NPASS Compound

Structure

NPC194979 OpenBabel07101718292D 25 27 0 0 1 0 0 0 0 0999 V2000 -0.7044 3.2564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9898 2.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6192 -0.7853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2219 0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6113 -2.6623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7452 -1.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4773 -2.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6113 -0.6623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4888 1.0151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3209 -1.2256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3653 -0.9309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0132 -1.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0388 2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1472 -0.6623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7452 -2.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4773 -1.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 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 3.8792 -2.6623 0.0000 C 0 0 0 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 7.3433 -0.6623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8792 -3.6623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0132 -2.1623 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 4 9 1 0 0 0 0 4 16 1 0 0 0 0 5 7 1 0 0 0 0 5 17 2 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 20 22 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.2
Volume:	373.951
LogP:	4.999
LogD:	4.253
LogS:	-4.657
# Rotatable Bonds:	5
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	3.415
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:	-4.646
MDCK Permeability:	1.9104159946436994e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.78
30% Bioavailability (F30%):	0.061

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	99.26783752441406%
Volume Distribution (VD):	3.076
Pgp-substrate:	1.2873224020004272%

ADMET: Metabolism

CYP1A2-inhibitor:	0.401
CYP1A2-substrate:	0.529
CYP2C19-inhibitor:	0.799
CYP2C19-substrate:	0.381
CYP2C9-inhibitor:	0.504
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.818
CYP2D6-substrate:	0.771
CYP3A4-inhibitor:	0.718
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	10.039
Half-life (T1/2):	0.537

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.037
Drug-inuced Liver Injury (DILI):	0.691
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.078
Carcinogencity:	0.925
Eye Corrosion:	0.003
Eye Irritation:	0.455
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC194979

Natural Product ID:	NPC194979
*Common Name:**	14-(4'-Hydroxybenzoyloxy)Dauc-4,8-Diene
IUPAC Name:	[(8aR)-8a-methyl-3-propan-2-yl-2,4,5,8-tetrahydro-1H-azulen-6-yl]methyl 4-hydroxybenzoate
Synonyms:
Standard InCHIKey:	OKXGQALERULNCC-QFIPXVFZSA-N
Standard InCHI:	InChI=1S/C22H28O3/c1-15(2)19-11-13-22(3)12-10-16(4-9-20(19)22)14-25-21(24)17-5-7-18(23)8-6-17/h5-8,10,15,23H,4,9,11-14H2,1-3H3/t22-/m0/s1
SMILES:	CC(C)C1=C2CCC(=CC[C@@]2(C)CC1)COC(=O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479149
PubChem CID:	10193495
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] 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
NPO33190	ferula hermonis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277769]
NPO33190	ferula hermonis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787464]

☑ 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	2
MIC	5

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	1.5	ug.mL-1	PMID[507997]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	2.0	ug.mL-1	PMID[507997]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	6.25	ug.mL-1	PMID[507997]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	6.25	ug.mL-1	PMID[507997]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	6.25	ug.mL-1	PMID[507997]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	6.25	ug.mL-1	PMID[507997]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	=	6.25	ug.mL-1	PMID[507997]

