NPASS Compound

Structure

NPC49938 OpenBabel07101718182D 25 26 0 0 1 0 0 0 0 0999 V2000 -0.6581 1.6872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9242 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0050 -0.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5443 -2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0594 -2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8025 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 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 -2.5981 1.5000 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7377 0.7737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0104 -0.6399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1988 -1.8917 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 16 2 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 18 2 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 15 1 6 0 0 0 20 21 1 0 0 0 0 21 25 1 6 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.22
Volume:	382.507
LogP:	5.389
LogD:	4.985
LogS:	-4.532
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	3.882
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.701
MDCK Permeability:	2.3571017663925886e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.862
30% Bioavailability (F30%):	0.35

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	98.95984649658203%
Volume Distribution (VD):	0.419
Pgp-substrate:	1.0316749811172485%

ADMET: Metabolism

CYP1A2-inhibitor:	0.339
CYP1A2-substrate:	0.453
CYP2C19-inhibitor:	0.864
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.719
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.715
CYP2D6-substrate:	0.381
CYP3A4-inhibitor:	0.631
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	6.905
Half-life (T1/2):	0.558

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.309
Carcinogencity:	0.025
Eye Corrosion:	0.011
Eye Irritation:	0.147
Respiratory Toxicity:	0.095

Download Data

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

Natural Product: NPC49938

Natural Product ID:	NPC49938
*Common Name:**	6-Beta-P-Hydroxybenzoyloxygermacra-1(10),4-Diene
IUPAC Name:	[(1R,2E,6E,10S)-3,7-dimethyl-10-propan-2-ylcyclodeca-2,6-dien-1-yl] 4-hydroxybenzoate
Synonyms:
Standard InCHIKey:	IZTPZZVRYDCHRL-LUZQIQEISA-N
Standard InCHI:	InChI=1S/C22H30O3/c1-15(2)20-13-8-16(3)6-5-7-17(4)14-21(20)25-22(24)18-9-11-19(23)12-10-18/h6,9-12,14-15,20-21,23H,5,7-8,13H2,1-4H3/b16-6+,17-14+/t20-,21-/m0/s1
SMILES:	C/C/1=C[C@H](OC(=O)c2ccc(cc2)O)[C@@H](CC/C(=C/CC1)/C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096917
PubChem CID:	13992126
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002456] Germacrane sesquiterpenoids

*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
NPO33092	ferula lycia	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20329739]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	25300.0	nM	PMID[531611]
NPT80	Cell Line	Raji	Homo sapiens	IC50	=	20900.0	nM	PMID[531611]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24700.0	nM	PMID[531611]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[531611]

