NPASS Compound

Structure

NPC139946 OpenBabel07101718192D 27 28 0 0 1 0 0 0 0 0999 V2000 3.3996 -0.8326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4154 -4.1383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8146 0.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0951 0.9955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8995 -2.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4401 -2.1144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9898 -3.3710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5375 -2.4804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5375 -0.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0375 -1.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5375 -2.4804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5375 -0.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5375 -0.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8995 -0.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9898 0.1423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7557 -2.5738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7557 -0.6549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4401 -1.1144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.2287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0375 -1.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0375 -1.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0375 -1.6144 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5375 -0.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0375 -1.6144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0375 0.1177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0375 -1.6144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 8 11 1 0 0 0 0 8 20 2 0 0 0 0 9 12 2 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 21 25 1 0 0 0 0 22 27 1 6 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.24
Volume:	414.463
LogP:	6.028
LogD:	4.883
LogS:	-5.237
# 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:	0.392
Synthetic Accessibility Score:	3.776
Fsp3:	0.458
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:	-4.704
MDCK Permeability:	2.7172865884494968e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.305
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.457
Plasma Protein Binding (PPB):	100.05968475341797%
Volume Distribution (VD):	0.435
Pgp-substrate:	0.5201465487480164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.265
CYP1A2-substrate:	0.301
CYP2C19-inhibitor:	0.774
CYP2C19-substrate:	0.198
CYP2C9-inhibitor:	0.682
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.781
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.715
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	4.818
Half-life (T1/2):	0.489

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.755
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.978
Carcinogencity:	0.09
Eye Corrosion:	0.015
Eye Irritation:	0.086
Respiratory Toxicity:	0.481

Download Data

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

Natural Product: NPC139946

Natural Product ID:	NPC139946
*Common Name:**	8-O-(P-Coumaroyl)-1(10)E,4(5)E-Humuladien-8-Ol
IUPAC Name:	[(1R,3E,7E)-3,7,10,10-tetramethylcycloundeca-3,7-dien-1-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	SPBVSJHMHZCQRT-WEOKXERDSA-N
Standard InCHI:	InChI=1S/C24H32O3/c1-18-6-5-7-19(2)16-22(17-24(3,4)15-14-18)27-23(26)13-10-20-8-11-21(25)12-9-20/h7-14,22,25H,5-6,15-17H2,1-4H3/b13-10+,18-14+,19-7+/t22-/m0/s1
SMILES:	O=C(O[C@H]1C/C(=C/CC/C(=C/CC(C1)(C)C)/C)/C)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL574685
PubChem CID:	45483026
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
NPO11344.1	Pilea cavaleriei	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19700322]

☑ 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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	12.01	ug.mL-1	PMID[481208]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	25.6	ug.mL-1	PMID[481208]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	40.51	ug.mL-1	PMID[481208]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	=	49.42	ug.mL-1	PMID[481208]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	27.82	ug.mL-1	PMID[481208]