☑ 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 NPC194979 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	250
0.1-0.2	1238
0.2-0.3	2831
0.3-0.4	6933
0.4-0.5	11537
0.5-0.6	5826
0.6-0.7	10684
0.7-0.8	3324
0.8-0.85	54
0.85-0.9	13
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.928	High Similarity	NPC204579
0.928	High Similarity	NPC110211
0.9237	High Similarity	NPC170718
0.9048	High Similarity	NPC49938
0.9016	High Similarity	NPC94298
0.9016	High Similarity	NPC27633
0.8968	High Similarity	NPC184219
0.8852	High Similarity	NPC131192
0.881	High Similarity	NPC67300
0.875	High Similarity	NPC51181
0.8692	High Similarity	NPC2596
0.8672	High Similarity	NPC221798
0.8613	High Similarity	NPC469911
0.8571	High Similarity	NPC302844
0.855	High Similarity	NPC473744
0.8516	High Similarity	NPC69403
0.8516	High Similarity	NPC291189
0.8492	Intermediate Similarity	NPC61779
0.8413	Intermediate Similarity	NPC273282
0.8413	Intermediate Similarity	NPC474890
0.8413	Intermediate Similarity	NPC161943
0.8397	Intermediate Similarity	NPC475236
0.8358	Intermediate Similarity	NPC473777
0.8358	Intermediate Similarity	NPC125153
0.8333	Intermediate Similarity	NPC122117
0.8333	Intermediate Similarity	NPC121104
0.831	Intermediate Similarity	NPC208293
0.8308	Intermediate Similarity	NPC174991
0.8264	Intermediate Similarity	NPC279442
0.8264	Intermediate Similarity	NPC161955
0.8254	Intermediate Similarity	NPC83718
0.8226	Intermediate Similarity	NPC17693
0.8209	Intermediate Similarity	NPC226855
0.8182	Intermediate Similarity	NPC137416
0.8175	Intermediate Similarity	NPC220540
0.8169	Intermediate Similarity	NPC469615
0.8162	Intermediate Similarity	NPC323379
0.8162	Intermediate Similarity	NPC327204
0.8148	Intermediate Similarity	NPC327457
0.8148	Intermediate Similarity	NPC86774
0.8145	Intermediate Similarity	NPC139946
0.814	Intermediate Similarity	NPC72977
0.8134	Intermediate Similarity	NPC229894
0.8134	Intermediate Similarity	NPC193203
0.813	Intermediate Similarity	NPC95172
0.8129	Intermediate Similarity	NPC119542
0.8129	Intermediate Similarity	NPC477592
0.812	Intermediate Similarity	NPC95309
0.8115	Intermediate Similarity	NPC29883
0.8112	Intermediate Similarity	NPC469683
0.811	Intermediate Similarity	NPC128249
0.8102	Intermediate Similarity	NPC477281
0.8102	Intermediate Similarity	NPC19719
0.8102	Intermediate Similarity	NPC477280
0.8102	Intermediate Similarity	NPC114116
0.8092	Intermediate Similarity	NPC475192
0.8082	Intermediate Similarity	NPC162569
0.8082	Intermediate Similarity	NPC179128
0.8082	Intermediate Similarity	NPC267469
0.8082	Intermediate Similarity	NPC35160
0.8082	Intermediate Similarity	NPC87630
0.8082	Intermediate Similarity	NPC116292
0.8074	Intermediate Similarity	NPC117899
0.8074	Intermediate Similarity	NPC214246
0.8071	Intermediate Similarity	NPC477593
0.8069	Intermediate Similarity	NPC66991
0.8069	Intermediate Similarity	NPC477483
0.8069	Intermediate Similarity	NPC325032
0.8062	Intermediate Similarity	NPC90522
0.8062	Intermediate Similarity	NPC328459
0.806	Intermediate Similarity	NPC158654
0.8058	Intermediate Similarity	NPC156892
0.8056	Intermediate Similarity	NPC97188
0.8049	Intermediate Similarity	NPC31274
0.8043	Intermediate Similarity	NPC477594
0.8042	Intermediate Similarity	NPC473281
0.8042	Intermediate Similarity	NPC77922
0.8042	Intermediate Similarity	NPC271451
0.8033	Intermediate Similarity	NPC184658
0.8029	Intermediate Similarity	NPC477407
0.8028	Intermediate Similarity	NPC477595
0.8016	Intermediate Similarity	NPC11824
0.8015	Intermediate Similarity	NPC109778
0.8014	Intermediate Similarity	NPC17600
0.8	Intermediate Similarity	NPC70380
0.8	Intermediate Similarity	NPC79332
0.8	Intermediate Similarity	NPC286038
0.8	Intermediate Similarity	NPC469498
0.8	Intermediate Similarity	NPC2401
0.7986	Intermediate Similarity	NPC18646
0.7986	Intermediate Similarity	NPC477596
0.7984	Intermediate Similarity	NPC94637
0.7971	Intermediate Similarity	NPC66158
0.7971	Intermediate Similarity	NPC239855
0.7967	Intermediate Similarity	NPC226699
0.7959	Intermediate Similarity	NPC327962
0.7959	Intermediate Similarity	NPC52931
0.7956	Intermediate Similarity	NPC18798