☑ 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 NPC49938 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	262
0.1-0.2	1201
0.2-0.3	2943
0.3-0.4	7392
0.4-0.5	11193
0.5-0.6	5229
0.6-0.7	10479
0.7-0.8	3871
0.8-0.85	104
0.85-0.9	15
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9322	High Similarity	NPC94298
0.9322	High Similarity	NPC27633
0.9268	High Similarity	NPC110211
0.9268	High Similarity	NPC204579
0.9153	High Similarity	NPC131192
0.9106	High Similarity	NPC184219
0.9048	High Similarity	NPC194979
0.8952	High Similarity	NPC221798
0.8943	High Similarity	NPC67300
0.8837	High Similarity	NPC302844
0.8819	High Similarity	NPC2596
0.8819	High Similarity	NPC473744
0.879	High Similarity	NPC69403
0.879	High Similarity	NPC291189
0.8788	High Similarity	NPC170718
0.877	High Similarity	NPC61779
0.8661	High Similarity	NPC475236
0.8615	High Similarity	NPC473777
0.8537	High Similarity	NPC273282
0.8537	High Similarity	NPC474890
0.8537	High Similarity	NPC161943
0.8485	Intermediate Similarity	NPC114116
0.8462	Intermediate Similarity	NPC226855
0.8456	Intermediate Similarity	NPC469911
0.845	Intermediate Similarity	NPC121104
0.8443	Intermediate Similarity	NPC220540
0.8409	Intermediate Similarity	NPC327204
0.8409	Intermediate Similarity	NPC323379
0.84	Intermediate Similarity	NPC72977
0.839	Intermediate Similarity	NPC29883
0.8374	Intermediate Similarity	NPC83718
0.8372	Intermediate Similarity	NPC95309
0.837	Intermediate Similarity	NPC70380
0.8346	Intermediate Similarity	NPC477280
0.8346	Intermediate Similarity	NPC477281
0.8346	Intermediate Similarity	NPC475192
0.8346	Intermediate Similarity	NPC19719
0.8321	Intermediate Similarity	NPC51181
0.832	Intermediate Similarity	NPC328459
0.832	Intermediate Similarity	NPC90522
0.8309	Intermediate Similarity	NPC33144
0.8309	Intermediate Similarity	NPC191835
0.8309	Intermediate Similarity	NPC478200
0.8309	Intermediate Similarity	NPC212693
0.8309	Intermediate Similarity	NPC94248
0.8308	Intermediate Similarity	NPC158654
0.8306	Intermediate Similarity	NPC122117
0.8305	Intermediate Similarity	NPC184658
0.8296	Intermediate Similarity	NPC291454
0.8286	Intermediate Similarity	NPC208293
0.8271	Intermediate Similarity	NPC477407
0.8261	Intermediate Similarity	NPC472035
0.8261	Intermediate Similarity	NPC313123
0.8261	Intermediate Similarity	NPC478201
0.8261	Intermediate Similarity	NPC478217
0.8258	Intermediate Similarity	NPC86774
0.8258	Intermediate Similarity	NPC327457
0.825	Intermediate Similarity	NPC95172
0.8248	Intermediate Similarity	NPC139634
0.8248	Intermediate Similarity	NPC105456
0.8244	Intermediate Similarity	NPC2401
0.824	Intermediate Similarity	NPC94637
0.8235	Intermediate Similarity	NPC71256
0.8222	Intermediate Similarity	NPC18646
0.8222	Intermediate Similarity	NPC142027
0.8222	Intermediate Similarity	NPC27407
0.8211	Intermediate Similarity	NPC81808
0.8197	Intermediate Similarity	NPC17693
0.8195	Intermediate Similarity	NPC214702
0.8195	Intermediate Similarity	NPC104854
0.8195	Intermediate Similarity	NPC470831
0.8188	Intermediate Similarity	NPC158472
0.8182	Intermediate Similarity	NPC214246
0.8175	Intermediate Similarity	NPC221104
0.8175	Intermediate Similarity	NPC472602
0.8169	Intermediate Similarity	NPC477483
0.8169	Intermediate Similarity	NPC325032
0.8167	Intermediate Similarity	NPC31274
0.8162	Intermediate Similarity	NPC475111
0.8162	Intermediate Similarity	NPC156892
0.8154	Intermediate Similarity	NPC137416
0.8148	Intermediate Similarity	NPC311339
0.8145	Intermediate Similarity	NPC322197
0.8143	Intermediate Similarity	NPC478202
0.8143	Intermediate Similarity	NPC469615
0.8143	Intermediate Similarity	NPC77922
0.8143	Intermediate Similarity	NPC473281
0.814	Intermediate Similarity	NPC174991
0.8134	Intermediate Similarity	NPC476389
0.813	Intermediate Similarity	NPC11824
0.8129	Intermediate Similarity	NPC158634
0.8129	Intermediate Similarity	NPC184053
0.8129	Intermediate Similarity	NPC470842
0.8129	Intermediate Similarity	NPC53649
0.8129	Intermediate Similarity	NPC1704
0.8129	Intermediate Similarity	NPC67650
0.812	Intermediate Similarity	NPC42292
0.812	Intermediate Similarity	NPC307732