☑ 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 NPC139946 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	200
0.1-0.2	1147
0.2-0.3	3352
0.3-0.4	8407
0.4-0.5	10512
0.5-0.6	9186
0.6-0.7	8337
0.7-0.8	1439
0.8-0.85	86
0.85-0.9	24
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.945	High Similarity	NPC122117
0.9223	High Similarity	NPC304638
0.9057	High Similarity	NPC260952
0.9029	High Similarity	NPC253746
0.8981	High Similarity	NPC183700
0.8932	High Similarity	NPC171843
0.8889	High Similarity	NPC471954
0.8889	High Similarity	NPC75272
0.8796	High Similarity	NPC206341
0.8692	High Similarity	NPC127676
0.8684	High Similarity	NPC203124
0.8684	High Similarity	NPC309434
0.8673	High Similarity	NPC281277
0.8655	High Similarity	NPC204579
0.8644	High Similarity	NPC474532
0.8644	High Similarity	NPC265413
0.8644	High Similarity	NPC10154
0.8636	High Similarity	NPC63345
0.8624	High Similarity	NPC31274
0.8624	High Similarity	NPC470039
0.8585	High Similarity	NPC94343
0.8584	High Similarity	NPC233669
0.8571	High Similarity	NPC137416
0.8544	High Similarity	NPC81010
0.8544	High Similarity	NPC32977
0.8519	High Similarity	NPC243677
0.8519	High Similarity	NPC303141
0.8505	High Similarity	NPC62351
0.85	High Similarity	NPC110211
0.8496	Intermediate Similarity	NPC33749
0.8496	Intermediate Similarity	NPC261453
0.8496	Intermediate Similarity	NPC41851
0.8496	Intermediate Similarity	NPC328593
0.8462	Intermediate Similarity	NPC470849
0.8462	Intermediate Similarity	NPC470848
0.8443	Intermediate Similarity	NPC288290
0.8443	Intermediate Similarity	NPC86257
0.844	Intermediate Similarity	NPC326447
0.844	Intermediate Similarity	NPC92623
0.844	Intermediate Similarity	NPC135464
0.8426	Intermediate Similarity	NPC2518
0.8421	Intermediate Similarity	NPC474967
0.8411	Intermediate Similarity	NPC472585
0.8407	Intermediate Similarity	NPC95381
0.8378	Intermediate Similarity	NPC79543
0.8364	Intermediate Similarity	NPC151530
0.8364	Intermediate Similarity	NPC157473
0.8349	Intermediate Similarity	NPC154899
0.8349	Intermediate Similarity	NPC233396
0.8348	Intermediate Similarity	NPC123559
0.8333	Intermediate Similarity	NPC179686
0.8333	Intermediate Similarity	NPC470202
0.8319	Intermediate Similarity	NPC199462
0.8293	Intermediate Similarity	NPC30174
0.8291	Intermediate Similarity	NPC141791
0.8291	Intermediate Similarity	NPC263386
0.8286	Intermediate Similarity	NPC286006
0.8276	Intermediate Similarity	NPC65791
0.8273	Intermediate Similarity	NPC176971
0.8269	Intermediate Similarity	NPC181709
0.8261	Intermediate Similarity	NPC296526
0.8241	Intermediate Similarity	NPC471578
0.8241	Intermediate Similarity	NPC101025
0.823	Intermediate Similarity	NPC226250
0.819	Intermediate Similarity	NPC128249
0.8182	Intermediate Similarity	NPC146886
0.8182	Intermediate Similarity	NPC20443
0.8182	Intermediate Similarity	NPC60517
0.8182	Intermediate Similarity	NPC128730
0.8174	Intermediate Similarity	NPC217472
0.8173	Intermediate Similarity	NPC270547
0.8158	Intermediate Similarity	NPC26615
0.8158	Intermediate Similarity	NPC17693
0.8155	Intermediate Similarity	NPC98772
0.8145	Intermediate Similarity	NPC194979
0.8142	Intermediate Similarity	NPC222905
0.8142	Intermediate Similarity	NPC473809
0.8131	Intermediate Similarity	NPC201967
0.812	Intermediate Similarity	NPC175799
0.812	Intermediate Similarity	NPC200988
0.812	Intermediate Similarity	NPC610
0.812	Intermediate Similarity	NPC145023
0.8115	Intermediate Similarity	NPC49938
0.8113	Intermediate Similarity	NPC257182
0.8113	Intermediate Similarity	NPC246679
0.811	Intermediate Similarity	NPC11266
0.8103	Intermediate Similarity	NPC23402
0.8095	Intermediate Similarity	NPC138117
0.8095	Intermediate Similarity	NPC325292
0.8087	Intermediate Similarity	NPC190212
0.8083	Intermediate Similarity	NPC147654
0.8077	Intermediate Similarity	NPC55561
0.807	Intermediate Similarity	NPC470355
0.8056	Intermediate Similarity	NPC78119
0.8056	Intermediate Similarity	NPC216468
0.8056	Intermediate Similarity	NPC130193
0.8056	Intermediate Similarity	NPC51333
0.8056	Intermediate Similarity	NPC132078
0.8053	Intermediate Similarity	NPC306045