0.7955	Intermediate Similarity	NPC472703
0.7953	Intermediate Similarity	NPC81808
0.7943	Intermediate Similarity	NPC191835
0.7943	Intermediate Similarity	NPC33144
0.7943	Intermediate Similarity	NPC94248
0.7943	Intermediate Similarity	NPC212693
0.7943	Intermediate Similarity	NPC478200
0.7933	Intermediate Similarity	NPC159692
0.7929	Intermediate Similarity	NPC475111
0.7929	Intermediate Similarity	NPC475955
0.7929	Intermediate Similarity	NPC474726
0.7929	Intermediate Similarity	NPC291454
0.7926	Intermediate Similarity	NPC37512
0.7914	Intermediate Similarity	NPC194970
0.7907	Intermediate Similarity	NPC174087
0.7905	Intermediate Similarity	NPC158546
0.7905	Intermediate Similarity	NPC289021
0.7905	Intermediate Similarity	NPC140133
0.7905	Intermediate Similarity	NPC37642
0.7902	Intermediate Similarity	NPC478201
0.7902	Intermediate Similarity	NPC478217
0.7902	Intermediate Similarity	NPC184053
0.7902	Intermediate Similarity	NPC472035
0.7902	Intermediate Similarity	NPC313123
0.7899	Intermediate Similarity	NPC128348
0.7899	Intermediate Similarity	NPC66384
0.7899	Intermediate Similarity	NPC309717
0.7899	Intermediate Similarity	NPC164236
0.7899	Intermediate Similarity	NPC189106
0.7899	Intermediate Similarity	NPC112192
0.7895	Intermediate Similarity	NPC472704
0.7891	Intermediate Similarity	NPC322197
0.7887	Intermediate Similarity	NPC112789
0.7887	Intermediate Similarity	NPC19622
0.7886	Intermediate Similarity	NPC6984
0.7883	Intermediate Similarity	NPC307732
0.7883	Intermediate Similarity	NPC42292
0.7877	Intermediate Similarity	NPC473149
0.7874	Intermediate Similarity	NPC242136
0.7872	Intermediate Similarity	NPC71256
0.7872	Intermediate Similarity	NPC187826
0.7857	Intermediate Similarity	NPC142027
0.7857	Intermediate Similarity	NPC236974
0.7857	Intermediate Similarity	NPC114682
0.7857	Intermediate Similarity	NPC27407
0.7857	Intermediate Similarity	NPC144027
0.7857	Intermediate Similarity	NPC212718
0.7852	Intermediate Similarity	NPC478235
0.7852	Intermediate Similarity	NPC474476
0.7852	Intermediate Similarity	NPC473751
0.7852	Intermediate Similarity	NPC475093
0.7852	Intermediate Similarity	NPC11892
0.7847	Intermediate Similarity	NPC478250
0.7847	Intermediate Similarity	NPC89317
0.7846	Intermediate Similarity	NPC293424
0.7846	Intermediate Similarity	NPC249435
0.7842	Intermediate Similarity	NPC153783
0.7842	Intermediate Similarity	NPC156124
0.7842	Intermediate Similarity	NPC304929
0.7842	Intermediate Similarity	NPC1321
0.7832	Intermediate Similarity	NPC172311
0.7832	Intermediate Similarity	NPC158472
0.7832	Intermediate Similarity	NPC275903
0.7829	Intermediate Similarity	NPC128825
0.7826	Intermediate Similarity	NPC470831
0.7826	Intermediate Similarity	NPC470977
0.7826	Intermediate Similarity	NPC104854
0.7826	Intermediate Similarity	NPC470976
0.7826	Intermediate Similarity	NPC214702
0.7826	Intermediate Similarity	NPC196979
0.7817	Intermediate Similarity	NPC23870
0.7817	Intermediate Similarity	NPC472602
0.7817	Intermediate Similarity	NPC221104
0.7815	Intermediate Similarity	NPC472807
0.781	Intermediate Similarity	NPC94810
0.7808	Intermediate Similarity	NPC258856
0.7808	Intermediate Similarity	NPC75295
0.7801	Intermediate Similarity	NPC71638
0.7801	Intermediate Similarity	NPC471345
0.7801	Intermediate Similarity	NPC64230
0.7793	Intermediate Similarity	NPC478202
0.7787	Intermediate Similarity	NPC304638
0.7786	Intermediate Similarity	NPC311339
0.7786	Intermediate Similarity	NPC27643
0.7786	Intermediate Similarity	NPC473767
0.7785	Intermediate Similarity	NPC243891
0.7778	Intermediate Similarity	NPC470842
0.7778	Intermediate Similarity	NPC307990
0.7778	Intermediate Similarity	NPC1704
0.7778	Intermediate Similarity	NPC53649
0.7778	Intermediate Similarity	NPC67650
0.7778	Intermediate Similarity	NPC16455
0.7778	Intermediate Similarity	NPC116842
0.7778	Intermediate Similarity	NPC95449
0.7778	Intermediate Similarity	NPC158634
0.7778	Intermediate Similarity	NPC165556
0.7778	Intermediate Similarity	NPC183700
0.777	Intermediate Similarity	NPC476389
0.777	Intermediate Similarity	NPC478234
0.7769	Intermediate Similarity	NPC469954
0.7762	Intermediate Similarity	NPC52358
0.7762	Intermediate Similarity	NPC139634

