0.9091	High Similarity	NPC42540
0.9091	High Similarity	NPC151607
0.9085	High Similarity	NPC471733
0.9085	High Similarity	NPC105648
0.9085	High Similarity	NPC96692
0.9067	High Similarity	NPC470339
0.9065	High Similarity	NPC84699
0.906	High Similarity	NPC150227
0.9058	High Similarity	NPC175943
0.9041	High Similarity	NPC233267
0.9041	High Similarity	NPC291049
0.9034	High Similarity	NPC125801
0.9034	High Similarity	NPC137296
0.9028	High Similarity	NPC473692
0.9021	High Similarity	NPC472610
0.9021	High Similarity	NPC471643
0.9021	High Similarity	NPC471639
0.9014	High Similarity	NPC220106
0.9007	High Similarity	NPC474655
0.9007	High Similarity	NPC275356
0.9007	High Similarity	NPC88269
0.9007	High Similarity	NPC247409
0.9007	High Similarity	NPC472055
0.9	High Similarity	NPC470397
0.9	High Similarity	NPC246466
0.8993	High Similarity	NPC199926
0.8993	High Similarity	NPC142027
0.8986	High Similarity	NPC474843
0.898	High Similarity	NPC56204
0.898	High Similarity	NPC96501
0.898	High Similarity	NPC60413
0.898	High Similarity	NPC119929
0.8973	High Similarity	NPC221352
0.8973	High Similarity	NPC37139
0.8973	High Similarity	NPC105415
0.8966	High Similarity	NPC260946
0.8966	High Similarity	NPC267509
0.8958	High Similarity	NPC184702
0.8951	High Similarity	NPC297985
0.8951	High Similarity	NPC49108
0.8951	High Similarity	NPC471644
0.8951	High Similarity	NPC82913
0.8951	High Similarity	NPC471640
0.8944	High Similarity	NPC155205
0.8936	High Similarity	NPC177307
0.8936	High Similarity	NPC9121
0.8936	High Similarity	NPC472403
0.8933	High Similarity	NPC472050
0.8933	High Similarity	NPC227062
0.8929	High Similarity	NPC158481
0.8929	High Similarity	NPC50455
0.8926	High Similarity	NPC472799
0.8919	High Similarity	NPC133856
0.8919	High Similarity	NPC204350
0.8913	High Similarity	NPC470160
0.8913	High Similarity	NPC476389
0.8912	High Similarity	NPC6923
0.8904	High Similarity	NPC471734
0.8904	High Similarity	NPC12305
0.8904	High Similarity	NPC166583
0.8904	High Similarity	NPC53362
0.8897	High Similarity	NPC293453
0.8897	High Similarity	NPC32470
0.8889	High Similarity	NPC354984
0.8889	High Similarity	NPC294432
0.8889	High Similarity	NPC73028
0.8889	High Similarity	NPC310340
0.8881	High Similarity	NPC307990
0.8881	High Similarity	NPC37530
0.8881	High Similarity	NPC16455
0.8874	High Similarity	NPC473395
0.8873	High Similarity	NPC52358
0.8873	High Similarity	NPC92655
0.8867	High Similarity	NPC89625
0.8867	High Similarity	NPC149618
0.8865	High Similarity	NPC240147
0.8865	High Similarity	NPC470398
0.8865	High Similarity	NPC121243
0.8859	High Similarity	NPC217447
0.8859	High Similarity	NPC113608
0.8859	High Similarity	NPC470340
0.8859	High Similarity	NPC271681
0.8859	High Similarity	NPC470338
0.8859	High Similarity	NPC268992
0.8859	High Similarity	NPC470337
0.8859	High Similarity	NPC175978
0.8859	High Similarity	NPC51824
0.8857	High Similarity	NPC27407

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 NPC51106 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	916
0.2-0.3	1831
0.3-0.4	2490
0.4-0.5	1858
0.5-0.6	1125
0.6-0.7	454
0.7-0.8	163
0.8-0.85	31
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9281	High Similarity	NPD970	Clinical (unspecified phase)
0.9161	High Similarity	NPD2534	Approved
0.9161	High Similarity	NPD2532	Approved
0.9161	High Similarity	NPD2533	Approved
0.8675	High Similarity	NPD7819	Suspended
0.8431	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6232	Discontinued
0.8403	Intermediate Similarity	NPD1510	Phase 2
0.8389	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1240	Approved
0.8366	Intermediate Similarity	NPD1934	Approved
0.8356	Intermediate Similarity	NPD1549	Phase 2
0.8355	Intermediate Similarity	NPD4380	Phase 2
0.8345	Intermediate Similarity	NPD2935	Discontinued