0.812	Intermediate Similarity	NPC109778
0.8115	Intermediate Similarity	NPC139946
0.8112	Intermediate Similarity	NPC161955
0.8112	Intermediate Similarity	NPC17600
0.8112	Intermediate Similarity	NPC279442
0.8106	Intermediate Similarity	NPC229894
0.8106	Intermediate Similarity	NPC193203
0.8102	Intermediate Similarity	NPC261292
0.8102	Intermediate Similarity	NPC119542
0.8102	Intermediate Similarity	NPC301915
0.8095	Intermediate Similarity	NPC249435
0.8085	Intermediate Similarity	NPC126882
0.8085	Intermediate Similarity	NPC151607
0.8085	Intermediate Similarity	NPC478203
0.8085	Intermediate Similarity	NPC210966
0.8085	Intermediate Similarity	NPC469683
0.8085	Intermediate Similarity	NPC42540
0.8083	Intermediate Similarity	NPC226699
0.808	Intermediate Similarity	NPC128249
0.808	Intermediate Similarity	NPC128825
0.8074	Intermediate Similarity	NPC66158
0.8074	Intermediate Similarity	NPC1321
0.8074	Intermediate Similarity	NPC239855
0.8074	Intermediate Similarity	NPC304929
0.8074	Intermediate Similarity	NPC156124
0.8074	Intermediate Similarity	NPC153783
0.8074	Intermediate Similarity	NPC43627
0.8071	Intermediate Similarity	NPC474385
0.806	Intermediate Similarity	NPC125153
0.8058	Intermediate Similarity	NPC472600
0.8058	Intermediate Similarity	NPC472601
0.8056	Intermediate Similarity	NPC87630
0.8056	Intermediate Similarity	NPC247219
0.8056	Intermediate Similarity	NPC327962
0.8056	Intermediate Similarity	NPC162569
0.8056	Intermediate Similarity	NPC116292
0.8056	Intermediate Similarity	NPC52931
0.8056	Intermediate Similarity	NPC179128
0.8056	Intermediate Similarity	NPC267469
0.8056	Intermediate Similarity	NPC35160
0.8051	Intermediate Similarity	NPC304638
0.8045	Intermediate Similarity	NPC117899
0.8045	Intermediate Similarity	NPC94810
0.8043	Intermediate Similarity	NPC177307
0.8043	Intermediate Similarity	NPC472403
0.8043	Intermediate Similarity	NPC9121
0.8042	Intermediate Similarity	NPC66991
0.8042	Intermediate Similarity	NPC81835
0.8033	Intermediate Similarity	NPC476003
0.8031	Intermediate Similarity	NPC473767
0.803	Intermediate Similarity	NPC37512
0.8029	Intermediate Similarity	NPC475955
0.8029	Intermediate Similarity	NPC64230
0.8029	Intermediate Similarity	NPC474726
0.8029	Intermediate Similarity	NPC71638
0.8029	Intermediate Similarity	NPC471345
0.8029	Intermediate Similarity	NPC235115
0.8028	Intermediate Similarity	NPC257558
0.8028	Intermediate Similarity	NPC472034
0.8028	Intermediate Similarity	NPC83272
0.8028	Intermediate Similarity	NPC97188
0.8017	Intermediate Similarity	NPC206341
0.8015	Intermediate Similarity	NPC165556
0.8015	Intermediate Similarity	NPC474097
0.8015	Intermediate Similarity	NPC194970
0.8014	Intermediate Similarity	NPC271451
0.8014	Intermediate Similarity	NPC51106
0.8014	Intermediate Similarity	NPC159721
0.8014	Intermediate Similarity	NPC472006
0.8	Intermediate Similarity	NPC164236
0.8	Intermediate Similarity	NPC112192
0.8	Intermediate Similarity	NPC289021
0.8	Intermediate Similarity	NPC158546
0.8	Intermediate Similarity	NPC472605
0.8	Intermediate Similarity	NPC128348
0.8	Intermediate Similarity	NPC472604
0.8	Intermediate Similarity	NPC475730
0.8	Intermediate Similarity	NPC66384
0.8	Intermediate Similarity	NPC37642
0.8	Intermediate Similarity	NPC189106
0.8	Intermediate Similarity	NPC6984
0.8	Intermediate Similarity	NPC472603
0.8	Intermediate Similarity	NPC309717
0.7986	Intermediate Similarity	NPC52358
0.7986	Intermediate Similarity	NPC478234
0.7986	Intermediate Similarity	NPC112789
0.7986	Intermediate Similarity	NPC88269
0.7986	Intermediate Similarity	NPC32360
0.7986	Intermediate Similarity	NPC19622
0.7985	Intermediate Similarity	NPC285776
0.7985	Intermediate Similarity	NPC245395
0.7984	Intermediate Similarity	NPC109241
0.7984	Intermediate Similarity	NPC242136
0.7972	Intermediate Similarity	NPC286038
0.7972	Intermediate Similarity	NPC472033
0.7972	Intermediate Similarity	NPC51513
0.7972	Intermediate Similarity	NPC469498
0.7972	Intermediate Similarity	NPC202112
0.7972	Intermediate Similarity	NPC473149
0.7971	Intermediate Similarity	NPC65837
0.7971	Intermediate Similarity	NPC187826
0.7971	Intermediate Similarity	NPC474771