0.8053	Intermediate Similarity	NPC265211
0.8051	Intermediate Similarity	NPC94298
0.8051	Intermediate Similarity	NPC27633
0.8051	Intermediate Similarity	NPC86198
0.8051	Intermediate Similarity	NPC275519
0.8049	Intermediate Similarity	NPC61181
0.8047	Intermediate Similarity	NPC173569
0.8047	Intermediate Similarity	NPC477874
0.8033	Intermediate Similarity	NPC184219
0.8019	Intermediate Similarity	NPC27323
0.8019	Intermediate Similarity	NPC316301
0.8018	Intermediate Similarity	NPC227255
0.8018	Intermediate Similarity	NPC473855
0.8018	Intermediate Similarity	NPC473393
0.8018	Intermediate Similarity	NPC288760
0.8017	Intermediate Similarity	NPC478058
0.8017	Intermediate Similarity	NPC325301
0.8017	Intermediate Similarity	NPC132518
0.8017	Intermediate Similarity	NPC235250
0.8017	Intermediate Similarity	NPC327070
0.8017	Intermediate Similarity	NPC52097
0.8017	Intermediate Similarity	NPC477151
0.8	Intermediate Similarity	NPC204466
0.8	Intermediate Similarity	NPC476872
0.8	Intermediate Similarity	NPC135784
0.8	Intermediate Similarity	NPC155908
0.7984	Intermediate Similarity	NPC471882
0.7984	Intermediate Similarity	NPC35288
0.7984	Intermediate Similarity	NPC249817
0.7984	Intermediate Similarity	NPC106677
0.7984	Intermediate Similarity	NPC471881
0.7984	Intermediate Similarity	NPC103533
0.7984	Intermediate Similarity	NPC156692
0.7984	Intermediate Similarity	NPC45224
0.7984	Intermediate Similarity	NPC173150
0.7983	Intermediate Similarity	NPC70084
0.7983	Intermediate Similarity	NPC470215
0.7983	Intermediate Similarity	NPC109371
0.7983	Intermediate Similarity	NPC470214
0.7982	Intermediate Similarity	NPC213730
0.7981	Intermediate Similarity	NPC280347
0.7981	Intermediate Similarity	NPC318325
0.7981	Intermediate Similarity	NPC177420
0.7981	Intermediate Similarity	NPC123273
0.7981	Intermediate Similarity	NPC242240
0.7969	Intermediate Similarity	NPC194970
0.7966	Intermediate Similarity	NPC263754
0.7966	Intermediate Similarity	NPC183154
0.7965	Intermediate Similarity	NPC317305
0.7963	Intermediate Similarity	NPC140619
0.7961	Intermediate Similarity	NPC184169
0.7953	Intermediate Similarity	NPC302844
0.7951	Intermediate Similarity	NPC14141
0.7946	Intermediate Similarity	NPC113457
0.7946	Intermediate Similarity	NPC136962
0.7944	Intermediate Similarity	NPC26244
0.7944	Intermediate Similarity	NPC313650
0.7934	Intermediate Similarity	NPC11724
0.7934	Intermediate Similarity	NPC70752
0.7931	Intermediate Similarity	NPC123175
0.7931	Intermediate Similarity	NPC176730
0.7928	Intermediate Similarity	NPC109637
0.7923	Intermediate Similarity	NPC475482
0.7923	Intermediate Similarity	NPC198621
0.7923	Intermediate Similarity	NPC22676
0.7923	Intermediate Similarity	NPC216940
0.792	Intermediate Similarity	NPC219923
0.7917	Intermediate Similarity	NPC202474
0.7909	Intermediate Similarity	NPC7686
0.7909	Intermediate Similarity	NPC40258
0.7909	Intermediate Similarity	NPC91461
0.7905	Intermediate Similarity	NPC300017
0.7903	Intermediate Similarity	NPC213552
0.7903	Intermediate Similarity	NPC120225
0.7903	Intermediate Similarity	NPC471157
0.7899	Intermediate Similarity	NPC206205
0.789	Intermediate Similarity	NPC128723
0.789	Intermediate Similarity	NPC245561
0.789	Intermediate Similarity	NPC92730
0.7886	Intermediate Similarity	NPC246704
0.7886	Intermediate Similarity	NPC469568
0.7885	Intermediate Similarity	NPC25493
0.7885	Intermediate Similarity	NPC104216
0.7885	Intermediate Similarity	NPC113460
0.7881	Intermediate Similarity	NPC131192
0.7881	Intermediate Similarity	NPC19290
0.7874	Intermediate Similarity	NPC235294
0.7874	Intermediate Similarity	NPC46137
0.787	Intermediate Similarity	NPC283711
0.787	Intermediate Similarity	NPC473388
0.7869	Intermediate Similarity	NPC469927
0.7869	Intermediate Similarity	NPC67300
0.7864	Intermediate Similarity	NPC197783
0.7863	Intermediate Similarity	NPC248287
0.7863	Intermediate Similarity	NPC182249
0.7863	Intermediate Similarity	NPC197513
0.7863	Intermediate Similarity	NPC285350
0.7863	Intermediate Similarity	NPC234548
0.7863	Intermediate Similarity	NPC116742
0.7863	Intermediate Similarity	NPC139243
0.7857	Intermediate Similarity	NPC83062