0.8344	Intermediate Similarity	NPD6959	Discontinued
0.8291	Intermediate Similarity	NPD5711	Approved
0.8291	Intermediate Similarity	NPD5710	Approved
0.8269	Intermediate Similarity	NPD7075	Discontinued
0.8264	Intermediate Similarity	NPD1607	Approved
0.825	Intermediate Similarity	NPD7473	Discontinued
0.8243	Intermediate Similarity	NPD3750	Approved
0.8243	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD2796	Approved
0.8205	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD6799	Approved
0.8194	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD230	Phase 1
0.8182	Intermediate Similarity	NPD7411	Suspended
0.8153	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5844	Phase 1
0.8141	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD3817	Phase 2
0.8129	Intermediate Similarity	NPD6801	Discontinued
0.8117	Intermediate Similarity	NPD6599	Discontinued
0.8112	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1551	Phase 2
0.8089	Intermediate Similarity	NPD7768	Phase 2
0.8079	Intermediate Similarity	NPD1511	Approved
0.8077	Intermediate Similarity	NPD2801	Approved
0.8075	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6166	Phase 2
0.8054	Intermediate Similarity	NPD2800	Approved
0.8038	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD4628	Phase 3
0.7988	Intermediate Similarity	NPD7074	Phase 3
0.7975	Intermediate Similarity	NPD3818	Discontinued
0.7975	Intermediate Similarity	NPD3882	Suspended
0.7974	Intermediate Similarity	NPD1512	Approved
0.7963	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7054	Approved
0.7911	Intermediate Similarity	NPD5402	Approved
0.7908	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD3748	Approved
0.7891	Intermediate Similarity	NPD6651	Approved
0.7881	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7472	Approved
0.7848	Intermediate Similarity	NPD1465	Phase 2
0.7844	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6797	Phase 2
0.7826	Intermediate Similarity	NPD9545	Approved
0.7821	Intermediate Similarity	NPD3226	Approved
0.7818	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1243	Approved
0.7806	Intermediate Similarity	NPD5403	Approved
0.7806	Intermediate Similarity	NPD920	Approved
0.7801	Intermediate Similarity	NPD9717	Approved
0.7785	Intermediate Similarity	NPD37	Approved
0.7785	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7251	Discontinued
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.775	Intermediate Similarity	NPD4966	Approved
0.775	Intermediate Similarity	NPD4967	Phase 2
0.775	Intermediate Similarity	NPD4965	Approved
0.7738	Intermediate Similarity	NPD7808	Phase 3
0.7733	Intermediate Similarity	NPD6099	Approved
0.7733	Intermediate Similarity	NPD6100	Approved
0.7727	Intermediate Similarity	NPD7390	Discontinued
0.7725	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5494	Approved
0.7703	Intermediate Similarity	NPD447	Suspended
0.7688	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2346	Discontinued
0.7681	Intermediate Similarity	NPD9493	Approved
0.7677	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5401	Approved
0.7667	Intermediate Similarity	NPD7033	Discontinued
0.7667	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2799	Discontinued
0.7662	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6234	Discontinued
0.7639	Intermediate Similarity	NPD1203	Approved
0.7619	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5953	Discontinued
0.7619	Intermediate Similarity	NPD411	Approved
0.7606	Intermediate Similarity	NPD422	Phase 1
0.7605	Intermediate Similarity	NPD7286	Phase 2
0.7603	Intermediate Similarity	NPD6832	Phase 2
0.7595	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4626	Approved
0.7584	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2654	Approved