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 NPC194979 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	854
0.2-0.3	1444
0.3-0.4	2519
0.4-0.5	2203
0.5-0.6	1333
0.6-0.7	486
0.7-0.8	70
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9016	High Similarity	NPD9545	Approved
0.8156	Intermediate Similarity	NPD4628	Phase 3
0.8115	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD3764	Approved
0.7958	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD230	Phase 1
0.7829	Intermediate Similarity	NPD9493	Approved
0.7687	Intermediate Similarity	NPD3972	Approved
0.7652	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1240	Approved
0.7556	Intermediate Similarity	NPD1608	Approved
0.7535	Intermediate Similarity	NPD1607	Approved
0.7517	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD3134	Approved
0.7447	Intermediate Similarity	NPD6663	Approved
0.7434	Intermediate Similarity	NPD6599	Discontinued
0.7431	Intermediate Similarity	NPD2799	Discontinued
0.7431	Intermediate Similarity	NPD1510	Phase 2
0.7415	Intermediate Similarity	NPD7003	Approved
0.741	Intermediate Similarity	NPD5736	Approved
0.7397	Intermediate Similarity	NPD1549	Phase 2
0.7386	Intermediate Similarity	NPD7411	Suspended
0.7383	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6799	Approved
0.7379	Intermediate Similarity	NPD2935	Discontinued
0.7368	Intermediate Similarity	NPD7458	Discontinued
0.7338	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD1778	Approved
0.7333	Intermediate Similarity	NPD2534	Approved
0.7333	Intermediate Similarity	NPD17	Approved
0.7333	Intermediate Similarity	NPD2533	Approved
0.7329	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1241	Discontinued
0.7319	Intermediate Similarity	NPD1876	Approved
0.7299	Intermediate Similarity	NPD9717	Approved
0.7297	Intermediate Similarity	NPD8166	Discontinued
0.7297	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3750	Approved
0.7286	Intermediate Similarity	NPD9494	Approved
0.7266	Intermediate Similarity	NPD2797	Approved
0.7261	Intermediate Similarity	NPD7075	Discontinued
0.726	Intermediate Similarity	NPD2796	Approved
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2344	Approved
0.7209	Intermediate Similarity	NPD9266	Approved
0.7209	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2182	Approved
0.7209	Intermediate Similarity	NPD74	Approved
0.7206	Intermediate Similarity	NPD2932	Approved
0.7206	Intermediate Similarity	NPD3019	Approved
0.7192	Intermediate Similarity	NPD7033	Discontinued
0.7185	Intermediate Similarity	NPD1894	Discontinued
0.7183	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7819	Suspended
0.7172	Intermediate Similarity	NPD6651	Approved
0.7143	Intermediate Similarity	NPD1203	Approved
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7133	Intermediate Similarity	NPD6190	Approved
0.7133	Intermediate Similarity	NPD3268	Approved
0.7132	Intermediate Similarity	NPD9264	Approved
0.7132	Intermediate Similarity	NPD1358	Approved
0.7132	Intermediate Similarity	NPD9263	Approved
0.7132	Intermediate Similarity	NPD9267	Approved
0.712	Intermediate Similarity	NPD1238	Approved
0.7115	Intermediate Similarity	NPD6801	Discontinued
0.7113	Intermediate Similarity	NPD6832	Phase 2
0.7105	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD422	Phase 1
0.7097	Intermediate Similarity	NPD4380	Phase 2
0.7095	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6004	Phase 3
0.7095	Intermediate Similarity	NPD6002	Phase 3
0.7095	Intermediate Similarity	NPD6005	Phase 3
0.7095	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2798	Approved
0.7089	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7768	Phase 2
0.7071	Intermediate Similarity	NPD1283	Approved
0.7059	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1481	Phase 2
0.705	Intermediate Similarity	NPD9269	Phase 2
0.7034	Intermediate Similarity	NPD3140	Approved
0.7034	Intermediate Similarity	NPD3142	Approved
0.7029	Intermediate Similarity	NPD3847	Discontinued
0.7029	Intermediate Similarity	NPD3496	Discontinued
0.7025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1164	Approved
0.702	Intermediate Similarity	NPD2309	Approved