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 NPC139946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	833
0.2-0.3	1434
0.3-0.4	2639
0.4-0.5	2131
0.5-0.6	1293
0.6-0.7	576
0.7-0.8	59
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.844	Intermediate Similarity	NPD3134	Approved
0.8198	Intermediate Similarity	NPD1358	Approved
0.8051	Intermediate Similarity	NPD9545	Approved
0.8019	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD2860	Approved
0.7944	Intermediate Similarity	NPD2859	Approved
0.785	Intermediate Similarity	NPD2934	Approved
0.785	Intermediate Similarity	NPD2933	Approved
0.784	Intermediate Similarity	NPD5736	Approved
0.7769	Intermediate Similarity	NPD4626	Approved
0.7727	Intermediate Similarity	NPD3020	Approved
0.7705	Intermediate Similarity	NPD3496	Discontinued
0.7686	Intermediate Similarity	NPD5691	Approved
0.767	Intermediate Similarity	NPD111	Approved
0.7652	Intermediate Similarity	NPD2684	Approved
0.7647	Intermediate Similarity	NPD7157	Approved
0.7615	Intermediate Similarity	NPD1809	Phase 2
0.7597	Intermediate Similarity	NPD6663	Approved
0.7583	Intermediate Similarity	NPD9493	Approved
0.7556	Intermediate Similarity	NPD8166	Discontinued
0.7542	Intermediate Similarity	NPD7843	Approved
0.7542	Intermediate Similarity	NPD5535	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.7479	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7266	Discontinued
0.7458	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD940	Approved
0.7434	Intermediate Similarity	NPD846	Approved
0.7426	Intermediate Similarity	NPD4628	Phase 3
0.7419	Intermediate Similarity	NPD3847	Discontinued
0.7414	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4140	Approved
0.7368	Intermediate Similarity	NPD6647	Phase 2
0.7345	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD1778	Approved
0.7333	Intermediate Similarity	NPD1241	Discontinued
0.7317	Intermediate Similarity	NPD3091	Approved
0.7317	Intermediate Similarity	NPD1894	Discontinued
0.7308	Intermediate Similarity	NPD7095	Approved
0.7297	Intermediate Similarity	NPD844	Approved
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD845	Approved
0.7266	Intermediate Similarity	NPD2797	Approved
0.7258	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD1357	Approved
0.7252	Intermediate Similarity	NPD3764	Approved
0.7252	Intermediate Similarity	NPD6798	Discontinued
0.725	Intermediate Similarity	NPD821	Approved
0.7244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9697	Approved
0.7227	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD6355	Discontinued
0.7213	Intermediate Similarity	NPD255	Approved
0.7213	Intermediate Similarity	NPD256	Approved
0.7213	Intermediate Similarity	NPD6671	Approved
0.7213	Intermediate Similarity	NPD4198	Discontinued
0.7203	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1282	Approved
0.7179	Intermediate Similarity	NPD968	Approved
0.717	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD228	Approved
0.7165	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD3021	Approved
0.7132	Intermediate Similarity	NPD2935	Discontinued
0.7131	Intermediate Similarity	NPD2629	Approved
0.7121	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5585	Approved
0.7119	Intermediate Similarity	NPD290	Approved
0.7111	Intermediate Similarity	NPD7097	Phase 1
0.7109	Intermediate Similarity	NPD6583	Phase 3
0.7109	Intermediate Similarity	NPD6582	Phase 2
0.7109	Intermediate Similarity	NPD3685	Discontinued
0.7101	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5124	Phase 1
0.7087	Intermediate Similarity	NPD3092	Approved
0.7087	Intermediate Similarity	NPD1535	Discovery
0.708	Intermediate Similarity	NPD288	Approved
0.7068	Intermediate Similarity	NPD6233	Phase 2
0.7068	Intermediate Similarity	NPD4248	Discontinued
0.7068	Intermediate Similarity	NPD4062	Phase 3
0.7063	Intermediate Similarity	NPD3019	Approved
0.7063	Intermediate Similarity	NPD2932	Approved
0.7059	Intermediate Similarity	NPD74	Approved
0.7059	Intermediate Similarity	NPD9266	Approved
0.705	Intermediate Similarity	NPD7003	Approved
0.7045	Intermediate Similarity	NPD5163	Phase 2
0.7042	Intermediate Similarity	NPD6273	Approved
0.7031	Intermediate Similarity	NPD1481	Phase 2
0.7031	Intermediate Similarity	NPD9717	Approved
0.7029	Intermediate Similarity	NPD4534	Discontinued