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 NPC49938 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	861
0.2-0.3	1477
0.3-0.4	2527
0.4-0.5	2115
0.5-0.6	1319
0.6-0.7	522
0.7-0.8	95
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9322	High Similarity	NPD9545	Approved
0.839	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4628	Phase 3
0.812	Intermediate Similarity	NPD3764	Approved
0.808	Intermediate Similarity	NPD9493	Approved
0.8074	Intermediate Similarity	NPD230	Phase 1
0.8058	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1608	Approved
0.7742	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1240	Approved
0.773	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD3134	Approved
0.7652	Intermediate Similarity	NPD3972	Approved
0.7626	Intermediate Similarity	NPD1607	Approved
0.7615	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1549	Phase 2
0.7591	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD17	Approved
0.7535	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD9717	Approved
0.7518	Intermediate Similarity	NPD1510	Phase 2
0.7518	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD9494	Approved
0.7481	Intermediate Similarity	NPD2797	Approved
0.7467	Intermediate Similarity	NPD7411	Suspended
0.7466	Intermediate Similarity	NPD6799	Approved
0.7465	Intermediate Similarity	NPD2796	Approved
0.7465	Intermediate Similarity	NPD2935	Discontinued
0.7451	Intermediate Similarity	NPD7075	Discontinued
0.7448	Intermediate Similarity	NPD6190	Approved
0.744	Intermediate Similarity	NPD2182	Approved
0.744	Intermediate Similarity	NPD74	Approved
0.744	Intermediate Similarity	NPD9266	Approved
0.7426	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD1241	Discontinued
0.7415	Intermediate Similarity	NPD2532	Approved
0.7415	Intermediate Similarity	NPD2534	Approved
0.7415	Intermediate Similarity	NPD2533	Approved
0.74	Intermediate Similarity	NPD6599	Discontinued
0.7379	Intermediate Similarity	NPD7003	Approved
0.7368	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7819	Suspended
0.7365	Intermediate Similarity	NPD6273	Approved
0.736	Intermediate Similarity	NPD1358	Approved
0.736	Intermediate Similarity	NPD9263	Approved
0.736	Intermediate Similarity	NPD9264	Approved
0.736	Intermediate Similarity	NPD9267	Approved
0.7355	Intermediate Similarity	NPD1238	Approved
0.7353	Intermediate Similarity	NPD1203	Approved
0.7347	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1551	Phase 2
0.7338	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD7458	Discontinued
0.732	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6355	Discontinued
0.7303	Intermediate Similarity	NPD6801	Discontinued
0.7299	Intermediate Similarity	NPD2798	Approved
0.7297	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1778	Approved
0.7292	Intermediate Similarity	NPD2344	Approved
0.7286	Intermediate Similarity	NPD6663	Approved
0.7285	Intermediate Similarity	NPD4380	Phase 2
0.7279	Intermediate Similarity	NPD1876	Approved
0.7279	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD1894	Discontinued
0.726	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD8166	Discontinued
0.7259	Intermediate Similarity	NPD9269	Phase 2
0.7248	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5736	Approved
0.7226	Intermediate Similarity	NPD1164	Approved
0.7218	Intermediate Similarity	NPD9268	Approved
0.7214	Intermediate Similarity	NPD6798	Discontinued
0.7211	Intermediate Similarity	NPD3887	Approved
0.7194	Intermediate Similarity	NPD6832	Phase 2
0.7185	Intermediate Similarity	NPD422	Phase 1
0.7181	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6004	Phase 3
0.7172	Intermediate Similarity	NPD6005	Phase 3
0.7172	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6002	Phase 3
0.717	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4626	Approved
0.7153	Intermediate Similarity	NPD3748	Approved
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2186	Approved
0.7132	Intermediate Similarity	NPD1481	Phase 2
0.712	Intermediate Similarity	NPD164	Approved
0.712	Intermediate Similarity	NPD5909	Discontinued
0.7119	Intermediate Similarity	NPD9256	Approved
0.7119	Intermediate Similarity	NPD9258	Approved