0.702	Intermediate Similarity	NPD3887	Approved
0.702	Intermediate Similarity	NPD2354	Approved
0.7015	Intermediate Similarity	NPD2629	Approved
0.7015	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6798	Discontinued
0.7013	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD9268	Approved
0.7	Intermediate Similarity	NPD1243	Approved
0.7	Intermediate Similarity	NPD2800	Approved
0.6994	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3882	Suspended
0.6978	Remote Similarity	NPD1535	Discovery
0.6974	Remote Similarity	NPD7236	Approved
0.6974	Remote Similarity	NPD7440	Discontinued
0.6974	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5647	Approved
0.6966	Remote Similarity	NPD8032	Phase 2
0.6963	Remote Similarity	NPD255	Approved
0.6963	Remote Similarity	NPD256	Approved
0.6962	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3748	Approved
0.6959	Remote Similarity	NPD4308	Phase 3
0.6957	Remote Similarity	NPD4626	Approved
0.6957	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4110	Phase 3
0.6954	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6647	Phase 2
0.6948	Remote Similarity	NPD2186	Approved
0.6944	Remote Similarity	NPD7008	Discontinued
0.6937	Remote Similarity	NPD3749	Approved
0.6937	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3455	Phase 2
0.6918	Remote Similarity	NPD4140	Approved
0.6913	Remote Similarity	NPD6100	Approved
0.6913	Remote Similarity	NPD4476	Approved
0.6913	Remote Similarity	NPD6099	Approved
0.6913	Remote Similarity	NPD4477	Approved
0.6903	Remote Similarity	NPD920	Approved
0.6899	Remote Similarity	NPD164	Approved
0.6899	Remote Similarity	NPD5909	Discontinued
0.6899	Remote Similarity	NPD1934	Approved
0.6897	Remote Similarity	NPD1296	Phase 2
0.6897	Remote Similarity	NPD2313	Discontinued
0.6889	Remote Similarity	NPD5951	Approved
0.6885	Remote Similarity	NPD9256	Approved
0.6885	Remote Similarity	NPD9258	Approved
0.6884	Remote Similarity	NPD5585	Approved
0.6884	Remote Similarity	NPD5691	Approved
0.6883	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.688	Remote Similarity	NPD2860	Approved
0.688	Remote Similarity	NPD2859	Approved
0.6867	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2353	Approved
0.6857	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1281	Approved
0.6857	Remote Similarity	NPD6287	Discontinued
0.6853	Remote Similarity	NPD1019	Discontinued
0.685	Remote Similarity	NPD3020	Approved
0.6849	Remote Similarity	NPD6233	Phase 2
0.6849	Remote Similarity	NPD4062	Phase 3
0.6845	Remote Similarity	NPD7685	Pre-registration
0.6835	Remote Similarity	NPD6385	Approved
0.6835	Remote Similarity	NPD6386	Approved
0.6835	Remote Similarity	NPD2672	Discontinued
0.6831	Remote Similarity	NPD3225	Approved
0.6822	Remote Similarity	NPD9261	Approved
0.6821	Remote Similarity	NPD4534	Discontinued
0.6818	Remote Similarity	NPD2684	Approved
0.6815	Remote Similarity	NPD3226	Approved
0.6813	Remote Similarity	NPD3817	Phase 2
0.681	Remote Similarity	NPD8127	Discontinued
0.6806	Remote Similarity	NPD2861	Phase 2
0.6806	Remote Similarity	NPD454	Approved
0.6803	Remote Similarity	NPD943	Approved
0.6803	Remote Similarity	NPD2979	Phase 3
0.68	Remote Similarity	NPD5408	Approved
0.68	Remote Similarity	NPD5405	Approved
0.68	Remote Similarity	NPD2934	Approved
0.68	Remote Similarity	NPD2933	Approved
0.68	Remote Similarity	NPD5406	Approved
0.68	Remote Similarity	NPD5404	Approved
0.6795	Remote Similarity	NPD5403	Approved
0.6792	Remote Similarity	NPD7577	Discontinued
0.6791	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5953	Discontinued
0.6783	Remote Similarity	NPD6362	Approved
0.6783	Remote Similarity	NPD3267	Approved
0.6783	Remote Similarity	NPD3266	Approved
0.6781	Remote Similarity	NPD411	Approved
0.6779	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1237	Approved
0.6768	Remote Similarity	NPD6232	Discontinued
0.6767	Remote Similarity	NPD2067	Discontinued
0.6766	Remote Similarity	NPD5844	Phase 1
0.6766	Remote Similarity	NPD7286	Phase 2
0.6765	Remote Similarity	NPD9281	Approved
0.6759	Remote Similarity	NPD2614	Approved
0.6757	Remote Similarity	NPD5124	Phase 1

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