0.7023	Intermediate Similarity	NPD4208	Discontinued
0.7016	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5909	Discontinued
0.7	Intermediate Similarity	NPD2067	Discontinued
0.7	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5451	Approved
0.7	Intermediate Similarity	NPD6362	Approved
0.6992	Remote Similarity	NPD3268	Approved
0.6977	Remote Similarity	NPD5327	Phase 3
0.6975	Remote Similarity	NPD9263	Approved
0.6975	Remote Similarity	NPD9267	Approved
0.6975	Remote Similarity	NPD9264	Approved
0.697	Remote Similarity	NPD6832	Phase 2
0.6963	Remote Similarity	NPD230	Phase 1
0.6963	Remote Similarity	NPD4340	Discontinued
0.696	Remote Similarity	NPD5536	Phase 2
0.6953	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5647	Approved
0.6947	Remote Similarity	NPD6584	Phase 3
0.6934	Remote Similarity	NPD2799	Discontinued
0.6929	Remote Similarity	NPD4110	Phase 3
0.6929	Remote Similarity	NPD3095	Discontinued
0.6929	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1283	Approved
0.6917	Remote Similarity	NPD2182	Approved
0.6912	Remote Similarity	NPD6653	Approved
0.6911	Remote Similarity	NPD2234	Approved
0.6911	Remote Similarity	NPD2229	Approved
0.6911	Remote Similarity	NPD2228	Approved
0.6909	Remote Similarity	NPD689	Discontinued
0.6905	Remote Similarity	NPD1548	Phase 1
0.6897	Remote Similarity	NPD3028	Approved
0.6897	Remote Similarity	NPD7458	Discontinued
0.6897	Remote Similarity	NPD1242	Phase 1
0.6894	Remote Similarity	NPD2861	Phase 2
0.6894	Remote Similarity	NPD9494	Approved
0.6889	Remote Similarity	NPD825	Approved
0.6889	Remote Similarity	NPD826	Approved
0.6885	Remote Similarity	NPD969	Suspended
0.688	Remote Similarity	NPD9568	Approved
0.6879	Remote Similarity	NPD6190	Approved
0.687	Remote Similarity	NPD9495	Approved
0.687	Remote Similarity	NPD987	Approved
0.687	Remote Similarity	NPD1203	Approved
0.687	Remote Similarity	NPD3094	Phase 2
0.687	Remote Similarity	NPD5926	Approved
0.687	Remote Similarity	NPD1164	Approved
0.6864	Remote Similarity	NPD9608	Approved
0.6864	Remote Similarity	NPD9610	Approved
0.6861	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4359	Approved
0.6846	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4207	Discontinued
0.6842	Remote Similarity	NPD4908	Phase 1
0.6838	Remote Similarity	NPD5735	Approved
0.6831	Remote Similarity	NPD7440	Discontinued
0.6825	Remote Similarity	NPD856	Approved
0.6825	Remote Similarity	NPD16	Approved
0.6822	Remote Similarity	NPD1610	Phase 2
0.6815	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5745	Approved
0.6815	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD8032	Phase 2
0.6812	Remote Similarity	NPD7033	Discontinued
0.681	Remote Similarity	NPD1238	Approved
0.6797	Remote Similarity	NPD2667	Approved
0.6797	Remote Similarity	NPD2668	Approved
0.6797	Remote Similarity	NPD5846	Approved
0.6797	Remote Similarity	NPD4059	Approved
0.6797	Remote Similarity	NPD6516	Phase 2
0.6794	Remote Similarity	NPD3225	Approved
0.6794	Remote Similarity	NPD8651	Approved
0.6791	Remote Similarity	NPD7008	Discontinued
0.6791	Remote Similarity	NPD3027	Phase 3
0.6791	Remote Similarity	NPD3136	Phase 2
0.6791	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6353	Approved
0.6781	Remote Similarity	NPD3455	Phase 2
0.6774	Remote Similarity	NPD6010	Discontinued
0.6774	Remote Similarity	NPD5283	Phase 1
0.6769	Remote Similarity	NPD1608	Approved
0.6767	Remote Similarity	NPD4212	Discontinued
0.6767	Remote Similarity	NPD454	Approved
0.6765	Remote Similarity	NPD3620	Phase 2
0.6765	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1240	Approved
0.6763	Remote Similarity	NPD4476	Approved
0.6763	Remote Similarity	NPD4477	Approved
0.6757	Remote Similarity	NPD9295	Approved
0.675	Remote Similarity	NPD1445	Approved
0.675	Remote Similarity	NPD1444	Approved
0.6746	Remote Similarity	NPD3596	Phase 2
0.6741	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD1048	Approved
0.6741	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1652	Phase 2
0.6723	Remote Similarity	NPD1237	Approved
0.6721	Remote Similarity	NPD4750	Phase 3
0.672	Remote Similarity	NPD5951	Approved
0.6719	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4659	Approved
0.6716	Remote Similarity	NPD2614	Approved
0.6714	Remote Similarity	NPD5865	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