0.7115	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3140	Approved
0.7113	Intermediate Similarity	NPD3142	Approved
0.7111	Intermediate Similarity	NPD3847	Discontinued
0.7105	Intermediate Similarity	NPD3455	Phase 2
0.7099	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2354	Approved
0.7095	Intermediate Similarity	NPD2309	Approved
0.709	Intermediate Similarity	NPD5691	Approved
0.7078	Intermediate Similarity	NPD1934	Approved
0.7073	Intermediate Similarity	NPD3020	Approved
0.7059	Intermediate Similarity	NPD1535	Discovery
0.7059	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1281	Approved
0.705	Intermediate Similarity	NPD1019	Discontinued
0.705	Intermediate Similarity	NPD5647	Approved
0.7047	Intermediate Similarity	NPD7440	Discontinued
0.7045	Intermediate Similarity	NPD256	Approved
0.7045	Intermediate Similarity	NPD255	Approved
0.7042	Intermediate Similarity	NPD6233	Phase 2
0.7042	Intermediate Similarity	NPD4062	Phase 3
0.704	Intermediate Similarity	NPD6647	Phase 2
0.704	Intermediate Similarity	NPD9261	Approved
0.7037	Intermediate Similarity	NPD5844	Phase 1
0.7034	Intermediate Similarity	NPD4308	Phase 3
0.7031	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3225	Approved
0.7021	Intermediate Similarity	NPD7008	Discontinued
0.7021	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6651	Approved
0.7012	Intermediate Similarity	NPD7685	Pre-registration
0.7006	Intermediate Similarity	NPD3749	Approved
0.7	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3226	Approved
0.6993	Remote Similarity	NPD2979	Phase 3
0.6993	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5404	Approved
0.6986	Remote Similarity	NPD5406	Approved
0.6986	Remote Similarity	NPD5405	Approved
0.6986	Remote Similarity	NPD4477	Approved
0.6986	Remote Similarity	NPD4476	Approved
0.6986	Remote Similarity	NPD5408	Approved
0.6984	Remote Similarity	NPD1237	Approved
0.6978	Remote Similarity	NPD3266	Approved
0.6978	Remote Similarity	NPD3267	Approved
0.6974	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5403	Approved
0.6972	Remote Similarity	NPD411	Approved
0.6972	Remote Similarity	NPD2313	Discontinued
0.697	Remote Similarity	NPD2629	Approved
0.697	Remote Similarity	NPD9281	Approved
0.6968	Remote Similarity	NPD7577	Discontinued
0.6967	Remote Similarity	NPD2860	Approved
0.6967	Remote Similarity	NPD2859	Approved
0.6966	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5585	Approved
0.6959	Remote Similarity	NPD1243	Approved
0.6944	Remote Similarity	NPD5124	Phase 1
0.6944	Remote Similarity	NPD447	Suspended
0.6944	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3882	Suspended
0.6939	Remote Similarity	NPD7266	Discontinued
0.6939	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2353	Approved
0.6937	Remote Similarity	NPD6232	Discontinued
0.6935	Remote Similarity	NPD2066	Phase 3
0.6934	Remote Similarity	NPD1201	Approved
0.6933	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5048	Discontinued
0.6923	Remote Similarity	NPD520	Approved
0.6914	Remote Similarity	NPD7473	Discontinued
0.6913	Remote Similarity	NPD4110	Phase 3
0.6913	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD2932	Approved
0.6912	Remote Similarity	NPD3019	Approved
0.6905	Remote Similarity	NPD1929	Approved
0.6905	Remote Similarity	NPD1930	Approved
0.6905	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6386	Approved
0.6903	Remote Similarity	NPD6385	Approved
0.6903	Remote Similarity	NPD2672	Discontinued
0.6899	Remote Similarity	NPD2684	Approved
0.6892	Remote Similarity	NPD5958	Discontinued
0.6892	Remote Similarity	NPD4534	Discontinued
0.6885	Remote Similarity	NPD2933	Approved
0.6885	Remote Similarity	NPD2934	Approved
0.6885	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5353	Approved
0.6879	Remote Similarity	NPD3817	Phase 2
0.6879	Remote Similarity	NPD454	Approved
0.6879	Remote Similarity	NPD2861	Phase 2
0.6875	Remote Similarity	NPD4060	Phase 1
0.6875	Remote Similarity	NPD943	Approved
0.6871	Remote Similarity	NPD2438	Suspended
0.6871	Remote Similarity	NPD6100	Approved
0.6871	Remote Similarity	NPD6099	Approved
0.6866	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD920	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