0.7561	Intermediate Similarity	NPD7199	Phase 2
0.7552	Intermediate Similarity	NPD1608	Approved
0.7546	Intermediate Similarity	NPD919	Approved
0.7518	Intermediate Similarity	NPD5691	Approved
0.7517	Intermediate Similarity	NPD943	Approved
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5124	Phase 1
0.7466	Intermediate Similarity	NPD1019	Discontinued
0.7451	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2344	Approved
0.7451	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6005	Phase 3
0.7451	Intermediate Similarity	NPD6002	Phase 3
0.7451	Intermediate Similarity	NPD6004	Phase 3
0.744	Intermediate Similarity	NPD7228	Approved
0.7432	Intermediate Similarity	NPD3027	Phase 3
0.7431	Intermediate Similarity	NPD9269	Phase 2
0.7427	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6273	Approved
0.7397	Intermediate Similarity	NPD2797	Approved
0.7394	Intermediate Similarity	NPD9268	Approved
0.7389	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7383	Intermediate Similarity	NPD3268	Approved
0.7383	Intermediate Similarity	NPD2313	Discontinued
0.7371	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4908	Phase 1
0.7362	Intermediate Similarity	NPD5353	Approved
0.7362	Intermediate Similarity	NPD4288	Approved
0.7351	Intermediate Similarity	NPD8151	Discontinued
0.7347	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2798	Approved
0.7343	Intermediate Similarity	NPD1778	Approved
0.7343	Intermediate Similarity	NPD17	Approved
0.7337	Intermediate Similarity	NPD3751	Discontinued
0.7329	Intermediate Similarity	NPD1283	Approved
0.7308	Intermediate Similarity	NPD7003	Approved
0.7305	Intermediate Similarity	NPD3787	Discontinued
0.7292	Intermediate Similarity	NPD3496	Discontinued
0.7285	Intermediate Similarity	NPD1613	Approved
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7285	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2979	Phase 3
0.7284	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7435	Discontinued
0.7267	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1296	Phase 2
0.7267	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3926	Phase 2
0.7262	Intermediate Similarity	NPD5242	Approved
0.7261	Intermediate Similarity	NPD2309	Approved
0.7261	Intermediate Similarity	NPD6190	Approved
0.726	Intermediate Similarity	NPD4749	Approved
0.7257	Intermediate Similarity	NPD8150	Discontinued
0.7246	Intermediate Similarity	NPD1247	Approved
0.7244	Intermediate Similarity	NPD1652	Phase 2
0.7241	Intermediate Similarity	NPD1201	Approved
0.7241	Intermediate Similarity	NPD1610	Phase 2
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7208	Intermediate Similarity	NPD4308	Phase 3
0.7207	Intermediate Similarity	NPD4360	Phase 2
0.7207	Intermediate Similarity	NPD4363	Phase 3
0.7205	Intermediate Similarity	NPD1653	Approved
0.72	Intermediate Similarity	NPD4625	Phase 3
0.7198	Intermediate Similarity	NPD6778	Approved
0.7198	Intermediate Similarity	NPD6779	Approved
0.7198	Intermediate Similarity	NPD6776	Approved
0.7198	Intermediate Similarity	NPD6777	Approved
0.7198	Intermediate Similarity	NPD6782	Approved
0.7198	Intermediate Similarity	NPD6780	Approved
0.7198	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD9494	Approved
0.7168	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1470	Approved
0.7162	Intermediate Similarity	NPD1164	Approved
0.7161	Intermediate Similarity	NPD2438	Suspended
0.7161	Intermediate Similarity	NPD4477	Approved
0.7161	Intermediate Similarity	NPD4476	Approved
0.716	Intermediate Similarity	NPD7458	Discontinued
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7135	Intermediate Similarity	NPD7177	Discontinued
0.7127	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1281	Approved
0.7123	Intermediate Similarity	NPD1547	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